#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/09/4030946.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_4030946
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            'C12 H6 F6 O4 S4'
_chemical_formula_weight         456.41
_chemical_name_common            o-(CF3)2-TTF-o-(CO2Me)
_chemical_name_systematic
;
4,5-bis(trifluoromethyl)-4',5'-bis(methoxycarbonyl)tetrathiafulvalene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 97.834(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4209(8)
_cell_length_b                   17.0659(17)
_cell_length_c                   13.5707(15)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      1.85
_cell_volume                     1702.6(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation, phi incr. 1.4 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  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12937
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.9013
_exptl_absorpt_correction_T_min  0.7816
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
a grid of  8 x  8 x  8 =   512 sampling points was used
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0320
_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)+(0.0434P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                2161
_reflns_number_total             3263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-11-73-S2.cif
_cod_data_source_block           3bc
_cod_depositor_comments
'Adding full bibliography for 4030944--4030949.cif.'
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4030946
#BEGIN Tags that were not found in dictionaries:
_exptl_absorpt_correction_t_ave  0.8597
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.78962(8) 0.84970(4) 0.57327(4) 0.05360(19) Uani 1 1 d .
S2 S 0.52343(8) 0.93762(4) 0.67401(4) 0.04925(18) Uani 1 1 d .
S3 S 0.22510(8) 0.92198(4) 0.47713(4) 0.05080(19) Uani 1 1 d .
S4 S 0.48771(8) 0.82752(4) 0.37998(4) 0.0546(2) Uani 1 1 d .
C1 C 0.5674(3) 0.88684(15) 0.56695(15) 0.0434(5) Uani 1 1 d .
C2 C 0.8376(3) 0.86146(14) 0.70161(15) 0.0416(5) Uani 1 1 d .
C3 C 0.7171(3) 0.90105(14) 0.74688(15) 0.0400(5) Uani 1 1 d .
C4 C 1.0112(4) 0.8239(2) 0.7490(2) 0.0587(7) Uani 1 1 d .
C5 C 0.7304(4) 0.91767(17) 0.85677(17) 0.0539(7) Uani 1 1 d .
C6 C 0.4423(3) 0.87963(15) 0.48567(15) 0.0428(6) Uani 1 1 d .
C7 C 0.1589(3) 0.89035(14) 0.35499(15) 0.0382(5) Uani 1 1 d .
C8 C 0.2763(3) 0.84722(13) 0.31138(15) 0.0379(5) Uani 1 1 d .
C9 C -0.0222(3) 0.91859(15) 0.30997(16) 0.0450(6) Uani 1 1 d .
C10 C -0.2335(3) 0.92750(18) 0.16457(19) 0.0625(7) Uani 1 1 d .
H10A H -0.2470 0.9105 0.0965 0.094 Uiso 1 1 calc R
H10B H -0.2373 0.9837 0.1669 0.094 Uiso 1 1 calc R
H10C H -0.3307 0.9064 0.1964 0.094 Uiso 1 1 calc R
C11 C 0.2424(3) 0.81311(15) 0.20865(16) 0.0416(5) Uani 1 1 d .
C12 C 0.2933(5) 0.8302(2) 0.04365(19) 0.0947(12) Uani 1 1 d .
H12A H 0.3520 0.8660 0.0038 0.142 Uiso 1 1 calc R
H12B H 0.1660 0.8274 0.0188 0.142 Uiso 1 1 calc R
H12C H 0.3467 0.7791 0.0407 0.142 Uiso 1 1 calc R
F1 F 1.1126(18) 0.8668(8) 0.8191(7) 0.078(2) Uani 0.58 1 d P
F2 F 0.9832(13) 0.7566(5) 0.7877(8) 0.085(2) Uani 0.58 1 d P
F3 F 1.1222(10) 0.8124(7) 0.6814(8) 0.084(3) Uani 0.58 1 d P
F4 F 0.7782(6) 0.8545(2) 0.9109(2) 0.0881(12) Uani 0.80 1 d P
F5 F 0.8558(8) 0.9708(3) 0.8866(4) 0.0875(15) Uani 0.80 1 d P
F6 F 0.5794(6) 0.9446(4) 0.8815(4) 0.100(2) Uani 0.80 1 d P
F'1 F 0.984(2) 0.7719(10) 0.8193(13) 0.154(8) Uani 0.42 1 d P
F'2 F 1.095(2) 0.7873(11) 0.6872(13) 0.137(7) Uani 0.42 1 d P
F'3 F 1.109(3) 0.8768(13) 0.7924(12) 0.123(6) Uani 0.42 1 d P
F'4 F 0.887(3) 0.9333(12) 0.9039(15) 0.093(7) Uani 0.20 1 d P
F'5 F 0.617(4) 0.9731(16) 0.8737(18) 0.130(12) Uani 0.20 1 d P
F'6 F 0.666(2) 0.8596(8) 0.9070(9) 0.074(4) Uani 0.20 1 d P
O1 O -0.1185(3) 0.95569(16) 0.35540(14) 0.0919(8) Uani 1 1 d .
O2 O -0.0608(2) 0.90017(11) 0.21575(11) 0.0572(5) Uani 1 1 d .
O3 O 0.1603(3) 0.75389(12) 0.18902(13) 0.0723(6) Uani 1 1 d .
