1-(5-Bromo-2-chloro­phen­yl)-2,2-di­chloro-1-(4-eth­oxy­phen­yl)cyclo­propane

Han, S.; Shi, Y.; Yuli, W.; Zhao, G.; Xu, W.

doi:10.1107/S1600536813003735

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o405

doi:10.1107/S1600536813003735

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1-(5-Bromo-2-chlorophenyl)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane

Shuwen Han,^a,^b Yongheng Shi,^a,^b Wang Yuli,^b Guilong Zhao ^b and Weiren Xu ^a,^b ^*

^aGraduate School, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: weiren.xu@yahoo.com

(Received 31 January 2013; accepted 6 February 2013; online 20 February 2013)

The asymmetric unit of the title compound, C₁₇H₁₄BrCl₃O, contains two independent molecules with different dihedral angles between the benzene rings [79.2 (1) and 72.7 (1)°]. In the crystal, weak C—H⋯π interactions link molecules related by translation along the b axis into two crystallographically independent chains.

Related literature

For background to sodium-glucose cotransporter 2 (SGLT2) inhibitors, see: Washburn (2009 ); Meng et al. (2008 ). For the crystal structures of related cyclopropane derivatives, see: DeLacy & Kennard (1972 ); Lauher & Ibers (1975 ).

Experimental

Crystal data

C₁₇H₁₄BrCl₃O
M_r = 420.54
Monoclinic, C 2/c
a = 27.447 (13) Å
b = 8.886 (4) Å
c = 28.861 (14) Å
β = 98.348 (8)°
V = 6965 (6) Å³
Z = 16
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009 ) T_min = 0.603, T_max = 0.694
26327 measured reflections
6143 independent reflections
4903 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.180
S = 1.09
6143 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 1.54 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring and Cg2 is the centroid of the C27–C32 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ⁱ	0.95	2.66	3.665 (3)	161
C20—H20⋯Cg2ⁱⁱ	0.95	2.60	3.480 (9)	155
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813003735/cv5386sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003735/cv5386Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003735/cv5386Isup3.cml

checkCIF report

Comment top

Sodium-glucose cotransporter 2 (SGLT2) inhibitors are a new class of anti-diabetic drugs with novel mechanism of action. The most advanced drug, dapagliflozin, has recently been approved in EU (Meng et al., 2008; Washburn, 2009). During our search for new SGLT2 inhibitors, we prepared the title compound as a key intermediate for the synthesis of a new class of cyclopropane-bearing SGLT2 inhibitors.

The asymmetric unit of the title compound, C₁₇H₁₄BrCl₃O, contains two independent molecules with different dihedral angles between the benzene rings [79.2 (1) and 72.7 (1)°]. Bond lengths are normal and in a good agreement with those reported previously for related structures (DeLacy & Kennard, 1972; Lauher & Ibers 1975). In the crystal, weak C—H···π interactions (Table 1) link the molecules related by translation along the axis b into two crystallographically independent chains.

Related literature top

For background to sodium-glucose cotransporter 2 (SGLT2) inhibitors, see: Washburn (2009); Meng et al. (2008). For the crystal structures of related cyclopropane derivatives, see: DeLacy & Kennard (1972); Lauher & Ibers (1975).

Experimental top

3.38 g (10 mmol) of 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethene was dissolved in 15 ml of chloroform and stirred at room temperature, followed by addition of 3 ml of 50% aqueous NaOH and 0.5 g of benzyltriethylammonium bromide. The reaction mixture was stirred vigorously at room temperature overnight until all the starting ethene was consumed as indicated by TLC. The reaction mixture was poured into 200 ml of water and extracted with three 50-ml portions of dichloromethane. The combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated on a rotary evaporator to afford the crude product as a colorless oil, which was purified by column chromatography to yield the pure product as colorless crystals. Single crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in petroleum ether.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2009); cell refinement: CrystalClear (Rigaku/MSC, 2009); data reduction: CrystalClear (Rigaku/MSC, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atomic numbering and 40% probability displacement ellipsoids.

