S1

Supporting Information
Nitrile Ylide Dimerisation - Investigation of the Carbene Reactivity of
Nitrile Ylides
Suzanne Fergus, Stephen J. Eustace and Anthony F. Hegarty*

Table of Contents

General experimental S4

Supplementary IR of compd 5f S5

Synthesis of 5f via 1,3-elimination pathway S5

Characterization of compd 5g S5

Characterization of compd 5h S6

Characterization of compd 5i S6

Characterization of compd 5j S7

Characterization of compd 5k S7

Characterization of compd 5l S8

Characterization of compd 5m S8

Characterization of compd 5n S8

Characterization of compd 5o S9

Supplementary IR of compd 13g S9

Characterization of compd 13h S9

Characterization of compd 13i S9

Characterization of compd 13j S10

Characterization of compd 13k S10

Characterization of compd 13l S10

Characterization of compd 13m S10

Synthesis of 12i S11

 S2

Synthesis of 2-Bromomesitylene 30 S12

Synthesis of 2-Mesitaldehyde 31 S12

Synthesis of 2,4,6-Trimethyl-benzonitrile 32 S13

Characterization of compd 16 S13

Characterization of compd 17b S14

Characterization of compd 18b S14

Crystal Structure of 5f S15

Proton NMR spectrum of 5f S16

Carbon NMR spectrum of 5f S16

COSY NMR spectrum of 5f S17

Proton NMR spectrum of 5g S17

Carbon NMR spectrum of 5g S18

COSY NMR spectrum of 5g S18

NOESY NMR of 5g S19

Crystal Structure of 5h S19

Proton NMR spectrum of 5h S20

Carbon NMR spectrum of 5h S20

COSY NMR spectrum of 5h S20

NOESY NMR of 5h S21

Proton NMR spectrum of 5i S21

Carbon NMR spectrum of 5i S22

COSY NMR spectrum of 5i S22

NOESY NMR of 5i S23

Proton NMR spectrum of 5j S23

Carbon NMR spectrum of 5j S24

 S3

COSY NMR spectrum of 5j S24

NOESY NMR of 5j S25

Crystal Structure of 5k S25

Proton NMR spectrum of 5k S26

Carbon NMR spectrum of 5k S26

COSY NMR spectrum of 5k S27

NOESY NMR of 5k S27

Crystal Structure of 5l S28

Proton NMR spectrum of 5l S28

Proton NMR spectrum of 5m S29

Carbon NMR spectrum of 5m S29

Proton NMR spectrum of 5n S30

Carbon NMR spectrum of 5n S31

Proton NMR spectrum of 5o S31

Carbon NMR spectrum of 5o S32

Proton NMR spectrum of 18a S33

Proton NMR spectrum of 18b S34

Crystal data for 5f S34

Crystal data for 5h S38

Crystal data for 5k S44

Crystal data for 5l S50

 S4

General Experimental Methods

All reactions were performed under an inert atmosphere. CH2Cl2, Toluene and

Benzene were distilled from CaH2 and THF was distilled from sodium/benzophenone.

Thin layer chromatography (tlc) was performed on Merck pre-coated silica gel 60F254

slides. Merck silica 9385, particle size 0.04 - 0.063 mm, was used for flash column

chromatography and Merck silica 7734, particle size 0.063 - 0.02 mm was used for

gravity filtrations. 1H NMR were recorded at 300 MHz and 500 MHz and 13C NMR

were recorded at 75.4 MHz and 126 MHz and referenced using tetramethylsilane as

an internal reference. Chemical shifts are quoted in ppm and coupling constants in Hz.
34
The crystal structure of 5f was solved by direct methods, SHELXS-86, and

refined by full matrix least squares using SHELXL-93.35 SHELX operations were
36
rendered paperless using ORTEX which was also used to obtain the drawings. Data

were corrected for Lorentz and polarization effects but not for absorption. Hydrogen

atoms were included in calculated positions with thermal parameters 30% larger than the

atom to which they were attached. The non-hydrogen atoms were refined

anisotropically. The crystal structures of 5h, 5k and 5l were solved by direct methods,
37
SHELXS-97 and refined by full matrix least squares using SHELXS-97.2.38 SHELX

operations were rendered paperless using SHELXTL39 software package. Drawings

were obtained with the Diamond 2.1e Demonstration Version.40 Lorentz and

polarization effects were corrected during integration, a numerical

absoption correction was performed afterwards by the program SADABS (which

is part of the intergration software). All hydrogen atoms could be located

in the difference fourier map. The non-hydrogen atom were refined

anisotropically, the hydrogen atoms isotropically.

 S5

1,1,3,4,6,6-Hexakisphenyl-2,5-diaza-1,3,5-hexatriene 5f

IR (KBr, cm-1): 3076, 3053 (as CH), 3020 (s CH).

Synthesis of 5f via 1,3-elimination of HCl from 18a

A solution of 18a (1.35 g, 4.41 mmol) in dry THF (20.0 mL) was cooled to -78C for

15 minutes using a dry ice/acetone bath. LDA was generated in situ by adding n-

butyllithium 2.5M (1.80 mL, 4.41 mmol) to a solution of diisopropylamine (0.62 mL,

4.41 mmol) in dry THF (20.0 mL) at -78C. The LDA was left for 10 minutes at -

78C before the addition via canula to the imidoyl chloride. The solution was allowed

to stir at room temperature overnight. The following day, the solvent was removed in

vacuo to give an orange/brown oil. Purification by column chromatography using

petroleum ether:ethyl acetate 9:1 as eluant did not prove satifactory in the purification

of the product however recrystallisation of the main fraction (Rf = 0.5-0.6) did yield

the trans phenyl dimer 5f.

1,1,6,6-Tetraphenyl-3,4-bis(2-methyl)-2,5-diaza-1,3,5-hexatriene 5g

Yield 5g (0.19g, 11%). Mp: 217-218C. UV (CH3CN, nm): 249nm ( = 24,658), 408

( = 5102). IR (KBr, cm-1): 3056 (as CH), 3020 (s CH), 2959 (as CH3), 2917 (s

CH3), 1611 (C=N), 1597 (C=C, aromatic). 1H NMR (500 MHz, CDCl3): 2.11 (6H,

s, CH3), 6.61 (4H, m, H10, H14), 6.93-7.01 (6H, m, H5, H6, H7), 7.13 (2H, d,

J=7.429Hz, H4), 7.21-7.24 (8H, m, H11, H13, H17, H19), 7.30-7.33 (4H, m, H12,
13
H18), 7.46 (4H, m, H16, H20). C NMR (126 MHz, CDCl3): 21.1, 124.5, 126.3,

127.7, 127.9, 128.16, 128.2, 128.3, 128.35, 128.4, 128.5, 128.8, 130.097, 130.12,

130.8, 132.5, 133.5, 137.2, 138.8, 165.2. Anal. Calcd for C42H34N2: C, 89.01; H, 6.05;

N, 4.94%. Found: C, 87.25; H, 6.00; N, 4.80. MS: 566 (M+, 90%), 489 (18%), 283

(M+/2, 52%), 165 (100%).

 S6

1,1,6,6-Tetraphenyl-3,4-bis(3-methyl)-2,5-diaza-1,3,5-hexatriene 5h

Yield 5h (0.62g, 25%). Mp: 206-207.5C. UV (CH3CN, nm): 250nm ( = 42,419),

408 ( = 5999). IR (KBr, cm-1): 3060 (as CH), 3020 (s CH), 2917 (as CH3), 2856 (s

CH3), 1598 (C=N), 1570 (C=C, aromatic). 1H NMR (500 MHz, CDCl3): 2.13 (6H,

s, CH3), 6.62 (4H, d, J=7.212Hz, H10, H14), 6.81 (2H, m, H6), 6.91 (2H, s, H8), 6.93

(4H, m, H4, H5), 7.12 (4H, m, H11, H13), 7.24 (2H, m, H12), 7.28 (4H, m, H17,
13
H19), 7.34 (2H, m, H18), 7.56 (4H, d, J=7.526Hz, H16, H20). C NMR (126 MHz,

CDCl3): 21.4, 126.2, 126.6, 127.2, 127.3, 127.8, 127.92, 127.96, 128.0, 128.1,

128.3, 129.1, 129.9, 130.0, 130.1, 132.6, 136.5, 137.8, 139.6, 139.8, 168.2. Anal.

Calcd for C42H34N2: C, 89.01; H, 6.05; N, 4.94%. Found: C, 89.06; H, 6.08; N, 4.99.

1,1,6,6-Tetraphenyl-3,4-bis(4-methyl)-2,5-diaza-1,3,5-hexatriene 5i

Yield 5i (0.16g, 13%) initially purified by gravity filtration using petroleum

ether:ethyl acetate 9:1 as eluant followed by recrystallization from

chloroform/acetonitrile. Mp: 196-197 C. UV (CH3CN, nm): 251nm ( = 41,663), 421

( = 7322). IR (KBr, cm-1): 3053 (as CH), 3024 (s CH), 2918 (as CH3), 2855 (s

CH3), 1620 (C=N), 1596 (C=C, aromatic). 1H NMR (500 MHz, CDCl3): 2.21 (6H,

s, CH3), 6.64 (4H, d, J = 7.409Hz, H10, H14), 6.84 (4H, d, J = 8.549Hz, H5, H7), 7.01

(4H, d, J = 8.454Hz, H4, H8), 7.11 (4H, m, H11, H13), 7.22 (2H, m, H12), 7.29 (4H,
13
m, H17, H19), 7.36 (2H, m, H18), 7.58 (4H, d, J = 7.409Hz, H16, H20). C NMR

(126 MHz, CDCl3): 21.2, 127.4, 127.9, 128.1, 128.9, 129.1, 130.1, 132.5, 135.4,

137.0, 138.0, 139.9, 168.4. Anal. Calcd for C42H34N2: C, 89.01; H, 6.05; N, 4.94%.

Found: C, 88.88; H, 6.21; N, 4.97. MS: 566 (M+, 11%), 283 (M+/2, 49%), 165

(100%), 77 (23%).
 S7

1,1,6,6-Tetraphenyl-3,4-bis(4-methoxy)-2,5-diaza-1,3,5-hexatriene 5j

Yield 5j (0.13g, 11%) initially purified by gravity filtration using petroleum

ether:ethyl acetate 9:1 as eluant followed by recrystallization from

chloroform/acetonitrile. Mp: 193-194C. UV (CH3CN, nm): 258nm ( = 36,415), 422

( = 6437). IR (KBr, cm-1): 3057 (as CH), 2998 (s CH), 2952 (as CH3), 2834 (s

CH3), 1605 (C=N), 1573 (C=C, aromatic), 1176 (C-O-C). 1H NMR (500 MHz,

CDCl3): 3.75 (6H, s, OCH3), 6.63 (4H, d, J=8.976Hz, H5, H7), 6.77 (4H, d,

J=7.428Hz, H10, H14), 7.08 (4H, d, J=8.976Hz, H4, H8), 7.18-7.22 (6H, m, H11-

H13), 7.27 (2H, m, H18), 7.33 (2H, m, H17), 7.41 (2H, m, H19), 7.63 (4H, d,
13
J=7.738Hz, H16, H20). C NMR (126 MHz, CDCl3): 55.2, 112.9, 125.4, 127.5,

127.97, 128.02, 128.2, 128.3, 129.1, 130.1, 130.3, 132.2, 132.7, 138.0, 139.9, 157.7,

168.6. Anal. Calcd for C42H34N2O2: C, 84.25; H, 5.72; N, 4.68%. Found: C, 84.94; H,

6.17; N, 3.97. MS: 598 (M+, 100%), 299 (M+/2, 68%), 284 (17%), 196 (10%), 166

(49%).

1,1,6,6-Tetraphenyl-3,4-bis(3-chloro)-2,5-diaza-1,3,5-hexatriene 5k

Yield 5k (0.066g, 4%). Mp: 217-218.5C. UV (CH3CN, nm): 251nm ( = 15,494),

408nm ( = 2835). IR (KBr, cm-1): 3059 (as CH), 3020 (s CH), 1610 (C=N), 1591

(C=C, aromatic), 694 (C-Cl). 1H NMR (500 MHz, CDCl3): 6.62 (4H, d, J=7.429Hz,

H10, H14), 6.98-7.01 (4H, m, H4, H5), 7.03-7.05 (2H, m, H6), 7.09 (2H, m, H8), 7.18

(4H, m, H11, H13), 7.27-7.33 (6H, m, H12, H17, H19), 7.38-7.41 (2H, m, H18), 7.57

(4H, d, J=7.429Hz, H16, H20). 13C NMR (126 MHz, CDCl3): 126.2, 127.1, 127.7,

127.95, 128.07, 128.3, 128.6, 128.6, 129.1, 129.2, 130.1, 130.6, 132.2, 133.4, 137.4,

139.2, 141.2, 169.2. Anal. Calcd for C40H28N2Cl2: C, 79.07; H, 4.65; N, 4.61; Cl,

11.67%. Found: C, 76.53; H, 4.60; N, 4.17; Cl, 11.75.

