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

The title compound, C(37)H(24)N(2)O(3), is a 1H-anthra[2,1-d]imidazole-2,6,11(3H)-trione derivative having naphthyl-methyl substitutents attached to the imidazole N atoms. The anthraquinone part of the mol-ecule is somewhat folded along the the line connecting the carbonyl bonds. The dihedral angle between the two benzene rings is 7.8 (1)°. The two naphthyl systems of the substituents of the imidazole ring are positioned on the same side of the five-membered ring; these are approximately coplanar, the dihedral angle between the napthyl systems being 4.3 (2)°.

Related literature

For the structure of 1,3-dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione, see: Afrakssou et al. (2011 ▶).

Experimental

Crystal data

C37H24N2O3

M = 544.58

Orthorhombic,

a = 8.0901 (1) Å

b = 12.8226 (2) Å

c = 26.1472 (4) Å

V = 2712.41 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer

34004 measured reflections

3781 independent reflections

3453 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.138

S = 1.10

3781 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.15 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/S1600536811029102/bt6819sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029102/bt6819Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029102/bt6819Isup3.cml

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

C37H24N2O3	F(000) = 1136
Mr = 544.58	Dx = 1.334 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9907 reflections
a = 8.0901 (1) Å	θ = 2.2–28.1°
b = 12.8226 (2) Å	µ = 0.09 mm−1
c = 26.1472 (4) Å	T = 293 K
V = 2712.41 (7) Å3	Prism, orange
Z = 4	0.25 × 0.20 × 0.15 mm

Bruker X8 APEXII diffractometer	3453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 28.3°, θmin = 1.6°
φ and ω scans	h = −10→10
34004 measured reflections	k = −16→17
3781 independent reflections	l = −34→33

