organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Washburn, W. N. (2009). J. Med. Chem. 52, 1785-1794.]); Meng et al. (2008[Meng, M., et al. (2008). J. Med. Chem. 51, 1145-1149.]). For the crystal structures of related cyclo­propane derivatives, see: DeLacy & Kennard (1972[DeLacy, T. P. & Kennard, C. H. L. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 2141-2147.]); Lauher & Ibers (1975[Lauher, J. W. & Ibers, J. A. (1975). J. Am. Chem. Soc. 97, 561-567.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14BrCl3O

  • Mr = 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[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.603, Tmax = 0.694

  • 26327 measured reflections

  • 6143 independent reflections

  • 4903 reflections with I > 2σ(I)

  • Rint = 0.104

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.180

  • S = 1.09

  • 6143 reflections

  • 399 parameters

  • H-atom parameters constrained

  • Δρmax = 1.54 e Å−3

  • Δρmin = −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 DA 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[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were geometrically positioned, with C–H = 0.95–0.99 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2–1.5 Ueq(C).

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
[Figure 1] 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
C17H14BrCl3OF(000) = 3360
Mr = 420.54Dx = 1.604 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 11664 reflections
a = 27.447 (13) Åθ = 1.5–28.0°
b = 8.886 (4) ŵ = 2.82 mm1
c = 28.861 (14) ÅT = 113 K
β = 98.348 (8)°Prism, colorless
V = 6965 (6) Å30.20 × 0.18 × 0.14 mm
Z = 16
Data collection top
Rigaku Saturn724 CCD
diffractometer
6143 independent reflections
Radiation source: rotating anode4903 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.104
Detector resolution: 14.22 pixels mm-1θmax = 25.0°, θmin = 1.5°
ω and ϕ scansh = 3232
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2009)
k = 1010
Tmin = 0.603, Tmax = 0.694l = 3433
26327 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0747P)2]
where P = (Fo2 + 2Fc2)/3
6143 reflections(Δ/σ)max = 0.003
399 parametersΔρmax = 1.54 e Å3
0 restraintsΔρmin = 0.89 e Å3
Crystal data top
C17H14BrCl3OV = 6965 (6) Å3
Mr = 420.54Z = 16
Monoclinic, C2/cMo Kα radiation
a = 27.447 (13) ŵ = 2.82 mm1
b = 8.886 (4) ÅT = 113 K
c = 28.861 (14) Å0.20 × 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)
Tmin = 0.603, Tmax = 0.694Rint = 0.104