1-(5-Bromo-2-chlorophenyl)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane top

Crystal data top

C₁₇H₁₄BrCl₃O	F(000) = 3360
M_r = 420.54	D_x = 1.604 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11664 reflections
a = 27.447 (13) Å	θ = 1.5–28.0°
b = 8.886 (4) Å	µ = 2.82 mm⁻¹
c = 28.861 (14) Å	T = 113 K
β = 98.348 (8)°	Prism, colorless
V = 6965 (6) Å³	0.20 × 0.18 × 0.14 mm
Z = 16

Data collection top

Rigaku Saturn724 CCD diffractometer	6143 independent reflections
Radiation source: rotating anode	4903 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.104
Detector resolution: 14.22 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω and ϕ scans	h = −32→32
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	k = −10→10
T_min = 0.603, T_max = 0.694	l = −34→33
26327 measured reflections

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0747P)²] where P = (F_o² + 2F_c²)/3
6143 reflections	(Δ/σ)_max = 0.003
399 parameters	Δρ_max = 1.54 e Å⁻³
0 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

C₁₇H₁₄BrCl₃O	V = 6965 (6) Å³
M_r = 420.54	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 27.447 (13) Å	µ = 2.82 mm⁻¹
b = 8.886 (4) Å	T = 113 K
c = 28.861 (14) Å	0.20 × 0.18 × 0.14 mm
β = 98.348 (8)°

