#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:53:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178586 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/97/4069742.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_4069742
loop_
_publ_author_name
'Ciric, Ana'
'Mathey, François'
_publ_section_title
;
 An Unexpected Sequence: From Phosphole Sulfide to Phosphole- and
 Thiophene-Annulated 1,2-Dithiole-3-thiones
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              4621
_journal_paper_doi               10.1021/om9003972
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C11 H4 O5 S4 W'
_chemical_formula_sum            'C11 H4 O5 S4 W'
_chemical_formula_weight         528.23
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.148(2)
_cell_angle_beta                 69.411(2)
_cell_angle_gamma                75.033(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6224(4)
_cell_length_b                   10.3544(6)
_cell_length_c                   10.5713(6)
_cell_measurement_reflns_used    8313
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.16
_cell_measurement_theta_min      2.64
_cell_volume                     739.06(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24950
_diffrn_reflns_theta_full        33.16
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    8.394
_exptl_absorpt_correction_T_max  0.4874
_exptl_absorpt_correction_T_min  0.1873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.986
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0169
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0120P)²+0.8582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0445
_reflns_number_gt                5182
_reflns_number_total             5523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9003972_si_002.cif
_cod_data_source_block           mat10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_sg_symbol_H-M      P-1
_cod_database_code               4069742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
W1 W 0.602786(12) 0.654026(9) 0.695140(9) 0.01904(3) Uani 1 1 d .
C1 C 0.0899(3) 1.0706(3) 1.1893(2) 0.0254(4) Uani 1 1 d .
H1 H 0.0376 1.0662 1.2859 0.030 Uiso 1 1 calc R
C2 C 0.2028(3) 0.9625(2) 1.1335(2) 0.0210(4) Uani 1 1 d .
C3 C 0.2596(4) 0.8257(3) 1.2167(2) 0.0274(5) Uani 1 1 d .
H3A H 0.2082 0.8288 1.3151 0.041 Uiso 1 1 calc R
H3B H 0.3988 0.8017 1.1910 0.041 Uiso 1 1 calc R
H3C H 0.2088 0.7570 1.1987 0.041 Uiso 1 1 calc R
C4 C 0.2591(3) 0.9992(2) 0.9851(2) 0.0181(4) Uani 1 1 d .
C5 C 0.1860(3) 1.1340(2) 0.9373(2) 0.0206(4) Uani 1 1 d .
C6 C 0.3687(3) 0.9212(2) 0.8819(2) 0.0183(4) Uani 1 1 d .
C7 C 0.4186(4) 0.5203(2) 0.8026(3) 0.0262(4) Uani 1 1 d .
C8 C 0.8058(4) 0.5363(3) 0.7853(3) 0.0268(5) Uani 1 1 d .
C9 C 0.7778(3) 0.7926(3) 0.5832(2) 0.0243(4) Uani 1 1 d .
C10 C 0.3990(3) 0.7564(2) 0.6022(2) 0.0239(4) Uani 1 1 d .
C11 C 0.7144(4) 0.5461(3) 0.5470(3) 0.0302(5) Uani 1 1 d .
O1 O 0.3120(3) 0.4488(2) 0.8589(2) 0.0408(5) Uani 1 1 d .
O2 O 0.9180(3) 0.4664(2) 0.8326(2) 0.0419(5) Uani 1 1 d .
O3 O 0.8771(3) 0.8671(2) 0.5166(2) 0.0372(5) Uani 1 1 d .
O4 O 0.2855(3) 0.8057(2) 0.5478(2) 0.0373(4) Uani 1 1 d .
O5 O 0.7801(4) 0.4817(2) 0.4631(2) 0.0498(6) Uani 1 1 d .
S1 S 0.04976(9) 1.21711(6) 1.06846(7) 0.02685(12) Uani 1 1 d .
S2 S 0.23380(9) 1.19733(6) 0.76242(6) 0.02580(11) Uani 1 1 d .
S3 S 0.39090(9) 1.01184(6) 0.71503(6) 0.02402(11) Uani 1 1 d .
S4 S 0.46827(8) 0.75644(6) 0.90863(6) 0.02180(10) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
W W -0.8490 6.8722 '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
C11 W1 C10 88.25(11)
C11 W1 C9 90.39(10)
C10 W1 C9 91.95(10)
C11 W1 C7 89.51(10)
C10 W1 C7 85.42(10)
C9 W1 C7 177.37(10)
C11 W1 C8 88.12(11)
C10 W1 C8 175.21(9)
C9 W1 C8 91.19(10)
C7 W1 C8 91.43(10)
C11 W1 S4 171.18(8)
C10 W1 S4 98.01(7)
C9 W1 S4 95.58(7)
C7 W1 S4 84.82(7)
C8 W1 S4 85.27(7)
C2 C1 S1 114.06(18)
C2 C1 H1 123.0
S1 C1 H1 123.0
C1 C2 C4 110.5(2)
C1 C2 C3 123.9(2)
C4 C2 C3 125.6(2)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C4 C6 115.89(19)
C5 C4 C2 112.47(19)
C6 C4 C2 131.6(2)
C4 C5 S1 112.43(17)
C4 C5 S2 119.72(16)
S1 C5 S2 127.83(14)
C4 C6 S4 126.48(17)
C4 C6 S3 113.99(16)
S4 C6 S3 119.52(12)
O1 C7 W1 177.3(2)
O2 C8 W1 176.8(2)
O3 C9 W1 177.2(2)
O4 C10 W1 175.4(2)
O5 C11 W1 178.7(3)
C5 S1 C1 90.59(11)
C5 S2 S3 92.61(8)
C6 S3 S2 97.79(8)
C6 S4 W1 114.64(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
W1 C11 1.989(3)
W1 C10 2.039(3)
W1 C9 2.047(2)
W1 C7 2.050(3)
W1 C8 2.054(3)
W1 S4 2.5274(6)
C1 C2 1.359(3)
C1 S1 1.733(3)
C1 H1 0.9500
C2 C4 1.441(3)
C2 C3 1.496(3)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C5 1.387(3)
C4 C6 1.425(3)
C5 S1 1.708(2)
C5 S2 1.723(2)
C6 S4 1.669(2)
C6 S3 1.728(2)
C7 O1 1.136(3)
C8 O2 1.135(3)
C9 O3 1.137(3)
C10 O4 1.141(3)
C11 O5 1.149(3)
S2 S3 2.0711(8)
