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

Each of the two unique mol­ecules of the title compound, C₁₆H₁₃BrO₂, is non-planar, the dihedral angle between the two benzene rings being 55.04 (7)° in one mol­ecule and 51.45 (6)° in the other. In the crystal structure, the mol­ecules are stabilized by short Br...O inter­actions which link the mol­ecules into chains along the a axis. These chains are stacked down the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 39.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1A   ..  O2A     ..       3.06 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1B   ..  O2B     ..       3.02 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.241     0.522
            Tmin(prime) and Tmax expected:      0.259     0.471
            RR(prime) =      0.839
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.902
            Tmax scaled      0.471 Tmin scaled      0.217

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun and I.A. Razak are supervisors of M.M. Rosli whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and V. Shettigar in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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).

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

Crystal data

C16H13BrO2	F(000) = 1280
Mr = 317.17	Dx = 1.612 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7613 reflections
a = 15.7797 (3) Å	θ = 1.4–37.5°
b = 5.8463 (1) Å	µ = 3.14 mm^−1
c = 32.4291 (6) Å	T = 100 K
β = 119.088 (1)°	Block, yellow
V = 2614.35 (9) Å^3	0.42 × 0.28 × 0.24 mm
Z = 8

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	13630 independent reflections
Radiation source: fine-focus sealed tube	10641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 8.33 pixels mm^-1	θmax = 37.5°, θmin = 1.4°
ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.241, Tmax = 0.522	l = −55→55
92812 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0399P)^2 + 4.617P] where P = (Fo^2 + 2Fc^2)/3
13630 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 1.13 e Å^−3
0 restraints	Δρmin = −2.11 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	0.551825 (15)	0.84118 (4)	0.197325 (7)	0.01928 (5)
O1A	0.14568 (12)	0.3065 (3)	0.17389 (7)	0.0221 (3)
O2A	−0.27435 (12)	1.0804 (3)	0.19901 (6)	0.0208 (3)
C1A	0.29405 (15)	0.8133 (4)	0.20164 (7)	0.0174 (3)
H1A	0.2584	0.9125	0.2108	0.021*
C2A	0.38343 (15)	0.8830 (4)	0.20723 (7)	0.0177 (3)
H2A	0.4100	1.0269	0.2211	0.021*
C3A	0.43313 (14)	0.7386 (4)	0.19226 (7)	0.0154 (3)
C4A	0.39733 (15)	0.5240 (4)	0.17327 (7)	0.0167 (3)
H4A	0.4327	0.4266	0.1636	0.020*
