(E)-3-(4-Methyl-phen-yl)-1-(4-nitro-phenyl)prop-2-en-1-one.

The asymmetric unit of the title compound, C(16)H(13)NO(3), contains two independent mol-ecules related approximately by a pseudo-twofold rotation axis. The dihedral angle between the nitro-benzene and methyl-phenyl rings is 42.18 (6)° in one mol-ecule and 12.97 (6)° in the other. In both mol-ecules, the nitro group is slightly twisted away from the attached benzene ring. In the crystal structure, the mol-ecules are stacked along the b axis and are linked via C-H⋯O and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2007 ▶); Patil et al. (2007 ▶ ▶); Patil, Dharmaprakash et al. (2007 ▶). For background to the applications of substituted chalcones, see: Agrinskaya et al. (1999 ▶); Gu et al. (2008 ▶); Patil et al. (2006 ▶); Patil, Dharmaprakash et al. (2007 ▶).

Experimental

Crystal data

C16H13NO3

M = 267.27

Triclinic,

a = 5.8857 (1) Å

b = 7.8800 (1) Å

c = 27.4745 (4) Å

α = 88.793 (1)°

β = 85.665 (1)°

γ = 82.645 (1)°

V = 1260.07 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.43 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.977

32268 measured reflections

6666 independent reflections

5182 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.09

6666 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012257/ci2586sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012257/ci2586Isup2.hkl

