Expedient radical phosphonylations <i>via</i> ligand to metal charge transfer on bismuth.
Patra, Jatin; Nair, Akshay M.; Volla, Chandra M. R.; Chemical science 15 (2024) 7136–7143; doi:10.1039/d4sc00692e

data_1571413
_publ_section_title
;
 Expedient radical phosphonylations <i>via</i> ligand to metal charge
 transfer on bismuth.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              7136
_journal_page_last               7143
_journal_paper_doi               10.1039/d4sc00692e
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C32 H23 O3 P, 1[CHCl3]'
_chemical_formula_sum            'C33 H24 Cl3 O3 P'
_chemical_formula_weight         605.84
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-10-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-20 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.713(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6015(3)
_cell_length_b                   16.8085(2)
_cell_length_c                   14.3074(3)
_cell_measurement_reflns_used    15170
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.5640
_cell_measurement_theta_min      1.8220
_cell_volume                     2795.47(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -114.56  77.44   1.00    4.00  77.88 -12.98  31.50    --   192
  2  \f   -177.73   6.27   1.00    4.00   9.41 -12.98 -31.50    --   184
  3  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25-135.92  124
  4  \w    -55.98   0.02   1.00    4.00    --   -6.49  94.56 -34.84   56
  5  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25 -84.92  124
  6  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25 173.08  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0437662000
_diffrn_orient_matrix_UB_12      0.0061889000
_diffrn_orient_matrix_UB_13      0.0188934000
_diffrn_orient_matrix_UB_21      0.0327415000
_diffrn_orient_matrix_UB_22      0.0312201000
_diffrn_orient_matrix_UB_23      0.0312080000
_diffrn_orient_matrix_UB_31      -0.0271431000
_diffrn_orient_matrix_UB_32      0.0277070000
_diffrn_orient_matrix_UB_33      -0.0394538000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            53767
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.962
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+6.8445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4210
_reflns_number_total             4896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00692e2.cif
_cod_data_source_block           cmrv_jp_395_a_autored
_cod_depositor_comments
'Adding full bibliography for 1571411--1571413.cif.'
_cod_database_code               1571413
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 90.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.56
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013)
2.c Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              59730
_shelx_fab_checksum              62321
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.567