2-(4-Bromo-phen-yl)-2-oxoethyl 4-chloro-benzoate.

The asymmetric unit of the title compound, C(15)H(10)BrClO(3), consists of three crystallographically independent mol-ecules. The dihedral angles between the benzene rings in the three mol-ecules are 68.8 (2), 0.7 (3) and 66.1 (2)°. In the crystal, the three independent mol-ecules are inter-connected by C-H⋯O hydrogen bonds, leading to isolated trimers.

Related literature

For background to phenacyl benzoate derivatives, see: Huang et al. (1996 ▶); Gandhi et al. (1995 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶). For related structures, see: Fun et al. (2011 ▶). For the preparation, see: Kelly & Howard (1932 ▶).

Experimental

Crystal data

C15H10BrClO3

M = 353.59

Monoclinic,

a = 17.1061 (11) Å

b = 5.3062 (4) Å

c = 24.0376 (16) Å

β = 101.502 (1)°

V = 2138.0 (3) Å3

Z = 6

Mo Kα radiation

μ = 3.07 mm−1

T = 297 K

0.41 × 0.19 × 0.15 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.364, T max = 0.657

18463 measured reflections

8890 independent reflections

5931 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.142

S = 1.04

8890 reflections

541 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 3590 Friedel pairs

Flack parameter: 0.065 (10)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022963/rz2606sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022963/rz2606Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022963/rz2606Isup3.cml

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

C15H10BrClO3	F(000) = 1056
Mr = 353.59	Dx = 1.648 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4899 reflections
a = 17.1061 (11) Å	θ = 2.3–26.1°
b = 5.3062 (4) Å	µ = 3.07 mm−1
c = 24.0376 (16) Å	T = 297 K
β = 101.502 (1)°	Block, colourless
V = 2138.0 (3) Å3	0.41 × 0.19 × 0.15 mm
Z = 6

Bruker APEXII DUO CCD area-detector diffractometer	8890 independent reflections
Radiation source: fine-focus sealed tube	5931 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −22→21
Tmin = 0.364, Tmax = 0.657	k = −6→6
18463 measured reflections	l = −31→31

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0741P)2 + 0.4681P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
8890 reflections	Δρmax = 0.67 e Å−3
541 parameters	Δρmin = −0.54 e Å−3
1 restraint	Absolute structure: Flack (1983), 3590 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.065 (10)

