#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:15:18 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229047 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/17/7231701.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_7231701
loop_
_publ_author_name
'Adonin, Sergey A.'
'Gorokh, Igor D.'
'Novikov, Alexander S.'
'Samsonenko, Denis G.'
'Yushina, Irina V.'
'Sokolov, Maxim N.'
'Fedin, Vladimir P.'
_publ_section_title
;
 Halobismuthates with halopyridinium cations: appearance or non-appearance
 of unusual colouring
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              7766
_journal_paper_doi               10.1039/C8CE01749B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C10 H9 Bi Br2 Cl4 N2'
_chemical_formula_weight         667.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.272(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.12752(19)
_cell_length_b                   17.6661(4)
_cell_length_c                   13.3872(3)
_cell_measurement_reflns_used    4174
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      3.90
_cell_volume                     1682.91(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         29.058
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    15.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.636
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.927
_refine_diff_density_min         -1.583
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0174P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3252
_reflns_number_total             3763
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c8ce01749b2.cif
_cod_data_source_block           IG296white
_cod_depositor_comments
'Adding full bibliography for 7231701--7231709.cif.'
_cod_original_cell_volume        1682.90(7)
_cod_database_code               7231701
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.070
_shelx_estimated_absorpt_t_max   0.163
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Bi1 Bi 0.75064(2) 0.43686(2) 0.01105(2) 0.01139(7) Uani 1 1 d . .
Cl1 Cl 0.60826(18) 0.32593(7) -0.08675(10) 0.0181(3) Uani 1 1 d . .
Cl2 Cl 0.89943(19) 0.35418(8) 0.14732(10) 0.0222(3) Uani 1 1 d . .
Cl3 Cl 0.94407(18) 0.57027(7) 0.10169(10) 0.0210(3) Uani 1 1 d . .
Cl4 Cl 0.55299(17) 0.54793(7) -0.12328(9) 0.0164(3) Uani 1 1 d . .
N1 N 0.7346(6) 0.5173(2) 0.4561(3) 0.0166(10) Uani 1 1 d . .
Br1 Br 0.82643(8) 0.58307(3) 0.63939(4) 0.02468(14) Uani 1 1 d . .
C11 C 0.7470(6) 0.5839(3) 0.5020(4) 0.0154(12) Uani 1 1 d . .
C12 C 0.7076(7) 0.6529(3) 0.4557(4) 0.0185(12) Uani 1 1 d . .
H12 H 0.718754 0.699198 0.491758 0.022 Uiso 1 1 calc R U
C13 C 0.6521(7) 0.6517(3) 0.3560(4) 0.0199(12) Uani 1 1 d . .
H13 H 0.624689 0.697720 0.321447 0.024 Uiso 1 1 calc R U
C14 C 0.6363(7) 0.5842(3) 0.3063(4) 0.0201(12) Uani 1 1 d . .
H14 H 0.596711 0.582680 0.237312 0.024 Uiso 1 1 calc R U
C15 C 0.6792(8) 0.5179(3) 0.3582(4) 0.0213(13) Uani 1 1 d . .
H15 H 0.669066 0.471052 0.323434 0.026 Uiso 1 1 calc R U
N2 N 0.7940(5) 0.3746(2) 0.5541(3) 0.0146(10) Uani 1 1 d . .
H2 H 0.780880 0.417472 0.520935 0.018 Uiso 1 1 calc R U
Br2 Br 0.68969(8) 0.31274(3) 0.36978(4) 0.02428(14) Uani 1 1 d . .
C21 C 0.7590(6) 0.3084(3) 0.5058(4) 0.0151(11) Uani 1 1 d . .
C22 C 0.7748(7) 0.2413(3) 0.5558(4) 0.0177(12) Uani 1 1 d . .
H22 H 0.746877 0.194932 0.522316 0.021 Uiso 1 1 calc R U
C23 C 0.8325(7) 0.2421(3) 0.6569(4) 0.0191(12) Uani 1 1 d . .
H23 H 0.846113 0.195905 0.692974 0.023 Uiso 1 1 calc R U
C24 C 0.8700(7) 0.3103(3) 0.7045(4) 0.0186(12) Uani 1 1 d . .
H24 H 0.910384 0.311497 0.773382 0.022 Uiso 1 1 calc R U
C25 C 0.8481(7) 0.3761(3) 0.6512(4) 0.0162(12) Uani 1 1 d . .
H25 H 0.871750 0.423264 0.683518 0.019 Uiso 1 1 calc R U
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_publ_flag
Cl1 Bi1 Cl3 89.26(4) . 3_765 yes
Cl1 Bi1 Cl3 172.53(4) . . yes
Cl1 Bi1 Cl4 92.07(4) . . yes
Cl1 Bi1 Cl4 93.09(4) . 3_665 yes
Cl2 Bi1 Cl1 93.74(4) . . yes
Cl2 Bi1 Cl3 89.87(4) . . yes
Cl2 Bi1 Cl3 93.32(4) . 3_765 yes
Cl2 Bi1 Cl4 88.43(4) . 3_665 yes
Cl2 Bi1 Cl4 171.08(4) . . yes
Cl3 Bi1 Cl3 84.01(4) 3_765 . yes
Cl3 Bi1 Cl4 85.16(4) . . yes
Cl3 Bi1 Cl4 93.53(4) 3_765 . yes
Cl4 Bi1 Cl3 93.54(4) 3_665 . yes
Cl4 Bi1 Cl3 176.98(4) 3_665 3_765 yes
Cl4 Bi1 Cl4 84.49(4) 3_665 . yes
Bi1 Cl3 Bi1 95.99(4) 3_765 . yes
Bi1 Cl4 Bi1 95.51(4) 3_665 . yes
C11 N1 C15 116.9(5) . . ?
N1 C11 Br1 116.8(4) . . ?
N1 C11 C12 124.4(5) . . ?
C12 C11 Br1 118.8(4) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.4(5) . . ?
C13 C12 H12 121.3 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(5) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.5(5) . . ?
N1 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C21 N2 H2 119.4 . . ?
C25 N2 H2 119.4 . . ?
C25 N2 C21 121.1(5) . . ?
N2 C21 Br2 117.6(4) . . ?
N2 C21 C22 120.6(5) . . ?
C22 C21 Br2 121.8(4) . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(5) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.1(5) . . ?
C25 C24 H24 120.5 . . ?
N2 C25 C24 120.7(5) . . ?
N2 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
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
Bi1 Cl1 2.5362(12) . yes
Bi1 Cl2 2.5229(13) . yes
Bi1 Cl3 2.7209(13) 3_765 yes
Bi1 Cl3 2.9559(13) . yes
Bi1 Cl4 2.7173(13) 3_665 yes
Bi1 Cl4 2.9630(13) . yes
N1 C11 1.327(7) . ?
N1 C15 1.347(6) . ?
Br1 C11 1.894(5) . ?
C11 C12 1.390(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.353(6) . ?
N2 C25 1.334(6) . ?
Br2 C21 1.861(5) . ?
C21 C22 1.362(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(7) . ?
C25 H25 0.9500 . ?
