#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2222994.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_2222994
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Shakuntala, K.'
'Fuess, Hartmut'
_publ_section_title
;
 2-Chlorobenzenesulfonamide
;
_journal_coeditor_code           BT5028
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2144
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H6 Cl N O2 S'
_chemical_formula_moiety         'C6 H6 Cl N O2 S'
_chemical_formula_sum            'C6 H6 Cl N O2 S'
_chemical_formula_weight         191.63
_chemical_name_systematic
;
2-Chlorobenzenesulfonamide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 91.510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9550(10)
_cell_length_b                   14.848(3)
_cell_length_c                   7.7510(10)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.63
_cell_volume                     800.2(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega and phi scans.
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0081
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1598
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.8423
_exptl_absorpt_correction_T_min  0.7350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.209
_refine_ls_abs_structure_details 'Flack (1983), 215 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1031
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.2306P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                1004
_reflns_number_total             1031
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bt5028.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C c'
_cod_database_code               2222994
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'
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
Cl Cl1 0.56409(10) 0.10747(7) 0.84733(11) 0.0700(3) Uani d . 1
S S1 0.18379(8) 0.20974(3) 0.98884(8) 0.03276(14) Uani d . 1
O O1 -0.0067(3) 0.22742(12) 1.0448(3) 0.0486(5) Uani d . 1
O O2 0.3434(3) 0.23916(13) 1.0939(2) 0.0535(5) Uani d . 1
N N1 0.2010(4) 0.25747(15) 0.8048(3) 0.0396(5) Uani d D 1
H H11 0.309(3) 0.251(2) 0.755(4) 0.048 Uiso d D 1
H H12 0.105(4) 0.249(2) 0.740(3) 0.048 Uiso d D 1
C C1 0.1995(4) 0.09052(15) 0.9649(3) 0.0335(5) Uani d . 1
C C2 0.3626(4) 0.04740(18) 0.9082(4) 0.0443(6) Uani d . 1
C C3 0.3663(6) -0.0459(2) 0.8966(4) 0.0588(8) Uani d . 1
H H3 0.4755 -0.0751 0.8582 0.071 Uiso calc R 1
C C4 0.2078(7) -0.0951(2) 0.9421(4) 0.0674(10) Uani d . 1
H H4 0.2106 -0.1576 0.9341 0.081 Uiso calc R 1
C C5 0.0464(6) -0.05329(19) 0.9990(4) 0.0590(8) Uani d . 1
H H5 -0.0600 -0.0872 1.0292 0.071 Uiso calc R 1
C C6 0.0415(4) 0.04025(18) 1.0117(4) 0.0432(6) Uani d . 1
H H6 -0.0677 0.0689 1.0515 0.052 Uiso calc R 1
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 0.0380(4) 0.0856(6) 0.0871(6) 0.0153(4) 0.0158(4) 0.0148(5)
S1 0.0338(3) 0.0335(2) 0.0310(2) -0.0015(3) 0.00213(18) -0.0023(2)
O1 0.0468(11) 0.0480(9) 0.0520(11) 0.0068(9) 0.0205(9) -0.0043(9)
O2 0.0590(14) 0.0501(11) 0.0506(11) -0.0152(10) -0.0172(10) -0.0031(9)
N1 0.0364(11) 0.0449(11) 0.0375(11) 0.0035(10) 0.0025(8) 0.0055(9)
C1 0.0381(12) 0.0343(10) 0.0280(11) 0.0023(11) -0.0025(9) 0.0013(8)
C2 0.0478(16) 0.0476(13) 0.0374(13) 0.0118(13) -0.0008(12) 0.0047(11)
C3 0.078(2) 0.0498(15) 0.0485(15) 0.0276(17) -0.0026(15) 0.0016(13)
C4 0.116(3) 0.0360(14) 0.0497(18) 0.0069(19) -0.0055(19) 0.0025(12)
C5 0.079(2) 0.0399(14) 0.0574(18) -0.0158(15) -0.0058(17) 0.0052(13)
C6 0.0445(16) 0.0412(12) 0.0436(14) -0.0049(12) -0.0026(12) 0.0022(11)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
O1 S1 O2 118.92(13)
O1 S1 N1 106.32(13)
O2 S1 N1 107.32(12)
O1 S1 C1 105.88(12)
O2 S1 C1 108.31(12)
N1 S1 C1 109.91(11)
S1 N1 H11 116(2)
S1 N1 H12 113(2)
H11 N1 H12 114(3)
C6 C1 C2 119.8(2)
C6 C1 S1 117.2(2)
C2 C1 S1 123.0(2)
C1 C2 C3 119.9(3)
C1 C2 Cl1 121.5(2)
C3 C2 Cl1 118.6(2)
C4 C3 C2 119.8(3)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 120.8(3)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 119.8(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 119.9(3)
C1 C6 H6 120.1
C5 C6 H6 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.737(3)
S1 O1 1.429(2)
S1 O2 1.4275(19)
S1 N1 1.600(2)
S1 C1 1.784(2)
N1 H11 0.857(19)
N1 H12 0.835(18)
C1 C6 1.385(4)
C1 C2 1.384(4)
C2 C3 1.389(4)
C3 C4 1.376(5)
C3 H3 0.9300
C4 C5 1.366(5)
C4 H4 0.9300
C5 C6 1.393(4)
C5 H5 0.9300
C6 H6 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H11 O1 4_554 0.857(19) 2.12(2) 2.908(3) 152(3)
N1 H12 O2 4_454 0.835(18) 2.12(2) 2.941(3) 166(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 C1 C6 -3.7(2)
O2 S1 C1 C6 124.8(2)
N1 S1 C1 C6 -118.19(19)
O1 S1 C1 C2 178.5(2)
O2 S1 C1 C2 -52.9(2)
N1 S1 C1 C2 64.0(2)
C6 C1 C2 C3 0.7(4)
S1 C1 C2 C3 178.4(2)
C6 C1 C2 Cl1 179.77(19)
S1 C1 C2 Cl1 -2.5(3)
C1 C2 C3 C4 -0.2(4)
Cl1 C2 C3 C4 -179.3(2)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 -0.1(5)
C2 C1 C6 C5 -1.0(4)
S1 C1 C6 C5 -178.8(2)
C4 C5 C6 C1 0.7(4)