#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180443 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/12/7211238.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_7211238
loop_
_publ_author_name
'Toma, Oksana'
'Mercier, Nicolas'
'Allain, Magali'
'Botta, Chiara'
_publ_section_title
;
 Protonated N-oxide-4,4′-bipyridine: from luminescent BiIII
 complexes to hybrids based on H-bonded dimers or H-bonded open 2D square
 supramolecular networks
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              8565
_journal_paper_doi               10.1039/c3ce41579a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C10 H9 Bi Cl4 N2 O'
_chemical_formula_weight         523.97
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2013-02-20T14:46:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.968(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8244(8)
_cell_length_b                   9.7773(2)
_cell_length_c                   16.5190(7)
_cell_measurement_temperature    293(2)
_cell_volume                     3028.93(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22424
_diffrn_reflns_theta_full        32.01
_diffrn_reflns_theta_max         32.01
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    12.336
_exptl_absorpt_correction_T_max  0.319
_exptl_absorpt_correction_T_min  0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.82
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         5215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0154P)²+2.7411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0626
_reflns_number_gt                2962
_reflns_number_total             5215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41579a.txt
_cod_data_source_block           sad
_cod_database_code               7211238
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
Bi1 Bi 0.815566(10) 0.109688(19) 0.066893(11) 0.03303(6) Uani 1 1 d .
Cl4 Cl 0.94656(7) 0.15750(17) 0.12071(10) 0.0628(4) Uani 1 1 d .
Cl2 Cl 0.85395(8) -0.05569(16) -0.05427(8) 0.0523(4) Uani 1 1 d .
Cl1 Cl 0.67168(7) 0.11630(15) 0.00509(8) 0.0478(3) Uani 1 1 d .
Cl3 Cl 0.81210(9) -0.10033(17) 0.15712(10) 0.0732(5) Uani 1 1 d .
N1 N 0.8117(2) 0.3233(5) 0.2155(2) 0.0367(10) Uani 1 1 d .
O1 O 0.76853(18) 0.2355(4) 0.1723(2) 0.0476(9) Uani 1 1 d .
C6 C 0.9492(3) 0.6018(5) 0.3473(3) 0.0361(11) Uani 1 1 d .
C1 C 0.8579(3) 0.2773(5) 0.2753(3) 0.0469(14) Uani 1 1 d .
H1 H 0.86 0.1843 0.2872 0.056 Uiso 1 1 calc R
N2 N 1.0394(3) 0.7793(6) 0.4317(3) 0.0608(15) Uani 1 1 d .
C4 C 0.8058(3) 0.4582(6) 0.1988(3) 0.0415(13) Uani 1 1 d .
H4 H 0.7722 0.4889 0.1583 0.05 Uiso 1 1 calc R
C3 C 0.8999(3) 0.5053(5) 0.3026(3) 0.0324(11) Uani 1 1 d .
C7 C 1.0118(3) 0.5580(6) 0.3899(3) 0.0486(14) Uani 1 1 d .
H7 H 1.0234 0.4656 0.3896 0.058 Uiso 1 1 calc R
C8 C 1.0561(3) 0.6464(7) 0.4318(4) 0.0557(16) Uani 1 1 d .
H8 H 1.0978 0.6153 0.4603 0.067 Uiso 1 1 calc R
C5 C 0.8494(3) 0.5496(5) 0.2418(3) 0.0385(12) Uani 1 1 d .
H5 H 0.8453 0.6425 0.2301 0.046 Uiso 1 1 calc R
C9 C 0.9349(3) 0.7413(6) 0.3500(4) 0.0538(15) Uani 1 1 d .
H9 H 0.8937 0.7758 0.3222 0.065 Uiso 1 1 calc R
C2 C 0.9019(3) 0.3661(5) 0.3187(3) 0.0439(14) Uani 1 1 d .