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

C16H13NO3	Z = 4
Mr = 267.27	F000 = 560
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.8857 (1) Å	Cell parameters from 6666 reflections
b = 7.8800 (1) Å	θ = 0.7–29.0º
c = 27.4745 (4) Å	µ = 0.10 mm−1
α = 88.793 (1)º	T = 100.0 (1) K
β = 85.665 (1)º	Block, yellow
γ = 82.645 (1)º	0.43 × 0.26 × 0.23 mm
V = 1260.07 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	6666 independent reflections
Radiation source: fine-focus sealed tube	5182 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 8.33 pixels mm-1	θmax = 29.0º
T = 100.0(1) K	θmin = 0.7º
ω scans	h = −8→8
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −10→8
Tmin = 0.959, Tmax = 0.977	l = −37→37
32268 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.061P)2 + 0.3735P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
6666 reflections	Δρmax = 0.38 e Å−3
363 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1A	0.21638 (17)	0.20887 (14)	0.77198 (4)	0.0239 (2)
O2A	0.88278 (19)	−0.18446 (17)	0.96280 (4)	0.0382 (3)
O3A	0.52447 (19)	−0.18264 (14)	0.98705 (4)	0.0271 (2)
N1A	0.6782 (2)	−0.14787 (16)	0.95730 (4)	0.0219 (3)
C1A	0.7223 (2)	0.03671 (18)	0.83164 (5)	0.0193 (3)
H1A	0.8340	0.0463	0.8063	0.023*
C2A	0.7813 (2)	−0.04744 (18)	0.87474 (5)	0.0196 (3)
H2A	0.9319	−0.0955	0.8785	0.024*
C3A	0.6122 (2)	−0.05826 (17)	0.91193 (5)	0.0171 (3)
C4A	0.3867 (2)	0.00997 (18)	0.90810 (5)	0.0203 (3)
H4A	0.2761	0.0009	0.9337	0.024*
C5A	0.3298 (2)	0.09255 (18)	0.86483 (5)	0.0197 (3)
H5A	0.1786	0.1394	0.8613	0.024*
C6A	0.4958 (2)	0.10657 (17)	0.82647 (5)	0.0158 (3)
C7A	0.4201 (2)	0.19297 (17)	0.77999 (5)	0.0169 (3)
C8A	0.5949 (2)	0.25902 (17)	0.74603 (5)	0.0174 (3)
H8A	0.7450	0.2555	0.7548	0.021*
C9A	0.5374 (2)	0.32427 (17)	0.70247 (5)	0.0170 (3)
H9A	0.3891	0.3156	0.6941	0.020*
C10A	0.6854 (2)	0.40782 (17)	0.66680 (5)	0.0158 (3)
C11A	0.6179 (2)	0.43784 (17)	0.61919 (5)	0.0172 (3)
H11A	0.4811	0.4026	0.6109	0.021*
C12A	0.7501 (2)	0.51888 (17)	0.58421 (5)	0.0185 (3)
H12A	0.7027	0.5350	0.5527	0.022*
C13A	0.9536 (2)	0.57638 (17)	0.59585 (5)	0.0179 (3)
C14A	1.0189 (2)	0.54932 (17)	0.64355 (5)	0.0181 (3)
H14A	1.1525	0.5887	0.6521	0.022*
C15A	0.8900 (2)	0.46549 (17)	0.67837 (5)	0.0177 (3)
H15A	0.9396	0.4474	0.7096	0.021*
C16A	1.0971 (2)	0.66602 (19)	0.55834 (5)	0.0224 (3)
H16A	0.9997	0.7509	0.5414	0.034*
H16B	1.1753	0.5841	0.5354	0.034*
H16C	1.2079	0.7203	0.5743	0.034*
O1B	−0.02096 (17)	0.84372 (13)	0.73497 (4)	0.0228 (2)
O2B	0.65858 (19)	1.10645 (15)	0.52474 (4)	0.0302 (3)
O3B	0.3249 (2)	1.25845 (15)	0.52514 (4)	0.0342 (3)
N1B	0.4637 (2)	1.14949 (16)	0.54285 (4)	0.0227 (3)
C1B	0.4905 (2)	0.88516 (18)	0.65652 (5)	0.0193 (3)
H1B	0.5979	0.8123	0.6726	0.023*
C2B	0.5542 (2)	0.95813 (18)	0.61183 (5)	0.0196 (3)
H2B	0.7030	0.9339	0.5976	0.024*
C3B	0.3911 (2)	1.06743 (17)	0.58920 (5)	0.0181 (3)
C4B	0.1681 (2)	1.10666 (18)	0.60879 (5)	0.0204 (3)
H4B	0.0625	1.1817	0.5928	0.024*
C5B	0.1060 (2)	1.03113 (18)	0.65291 (5)	0.0192 (3)
H5B	−0.0441	1.0541	0.6665	0.023*
C6B	0.2662 (2)	0.92085 (17)	0.67722 (5)	0.0167 (3)
C7B	0.1851 (2)	0.84063 (17)	0.72448 (5)	0.0175 (3)
C8B	0.3587 (2)	0.75994 (18)	0.75670 (5)	0.0190 (3)
H8B	0.5139	0.7541	0.7466	0.023*
C9B	0.2950 (2)	0.69516 (17)	0.80024 (5)	0.0186 (3)
H9B	0.1380	0.7050	0.8089	0.022*
C10B	0.4455 (2)	0.61059 (17)	0.83569 (5)	0.0176 (3)
C11B	0.3559 (2)	0.57945 (18)	0.88324 (5)	0.0196 (3)
H11B	0.2014	0.6141	0.8919	0.024*
C12B	0.4946 (2)	0.49752 (18)	0.91766 (5)	0.0203 (3)
H12B	0.4320	0.4792	0.9491	0.024*
C13B	0.7260 (2)	0.44249 (18)	0.90559 (5)	0.0194 (3)
C14B	0.8147 (2)	0.47184 (18)	0.85790 (5)	0.0197 (3)
H14B	0.9684	0.4348	0.8490	0.024*
C15B	0.6776 (2)	0.55527 (18)	0.82360 (5)	0.0192 (3)
H15B	0.7408	0.5746	0.7922	0.023*
C16B	0.8747 (3)	0.3557 (2)	0.94323 (5)	0.0236 (3)
H16D	0.8475	0.4184	0.9731	0.035*
H16E	1.0334	0.3520	0.9317	0.035*
H16F	0.8385	0.2413	0.9489	0.035*