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
Br1A	0.67824 (3)	1.30681 (17)	0.56131 (3)	0.0834 (2)
Cl1A	−0.15600 (8)	0.7707 (5)	0.61298 (7)	0.0905 (6)
O1A	0.3290 (2)	0.9241 (10)	0.63191 (17)	0.0841 (16)
O2A	0.1988 (2)	1.1811 (8)	0.58442 (16)	0.0632 (10)
O3A	0.1936 (2)	0.8415 (10)	0.52826 (15)	0.0736 (12)
C1A	0.4376 (3)	1.3623 (11)	0.56106 (19)	0.0501 (12)
H1AA	0.3959	1.4676	0.5447	0.060*
C2A	0.5157 (3)	1.4119 (11)	0.55351 (19)	0.0526 (13)
H2AA	0.5265	1.5531	0.5334	0.063*
C3A	0.5759 (3)	1.2477 (12)	0.57638 (18)	0.0502 (13)
C4A	0.5622 (3)	1.0413 (15)	0.60918 (18)	0.0556 (12)
H4AA	0.6038	0.9348	0.6252	0.067*
C5A	0.4865 (3)	0.9992 (11)	0.61718 (18)	0.0503 (12)
H5AA	0.4771	0.8628	0.6392	0.060*
C6A	0.4229 (3)	1.1541 (10)	0.59333 (17)	0.0462 (12)
C7A	0.3413 (3)	1.0949 (12)	0.60142 (19)	0.0533 (15)
C8A	0.2734 (3)	1.2495 (13)	0.5706 (2)	0.0622 (15)
H8AA	0.2839	1.4259	0.5798	0.075*
H8AB	0.2698	1.2297	0.5300	0.075*
C9A	0.1655 (3)	0.9666 (12)	0.5602 (2)	0.0533 (15)
C10A	0.0870 (3)	0.9183 (11)	0.57661 (18)	0.0471 (12)
C11A	0.0551 (3)	1.0787 (13)	0.61134 (18)	0.0536 (13)
H11A	0.0844	1.2180	0.6271	0.064*
C12A	−0.0192 (3)	1.0367 (17)	0.6231 (2)	0.0652 (14)
H12A	−0.0405	1.1465	0.6464	0.078*
C13A	−0.0615 (3)	0.8289 (14)	0.5998 (2)	0.0604 (15)
C14A	−0.0303 (3)	0.6605 (12)	0.56479 (19)	0.0569 (14)
H14A	−0.0592	0.5200	0.5493	0.068*
C15A	0.0445 (3)	0.7093 (13)	0.55400 (19)	0.0548 (14)
H15A	0.0665	0.5996	0.5312	0.066*
Br1B	0.06535 (3)	0.5564 (2)	0.73157 (2)	0.0802 (2)
Cl1B	0.92955 (6)	−0.0329 (3)	0.77621 (5)	0.0628 (4)
O1B	0.4359 (2)	0.0185 (11)	0.78999 (16)	0.0786 (11)
O2B	0.54903 (19)	0.2829 (8)	0.75497 (14)	0.0627 (10)
O3B	0.5851 (2)	0.5857 (10)	0.70158 (16)	0.0768 (12)
C1B	0.2738 (3)	0.1656 (11)	0.7806 (2)	0.0593 (14)
H1BA	0.2901	0.0219	0.8020	0.071*
C2B	0.1972 (3)	0.2425 (14)	0.7741 (2)	0.0666 (17)
H2BA	0.1620	0.1554	0.7920	0.080*
C3B	0.1714 (3)	0.4476 (12)	0.74136 (18)	0.0525 (14)
C4B	0.2241 (3)	0.5826 (13)	0.71591 (19)	0.0553 (14)
H4BA	0.2066	0.7235	0.6939	0.066*
C5B	0.3026 (3)	0.5066 (13)	0.72344 (19)	0.0552 (14)
H5BA	0.3382	0.5967	0.7065	0.066*
C6B	0.3285 (3)	0.2963 (12)	0.75623 (17)	0.0495 (12)
C7B	0.4133 (3)	0.2139 (12)	0.76452 (19)	0.0579 (14)
C8B	0.4699 (3)	0.3840 (13)	0.74273 (18)	0.0605 (16)
H8BA	0.4527	0.4044	0.7020	0.073*
H8BB	0.4697	0.5487	0.7602	0.073*
C9B	0.6007 (3)	0.4055 (12)	0.7307 (2)	0.0558 (14)
C10B	0.6816 (3)	0.2864 (12)	0.74456 (18)	0.0488 (11)
C11B	0.7416 (3)	0.3983 (13)	0.7210 (2)	0.0677 (16)
H11B	0.7300	0.5398	0.6980	0.081*
C12B	0.8182 (3)	0.2997 (15)	0.7317 (2)	0.0657 (15)
H12B	0.8586	0.3755	0.7168	0.079*
C13B	0.8332 (3)	0.0859 (12)	0.76505 (18)	0.0497 (12)
C14B	0.7754 (3)	−0.0248 (12)	0.78855 (18)	0.0545 (15)
H14B	0.7873	−0.1653	0.8118	0.065*
C15B	0.6984 (3)	0.0746 (13)	0.77740 (18)	0.0525 (13)
H15B	0.6584	−0.0031	0.7923	0.063*
Br1C	0.32100 (3)	−0.72787 (16)	0.94037 (3)	0.0849 (3)
Cl1C	1.15846 (7)	−0.2313 (4)	0.89129 (6)	0.0805 (5)
O1C	0.6700 (2)	−0.3571 (9)	0.86746 (17)	0.0800 (14)
O2C	0.7989 (2)	−0.6225 (9)	0.91351 (17)	0.0693 (12)
O3C	0.8057 (2)	−0.2890 (10)	0.97126 (16)	0.0758 (12)
C1C	0.5592 (3)	−0.7933 (11)	0.93756 (19)	0.0515 (13)
H1CA	0.5997	−0.9063	0.9520	0.062*
C2C	0.4832 (3)	−0.8341 (12)	0.9467 (2)	0.0552 (14)
H2CA	0.4729	−0.9727	0.9678	0.066*
C3C	0.4234 (3)	−0.6727 (13)	0.92500 (19)	0.0533 (13)
C4C	0.4372 (3)	−0.4662 (16)	0.89371 (19)	0.0611 (14)
H4CA	0.3958	−0.3569	0.8788	0.073*
C5C	0.5134 (3)	−0.4232 (13)	0.88469 (18)	0.0549 (13)
H5CA	0.5231	−0.2843	0.8635	0.066*
C6C	0.5757 (3)	−0.5854 (10)	0.90700 (18)	0.0450 (12)
C7C	0.6575 (3)	−0.5282 (11)	0.8977 (2)	0.0519 (14)
C8C	0.7228 (3)	−0.6899 (14)	0.9273 (2)	0.0642 (15)
H8CA	0.7264	−0.6749	0.9679	0.077*
H8CB	0.7108	−0.8643	0.9168	0.077*
C9C	0.8341 (3)	−0.4191 (13)	0.93900 (19)	0.0511 (13)
C10C	0.9124 (3)	−0.3701 (10)	0.92392 (18)	0.0482 (13)
C11C	0.9457 (3)	−0.5376 (11)	0.89043 (19)	0.0517 (13)
H11C	0.9170	−0.6783	0.8748	0.062*
C12C	1.0218 (3)	−0.4933 (14)	0.8805 (2)	0.0573 (14)
H12C	1.0445	−0.6050	0.8585	0.069*
C13C	1.0634 (3)	−0.2850 (12)	0.9034 (2)	0.0514 (13)
C14C	1.0313 (3)	−0.1212 (12)	0.9361 (2)	0.0566 (13)
H14C	1.0605	0.0188	0.9516	0.068*
C15C	0.9556 (3)	−0.1613 (13)	0.9465 (2)	0.0542 (13)
H15C	0.9339	−0.0477	0.9687	0.065*

