Bis[4-(diphenyl-methyl-eneamino)phen-yl]methanone.

The title mol-ecule, C(39)H(28)N(2)O, is a well known dendron used in the synthesis of phenyl-azomethine dendrimers. The central benzophenone core is twisted, as expected, due to hindrance between H atoms: the dihedral angle between core benzene rings is 54.49 (5)°, identical to that of the stable polymorph of benzophenone (56°). For the same reason, phenyl groups substituting imine C atoms make a large dihedral angle, although similar for each imine: 71.83 (6) and 67.64 (5)°. The six aromatic rings in the mol-ecule thus seem to be quite randomly oriented, and such an arrangement is not favorable for efficient stacking inter-actions in the crystal. The same behaviour is observed in the vast majority of diphenyl-imino-containing organics. The low triclinic crystal symmetry may be a consequence of these features.

Related literature

For the use of the title mol­ecule in the synthesis of dendritic systems, see: Higuchi et al. (2001 ▶); Takanashi et al. (2004 ▶); Yamamoto & Higuchi (2004 ▶). For the structure of benzophenone, see: Fleischer et al. (1968 ▶); Kutzke et al. (2000 ▶). For related structures including the diphenyl­imino fragment, see: Appel et al. (1985 ▶); Buhmann et al. (1993 ▶). For geometrical analysis using the Cambridge Structural Database, see: Bruno et al. (2002 ▶).

Experimental

Crystal data

C39H28N2O

M = 540.63

Triclinic,

a = 11.1723 (10) Å

b = 11.3487 (13) Å

c = 13.2331 (15) Å

α = 103.121 (9)°

β = 105.170 (8)°

γ = 108.746 (8)°

V = 1441.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.55 × 0.28 × 0.24 mm

Data collection

Bruker P4 diffractometer

6892 measured reflections

5865 independent reflections

4471 reflections with I > 2σ(I)

R int = 0.018

3 standard reflections every 97 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.03

5865 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 .

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016375/fl2303sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016375/fl2303Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C39H28N2O	Z = 2
Mr = 540.63	F(000) = 568
Triclinic, P1	Dx = 1.245 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1723 (10) Å	Cell parameters from 82 reflections
b = 11.3487 (13) Å	θ = 4.6–12.5°
c = 13.2331 (15) Å	µ = 0.08 mm−1
α = 103.121 (9)°	T = 296 K
β = 105.170 (8)°	Prism, yellow
γ = 108.746 (8)°	0.55 × 0.28 × 0.24 mm
V = 1441.9 (3) Å3

