#------------------------------------------------------------------------------
#$Date: 2018-10-29 09:33:49 +0200 (Mon, 29 Oct 2018) $
#$Revision: 211691 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/22/7202257.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_7202257
loop_
_publ_author_name
'Liu, Guang-Xiang'
'Xu, Heng'
'Ren, Xiao-Ming'
'Sun, Wei-Yin'
_publ_section_title
;
 A series of novel ion-pair complexes based on TCNQ: syntheses, crystal
 structures and properties
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1574
_journal_paper_doi               10.1039/b808390h
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C16 H13 Br N, C12 H4 N4, 0.5(C2 H3 N)'
_chemical_formula_sum            'C29 H18.5 Br N5.5'
_chemical_formula_weight         523.90
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 124.01(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.313(18)
_cell_length_b                   7.272(4)
_cell_length_c                   22.982(11)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.95
_cell_measurement_theta_min      2.78
_cell_volume                     4892(5)
_computing_cell_refinement       'SAINT-PLUS, Ver. 6.0, 1997'
_computing_data_collection       'SMART, 1998'
_computing_data_reduction        'SAINT-PLUS, Ver. 6.0, 1997'
_computing_molecular_graphics    'XP, Ver. 6.10, Bruker AXS Inc., 2000'
_computing_publication_material  'SHELXTL-Bruker AXS Inc., 1998'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11529
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.709
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_correction_T_min  0.7262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.926
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.0804
_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)+(0.0107P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                2525
_reflns_number_total             4256
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b808390h.txt
_cod_data_source_block           TQ4
_cod_depositor_comments
;

2018-10-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C58 H37 Br2 N11'
_cod_original_formula_weight         1047.81
_cod_original_formula_moiety         '2(C16 H13 Br N), 2(C12 H4 N4), C2 H3 N'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4892(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7202257
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21837(3) 0.83030(12) 0.21516(5) 0.1003(4) Uani 1 1 d . . .
C1 C 0.1841(2) 0.6091(9) 0.1923(4) 0.058(2) Uani 1 1 d . . .
C2 C 0.1690(2) 0.5533(11) 0.2325(4) 0.067(2) Uani 1 1 d . . .
H2 H 0.1757 0.6212 0.2715 0.080 Uiso 1 1 calc R . .
C3 C 0.1436(2) 0.3944(11) 0.2144(4) 0.064(2) Uani 1 1 d . . .
H3 H 0.1326 0.3573 0.2411 0.077 Uiso 1 1 calc R . .
C4 C 0.1340(2) 0.2896(9) 0.1583(3) 0.0379(17) Uani 1 1 d . . .
C5 C 0.1498(2) 0.3492(9) 0.1182(3) 0.0463(19) Uani 1 1 d . . .
H5 H 0.1436 0.2797 0.0799 0.056 Uiso 1 1 calc R . .
C6 C 0.1745(2) 0.5098(10) 0.1343(4) 0.061(2) Uani 1 1 d . . .
H6 H 0.1844 0.5503 0.1067 0.073 Uiso 1 1 calc R . .
C7 C 0.1051(2) 0.1194(8) 0.1387(3) 0.0438(18) Uani 1 1 d . . .
H7A H 0.1172 0.0413 0.1796 0.053 Uiso 1 1 calc R . .
H7B H 0.1062 0.0512 0.1034 0.053 Uiso 1 1 calc R . .
C8 C 0.0435(3) 0.1769(9) 0.1555(4) 0.054(2) Uani 1 1 d . . .
H8 H 0.0645 0.1390 0.2014 0.065 Uiso 1 1 calc R . .
C9 C 0.0029(3) 0.2364(9) 0.1391(4) 0.052(2) Uani 1 1 d . . .
H9 H -0.0040 0.2440 0.1726 0.063 Uiso 1 1 calc R . .
C10 C -0.0274(3) 0.2847(9) 0.0720(5) 0.057(2) Uani 1 1 d . . .