 S8

1,1,6,6-Tetraphenyl-3,4-bis(2,4,6-trimethylbenzene)-2,5-diaza-1,3,5-hexatriene 5l

Yield 5l (0.081g, 2.4%) initially purified by gravity filtration using petroleum

ether:ethyl acetate 9:1 as eluant followed by recrystallization from

chloroform/acetonitrile. Mp: 216-218C. UV (CH3CN, nm): 250nm ( = 70,156),

363nm ( = 5409). IR (KBr, cm-1): 3059 (as CH), 3020 (s CH), 2919 (as CH3), 2851

(s CH3), 1631 (C=N), 1596 (C=C, aromatic). 1H NMR (300 MHz, CDCl3): 1.54

(3H, s), 1.63 (9H, s), 2.06 (6H, s), 6.43 (4H, s), 7.22-7.33 (16H, m), 7.65 (4H, s).

Anal. Calcd for C58H42N2: C, 88.71; H, 6.80; N, 4.50%. Found: C, 87.71; H, 6.69; N,

4.49.

1,1,3,4,6,6-Hexakisphenmesityl-2,5-diaza-1,3,5-hexatriene 5m

Yield 5m (0.080g, 6%) initially purified by gravity filtration using petroleum

ether:ethyl acetate 9:1 as eluant followed by recrystallization from

chloroform/acetonitrile. Mp: 313-314C. UV (CH3CN, nm): 267nm ( = 7251),

372nm ( = 7647). IR (KBr, cm-1): 2996 (as CH), 2966 (s CH), 2917 (as CH3), 2853

(s CH3), 1609 (C=N), 1540 (C=C, aromatic). 1H NMR (300 MHz, CDCl3): 1.78

(30H, s), 2.06 (6H, s), 2.10 (9H, s), 2.16 (9H, s), 6.28 (4H, m), 6.42 (8H, s). 13C NMR

(126 MHz, CDCl3): 21.0, 22.45, 23.27, 126.73, 129.31, 134.97, 135.46, 136.75,

136.82, 137.30, 138.16, 147.64, 162.54. Anal. Calcd for C58H66N2: C, 88.05; H, 8.41;

N, 3.54%. Found: C, 84.79; H, 8.09; N, 3.45.

1,1,6,6-Tetrakis(p-toluyl)-3,4-bisphenyl-2,5,diaza-1,3,5-hexatriene 5n

Yield 5n (6%) Mp: 230-213C. IR (KBr, cm-1): 1600 (C=N). UV (THF, nm): 257 (

= 38,200), 410 ( = 5,160). 1H NMR (500 MHz, CDCl3): 2.31 (6H, s) 2.34 (6H, s,),

6.55 (4H, d, J = 7.97 Hz), 6.91 (4H, d, J = 7.97 Hz), 6.95-7.04 (6H, m), 7.09-7.13

(8H, m), 7.48 (4H, d, J = 7.97 Hz). 13C NMR (75 MHz, CDCl3): 21.4, 125.7, 127.2,

127.4, 128.1, 128.6, 129.1, 129.2, 133.1, 135.3, 137.3, 137.9, 139.9, 140.3, 168.9.
 S9

Anal. Calcd for C44H38N2: C, 88.85; H, 6.44; N, 4.71%. Found: C, 87.60; H, 6.50; N,

4.72. MS: 594 (M+, 100%), 297 (M+/2, 60), 194(51), 179 (81).

1,1,3,4,6,6-Hexakis(p-toluyl)-2,5,diaza-1,3,5-hexatriene 5o

Yield 5o (7%) Mp: 257-258C. IR (KBr, cm-1): 3026, 2916, 2361 (C-H), 1601

(C=N). UV (THF, nm): 258 ( = 35,0000), 410 ( = 3,600). 1H NMR (500 MHz,

CDCl3): 2.17 (6H, s), 2.20 (6H, s) 2.27 (6H, s), 6.53 (4H, d, J = 7.69 Hz), 6.82 (4H,

d, J = 7.97 Hz), 6.90 (4H, d, J = 7.69 Hz), 7.00 (4H, d, J = 7.97 Hz), 7.09 (4H, d, J =

7.97 Hz), 7.48 (4H, d, J = 7.97 Hz). 13C NMR (75 MHz, CDCl3): 21.2, 21.4, 127.9,

128.0, 128.6, 128.9, 129.1, 129.4, 132.5, 135.1, 135.2, 137.1, 137.5, 137.7, 140.1,

168.48. Anal. Calcd for C46H42N2: C, 88.71; H, 6.80; N, 4.50%. Found: C, 80.00; H,

6.14; N, 3.89. MS: 622 (M+, 95%), 311 (M+/2, 54%), 194 (48), 179 (100).

1-Dichloromethyl-2-methyl-benzene 13g

IR (liq.film, cm-1): 3071 (as CH), 3027 (s CH), 2977 (as CH3), 2894 (s CH3).

1-Dichloromethyl-3-methyl-benzene 13h

Yield 13h (3.22g, 74%). Bp: 83-84C/0.2mbar Hg (lit. 110-111C/15 Torr).41 IR

(liq.film, cm-1): 3030 (C-H), 2922 (as CH3), 2865 (s CH3), 1607 (C=C, aromatic),

724 (C-Cl). 1H NMR (300 MHz, CDCl3): 2.36 (3H, s), 6.65 (1H, s), 7.15-7.37 (4H,
13
m). C NMR (75 MHz, CDC13): 21.61, 72.22, 123.46, 126.98, 128.93, 130.99,

138.95, 140.63.

1-Dichloromethyl-4-methyl-benzene 13i

Yield 13i (1.32g, 75%). Bp: 74C/0.2mbar Hg (lit. 113-114C/18 Torr).42 IR

(liq.film, cm-1): 3029 (C-H), 2993 (as CH3), 2927 (s CH3), 1608 (C=C, aromatic),

687 (C-Cl). 1H NMR H (300 MHz, CDCl3): 2.36 (3H, s), 6.68 (1H, s), 7.20 (2H, d,
 S10

13
J=8.2Hz), 7.45 (2H, d, J=8.2Hz). C NMR (75 MHz, CDC13): 21.48, 72.10,

126.26, 129.62, 137.93, 140.34.

1-Dichloromethyl-4-methoxy-benzene 13j

Yield 13j (3.79g, 40 %). Bp: 80-81C/0.02mbar Hg (lit. 79C/0.1 Torr).43 IR (liq.film,

cm-1): 2961 (as CH3), 2838 (s CH3), 1608 (C=C, aromatic), 1114 (C-O-C) 694 (C-

Cl). 1H NMR (300 MHz, CDCl3): 3.85 (3H, s), 6.73 (1H, s), 6.94 (2H, d,
13
J=8.639Hz), 7.54 (2H, d, J=8.639Hz). C NMR (75 MHz, CDC13): 55.66, 72.04,

114.27, 127.85, 133.06, 160.94.

1-Dichloromethyl-3-chloro-benzene 13k

Yield 13k (4.84g, 70%). Bp: 66C/0.2mbar Hg (lit. 105C/11 Torr). 44 IR (liq.film,

cm-1): 3066 (as CH), 3000 (s CH3), 1576 (C=C, aromatic), 726 (C-Cl). 1H NMR

(300 MHz, CDCl3): 6.63 (1H, s), 7.30-7.57 (4H, m). 13C NMR (75 MHz, CDC13):

70.91, 124.62, 126.79, 130.36, 134.97, 142.32.

2-Dichloromethyl-1,3,5-trimethyl-benzene 13l

Yield 13l (3.80, 75%). Bp: 57.5-58C/0.01mbar Hg (lit. 78-78.5C/0.7 Torr).45 Mp:
46
35-36C (lit 36C) IR (KBr, cm-1): 2974 (as CH3), 2863 (s CH3), 1611 (C=C,

aromatic), 688 (C-Cl). 1H NMR (300 MHz, CDCl3): 2.26 (3H, s), 2.58 (6H, s), 6.86
13
(2H, s), 7.19 (1H, s). C NMR (75 MHz, CDC13): 20.36, 21.13, 68.47, 130.76,

133.12, 139.79, 141.71.

1-Dichloromethyl-4-nitro-benzene 13m

Yield 13m (6.69g, 65%). Mp: 38-39C (lit. 42C).43 IR (KBr, cm-1): 3079 (as CH3),

2858 (s CH3), 1610 (C=C, aromatic), 1525 (as NO2), 1347(s NO2), 713 (C-Cl). 1H

NMR (300 MHz, CDCl3): 6.78 (1H, s), 7.78 (2H, d, J=8.64Hz), 8.29 (2H, d,

J=8.64Hz). 13C NMR (75 MHz, CDC13): 70.06, 124.39, 127.63, 146.50.
 S11

Benzophenone imine 12i

Bromobenzene (157.02g, 1.0 mol) in 100 mL of dry ether was added drop wise to

magnesium turnings (24.0g, 1.0 mol) in 50 mL of dry THF under an atmosphere of

nitrogen. A crystal of iodine was necessary to initiate the Grignard reaction. The

reaction was refluxed for one hour. A solution of benzonitrile (103.12g, 1.0 mol) in

dry ether (100 mL) was added drop wise leading to the formation of a viscous fawn

colored suspension. The reaction mixture was left to stir overnight at ambient

temperature.

Methanol (45 mL) was added slowly as due to the large scale a vigorous reaction

results. The gummy mixture was filtered and the filtered solid was washed with ether.

The solvent was removed in vacuo and the brown oil was purified by vacuum

distillation twice to give 12i (105.12g). Bp 108C/2 mbar Hg (lit. 90-95C/0.1 Torr).47

IR (liq.film, cm-1): 3058 (N-H), 2961 (as CH3), 2916 (s CH3), 1602 (C=N), 1598

(C=C, aromatic); 1H NMR (300 MHz, CDCl3): 7.38- 7.47 (10H, m), 9.72 (1H, s).
13
C NMR (75 MHz, CDCl3): 128.5, 130.2, 130.4, 177.9. Anal. Calcd for C13H11N:

C, 86.15; H, 6.12; N, 7.73%. Found: C, 85.93; H, 6.15; N, 7.82.

 S12

Synthesis of Mesitonitrile

2-Bromomesitylene 30

Mesitylene (55 mL, 0.4 mol) was stirred in carbon tetrachloride (80 mL) and cooled

to 0C prior to the addition of I2 (0.5g). Br2 (22.5 mL, 0.44 mol) in CCl4 (50 mL) was

added dropwise over 2 h to the cooled solution. After the addition was complete, the

solution was stirred at ambient temperature overnight. The wine solution was washed

with sodium metabisulphite solution, then with deionised water and finally, with a

saturated NaCl solution.

The organic layer was dried over CaCl2, filtered and solvent removed in vacuo to give

red/brown oil. Fractional distillation gave 30 (66.89g, 84%) as a clear oil. Bp 64-

69/1 mbar Hg (lit 69-72/2Torr).48 IR (liq. film, cm-1): 3023, 2997, 2950 (C-H), 2922

(as CH3), 2855 (s CH3), 1585 (C=C, aromatic), 697 (C-Br). 1H NMR (300 MHz,
13
CDC13): 2.72 (s, 3H), 2.36 (s, 6H), 6.87 (s, 2H). C NMR (75 MHz, CDC13):

20.7, 23.7, 124.2, 129.0, 136.3, 137.9. Anal. Calcd for C9H11Br: C, 54.30; H, 5.57; Br,

40.14. Found: C, 54.11; H, 5.51; Br 40.49. MS: 198 (M+ 39%), 119 (M+-Br, 100%),

91 (31%), 77 (16%).

2-Mesitaldehyde 31

30 (14.96g, 0.075 mol) was dissolved in dry THF (150 mL ) under a dry nitrogen

atmosphere. The solution was cooled to 78C and 1.1 equivalents of n-butyllithium

(2.5M, 33 mL, 0.083 mol) were added. The resulting solution was stirred at 78C for

1.5 hours. Dry DMF (10.95g, 0.15 mol) was added and the solution was stirred at

78C for 30 minutes and allowed to stir at room temperature overnight. HCl (5%) was

added and the biphasic mixture was transferred to a separatory funnel. The flask was

washed with diethyl ether and the organic layer when separated was washed with

deionised water and sat. NaCl solution. The aqueous layers were back-extracted using
 S13

CH2Cl2. The organic layers combined were dried over MgSO4, filtered and solvent

removed in vacuo to give pale yellow oil which was purified by distillation to give 31

(9.74g, 75%) as a colorless oil. Bp: 97.5-99 C/5mbar Hg (lit. 96-98 C/6 Torr). 49 IR

(liq. film, cm-1): 2922 (as CH3), 2863 (as CH3), 2766 (C-H), 1682 (C=O). 1H NMR

(300 MHz, CDC13): 2.30 (3H, s), 2.57 (6H, s), 6.88 (2H, s), 10.55 (s, 1H). 13C NMR

(75 MHz, CDC13): 20.5, 21.5, 130.1, 130.5, 141.5, 143.8, 192.9. Anal. Calcd for

C10H12O: C, 81.04; H, 8.12. Found: C, 80.86; H, 8.20. MS: 149 (M++1, 72%), 147

(M+-1, 100%), 119 (72%), 91 (29%), 77 (24%).

