1-Benz-yloxy-4-(2-nitro-ethen-yl)benzene.

The title compound, C(15)H(13)NO(3), crystallizes with three independent mol-ecules per asymmetric unit (Z' = 3). One of these mol-ecules is found to have a configuration with a greater twist between its two aromatic rings than the other two [compare 70.26 (13) and 72.31 (12)° with 84.22 (12)°]. There are also differences in the number and nature of the weak inter-molecular C-H⋯O contacts formed by each of the three mol-ecules.

Related literature

For discussion of C—H⋯O contacts in related derivatives, see: Gerkin (1999 ▶). For other related structures, see: Gao et al. (2008 ▶); Stomberg & Lundquist (1994 ▶); Wang et al. (2007 ▶); Zheng et al. (2008 ▶); Kennedy et al. (2010 ▶). On the design of new small mol­ecules that target HIV-1 binding sites, see: Younis et al. (2010 ▶); Hunter et al. (2008 ▶); Jones et al. (2006 ▶). For background to the anti­retroviral treatment programme for AIDS, see: UNAIDS/WHO (2009 ▶).

Experimental

Crystal data

C15H13NO3

M = 255.26

Triclinic,

a = 9.9522 (8) Å

b = 14.0456 (13) Å

c = 14.2506 (10) Å

α = 74.416 (5)°

β = 84.188 (5)°

γ = 80.888 (4)°

V = 1891.0 (3) Å3

Z = 6

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.12 × 0.10 × 0.05 mm

Data collection

Bruker–Nonius APEXII CCD diffractometer

25754 measured reflections

7366 independent reflections

4735 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.170

S = 1.14

7366 reflections

514 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.28 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042960/si2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042960/si2304Isup2.hkl

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

C15H13NO3	Z = 6
Mr = 255.26	F(000) = 804
Triclinic, P1	Dx = 1.345 Mg m−3
a = 9.9522 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.0456 (13) Å	Cell parameters from 78718 reflections
c = 14.2506 (10) Å	θ = 2.9–27.5°
α = 74.416 (5)°	µ = 0.09 mm−1
β = 84.188 (5)°	T = 120 K
γ = 80.888 (4)°	Cut slab, pale yellow
V = 1891.0 (3) Å3	0.12 × 0.10 × 0.05 mm

Bruker–Nonius APEXII CCD diffractometer	4735 reflections with I > 2σ(I)
Radiation source: Bruker-Nonius FR591 rotating anode	Rint = 0.063
10cm confocal mirrors	θmax = 26.0°, θmin = 3.0°
Detector resolution: 4096x4096pixels / 62x62mm pixels mm-1	h = −12→12
φ & ω scans	k = −17→17
25754 measured reflections	l = −17→17
7366 independent reflections