Data collection top

Rigaku Saturn724 CCD diffractometer	6143 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)	4903 reflections with I > 2σ(I)
T_min = 0.603, T_max = 0.694	R_int = 0.104
26327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.09	Δρ_max = 1.54 e Å⁻³
6143 reflections	Δρ_min = −0.89 e Å⁻³
399 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.67589 (2)	−0.00608 (7)	0.06050 (2)	0.0372 (2)
Br2	0.43550 (2)	0.53077 (7)	0.20897 (2)	0.0428 (2)
Cl1	0.83567 (5)	0.28486 (18)	0.22003 (5)	0.0403 (4)
Cl2	0.65376 (5)	0.41196 (18)	0.19345 (5)	0.0439 (4)
Cl3	0.67918 (6)	0.70547 (18)	0.15844 (6)	0.0478 (4)
Cl4	0.58075 (5)	0.28004 (17)	0.07179 (5)	0.0386 (4)
Cl5	0.58547 (5)	0.14483 (17)	0.24050 (5)	0.0392 (4)
Cl6	0.55111 (5)	−0.15899 (17)	0.21433 (5)	0.0427 (4)
O1	0.85763 (13)	0.7592 (4)	0.03892 (12)	0.0354 (9)
O2	0.38664 (14)	−0.2563 (5)	0.03844 (13)	0.0373 (10)
C1	0.7900 (2)	0.2085 (7)	0.17851 (18)	0.0329 (13)
C2	0.7932 (2)	0.0558 (7)	0.1666 (2)	0.0361 (14)
H2	0.8188	−0.0044	0.1828	0.043*
C3	0.7602 (2)	−0.0070 (6)	0.1322 (2)	0.0356 (14)
H3	0.7634	−0.1093	0.1236	0.043*
C4	0.7210 (2)	0.0825 (6)	0.10951 (18)	0.0321 (13)
C5	0.71635 (19)	0.2331 (6)	0.12209 (19)	0.0308 (12)
H5	0.6896	0.2911	0.1070	0.037*
C6	0.7505 (2)	0.2992 (6)	0.15645 (19)	0.0321 (13)
C7	0.74841 (19)	0.4669 (6)	0.1662 (2)	0.0322 (13)
C8	0.7021 (2)	0.5333 (6)	0.1829 (2)	0.0369 (14)
C9	0.7478 (2)	0.5258 (7)	0.2166 (2)	0.0377 (14)
H9A	0.7494	0.4505	0.2421	0.045*
H9B	0.7651	0.6215	0.2256	0.045*
C10	0.77570 (19)	0.5583 (6)	0.13452 (19)	0.0295 (12)
C11	0.7582 (2)	0.5712 (6)	0.08606 (19)	0.0321 (13)
H11	0.7268	0.5310	0.0742	0.038*
C12	0.7856 (2)	0.6408 (6)	0.05556 (19)	0.0328 (13)
H12	0.7727	0.6478	0.0233	0.039*
C13	0.83215 (19)	0.7009 (6)	0.07179 (18)	0.0277 (12)
C14	0.8501 (2)	0.6955 (6)	0.12017 (19)	0.0330 (13)
H14	0.8807	0.7411	0.1321	0.040*
C15	0.82230 (19)	0.6219 (6)	0.15032 (19)	0.0315 (13)
H15	0.8353	0.6145	0.1826	0.038*
C16	0.9085 (2)	0.8066 (7)	0.0533 (2)	0.0426 (15)
H16A	0.9278	0.7234	0.0697	0.051*
H16B	0.9096	0.8936	0.0748	0.051*
C17	0.9298 (3)	0.8496 (8)	0.0099 (2)	0.0550 (18)
H17A	0.9298	0.7617	−0.0106	0.082*
H17B	0.9637	0.8854	0.0188	0.082*
