3-(4-Bromo­phen­yl)-1-(4-nitro­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₀BrNO₃, the mol­ecules are arranged into infinite chains through Br...O short inter­actions. The chains are stacked to form layers. These layers are inter­connected by C—H...O inter­actions. There are two molecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.085
• Data-to-parameter ratio = 30.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1A   ..  O2B     ..       3.04 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1B   ..  O2A     ..       2.99 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.286     0.444
            Tmin and Tmax expected:      0.232     0.444
            RR =      1.234
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.20
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(4-bromophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Crystal data

C15H10BrNO3	Z = 4
Mr = 332.15	F(000) = 664
Triclinic, P1	Dx = 1.740 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9341 (1) Å	Cell parameters from 6533 reflections
b = 7.9193 (1) Å	θ = 0.8–35.0°
c = 27.2996 (4) Å	µ = 3.25 mm^−1
α = 89.938 (1)°	T = 100 K
β = 85.622 (1)°	Block, yellow
γ = 82.357 (1)°	0.55 × 0.39 × 0.25 mm
V = 1267.75 (3) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	11069 independent reflections
Radiation source: fine-focus sealed tube	9020 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 0.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.286, Tmax = 0.444	l = −44→39
41078 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 0.3692P] where P = (Fo^2 + 2Fc^2)/3
11069 reflections	(Δ/σ)max = 0.002
361 parameters	Δρmax = 0.94 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

Experimental. The 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1A	0.11160 (3)	0.65694 (2)	0.548170 (5)	0.01771 (4)
O1A	1.0276 (2)	0.15693 (16)	0.76642 (4)	0.0191 (2)
O2A	0.3440 (2)	−0.10525 (17)	0.97481 (5)	0.0239 (2)
O3A	0.6758 (3)	−0.25926 (17)	0.97398 (5)	0.0265 (3)
N1A	0.5394 (3)	−0.14924 (17)	0.95686 (5)	0.0172 (2)
C1A	0.3362 (3)	0.43903 (19)	0.67693 (5)	0.0154 (2)
H1AA	0.2721	0.4185	0.7082	0.019*
C2A	0.2009 (3)	0.5226 (2)	0.64287 (6)	0.0164 (3)
H2AA	0.0478	0.5604	0.6514	0.020*
C3A	0.2961 (3)	0.54974 (19)	0.59563 (5)	0.0152 (2)
C4A	0.5262 (3)	0.4973 (2)	0.58252 (6)	0.0166 (3)
H4AA	0.5888	0.5163	0.5511	0.020*
C5A	0.6605 (3)	0.4160 (2)	0.61741 (6)	0.0172 (3)
H5AA	0.8145	0.3814	0.6090	0.021*
C6A	0.5687 (3)	0.38498 (18)	0.66497 (5)	0.0144 (2)
C7A	0.7172 (3)	0.30142 (19)	0.70069 (5)	0.0156 (3)
H7AA	0.8734	0.2927	0.6926	0.019*
