#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102168.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_2102168
loop_
_publ_author_name
'Chohan, Zahid H.'
'Harrison, William T. A.'
'Howie, R. Alan'
'Milne, Bruce F.'
'Wardell, James L.'
_publ_section_title
;
 Crystallographic and molecular mechanics investigation of an
 order--disorder transition and dimorphism in
 5H,10H-dithiolo[2,3-b]-2,5-benzodithiocine-2-thione
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1011
_journal_page_last               1017
_journal_paper_doi               10.1107/S0108768100010636
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C11 H8 S5'
_chemical_formula_sum            'C11 H8 S5'
_chemical_formula_weight         300.47
_chemical_melting_point          479
_chemical_name_systematic
;5H,10H-Dithiolo[2,3-b][2,5]benzodithiocine-2-thione (C-centred monoclinic
 form)
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 102.80(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.075(8)
_cell_length_b                   11.825(8)
_cell_length_c                   9.063(6)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.9
_cell_measurement_theta_min      10.8
_cell_volume                     1261.9(15)
_computing_cell_refinement       'Nicolet P3 software (Nicolet, 1980)'
_computing_data_collection       'Nicolet P3 software (Nicolet, 1980)'
_computing_data_reduction        'RDNIC (Howie, 1980)'
_computing_molecular_graphics    'ORTEX (McArdle, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.498
_diffrn_measured_fraction_theta_max 0.498
_diffrn_measurement_device_type  'Nicolet P3'
_diffrn_measurement_method       θ--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2034
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  0.719
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   \y
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.95
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0862
_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)+(0.0535P)²+8.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1847
_refine_ls_wR_factor_ref         0.2153
_reflns_number_gt                1166
_reflns_number_total             1932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm0027.cif
_cod_data_source_block           alphaprime-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+8.1837P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+8.1837P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2102168
_cod_database_fobs_code          2102168
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x, y, -z'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
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_calc_flag
_atom_site_refinement_flags
S1 S 0.3778(2) 0.0000 0.3365(3) 0.147(2) Uani 1 d S
S2 S 0.34509(12) 0.12081(14) 0.04410(17) 0.0728(5) Uani 1 d .
S3 S 0.32964(15) 0.1438(2) -0.2844(2) 0.1171(10) Uani 1 d .
C1 C 0.3580(6) 0.0000 0.1521(8) 0.076(3) Uani 1 d S
C2 C 0.3363(3) 0.0564(4) -0.1288(5) 0.0438(10) Uani 1 d .
C3 C 0.1916(4) 0.1264(5) -0.3999(6) 0.0654(15) Uani 1 d .
H3A H 0.1592 0.2008 -0.4259 0.12(2) Uiso 1 calc R
H3B H 0.1987 0.0901 -0.4933 0.12(2) Uiso 1 calc R
C4 C 0.1097(3) 0.0589(4) -0.3320(5) 0.0430(10) Uani 1 d .
C5 C 0.0330(4) 0.1159(4) -0.2676(6) 0.0541(12) Uani 1 d .
H5 H 0.0330 0.1946 -0.2675 0.074(13) Uiso 1 calc R
C6 C -0.0439(4) 0.0585(5) -0.2031(6) 0.0669(15) Uani 1 d .
H6 H -0.0953 0.0982 -0.1600 0.074(13) Uiso 1 calc R
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 0.0658(15) 0.340(6) 0.0355(10) 0.000 0.0101(10) 0.000
S2 0.0597(8) 0.0762(10) 0.0714(9) -0.0334(8) -0.0094(6) 0.0100(7)
S3 0.0766(11) 0.148(2) 0.1040(14) 0.0790(14) -0.0280(9) -0.0657(12)
C1 0.030(3) 0.153(9) 0.043(4) 0.000 0.002(3) 0.000
C2 0.036(2) 0.051(2) 0.043(2) 0.006(2) 0.0052(16) -0.0041(18)
C3 0.059(3) 0.079(4) 0.054(3) 0.018(3) 0.003(2) -0.013(3)
C4 0.037(2) 0.051(2) 0.0369(19) 0.0057(18) -0.0012(16) 0.0004(18)
C5 0.045(2) 0.047(3) 0.063(3) -0.004(2) -0.002(2) 0.008(2)
C6 0.043(3) 0.087(4) 0.069(3) -0.012(3) 0.010(2) 0.011(3)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S2 C2 97.5(3) . . yes
C2 S3 C3 106.2(2) . . yes
S1 C1 S2 123.8(2) . 2 yes
S1 C1 S2 123.8(2) . . yes
S2 C1 S2 112.4(4) 2 . yes
C2 C2 S2 116.20(16) 2 . yes
C2 C2 S3 126.55(18) 2 . yes
S2 C2 S3 117.2(3) . . yes
C4 C3 S3 115.9(3) . . yes
C5 C4 C4 119.4(3) . 2 yes
C5 C4 C3 118.6(5) . . yes
C4 C4 C3 122.1(3) 2 . yes
C4 C5 C6 121.2(5) . . yes
C5 C6 C6 119.5(3) . 2 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.635(8) . yes
S2 C1 1.719(4) . yes
S2 C2 1.724(5) . yes
S3 C2 1.735(5) . yes
S3 C3 1.773(5) . yes
C1 S2 1.719(4) 2 yes
C2 C2 1.334(9) 2 yes
C3 C4 1.506(7) . yes
C4 C5 1.376(6) . yes
C4 C4 1.392(9) 2 yes
C5 C6 1.380(7) . yes
C6 C6 1.384(12) 2 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 S2 C1 S1 176.4(4) . . .
C2 S2 C1 S2 -4.8(4) . . 2
C1 S2 C2 C2 3.0(3) . . 2
C1 S2 C2 S3 -176.4(3) . . .
C3 S3 C2 C2 68.6(3) . . 2
C3 S3 C2 S2 -112.1(3) . . .
C2 S3 C3 C4 8.7(5) . . .
S3 C3 C4 C5 98.5(5) . . .
S3 C3 C4 C4 -81.2(4) . . 2
C4 C4 C5 C6 0.0(5) 2 . .
C3 C4 C5 C6 -179.8(4) . . .
C4 C5 C6 C6 0.0(5) . . 2
S2 C2 C2 S2 0.0 . 2 2
S2 C2 C2 S3 -179.4(3) . 2 2
C3 C4 C4 C3 0.0 . 2 2
C3 C4 C4 C5 179.7(5) . 2 2
C5 C6 C6 C5 0.0 . 2 2
