#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229352.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_2229352
loop_
_publ_author_name
'Abdireymov, K. B.'
'Mukhamedov, N. S.'
'Okmanov, R. Ya.'
'Ayimbetov, M. J.'
'Shakhidoyatov, Kh. M.'
_publ_section_title
;
 1-[(4-tert-Butylphenyl)sulfonyl]-1H-benzimidazole
;
_journal_coeditor_code           CV5052
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o709
_journal_paper_doi               10.1107/S1600536811005551
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H18 N2 O2 S'
_chemical_formula_moiety         'C17 H18 N2 O2 S'
_chemical_formula_sum            'C17 H18 N2 O2 S'
_chemical_formula_weight         314.39
_chemical_melting_point          395.0(10)
_chemical_name_systematic
;
1-[(4-tert-Butylphenyl)sulfonyl]-1H-benzimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.142(2)
_cell_length_b                   8.8940(18)
_cell_length_c                   15.324(3)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     1643.3(5)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED  (Stoe & Cie, 1997)'
_computing_molecular_graphics    'XP (Bruker, 1998)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Stoe STADI4 4-circle-diffractometer D092'
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method
;
Scan width (omega) = 1.56 - 1.80, scan ratio 2theta:omega = 1.00
I(Net) and sigma(I) calculated according to Blessing (1987)
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2727
_diffrn_reflns_theta_full        60.03
_diffrn_reflns_theta_max         60.03
_diffrn_reflns_theta_min         4.40
_diffrn_standards_decay_%        5.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.817
_exptl_absorpt_correction_T_max  0.6704
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North et al., 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.270
_refine_ls_extinction_coef       0.0054(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0583
_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)+(0.0478P)²+1.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                1813
_reflns_number_total             2429
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5052.cif
_cod_data_source_block           I
_cod_original_cell_volume        1643.3(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229352
_cod_database_fobs_code          2229352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S S1 0.15656(9) 0.56256(13) 0.30146(7) 0.0817(4) Uani d . 1 . .
O O1 0.2287(3) 0.6147(4) 0.24143(18) 0.1059(11) Uani d . 1 . .
O O2 0.0939(3) 0.4275(3) 0.2866(2) 0.1116(11) Uani d . 1 . .
N N1 0.2366(2) 0.5318(4) 0.39620(19) 0.0695(8) Uani d . 1 . .
N N3 0.2705(3) 0.4528(4) 0.5352(3) 0.0882(11) Uani d . 1 . .
C C2 0.2092(4) 0.4382(5) 0.4623(3) 0.0855(12) Uani d . 1 . .
H H2B 0.1509 0.3700 0.4542 0.103 Uiso calc R 1 . .
C C3A 0.3453(3) 0.5650(4) 0.5199(3) 0.0678(10) Uani d . 1 . .
C C4 0.4313(4) 0.6232(5) 0.5767(3) 0.0857(12) Uani d . 1 . .
H H4A 0.4460 0.5875 0.6340 0.103 Uiso calc R 1 . .
C C5 0.4939(4) 0.7339(6) 0.5467(4) 0.0924(13) Uani d . 1 . .
H H5A 0.5514 0.7757 0.5845 0.111 Uiso calc R 1 . .
C C6 0.4741(4) 0.7862(5) 0.4611(4) 0.0907(13) Uani d . 1 . .
H H6A 0.5189 0.8618 0.4425 0.109 Uiso calc R 1 . .
C C7 0.3901(3) 0.7286(4) 0.4032(3) 0.0764(11) Uani d . 1 . .
H H7A 0.3773 0.7625 0.3455 0.092 Uiso calc R 1 . .
C C7A 0.3259(3) 0.6188(4) 0.4344(2) 0.0621(9) Uani d . 1 . .
C C8 0.0676(3) 0.7078(4) 0.3232(2) 0.0593(9) Uani d . 1 . .
C C9 -0.0313(3) 0.6758(4) 0.3528(2) 0.0639(9) Uani d . 1 . .
H H9A -0.0507 0.5766 0.3627 0.077 Uiso calc R 1 . .
C C10 -0.1020(3) 0.7904(4) 0.3678(2) 0.0635(9) Uani d . 1 . .