2,4,6-Trimethyl-benzonitrile 32

31 (2.29g, 0.019 mol) in EtOH (30 mL) was reacted with hydroxylamine

hydrochloride (2.37g, 0.034 mol) and concentrated HCl (7 drops). After refluxing for

4 h, the pale yellow reaction mixture was poured onto ice and the white solid

precipitate was filtered and dried. Recrystallization was carried out using absolute

alcohol to give 32 (2.43g, 89%). Mp: 49.5-52C (lit. 53C).50 IR (KBr, cm-1): 2975

(as CH), 2921 (s CH), 2216 (CN), 1608 (C=C, aromatic). 1H NMR (300 MHz,
13
CDC13): 2.32 (3H, s), 2.48 (6H, s), 6.93 (2H, s). C NMR (75 MHz, CDC13):

20.8, 21.8, 110.6, 117.8, 128.4, 142.2, 143.0. Anal. Calcd for C10H11N: C, 82.83; H,

7.65; N, 9.66%. Found: C, 82.54; H, 7.63; N, 9.53. MS: 145 (M+, 62%), 144 (M+-1,

14%), 130 (100), 115 (8), 103 (11).

(E)-,'-Dichloro-4,4'-dinitrostilbene 16

Mp: 195-199C (lit 213-214C).16 IR (KBr, cm-1): 1559 (C=C), 1521 (as NO2), 1347

(s NO2), 692 (C-Cl). 1H NMR (300 MHz, CDC13): 7.81 (2H, d, J=9.08Hz), 8.33

(2H, d, J=9.08Hz). Anal. Calcd for C14H8Cl2N2O4: C, 49.75; H, 2.39; N, 8.29; Cl,

20.98. Found: C, 49.01; H, 2.46; N, 7.42; Cl, 21.38. MS: 342 (M++4, 5 %), 340
 S14

(M++2, 29%), 338 (M+, 48%), 246 (18%), 210 (24%), 199 (92%), 176 (100%), 163

(34%).

N-Benzhydryl-4-nitro-benzamide 17b

Yield 17b (8.61, 74%) as cream colored crystals. Mp: 227.5-229.5C (lit 218-

219C).51 UV (CH3CN, nm): 262nm ( = 17140). IR (KBr, cm-1): 3239 (N-H), 2924

(as CH), 2854 (s CH), 1634 (C=O), 1598 (C=C, aromatic), 1516 (as NO2), 1349 (s

NO2). 1H NMR (300 MHz, CDCl3): 6.43 (2H, d, J=7.761Hz), 6.88 (2H, d,

J=7.761Hz), 7.28-7.39 (10H, m), 7.94 (2H, d, J=9.079Hz), 8.24 (2H, d, J=9.079Hz).
13
C NMR (75.4 MHz, CDCl3): 58.14, 129.13, 128.55, 128.11, 127.71, 124.09,

140.00, 141.07, 150.05, 164.82. Anal. Calcd for C20H16N2O3: C, 72.28; H, 4.86; N,

8.43%. Found: C, 72.25; H, 4.86; N, 8.45. MS: 332 (M+, 40%), 331 (M+-1, 10%),

255 (11%), 182 (M+-COArNO2, 120%), 165 (43%), 150 (M+-Ph2CHNH, 66%), 104

(100).

N-Benzhydryl 4-nitrobenzimidoyl chloride 18b

Yield 18b (0.54g). IR (liq.film, cm-1): 2923 (as CH), 2853 (s CH), 1659 (C=N), 1604

(C=C, aromatic), 1521 (as NO2), 1346 (s NO2), 700 (C-Cl). 1H NMR (300 MHz,

CDCl3): 6.26 (1H, s), 7.28-7.46 (10H, m), 8.27 (4H, s). 13C NMR (75 MHz, CDCl3):

71.86, 123.71, 127.79, 128.59, 128.93, 130.37, 140.71, 141.64, 142.28, 149.85.
 C(4)
C(3)
C(2)
C(10)
N(1)
C(9)
C(1)
C(15)

C(16)

FIGURE S1. X-Ray Crystal structure of 5f

 S15

5
6
4
1
N 2
3 7

8 11
10
12
9
N 13
14
15
20 16

19 17
18

FIGURE S2. Proton NMR of 5f

FIGURE S3. Carbon NMR of 5f

 S16

FIGURE S4. COSY NMR of 5f

5
6
4
1
N 2
3 7

8 11
10
12
9
N 13
14
15
20 16

19 17
18

FIGURE S5. Proton NMR of 5g

 S17

FIGURE S6. Carbon NMR of 5g

FIGURE S7. COSY NMR of 5g

 S18

FIGURE S8. NOESY of 5g

C19A
C11A C18A
C10A C20A
C12A C15A C17A
C9A
21A C13A
C6A C16A
C14A
C7A C5A C1A
C4A
C8A NA
C3A
C2 C2A
C3
N
C4 C8
C5
C14 C7
C1 C6
C16 C13 C21
C15 C9
C17 C12
C20 C10
C18
C19 C11

FIGURE S9. X-Ray Crystal Structure of 5h

 S19

5
6
4
1
N 2
3 7

8 11
10
12
9
N 13
14
15
20 16

19 17
18

FIGURE S10. Proton NMR of 5h

FIGURE S11. Carbon NMR of 5h

FIGURE S12. COSY of 5h

 S20

FIGURE S13. NOESY of 5h

5
6
4
1
N 2
3 7

8 11
10
12
9
N 13
14
15
20 16

19 17
18

FIGURE S14. Proton NMR of 5i

 S21

FIGURE S15. Carbon NMR of 5i

FIGURE S16. COSY NMR of 5i

 S22

FIGURE S17. NOESY of 5i

5
6 OCH3
4
1
N 2
3 7

8 11
10
12
9
N 13
14
15
20 16
H3CO
19 17
18

FIGURE S18. Proton of 5j

 S23

FIGURE S19. Carbon NMR of 5j

FIGURE S20. COSY NMR of 5j

 S24

FIGURE S21. NOESY of 5j

Cl
C19A

C5 C20A
C6 C18A
C7 C11A
C15A C10A
C4 C8 C17A C12A
C3 C9A
C16A C13A
C1A
C14A
N C2 NA
C2A
C1
C14 C16
C8A C3A
C13 C9
C12 C10 C15 C17
C11 C7A C4A
C18
C20 C5A
C19 C6A

ClA

FIGURE S22. X-Ray Crystal Structure of 5k

 S25

5
6
4
1
N 2
3 7

8
10
Cl 11
12
9
Cl N 13
14
15
20 16

19 17
18

FIGURE S23. Proton NMR of 5k

FIGURE S24. Carbon NMR of 5k

 S26

FIGURE S25. COSY NMR of 5k

FIGURE S26. NOESY of 5k

 S27

C9'
C23
C1'
C21' C15'
N1
N2
C15
C3 C2 C2'
C3'
C1
C22 C22'
C9
C23'
C21

FIGURE S27. X-Ray Crystal Structure of 5l

FIGURE S28. Proton NMR of 5l

 S28

N
Mes
N
Mes

FIGURE S29. Proton NMR of 5m

FIGURE S30. Carbon NMR of 5m

 S29

FIGURE S31. Proton NMR of 5n

 S30

FIGURE S32. Carbon NMR of 5n

FIGURE S33. Proton NMR of 5o

 S31

FIGURE S34. Carbon NMR of 5o

 S32

Cl
N

FIGURE S35. Proton NMR of 18a

 S33

Cl
N

NO2

FIGURE S36. Proton NMR of 18b

TABLE S1. Crystal data and structure refinement for 5f.

Empirical formula C20 H16 N

Formula weight 270.34
Temperature 293(2) K
Wavelength 0.71069
Crystal system Monoclinic
Space group P21/c
Unit cell dimensions a = 10.20(2) = 90
b = 11.47(2) = 92.69(2)
c = 12.75(2) = 90
3
Volume 1490(5)
Z 4
3
Density (calculated) 1.205 Mg/m
-1
Absorption coefficient 0.070 mm
F(000) 572
 S34

Crystal size 0.45 x 0.22 x 0.20 mm

Theta range for data collection 2.00 to 21.97 .
Index ranges -1<=h<=10; 0<=k<=12; -13<=l<=13
Reflections collected 2000
Independent reflections 1823 [R(int) = 0.0993]
Reflections observed (>2) 1092
2
Refinement method Full-matrix least-squares on F
Data / restraints / parameters 1823 / 0 / 190
2
Goodness-of-fit on F 1.250
Final R indices [I>2(I)] R1 = 0.0819 wR2 = 0.2038
R indices (all data) R1 = 0.1230 wR2 = 0.2181
-3
Largest diff. peak and hole 0.251 and -0.552 e.

R indices ; R1 = [ Fo - Fc ]/ Fo (based on F),

wR2 = [[w ( Fo 2 - Fc2 ) 2]/[w (Fo 2)2]]1/2 (based on F2). w = 1/[(Fo)2 + (0.1*P)2].
Goodness-of-fit = [w ( Fo2 - Fc2 )2/(Nobs-Nparameters)]1/2.

TABLE S2. Atomic coordinates (x 104) and equivalent isotropic displacement

parameters (2 x 103) .U(eq) is defined as one third of the trace of the orthogonalized
Uij tensor.

Atom x y z U(eq)

N(1) 9189(3) 1451(3) 9756(3) 45(1)

C(1) 8528(4) 1549(4) 8883(3) 40(1)
C(2) 10158(4) 555(4) 9938(3) 45(1)
C(3) 11508(5) 1038(4) 9983(4) 48(1)
C(4) 11813(5) 2009(4) 10568(4) 65(2)
C(5) 13046(8) 2492(6) 10627(6) 95(2)
C(6) 14024(7) 1950(7) 10060(7) 103(3)
C(7) 13731(6) 1005(7) 9480(6) 99(2)
C(8) 12503(5) 507(5) 9429(4) 65(2)
C(9) 8750(4) 771(4) 7967(3) 44(1)
C(10) 9884(5) 859(5) 7458(4) 58(1)
C(11) 10167(6) 112(5) 6628(4) 70(2)
C(12) 9230(7) -700(5) 6319(4) 72(2)
C(13) 8101(6) -794(5) 6802(4) 67(2)
C(14) 7833(5) -47(4) 7623(4) 52(1)
C(15) 7569(4) 2503(4) 8773(3) 41(1)
C(16) 6826(4) 2677(4) 7845(4) 60(1)
C(17) 5945(5) 3599(5) 7753(4) 75(2)
C(18) 5798(5) 4360(4) 8563(5) 66(2)
C(19) 6535(5) 4193(4) 9485(4) 57(1)
C(20) 7406(4) 3283(4) 9587(4) 51(1)
 S35

TABLE S3. Bond lengths [] and angles [] for 5f.

