#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226531.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_2226531
loop_
_publ_author_name
'Gelbrich, Thomas'
'Haddow, Mairi F.'
'Griesser, Ulrich J.'
_publ_section_title
;
 Polymorphic form II of 4,4'-methylenebis(benzenesulfonamide)
;
_journal_coeditor_code           IM2209
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1619
_journal_paper_doi               10.1107/S1600536810021409
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 N2 O4 S2'
_chemical_formula_moiety         'C13 H14 N2 O4 S2'
_chemical_formula_sum            'C13 H14 N2 O4 S2'
_chemical_formula_weight         326.38
_chemical_name_common            diphenylmethanesulfonamide
_chemical_name_systematic
;
4,4'-methylenebis(benzenesulfonamide)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90.931(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8251(5)
_cell_length_b                   5.0791(3)
_cell_length_c                   12.6912(5)
_cell_measurement_reflns_used    6304
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      2.91
_cell_volume                     697.69(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7877
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.7
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.457
_refine_ls_abs_structure_details 'Flack (1983), 904 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.18(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                2152
_reflns_number_total             2438
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2209.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2226531
_cod_database_fobs_code          2226531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.20189(6) -0.23188(15) 0.54432(5) 0.01593(18) Uani d . 1 . .
S S2 0.88754(6) 0.73072(17) 0.14221(5) 0.01695(19) Uani d . 1 . .
O O1 0.1335(2) -0.4632(4) 0.51332(16) 0.0205(5) Uani d . 1 . .
O O2 0.30683(18) -0.2579(6) 0.61295(14) 0.0238(5) Uani d . 1 . .
O O3 0.90887(19) 0.8314(5) 0.03829(15) 0.0249(6) Uani d . 1 . .
O O4 0.90645(19) 0.9060(4) 0.23016(16) 0.0208(5) Uani d . 1 . .
N N1 0.1033(3) -0.0417(6) 0.6023(2) 0.0189(6) Uani d D 1 . .
H H1 0.035(3) -0.039(10) 0.563(3) 0.053(13) Uiso d D 1 . .
H H2 0.129(3) 0.124(4) 0.608(3) 0.035(11) Uiso d D 1 . .
N N2 0.9759(2) 0.4794(6) 0.1575(2) 0.0197(6) Uani d D 1 . .
H H3 0.994(3) 0.410(7) 0.0960(18) 0.030(10) Uiso d D 1 . .
H H4 0.965(3) 0.381(7) 0.213(2) 0.042(12) Uiso d D 1 . .
C C1 0.3517(3) 0.3849(7) 0.1577(2) 0.0208(7) Uani d . 1 . .
H H1A 0.3319 0.2784 0.0943 0.024(8) Uiso calc R 1 . .
H H1B 0.2990 0.5441 0.1550 0.028(10) Uiso calc R 1 . .
C C11 0.2504(3) -0.0654(6) 0.4304(2) 0.0169(7) Uani d . 1 . .
C C12 0.1806(3) -0.0834(7) 0.3372(2) 0.0212(7) Uani d . 1 . .
H H12 0.1097 -0.1934 0.3335 0.021(8) Uiso calc R 1 . .
C C13 0.2160(3) 0.0610(7) 0.2502(2) 0.0200(7) Uani d . 1 . .
H H13 0.1696 0.0470 0.1863 0.032(10) Uiso calc R 1 . .
C C14 0.3184(2) 0.2261(7) 0.2547(2) 0.0164(6) Uani d . 1 . .
C C15 0.3882(2) 0.2386(8) 0.3479(2) 0.0189(6) Uani d . 1 . .
H H15 0.4599 0.3463 0.3514 0.045(12) Uiso calc R 1 . .
C C16 0.3538(3) 0.0945(7) 0.4360(2) 0.0188(7) Uani d . 1 . .
H H16 0.4011 0.1058 0.4995 0.026(9) Uiso calc R 1 . .
C C21 0.7330(3) 0.6228(6) 0.1479(2) 0.0151(6) Uani d . 1 . .
C C22 0.6511(2) 0.7639(7) 0.2093(2) 0.0174(6) Uani d . 1 . .
H H22 0.6786 0.9108 0.2497 0.037(11) Uiso calc R 1 . .
C C23 0.5271(3) 0.6854(6) 0.2106(2) 0.0179(7) Uani d . 1 . .
H H23 0.4702 0.7814 0.2520 0.021(8) Uiso calc R 1 . .
C C24 0.4857(3) 0.4701(6) 0.1528(2) 0.0170(7) Uani d . 1 . .