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0817P)2 + 0.4504P] where P = (Fo2 + 2Fc2)/3
3781 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.8235 (3)	0.91407 (16)	0.22345 (10)	0.0663 (6)
O2	0.2782 (2)	0.69294 (15)	0.20827 (8)	0.0520 (5)
O3	0.5179 (3)	0.31578 (14)	0.17289 (9)	0.0622 (5)
N1	0.7325 (3)	0.42761 (15)	0.19328 (7)	0.0405 (4)
N2	0.4839 (2)	0.49636 (14)	0.17989 (7)	0.0376 (4)
C1	0.7480 (3)	0.53404 (17)	0.19934 (8)	0.0356 (4)
C2	0.8853 (3)	0.59225 (19)	0.21178 (9)	0.0415 (5)
H2	0.9873	0.5609	0.2174	0.050*
C3	0.8656 (3)	0.6996 (2)	0.21557 (9)	0.0414 (5)
H3	0.9567	0.7412	0.2230	0.050*
C4	0.7118 (3)	0.74609 (18)	0.20846 (8)	0.0361 (4)
C5	0.7031 (3)	0.86234 (19)	0.21094 (9)	0.0427 (5)
C6	0.5463 (3)	0.91261 (18)	0.19539 (8)	0.0402 (5)
C7	0.5391 (4)	1.02130 (19)	0.18900 (9)	0.0490 (6)
H7	0.6329	1.0619	0.1943	0.059*
C8	0.3913 (4)	1.0677 (2)	0.17469 (10)	0.0555 (7)
H8	0.3866	1.1395	0.1701	0.067*
C9	0.2520 (4)	1.0085 (2)	0.16729 (11)	0.0583 (7)
H9	0.1543	1.0405	0.1570	0.070*
C10	0.2556 (3)	0.9011 (2)	0.17499 (10)	0.0495 (6)
H10	0.1599	0.8617	0.1711	0.059*
C11	0.4040 (3)	0.85298 (17)	0.18862 (8)	0.0392 (5)
C12	0.4052 (3)	0.73869 (18)	0.19823 (8)	0.0372 (4)
C13	0.5687 (3)	0.68596 (17)	0.19743 (8)	0.0328 (4)
C14	0.5893 (3)	0.57835 (16)	0.19155 (7)	0.0327 (4)
C15	0.5716 (3)	0.40268 (18)	0.18116 (9)	0.0428 (5)
C16	0.8669 (3)	0.35269 (19)	0.18985 (10)	0.0481 (6)
H16A	0.8266	0.2849	0.2005	0.058*
H16B	0.9538	0.3732	0.2133	0.058*
C17	0.9387 (3)	0.34343 (17)	0.13695 (10)	0.0429 (5)
C18	0.9014 (3)	0.40959 (18)	0.09759 (10)	0.0451 (5)
H18	0.8293	0.4648	0.1034	0.054*
C19	0.9701 (3)	0.3961 (2)	0.04800 (10)	0.0484 (6)
C20	0.9316 (4)	0.4642 (3)	0.00705 (12)	0.0637 (7)
H20	0.8620	0.5207	0.0126	0.076*
C21	0.9959 (5)	0.4474 (3)	−0.04074 (13)	0.0794 (10)
H21	0.9703	0.4927	−0.0674	0.095*
C22	1.1008 (5)	0.3617 (4)	−0.04943 (16)	0.0898 (13)
H22	1.1429	0.3497	−0.0820	0.108*
C23	1.1405 (5)	0.2970 (3)	−0.01072 (16)	0.0841 (12)
H23	1.2102	0.2410	−0.0172	0.101*
C24	1.0795 (3)	0.3116 (2)	0.03943 (13)	0.0601 (7)
C25	1.1201 (4)	0.2469 (3)	0.08101 (14)	0.0707 (9)
H25	1.1950	0.1928	0.0762	0.085*
C26	1.0524 (4)	0.2618 (2)	0.12796 (13)	0.0621 (8)
H26	1.0814	0.2175	0.1547	0.075*
C27	0.3236 (3)	0.49777 (19)	0.15322 (9)	0.0425 (5)
H27A	0.2505	0.5473	0.1698	0.051*
H27B	0.2730	0.4293	0.1554	0.051*
C28	0.3448 (3)	0.5277 (2)	0.09756 (10)	0.0464 (5)
C29	0.2724 (4)	0.6134 (2)	0.07760 (12)	0.0582 (7)
H29	0.2112	0.6569	0.0988	0.070*
C30	0.2880 (4)	0.6389 (3)	0.02394 (12)	0.0637 (8)
C31	0.2094 (8)	0.7273 (4)	0.00331 (19)	0.1075 (16)
H31	0.1466	0.7711	0.0240	0.129*
C32	0.2270 (9)	0.7476 (5)	−0.0475 (2)	0.124 (2)
H32	0.1783	0.8069	−0.0614	0.149*
C33	0.3171 (9)	0.6806 (5)	−0.07904 (17)	0.123 (2)
H33	0.3223	0.6946	−0.1139	0.147*
C34	0.3971 (7)	0.5962 (5)	−0.06056 (15)	0.1035 (15)
H34	0.4607	0.5546	−0.0820	0.124*
C35	0.3817 (5)	0.5718 (3)	−0.00662 (13)	0.0732 (9)
C36	0.4562 (5)	0.4837 (3)	0.01427 (14)	0.0783 (10)
H36	0.5183	0.4397	−0.0064	0.094*
C37	0.4385 (4)	0.4619 (3)	0.06506 (12)	0.0638 (7)
H37	0.4889	0.4028	0.0786	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0528 (11)	0.0477 (10)	0.0982 (16)	−0.0092 (9)	−0.0213 (11)	−0.0135 (11)