26327 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.180H-atom parameters constrained
S = 1.09Δρmax = 1.54 e Å3
6143 reflectionsΔρmin = 0.89 e Å3
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
xyzUiso*/Ueq
Br10.67589 (2)0.00608 (7)0.06050 (2)0.0372 (2)
Br20.43550 (2)0.53077 (7)0.20897 (2)0.0428 (2)
Cl10.83567 (5)0.28486 (18)0.22003 (5)0.0403 (4)
Cl20.65376 (5)0.41196 (18)0.19345 (5)0.0439 (4)
Cl30.67918 (6)0.70547 (18)0.15844 (6)0.0478 (4)
Cl40.58075 (5)0.28004 (17)0.07179 (5)0.0386 (4)
Cl50.58547 (5)0.14483 (17)0.24050 (5)0.0392 (4)
Cl60.55111 (5)0.15899 (17)0.21433 (5)0.0427 (4)
O10.85763 (13)0.7592 (4)0.03892 (12)0.0354 (9)
O20.38664 (14)0.2563 (5)0.03844 (13)0.0373 (10)
C10.7900 (2)0.2085 (7)0.17851 (18)0.0329 (13)
C20.7932 (2)0.0558 (7)0.1666 (2)0.0361 (14)
H20.81880.00440.18280.043*
C30.7602 (2)0.0070 (6)0.1322 (2)0.0356 (14)
H30.76340.10930.12360.043*
C40.7210 (2)0.0825 (6)0.10951 (18)0.0321 (13)
C50.71635 (19)0.2331 (6)0.12209 (19)0.0308 (12)
H50.68960.29110.10700.037*
C60.7505 (2)0.2992 (6)0.15645 (19)0.0321 (13)
C70.74841 (19)0.4669 (6)0.1662 (2)0.0322 (13)
C80.7021 (2)0.5333 (6)0.1829 (2)0.0369 (14)
C90.7478 (2)0.5258 (7)0.2166 (2)0.0377 (14)
H9A0.74940.45050.24210.045*
H9B0.76510.62150.22560.045*
C100.77570 (19)0.5583 (6)0.13452 (19)0.0295 (12)
C110.7582 (2)0.5712 (6)0.08606 (19)0.0321 (13)
H110.72680.53100.07420.038*
C120.7856 (2)0.6408 (6)0.05556 (19)0.0328 (13)
H120.77270.64780.02330.039*
C130.83215 (19)0.7009 (6)0.07179 (18)0.0277 (12)
C140.8501 (2)0.6955 (6)0.12017 (19)0.0330 (13)
H140.88070.74110.13210.040*
C150.82230 (19)0.6219 (6)0.15032 (19)0.0315 (13)
H150.83530.61450.18260.038*
C160.9085 (2)0.8066 (7)0.0533 (2)0.0426 (15)
H16A0.92780.72340.06970.051*
H16B0.90960.89360.07480.051*
C170.9298 (3)0.8496 (8)0.0099 (2)0.0550 (18)
H17A0.92980.76170.01060.082*
H17B0.96370.88540.01880.082*
H17C0.90990.92980.00670.082*
C180.54406 (19)0.3437 (6)0.11248 (17)0.0292 (12)
C190.5307 (2)0.4958 (7)0.1094 (2)0.0367 (14)
H190.54340.55980.08760.044*
C200.4985 (2)0.5532 (7)0.1387 (2)0.0376 (14)
H200.48860.65580.13680.045*
C210.4812 (2)0.4555 (6)0.1706 (2)0.0367 (14)
C220.49516 (19)0.3061 (6)0.17397 (18)0.0310 (13)
H220.48280.24320.19620.037*
C230.52744 (18)0.2449 (6)0.14489 (17)0.0265 (12)
C240.53880 (19)0.0807 (6)0.14758 (18)0.0293 (12)
C250.5670 (2)0.0172 (6)0.1931 (2)0.0338 (13)
C260.5933 (2)0.0272 (7)0.1520 (2)0.0357 (14)
H26A0.60000.06770.13610.043*
H26B0.61910.10520.15240.043*
C270.4984 (2)0.0153 (6)0.12023 (18)0.0263 (12)
C280.50266 (19)0.0656 (6)0.07508 (18)0.0300 (12)
H280.53200.04540.06230.036*
