#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225983.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_2225983
loop_
_publ_author_name
'Lian, Guo-Jun'
'Chen, Bo'
'Zhang, Ting-Ting'
'Zhuang, Li-Zhen'
'Liang, Hong-Ze'
_publ_section_title
;
 6-Methylpyridine-2(1H)-thione
;
_journal_coeditor_code           SJ2766
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1154
_journal_page_last               o1155
_journal_paper_doi               10.1107/S1600536810014273
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H7 N S'
_chemical_formula_moiety         'C6 H7 N S'
_chemical_formula_sum            'C6 H7 N S'
_chemical_formula_weight         125.19
_chemical_name_systematic
;
6-Methylpyridine-2(1H)-thione
;
_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                90.00
_cell_angle_beta                 94.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4608(15)
_cell_length_b                   14.902(3)
_cell_length_c                   11.665(2)
_cell_measurement_reflns_used    12782
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1292.3(4)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12472
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.3029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2088
_reflns_number_total             2944
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2766.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225983
_cod_database_fobs_code          2225983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.52754(9) 0.10281(4) 0.87258(5) 0.0561(2) Uani d . 1 . .
S S2 0.90012(12) 0.13575(4) 0.50014(6) 0.0743(3) Uani d . 1 . .
N N1 0.5873(2) -0.07318(12) 0.85963(15) 0.0470(4) Uani d . 1 . .
H H1A 0.5725 -0.0723 0.9319 0.056 Uiso calc R 1 . .
N N2 0.9262(2) 0.02468(12) 0.32400(15) 0.0488(4) Uani d . 1 . .
H H2A 0.9555 -0.0139 0.3771 0.059 Uiso calc R 1 . .
C C1 0.6385(5) -0.23318(17) 0.8905(2) 0.0746(8) Uani d . 1 . .
H H1B 0.6160 -0.2149 0.9669 0.112 Uiso calc R 1 . .
H H1C 0.7568 -0.2587 0.8916 0.112 Uiso calc R 1 . .
H H1D 0.5509 -0.2772 0.8633 0.112 Uiso calc R 1 . .
C C2 0.6257(3) -0.15375(16) 0.8125(2) 0.0541(6) Uani d . 1 . .
C C3 0.6503(4) -0.15630(18) 0.6979(2) 0.0626(6) Uani d . 1 . .
H H3A 0.6773 -0.2102 0.6631 0.075 Uiso calc R 1 . .
C C4 0.6350(4) -0.0782(2) 0.6339(2) 0.0658(7) Uani d . 1 . .
H H4A 0.6513 -0.0800 0.5557 0.079 Uiso calc R 1 . .
C C5 0.5961(3) 0.00181(18) 0.68372(19) 0.0593(6) Uani d . 1 . .
H H5A 0.5868 0.0536 0.6392 0.071 Uiso calc R 1 . .
C C6 0.5702(3) 0.00646(15) 0.80167(18) 0.0469(5) Uani d . 1 . .
C C7 0.9694(4) -0.10058(16) 0.1955(2) 0.0609(6) Uani d . 1 . .
H H7A 0.9963 -0.1291 0.2687 0.091 Uiso calc R 1 . .
H H7B 1.0723 -0.1042 0.1516 0.091 Uiso calc R 1 . .
H H7C 0.8693 -0.1303 0.1546 0.091 Uiso calc R 1 . .
C C8 0.9229(3) -0.00394(16) 0.21353(19) 0.0499(5) Uani d . 1 . .
C C9 0.8776(3) 0.05620(18) 0.1275(2) 0.0590(6) Uani d . 1 . .
H H9A 0.8744 0.0386 0.0508 0.071 Uiso calc R 1 . .
C C10 0.8365(4) 0.14393(18) 0.1558(2) 0.0634(7) Uani d . 1 . .
H H10A 0.8072 0.1853 0.0975 0.076 Uiso calc R 1 . .
C C11 0.8384(3) 0.17037(16) 0.2678(2) 0.0581(6) Uani d . 1 . .
H H11A 0.8074 0.2290 0.2849 0.070 Uiso calc R 1 . .
C C12 0.8870(3) 0.10976(15) 0.3583(2) 0.0517(5) Uani d . 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'
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 N1 C6 . . 125.47(18) ?
C2 N1 H1A . . 117.3 ?
C6 N1 H1A . . 117.3 ?
C8 N2 C12 . . 125.61(19) ?
C8 N2 H2A . . 117.2 ?
C12 N2 H2A . . 117.2 ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
N1 C2 C3 . . 118.1(2) ?
N1 C2 C1 . . 117.3(2) ?
C3 C2 C1 . . 124.6(2) ?
C2 C3 C4 . . 119.6(2) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C5 C4 C3 . . 121.0(2) ?
C5 C4 H4A . . 119.5 ?
C3 C4 H4A . . 119.5 ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5A . . 119.7 ?
C6 C5 H5A . . 119.7 ?
N1 C6 C5 . . 115.2(2) ?
N1 C6 S1 . . 120.41(15) ?
C5 C6 S1 . . 124.34(19) ?
C8 C7 H7A . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C8 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 118.4(2) ?
N2 C8 C7 . . 116.7(2) ?
C9 C8 C7 . . 124.9(2) ?
C8 C9 C10 . . 119.2(2) ?
C8 C9 H9A . . 120.4 ?
C10 C9 H9A . . 120.4 ?
C11 C10 C9 . . 121.0(2) ?
C11 C10 H10A . . 119.5 ?
C9 C10 H10A . . 119.5 ?
C10 C11 C12 . . 120.8(2) ?
C10 C11 H11A . . 119.6 ?
C12 C11 H11A . . 119.6 ?
N2 C12 C11 . . 114.9(2) ?
N2 C12 S2 . . 120.08(17) ?
C11 C12 S2 . . 125.00(19) ?
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 C6 . 1.700(2) ?
S2 C12 . 1.694(3) ?
N1 C2 . 1.361(3) ?
N1 C6 . 1.367(3) ?
N1 H1A . 0.8600 ?
N2 C8 . 1.356(3) ?
N2 C12 . 1.369(3) ?
N2 H2A . 0.8600 ?
C1 C2 . 1.491(4) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 C3 . 1.366(3) ?
C3 C4 . 1.383(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.368(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.407(3) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.500(3) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.367(3) ?
C9 C10 . 1.389(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.363(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.413(3) ?
C11 H11A . 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 H1A S1 3_657 0.86 2.50 3.3376(19) 165 y
N2 H2A S2 3_756 0.86 2.50 3.340(2) 166 y
C1 H1B S1 3_657 0.96 2.79 3.678(3) 154 y
C7 H7A S2 3_756 0.96 2.74 3.639(3) 156 y