H17C	0.9099	0.9298	−0.0067	0.082*
C18	0.54406 (19)	0.3437 (6)	0.11248 (17)	0.0292 (12)
C19	0.5307 (2)	0.4958 (7)	0.1094 (2)	0.0367 (14)
H19	0.5434	0.5598	0.0876	0.044*
C20	0.4985 (2)	0.5532 (7)	0.1387 (2)	0.0376 (14)
H20	0.4886	0.6558	0.1368	0.045*
C21	0.4812 (2)	0.4555 (6)	0.1706 (2)	0.0367 (14)
C22	0.49516 (19)	0.3061 (6)	0.17397 (18)	0.0310 (13)
H22	0.4828	0.2432	0.1962	0.037*
C23	0.52744 (18)	0.2449 (6)	0.14489 (17)	0.0265 (12)
C24	0.53880 (19)	0.0807 (6)	0.14758 (18)	0.0293 (12)
C25	0.5670 (2)	0.0172 (6)	0.1931 (2)	0.0338 (13)
C26	0.5933 (2)	0.0272 (7)	0.1520 (2)	0.0357 (14)
H26A	0.6000	−0.0677	0.1361	0.043*
H26B	0.6191	0.1052	0.1524	0.043*
C27	0.4984 (2)	−0.0153 (6)	0.12023 (18)	0.0263 (12)
C28	0.50266 (19)	−0.0656 (6)	0.07508 (18)	0.0300 (12)
H28	0.5320	−0.0454	0.0623	0.036*
C29	0.4652 (2)	−0.1437 (6)	0.04900 (19)	0.0332 (13)
H29	0.4687	−0.1757	0.0182	0.040*
C30	0.42187 (19)	−0.1767 (6)	0.06726 (17)	0.0283 (12)
C31	0.4166 (2)	−0.1279 (6)	0.11244 (18)	0.0297 (12)
H31	0.3874	−0.1492	0.1252	0.036*
C32	0.45541 (19)	−0.0464 (6)	0.13867 (19)	0.0298 (12)
H32	0.4521	−0.0125	0.1693	0.036*
C33	0.3404 (2)	−0.2861 (7)	0.05542 (19)	0.0340 (13)
H33A	0.3243	−0.1905	0.0621	0.041*
H33B	0.3461	−0.3464	0.0845	0.041*
C34	0.3086 (2)	−0.3721 (7)	0.0173 (2)	0.0386 (14)
H34A	0.3027	−0.3104	−0.0111	0.058*
H34B	0.2770	−0.3965	0.0276	0.058*
H34C	0.3253	−0.4654	0.0106	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0356 (4)	0.0322 (4)	0.0441 (4)	−0.0030 (3)	0.0068 (3)	−0.0046 (3)
Br2	0.0407 (4)	0.0353 (4)	0.0537 (4)	0.0065 (3)	0.0111 (3)	−0.0098 (3)
Cl1	0.0385 (8)	0.0353 (9)	0.0449 (9)	0.0014 (6)	−0.0016 (6)	−0.0038 (6)
Cl2	0.0396 (8)	0.0374 (9)	0.0579 (10)	−0.0057 (7)	0.0182 (7)	−0.0038 (7)
Cl3	0.0488 (9)	0.0329 (9)	0.0652 (10)	0.0102 (7)	0.0195 (7)	0.0036 (7)
Cl4	0.0384 (8)	0.0356 (9)	0.0433 (8)	0.0013 (6)	0.0107 (6)	−0.0006 (6)
Cl5	0.0407 (8)	0.0373 (9)	0.0379 (8)	−0.0026 (6)	−0.0002 (6)	0.0011 (6)
Cl6	0.0409 (8)	0.0288 (8)	0.0557 (9)	−0.0014 (6)	−0.0019 (7)	0.0141 (7)
O1	0.035 (2)	0.034 (2)	0.036 (2)	−0.0050 (18)	0.0020 (17)	0.0074 (17)
O2	0.035 (2)	0.041 (3)	0.037 (2)	−0.0066 (18)	0.0090 (17)	−0.0073 (18)
C1	0.031 (3)	0.035 (4)	0.031 (3)	−0.005 (3)	0.001 (2)	0.003 (2)