C290.4652 (2)0.1437 (6)0.04900 (19)0.0332 (13)
H290.46870.17570.01820.040*
C300.42187 (19)0.1767 (6)0.06726 (17)0.0283 (12)
C310.4166 (2)0.1279 (6)0.11244 (18)0.0297 (12)
H310.38740.14920.12520.036*
C320.45541 (19)0.0464 (6)0.13867 (19)0.0298 (12)
H320.45210.01250.16930.036*
C330.3404 (2)0.2861 (7)0.05542 (19)0.0340 (13)
H33A0.32430.19050.06210.041*
H33B0.34610.34640.08450.041*
C340.3086 (2)0.3721 (7)0.0173 (2)0.0386 (14)
H34A0.30270.31040.01110.058*
H34B0.27700.39650.02760.058*
H34C0.32530.46540.01060.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0356 (4)0.0322 (4)0.0441 (4)0.0030 (3)0.0068 (3)0.0046 (3)
Br20.0407 (4)0.0353 (4)0.0537 (4)0.0065 (3)0.0111 (3)0.0098 (3)
Cl10.0385 (8)0.0353 (9)0.0449 (9)0.0014 (6)0.0016 (6)0.0038 (6)
Cl20.0396 (8)0.0374 (9)0.0579 (10)0.0057 (7)0.0182 (7)0.0038 (7)
Cl30.0488 (9)0.0329 (9)0.0652 (10)0.0102 (7)0.0195 (7)0.0036 (7)
Cl40.0384 (8)0.0356 (9)0.0433 (8)0.0013 (6)0.0107 (6)0.0006 (6)
Cl50.0407 (8)0.0373 (9)0.0379 (8)0.0026 (6)0.0002 (6)0.0011 (6)
Cl60.0409 (8)0.0288 (8)0.0557 (9)0.0014 (6)0.0019 (7)0.0141 (7)
O10.035 (2)0.034 (2)0.036 (2)0.0050 (18)0.0020 (17)0.0074 (17)
O20.035 (2)0.041 (3)0.037 (2)0.0066 (18)0.0090 (17)0.0073 (18)
C10.031 (3)0.035 (4)0.031 (3)0.005 (3)0.001 (2)0.003 (2)
C20.030 (3)0.028 (3)0.049 (4)0.006 (3)0.005 (3)0.002 (3)
C30.037 (3)0.026 (3)0.048 (4)0.007 (3)0.017 (3)0.003 (3)
C40.034 (3)0.025 (3)0.039 (3)0.002 (2)0.010 (2)0.000 (2)
C50.027 (3)0.025 (3)0.042 (3)0.000 (2)0.011 (2)0.003 (2)
C60.035 (3)0.027 (3)0.037 (3)0.001 (2)0.013 (2)0.004 (2)
C70.026 (3)0.024 (3)0.048 (4)0.003 (2)0.012 (2)0.002 (2)
C80.042 (3)0.020 (3)0.052 (4)0.004 (3)0.017 (3)0.005 (3)
C90.039 (3)0.031 (4)0.044 (4)0.006 (3)0.012 (3)0.005 (3)
C100.026 (3)0.024 (3)0.039 (3)0.001 (2)0.008 (2)0.005 (2)
C110.031 (3)0.026 (3)0.038 (3)0.001 (2)0.000 (2)0.003 (2)
C120.036 (3)0.027 (3)0.034 (3)0.002 (2)0.001 (2)0.003 (2)
C130.033 (3)0.020 (3)0.029 (3)0.004 (2)0.005 (2)0.002 (2)
C140.034 (3)0.025 (3)0.040 (3)0.001 (3)0.004 (2)0.001 (2)
C150.030 (3)0.030 (3)0.034 (3)0.008 (2)0.003 (2)0.002 (2)
C160.032 (3)0.045 (4)0.052 (4)0.004 (3)0.010 (3)0.005 (3)
C170.059 (4)0.051 (5)0.061 (4)0.001 (4)0.026 (3)0.005 (3)
C180.031 (3)0.028 (3)0.028 (3)0.005 (2)0.002 (2)0.003 (2)
C190.039 (3)0.034 (4)0.037 (3)0.001 (3)0.004 (3)0.008 (3)
C200.046 (4)0.021 (3)0.043 (4)0.002 (3)0.002 (3)0.001 (3)
C210.040 (3)0.024 (3)0.043 (3)0.006 (3)0.002 (3)0.010 (3)
C220.034 (3)0.021 (3)0.034 (3)0.006 (2)0.007 (2)0.000 (2)
C230.021 (3)0.025 (3)0.031 (3)0.000 (2)0.003 (2)0.003 (2)