O4 O 0.3162(2) 0.85732(11) 0.14603(11) 0.0569(5) 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
C2 S1 C1 93.99(10)
C3 S2 C1 93.47(11)
C7 S3 C6 94.14(10)
C8 S4 C6 94.55(10)
C6 C1 S1 122.99(17)
C6 C1 S2 122.40(17)
S1 C1 S2 114.57(11)
C3 C2 C4 127.4(2)
C3 C2 S1 117.41(16)
C4 C2 S1 115.18(18)
C2 C3 C5 126.3(2)
C2 C3 S2 118.14(16)
C5 C3 S2 115.52(18)
F'3 C4 F'2 111.1(12)
F'3 C4 F2 124.4(9)
F'2 C4 F2 87.1(10)
F'3 C4 F3 93.1(11)
F'2 C4 F3 21.5(12)
F2 C4 F3 107.4(7)
F'3 C4 F'1 106.1(11)
F'2 C4 F'1 106.1(11)
F2 C4 F'1 21.9(11)
F3 C4 F'1 124.2(9)
F'3 C4 F1 17.2(14)
F'2 C4 F1 117.2(10)
F2 C4 F1 107.6(8)
F3 C4 F1 103.2(8)
F'1 C4 F1 88.9(10)
F'3 C4 C2 107.6(9)
F'2 C4 C2 113.1(8)
F2 C4 C2 112.2(5)
F3 C4 C2 110.1(5)
F'1 C4 C2 112.6(8)
F1 C4 C2 115.8(5)
F'4 C5 F6 123.9(11)
F'4 C5 F'5 109.0(15)
F6 C5 F'5 25.7(15)
F'4 C5 F5 31.6(9)
F6 C5 F5 105.9(4)
F'5 C5 F5 83.8(13)
F'4 C5 F4 74.7(9)
F6 C5 F4 108.7(4)
F'5 C5 F4 128.4(13)
F5 C5 F4 105.3(3)
F'4 C5 F'6 105.5(10)
F6 C5 F'6 75.3(7)
F'5 C5 F'6 99.5(14)
F5 C5 F'6 129.9(6)
F4 C5 F'6 36.6(6)
F'4 C5 C3 117.7(10)
F6 C5 C3 112.3(3)
F'5 C5 C3 110.7(11)
F5 C5 C3 112.3(3)
F4 C5 C3 111.8(3)
F'6 C5 C3 112.8(6)
C1 C6 S3 122.73(17)
C1 C6 S4 121.75(17)
S3 C6 S4 115.52(11)
C8 C7 C9 127.32(19)
C8 C7 S3 118.22(15)
C9 C7 S3 114.40(16)
C7 C8 C11 125.96(18)
C7 C8 S4 117.54(15)
C11 C8 S4 116.49(15)
O1 C9 O2 124.6(2)
O1 C9 C7 122.4(2)
O2 C9 C7 113.0(2)
O3 C11 O4 126.1(2)
O3 C11 C8 123.6(2)
O4 C11 C8 110.3(2)
F'1 F2 C4 84(3)
F'1 F2 F'2 124(3)
C4 F2 F'2 46.0(7)
F'6 F4 C5 71.9(11)
F'6 F4 F'4 115.2(15)
C5 F4 F'4 51.3(7)
F'4 F5 C5 71(2)
F'4 F5 F'5 110(3)
C5 F5 F'5 47.7(9)
F'5 F6 C5 78(3)
F'5 F6 F'6 128(3)
C5 F6 F'6 53.3(5)
F2 F'1 C4 74(3)
C4 F'2 F2 46.9(6)
F5 F'4 C5 78(2)
F5 F'4 F4 130(3)
C5 F'4 F4 54.0(8)
F6 F'5 C5 76(3)
F6 F'5 F5 118(3)
C5 F'5 F5 48.5(9)
F4 F'6 C5 71.5(11)
F4 F'6 F6 118.4(15)
C5 F'6 F6 51.4(6)
C9 O2 C10 116.86(19)
C11 O4 C12 115.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.741(2)
S1 C1 1.758(2)
S2 C3 1.745(2)
S2 C1 1.760(2)
S3 C7 1.749(2)
S3 C6 1.756(2)
S4 C8 1.744(2)
S4 C6 1.759(2)
C1 C6 1.348(3)
C2 C3 1.335(3)
C2 C4 1.503(3)
C3 C5 1.508(3)
C4 F'3 1.25(2)
C4 F'2 1.273(16)
C4 F2 1.291(9)
C4 F3 1.330(9)
C4 F'1 1.339(18)
C4 F1 1.346(13)
C5 F'4 1.28(2)
C5 F6 1.297(5)
C5 F'5 1.31(2)
C5 F5 1.323(7)
C5 F4 1.326(5)
C5 F'6 1.329(14)
C7 C8 1.339(3)
C7 C9 1.479(3)
C8 C11 1.500(3)
C9 O1 1.188(3)
C9 O2 1.310(3)
C10 O2 1.449(3)
C11 O3 1.192(3)
C11 O4 1.311(3)
C12 O4 1.452(3)
F2 F'1 0.50(3)
F2 F'2 1.767(19)
F4 F'6 0.833(12)
F4 F'4 1.58(2)
F5 F'4 0.71(2)
F5 F'5 1.76(3)
F6 F'5 0.58(3)
F6 F'6 1.605(16)
