#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154571.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_7154571
loop_
_publ_author_name
'Le Gal, Y.'
'Ameline, D.'
'Bellec, N.'
'Vacher, A.'
'Roisnel, T.'
'Dorcet, V.'
'Jeannin, O.'
'Lorcy, D.'
_publ_section_title
;
 Efficient routes towards a series of 5,5'-bithiazolidinylidenes as
 π-electron acceptors.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8479
_journal_page_last               8486
_journal_paper_doi               10.1039/c5ob01169h
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H5 N O2 S3'
_chemical_formula_sum            'C6 H5 N O2 S3'
_chemical_formula_weight         219.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-02-18T09:20:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-06-08 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.442(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5086(16)
_cell_length_b                   9.106(3)
_cell_length_c                   11.589(2)
_cell_measurement_reflns_used    246
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.55
_cell_measurement_wavelength     0.71073
_cell_volume                     841.4(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
          WinGX publication routines (Farrugia, 2012),
          CRYSCALc (T. Roisnel, local program, 2014)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5513
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                1679
_reflns_number_total             1912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01169h2.cif
_cod_data_source_block           compound6d
_cod_depositor_comments
'Adding full bibliography for 7154565--7154571.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154571
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_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 0.89399(6) 0.51947(5) 0.64100(5) 0.02148(15) Uani 1 1 d .
S2 S 0.79653(6) 0.72302(5) 0.42274(5) 0.01938(15) Uani 1 1 d .
S3 S 0.52065(6) 0.48845(5) 0.28856(4) 0.01808(14) Uani 1 1 d .
C1 C 0.7362(2) 0.4656(2) 0.50663(18) 0.0169(4) Uani 1 1 d .
N2 N 0.63775(19) 0.34028(17) 0.49188(14) 0.0167(3) Uani 1 1 d .
C3 C 0.6622(3) 0.2207(2) 0.58203(19) 0.0199(4) Uani 1 1 d .
H3A H 0.5516 0.1794 0.5748 0.024 Uiso 1 1 calc R
H3B H 0.7136 0.2614 0.6661 0.024 Uiso 1 1 calc R
C4 C 0.7722(3) 0.0992(2) 0.5645(2) 0.0284(5) Uani 1 1 d .
H4A H 0.7254 0.062 0.4799 0.043 Uiso 1 1 calc R
H4B H 0.7774 0.0193 0.6224 0.043 Uiso 1 1 calc R
H4C H 0.8854 0.1372 0.5797 0.043 Uiso 1 1 calc R
C5 C 0.5135(2) 0.3314(2) 0.37922(17) 0.0169(4) Uani 1 1 d .
O6 O 0.41109(18) 0.23178(15) 0.34358(13) 0.0227(3) Uani 1 1 d .
C7 C 0.6923(2) 0.5562(2) 0.40807(17) 0.0164(4) Uani 1 1 d .
C8 C 0.9260(2) 0.6932(2) 0.57916(19) 0.0220(4) Uani 1 1 d .
O9 O 1.03028(19) 0.77930(17) 0.63750(15) 0.0335(4) Uani 1 1 d .
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 0 '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'
O O 0.0106 0.006 '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 S1 C8 93.94(9)
C7 S2 C8 94.56(9)
C7 S3 C5 90.43(9)
C7 C1 N2 114.87(17)
C7 C1 S1 118.98(15)
N2 C1 S1 125.94(15)
C5 N2 C1 113.45(16)
C5 N2 C3 120.35(16)
C1 N2 C3 126.14(16)
N2 C3 C4 112.80(16)
N2 C3 H3A 109
C4 C3 H3A 109
N2 C3 H3B 109
C4 C3 H3B 109
H3A C3 H3B 107.8
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O6 C5 N2 126.00(18)
O6 C5 S3 124.08(15)
N2 C5 S3 109.92(14)
C1 C7 S2 118.05(15)
C1 C7 S3 111.33(15)
S2 C7 S3 130.32(12)
O9 C8 S2 123.10(17)
O9 C8 S1 122.40(16)
S2 C8 S1 114.44(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.734(2)
S1 C8 1.796(2)
S2 C7 1.737(2)
S2 C8 1.783(2)
S3 C7 1.7375(19)
S3 C5 1.788(2)
C1 C7 1.352(3)
C1 N2 1.390(2)
N2 C5 1.366(2)
N2 C3 1.472(2)
C3 C4 1.508(3)
C3 H3A 0.99
C3 H3B 0.99
C4 H4A 0.98
C4 H4B 0.98
C4 H4C 0.98
C5 O6 1.225(2)
C8 O9 1.200(2)
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
C8 S1 C1 C7 1.13(18)
C8 S1 C1 N2 -173.29(17)
C7 C1 N2 C5 0.1(2)
S1 C1 N2 C5 174.72(14)
C7 C1 N2 C3 177.22(17)
S1 C1 N2 C3 -8.2(3)
C5 N2 C3 C4 85.8(2)
C1 N2 C3 C4 -91.1(2)
C1 N2 C5 O6 179.59(18)
C3 N2 C5 O6 2.3(3)
C1 N2 C5 S3 -0.3(2)
C3 N2 C5 S3 -177.63(13)
C7 S3 C5 O6 -179.56(18)
C7 S3 C5 N2 0.36(14)
N2 C1 C7 S2 174.56(13)
S1 C1 C7 S2 -0.5(2)
N2 C1 C7 S3 0.2(2)
S1 C1 C7 S3 -174.83(10)
C8 S2 C7 C1 -0.49(18)
C8 S2 C7 S3 172.63(15)
C5 S3 C7 C1 -0.31(16)
C5 S3 C7 S2 -173.79(15)
C7 S2 C8 O9 178.7(2)
C7 S2 C8 S1 1.22(13)
C1 S1 C8 O9 -178.88(19)
C1 S1 C8 S2 -1.39(13)
