1,3-Bis[3-(1,3-dioxoisoindolin-2-yl)prop-yl]-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione.

The title compound, C(37)H(26)N(4)O(7), is a 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione derivative having isoindolindionylpropyl substitutents attached to the imidazole N atoms. The anthraquinone fragment is buckled, the dihedral angle between the two benzene rings being 1.6 (1)°. The two isoindoline rings of the substituents of the imidazole ring are positioned on opposite sides of the five-membered ring; these are nearly mutually perpendicular [dihedral angle between isoindoline rings = 88.3 (1)°].

Related literature

For the structure of 1,3-dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione, see: Afrakssou et al. (2010 ▶).

Experimental

Crystal data

C37H26N4O7

M = 638.62

Triclinic,

a = 8.4278 (2) Å

b = 13.1258 (3) Å

c = 13.7966 (3) Å

α = 94.359 (1)°

β = 92.472 (1)°

γ = 105.351 (1)°

V = 1464.31 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.24 × 0.12 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer

36987 measured reflections

5996 independent reflections

3420 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 0.99

5996 reflections

433 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029096/bt6818sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029096/bt6818Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029096/bt6818Isup3.cml

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

C37H26N4O7	Z = 2
Mr = 638.62	F(000) = 664
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4278 (2) Å	Cell parameters from 4182 reflections
b = 13.1258 (3) Å	θ = 2.3–21.6°
c = 13.7966 (3) Å	µ = 0.10 mm−1
α = 94.359 (1)°	T = 293 K
β = 92.472 (1)°	Prism, orange
γ = 105.351 (1)°	0.24 × 0.12 × 0.10 mm
V = 1464.31 (6) Å3