C5A	0.30883 (15)	0.4546 (4)	0.16870 (7)	0.0161 (3)
H5A	0.2837	0.3080	0.1560	0.019*
C6A	0.25634 (14)	0.5985 (4)	0.18266 (7)	0.0146 (3)
C7A	0.16270 (14)	0.5135 (4)	0.17761 (7)	0.0167 (3)
C8A	0.09262 (14)	0.6812 (4)	0.17766 (7)	0.0172 (3)
H8A	0.0963	0.8377	0.1708	0.021*
C9A	0.02404 (14)	0.6093 (4)	0.18755 (7)	0.0168 (3)
H9A	0.0246	0.4505	0.1939	0.020*
C10A	−0.05152 (13)	0.7434 (4)	0.18988 (7)	0.0143 (3)
C11A	−0.09555 (15)	0.6543 (4)	0.21497 (7)	0.0170 (3)
H11A	−0.0753	0.5098	0.2300	0.020*
C12A	−0.16792 (15)	0.7730 (4)	0.21820 (7)	0.0174 (3)
H12A	−0.1953	0.7126	0.2363	0.021*
C13A	−0.20063 (14)	0.9812 (4)	0.19488 (7)	0.0159 (3)
C14A	−0.15804 (14)	1.0737 (4)	0.16944 (7)	0.0168 (3)
H14A	−0.1799	1.2161	0.1536	0.020*
C15A	−0.08377 (14)	0.9557 (4)	0.16755 (7)	0.0158 (3)
H15A	−0.0542	1.0200	0.1508	0.019*
C16A	−0.32139 (17)	1.2747 (4)	0.17007 (10)	0.0235 (4)
H16A	−0.3723	1.3291	0.1767	0.035*
H16B	−0.3503	1.2314	0.1367	0.035*
H16C	−0.2738	1.3968	0.1769	0.035*
Br1B	1.414629 (15)	0.32797 (4)	0.062736 (7)	0.01849 (5)
O1B	1.02969 (13)	−0.2008 (3)	0.06331 (7)	0.0228 (3)
O2B	0.57938 (11)	0.5731 (3)	0.05898 (6)	0.0195 (3)
C1B	1.13787 (14)	0.3087 (3)	0.04661 (7)	0.0161 (3)
H1B	1.0842	0.4100	0.0360	0.019*
C2B	1.22092 (15)	0.3775 (4)	0.04530 (7)	0.0163 (3)
H2B	1.2235	0.5225	0.0328	0.020*
C3B	1.30006 (14)	0.2303 (4)	0.06265 (7)	0.0144 (3)
C4B	1.29714 (14)	0.0146 (4)	0.08002 (7)	0.0157 (3)
H4B	1.3519	−0.0837	0.0917	0.019*
C5B	1.21316 (14)	−0.0543 (4)	0.07994 (7)	0.0155 (3)
H5B	1.2099	−0.2022	0.0912	0.019*
C6B	1.13274 (14)	0.0926 (3)	0.06336 (7)	0.0140 (3)
C7B	1.04296 (14)	0.0071 (4)	0.06295 (7)	0.0162 (3)
C8B	0.97276 (14)	0.1753 (4)	0.06255 (7)	0.0166 (3)
H8B	0.9915	0.3303	0.0708	0.020*
C9B	0.88258 (14)	0.1081 (4)	0.05050 (7)	0.0157 (3)
H9B	0.8665	−0.0453	0.0399	0.019*
C10B	0.80566 (14)	0.2435 (3)	0.05180 (7)	0.0143 (3)
C11B	0.71169 (14)	0.1539 (4)	0.03125 (7)	0.0163 (3)
H11B	0.6986	0.0107	0.0155	0.020*
C12B	0.63739 (14)	0.2696 (4)	0.03338 (7)	0.0164 (3)
H12B	0.5737	0.2076	0.0186	0.020*
C13B	0.65629 (13)	0.4772 (4)	0.05735 (7)	0.0148 (3)
C14B	0.74943 (14)	0.5721 (4)	0.07817 (7)	0.0165 (3)
H14B	0.7626	0.7137	0.0945	0.020*
C15B	0.82234 (14)	0.4559 (4)	0.07454 (7)	0.0161 (3)
H15B	0.8852	0.5221	0.0878	0.019*
C16B	0.59646 (17)	0.7679 (4)	0.08862 (9)	0.0213 (4)
H16D	0.5351	0.8186	0.0863	0.032*
H16E	0.6239	0.8919	0.0785	0.032*
H16F	0.6421	0.7270	0.1214	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.01606 (8)	0.02374 (10)	0.01930 (9)	−0.00176 (7)	0.00958 (7)	0.00075 (7)
O1A	0.0206 (7)	0.0187 (7)	0.0289 (8)	−0.0007 (6)	0.0135 (6)	−0.0020 (6)
O2A	0.0175 (6)	0.0240 (8)	0.0245 (7)	0.0035 (6)	0.0130 (6)	0.0022 (6)