	U11	U22	U33	U12	U13	U23
Br1A	0.0459 (3)	0.1128 (7)	0.0917 (4)	−0.0160 (4)	0.0140 (3)	0.0005 (4)
Cl1A	0.0560 (7)	0.1171 (17)	0.1044 (11)	−0.0214 (11)	0.0302 (8)	0.0042 (12)
O1A	0.065 (2)	0.102 (4)	0.087 (3)	−0.003 (2)	0.019 (2)	0.047 (3)
O2A	0.0488 (19)	0.057 (3)	0.090 (2)	−0.005 (2)	0.0276 (18)	−0.009 (2)
O3A	0.065 (2)	0.082 (3)	0.082 (2)	0.003 (3)	0.0341 (19)	−0.015 (3)
C1A	0.050 (2)	0.043 (3)	0.057 (3)	0.000 (3)	0.008 (2)	0.003 (3)
C2A	0.058 (3)	0.045 (3)	0.057 (3)	−0.004 (3)	0.017 (2)	0.009 (2)
C3A	0.043 (2)	0.056 (4)	0.048 (2)	−0.009 (3)	0.003 (2)	−0.003 (3)
C4A	0.050 (2)	0.053 (3)	0.060 (3)	0.004 (4)	0.000 (2)	0.004 (3)
C5A	0.053 (3)	0.041 (3)	0.054 (2)	0.003 (3)	0.004 (2)	0.013 (3)
C6A	0.050 (3)	0.044 (3)	0.042 (2)	−0.004 (2)	0.004 (2)	0.004 (2)
C7A	0.052 (3)	0.058 (4)	0.049 (2)	−0.008 (3)	0.010 (2)	0.001 (3)
C8A	0.050 (3)	0.054 (4)	0.087 (3)	0.004 (3)	0.024 (3)	0.012 (3)
C9A	0.048 (3)	0.055 (4)	0.057 (3)	0.008 (3)	0.011 (2)	0.003 (3)
C10A	0.044 (2)	0.049 (3)	0.048 (2)	−0.003 (2)	0.007 (2)	0.002 (2)
C11A	0.053 (3)	0.048 (3)	0.062 (3)	−0.007 (3)	0.018 (2)	−0.009 (3)
C12A	0.062 (3)	0.069 (4)	0.071 (3)	0.000 (4)	0.029 (2)	−0.011 (4)
C13A	0.046 (3)	0.071 (4)	0.065 (3)	0.001 (3)	0.011 (2)	0.015 (3)
C14A	0.052 (3)	0.057 (4)	0.058 (3)	−0.014 (3)	0.001 (2)	0.000 (3)
C15A	0.060 (3)	0.055 (4)	0.050 (3)	0.010 (3)	0.012 (2)	−0.002 (3)
Br1B	0.0535 (3)	0.1015 (6)	0.0861 (4)	0.0141 (4)	0.0153 (3)	−0.0053 (4)
Cl1B	0.0359 (5)	0.0806 (12)	0.0704 (7)	0.0202 (6)	0.0067 (5)	−0.0083 (7)
O1B	0.072 (2)	0.070 (3)	0.091 (2)	0.030 (3)	0.0089 (19)	0.019 (3)
O2B	0.0516 (18)	0.073 (3)	0.0619 (19)	0.024 (2)	0.0083 (15)	0.008 (2)
O3B	0.073 (2)	0.072 (3)	0.085 (2)	0.028 (3)	0.0124 (19)	0.023 (3)
C1B	0.073 (3)	0.045 (3)	0.062 (3)	0.013 (3)	0.018 (3)	0.016 (3)
C2B	0.076 (4)	0.064 (4)	0.064 (3)	−0.008 (3)	0.026 (3)	0.016 (3)
C3B	0.044 (2)	0.068 (4)	0.046 (2)	0.003 (2)	0.0098 (19)	−0.006 (3)
C4B	0.053 (3)	0.049 (4)	0.062 (3)	0.012 (3)	0.009 (2)	0.015 (3)
C5B	0.044 (2)	0.058 (4)	0.062 (3)	0.007 (3)	0.008 (2)	0.015 (3)