Bruker X8 APEXII diffractometer	3420 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 26.4°, θmin = 2.6°
φ and ω scans	h = −10→10
36987 measured reflections	k = −16→16
5996 independent reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1461P] where P = (Fo2 + 2Fc2)/3
5996 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.5704 (2)	0.47298 (13)	0.63443 (11)	0.0694 (5)
O2	0.8925 (2)	0.66460 (14)	0.34484 (13)	0.0834 (6)
O3	0.6768 (2)	0.09268 (12)	0.57598 (11)	0.0700 (5)
O4	0.56768 (19)	−0.10043 (13)	0.05066 (11)	0.0656 (5)
O5	1.0169 (2)	0.15662 (14)	0.18456 (12)	0.0761 (5)
O6	0.3403 (2)	0.29911 (13)	0.84710 (13)	0.0740 (5)
O7	0.81157 (19)	0.56947 (14)	0.87580 (13)	0.0761 (5)
N1	0.7796 (2)	0.19318 (13)	0.44979 (11)	0.0488 (5)
N2	0.6754 (2)	0.27021 (13)	0.57085 (11)	0.0455 (4)
N3	0.7825 (2)	0.02105 (13)	0.14120 (11)	0.0480 (4)
N4	0.5986 (2)	0.41622 (14)	0.85923 (11)	0.0458 (4)
C1	0.8001 (2)	0.29730 (16)	0.43109 (13)	0.0419 (5)
C2	0.8724 (3)	0.34823 (17)	0.35428 (14)	0.0492 (5)
H2	0.9146	0.3125	0.3053	0.059*
C3	0.8798 (3)	0.45430 (17)	0.35264 (14)	0.0491 (5)
H3	0.9291	0.4908	0.3018	0.059*
C4	0.8152 (2)	0.50800 (16)	0.42506 (14)	0.0417 (5)
C5	0.8291 (3)	0.62185 (18)	0.41471 (16)	0.0526 (6)
C6	0.7666 (3)	0.68337 (16)	0.49133 (15)	0.0482 (5)
C7	0.7802 (3)	0.79040 (18)	0.48487 (19)	0.0663 (7)
H7	0.8287	0.8236	0.4322	0.080*
C8	0.7220 (3)	0.8473 (2)	0.5563 (2)	0.0753 (8)
H8	0.7313	0.9189	0.5518	0.090*
C9	0.6501 (3)	0.7985 (2)	0.6346 (2)	0.0742 (8)
H9	0.6134	0.8378	0.6834	0.089*
C10	0.6322 (3)	0.69125 (19)	0.64095 (17)	0.0626 (6)
H10	0.5808	0.6583	0.6930	0.075*
C11	0.6910 (2)	0.63279 (16)	0.56949 (14)	0.0454 (5)
C12	0.6631 (3)	0.51677 (17)	0.57502 (14)	0.0443 (5)
C13	0.7390 (2)	0.45596 (15)	0.50464 (13)	0.0379 (5)
C14	0.7336 (2)	0.34809 (15)	0.50730 (13)	0.0390 (5)
C15	0.7069 (3)	0.17553 (17)	0.53637 (15)	0.0509 (6)
C16	0.8255 (3)	0.11176 (17)	0.38722 (14)	0.0545 (6)
H16A	0.8468	0.0583	0.4269	0.065*
H16B	0.9265	0.1439	0.3572	0.065*
C17	0.6929 (3)	0.05910 (18)	0.30844 (15)	0.0559 (6)
H17A	0.6633	0.1132	0.2730	0.067*
H17B	0.5954	0.0205	0.3383	0.067*
C18	0.7492 (3)	−0.01791 (17)	0.23662 (15)	0.0583 (6)
H18A	0.8483	−0.0314	0.2647	0.070*
H18B	0.6644	−0.0849	0.2281	0.070*
C19	0.6909 (3)	−0.02707 (17)	0.05504 (15)	0.0464 (5)
C20	0.7736 (2)	0.03117 (16)	−0.02462 (14)	0.0442 (5)
C21	0.7354 (3)	0.01664 (19)	−0.12347 (16)	0.0576 (6)
H21	0.6448	−0.0368	−0.1503	0.069*
C22	0.8359 (3)	0.0838 (2)	−0.18175 (17)	0.0626 (6)
H22	0.8122	0.0757	−0.2488	0.075*
C23	0.9712 (3)	0.16276 (19)	−0.14178 (17)	0.0588 (6)
H23	1.0372	0.2069	−0.1824	0.071*
C24	1.0101 (3)	0.17735 (18)	−0.04189 (16)	0.0552 (6)
H24	1.1009	0.2305	−0.0148	0.066*
C25	0.9092 (2)	0.11015 (16)	0.01541 (14)	0.0443 (5)
C26	0.9174 (3)	0.10351 (17)	0.12263 (16)	0.0512 (6)
C27	0.6156 (3)	0.27580 (16)	0.66910 (13)	0.0484 (5)
H27A	0.5691	0.2045	0.6872	0.058*
H27B	0.5291	0.3120	0.6691	0.058*
C28	0.7529 (3)	0.33381 (17)	0.74275 (14)	0.0490 (5)
H28A	0.7990	0.4049	0.7242	0.059*
H28B	0.8395	0.2977	0.7418	0.059*
C29	0.6973 (3)	0.34116 (19)	0.84581 (14)	0.0530 (6)
H29A	0.6331	0.2716	0.8602	0.064*
H29B	0.7935	0.3628	0.8914	0.064*
C30	0.4274 (3)	0.38945 (19)	0.85898 (14)	0.0493 (5)
C31	0.3814 (2)	0.49031 (18)	0.87553 (13)	0.0469 (5)
C32	0.2294 (3)	0.5099 (2)	0.88355 (16)	0.0610 (6)
H32	0.1332	0.4546	0.8790	0.073*
C33	0.2245 (3)	0.6145 (2)	0.89860 (16)	0.0685 (7)
H33	0.1233	0.6297	0.9035	0.082*
C34	0.3671 (3)	0.6964 (2)	0.90647 (16)	0.0679 (7)
H34	0.3606	0.7660	0.9170	0.082*
C35	0.5202 (3)	0.6767 (2)	0.89889 (16)	0.0620 (6)
H35	0.6166	0.7319	0.9043	0.074*
C36	0.5244 (2)	0.57277 (18)	0.88312 (14)	0.0472 (5)
C37	0.6653 (3)	0.52552 (18)	0.87256 (15)	0.0510 (6)