C1A	0.0161 (8)	0.0184 (9)	0.0185 (8)	0.0013 (7)	0.0091 (6)	−0.0022 (7)
C2A	0.0173 (8)	0.0169 (8)	0.0176 (8)	−0.0004 (7)	0.0076 (7)	−0.0017 (6)
C3A	0.0139 (7)	0.0182 (8)	0.0135 (7)	0.0004 (6)	0.0063 (6)	0.0007 (6)
C4A	0.0162 (7)	0.0191 (8)	0.0155 (7)	0.0017 (7)	0.0082 (6)	−0.0015 (6)
C5A	0.0162 (7)	0.0154 (8)	0.0160 (7)	0.0003 (6)	0.0074 (6)	−0.0011 (6)
C6A	0.0139 (7)	0.0155 (8)	0.0140 (7)	0.0024 (6)	0.0065 (6)	0.0009 (6)
C7A	0.0149 (7)	0.0188 (8)	0.0156 (7)	0.0008 (7)	0.0069 (6)	0.0005 (6)
C8A	0.0146 (7)	0.0177 (8)	0.0189 (8)	0.0016 (7)	0.0079 (6)	0.0007 (7)
C9A	0.0123 (7)	0.0191 (8)	0.0164 (8)	0.0019 (6)	0.0049 (6)	−0.0010 (6)
C10A	0.0121 (7)	0.0158 (8)	0.0132 (7)	−0.0003 (6)	0.0049 (6)	−0.0007 (6)
C11A	0.0162 (7)	0.0180 (8)	0.0149 (7)	−0.0017 (7)	0.0060 (6)	0.0007 (6)
C12A	0.0160 (8)	0.0208 (9)	0.0159 (8)	0.0002 (7)	0.0082 (6)	0.0017 (7)
C13A	0.0130 (7)	0.0187 (8)	0.0156 (7)	0.0000 (6)	0.0067 (6)	−0.0015 (6)
C14A	0.0134 (7)	0.0167 (8)	0.0192 (8)	0.0004 (6)	0.0070 (6)	0.0017 (7)
C15A	0.0130 (7)	0.0174 (8)	0.0172 (7)	−0.0004 (6)	0.0074 (6)	0.0028 (6)
C16A	0.0176 (9)	0.0185 (9)	0.0348 (12)	0.0023 (7)	0.0132 (8)	0.0007 (8)
Br1B	0.01554 (8)	0.02289 (10)	0.01906 (9)	−0.00320 (7)	0.01000 (7)	−0.00199 (7)
O1B	0.0201 (7)	0.0166 (7)	0.0340 (9)	−0.0010 (6)	0.0149 (7)	−0.0004 (6)
O2B	0.0127 (6)	0.0244 (7)	0.0220 (7)	0.0007 (5)	0.0090 (5)	−0.0050 (6)
C1B	0.0151 (7)	0.0145 (8)	0.0179 (8)	0.0018 (6)	0.0073 (6)	0.0009 (6)
C2B	0.0174 (8)	0.0152 (8)	0.0161 (7)	0.0002 (6)	0.0079 (6)	0.0006 (6)
C3B	0.0137 (7)	0.0167 (8)	0.0134 (7)	−0.0002 (6)	0.0070 (6)	−0.0006 (6)
C4B	0.0128 (7)	0.0187 (8)	0.0152 (7)	0.0030 (6)	0.0066 (6)	0.0013 (6)
C5B	0.0150 (7)	0.0160 (8)	0.0160 (7)	0.0014 (6)	0.0080 (6)	0.0005 (6)
C6B	0.0131 (7)	0.0151 (7)	0.0138 (7)	0.0011 (6)	0.0065 (6)	−0.0003 (6)
C7B	0.0135 (7)	0.0189 (8)	0.0157 (7)	0.0000 (6)	0.0068 (6)	−0.0016 (7)
C8B	0.0139 (7)	0.0177 (8)	0.0196 (8)	−0.0002 (6)	0.0092 (6)	−0.0018 (7)
C9B	0.0143 (7)	0.0178 (8)	0.0140 (7)	0.0017 (6)	0.0061 (6)	−0.0019 (6)
C10B	0.0125 (7)	0.0160 (8)	0.0137 (7)	−0.0016 (6)	0.0058 (6)	−0.0008 (6)
C11B	0.0135 (7)	0.0195 (8)	0.0160 (7)	−0.0028 (6)	0.0072 (6)	−0.0029 (7)
C12B	0.0120 (7)	0.0197 (8)	0.0171 (8)	−0.0019 (6)	0.0067 (6)	−0.0020 (7)
C13B	0.0120 (7)	0.0182 (8)	0.0143 (7)	0.0011 (6)	0.0063 (6)	0.0009 (6)
C14B	0.0126 (7)	0.0170 (8)	0.0191 (8)	−0.0018 (6)	0.0071 (6)	−0.0021 (7)
C15B	0.0127 (7)	0.0173 (8)	0.0184 (8)	−0.0023 (6)	0.0076 (6)	−0.0029 (6)
C16B	0.0202 (9)	0.0194 (9)	0.0282 (10)	0.0014 (7)	0.0147 (8)	−0.0026 (8)

Geometric parameters (Å, º)

Br1A—C3A	1.896 (2)	Br1B—C3B	1.8946 (19)
O1A—C7A	1.233 (3)	O1B—C7B	1.234 (3)