C6B	0.055 (3)	0.050 (3)	0.040 (2)	0.012 (3)	0.0021 (19)	−0.002 (2)
C7B	0.068 (3)	0.051 (4)	0.048 (3)	0.029 (3)	−0.005 (2)	−0.001 (2)
C8B	0.057 (3)	0.079 (4)	0.045 (2)	0.030 (3)	0.007 (2)	0.006 (2)
C9B	0.062 (3)	0.061 (4)	0.046 (2)	0.014 (3)	0.015 (2)	0.000 (3)
C10B	0.055 (2)	0.047 (3)	0.044 (2)	0.011 (3)	0.009 (2)	0.007 (2)
C11B	0.077 (3)	0.065 (4)	0.065 (3)	0.014 (3)	0.021 (3)	0.016 (3)
C12B	0.057 (3)	0.074 (4)	0.073 (3)	0.005 (3)	0.030 (2)	0.006 (3)
C13B	0.050 (2)	0.046 (3)	0.053 (2)	0.012 (3)	0.010 (2)	0.001 (3)
C14B	0.050 (3)	0.059 (4)	0.054 (2)	0.012 (3)	0.008 (2)	0.014 (3)
C15B	0.053 (3)	0.054 (4)	0.053 (2)	0.003 (3)	0.017 (2)	0.005 (3)
Br1C	0.0474 (3)	0.1115 (7)	0.0968 (4)	−0.0085 (4)	0.0169 (3)	−0.0075 (4)
Cl1C	0.0425 (6)	0.1100 (15)	0.0921 (9)	−0.0088 (9)	0.0205 (6)	0.0061 (10)
O1C	0.066 (2)	0.087 (4)	0.090 (3)	−0.011 (2)	0.022 (2)	0.036 (3)
O2C	0.055 (2)	0.064 (3)	0.096 (3)	−0.001 (2)	0.034 (2)	−0.004 (3)
O3C	0.065 (2)	0.086 (3)	0.082 (2)	−0.006 (2)	0.0283 (19)	−0.024 (3)
C1C	0.054 (3)	0.044 (3)	0.059 (3)	0.006 (3)	0.017 (2)	0.010 (3)
C2C	0.052 (3)	0.053 (4)	0.060 (3)	−0.007 (3)	0.012 (2)	0.007 (3)
C3C	0.047 (2)	0.057 (4)	0.057 (3)	−0.005 (3)	0.012 (2)	−0.010 (3)
C4C	0.052 (3)	0.064 (4)	0.062 (3)	0.009 (4)	−0.002 (2)	−0.001 (4)
C5C	0.064 (3)	0.048 (4)	0.051 (2)	−0.008 (3)	0.006 (2)	−0.002 (3)
C6C	0.052 (3)	0.038 (3)	0.046 (2)	−0.002 (2)	0.013 (2)	−0.005 (2)
C7C	0.057 (3)	0.046 (4)	0.056 (3)	−0.008 (3)	0.018 (2)	0.004 (3)
C8C	0.052 (3)	0.056 (4)	0.089 (4)	−0.012 (3)	0.024 (3)	−0.003 (3)
C9C	0.051 (3)	0.050 (4)	0.052 (2)	0.002 (3)	0.011 (2)	0.001 (3)
C10C	0.049 (3)	0.048 (4)	0.047 (2)	0.012 (2)	0.007 (2)	0.005 (2)
C11C	0.052 (3)	0.048 (4)	0.057 (2)	0.004 (3)	0.016 (2)	0.004 (2)
C12C	0.055 (3)	0.059 (4)	0.063 (3)	0.006 (3)	0.022 (2)	0.005 (3)
C13C	0.041 (2)	0.058 (4)	0.056 (3)	0.002 (3)	0.012 (2)	0.009 (3)
C14C	0.057 (3)	0.049 (3)	0.061 (3)	−0.004 (3)	0.004 (2)	0.001 (3)
C15C	0.057 (3)	0.049 (4)	0.057 (3)	0.000 (3)	0.012 (2)	−0.001 (3)