C2	0.030 (3)	0.028 (3)	0.049 (4)	0.006 (3)	0.005 (3)	0.002 (3)
C3	0.037 (3)	0.026 (3)	0.048 (4)	0.007 (3)	0.017 (3)	0.003 (3)
C4	0.034 (3)	0.025 (3)	0.039 (3)	−0.002 (2)	0.010 (2)	0.000 (2)
C5	0.027 (3)	0.025 (3)	0.042 (3)	0.000 (2)	0.011 (2)	0.003 (2)
C6	0.035 (3)	0.027 (3)	0.037 (3)	0.001 (2)	0.013 (2)	0.004 (2)
C7	0.026 (3)	0.024 (3)	0.048 (4)	−0.003 (2)	0.012 (2)	−0.002 (2)
C8	0.042 (3)	0.020 (3)	0.052 (4)	−0.004 (3)	0.017 (3)	−0.005 (3)
C9	0.039 (3)	0.031 (4)	0.044 (4)	−0.006 (3)	0.012 (3)	−0.005 (3)
C10	0.026 (3)	0.024 (3)	0.039 (3)	0.001 (2)	0.008 (2)	−0.005 (2)
C11	0.031 (3)	0.026 (3)	0.038 (3)	0.001 (2)	0.000 (2)	−0.003 (2)
C12	0.036 (3)	0.027 (3)	0.034 (3)	0.002 (2)	0.001 (2)	−0.003 (2)
C13	0.033 (3)	0.020 (3)	0.029 (3)	0.004 (2)	0.005 (2)	−0.002 (2)
C14	0.034 (3)	0.025 (3)	0.040 (3)	0.001 (3)	0.004 (2)	−0.001 (2)
C15	0.030 (3)	0.030 (3)	0.034 (3)	0.008 (2)	0.003 (2)	0.002 (2)
C16	0.032 (3)	0.045 (4)	0.052 (4)	−0.004 (3)	0.010 (3)	0.005 (3)
C17	0.059 (4)	0.051 (5)	0.061 (4)	0.001 (4)	0.026 (3)	0.005 (3)
C18	0.031 (3)	0.028 (3)	0.028 (3)	−0.005 (2)	0.002 (2)	−0.003 (2)
C19	0.039 (3)	0.034 (4)	0.037 (3)	0.001 (3)	0.004 (3)	0.008 (3)
C20	0.046 (4)	0.021 (3)	0.043 (4)	0.002 (3)	−0.002 (3)	−0.001 (3)
C21	0.040 (3)	0.024 (3)	0.043 (3)	0.006 (3)	−0.002 (3)	−0.010 (3)
C22	0.034 (3)	0.021 (3)	0.034 (3)	0.006 (2)	−0.007 (2)	0.000 (2)
C23	0.021 (3)	0.025 (3)	0.031 (3)	0.000 (2)	−0.003 (2)	−0.003 (2)
C24	0.026 (3)	0.022 (3)	0.038 (3)	0.002 (2)	−0.001 (2)	0.002 (2)
C25	0.028 (3)	0.024 (3)	0.048 (4)	−0.004 (2)	0.002 (3)	0.005 (3)
C26	0.028 (3)	0.033 (4)	0.047 (4)	0.005 (3)	0.009 (3)	−0.003 (3)
C27	0.031 (3)	0.014 (3)	0.034 (3)	0.001 (2)	0.002 (2)	0.001 (2)
C28	0.026 (3)	0.031 (3)	0.033 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C29	0.035 (3)	0.033 (3)	0.033 (3)	0.002 (3)	0.009 (2)	−0.001 (2)
C30	0.034 (3)	0.018 (3)	0.032 (3)	0.001 (2)	0.000 (2)	0.003 (2)
C31	0.033 (3)	0.020 (3)	0.037 (3)	0.001 (2)	0.007 (2)	0.002 (2)
C32	0.034 (3)	0.021 (3)	0.034 (3)	0.002 (2)	0.002 (2)	−0.001 (2)
C33	0.033 (3)	0.031 (3)	0.039 (3)	−0.002 (3)	0.006 (2)	−0.001 (2)
C34	0.034 (3)	0.030 (4)	0.053 (4)	−0.001 (3)	0.011 (3)	0.001 (3)