H10 H -0.0560 0.3267 0.0590 0.068 Uiso 1 1 calc R . .
C11 C -0.0177(2) 0.2742(8) 0.0203(4) 0.0404(17) Uani 1 1 d . . .
C12 C -0.0498(2) 0.3148(8) -0.0514(4) 0.056(2) Uani 1 1 d . . .
H12 H -0.0789 0.3554 -0.0663 0.068 Uiso 1 1 calc R . .
C13 C -0.0383(3) 0.2948(9) -0.0991(4) 0.056(2) Uani 1 1 d . . .
H13 H -0.0599 0.3211 -0.1462 0.067 Uiso 1 1 calc R . .
C14 C 0.0042(2) 0.2368(8) -0.0787(4) 0.0485(19) Uani 1 1 d . . .
H14 H 0.0113 0.2235 -0.1119 0.058 Uiso 1 1 calc R . .
C15 C 0.0365(2) 0.1983(7) -0.0098(4) 0.0403(17) Uani 1 1 d . . .
H15 H 0.0658 0.1625 0.0045 0.048 Uiso 1 1 calc R . .
C16 C 0.0247(2) 0.2136(7) 0.0398(3) 0.0353(17) Uani 1 1 d . . .
C17 C 0.1333(2) 0.8246(10) 0.3341(4) 0.049(2) Uani 1 1 d . . .
C18 C 0.1245(2) 0.6953(10) 0.4223(4) 0.051(2) Uani 1 1 d . . .
C19 C 0.1529(2) 0.7607(9) 0.4029(3) 0.0423(18) Uani 1 1 d . . .
C20 C 0.2014(2) 0.7562(8) 0.4514(3) 0.0404(17) Uani 1 1 d . . .
C21 C 0.2321(2) 0.8182(8) 0.4332(3) 0.0441(18) Uani 1 1 d . . .
H21 H 0.2201 0.8650 0.3884 0.053 Uiso 1 1 calc R . .
C22 C 0.2221(2) 0.6897(8) 0.5208(3) 0.0414(18) Uani 1 1 d . . .
H22 H 0.2035 0.6501 0.5352 0.050 Uiso 1 1 calc R . .
C23 C 0.1223(3) 0.2556(9) 0.3749(4) 0.051(2) Uani 1 1 d . . .
C24 C 0.1410(2) 0.1300(10) 0.4845(4) 0.046(2) Uani 1 1 d . . .
C25 C 0.1554(2) 0.2027(9) 0.4428(3) 0.0405(17) Uani 1 1 d . . .
C26 C 0.2025(2) 0.2275(8) 0.4720(4) 0.0399(17) Uani 1 1 d . . .
C27 C 0.2185(2) 0.2988(9) 0.4322(3) 0.0434(18) Uani 1 1 d . . .
H27 H 0.1971 0.3326 0.3859 0.052 Uiso 1 1 calc R . .
C28 C 0.2360(2) 0.1794(8) 0.5417(3) 0.0436(17) Uani 1 1 d . . .
H28 H 0.2274 0.1324 0.5703 0.052 Uiso 1 1 calc R . .
C29 C 0.0000 0.5967(16) 0.2500 0.098(5) Uani 1 2 d S . .
C30 C 0.0000 0.7902(19) 0.2500 0.075(4) Uani 1 2 d S . .
N1 N 0.05618(17) 0.1680(6) 0.1105(3) 0.0401(14) Uani 1 1 d . . .
N2 N 0.0000 0.9492(16) 0.2500 0.126(5) Uani 1 2 d S . .
N3 N 0.1177(2) 0.8700(9) 0.2774(3) 0.078(2) Uani 1 1 d . . .
N4 N 0.1007(2) 0.6379(9) 0.4364(3) 0.074(2) Uani 1 1 d . . .
N5 N 0.0944(2) 0.3001(8) 0.3180(3) 0.0668(19) Uani 1 1 d . . .