O2	0.0314 (8)	0.0470 (9)	0.0776 (13)	−0.0005 (7)	0.0068 (8)	0.0009 (9)
O3	0.0635 (12)	0.0356 (8)	0.0875 (15)	−0.0069 (9)	−0.0111 (11)	0.0065 (9)
N1	0.0402 (10)	0.0359 (9)	0.0454 (10)	0.0041 (8)	−0.0029 (8)	0.0030 (7)
N2	0.0343 (9)	0.0368 (9)	0.0418 (9)	−0.0045 (7)	−0.0033 (7)	0.0025 (7)
C1	0.0351 (10)	0.0383 (10)	0.0333 (9)	0.0020 (9)	0.0013 (8)	0.0009 (8)
C2	0.0287 (9)	0.0492 (12)	0.0465 (11)	0.0044 (9)	−0.0021 (9)	−0.0016 (10)
C3	0.0307 (10)	0.0475 (12)	0.0459 (11)	−0.0054 (9)	−0.0031 (9)	−0.0048 (10)
C4	0.0342 (10)	0.0396 (10)	0.0344 (10)	−0.0034 (9)	−0.0004 (8)	−0.0034 (8)
C5	0.0413 (12)	0.0409 (11)	0.0459 (12)	−0.0061 (10)	−0.0018 (10)	−0.0069 (9)
C6	0.0465 (12)	0.0382 (10)	0.0360 (10)	−0.0002 (10)	0.0000 (9)	−0.0061 (8)
C7	0.0627 (15)	0.0388 (11)	0.0456 (12)	−0.0025 (11)	0.0005 (11)	−0.0051 (9)
C8	0.0768 (19)	0.0363 (11)	0.0536 (14)	0.0082 (12)	−0.0006 (14)	−0.0017 (10)
C9	0.0631 (16)	0.0454 (13)	0.0666 (16)	0.0169 (13)	−0.0063 (14)	0.0005 (12)
C10	0.0449 (13)	0.0454 (12)	0.0582 (14)	0.0075 (11)	−0.0040 (11)	0.0011 (11)
C11	0.0415 (11)	0.0391 (10)	0.0372 (11)	0.0038 (9)	0.0014 (9)	−0.0009 (8)
C12	0.0323 (10)	0.0388 (10)	0.0406 (10)	0.0015 (8)	−0.0008 (8)	−0.0008 (8)
C13	0.0290 (9)	0.0382 (10)	0.0311 (9)	−0.0002 (8)	0.0012 (7)	0.0008 (7)
C14	0.0310 (9)	0.0377 (10)	0.0294 (8)	−0.0012 (8)	−0.0005 (7)	0.0007 (7)
C15	0.0460 (12)	0.0374 (10)	0.0449 (11)	−0.0030 (10)	−0.0025 (10)	0.0060 (9)
C16	0.0513 (14)	0.0390 (11)	0.0540 (14)	0.0114 (11)	−0.0060 (11)	0.0074 (10)
C17	0.0383 (11)	0.0326 (10)	0.0578 (13)	0.0037 (9)	−0.0077 (10)	−0.0053 (9)
C18	0.0432 (12)	0.0385 (11)	0.0535 (13)	0.0080 (10)	−0.0014 (10)	−0.0052 (9)
C19	0.0401 (12)	0.0501 (13)	0.0548 (13)	−0.0045 (11)	−0.0018 (10)	−0.0140 (11)
C20	0.0662 (18)	0.0668 (17)	0.0582 (16)	−0.0060 (16)	0.0029 (14)	−0.0079 (13)
C21	0.083 (2)	0.102 (3)	0.0535 (16)	−0.020 (2)	0.0029 (17)	−0.0042 (17)
C22	0.083 (3)	0.120 (3)	0.066 (2)	−0.014 (3)	0.018 (2)	−0.030 (2)
C23	0.064 (2)	0.096 (3)	0.092 (3)	0.002 (2)	0.016 (2)	−0.041 (2)
C24	0.0433 (13)	0.0601 (16)	0.0768 (18)	−0.0004 (13)	0.0029 (13)	−0.0247 (14)
C25	0.0575 (18)	0.0581 (17)	0.096 (2)	0.0236 (15)	−0.0032 (17)	−0.0215 (17)
C26	0.0557 (16)	0.0442 (13)	0.086 (2)	0.0194 (13)	−0.0112 (15)	−0.0067 (13)
C27	0.0316 (10)	0.0443 (11)	0.0517 (12)	−0.0095 (9)	−0.0044 (9)	−0.0003 (10)
C28	0.0399 (11)	0.0481 (13)	0.0512 (12)	−0.0100 (10)	−0.0136 (10)	0.0003 (10)
C29	0.0518 (14)	0.0605 (16)	0.0624 (16)	0.0023 (13)	−0.0105 (13)	−0.0016 (12)
C30	0.0605 (17)	0.0708 (18)	0.0599 (16)	−0.0016 (16)	−0.0144 (14)	0.0034 (14)
C31	0.120 (4)	0.115 (4)	0.088 (3)	0.024 (3)	−0.026 (3)	0.025 (3)
C32	0.152 (5)	0.144 (4)	0.076 (3)	0.003 (4)	−0.032 (3)	0.033 (3)
C33	0.151 (5)	0.164 (5)	0.053 (2)	−0.019 (5)	−0.033 (3)	0.028 (3)
C34	0.113 (4)	0.140 (4)	0.058 (2)	−0.012 (3)	−0.014 (2)	0.003 (2)
C35	0.068 (2)	0.092 (2)	0.0599 (17)	−0.0076 (19)	−0.0178 (15)	−0.0041 (17)
C36	0.081 (2)	0.093 (2)	0.0611 (17)	0.009 (2)	−0.0021 (17)	−0.0191 (18)
C37	0.0654 (18)	0.0679 (17)	0.0583 (15)	0.0064 (16)	−0.0097 (14)	−0.0098 (13)