Bruker P4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 26.4°, θmin = 2.0°
graphite	h = −13→2
2θ/ω scans	k = −13→13
6892 measured reflections	l = −16→16
5865 independent reflections	3 standard reflections every 97 reflections
4471 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.275P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5865 reflections	Δρmax = 0.19 e Å−3
380 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0198 (18)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.81457 (15)	0.23158 (15)	0.66331 (12)	0.0425 (3)
O1	0.92972 (12)	0.26828 (14)	0.66240 (11)	0.0658 (4)
C2	0.70743 (14)	0.24601 (14)	0.57791 (12)	0.0383 (3)
C3	0.72166 (15)	0.24315 (15)	0.47594 (12)	0.0425 (3)
H3A	0.7902	0.2224	0.4599	0.051*
C4	0.63532 (15)	0.27069 (15)	0.39873 (12)	0.0407 (3)
H4A	0.6459	0.2673	0.3309	0.049*
C5	0.53212 (14)	0.30355 (13)	0.42020 (11)	0.0373 (3)
C6	0.51690 (15)	0.30587 (15)	0.52197 (12)	0.0424 (3)
H6A	0.4486	0.3270	0.5381	0.051*
C7	0.60322 (15)	0.27683 (15)	0.59917 (12)	0.0416 (3)
H7A	0.5914	0.2779	0.6663	0.050*
N8	0.46589 (12)	0.34758 (12)	0.33981 (10)	0.0419 (3)
C9	0.34487 (14)	0.34189 (13)	0.31471 (11)	0.0374 (3)
C10	0.30371 (14)	0.40362 (14)	0.23057 (12)	0.0395 (3)
C11	0.39664 (17)	0.46820 (17)	0.18792 (13)	0.0505 (4)
H11A	0.4834	0.4696	0.2098	0.061*
C12	0.3613 (2)	0.5302 (2)	0.11344 (15)	0.0614 (5)
H12A	0.4245	0.5732	0.0858	0.074*
C13	0.23276 (19)	0.52870 (18)	0.07989 (14)	0.0585 (4)
H13A	0.2094	0.5712	0.0304	0.070*
C14	0.14043 (18)	0.46438 (19)	0.11986 (15)	0.0614 (5)
H14A	0.0534	0.4622	0.0968	0.074*
C15	0.17516 (16)	0.40203 (17)	0.19474 (14)	0.0536 (4)
H15A	0.1109	0.3585	0.2212	0.064*
C16	0.24182 (14)	0.27839 (14)	0.36114 (11)	0.0372 (3)
C17	0.20701 (16)	0.35573 (16)	0.43619 (13)	0.0473 (4)
H17A	0.2458	0.4474	0.4564	0.057*
C18	0.11442 (17)	0.29636 (18)	0.48108 (13)	0.0529 (4)
H18A	0.0925	0.3485	0.5321	0.064*
C19	0.05504 (17)	0.16072 (18)	0.45026 (14)	0.0547 (4)
H19A	−0.0065	0.1214	0.4808	0.066*
C20	0.08672 (18)	0.08337 (17)	0.37436 (16)	0.0575 (4)
H20A	0.0454	−0.0083	0.3527	0.069*
C21	0.18011 (16)	0.14185 (15)	0.33012 (14)	0.0477 (4)
H21A	0.2015	0.0890	0.2792	0.057*
C22	0.78337 (15)	0.17280 (14)	0.74811 (12)	0.0404 (3)
C23	0.89013 (16)	0.20074 (16)	0.84510 (13)	0.0475 (4)
H23A	0.9765	0.2609	0.8578	0.057*
C24	0.87042 (17)	0.14101 (16)	0.92269 (13)	0.0513 (4)
H24A	0.9428	0.1621	0.9875	0.062*
C25	0.74229 (16)	0.04910 (14)	0.90414 (12)	0.0436 (3)
C26	0.63567 (16)	0.02012 (16)	0.80788 (13)	0.0465 (4)
H26A	0.5500	−0.0420	0.7944	0.056*
C27	0.65529 (16)	0.08267 (15)	0.73147 (12)	0.0448 (3)
H27A	0.5820	0.0642	0.6683	0.054*
N28	0.72437 (15)	−0.02708 (13)	0.97419 (11)	0.0495 (3)
C29	0.73136 (14)	0.02098 (14)	1.07383 (12)	0.0391 (3)
C30	0.72464 (14)	−0.06736 (14)	1.14219 (12)	0.0409 (3)
C31	0.7430 (2)	−0.18335 (17)	1.10693 (15)	0.0584 (4)
H31A	0.7576	−0.2060	1.0405	0.070*
C32	0.7397 (2)	−0.2648 (2)	1.17030 (18)	0.0717 (6)
H32A	0.7527	−0.3419	1.1465	0.086*
C33	0.7174 (2)	−0.23299 (19)	1.26838 (16)	0.0657 (5)
H33A	0.7156	−0.2883	1.3107	0.079*
C34	0.69800 (19)	−0.11972 (19)	1.30364 (15)	0.0598 (5)
H34A	0.6823	−0.0985	1.3697	0.072*
C35	0.70164 (16)	−0.03645 (16)	1.24098 (13)	0.0487 (4)
H35A	0.6886	0.0404	1.2654	0.058*
C36	0.74461 (14)	0.15897 (14)	1.12429 (12)	0.0386 (3)
C37	0.85587 (15)	0.24739 (15)	1.21870 (13)	0.0452 (3)
H37A	0.9195	0.2189	1.2534	0.054*
C38	0.8732 (2)	0.37737 (17)	1.26174 (15)	0.0577 (4)
H38A	0.9499	0.4367	1.3232	0.069*
C39	0.7766 (2)	0.41837 (19)	1.21333 (17)	0.0657 (5)
H39A	0.7879	0.5056	1.2423	0.079*
C40	0.6634 (2)	0.3310 (2)	1.12217 (16)	0.0655 (5)
H40A	0.5973	0.3588	1.0911	0.079*
C41	0.64726 (18)	0.20148 (18)	1.07617 (14)	0.0513 (4)
H41A	0.5716	0.1434	1.0134	0.062*

