#------------------------------------------------------------------------------
#$Date: 2013-12-29 13:49:26 +0200 (Sun, 29 Dec 2013) $
#$Revision: 91935 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/46/4064682.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_4064682
loop_
_publ_author_name
'Vacher, Antoine'
'Barri\`ere, Fr\'ed\'eric'
'Roisnel, Thierry'
'Piekara-Sady, Lidia'
'Lorcy, Dominique'
_publ_section_title
;
 Electronically Coupled Tetrathiafulvalene Electrophores across a
 Non-innocent Acetylide--Ruthenium Bridge
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3570
_journal_volume                  30
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H10 S4'
_chemical_formula_sum            'C11 H10 S4'
_chemical_formula_weight         270.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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      2.3
_audit_creation_date             2011-04-26T16:28:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.350(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6755(6)
_cell_length_b                   7.6302(6)
_cell_length_c                   20.4398(15)
_cell_measurement_reflns_used    99451
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     1196.74(16)
_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),
           CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'KappaCCD, Nonius'
_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  0.0883
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16839
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.77
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.838
_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    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.652
_refine_diff_density_min         -1.068
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.097
_refine_ls_R_factor_gt           0.0795
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1143P)^2^+4.6537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2322
_reflns_number_gt                2112
_reflns_number_total             2724
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    om200266q_si_002.cif
_[local]_cod_data_source_block   TTF2
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               4064682
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.2982(7) 0.1520(7) 0.4676(3) 0.0421(12) Uani 1 1 d .
H1A H 0.1756 0.1694 0.4783 0.063 Uiso 1 1 calc R
H1B H 0.3599 0.2642 0.4705 0.063 Uiso 1 1 calc R
H1C H 0.3517 0.0687 0.4985 0.063 Uiso 1 1 calc R
C2 C 0.3099(6) 0.0789(6) 0.3973(2) 0.0332(10) Uani 1 1 d .
C3 C 0.1838(6) -0.0088(6) 0.3644(2) 0.0327(10) Uani 1 1 d .
C4 C 0.0040(6) -0.0534(7) 0.3878(3) 0.0397(12) Uani 1 1 d .
H4A H -0.0096 -0.0084 0.4323 0.06 Uiso 1 1 calc R
H4B H -0.0112 -0.181 0.3878 0.06 Uiso 1 1 calc R
H4C H -0.0838 0.0001 0.3585 0.06 Uiso 1 1 calc R
C5 C 0.4365(6) 0.0250(6) 0.2823(2) 0.0306(10) Uani 1 1 d .
C6 C 0.5368(6) 0.0255(6) 0.2290(2) 0.0307(10) Uani 1 1 d .
C7 C 0.9699(6) 0.1097(7) 0.1251(2) 0.0378(11) Uani 1 1 d .
H7A H 0.9843 0.0624 0.0809 0.057 Uiso 1 1 calc R
H7B H 1.0611 0.0624 0.1544 0.057 Uiso 1 1 calc R
H7C H 0.9789 0.2378 0.1238 0.057 Uiso 1 1 calc R
C8 C 0.7942(6) 0.0583(6) 0.1496(2) 0.0308(10) Uani 1 1 d .
C9 C 0.6722(6) -0.0353(6) 0.1160(2) 0.0311(10) Uani 1 1 d .
C10 C 0.6928(6) -0.1045(7) 0.0528(2) 0.0347(11) Uani 1 1 d .
C11 C 0.7102(8) -0.1642(8) 0.0016(3) 0.0503(14) Uani 1 1 d .
H11 H 0.7246 -0.2136 -0.0406 0.06 Uiso 1 1 calc R
S1 S 0.50232(16) 0.12545(16) 0.35647(6) 0.0339(4) Uani 1 1 d .
S2 S 0.22839(16) -0.07050(17) 0.28362(6) 0.0343(4) Uani 1 1 d .
S3 S 0.74118(16) 0.13047(17) 0.22794(6) 0.0344(4) Uani 1 1 d .