	U11	U22	U33	U12	U13	U23
O1A	0.0172 (5)	0.0334 (6)	0.0213 (5)	−0.0041 (4)	−0.0029 (4)	0.0080 (4)
O2A	0.0253 (6)	0.0570 (8)	0.0311 (6)	0.0002 (5)	−0.0093 (5)	0.0183 (6)
O3A	0.0333 (6)	0.0294 (6)	0.0187 (5)	−0.0066 (5)	0.0006 (4)	0.0073 (4)
N1A	0.0267 (6)	0.0219 (6)	0.0173 (6)	−0.0033 (5)	−0.0037 (5)	0.0040 (5)
C1A	0.0173 (6)	0.0225 (7)	0.0174 (6)	−0.0017 (5)	0.0016 (5)	0.0022 (5)
C2A	0.0172 (6)	0.0226 (7)	0.0187 (7)	−0.0005 (5)	−0.0023 (5)	0.0035 (5)
C3A	0.0205 (7)	0.0170 (6)	0.0143 (6)	−0.0036 (5)	−0.0030 (5)	0.0023 (5)
C4A	0.0190 (7)	0.0243 (7)	0.0175 (6)	−0.0040 (5)	0.0014 (5)	0.0032 (5)
C5A	0.0165 (6)	0.0232 (7)	0.0187 (6)	−0.0009 (5)	−0.0009 (5)	0.0037 (5)
C6A	0.0171 (6)	0.0146 (6)	0.0161 (6)	−0.0034 (5)	−0.0014 (5)	0.0010 (5)
C7A	0.0186 (6)	0.0172 (6)	0.0147 (6)	−0.0024 (5)	−0.0002 (5)	0.0017 (5)
C8A	0.0159 (6)	0.0177 (6)	0.0184 (6)	−0.0025 (5)	0.0000 (5)	0.0012 (5)
C9A	0.0159 (6)	0.0181 (6)	0.0166 (6)	−0.0015 (5)	−0.0002 (5)	0.0005 (5)
C10A	0.0166 (6)	0.0146 (6)	0.0155 (6)	−0.0002 (5)	0.0001 (5)	0.0012 (5)
C11A	0.0163 (6)	0.0178 (6)	0.0176 (6)	−0.0027 (5)	−0.0010 (5)	−0.0002 (5)
C12A	0.0223 (7)	0.0190 (7)	0.0132 (6)	−0.0001 (5)	−0.0004 (5)	0.0014 (5)
C13A	0.0190 (6)	0.0149 (6)	0.0184 (6)	0.0005 (5)	0.0028 (5)	0.0013 (5)
C14A	0.0150 (6)	0.0189 (7)	0.0204 (7)	−0.0028 (5)	−0.0001 (5)	−0.0006 (5)
C15A	0.0185 (6)	0.0187 (7)	0.0155 (6)	−0.0010 (5)	−0.0011 (5)	0.0005 (5)
C16A	0.0235 (7)	0.0222 (7)	0.0208 (7)	−0.0040 (6)	0.0038 (5)	0.0027 (5)
O1B	0.0193 (5)	0.0286 (6)	0.0201 (5)	−0.0027 (4)	−0.0007 (4)	0.0026 (4)
O2B	0.0307 (6)	0.0363 (6)	0.0235 (5)	−0.0083 (5)	0.0044 (4)	0.0055 (5)
O3B	0.0455 (7)	0.0300 (6)	0.0249 (6)	0.0027 (5)	−0.0036 (5)	0.0107 (5)
N1B	0.0318 (7)	0.0202 (6)	0.0169 (6)	−0.0065 (5)	−0.0013 (5)	0.0020 (5)
C1B	0.0185 (6)	0.0180 (7)	0.0209 (7)	−0.0001 (5)	−0.0033 (5)	0.0033 (5)
C2B	0.0173 (6)	0.0197 (7)	0.0212 (7)	−0.0014 (5)	0.0009 (5)	−0.0002 (5)
C3B	0.0255 (7)	0.0152 (6)	0.0140 (6)	−0.0045 (5)	−0.0020 (5)	0.0012 (5)
C4B	0.0227 (7)	0.0179 (7)	0.0201 (7)	0.0006 (5)	−0.0052 (5)	0.0019 (5)
C5B	0.0181 (6)	0.0191 (7)	0.0199 (7)	−0.0002 (5)	−0.0016 (5)	0.0002 (5)
C6B	0.0187 (6)	0.0160 (6)	0.0156 (6)	−0.0029 (5)	−0.0022 (5)	0.0001 (5)
C7B	0.0191 (6)	0.0163 (6)	0.0170 (6)	−0.0021 (5)	−0.0015 (5)	−0.0004 (5)
C8B	0.0176 (6)	0.0206 (7)	0.0187 (7)	−0.0014 (5)	−0.0022 (5)	0.0017 (5)
C9B	0.0193 (6)	0.0181 (7)	0.0184 (6)	−0.0020 (5)	−0.0016 (5)	0.0008 (5)
C10B	0.0204 (7)	0.0177 (6)	0.0155 (6)	−0.0047 (5)	−0.0028 (5)	0.0018 (5)
C11B	0.0181 (6)	0.0225 (7)	0.0179 (6)	−0.0024 (5)	−0.0003 (5)	0.0024 (5)
C12B	0.0234 (7)	0.0222 (7)	0.0152 (6)	−0.0036 (6)	−0.0010 (5)	0.0035 (5)
C13B	0.0215 (7)	0.0175 (7)	0.0198 (7)	−0.0043 (5)	−0.0032 (5)	0.0011 (5)
C14B	0.0179 (6)	0.0214 (7)	0.0194 (7)	−0.0015 (5)	−0.0012 (5)	0.0018 (5)
C15B	0.0226 (7)	0.0200 (7)	0.0150 (6)	−0.0040 (5)	−0.0001 (5)	0.0012 (5)
C16B	0.0237 (7)	0.0290 (8)	0.0177 (7)	−0.0020 (6)	−0.0027 (5)	0.0057 (6)