	U11	U22	U33	U12	U13	U23
C1	0.0422 (8)	0.0497 (9)	0.0425 (8)	0.0226 (7)	0.0182 (6)	0.0192 (7)
O1	0.0458 (7)	0.1042 (10)	0.0667 (8)	0.0347 (7)	0.0264 (6)	0.0504 (8)
C2	0.0402 (7)	0.0395 (7)	0.0392 (7)	0.0174 (6)	0.0164 (6)	0.0164 (6)
C3	0.0430 (8)	0.0527 (9)	0.0414 (8)	0.0253 (7)	0.0209 (7)	0.0179 (7)
C4	0.0414 (8)	0.0510 (8)	0.0347 (7)	0.0192 (7)	0.0181 (6)	0.0177 (6)
C5	0.0350 (7)	0.0376 (7)	0.0397 (7)	0.0130 (6)	0.0138 (6)	0.0161 (6)
C6	0.0424 (8)	0.0517 (8)	0.0437 (8)	0.0243 (7)	0.0220 (7)	0.0200 (7)
C7	0.0468 (8)	0.0499 (8)	0.0364 (7)	0.0229 (7)	0.0201 (6)	0.0186 (6)
N8	0.0394 (7)	0.0496 (7)	0.0434 (7)	0.0193 (6)	0.0172 (5)	0.0232 (6)
C9	0.0381 (7)	0.0367 (7)	0.0374 (7)	0.0149 (6)	0.0144 (6)	0.0123 (6)
C10	0.0392 (8)	0.0399 (8)	0.0383 (7)	0.0154 (6)	0.0130 (6)	0.0137 (6)
C11	0.0499 (9)	0.0678 (11)	0.0520 (9)	0.0316 (8)	0.0268 (8)	0.0320 (8)
C12	0.0657 (11)	0.0802 (13)	0.0621 (11)	0.0352 (10)	0.0355 (9)	0.0438 (10)
C13	0.0653 (11)	0.0697 (11)	0.0510 (9)	0.0329 (9)	0.0185 (8)	0.0343 (9)
C14	0.0475 (9)	0.0747 (12)	0.0651 (11)	0.0275 (9)	0.0112 (8)	0.0360 (10)
C15	0.0381 (8)	0.0637 (10)	0.0615 (10)	0.0174 (8)	0.0157 (7)	0.0329 (9)
C16	0.0337 (7)	0.0412 (7)	0.0382 (7)	0.0161 (6)	0.0121 (6)	0.0160 (6)
C17	0.0423 (8)	0.0450 (8)	0.0481 (8)	0.0151 (7)	0.0154 (7)	0.0089 (7)
C18	0.0487 (9)	0.0704 (11)	0.0422 (8)	0.0269 (8)	0.0210 (7)	0.0142 (8)
C19	0.0466 (9)	0.0738 (12)	0.0572 (10)	0.0240 (8)	0.0268 (8)	0.0376 (9)
C20	0.0563 (10)	0.0488 (9)	0.0772 (12)	0.0199 (8)	0.0311 (9)	0.0328 (9)
C21	0.0514 (9)	0.0426 (8)	0.0591 (9)	0.0223 (7)	0.0282 (8)	0.0205 (7)
C22	0.0453 (8)	0.0446 (8)	0.0380 (7)	0.0234 (7)	0.0167 (6)	0.0168 (6)
C23	0.0447 (8)	0.0502 (9)	0.0439 (8)	0.0159 (7)	0.0120 (7)	0.0189 (7)
C24	0.0524 (9)	0.0550 (9)	0.0376 (8)	0.0181 (8)	0.0059 (7)	0.0176 (7)
C25	0.0571 (9)	0.0407 (8)	0.0372 (7)	0.0219 (7)	0.0195 (7)	0.0147 (6)
C26	0.0461 (8)	0.0487 (9)	0.0441 (8)	0.0167 (7)	0.0170 (7)	0.0176 (7)
C27	0.0437 (8)	0.0519 (9)	0.0389 (7)	0.0208 (7)	0.0119 (6)	0.0173 (7)
N28	0.0639 (9)	0.0438 (7)	0.0414 (7)	0.0212 (6)	0.0180 (6)	0.0181 (6)
C29	0.0350 (7)	0.0417 (8)	0.0405 (8)	0.0147 (6)	0.0114 (6)	0.0180 (6)
C30	0.0374 (7)	0.0428 (8)	0.0423 (8)	0.0152 (6)	0.0111 (6)	0.0194 (6)
C31	0.0796 (12)	0.0550 (10)	0.0570 (10)	0.0361 (9)	0.0311 (9)	0.0284 (8)
C32	0.0982 (16)	0.0598 (11)	0.0783 (13)	0.0440 (11)	0.0347 (12)	0.0407 (10)
C33	0.0734 (12)	0.0606 (11)	0.0667 (12)	0.0231 (10)	0.0186 (10)	0.0418 (10)
C34	0.0614 (11)	0.0696 (12)	0.0512 (9)	0.0185 (9)	0.0243 (8)	0.0328 (9)
C35	0.0497 (9)	0.0516 (9)	0.0509 (9)	0.0203 (7)	0.0217 (7)	0.0246 (7)
C36	0.0397 (7)	0.0448 (8)	0.0427 (7)	0.0204 (6)	0.0213 (6)	0.0230 (6)
C37	0.0415 (8)	0.0470 (8)	0.0523 (9)	0.0195 (7)	0.0203 (7)	0.0201 (7)
C38	0.0665 (11)	0.0458 (9)	0.0624 (10)	0.0193 (8)	0.0317 (9)	0.0165 (8)
C39	0.1079 (16)	0.0549 (10)	0.0672 (12)	0.0482 (11)	0.0528 (12)	0.0327 (9)
C40	0.0996 (15)	0.0870 (14)	0.0656 (12)	0.0726 (13)	0.0506 (12)	0.0506 (11)
C41	0.0556 (10)	0.0696 (11)	0.0486 (9)	0.0373 (9)	0.0239 (8)	0.0322 (8)