S4 S 0.47169(15) -0.07333(17) 0.15461(6) 0.0333(4) 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 0.038(3) 0.039(3) 0.050(3) 0.006(2) -0.002(2) -0.003(2)
C2 0.037(2) 0.027(2) 0.035(2) 0.0089(19) -0.0044(19) 0.0000(19)
C3 0.037(2) 0.026(2) 0.036(2) 0.0096(19) -0.0063(19) -0.0016(19)
C4 0.037(3) 0.039(3) 0.043(3) 0.004(2) -0.001(2) -0.006(2)
C5 0.036(2) 0.028(2) 0.028(2) 0.0043(18) -0.0060(18) -0.0063(19)
C6 0.034(2) 0.026(2) 0.032(2) 0.0013(18) -0.0081(18) -0.0073(19)
C7 0.034(2) 0.042(3) 0.038(3) 0.004(2) -0.001(2) -0.007(2)
C8 0.035(2) 0.027(2) 0.030(2) 0.0062(18) -0.0013(18) -0.0001(18)
C9 0.031(2) 0.028(2) 0.034(2) 0.0065(19) -0.0006(18) 0.0002(18)
C10 0.032(2) 0.034(2) 0.038(3) 0.003(2) -0.001(2) -0.0005(19)
C11 0.050(3) 0.054(4) 0.047(3) -0.004(3) 0.003(3) -0.008(3)
S1 0.0365(7) 0.0344(7) 0.0303(6) 0.0024(5) -0.0061(5) -0.0112(5)
S2 0.0357(7) 0.0359(7) 0.0309(6) 0.0047(5) -0.0065(5) -0.0114(5)
S3 0.0363(7) 0.0357(7) 0.0307(6) 0.0039(5) -0.0060(5) -0.0121(5)
S4 0.0338(6) 0.0354(7) 0.0304(6) -0.0010(5) -0.0049(5) -0.0098(5)
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'
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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C1 126.1(5)
C3 C2 S1 117.9(4)
C1 C2 S1 116.0(3)
C2 C3 C4 127.3(5)
C2 C3 S2 116.8(4)
C4 C3 S2 115.9(4)
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
C6 C5 S2 123.4(4)
C6 C5 S1 122.4(4)
S2 C5 S1 114.2(3)
C5 C6 S4 122.8(4)
C5 C6 S3 122.4(4)
S4 C6 S3 114.8(3)
C8 C7 H7A 109.5
C8 C7 H7B 109.5
H7A C7 H7B 109.5
C8 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C7 125.8(4)
C9 C8 S3 117.2(4)
C7 C8 S3 117.0(3)
C8 C9 C10 124.9(4)
C8 C9 S4 117.4(4)
C10 C9 S4 117.7(4)
C11 C10 C9 178.6(6)
C10 C11 H11 180
C2 S1 C5 95.4(2)
C5 S2 C3 95.8(2)
C8 S3 C6 95.4(2)
C6 S4 C9 94.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.545(7)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C2 C3 1.344(7)
C2 S1 1.750(5)
C3 C4 1.510(7)
C3 S2 1.758(5)
C4 H4A 0.98
C4 H4B 0.98
C4 H4C 0.98
C5 C6 1.348(7)
C5 S2 1.757(5)
C5 S1 1.763(5)
C6 S4 1.759(5)
C6 S3 1.762(5)
C7 C8 1.502(6)
C7 H7A 0.98
C7 H7B 0.98
C7 H7C 0.98
C8 C9 1.352(7)
C8 S3 1.750(5)
C9 C10 1.409(7)
C9 S4 1.769(5)
C10 C11 1.152(8)
C11 H11 0.95
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
C1 C2 C3 C4 0.8(8)
S1 C2 C3 C4 -175.9(4)
C1 C2 C3 S2 177.7(4)
S1 C2 C3 S2 1.0(5)
S2 C5 C6 S4 -1.1(6)
S1 C5 C6 S4 -179.6(3)
S2 C5 C6 S3 177.2(3)
S1 C5 C6 S3 -1.3(6)
C7 C8 C9 C10 2.0(8)
S3 C8 C9 C10 -179.6(4)
C7 C8 C9 S4 -178.0(4)
S3 C8 C9 S4 0.5(5)
C3 C2 S1 C5 0.0(4)
C1 C2 S1 C5 -177.0(4)
C6 C5 S1 C2 177.7(4)
S2 C5 S1 C2 -1.0(3)
C6 C5 S2 C3 -177.3(4)
S1 C5 S2 C3 1.4(3)
C2 C3 S2 C5 -1.4(4)
C4 C3 S2 C5 175.8(4)
C9 C8 S3 C6 3.7(4)
C7 C8 S3 C6 -177.7(4)
C5 C6 S3 C8 174.9(4)
S4 C6 S3 C8 -6.7(3)
C5 C6 S4 C9 -174.8(4)
S3 C6 S4 C9 6.8(3)
C8 C9 S4 C6 -4.4(4)
C10 C9 S4 C6 175.6(4)
_journal_paper_doi 10.1021/om200266q