#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/22/2212262.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_2212262
loop_
_publ_author_name
'Singh, N. K.'
'Butcher, Ray J.'
'Tripathi, Pratibha'
'Srivastava, Ajay K.'
'Bharty, Manoj Kumar'
_publ_section_title
;
 5-Phenyl-1,3,4-oxadiazole-2(3H)-thione
;
_journal_coeditor_code           KJ2029
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o782
_journal_page_last               o784
_journal_paper_doi               10.1107/S1600536806052238
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H6 N2 O S'
_chemical_formula_moiety         'C8 H6 N2 O S'
_chemical_formula_sum            'C8 H6 N2 O S'
_chemical_formula_weight         178.21
_chemical_name_systematic
;
5-Phenyl-1,3,4-oxadiazole-2(3H)-thione
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.845(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3414(15)
_cell_length_b                   4.6589(16)
_cell_length_c                   16.0242(7)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      3.70
_cell_volume                     822.1(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'Bruker APEXII 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     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12966
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.73
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.9766
_exptl_absorpt_correction_T_min  0.7748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0395
_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)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                2386
_reflns_number_total             2888
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2029.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2212262
_cod_database_fobs_code          2212262
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
S S1 0.68387(3) 1.03196(9) 0.45854(2) 0.04557(13) Uani d . 1
O O1 0.60441(7) 0.6440(2) 0.33504(6) 0.0379(2) Uani d . 1
C C1 0.49558(11) 0.2792(3) 0.23604(8) 0.0372(3) Uani d . 1
C C7 0.50227(11) 0.4791(3) 0.30667(9) 0.0374(3) Uani d . 1
C C8 0.58430(11) 0.8025(3) 0.40210(8) 0.0375(3) Uani d . 1
N N1 0.42105(12) 0.5232(3) 0.34905(9) 0.0477(3) Uani d . 1
C C6 0.59515(12) 0.2282(4) 0.20132(10) 0.0454(3) Uani d . 1
H H6A 0.6678 0.3252 0.2226 0.055 Uiso calc R 1
N N2 0.47371(10) 0.7277(3) 0.40827(8) 0.0475(3) Uani d . 1
H H2B 0.4386 0.7996 0.4455 0.057 Uiso calc R 1
C C5 0.58552(15) 0.0333(4) 0.13530(10) 0.0531(4) Uani d . 1
H H5A 0.6521 -0.0037 0.1126 0.064 Uiso calc R 1
C C2 0.38610(12) 0.1370(4) 0.20291(10) 0.0470(3) Uani d . 1
H H2A 0.3193 0.1714 0.2257 0.056 Uiso calc R 1
C C4 0.47638(15) -0.1079(4) 0.10273(10) 0.0544(4) Uani d . 1
H H4A 0.4702 -0.2389 0.0581 0.065 Uiso calc R 1
C C3 0.37748(16) -0.0554(4) 0.13593(11) 0.0536(4) Uani d . 1
H H3A 0.3045 -0.1496 0.1133 0.064 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.04042(19) 0.0496(2) 0.0479(2) -0.00313(15) 0.01284(15) -0.00394(16)
O1 0.0333(4) 0.0403(5) 0.0424(5) 0.0001(4) 0.0134(4) -0.0003(4)
C1 0.0347(6) 0.0375(7) 0.0395(6) 0.0024(5) 0.0092(5) 0.0031(5)
C7 0.0303(5) 0.0392(7) 0.0431(6) 0.0015(5) 0.0093(5) 0.0041(6)
C8 0.0378(6) 0.0369(7) 0.0396(6) 0.0051(5) 0.0125(5) 0.0047(5)
N1 0.0366(6) 0.0552(8) 0.0547(7) -0.0038(5) 0.0174(5) -0.0099(6)
C6 0.0361(6) 0.0533(9) 0.0487(7) -0.0028(6) 0.0136(6) -0.0039(6)
N2 0.0400(6) 0.0553(8) 0.0522(7) -0.0027(6) 0.0211(5) -0.0110(6)
C5 0.0478(8) 0.0624(11) 0.0543(9) 0.0004(7) 0.0227(7) -0.0050(8)
C2 0.0351(6) 0.0533(9) 0.0538(8) -0.0028(6) 0.0130(6) -0.0025(7)
C4 0.0616(10) 0.0552(10) 0.0466(8) -0.0018(8) 0.0131(7) -0.0085(7)
C3 0.0478(8) 0.0555(10) 0.0546(9) -0.0086(7) 0.0069(7) -0.0066(7)
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
C8 O1 C7 106.03(10)
C6 C1 C2 119.97(14)
C6 C1 C7 121.59(12)
C2 C1 C7 118.44(12)
N1 C7 O1 112.96(12)
N1 C7 C1 127.12(13)
O1 C7 C1 119.92(12)
N2 C8 O1 104.77(12)
N2 C8 S1 131.38(12)
O1 C8 S1 123.86(10)
C7 N1 N2 103.14(12)
C5 C6 C1 119.71(14)
C5 C6 H6A 120.1
C1 C6 H6A 120.1
C8 N2 N1 113.09(12)
C8 N2 H2B 123.5
N1 N2 H2B 123.5
C6 C5 C4 120.02(15)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C3 C2 C1 119.60(14)
C3 C2 H2A 120.2
C1 C2 H2A 120.2
C3 C4 C5 120.48(15)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C4 C3 C2 120.20(15)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.6574(15) y
O1 C8 1.3672(16) y
O1 C7 1.3739(16) y
C1 C6 1.3936(19) ?
C1 C2 1.3953(19) ?
C1 C7 1.454(2) ?
C7 N1 1.2850(19) y
C8 N2 1.3281(17) y
N1 N2 1.3761(18) y
C6 C5 1.378(2) ?
C6 H6A 0.9300 ?
N2 H2B 0.8600 ?
C5 C4 1.389(2) ?
C5 H5A 0.9300 ?
C2 C3 1.384(2) ?
C2 H2A 0.9300 ?
C4 C3 1.373(2) ?
C4 H4A 0.9300 ?
C3 H3A 0.9300 ?
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
N2 H2B S1 3_676 0.86 2.44 3.2907(13) 172.6
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
C8 O1 C7 N1 0.75(15)
C8 O1 C7 C1 -178.73(11)
C6 C1 C7 N1 -172.88(15)
C2 C1 C7 N1 7.2(2)
C6 C1 C7 O1 6.5(2)
C2 C1 C7 O1 -173.42(13)
C7 O1 C8 N2 -1.02(14)
C7 O1 C8 S1 179.01(10)
O1 C7 N1 N2 -0.13(16)
C1 C7 N1 N2 179.30(13)
C2 C1 C6 C5 -1.2(2)
C7 C1 C6 C5 178.92(14)
O1 C8 N2 N1 1.02(17)
S1 C8 N2 N1 -179.02(12)
C7 N1 N2 C8 -0.58(18)
C1 C6 C5 C4 1.0(3)
C6 C1 C2 C3 0.4(2)
C7 C1 C2 C3 -179.69(14)
C6 C5 C4 C3 -0.1(3)
C5 C4 C3 C2 -0.6(3)
C1 C2 C3 C4 0.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 642445
