data_shelxl


_publ_section_figure_captions
;
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.
;


_publ_section_acknowledgements
;
The authors thank Dr. David Lonergan for suggesting a list of possibly 
crystalline reagents.

;

_audit_update_record
;
2007-03-06 # Formatted by publCIF
;

_publ_section_exptl_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.
;


_publ_section_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 <i>et al.</i>, 2006).
;


_publ_contact_letter 
;
Please consider this CIF for publication. I certify that this contibution is 
the original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;

_publ_requested_category 'EO'

_publ_requested_journal 'Acta Cryst. E'

_publ_section_abstract
;
The structure of 3-chloro-2-methylbenzene-1-sulfonyl chloride,
C~7~H~6~Cl~2~O~2~S, has monoclinic (<i>C</i>2/<i>c</i>) symmetry. The
structure exhibits a very slight disorder of the main molecule, <i>i.e.</i>
there are two observable orientations of the 3 methyl H atoms.
;

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

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


_publ_contact_author_name        'Lee M. Daniels'

_publ_contact_author_address     
;
Rigaku Americas Corp.
9009 New Trails Dr.
The Woodlands, TX 77381
;

_publ_contact_author_email       'lee.daniels@rigaku.com'
_publ_contact_author_phone       '281 362 2300'
_publ_contact_author_fax         '281 364 3628'

loop_
_publ_author_name
_publ_author_address
'Chan, Luisa'
;
Nanosyn
3760 Haven Ave.
Menlo Park, CA 94025
;
'Daniels, Lee'
;
Rigaku Americas Corp.
9009 New Trails Dr.
The Woodlands, TX 77381
;

_publ_section_references
;
Higashi, T. (1995). <i>ABSCOR</i>: Empirical Absorption Correction based on
Fourier Series Approximation. Rigaku Corporation, 3-9-12 Matsubara, Akishima,
Tokyo 196-8666, JAPAN.

Rigaku (1998). <i>Process-Auto</i>: Automatic Data Acquisition and Processing
Package for Imaging Plate and CCD Diffractometers. Rigaku Corporation, 3-9-12
Matsubara, Akishima, Tokyo 196-8666, JAPAN.

Rigaku (2005). <i>CrystalStructure</i>: Structure Solution and Refinement
program, Version 3.7. Rigaku Americas Corp., 9009 New Trails Drive, The
Woodlands, TX 77381-5209, USA.

Rigaku (2006). <i>SCXmini Benchtop Crystallography System software</i>, Version
1.0. Rigaku Americas Corp., 9009 New Trails Drive, The Woodlands, TX
77381-5209, USA.

Sheldrick, G. M. (1990). <i>Acta Cryst.</i> A<b>46</b>, 467--473.

Sheldrick, G. M. (1997). <i>SHELXL97</i>. University of G\"ottingen, Germany.

Brennan, N. K., Chang, E., Kaldor, S. W., Kiryanov, A. A., Jennings, A. J. &
Stafford, J. A. (2006). Patent No. WO/2006/066109, "Hydroxysteroid
Dehydrogenase Inhibitors"

Westrip, S. P., (2006). <i>publCIF</i>. A CIF editor for authors. 
International Union of Crystallography.