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0086P)2 + 3.8491P] where P = (Fo2 + 2Fc2)/3
7366 reflections	(Δ/σ)max < 0.001
514 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.9330 (2)	0.37883 (19)	0.37919 (17)	0.0306 (6)
O2	1.0417 (3)	−0.0863 (2)	0.9274 (2)	0.0468 (8)
O3	0.8252 (3)	−0.0489 (2)	0.9037 (2)	0.0426 (7)
O4	0.7595 (2)	0.6336 (2)	0.93137 (18)	0.0337 (6)
O5	0.8521 (3)	1.0608 (2)	0.40189 (19)	0.0382 (7)
O6	0.6349 (3)	1.1069 (2)	0.3947 (2)	0.0458 (8)
O7	0.4798 (2)	0.3091 (2)	0.71568 (17)	0.0328 (6)
O8	0.6922 (3)	−0.0535 (2)	1.2632 (2)	0.0462 (8)
O9	0.4823 (3)	−0.0710 (2)	1.31177 (19)	0.0412 (7)
N1	0.9451 (3)	−0.0400 (2)	0.8780 (2)	0.0342 (8)
N2	0.7348 (3)	1.0530 (2)	0.4349 (2)	0.0320 (7)
N3	0.5696 (3)	−0.0360 (2)	1.2495 (2)	0.0322 (8)
C1	0.9316 (4)	0.3020 (3)	0.4612 (2)	0.0274 (8)
C2	1.0458 (3)	0.2566 (3)	0.5139 (3)	0.0271 (8)
H2	1.1326	0.2769	0.4915	0.033*
C3	1.0318 (4)	0.1819 (3)	0.5989 (3)	0.0285 (8)
H3	1.1099	0.1507	0.6343	0.034*
C4	0.9047 (4)	0.1516 (3)	0.6337 (3)	0.0271 (8)
C5	0.7925 (4)	0.1967 (3)	0.5792 (3)	0.0309 (9)
H5	0.7056	0.1766	0.6014	0.037*
C6	0.8055 (4)	0.2702 (3)	0.4936 (3)	0.0292 (8)
H6	0.7282	0.2992	0.4567	0.035*
C7	0.8843 (4)	0.0774 (3)	0.7258 (3)	0.0279 (8)
H7	0.7942	0.0619	0.7438	0.034*
C8	0.9796 (4)	0.0295 (3)	0.7866 (3)	0.0319 (9)
H8	1.0716	0.0408	0.7700	0.038*
C9	1.0559 (4)	0.4252 (3)	0.3534 (3)	0.0299 (9)
H9A	1.1305	0.3788	0.3316	0.036*
H9B	1.0846	0.4423	0.4107	0.036*
C10	1.0263 (3)	0.5182 (3)	0.2724 (3)	0.0276 (8)
C11	0.9907 (4)	0.5121 (3)	0.1823 (3)	0.0322 (9)
H11	0.9836	0.4490	0.1723	0.039*
C12	0.9657 (4)	0.5980 (3)	0.1072 (3)	0.0358 (10)
H12	0.9412	0.5929	0.0462	0.043*
C13	0.9756 (4)	0.6894 (3)	0.1196 (3)	0.0349 (9)
H13	0.9580	0.7477	0.0678	0.042*
C14	1.0117 (4)	0.6963 (3)	0.2085 (3)	0.0377 (10)
H14	1.0200	0.7597	0.2176	0.045*
C15	1.0359 (4)	0.6109 (3)	0.2849 (3)	0.0340 (9)
H15	1.0591	0.6165	0.3460	0.041*
C16	0.7608 (4)	0.7089 (3)	0.8479 (2)	0.0265 (8)
C17	0.6479 (4)	0.7507 (3)	0.7931 (3)	0.0305 (9)
H17	0.5614	0.7295	0.8147	0.037*
C18	0.6632 (4)	0.8231 (3)	0.7073 (3)	0.0306 (9)
H18	0.5859	0.8514	0.6702	0.037*
