#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220489.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_2220489
loop_
_publ_author_name
'Meneghetti, Fiorella'
'Bombieri, Gabriella'
'Logoteta, Patrizia'
'De Luca, Laura'
_publ_section_title
6-Chloro-1-(3,5-dimethylphenylsulfonyl)-1H-benzimidazol-2(3H)-one
_journal_coeditor_code           FJ2178
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o159
_journal_paper_doi               10.1107/S1600536808042694
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H13 Cl N2 O3 S'
_chemical_formula_moiety         'C15 H13 Cl N2 O3 S'
_chemical_formula_sum            'C15 H13 Cl N2 O3 S'
_chemical_formula_weight         336.78
_chemical_name_systematic
6-Chloro-1-(3,5-dimethylphenylsulfonyl)-1H-benzimidazol-2(3H)-one
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.77(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.173(3)
_cell_length_b                   14.036(3)
_cell_length_c                   8.949(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10
_cell_measurement_theta_min      9
_cell_volume                     1521.3(6)
_computing_cell_refinement       'SHELXL97 (Sheldrick, 2008)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3964
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0188P)²+1.7615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                3214
_reflns_number_total             3634
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fj2178.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220489
_cod_database_fobs_code          2220489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S1 0.78957(6) 0.45343(4) 0.18441(6) 0.04124(17) Uani d . 1 . .
Cl Cl1 0.89540(9) 0.73749(6) 0.67132(11) 0.0776(3) Uani d . 1 . .
O O3 0.81132(18) 0.55252(13) 0.1756(2) 0.0524(5) Uani d . 1 . .
O O1 0.80048(19) 0.25911(13) 0.3298(2) 0.0545(5) Uani d . 1 . .
N N2 0.85398(19) 0.32965(15) 0.5597(2) 0.0426(5) Uani d . 1 . .
H H2 0.8602 0.2802 0.6166 0.051 Uiso calc R 1 . .
N N1 0.83211(18) 0.42285(14) 0.3607(2) 0.0371(4) Uani d . 1 . .
O O2 0.83888(19) 0.38810(15) 0.0896(2) 0.0567(5) Uani d . 1 . .
C C2 0.8705(2) 0.42257(18) 0.6105(3) 0.0387(5) Uani d . 1 . .
C C8 0.6470(2) 0.4341(2) 0.1704(3) 0.0508(6) Uani d . 1 . .
C C7 0.85543(19) 0.48366(17) 0.4866(2) 0.0351(5) Uani d . 1 . .
C C1 0.8269(2) 0.32671(17) 0.4093(3) 0.0417(5) Uani d . 1 . .
C C4 0.9024(2) 0.5555(2) 0.7717(3) 0.0519(7) Uani d . 1 . .
H H4 0.9177 0.5817 0.8670 0.062 Uiso calc R 1 . .
C C6 0.8637(2) 0.58080(18) 0.5011(3) 0.0425(5) Uani d . 1 . .
H H6 0.8547 0.6215 0.4188 0.051 Uiso calc R 1 . .
C C3 0.8955(2) 0.4574(2) 0.7537(3) 0.0464(6) Uani d . 1 . .
H H3 0.9074 0.4166 0.8356 0.056 Uiso calc R 1 . .
C C5 0.8864(2) 0.61419(19) 0.6469(3) 0.0491(6) Uani d . 1 . .
C C13 0.6006(3) 0.3614(3) 0.0822(4) 0.0734(10) Uani d . 1 . .
H H13 0.6452 0.3204 0.0334 0.088 Uiso calc R 1 . .
C C9 0.5842(3) 0.4951(3) 0.2471(4) 0.0671(9) Uani d . 1 . .
H H9 0.6174 0.5437 0.3060 0.081 Uiso calc R 1 . .
C C11 0.4255(4) 0.4091(4) 0.1443(5) 0.0941(15) Uani d . 1 . .
H H11 0.3495 0.3998 0.1362 0.113 Uiso calc R 1 . .
C C10 0.4705(3) 0.4829(4) 0.2352(5) 0.0858(12) Uani d . 1 . .
C C12 0.4884(4) 0.3499(3) 0.0666(6) 0.0954(15) Uani d . 1 . .
C C15 0.4332(5) 0.2721(4) -0.0324(8) 0.152(2) Uani d . 1 . .
H H15A 0.3928 0.2305 0.0274 0.229 Uiso calc R 1 . .