N(1)-C(1) 1.279(5)
N(1)-C(2) 1.438(6)
C(1)-C(15) 1.470(6)
C(1)-C(9) 1.495(6)
C(2)-C(2)#1 1.325(9)
C(2)-C(3) 1.483(7)
C(3)-C(4) 1.368(7)
C(3)-C(8) 1.403(7)
C(4)-C(5) 1.373(8)
C(5)-C(6) 1.404(10)
C(6)-C(7) 1.338(10)
C(7)-C(8) 1.376(8)
C(9)-C(10) 1.356(6)
C(9)-C(14) 1.383(6)
C(10)-C(11) 1.401(7)
C(11)-C(12) 1.378(8)
C(12)-C(13) 1.335(8)
C(13)-C(14) 1.391(7)
C(15)-C(20) 1.386(6)
C(15)-C(16) 1.390(6)
C(16)-C(17) 1.389(7)
C(17)-C(18) 1.366(7)
C(18)-C(19) 1.379(7)
C(19)-C(20) 1.373(6)

C(1)-N(1)-C(2) 122.2(4)
N(1)-C(1)-C(15) 117.9(4)
N(1)-C(1)-C(9) 122.4(4)
C(15)-C(1)-C(9) 119.6(4)
C(2)#1-C(2)-N(1) 122.5(5)
C(2)#1-C(2)-C(3) 125.8(6)
N(1)-C(2)-C(3) 111.7(4)
C(4)-C(3)-C(8) 118.5(5)
C(4)-C(3)-C(2) 120.8(5)
C(8)-C(3)-C(2) 120.7(4)
C(3)-C(4)-C(5) 122.9(6)
C(4)-C(5)-C(6) 117.7(6)
C(7)-C(6)-C(5) 119.8(7)
C(6)-C(7)-C(8) 122.9(7)
C(7)-C(8)-C(3) 118.3(6)
C(10)-C(9)-C(14) 118.6(5)
C(10)-C(9)-C(1) 119.6(4)
C(14)-C(9)-C(1) 121.9(4)
C(9)-C(10)-C(11) 121.7(5)
C(12)-C(11)-C(10) 117.7(5)
C(13)-C(12)-C(11) 121.6(5)
C(12)-C(13)-C(14) 120.1(5)
C(9)-C(14)-C(13) 120.2(5)
 S36

C(20)-C(15)-C(16) 117.6(4)
C(20)-C(15)-C(1) 120.9(4)
C(16)-C(15)-C(1) 121.5(4)
C(17)-C(16)-C(15) 120.4(5)
C(18)-C(17)-C(16) 121.1(5)
C(17)-C(18)-C(19) 118.7(5)
C(20)-C(19)-C(18) 120.7(5)
C(19)-C(20)-C(15) 121.4(5)

Symmetry transformations used to generate equivalent atoms:

#1 -x+2,-y,-z+2

TABLE S4. Anisotropic displacement parameters (2 x 103). The anisotropic

displacement factor exponent takes the form: -2 2 [h2 a*2 U11 + ... + 2 h k a* b* U

Atom U11 U22 U33 U23 U13 U12

N(1) 55(2) 38(2) 42(2) -3(2) -8(2) 12(2)

C(1) 45(3) 38(3) 37(3) -3(2) 0(2) 0(2)
C(2) 65(3) 46(3) 24(2) -14(2) -3(2) -4(3)
C(3) 56(3) 39(3) 46(3) 4(2) -12(2) -3(3)
C(4) 83(4) 43(3) 66(3) 12(3) -19(3) -4(3)
C(5) 104(5) 52(4) 124(6) 24(4) -50(5) -29(4)
C(6) 83(5) 81(5) 142(7) 57(5) -39(5) -30(5)
C(7) 67(4) 106(6) 123(6) 34(5) 7(4) -11(4)
C(8) 68(4) 61(4) 67(4) 4(3) 1(3) 4(3)
C(9) 53(3) 45(3) 33(2) 7(2) -2(2) 6(2)
C(10) 64(3) 68(4) 43(3) 2(3) 5(2) 3(3)
C(11) 81(4) 78(4) 50(3) -5(3) 14(3) 14(4)
C(12) 100(5) 71(4) 44(3) -13(3) -2(3) 24(4)
C(13) 99(4) 51(3) 49(3) -7(3) -17(3) 1(3)
C(14) 64(3) 46(3) 45(3) 0(3) -7(2) -1(3)
C(15) 44(3) 41(3) 38(3) -6(2) 1(2) 2(2)
C(16) 73(3) 52(3) 53(3) -9(3) -15(3) 18(3)
C(17) 83(4) 68(4) 70(4) 0(3) -27(3) 30(3)
C(18) 63(3) 47(3) 87(4) -1(3) 1(3) 19(3)
C(19) 62(3) 48(3) 63(3) -12(3) 3(3) 6(3)
C(20) 58(3) 47(3) 48(3) -3(3) 1(2) 6(3)

TABLE S5. Hydrogen coordinates (x 104) and isotropic displacement parameters

(2 x 103) for 5f.

Atom x y z U(eq)

H(2) 10202 435 9179 59

H(4) 11157 2356 10943 84
H(5) 13227 3155 11028 123
H(6) 14874 2247 10088 134
H(7) 14386 671 9095 129
H(8) 12337 -165 9037 85
 S37

H(10) 10490 1430 7664 75

H(11) 10959 162 6299 90
H(12) 9388 -1193 5760 93
H(13) 7494 -1361 6589 87
H(14) 7033 -97 7942 67
H(16) 6919 2174 7282 78
H(17) 5447 3700 7130 97
H(18) 5212 4979 8493 86
H(19) 6440 4702 10044 75
H(20) 7897 3189 10214 66

TABLE S6. Crystal data and structure refinement for 5h.

Empirical formula C42 H34 N2

Formula weight 566.71
Temperature 293(2) K
Wavelength 0.71073
Crystal system, space group Monoclinic, P21/c
Unit cell dimensions a = 10.3406(8) = 90
b = 12.6359(10) = 90.2880(10)
c = 12.1272(10) = 90
3
Volume 1584.6(2)
3
Z, Calculated density 2, 1.188 Mg/m
-1
Absorption coefficient 0.069 mm
F(000) 600
Crystal size 0.50 x 0.50 x 0.50 mm
Theta range for data collection 1.97 to 28.29
Limiting indices -13<=h<=13, -16<=k<=16, -16<=l<=15
Reflections collected / unique 26138 / 3785 [R(int) = 0.0220]
Completeness to theta = 28.29 96.3 %
Absorption correction Numerical
Max. and min. transmission 0.9665 and 0.9665
2
Refinement method Full-matrix least-squares on F
Data / restraints / parameters 3785 / 0 / 279
Goodness-of-fit on F^2 1.053
Final R indices [I>2sigma(I)] R1 = 0.0495, wR2 = 0.1205
R indices (all data) R1 = 0.0601, wR2 = 0.1274
-3
Largest diff. peak and hole 0.228 and -0.137 e.

TABLE S7. Atomic coordinates (x 104) and equivalent isotropic displacement

parameters (2 x 103) for 5h.
U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

Atom x y z U(eq)

N 744(1) 1330(1) 5271(1) 41(1)

 S38

C(1) 1440(1) 1389(1 6144(1) 36(1)

C(2) -171(1) 503(1) 5109(1) 39(1)
C(3) -1529(1) 893(1) 5119(1) 40(1)
C(4) -2489(1) 371(1) 5709(1) 51(1)
C(5) -3738(1) 768(1) 5709(1) 60(1)
C(6) -4042(1) 1673(1) 5127(1) 59(1)
C(7) -3104(1) 2207(1) 4537(1) 52(1)
C(8) -1846(1) 1812(1) 4551(1) 45(1)
C(9) 1328(1) 628(1) 7084(1) 41(1)
C(10) 2319(2) -62(1) 7362(1) 51(1)
C(11) 2139(2) -813(1) 8180(1) 68(1)
C(12) 981(2) -872(2) 8721(2) 82(1)
C(13) 12(2) -177(2) 8469(2) 86(1)
C(14) 174(2) 573(2) 7658(1) 62(1)
C(21) -3421(2) 3185(2) 3891(2) 74(1)
C(15) 2369(1) 2286(1) 6225(1) 38(1)
C(16) 2501(1) 2989(1) 5346(1) 46(1)
C(17) 3330(1) 3838(1) 5421(1) 57(1)
C(18) 4050(2) 4006(1) 6369(2) 61(1)
C(19) 3933(2) 3328(1) 7239(2) 63(1)
C(20) 3095(1) 2469(1) 7173(1) 52(1)

TABLE S8. Bond lengths [] and angles [] for 5h.

N-C(1) 1.2788(14)
N-C(2) 1.4223(15)
C(1)-C(15) 1.4897(16)
C(1)-C(9) 1.4967(16)
C(2)-C(2)#1 1.346(2)
C(2)-C(3) 1.4883(17)
C(3)-C(8) 1.3881(18)
C(3)-C(4) 1.3939(19)
C(4)-C(5) 1.385(2)
C(4)-H(4) 1.038(17)
C(5)-C(6) 1.380(2)
C(5)-H(5) 0.965(17)
C(6)-C(7) 1.383(2)
C(6)-H(6) 0.975(17)
C(7)-C(8) 1.3936(19)
C(7)-C(21) 1.498(2)
C(8)-H(8) 0.959(14)
C(9)-C(10) 1.3852(18)
C(9)-C(14) 1.3864(19)
C(10)-C(11) 1.387(2)
C(10)-H(10) 0.980(16)
C(11)-C(12) 1.371(3)
C(11)-H(11) 0.935(19)
C(12)-C(13) 1.366(3)
C(12)-H(12) 0.95(2)
C(13)-C(14) 1.377(2)
 S39

C(13)-H(13) 0.92(2)
C(14)-H(14) 0.977(18)
C(21)-H(21A) 0.98(3)
C(21)-H(21B) 1.05(3)
C(21)-H(21C) 1.00(4)
C(21)-H(21D) 1.07(5)
C(21)-H(21E) 1.06(4)
C(21)-H(21F) 1.05(4)
C(15)-C(20) 1.3884(18)
C(15)-C(16) 1.3941(18)
C(16)-C(17) 1.3765(19)
C(16)-H(16) 0.952(15)
C(17)-C(18) 1.382(2)
C(17)-H(17) 0.930(18)
C(18)-C(19) 1.366(2)
C(18)-H(18) 0.961(18)
C(19)-C(20) 1.391(2)
C(19)-H(19) 0.963(18)
C(20)-H(20) 0.924(17)

C(1)-N-C(2) 121.90(10)
N-C(1)-C(15) 117.35(10)
N-C(1)-C(9) 123.23(10)
C(15)-C(1)-C(9) 119.39(10)
C(2)#1-C(2)-N 123.08(13)
C(2)#1-C(2)-C(3) 124.28(13)
N-C(2)-C(3) 112.47(10)
C(8)-C(3)-C(4) 118.93(12)
C(8)-C(3)-C(2) 119.58(11)
C(4)-C(3)-C(2) 121.47(11)
C(5)-C(4)-C(3) 119.69(14)
C(5)-C(4)-H(4) 122.0(9)
C(3)-C(4)-H(4) 118.3(9)
C(6)-C(5)-C(4) 120.63(15)
C(6)-C(5)-H(5) 116.0(10)
C(4)-C(5)-H(5) 123.1(10)
C(5)-C(6)-C(7) 120.74(13)
C(5)-C(6)-H(6) 119.3(10)
C(7)-C(6)-H(6) 120.0(10)
C(6)-C(7)-C(8) 118.40(13)
C(6)-C(7)-C(21) 121.38(15)
C(8)-C(7)-C(21) 120.22(15)
C(3)-C(8)-C(7) 121.58(13)
C(3)-C(8)-H(8) 118.4(8)
C(7)-C(8)-H(8) 120.0(8)
C(10)-C(9)-C(14) 118.96(13)
C(10)-C(9)-C(1) 121.96(11)
C(14)-C(9)-C(1) 118.98(12)
C(9)-C(10)-C(11) 120.22(15)
C(9)-C(10)-H(10) 118.9(10)
 S40

C(11)-C(10)-H(10) 120.8(10)
C(12)-C(11)-C(10) 119.99(17)
C(12)-C(11)-H(11) 120.9(12)
C(10)-C(11)-H(11) 119.0(12)
C(13)-C(12)-C(11) 120.01(16)
C(13)-C(12)-H(12) 120.0(13)
C(11)-C(12)-H(12) 119.9(13)
C(12)-C(13)-C(14) 120.71(18)
C(12)-C(13)-H(13) 121.6(15)
C(14)-C(13)-H(13) 117.7(15)
C(13)-C(14)-C(9) 120.07(17)
C(13)-C(14)-H(14) 122.2(11)
C(9)-C(14)-H(14) 117.7(11)
C(7)-C(21)-H(21A) 108.3(17)
C(7)-C(21)-H(21B) 113.3(17)
H(21A)-C(21)-H(21B) 109(3)
C(7)-C(21)-H(21C) 109.4(19)
H(21A)-C(21)-H(21C) 102(3)
H(21B)-C(21)-H(21C) 113(3)
C(7)-C(21)-H(21D) 111(2)
H(21A)-C(21)-H(21D) 141(3)
H(21B)-C(21)-H(21D) 53(2)
H(21C)-C(21)-H(21D) 65(3)
C(7)-C(21)-H(21E) 106(2)
H(21A)-C(21)-H(21E) 47(2)
H(21B)-C(21)-H(21E) 67(3)
H(21C)-C(21)-H(21E) 139(3)
H(21D)-C(21)-H(21E) 118(3)
C(7)-C(21)-H(21F) 113(2)
H(21A)-C(21)-H(21F) 56(2)
H(21B)-C(21)-H(21F) 134(3)
H(21C)-C(21)-H(21F) 47(2)
H(21D)-C(21)-H(21F) 108(3)
H(21E)-C(21)-H(21F) 101(3)
C(20)-C(15)-C(16) 118.19(12)
C(20)-C(15)-C(1) 121.83(11)
C(16)-C(15)-C(1) 119.96(11)
C(17)-C(16)-C(15) 120.60(13)
C(17)-C(16)-H(16) 119.5(9)
C(15)-C(16)-H(16) 119.9(9)
C(16)-C(17)-C(18) 120.46(14)
C(16)-C(17)-H(17) 118.7(11)
C(18)-C(17)-H(17) 120.9(11)
C(19)-C(18)-C(17) 119.84(14)
C(19)-C(18)-H(18) 119.4(10)
C(17)-C(18)-H(18) 120.8(10)
C(18)-C(19)-C(20) 120.10(14)
C(18)-C(19)-H(19) 121.7(11)
C(20)-C(19)-H(19) 118.2(11)
C(15)-C(20)-C(19) 120.81(14)
 S41

C(15)-C(20)-H(20) 118.8(10)
C(19)-C(20)-H(20) 120.4(10)

Symmetry transformations used to generate equivalent atoms:

#1 -x,-y,-z+1

TABLE S9. Anisotropic displacement parameters (2 x 103) for 5h.