;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '3-chloro-2-methylbenzene-1-sulfonyl chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 Cl2 O2 S'
_chemical_formula_sum            'C7 H6 Cl2 O2 S'
_chemical_formula_weight         225.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.7233(16)
_cell_length_b                   9.8849(13)
_cell_length_c                   16.216(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.143(2)
_cell_angle_gamma                90.00
_cell_volume                     1849.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5438
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'long-fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 6.85
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        <0.2
_diffrn_reflns_number            6310
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2101
_reflns_number_gt                1551
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SCXmini (Rigaku, 2006)'
_computing_cell_refinement       'Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure V3.7 (Rigaku, 2005)'
_computing_publication_material  
'CrystalStructure V3.7 (Rigaku, 2005) and publCIF (Westrip, 2006)'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+2.2518P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2101
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.34739(8) -0.05390(11) 0.72960(6) 0.0881(4) Uani 1 1 d . . . 
Cl2 Cl 0.00368(8) -0.33397(9) 0.46807(7) 0.0842(3) Uani 1 1 d . . . 
S1 S 0.22728(7) 0.07269(8) 0.66422(5) 0.0567(2) Uani 1 1 d . . . 
O1 O 0.1375(2) 0.0813(3) 0.71120(13) 0.0744(7) Uani 1 1 d . . . 
O2 O 0.2877(3) 0.1917(3) 0.64869(16) 0.0909(8) Uani 1 1 d . . . 
C1 C 0.1833(2) -0.0162(3) 0.56917(16) 0.0440(6) Uani 1 1 d . . . 
C2 C 0.2169(3) 0.0433(3) 0.49984(19) 0.0553(7) Uani 1 1 d . . . 
H1 H 0.2617 0.1214 0.5059 0.077 Uiso 1 1 calc R . . 
C3 C 0.1835(3) -0.0139(3) 0.42236(18) 0.0614(8) Uani 1 1 d . . . 
H3 H 0.2052 0.0257 0.3755 0.086 Uiso 1 1 calc R . . 
C4 C 0.1182(3) -0.1296(3) 0.41408(18) 0.0561(7) Uani 1 1 d . . . 
H2 H 0.0953 -0.1687 0.3616 0.079 Uiso 1 1 calc R . . 
C5 C 0.0868(2) -0.1876(3) 0.48380(18) 0.0496(6) Uani 1 1 d . . . 
C6 C 0.1180(2) -0.1350(3) 0.56484(16) 0.0450(6) Uani 1 1 d . A . 
C7 C 0.0831(3) -0.2042(4) 0.6395(2) 0.0720(9) Uani 1 1 d . . . 
H4A H 0.1392(3) -0.2724(4) 0.6602(2) 0.101 Uiso 0.51(4) 1 d PR A 1 
H5A H 0.0796(3) -0.1387(4) 0.6827(2) 0.101 Uiso 0.51(4) 1 d PR A 1 
H6A H 0.0084(3) -0.2454(4) 0.6232(2) 0.101 Uiso 0.51(4) 1 d PR A 1 
H4B H 0.0100(3) -0.1690(4) 0.6485(2) 0.101 Uiso 0.49(4) 1 d PR A 2 
H5B H 0.0763(3) -0.2997(4) 0.6293(2) 0.101 Uiso 0.49(4) 1 d PR A 2 
H6B H 0.1409(3) -0.1877(4) 0.6883(2) 0.101 Uiso 0.49(4) 1 d PR A 2 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
Cl1 0.0692(5) 0.1192(8) 0.0678(6) -0.0142(5) -0.0101(4) 0.0225(5) 
Cl2 0.0835(6) 0.0593(5) 0.1071(7) -0.0104(5) 0.0097(5) -0.0258(4) 
S1 0.0602(4) 0.0650(5) 0.0453(4) -0.0092(3) 0.0105(3) -0.0035(3) 
O1 0.0691(14) 0.1077(19) 0.0487(12) -0.0114(12) 0.0169(10) 0.0131(13) 
O2 0.121(2) 0.0754(15) 0.0774(16) -0.0218(13) 0.0193(15) -0.0412(15) 
C1 0.0435(13) 0.0500(14) 0.0401(13) 0.0021(11) 0.0115(11) -0.0022(11) 
C2 0.0644(17) 0.0526(16) 0.0533(16) -0.0003(13) 0.0224(14) -0.0148(14) 
C3 0.075(2) 0.071(2) 0.0429(15) 0.0036(14) 0.0237(15) -0.0047(16) 
C4 0.0595(17) 0.0640(17) 0.0445(15) -0.0060(14) 0.0081(13) 0.0028(14) 
C5 0.0428(13) 0.0428(13) 0.0617(17) -0.0009(12) 0.0051(12) -0.0012(11) 
C6 0.0402(12) 0.0478(14) 0.0478(14) 0.0106(12) 0.0102(11) 0.0014(11) 
C7 0.079(2) 0.074(2) 0.065(2) 0.0248(17) 0.0178(17) -0.0148(17) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cl1 S1 2.0363(12) . y 
Cl2 C5 1.738(3) . y 
S1 O1 1.406(2) . y 
S1 O2 1.419(3) . y 
S1 C1 1.770(3) . y 
C1 C2 1.386(4) . y 
C1 C6 1.397(4) . y 
C2 C3 1.371(4) . y 
C3 C4 1.370(4) . y 
C4 C5 1.374(4) . y 
C5 C6 1.401(4) . y 
C6 C7 1.508(4) . y 
C7 H4B 0.9600 . ? 
C7 H6A 0.9600 . ? 
C7 H4A 0.9600 . ? 
C7 H5B 0.9600 . ? 
C7 H6B 0.9600 . ? 
C7 H5A 0.9600 . ? 

loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetyy_3 
 _geom_angle_publ_flag 
O1 S1 O2 119.41(17) . . y 
O1 S1 C1 111.75(13) . . y 
O2 S1 C1 109.58(14) . . y 
O1 S1 Cl1 105.65(11) . . y 
O2 S1 Cl1 106.32(14) . . y 
C1 S1 Cl1 102.52(10) . . y 
C2 C1 C6 123.2(2) . . ? 
C2 C1 S1 114.5(2) . . y 
C6 C1 S1 122.28(19) . . y 
C3 C2 C1 119.5(3) . . ? 
C4 C3 C2 119.9(3) . . ? 
C3 C4 C5 119.6(3) . . ? 
C4 C5 C6 123.6(3) . . ? 
C4 C5 Cl2 116.8(2) . . ? 
C6 C5 Cl2 119.6(2) . . ? 
C1 C6 C5 114.2(2) . . ? 
C1 C6 C7 124.4(3) . . ? 
C5 C6 C7 121.5(3) . . ? 
H6A C7 H4A 109.5 . . ? 
H6A C7 H5A 109.5 . . ? 
H4A C7 H5A 109.5 . . ? 
H4B C7 H5B 109.5 . . ? 
H4B C7 H6B 109.5 . . ? 
H5B C7 H6B 109.5 . . ? 
H4A C7 C6 109.5 . . ? 
H5A C7 C6 109.5 . . ? 
H6A C7 C6 109.5 . . ? 
H4B C7 C6 109.5 . . ? 
H5B C7 C6 109.5 . . ? 
H6B C7 C6 109.5 . . ? 

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.053
_chemical_compound_source        "Sigma-Aldrich"