O1—C5	1.223 (3)	C18—H18	0.9300
O2—C12	1.212 (3)	C19—C20	1.416 (4)
O3—C15	1.215 (3)	C19—C24	1.417 (4)
N1—C15	1.377 (3)	C20—C21	1.370 (5)
N1—C1	1.380 (3)	C20—H20	0.9300
N1—C16	1.454 (3)	C21—C22	1.407 (6)
N2—C14	1.388 (3)	C21—H21	0.9300
N2—C15	1.395 (3)	C22—C23	1.347 (6)
N2—C27	1.473 (3)	C22—H22	0.9300
C1—C2	1.377 (3)	C23—C24	1.413 (5)
C1—C14	1.419 (3)	C23—H23	0.9300
C2—C3	1.390 (3)	C24—C25	1.406 (5)
C2—H2	0.9300	C25—C26	1.357 (5)
C3—C4	1.392 (3)	C25—H25	0.9300
C3—H3	0.9300	C26—H26	0.9300
C4—C13	1.420 (3)	C27—C28	1.515 (3)
C4—C5	1.494 (3)	C27—H27A	0.9700
C5—C6	1.480 (4)	C27—H27B	0.9700
C6—C11	1.394 (3)	C28—C29	1.350 (4)
C6—C7	1.405 (3)	C28—C37	1.418 (4)
C7—C8	1.387 (4)	C29—C30	1.446 (4)
C7—H7	0.9300	C29—H29	0.9300
C8—C9	1.373 (4)	C30—C35	1.398 (5)
C8—H8	0.9300	C30—C31	1.407 (6)
C9—C10	1.393 (4)	C31—C32	1.362 (7)
C9—H9	0.9300	C31—H31	0.9300
C10—C11	1.396 (3)	C32—C33	1.396 (9)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.487 (3)	C33—C34	1.350 (8)
C12—C13	1.486 (3)	C33—H33	0.9300
C13—C14	1.398 (3)	C34—C35	1.450 (5)
C16—C17	1.505 (4)	C34—H34	0.9300
C16—H16A	0.9700	C35—C36	1.392 (6)
C16—H16B	0.9700	C36—C37	1.365 (5)
C17—C18	1.368 (3)	C36—H36	0.9300
C17—C26	1.413 (3)	C37—H37	0.9300
C18—C19	1.421 (4)
C15—N1—C1	110.01 (19)	C19—C18—H18	119.2
C15—N1—C16	122.6 (2)	C20—C19—C18	122.0 (2)
C1—N1—C16	126.3 (2)	C20—C19—C24	119.3 (3)
C14—N2—C15	109.52 (18)	C18—C19—C24	118.8 (3)
C14—N2—C27	129.50 (19)	C21—C20—C19	120.6 (3)
C15—N2—C27	118.01 (19)	C21—C20—H20	119.7
C2—C1—N1	129.6 (2)	C19—C20—H20	119.7
C2—C1—C14	123.14 (19)	C20—C21—C22	119.9 (4)
N1—C1—C14	107.28 (19)	C20—C21—H21	120.1
C1—C2—C3	117.5 (2)	C22—C21—H21	120.1
C1—C2—H2	121.3	C23—C22—C21	120.2 (3)
C3—C2—H2	121.3	C23—C22—H22	119.9
C2—C3—C4	121.1 (2)	C21—C22—H22	119.9
C2—C3—H3	119.4	C22—C23—C24	122.2 (4)
C4—C3—H3	119.4	C22—C23—H23	118.9
C3—C4—C13	121.6 (2)	C24—C23—H23	118.9
C3—C4—C5	117.6 (2)	C25—C24—C23	123.9 (3)
C13—C4—C5	120.8 (2)	C25—C24—C19	118.3 (3)
O1—C5—C6	121.3 (2)	C23—C24—C19	117.8 (3)
O1—C5—C4	121.0 (2)	C26—C25—C24	121.5 (3)
C6—C5—C4	117.6 (2)	C26—C25—H25	119.3
C11—C6—C7	119.7 (2)	C24—C25—H25	119.3
