Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017059/sg2163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017059/sg2163Isup2.hkl |
CCDC reference: 647572
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.126
- Data-to-parameter ratio = 19.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.530 0.760 Tmin(prime) and Tmax expected: 0.636 0.748 RR(prime) = 0.819 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The data collection sample was selected directly from many nicely formed specimens found in the bottle from the manufacturer.
A Fourier map around the expected positions of the methyl group H atoms clearly indicated two equivalent orientations. Both sets were included (riding model) and their occupancies refined, although the refined value is indistinguishable from 0.50. The C—H distance and C—C—H angles for the methyl H atoms were fixed, but the groups were allowed to rotate around the C—C bond.
3-chloro-2-methylbenzenesulfyl derivatives have shown biological activity as hydroxysteroid dehydrogenase inhibitors. These derivatives have potential as medicants to treat diseases mediated by hydroxysteroid dehydrogenase, such as type-2 diabetes (Brennan et al., 2006).
For related literature, see: Brennan et al. (2006).
Data collection: SCXmini (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku, 2005); software used to prepare material for publication: CrystalStructure and publCIF (Westrip, 2007\bbr08).
Fig. 1. View of the title molecule, with ellipsoids drawn at the 50% probability level. Bonds to the methyl H atoms are drawn with different line styles to distinguish the two alternate orientations. |
C7H6Cl2O2S | F(000) = 912 |
Mr = 225.08 | Dx = 1.616 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
a = 11.7233 (16) Å | Cell parameters from 5438 reflections |
b = 9.8849 (13) Å | θ = 3.1–27.5° |
c = 16.216 (2) Å | µ = 0.88 mm−1 |
β = 100.143 (2)° | T = 293 K |
V = 1849.8 (4) Å3 | Prism, colourless |
Z = 8 | 0.50 × 0.44 × 0.33 mm |
Rigaku SCXmini diffractometer | 2101 independent reflections |
Radiation source: long-fine-focus sealed tube | 1551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 6.85 pixels mm-1 | θmax = 27.5°, θmin = 3.5° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.53, Tmax = 0.76 | l = −16→20 |
6310 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0529P)2 + 2.2518P] where P = (Fo2 + 2Fc2)/3 |
2101 reflections | (Δ/σ)max < 0.001 |
110 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C7H6Cl2O2S | V = 1849.8 (4) Å3 |
Mr = 225.08 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.7233 (16) Å | µ = 0.88 mm−1 |
b = 9.8849 (13) Å | T = 293 K |
c = 16.216 (2) Å | 0.50 × 0.44 × 0.33 mm |
β = 100.143 (2)° |
Rigaku SCXmini diffractometer | 2101 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1551 reflections with I > 2σ(I) |
Tmin = 0.53, Tmax = 0.76 | Rint = 0.028 |
6310 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.49 e Å−3 |
2101 reflections | Δρmin = −0.47 e Å−3 |
110 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 | Occ. (<1) | |
Cl1 | 0.34739 (8) | −0.05390 (11) | 0.72960 (6) | 0.0881 (4) | |
Cl2 | 0.00368 (8) | −0.33397 (9) | 0.46807 (7) | 0.0842 (3) | |
S1 | 0.22728 (7) | 0.07269 (8) | 0.66422 (5) | 0.0567 (2) | |
O1 | 0.1375 (2) | 0.0813 (3) | 0.71120 (13) | 0.0744 (7) | |
O2 | 0.2877 (3) | 0.1917 (3) | 0.64869 (16) | 0.0909 (8) | |
C1 | 0.1833 (2) | −0.0162 (3) | 0.56917 (16) | 0.0440 (6) | |
C2 | 0.2169 (3) | 0.0433 (3) | 0.49984 (19) | 0.0553 (7) | |
H1 | 0.2617 | 0.1214 | 0.5059 | 0.077* | |
C3 | 0.1835 (3) | −0.0139 (3) | 0.42236 (18) | 0.0614 (8) | |
H3 | 0.2052 | 0.0257 | 0.3755 | 0.086* | |
C4 | 0.1182 (3) | −0.1296 (3) | 0.41408 (18) | 0.0561 (7) | |
H2 | 0.0953 | −0.1687 | 0.3616 | 0.079* | |
C5 | 0.0868 (2) | −0.1876 (3) | 0.48380 (18) | 0.0496 (6) | |
C6 | 0.1180 (2) | −0.1350 (3) | 0.56484 (16) | 0.0450 (6) | |
C7 | 0.0831 (3) | −0.2042 (4) | 0.6395 (2) | 0.0720 (9) | |
H4A | 0.1392 (3) | −0.2724 (4) | 0.6602 (2) | 0.101* | 0.51 (4) |