The anisotropic displacement factor exponent takes the form:
-2 2 [h2 a*2 U11 + ... + 2 h k a* b* U12

Atom U11 U22 U33 U23 U13 U12

N 41(1) 38(1) 43(1) 3(1) -5(1) 2(1)

C(1) 35(1) 36(1) 37(1) -1(1) 1(1) 3(1)
C(2) 39(1) 40(1) 37(1) 5(1) -5(1) -2(1)
C(3) 42(1) 39(1) 40(1) -5(1 -7(1) 0(1)
C(4) 48(1) 52(1) 54(1) 3(1) 1(1) 0(1)
C(5) 47(1) 65(1) 68(1) 0(1) 9(1) -2(1)
C(6) 45(1) 58(1) 75(1) -12(1) -3(1) 9(1)
C(7) 54(1) 39(1) 62(1) -8(1) -13(1) 7(1)
C(8) 46(1) 39(1) 50(1) -2(1) -7(1) -2(1)
C(9) 45(1) 42(1) 35(1) -1(1) -4(1) -6(1)
C(10) 58(1) 49(1) 45(1) 0(1) -7(1) 3(1)
C(11) 96(1) 53(1) 55(1) 7(1) -22(1) 5(1)
C(12) 105(2) 82(1) 58(1) 31(1) -11(1) -25(1)
C(13) 73(1) 124(2) 59(1) 33(1) 9(1) -20(1)
C(14) 51(1) 87(1) 48(1) 14(1) 3(1) -2(1)
C(21) 70(1) 52(1) 100(2) 9(1) -17(1) 12(1)
C(15) 36(1) 36(1) 43(1) -3(1) 2(1) 2(1)
C(16) 43(1) 46(1) 49(1) 3(1) 0(1) -1(1)
C(17) 55(1) 43(1) 74(1) 12(1) 5(1) -2(1)
C(18) 52(1) 38(1) 94(1) -3(1) -7(1) -7(1)
C(19) 66(1) 51(1) 70(1) -9(1) -20(1) -8(1)
C(20) 62(1) 47(1) 48(1) -1(1) -9(1) -7(1)
 S42

TABLE S10. Hydrogen coordinates (x 104) and isotropic displacement parameters

(2 x 103) for 5h.

Atom x y z U(eq)

H(4) -2237(15) -308(14) 6143(13) 66(5)

H(5) -4419(16) 480(13) 6161(14) 68(5)
H(6) -4928(17) 1936(13) 5134(13) 66(4)
H(8) -1180(13) 2165(11) 4144(11) 39(3)
H(10) 3130(16) -29(13) 6949(13) 62(4)
H(11) 2803(18) -1297(16) 8329(15) 82(6)
H(12) 830(20) -1426(17) 9234(18) 95(6)
H(13) -780(20) -207(18) 8814(19) 104(7)
H(14) -513(17) 1066(14) 7449(15) 75(5)
H(16) 1987(14) 2899(12) 4699(12) 51(4)
H(17) 3393(16) 4295(14) 4823(15) 66(5)
H(18) 4642(17) 4590(14) 6420(14) 74(5)
H(19) 4420(16) 3426(14) 7911(15) 72(5)
H(20) 3006(15) 2013(13) 7763(14) 62(5)
H(21A) -2990(30) 3140(30) 3180(30) 67(9)
H(21B) -4410(30) 3290(30) 3770(30) 79(9)
H(21C) -2990(40) 3800(30) 4240(30) 84(10)
H(21D) -4050(50) 3690(40) 4350(40) 60(12)
H(21E) -3730(50) 2930(30) 3100(40) 51(11)
H(21F) -2600(40) 3630(30) 3680(40) 39(9)

TABLE S11. Torsion angles [] for 5h.

C(2)-N-C(1)-C(15) 179.81(10)
C(2)-N-C(1)-C(9) -2.28(17)
C(1)-N-C(2)-C(2)#1 -72.10(19)
C(1)-N-C(2)-C(3) 112.38(12)
C(2)#1-C(2)-C(3)-C(8) -131.55(16)
N-C(2)-C(3)-C(8) 43.90(15)
C(2)#1-C(2)-C(3)-C(4) 50.1(2)
N-C(2)-C(3)-C(4) -134.49(12)
C(8)-C(3)-C(4)-C(5) 0.8(2)
C(2)-C(3)-C(4)-C(5) 179.16(13)
C(3)-C(4)-C(5)-C(6) 0.3(2)
C(4)-C(5)-C(6)-C(7) -0.4(2)
C(5)-C(6)-C(7)-C(8) -0.4(2)
C(5)-C(6)-C(7)-C(21) 179.42(17)
C(4)-C(3)-C(8)-C(7) -1.62(19)
C(2)-C(3)-C(8)-C(7) 179.95(11)
C(6)-C(7)-C(8)-C(3) 1.4(2)
C(21)-C(7)-C(8)-C(3) -178.38(15)
N-C(1)-C(9)-C(10) 113.83(14)
C(15)-C(1)-C(9)-C(10) -68.31(15)
N-C(1)-C(9)-C(14) -62.72(17)
 S43

C(15)-C(1)-C(9)-C(14) 115.14(14)
C(14)-C(9)-C(10)-C(11) 1.8(2)
C(1)-C(9)-C(10)-C(11) -174.72(12)
C(9)-C(10)-C(11)-C(12) -0.3(2)
C(10)-C(11)-C(12)-C(13) -1.3(3)
C(11)-C(12)-C(13)-C(14) 1.4(3)
C(12)-C(13)-C(14)-C(9) 0.1(3)
C(10)-C(9)-C(14)-C(13) -1.7(2)
C(1)-C(9)-C(14)-C(13) 174.91(16)
N-C(1)-C(15)-C(20) 174.84(12)
C(9)-C(1)-C(15)-C(20) -3.14(17)
N-C(1)-C(15)-C(16) -3.25(16)
C(9)-C(1)-C(15)-C(16) 178.76(11)
C(20)-C(15)-C(16)-C(17) 0.09(19)
C(1)-C(15)-C(16)-C(17) 178.25(12)
C(15)-C(16)-C(17)-C(18) 0.2(2)
C(16)-C(17)-C(18)-C(19) -0.3(2)
C(17)-C(18)-C(19)-C(20) 0.1(3)
C(16)-C(15)-C(20)-C(19) -0.3(2)
C(1)-C(15)-C(20)-C(19) -178.39(13)
C(18)-C(19)-C(20)-C(15) 0.1(2)
Symmetry transformations used to generate equivalent atoms:
#1 -x,-y,-z+1

TABLE 12. Crystal data and structure refinement for 5k.

Empirical formula C40 H28 Cl2 N2

Formula weight 607.54
Temperature 293(2) K
Wavelength 0.71073
Crystal system, space group Monoclinic, P21/c
Unit cell dimensions a = 10.274(5) A = 90 deg
b = 12.574(6) A = 90.626(7) deg.
c = 12.144(6) A = 90 deg.
3
Volume 1568.7(13)
3
Z, Calculated density 2, 1.286 Mg/m
3
Absorption coefficient 0.239 Mg/m
F(000) 632
Crystal size 0.70 x 0.70 x 0.50 mm
Theta range for data collection 1.98 to 28.33.
Limiting indices -13<=h<=13, -16<=k<=16, -16<=l<=15
Reflections collected / unique 24350 / 3687 [R(int) = 0.0316]
Completeness to theta = 28.33 94.2 %
Absorption correction Numerical
Max. and min. transmission 0.8899 and 0.8507
2
Refinement method Full-matrix least-squares on F
Data / restraints / parameters 3687 / 0 / 255
 S44

Goodness-of-fit on F^2 1.024

Final R indices [I>2sigma(I)] R1 = 0.0476, wR2 = 0.1142
R indices (all data) R1 = 0.0653, wR2 = 0.1267
-3
Largest diff. peak and hole 0.316 and -0.361 e.

TABLE 13. Atomic coordinates (x 104) and equivalent isotropic displacement

parameters (2 x 103) for 5k.
U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

Atom x y z U(eq)

Cl 8428(1) 1670(1) 3778(1) 79(1)

N 4238(1) 3664(1) 5263(1) 36(1)
C(1) 3559(1) 3603(1) 6135(1) 33(1)
C(2) 5165(1) 4492(1) 5110(1) 35(1)
C(3) 6524(2) 4095(1) 5118(1) 37(1)
C(4) 6818(2) 3172(1) 4542(1) 41(1)
C(5) 8080(2) 2801(1) 4542(2) 48(1)
C(6) 9062(2) 3304(2) 5119(2) 55(1)
C(7) 8758(2) 4209(2) 5703(2) 56(1)
C(8) 7509(2) 4610(1) 5710(1) 46(1)
C(9) 3705(2) 4360(1) 7080(1) 37(1)
C(10) 4878(2) 4383(2) 7657(2) 54(1)
C(11) 5073(2) 5126(2) 8480(2) 75(1)
C(12) 4119(3) 5844(2) 8734(2) 75(1)
C(13) 2946(3) 5815(2) 8187(2) 63(1)
C(14) 2733(2) 5068(1) 7364(1) 46(1)
C(15) 2608(1) 2712(1) 6212(1) 35(1)
C(16) 1862(2) 2554(2) 7143(2) 49(1)
C(17) 999(2) 1708(2) 7201(2) 59(1)
C(18) 875(2) 1013(1) 6341(2) 57(1)
C(19) 1622(2) 1157(1) 5410(2) 53(1)
C(20) 2471(2) 1996(1) 5338(2) 43(1)

TABLE 14. Bond lengths [] and angles [] for 5k.

Cl-C(5) 1.7378(19)
N-C(1) 1.2767(19)
N-C(2) 1.4251(19)
C(1)-C(15) 1.490(2)
C(1)-C(9) 1.497(2)
C(2)-C(2)#1 1.347(3)
C(2)-C(3) 1.483(2)
C(3)-C(4) 1.389(2)
C(3)-C(8) 1.394(2)
C(4)-C(5) 1.378(2)
C(4)-H(4) 0.900(19)
 S45

C(5)-C(6) 1.376(3)
C(6)-C(7) 1.379(3)
C(6)-H(6) 0.93(2)
C(7)-C(8) 1.379(3)
C(7)-H(7) 0.90(2)
C(8)-H(8) 1.01(2)
C(9)-C(14) 1.385(2)
C(9)-C(10) 1.388(2)
C(10)-C(11) 1.381(3)
C(10)-H(10) 0.91(2)
C(11)-C(12) 1.370(4)
C(11)-H(11) 0.99(3)
C(12)-C(13) 1.370(4)
C(12)-H(12) 0.97(3)
C(13)-C(14) 1.387(3)
C(13)-H(13) 0.91(2)
C(14)-H(14) 0.969(19)
C(15)-C(16) 1.387(2)
C(15)-C(20) 1.398(2)
C(16)-C(17) 1.388(3)
C(16)-H(16) 0.92(2)
C(17)-C(18) 1.365(3)
C(17)-H(17) 0.95(2)
C(18)-C(19) 1.386(3)
C(18)-H(18) 0.98(2)
C(19)-C(20) 1.372(3)
C(19)-H(19) 0.90(2)
C(20)-H(20) 0.935(19)

C(1)-N-C(2) 121.64(12)
N-C(1)-C(15) 117.52(13)
N-C(1)-C(9) 123.10(13)
C(15)-C(1)-C(9) 119.36(13)
C(2)#1-C(2)-N 123.48(17)
C(2)#1-C(2)-C(3) 123.78(17)
N-C(2)-C(3) 112.52(13)
C(4)-C(3)-C(8) 119.15(15)
C(4)-C(3)-C(2) 119.18(14)
C(8)-C(3)-C(2) 121.65(14)
C(5)-C(4)-C(3) 119.52(16)
C(5)-C(4)-H(4) 119.6(12)
C(3)-C(4)-H(4) 120.8(12)
C(6)-C(5)-C(4) 121.93(17)
C(6)-C(5)-Cl 119.59(14)
C(4)-C(5)-Cl 118.47(15)
C(5)-C(6)-C(7) 118.15(17)
C(5)-C(6)-H(6) 123.4(13)
C(7)-C(6)-H(6) 118.4(13)
C(6)-C(7)-C(8) 121.43(18)
C(6)-C(7)-H(7) 118.0(15)
 S46