C240.026 (3)0.022 (3)0.038 (3)0.002 (2)0.001 (2)0.002 (2)
C250.028 (3)0.024 (3)0.048 (4)0.004 (2)0.002 (3)0.005 (3)
C260.028 (3)0.033 (4)0.047 (4)0.005 (3)0.009 (3)0.003 (3)
C270.031 (3)0.014 (3)0.034 (3)0.001 (2)0.002 (2)0.001 (2)
C280.026 (3)0.031 (3)0.033 (3)0.000 (2)0.005 (2)0.001 (2)
C290.035 (3)0.033 (3)0.033 (3)0.002 (3)0.009 (2)0.001 (2)
C300.034 (3)0.018 (3)0.032 (3)0.001 (2)0.000 (2)0.003 (2)
C310.033 (3)0.020 (3)0.037 (3)0.001 (2)0.007 (2)0.002 (2)
C320.034 (3)0.021 (3)0.034 (3)0.002 (2)0.002 (2)0.001 (2)
C330.033 (3)0.031 (3)0.039 (3)0.002 (3)0.006 (2)0.001 (2)
C340.034 (3)0.030 (4)0.053 (4)0.001 (3)0.011 (3)0.001 (3)
Geometric parameters (Å, º) top
Br1—C41.908 (5)C16—C171.505 (8)
Br2—C211.912 (6)C16—H16A0.9900
Cl1—C11.742 (5)C16—H16B0.9900
Cl2—C81.770 (6)C17—H17A0.9800
Cl3—C81.763 (6)C17—H17B0.9800
Cl4—C181.748 (6)C17—H17C0.9800
Cl5—C251.793 (6)C18—C191.400 (8)
Cl6—C251.759 (6)C18—C231.406 (7)
O1—C131.360 (6)C19—C201.406 (8)
O1—C161.459 (6)C19—H190.9500
O2—C301.376 (6)C20—C211.397 (9)
O2—C331.449 (6)C20—H200.9500
C1—C21.405 (8)C21—C221.382 (7)
C1—C61.425 (8)C22—C231.415 (7)
C2—C31.363 (8)C22—H220.9500
C2—H20.9500C23—C241.491 (7)
C3—C41.421 (8)C24—C271.526 (7)
C3—H30.9500C24—C251.532 (8)
C4—C51.398 (7)C24—C261.557 (7)
C5—C61.391 (8)C25—C261.479 (8)
C5—H50.9500C26—H26A0.9900
C6—C71.519 (7)C26—H26B0.9900
C7—C101.503 (7)C27—C321.390 (7)
C7—C81.541 (8)C27—C281.399 (7)
C7—C91.548 (8)C28—C291.372 (7)
C8—C91.473 (8)C28—H280.9500
C9—H9A0.9900C29—C301.400 (7)
C9—H9B0.9900C29—H290.9500
C10—C151.412 (7)C30—C311.402 (7)
C10—C111.416 (7)C31—C321.413 (7)
C11—C121.384 (8)C31—H310.9500
C11—H110.9500C32—H320.9500
C12—C131.401 (7)C33—C341.511 (8)
C12—H120.9500C33—H33A0.9900
C13—C141.413 (7)C33—H33B0.9900
C14—C151.400 (8)C34—H34A0.9800
C14—H140.9500C34—H34B0.9800
C15—H150.9500C34—H34C0.9800
C13—O1—C16118.7 (4)H17B—C17—H17C109.5
C30—O2—C33117.5 (4)C19—C18—C23122.6 (5)
C2—C1—C6120.5 (5)C19—C18—Cl4116.1 (4)
C2—C1—Cl1118.6 (4)C23—C18—Cl4121.3 (4)
C6—C1—Cl1120.8 (5)C18—C19—C20119.6 (5)
C3—C2—C1121.0 (5)C18—C19—H19120.2
C3—C2—H2119.5C20—C19—H19120.2
C1—C2—H2119.5C21—C20—C19118.3 (5)
C2—C3—C4119.1 (5)C21—C20—H20120.8
C2—C3—H3120.5C19—C20—H20120.8
C4—C3—H3120.5C22—C21—C20121.8 (6)
C5—C4—C3120.5 (5)C22—C21—Br2119.5 (5)
C5—C4—Br1120.9 (4)C20—C21—Br2118.6 (4)
C3—C4—Br1118.5 (4)C21—C22—C23121.2 (5)
C6—C5—C4120.8 (5)C21—C22—H22119.4
C6—C5—H5119.6C23—C22—H22119.4
C4—C5—H5119.6C18—C23—C22116.5 (5)
C5—C6—C1118.0 (5)C18—C23—C24124.0 (5)
C5—C6—C7120.5 (5)C22—C23—C24119.3 (5)
