#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200637.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_2200637
loop_
_publ_author_name
'Beloso, Inmaculada'
'Castro, Jesús'
'Pérez-Lourido, Paulo'
_publ_section_title
1-Methyl-3-(4-methylphenylsulfonyl)-2-(4-methylphenylsulfonylimino)benzimidazole
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1067
_journal_page_last               o1069
_journal_paper_doi               10.1107/S1600536801016075
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C22 H21 N3 O4 S2'
_chemical_formula_moiety         'C22 H21 N3 O4 S2'
_chemical_formula_sum            'C22 H21 N3 O4 S2'
_chemical_formula_weight         455.54
_chemical_name_systematic
1-Methyl-3-(4-methylphenylsulfonyl)-2-(4-methylphenylsulfonylimino)benzimidazole
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.529(2)
_cell_angle_beta                 104.567(2)
_cell_angle_gamma                101.135(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9692(8)
_cell_length_b                   11.1288(11)
_cell_length_c                   13.5622(13)
_cell_measurement_reflns_used    57
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1061.92(18)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 1996)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .948
_diffrn_measured_fraction_theta_max .901
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .031
_diffrn_reflns_av_sigmaI/netI    .050
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6648
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .286
_exptl_absorpt_correction_T_max  .956
_exptl_absorpt_correction_T_min  .777
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          .53
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .16
_refine_diff_density_max         .33
_refine_diff_density_min         -.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          .067
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          .004
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0685P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .127
_reflns_number_gt                3401
_reflns_number_total             4641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6059.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2200637
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
S1 .12729(7) .25990(5) .57943(4) .03998(16) Uani d . 1 . . S
S2 -.05559(8) .12341(6) .82726(5) .04310(17) Uani d . 1 . . S
N1 .0689(3) .1812(2) .65154(15) .0476(5) Uani d . 1 . . N
N2 .2770(2) .04984(16) .67270(13) .0372(4) Uani d . 1 . . N
N3 .0881(2) .06266(17) .76769(14) .0390(4) Uani d . 1 . . N
O1 .3164(2) .32984(17) .62160(14) .0564(5) Uani d . 1 . . O
O11 -.2011(2) .12635(17) .74388(13) .0523(4) Uani d . 1 . . O
O22 -.0881(2) .04561(17) .89057(14) .0590(5) Uani d . 1 . . O
O2 .0564(2) .17681(16) .46560(12) .0566(5) Uani d . 1 . . O
C1 .3574(3) .0488(2) .58711(19) .0488(6) Uani d . 1 . . C
H1A .2644 .0338 .5203 .073 Uiso calc R 1 . . H
H1B .4149 -.0201 .5757 .073 Uiso calc R 1 . . H
H1C .4459 .1322 .6090 .073 Uiso calc R 1 . . H
C2 .3140(3) -.0210(2) .74101(17) .0412(5) Uani d . 1 . . C
