#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/41/4344172.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_4344172
loop_
_publ_author_name
'Higashino, Toshiki'
'Jeannin, Olivier'
'Kawamoto, Tadashi'
'Lorcy, Dominique'
'Mori, Takehiko'
'Fourmigué, Marc'
_publ_section_title
;
 A Single-Component Conductor Based on a Radical Gold Dithiolene Complex
 with Alkyl-Substituted Thiophene-2,3-dithiolate Ligand.
;
_journal_issue                   20
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9908
_journal_page_last               9913
_journal_paper_doi               10.1021/acs.inorgchem.5b01678
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C8 H8 S4'
_chemical_formula_sum            'C8 H8 S4'
_chemical_formula_weight         232.38
_chemical_name_common
;
5-methyl-6-ethyl-thieno[2,3-d][1,3]dithiole-2-thione
;
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.974(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6042(3)
_cell_length_b                   10.2419(4)
_cell_length_c                   10.5970(4)
_cell_measurement_reflns_used    7665
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.81
_cell_volume                     1015.77(7)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24921
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0190(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0301P)²+0.5415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                1855
_reflns_number_total             2325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic5b01678_si_002.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 4344171--4344175.cif.'
_cod_original_cell_volume        1015.77(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4344172
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
C1 C 0.6502(2) 0.30556(18) 1.02523(17) 0.0392(4) Uani 1 1 d .
C2 C 0.51377(19) 0.12512(18) 0.87841(16) 0.0348(4) Uani 1 1 d .
C3 C 0.41004(19) 0.19717(16) 0.91453(16) 0.0337(4) Uani 1 1 d .
C4 C 0.26846(19) 0.14879(18) 0.86854(17) 0.0370(4) Uani 1 1 d .
C5 C 0.27005(19) 0.03752(18) 0.79756(17) 0.0372(4) Uani 1 1 d .
C6 C 0.1386(2) 0.2108(2) 0.9003(2) 0.0536(5) Uani 1 1 d .
H6A H 0.0539 0.1798 0.8397 0.064 Uiso 1 1 calc R
H6B H 0.1438 0.3047 0.8901 0.064 Uiso 1 1 calc R
C7 C 0.1250(3) 0.1804(3) 1.0376(3) 0.0851(9) Uani 1 1 d .
H7A H 0.1116 0.0882 1.0462 0.128 Uiso 1 1 calc R
H7B H 0.0444 0.2264 1.0554 0.128 Uiso 1 1 calc R
H7C H 0.2104 0.2074 1.0979 0.128 Uiso 1 1 calc R
C8 C 0.1468(2) -0.0457(2) 0.7319(2) 0.0529(5) Uani 1 1 d .
H8A H 0.0626 -0.0204 0.7605 0.079 Uiso 1 1 calc R
H8B H 0.1679 -0.1357 0.7532 0.079 Uiso 1 1 calc R
H8C H 0.1306 -0.0342 0.6398 0.079 Uiso 1 1 calc R
S1 S 0.68830(5) 0.17551(5) 0.93301(5) 0.04276(15) Uani 1 1 d .
S2 S 0.46961(5) 0.32973(5) 1.01409(5) 0.04024(14) Uani 1 1 d .
S3 S 0.44244(5) -0.00829(5) 0.78791(4) 0.03901(14) Uani 1 1 d .
S4 S 0.77492(6) 0.39964(6) 1.11252(6) 0.05593(18) Uani 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
C1 0.0398(9) 0.0365(10) 0.0386(9) 0.0058(8) 0.0029(7) 0.0002(8)
C2 0.0394(9) 0.0334(9) 0.0317(8) 0.0015(7) 0.0085(7) 0.0004(7)
C3 0.0384(9) 0.0293(9) 0.0323(8) -0.0004(7) 0.0054(7) 0.0012(7)
C4 0.0371(9) 0.0330(9) 0.0389(9) 0.0011(7) 0.0043(7) 0.0040(7)
C5 0.0411(9) 0.0324(9) 0.0359(9) 0.0009(7) 0.0040(7) 0.0007(7)
C6 0.0355(10) 0.0447(12) 0.0770(15) -0.0141(11) 0.0049(10) 0.0054(9)
C7 0.0629(16) 0.109(2) 0.095(2) -0.0252(18) 0.0413(15) 0.0076(16)
C8 0.0495(12) 0.0452(12) 0.0581(12) -0.0085(10) -0.0003(9) -0.0045(9)
S1 0.0365(2) 0.0437(3) 0.0496(3) -0.0004(2) 0.0129(2) 0.0008(2)
S2 0.0407(3) 0.0331(3) 0.0450(3) -0.00770(19) 0.00565(19) 0.00078(18)
S3 0.0496(3) 0.0341(3) 0.0351(2) -0.00351(18) 0.01332(19) 0.00161(19)
S4 0.0467(3) 0.0494(3) 0.0634(3) -0.0037(3) -0.0052(2) -0.0091(2)
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
S4 C1 S2 123.04(12)
S4 C1 S1 123.02(12)
S2 C1 S1 113.92(10)
C3 C2 S3 111.23(14)
C3 C2 S1 117.43(14)
S3 C2 S1 131.29(11)
C2 C3 C4 114.65(16)
C2 C3 S2 115.63(14)
C4 C3 S2 129.66(14)
C5 C4 C3 110.48(16)
C5 C4 C6 125.99(17)
C3 C4 C6 123.48(16)
C4 C5 C8 128.64(18)
C4 C5 S3 112.59(14)
C8 C5 S3 118.77(14)
C4 C6 C7 112.41(19)
C4 C6 H6A 109.1
C7 C6 H6A 109.1
C4 C6 H6B 109.1
C7 C6 H6B 109.1
H6A C6 H6B 107.9
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 S1 C1 96.12(9)
C1 S2 C3 96.78(9)
C2 S3 C5 91.04(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 S4 1.6495(19)
C1 S2 1.7301(19)
C1 S1 1.739(2)
C2 C3 1.362(3)
C2 S3 1.7208(18)
C2 S1 1.7249(18)
C3 C4 1.426(2)
C3 S2 1.7357(17)
C4 C5 1.367(3)
C4 C6 1.504(3)
C5 C8 1.497(3)
C5 S3 1.7458(19)
C6 C7 1.522(4)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
S3 C2 C3 C4 -1.1(2)
S1 C2 C3 C4 -178.72(12)
S3 C2 C3 S2 176.55(9)
S1 C2 C3 S2 -1.07(19)
C2 C3 C4 C5 0.4(2)
S2 C3 C4 C5 -176.80(14)
C2 C3 C4 C6 178.05(18)
S2 C3 C4 C6 0.8(3)
C3 C4 C5 C8 179.74(18)
C6 C4 C5 C8 2.2(3)
C3 C4 C5 S3 0.4(2)
C6 C4 C5 S3 -177.12(16)
C5 C4 C6 C7 101.2(3)
C3 C4 C6 C7 -76.0(3)
C3 C2 S1 C1 2.67(16)
S3 C2 S1 C1 -174.37(13)
S4 C1 S1 C2 178.12(12)
S2 C1 S1 C2 -3.33(12)
S4 C1 S2 C3 -178.56(12)
S1 C1 S2 C3 2.90(12)
C2 C3 S2 C1 -1.14(15)
C4 C3 S2 C1 176.08(17)
C3 C2 S3 C5 1.10(14)
S1 C2 S3 C5 178.29(14)
C4 C5 S3 C2 -0.87(15)
C8 C5 S3 C2 179.73(16)
