#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/75/1507515.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_1507515
loop_
_publ_author_name
'Jia, Chunyang'
'Zhang, Deqing'
'Xu, Wei'
'Zhu, Daoben'
_publ_section_title
;
 A New Approach to 4-Alkylthio-1,3-dithiole-2-thione:  An Unusual
 Reaction of a Zinc Complex of 1,3-Dithole-2-thione-4,5-dithiolate
;
_journal_issue                   12
_journal_name_full               'Organic Letters'
_journal_page_first              1941
_journal_paper_doi               10.1021/ol015990n
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C9 H7 N S4'
_chemical_formula_weight         257.40
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.996(3)
_cell_length_b                   7.934(2)
_cell_length_c                   22.205(4)
_cell_measurement_reflns_used    2434
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.04
_cell_volume                     2156.6(9)
_computing_cell_refinement
'Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA.''
_computing_data_collection
'Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.''
_computing_data_reduction
'Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany.''
_computing_molecular_graphics
'Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.''
_computing_publication_material
'Sheldrick, G. M. (1997) SHELXL97, Program for the refinement of Crystal Structure, University of Gottingen, Germany.''
_computing_structure_refinement
'Sheldrick, G. M. (1997) SHELXL97, Program for the Refinement of Crystal Structure, University of Gottingen, Germany.''
_computing_structure_solution
'Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany.''
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku RAXIS RIPAD IP'
_diffrn_measurement_method       Oscillation
_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  0.02563
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            2434
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.0957
_exptl_absorpt_correction_T_min  0.8490
_exptl_absorpt_correction_type   'ABSOR by T. Higashi'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          '0.1 mm'
_exptl_crystal_size_mid          '0.1 mm'
_exptl_crystal_size_min          '0.1 mm'
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.072
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+4.0078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2152
_reflns_number_total             2434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol015990n_s1.cif
_cod_data_source_block           compound_3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2156.6(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1507515
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_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 0.42355(5) 0.35936(7) 0.33499(3) 0.02110(16) Uani 1 1 d .
S2 S 0.40664(4) 0.07857(7) 0.42260(3) 0.01863(16) Uani 1 1 d .
S3 S 0.34947(5) -0.17331(7) 0.32283(3) 0.02018(16) Uani 1 1 d .
S4 S 0.35079(5) -0.26616(8) 0.45400(3) 0.02653(18) Uani 1 1 d .
N1 N 0.64905(19) 0.8187(3) 0.42516(12) 0.0341(5) Uani 1 1 d .
C1 C 0.65237(16) 0.7890(3) 0.31776(10) 0.0131(4) Uani 1 1 d .
H1 H 0.6632 0.8350 0.2818 0.016 Uiso 1 1 calc R
C2 C 0.62348(18) 0.6281(3) 0.31951(11) 0.0187(4) Uani 1 1 d .
H2 H 0.6147 0.5622 0.2835 0.022 Uiso 1 1 calc R
C3 C 0.60548(17) 0.5521(3) 0.37178(11) 0.0183(4) Uani 1 1 d .
C4 C 0.61790(19) 0.6509(3) 0.42580(11) 0.0214(5) Uani 1 1 d .
H4 H 0.6057 0.6056 0.4614 0.026 Uiso 1 1 calc R
C5 C 0.66491(19) 0.8808(3) 0.37040(12) 0.0217(5) Uani 1 1 d .
H5 H 0.6855 0.9930 0.3703 0.026 Uiso 1 1 calc R
C6 C 0.57277(19) 0.3698(3) 0.36848(13) 0.0232(5) Uani 1 1 d .
H6A H 0.5981 0.3203 0.4109 0.028 Uiso 1 1 calc R
H6B H 0.6050 0.3079 0.3416 0.028 Uiso 1 1 calc R
C7 C 0.40269(18) 0.1450(3) 0.34673(11) 0.0174(4) Uani 1 1 d .
C8 C 0.37664(19) 0.0267(3) 0.30119(11) 0.0194(4) Uani 1 1 d .
C9 C 0.36835(18) -0.1284(3) 0.40265(11) 0.0189(4) Uani 1 1 d .
H11 H 0.372(4) 0.043(7) 0.260(2) 0.080 Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0189(3) 0.0141(3) 0.0271(3) 0.0033(2) 0.0036(2) -0.0014(2)
S2 0.0218(3) 0.0169(3) 0.0173(3) -0.0029(2) 0.0067(2) -0.0049(2)
S3 0.0250(3) 0.0143(3) 0.0196(3) -0.0028(2) 0.0053(2) -0.0020(2)
S4 0.0292(3) 0.0245(3) 0.0238(3) 0.0051(2) 0.0060(3) -0.0096(2)
N1 0.0295(12) 0.0385(13) 0.0318(12) -0.0053(11) 0.0068(10) 0.0005(10)
C1 0.0146(9) 0.0116(9) 0.0126(9) 0.0028(8) 0.0038(7) -0.0016(7)
C2 0.0181(10) 0.0188(11) 0.0169(10) -0.0016(8) 0.0030(8) -0.0010(8)
C3 0.0147(9) 0.0174(10) 0.0205(11) 0.0032(8) 0.0029(8) 0.0007(8)
C4 0.0205(11) 0.0277(12) 0.0161(10) 0.0043(9) 0.0063(8) 0.0012(9)
C5 0.0211(11) 0.0148(10) 0.0273(12) -0.0001(9) 0.0055(9) -0.0015(9)
C6 0.0176(10) 0.0187(11) 0.0315(13) 0.0065(10) 0.0058(9) -0.0004(9)
C7 0.0169(10) 0.0162(10) 0.0191(10) 0.0014(8) 0.0059(8) -0.0003(8)
C8 0.0214(10) 0.0174(11) 0.0199(11) 0.0008(9) 0.0075(9) 0.0000(8)
C9 0.0168(10) 0.0175(11) 0.0204(11) 0.0002(9) 0.0037(8) -0.0035(8)
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
C7 S1 C6 100.30(11)
C9 S2 C7 97.26(11)
C8 S3 C9 97.05(11)
C4 N1 C5 118.5(2)
C2 C1 C5 116.6(2)
C1 C2 C3 124.4(2)
C2 C3 C4 118.0(2)
C2 C3 C6 119.9(2)
C4 C3 C6 122.1(2)
N1 C4 C3 118.6(2)
C1 C5 N1 124.1(2)
C3 C6 S1 107.89(15)
C8 C7 S2 115.78(18)
C8 C7 S1 125.47(19)
S2 C7 S1 118.60(13)
C7 C8 S3 117.24(19)
S4 C9 S2 123.14(15)
S4 C9 S3 124.23(14)
S2 C9 S3 112.63(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.756(2)
S1 C6 1.831(2)
S2 C9 1.730(2)
S2 C7 1.749(2)
S3 C8 1.728(2)
S3 C9 1.743(2)
S4 C9 1.650(2)
N1 C4 1.393(4)
N1 C5 1.390(4)
C1 C2 1.335(3)
C1 C5 1.340(3)
C2 C3 1.396(3)
C3 C4 1.396(3)
C3 C6 1.502(3)
C7 C8 1.337(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651841