	U11	U22	U33	U12	U13	U23
O1	0.1019 (13)	0.0556 (11)	0.0652 (10)	0.0393 (10)	0.0356 (10)	0.0145 (8)
O2	0.1093 (15)	0.0583 (12)	0.0925 (13)	0.0271 (10)	0.0426 (11)	0.0323 (10)
O3	0.1239 (15)	0.0381 (10)	0.0533 (9)	0.0289 (9)	0.0149 (9)	0.0073 (8)
O4	0.0659 (10)	0.0502 (10)	0.0693 (10)	−0.0027 (9)	0.0061 (8)	−0.0011 (8)
O5	0.0816 (12)	0.0678 (12)	0.0598 (10)	−0.0074 (10)	−0.0119 (9)	−0.0057 (9)
O6	0.0671 (11)	0.0524 (11)	0.0929 (13)	−0.0004 (9)	0.0043 (9)	0.0065 (9)
O7	0.0459 (10)	0.0699 (12)	0.1047 (14)	0.0042 (9)	0.0047 (9)	0.0001 (10)
N1	0.0769 (13)	0.0369 (10)	0.0363 (9)	0.0233 (9)	0.0055 (9)	−0.0037 (7)
N2	0.0698 (12)	0.0332 (10)	0.0358 (9)	0.0186 (8)	0.0067 (8)	−0.0003 (7)
N3	0.0614 (11)	0.0369 (10)	0.0428 (10)	0.0097 (9)	0.0079 (8)	−0.0052 (8)
N4	0.0468 (10)	0.0469 (11)	0.0435 (10)	0.0125 (9)	0.0083 (8)	−0.0004 (8)
C1	0.0549 (12)	0.0362 (12)	0.0350 (10)	0.0152 (10)	−0.0013 (9)	−0.0020 (9)
C2	0.0593 (14)	0.0503 (14)	0.0388 (11)	0.0173 (11)	0.0075 (10)	−0.0027 (10)
C3	0.0560 (13)	0.0482 (14)	0.0421 (12)	0.0109 (11)	0.0073 (10)	0.0056 (10)
C4	0.0451 (12)	0.0377 (12)	0.0419 (11)	0.0115 (9)	−0.0021 (9)	0.0032 (9)
C5	0.0545 (13)	0.0476 (14)	0.0572 (14)	0.0138 (11)	0.0051 (11)	0.0125 (11)
C6	0.0519 (13)	0.0353 (12)	0.0579 (13)	0.0151 (10)	−0.0078 (11)	0.0024 (10)
C7	0.0750 (17)	0.0406 (15)	0.0838 (17)	0.0164 (13)	−0.0008 (14)	0.0084 (13)
C8	0.092 (2)	0.0415 (15)	0.094 (2)	0.0245 (14)	−0.0082 (17)	0.0013 (15)
C9	0.094 (2)	0.0526 (17)	0.0812 (18)	0.0387 (15)	−0.0088 (16)	−0.0173 (14)
C10	0.0846 (17)	0.0518 (15)	0.0572 (14)	0.0322 (13)	−0.0012 (12)	−0.0050 (11)
C11	0.0536 (13)	0.0367 (12)	0.0471 (12)	0.0188 (10)	−0.0099 (10)	−0.0046 (10)
C12	0.0541 (13)	0.0450 (13)	0.0378 (11)	0.0216 (10)	−0.0011 (10)	0.0014 (9)
C13	0.0430 (11)	0.0359 (12)	0.0355 (10)	0.0136 (9)	−0.0024 (9)	−0.0001 (9)
