#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104962.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104962
loop_
_publ_author_name
'García-Orduña, Pilar'
'Dahaoui, Slimane'
'Lecomte, Claude'
_publ_section_title
;
 Intermolecular interactions and charge transfer in the 2:1
 tetrathiafulvalene bromanil complex, (TTF)₂-BA
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              244
_journal_page_last               249
_journal_paper_doi               10.1107/S0108768111015801
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2(C6 H4 S4),( C6 Br4 O2)'
_chemical_formula_moiety         '2(C6 H4 S4),(C6 Br4 O2)'
_chemical_formula_structural     '(C6 H4 S4)2,(C6 Br4 O2)'
_chemical_formula_sum            'C18 H8 Br4 O2 S8'
_chemical_formula_weight         832.40
_chemical_name_common            'bis-tetrathiafulvalene p-bromanil'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.434(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2781(9)
_cell_length_b                   11.5982(8)
_cell_length_c                   11.0418(9)
_cell_measurement_reflns_used    51302
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.12
_cell_measurement_theta_min      3.36
_cell_volume                     1233.44(18)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Nonius, 1998) '
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Xcalibur-Saphire2
_diffrn_measurement_method       φ
_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  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            51302
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    7.221
_exptl_absorpt_correction_T_max  0.282
_exptl_absorpt_correction_T_min  0.086
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Absorb, (DeTitta, 1985)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.307
_refine_diff_density_min         -0.703
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0330
_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)+(0.0599P)²+0.3946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                3905
_reflns_number_total             3972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            gw5013.cif
_cod_data_source_block           100K
_cod_original_cell_volume        1233.44(17)
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'p 21/n '
_cod_database_code               2104962
_cod_database_fobs_code          2104962
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.32390(17) 0.00682(15) -0.24724(16) 0.0218(3) Uani d . 1 1 . .
Br Br1 0.19466(2) -0.13098(2) -0.08665(2) 0.02120(7) Uani d . 1 1 . .
Br Br2 0.42377(2) -0.152668(18) 0.21952(2) 0.01911(7) Uani d . 1 1 . .
C C1 0.4028(2) 0.00561(18) -0.1342(2) 0.0173(3) Uani d . 1 1 . .
C C2 0.3688(2) -0.05780(18) -0.0314(2) 0.0172(3) Uani d . 1 1 . .
C C3 0.4598(2) -0.06521(17) 0.0919(2) 0.0168(3) Uani d . 1 1 . .
C C8 0.4030(2) 0.21988(18) 0.1589(2) 0.0170(3) Uani d . 1 1 . .
C C11 0.3511(2) 0.15768(19) 0.2361(2) 0.0180(4) Uani d . 1 1 . .
S S1 0.30860(6) 0.23785(5) -0.00639(5) 0.01955(11) Uani d . 1 1 . .
S S2 0.56075(5) 0.29656(5) 0.21720(5) 0.01841(10) Uani d . 1 1 . .
S S3 0.43916(6) 0.14075(5) 0.40332(5) 0.02055(11) Uani d . 1 1 . .
S S4 0.18647(6) 0.09187(5) 0.17688(5) 0.02073(11) Uani d . 1 1 . .
C C7 0.4274(3) 0.3335(2) -0.0334(2) 0.0217(4) Uani d . 1 1 . .
H H7 0.4112 0.3666 -0.1160 0.026 Uiso calc R 1 1 . .
C C9 0.5425(3) 0.35789(19) 0.0678(2) 0.0209(4) Uani d . 1 1 . .
H H9 0.6121 0.4072 0.0583 0.025 Uiso calc R 1 1 . .
C C10 0.3074(3) 0.0619(2) 0.4299(2) 0.0241(4) Uani d . 1 1 . .
H H10 0.3161 0.0362 0.5141 0.029 Uiso calc R 1 1 . .
C C12 0.1927(3) 0.0388(2) 0.3270(2) 0.0240(4) Uani d . 1 1 . .
H H12 0.1181 -0.0046 0.3357 0.029 Uiso calc R 1 1 . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 122.12(19) ?