Br1A—C3A	1.884 (4)	C6B—C7B	1.488 (7)
Cl1A—C13A	1.735 (5)	C7B—C8B	1.493 (9)
O1A—C7A	1.210 (7)	C8B—H8BA	0.9700
O2A—C9A	1.351 (7)	C8B—H8BB	0.9700
O2A—C8A	1.428 (6)	C9B—C10B	1.497 (7)
O3A—C9A	1.187 (6)	C10B—C15B	1.370 (8)
C1A—C6A	1.401 (7)	C10B—C11B	1.401 (7)
C1A—C2A	1.409 (6)	C11B—C12B	1.386 (8)
C1A—H1AA	0.9300	C11B—H11B	0.9300
C2A—C3A	1.376 (7)	C12B—C13B	1.384 (9)
C2A—H2AA	0.9300	C12B—H12B	0.9300
C3A—C4A	1.396 (9)	C13B—C14B	1.365 (6)
C4A—C5A	1.366 (6)	C14B—C15B	1.395 (6)
C4A—H4AA	0.9300	C14B—H14B	0.9300
C5A—C6A	1.392 (7)	C15B—H15B	0.9300
C5A—H5AA	0.9300	Br1C—C3C	1.884 (4)
C6A—C7A	1.481 (6)	Cl1C—C13C	1.732 (5)
C7A—C8A	1.493 (7)	O1C—C7C	1.208 (6)
C8A—H8AA	0.9700	O2C—C9C	1.325 (8)
C8A—H8AB	0.9700	O2C—C8C	1.451 (5)
C9A—C10A	1.495 (6)	O3C—C9C	1.210 (6)
C10A—C15A	1.377 (8)	C1C—C2C	1.378 (6)
C10A—C11A	1.379 (7)	C1C—C6C	1.386 (7)
C11A—C12A	1.375 (6)	C1C—H1CA	0.9300
C11A—H11A	0.9300	C2C—C3C	1.356 (8)
C12A—C13A	1.375 (10)	C2C—H2CA	0.9300
C12A—H12A	0.9300	C3C—C4C	1.376 (10)
C13A—C14A	1.405 (8)	C4C—C5C	1.382 (6)
C14A—C15A	1.379 (7)	C4C—H4CA	0.9300
C14A—H14A	0.9300	C5C—C6C	1.392 (7)
C15A—H15A	0.9300	C5C—H5CA	0.9300
Br1B—C3B	1.873 (5)	C6C—C7C	1.491 (6)
Cl1B—C13B	1.735 (5)	C7C—C8C	1.474 (8)
O1B—C7B	1.227 (8)	C8C—H8CA	0.9700
O2B—C9B	1.324 (7)	C8C—H8CB	0.9700
O2B—C8B	1.431 (5)	C9C—C10C	1.477 (6)
O3B—C9B	1.183 (7)	C10C—C15C	1.382 (8)
C1B—C2B	1.351 (7)	C10C—C11C	1.395 (7)
C1B—C6B	1.387 (7)	C11C—C12C	1.390 (6)
C1B—H1BA	0.9300	C11C—H11C	0.9300
C2B—C3B	1.364 (9)	C12C—C13C	1.368 (9)
C2B—H2BA	0.9300	C12C—H12C	0.9300
C3B—C4B	1.385 (7)	C13C—C14C	1.358 (7)
C4B—C5B	1.379 (6)	C14C—C15C	1.383 (7)
C4B—H4BA	0.9300	C14C—H14C	0.9300
C5B—C6B	1.387 (8)	C15C—H15C	0.9300
C5B—H5BA	0.9300
C9A—O2A—C8A	115.7 (5)	O2B—C8B—H8BB	109.5
C6A—C1A—C2A	119.9 (5)	C7B—C8B—H8BB	109.5
C6A—C1A—H1AA	120.1	H8BA—C8B—H8BB	108.1
C2A—C1A—H1AA	120.1	O3B—C9B—O2B	124.5 (5)
C3A—C2A—C1A	118.9 (5)	O3B—C9B—C10B	124.2 (5)
C3A—C2A—H2AA	120.6	O2B—C9B—C10B	111.2 (5)
C1A—C2A—H2AA	120.6	C15B—C10B—C11B	119.6 (5)