C14	0.0474 (12)	0.0371 (12)	0.0325 (10)	0.0135 (9)	−0.0006 (9)	−0.0019 (9)
C15	0.0783 (16)	0.0341 (13)	0.0424 (12)	0.0201 (11)	0.0013 (11)	0.0003 (10)
C16	0.0792 (16)	0.0467 (14)	0.0438 (12)	0.0307 (12)	0.0026 (11)	−0.0064 (10)
C17	0.0644 (15)	0.0515 (14)	0.0499 (12)	0.0150 (12)	0.0116 (11)	−0.0091 (11)
C18	0.0866 (17)	0.0415 (13)	0.0464 (12)	0.0180 (12)	0.0127 (12)	−0.0046 (10)
C19	0.0501 (13)	0.0362 (12)	0.0522 (13)	0.0132 (11)	0.0060 (10)	−0.0061 (10)
C20	0.0462 (12)	0.0402 (12)	0.0468 (12)	0.0146 (10)	0.0044 (10)	−0.0042 (9)
C21	0.0586 (14)	0.0585 (15)	0.0515 (14)	0.0123 (12)	−0.0025 (11)	−0.0047 (11)
C22	0.0748 (17)	0.0716 (18)	0.0472 (13)	0.0297 (15)	0.0055 (12)	0.0043 (12)
C23	0.0594 (15)	0.0625 (16)	0.0627 (15)	0.0253 (13)	0.0172 (12)	0.0188 (12)
C24	0.0460 (13)	0.0545 (15)	0.0648 (15)	0.0133 (11)	0.0032 (11)	0.0048 (12)
C25	0.0445 (12)	0.0408 (12)	0.0490 (12)	0.0150 (10)	0.0038 (10)	−0.0003 (10)
C26	0.0569 (14)	0.0416 (13)	0.0517 (13)	0.0104 (11)	0.0005 (11)	−0.0050 (10)
C27	0.0669 (14)	0.0354 (12)	0.0428 (12)	0.0119 (10)	0.0130 (10)	0.0039 (9)
C28	0.0560 (13)	0.0521 (14)	0.0439 (12)	0.0224 (11)	0.0084 (10)	0.0047 (10)
C29	0.0640 (14)	0.0591 (15)	0.0415 (12)	0.0263 (12)	0.0058 (10)	0.0026 (10)
C30	0.0521 (14)	0.0520 (15)	0.0386 (11)	0.0056 (11)	0.0041 (10)	0.0016 (10)
C31	0.0471 (13)	0.0558 (14)	0.0365 (11)	0.0128 (11)	0.0057 (9)	−0.0026 (10)
C32	0.0497 (14)	0.0784 (19)	0.0524 (13)	0.0155 (13)	0.0014 (11)	−0.0026 (12)
C33	0.0639 (16)	0.100 (2)	0.0486 (14)	0.0408 (16)	−0.0043 (12)	−0.0118 (14)
C34	0.0821 (19)	0.0726 (19)	0.0551 (14)	0.0400 (16)	−0.0119 (13)	−0.0162 (13)
C35	0.0685 (16)	0.0545 (16)	0.0581 (14)	0.0144 (13)	−0.0081 (12)	−0.0112 (11)
C36	0.0482 (13)	0.0520 (14)	0.0391 (11)	0.0119 (11)	0.0015 (9)	−0.0046 (10)
C37	0.0488 (13)	0.0543 (15)	0.0458 (12)	0.0080 (11)	0.0040 (10)	−0.0014 (10)