H2 H 0.934 0.3327 0.36 0.053 Uiso 1 1 calc R
C10 C 0.9806(4) 0.8276(6) 0.3929(4) 0.0652(19) Uani 1 1 d .
H10 H 0.9703 0.9205 0.3949 0.078 Uiso 1 1 calc R
H3 H 1.069(3) 0.837(6) 0.461(4) 0.07(2) 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 0 '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 0.006 '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_3
O1 Bi1 Cl3 87.62(10) .
O1 Bi1 Cl4 93.41(9) .
Cl3 Bi1 Cl4 90.95(6) .
O1 Bi1 Cl2 172.45(9) .
Cl3 Bi1 Cl2 88.46(5) .
Cl4 Bi1 Cl2 93.11(5) .
O1 Bi1 Cl1 81.08(9) .
Cl3 Bi1 Cl1 99.13(5) .
Cl4 Bi1 Cl1 168.25(5) .
Cl2 Bi1 Cl1 93.18(4) .
O1 Bi1 Cl1 82.70(9) 7_655
Cl3 Bi1 Cl1 167.82(5) 7_655
Cl4 Bi1 Cl1 82.31(4) 7_655
Cl2 Bi1 Cl1 101.96(4) 7_655
Cl1 Bi1 Cl1 86.69(4) 7_655
Bi1 Cl1 Bi1 93.31(4) 7_655
C1 N1 O1 120.2(4) .
C1 N1 C4 121.2(5) .
O1 N1 C4 118.6(4) .
N1 O1 Bi1 118.4(2) .
C7 C6 C9 116.4(5) .
C7 C6 C3 121.7(5) .
C9 C6 C3 121.9(5) .
N1 C1 C2 120.1(5) .
N1 C1 H1 120 .
C2 C1 H1 120 .
C10 N2 C8 122.5(6) .
C10 N2 H3 119(4) .
C8 N2 H3 118(4) .
N1 C4 C5 119.8(5) .
N1 C4 H4 120.1 .
C5 C4 H4 120.1 .
C2 C3 C5 116.7(5) .
C2 C3 C6 121.8(5) .
C5 C3 C6 121.5(4) .
C8 C7 C6 121.5(6) .
C8 C7 H7 119.2 .
C6 C7 H7 119.2 .
N2 C8 C7 119.1(6) .
N2 C8 H8 120.4 .
C7 C8 H8 120.4 .
C4 C5 C3 120.8(5) .
C4 C5 H5 119.6 .
C3 C5 H5 119.6 .
C10 C9 C6 120.7(6) .
C10 C9 H9 119.6 .
C6 C9 H9 119.6 .
C1 C2 C3 121.4(5) .
C1 C2 H2 119.3 .
C3 C2 H2 119.3 .
N2 C10 C9 119.8(6) .
N2 C10 H10 120.1 .
C9 C10 H10 120.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O1 2.365(3) .
Bi1 Cl3 2.5415(14) .
Bi1 Cl4 2.5904(14) .
Bi1 Cl2 2.7191(13) .
Bi1 Cl1 2.8114(13) .
Bi1 Cl1 2.9493(14) 7_655
Cl1 Bi1 2.9493(14) 7_655
N1 C1 1.336(6) .
N1 O1 1.345(5) .
N1 C4 1.350(6) .
C6 C7 1.387(7) .
C6 C9 1.391(7) .
C6 C3 1.476(7) .
C1 C2 1.360(7) .
C1 H1 0.93 .
N2 C10 1.318(8) .
N2 C8 1.337(7) .
N2 H3 0.91(6) .
C4 C5 1.370(7) .
C4 H4 0.93 .
C3 C2 1.387(6) .
C3 C5 1.391(7) .
C7 C8 1.350(7) .
C7 H7 0.93 .
C8 H8 0.93 .
C5 H5 0.93 .
C9 C10 1.359(8) .
C9 H9 0.93 .
C2 H2 0.93 .
C10 H10 0.93 .