O1A—C7A	1.2256 (16)	O1B—C7B	1.2224 (17)
O2A—N1A	1.2219 (16)	O2B—N1B	1.2245 (16)
O3A—N1A	1.2263 (16)	O3B—N1B	1.2264 (16)
N1A—C3A	1.4728 (17)	N1B—C3B	1.4751 (17)
C1A—C2A	1.3903 (18)	C1B—C2B	1.3909 (19)
C1A—C6A	1.3919 (18)	C1B—C6B	1.3944 (19)
C1A—H1A	0.93	C1B—H1B	0.93
C2A—C3A	1.3805 (19)	C2B—C3B	1.3808 (19)
C2A—H2A	0.93	C2B—H2B	0.93
C3A—C4A	1.3780 (19)	C3B—C4B	1.380 (2)
C4A—C5A	1.3857 (18)	C4B—C5B	1.3839 (19)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.3944 (18)	C5B—C6B	1.3969 (18)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.5048 (18)	C6B—C7B	1.5039 (18)
C7A—C8A	1.4735 (18)	C7B—C8B	1.4759 (18)
C8A—C9A	1.3422 (18)	C8B—C9B	1.3370 (19)
C8A—H8A	0.93	C8B—H8B	0.93
C9A—C10A	1.4644 (18)	C9B—C10B	1.4594 (18)
C9A—H9A	0.93	C9B—H9B	0.93
C10A—C15A	1.4002 (19)	C10B—C15B	1.3966 (19)
C10A—C11A	1.4024 (18)	C10B—C11B	1.4002 (18)
C11A—C12A	1.3876 (18)	C11B—C12B	1.3903 (18)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.395 (2)	C12B—C13B	1.393 (2)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.3976 (19)	C13B—C14B	1.3992 (19)
C13A—C16A	1.5050 (18)	C13B—C16B	1.5024 (19)
C14A—C15A	1.3853 (18)	C14B—C15B	1.3874 (19)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—H15A	0.93	C15B—H15B	0.93
C16A—H16A	0.96	C16B—H16D	0.96
C16A—H16B	0.96	C16B—H16E	0.96
C16A—H16C	0.96	C16B—H16F	0.96
O2A—N1A—O3A	123.99 (12)	O2B—N1B—O3B	124.08 (12)
O2A—N1A—C3A	117.98 (12)	O2B—N1B—C3B	118.32 (12)
O3A—N1A—C3A	118.03 (12)	O3B—N1B—C3B	117.60 (12)
C2A—C1A—C6A	119.95 (12)	C2B—C1B—C6B	120.27 (12)
C2A—C1A—H1A	120.0	C2B—C1B—H1B	119.9
C6A—C1A—H1A	120.0	C6B—C1B—H1B	119.9
C3A—C2A—C1A	118.73 (12)	C3B—C2B—C1B	118.31 (13)
C3A—C2A—H2A	120.6	C3B—C2B—H2B	120.8
C1A—C2A—H2A	120.6	C1B—C2B—H2B	120.8
C4A—C3A—C2A	122.82 (12)	C4B—C3B—C2B	122.99 (12)
C4A—C3A—N1A	119.25 (12)	C4B—C3B—N1B	119.29 (12)
C2A—C3A—N1A	117.92 (12)	C2B—C3B—N1B	117.69 (12)
C3A—C4A—C5A	117.86 (12)	C3B—C4B—C5B	118.12 (12)
C3A—C4A—H4A	121.1	C3B—C4B—H4B	120.9
C5A—C4A—H4A	121.1	C5B—C4B—H4B	120.9
C4A—C5A—C6A	121.03 (13)	C4B—C5B—C6B	120.75 (13)
C4A—C5A—H5A	119.5	C4B—C5B—H5B	119.6
C6A—C5A—H5A	119.5	C6B—C5B—H5B	119.6
