Aryl bismuth phosphinates [BiAr<sub>2</sub>(O(O)PRR')]: structure-activity relationships for antibacterial activity and cytotoxicity.
Herdman, Megan E.; Werrett, Melissa V.; Andrews, Philip C.; Dalton transactions (Cambridge, England : 2003) 51 (2022) 9323–9335; doi:10.1039/d2dt00346e

data_7710328
_publ_section_title
;
 Aryl bismuth phosphinates [BiAr<sub>2</sub>(O(O)PRR')]:
 structure-activity relationships for antibacterial activity and
 cytotoxicity.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9323
_journal_page_last               9335
_journal_paper_doi               10.1039/d2dt00346e
_journal_volume                  51
_journal_year                    2022
_chemical_formula_moiety         'C20 H20 Bi O2 P'
_chemical_formula_sum            'C20 H20 Bi O2 P'
_chemical_formula_weight         532.31
_chemical_name_systematic
catena-((\m-phenylphosphinate)-bis(4-tolyl)-bismuth)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.783(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7237(4)
_cell_length_b                   9.2659(2)
_cell_length_c                   23.2109(5)
_cell_measurement_reflns_used    12841
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      79.5710
_cell_measurement_theta_min      3.9140
_cell_volume                     3834.50(15)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00   0.00   0.50    0.42    --  -47.61 108.00 153.00  164
  2  \w     21.00  86.00   0.50    0.42    --   47.61-108.00  57.00  130
  3  \w    -82.00 -19.00   0.50    1.67    --  -91.75 108.00 153.00  126
  4  \w   -163.00 -82.00   0.50    1.67    --  -91.75-108.00  57.00  162
  5  \w    104.00 178.00   0.50    1.67    --  113.25 108.00 153.00  148
  6  \w     42.00 108.00   0.50    1.67    --  113.25-108.00  57.00  132
  7  \w   -120.00 -73.00   0.50    0.42    --  -47.61-125.00 -60.00   94
  8  \w   -120.00 -73.00   0.50    0.42    --  -47.61-125.00-150.00   94
  9  \w   -120.00 -73.00   0.50    0.42    --  -47.61-125.00 -90.00   94
 10  \w   -120.00 -73.00   0.50    0.42    --  -47.61-125.00 120.00   94
 11  \w    -25.00  61.00   0.50    0.42    --   47.61 -38.00 -90.00  172
 12  \w   -163.00 -79.00   0.50    1.67    --  -91.75 -45.00  90.00  168
 13  \w     42.00  76.00   0.50    1.67    --  113.25 -45.00-150.00   68
 14  \w     42.00  76.00   0.50    1.67    --  113.25 -45.00 150.00   68
 15  \w     39.00  66.00   0.50    1.67    --  113.25 -30.00 -60.00   54
 16  \w     39.00  66.00   0.50    1.67    --  113.25 -30.00-150.00   54
 17  \w     39.00  66.00   0.50    1.67    --  113.25 -30.00   0.00   54
 18  \w     42.00 106.00   0.50    1.67    --  113.25 -94.00  90.00  128
 19  \w     42.00  76.00   0.50    1.67    --  113.25 -45.00 -60.00   68
 20  \w     95.00 178.00   0.50    1.67    --  113.25 125.00 -60.00  166
 21  \w     39.00  66.00   0.50    1.67    --  113.25 -30.00  30.00   54
 22  \w     42.00  76.00   0.50    1.67    --  113.25 -45.00  60.00   68
 23  \w     42.00 111.00   0.50    1.67    --  113.25-125.00-180.00  138
 24  \w     42.00  76.00   0.50    1.67    --  113.25 -45.00 120.00   68
 25  \w     39.00  64.00   0.50    1.67    --  113.25 -30.00-180.00   50
 26  \w     45.00  74.00   0.50    1.67    --  113.25 -45.00 -90.00   58
 27  \w     42.00  75.00   0.50    1.67    --  113.25 -45.00   0.00   66
 28  \w     85.00 129.00   0.50    1.67    --  113.25 -61.00  30.00   88
 29  \w     42.00  70.00   0.50    1.67    --  113.25 -45.00-180.00   56
 30  \w     40.00  65.00   0.50    1.67    --  113.25 -30.00 120.00   50
 31  \w     43.00 106.00   0.50    1.67    --  113.25 -95.00  97.04  126
 32  \w     44.00  70.00   0.50    1.67    --  113.25 -61.00  60.00   52
 33  \w     94.00 121.00   0.50    1.67    --  113.25 -61.00  60.00   54
 34  \w     46.00  76.00   0.50    1.67    --  113.25 -45.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105536000
_diffrn_orient_matrix_UB_12      0.0426987000
_diffrn_orient_matrix_UB_13      0.0610304000
_diffrn_orient_matrix_UB_21      0.0170557000
_diffrn_orient_matrix_UB_22      -0.1563922000
_diffrn_orient_matrix_UB_23      0.0225989000
_diffrn_orient_matrix_UB_31      0.0840289000
_diffrn_orient_matrix_UB_32      0.0370826000
_diffrn_orient_matrix_UB_33      0.0249009000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20042
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.977
_diffrn_reflns_theta_min         4.000
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_description       needle
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.472
_refine_diff_density_min         -2.737
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0386
_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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3574
_reflns_number_total             4101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt00346e2.cif
_cod_data_source_block           mh_biptolp_auto
_cod_depositor_comments
'Adding full bibliography for 7710326--7710330.cif.'
_cod_database_code               7710328
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'Bi C H O P S'
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.397
_diffrn_oxdiff_digest_frames
;
016f1255aa96474646f60c335c7c719361000493d08
;
_diffrn_oxdiff_digest_hkl
;
017b70b7874224d4282e29c0731b1971c77843
;
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C2(H2), C3(H3), C5(H5), C20(H20), C16(H16), C9(H9),
 C12(H12), C10(H10), C18(H18), C19(H19), C17(H17)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              87618
_shelx_hkl_checksum              52754
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.683
_oxdiff_exptl_absorpt_empirical_full_min 0.710