C C25 0.5703(3) 0.3302(7) 0.0928(2) 0.0183(7) Uani d . 1 . .
H H25 0.5432 0.1810 0.0536 0.030(10) Uiso calc R 1 . .
C C26 0.6932(3) 0.4053(7) 0.0892(2) 0.0187(7) Uani d . 1 . .
H H26 0.7498 0.3100 0.0473 0.043(11) 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'
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
O2 S1 O1 . . 119.49(15) ?
O2 S1 N1 . . 107.52(14) ?
O1 S1 N1 . . 105.68(14) ?
O2 S1 C11 . . 107.49(13) ?
O1 S1 C11 . . 109.03(14) ?
N1 S1 C11 . . 107.02(15) ?
O3 S2 O4 . . 117.93(14) ?
O3 S2 N2 . . 106.86(13) ?
O4 S2 N2 . . 108.72(13) ?
O3 S2 C21 . . 108.36(13) ?
O4 S2 C21 . . 106.48(13) ?
N2 S2 C21 . . 108.18(15) ?
S1 N1 H1 . . 108(3) ?
S1 N1 H2 . . 114(2) ?
H1 N1 H2 . . 107(4) ?
S2 N2 H3 . . 111(2) ?
S2 N2 H4 . . 118(3) ?
H3 N2 H4 . . 121(4) ?
C24 C1 C14 . . 115.1(2) ?
C24 C1 H1A . . 108.5 ?
C14 C1 H1A . . 108.5 ?
C24 C1 H1B . . 108.5 ?
C14 C1 H1B . . 108.5 ?
H1A C1 H1B . . 107.5 ?
C16 C11 C12 . . 120.5(3) ?
C16 C11 S1 . . 119.5(2) ?
C12 C11 S1 . . 120.0(2) ?
C13 C12 C11 . . 119.2(3) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 121.1(3) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C13 C14 C15 . . 118.9(3) ?
C13 C14 C1 . . 119.1(3) ?
C15 C14 C1 . . 122.0(3) ?
C16 C15 C14 . . 120.6(3) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C11 C16 C15 . . 119.7(3) ?
C11 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C22 C21 C26 . . 120.9(3) ?
C22 C21 S2 . . 118.5(2) ?
C26 C21 S2 . . 120.6(2) ?
C21 C22 C23 . . 118.7(3) ?
C21 C22 H22 . . 120.6 ?
C23 C22 H22 . . 120.6 ?
C24 C23 C22 . . 121.3(3) ?
C24 C23 H23 . . 119.4 ?
C22 C23 H23 . . 119.4 ?
C23 C24 C25 . . 118.8(3) ?
C23 C24 C1 . . 120.2(3) ?
C25 C24 C1 . . 120.9(3) ?
C26 C25 C24 . . 121.1(3) ?
C26 C25 H25 . . 119.4 ?
C24 C25 H25 . . 119.4 ?
C25 C26 C21 . . 119.2(3) ?
C25 C26 H26 . . 120.4 ?
C21 C26 H26 . . 120.4 ?
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 O2 . 1.4263(19) ?
S1 O1 . 1.440(2) ?
S1 N1 . 1.624(3) ?
S1 C11 . 1.762(3) ?
S2 O3 . 1.437(2) ?
S2 O4 . 1.440(2) ?
S2 N2 . 1.605(3) ?
S2 C21 . 1.763(3) ?
N1 H1 . 0.881(19) ?
N1 H2 . 0.887(19) ?
N2 H3 . 0.883(18) ?
N2 H4 . 0.875(19) ?
C1 C24 . 1.516(4) ?
C1 C14 . 1.520(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C11 C16 . 1.384(4) ?
C11 C12 . 1.396(4) ?
C12 C13 . 1.385(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.395(4) ?
C15 C16 . 1.391(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.389(4) ?
C21 C26 . 1.397(4) ?
C22 C23 . 1.401(4) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.387(4) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.395(4) ?
C25 C26 . 1.386(4) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
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 H1 O1 2_556 0.881(19) 2.09(2) 2.960(4) 168(4)
N1 H2 O1 1_565 0.887(19) 2.42(3) 3.166(4) 142(3)
N1 H2 O4 2_646 0.887(19) 2.53(3) 3.116(4) 124(3)
N2 H3 O3 2_745 0.883(18) 2.06(2) 2.898(3) 159(3)
N2 H4 N1 2_656 0.875(19) 2.50(3) 3.182(3) 135(3)
N2 H4 O4 1_545 0.875(19) 2.50(3) 3.149(4) 131(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 655579