H5A | 0.0796 (3) | −0.1387 (4) | 0.6827 (2) | 0.101* | 0.51 (4) |
H6A | 0.0084 (3) | −0.2454 (4) | 0.6232 (2) | 0.101* | 0.51 (4) |
H4B | 0.0100 (3) | −0.1690 (4) | 0.6485 (2) | 0.101* | 0.49 (4) |
H5B | 0.0763 (3) | −0.2997 (4) | 0.6293 (2) | 0.101* | 0.49 (4) |
H6B | 0.1409 (3) | −0.1877 (4) | 0.6883 (2) | 0.101* | 0.49 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0692 (5) | 0.1192 (8) | 0.0678 (6) | 0.0225 (5) | −0.0101 (4) | −0.0142 (5) |
Cl2 | 0.0835 (6) | 0.0593 (5) | 0.1071 (7) | −0.0258 (4) | 0.0097 (5) | −0.0104 (5) |
S1 | 0.0602 (4) | 0.0650 (5) | 0.0453 (4) | −0.0035 (3) | 0.0105 (3) | −0.0092 (3) |
O1 | 0.0691 (14) | 0.1077 (19) | 0.0487 (12) | 0.0131 (13) | 0.0169 (10) | −0.0114 (12) |
O2 | 0.121 (2) | 0.0754 (15) | 0.0774 (16) | −0.0412 (15) | 0.0193 (15) | −0.0218 (13) |
C1 | 0.0435 (13) | 0.0500 (14) | 0.0401 (13) | −0.0022 (11) | 0.0115 (11) | 0.0021 (11) |
C2 | 0.0644 (17) | 0.0526 (16) | 0.0533 (16) | −0.0148 (14) | 0.0224 (14) | −0.0003 (13) |
C3 | 0.075 (2) | 0.071 (2) | 0.0429 (15) | −0.0047 (16) | 0.0237 (15) | 0.0036 (14) |
C4 | 0.0595 (17) | 0.0640 (17) | 0.0445 (15) | 0.0028 (14) | 0.0081 (13) | −0.0060 (14) |
C5 | 0.0428 (13) | 0.0428 (13) | 0.0617 (17) | −0.0012 (11) | 0.0051 (12) | −0.0009 (12) |
C6 | 0.0402 (12) | 0.0478 (14) | 0.0478 (14) | 0.0014 (11) | 0.0102 (11) | 0.0106 (12) |
C7 | 0.079 (2) | 0.074 (2) | 0.065 (2) | −0.0148 (17) | 0.0178 (17) | 0.0248 (17) |
Cl1—S1 | 2.0363 (12) | C4—C5 | 1.374 (4) |
Cl2—C5 | 1.738 (3) | C5—C6 | 1.401 (4) |
S1—O1 | 1.406 (2) | C6—C7 | 1.508 (4) |
S1—O2 | 1.419 (3) | C7—H4B | 0.9600 |
S1—C1 | 1.770 (3) | C7—H6A | 0.9600 |
C1—C2 | 1.386 (4) | C7—H4A | 0.9600 |
C1—C6 | 1.397 (4) | C7—H5B | 0.9600 |
C2—C3 | 1.371 (4) | C7—H6B | 0.9600 |
C3—C4 | 1.370 (4) | C7—H5A | 0.9600 |
O1—S1—O2 | 119.41 (17) | C1—C6—C5 | 114.2 (2) |
O1—S1—C1 | 111.75 (13) | C1—C6—C7 | 124.4 (3) |
O2—S1—C1 | 109.58 (14) | C5—C6—C7 | 121.5 (3) |
O1—S1—Cl1 | 105.65 (11) | H6A—C7—H4A | 109.5 |
O2—S1—Cl1 | 106.32 (14) | H6A—C7—H5A | 109.5 |
C1—S1—Cl1 | 102.52 (10) | H4A—C7—H5A | 109.5 |
C2—C1—C6 | 123.2 (2) | H4B—C7—H5B | 109.5 |
C2—C1—S1 | 114.5 (2) | H4B—C7—H6B | 109.5 |
C6—C1—S1 | 122.28 (19) | H5B—C7—H6B | 109.5 |
C3—C2—C1 | 119.5 (3) | H4A—C7—C6 | 109.5 |
C4—C3—C2 | 119.9 (3) | H5A—C7—C6 | 109.5 |
C3—C4—C5 | 119.6 (3) | H6A—C7—C6 | 109.5 |
C4—C5—C6 | 123.6 (3) | H4B—C7—C6 | 109.5 |
C4—C5—Cl2 | 116.8 (2) | H5B—C7—C6 | 109.5 |
C6—C5—Cl2 | 119.6 (2) | H6B—C7—C6 | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C7H6Cl2O2S |
Mr | 225.08 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.7233 (16), 9.8849 (13), 16.216 (2) |
β (°) | 100.143 (2) |
V (Å3) | 1849.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.88 |
Crystal size (mm) | 0.50 × 0.44 × 0.33 |
Data collection | |
Diffractometer | Rigaku SCXmini |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.53, 0.76 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6310, 2101, 1551 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.126, 1.04 |
No. of reflections | 2101 |
No. of parameters | 110 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.47 |
Computer programs: SCXmini (Rigaku, 2006), PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku, 2005), CrystalStructure and publCIF (Westrip, 2007\bbr08).
Cl1—S1 | 2.0363 (12) | C1—C6 | 1.397 (4) |
Cl2—C5 | 1.738 (3) | C2—C3 | 1.371 (4) |
S1—O1 | 1.406 (2) | C3—C4 | 1.370 (4) |
S1—O2 | 1.419 (3) | C4—C5 | 1.374 (4) |
S1—C1 | 1.770 (3) | C5—C6 | 1.401 (4) |
C1—C2 | 1.386 (4) | C6—C7 | 1.508 (4) |
O1—S1—O2 | 119.41 (17) | O2—S1—Cl1 | 106.32 (14) |
O1—S1—C1 | 111.75 (13) | C1—S1—Cl1 | 102.52 (10) |
O2—S1—C1 | 109.58 (14) | C2—C1—S1 | 114.5 (2) |
O1—S1—Cl1 | 105.65 (11) | C6—C1—S1 | 122.28 (19) |
3-chloro-2-methylbenzenesulfyl derivatives have shown biological activity as hydroxysteroid dehydrogenase inhibitors. These derivatives have potential as medicants to treat diseases mediated by hydroxysteroid dehydrogenase, such as type-2 diabetes (Brennan et al., 2006).