#------------------------------------------------------------------------------
#$Date: 2017-09-01 10:05:54 +0300 (Fri, 01 Sep 2017) $
#$Revision: 200067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/69/1546923.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_1546923
loop_
_publ_author_name
'Lampl, Martin'
'Laus, Gerhard'
'Wurst, Klaus'
'Huppertz, Hubert'
'Schottenberger, Herwig'
_publ_section_title
;
 1-Vinyl-4-imidazoline-2-thione
;
_journal_coeditor_code           QM4003
_journal_issue                   8
_journal_name_full               IUCrData
_journal_page_first              x171207
_journal_paper_doi               10.1107/S241431461701207X
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C5 H6 N2 S'
_chemical_formula_moiety         'C5 H6 N2 S'
_chemical_formula_sum            'C5 H6 N2 S'
_chemical_formula_weight         126.18
_chemical_melting_point          418
_chemical_name_systematic
;
1-Vinyl-4-imidazoline-2-thione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'SHELXL-2014/7 (Sheldrick, 2015)'
_cell_angle_alpha                90
_cell_angle_beta                 108.1390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7775(3)
_cell_length_b                   9.6848(3)
_cell_length_c                   12.1792(4)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.9
_cell_volume                     1208.06(6)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae et al.,  2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
XT in SHELXTL (Bruker, 2014)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.895
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.215
_refine_ls_extinction_coef       0.0068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1187
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+1.0869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0649
_reflns_number_gt                1114
_reflns_number_total             1187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qm4003sup1.cif
_cod_data_source_block           I
_cod_database_code               1546923
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_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_occupancy
S S1 0.11344(3) 0.54728(4) 0.42718(3) 0.02539(14) Uani d 1
N N1 0.31623(10) 0.38500(11) 0.41324(9) 0.0200(2) Uani d 1
N N2 0.17797(11) 0.43417(12) 0.24678(9) 0.0225(2) Uani d 1
H H2N 0.1110(15) 0.4659(17) 0.1942(13) 0.034(4) Uiso d 1
C C1 0.20309(12) 0.45566(12) 0.36118(11) 0.0192(3) Uani d 1
C C2 0.35897(13) 0.32017(14) 0.32890(11) 0.0241(3) Uani d 1
H H2 0.4349 0.2647 0.3421 0.029 Uiso calc 1
C C3 0.27288(13) 0.35079(14) 0.22622(11) 0.0250(3) Uani d 1
H H3 0.2762 0.3209 0.1529 0.030 Uiso calc 1
C C4 0.37875(13) 0.38285(14) 0.53361(11) 0.0262(3) Uani d 1
H H4 0.3320 0.4176 0.5821 0.031 Uiso calc 1
C C5 0.49716(14) 0.33608(16) 0.58291(12) 0.0327(3) Uani d 1
H H5A 0.5466 0.3006 0.5369 0.039 Uiso calc 1
H H5B 0.5335 0.3376 0.6647 0.039 Uiso calc 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
C1 N1 C2 109.49(10)
C1 N1 C4 123.85(11)
C2 N1 C4 126.64(11)
C1 N2 C3 110.74(11)
C1 N2 H2N 124.5(11)
C3 N2 H2N 124.7(11)
N2 C1 N1 105.33(11)
N2 C1 S1 127.71(10)
N1 C1 S1 126.95(10)
C3 C2 N1 107.21(11)
C3 C2 H2 126.4
N1 C2 H2 126.4
C2 C3 N2 107.24(11)
C2 C3 H3 126.4
N2 C3 H3 126.4
C5 C4 N1 124.29(13)
C5 C4 H4 117.9
N1 C4 H4 117.9
C4 C5 H5A 120.0
C4 C5 H5B 120.0
H5A C5 H5B 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6884(13)
N1 C1 1.3695(16)
N1 C2 1.3986(16)
N1 C4 1.4102(16)
N2 C1 1.3502(16)
N2 C3 1.3858(17)
N2 H2N 0.859(14)
C2 C3 1.3380(19)
C2 H2 0.9500
C3 H3 0.9500
C4 C5 1.3104(19)
C4 H4 0.9500
C5 H5A 0.9500
C5 H5B 0.9500
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
N2 H2N S1 2_555 0.860(10) 2.540(10) 3.3780(10) 167.0(10) y
C2 H2 S1 3_545 0.95 2.82 3.7280(10) 160 y
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
C3 N2 C1 N1 0.31(14)
C3 N2 C1 S1 -178.63(10)
C2 N1 C1 N2 -0.18(14)
C4 N1 C1 N2 178.55(11)
C2 N1 C1 S1 178.77(10)
C4 N1 C1 S1 -2.51(18)
C1 N1 C2 C3 -0.01(15)
C4 N1 C2 C3 -178.69(12)
N1 C2 C3 N2 0.19(15)
C1 N2 C3 C2 -0.32(15)
C1 N1 C4 C5 -167.81(14)
C2 N1 C4 C5 10.7(2)

_cod_database_fobs_code 1546923