C1—O1	1.2225 (18)	C21—H21A	0.9300
C1—C22	1.490 (2)	C22—C27	1.391 (2)
C1—C2	1.496 (2)	C22—C23	1.393 (2)
C2—C7	1.395 (2)	C23—C24	1.379 (2)
C2—C3	1.394 (2)	C23—H23A	0.9300
C3—C4	1.377 (2)	C24—C25	1.392 (2)
C3—H3A	0.9300	C24—H24A	0.9300
C4—C5	1.396 (2)	C25—C26	1.383 (2)
C4—H4A	0.9300	C25—N28	1.4130 (19)
C5—C6	1.3964 (19)	C26—C27	1.384 (2)
C5—N8	1.4127 (18)	C26—H26A	0.9300
C6—C7	1.387 (2)	C27—H27A	0.9300
C6—H6A	0.9300	N28—C29	1.2784 (19)
C7—H7A	0.9300	C29—C30	1.4926 (19)
N8—C9	1.2813 (18)	C29—C36	1.498 (2)
C9—C10	1.4950 (19)	C30—C35	1.387 (2)
C9—C16	1.5033 (19)	C30—C31	1.392 (2)
C10—C15	1.382 (2)	C31—C32	1.380 (2)
C10—C11	1.393 (2)	C31—H31A	0.9300
C11—C12	1.383 (2)	C32—C33	1.375 (3)
C11—H11A	0.9300	C32—H32A	0.9300
C12—C13	1.381 (3)	C33—C34	1.370 (3)
C12—H12A	0.9300	C33—H33A	0.9300
C13—C14	1.361 (2)	C34—C35	1.390 (2)
C13—H13A	0.9300	C34—H34A	0.9300
C14—C15	1.388 (2)	C35—H35A	0.9300
C14—H14A	0.9300	C36—C37	1.389 (2)
C15—H15A	0.9300	C36—C41	1.391 (2)
C16—C21	1.386 (2)	C37—C38	1.384 (2)
C16—C17	1.391 (2)	C37—H37A	0.9300
C17—C18	1.390 (2)	C38—C39	1.373 (3)
C17—H17A	0.9300	C38—H38A	0.9300
C18—C19	1.376 (2)	C39—C40	1.375 (3)
C18—H18A	0.9300	C39—H39A	0.9300
C19—C20	1.375 (2)	C40—C41	1.389 (3)
C19—H19A	0.9300	C40—H40A	0.9300
C20—C21	1.387 (2)	C41—H41A	0.9300
C20—H20A	0.9300
O1—C1—C22	119.75 (13)	C20—C21—H21A	119.7
O1—C1—C2	118.82 (13)	C27—C22—C23	118.10 (13)
C22—C1—C2	121.43 (13)	C27—C22—C1	123.37 (13)
C7—C2—C3	118.23 (13)	C23—C22—C1	118.30 (14)
C7—C2—C1	123.51 (13)	C24—C23—C22	121.35 (15)
C3—C2—C1	117.86 (13)	C24—C23—H23A	119.3
C4—C3—C2	120.68 (13)	C22—C23—H23A	119.3
C4—C3—H3A	119.7	C23—C24—C25	120.03 (14)
C2—C3—H3A	119.7	C23—C24—H24A	120.0
C3—C4—C5	121.35 (13)	C25—C24—H24A	120.0
C3—C4—H4A	119.3	C26—C25—C24	119.11 (14)
C5—C4—H4A	119.3	C26—C25—N28	119.71 (14)
C4—C5—C6	118.22 (13)	C24—C25—N28	120.61 (14)
C4—C5—N8	114.03 (12)	C25—C26—C27	120.64 (15)
C6—C5—N8	127.22 (13)	C25—C26—H26A	119.7
C7—C6—C5	120.31 (13)	C27—C26—H26A	119.7
