#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/30/2213092.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_2213092
loop_
_publ_author_name
'Yong Wang'
'Wei Wang'
'Jing Wang'
'Xi-Fei Zhou'
'Ling-Ling Mao'
_publ_section_title
;
 2,2'-(m-Phenylenedimethylenedithio)bis(1,3-thiazoline)
;
_journal_coeditor_code           AT2262
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2440
_journal_page_last               o2441
_journal_paper_doi               10.1107/S1600536807016716
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H16 N2 S4'
_chemical_formula_moiety         'C14 H16 N2 S4'
_chemical_formula_sum            'C14 H16 N2 S4'
_chemical_formula_weight         340.53
_chemical_melting_point          335
_chemical_name_systematic
;
2,2'-(m-Phenylenedimethylenedithio)bis(1,3-thiazoline)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.61(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.47(2)
_cell_length_b                   7.195(6)
_cell_length_c                   9.097(8)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.95
_cell_volume                     1601(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3865
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0386
_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)+(0.0684P)²+0.4326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                1024
_reflns_number_total             1420
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2262.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213092
_cod_database_fobs_code          2213092
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
S S1 0.28316(3) 0.28032(14) 0.82060(11) 0.0723(4) Uani d . 1
S S2 0.35173(3) 0.05214(12) 0.62772(9) 0.0599(3) Uani d . 1
N N1 0.38555(10) 0.3579(4) 0.7746(3) 0.0599(7) Uani d . 1
C C1 0.31168(17) 0.4628(6) 0.9315(5) 0.0813(11) Uani d . 1
H H1A 0.2879 0.5706 0.9287 0.098 Uiso calc R 1
H H1B 0.3163 0.4223 1.0328 0.098 Uiso calc R 1
C C2 0.36616(15) 0.5096(5) 0.8683(4) 0.0688(9) Uani d . 1
H H2A 0.3628 0.6227 0.8107 0.083 Uiso calc R 1
H H2B 0.3926 0.5316 0.9477 0.083 Uiso calc R 1
C C3 0.34814(11) 0.2437(4) 0.7452(3) 0.0438(7) Uani d . 1
C C4 0.42161(12) 0.0664(5) 0.5653(3) 0.0562(8) Uani d . 1
H H4A 0.4228 0.0167 0.4663 0.067 Uiso calc R 1
H H4B 0.4323 0.1961 0.5611 0.067 Uiso calc R 1
C C5 0.46223(10) -0.0362(4) 0.6613(3) 0.0429(7) Uani d . 1
C C6 0.46310(14) -0.2285(4) 0.6614(4) 0.0664(9) Uani d . 1
H H6 0.4386 -0.2940 0.6011 0.080 Uiso calc R 1
C C7 0.5000 -0.3232(7) 0.7500 0.0853(18) Uani d S 1
H H7 0.5000 -0.4524 0.7500 0.102 Uiso calc SR 1
C C8 0.5000 0.0582(5) 0.7500 0.0402(9) Uani d S 1
H H8 0.5000 0.1874 0.7500 0.048 Uiso calc SR 1
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 0.0527(5) 0.0828(7) 0.0829(7) -0.0076(4) 0.0274(4) -0.0170(5)
S2 0.0384(4) 0.0697(6) 0.0719(6) -0.0033(4) 0.0040(3) -0.0206(4)
N1 0.0494(15) 0.0616(16) 0.0690(18) -0.0057(14) 0.0054(12) -0.0093(15)
C1 0.081(3) 0.085(3) 0.078(2) 0.000(2) 0.018(2) -0.025(2)
C2 0.073(2) 0.065(2) 0.068(2) -0.0025(18) 0.0008(17) -0.0111(18)
C3 0.0399(15) 0.0529(18) 0.0386(15) 0.0031(14) 0.0035(11) 0.0042(13)
C4 0.0414(15) 0.083(2) 0.0446(16) 0.0046(16) 0.0108(12) -0.0038(16)
C5 0.0356(14) 0.0505(17) 0.0434(15) 0.0004(13) 0.0146(11) -0.0051(14)
C6 0.0502(18) 0.0503(19) 0.099(3) -0.0081(16) 0.0072(17) -0.0214(19)
C7 0.074(4) 0.032(2) 0.150(6) 0.000 0.011(4) 0.000
C8 0.043(2) 0.036(2) 0.042(2) 0.000 0.0167(16) 0.000
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
_geom_angle_publ_flag
C3 S1 C1 . 89.28(16) ?
C3 S2 C4 . 102.13(15) yes
C3 N1 C2 . 111.4(3) ?
C2 C1 S1 . 106.6(2) ?
C2 C1 H1A . 110.4 ?
S1 C1 H1A . 110.4 ?
C2 C1 H1B . 110.4 ?
S1 C1 H1B . 110.4 ?
H1A C1 H1B . 108.6 ?
N1 C2 C1 . 111.0(3) ?
N1 C2 H2A . 109.4 ?
C1 C2 H2A . 109.4 ?
N1 C2 H2B . 109.4 ?
C1 C2 H2B . 109.4 ?
H2A C2 H2B . 108.0 ?
N1 C3 S2 . 126.8(2) yes
N1 C3 S1 . 118.6(2) ?
S2 C3 S1 . 114.56(16) yes
C5 C4 S2 . 113.8(2) ?
C5 C4 H4A . 108.8 ?
S2 C4 H4A . 108.8 ?
C5 C4 H4B . 108.8 ?
S2 C4 H4B . 108.8 ?
H4A C4 H4B . 107.7 ?
C6 C5 C8 . 118.6(3) ?
C6 C5 C4 . 120.2(3) ?
C8 C5 C4 . 121.2(3) ?
C7 C6 C5 . 120.4(3) ?
C7 C6 H6 . 119.8 ?
C5 C6 H6 . 119.8 ?
C6 C7 C6 2_656 120.6(4) ?
C6 C7 H7 2_656 119.7 ?
C6 C7 H7 . 119.7 ?
C5 C8 C5 2_656 121.4(4) ?
C5 C8 H8 2_656 119.3 ?
C5 C8 H8 . 119.3 ?
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 C3 . 1.769(3) ?
S1 C1 . 1.786(4) ?
S2 C3 . 1.748(3) yes
S2 C4 . 1.820(3) yes
N1 C3 . 1.253(4) ?
N1 C2 . 1.472(4) ?
C1 C2 . 1.505(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C4 C5 . 1.499(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.384(4) ?
C5 C8 . 1.387(3) ?
C6 C7 . 1.374(4) ?
C6 H6 . 0.9300 ?
C7 C6 2_656 1.374(4) ?
C7 H7 . 0.9300 ?
C8 C5 2_656 1.387(3) ?
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_site_symmetry_4
_geom_torsion
C3 S1 C1 C2 . 14.8(3)
C3 N1 C2 C1 . 13.4(4)
S1 C1 C2 N1 . -18.7(4)
C2 N1 C3 S2 . 175.2(2)
C2 N1 C3 S1 . -1.4(4)
C4 S2 C3 N1 . 0.2(3)
C4 S2 C3 S1 . 176.94(16)
C1 S1 C3 N1 . -8.7(3)
C1 S1 C3 S2 . 174.3(2)
C3 S2 C4 C5 . 89.4(3)
S2 C4 C5 C6 . 71.9(3)
S2 C4 C5 C8 . -108.9(2)
C8 C5 C6 C7 . 1.3(4)
C4 C5 C6 C7 . -179.5(2)
C5 C6 C7 C6 2_656 -0.7(2)
C6 C5 C8 C5 2_656 -0.6(2)
C4 C5 C8 C5 2_656 -179.8(3)