C19	0.7888 (4)	0.8564 (3)	0.6729 (3)	0.0277 (8)
C20	0.8995 (4)	0.8146 (3)	0.7303 (3)	0.0284 (8)
H20	0.9861	0.8358	0.7092	0.034*
C21	0.8855 (4)	0.7429 (3)	0.8170 (3)	0.0291 (9)
H21	0.9617	0.7167	0.8558	0.035*
C22	0.8072 (4)	0.9304 (3)	0.5808 (3)	0.0279 (8)
H22	0.8975	0.9437	0.5594	0.033*
C23	0.7081 (4)	0.9805 (3)	0.5246 (3)	0.0330 (9)
H23	0.6170	0.9683	0.5441	0.040*
C24	0.6366 (4)	0.5879 (3)	0.9591 (3)	0.0381 (10)
H24A	0.6056	0.5710	0.9024	0.046*
H24B	0.5634	0.6345	0.9819	0.046*
C25	0.6680 (3)	0.4951 (3)	1.0395 (3)	0.0287 (9)
C26	0.7175 (4)	0.4054 (3)	1.0175 (3)	0.0364 (10)
H26	0.7309	0.4024	0.9514	0.044*
C27	0.7477 (4)	0.3194 (3)	1.0922 (3)	0.0418 (10)
H27	0.7823	0.2581	1.0766	0.050*
C28	0.7279 (4)	0.3225 (3)	1.1887 (3)	0.0402 (10)
H28	0.7468	0.2635	1.2395	0.048*
C29	0.6802 (4)	0.4122 (3)	1.2100 (3)	0.0392 (10)
H29	0.6683	0.4155	1.2761	0.047*
C30	0.6495 (4)	0.4976 (3)	1.1359 (3)	0.0339 (9)
H30	0.6151	0.5588	1.1518	0.041*
C31	0.5003 (4)	0.2542 (3)	0.8087 (2)	0.0272 (8)
C32	0.3980 (4)	0.2181 (3)	0.8771 (3)	0.0306 (9)
H32	0.3055	0.2335	0.8608	0.037*
C33	0.4313 (4)	0.1599 (3)	0.9687 (3)	0.0312 (9)
H33	0.3611	0.1355	1.0150	0.037*
C34	0.5662 (4)	0.1366 (3)	0.9941 (3)	0.0293 (8)
C35	0.6680 (4)	0.1754 (3)	0.9255 (3)	0.0326 (9)
H35	0.7604	0.1613	0.9421	0.039*
C36	0.6354 (4)	0.2333 (3)	0.8347 (3)	0.0330 (9)
H36	0.7053	0.2595	0.7892	0.040*
C37	0.6052 (4)	0.0718 (3)	1.0889 (3)	0.0319 (9)
H37	0.6991	0.0605	1.1013	0.038*
C38	0.5207 (4)	0.0273 (3)	1.1591 (3)	0.0317 (9)
H38	0.4259	0.0375	1.1494	0.038*
C39	0.3446 (4)	0.3208 (3)	0.6810 (3)	0.0317 (9)
H39A	0.2796	0.3651	0.7130	0.038*
H39B	0.3113	0.2552	0.6951	0.038*
C40	0.3582 (3)	0.3660 (3)	0.5727 (3)	0.0298 (9)
C41	0.4149 (4)	0.3069 (3)	0.5108 (3)	0.0341 (9)
H41	0.4414	0.2374	0.5365	0.041*
C42	0.4326 (4)	0.3493 (3)	0.4114 (3)	0.0365 (10)
H42	0.4705	0.3086	0.3691	0.044*
C43	0.3955 (4)	0.4507 (3)	0.3735 (3)	0.0375 (10)
H43	0.4090	0.4797	0.3055	0.045*
C44	0.3390 (4)	0.5096 (3)	0.4347 (3)	0.0354 (9)
H44	0.3132	0.5791	0.4089	0.043*
C45	0.3199 (4)	0.4670 (3)	0.5338 (3)	0.0319 (9)
