organic compounds
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
The 17H14BrCl3O, 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.
of the title compound, CRelated 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
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2009); cell 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
10.1107/S1600536813003735/cv5386sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813003735/cv5386Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813003735/cv5386Isup3.cml
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
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.All H atoms were geometrically positioned, with C–H = 0.95–0.99 Å, and included in the final cycles of
using a riding model, with Uiso(H) = 1.2–1.5 Ueq(C).Data collection: CrystalClear (Rigaku/MSC, 2009); cell
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).Fig. 1. View of the title compound showing the atomic numbering and 40% probability displacement ellipsoids. |
C17H14BrCl3O | F(000) = 3360 |
Mr = 420.54 | Dx = 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 |
Rigaku Saturn724 CCD diffractometer | 6143 independent reflections |
Radiation source: rotating anode | 4903 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.104 |
Detector resolution: 14.22 pixels mm-1 | θmax = 25.0°, θmin = 1.5° |
ω and ϕ scans | h = −32→32 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) | k = −10→10 |
Tmin = 0.603, Tmax = 0.694 | l = −34→33 |
26327 measured reflections |
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(Fo2) + (0.0747P)2] where P = (Fo2 + 2Fc2)/3 |
6143 reflections | (Δ/σ)max = 0.003 |
399 parameters | Δρmax = 1.54 e Å−3 |
0 restraints | Δρmin = −0.89 e Å−3 |
C17H14BrCl3O | V = 6965 (6) Å3 |
Mr = 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)° |
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 = 0.694 | Rint = 0.104 |
26327 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.54 e Å−3 |
6143 reflections | Δρmin = −0.89 e Å−3 |
399 parameters |
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 | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.603, 0.694 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26327, 6143, 4903 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 1.54, −0.89 |
Computer programs: CrystalClear (Rigaku/MSC, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.