#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/89/2018915.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_2018915
loop_
_publ_author_name
'Fu, Wei-Wei'
'Chen, Man-Sheng'
'Liu, Yang'
'Zhang, Fu-Xing'
_publ_section_title
;
 (4,6-Dimethyl-2-sulfanylidenepyrimidin-1-ium)
 trichlorido(thiourea-κS)zinc(II)
;
_journal_coeditor_code           KY3022
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              384
_journal_page_last               387
_journal_paper_doi               10.1107/S0108270113006380
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '(C6 H9 N2 S) [Zn Cl3 (C H4 N2 S)]'
_chemical_formula_moiety         'C6 H9 N2 S +, C H4 Cl3 N2 S Zn -'
_chemical_formula_sum            'C7 H13 Cl3 N4 S2 Zn'
_chemical_formula_weight         389.05
_chemical_name_systematic
;
(4,6-Dimethyl-2-sulfanylidenepyrimidin-1-ium)
trichlorido(thiourea-κS)zinc(II)
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3648(4)
_cell_length_b                   7.3374(2)
_cell_length_c                   26.7111(6)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      36.28
_cell_measurement_theta_min      3.06
_cell_volume                     3004.31(13)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            40204
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    2.430
_exptl_absorpt_correction_T_max  0.7272
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0153
_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)+(0.0175P)²+3.2453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0396
_refine_ls_wR_factor_ref         0.0401
_reflns_number_gt                3166
_reflns_number_total             3285
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ky3022.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018915
_cod_database_fobs_code          2018915
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_symmetry_multiplicity
Zn Zn1 0.158445(9) 0.36606(2) 0.143070(5) 0.01699(5) Uani d . 1 1
C C1 1.01043(8) 0.83474(17) 0.13185(5) 0.0191(2) Uani d . 1 1
C C2 1.06449(8) 0.83285(17) 0.04895(5) 0.0178(2) Uani d . 1 1
C C3 0.92225(8) 0.71085(18) 0.06348(5) 0.0203(2) Uani d . 1 1
C C4 0.93385(8) 0.75250(18) 0.11398(5) 0.0213(3) Uani d . 1 1
H H4 0.8897 0.7249 0.1360 0.026 Uiso calc R 1 1
C C5 1.02883(9) 0.8889(2) 0.18534(5) 0.0255(3) Uani d . 1 1
H H5A 1.0834 0.8320 0.1986 0.038 Uiso calc R 1 1
H H5B 0.9809 0.8485 0.2050 0.038 Uiso calc R 1 1
H H5C 1.0344 1.0217 0.1876 0.038 Uiso calc R 1 1
C C6 0.84299(9) 0.6208(2) 0.03986(6) 0.0292(3) Uani d . 1 1
H H6A 0.8289 0.6733 0.0066 0.044 Uiso calc R 1 1
H H6B 0.7939 0.6398 0.0609 0.044 Uiso calc R 1 1
H H6C 0.8539 0.4899 0.0366 0.044 Uiso calc R 1 1
C C7 0.31245(9) 0.66412(17) 0.16888(5) 0.0213(3) Uani d . 1 1
Cl Cl1 0.04641(2) 0.33090(5) 0.083500(11) 0.02363(7) Uani d . 1 1
Cl Cl2 0.09307(2) 0.43667(4) 0.214950(11) 0.02243(7) Uani d . 1 1
Cl Cl3 0.228033(19) 0.09711(4) 0.159042(11) 0.01977(7) Uani d . 1 1
N N1 1.07231(7) 0.86972(15) 0.09959(4) 0.0181(2) Uani d D 1 1
H H1 1.1205(7) 0.921(2) 0.1108(6) 0.022 Uiso d D 1 1
N N2 0.98620(7) 0.75282(15) 0.03367(4) 0.0187(2) Uani d D 1 1
H H2 0.9787(10) 0.732(2) 0.0020(3) 0.022 Uiso d D 1 1
N N3 0.38639(8) 0.75308(17) 0.16300(6) 0.0283(3) Uani d . 1 1
H H3A 0.4115(12) 0.806(3) 0.1873(7) 0.034 Uiso d . 1 1
H H3B 0.4036(11) 0.764(3) 0.1328(7) 0.034 Uiso d . 1 1
N N4 0.28743(9) 0.64036(18) 0.21465(5) 0.0281(3) Uani d . 1 1
H H4B 0.3136(12) 0.692(3) 0.2380(7) 0.034 Uiso d . 1 1
H H4A 0.2399(13) 0.593(3) 0.2192(7) 0.034 Uiso d . 1 1
S S1 1.14037(2) 0.87802(5) 0.010083(12) 0.02336(7) Uani d . 1 1
S S2 0.25353(2) 0.58583(4) 0.115888(12) 0.02081(7) Uani d . 1 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
Cl3 Zn1 Cl1 110.883(13) y
Cl3 Zn1 Cl2 105.508(12) y
Cl1 Zn1 Cl2 104.946(13) y
Cl3 Zn1 S2 111.316(13) y
Cl1 Zn1 S2 108.749(13) y
Cl2 Zn1 S2 115.248(13) y
N1 C1 C4 118.92(12) ?