C(8)-C(7)-H(7) 120.3(15)
C(7)-C(8)-C(3) 119.78(17)
C(7)-C(8)-H(8) 120.9(11)
C(3)-C(8)-H(8) 119.3(11)
C(14)-C(9)-C(10) 119.02(16)
C(14)-C(9)-C(1) 122.22(14)
C(10)-C(9)-C(1) 118.69(15)
C(11)-C(10)-C(9) 119.9(2)
C(11)-C(10)-H(10) 121.2(13)
C(9)-C(10)-H(10) 118.9(12)
C(12)-C(11)-C(10) 120.7(2)
C(12)-C(11)-H(11) 122.9(15)
C(10)-C(11)-H(11) 116.4(16)
C(11)-C(12)-C(13) 120.1(2)
C(11)-C(12)-H(12) 116.4(17)
C(13)-C(12)-H(12) 123.4(17)
C(12)-C(13)-C(14) 119.9(2)
C(12)-C(13)-H(13) 121.2(14)
C(14)-C(13)-H(13) 118.9(14)
C(9)-C(14)-C(13) 120.43(18)
C(9)-C(14)-H(14) 118.9(11)
C(13)-C(14)-H(14) 120.6(11)
C(16)-C(15)-C(20) 118.33(15)
C(16)-C(15)-C(1) 121.84(14)
C(20)-C(15)-C(1) 119.82(14)
C(15)-C(16)-C(17) 120.68(18)
C(15)-C(16)-H(16) 119.3(12)
C(17)-C(16)-H(16) 120.0(12)
C(18)-C(17)-C(16) 120.39(19)
C(18)-C(17)-H(17) 120.9(13)
C(16)-C(17)-H(17) 118.7(13)
C(17)-C(18)-C(19) 119.54(17)
C(17)-C(18)-H(18) 118.0(13)
C(19)-C(18)-H(18) 122.4(13)
C(20)-C(19)-C(18) 120.63(18)
C(20)-C(19)-H(19) 117.8(15)
C(18)-C(19)-H(19) 121.5(15)
C(19)-C(20)-C(15) 120.42(17)
C(19)-C(20)-H(20) 120.9(12)
C(15)-C(20)-H(20) 118.6(12)

Symmetry transformations used to generate equivalent atoms:

#1 -x+1,-y+1,-z+1
 S47

TABLE 15. Anisotropic displacement parameters (2 x 103) for 5k.

The anisotropic displacement factor exponent takes the form:
-2 2 [h2 a*2 U11 + ... + 2 h k a* b* U12

Atom U11 U22 U33 U23 U13 U12

Cl 71(1) 50(1) 117(1) -19(1) 17(1) 17(1)

N 37(1) 33(1) 39(1) -3(1) 4(1) -2(1)
C(1) 31(1) 33(1) 36(1) 1(1) -4(1) 2(1)
C(2) 35(1) 35(1) 35(1) -5(1) 4(1) -3(1)
C(3) 37(1) 35(1) 37(1) 3(1) 5(1) -1(1)
C(4) 41(1) 35(1) 47(1) 2(1) 5(1) -2(1)
C(5) 50(1) 34(1) 59(1) 7(1) 13(1) 7(1)
C(6) 39(1) 54(1) 73(1) 13(1) 1(1) 10(1)
C(7) 42(1) 62(1) 64(1) 1(1) -10(1) -1(1)
C(8) 43(1) 47(1) 48(1) -4(1) -2(1) -1(1)
C(9) 42(1) 37(1) 32(1) 0(1) 2(1) -6(1)
C(10) 46(1) 71(1) 44(1) -10(1) -4(1) -2(1)
C(11) 67(1) 105(2) 52(1) -24(1) -11(1) -18(1)
C(12) 95(2) 78(2) 53(1) -30(1) 6(1) -20(1)
C(13) 85(2) 51(1) 54(1) -10(1) 19(1) 4(1)
C(14) 51(1) 46(1) 42(1) -2(1) 4(1) 2(1)
C(15) 32(1) 32(1) 40(1) 3(1) -4(1) 1(1)
C(16) 55(1) 45(1) 46(1) 0(1) 6(1) -8(1)
C(17) 58(1) 49(1) 69(1) 9(1) 17(1) -8(1)
C(18) 45(1) 34(1) 92(2) 3(1) 4(1) -8(1)
C(19) 49(1) 38(1) 73(1) -13(1) -6(1) -3(1)
C(20) 38(1) 41(1) 48(1) -5(1) -2(1) -1(1)
 S48

TABLE 16. Hydrogen coordinates (x 104) and isotropic displacement parameters (2

x 103) for 5k.

Atom x y z U(eq)

H(4) 6200(18) 2828(15) 4151(15) 47(5)

H(6) 9920(20) 3066(17) 5132(18) 64(6)
H(7) 9380(20) 4498(18) 6133(19) 71(7)
H(8) 7294(19) 5272(17) 6141(16) 58(5)
H(10) 5520(20) 3926(16) 7458(16) 51(5)
H(11) 5940(30) 5110(20) 8860(20) 91(8)
H(12) 4310(30) 6330(20) 9330(20) 102(9)
H(13) 2300(20) 6280(18) 8352(18) 64(6)
H(14) 1917(19) 5054(15) 6956(15) 50(5)
H(16) 1953(19) 3014(16) 7732(16) 51(5)
H(17) 490(20) 1626(17) 7847(19) 65(6)
H(18) 240(20) 436(17) 6405(17) 68(6)
H(19) 1560(20) 714(18) 4831(19) 68(6)
H(20) 2990(19) 2087(15) 4718(16) 48(5)

TABLE 17. Torsion angles [] for 5k.

C(2)-N-C(1)-C(15) 179.50(12)
C(2)-N-C(1)-C(9) -2.3(2)
C(1)-N-C(2)-C(2)#1 -73.1(2)
C(1)-N-C(2)-C(3) 112.12(16)
C(2)#1-C(2)-C(3)-C(4) -131.0(2)
N-C(2)-C(3)-C(4) 43.82(19)
C(2)#1-C(2)-C(3)-C(8) 50.4(3)
N-C(2)-C(3)-C(8) -134.76(15)
C(8)-C(3)-C(4)-C(5) -1.7(2)
C(2)-C(3)-C(4)-C(5) 179.66(14)
C(3)-C(4)-C(5)-C(6) 1.5(3)
C(3)-C(4)-C(5)-Cl -177.98(12)
C(4)-C(5)-C(6)-C(7) -0.5(3)
Cl-C(5)-C(6)-C(7) 179.05(15)
C(5)-C(6)-C(7)-C(8) -0.4(3)
C(6)-C(7)-C(8)-C(3) 0.2(3)
C(4)-C(3)-C(8)-C(7) 0.9(3)
C(2)-C(3)-C(8)-C(7) 179.46(16)
N-C(1)-C(9)-C(14) 113.20(18)
C(15)-C(1)-C(9)-C(14) -68.6(2)
N-C(1)-C(9)-C(10) -63.8(2)
C(15)-C(1)-C(9)-C(10) 114.32(17)
C(14)-C(9)-C(10)-C(11) -1.8(3)
C(1)-C(9)-C(10)-C(11) 175.31(19)
C(9)-C(10)-C(11)-C(12) 0.0(4)
C(10)-C(11)-C(12)-C(13) 1.5(4)
C(11)-C(12)-C(13)-C(14) -1.0(4)
 S49

C(10)-C(9)-C(14)-C(13) 2.3(3)
C(1)-C(9)-C(14)-C(13) -174.76(16)
C(12)-C(13)-C(14)-C(9) -0.9(3)
N-C(1)-C(15)-C(16) 177.51(15)
C(9)-C(1)-C(15)-C(16) -0.8(2)
N-C(1)-C(15)-C(20) -1.3(2)
C(9)-C(1)-C(15)-C(20) -179.56(14)
C(20)-C(15)-C(16)-C(17) -0.1(3)
C(1)-C(15)-C(16)-C(17) - 178.93(16)
C(15)-C(16)-C(17)-C(18) 0.2(3)
C(16)-C(17)-C(18)-C(19) 0.3(3)
C(17)-C(18)-C(19)-C(20) -0.8(3)
C(18)-C(19)-C(20)-C(15) 0.9(3)
C(16)-C(15)-C(20)-C(19) -0.5(2)
C(1)-C(15)-C(20)-C(19) 178.38(15)

Symmetry transformations used to generate equivalent atoms:

#1 -x+1,-y+1,-z+1

TABLE 18. Crystal data and structure refinement for 5l.

Empirical formula C46 H42 N2

Formula weight 622.82
Temperature 100(2) K
Wavelength 0.71073
Crystal system Triclinic
Space group P1
Unit cell dimensions a = 10.2213(13) = 92.073(2).
b = 11.4011(14) = 97.155(2).
c = 15.1911(19) = 101.554(2).
Volume 1717.5(4) 3
Z 2
Density (calculated) 1.204 Mg/m3
Absorption coefficient 0.069 mm1
F(000) 664
Crystal size 0.20 x 0.20 x 0.20 mm3
Theta range for data collection 1.83 to 25.00.
Index ranges 12<=h<=12, 13<=k<=13, 18<=l<=18
Reflections collected 12141
Independent reflections 5955 [R(int) = 0.0264]
Completeness to theta = 25.00 98.5 %
Absorption correction Numerical
 S50

Max. and min. transmission 0.9863 and 0.9863

Refinement method Fullmatrix leastsquares on F2
Data / restraints / parameters 5955 / 0 / 601
Goodnessoffit on F2 1.005
Final R indices [I>2sigma(I)] R1 = 0.0428, wR2 = 0.0970
R indices (all data) R1 = 0.0746, wR2 = 0.1049
Largest diff. Peak and hole 0.249 and 0.195 e.3

TABLE 19. Atomic coordinates (x 104) and equivalent isotropic displacement

parameters (2 x 103) for 5l. U(eq) is defined as one third of the trace of the
orthogonalized Uij tensor.

Atom x y z U(eq)

C(2) 2894(2) 7718(2) 2308(1) 23(1)

C(3) 3514(2) 7349(2) 1526(1) 23(1)
C(4) 4913(2) 7593(2) 1505(1) 25(1)
C(21) 5930(2) 8220(2) 2262(1) 28(1)
C(5) 5406(2) 7234(2) 739(1) 28(1)
C(6) 4571(2) 6635(2) 6(1) 30(1)
C(22) 5144(3) 6239(2) 794(2) 39(1)
C(7) 3194(2) 6394(2) 44(1) 30(1)
C(8) 2649(2) 6741(2) 784(1) 28(1)
C(23) 1145(2) 6409(2) 766(2) 37(1)
N(1) 1884(1) 8415(1) 2093(1) 26(1)
C(1) 2224(2) 9512(2) 1916(1) 24(1)
C(9) 3653(2) 10199(2) 2023(1) 26(1)
C(10) 4314(2) 10615(2) 2865(1) 32(1)
C(11) 5645(2) 11239(2) 2966(2) 38(1)
C(12) 6317(2) 11429(2) 2235(2) 39(1)
C(13) 5661(2) 11030(2) 1396(2) 36(1)
C(14) 4330(2) 10427(2) 1285(1) 31(1)
C(15) 1152(2) 10153(2) 1581(1) 26(1)
C(16) 1426(2) 11394(2) 1536(1) 30(1)
C(17) 424(2) 11984(2) 1212(1) 35(1)
C(18) 854(2) 11342(2) 919(1) 36(1)
C(19) 1144(2) 10108(2) 956(1) 33(1)
 S51

C(20) 156(2) 9515(2) 1284(1) 29(1)

C(2') 3093(2) 7334(2) 3132(1) 24(1)
C(3') 4064(2) 6566(2) 3436(1) 23(1)
C(4') 3938(2) 5391(2) 3068(1) 24(1)
C(21') 2833(2) 4804(2) 2350(1) 28(1)
C(5') 4877(2) 4712(2) 3380(1) 27(1)
C(6') 5926(2) 5148(2) 4050(1) 28(1)
C(22') 6916(2) 4406(2) 4386(2) 36(1)
C(7') 6021(2) 6302(2) 4413(1) 28(1)
C(8') 5126(2) 7018(2) 4129(1) 26(1)
C(23') 5352(2) 8265(2) 4566(1) 32(1)
N(2) 2530(1) 7823(1) 3845(1) 24(1)
C(1') 1309(2) 7481(2) 3981(1) 24(1)
C(9') 287(2) 6523(2) 3432(1) 25(1)
C(10') 389(2) 5333(2) 3449(1) 30(1)
C(11') 566(2) 4450(2) 2938(1) 34(1)
C(12') 1622(2) 4747(2) 2418(1) 32(1)
C(13') 1750(2) 5935(2) 2398(1) 35(1)
C(14') 803(2) 6818(2) 2909(1) 30(1)
C(15') 889(2) 8072(2) 4769(1) 25(1)
C(16') 258(2) 7556(2) 5126(1) 32(1)
C(17') 607(2) 8088(2) 5875(1) 37(1)
C(18') 189(2) 9142(2) 6267(1) 39(1)
C(19') 1324(2) 9675(2) 5912(1) 39(1)
C(20') 1670(2) 9140(2) 5166(1) 32(1)

Table 20. Bond lengths [] and angles [] for 5l.