Geometric parameters (Å, º) top

Br1—C4	1.908 (5)	C16—C17	1.505 (8)
Br2—C21	1.912 (6)	C16—H16A	0.9900
Cl1—C1	1.742 (5)	C16—H16B	0.9900
Cl2—C8	1.770 (6)	C17—H17A	0.9800
Cl3—C8	1.763 (6)	C17—H17B	0.9800
Cl4—C18	1.748 (6)	C17—H17C	0.9800
Cl5—C25	1.793 (6)	C18—C19	1.400 (8)
Cl6—C25	1.759 (6)	C18—C23	1.406 (7)
O1—C13	1.360 (6)	C19—C20	1.406 (8)
O1—C16	1.459 (6)	C19—H19	0.9500
O2—C30	1.376 (6)	C20—C21	1.397 (9)
O2—C33	1.449 (6)	C20—H20	0.9500
C1—C2	1.405 (8)	C21—C22	1.382 (7)
C1—C6	1.425 (8)	C22—C23	1.415 (7)
C2—C3	1.363 (8)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.491 (7)
C3—C4	1.421 (8)	C24—C27	1.526 (7)
C3—H3	0.9500	C24—C25	1.532 (8)
C4—C5	1.398 (7)	C24—C26	1.557 (7)
C5—C6	1.391 (8)	C25—C26	1.479 (8)
C5—H5	0.9500	C26—H26A	0.9900
C6—C7	1.519 (7)	C26—H26B	0.9900
C7—C10	1.503 (7)	C27—C32	1.390 (7)
C7—C8	1.541 (8)	C27—C28	1.399 (7)
C7—C9	1.548 (8)	C28—C29	1.372 (7)
C8—C9	1.473 (8)	C28—H28	0.9500
C9—H9A	0.9900	C29—C30	1.400 (7)
C9—H9B	0.9900	C29—H29	0.9500
C10—C15	1.412 (7)	C30—C31	1.402 (7)
C10—C11	1.416 (7)	C31—C32	1.413 (7)
C11—C12	1.384 (8)	C31—H31	0.9500
C11—H11	0.9500	C32—H32	0.9500
C12—C13	1.401 (7)	C33—C34	1.511 (8)
C12—H12	0.9500	C33—H33A	0.9900
C13—C14	1.413 (7)	C33—H33B	0.9900
C14—C15	1.400 (8)	C34—H34A	0.9800
C14—H14	0.9500	C34—H34B	0.9800
C15—H15	0.9500	C34—H34C	0.9800

