#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/09/4030945.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_4030945
loop_
_publ_author_name
'Jeannin, Olivier'
'Barrière, Frédéric'
'Fourmigué, Marc'
_publ_section_title
;
 Trifluoromethyl-substituted tetrathiafulvalenes.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              647
_journal_page_last               658
_journal_paper_doi               10.3762/bjoc.11.73
_journal_volume                  11
_journal_year                    2015
_chemical_formula_sum            'C11 H7 F3 O2 S6'
_chemical_formula_weight         420.53
_chemical_name_common            EDT-TTF(CO2Me)(CF3)
_chemical_name_systematic
;
3,4-ethylendithio-3'-carbomethoxy-4'-trifluoromethyltetrathiafulvalene
 ?
;
_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                103.96(3)
_cell_angle_beta                 90.02(3)
_cell_angle_gamma                90.45(3)
_cell_formula_units_Z            2
_cell_length_a                   5.1515(12)
_cell_length_b                   11.998(2)
_cell_length_c                   12.974(3)
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      1.7
_cell_volume                     778.2(3)
_computing_cell_refinement       'CELL, Stoe-IPDS'
_computing_data_collection       'EXPOSE, Stoe-IPDS'
_computing_data_reduction        'INTEGRATE, Stoe-IPDS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation, phi incr. 1.8 deg'
_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  0.1265
_diffrn_reflns_av_sigmaI/netI    0.2045
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7498
_diffrn_reflns_theta_full        25.94
_diffrn_reflns_theta_max         25.94
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    constrain
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0167P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                989
_reflns_number_total             2778
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-11-73-S2.cif
_cod_data_source_block           2bc
_cod_depositor_comments
'Adding full bibliography for 4030944--4030949.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030945
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
S1 S 0.8057(4) 0.34166(13) 0.22964(15) 0.0464(5) Uani 1 1 d .
S3 S 0.2079(4) 0.12987(13) 0.03126(15) 0.0474(6) Uani 1 1 d .
S2 S 0.5859(4) 0.11211(14) 0.22628(16) 0.0505(6) Uani 1 1 d .
S4 S 0.4142(4) 0.36299(13) 0.04205(16) 0.0511(6) Uani 1 1 d .
S5 S 0.0942(4) 0.40266(15) -0.13245(18) 0.0657(7) Uani 1 1 d .
S6 S -0.1549(4) 0.12743(16) -0.14383(17) 0.0623(7) Uani 1 1 d .
C2 C 0.5795(14) 0.2347(5) 0.1736(5) 0.0391(17) Uani 1 1 d .
C1 C 0.4191(13) 0.2410(4) 0.0923(5) 0.0383(17) Uani 1 1 d .
C4 C 0.8030(13) 0.1706(5) 0.3251(5) 0.0405(19) Uani 1 1 d .
C3 C 0.9102(12) 0.2750(5) 0.3260(5) 0.0369(16) Uani 1 1 d .
C5 C 0.0796(13) 0.2044(5) -0.0571(6) 0.0451(19) Uani 1 1 d .
C6 C 0.1720(12) 0.3107(5) -0.0521(5) 0.0387(18) Uani 1 1 d .
C7 C -0.189(2) 0.2148(7) -0.2347(7) 0.113(4) Uani 1 1 d .
H7A H -0.1085 0.1724 -0.2998 0.135 Uiso 1 1 calc R
H7B H -0.3739 0.2147 -0.2497 0.135 Uiso 1 1 calc R
C8 C -0.115(3) 0.3177(10) -0.2236(9) 0.188(8) Uani 1 1 d .
H8A H -0.2750 0.3612 -0.2169 0.226 Uiso 1 1 calc R
H8B H -0.0442 0.3201 -0.2922 0.226 Uiso 1 1 calc R
C9 C 0.8545(17) 0.0973(6) 0.4020(6) 0.051(2) Uani 1 1 d .
C10 C 1.1062(14) 0.3461(6) 0.4006(6) 0.045(2) Uani 1 1 d .
C11 C 1.3685(15) 0.3671(6) 0.5517(6) 0.082(3) Uani 1 1 d .
H11A H 1.4107 0.3273 0.6054 0.123 Uiso 1 1 calc R
H11B H 1.2981 0.4410 0.5846 0.123 Uiso 1 1 calc R
H11C H 1.5226 0.3770 0.5132 0.123 Uiso 1 1 calc R
O1 O 1.1781(10) 0.3006(4) 0.4791(4) 0.0692(16) Uani 1 1 d .
O2 O 1.1693(10) 0.4388(4) 0.3884(4) 0.0716(16) Uani 1 1 d .
F1 F 1.1023(9) 0.0676(3) 0.4072(3) 0.0692(13) Uani 1 1 d .
F2 F 0.7833(9) 0.1477(3) 0.5019(3) 0.0783(14) Uani 1 1 d .
F3 F 0.7175(9) 0.0000(3) 0.3765(3) 0.0770(14) 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 S1 C2 95.0(3)
C1 S3 C5 94.5(3)
C4 S2 C2 94.4(3)
C1 S4 C6 94.8(3)
C8 S5 C6 101.6(4)
C5 S6 C7 101.3(4)
C1 C2 S1 123.6(4)
C1 C2 S2 121.6(4)
S1 C2 S2 114.7(4)
C2 C1 S4 120.9(4)
C2 C1 S3 123.3(4)
S4 C1 S3 115.8(4)
C3 C4 C9 127.2(6)
C3 C4 S2 118.3(5)
C9 C4 S2 114.5(5)
C4 C3 C10 130.3(7)
C4 C3 S1 117.0(5)
C10 C3 S1 112.7(5)
C6 C5 S3 117.7(5)
C6 C5 S6 128.1(5)
S3 C5 S6 114.2(4)
C5 C6 S5 128.4(5)
C5 C6 S4 117.1(5)
S5 C6 S4 114.4(3)
C8 C7 S6 127.8(7)
C7 C8 S5 131.1(9)
F3 C9 F1 106.6(6)
F3 C9 F2 105.0(6)
F1 C9 F2 106.3(6)
F3 C9 C4 111.0(6)
F1 C9 C4 114.3(7)
F2 C9 C4 113.0(6)
O2 C10 O1 126.4(6)
O2 C10 C3 119.3(7)
O1 C10 C3 114.1(6)
C10 O1 C11 115.2(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C3 1.726(7)
S1 C2 1.750(6)
S3 C1 1.748(6)
S3 C5 1.748(7)
S2 C4 1.714(6)
S2 C2 1.766(6)
S4 C1 1.741(6)
S4 C6 1.749(6)
S5 C8 1.733(8)
S5 C6 1.739(7)
S6 C5 1.748(7)
S6 C7 1.767(8)
C2 C1 1.356(7)
C4 C3 1.363(8)
C4 C9 1.505(9)
C3 C10 1.507(9)
C5 C6 1.345(8)
C7 C8 1.264(10)
C9 F3 1.331(7)
C9 F1 1.334(8)
C9 F2 1.344(8)
C10 O2 1.202(8)
C10 O1 1.321(8)
C11 O1 1.453(7)