C3 .4389(3) -.0902(2) .7524(2) .0548(6) Uani d . 1 . . C
H3 .5133 -.0982 .7094 .066 Uiso calc R 1 . . H
C4 .4491(4) -.1468(3) .8297(2) .0673(8) Uani d . 1 . . C
H4 .5322 -.1941 .8394 .081 Uiso calc R 1 . . H
C5 .3379(4) -.1349(3) .8937(2) .0629(7) Uani d . 1 . . C
H5 .3497 -.1733 .9462 .075 Uiso calc R 1 . . H
C6 .2105(4) -.0681(2) .88192(19) .0526(6) Uani d . 1 . . C
H6 .1354 -.0612 .9246 .063 Uiso calc R 1 . . H
C7 .1995(3) -.0115(2) .80293(17) .0406(5) Uani d . 1 . . C
C8 .1440(3) .1038(2) .68986(16) .0364(5) Uani d . 1 . . C
C9 .0074(3) .3769(2) .60305(16) .0391(5) Uani d . 1 . . C
C10 .0957(3) .5088(2) .63734(18) .0459(5) Uani d . 1 . . C
H10 .2191 .5365 .6486 .055 Uiso calc R 1 . . H
C11 .0000(4) .6002(2) .65505(19) .0526(6) Uani d . 1 . . C
H11 .0608 .6891 .6776 .063 Uiso calc R 1 . . H
C12 -.1818(4) .5635(3) .64023(19) .0518(6) Uani d . 1 . . C
C13 -.2687(4) .4298(3) .6058(2) .0607(7) Uani d . 1 . . C
H13 -.3917 .4022 .5957 .073 Uiso calc R 1 . . H
C14 -.1767(3) .3372(3) .5863(2) .0571(7) Uani d . 1 . . C
H14 -.2380 .2482 .5620 .069 Uiso calc R 1 . . H
C15 -.2841(4) .6631(3) .6611(3) .0739(9) Uani d . 1 . . C
H15A -.2205 .7308 .7321 .111 Uiso calc R 1 . . H
H15B -.4030 .6207 .6585 .111 Uiso calc R 1 . . H
H15C -.2944 .7015 .6061 .111 Uiso calc R 1 . . H
C29 .0756(3) .2835(2) .91432(17) .0408(5) Uani d . 1 . . C
C210 .0734(3) .3863(2) .87804(18) .0467(6) Uani d . 1 . . C
H210 -.0041 .3724 .8091 .056 Uiso calc R 1 . . H
C211 .1888(3) .5111(2) .94575(19) .0515(6) Uani d . 1 . . C
H211 .1876 .5810 .9218 .062 Uiso calc R 1 . . H
C212 .3054(3) .5329(2) 1.04829(18) .0499(6) Uani d . 1 . . C
C213 .3018(4) .4289(3) 1.0832(2) .0607(7) Uani d . 1 . . C
H213 .3773 .4431 1.1528 .073 Uiso calc R 1 . . H
C214 .1887(4) .3037(3) 1.01752(19) .0553(6) Uani d . 1 . . C
H214 .1886 .2342 1.0422 .066 Uiso calc R 1 . . H
C215 .4326(4) .6677(3) 1.1211(2) .0684(8) Uani d . 1 . . C
H21A .4187 .7280 1.0839 .103 Uiso calc R 1 . . H
H21B .5552 .6634 1.1381 .103 Uiso calc R 1 . . H
H21C .4048 .6975 1.1876 .103 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
_geom_angle_publ_flag
O1 S1 O2 116.39(11) ?
O1 S1 N1 112.76(10) ?
O2 S1 N1 110.34(11) ?
O1 S1 C9 107.62(10) ?
O2 S1 C9 108.91(10) ?
N1 S1 C9 99.34(10) y
O11 S2 O22 120.35(11) ?
O11 S2 N3 107.70(9) ?
O22 S2 N3 104.02(10) ?
O11 S2 C29 110.36(11) ?
O22 S2 C29 109.66(11) ?
N3 S2 C29 103.17(10) y
C8 N1 S1 129.56(17) y
C8 N2 C2 110.05(18) y
C8 N2 C1 126.40(18) ?
C2 N2 C1 123.12(19) ?
C8 N3 C7 108.79(18) y
C8 N3 S2 123.26(15) y
C7 N3 S2 126.58(15) ?
N2 C1 H1A 109.5 ?
N2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
N2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C3 C2 C7 121.6(2) ?
C3 C2 N2 130.3(2) ?
C7 C2 N2 108.1(2) y
C4 C3 C2 117.4(3) ?
C4 C3 H3 121.3 ?
C2 C3 H3 121.3 ?
C3 C4 C5 121.2(3) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C4 122.1(2) ?
C6 C5 H5 119.0 ?
C4 C5 H5 119.0 ?
C5 C6 C7 116.6(3) ?
C5 C6 H6 121.7 ?
C7 C6 H6 121.7 ?
C2 C7 C6 121.1(2) ?
C2 C7 N3 106.10(18) y
C6 C7 N3 132.8(2) ?
N1 C8 N2 133.5(2) y
N1 C8 N3 119.6(2) y
N2 C8 N3 106.85(17) y
C10 C9 C14 119.4(2) ?
C10 C9 S1 120.09(18) ?
C14 C9 S1 120.49(18) ?
