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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/39/4503932.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_4503932
loop_
_publ_author_name
'Lu, Wen'
'Zhu, Qin-Yu'
'Dai, Jie'
'Zhang, Yong'
'Bian, Guo-Qing'
'Liu, Yu'
'Zhang, De-Qing'
_publ_section_title
;
 Tetrathiafulvalene-Diamide Salts with S···S and
 C···C Stacked Radical Couples
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              652
_journal_paper_doi               10.1021/cg060490s
_journal_volume                  7
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 N4 O4 S12, Br4 Cu'
_chemical_formula_sum            'C24 H28 Br4 Cu N4 O4 S12'
_chemical_formula_weight         1204.40
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.537(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.140(3)
_cell_length_b                   11.7092(12)
_cell_length_c                   14.2102(17)
_cell_measurement_reflns_used    8474
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3972.2(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21856
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    5.243
_exptl_absorpt_correction_T_max  0.5068
_exptl_absorpt_correction_T_min  0.1791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             2372
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.215
_refine_diff_density_min         -1.849
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0406
_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)+(0.0352P)²+21.0870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                4181
_reflns_number_total             4552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060490ssi20060725_112737.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_Hall     '-c 2yc'
_cod_original_sg_symbol_H-M      'c 2/c'
_cod_database_code               4503932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Br1 Br 0.506235(18) 0.70078(4) 0.10832(3) 0.04387(13) Uani 1 1 d .
Br2 Br 0.414387(18) 0.49601(4) 0.20738(3) 0.04043(12) Uani 1 1 d .
Cu1 Cu 0.5000 0.59374(5) 0.2500 0.02537(14) Uani 1 2 d S
S2 S 0.44931(3) 0.02526(7) 0.39255(6) 0.02263(17) Uani 1 1 d .
S3 S 0.60516(3) 0.19655(7) 0.36476(6) 0.02437(18) Uani 1 1 d .
S4 S 0.57323(3) -0.04263(7) 0.34086(6) 0.02427(18) Uani 1 1 d .
S5 S 0.72586(4) 0.14787(8) 0.34375(7) 0.0293(2) Uani 1 1 d .
S6 S 0.69013(4) -0.11628(9) 0.31584(8) 0.0341(2) Uani 1 1 d .
S1 S 0.47727(3) 0.26487(7) 0.36401(6) 0.02207(17) Uani 1 1 d .
O1 O 0.34655(11) -0.0342(2) 0.4382(2) 0.0321(6) Uani 1 1 d .
O2 O 0.32650(10) 0.3440(2) 0.3497(2) 0.0322(6) Uani 1 1 d .
N1 N 0.29753(12) 0.1312(3) 0.4110(2) 0.0293(7) Uani 1 1 d .
N2 N 0.39761(13) 0.4255(3) 0.4483(2) 0.0271(6) Uani 1 1 d .
C1 C 0.39648(13) 0.1256(3) 0.3981(2) 0.0210(6) Uani 1 1 d .
C2 C 0.41035(13) 0.2366(3) 0.3896(2) 0.0208(6) Uani 1 1 d .
C3 C 0.49878(13) 0.1248(3) 0.3707(2) 0.0212(6) Uani 1 1 d .
C4 C 0.55326(14) 0.0947(3) 0.3605(2) 0.0216(7) Uani 1 1 d .
C5 C 0.65729(13) 0.1020(3) 0.3441(2) 0.0225(7) Uani 1 1 d .
C6 C 0.64202(14) -0.0101(3) 0.3323(2) 0.0230(7) Uani 1 1 d .
C7 C 0.72214(16) 0.2963(3) 0.3749(3) 0.0345(9) Uani 1 1 d .
H7A H 0.6981 0.3369 0.3240 0.052 Uiso 1 1 calc R
H7B H 0.7598 0.3295 0.3830 0.052 Uiso 1 1 calc R
H7C H 0.7065 0.3034 0.4344 0.052 Uiso 1 1 calc R
C8 C 0.64602(19) -0.2235(4) 0.2550(5) 0.0563(14) Uani 1 1 d .
H8A H 0.6197 -0.2509 0.2963 0.084 Uiso 1 1 calc R
H8B H 0.6690 -0.2874 0.2386 0.084 Uiso 1 1 calc R
H8C H 0.6251 -0.1912 0.1968 0.084 Uiso 1 1 calc R
C9 C 0.34371(14) 0.0686(3) 0.4174(2) 0.0235(7) Uani 1 1 d .
C10 C 0.24434(15) 0.0847(4) 0.4287(3) 0.0374(9) Uani 1 1 d .
H10A H 0.2240 0.0539 0.3693 0.056 Uiso 1 1 calc R
H10B H 0.2221 0.1452 0.4525 0.056 Uiso 1 1 calc R
H10C H 0.2510 0.0235 0.4761 0.056 Uiso 1 1 calc R
C11 C 0.37428(14) 0.3410(3) 0.3948(2) 0.0233(7) Uani 1 1 d .
C12 C 0.37019(17) 0.5356(3) 0.4523(3) 0.0333(8) Uani 1 1 d .
H12A H 0.3517 0.5566 0.3885 0.050 Uiso 1 1 calc R
H12B H 0.3981 0.5936 0.4756 0.050 Uiso 1 1 calc R
H12C H 0.3422 0.5307 0.4955 0.050 Uiso 1 1 calc R
H1 H 0.2992(19) 0.192(4) 0.392(3) 0.035(13) Uiso 1 1 d .