O2A—C13A	1.364 (2)	O2B—C13B	1.361 (2)
O2A—C16A	1.430 (3)	O2B—C16B	1.429 (3)
C1A—C2A	1.393 (3)	C1B—C2B	1.391 (3)
C1A—C6A	1.398 (3)	C1B—C6B	1.393 (3)
C1A—H1A	0.95	C1B—H1B	0.95
C2A—C3A	1.391 (3)	C2B—C3B	1.390 (3)
C2A—H2A	0.95	C2B—H2B	0.95
C3A—C4A	1.391 (3)	C3B—C4B	1.391 (3)
C4A—C5A	1.391 (3)	C4B—C5B	1.384 (3)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—C6A	1.401 (3)	C5B—C6B	1.405 (3)
C5A—H5A	0.95	C5B—H5B	0.95
C6A—C7A	1.491 (3)	C6B—C7B	1.496 (3)
C7A—C8A	1.479 (3)	C7B—C8B	1.477 (3)
C8A—C9A	1.337 (3)	C8B—C9B	1.339 (3)
C8A—H8A	0.95	C8B—H8B	0.95
C9A—C10A	1.459 (3)	C9B—C10B	1.467 (3)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C15A	1.402 (3)	C10B—C11B	1.399 (3)
C10A—C11A	1.402 (3)	C10B—C15B	1.402 (3)
C11A—C12A	1.383 (3)	C11B—C12B	1.384 (3)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.393 (3)	C12B—C13B	1.393 (3)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—C14A	1.401 (3)	C13B—C14B	1.400 (3)
C14A—C15A	1.387 (3)	C14B—C15B	1.390 (3)
C14A—H14A	0.95	C14B—H14B	0.95
C15A—H15A	0.95	C15B—H15B	0.95
C16A—H16A	0.98	C16B—H16D	0.98
C16A—H16B	0.98	C16B—H16E	0.98
C16A—H16C	0.98	C16B—H16F	0.98
C13A—O2A—C16A	117.96 (17)	C13B—O2B—C16B	118.31 (16)
C2A—C1A—C6A	120.50 (19)	C2B—C1B—C6B	120.54 (18)
C2A—C1A—H1A	119.7	C2B—C1B—H1B	119.7
C6A—C1A—H1A	119.7	C6B—C1B—H1B	119.7
C3A—C2A—C1A	118.97 (19)	C3B—C2B—C1B	118.89 (19)
C3A—C2A—H2A	120.5	C3B—C2B—H2B	120.6
C1A—C2A—H2A	120.5	C1B—C2B—H2B	120.6
C2A—C3A—C4A	121.71 (18)	C2B—C3B—C4B	121.66 (18)
C2A—C3A—Br1A	118.61 (16)	C2B—C3B—Br1B	118.87 (15)
C4A—C3A—Br1A	119.67 (15)	C4B—C3B—Br1B	119.48 (14)
C3A—C4A—C5A	118.73 (18)	C5B—C4B—C3B	118.90 (18)
C3A—C4A—H4A	120.6	C5B—C4B—H4B	120.5
C5A—C4A—H4A	120.6	C3B—C4B—H4B	120.5
C4A—C5A—C6A	120.72 (19)	C4B—C5B—C6B	120.59 (19)
C4A—C5A—H5A	119.6	C4B—C5B—H5B	119.7
C6A—C5A—H5A	119.6	C6B—C5B—H5B	119.7
C1A—C6A—C5A	119.33 (18)	C1B—C6B—C5B	119.38 (18)
C1A—C6A—C7A	122.34 (18)	C1B—C6B—C7B	122.27 (18)
C5A—C6A—C7A	118.32 (18)	C5B—C6B—C7B	118.32 (18)
O1A—C7A—C8A	121.58 (19)	O1B—C7B—C8B	121.73 (19)
O1A—C7A—C6A	119.68 (19)	O1B—C7B—C6B	119.56 (18)
C8A—C7A—C6A	118.74 (18)	C8B—C7B—C6B	118.71 (18)
C9A—C8A—C7A	119.0 (2)	C9B—C8B—C7B	119.56 (19)
C9A—C8A—H8A	120.5	C9B—C8B—H8B	120.2
C7A—C8A—H8A	120.5	C7B—C8B—H8B	120.2
C8A—C9A—C10A	128.3 (2)	C8B—C9B—C10B	127.59 (19)
C8A—C9A—H9A	115.8	C8B—C9B—H9B	116.2
C10A—C9A—H9A	115.8	C10B—C9B—H9B	116.2
C15A—C10A—C11A	118.07 (18)	C11B—C10B—C15B	117.82 (18)
C15A—C10A—C9A	123.34 (18)	C11B—C10B—C9B	118.97 (18)
C11A—C10A—C9A	118.58 (19)	C15B—C10B—C9B	123.14 (17)
C12A—C11A—C10A	121.2 (2)	C12B—C11B—C10B	121.39 (19)
C12A—C11A—H11A	119.4	C12B—C11B—H11B	119.3
C10A—C11A—H11A	119.4	C10B—C11B—H11B	119.3