O1—C12	1.226 (2)	C16—C17	1.510 (3)
O2—C5	1.224 (3)	C16—H16A	0.9700
O3—C15	1.225 (2)	C16—H16B	0.9700
O4—C19	1.211 (2)	C17—C18	1.540 (3)
O5—C26	1.208 (2)	C17—H17A	0.9700
O6—C30	1.213 (2)	C17—H17B	0.9700
O7—C37	1.212 (2)	C18—H18A	0.9700
N1—C15	1.373 (3)	C18—H18B	0.9700
N1—C1	1.377 (3)	C19—C20	1.480 (3)
N1—C16	1.465 (2)	C20—C21	1.375 (3)
N2—C15	1.392 (3)	C20—C25	1.385 (3)
N2—C14	1.401 (2)	C21—C22	1.383 (3)
N2—C27	1.469 (2)	C21—H21	0.9300
N3—C26	1.395 (3)	C22—C23	1.382 (3)
N3—C19	1.399 (2)	C22—H22	0.9300
N3—C18	1.460 (3)	C23—C24	1.390 (3)
N4—C37	1.390 (3)	C23—H23	0.9300
N4—C30	1.392 (3)	C24—C25	1.376 (3)
N4—C29	1.454 (3)	C24—H24	0.9300
C1—C2	1.374 (3)	C25—C26	1.488 (3)
C1—C14	1.417 (3)	C27—C28	1.505 (3)
C2—C3	1.379 (3)	C27—H27A	0.9700
C2—H2	0.9300	C27—H27B	0.9700
C3—C4	1.391 (3)	C28—C29	1.521 (3)
C3—H3	0.9300	C28—H28A	0.9700
C4—C13	1.424 (3)	C28—H28B	0.9700
C4—C5	1.486 (3)	C29—H29A	0.9700
C5—C6	1.480 (3)	C29—H29B	0.9700
C6—C7	1.389 (3)	C30—C31	1.479 (3)
C6—C11	1.398 (3)	C31—C32	1.379 (3)
C7—C8	1.376 (3)	C31—C36	1.384 (3)
C7—H7	0.9300	C32—C33	1.385 (3)
C8—C9	1.378 (4)	C32—H32	0.9300
C8—H8	0.9300	C33—C34	1.378 (4)
C9—C10	1.386 (3)	C33—H33	0.9300
C9—H9	0.9300	C34—C35	1.388 (3)
C10—C11	1.391 (3)	C34—H34	0.9300
C10—H10	0.9300	C35—C36	1.375 (3)
C11—C12	1.487 (3)	C35—H35	0.9300
C12—C13	1.481 (3)	C36—C37	1.486 (3)
C13—C14	1.408 (3)
C15—N1—C1	109.88 (16)	C17—C18—H18A	108.8
C15—N1—C16	124.23 (18)	N3—C18—H18B	108.8
C1—N1—C16	125.89 (17)	C17—C18—H18B	108.8
C15—N2—C14	109.76 (16)	H18A—C18—H18B	107.7
C15—N2—C27	117.23 (17)	O4—C19—N3	124.8 (2)
C14—N2—C27	132.17 (16)	O4—C19—C20	129.10 (19)
C26—N3—C19	111.35 (17)	N3—C19—C20	106.09 (17)
C26—N3—C18	124.79 (17)	C21—C20—C25	121.1 (2)
C19—N3—C18	123.59 (17)	C21—C20—C19	130.41 (19)
C37—N4—C30	111.15 (18)	C25—C20—C19	108.54 (17)
C37—N4—C29	123.58 (18)	C20—C21—C22	118.0 (2)
C30—N4—C29	125.26 (18)	C20—C21—H21	121.0
C2—C1—N1	128.55 (18)	C22—C21—H21	121.0
C2—C1—C14	123.38 (19)	C21—C22—C23	121.0 (2)
N1—C1—C14	108.07 (17)	C21—C22—H22	119.5
C1—C2—C3	117.46 (19)	C23—C22—H22	119.5
C1—C2—H2	121.3	C22—C23—C24	121.1 (2)
C3—C2—H2	121.3	C22—C23—H23	119.4
C2—C3—C4	121.64 (19)	C24—C23—H23	119.4
C2—C3—H3	119.2	C25—C24—C23	117.5 (2)
C4—C3—H3	119.2	C25—C24—H24	121.3
C3—C4—C13	121.45 (19)	C23—C24—H24	121.3
C3—C4—C5	116.62 (18)	C24—C25—C20	121.42 (19)
C13—C4—C5	121.93 (18)	C24—C25—C26	130.91 (19)
O2—C5—C6	120.4 (2)	C20—C25—C26	107.67 (18)
O2—C5—C4	120.9 (2)	O5—C26—N3	124.3 (2)