C2A—C3A—C4A	121.8 (4)	C15B—C10B—C9B	123.6 (5)
C2A—C3A—Br1A	117.9 (4)	C11B—C10B—C9B	116.8 (5)
C4A—C3A—Br1A	120.4 (4)	C12B—C11B—C10B	120.5 (6)
C5A—C4A—C3A	118.6 (5)	C12B—C11B—H11B	119.8
C5A—C4A—H4AA	120.7	C10B—C11B—H11B	119.8
C3A—C4A—H4AA	120.7	C13B—C12B—C11B	118.4 (5)
C4A—C5A—C6A	122.0 (5)	C13B—C12B—H12B	120.8
C4A—C5A—H5AA	119.0	C11B—C12B—H12B	120.8
C6A—C5A—H5AA	119.0	C14B—C13B—C12B	121.8 (5)
C5A—C6A—C1A	118.8 (4)	C14B—C13B—Cl1B	121.6 (4)
C5A—C6A—C7A	120.0 (5)	C12B—C13B—Cl1B	116.6 (4)
C1A—C6A—C7A	121.2 (5)	C13B—C14B—C15B	119.5 (5)
O1A—C7A—C6A	121.4 (5)	C13B—C14B—H14B	120.3
O1A—C7A—C8A	120.0 (4)	C15B—C14B—H14B	120.3
C6A—C7A—C8A	118.6 (5)	C10B—C15B—C14B	120.2 (5)
O2A—C8A—C7A	112.8 (5)	C10B—C15B—H15B	119.9
O2A—C8A—H8AA	109.0	C14B—C15B—H15B	119.9
C7A—C8A—H8AA	109.0	C9C—O2C—C8C	116.2 (4)
O2A—C8A—H8AB	109.0	C2C—C1C—C6C	120.6 (5)
C7A—C8A—H8AB	109.0	C2C—C1C—H1CA	119.7
H8AA—C8A—H8AB	107.8	C6C—C1C—H1CA	119.7
O3A—C9A—O2A	124.0 (5)	C3C—C2C—C1C	120.2 (5)
O3A—C9A—C10A	125.1 (5)	C3C—C2C—H2CA	119.9
O2A—C9A—C10A	110.8 (5)	C1C—C2C—H2CA	119.9
C15A—C10A—C11A	119.6 (4)	C2C—C3C—C4C	121.0 (4)
C15A—C10A—C9A	117.7 (5)	C2C—C3C—Br1C	119.1 (4)
C11A—C10A—C9A	122.6 (5)	C4C—C3C—Br1C	119.9 (4)
C12A—C11A—C10A	121.2 (6)	C3C—C4C—C5C	119.1 (6)
C12A—C11A—H11A	119.4	C3C—C4C—H4CA	120.4
C10A—C11A—H11A	119.4	C5C—C4C—H4CA	120.4
C11A—C12A—C13A	118.7 (6)	C4C—C5C—C6C	120.8 (6)
C11A—C12A—H12A	120.7	C4C—C5C—H5CA	119.6
C13A—C12A—H12A	120.7	C6C—C5C—H5CA	119.6
C12A—C13A—C14A	121.4 (4)	C1C—C6C—C5C	118.4 (4)
C12A—C13A—Cl1A	120.1 (5)	C1C—C6C—C7C	122.6 (5)
C14A—C13A—Cl1A	118.4 (5)	C5C—C6C—C7C	119.0 (5)
C15A—C14A—C13A	118.1 (5)	O1C—C7C—C8C	121.3 (5)
C15A—C14A—H14A	120.9	O1C—C7C—C6C	121.8 (5)
C13A—C14A—H14A	120.9	C8C—C7C—C6C	116.9 (4)
C10A—C15A—C14A	120.9 (5)	O2C—C8C—C7C	112.0 (5)
C10A—C15A—H15A	119.6	O2C—C8C—H8CA	109.2
C14A—C15A—H15A	119.6	C7C—C8C—H8CA	109.2
C9B—O2B—C8B	114.3 (5)	O2C—C8C—H8CB	109.2
C2B—C1B—C6B	121.4 (5)	C7C—C8C—H8CB	109.2
C2B—C1B—H1BA	119.3	H8CA—C8C—H8CB	107.9
