#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/09/4030948.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_4030948
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_moiety         'C9 H5 F3 S6, 0.5(C12 H4 N4)'
_chemical_formula_sum            'C15 H7 F3 N2 S6'
_chemical_formula_weight         464.59
_chemical_name_common            '(EDT TTF CF3)2 TCNQ'
_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                 106.997(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2146(15)
_cell_length_b                   11.1448(8)
_cell_length_c                   13.1662(15)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.4
_cell_volume                     1854.3(4)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'oscillation, phi incr. 1.7 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  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13683
_diffrn_reflns_theta_full        25.83
_diffrn_reflns_theta_max         25.83
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.9119
_exptl_absorpt_correction_T_min  0.8216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0000(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constrain
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          4.925
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                2190
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-11-73-S2.cif
_cod_data_source_block           (1c)2-TCNQ
_cod_depositor_comments
'Adding full bibliography for 4030944--4030949.cif.'
_cod_original_cell_volume        1854.3(3)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4030948
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
S1 S 0.94722(5) 0.22237(7) 0.16058(5) 0.0466(2) Uani 1 1 d .
S2 S 0.88591(5) 0.17779(7) -0.07090(5) 0.0466(2) Uani 1 1 d .
S3 S 1.18766(5) 0.15446(7) 0.17929(5) 0.0509(2) Uani 1 1 d .
S4 S 0.66283(5) 0.25729(8) -0.10515(5) 0.0529(2) Uani 1 1 d .
S5 S 1.13058(6) 0.11560(8) -0.05361(6) 0.0532(2) Uani 1 1 d .
S6 S 0.74352(6) 0.32432(9) 0.16200(6) 0.0693(3) Uani 1 1 d .
C6 C 0.79027(19) 0.2388(2) -0.0175(2) 0.0395(6) Uani 1 1 d .
F1 F 1.43171(15) 0.2121(2) 0.23372(18) 0.0932(7) Uani 1 1 d .
C4 C 1.3971(2) 0.1052(3) 0.1948(3) 0.0595(8) Uani 1 1 d .
C'1 C 1.1083(2) 0.4768(2) 0.0502(2) 0.0489(7) Uani 1 1 d .
C3 C 1.2608(2) 0.0955(3) 0.0198(2) 0.0520(7) Uani 1 1 d .
H3 H 1.3115 0.0735 -0.0130 0.062 Uiso 1 1 calc R
C5 C 0.98804(19) 0.1839(2) 0.04926(19) 0.0407(6) Uani 1 1 d .
C1 C 1.0885(2) 0.1571(2) 0.0568(2) 0.0415(6) Uani 1 1 d .
F2 F 1.46402(14) 0.0682(2) 0.14364(18) 0.0977(8) Uani 1 1 d .
F3 F 1.40765(15) 0.0329(2) 0.27556(18) 0.0996(8) Uani 1 1 d .
C9 C 0.8180(2) 0.2611(2) 0.0864(2) 0.0428(6) Uani 1 1 d .
C'5 C 1.0396(2) 0.5177(3) 0.1091(2) 0.0531(7) Uani 1 1 d .
H'5 H 1.0672 0.5295 0.1819 0.064 Uiso 1 1 calc R
C2 C 1.2869(2) 0.1118(3) 0.1233(2) 0.0461(7) Uani 1 1 d .
C'2 C 1.2135(3) 0.4543(3) 0.0989(2) 0.0532(7) Uani 1 1 d .
C'6 C 1.0633(3) 0.4607(3) -0.0625(2) 0.0531(7) Uani 1 1 d .
H'6 H 1.1059 0.4350 -0.1033 0.064 Uiso 1 1 calc R
N2 N 1.2962(3) 0.4843(3) 0.3000(2) 0.0908(10) Uani 1 1 d .
C7 C 0.5885(2) 0.2292(4) -0.0117(3) 0.0685(9) Uani 1 1 d .
H7A H 0.5136 0.2324 -0.0495 0.082 Uiso 1 1 calc R
H7B H 0.6042 0.1486 0.0162 0.082 Uiso 1 1 calc R
C'3 C 1.2840(3) 0.4121(3) 0.0425(3) 0.0612(8) Uani 1 1 d .
N1 N 1.3407(3) 0.3774(3) -0.0013(3) 0.0829(9) Uani 1 1 d .
C'4 C 1.2597(3) 0.4712(3) 0.2107(3) 0.0641(9) Uani 1 1 d .
C8 C 0.6102(2) 0.3133(4) 0.0774(3) 0.0686(10) Uani 1 1 d .
H8A H 0.5655 0.2915 0.1213 0.082 Uiso 1 1 calc R
H8B H 0.5884 0.3925 0.0488 0.082 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
C9 S1 C5 94.68(12) .
C6 S2 C5 94.48(12) .
C2 S3 C1 93.87(13) .
C6 S4 C7 98.05(13) .
C3 S5 C1 94.32(13) .
C9 S6 C8 103.54(14) .
C9 C6 S4 125.2(2) .
C9 C6 S2 118.0(2) .
S4 C6 S2 116.62(15) .
F3 C4 F2 107.0(3) .
F3 C4 F1 107.3(3) .
F2 C4 F1 105.7(3) .
F3 C4 C2 113.4(3) .
F2 C4 C2 111.7(3) .
F1 C4 C2 111.4(3) .
C'2 C'1 C'5 121.4(3) .
C'2 C'1 C'6 121.1(3) .
C'5 C'1 C'6 117.6(3) .
C2 C3 S5 118.6(2) .
C1 C5 S2 122.9(2) .
C1 C5 S1 122.26(19) .
S2 C5 S1 114.76(14) .
C5 C1 S3 122.0(2) .
C5 C1 S5 122.95(19) .
S3 C1 S5 114.99(15) .
C6 C9 S6 129.1(2) .
C6 C9 S1 117.2(2) .
S6 C9 S1 113.69(15) .
C'6 C'5 C'1 121.9(3) 3_765
C3 C2 C4 124.1(3) .
C3 C2 S3 118.2(2) .
C4 C2 S3 117.6(2) .
C'1 C'2 C'3 122.7(3) .
C'1 C'2 C'4 121.7(3) .
C'3 C'2 C'4 115.5(3) .
C'5 C'6 C'1 120.5(3) 3_765
C8 C7 S4 114.5(2) .
N1 C'3 C'2 179.0(4) .
N2 C'4 C'2 179.6(4) .
C7 C8 S6 118.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C9 1.755(3) .
S1 C5 1.757(3) .
S2 C6 1.753(3) .
S2 C5 1.755(2) .
S3 C2 1.748(3) .
S3 C1 1.756(3) .
S4 C6 1.753(3) .
S4 C7 1.812(3) .
S5 C3 1.724(3) .
S5 C1 1.763(3) .
S6 C9 1.741(3) .
S6 C8 1.792(3) .
C6 C9 1.332(4) .
F1 C4 1.325(4) .
C4 F3 1.309(3) .
C4 F2 1.324(4) .
C4 C2 1.486(4) .
C'1 C'2 1.374(4) .
C'1 C'5 1.430(4) .
C'1 C'6 1.439(4) .
C3 C2 1.316(4) .
C5 C1 1.336(4) .
C'5 C'6 1.340(4) 3_765
C'2 C'3 1.431(5) .
C'2 C'4 1.431(5) .
C'6 C'5 1.340(4) 3_765
N2 C'4 1.141(4) .
C7 C8 1.463(4) .
C'3 N1 1.137(4) .