H45	0.2801	0.5076	0.5757	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0257 (13)	0.0339 (16)	0.0294 (14)	−0.0089 (11)	−0.0034 (11)	0.0002 (12)
O2	0.0388 (17)	0.0464 (19)	0.0431 (17)	−0.0049 (14)	−0.0069 (14)	0.0104 (14)
O3	0.0341 (16)	0.0445 (18)	0.0417 (17)	−0.0109 (13)	0.0066 (13)	0.0016 (14)
O4	0.0312 (14)	0.0374 (16)	0.0290 (14)	−0.0146 (12)	−0.0044 (11)	0.0044 (12)
O5	0.0268 (14)	0.0438 (18)	0.0378 (16)	−0.0080 (12)	0.0017 (12)	0.0005 (13)
O6	0.0315 (16)	0.0483 (19)	0.0454 (17)	0.0029 (14)	−0.0119 (13)	0.0071 (14)
O7	0.0235 (13)	0.0436 (17)	0.0276 (14)	−0.0091 (12)	−0.0047 (10)	0.0006 (12)
O8	0.0308 (16)	0.059 (2)	0.0412 (17)	−0.0091 (14)	−0.0093 (13)	0.0045 (15)
O9	0.0378 (16)	0.0431 (18)	0.0361 (16)	−0.0109 (13)	0.0046 (13)	0.0017 (13)
N1	0.0334 (19)	0.0282 (19)	0.0377 (19)	−0.0061 (15)	0.0011 (15)	−0.0028 (15)
N2	0.0301 (18)	0.034 (2)	0.0288 (17)	−0.0060 (15)	−0.0038 (14)	−0.0022 (15)
N3	0.038 (2)	0.0303 (19)	0.0262 (17)	−0.0060 (15)	−0.0031 (14)	−0.0018 (14)
C1	0.030 (2)	0.027 (2)	0.0239 (19)	−0.0026 (16)	−0.0026 (15)	−0.0059 (16)
C2	0.0233 (18)	0.031 (2)	0.029 (2)	−0.0083 (16)	0.0009 (15)	−0.0090 (17)
C3	0.0261 (19)	0.029 (2)	0.028 (2)	−0.0006 (16)	−0.0049 (15)	−0.0036 (17)
C4	0.029 (2)	0.026 (2)	0.0272 (19)	−0.0054 (16)	−0.0015 (15)	−0.0071 (16)
C5	0.0248 (19)	0.032 (2)	0.036 (2)	−0.0105 (17)	0.0019 (16)	−0.0062 (18)
C6	0.0233 (19)	0.034 (2)	0.030 (2)	−0.0074 (16)	−0.0011 (15)	−0.0058 (17)
C7	0.0268 (19)	0.028 (2)	0.030 (2)	−0.0069 (16)	0.0003 (16)	−0.0076 (17)
C8	0.032 (2)	0.028 (2)	0.032 (2)	−0.0109 (17)	0.0018 (17)	0.0002 (17)
C9	0.0268 (19)	0.033 (2)	0.028 (2)	−0.0094 (17)	−0.0036 (15)	0.0000 (17)
C10	0.0179 (17)	0.032 (2)	0.033 (2)	−0.0075 (15)	−0.0007 (15)	−0.0066 (17)
C11	0.032 (2)	0.030 (2)	0.036 (2)	−0.0085 (17)	−0.0025 (17)	−0.0089 (18)
C12	0.033 (2)	0.046 (3)	0.027 (2)	−0.0087 (19)	−0.0079 (16)	−0.0023 (19)
C13	0.027 (2)	0.037 (3)	0.035 (2)	−0.0066 (18)	0.0005 (16)	0.0012 (19)
C14	0.037 (2)	0.026 (2)	0.048 (3)	−0.0057 (18)	−0.0028 (19)	−0.0046 (19)
C15	0.034 (2)	0.038 (3)	0.032 (2)	−0.0079 (18)	−0.0061 (17)	−0.0081 (18)
C16	0.0287 (19)	0.027 (2)	0.0235 (19)	−0.0093 (16)	−0.0039 (15)	−0.0026 (16)