C6—C5—C4	118.74 (19)	O5—C26—C25	129.3 (2)
C7—C6—C11	120.0 (2)	N3—C26—C25	106.34 (17)
C7—C6—C5	120.3 (2)	N2—C27—C28	111.20 (17)
C11—C6—C5	119.67 (19)	N2—C27—H27A	109.4
C8—C7—C6	120.1 (2)	C28—C27—H27A	109.4
C8—C7—H7	120.0	N2—C27—H27B	109.4
C6—C7—H7	120.0	C28—C27—H27B	109.4
C7—C8—C9	120.3 (2)	H27A—C27—H27B	108.0
C7—C8—H8	119.9	C27—C28—C29	113.17 (18)
C9—C8—H8	119.9	C27—C28—H28A	108.9
C8—C9—C10	120.4 (2)	C29—C28—H28A	108.9
C8—C9—H9	119.8	C27—C28—H28B	108.9
C10—C9—H9	119.8	C29—C28—H28B	108.9
C9—C10—C11	120.0 (2)	H28A—C28—H28B	107.8
C9—C10—H10	120.0	N4—C29—C28	112.29 (17)
C11—C10—H10	120.0	N4—C29—H29A	109.1
C10—C11—C6	119.2 (2)	C28—C29—H29A	109.1
C10—C11—C12	119.2 (2)	N4—C29—H29B	109.1
C6—C11—C12	121.51 (18)	C28—C29—H29B	109.1
O1—C12—C13	121.66 (19)	H29A—C29—H29B	107.9
O1—C12—C11	118.85 (19)	O6—C30—N4	123.9 (2)
C13—C12—C11	119.37 (19)	O6—C30—C31	129.7 (2)
C14—C13—C4	117.03 (17)	N4—C30—C31	106.47 (18)
C14—C13—C12	124.79 (18)	C32—C31—C36	120.9 (2)
C4—C13—C12	118.08 (18)	C32—C31—C30	130.9 (2)
N2—C14—C13	135.45 (17)	C36—C31—C30	108.20 (18)
N2—C14—C1	105.52 (16)	C31—C32—C33	117.9 (2)
C13—C14—C1	119.03 (17)	C31—C32—H32	121.0
O3—C15—N1	126.6 (2)	C33—C32—H32	121.0
O3—C15—N2	126.6 (2)	C34—C33—C32	121.1 (2)
N1—C15—N2	106.73 (18)	C34—C33—H33	119.5
N1—C16—C17	112.36 (18)	C32—C33—H33	119.5
N1—C16—H16A	109.1	C33—C34—C35	121.1 (2)
C17—C16—H16A	109.1	C33—C34—H34	119.5
N1—C16—H16B	109.1	C35—C34—H34	119.5
C17—C16—H16B	109.1	C36—C35—C34	117.6 (2)
H16A—C16—H16B	107.9	C36—C35—H35	121.2
C16—C17—C18	112.01 (19)	C34—C35—H35	121.2
C16—C17—H17A	109.2	C35—C36—C31	121.4 (2)
C18—C17—H17A	109.2	C35—C36—C37	131.0 (2)
C16—C17—H17B	109.2	C31—C36—C37	107.57 (19)
C18—C17—H17B	109.2	O7—C37—N4	124.3 (2)
H17A—C17—H17B	107.9	O7—C37—C36	129.1 (2)
N3—C18—C17	113.82 (18)	N4—C37—C36	106.59 (18)
N3—C18—H18A	108.8
C15—N1—C1—C2	177.7 (2)	C26—N3—C18—C17	71.5 (3)
C16—N1—C1—C2	−3.0 (3)	C19—N3—C18—C17	−115.0 (2)
C15—N1—C1—C14	−1.8 (2)	C16—C17—C18—N3	−107.3 (2)
C16—N1—C1—C14	177.54 (18)	C26—N3—C19—O4	−179.8 (2)
N1—C1—C2—C3	−179.2 (2)	C18—N3—C19—O4	5.9 (3)
C14—C1—C2—C3	0.2 (3)	C26—N3—C19—C20	−1.0 (2)
C1—C2—C3—C4	−0.7 (3)	C18—N3—C19—C20	−175.24 (18)
C2—C3—C4—C13	0.3 (3)	O4—C19—C20—C21	−1.5 (4)
C2—C3—C4—C5	−179.38 (18)	N3—C19—C20—C21	179.7 (2)
C3—C4—C5—O2	1.0 (3)	O4—C19—C20—C25	179.0 (2)
C13—C4—C5—O2	−178.7 (2)	N3—C19—C20—C25	0.3 (2)
C3—C4—C5—C6	−178.26 (18)	C25—C20—C21—C22	−0.5 (3)
C13—C4—C5—C6	2.1 (3)	C19—C20—C21—C22	−179.9 (2)
O2—C5—C6—C7	−0.4 (3)	C20—C21—C22—C23	0.4 (4)