C9 C10 C11 119.7(2) ?
C9 C10 H10 120.1 ?
C11 C10 H10 120.1 ?
C12 C11 C10 121.9(2) ?
C12 C11 H11 119.0 ?
C10 C11 H11 119.0 ?
C11 C12 C13 117.5(2) ?
C11 C12 C15 121.7(3) ?
C13 C12 C15 120.8(3) ?
C14 C13 C12 121.5(2) ?
C14 C13 H13 119.3 ?
C12 C13 H13 119.3 ?
C13 C14 C9 119.9(2) ?
C13 C14 H14 120.0 ?
C9 C14 H14 120.0 ?
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 ?
C210 C29 C214 120.8(2) ?
C210 C29 S2 120.10(17) ?
C214 C29 S2 118.98(19) ?
C29 C210 C211 119.1(2) ?
C29 C210 H210 120.5 ?
C211 C210 H210 120.5 ?
C212 C211 C210 121.0(2) ?
C212 C211 H211 119.5 ?
C210 C211 H211 119.5 ?
C213 C212 C211 118.5(2) ?
C213 C212 C215 120.4(2) ?
C211 C212 C215 121.1(2) ?
C212 C213 C214 121.7(2) ?
C212 C213 H213 119.2 ?
C214 C213 H213 119.2 ?
C213 C214 C29 118.8(2) ?
C213 C214 H214 120.6 ?
C29 C214 H214 120.6 ?
C212 C215 H21A 109.5 ?
C212 C215 H21B 109.5 ?
H21A C215 H21B 109.5 ?
C212 C215 H21C 109.5 ?
H21A C215 H21C 109.5 ?
H21B C215 H21C 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 . 1.4319(16) y
S1 O2 . 1.4342(16) y
S1 N1 . 1.5896(18) y
S1 C9 . 1.759(2) y
S2 O11 . 1.4148(16) y
S2 O22 . 1.4238(17) y
S2 N3 . 1.6900(19) y
S2 C29 . 1.747(2) y
N1 C8 . 1.297(3) y
N2 C8 . 1.351(3) y
N2 C2 . 1.399(3) y
N2 C1 . 1.458(3) y
N3 C8 . 1.404(3) y
N3 C7 . 1.416(3) y
C1 H1A . .96 ?
C1 H1B . .96 ?
C1 H1C . .96 ?
C2 C3 . 1.378(3) ?
C2 C7 . 1.385(3) y
C3 C4 . 1.370(4) ?
C3 H3 . .93 ?
C4 C5 . 1.385(4) ?
C4 H4 . .93 ?
C5 C6 . 1.374(4) ?
C5 H5 . .93 ?
C6 C7 . 1.390(3) ?
C6 H6 . .93 ?
C9 C10 . 1.376(3) ?
C9 C14 . 1.386(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . .93 ?
C11 C12 . 1.372(3) ?
C11 H11 . .93 ?
C12 C13 . 1.390(4) ?
C12 C15 . 1.500(4) ?
C13 C14 . 1.375(4) ?
C13 H13 . .93 ?
C14 H14 . .93 ?
C15 H15A . .96 ?
C15 H15B . .96 ?
C15 H15C . .96 ?
C29 C210 . 1.376(3) ?
C29 C214 . 1.386(3) ?
C210 C211 . 1.389(3) ?
C210 H210 . .93 ?
C211 C212 . 1.384(3) ?
C211 H211 . .93 ?
C212 C213 . 1.375(4) ?
C212 C215 . 1.506(3) ?
C213 C214 . 1.382(4) ?
C213 H213 . .93 ?
C214 H214 . .93 ?
C215 H21A . .96 ?
C215 H21B . .96 ?
C215 H21C . .96 ?