C17	0.027 (2)	0.034 (2)	0.031 (2)	−0.0112 (17)	−0.0017 (16)	−0.0056 (18)
C18	0.0242 (19)	0.035 (2)	0.031 (2)	−0.0030 (17)	−0.0064 (15)	−0.0043 (18)
C19	0.030 (2)	0.024 (2)	0.028 (2)	−0.0050 (16)	−0.0020 (16)	−0.0051 (16)
C20	0.0242 (19)	0.029 (2)	0.031 (2)	−0.0067 (16)	−0.0023 (15)	−0.0031 (17)
C21	0.0259 (19)	0.032 (2)	0.029 (2)	−0.0050 (16)	−0.0050 (15)	−0.0049 (17)
C22	0.0256 (19)	0.030 (2)	0.028 (2)	−0.0066 (16)	0.0027 (15)	−0.0071 (17)
C23	0.030 (2)	0.037 (2)	0.030 (2)	−0.0100 (18)	0.0024 (16)	−0.0046 (18)
C24	0.032 (2)	0.044 (3)	0.036 (2)	−0.0197 (19)	−0.0011 (17)	0.0021 (19)
C25	0.0201 (18)	0.034 (2)	0.031 (2)	−0.0105 (16)	−0.0023 (15)	−0.0025 (17)
C26	0.028 (2)	0.047 (3)	0.034 (2)	−0.0096 (19)	0.0008 (17)	−0.010 (2)
C27	0.036 (2)	0.036 (3)	0.056 (3)	−0.0060 (19)	−0.003 (2)	−0.015 (2)
C28	0.031 (2)	0.038 (3)	0.043 (2)	−0.0072 (19)	−0.0041 (18)	0.006 (2)
C29	0.035 (2)	0.050 (3)	0.031 (2)	−0.014 (2)	0.0031 (17)	−0.006 (2)
C30	0.031 (2)	0.035 (2)	0.037 (2)	−0.0067 (17)	−0.0020 (17)	−0.0096 (19)
C31	0.032 (2)	0.025 (2)	0.0238 (19)	−0.0052 (16)	−0.0023 (15)	−0.0042 (16)
C32	0.0274 (19)	0.031 (2)	0.031 (2)	−0.0023 (16)	−0.0003 (16)	−0.0062 (17)
C33	0.031 (2)	0.036 (2)	0.026 (2)	−0.0092 (17)	0.0047 (16)	−0.0075 (18)
C34	0.033 (2)	0.026 (2)	0.028 (2)	−0.0063 (17)	−0.0012 (16)	−0.0052 (16)
C35	0.026 (2)	0.041 (2)	0.032 (2)	−0.0053 (17)	−0.0038 (16)	−0.0104 (18)
C36	0.029 (2)	0.042 (2)	0.026 (2)	−0.0076 (18)	0.0017 (16)	−0.0042 (18)
C37	0.030 (2)	0.032 (2)	0.034 (2)	−0.0033 (17)	0.0007 (17)	−0.0116 (18)
C38	0.030 (2)	0.034 (2)	0.029 (2)	−0.0006 (17)	−0.0053 (16)	−0.0069 (18)
C39	0.0252 (19)	0.038 (2)	0.029 (2)	−0.0053 (17)	−0.0062 (15)	−0.0024 (18)
C40	0.0206 (18)	0.036 (2)	0.032 (2)	−0.0080 (16)	−0.0051 (15)	−0.0042 (18)
C41	0.028 (2)	0.034 (2)	0.040 (2)	−0.0067 (17)	−0.0052 (17)	−0.0063 (19)
C42	0.028 (2)	0.045 (3)	0.040 (2)	−0.0072 (19)	−0.0011 (17)	−0.016 (2)
C43	0.030 (2)	0.050 (3)	0.029 (2)	−0.0078 (19)	−0.0063 (17)	−0.003 (2)
C44	0.028 (2)	0.038 (2)	0.035 (2)	−0.0027 (18)	−0.0040 (17)	0.0009 (19)
C45	0.0229 (19)	0.037 (2)	0.035 (2)	−0.0022 (17)	−0.0033 (16)	−0.0074 (18)