C1—C6—C7121.2 (5)C23—C24—C27112.9 (4)
C10—C7—C6112.4 (5)C23—C24—C25118.8 (4)
C10—C7—C8119.4 (5)C27—C24—C25118.4 (5)
C6—C7—C8119.2 (5)C23—C24—C26119.6 (5)
C10—C7—C9117.7 (5)C27—C24—C26119.3 (5)
C6—C7—C9120.8 (5)C25—C24—C2657.2 (3)
C8—C7—C956.9 (4)C26—C25—C2462.2 (4)
C9—C8—C761.8 (4)C26—C25—Cl6120.5 (4)
C9—C8—Cl3121.6 (4)C24—C25—Cl6120.5 (4)
C7—C8—Cl3118.0 (4)C26—C25—Cl5117.2 (4)
C9—C8—Cl2116.5 (4)C24—C25—Cl5118.2 (4)
C7—C8—Cl2119.6 (4)Cl6—C25—Cl5110.7 (3)
Cl3—C8—Cl2111.4 (3)C25—C26—C2460.6 (4)
C8—C9—C761.3 (4)C25—C26—H26A117.7
C8—C9—H9A117.6C24—C26—H26A117.7
C7—C9—H9A117.6C25—C26—H26B117.7
C8—C9—H9B117.6C24—C26—H26B117.7
C7—C9—H9B117.6H26A—C26—H26B114.8
H9A—C9—H9B114.7C32—C27—C28118.9 (5)
C15—C10—C11116.6 (5)C32—C27—C24120.5 (5)
C15—C10—C7121.8 (5)C28—C27—C24120.5 (5)
C11—C10—C7121.2 (5)C29—C28—C27121.0 (5)
C12—C11—C10121.8 (5)C29—C28—H28119.5
C12—C11—H11119.1C27—C28—H28119.5
C10—C11—H11119.1C28—C29—C30120.6 (5)
C11—C12—C13120.7 (5)C28—C29—H29119.7
C11—C12—H12119.6C30—C29—H29119.7
C13—C12—H12119.6O2—C30—C29116.2 (5)
O1—C13—C12116.6 (5)O2—C30—C31124.3 (5)
O1—C13—C14124.2 (5)C29—C30—C31119.6 (5)
C12—C13—C14119.2 (5)C30—C31—C32119.0 (5)
C15—C14—C13119.1 (5)C30—C31—H31120.5
C15—C14—H14120.4C32—C31—H31120.5
C13—C14—H14120.4C27—C32—C31120.8 (5)
C14—C15—C10122.4 (5)C27—C32—H32119.6
C14—C15—H15118.8C31—C32—H32119.6
C10—C15—H15118.8O2—C33—C34106.8 (4)
O1—C16—C17108.0 (5)O2—C33—H33A110.4
O1—C16—H16A110.1C34—C33—H33A110.4
C17—C16—H16A110.1O2—C33—H33B110.4
O1—C16—H16B110.1C34—C33—H33B110.4
C17—C16—H16B110.1H33A—C33—H33B108.6
H16A—C16—H16B108.4C33—C34—H34A109.5
C16—C17—H17A109.5C33—C34—H34B109.5
C16—C17—H17B109.5H34A—C34—H34B109.5
H17A—C17—H17B109.5C33—C34—H34C109.5
C16—C17—H17C109.5H34A—C34—H34C109.5
H17A—C17—H17C109.5H34B—C34—H34C109.5
C6—C1—C2—C33.2 (9)C23—C18—C19—C201.7 (8)
Cl1—C1—C2—C3175.8 (5)Cl4—C18—C19—C20175.6 (4)
C1—C2—C3—C42.4 (9)C18—C19—C20—C210.8 (8)
C2—C3—C4—C50.2 (8)C19—C20—C21—C220.2 (8)
C2—C3—C4—Br1178.6 (4)C19—C20—C21—Br2177.8 (4)
C3—C4—C5—C61.1 (8)C20—C21—C22—C230.4 (8)
Br1—C4—C5—C6177.2 (4)Br2—C21—C22—C23177.6 (4)
C4—C5—C6—C10.3 (8)C19—C18—C23—C221.5 (7)
C4—C5—C6—C7173.4 (5)Cl4—C18—C23—C22175.7 (4)
C2—C1—C6—C51.8 (8)C19—C18—C23—C24176.8 (5)
Cl1—C1—C6—C5177.2 (4)Cl4—C18—C23—C240.4 (7)
C2—C1—C6—C7175.5 (5)C21—C22—C23—C180.4 (7)
Cl1—C1—C6—C73.6 (7)C21—C22—C23—C24176.0 (5)
C5—C6—C7—C1085.9 (6)C18—C23—C24—C2795.2 (6)
C1—C6—C7—C1087.5 (6)C22—C23—C24—C2780.0 (6)
C5—C6—C7—C861.1 (7)C18—C23—C24—C25119.6 (6)
C1—C6—C7—C8125.4 (6)C22—C23—C24—C2565.2 (6)
C5—C6—C7—C9127.9 (6)C18—C23—C24—C2653.1 (7)