C13—O1—C16	118.7 (4)	H17B—C17—H17C	109.5
C30—O2—C33	117.5 (4)	C19—C18—C23	122.6 (5)
C2—C1—C6	120.5 (5)	C19—C18—Cl4	116.1 (4)
C2—C1—Cl1	118.6 (4)	C23—C18—Cl4	121.3 (4)
C6—C1—Cl1	120.8 (5)	C18—C19—C20	119.6 (5)
C3—C2—C1	121.0 (5)	C18—C19—H19	120.2
C3—C2—H2	119.5	C20—C19—H19	120.2
C1—C2—H2	119.5	C21—C20—C19	118.3 (5)
C2—C3—C4	119.1 (5)	C21—C20—H20	120.8
C2—C3—H3	120.5	C19—C20—H20	120.8
C4—C3—H3	120.5	C22—C21—C20	121.8 (6)
C5—C4—C3	120.5 (5)	C22—C21—Br2	119.5 (5)
C5—C4—Br1	120.9 (4)	C20—C21—Br2	118.6 (4)
C3—C4—Br1	118.5 (4)	C21—C22—C23	121.2 (5)
C6—C5—C4	120.8 (5)	C21—C22—H22	119.4
C6—C5—H5	119.6	C23—C22—H22	119.4
C4—C5—H5	119.6	C18—C23—C22	116.5 (5)
C5—C6—C1	118.0 (5)	C18—C23—C24	124.0 (5)
C5—C6—C7	120.5 (5)	C22—C23—C24	119.3 (5)
C1—C6—C7	121.2 (5)	C23—C24—C27	112.9 (4)
C10—C7—C6	112.4 (5)	C23—C24—C25	118.8 (4)
C10—C7—C8	119.4 (5)	C27—C24—C25	118.4 (5)
C6—C7—C8	119.2 (5)	C23—C24—C26	119.6 (5)
C10—C7—C9	117.7 (5)	C27—C24—C26	119.3 (5)
C6—C7—C9	120.8 (5)	C25—C24—C26	57.2 (3)
C8—C7—C9	56.9 (4)	C26—C25—C24	62.2 (4)
C9—C8—C7	61.8 (4)	C26—C25—Cl6	120.5 (4)
C9—C8—Cl3	121.6 (4)	C24—C25—Cl6	120.5 (4)
C7—C8—Cl3	118.0 (4)	C26—C25—Cl5	117.2 (4)
C9—C8—Cl2	116.5 (4)	C24—C25—Cl5	118.2 (4)
C7—C8—Cl2	119.6 (4)	Cl6—C25—Cl5	110.7 (3)
Cl3—C8—Cl2	111.4 (3)	C25—C26—C24	60.6 (4)
C8—C9—C7	61.3 (4)	C25—C26—H26A	117.7
C8—C9—H9A	117.6	C24—C26—H26A	117.7
C7—C9—H9A	117.6	C25—C26—H26B	117.7
C8—C9—H9B	117.6	C24—C26—H26B	117.7
C7—C9—H9B	117.6	H26A—C26—H26B	114.8
H9A—C9—H9B	114.7	C32—C27—C28	118.9 (5)
C15—C10—C11	116.6 (5)	C32—C27—C24	120.5 (5)
C15—C10—C7	121.8 (5)	C28—C27—C24	120.5 (5)
C11—C10—C7	121.2 (5)	C29—C28—C27	121.0 (5)
C12—C11—C10	121.8 (5)	C29—C28—H28	119.5
C12—C11—H11	119.1	C27—C28—H28	119.5
C10—C11—H11	119.1	C28—C29—C30	120.6 (5)
C11—C12—C13	120.7 (5)	C28—C29—H29	119.7
C11—C12—H12	119.6	C30—C29—H29	119.7
C13—C12—H12	119.6	O2—C30—C29	116.2 (5)
O1—C13—C12	116.6 (5)	O2—C30—C31	124.3 (5)
O1—C13—C14	124.2 (5)	C29—C30—C31	119.6 (5)
C12—C13—C14	119.2 (5)	C30—C31—C32	119.0 (5)
C15—C14—C13	119.1 (5)	C30—C31—H31	120.5
C15—C14—H14	120.4	C32—C31—H31	120.5
C13—C14—H14	120.4	C27—C32—C31	120.8 (5)
C14—C15—C10	122.4 (5)	C27—C32—H32	119.6
C14—C15—H15	118.8	C31—C32—H32	119.6
C10—C15—H15	118.8	O2—C33—C34	106.8 (4)
O1—C16—C17	108.0 (5)	O2—C33—H33A	110.4
O1—C16—H16A	110.1	C34—C33—H33A	110.4
C17—C16—H16A	110.1	O2—C33—H33B	110.4
O1—C16—H16B	110.1	C34—C33—H33B	110.4
C17—C16—H16B	110.1	H33A—C33—H33B	108.6
H16A—C16—H16B	108.4	C33—C34—H34A	109.5
C16—C17—H17A	109.5	C33—C34—H34B	109.5
C16—C17—H17B	109.5	H34A—C34—H34B	109.5
H17A—C17—H17B	109.5	C33—C34—H34C	109.5
C16—C17—H17C	109.5	H34A—C34—H34C	109.5
H17A—C17—H17C	109.5	H34B—C34—H34C	109.5