O1—C1	1.362 (4)	C19—C22	1.454 (5)
O1—C9	1.445 (4)	C20—C21	1.379 (5)
O2—N1	1.239 (4)	C20—H20	0.9500
O3—N1	1.228 (4)	C21—H21	0.9500
O4—C16	1.364 (4)	C22—C23	1.321 (5)
O4—C24	1.441 (4)	C22—H22	0.9500
O5—N2	1.224 (4)	C23—H23	0.9500
O6—N2	1.239 (4)	C24—C25	1.500 (5)
O7—C31	1.359 (4)	C24—H24A	0.9900
O7—C39	1.451 (4)	C24—H24B	0.9900
O8—N3	1.231 (4)	C25—C30	1.376 (5)
O9—N3	1.237 (4)	C25—C26	1.383 (5)
N1—C8	1.449 (5)	C26—C27	1.393 (6)
N2—C23	1.435 (5)	C26—H26	0.9500
N3—C38	1.435 (5)	C27—C28	1.380 (6)
C1—C6	1.391 (5)	C27—H27	0.9500
C1—C2	1.396 (5)	C28—C29	1.376 (6)
C2—C3	1.385 (5)	C28—H28	0.9500
C2—H2	0.9500	C29—C30	1.385 (6)
C3—C4	1.399 (5)	C29—H29	0.9500
C3—H3	0.9500	C30—H30	0.9500
C4—C5	1.392 (5)	C31—C32	1.393 (5)
C4—C7	1.458 (5)	C31—C36	1.397 (5)
C5—C6	1.381 (5)	C32—C33	1.383 (5)
C5—H5	0.9500	C32—H32	0.9500
C6—H6	0.9500	C33—C34	1.392 (5)
C7—C8	1.324 (5)	C33—H33	0.9500
C7—H7	0.9500	C34—C35	1.402 (5)
C8—H8	0.9500	C34—C37	1.462 (5)
C9—C10	1.504 (5)	C35—C36	1.369 (5)
C9—H9A	0.9900	C35—H35	0.9500
C9—H9B	0.9900	C36—H36	0.9500
C10—C15	1.379 (5)	C37—C38	1.325 (5)
C10—C11	1.393 (5)	C37—H37	0.9500
C11—C12	1.388 (5)	C38—H38	0.9500
C11—H11	0.9500	C39—C40	1.504 (5)
C12—C13	1.362 (6)	C39—H39A	0.9900
C12—H12	0.9500	C39—H39B	0.9900
C13—C14	1.383 (5)	C40—C45	1.384 (5)
C13—H13	0.9500	C40—C41	1.389 (5)
C14—C15	1.393 (5)	C41—C42	1.386 (5)
C14—H14	0.9500	C41—H41	0.9500
C15—H15	0.9500	C42—C43	1.385 (6)
C16—C21	1.388 (5)	C42—H42	0.9500
C16—C17	1.392 (5)	C43—C44	1.378 (6)
C17—C18	1.377 (5)	C43—H43	0.9500
C17—H17	0.9500	C44—C45	1.385 (5)
C18—C19	1.400 (5)	C44—H44	0.9500
C18—H18	0.9500	C45—H45	0.9500
C19—C20	1.395 (5)
C1—O1—C9	117.4 (3)	C23—C22—C19	125.1 (3)
C16—O4—C24	117.4 (3)	C23—C22—H22	117.4
C31—O7—C39	117.7 (3)	C19—C22—H22	117.4
O3—N1—O2	123.5 (3)	C22—C23—N2	121.6 (3)
O3—N1—C8	120.0 (3)	C22—C23—H23	119.2
O2—N1—C8	116.5 (3)	N2—C23—H23	119.2
O5—N2—O6	122.7 (3)	O4—C24—C25	107.8 (3)
O5—N2—C23	120.3 (3)	O4—C24—H24A	110.1
O6—N2—C23	117.0 (3)	C25—C24—H24A	110.1
O8—N3—O9	122.5 (3)	O4—C24—H24B	110.1
O8—N3—C38	121.0 (3)	C25—C24—H24B	110.1
O9—N3—C38	116.4 (3)	H24A—C24—H24B	108.5
O1—C1—C6	116.0 (3)	C30—C25—C26	118.9 (4)
O1—C1—C2	124.3 (3)	C30—C25—C24	121.0 (4)
C6—C1—C2	119.6 (3)	C26—C25—C24	120.2 (4)
C3—C2—C1	119.6 (3)	C25—C26—C27	120.2 (4)
C3—C2—H2	120.2	C25—C26—H26	119.9
C1—C2—H2	120.2	C27—C26—H26	119.9
C2—C3—C4	121.1 (3)	C28—C27—C26	120.6 (4)
C2—C3—H3	119.4	C28—C27—H27	119.7
C4—C3—H3	119.4	C26—C27—H27	119.7
C5—C4—C3	118.3 (3)	C29—C28—C27	119.0 (4)
C5—C4—C7	118.9 (3)	C29—C28—H28	120.5