C8A	0.6514 (3)	0.2364 (2)	0.74378 (5)	0.0158 (3)
H8AA	0.4968	0.2407	0.7533	0.019*
C9A	0.8223 (3)	0.15767 (18)	0.77650 (5)	0.0145 (2)
C10A	0.7411 (3)	0.07864 (18)	0.82339 (5)	0.0133 (2)
C11A	0.9000 (3)	−0.03066 (19)	0.84773 (6)	0.0157 (3)
H11A	1.0497	−0.0532	0.8342	0.019*
C12A	0.8374 (3)	−0.10573 (19)	0.89164 (6)	0.0163 (3)
H12A	0.9423	−0.1794	0.9077	0.020*
C13A	0.6126 (3)	−0.06743 (18)	0.91099 (5)	0.0144 (2)
C14A	0.4509 (3)	0.04243 (19)	0.88839 (6)	0.0156 (3)
H14A	0.3027	0.0673	0.9026	0.019*
C15A	0.5160 (3)	0.11443 (19)	0.84392 (5)	0.0152 (2)
H15A	0.4098	0.1866	0.8277	0.018*
Br1B	1.11967 (3)	0.685636 (19)	0.050725 (5)	0.01636 (4)
O1B	0.2120 (2)	0.21630 (17)	0.27257 (4)	0.0216 (2)
O2B	0.8959 (2)	−0.1711 (2)	0.46025 (5)	0.0304 (3)
N1B	0.6911 (3)	−0.13967 (17)	0.45522 (5)	0.0179 (2)
C1B	0.8806 (3)	0.46306 (19)	0.17840 (5)	0.0142 (2)
H1BA	0.9290	0.4440	0.2098	0.017*
C2B	1.0106 (3)	0.54556 (18)	0.14408 (5)	0.0144 (2)
H2BA	1.1438	0.5839	0.1527	0.017*
C3B	0.9415 (3)	0.57110 (17)	0.09664 (5)	0.0136 (2)
C4B	0.7405 (3)	0.51793 (18)	0.08327 (5)	0.0142 (2)
H4BA	0.6948	0.5351	0.0516	0.017*
C5B	0.6092 (3)	0.43819 (18)	0.11848 (5)	0.0136 (2)
H5BA	0.4731	0.4040	0.1101	0.016*
C6B	0.6765 (2)	0.40813 (17)	0.16614 (5)	0.0126 (2)
C7B	0.5286 (3)	0.32658 (18)	0.20179 (5)	0.0143 (2)
H7BA	0.3813	0.3184	0.1935	0.017*
C8B	0.5869 (3)	0.26277 (19)	0.24523 (5)	0.0143 (2)
H8BA	0.7365	0.2587	0.2536	0.017*
C9B	0.4149 (3)	0.19877 (19)	0.28002 (5)	0.0145 (2)
C10B	0.4942 (3)	0.11280 (18)	0.32567 (5)	0.0132 (2)
C11B	0.3317 (3)	0.0978 (2)	0.36500 (6)	0.0162 (3)
H11B	0.1806	0.1439	0.3624	0.019*
C12B	0.3931 (3)	0.0152 (2)	0.40772 (6)	0.0172 (3)
H12B	0.2854	0.0046	0.4337	0.021*
C13B	0.6196 (3)	−0.05111 (19)	0.41051 (5)	0.0147 (2)
C14B	0.7850 (3)	−0.0376 (2)	0.37247 (6)	0.0171 (3)
H14B	0.9361	−0.0831	0.3754	0.021*
C15B	0.7204 (3)	0.0452 (2)	0.32999 (6)	0.0168 (3)
H15B	0.8291	0.0556	0.3042	0.020*
O3B	0.5423 (2)	−0.17919 (17)	0.48512 (5)	0.0235 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.01561 (7)	0.02389 (7)	0.01348 (7)	−0.00129 (5)	−0.00246 (5)	0.00455 (5)
O1A	0.0150 (5)	0.0259 (5)	0.0163 (5)	−0.0027 (4)	0.0002 (4)	0.0027 (4)
O2A	0.0240 (6)	0.0279 (6)	0.0195 (6)	−0.0058 (5)	0.0037 (5)	0.0049 (4)
O3A	0.0351 (7)	0.0239 (6)	0.0190 (6)	0.0020 (5)	−0.0025 (5)	0.0084 (4)
N1A	0.0231 (7)	0.0157 (5)	0.0135 (6)	−0.0045 (5)	−0.0015 (5)	0.0013 (4)
C1A	0.0154 (6)	0.0190 (6)	0.0118 (6)	−0.0023 (5)	0.0002 (5)	0.0015 (5)
C2A	0.0140 (6)	0.0210 (6)	0.0139 (6)	−0.0010 (5)	−0.0001 (5)	0.0023 (5)
C3A	0.0154 (6)	0.0175 (6)	0.0132 (6)	−0.0022 (5)	−0.0033 (5)	0.0021 (5)