C1A—C6A—C5A	119.60 (12)	C1B—C6B—C5B	119.56 (12)
C1A—C6A—C7A	122.29 (12)	C1B—C6B—C7B	122.63 (12)
C5A—C6A—C7A	118.08 (12)	C5B—C6B—C7B	117.79 (12)
O1A—C7A—C8A	122.24 (12)	O1B—C7B—C8B	122.13 (12)
O1A—C7A—C6A	119.41 (12)	O1B—C7B—C6B	119.37 (12)
C8A—C7A—C6A	118.34 (11)	C8B—C7B—C6B	118.50 (12)
C9A—C8A—C7A	120.01 (12)	C9B—C8B—C7B	120.66 (13)
C9A—C8A—H8A	120.0	C9B—C8B—H8B	119.7
C7A—C8A—H8A	120.0	C7B—C8B—H8B	119.7
C8A—C9A—C10A	126.33 (13)	C8B—C9B—C10B	126.94 (13)
C8A—C9A—H9A	116.8	C8B—C9B—H9B	116.5
C10A—C9A—H9A	116.8	C10B—C9B—H9B	116.5
C15A—C10A—C11A	117.72 (12)	C15B—C10B—C11B	118.17 (12)
C15A—C10A—C9A	122.96 (12)	C15B—C10B—C9B	122.17 (12)
C11A—C10A—C9A	119.28 (12)	C11B—C10B—C9B	119.65 (12)
C12A—C11A—C10A	121.57 (13)	C12B—C11B—C10B	120.96 (13)
C12A—C11A—H11A	119.2	C12B—C11B—H11B	119.5
C10A—C11A—H11A	119.2	C10B—C11B—H11B	119.5
C11A—C12A—C13A	120.58 (12)	C11B—C12B—C13B	120.84 (13)
C11A—C12A—H12A	119.7	C11B—C12B—H12B	119.6
C13A—C12A—H12A	119.7	C13B—C12B—H12B	119.6
C12A—C13A—C14A	117.86 (12)	C12B—C13B—C14B	118.14 (12)
C12A—C13A—C16A	121.01 (12)	C12B—C13B—C16B	120.38 (12)
C14A—C13A—C16A	121.13 (13)	C14B—C13B—C16B	121.47 (13)
C15A—C14A—C13A	121.84 (13)	C15B—C14B—C13B	121.19 (13)
C15A—C14A—H14A	119.1	C15B—C14B—H14B	119.4
C13A—C14A—H14A	119.1	C13B—C14B—H14B	119.4
C14A—C15A—C10A	120.40 (12)	C14B—C15B—C10B	120.68 (12)
C14A—C15A—H15A	119.8	C14B—C15B—H15B	119.7
C10A—C15A—H15A	119.8	C10B—C15B—H15B	119.7
C13A—C16A—H16A	109.5	C13B—C16B—H16D	109.5
C13A—C16A—H16B	109.5	C13B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C13A—C16A—H16C	109.5	C13B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C6A—C1A—C2A—C3A	−0.6 (2)	C6B—C1B—C2B—C3B	0.8 (2)
C1A—C2A—C3A—C4A	0.4 (2)	C1B—C2B—C3B—C4B	−0.3 (2)
C1A—C2A—C3A—N1A	−179.99 (13)	C1B—C2B—C3B—N1B	177.49 (12)
O2A—N1A—C3A—C4A	−169.19 (14)	O2B—N1B—C3B—C4B	−176.27 (13)
O3A—N1A—C3A—C4A	11.5 (2)	O3B—N1B—C3B—C4B	4.54 (19)
O2A—N1A—C3A—C2A	11.2 (2)	O2B—N1B—C3B—C2B	5.84 (19)
O3A—N1A—C3A—C2A	−168.15 (13)	O3B—N1B—C3B—C2B	−173.35 (13)
C2A—C3A—C4A—C5A	0.0 (2)	C2B—C3B—C4B—C5B	−0.7 (2)