C3—C4—C7	122.8 (3)	C27—C28—H28	120.5
C6—C5—C4	121.1 (3)	C28—C29—C30	120.5 (4)
C6—C5—H5	119.5	C28—C29—H29	119.8
C4—C5—H5	119.5	C30—C29—H29	119.8
C5—C6—C1	120.2 (3)	C25—C30—C29	120.9 (4)
C5—C6—H6	119.9	C25—C30—H30	119.5
C1—C6—H6	119.9	C29—C30—H30	119.5
C8—C7—C4	126.1 (3)	O7—C31—C32	124.9 (3)
C8—C7—H7	116.9	O7—C31—C36	115.8 (3)
C4—C7—H7	116.9	C32—C31—C36	119.3 (3)
C7—C8—N1	120.8 (3)	C33—C32—C31	120.0 (3)
C7—C8—H8	119.6	C33—C32—H32	120.0
N1—C8—H8	119.6	C31—C32—H32	120.0
O1—C9—C10	108.1 (3)	C32—C33—C34	120.9 (3)
O1—C9—H9A	110.1	C32—C33—H33	119.5
C10—C9—H9A	110.1	C34—C33—H33	119.5
O1—C9—H9B	110.1	C33—C34—C35	118.6 (3)
C10—C9—H9B	110.1	C33—C34—C37	122.2 (3)
H9A—C9—H9B	108.4	C35—C34—C37	119.2 (3)
C15—C10—C11	118.6 (3)	C36—C35—C34	120.7 (4)
C15—C10—C9	121.0 (3)	C36—C35—H35	119.7
C11—C10—C9	120.4 (3)	C34—C35—H35	119.7
C12—C11—C10	120.3 (4)	C35—C36—C31	120.5 (3)
C12—C11—H11	119.9	C35—C36—H36	119.7
C10—C11—H11	119.9	C31—C36—H36	119.7
C13—C12—C11	121.1 (4)	C38—C37—C34	125.7 (4)
C13—C12—H12	119.5	C38—C37—H37	117.2
C11—C12—H12	119.5	C34—C37—H37	117.2
C12—C13—C14	119.2 (4)	C37—C38—N3	121.3 (4)
C12—C13—H13	120.4	C37—C38—H38	119.3
C14—C13—H13	120.4	N3—C38—H38	119.3
C13—C14—C15	120.4 (4)	O7—C39—C40	106.1 (3)
C13—C14—H14	119.8	O7—C39—H39A	110.5
C15—C14—H14	119.8	C40—C39—H39A	110.5
C10—C15—C14	120.5 (4)	O7—C39—H39B	110.5
C10—C15—H15	119.8	C40—C39—H39B	110.5
C14—C15—H15	119.8	H39A—C39—H39B	108.7
O4—C16—C21	115.9 (3)	C45—C40—C41	119.2 (3)
O4—C16—C17	124.4 (3)	C45—C40—C39	120.8 (3)
C21—C16—C17	119.7 (3)	C41—C40—C39	120.0 (4)
C18—C17—C16	119.2 (3)	C42—C41—C40	120.0 (4)
C18—C17—H17	120.4	C42—C41—H41	120.0
C16—C17—H17	120.4	C40—C41—H41	120.0
C17—C18—C19	122.2 (3)	C43—C42—C41	120.3 (4)
C17—C18—H18	118.9	C43—C42—H42	119.9
C19—C18—H18	118.9	C41—C42—H42	119.9
C20—C19—C18	117.3 (3)	C44—C43—C42	119.9 (4)
C20—C19—C22	120.0 (3)	C44—C43—H43	120.0
C18—C19—C22	122.7 (3)	C42—C43—H43	120.0
C21—C20—C19	121.2 (3)	C43—C44—C45	119.8 (4)
C21—C20—H20	119.4	C43—C44—H44	120.1
C19—C20—H20	119.4	C45—C44—H44	120.1
C20—C21—C16	120.3 (3)	C40—C45—C44	120.8 (4)
C20—C21—H21	119.8	C40—C45—H45	119.6
C16—C21—H21	119.8	C44—C45—H45	119.6
C9—O1—C1—C6	169.3 (3)	C19—C22—C23—N2	179.5 (3)
C9—O1—C1—C2	−9.1 (5)	O5—N2—C23—C22	9.6 (6)
O1—C1—C2—C3	177.1 (3)	O6—N2—C23—C22	−169.3 (4)
C6—C1—C2—C3	−1.3 (5)	C16—O4—C24—C25	168.5 (3)
C1—C2—C3—C4	−0.7 (6)	O4—C24—C25—C30	91.2 (4)
C2—C3—C4—C5	1.6 (6)	O4—C24—C25—C26	−88.2 (4)
C2—C3—C4—C7	−176.3 (3)	C30—C25—C26—C27	0.0 (5)
C3—C4—C5—C6	−0.6 (6)	C24—C25—C26—C27	179.4 (3)