C(2)C(2') 1.345(2)
C(2)N(1) 1.437(2)
C(2)C(3) 1.500(2)
C(3)C(4) 1.406(2)
C(3)C(8) 1.409(2)
C(4)C(5) 1.402(2)
C(4)C(21) 1.503(3)
C(21)H(21A) 0.975(18)
C(21)H(21B) 1.03(2)
C(21)H(21C) 1.00(2)
 S52

C(5)C(6) 1.382(3)
C(5)H(5) 1.009(17)
C(6)C(7) 1.387(3)
C(6)C(22) 1.506(3)
C(22)H(22A) 0.99(2)
C(22)H(22B) 0.94(3)
C(22)H(22C) 0.96(3)
C(7)C(8) 1.394(2)
C(7)H(7) 0.948(18)
C(8)C(23) 1.505(3)
C(23)H(23A) 1.00(3)
C(23)H(23B) 0.99(2)
C(23)H(23C) 0.98(2)
N(1)C(1) 1.277(2)
C(1)C(15) 1.484(2)
C(1)C(9) 1.499(2)
C(9)C(10) 1.390(2)
C(9)C(14) 1.395(3)
C(10)C(11) 1.390(3)
C(10)H(10) 1.017(18)
C(11)C(12) 1.377(3)
C(11)H(11) 0.959(19)
C(12)C(13) 1.381(3)
C(12)H(12) 0.95(2)
C(13)C(14) 1.382(3)
C(13)H(13) 0.99(2)
C(14)H(14) 0.997(18)
C(15)C(16) 1.392(2)
C(15)C(20) 1.399(2)
C(16)C(17) 1.385(3)
C(16)H(16) 0.987(19)
C(17)C(18) 1.375(3)
C(17)H(17) 0.98(2)
C(18)C(19) 1.383(3)
C(18)H(18) 0.952(18)
C(19)C(20) 1.377(3)
C(19)H(19) 0.936(19)
C(20)H(20) 0.973(18)
 S53

C(2')N(2) 1.434(2)
C(2')C(3') 1.493(2)
C(3')C(4') 1.409(2)
C(3')C(8') 1.415(2)
C(4')C(5') 1.398(2)
C(4')C(21') 1.500(2)
C(21')H(211) 0.981(17)
C(21')H(212) 0.99(2)
C(21')H(213) 0.99(2)
C(5')C(6') 1.382(2)
C(5')H(5') 0.978(16)
C(6')C(7') 1.388(3)
C(6')C(22') 1.500(3)
C(22')H(221) 0.98(2)
C(22')H(222) 0.92(3)
C(22')H(223) 1.00(2)
C(7')C(8') 1.384(2)
C(7')H(7') 0.954(17)
C(8')C(23') 1.510(2)
C(23')H(231) 1.02(2)
C(23')H(232) 1.05(2)
C(23')H(233) 0.97(2)
N(2)C(1') 1.276(2)
C(1')C(9') 1.496(2)
C(1')C(15') 1.502(2)
C(9')C(10') 1.382(2)
C(9')C(14') 1.390(2)
C(10')C(11') 1.389(3)
C(10')H(10') 0.956(18)
C(11')C(12') 1.364(3)
C(11')H(11') 0.98(2)
C(12')C(13') 1.388(3)
C(12')H(12') 0.947(19)
C(13')C(14') 1.386(3)
C(13')H(13') 1.010(19)
C(14')H(14') 1.001(18)
C(15')C(16') 1.386(2)
C(15')C(20') 1.386(2)
 S54

C(16')C(17') 1.389(3)
C(16')H(16') 0.966(18)
C(17')C(18') 1.377(3)
C(17')H(17') 0.992(18)
C(18')C(19') 1.380(3)
C(18')H(18') 0.947(19)
C(19')C(20') 1.384(3)
C(19')H(19') 0.93(2)
C(20')H(20') 1.027(19)

C(2')C(2)N(1) 119.85(14)
C(2')C(2)C(3) 125.39(15)
N(1)C(2)C(3) 114.24(14)
C(4)C(3)C(8) 119.18(15)
C(4)C(3)C(2) 122.71(15)
C(8)C(3)C(2) 118.10(14)
C(5)C(4)C(3) 118.94(16)
C(5)C(4)C(21) 117.35(15)
C(3)C(4)C(21) 123.71(15)
C(4)C(21)H(21A) 112.9(10)
C(4)C(21)H(21B) 112.9(10)
H(21A)C(21)H(21B) 105.4(14)
C(4)C(21)H(21C) 109.7(11)
H(21A)C(21)H(21C) 106.5(15)
H(21B)C(21)H(21C) 109.1(14)
C(6)C(5)C(4) 122.59(17)
C(6)C(5)H(5) 118.5(10)
C(4)C(5)H(5) 118.9(10)
C(5)C(6)C(7) 117.55(16)
C(5)C(6)C(22) 120.91(18)
C(7)C(6)C(22) 121.53(18)
C(6)C(22)H(22A) 108.4(14)
C(6)C(22)H(22B) 112.8(14)
H(22A)C(22)H(22B) 106(2)
C(6)C(22)H(22C) 113.7(14)
H(22A)C(22)H(22C) 108.2(19)
H(22B)C(22)H(22C) 108(2)
C(6)C(7)C(8) 122.27(18)
 S55

C(6)C(7)H(7) 119.2(10)
C(8)C(7)H(7) 118.5(10)
C(7)C(8)C(3) 119.47(16)
C(7)C(8)C(23) 118.04(17)
C(3)C(8)C(23) 122.46(16)
C(8)C(23)H(23A) 117.4(14)
C(8)C(23)H(23B) 114.7(11)
H(23A)C(23)H(23B) 98.6(17)
C(8)C(23)H(23C) 109.8(12)
H(23A)C(23)H(23C) 108.3(18)
H(23B)C(23)H(23C) 107.2(17)
C(1)N(1)C(2) 120.40(14)
N(1)C(1)C(15) 118.68(15)
N(1)C(1)C(9) 123.80(15)
C(15)C(1)C(9) 117.52(15)
C(10)C(9)C(14) 119.48(17)
C(10)C(9)C(1) 119.81(16)
C(14)C(9)C(1) 120.72(16)
C(9)C(10)C(11) 119.82(19)
C(9)C(10)H(10) 118.2(10)
C(11)C(10)H(10) 122.0(10)
C(12)C(11)C(10) 120.3(2)
C(12)C(11)H(11) 120.6(11)
C(10)C(11)H(11) 119.1(11)
C(11)C(12)C(13) 120.17(19)
C(11)C(12)H(12) 120.0(12)
C(13)C(12)H(12) 119.8(12)
C(12)C(13)C(14) 120.1(2)
C(12)C(13)H(13) 119.3(11)
C(14)C(13)H(13) 120.5(11)
C(13)C(14)C(9) 120.08(19)
C(13)C(14)H(14) 118.6(10)
C(9)C(14)H(14) 121.2(10)
C(16)C(15)C(20) 118.41(16)
C(16)C(15)C(1) 121.13(16)
C(20)C(15)C(1) 120.45(16)
C(17)C(16)C(15) 120.80(18)
C(17)C(16)H(16) 120.5(11)
 S56

C(15)C(16)H(16) 118.7(11)
C(18)C(17)C(16) 119.9(2)
C(18)C(17)H(17) 118.8(11)
C(16)C(17)H(17) 121.3(11)
C(17)C(18)C(19) 120.08(18)
C(17)C(18)H(18) 121.1(11)
C(19)C(18)H(18) 118.8(11)
C(20)C(19)C(18) 120.31(19)
C(20)C(19)H(19) 121.8(12)
C(18)C(19)H(19) 117.9(12)
C(19)C(20)C(15) 120.45(19)
C(19)C(20)H(20) 122.4(10)
C(15)C(20)H(20) 117.1(10)
C(2)C(2')N(2) 120.34(15)
C(2)C(2')C(3') 125.56(15)
N(2)C(2')C(3') 113.26(14)
C(4')C(3')C(8') 118.77(15)
C(4')C(3')C(2') 121.90(15)
C(8')C(3')C(2') 119.31(15)
C(5')C(4')C(3') 119.41(16)
C(5')C(4')C(21') 117.00(16)
C(3')C(4')C(21') 123.59(15)
C(4')C(21')H(211) 113.2(10)
C(4')C(21')H(212) 109.7(11)
H(211)C(21')H(212) 105.7(14)
C(4')C(21')H(213) 109.9(11)
H(211)C(21')H(213) 107.8(15)
H(212)C(21')H(213) 110.4(15)
C(6')C(5')C(4') 122.31(17)
C(6')C(5')H(5') 120.8(9)
C(4')C(5')H(5') 116.9(9)
C(5')C(6')C(7') 117.38(16)
C(5')C(6')C(22') 121.76(18)
C(7')C(6')C(22') 120.85(17)
C(6')C(22')H(221) 111.7(13)
C(6')C(22')H(222) 111.0(14)
H(221)C(22')H(222) 109(2)
C(6')C(22')H(223) 113.4(11)
 S57

H(221)C(22')H(223) 108.4(17)
H(222)C(22')H(223) 103.3(18)
C(8')C(7')C(6') 122.93(17)
C(8')C(7')H(7') 117.8(10)
C(6')C(7')H(7') 119.3(10)
C(7')C(8')C(3') 119.18(16)
C(7')C(8')C(23') 117.86(16)
C(3')C(8')C(23') 122.95(16)
C(8')C(23')H(231) 110.5(10)
C(8')C(23')H(232) 111.8(11)
H(231)C(23')H(232) 105.1(14)
C(8')C(23')H(233) 108.5(11)
H(231)C(23')H(233) 111.0(15)
H(232)C(23')H(233) 109.9(15)
C(1')N(2)C(2') 123.64(14)
N(2)C(1')C(9') 125.05(15)
N(2)C(1')C(15') 116.79(15)
C(9')C(1')C(15') 118.14(14)
C(10')C(9')C(14') 118.82(17)
C(10')C(9')C(1') 120.99(16)
C(14')C(9')C(1') 120.17(16)
C(9')C(10')C(11') 120.58(18)
C(9')C(10')H(10') 119.4(11)
C(11')C(10')H(10') 120.0(11)
C(12')C(11')C(10') 120.26(19)
C(12')C(11')H(11') 121.1(11)
C(10')C(11')H(11') 118.7(11)
C(11')C(12')C(13') 120.08(19)
C(11')C(12')H(12') 120.2(11)
C(13')C(12')H(12') 119.7(11)
C(14')C(13')C(12') 119.78(18)
C(14')C(13')H(13') 119.9(11)
C(12')C(13')H(13') 120.3(11)
C(13')C(14')C(9') 120.46(18)
C(13')C(14')H(14') 120.1(10)
C(9')C(14')H(14') 119.5(10)
C(16')C(15')C(20') 118.70(16)
C(16')C(15')C(1') 121.22(16)
 S58

C(20')C(15')C(1') 120.06(16)
C(15')C(16')C(17') 120.66(19)
C(15')C(16')H(16') 119.7(10)
C(17')C(16')H(16') 119.6(10)
C(18')C(17')C(16') 119.85(19)
C(18')C(17')H(17') 115.7(10)
C(16')C(17')H(17') 124.3(11)
C(17')C(18')C(19') 120.14(18)
C(17')C(18')H(18') 120.1(12)
C(19')C(18')H(18') 119.8(12)
C(18')C(19')C(20') 119.8(2)
C(18')C(19')H(19') 119.3(12)
C(20')C(19')H(19') 120.9(13)
C(19')C(20')C(15') 120.81(19)
C(19')C(20')H(20') 120.8(10)
C(15')C(20')H(20') 118.4(10)
Symmetry transformations used to generate equivalent atoms:

TABLE 21. Anisotropic displacement parameters (2 x 103) for 5l.