C11—C6—C5	120.3 (2)	C25—C26—C17	121.1 (3)
C7—C6—C5	120.0 (2)	C25—C26—H26	119.4
C8—C7—C6	119.5 (3)	C17—C26—H26	119.4
C8—C7—H7	120.2	N2—C27—C28	111.01 (19)
C6—C7—H7	120.2	N2—C27—H27A	109.4
C9—C8—C7	120.6 (2)	C28—C27—H27A	109.4
C9—C8—H8	119.7	N2—C27—H27B	109.4
C7—C8—H8	119.7	C28—C27—H27B	109.4
C8—C9—C10	120.6 (3)	H27A—C27—H27B	108.0
C8—C9—H9	119.7	C29—C28—C37	119.0 (3)
C10—C9—H9	119.7	C29—C28—C27	121.9 (3)
C11—C10—C9	119.5 (3)	C37—C28—C27	119.1 (2)
C11—C10—H10	120.3	C28—C29—C30	121.5 (3)
C9—C10—H10	120.3	C28—C29—H29	119.3
C6—C11—C10	120.1 (2)	C30—C29—H29	119.3
C6—C11—C12	120.9 (2)	C35—C30—C31	121.5 (4)
C10—C11—C12	119.0 (2)	C35—C30—C29	117.5 (3)
O2—C12—C13	122.5 (2)	C31—C30—C29	121.0 (4)
O2—C12—C11	120.5 (2)	C32—C31—C30	118.7 (6)
C13—C12—C11	116.9 (2)	C32—C31—H31	120.6
C14—C13—C4	117.43 (19)	C30—C31—H31	120.6
C14—C13—C12	123.84 (19)	C31—C32—C33	120.9 (5)
C4—C13—C12	118.40 (18)	C31—C32—H32	119.6
N2—C14—C13	134.28 (19)	C33—C32—H32	119.6
N2—C14—C1	106.53 (17)	C34—C33—C32	122.2 (4)
C13—C14—C1	119.17 (19)	C34—C33—H33	118.9
O3—C15—N1	126.2 (2)	C32—C33—H33	118.9
O3—C15—N2	127.1 (2)	C33—C34—C35	118.7 (5)
N1—C15—N2	106.64 (19)	C33—C34—H34	120.7
N1—C16—C17	113.45 (19)	C35—C34—H34	120.7
N1—C16—H16A	108.9	C30—C35—C36	120.7 (3)
C17—C16—H16A	108.9	C30—C35—C34	118.0 (4)
N1—C16—H16B	108.9	C36—C35—C34	121.3 (4)
C17—C16—H16B	108.9	C37—C36—C35	120.2 (3)
H16A—C16—H16B	107.7	C37—C36—H36	119.9
C18—C17—C26	118.5 (3)	C35—C36—H36	119.9
C18—C17—C16	123.9 (2)	C36—C37—C28	121.1 (3)
C26—C17—C16	117.6 (2)	C36—C37—H37	119.4
C17—C18—C19	121.7 (2)	C28—C37—H37	119.4
C17—C18—H18	119.2
C15—N1—C1—C2	179.5 (2)	C1—N1—C15—N2	−0.3 (3)
C16—N1—C1—C2	−11.8 (4)	C16—N1—C15—N2	−169.48 (19)
C15—N1—C1—C14	1.0 (3)	C14—N2—C15—O3	180.0 (3)
C16—N1—C1—C14	169.6 (2)	C27—N2—C15—O3	−17.6 (4)
N1—C1—C2—C3	−179.8 (2)	C14—N2—C15—N1	−0.5 (2)
C14—C1—C2—C3	−1.5 (3)	C27—N2—C15—N1	161.88 (19)
C1—C2—C3—C4	1.8 (3)	C15—N1—C16—C17	84.1 (3)
C2—C3—C4—C13	0.5 (3)	C1—N1—C16—C17	−83.2 (3)
C2—C3—C4—C5	−177.3 (2)	N1—C16—C17—C18	9.9 (4)
C3—C4—C5—O1	−6.7 (4)	N1—C16—C17—C26	−170.7 (2)
C13—C4—C5—O1	175.5 (2)	C26—C17—C18—C19	1.9 (4)