C7—C6—H6A	119.8	C26—C27—C22	120.73 (14)
C5—C6—H6A	119.8	C26—C27—H27A	119.6
C6—C7—C2	121.20 (13)	C22—C27—H27A	119.6
C6—C7—H7A	119.4	C29—N28—C25	123.09 (13)
C2—C7—H7A	119.4	N28—C29—C30	117.26 (13)
C9—N8—C5	127.61 (12)	N28—C29—C36	123.77 (13)
N8—C9—C10	116.13 (13)	C30—C29—C36	118.97 (12)
N8—C9—C16	126.07 (13)	C35—C30—C31	118.81 (14)
C10—C9—C16	117.80 (12)	C35—C30—C29	121.70 (14)
C15—C10—C11	117.84 (14)	C31—C30—C29	119.49 (14)
C15—C10—C9	121.89 (13)	C32—C31—C30	120.19 (17)
C11—C10—C9	120.25 (13)	C32—C31—H31A	119.9
C12—C11—C10	120.72 (15)	C30—C31—H31A	119.9
C12—C11—H11A	119.6	C33—C32—C31	120.56 (18)
C10—C11—H11A	119.6	C33—C32—H32A	119.7
C13—C12—C11	120.39 (16)	C31—C32—H32A	119.7
C13—C12—H12A	119.8	C34—C33—C32	119.89 (16)
C11—C12—H12A	119.8	C34—C33—H33A	120.1
C14—C13—C12	119.44 (15)	C32—C33—H33A	120.1
C14—C13—H13A	120.3	C33—C34—C35	120.21 (17)
C12—C13—H13A	120.3	C33—C34—H34A	119.9
C13—C14—C15	120.52 (16)	C35—C34—H34A	119.9
C13—C14—H14A	119.7	C30—C35—C34	120.34 (16)
C15—C14—H14A	119.7	C30—C35—H35A	119.8
C10—C15—C14	121.07 (15)	C34—C35—H35A	119.8
C10—C15—H15A	119.5	C37—C36—C41	118.92 (14)
C14—C15—H15A	119.5	C37—C36—C29	120.45 (13)
C21—C16—C17	118.85 (14)	C41—C36—C29	120.62 (14)
C21—C16—C9	120.62 (13)	C38—C37—C36	120.79 (15)
C17—C16—C9	120.53 (13)	C38—C37—H37A	119.6
C16—C17—C18	120.17 (15)	C36—C37—H37A	119.6
C16—C17—H17A	119.9	C39—C38—C37	119.74 (18)
C18—C17—H17A	119.9	C39—C38—H38A	120.1
C19—C18—C17	120.25 (15)	C37—C38—H38A	120.1
C19—C18—H18A	119.9	C38—C39—C40	120.28 (17)
C17—C18—H18A	119.9	C38—C39—H39A	119.9
C20—C19—C18	119.98 (15)	C40—C39—H39A	119.9
C20—C19—H19A	120.0	C39—C40—C41	120.41 (17)
C18—C19—H19A	120.0	C39—C40—H40A	119.8
C19—C20—C21	120.12 (16)	C41—C40—H40A	119.8
C19—C20—H20A	119.9	C40—C41—C36	119.79 (17)
C21—C20—H20A	119.9	C40—C41—H41A	120.1
C16—C21—C20	120.60 (15)	C36—C41—H41A	120.1
C16—C21—H21A	119.7
O1—C1—C2—C7	−144.52 (16)	O1—C1—C22—C27	−152.96 (16)
C22—C1—C2—C7	36.0 (2)	C2—C1—C22—C27	26.6 (2)
O1—C1—C2—C3	28.0 (2)	O1—C1—C22—C23	21.4 (2)
C22—C1—C2—C3	−151.51 (14)	C2—C1—C22—C23	−159.09 (14)
C7—C2—C3—C4	0.3 (2)	C27—C22—C23—C24	0.2 (2)
C1—C2—C3—C4	−172.64 (14)	C1—C22—C23—C24	−174.49 (14)
C2—C3—C4—C5	0.7 (2)	C22—C23—C24—C25	1.0 (3)
C3—C4—C5—C6	−1.0 (2)	C23—C24—C25—C26	−0.7 (2)
C3—C4—C5—N8	171.19 (13)	C23—C24—C25—N28	170.63 (14)
C4—C5—C6—C7	0.4 (2)	C24—C25—C26—C27	−0.8 (2)
N8—C5—C6—C7	−170.67 (14)	N28—C25—C26—C27	−172.23 (14)
C5—C6—C7—C2	0.6 (2)	C25—C26—C27—C22	2.0 (2)
C3—C2—C7—C6	−0.9 (2)	C23—C22—C27—C26	−1.7 (2)
C1—C2—C7—C6	171.58 (14)	C1—C22—C27—C26	172.67 (14)
C4—C5—N8—C9	154.35 (15)	C26—C25—N28—C29	−115.96 (18)
C6—C5—N8—C9	−34.3 (2)	C24—C25—N28—C29	72.8 (2)
C5—N8—C9—C10	176.47 (13)	C25—N28—C29—C30	−173.82 (14)
C5—N8—C9—C16	−4.1 (2)	C25—N28—C29—C36	6.7 (2)
N8—C9—C10—C15	178.78 (15)	N28—C29—C30—C35	−165.71 (15)
C16—C9—C10—C15	−0.7 (2)	C36—C29—C30—C35	13.8 (2)
N8—C9—C10—C11	−3.0 (2)	N28—C29—C30—C31	14.9 (2)
C16—C9—C10—C11	177.57 (14)	C36—C29—C30—C31	−165.62 (15)
C15—C10—C11—C12	1.0 (2)	C35—C30—C31—C32	−0.7 (3)
C9—C10—C11—C12	−177.38 (15)	C29—C30—C31—C32	178.75 (17)
C10—C11—C12—C13	−0.2 (3)	C30—C31—C32—C33	0.4 (3)
C11—C12—C13—C14	−0.7 (3)	C31—C32—C33—C34	0.2 (3)
C12—C13—C14—C15	0.7 (3)	C32—C33—C34—C35	−0.4 (3)
C11—C10—C15—C14	−0.9 (3)	C31—C30—C35—C34	0.4 (2)
C9—C10—C15—C14	177.43 (16)	C29—C30—C35—C34	−179.01 (15)
C13—C14—C15—C10	0.0 (3)	C33—C34—C35—C30	0.1 (3)
N8—C9—C16—C21	−72.1 (2)	N28—C29—C36—C37	−120.14 (17)
C10—C9—C16—C21	107.31 (16)	C30—C29—C36—C37	60.38 (18)
N8—C9—C16—C17	107.75 (18)	N28—C29—C36—C41	58.6 (2)
C10—C9—C16—C17	−72.83 (18)	C30—C29—C36—C41	−120.93 (15)
C21—C16—C17—C18	1.6 (2)	C41—C36—C37—C38	−2.8 (2)
C9—C16—C17—C18	−178.23 (14)	C29—C36—C37—C38	175.92 (14)
C16—C17—C18—C19	−1.0 (2)	C36—C37—C38—C39	2.6 (2)
C17—C18—C19—C20	−0.3 (3)	C37—C38—C39—C40	−0.3 (3)
C18—C19—C20—C21	1.0 (3)	C38—C39—C40—C41	−1.8 (3)
C17—C16—C21—C20	−0.9 (2)	C39—C40—C41—C36	1.6 (3)
C9—C16—C21—C20	178.93 (15)	C37—C36—C41—C40	0.7 (2)
C19—C20—C21—C16	−0.4 (3)	C29—C36—C41—C40	−178.01 (14)