The anisotropic displacement factor exponent takes the form:
-2 2 [h2 a*2 U11 + ... + 2 h k a* b* U12

Atom U11 U22 U33 U23 U13 U12

C(2) 20(1) 21(1) 26(1) 2(1) 2(1) 1(1)

C(3) 26(1) 19(1) 24(1) 1(1) 2(1) 7(1)
C(4) 31(1) 19(1) 29(1) 4(1) 6(1) 10(1)
C(21) 25(1) 26(1) 32(1) 1(1) 6(1) 5(1)
C(5) 31(1) 24(1) 31(1) 6(1) 9(1) 10(1)
C(6) 43(1) 27(1) 27(1) 5(1) 9(1) 16(1)
C(22) 53(2) 39(1) 31(1) 3(1) 15(1) 21(1)
C(7) 41(1) 28(1) 22(1) 0(1) 0(1) 10(1)
C(8) 33(1) 24(1) 27(1) 3(1) 4(1) 9(1)
C(23) 32(1) 43(1) 32(1) 10(1) 2(1) 3(1)
N(1) 26(1) 27(1) 25(1) 1(1) 5(1) 6(1)
C(1) 27(1) 26(1) 19(1) 4(1) 4(1) 5(1)
C(9) 26(1) 21(1) 33(1) 0(1) 1(1) 9(1)
C(10) 33(1) 27(1) 36(1) 5(1) 1(1) 8(1)
C(11) 34(1) 29(1) 46(1) 10(1) 9(1) 7(1)
 S59

C(12) 26(1) 25(1) 65(2) 5(1) 1(1) 4(1)

C(13) 30(1) 31(1) 49(1) 13(1) 9(1) 10(1)
C(14) 28(1) 30(1) 34(1) 5(1) 2(1) 9(1)
C(15) 29(1) 30(1) 19(1) 1(1) 6(1) 8(1)
C(16) 28(1) 30(1) 32(1) 3(1) 1(1) 6(1)
C(17) 32(1) 31(1) 42(1) 3(1) 2(1) 9(1)
C(18) 28(1) 44(1) 39(1) 13(1) 6(1) 16(1)
C(19) 23(1) 43(1) 33(1) 7(1) 3(1) 5(1)
C(20) 27(1) 32(1) 27(1) 1(1) 4(1) 5(1)
C(2') 22(1) 22(1) 24(1) 5(1) 4(1) 0(1)
C(3') 24(1) 26(1) 21(1) 2(1) 7(1) 3(1)
C(4') 24(1) 26(1) 21(1) 1(1) 6(1) 2(1)
C(21') 32(1) 24(1) 28(1) 2(1) 5(1) 6(1)
C(5') 31(1) 24(1) 26(1) 1(1) 9(1) 5(1)
C(6') 26(1) 33(1) 25(1) 7(1) 8(1) 5(1)
C(22') 31(1) 41(1) 35(1) 8(1) 2(1) 9(1)
C(7') 21(1) 39(1) 22(1) 1(1) 2(1) 1(1)
C(8') 23(1) 30(1) 23(1) 0(1) 7(1) 1(1)
C(23') 27(1) 35(1) 30(1) 7(1) 2(1) 1(1)
N(2) 24(1) 26(1) 23(1) 2(1) 3(1) 5(1)
C(1') 24(1) 24(1) 24(1) 2(1) 1(1) 8(1)
C(9') 25(1) 28(1) 23(1) 2(1) 7(1) 3(1)
C(10') 27(1) 30(1) 31(1) 0(1) 1(1) 6(1)
C(11') 36(1) 26(1) 38(1) 3(1) 6(1) 5(1)
C(12') 34(1) 34(1) 25(1) 5(1) 2(1) 2(1)
C(13') 32(1) 41(1) 30(1) 3(1) 3(1) 6(1)
C(14') 31(1) 28(1) 30(1) 2(1) 1(1) 4(1)
C(15') 24(1) 27(1) 23(1) 1(1) 0(1) 10(1)
C(16') 33(1) 32(1) 29(1) 4(1) 7(1) 4(1)
C(17') 34(1) 47(1) 32(1) 2(1) 8(1) 9(1)
C(18') 39(1) 54(1) 28(1) 10(1) 5(1) 19(1)
C(19') 34(1) 43(1) 38(1) 14(1) 2(1) 9(1)
C(20') 27(1) 37(1) 32(1) 7(1) 3(1) 8(1)
 S60

TABLE 22. Hydrogen coordinates (x 104) and isotropic displacement parameters (2

x 103) for 5l.

Atom x y z U(eq)

H(21A) 5572(17) 8767(16) 2630(12) 31(5)

H(21B) 6772(19) 8737(17) 2053(12) 40(5)
H(21C) 6217(18) 7615(18) 2663(13) 40(5)
H(5) 6411(18) 7403(15) 726(11) 30(5)
H(22A) 6140(30) 6380(20) 647(16) 74(8)
H(22B) 4980(20) 6690(20) 1286(17) 73(8)
H(22C) 4810(20) 5400(20) 981(15) 70(8)
H(7) 2601(17) 5974(16) 447(12) 32(5)
H(23A) 620(20) 7050(20) 624(16) 80(8)
H(23B) 843(19) 6204(18) 1346(15) 48(6)
H(23C) 770(20) 5720(20) 350(15) 58(7)
H(10) 3792(17) 10463(15) 3392(12) 30(5)
H(11) 6091(18) 11523(17) 3550(13) 35(5)
H(12) 7240(20) 11835(18) 2308(13) 47(6)
H(13) 6139(19) 11212(17) 876(13) 44(6)
H(14) 3887(17) 10125(16) 674(12) 32(5)
H(16) 2349(19) 11848(17) 1742(12) 40(5)
H(17) 607(18) 12861(18) 1185(12) 41(6)
H(18) 1549(18) 11730(16) 680(12) 35(5)
H(19) 2020(20) 9698(17) 750(13) 40(6)
H(20) 311(16) 8645(17) 1285(11) 30(5)
H(211) 2053(17) 5190(15) 2298(11) 27(5)
H(212) 2485(17) 3965(19) 2486(12) 38(5)
H(213) 3177(19) 4826(17) 1769(14) 46(6)
H(5') 4753(15) 3900(15) 3108(10) 20(4)
H(221) 6760(20) 3640(20) 4043(15) 61(7)
H(222) 6870(20) 4260(20) 4976(18) 70(8)
H(223) 7880(20) 4819(18) 4387(13) 49(6)
H(7') 6725(16) 6623(14) 4883(11) 21(4)
H(231) 5214(17) 8870(17) 4102(12) 34(5)
H(232) 4650(20) 8332(18) 5005(14) 51(6)
H(233) 6250(20) 8464(17) 4885(13) 41(5)
H(10') 1135(18) 5123(16) 3806(12) 33(5)
H(11') 458(18) 3613(19) 2957(12) 42(5)
 S61

H(12') 2280(18) 4143(17) 2077(12) 34(5)

H(13') 2555(19) 6153(17) 2036(13) 43(5)
H(14') 899(16) 7673(17) 2905(11) 33(5)
H(16') 802(17) 6803(17) 4865(11) 30(5)
H(17') 1451(18) 7798(16) 6131(12) 36(5)
H(18') 50(18) 9511(17) 6775(13) 39(5)
H(19') 1840(20) 10398(19) 6171(14) 49(6)
H(20') 2531(19) 9509(17) 4908(12) 42(5)

TABLE 23. Torsion angles [] for 5l.

C(2')C(2)C(3)C(4) 62.4(2)
N(1)C(2)C(3)C(4) 125.85(17)
C(2')C(2)C(3)C(8) 117.95(19)
N(1)C(2)C(3)C(8) 53.7(2)
C(8)C(3)C(4)C(5) 0.7(2)
C(2)C(3)C(4)C(5) 178.88(16)
C(8)C(3)C(4)C(21) 179.11(16)
C(2)C(3)C(4)C(21) 1.3(3)
C(3)C(4)C(5)C(6) 0.9(3)
C(21)C(4)C(5)C(6) 178.97(17)
C(4)C(5)C(6)C(7) 0.3(3)
C(4)C(5)C(6)C(22) 178.50(18)
C(5)C(6)C(7)C(8) 0.3(3)
C(22)C(6)C(7)C(8) 179.17(19)
C(6)C(7)C(8)C(3) 0.5(3)
C(6)C(7)C(8)C(23) 178.47(18)
C(4)C(3)C(8)C(7) 0.1(2)
C(2)C(3)C(8)C(7) 179.54(16)
C(4)C(3)C(8)C(23) 177.83(17)
C(2)C(3)C(8)C(23) 2.6(3)
C(2')C(2)N(1)C(1) 113.32(19)
C(3)C(2)N(1)C(1) 74.5(2)
C(2)N(1)C(1)C(15) 171.95(14)
C(2)N(1)C(1)C(9) 7.7(2)
N(1)C(1)C(9)C(10) 76.7(2)
C(15)C(1)C(9)C(10) 103.63(19)
N(1)C(1)C(9)C(14) 103.3(2)
 S62

C(15)C(1)C(9)C(14) 76.4(2)
C(14)C(9)C(10)C(11) 0.8(3)
C(1)C(9)C(10)C(11) 179.17(16)
C(9)C(10)C(11)C(12) 1.0(3)
C(10)C(11)C(12)C(13) 1.7(3)
C(11)C(12)C(13)C(14) 0.6(3)
C(12)C(13)C(14)C(9) 1.3(3)
C(10)C(9)C(14)C(13) 2.0(3)
C(1)C(9)C(14)C(13) 178.05(16)
N(1)C(1)C(15)C(16) 167.84(16)
C(9)C(1)C(15)C(16) 12.5(2)
N(1)C(1)C(15)C(20) 13.6(2)
C(9)C(1)C(15)C(20) 166.06(15)
C(20)C(15)C(16)C(17) 0.6(3)
C(1)C(15)C(16)C(17) 179.20(16)
C(15)C(16)C(17)C(18) 0.9(3)
C(16)C(17)C(18)C(19) 0.7(3)
C(17)C(18)C(19)C(20) 0.2(3)
C(18)C(19)C(20)C(15) 0.1(3)
C(16)C(15)C(20)C(19) 0.1(3)
C(1)C(15)C(20)C(19) 178.71(16)
N(1)C(2)C(2')N(2) 13.8(2)
C(3)C(2)C(2')N(2) 174.98(15)
N(1)C(2)C(2')C(3') 177.48(15)
C(3)C(2)C(2')C(3') 6.2(3)
C(2)C(2')C(3')C(4') 63.2(2)
N(2)C(2')C(3')C(4') 127.39(16)
C(2)C(2')C(3')C(8') 118.33(19)
N(2)C(2')C(3')C(8') 51.1(2)
C(8')C(3')C(4')C(5') 1.4(2)
C(2')C(3')C(4')C(5') 179.95(15)
C(8')C(3')C(4')C(21') 178.28(16)
C(2')C(3')C(4')C(21') 0.2(2)
C(3')C(4')C(5')C(6') 0.8(2)
C(21')C(4')C(5')C(6') 178.91(16)
C(4')C(5')C(6')C(7') 0.1(2)
C(4')C(5')C(6')C(22') 179.25(17)
C(5')C(6')C(7')C(8') 0.4(3)
 S63

C(22')C(6')C(7')C(8') 179.54(18)
C(6')C(7')C(8')C(3') 0.2(3)
C(6')C(7')C(8')C(23') 178.97(16)
C(4')C(3')C(8')C(7') 1.1(2)
C(2')C(3')C(8')C(7') 179.71(15)
C(4')C(3')C(8')C(23') 179.80(16)
C(2')C(3')C(8')C(23') 1.6(2)
C(2)C(2')N(2)C(1') 81.2(2)
C(3')C(2')N(2)C(1') 108.74(18)
C(2')N(2)C(1')C(9') 0.6(3)
C(2')N(2)C(1')C(15') 178.90(15)
N(2)C(1')C(9')C(10') 69.3(2)
C(15')C(1')C(9')C(10') 108.97(18)
N(2)C(1')C(9')C(14') 112.1(2)
C(15')C(1')C(9')C(14') 69.6(2)
C(14')C(9')C(10')C(11') 1.3(3)
C(1')C(9')C(10')C(11') 179.94(16)
C(9')C(10')C(11')C(12') 0.5(3)
C(10')C(11')C(12')C(13') 0.1(3)
C(11')C(12')C(13')C(14') 0.1(3)
C(12')C(13')C(14')C(9') 0.9(3)
C(10')C(9')C(14')C(13') 1.5(3)
C(1')C(9')C(14')C(13') 179.82(16)
N(2)C(1')C(15')C(16') 161.51(16)
C(9')C(1')C(15')C(16') 16.9(2)
N(2)C(1')C(15')C(20') 17.1(2)
C(9')C(1')C(15')C(20') 164.46(16)
C(20')C(15')C(16')C(17') 1.1(3)
C(1')C(15')C(16')C(17') 177.50(17)
C(15')C(16')C(17')C(18') 0.4(3)
C(16')C(17')C(18')C(19') 0.5(3)
C(17')C(18')C(19')C(20') 0.6(3)
C(18')C(19')C(20')C(15') 0.1(3)
C(16')C(15')C(20')C(19') 1.0(3)
C(1')C(15')C(20')C(19') 177.67(17)
Symmetry transformations used to generate equivalent atoms:
 S64

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