O1 C1 C3 . 3_655 121.97(19) ?
C2 C1 C3 . 3_655 115.89(17) ?
C3 C2 C1 . . 122.08(18) ?
C3 C2 Br1 . . 122.77(16) ?
C1 C2 Br1 . . 115.12(14) ?
C2 C3 C1 . 3_655 121.97(18) ?
C2 C3 Br2 . . 122.65(16) ?
C1 C3 Br2 3_655 . 115.37(14) ?
C11 C8 S1 . . 121.32(16) ?
C11 C8 S2 . . 123.42(16) ?
S1 C8 S2 . . 115.09(12) ?
C8 C11 S4 . . 122.23(17) ?
C8 C11 S3 . . 123.10(17) ?
S4 C11 S3 . . 114.63(12) ?
C7 S1 C8 . . 95.00(10) ?
C9 S2 C8 . . 94.52(11) ?
C10 S3 C11 . . 95.17(11) ?
C12 S4 C11 . . 95.05(11) ?
C9 C7 S1 . . 117.14(17) ?
C9 C7 H7 . . 121.4 ?
S1 C7 H7 . . 121.4 ?
C7 C9 S2 . . 118.21(18) ?
C7 C9 H9 . . 120.9 ?
S2 C9 H9 . . 120.9 ?
C12 C10 S3 . . 117.69(18) ?
C12 C10 H10 . . 121.2 ?
S3 C10 H10 . . 121.2 ?
C10 C12 S4 . . 117.46(18) ?
C10 C12 H12 . . 121.3 ?
S4 C12 H12 . . 121.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.229(3) ?
Br1 C2 . 1.880(2) ?
Br2 C3 . 1.876(2) ?
C1 C2 . 1.493(3) ?
C1 C3 3_655 1.493(3) ?
C2 C3 . 1.358(3) ?
C3 C1 3_655 1.493(3) ?
C8 C11 . 1.360(3) ?
C8 S1 . 1.755(2) ?
C8 S2 . 1.763(2) ?
C11 S4 . 1.761(2) ?
C11 S3 . 1.761(2) ?
S1 C7 . 1.750(2) ?
S2 C9 . 1.746(2) ?
S3 C10 . 1.742(3) ?
S4 C12 . 1.748(3) ?
C7 C9 . 1.344(3) ?
C7 H7 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C12 . 1.348(4) ?
C10 H10 . 0.9500 ?
C12 H12 . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 175.7(2) ?
C3 C1 C2 C3 3_655 . . . -2.8(3) ?
O1 C1 C2 Br1 . . . . -2.0(3) ?
C3 C1 C2 Br1 3_655 . . . 179.46(14) ?
C1 C2 C3 C1 . . . 3_655 3.0(3) ?
Br1 C2 C3 C1 . . . 3_655 -179.46(15) ?
C1 C2 C3 Br2 . . . . -175.80(16) ?
Br1 C2 C3 Br2 . . . . 1.7(3) ?
S1 C8 C11 S4 . . . . -0.4(3) ?
S2 C8 C11 S4 . . . . 174.65(12) ?
S1 C8 C11 S3 . . . . -177.99(12) ?
S2 C8 C11 S3 . . . . -2.9(3) ?
C11 C8 S1 C7 . . . . 174.49(19) ?
S2 C8 S1 C7 . . . . -0.94(14) ?
C11 C8 S2 C9 . . . . -175.2(2) ?
S1 C8 S2 C9 . . . . 0.11(14) ?
C8 C11 S3 C10 . . . . 177.0(2) ?
S4 C11 S3 C10 . . . . -0.76(14) ?
C8 C11 S4 C12 . . . . -177.3(2) ?
S3 C11 S4 C12 . . . . 0.44(14) ?
C8 S1 C7 C9 . . . . 1.8(2) ?
S1 C7 C9 S2 . . . . -2.1(3) ?
C8 S2 C9 C7 . . . . 1.2(2) ?
C11 S3 C10 C12 . . . . 0.9(2) ?
S3 C10 C12 S4 . . . . -0.8(3) ?
C11 S4 C12 C10 . . . . 0.2(2) ?