C11A—C12A—C13A	119.94 (19)	C11B—C12B—C13B	119.78 (18)
C11A—C12A—H12A	120.0	C11B—C12B—H12B	120.1
C13A—C12A—H12A	120.0	C13B—C12B—H12B	120.1
O2A—C13A—C12A	115.28 (18)	O2B—C13B—C12B	115.31 (17)
O2A—C13A—C14A	124.74 (19)	O2B—C13B—C14B	124.41 (19)
C12A—C13A—C14A	119.97 (18)	C12B—C13B—C14B	120.28 (18)
C15A—C14A—C13A	119.45 (19)	C15B—C14B—C13B	118.94 (19)
C15A—C14A—H14A	120.3	C15B—C14B—H14B	120.5
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.5
C14A—C15A—C10A	121.33 (18)	C14B—C15B—C10B	121.74 (18)
C14A—C15A—H15A	119.3	C14B—C15B—H15B	119.1
C10A—C15A—H15A	119.3	C10B—C15B—H15B	119.1
O2A—C16A—H16A	109.5	O2B—C16B—H16D	109.5
O2A—C16A—H16B	109.5	O2B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O2A—C16A—H16C	109.5	O2B—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	2.0 (3)	C6B—C1B—C2B—C3B	−2.4 (3)
C1A—C2A—C3A—C4A	−2.1 (3)	C1B—C2B—C3B—C4B	1.8 (3)
C1A—C2A—C3A—Br1A	177.09 (16)	C1B—C2B—C3B—Br1B	−177.98 (15)
C2A—C3A—C4A—C5A	0.9 (3)	C2B—C3B—C4B—C5B	0.0 (3)
Br1A—C3A—C4A—C5A	−178.28 (15)	Br1B—C3B—C4B—C5B	179.74 (15)
C3A—C4A—C5A—C6A	0.4 (3)	C3B—C4B—C5B—C6B	−1.1 (3)
C2A—C1A—C6A—C5A	−0.8 (3)	C2B—C1B—C6B—C5B	1.3 (3)
C2A—C1A—C6A—C7A	177.79 (19)	C2B—C1B—C6B—C7B	−176.61 (19)
C4A—C5A—C6A—C1A	−0.4 (3)	C4B—C5B—C6B—C1B	0.5 (3)
C4A—C5A—C6A—C7A	−179.07 (18)	C4B—C5B—C6B—C7B	178.49 (18)
C1A—C6A—C7A—O1A	−159.1 (2)	C1B—C6B—C7B—O1B	156.7 (2)
C5A—C6A—C7A—O1A	19.5 (3)	C5B—C6B—C7B—O1B	−21.3 (3)
C1A—C6A—C7A—C8A	20.3 (3)	C1B—C6B—C7B—C8B	−23.8 (3)
C5A—C6A—C7A—C8A	−161.12 (18)	C5B—C6B—C7B—C8B	158.20 (18)
O1A—C7A—C8A—C9A	19.6 (3)	O1B—C7B—C8B—C9B	−17.1 (3)
C6A—C7A—C8A—C9A	−159.85 (19)	C6B—C7B—C8B—C9B	163.48 (19)
C7A—C8A—C9A—C10A	179.60 (19)	C7B—C8B—C9B—C10B	174.44 (19)
C8A—C9A—C10A—C15A	21.4 (3)	C8B—C9B—C10B—C11B	170.6 (2)
C8A—C9A—C10A—C11A	−159.8 (2)	C8B—C9B—C10B—C15B	−12.2 (3)
C15A—C10A—C11A—C12A	−0.8 (3)	C15B—C10B—C11B—C12B	−0.4 (3)
C9A—C10A—C11A—C12A	−179.65 (19)	C9B—C10B—C11B—C12B	176.95 (19)
C10A—C11A—C12A—C13A	2.3 (3)	C10B—C11B—C12B—C13B	−1.5 (3)
C16A—O2A—C13A—C12A	−170.33 (19)	C16B—O2B—C13B—C12B	171.05 (19)
C16A—O2A—C13A—C14A	9.6 (3)	C16B—O2B—C13B—C14B	−8.2 (3)
C11A—C12A—C13A—O2A	177.86 (19)	C11B—C12B—C13B—O2B	−177.58 (19)
C11A—C12A—C13A—C14A	−2.1 (3)	C11B—C12B—C13B—C14B	1.7 (3)
O2A—C13A—C14A—C15A	−179.56 (19)	O2B—C13B—C14B—C15B	179.17 (19)
C12A—C13A—C14A—C15A	0.4 (3)	C12B—C13B—C14B—C15B	0.0 (3)
C13A—C14A—C15A—C10A	1.2 (3)	C13B—C14B—C15B—C10B	−1.9 (3)
C11A—C10A—C15A—C14A	−1.0 (3)	C11B—C10B—C15B—C14B	2.1 (3)
C9A—C10A—C15A—C14A	177.87 (19)	C9B—C10B—C15B—C14B	−175.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9A···O1A	0.95	2.45	2.800 (3)	102
C9B—H9B···O1B	0.95	2.48	2.808 (3)	100