H H10A -0.1696 0.7674 0.3875 0.076 Uiso calc R 1 . .
C C11 -0.0760(3) 0.9392(4) 0.3545(2) 0.0542(8) Uani d . 1 A .
C C12 0.0251(3) 0.9681(4) 0.3244(2) 0.0673(10) Uani d . 1 . .
H H12A 0.0450 1.0670 0.3146 0.081 Uiso calc R 1 . .
C C13 0.0966(3) 0.8541(4) 0.3086(2) 0.0672(10) Uani d . 1 . .
H H13A 0.1640 0.8759 0.2883 0.081 Uiso calc R 1 . .
C C14 -0.1562(3) 1.0652(5) 0.3703(3) 0.0709(10) Uani d . 1 . .
C C15 -0.2610(16) 1.044(3) 0.3059(11) 0.131(7) Uani d P 0.51(2) A 1
H H15A -0.3100 1.1275 0.3104 0.197 Uiso calc PR 0.51(2) A 1
H H15B -0.2974 0.9526 0.3196 0.197 Uiso calc PR 0.51(2) A 1
H H15C -0.2413 1.0382 0.2471 0.197 Uiso calc PR 0.51(2) A 1
C C16 -0.113(2) 1.2215(18) 0.361(3) 0.234(18) Uani d P 0.51(2) A 1
H H16A -0.0440 1.2326 0.3985 0.351 Uiso calc PR 0.51(2) A 1
H H16B -0.1658 1.2926 0.3788 0.351 Uiso calc PR 0.51(2) A 1
H H16C -0.1015 1.2394 0.3015 0.351 Uiso calc PR 0.51(2) A 1
C C17 -0.1958(18) 1.047(2) 0.4597(8) 0.142(10) Uani d P 0.51(2) A 1
H H17A -0.1330 1.0447 0.5041 0.214 Uiso calc PR 0.51(2) A 1
H H17B -0.2367 0.9549 0.4613 0.214 Uiso calc PR 0.51(2) A 1
H H17C -0.2428 1.1302 0.4706 0.214 Uiso calc PR 0.51(2) A 1
C C15A -0.0948(12) 1.1855(16) 0.4249(10) 0.093(5) Uani d P 0.49(2) A 2
H H15D -0.1469 1.2544 0.4454 0.140 Uiso calc PR 0.49(2) A 2
H H15E -0.0470 1.2386 0.3899 0.140 Uiso calc PR 0.49(2) A 2
H H15F -0.0511 1.1403 0.4743 0.140 Uiso calc PR 0.49(2) A 2
C C16A -0.248(2) 1.013(2) 0.415(3) 0.233(19) Uani d P 0.49(2) A 2
H H16D -0.2963 1.0962 0.4239 0.350 Uiso calc PR 0.49(2) A 2
H H16E -0.2204 0.9706 0.4708 0.350 Uiso calc PR 0.49(2) A 2
H H16F -0.2894 0.9380 0.3797 0.350 Uiso calc PR 0.49(2) A 2
C C17A -0.192(3) 1.141(3) 0.2816(11) 0.150(10) Uani d P 0.49(2) A 2
H H17D -0.2465 1.2174 0.2891 0.226 Uiso calc PR 0.49(2) A 2
H H17E -0.2240 1.0676 0.2403 0.226 Uiso calc PR 0.49(2) A 2
H H17F -0.1290 1.1865 0.2600 0.226 Uiso calc PR 0.49(2) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 . . 122.0(2) ?
O1 S1 N1 . . 106.03(18) ?
O2 S1 N1 . . 104.21(19) ?
O1 S1 C8 . . 109.00(19) ?
O2 S1 C8 . . 108.89(18) ?
N1 S1 C8 . . 105.39(15) ?
C2 N1 C7A . . 105.5(3) ?
C2 N1 S1 . . 124.7(3) ?
C7A N1 S1 . . 127.9(3) ?
C2 N3 C3A . . 104.6(4) ?
N3 C2 N1 . . 114.5(4) ?
N3 C2 H2B . . 122.7 ?
N1 C2 H2B . . 122.7 ?