C6B—C1B—H1BA	119.3	O3C—C9C—O2C	123.9 (5)
C1B—C2B—C3B	120.2 (5)	O3C—C9C—C10C	123.8 (6)
C1B—C2B—H2BA	119.9	O2C—C9C—C10C	112.3 (5)
C3B—C2B—H2BA	119.9	C15C—C10C—C11C	119.3 (4)
C2B—C3B—C4B	120.2 (5)	C15C—C10C—C9C	119.0 (5)
C2B—C3B—Br1B	120.8 (4)	C11C—C10C—C9C	121.6 (5)
C4B—C3B—Br1B	119.0 (4)	C12C—C11C—C10C	119.7 (5)
C5B—C4B—C3B	119.5 (6)	C12C—C11C—H11C	120.2
C5B—C4B—H4BA	120.2	C10C—C11C—H11C	120.2
C3B—C4B—H4BA	120.2	C13C—C12C—C11C	119.8 (5)
C4B—C5B—C6B	120.2 (5)	C13C—C12C—H12C	120.1
C4B—C5B—H5BA	119.9	C11C—C12C—H12C	120.1
C6B—C5B—H5BA	119.9	C14C—C13C—C12C	120.8 (5)
C1B—C6B—C5B	118.4 (4)	C14C—C13C—Cl1C	119.5 (5)
C1B—C6B—C7B	121.2 (5)	C12C—C13C—Cl1C	119.7 (4)
C5B—C6B—C7B	120.4 (5)	C13C—C14C—C15C	120.4 (5)
O1B—C7B—C6B	121.1 (6)	C13C—C14C—H14C	119.8
O1B—C7B—C8B	121.6 (5)	C15C—C14C—H14C	119.8
C6B—C7B—C8B	117.2 (5)	C10C—C15C—C14C	120.0 (5)
O2B—C8B—C7B	110.8 (5)	C10C—C15C—H15C	120.0
O2B—C8B—H8BA	109.5	C14C—C15C—H15C	120.0
C7B—C8B—H8BA	109.5
C6A—C1A—C2A—C3A	2.5 (7)	C8B—O2B—C9B—O3B	0.8 (8)
C1A—C2A—C3A—C4A	−3.3 (8)	C8B—O2B—C9B—C10B	−179.0 (4)
C1A—C2A—C3A—Br1A	175.9 (4)	O3B—C9B—C10B—C15B	−178.7 (6)
C2A—C3A—C4A—C5A	1.8 (8)	O2B—C9B—C10B—C15B	1.2 (7)
Br1A—C3A—C4A—C5A	−177.3 (4)	O3B—C9B—C10B—C11B	−0.2 (8)
C3A—C4A—C5A—C6A	0.5 (8)	O2B—C9B—C10B—C11B	179.6 (5)
C4A—C5A—C6A—C1A	−1.3 (8)	C15B—C10B—C11B—C12B	−1.5 (9)
C4A—C5A—C6A—C7A	177.7 (5)	C9B—C10B—C11B—C12B	−180.0 (5)
C2A—C1A—C6A—C5A	−0.2 (7)	C10B—C11B—C12B—C13B	1.4 (9)
C2A—C1A—C6A—C7A	−179.2 (5)	C11B—C12B—C13B—C14B	−1.7 (9)
C5A—C6A—C7A—O1A	5.4 (8)	C11B—C12B—C13B—Cl1B	179.0 (5)
C1A—C6A—C7A—O1A	−175.7 (5)	C12B—C13B—C14B—C15B	2.0 (8)
C5A—C6A—C7A—C8A	−174.0 (5)	Cl1B—C13B—C14B—C15B	−178.7 (4)
C1A—C6A—C7A—C8A	4.9 (7)	C11B—C10B—C15B—C14B	1.8 (8)
C9A—O2A—C8A—C7A	−76.3 (6)	C9B—C10B—C15B—C14B	−179.8 (5)
O1A—C7A—C8A—O2A	3.6 (8)	C13B—C14B—C15B—C10B	−2.0 (8)
C6A—C7A—C8A—O2A	−177.0 (5)	C6C—C1C—C2C—C3C	1.0 (8)
C8A—O2A—C9A—O3A	−1.7 (7)	C1C—C2C—C3C—C4C	−0.1 (8)
C8A—O2A—C9A—C10A	−178.6 (4)	C1C—C2C—C3C—Br1C	−178.0 (4)