H H15B 0.4884 0.2362 -0.0772 0.229 Uiso calc R 1 . .
H H15C 0.3835 0.3005 -0.1099 0.229 Uiso calc R 1 . .
C C14 0.4004(4) 0.5506(5) 0.3165(7) 0.1339(17) Uani d . 1 . .
H H14A 0.4464 0.5843 0.3924 0.201 Uiso calc R 1 . .
H H14B 0.3454 0.5152 0.3626 0.201 Uiso calc R 1 . .
H H14C 0.3650 0.5953 0.2462 0.201 Uiso calc R 1 . .
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'
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O2 . . 120.41(13) ?
O3 S1 N1 . . 105.25(11) ?
O2 S1 N1 . . 106.81(11) ?
O3 S1 C8 . . 109.74(14) ?
O2 S1 C8 . . 109.40(14) ?
N1 S1 C8 . . 103.86(12) ?
C1 N2 C2 . . 111.5(2) ?
C1 N2 H2 . . 124.2 ?
C2 N2 H2 . . 124.2 ?
C7 N1 C1 . . 109.87(18) ?
C7 N1 S1 . . 127.94(16) ?
C1 N1 S1 . . 120.99(16) ?
C3 C2 N2 . . 130.5(2) ?
C3 C2 C7 . . 121.3(2) ?
N2 C2 C7 . . 108.2(2) ?
C13 C8 C9 . . 122.0(3) ?
C13 C8 S1 . . 120.2(3) ?
C9 C8 S1 . . 117.7(2) ?
C6 C7 C2 . . 122.1(2) ?
C6 C7 N1 . . 132.8(2) ?
C2 C7 N1 . . 105.1(2) ?
O1 C1 N2 . . 129.2(2) ?
O1 C1 N1 . . 125.6(2) ?
N2 C1 N1 . . 105.1(2) ?
C5 C4 C3 . . 119.6(2) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C7 C6 C5 . . 115.5(2) ?
C7 C6 H6 . . 122.3 ?
C5 C6 H6 . . 122.3 ?
C2 C3 C4 . . 117.7(2) ?
C2 C3 H3 . . 121.1 ?
C4 C3 H3 . . 121.1 ?
C4 C5 C6 . . 123.8(3) ?
C4 C5 Cl1 . . 119.1(2) ?
C6 C5 Cl1 . . 117.1(2) ?
C12 C13 C8 . . 119.6(4) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
C8 C9 C10 . . 119.0(4) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C12 C11 C10 . . 122.8(4) ?
C12 C11 H11 . . 118.6 ?
C10 C11 H11 . . 118.6 ?
C9 C10 C11 . . 117.8(4) ?
C9 C10 C14 . . 119.5(5) ?
C11 C10 C14 . . 122.7(4) ?
C11 C12 C13 . . 118.7(4) ?
C11 C12 C15 . . 119.7(5) ?
C13 C12 C15 . . 121.5(5) ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 . 1.419(2) ?
S1 O2 . 1.423(2) ?
S1 N1 . 1.6667(19) ?
S1 C8 . 1.749(3) ?
Cl1 C5 . 1.746(3) ?
O1 C1 . 1.210(3) ?
N2 C1 . 1.354(3) ?
N2 C2 . 1.389(3) ?
N2 H2 . 0.8600 ?
N1 C7 . 1.419(3) ?
N1 C1 . 1.421(3) ?
C2 C3 . 1.376(3) ?
C2 C7 . 1.399(3) ?
C8 C13 . 1.375(4) ?
C8 C9 . 1.376(5) ?
C7 C6 . 1.372(3) ?
C4 C5 . 1.385(4) ?
C4 C3 . 1.389(4) ?
C4 H4 . 0.9300 ?
C6 C5 . 1.388(4) ?
C6 H6 . 0.9300 ?
C3 H3 . 0.9300 ?
C13 C12 . 1.368(6) ?
C13 H13 . 0.9300 ?
C9 C10 . 1.388(5) ?
C9 H9 . 0.9300 ?
C11 C12 . 1.367(7) ?
C11 C10 . 1.395(7) ?
C11 H11 . 0.9300 ?
C10 C14 . 1.512(7) ?
C12 C15 . 1.520(7) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
_geom_hbond_publ_flag
N2 H2 O1 4_566 0.86 2.18 2.852(3) 134.8(9) y
N2 H2 O2 4_566 0.86 2.39 3.075(3) 137.5(9) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20560129
