Self-association of diphenylpnictoginic acids in solution and solid state: covalent vs hydrogen bonding
Yakubenko, Artyom A.; Puzyk, Aleksandra M.; Korostelev, Vladislav O.; Mulloyarova, Valeriia V.; Tupikina, Elena Yu.; Tolstoy, Peter; Antonov, Alexander S.; Physical Chemistry Chemical Physics  (2022) –; doi:10.1039/D2CP00286H

data_7244600
_publ_section_title
;
 Self-association of diphenylpnictoginic acids in solution and solid
 state: covalent vs hydrogen bonding
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D2CP00286H
_journal_year                    2022
_chemical_formula_moiety         'C18 H15 Bi Cl2'
_chemical_formula_sum            'C18 H15 Bi Cl2'
_chemical_formula_weight         511.18
_chemical_melting_point          153.5(15)
_chemical_name_systematic        'Triphenylbismuth dichloride'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-11
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2021-10-08 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1006(3)
_cell_length_b                   17.0456(4)
_cell_length_c                   22.1478(5)
_cell_measurement_reflns_used    9025
_cell_measurement_temperature    100.00(2)
_cell_measurement_theta_max      34.5710
_cell_measurement_theta_min      3.2610
_cell_volume                     3435.68(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -102.00  -38.00   1.0000  200.5400
omega____ theta____ kappa____ phi______ frames
    -      -31.2658 -178.0000    0.0000 64

  2 omega  -71.00   26.00   1.0000  200.5400
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   19.0000  -90.0000 97

  3 omega   -6.00   46.00   1.0000  200.5400
omega____ theta____ kappa____ phi______ frames
    -       32.3596  -57.0000  -30.0000 52

  4 omega   -5.00   40.00   1.0000  200.5400
omega____ theta____ kappa____ phi______ frames
    -      -31.2658   38.0000  -30.0000 45

  5 omega  -58.00  -10.00   1.0000  200.5400
omega____ theta____ kappa____ phi______ frames
    -      -31.2658  -57.0000  150.0000 48
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0517632000
_diffrn_orient_matrix_UB_12      0.0201121000
_diffrn_orient_matrix_UB_13      -0.0182878000
_diffrn_orient_matrix_UB_21      -0.0518398000
_diffrn_orient_matrix_UB_22      -0.0013079000
_diffrn_orient_matrix_UB_23      0.0238866000
_diffrn_orient_matrix_UB_31      0.0268485000
_diffrn_orient_matrix_UB_32      0.0363795000
_diffrn_orient_matrix_UB_33      0.0109345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18050
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.561
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    10.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_description       prism
_exptl_crystal_F_000             1920
_exptl_crystal_recrystallization_method 'Solvent evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 2532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0111P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0361
_refine_ls_wR_factor_ref         0.0370
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                6214
_reflns_number_total             6672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cp00286h3.cif
_cod_data_source_block           15376_art-01
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '152-155' was changed to
'153.5(15)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7244600
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H11 Bi O2'
_shelx_estimated_absorpt_t_max   0.340
_shelx_estimated_absorpt_t_min   0.252
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C30(H30), C28(H28), C22(H22), C26(H26), C11(H11), C4(H4), C24(H24),
 C5(H5), C15(H15), C23(H23), C21(H21), C27(H27), C2(H2), C10(H10), C32(H32),
 C9(H9), C20(H20), C36(H36), C8(H8), C6(H6), C33(H33), C12(H12), C34(H34),
 C3(H3), C17(H17), C16(H16), C14(H14), C35(H35), C18(H18)
;
_shelx_res_checksum              45617
_olex2_submission_special_instructions 'No special instructions were received'