C4A	0.0152 (6)	0.0209 (6)	0.0137 (6)	−0.0033 (5)	0.0003 (5)	0.0016 (5)
C5A	0.0151 (7)	0.0212 (6)	0.0151 (6)	−0.0021 (5)	0.0006 (5)	0.0032 (5)
C6A	0.0160 (6)	0.0163 (6)	0.0115 (6)	−0.0035 (5)	−0.0014 (5)	0.0017 (4)
C7A	0.0155 (6)	0.0187 (6)	0.0128 (6)	−0.0024 (5)	−0.0020 (5)	0.0024 (5)
C8A	0.0137 (6)	0.0208 (6)	0.0127 (6)	−0.0014 (5)	−0.0020 (5)	0.0030 (5)
C9A	0.0159 (6)	0.0154 (6)	0.0120 (6)	−0.0016 (5)	−0.0009 (5)	0.0002 (4)
C10A	0.0133 (6)	0.0149 (5)	0.0116 (6)	−0.0016 (5)	−0.0013 (5)	0.0005 (4)
C11A	0.0142 (6)	0.0170 (6)	0.0154 (6)	0.0002 (5)	−0.0016 (5)	0.0013 (5)
C12A	0.0165 (7)	0.0166 (6)	0.0157 (6)	−0.0006 (5)	−0.0030 (5)	0.0029 (5)
C13A	0.0171 (6)	0.0135 (5)	0.0127 (6)	−0.0028 (5)	−0.0005 (5)	0.0011 (4)
C14A	0.0144 (6)	0.0165 (6)	0.0152 (6)	−0.0008 (5)	0.0003 (5)	0.0019 (5)
C15A	0.0139 (6)	0.0176 (6)	0.0133 (6)	0.0003 (5)	−0.0008 (5)	0.0035 (5)
Br1B	0.01656 (7)	0.01795 (7)	0.01456 (7)	−0.00455 (5)	0.00272 (5)	0.00316 (5)
O1B	0.0137 (5)	0.0341 (6)	0.0174 (5)	−0.0043 (5)	−0.0020 (4)	0.0077 (4)
O2B	0.0202 (6)	0.0468 (8)	0.0236 (6)	0.0003 (6)	−0.0059 (5)	0.0158 (6)
N1B	0.0213 (6)	0.0184 (6)	0.0140 (6)	−0.0021 (5)	−0.0021 (5)	0.0031 (4)
C1B	0.0134 (6)	0.0181 (6)	0.0110 (6)	−0.0019 (5)	−0.0012 (5)	0.0019 (4)
C2B	0.0129 (6)	0.0164 (6)	0.0143 (6)	−0.0035 (5)	−0.0003 (5)	0.0004 (5)
C3B	0.0145 (6)	0.0124 (5)	0.0135 (6)	−0.0012 (5)	0.0018 (5)	0.0014 (4)
C4B	0.0146 (6)	0.0171 (6)	0.0109 (6)	−0.0022 (5)	−0.0007 (5)	0.0013 (4)
C5B	0.0132 (6)	0.0156 (6)	0.0122 (6)	−0.0020 (5)	−0.0015 (5)	0.0017 (4)
C6B	0.0124 (6)	0.0136 (5)	0.0117 (6)	−0.0014 (4)	−0.0001 (4)	0.0016 (4)
C7B	0.0131 (6)	0.0167 (6)	0.0132 (6)	−0.0027 (5)	−0.0004 (5)	0.0025 (4)
C8B	0.0124 (6)	0.0174 (6)	0.0130 (6)	−0.0030 (5)	0.0004 (5)	0.0020 (5)
C9B	0.0146 (6)	0.0180 (6)	0.0111 (6)	−0.0029 (5)	−0.0005 (5)	0.0025 (4)
C10B	0.0132 (6)	0.0163 (6)	0.0101 (6)	−0.0028 (5)	−0.0003 (4)	0.0016 (4)
C11B	0.0119 (6)	0.0232 (7)	0.0133 (6)	−0.0020 (5)	0.0004 (5)	0.0033 (5)
C12B	0.0149 (6)	0.0241 (7)	0.0122 (6)	−0.0028 (5)	0.0014 (5)	0.0034 (5)
C13B	0.0162 (6)	0.0173 (6)	0.0108 (6)	−0.0028 (5)	−0.0025 (5)	0.0026 (4)
C14B	0.0130 (6)	0.0219 (7)	0.0157 (6)	−0.0005 (5)	0.0004 (5)	0.0032 (5)
C15B	0.0145 (6)	0.0220 (7)	0.0131 (6)	−0.0007 (5)	0.0013 (5)	0.0038 (5)
O3B	0.0262 (6)	0.0296 (6)	0.0149 (5)	−0.0061 (5)	0.0014 (5)	0.0070 (4)

Geometric parameters (Å, º)

Br1A—C3A	1.8880 (15)	Br1B—C3B	1.8874 (14)
O1A—C9A	1.2278 (19)	O1B—C9B	1.2264 (19)
O2A—N1A	1.2294 (19)	O2B—N1B	1.226 (2)
O3A—N1A	1.2256 (19)	N1B—O3B	1.2278 (18)
N1A—C13A	1.472 (2)	N1B—C13B	1.469 (2)
C1A—C2A	1.385 (2)	C1B—C2B	1.386 (2)