C1—C6—C7—C958.7 (7)C22—C23—C24—C26131.7 (5)
C10—C7—C8—C9105.7 (6)C23—C24—C25—C26108.5 (6)
C6—C7—C8—C9109.6 (6)C27—C24—C25—C26108.2 (6)
C10—C7—C8—Cl37.2 (7)C23—C24—C25—Cl6140.7 (4)
C6—C7—C8—Cl3137.5 (5)C27—C24—C25—Cl62.6 (7)
C9—C7—C8—Cl3112.9 (5)C26—C24—C25—Cl6110.9 (5)
C10—C7—C8—Cl2148.2 (4)C23—C24—C25—Cl50.8 (7)
C6—C7—C8—Cl23.5 (7)C27—C24—C25—Cl5144.1 (4)
C9—C7—C8—Cl2106.2 (5)C26—C24—C25—Cl5107.7 (5)
Cl3—C8—C9—C7107.2 (5)Cl6—C25—C26—C24110.8 (5)
Cl2—C8—C9—C7111.0 (5)Cl5—C25—C26—C24109.3 (5)
C10—C7—C9—C8108.6 (5)C23—C24—C26—C25107.0 (5)
C6—C7—C9—C8106.9 (6)C27—C24—C26—C25106.7 (5)
C6—C7—C10—C15104.4 (6)C23—C24—C27—C3278.0 (6)
C8—C7—C10—C15108.6 (6)C25—C24—C27—C3267.4 (7)
C9—C7—C10—C1542.9 (7)C26—C24—C27—C32133.6 (5)
C6—C7—C10—C1168.8 (7)C23—C24—C27—C2898.1 (6)
C8—C7—C10—C1178.1 (7)C25—C24—C27—C28116.6 (6)
C9—C7—C10—C11143.8 (5)C26—C24—C27—C2850.3 (7)
C15—C10—C11—C120.8 (8)C32—C27—C28—C290.4 (8)
C7—C10—C11—C12172.7 (5)C24—C27—C28—C29175.7 (5)
C10—C11—C12—C130.2 (8)C27—C28—C29—C300.8 (8)
C16—O1—C13—C12172.7 (5)C33—O2—C30—C29177.1 (5)
C16—O1—C13—C146.1 (8)C33—O2—C30—C312.5 (7)
C11—C12—C13—O1176.2 (5)C28—C29—C30—O2179.6 (5)
C11—C12—C13—C142.6 (8)C28—C29—C30—C310.7 (8)
O1—C13—C14—C15174.9 (5)O2—C30—C31—C32179.8 (5)
C12—C13—C14—C153.9 (8)C29—C30—C31—C320.2 (8)
C13—C14—C15—C102.9 (8)C28—C27—C32—C310.2 (8)
C11—C10—C15—C140.5 (8)C24—C27—C32—C31176.3 (5)
C7—C10—C15—C14174.0 (5)C30—C31—C32—C270.3 (8)
C13—O1—C16—C17173.7 (5)C30—O2—C33—C34179.3 (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···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.952.663.665 (3)161
C20—H20···Cg2ii0.952.603.480 (9)155
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H14BrCl3O
Mr420.54
Crystal system, space groupMonoclinic, C2/c
Temperature (K)113
a, b, c (Å)27.447 (13), 8.886 (4), 28.861 (14)
β (°) 98.348 (8)
V3)6965 (6)
Z16
Radiation typeMo Kα
µ (mm1)2.82
Crystal size (mm)0.20 × 0.18 × 0.14
Data collection
DiffractometerRigaku Saturn724 CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2009)
Tmin, Tmax0.603, 0.694
No. of measured, independent and
observed [I > 2σ(I)] reflections
26327, 6143, 4903
Rint0.104
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.180, 1.09
No. of reflections6143
No. of parameters399
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.952.663.665 (3)161
C20—H20···Cg2ii0.952.603.480 (9)155
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

References

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

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