#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233818.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_2233818
loop_
_publ_author_name
'Sohail, Muhammad'
'Asghar, Muhammad Nadeem'
'Tahir, M. Nawaz'
'Shafique, Muhammad'
'Ashfaq, Muhammad'
_publ_section_title
;
 4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}benzenesulfonamide
;
_journal_coeditor_code           GK2455
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o693
_journal_paper_doi               10.1107/S1600536812005260
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H17 N3 O5 S2'
_chemical_formula_moiety         'C17 H17 N3 O5 S2'
_chemical_formula_sum            'C17 H17 N3 O5 S2'
_chemical_formula_weight         407.46
_chemical_name_systematic
;
4-Methyl-N-{4-[(5-methyl-1,2-oxazol-3-
yl)sulfamoyl]phenyl}benzenesulfonamide
;
_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
_cell_angle_beta                 106.863(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6294(6)
_cell_length_b                   12.2394(7)
_cell_length_c                   14.9673(11)
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.19
_cell_volume                     1863.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.50
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17943
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.370
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0549
_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)+(0.0577P)²+0.1435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2488
_reflns_number_total             4629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2455.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233818
_cod_database_fobs_code          2233818
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
S S1 0.17178(7) 0.12476(6) 0.43330(5) 0.0475(3) Uani 1.000 -16
S S2 0.42023(7) 0.58034(6) 0.24478(5) 0.0485(3) Uani 1.000 -16
O O1 0.20899(18) 0.03512(15) 0.49755(15) 0.0596(8) Uani 1.000 -16
O O2 0.09435(18) 0.10311(16) 0.33965(14) 0.0575(7) Uani 1.000 -16
O O3 0.54004(19) 0.62547(15) 0.30218(14) 0.0594(7) Uani 1.000 -16
O O4 0.30436(19) 0.64578(16) 0.21489(15) 0.0642(8) Uani 1.000 -16
O O5 0.65024(19) 0.33654(16) 0.10010(15) 0.0618(8) Uani 1.000 -16
N N1 0.3101(2) 0.18092(19) 0.43406(16) 0.0519(8) Uani 1.000 -16
N N2 0.4456(2) 0.53685(18) 0.14776(16) 0.0486(8) Uani 1.000 -16
N N3 0.5291(2) 0.3918(2) 0.08307(18) 0.0605(9) Uani 1.000 -16
C C1 0.0863(2) 0.2224(2) 0.47933(18) 0.0398(8) Uani 1.000 -16
C C2 -0.0473(3) 0.2308(3) 0.4409(2) 0.0573(11) Uani 1.000 -16
C C3 -0.1174(3) 0.3048(3) 0.4774(2) 0.0684(14) Uani 1.000 -16
C C4 -0.0567(3) 0.3690(3) 0.5522(2) 0.0615(12) Uani 1.000 -16
C C5 0.0766(4) 0.3572(3) 0.5909(3) 0.0703(14) Uani 1.000 -16
C C6 0.1495(3) 0.2850(3) 0.5556(2) 0.0592(11) Uani 1.000 -16
C C7 -0.1339(4) 0.4484(3) 0.5932(3) 0.1003(19) Uani 1.000 -16
C C8 0.3303(2) 0.2762(2) 0.38676(19) 0.0440(9) Uani 1.000 -16
C C9 0.4465(3) 0.3330(3) 0.4242(2) 0.0607(11) Uani 1.000 -16
C C10 0.4738(3) 0.4247(3) 0.3811(2) 0.0578(11) Uani 1.000 -16
C C11 0.3859(2) 0.4623(2) 0.30027(18) 0.0427(9) Uani 1.000 -16
C C12 0.2695(3) 0.4061(2) 0.2627(2) 0.0509(10) Uani 1.000 -16
C C13 0.2425(3) 0.3132(2) 0.3054(2) 0.0513(10) Uani 1.000 -16
C C14 0.5480(3) 0.4644(2) 0.14888(19) 0.0430(9) Uani 1.000 -16
C C15 0.6744(3) 0.4591(2) 0.2104(2) 0.0498(10) Uani 1.000 -16
C C16 0.7342(3) 0.3799(2) 0.1768(2) 0.0482(10) Uani 1.000 -16
C C17 0.8701(3) 0.3364(3) 0.2031(2) 0.0661(11) Uani 1.000 -16
H H1 0.37992 0.14872 0.46739 0.0623 Uiso 1.000 -16
H H2 -0.09040 0.18700 0.39052 0.0687 Uiso 1.000 -16
H H2A 0.39496 0.55907 0.09507 0.0583 Uiso 1.000 -16
H H3 -0.20773 0.31110 0.45045 0.0821 Uiso 1.000 -16
H H5 0.11898 0.39923 0.64258 0.0842 Uiso 1.000 -16
H H6 0.23972 0.27863 0.58283 0.0707 Uiso 1.000 -16
H H7A -0.22555 0.42985 0.57205 0.1503 Uiso 1.000 -16
H H7B -0.12163 0.52121 0.57344 0.1503 Uiso 1.000 -16
H H7C -0.10358 0.44443 0.66009 0.1503 Uiso 1.000 -16
H H9 0.50638 0.30849 0.47898 0.0729 Uiso 1.000 -16
H H10 0.55227 0.46190 0.40663 0.0696 Uiso 1.000 -16
H H12 0.20926 0.43125 0.20833 0.0610 Uiso 1.000 -16
H H13 0.16469 0.27516 0.27928 0.0614 Uiso 1.000 -16
H H15 0.70953 0.50155 0.26337 0.0597 Uiso 1.000 -16
H H17A 0.90803 0.34876 0.15310 0.0992 Uiso 1.000 -16
H H17B 0.86837 0.25935 0.21492 0.0992 Uiso 1.000 -16
H H17C 0.92184 0.37272 0.25840 0.0992 Uiso 1.000 -16
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
_geom_angle_publ_flag
O1 S1 O2 118.90(12) no
O1 S1 N1 104.26(12) no
O1 S1 C1 109.27(12) no
O2 S1 N1 110.41(12) no
O2 S1 C1 107.11(12) no
N1 S1 C1 106.26(12) no
O3 S2 O4 120.68(12) no
O3 S2 N2 108.17(12) no
O3 S2 C11 107.80(12) no
O4 S2 N2 104.65(12) no
O4 S2 C11 109.32(12) no
N2 S2 C11 105.17(12) no
N3 O5 C16 108.1(2) no
S1 N1 C8 128.05(18) no
S2 N2 C14 121.44(19) no
O5 N3 C14 105.0(2) no
C8 N1 H1 116.00 no
S1 N1 H1 116.00 no
S2 N2 H2A 119.00 no
C14 N2 H2A 119.00 no
S1 C1 C6 121.3(2) no
C2 C1 C6 120.2(3) no
S1 C1 C2 118.4(2) no
C1 C2 C3 119.6(3) no
C2 C3 C4 121.3(3) no
C3 C4 C5 118.0(3) no
C3 C4 C7 121.3(3) no
C5 C4 C7 120.7(3) no
C4 C5 C6 122.1(4) no
C1 C6 C5 118.8(3) no
N1 C8 C9 117.3(2) no
N1 C8 C13 123.5(2) no
C9 C8 C13 119.2(3) no
C8 C9 C10 120.5(3) no
C9 C10 C11 120.4(3) no
S2 C11 C12 120.0(2) no
C10 C11 C12 119.3(3) no
S2 C11 C10 120.6(2) no
C11 C12 C13 120.3(3) no
C8 C13 C12 120.2(3) no
N2 C14 N3 118.4(3) no
N2 C14 C15 129.4(2) no
N3 C14 C15 112.2(3) no
C14 C15 C16 105.0(3) no
O5 C16 C17 116.1(2) no
C15 C16 C17 134.0(3) no
O5 C16 C15 109.8(3) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 119.00 no
C4 C3 H3 119.00 no
C4 C5 H5 119.00 no
C6 C5 H5 119.00 no
C1 C6 H6 121.00 no
C5 C6 H6 121.00 no
C4 C7 H7A 109.00 no
C4 C7 H7B 109.00 no
C4 C7 H7C 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 110.00 no
C8 C9 H9 120.00 no
C10 C9 H9 120.00 no
C9 C10 H10 120.00 no
C11 C10 H10 120.00 no
C11 C12 H12 120.00 no
C13 C12 H12 120.00 no
C8 C13 H13 120.00 no
C12 C13 H13 120.00 no
C14 C15 H15 128.00 no
C16 C15 H15 128.00 no
C16 C17 H17A 110.00 no
C16 C17 H17B 109.00 no
C16 C17 H17C 109.00 no
H17A C17 H17B 109.00 no
H17A C17 H17C 110.00 no
H17B C17 H17C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 1.437(2) no
S1 O2 1.429(2) no
S1 N1 1.620(2) no
S1 C1 1.758(3) no
S2 O3 1.425(2) no
S2 O4 1.428(2) no
S2 N2 1.641(2) no
S2 C11 1.757(3) no
O5 N3 1.411(3) no
O5 C16 1.342(4) no
N1 C8 1.413(3) no
N2 C14 1.400(4) no
N3 C14 1.298(4) no
N1 H1 0.8600 no
N2 H2A 0.8600 no
C1 C2 1.373(4) no
C1 C6 1.377(4) no
C2 C3 1.382(5) no
C3 C4 1.367(4) no
C4 C7 1.512(5) no
C4 C5 1.374(5) no
C5 C6 1.378(5) no
C8 C13 1.378(4) no
C8 C9 1.386(4) no
C9 C10 1.367(5) no
C10 C11 1.376(4) no
C11 C12 1.384(4) no
C12 C13 1.375(4) no
C14 C15 1.393(4) no
C15 C16 1.335(4) no
C16 C17 1.482(5) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C9 H9 0.9300 no
C10 H10 0.9300 no
C12 H12 0.9300 no
C13 H13 0.9300 no
C15 H15 0.9300 no
C17 H17A 0.9600 no
C17 H17B 0.9600 no
C17 H17C 0.9600 no
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
N1 H1 N3 4_555 0.86 2.04 2.859(3) 159 yes
N2 H2A O1 4_554 0.86 2.39 2.979(3) 127 yes
C2 H2 O4 2_545 0.93 2.42 3.208(4) 143 yes
C13 H13 O2 . 0.93 2.49 3.134(3) 126 yes
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 -176.4(2) no
O2 S1 N1 C8 54.8(3) no
C1 S1 N1 C8 -61.0(3) no
O1 S1 C1 C2 -106.2(2) no
O1 S1 C1 C6 70.1(3) no
O2 S1 C1 C2 23.9(3) no
O2 S1 C1 C6 -159.9(2) no
N1 S1 C1 C2 141.9(2) no
N1 S1 C1 C6 -41.9(3) no
O3 S2 N2 C14 53.7(2) no
O4 S2 N2 C14 -176.5(2) no
C11 S2 N2 C14 -61.3(2) no
O3 S2 C11 C10 -4.6(3) no
O3 S2 C11 C12 175.4(2) no
O4 S2 C11 C10 -137.5(2) no
O4 S2 C11 C12 42.5(3) no
N2 S2 C11 C10 110.6(2) no
N2 S2 C11 C12 -69.4(2) no
C16 O5 N3 C14 0.7(3) no
N3 O5 C16 C15 0.4(3) no
N3 O5 C16 C17 -176.7(2) no
S1 N1 C8 C9 154.9(2) no
S1 N1 C8 C13 -26.6(4) no
S2 N2 C14 N3 145.2(2) no
S2 N2 C14 C15 -37.0(4) no
O5 N3 C14 N2 176.8(2) no
O5 N3 C14 C15 -1.4(3) no
S1 C1 C2 C3 178.3(2) no
C6 C1 C2 C3 2.0(5) no
S1 C1 C6 C5 -177.5(3) no
C2 C1 C6 C5 -1.3(5) no
C1 C2 C3 C4 -1.0(5) no
C2 C3 C4 C5 -0.6(5) no
C2 C3 C4 C7 -178.8(3) no
C3 C4 C5 C6 1.2(6) no
C7 C4 C5 C6 179.5(3) no
C4 C5 C6 C1 -0.3(5) no
N1 C8 C9 C10 178.7(3) no
C13 C8 C9 C10 0.1(5) no
N1 C8 C13 C12 -179.3(3) no
C9 C8 C13 C12 -0.8(4) no
C8 C9 C10 C11 0.4(5) no
C9 C10 C11 S2 179.8(2) no
C9 C10 C11 C12 -0.2(4) no
S2 C11 C12 C13 179.5(2) no
C10 C11 C12 C13 -0.5(4) no
C11 C12 C13 C8 1.0(4) no
N2 C14 C15 C16 -176.3(3) no
N3 C14 C15 C16 1.6(3) no
C14 C15 C16 O5 -1.1(3) no
C14 C15 C16 C17 175.2(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2087322
