#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/35/2213541.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213541
loop_
_publ_author_name
'Chan, Luisa'
'Daniels, Lee'
_publ_section_title
;
 3-Chloro-2-methylbenzene-1-sulfonyl chloride
;
_journal_coeditor_code           SG2163
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2435
_journal_page_last               o2435
_journal_paper_doi               10.1107/S1600536807017059
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H6 Cl2 O2 S'
_chemical_formula_moiety         'C7 H6 Cl2 O2 S'
_chemical_formula_sum            'C7 H6 Cl2 O2 S'
_chemical_formula_weight         225.08
_chemical_name_systematic
'3-chloro-2-methylbenzene-1-sulfonyl chloride'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.143(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.7233(16)
_cell_length_b                   9.8849(13)
_cell_length_c                   16.216(2)
_cell_measurement_reflns_used    5438
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1849.8(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'SCXmini (Rigaku, 2006)'
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2005)'
_computing_publication_material
'CrystalStructure and publCIF (Westrip, 2007\\bbr08)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.85
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6310
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.51
_diffrn_standards_decay_%        <0.2
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.473
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+2.2518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                1551
_reflns_number_total             2101
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2163.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213541
_cod_database_fobs_code          2213541
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.34739(8) -0.05390(11) 0.72960(6) 0.0881(4) Uani d . 1 . .
Cl Cl2 0.00368(8) -0.33397(9) 0.46807(7) 0.0842(3) Uani d . 1 . .
S S1 0.22728(7) 0.07269(8) 0.66422(5) 0.0567(2) Uani d . 1 . .
O O1 0.1375(2) 0.0813(3) 0.71120(13) 0.0744(7) Uani d . 1 . .
O O2 0.2877(3) 0.1917(3) 0.64869(16) 0.0909(8) Uani d . 1 . .
C C1 0.1833(2) -0.0162(3) 0.56917(16) 0.0440(6) Uani d . 1 . .
C C2 0.2169(3) 0.0433(3) 0.49984(19) 0.0553(7) Uani d . 1 . .
H H1 0.2617 0.1214 0.5059 0.077 Uiso calc R 1 . .
C C3 0.1835(3) -0.0139(3) 0.42236(18) 0.0614(8) Uani d . 1 . .
H H3 0.2052 0.0257 0.3755 0.086 Uiso calc R 1 . .
C C4 0.1182(3) -0.1296(3) 0.41408(18) 0.0561(7) Uani d . 1 . .
H H2 0.0953 -0.1687 0.3616 0.079 Uiso calc R 1 . .
C C5 0.0868(2) -0.1876(3) 0.48380(18) 0.0496(6) Uani d . 1 . .
C C6 0.1180(2) -0.1350(3) 0.56484(16) 0.0450(6) Uani d . 1 A .
C C7 0.0831(3) -0.2042(4) 0.6395(2) 0.0720(9) Uani d . 1 . .
H H4A 0.1392(3) -0.2724(4) 0.6602(2) 0.101 Uiso d PR 0.51(4) A 1
H H5A 0.0796(3) -0.1387(4) 0.6827(2) 0.101 Uiso d PR 0.51(4) A 1
H H6A 0.0084(3) -0.2454(4) 0.6232(2) 0.101 Uiso d PR 0.51(4) A 1
H H4B 0.0100(3) -0.1690(4) 0.6485(2) 0.101 Uiso d PR 0.49(4) A 2
H H5B 0.0763(3) -0.2997(4) 0.6293(2) 0.101 Uiso d PR 0.49(4) A 2
H H6B 0.1409(3) -0.1877(4) 0.6883(2) 0.101 Uiso d PR 0.49(4) 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_12
_atom_site_aniso_U_13
_atom_site_aniso_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)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_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 ?
