3-Chloro-2-methyl­benzene-1-sulfonyl chloride

In the structure of the title compound, C₇H₆Cl₂O₂S, the three methyl hydrogen atoms are disordered over two sets of positions with essentially equal occupancy.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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S1. Comment

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).

Related literature

For related literature, see: Brennan et al. (2006).

S2. Experimental

The data collection sample was selected directly from many nicely formed specimens found in the bottle from the manufacturer.

S3. Refinement

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.

Computing details

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).

Figures

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.

3-chloro-2-methylbenzene-1-sulfonyl chloride

Crystal data

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) Å^3	Prism, colourless
Z = 8	0.50 × 0.44 × 0.33 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 2.2518P] where P = (Fo^2 + 2Fc^2)/3
2101 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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