N6 N 0.12925(19) 0.0773(8) 0.5187(3) 0.0625(19) 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
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
C2 C1 C6 121.4(7) . . ?
C2 C1 Br1 119.7(6) . . ?
C6 C1 Br1 119.0(6) . . ?
C1 C2 C3 118.8(7) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.9(7) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 C7 120.7(6) . . ?
C5 C4 C7 121.1(6) . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.6(7) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C4 C7 N1 111.0(5) . . ?
C4 C7 H7A 109.4 . . ?
N1 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
N1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 N1 124.7(7) . . ?
C9 C8 H8 117.7 . . ?
N1 C8 H8 117.7 . . ?
C8 C9 C10 116.6(7) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C9 C10 C11 122.7(7) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C16 C11 C10 118.5(7) . . ?
C16 C11 C12 117.8(7) . . ?
C10 C11 C12 123.7(7) . . ?
C13 C12 C11 120.4(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 121.2(7) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 120.3(7) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.1(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 N1 117.9(6) . . ?
C11 C16 C15 121.2(7) . . ?
N1 C16 C15 120.9(6) . . ?
N3 C17 C19 177.2(8) . . ?
N4 C18 C19 177.8(8) . . ?
C18 C19 C17 118.9(6) . . ?
C18 C19 C20 120.5(6) . . ?
C17 C19 C20 120.5(6) . . ?
C22 C20 C19 121.6(6) . . ?
C22 C20 C21 115.9(6) . . ?
C19 C20 C21 122.4(6) . . ?
C22 C21 C20 121.8(6) 7_566 . ?
C22 C21 H21 119.1 7_566 . ?
C20 C21 H21 119.1 . . ?
C21 C22 C20 122.2(6) 7_566 . ?
C21 C22 H22 118.9 7_566 . ?
C20 C22 H22 118.9 . . ?
N5 C23 C25 179.8(9) . . ?
N6 C24 C25 177.7(8) . . ?
C23 C25 C26 122.0(6) . . ?
C23 C25 C24 118.0(6) . . ?
C26 C25 C24 119.9(6) . . ?
C28 C26 C25 121.9(7) . . ?
C28 C26 C27 116.2(6) . . ?
C25 C26 C27 121.9(6) . . ?
C28 C27 C26 123.5(6) 7_556 . ?
C28 C27 H27 118.2 7_556 . ?
C26 C27 H27 118.2 . . ?
C27 C28 C26 120.3(6) 7_556 . ?
C27 C28 H28 119.9 7_556 . ?
C26 C28 H28 119.9 . . ?
N2 C30 C29 180.000(7) . . ?
C8 N1 C16 119.5(6) . . ?
C8 N1 C7 118.5(6) . . ?
C16 N1 C7 121.9(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.902(7) . ?
C1 C2 1.361(8) . ?
C1 C6 1.380(8) . ?
C2 C3 1.377(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(7) . ?
C4 C7 1.505(8) . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.508(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.335(9) . ?
C8 N1 1.338(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.343(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.412(8) . ?
C10 H10 0.9300 . ?
C11 C16 1.372(8) . ?
C11 C12 1.414(8) . ?
C12 C13 1.372(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.419(7) . ?
C15 H15 0.9300 . ?
C16 N1 1.401(7) . ?
C17 N3 1.144(7) . ?
C17 C19 1.404(8) . ?
C18 N4 1.135(8) . ?
C18 C19 1.389(9) . ?
C19 C20 1.428(8) . ?
C20 C22 1.418(7) . ?
C20 C21 1.434(8) . ?
C21 C22 1.351(8) 7_566 ?
C21 H21 0.9300 . ?
C22 C21 1.351(8) 7_566 ?
C22 H22 0.9300 . ?
C23 N5 1.160(8) . ?
C23 C25 1.383(9) . ?
C24 N6 1.141(7) . ?
C24 C25 1.416(8) . ?
