#------------------------------------------------------------------------------
#$Date: 2015-06-04 06:06:32 +0300 (Thu, 04 Jun 2015) $
#$Revision: 137789 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/30/4513073.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_4513073
loop_
_publ_author_name
'Carletta, Andrea'
'Meinguet, Céline'
'Wouters, Johan'
'Tilborg, Anaëlle'
_publ_section_title
;
 Solid-State Investigation of Polymorphism and Tautomerism of
 Phenylthiazole-thione: A Combined Crystallographic, Calorimetric, and
 Theoretical Survey
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2461
_journal_paper_doi               10.1021/acs.cgd.5b00237
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C9 H7 N S2'
_chemical_formula_sum            'C9 H7 N S2'
_chemical_formula_weight         193.28
_chemical_name_common            'C33 Polymorph I'
_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           SHELXL-97
_audit_update_record
;
2015-02-09 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.780(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2423(2)
_cell_length_b                   11.5747(3)
_cell_length_c                   12.7785(4)
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.4964
_cell_measurement_theta_min      3.5303
_cell_volume                     903.84(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    sir92
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3637
_diffrn_reflns_theta_full        67.61
_diffrn_reflns_theta_max         67.61
_diffrn_reflns_theta_min         5.21
_exptl_absorpt_coefficient_mu    4.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0276
_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/[σ²(Fo²)+(0.0381P)²+0.2281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                1483
_reflns_number_total             1632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00237_si_001.cif
_cod_data_source_block           jw_c33
_cod_database_code               4513073
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.20664(7) 0.26810(4) 0.69185(4) 0.04991(16) Uani 1 1 d .
S2 S 0.26396(8) 0.01637(4) 0.64219(4) 0.05223(17) Uani 1 1 d .
N1 N -0.0634(2) 0.16082(11) 0.55507(10) 0.0410(3) Uani 1 1 d .
HN1 H -0.1303 0.1068 0.5151 0.049 Uiso 1 1 calc R
C4 C -0.3496(3) 0.30037(15) 0.47461(13) 0.0416(4) Uani 1 1 d .
C3 C -0.1456(3) 0.27244(14) 0.55088(13) 0.0407(4) Uani 1 1 d .
C1 C 0.1257(3) 0.14111(14) 0.62448(12) 0.0411(4) Uani 1 1 d .
C5 C -0.5191(3) 0.22014(17) 0.45179(15) 0.0506(4) Uani 1 1 d .
H5 H -0.5052 0.1488 0.4860 0.061 Uiso 1 1 calc R
C6 C -0.7081(3) 0.2464(2) 0.37838(18) 0.0639(6) Uani 1 1 d .
H6 H -0.8206 0.1925 0.3629 0.077 Uiso 1 1 calc R
C7 C -0.7301(3) 0.3523(2) 0.32816(17) 0.0673(6) Uani 1 1 d .
H7 H -0.8573 0.3697 0.2788 0.081 Uiso 1 1 calc R
C9 C -0.3742(3) 0.40684(17) 0.42419(15) 0.0517(4) Uani 1 1 d .
H9 H -0.2630 0.4615 0.4395 0.062 Uiso 1 1 calc R
C2 C -0.0164(3) 0.34154(15) 0.62135(14) 0.0471(4) Uani 1 1 d .
H2 H -0.0440 0.4194 0.6308 0.057 Uiso 1 1 calc R
C8 C -0.5650(4) 0.4319(2) 0.35085(17) 0.0634(6) Uani 1 1 d .
H8 H -0.5808 0.5034 0.3169 0.076 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 '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
C2 S1 C1 92.08(8)
C1 N1 C3 116.87(13)
C1 N1 HN1 121.6
C3 N1 HN1 121.6
C9 C4 C5 119.24(16)
C9 C4 C3 120.14(16)
C5 C4 C3 120.62(16)
C2 C3 N1 111.21(15)
C2 C3 C4 129.24(16)
N1 C3 C4 119.55(15)
N1 C1 S2 126.52(12)
N1 C1 S1 108.24(12)
S2 C1 S1 125.22(10)
C6 C5 C4 120.11(19)
C6 C5 H5 119.9
C4 C5 H5 119.9
C7 C6 C5 120.1(2)
C7 C6 H6 119.9
C5 C6 H6 119.9
C8 C7 C6 120.09(18)
C8 C7 H7 120.0
C6 C7 H7 120.0
C4 C9 C8 119.95(19)
C4 C9 H9 120.0
C8 C9 H9 120.0
C3 C2 S1 111.58(13)
C3 C2 H2 124.2
S1 C2 H2 124.2
C7 C8 C9 120.5(2)
C7 C8 H8 119.8
C9 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.7206(18)
S1 C1 1.7261(16)
S2 C1 1.6737(17)
N1 C1 1.343(2)
N1 C3 1.387(2)
N1 HN1 0.8600
C4 C9 1.385(3)
C4 C5 1.393(3)
C4 C3 1.473(2)
C3 C2 1.343(2)
C5 C6 1.383(3)
C5 H5 0.9300
C6 C7 1.377(3)
C6 H6 0.9300
C7 C8 1.369(3)
C7 H7 0.9300
C9 C8 1.387(3)
C9 H9 0.9300
C2 H2 0.9300
C8 H8 0.9300
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 C3 C2 -1.0(2)
C1 N1 C3 C4 178.56(15)
C9 C4 C3 C2 36.1(3)
C5 C4 C3 C2 -144.3(2)
C9 C4 C3 N1 -143.44(17)
C5 C4 C3 N1 36.1(2)
C3 N1 C1 S2 -177.65(13)
C3 N1 C1 S1 1.28(18)
C2 S1 C1 N1 -0.90(13)
C2 S1 C1 S2 178.04(13)
C9 C4 C5 C6 0.9(3)
C3 C4 C5 C6 -178.65(17)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 -0.1(3)
C5 C4 C9 C8 -0.8(3)
C3 C4 C9 C8 178.75(17)
N1 C3 C2 S1 0.28(19)
C4 C3 C2 S1 -179.28(15)
C1 S1 C2 C3 0.36(15)
C6 C7 C8 C9 0.2(3)
C4 C9 C8 C7 0.3(3)
