#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203362
loop_
_publ_author_name
'Du, Miao'
'Zhao, Xiao-Jun'
'Guo, Jian-Hua'
_publ_section_title
;
5-(4-Pyridyl)-1,3,4-oxadiazole-2(3H)-thione
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o327
_journal_page_last             o328
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C7 H5 N3 O S'
_chemical_formula_moiety       'C7 H5 N3 O S'
_chemical_formula_sum          'C7 H5 N3 O S'
_chemical_formula_weight       179.20
_chemical_name_systematic
;
5-(4-Pyridyl)-1,3,4-oxadiazole-2(3H)-thione
;
_symmetry_cell_setting         Monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 21/n'
_cell_angle_alpha              90.00
_cell_angle_beta               97.930(6)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 4.869(2)
_cell_length_b                 13.902(5)
_cell_length_c                 11.839(4)
_cell_measurement_reflns_used  683
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    24.10
_cell_measurement_theta_min    2.27
_cell_volume                   793.6(5)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_data_reduction      'SAINT (Bruker, 1998)'
_computing_molecular_graphics  'DIAMOND (Brandenburg & Berndt, 1999)'
_computing_publication_material 'SHELXTL (Bruker, 1998)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device     'Bruker SMART 1000'
_diffrn_measurement_method     \w
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0395
_diffrn_reflns_av_sigmaI/netI  0.0465
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_number          4439
_diffrn_reflns_theta_full      26.39
_diffrn_reflns_theta_max       26.39
_diffrn_reflns_theta_min       2.27
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.356
_exptl_absorpt_correction_T_max 0.9684
_exptl_absorpt_correction_T_min 0.9546
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour          yellow
_exptl_crystal_density_diffrn  1.500
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           368
_exptl_crystal_size_max        0.24
_exptl_crystal_size_mid        0.12
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.208
_refine_diff_density_min       -0.221
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.085
_refine_ls_hydrogen_treatment  constr
_refine_ls_number_parameters   109
_refine_ls_number_reflns       1616
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.085
_refine_ls_R_factor_all        0.0791
_refine_ls_R_factor_gt         0.0447
_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/[\s^2^(Fo^2^)+(0.0325P)^2^+0.1604P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0818
_refine_ls_wR_factor_ref       0.0920
_reflns_number_gt              1112
_reflns_number_total           1616
_reflns_threshold_expression   I>2\s(I)
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_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 0.20965(15) 0.47730(5) 0.22950(6) 0.0613(3) Uani d . 1 . . S
O1 0.5789(3) 0.58746(11) 0.35848(13) 0.0413(4) Uani d . 1 . . O
N1 0.2735(4) 0.66994(13) 0.25196(15) 0.0400(5) Uani d . 1 . . N
H1 0.1328 0.6853 0.2031 0.048 Uiso calc R 1 . . H
N2 0.4459(4) 0.73605(13) 0.31172(16) 0.0410(5) Uani d . 1 . . N
N3 1.3180(4) 0.77811(14) 0.60246(16) 0.0445(5) Uani d . 1 . . N
C1 0.3472(4) 0.57973(17) 0.27766(18) 0.0393(6) Uani d . 1 . . C