O3A—C9A—C10A—C15A	1.5 (8)	C2C—C3C—C4C—C5C	−0.3 (8)
O2A—C9A—C10A—C15A	178.3 (5)	Br1C—C3C—C4C—C5C	177.5 (4)
O3A—C9A—C10A—C11A	−176.0 (5)	C3C—C4C—C5C—C6C	−0.2 (8)
O2A—C9A—C10A—C11A	0.8 (7)	C2C—C1C—C6C—C5C	−1.6 (7)
C15A—C10A—C11A—C12A	−1.2 (8)	C2C—C1C—C6C—C7C	177.8 (5)
C9A—C10A—C11A—C12A	176.3 (5)	C4C—C5C—C6C—C1C	1.2 (7)
C10A—C11A—C12A—C13A	0.5 (9)	C4C—C5C—C6C—C7C	−178.3 (5)
C11A—C12A—C13A—C14A	0.2 (9)	C1C—C6C—C7C—O1C	174.4 (5)
C11A—C12A—C13A—Cl1A	−179.3 (5)	C5C—C6C—C7C—O1C	−6.2 (7)
C12A—C13A—C14A—C15A	−0.2 (8)	C1C—C6C—C7C—C8C	−5.8 (7)
Cl1A—C13A—C14A—C15A	179.3 (4)	C5C—C6C—C7C—C8C	173.6 (5)
C11A—C10A—C15A—C14A	1.2 (8)	C9C—O2C—C8C—C7C	77.1 (6)
C9A—C10A—C15A—C14A	−176.4 (5)	O1C—C7C—C8C—O2C	−2.3 (8)
C13A—C14A—C15A—C10A	−0.5 (8)	C6C—C7C—C8C—O2C	178.0 (4)
C6B—C1B—C2B—C3B	2.3 (9)	C8C—O2C—C9C—O3C	−1.4 (8)
C1B—C2B—C3B—C4B	−1.9 (9)	C8C—O2C—C9C—C10C	178.1 (4)
C1B—C2B—C3B—Br1B	179.8 (5)	O3C—C9C—C10C—C15C	−1.6 (8)
C2B—C3B—C4B—C5B	0.7 (8)	O2C—C9C—C10C—C15C	178.9 (5)
Br1B—C3B—C4B—C5B	179.1 (4)	O3C—C9C—C10C—C11C	174.3 (5)
C3B—C4B—C5B—C6B	0.1 (8)	O2C—C9C—C10C—C11C	−5.2 (7)
C2B—C1B—C6B—C5B	−1.5 (8)	C15C—C10C—C11C—C12C	0.4 (7)
C2B—C1B—C6B—C7B	178.7 (5)	C9C—C10C—C11C—C12C	−175.5 (5)
C4B—C5B—C6B—C1B	0.3 (8)	C10C—C11C—C12C—C13C	−0.5 (8)
C4B—C5B—C6B—C7B	−179.9 (5)	C11C—C12C—C13C—C14C	0.5 (8)
C1B—C6B—C7B—O1B	4.9 (8)	C11C—C12C—C13C—Cl1C	179.6 (4)
C5B—C6B—C7B—O1B	−174.8 (5)	C12C—C13C—C14C—C15C	−0.6 (8)
C1B—C6B—C7B—C8B	−172.6 (5)	Cl1C—C13C—C14C—C15C	−179.7 (4)
C5B—C6B—C7B—C8B	7.7 (7)	C11C—C10C—C15C—C14C	−0.4 (7)
C9B—O2B—C8B—C7B	171.7 (4)	C9C—C10C—C15C—C14C	175.6 (5)
O1B—C7B—C8B—O2B	1.1 (7)	C13C—C14C—C15C—C10C	0.5 (8)
C6B—C7B—C8B—O2B	178.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5A—H5AA···O3B	0.93	2.59	3.227 (7)	126
C5B—H5BA···O1A	0.93	2.48	3.217 (7)	136
C15B—H15B···O1C	0.93	2.59	3.254 (7)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5A—H5AA⋯O3B	0.93	2.59	3.227 (7)	126
C5B—H5BA⋯O1A	0.93	2.48	3.217 (7)	136
C15B—H15B⋯O1C	0.93	2.59	3.254 (7)	129