H2 H 0.4264(17) 0.416(3) 0.482(3) 0.019(10) Uiso 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Br2 Cu1 Br2 122.03(4) . 2_655
Br2 Cu1 Br1 107.900(17) . 2_655
Br2 Cu1 Br1 101.528(15) 2_655 2_655
Br2 Cu1 Br1 101.528(15) . .
Br2 Cu1 Br1 107.900(17) 2_655 .
Br1 Cu1 Br1 116.89(4) 2_655 .
C3 S2 C1 94.77(16) . .
C4 S3 C5 95.41(16) . .
C4 S4 C6 95.79(17) . .
C5 S5 C7 102.43(17) . .
C6 S6 C8 101.88(19) . .
C3 S1 C2 95.12(16) . .
C9 N1 C10 122.5(3) . .
C9 N1 H1 117(3) . .
C10 N1 H1 120(3) . .
C11 N2 C12 121.9(3) . .
C11 N2 H2 120(3) . .
C12 N2 H2 118(3) . .
C2 C1 C9 132.3(3) . .
C2 C1 S2 116.8(2) . .
C9 C1 S2 110.8(2) . .
C1 C2 C11 128.5(3) . .
C1 C2 S1 116.8(3) . .
C11 C2 S1 114.6(2) . .
C4 C3 S1 121.2(3) . .
C4 C3 S2 122.5(3) . .
S1 C3 S2 116.22(18) . .
C3 C4 S4 123.2(3) . .
C3 C4 S3 121.0(3) . .
S4 C4 S3 115.73(19) . .
C6 C5 S3 116.4(3) . .
C6 C5 S5 122.3(3) . .
S3 C5 S5 121.2(2) . .
C5 C6 S4 116.6(3) . .
C5 C6 S6 122.0(3) . .
S4 C6 S6 121.3(2) . .
S5 C7 H7A 109.5 . .
S5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
S5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
S6 C8 H8A 109.5 . .
S6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
S6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O1 C9 N1 124.7(3) . .
O1 C9 C1 117.2(3) . .
N1 C9 C1 118.1(3) . .
N1 C10 H10A 109.5 . .
N1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
N1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O2 C11 N2 124.3(3) . .
O2 C11 C2 119.9(3) . .
N2 C11 C2 115.8(3) . .
N2 C12 H12A 109.5 . .
N2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.3953(6) .
Br2 Cu1 2.3614(5) .
Cu1 Br2 2.3614(5) 2_655
Cu1 Br1 2.3953(6) 2_655
S2 C3 1.729(3) .
S2 C1 1.744(3) .
S3 C4 1.724(3) .
S3 C5 1.733(3) .
S4 C4 1.714(3) .
S4 C6 1.726(3) .
S5 C5 1.741(3) .
S5 C7 1.799(4) .
S6 C6 1.741(3) .
S6 C8 1.785(5) .
S1 C3 1.719(3) .
S1 C2 1.739(3) .
O1 C9 1.239(4) .
O2 C11 1.234(4) .
N1 C9 1.326(5) .
N1 C10 1.450(5) .
N1 H1 0.76(5) .
N2 C11 1.322(5) .
N2 C12 1.453(5) .
N2 H2 0.79(4) .
C1 C2 1.352(5) .
C1 C9 1.499(5) .
C2 C11 1.509(5) .
C3 C4 1.389(4) .
C5 C6 1.366(5) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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
C3 S2 C1 C2 -3.1(3)
C3 S2 C1 C9 -179.8(2)
C9 C1 C2 C11 -1.9(6)
S2 C1 C2 C11 -177.8(3)
C9 C1 C2 S1 -178.7(3)
S2 C1 C2 S1 5.4(4)
C3 S1 C2 C1 -4.6(3)
C3 S1 C2 C11 178.1(2)
C2 S1 C3 C4 -176.6(3)
C2 S1 C3 S2 2.4(2)
C1 S2 C3 C4 178.8(3)
C1 S2 C3 S1 -0.2(2)
S1 C3 C4 S4 -165.44(19)
S2 C3 C4 S4 15.6(4)
S1 C3 C4 S3 13.2(4)
S2 C3 C4 S3 -165.74(19)
C6 S4 C4 C3 177.9(3)
C6 S4 C4 S3 -0.8(2)
C5 S3 C4 C3 -178.2(3)
C5 S3 C4 S4 0.5(2)
C4 S3 C5 C6 0.1(3)
C4 S3 C5 S5 -177.2(2)
C7 S5 C5 C6 -173.9(3)
C7 S5 C5 S3 3.3(3)
S3 C5 C6 S4 -0.7(4)
S5 C5 C6 S4 176.62(19)
S3 C5 C6 S6 -177.36(19)
S5 C5 C6 S6 0.0(4)
C4 S4 C6 C5 0.9(3)
C4 S4 C6 S6 177.6(2)
C8 S6 C6 C5 -155.8(3)
C8 S6 C6 S4 27.8(3)
C10 N1 C9 O1 0.4(6)
C10 N1 C9 C1 -179.7(3)
C2 C1 C9 O1 -167.3(3)
S2 C1 C9 O1 8.8(4)
C2 C1 C9 N1 12.8(5)
S2 C1 C9 N1 -171.1(3)
C12 N2 C11 O2 -5.4(6)
C12 N2 C11 C2 173.6(3)
C1 C2 C11 O2 -47.2(5)
S1 C2 C11 O2 129.7(3)
C1 C2 C11 N2 133.8(4)
S1 C2 C11 N2 -49.3(4)