C4 C3A N3 . . 128.7(4) ?
C4 C3A C7A . . 119.9(4) ?
N3 C3A C7A . . 111.4(4) ?
C5 C4 C3A . . 118.1(4) ?
C5 C4 H4A . . 120.9 ?
C3A C4 H4A . . 120.9 ?
C4 C5 C6 . . 121.5(4) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C7 C6 C5 . . 121.4(4) ?
C7 C6 H6A . . 119.3 ?
C5 C6 H6A . . 119.3 ?
C6 C7 C7A . . 116.8(4) ?
C6 C7 H7A . . 121.6 ?
C7A C7 H7A . . 121.6 ?
C7 C7A C3A . . 122.3(4) ?
C7 C7A N1 . . 133.7(4) ?
C3A C7A N1 . . 104.0(3) ?
C9 C8 C13 . . 120.4(3) ?
C9 C8 S1 . . 120.0(3) ?
C13 C8 S1 . . 119.7(3) ?
C8 C9 C10 . . 119.6(3) ?
C8 C9 H9A . . 120.2 ?
C10 C9 H9A . . 120.2 ?
C9 C10 C11 . . 122.0(3) ?
C9 C10 H10A . . 119.0 ?
C11 C10 H10A . . 119.0 ?
C10 C11 C12 . . 117.0(3) ?
C10 C11 C14 . . 121.3(3) ?
C12 C11 C14 . . 121.7(3) ?
C13 C12 C11 . . 121.7(3) ?
C13 C12 H12A . . 119.2 ?
C11 C12 H12A . . 119.2 ?
C8 C13 C12 . . 119.4(3) ?
C8 C13 H13A . . 120.3 ?
C12 C13 H13A . . 120.3 ?
C16A C14 C15A . . 109.0(13) ?
C16 C14 C17 . . 109.4(14) ?
C16A C14 C11 . . 112.5(8) ?
C16 C14 C11 . . 115.5(8) ?
C15A C14 C11 . . 109.1(6) ?
C17 C14 C11 . . 110.1(7) ?
C16 C14 C15 . . 109.3(12) ?
C17 C14 C15 . . 104.1(10) ?
C11 C14 C15 . . 107.8(7) ?
C16A C14 C17A . . 113.7(12) ?
C15A C14 C17A . . 104.5(10) ?
C11 C14 C17A . . 107.7(7) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
C14 C15A H15D . . 109.5 ?
C14 C15A H15E . . 109.5 ?
H15D C15A H15E . . 109.5 ?
C14 C15A H15F . . 109.5 ?
H15D C15A H15F . . 109.5 ?
H15E C15A H15F . . 109.5 ?
C14 C16A H16D . . 109.5 ?
C14 C16A H16E . . 109.5 ?
H16D C16A H16E . . 109.5 ?
C14 C16A H16F . . 109.5 ?
H16D C16A H16F . . 109.5 ?
H16E C16A H16F . . 109.5 ?
C14 C17A H17D . . 109.5 ?
C14 C17A H17E . . 109.5 ?
H17D C17A H17E . . 109.5 ?
C14 C17A H17F . . 109.5 ?
H17D C17A H17F . . 109.5 ?
H17E C17A H17F . . 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 O1 . 1.421(3) ?
S1 O2 . 1.426(3) ?
S1 N1 . 1.671(3) ?
S1 C8 . 1.742(3) ?
N1 C2 . 1.381(5) ?
N1 C7A . 1.402(5) ?
N3 C2 . 1.274(5) ?
N3 C3A . 1.387(5) ?
C2 H2B . 0.9300 ?
C3A C4 . 1.379(5) ?
C3A C7A . 1.389(5) ?
C4 C5 . 1.357(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.386(6) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.369(6) ?
C6 H6A . 0.9300 ?
C7 C7A . 1.371(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.363(5) ?
C8 C13 . 1.373(5) ?
C9 C10 . 1.369(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.381(5) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.385(5) ?
C11 C14 . 1.523(5) ?
C12 C13 . 1.375(5) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 C16A . 1.455(17) ?
C14 C16 . 1.498(17) ?
C14 C15A . 1.501(12) ?