C7—C4—C5—C6	177.4 (3)	C25—C26—C27—C28	0.5 (6)
C4—C5—C6—C1	−1.3 (6)	C26—C27—C28—C29	−1.3 (6)
O1—C1—C6—C5	−176.2 (3)	C27—C28—C29—C30	1.6 (6)
C2—C1—C6—C5	2.3 (6)	C26—C25—C30—C29	0.3 (5)
C5—C4—C7—C8	−178.6 (4)	C24—C25—C30—C29	−179.1 (3)
C3—C4—C7—C8	−0.6 (6)	C28—C29—C30—C25	−1.1 (6)
C4—C7—C8—N1	177.6 (3)	C39—O7—C31—C32	−8.1 (5)
O3—N1—C8—C7	−6.0 (6)	C39—O7—C31—C36	171.5 (3)
O2—N1—C8—C7	175.5 (4)	O7—C31—C32—C33	177.7 (4)
C1—O1—C9—C10	−170.1 (3)	C36—C31—C32—C33	−1.8 (6)
O1—C9—C10—C15	118.0 (4)	C31—C32—C33—C34	0.1 (6)
O1—C9—C10—C11	−63.0 (4)	C32—C33—C34—C35	1.5 (6)
C15—C10—C11—C12	0.0 (5)	C32—C33—C34—C37	−177.4 (4)
C9—C10—C11—C12	−179.0 (3)	C33—C34—C35—C36	−1.2 (6)
C10—C11—C12—C13	0.2 (6)	C37—C34—C35—C36	177.6 (4)
C11—C12—C13—C14	0.2 (6)	C34—C35—C36—C31	−0.5 (6)
C12—C13—C14—C15	−0.8 (6)	O7—C31—C36—C35	−177.5 (3)
C11—C10—C15—C14	−0.7 (5)	C32—C31—C36—C35	2.0 (6)
C9—C10—C15—C14	178.3 (3)	C33—C34—C37—C38	1.3 (6)
C13—C14—C15—C10	1.0 (6)	C35—C34—C37—C38	−177.5 (4)
C24—O4—C16—C21	−172.4 (3)	C34—C37—C38—N3	179.3 (3)
C24—O4—C16—C17	6.4 (5)	O8—N3—C38—C37	−2.5 (6)
O4—C16—C17—C18	−176.7 (3)	O9—N3—C38—C37	177.4 (4)
C21—C16—C17—C18	2.1 (6)	C31—O7—C39—C40	−169.0 (3)
C16—C17—C18—C19	0.0 (6)	O7—C39—C40—C45	−100.5 (4)
C17—C18—C19—C20	−1.1 (6)	O7—C39—C40—C41	76.8 (4)
C17—C18—C19—C22	177.9 (4)	C45—C40—C41—C42	0.1 (5)
C18—C19—C20—C21	0.3 (6)	C39—C40—C41—C42	−177.3 (3)
C22—C19—C20—C21	−178.7 (3)	C40—C41—C42—C43	0.7 (5)
C19—C20—C21—C16	1.7 (6)	C41—C42—C43—C44	−0.8 (6)
O4—C16—C21—C20	176.0 (3)	C42—C43—C44—C45	0.2 (6)
C17—C16—C21—C20	−2.9 (6)	C41—C40—C45—C44	−0.8 (5)
C20—C19—C22—C23	−174.4 (4)	C39—C40—C45—C44	176.6 (3)
C18—C19—C22—C23	6.6 (6)	C43—C44—C45—C40	0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O8i	0.95	2.56	3.503 (5)	175
C8—H8···O8i	0.95	2.38	3.322 (5)	175
C5—H5···O9ii	0.95	2.58	3.493 (4)	162
C12—H12···O4iii	0.95	2.46	3.284 (5)	145
C20—H20···O5iv	0.95	2.49	3.373 (4)	155
C22—H22···O5iv	0.95	2.59	3.448 (4)	150
C18—H18···O6v	0.95	2.40	3.326 (4)	166
C33—H33···O3ii	0.95	2.40	3.325 (4)	163
C45—H45···O1vi	0.95	2.58	3.413 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O8i	0.95	2.56	3.503 (5)	175
C8—H8⋯O8i	0.95	2.38	3.322 (5)	175
C5—H5⋯O9ii	0.95	2.58	3.493 (4)	162
C12—H12⋯O4iii	0.95	2.46	3.284 (5)	145
C20—H20⋯O5iv	0.95	2.49	3.373 (4)	155
C22—H22⋯O5iv	0.95	2.59	3.448 (4)	150
C18—H18⋯O6v	0.95	2.40	3.326 (4)	166
C33—H33⋯O3ii	0.95	2.40	3.325 (4)	163
C45—H45⋯O1vi	0.95	2.58	3.413 (5)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .