#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/91/2209162.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_2209162
loop_
_publ_author_name
'Zareef, Muhammad'
'Iqbal, Rashid'
'Zaidi, Javid H.'
'Arfan, Muhammad'
'Parvez, Masood'
_publ_section_title
4-Methyl-N-[1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl]benzenesulfonamide
_journal_coeditor_code           FL2023
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2481
_journal_page_last               o2483
_journal_paper_doi               10.1107/S1600536806018265
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H15 N3 O3 S2'
_chemical_formula_moiety         'C12 H15 N3 O3 S2'
_chemical_formula_sum            'C12 H15 N3 O3 S2'
_chemical_formula_weight         313.39
_chemical_name_common
;
?
;
_chemical_name_systematic
;
4-Methyl-N-[1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-
yl)propyl]benzenesulfonamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 114.05(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.098(5)
_cell_length_b                   16.575(8)
_cell_length_c                   13.695(5)
_cell_measurement_reflns_used    5916
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.2
_cell_volume                     2922(2)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ'
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5916
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.2
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.048
_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)+(0.038P)²+4.48P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.104
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                3265
_reflns_number_total             4257
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2023.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times).

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 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (16 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209162
_cod_database_fobs_code          2209162
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.55151(5) 0.44288(3) 0.12394(4) 0.04341(16) Uani d . 1 . .
O O1 0.68687(10) 0.42991(8) 0.32887(10) 0.0297(3) Uani d . 1 . .
S S2 0.98905(6) 0.35917(4) 0.51816(5) 0.02780(16) Uani d P 0.898(2) A 1
O O2 1.01417(13) 0.30440(10) 0.60736(12) 0.0359(4) Uani d P 0.898(2) A 1
O O3 1.06947(14) 0.41251(10) 0.51767(16) 0.0380(4) Uani d P 0.898(2) A 1
S S2' 0.9946(6) 0.3427(4) 0.5300(3) 0.02780(16) Uani d PD 0.102(2) A 2
O O2' 1.0629(11) 0.2815(7) 0.5962(11) 0.0359(4) Uani d PD 0.102(2) A 2
O O3' 1.0267(12) 0.4178(7) 0.5002(15) 0.0380(4) Uani d PD 0.102(2) A 2
N N1 0.61995(12) 0.31653(10) 0.25982(12) 0.0289(3) Uani d . 1 . .
H H1 0.5828 0.2796 0.2141 0.035 Uiso calc R 1 . .
N N2 0.68669(12) 0.29961(10) 0.36459(12) 0.0308(3) Uani d . 1 . .
N N3 0.89695(12) 0.41784(10) 0.51639(14) 0.0272(4) Uani d P 0.898(2) A 1
H H3 0.9059 0.4704 0.5170 0.033 Uiso calc PR 0.898(2) A 1
C C3 0.79995(14) 0.38655(12) 0.51386(15) 0.0310(4) Uani d . 1 A 1
H H3A 0.8158 0.3344 0.5540 0.037 Uiso calc PR 0.898(2) A 1
N N3' 0.8897(8) 0.3515(9) 0.5490(12) 0.0272(4) Uani d PD 0.102(2) A 2
H H3' 0.8955 0.3210 0.6039 0.033 Uiso calc PR 0.102(2) A 2
C C3' 0.79995(14) 0.38655(12) 0.51386(15) 0.0310(4) Uani d P 0.00 A 2
H H3'1 0.8281 0.4333 0.4880 0.037 Uiso calc PR 0.102(2) A 2
C C1 0.61794(14) 0.39442(12) 0.23564(14) 0.0289(4) Uani d . 1 . .
C C2 0.72397(14) 0.36881(11) 0.40198(14) 0.0274(4) Uani d . 1 . .
C C4 0.75528(15) 0.44336(12) 0.57119(15) 0.0314(4) Uani d . 1 . .
H H4A 0.7487 0.4980 0.5398 0.038 Uiso calc R 1 A 1
H H4B 0.6848 0.4248 0.5599 0.038 Uiso calc R 1 A 1
C C5 0.82184(19) 0.44806(17) 0.69008(18) 0.0522(6) Uani d . 1 A .
H H5A 0.7882 0.4831 0.7241 0.063 Uiso calc R 1 . .
H H5B 0.8901 0.4702 0.7019 0.063 Uiso calc R 1 . .
H H5C 0.8303 0.3939 0.7212 0.063 Uiso calc R 1 . .
C C6 0.94094(14) 0.30011(12) 0.40061(15) 0.0297(4) Uani d D 1 . .
C C7 0.90145(16) 0.34027(13) 0.30256(17) 0.0365(4) Uani d . 1 A .
H H7 0.9019 0.3975 0.2999 0.044 Uiso calc R 1 . .
C C8 0.86155(17) 0.29546(15) 0.20917(17) 0.0419(5) Uani d . 1 . .
H H8 0.8337 0.3225 0.1422 0.050 Uiso calc R 1 A .
C C9 0.86159(16) 0.21148(15) 0.21175(18) 0.0407(5) Uani d . 1 A .
C C10 0.90142(17) 0.17321(14) 0.31084(19) 0.0404(5) Uani d . 1 . .
H H10 0.9019 0.1159 0.3138 0.048 Uiso calc R 1 A .
C C11 0.94046(15) 0.21708(12) 0.40547(17) 0.0345(4) Uani d . 1 A .
H H11 0.9665 0.1902 0.4726 0.041 Uiso calc R 1 . .
C C12 0.8198(2) 0.16219(19) 0.1102(2) 0.0587(7) Uani d . 1 . .
H H12A 0.8538 0.1093 0.1237 0.070 Uiso calc R 1 A .
H H12B 0.8337 0.1903 0.0545 0.070 Uiso calc R 1 . .
H H12C 0.7447 0.1550 0.0866 0.070 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
_geom_angle_publ_flag
C2 O1 C1 106.02(14) y
O3 S2 O2 117.87(11) y
O3 S2 N3 105.07(11) y
O2 S2 N3 108.03(11) y
O3 S2 C6 110.29(11) y
O2 S2 C6 107.04(10) y
N3 S2 C6 108.20(10) y
O2' S2' O3' 125.6(11) y
O2' S2' N3' 112.6(10) y
O3' S2' N3' 112.6(10) y
O2' S2' C6 104.6(7) y
O3' S2' C6 96.7(9) y
N3' S2' C6 98.8(7) y
C1 N1 N2 112.98(15) y
C1 N1 H1 123.5 ?
N2 N1 H1 123.5 ?
C2 N2 N1 103.17(15) y
C3 N3 S2 122.00(14) y
C3 N3 H3 119.0 ?
S2 N3 H3 119.0 ?
N3 C3 C2 111.65(16) ?
N3 C3 C4 110.61(16) ?
C2 C3 C4 112.12(15) ?
N3 C3 H3A 107.4 ?
C2 C3 H3A 107.4 ?
C4 C3 H3A 107.4 ?
S2' N3' H3' 108.3 ?
N1 C1 O1 104.34(15) ?
N1 C1 S1 130.77(14) ?
O1 C1 S1 124.89(14) ?
N2 C2 O1 113.49(16) ?
N2 C2 C3 126.27(17) ?
O1 C2 C3 120.24(16) ?
C5 C4 C3 112.47(17) ?
C5 C4 H4A 109.1 ?
C3 C4 H4A 109.1 ?
C5 C4 H4B 109.1 ?
C3 C4 H4B 109.1 ?
H4A C4 H4B 107.8 ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C11 C6 C7 121.00(19) ?
C11 C6 S2' 111.1(3) ?
C7 C6 S2' 127.9(3) ?
C11 C6 S2 121.14(15) ?
C7 C6 S2 117.85(16) ?
S2' C6 S2 10.1(3) ?
C8 C7 C6 119.0(2) ?
C8 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
C7 C8 C9 121.1(2) ?
C7 C8 H8 119.4 ?
C9 C8 H8 119.4 ?
C10 C9 C8 118.4(2) ?
C10 C9 C12 120.1(2) ?
C8 C9 C12 121.4(2) ?
C11 C10 C9 121.3(2) ?
C11 C10 H10 119.3 ?
C9 C10 H10 119.3 ?
C6 C11 C10 119.05(19) ?
C6 C11 H11 120.5 ?
C10 C11 H11 120.5 ?
C9 C12 H12A 109.5 ?
C9 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C9 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.642(2) y
O1 C2 1.369(2) y
O1 C1 1.382(2) y
S2 O3 1.440(2) y
S2 O2 1.445(2) y
S2 N3 1.615(2) y
S2 C6 1.766(2) y
S2' O2' 1.439(2) y
S2' O3' 1.440(2) y
S2' N3' 1.610(2) y
S2' C6 1.766(2) y
N1 C1 1.330(2) y
N1 N2 1.387(2) y
N1 H1 0.8800 ?
N2 C2 1.279(2) y
N3 C3 1.450(3) y
N3 H3 0.8800 ?
C3 C2 1.498(2) ?
C3 C4 1.517(3) ?
C3 H3A 1.0000 ?
N3' H3' 0.8800 ?
C4 C5 1.514(3) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C6 C11 1.378(3) ?
C6 C7 1.395(3) ?
C7 C8 1.385(3) ?
C7 H7 0.9500 ?
C8 C9 1.392(3) ?
C8 H8 0.9500 ?
C9 C10 1.392(3) ?
C9 C12 1.510(3) ?
C10 C11 1.389(3) ?
C10 H10 0.9500 ?
C11 H11 0.9500 ?
C12 H12A 0.9800 ?
C12 H12B 0.9800 ?
C12 H12C 0.9800 ?
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 O2 8_455 0.88 1.96 2.840(2) 173
N1 H1 O2' 8_455 0.88 1.83 2.615(10) 148
N3 H3 O3 5_766 0.88 2.06 2.920(3) 165
N3' H3' N2 7_656 0.88 2.44 3.141(14) 137
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
C1 N1 N2 C2 0.1(2)
O3 S2 N3 C3 178.56(16)
O2 S2 N3 C3 -54.81(17)
C6 S2 N3 C3 60.74(18)
S2 N3 C3 C2 -85.42(19)
S2 N3 C3 C4 148.98(14)
N2 N1 C1 O1 0.2(2)
N2 N1 C1 S1 -179.52(15)
C2 O1 C1 N1 -0.4(2)
C2 O1 C1 S1 179.33(15)
N1 N2 C2 O1 -0.4(2)
N1 N2 C2 C3 178.92(18)
C1 O1 C2 N2 0.5(2)
C1 O1 C2 C3 -178.81(16)
N3 C3 C2 N2 117.2(2)
C4 C3 C2 N2 -118.1(2)
N3 C3 C2 O1 -63.6(2)
C4 C3 C2 O1 61.2(2)
N3 C3 C4 C5 -66.6(2)
C2 C3 C4 C5 168.09(19)
O2' S2' C6 C11 26.0(9)
O3' S2' C6 C11 155.5(8)
N3' S2' C6 C11 -90.3(6)
O2' S2' C6 C7 -154.7(8)
O3' S2' C6 C7 -25.2(9)
N3' S2' C6 C7 89.0(7)
O2' S2' C6 S2 -157(2)
O3' S2' C6 S2 -27.6(16)
N3' S2' C6 S2 86.6(19)
O3 S2 C6 C11 124.39(18)
O2 S2 C6 C11 -5.0(2)
N3 S2 C6 C11 -121.19(17)
O3 S2 C6 C7 -56.87(19)
O2 S2 C6 C7 173.75(16)
N3 S2 C6 C7 57.55(18)
O3 S2 C6 S2' 121.0(19)
O2 S2 C6 S2' -8.4(18)
N3 S2 C6 S2' -124.6(19)
C11 C6 C7 C8 -0.1(3)
S2' C6 C7 C8 -179.4(4)
S2 C6 C7 C8 -178.88(17)
C6 C7 C8 C9 -0.9(3)
C7 C8 C9 C10 0.9(3)
C7 C8 C9 C12 -179.0(2)
C8 C9 C10 C11 0.0(3)
C12 C9 C10 C11 179.9(2)
C7 C6 C11 C10 1.0(3)
S2' C6 C11 C10 -179.6(4)
S2 C6 C11 C10 179.73(16)
C9 C10 C11 C6 -1.0(3)