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
C1 H1C O1 . .96 2.58 3.114(3) 115.1 y
C6 H6 O22 . .93 2.35 2.914(3) 118.6 y
C10 H10 O1 . .93 2.52 2.897(3) 104.6 y
C6 H6 O22 2_557 .93 2.59 3.417(3) 148.9 y
C13 H13 O1 1_455 .93 2.46 3.361(3) 163.8 y
C210 H210 Cg3 . .93 3.03 3.844(3) 147.2 y
C11 H11 Cg2 1_565 .93 2.76 3.624(3) 154.3 y
C215 H21B Cg1 2_667 .96 3.19 3.551(3) 104.3 y
C215 H21B Cg4 2_667 .96 2.98 3.756(3) 138.2 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
_geom_torsion_publ_flag
O1 S1 N1 C8 -47.6(2) ?
O2 S1 N1 C8 84.4(2) ?
C9 S1 N1 C8 -161.3(2) ?
O11 S2 N3 C8 45.53(19) ?
O22 S2 N3 C8 174.32(16) ?
C29 S2 N3 C8 -71.19(18) ?
O11 S2 N3 C7 -149.34(17) ?
O22 S2 N3 C7 -20.5(2) ?
C29 S2 N3 C7 93.94(19) ?
C8 N2 C2 C3 -179.2(2) ?
C1 N2 C2 C3 7.8(4) ?
C8 N2 C2 C7 .2(2) ?
C1 N2 C2 C7 -172.69(19) ?
C7 C2 C3 C4 -1.7(4) ?
N2 C2 C3 C4 177.7(2) ?
C2 C3 C4 C5 .1(4) ?
C3 C4 C5 C6 1.1(4) ?
C4 C5 C6 C7 -.6(4) ?
C3 C2 C7 C6 2.2(3) ?
N2 C2 C7 C6 -177.4(2) ?
C3 C2 C7 N3 -178.4(2) ?
N2 C2 C7 N3 2.0(2) ?
C5 C6 C7 C2 -1.0(3) ?
C5 C6 C7 N3 179.8(2) ?
C8 N3 C7 C2 -3.6(2) ?
S2 N3 C7 C2 -170.45(15) y
C8 N3 C7 C6 175.7(2) ?
S2 N3 C7 C6 8.8(4) ?
S1 N1 C8 N2 -9.8(4) ?
S1 N1 C8 N3 168.85(16) ?
C2 N2 C8 N1 176.3(2) y
C1 N2 C8 N1 -11.0(4) ?
C2 N2 C8 N3 -2.4(2) ?
C1 N2 C8 N3 170.20(19) ?
C7 N3 C8 N1 -175.25(19) y
S2 N3 C8 N1 -7.8(3) ?
C7 N3 C8 N2 3.7(2) ?
S2 N3 C8 N2 171.15(14) y
O1 S1 C9 C10 10.7(2) ?
O2 S1 C9 C10 -116.29(18) ?
N1 S1 C9 C10 128.33(19) ?
O1 S1 C9 C14 -169.92(18) ?
O2 S1 C9 C14 63.1(2) ?
N1 S1 C9 C14 -52.3(2) ?
C14 C9 C10 C11 .2(3) ?
S1 C9 C10 C11 179.57(17) ?
C9 C10 C11 C12 .5(4) ?
C10 C11 C12 C13 -.4(4) ?
C10 C11 C12 C15 179.1(2) ?
C11 C12 C13 C14 -.5(4) ?
C15 C12 C13 C14 -180.0(2) ?
C12 C13 C14 C9 1.2(4) ?
C10 C9 C14 C13 -1.1(4) ?
S1 C9 C14 C13 179.6(2) ?
O11 S2 C29 C210 -22.8(2) ?
O22 S2 C29 C210 -157.65(19) ?
N3 S2 C29 C210 92.0(2) ?
O11 S2 C29 C214 160.82(18) ?
O22 S2 C29 C214 26.0(2) ?
N3 S2 C29 C214 -84.4(2) ?
C214 C29 C210 C211 1.0(4) ?
S2 C29 C210 C211 -175.29(18) ?
C29 C210 C211 C212 .3(4) ?
C210 C211 C212 C213 -1.6(4) ?
C210 C211 C212 C215 179.0(2) ?
C211 C212 C213 C214 1.7(4) ?
C215 C212 C213 C214 -178.9(2) ?
C212 C213 C214 C29 -.5(4) ?
C210 C29 C214 C213 -.9(4) ?
S2 C29 C214 C213 175.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654628