C1A—C6A	1.402 (2)	C1B—C6B	1.404 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.396 (2)	C2B—C3B	1.395 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.393 (2)	C3B—C4B	1.390 (2)
C4A—C5A	1.391 (2)	C4B—C5B	1.395 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.404 (2)	C5B—C6B	1.401 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.463 (2)	C6B—C7B	1.467 (2)
C7A—C8A	1.336 (2)	C7B—C8B	1.340 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.478 (2)	C8B—C9B	1.479 (2)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.499 (2)	C9B—C10B	1.497 (2)
C10A—C11A	1.399 (2)	C10B—C15B	1.391 (2)
C10A—C15A	1.401 (2)	C10B—C11B	1.403 (2)
C11A—C12A	1.385 (2)	C11B—C12B	1.386 (2)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.391 (2)	C12B—C13B	1.384 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.388 (2)	C13B—C14B	1.387 (2)
C14A—C15A	1.391 (2)	C14B—C15B	1.386 (2)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
O3A—N1A—O2A	124.46 (14)	O2B—N1B—O3B	123.86 (14)
O3A—N1A—C13A	117.71 (14)	O2B—N1B—C13B	118.08 (13)
O2A—N1A—C13A	117.81 (14)	O3B—N1B—C13B	118.06 (14)
C2A—C1A—C6A	120.90 (14)	C2B—C1B—C6B	120.49 (13)
C2A—C1A—H1AA	119.6	C2B—C1B—H1BA	119.8
C6A—C1A—H1AA	119.6	C6B—C1B—H1BA	119.8
C1A—C2A—C3A	119.51 (15)	C1B—C2B—C3B	119.99 (13)
C1A—C2A—H2AA	120.2	C1B—C2B—H2BA	120.0
C3A—C2A—H2AA	120.2	C3B—C2B—H2BA	120.0
C4A—C3A—C2A	121.02 (14)	C4B—C3B—C2B	120.95 (13)
C4A—C3A—Br1A	118.97 (11)	C4B—C3B—Br1B	119.79 (11)
C2A—C3A—Br1A	120.01 (12)	C2B—C3B—Br1B	119.23 (11)
C5A—C4A—C3A	118.73 (14)	C3B—C4B—C5B	118.41 (13)
C5A—C4A—H4AA	120.6	C3B—C4B—H4BA	120.8
C3A—C4A—H4AA	120.6	C5B—C4B—H4BA	120.8
C4A—C5A—C6A	121.47 (15)	C4B—C5B—C6B	121.86 (13)
C4A—C5A—H5AA	119.3	C4B—C5B—H5BA	119.1
C6A—C5A—H5AA	119.3	C6B—C5B—H5BA	119.1
C1A—C6A—C5A	118.35 (14)	C5B—C6B—C1B	118.27 (13)
C1A—C6A—C7A	122.07 (13)	C5B—C6B—C7B	119.24 (13)
C5A—C6A—C7A	119.56 (14)	C1B—C6B—C7B	122.46 (13)
C8A—C7A—C6A	126.65 (15)	C8B—C7B—C6B	125.83 (14)
C8A—C7A—H7AA	116.7	C8B—C7B—H7BA	117.1
C6A—C7A—H7AA	116.7	C6B—C7B—H7BA	117.1
C7A—C8A—C9A	120.50 (14)	C7B—C8B—C9B	120.52 (14)
C7A—C8A—H8AA	119.8	C7B—C8B—H8BA	119.7
C9A—C8A—H8AA	119.8	C9B—C8B—H8BA	119.7
O1A—C9A—C8A	121.71 (14)	O1B—C9B—C8B	121.81 (14)
O1A—C9A—C10A	119.55 (14)	O1B—C9B—C10B	120.01 (13)
C8A—C9A—C10A	118.74 (13)	C8B—C9B—C10B	118.17 (13)
C11A—C10A—C15A	119.68 (14)	C15B—C10B—C11B	119.32 (14)
C11A—C10A—C9A	117.90 (13)	C15B—C10B—C9B	122.50 (13)
C15A—C10A—C9A	122.40 (13)	C11B—C10B—C9B	118.17 (14)
C12A—C11A—C10A	120.91 (14)	C12B—C11B—C10B	120.94 (15)
C12A—C11A—H11A	119.5	C12B—C11B—H11B	119.5
C10A—C11A—H11A	119.5	C10B—C11B—H11B	119.5
C11A—C12A—C13A	117.91 (14)	C13B—C12B—C11B	118.01 (14)