C14 C17 . 1.513(15) ?
C14 C15 . 1.527(15) ?
C14 C17A . 1.535(18) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C15A H15D . 0.9600 ?
C15A H15E . 0.9600 ?
C15A H15F . 0.9600 ?
C16A H16D . 0.9600 ?
C16A H16E . 0.9600 ?
C16A H16F . 0.9600 ?
C17A H17D . 0.9600 ?
C17A H17E . 0.9600 ?
C17A H17F . 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
C7 H7A O2 2_555 0.93 2.558 3.430(5) 156 y
C13 H13A O1 2_555 0.93 2.560 3.292(5) 136 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C2 . . . . -158.3(3) ?
O2 S1 N1 C2 . . . . -28.4(4) ?
C8 S1 N1 C2 . . . . 86.2(3) ?
O1 S1 N1 C7A . . . . 39.6(4) ?
O2 S1 N1 C7A . . . . 169.5(3) ?
C8 S1 N1 C7A . . . . -75.9(3) ?
C3A N3 C2 N1 . . . . 0.6(5) ?
C7A N1 C2 N3 . . . . -1.4(5) ?
S1 N1 C2 N3 . . . . -166.9(3) ?
C2 N3 C3A C4 . . . . -178.8(4) ?
C2 N3 C3A C7A . . . . 0.5(5) ?
N3 C3A C4 C5 . . . . -179.9(4) ?
C7A C3A C4 C5 . . . . 0.8(6) ?
C3A C4 C5 C6 . . . . -1.2(7) ?
C4 C5 C6 C7 . . . . 0.3(7) ?
C5 C6 C7 C7A . . . . 0.9(6) ?
C6 C7 C7A C3A . . . . -1.2(5) ?
C6 C7 C7A N1 . . . . -178.1(4) ?
C4 C3A C7A C7 . . . . 0.4(6) ?
N3 C3A C7A C7 . . . . -179.0(3) ?
C4 C3A C7A N1 . . . . 178.0(3) ?
N3 C3A C7A N1 . . . . -1.3(4) ?
C2 N1 C7A C7 . . . . 178.8(4) ?
S1 N1 C7A C7 . . . . -16.3(6) ?
C2 N1 C7A C3A . . . . 1.6(4) ?
S1 N1 C7A C3A . . . . 166.4(3) ?
O1 S1 C8 C9 . . . . 157.3(3) ?
O2 S1 C8 C9 . . . . 22.1(3) ?
N1 S1 C8 C9 . . . . -89.2(3) ?
O1 S1 C8 C13 . . . . -21.3(3) ?
O2 S1 C8 C13 . . . . -156.6(3) ?
N1 S1 C8 C13 . . . . 92.1(3) ?
C13 C8 C9 C10 . . . . 0.2(5) ?
S1 C8 C9 C10 . . . . -178.5(3) ?
C8 C9 C10 C11 . . . . -0.5(5) ?
C9 C10 C11 C12 . . . . 0.5(5) ?
C9 C10 C11 C14 . . . . 179.2(3) ?
C10 C11 C12 C13 . . . . -0.2(5) ?
C14 C11 C12 C13 . . . . -178.8(3) ?
C9 C8 C13 C12 . . . . 0.1(5) ?
S1 C8 C13 C12 . . . . 178.8(3) ?
C11 C12 C13 C8 . . . . -0.1(5) ?
C10 C11 C14 C16A . . . . 10.7(19) ?
C12 C11 C14 C16A . . . . -170.7(19) ?
C10 C11 C14 C16 . . . . 174(2) ?
C12 C11 C14 C16 . . . . -7(2) ?
C10 C11 C14 C15A . . . . 131.8(8) ?
C12 C11 C14 C15A . . . . -49.7(8) ?
C10 C11 C14 C17 . . . . 49.9(10) ?
C12 C11 C14 C17 . . . . -131.5(10) ?
C10 C11 C14 C15 . . . . -63.0(13) ?
C12 C11 C14 C15 . . . . 115.6(13) ?
C10 C11 C14 C17A . . . . -115.3(15) ?
C12 C11 C14 C17A . . . . 63.2(15) ?