C4—C5—C6—C7	178.88 (19)	C21—C22—C23—C24	−0.2 (4)
O2—C5—C6—C11	178.4 (2)	C22—C23—C24—C25	0.2 (3)
C4—C5—C6—C11	−2.3 (3)	C23—C24—C25—C20	−0.3 (3)
C11—C6—C7—C8	1.2 (3)	C23—C24—C25—C26	179.1 (2)
C5—C6—C7—C8	−180.0 (2)	C21—C20—C25—C24	0.5 (3)
C6—C7—C8—C9	0.0 (4)	C19—C20—C25—C24	−179.99 (19)
C7—C8—C9—C10	−1.5 (4)	C21—C20—C25—C26	−179.0 (2)
C8—C9—C10—C11	1.8 (4)	C19—C20—C25—C26	0.5 (2)
C9—C10—C11—C6	−0.5 (3)	C19—N3—C26—O5	−178.9 (2)
C9—C10—C11—C12	−177.0 (2)	C18—N3—C26—O5	−4.8 (4)
C7—C6—C11—C10	−1.0 (3)	C19—N3—C26—C25	1.3 (2)
C5—C6—C11—C10	−179.78 (19)	C18—N3—C26—C25	175.46 (18)
C7—C6—C11—C12	175.42 (19)	C24—C25—C26—O5	−0.3 (4)
C5—C6—C11—C12	−3.4 (3)	C20—C25—C26—O5	179.1 (2)
C10—C11—C12—O1	9.8 (3)	C24—C25—C26—N3	179.5 (2)
C6—C11—C12—O1	−166.6 (2)	C20—C25—C26—N3	−1.1 (2)
C10—C11—C12—C13	−174.23 (18)	C15—N2—C27—C28	100.4 (2)
C6—C11—C12—C13	9.4 (3)	C14—N2—C27—C28	−67.9 (3)
C3—C4—C13—C14	0.7 (3)	N2—C27—C28—C29	−179.70 (18)
C5—C4—C13—C14	−179.66 (17)	C37—N4—C29—C28	−78.3 (2)
C3—C4—C13—C12	−175.86 (18)	C30—N4—C29—C28	100.6 (2)
C5—C4—C13—C12	3.8 (3)	C27—C28—C29—N4	−73.0 (2)
O1—C12—C13—C14	−9.7 (3)	C37—N4—C30—O6	178.8 (2)
C11—C12—C13—C14	174.41 (17)	C29—N4—C30—O6	−0.2 (3)
O1—C12—C13—C4	166.55 (19)	C37—N4—C30—C31	−1.2 (2)
C11—C12—C13—C4	−9.3 (3)	C29—N4—C30—C31	179.77 (16)
C15—N2—C14—C13	−178.8 (2)	O6—C30—C31—C32	1.1 (4)
C27—N2—C14—C13	−9.9 (4)	N4—C30—C31—C32	−178.8 (2)
C15—N2—C14—C1	0.9 (2)	O6—C30—C31—C36	−178.9 (2)
C27—N2—C14—C1	169.8 (2)	N4—C30—C31—C36	1.1 (2)
C4—C13—C14—N2	178.53 (19)	C36—C31—C32—C33	0.5 (3)
C12—C13—C14—N2	−5.2 (3)	C30—C31—C32—C33	−179.6 (2)
C4—C13—C14—C1	−1.2 (3)	C31—C32—C33—C34	−0.8 (3)
C12—C13—C14—C1	175.10 (17)	C32—C33—C34—C35	0.4 (4)
C2—C1—C14—N2	−179.00 (18)	C33—C34—C35—C36	0.1 (3)
N1—C1—C14—N2	0.5 (2)	C34—C35—C36—C31	−0.3 (3)
C2—C1—C14—C13	0.8 (3)	C34—C35—C36—C37	−179.4 (2)
N1—C1—C14—C13	−179.72 (16)	C32—C31—C36—C35	0.0 (3)
C1—N1—C15—O3	−177.2 (2)	C30—C31—C36—C35	−179.91 (19)
C16—N1—C15—O3	3.5 (4)	C32—C31—C36—C37	179.31 (18)
C1—N1—C15—N2	2.3 (2)	C30—C31—C36—C37	−0.6 (2)
C16—N1—C15—N2	−177.00 (18)	C30—N4—C37—O7	179.8 (2)
C14—N2—C15—O3	177.5 (2)	C29—N4—C37—O7	−1.1 (3)
C27—N2—C15—O3	6.7 (3)	C30—N4—C37—C36	0.8 (2)
C14—N2—C15—N1	−2.0 (2)	C29—N4—C37—C36	179.88 (16)
C27—N2—C15—N1	−172.75 (17)	C35—C36—C37—O7	0.1 (4)
C15—N1—C16—C17	94.3 (2)	C31—C36—C37—O7	−179.0 (2)
C1—N1—C16—C17	−84.9 (3)	C35—C36—C37—N4	179.1 (2)
N1—C16—C17—C18	174.04 (18)	C31—C36—C37—N4	−0.1 (2)