C6—C1—C2—C3	3.2 (9)	C23—C18—C19—C20	−1.7 (8)
Cl1—C1—C2—C3	−175.8 (5)	Cl4—C18—C19—C20	175.6 (4)
C1—C2—C3—C4	−2.4 (9)	C18—C19—C20—C21	0.8 (8)
C2—C3—C4—C5	0.2 (8)	C19—C20—C21—C22	0.2 (8)
C2—C3—C4—Br1	178.6 (4)	C19—C20—C21—Br2	−177.8 (4)
C3—C4—C5—C6	1.1 (8)	C20—C21—C22—C23	−0.4 (8)
Br1—C4—C5—C6	−177.2 (4)	Br2—C21—C22—C23	177.6 (4)
C4—C5—C6—C1	−0.3 (8)	C19—C18—C23—C22	1.5 (7)
C4—C5—C6—C7	173.4 (5)	Cl4—C18—C23—C22	−175.7 (4)
C2—C1—C6—C5	−1.8 (8)	C19—C18—C23—C24	176.8 (5)
Cl1—C1—C6—C5	177.2 (4)	Cl4—C18—C23—C24	−0.4 (7)
C2—C1—C6—C7	−175.5 (5)	C21—C22—C23—C18	−0.4 (7)
Cl1—C1—C6—C7	3.6 (7)	C21—C22—C23—C24	−176.0 (5)
C5—C6—C7—C10	−85.9 (6)	C18—C23—C24—C27	−95.2 (6)
C1—C6—C7—C10	87.5 (6)	C22—C23—C24—C27	80.0 (6)
C5—C6—C7—C8	61.1 (7)	C18—C23—C24—C25	119.6 (6)
C1—C6—C7—C8	−125.4 (6)	C22—C23—C24—C25	−65.2 (6)
C5—C6—C7—C9	127.9 (6)	C18—C23—C24—C26	53.1 (7)
C1—C6—C7—C9	−58.7 (7)	C22—C23—C24—C26	−131.7 (5)
C10—C7—C8—C9	−105.7 (6)	C23—C24—C25—C26	−108.5 (6)
C6—C7—C8—C9	109.6 (6)	C27—C24—C25—C26	108.2 (6)
C10—C7—C8—Cl3	7.2 (7)	C23—C24—C25—Cl6	140.7 (4)
C6—C7—C8—Cl3	−137.5 (5)	C27—C24—C25—Cl6	−2.6 (7)
C9—C7—C8—Cl3	112.9 (5)	C26—C24—C25—Cl6	−110.9 (5)
C10—C7—C8—Cl2	148.2 (4)	C23—C24—C25—Cl5	−0.8 (7)
C6—C7—C8—Cl2	3.5 (7)	C27—C24—C25—Cl5	−144.1 (4)
C9—C7—C8—Cl2	−106.2 (5)	C26—C24—C25—Cl5	107.7 (5)
Cl3—C8—C9—C7	−107.2 (5)	Cl6—C25—C26—C24	110.8 (5)
Cl2—C8—C9—C7	111.0 (5)	Cl5—C25—C26—C24	−109.3 (5)
C10—C7—C9—C8	108.6 (5)	C23—C24—C26—C25	107.0 (5)
C6—C7—C9—C8	−106.9 (6)	C27—C24—C26—C25	−106.7 (5)
C6—C7—C10—C15	−104.4 (6)	C23—C24—C27—C32	−78.0 (6)
C8—C7—C10—C15	108.6 (6)	C25—C24—C27—C32	67.4 (7)
C9—C7—C10—C15	42.9 (7)	C26—C24—C27—C32	133.6 (5)
C6—C7—C10—C11	68.8 (7)	C23—C24—C27—C28	98.1 (6)
C8—C7—C10—C11	−78.1 (7)	C25—C24—C27—C28	−116.6 (6)
C9—C7—C10—C11	−143.8 (5)	C26—C24—C27—C28	−50.3 (7)
C15—C10—C11—C12	0.8 (8)	C32—C27—C28—C29	0.4 (8)
C7—C10—C11—C12	−172.7 (5)	C24—C27—C28—C29	−175.7 (5)
C10—C11—C12—C13	0.2 (8)	C27—C28—C29—C30	−0.8 (8)
C16—O1—C13—C12	−172.7 (5)	C33—O2—C30—C29	−177.1 (5)
C16—O1—C13—C14	6.1 (8)	C33—O2—C30—C31	2.5 (7)
C11—C12—C13—O1	176.2 (5)	C28—C29—C30—O2	−179.6 (5)
C11—C12—C13—C14	−2.6 (8)	C28—C29—C30—C31	0.7 (8)
O1—C13—C14—C15	−174.9 (5)	O2—C30—C31—C32	−179.8 (5)
C12—C13—C14—C15	3.9 (8)	C29—C30—C31—C32	−0.2 (8)
C13—C14—C15—C10	−2.9 (8)	C28—C27—C32—C31	0.2 (8)
C11—C10—C15—C14	0.5 (8)	C24—C27—C32—C31	176.3 (5)
C7—C10—C15—C14	174.0 (5)	C30—C31—C32—C27	−0.3 (8)
C13—O1—C16—C17	173.7 (5)	C30—O2—C33—C34	179.3 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring. Cg2 is the centroid of the C27–C32 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.95	2.66	3.665 (3)	161
C20—H20···Cg2ⁱⁱ	0.95	2.60	3.480 (9)	155

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄BrCl₃O
M_r	420.54
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	27.447 (13), 8.886 (4), 28.861 (14)
β (°)	98.348 (8)
V (Å³)	6965 (6)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	2.82
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2009)
T_min, T_max	0.603, 0.694
No. of measured, independent and observed [I > 2σ(I)] reflections	26327, 6143, 4903
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.180, 1.09
No. of reflections	6143
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.54, −0.89

Computer programs: CrystalClear (Rigaku/MSC, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring. Cg2 is the centroid of the C27–C32 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.95	2.66	3.665 (3)	161
C20—H20···Cg2ⁱⁱ	0.95	2.60	3.480 (9)	155

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

References

DeLacy, T. P. & Kennard, C. H. L. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 2141–2147. CSD CrossRef Google Scholar
Lauher, J. W. & Ibers, J. A. (1975). J. Am. Chem. Soc. 97, 561–567. CSD CrossRef CAS Web of Science Google Scholar
Meng, M., et al. (2008). J. Med. Chem. 51, 1145–1149. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Washburn, W. N. (2009). J. Med. Chem. 52, 1785–1794. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 69| Part 3| March 2013| Page o405

doi:10.1107/S1600536813003735

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