N1 C1 C5 117.71(12) ?
C4 C1 C5 123.36(12) ?
N2 C2 N1 113.03(11) ?
N2 C2 S1 122.78(10) ?
N1 C2 S1 124.19(10) ?
N2 C3 C4 118.51(12) ?
N2 C3 C6 117.49(12) ?
C4 C3 C6 124.00(12) ?
C1 C4 C3 119.00(12) ?
C1 C4 H4 120.5 ?
C3 C4 H4 120.5 ?
C1 C5 H5A 109.5 ?
C1 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C1 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C3 C6 H6A 109.5 ?
C3 C6 H6B 109.5 ?
H6A C6 H6B 109.5 ?
C3 C6 H6C 109.5 ?
H6A C6 H6C 109.5 ?
H6B C6 H6C 109.5 ?
N4 C7 N3 118.73(13) ?
N4 C7 S2 123.16(11) ?
N3 C7 S2 118.12(11) ?
C1 N1 C2 124.86(11) ?
C1 N1 H1 119.0(10) ?
C2 N1 H1 116.1(10) ?
C3 N2 C2 125.65(11) ?
C3 N2 H2 119.3(10) ?
C2 N2 H2 115.0(10) ?
C7 N3 H3A 119.6(13) ?
C7 N3 H3B 118.1(12) ?
H3A N3 H3B 122.0(17) ?
C7 N4 H4B 119.3(13) ?
C7 N4 H4A 120.6(13) ?
H4B N4 H4A 118.6(18) ?
C7 S2 Zn1 106.28(5) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 Cl3 2.2710(3) y
Zn1 Cl1 2.2775(3) y
Zn1 Cl2 2.2863(3) y
Zn1 S2 2.3252(4) y
C1 N1 1.3507(17) y
C1 C4 1.3782(18) y
C1 C5 1.4912(18) y
C2 N2 1.3753(16) y
C2 N1 1.3767(16) y
C2 S1 1.6469(13) y
C3 N2 1.3422(17) y
C3 C4 1.3826(18) y
C3 C6 1.4876(18) y
C4 H4 0.9500 ?
C5 H5A 0.9800 ?
C5 H5B 0.9800 ?
C5 H5C 0.9800 ?
C6 H6A 0.9800 ?
C6 H6B 0.9800 ?
C6 H6C 0.9800 ?
C7 N4 1.3179(19) ?
C7 N3 1.3289(18) ?
C7 S2 1.7257(14) ?
N1 H1 0.866(9) ?
N2 H2 0.860(9) ?
N3 H3A 0.828(19) ?
N3 H3B 0.869(19) ?
N4 H4B 0.81(2) ?
N4 H4A 0.82(2) ?
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 Cl3 1_665 0.866(9) 2.402(14) 3.2420(11) 163.8(12)
N2 H2 Cl1 5_665 0.860(9) 2.336(8) 3.1952(11) 177.8(16)
N3 H3A Cl2 4 0.828(19) 2.787(19) 3.5216(16) 148.7(16)
N3 H3B Cl1 3 0.869(19) 2.680(18) 3.4050(14) 141.6(15)
N4 H4B Cl2 4 0.81(2) 2.57(2) 3.3410(14) 158.6(18)
N4 H4A Cl2 . 0.82(2) 2.53(2) 3.3399(14) 168.8(18)
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
N1 C1 C4 C3 -0.94(19)
C5 C1 C4 C3 178.69(12)
N2 C3 C4 C1 -0.20(19)
C6 C3 C4 C1 179.44(13)
C4 C1 N1 C2 1.48(19)
C5 C1 N1 C2 -178.17(12)
N2 C2 N1 C1 -0.76(17)
S1 C2 N1 C1 179.48(10)
C4 C3 N2 C2 0.97(19)
C6 C3 N2 C2 -178.69(12)
N1 C2 N2 C3 -0.51(18)
S1 C2 N2 C3 179.26(10)
N4 C7 S2 Zn1 -18.07(13)
N3 C7 S2 Zn1 162.16(10)
Cl3 Zn1 S2 C7 -78.35(5)
Cl1 Zn1 S2 C7 159.20(5)
Cl2 Zn1 S2 C7 41.74(5)