C11A—C12A—H12A	121.0	C13B—C12B—H12B	121.0
C13A—C12A—H12A	121.0	C11B—C12B—H12B	121.0
C14A—C13A—C12A	122.94 (14)	C12B—C13B—C14B	122.57 (14)
C14A—C13A—N1A	117.92 (14)	C12B—C13B—N1B	119.56 (13)
C12A—C13A—N1A	119.13 (14)	C14B—C13B—N1B	117.87 (14)
C13A—C14A—C15A	118.31 (14)	C15B—C14B—C13B	118.62 (15)
C13A—C14A—H14A	120.8	C15B—C14B—H14B	120.7
C15A—C14A—H14A	120.8	C13B—C14B—H14B	120.7
C14A—C15A—C10A	120.24 (14)	C14B—C15B—C10B	120.53 (14)
C14A—C15A—H15A	119.9	C14B—C15B—H15B	119.7
C10A—C15A—H15A	119.9	C10B—C15B—H15B	119.7
C6A—C1A—C2A—C3A	1.6 (2)	C6B—C1B—C2B—C3B	−1.5 (2)
C1A—C2A—C3A—C4A	−1.4 (2)	C1B—C2B—C3B—C4B	1.3 (2)
C1A—C2A—C3A—Br1A	177.96 (11)	C1B—C2B—C3B—Br1B	179.41 (11)
C2A—C3A—C4A—C5A	0.4 (2)	C2B—C3B—C4B—C5B	0.0 (2)
Br1A—C3A—C4A—C5A	−178.99 (11)	Br1B—C3B—C4B—C5B	−178.10 (11)
C3A—C4A—C5A—C6A	0.5 (2)	C3B—C4B—C5B—C6B	−1.2 (2)
C2A—C1A—C6A—C5A	−0.7 (2)	C4B—C5B—C6B—C1B	1.0 (2)
C2A—C1A—C6A—C7A	177.95 (14)	C4B—C5B—C6B—C7B	178.85 (13)
C4A—C5A—C6A—C1A	−0.3 (2)	C2B—C1B—C6B—C5B	0.3 (2)
C4A—C5A—C6A—C7A	−179.03 (14)	C2B—C1B—C6B—C7B	−177.45 (14)
C1A—C6A—C7A—C8A	14.1 (2)	C5B—C6B—C7B—C8B	167.40 (15)
C5A—C6A—C7A—C8A	−167.28 (15)	C1B—C6B—C7B—C8B	−14.9 (2)
C6A—C7A—C8A—C9A	−179.07 (14)	C6B—C7B—C8B—C9B	173.99 (13)
C7A—C8A—C9A—O1A	3.6 (2)	C7B—C8B—C9B—O1B	−7.0 (2)
C7A—C8A—C9A—C10A	−177.05 (14)	C7B—C8B—C9B—C10B	173.87 (14)
O1A—C9A—C10A—C11A	−16.1 (2)	O1B—C9B—C10B—C15B	160.90 (15)
C8A—C9A—C10A—C11A	164.49 (13)	C8B—C9B—C10B—C15B	−19.9 (2)
O1A—C9A—C10A—C15A	161.97 (14)	O1B—C9B—C10B—C11B	−17.9 (2)
C8A—C9A—C10A—C15A	−17.4 (2)	C8B—C9B—C10B—C11B	161.32 (13)
C15A—C10A—C11A—C12A	0.7 (2)	C15B—C10B—C11B—C12B	−0.7 (2)
C9A—C10A—C11A—C12A	178.90 (13)	C9B—C10B—C11B—C12B	178.12 (14)
C10A—C11A—C12A—C13A	−0.7 (2)	C10B—C11B—C12B—C13B	0.4 (2)
C11A—C12A—C13A—C14A	−0.3 (2)	C11B—C12B—C13B—C14B	0.1 (2)
C11A—C12A—C13A—N1A	178.22 (13)	C11B—C12B—C13B—N1B	−179.95 (14)
O3A—N1A—C13A—C14A	172.60 (14)	O2B—N1B—C13B—C12B	−167.72 (15)
O2A—N1A—C13A—C14A	−5.8 (2)	O3B—N1B—C13B—C12B	12.9 (2)
O3A—N1A—C13A—C12A	−6.0 (2)	O2B—N1B—C13B—C14B	12.2 (2)
O2A—N1A—C13A—C12A	175.54 (14)	O3B—N1B—C13B—C14B	−167.09 (14)
C12A—C13A—C14A—C15A	1.4 (2)	C12B—C13B—C14B—C15B	−0.2 (2)
N1A—C13A—C14A—C15A	−177.21 (13)	N1B—C13B—C14B—C15B	179.83 (14)
C13A—C14A—C15A—C10A	−1.3 (2)	C13B—C14B—C15B—C10B	−0.1 (2)
C11A—C10A—C15A—C14A	0.3 (2)	C11B—C10B—C15B—C14B	0.5 (2)
C9A—C10A—C15A—C14A	−177.76 (13)	C9B—C10B—C15B—C14B	−178.20 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···O1A	0.93	2.46	2.804 (2)	102
C7B—H7BA···O1B	0.93	2.49	2.812 (2)	100
C15B—H15B···O1A^i	0.93	2.58	3.240 (2)	129

Symmetry code: (i) −x+2, −y, −z+1.