#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:05:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179439 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/36/4333647.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_4333647
loop_
_publ_author_name
'Rong-Guang Lin'
'Gang Xu'
'Ming-Sheng Wang'
'Gang Lu'
'Pei-Xin Li'
'Guo-Cong Guo'
_publ_contact_author_address
;
State Key Laboratory of Structural Chemistry
Fujian Institute of Research on the Structure of Matter,
Chinese Academy of Sciences
Fuzhou, Fujian 350002
P. R. China
;
_publ_contact_author_email       gcguo@fjirsm.ac.cn
_publ_contact_author_name        'Prof. Guo-Cong Guo'
_publ_section_title
;
 Improved Photochromic Properties on Viologen-Based Inorganic-Organic
 Hybrids by Using π-Conjugated Substituents as Electron Donors and
 Stabilizers
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1199
_journal_page_last               1205
_journal_paper_doi               10.1021/ic301181b
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         (HMQ)2Bi2Cl10
_chemical_formula_sum            'C22 H24 Bi2 Cl10 N4 O0'
_chemical_formula_weight         1116.91
_chemical_name_common            (HMQ)2Bi2Cl10
_chemical_name_systematic        (HMQ)2Bi2Cl10
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.049(3)
_cell_length_b                   13.957(3)
_cell_length_c                   18.266(4)
_cell_measurement_reflns_used    8660
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      2.6655
_cell_volume                     3326.7(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'AFC10: Fixed Chi 2 circle'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22528
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    11.390
_exptl_absorpt_correction_T_max  0.2630
_exptl_absorpt_correction_T_min  0.0867
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.374
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.374
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0170P)²+17.9223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                2999
_reflns_number_total             3030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301181b_si_002_1.cif
_cod_data_source_block           1
_cod_original_cell_volume        3326.7(12)
_cod_database_code               4333647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
Bi1 Bi 0.10223(2) 0.01136(2) 0.597335(16) 0.03718(12) Uani 1 1 d .
Cl1 Cl 0.24086(18) 0.13572(19) 0.62671(14) 0.0599(6) Uani 1 1 d .
Cl2 Cl 0.1354(2) -0.08665(18) 0.71394(13) 0.0592(6) Uani 1 1 d .
Cl3 Cl -0.03940(18) 0.11488(19) 0.66639(13) 0.0593(6) Uani 1 1 d .
Cl4 Cl 0.23444(17) -0.10417(17) 0.52594(14) 0.0554(6) Uani 1 1 d .
Cl5 Cl 0.05753(16) 0.11834(16) 0.45894(12) 0.0459(5) Uani 1 1 d .
N101 N -0.1117(5) 0.7326(5) 0.6989(4) 0.0448(17) Uani 1 1 d .
N102 N -0.0803(7) 0.2826(6) 0.5375(4) 0.057(2) Uani 1 1 d .
H10J H -0.0768 0.2263 0.5186 0.068 Uiso 1 1 calc R
C101 C -0.1191(8) 0.8242(8) 0.7391(6) 0.071(3) Uiso 1 1 d .
H10A H -0.0533 0.8550 0.7396 0.106 Uiso 1 1 calc R
H10B H -0.1407 0.8121 0.7885 0.106 Uiso 1 1 calc R
H10C H -0.1681 0.8650 0.7154 0.106 Uiso 1 1 calc R
C102 C -0.0224(7) 0.7033(6) 0.6723(5) 0.049(2) Uani 1 1 d .
H10D H 0.0351 0.7422 0.6773 0.059 Uiso 1 1 calc R
C103 C -0.0133(7) 0.6161(6) 0.6371(5) 0.045(2) Uani 1 1 d .
H10E H 0.0494 0.5969 0.6179 0.054 Uiso 1 1 calc R
C104 C -0.0989(6) 0.5573(6) 0.6308(4) 0.0376(18) Uani 1 1 d .
C105 C -0.1908(6) 0.5913(7) 0.6582(5) 0.049(2) Uani 1 1 d .
H10F H -0.2498 0.5546 0.6536 0.059 Uiso 1 1 calc R
C106 C -0.1954(7) 0.6786(7) 0.6921(5) 0.050(2) Uani 1 1 d .
H10G H -0.2575 0.7006 0.7105 0.060 Uiso 1 1 calc R
C107 C -0.0905(6) 0.4617(6) 0.5969(4) 0.0388(18) Uani 1 1 d .
C108 C -0.1795(7) 0.4117(6) 0.5756(5) 0.049(2) Uani 1 1 d .
H10H H -0.2435 0.4399 0.5814 0.059 Uiso 1 1 calc R
C109 C -0.1716(8) 0.3215(7) 0.5466(5) 0.056(2) Uani 1 1 d .