C3—C4—C5—C6	170.6 (2)	C16—C17—C18—C19	−178.6 (2)
C13—C4—C5—C6	−7.3 (3)	C17—C18—C19—C20	179.8 (3)
O1—C5—C6—C11	−170.5 (2)	C17—C18—C19—C24	0.2 (4)
C4—C5—C6—C11	12.3 (3)	C18—C19—C20—C21	−178.1 (3)
O1—C5—C6—C7	7.5 (4)	C24—C19—C20—C21	1.6 (5)
C4—C5—C6—C7	−169.7 (2)	C19—C20—C21—C22	0.2 (5)
C11—C6—C7—C8	−1.7 (4)	C20—C21—C22—C23	−1.1 (6)
C5—C6—C7—C8	−179.7 (2)	C21—C22—C23—C24	0.2 (6)
C6—C7—C8—C9	0.7 (4)	C22—C23—C24—C25	−178.9 (4)
C7—C8—C9—C10	1.3 (4)	C22—C23—C24—C19	1.6 (5)
C8—C9—C10—C11	−2.3 (4)	C20—C19—C24—C25	178.0 (3)
C7—C6—C11—C10	0.7 (3)	C18—C19—C24—C25	−2.3 (4)
C5—C6—C11—C10	178.7 (2)	C20—C19—C24—C23	−2.4 (4)
C7—C6—C11—C12	−176.2 (2)	C18—C19—C24—C23	177.3 (3)
C5—C6—C11—C12	1.8 (3)	C23—C24—C25—C26	−177.1 (3)
C9—C10—C11—C6	1.3 (4)	C19—C24—C25—C26	2.4 (5)
C9—C10—C11—C12	178.2 (2)	C24—C25—C26—C17	−0.3 (5)
C6—C11—C12—O2	156.5 (2)	C18—C17—C26—C25	−1.9 (4)
C10—C11—C12—O2	−20.5 (3)	C16—C17—C26—C25	178.6 (3)
C6—C11—C12—C13	−20.6 (3)	C14—N2—C27—C28	67.3 (3)
C10—C11—C12—C13	162.5 (2)	C15—N2—C27—C28	−91.0 (2)
C3—C4—C13—C14	−3.0 (3)	N2—C27—C28—C29	−119.1 (3)
C5—C4—C13—C14	174.77 (19)	N2—C27—C28—C37	63.1 (3)
C3—C4—C13—C12	170.7 (2)	C37—C28—C29—C30	0.3 (4)
C5—C4—C13—C12	−11.5 (3)	C27—C28—C29—C30	−177.5 (3)
O2—C12—C13—C14	21.4 (3)	C28—C29—C30—C35	−0.3 (5)
C11—C12—C13—C14	−161.59 (19)	C28—C29—C30—C31	178.7 (4)
O2—C12—C13—C4	−151.9 (2)	C35—C30—C31—C32	−0.6 (7)
C11—C12—C13—C4	25.1 (3)	C29—C30—C31—C32	−179.6 (5)
C15—N2—C14—C13	−177.5 (2)	C30—C31—C32—C33	1.9 (9)
C27—N2—C14—C13	22.8 (4)	C31—C32—C33—C34	−3.3 (10)
C15—N2—C14—C1	1.1 (2)	C32—C33—C34—C35	3.1 (9)
C27—N2—C14—C1	−158.6 (2)	C31—C30—C35—C36	−178.9 (4)
C4—C13—C14—N2	−178.4 (2)	C29—C30—C35—C36	0.1 (5)
C12—C13—C14—N2	8.3 (4)	C31—C30—C35—C34	0.5 (6)
C4—C13—C14—C1	3.2 (3)	C29—C30—C35—C34	179.5 (4)
C12—C13—C14—C1	−170.13 (19)	C33—C34—C35—C30	−1.7 (7)
C2—C1—C14—N2	−179.9 (2)	C33—C34—C35—C36	177.6 (5)
N1—C1—C14—N2	−1.3 (2)	C30—C35—C36—C37	0.0 (6)
C2—C1—C14—C13	−1.1 (3)	C34—C35—C36—C37	−179.3 (4)
N1—C1—C14—C13	177.57 (18)	C35—C36—C37—C28	0.0 (6)
C1—N1—C15—O3	179.2 (2)	C29—C28—C37—C36	−0.1 (5)
C16—N1—C15—O3	10.0 (4)	C27—C28—C37—C36	177.7 (3)