N1A—C3A—C4A—C5A	−179.61 (13)	N1B—C3B—C4B—C5B	−178.43 (12)
C3A—C4A—C5A—C6A	−0.2 (2)	C3B—C4B—C5B—C6B	1.2 (2)
C2A—C1A—C6A—C5A	0.5 (2)	C2B—C1B—C6B—C5B	−0.3 (2)
C2A—C1A—C6A—C7A	−177.56 (13)	C2B—C1B—C6B—C7B	177.65 (13)
C4A—C5A—C6A—C1A	0.0 (2)	C4B—C5B—C6B—C1B	−0.7 (2)
C4A—C5A—C6A—C7A	178.06 (13)	C4B—C5B—C6B—C7B	−178.75 (13)
C1A—C6A—C7A—O1A	159.57 (14)	C1B—C6B—C7B—O1B	−162.74 (14)
C5A—C6A—C7A—O1A	−18.5 (2)	C5B—C6B—C7B—O1B	15.3 (2)
C1A—C6A—C7A—C8A	−21.7 (2)	C1B—C6B—C7B—C8B	17.1 (2)
C5A—C6A—C7A—C8A	160.26 (13)	C5B—C6B—C7B—C8B	−164.91 (12)
O1A—C7A—C8A—C9A	−6.7 (2)	O1B—C7B—C8B—C9B	−3.8 (2)
C6A—C7A—C8A—C9A	174.58 (12)	C6B—C7B—C8B—C9B	176.38 (13)
C7A—C8A—C9A—C10A	174.30 (12)	C7B—C8B—C9B—C10B	179.38 (13)
C8A—C9A—C10A—C15A	−15.3 (2)	C8B—C9B—C10B—C15B	−13.8 (2)
C8A—C9A—C10A—C11A	167.03 (13)	C8B—C9B—C10B—C11B	167.69 (14)
C15A—C10A—C11A—C12A	1.2 (2)	C15B—C10B—C11B—C12B	0.7 (2)
C9A—C10A—C11A—C12A	179.00 (12)	C9B—C10B—C11B—C12B	179.31 (13)
C10A—C11A—C12A—C13A	−1.3 (2)	C10B—C11B—C12B—C13B	−0.7 (2)
C11A—C12A—C13A—C14A	0.1 (2)	C11B—C12B—C13B—C14B	−0.1 (2)
C11A—C12A—C13A—C16A	−179.37 (13)	C11B—C12B—C13B—C16B	179.37 (14)
C12A—C13A—C14A—C15A	1.2 (2)	C12B—C13B—C14B—C15B	0.8 (2)
C16A—C13A—C14A—C15A	−179.32 (13)	C16B—C13B—C14B—C15B	−178.62 (14)
C13A—C14A—C15A—C10A	−1.3 (2)	C13B—C14B—C15B—C10B	−0.8 (2)
C11A—C10A—C15A—C14A	0.09 (19)	C11B—C10B—C15B—C14B	0.0 (2)
C9A—C10A—C15A—C14A	−177.62 (12)	C9B—C10B—C15B—C14B	−178.54 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O1Bi	0.93	2.58	3.2597 (17)	131
C9A—H9A···O1A	0.93	2.48	2.8045 (17)	101
C9B—H9B···O1B	0.93	2.48	2.8112 (17)	101
C1B—H1B···Cg1	0.93	2.90	3.4853 (15)	123
C4B—H4B···Cg1ii	0.93	2.86	3.4837 (15)	126
C16A—H16C···Cg2iii	0.96	2.91	3.7837 (15)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯O1Bi	0.93	2.58	3.2597 (17)	131
C9A—H9A⋯O1A	0.93	2.48	2.8045 (17)	101
C9B—H9B⋯O1B	0.93	2.48	2.8112 (17)	101
C1B—H1B⋯Cg1	0.93	2.90	3.4853 (15)	123
C4B—H4B⋯Cg1ii	0.93	2.86	3.4837 (15)	126
C16A—H16C⋯Cg2iii	0.96	2.91	3.7837 (15)	151

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the C10A–C15A and C1B–C6B rings, ,respectively.