H10I H -0.2302 0.2879 0.5333 0.068 Uiso 1 1 calc R
C110 C 0.0070(8) 0.3261(7) 0.5563(6) 0.060(3) Uani 1 1 d .
H11A H 0.0695 0.2954 0.5493 0.072 Uiso 1 1 calc R
C111 C 0.0036(7) 0.4166(7) 0.5860(5) 0.052(2) Uani 1 1 d .
H11B H 0.0640 0.4477 0.5989 0.063 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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
Cl1 Bi1 Cl2 93.90(8) . .
Cl1 Bi1 Cl3 91.33(8) . .
Cl2 Bi1 Cl3 90.76(8) . .
Cl1 Bi1 Cl4 93.13(8) . .
Cl2 Bi1 Cl4 88.55(8) . .
Cl3 Bi1 Cl4 175.52(8) . .
Cl1 Bi1 Cl5 171.23(7) . 5_556
Cl2 Bi1 Cl5 94.66(7) . 5_556
Cl3 Bi1 Cl5 90.43(7) . 5_556
Cl4 Bi1 Cl5 85.22(7) . 5_556
Cl1 Bi1 Cl5 88.66(7) . .
Cl2 Bi1 Cl5 177.39(7) . .
Cl3 Bi1 Cl5 89.66(7) . .
Cl4 Bi1 Cl5 90.83(7) . .
Cl5 Bi1 Cl5 82.76(6) 5_556 .
Bi1 Cl5 Bi1 97.24(6) 5_556 .
C102 N101 C106 120.7(8) . .
C102 N101 C101 120.4(8) . .
C106 N101 C101 118.8(8) . .
C109 N102 C110 123.4(8) . .
C109 N102 H10J 118.3 . .
C110 N102 H10J 118.3 . .
N101 C101 H10A 109.5 . .
N101 C101 H10B 109.5 . .
H10A C101 H10B 109.5 . .
N101 C101 H10C 109.5 . .
H10A C101 H10C 109.5 . .
H10B C101 H10C 109.5 . .
N101 C102 C103 121.1(8) . .
N101 C102 H10D 119.4 . .
C103 C102 H10D 119.4 . .
C102 C103 C104 119.4(8) . .
C102 C103 H10E 120.3 . .
C104 C103 H10E 120.3 . .
C105 C104 C103 117.5(8) . .
C105 C104 C107 121.8(7) . .
C103 C104 C107 120.6(7) . .
C106 C105 C104 120.5(8) . .
C106 C105 H10F 119.7 . .
C104 C105 H10F 119.7 . .
N101 C106 C105 120.7(8) . .
N101 C106 H10G 119.7 . .
C105 C106 H10G 119.7 . .
C111 C107 C108 117.6(8) . .
C111 C107 C104 122.2(7) . .
C108 C107 C104 120.2(7) . .
C109 C108 C107 120.0(8) . .
C109 C108 H10H 120.0 . .
C107 C108 H10H 120.0 . .
N102 C109 C108 119.6(9) . .
N102 C109 H10I 120.2 . .
C108 C109 H10I 120.2 . .
N102 C110 C111 119.4(9) . .
N102 C110 H11A 120.3 . .
C111 C110 H11A 120.3 . .
C110 C111 C107 120.0(9) . .
C110 C111 H11B 120.0 . .
C107 C111 H11B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Cl1 2.564(2) .
Bi1 Cl2 2.568(2) .
Bi1 Cl3 2.664(2) .
Bi1 Cl4 2.698(2) .
Bi1 Cl5 2.946(2) 5_556
Bi1 Cl5 2.993(2) .
Cl5 Bi1 2.946(2) 5_556
N101 C102 1.327(11) .
N101 C106 1.333(11) .
N101 C101 1.477(12) .
N102 C109 1.319(12) .
N102 C110 1.335(12) .
N102 H10J 0.8600 .
C101 H10A 0.9600 .
C101 H10B 0.9600 .
C101 H10C 0.9600 .
C102 C103 1.381(12) .
C102 H10D 0.9300 .
C103 C104 1.391(11) .
C103 H10E 0.9300 .
C104 C105 1.383(11) .
C104 C107 1.476(11) .
C105 C106 1.368(12) .
C105 H10F 0.9300 .
C106 H10G 0.9300 .
C107 C111 1.393(12) .
C107 C108 1.408(11) .
C108 C109 1.370(12) .
C108 H10H 0.9300 .
C109 H10I 0.9300 .
C110 C111 1.376(13) .
C110 H11A 0.9300 .
C111 H11B 0.9300 .