C25 C26 1.412(8) . ?
C26 C28 1.402(8) . ?
C26 C27 1.417(8) . ?
C27 C28 1.375(8) 7_556 ?
C27 H27 0.9300 . ?
C28 C27 1.375(8) 7_556 ?
C28 H28 0.9300 . ?
C29 C30 1.407(15) . ?
C30 N2 1.156(14) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(12) . . . . ?
Br1 C1 C2 C3 178.9(6) . . . . ?
C1 C2 C3 C4 1.4(12) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C2 C3 C4 C7 -178.3(7) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C7 C4 C5 C6 176.9(6) . . . . ?
C4 C5 C6 C1 1.3(10) . . . . ?
C2 C1 C6 C5 -1.2(11) . . . . ?
Br1 C1 C6 C5 179.7(5) . . . . ?
C3 C4 C7 N1 69.0(7) . . . . ?
C5 C4 C7 N1 -107.9(6) . . . . ?
N1 C8 C9 C10 2.2(10) . . . . ?
C8 C9 C10 C11 0.0(10) . . . . ?
C9 C10 C11 C16 -0.5(9) . . . . ?
C9 C10 C11 C12 176.5(6) . . . . ?
C16 C11 C12 C13 -0.5(9) . . . . ?
C10 C11 C12 C13 -177.5(6) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C15 -0.3(10) . . . . ?
C13 C14 C15 C16 2.0(9) . . . . ?
C10 C11 C16 N1 -1.0(8) . . . . ?
C12 C11 C16 N1 -178.1(5) . . . . ?
C10 C11 C16 C15 179.4(5) . . . . ?
C12 C11 C16 C15 2.2(9) . . . . ?
C14 C15 C16 C11 -3.0(9) . . . . ?
C14 C15 C16 N1 177.3(5) . . . . ?
N4 C18 C19 C17 57(24) . . . . ?
N4 C18 C19 C20 -121(23) . . . . ?
N3 C17 C19 C18 -98(18) . . . . ?
N3 C17 C19 C20 79(18) . . . . ?
C18 C19 C20 C22 -1.5(10) . . . . ?
C17 C19 C20 C22 -179.0(6) . . . . ?
C18 C19 C20 C21 178.5(6) . . . . ?
C17 C19 C20 C21 1.0(10) . . . . ?
C22 C20 C21 C22 1.1(10) . . . 7_566 ?
C19 C20 C21 C22 -178.9(6) . . . 7_566 ?
C19 C20 C22 C21 178.9(6) . . . 7_566 ?
C21 C20 C22 C21 -1.2(10) . . . 7_566 ?
N5 C23 C25 C26 -145(100) . . . . ?
N5 C23 C25 C24 32(100) . . . . ?
N6 C24 C25 C23 -85(20) . . . . ?
N6 C24 C25 C26 91(20) . . . . ?
C23 C25 C26 C28 177.9(6) . . . . ?
C24 C25 C26 C28 1.1(9) . . . . ?
C23 C25 C26 C27 -3.6(10) . . . . ?
C24 C25 C26 C27 179.7(6) . . . . ?
C28 C26 C27 C28 0.3(10) . . . 7_556 ?
C25 C26 C27 C28 -178.3(6) . . . 7_556 ?
C25 C26 C28 C27 178.3(6) . . . 7_556 ?
C27 C26 C28 C27 -0.3(10) . . . 7_556 ?
C9 C8 N1 C16 -3.7(10) . . . . ?
C9 C8 N1 C7 172.8(6) . . . . ?
C11 C16 N1 C8 3.0(8) . . . . ?
C15 C16 N1 C8 -177.4(5) . . . . ?
C11 C16 N1 C7 -173.4(5) . . . . ?
C15 C16 N1 C7 6.2(8) . . . . ?
C4 C7 N1 C8 -91.6(7) . . . . ?
C4 C7 N1 C16 84.9(7) . . . . ?