C2 0.6246(4) 0.68426(16) 0.37347(17) 0.0336(5) Uani d . 1 . . C
C3 1.2454(5) 0.68580(19) 0.5961(2) 0.0488(6) Uani d . 1 . . C
H3 1.3513 0.6420 0.6430 0.059 Uiso calc R 1 . . H
C4 1.0208(5) 0.65194(17) 0.52339(19) 0.0435(6) Uani d . 1 . . C
H4 0.9774 0.5868 0.5212 0.052 Uiso calc R 1 . . H
C5 0.8613(4) 0.71618(16) 0.45382(18) 0.0346(5) Uani d . 1 . . C
C6 0.9336(5) 0.81280(17) 0.46052(19) 0.0424(6) Uani d . 1 . . C
H6 0.8303 0.8583 0.4154 0.051 Uiso calc R 1 . . H
C7 1.1627(5) 0.83948(17) 0.5359(2) 0.0467(6) Uani d . 1 . . C
H7 1.2110 0.9042 0.5403 0.056 Uiso calc R 1 . . H
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 0.0599(5) 0.0484(4) 0.0689(5) -0.0058(3) -0.0151(3) -0.0094(4)
O1 0.0405(9) 0.0359(9) 0.0435(9) 0.0024(7) -0.0087(7) -0.0030(7)
N1 0.0359(11) 0.0437(12) 0.0370(11) 0.0028(9) -0.0070(8) 0.0013(9)
N2 0.0403(11) 0.0409(11) 0.0392(11) -0.0002(9) -0.0037(9) 0.0017(9)
N3 0.0384(11) 0.0518(13) 0.0415(12) -0.0029(10) -0.0015(9) -0.0045(10)
C1 0.0363(13) 0.0466(14) 0.0337(13) 0.0015(11) 0.0003(10) -0.0014(11)
C2 0.0352(12) 0.0348(12) 0.0309(12) 0.0020(10) 0.0043(9) 0.0014(11)
C3 0.0451(14) 0.0521(16) 0.0453(14) 0.0081(13) -0.0073(11) 0.0012(12)
C4 0.0483(15) 0.0347(14) 0.0447(15) 0.0012(11) -0.0034(11) -0.0006(11)
C5 0.0309(12) 0.0385(13) 0.0344(12) 0.0012(10) 0.0046(10) -0.0016(10)
C6 0.0410(13) 0.0406(14) 0.0436(14) 0.0027(11) -0.0010(11) 0.0056(11)
C7 0.0457(15) 0.0423(15) 0.0507(16) -0.0054(11) 0.0019(12) -0.0015(11)
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
C2 O1 C1 . . 105.59(16) yes
C1 N1 N2 . . 112.78(18) yes
C1 N1 H1 . . 123.6 ?
N2 N1 H1 . . 123.6 ?
C2 N2 N1 . . 103.71(18) yes
C7 N3 C3 . . 117.5(2) yes
N1 C1 O1 . . 104.75(19) ?
N1 C1 S1 . . 130.91(17) yes
O1 C1 S1 . . 124.33(17) yes
N2 C2 O1 . . 113.16(18) ?
N2 C2 C5 . . 128.0(2) ?
O1 C2 C5 . . 118.84(18) ?
N3 C3 C4 . . 123.1(2) ?
N3 C3 H3 . . 118.4 ?
C4 C3 H3 . . 118.4 ?
C3 C4 C5 . . 119.0(2) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 118.4(2) ?
C4 C5 C2 . . 121.4(2) ?
C6 C5 C2 . . 120.20(19) ?
C7 C6 C5 . . 118.2(2) ?
C7 C6 H6 . . 120.9 ?
C5 C6 H6 . . 120.9 ?
N3 C7 C6 . . 123.7(2) ?
N3 C7 H7 . . 118.1 ?
C6 C7 H7 . . 118.1 ?
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 C1 . 1.642(2) yes
O1 C2 . 1.371(2) ?
O1 C1 . 1.379(3) ?
N1 C1 . 1.328(3) yes
N1 N2 . 1.373(2) yes
N1 H1 . 0.8600 ?
N2 C2 . 1.278(3) yes
N3 C7 . 1.325(3) yes
N3 C3 . 1.330(3) yes
C2 C5 . 1.458(3) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(3) ?
C6 C7 . 1.380(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 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
_geom_hbond_publ_flag
N1 H1 N3 4_475 0.86 1.88 2.737(3) 177 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 0.1(3) ?
N2 N1 C1 O1 . . . . 0.2(2) ?
N2 N1 C1 S1 . . . . -179.75(18) ?
C2 O1 C1 N1 . . . . -0.4(2) ?
C2 O1 C1 S1 . . . . 179.54(16) ?
N1 N2 C2 O1 . . . . -0.4(2) ?
N1 N2 C2 C5 . . . . 179.2(2) ?
C1 O1 C2 N2 . . . . 0.5(2) ?
C1 O1 C2 C5 . . . . -179.15(18) ?
C7 N3 C3 C4 . . . . 0.7(4) ?
N3 C3 C4 C5 . . . . -0.3(4) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
C3 C4 C5 C2 . . . . 178.7(2) ?
N2 C2 C5 C4 . . . . 173.3(2) ?
O1 C2 C5 C4 . . . . -7.1(3) ?
N2 C2 C5 C6 . . . . -7.7(4) ?
O1 C2 C5 C6 . . . . 171.9(2) ?
C4 C5 C6 C7 . . . . 0.5(3) ?
C2 C5 C6 C7 . . . . -178.6(2) ?
C3 N3 C7 C6 . . . . -0.6(4) ?
C5 C6 C7 N3 . . . . 0.0(4) ?