Palladium-catalysed C–H arylation of benzophospholes with aryl halides
Xu, Shibo; Nishimura, Kazutoshi; Saito, Kosuke; Hirano, Koji; Miura, Masahiro; Chemical Science  (2022) –; doi:10.1039/D2SC04311D

data_1567590
_publ_section_title
;
 Palladium-catalysed C--H arylation of benzophospholes with aryl halides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04311D
_journal_year                    2022
_chemical_formula_moiety         'C28 H18 O P, 2(C H Cl3)'
_chemical_formula_sum            'C30 H20 Cl6 O P'
_chemical_formula_weight         640.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                73.955(2)
_cell_angle_beta                 87.469(2)
_cell_angle_gamma                73.633(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0941(3)
_cell_length_b                   10.4249(3)
_cell_length_c                   15.3161(3)
_cell_measurement_reflns_used    9019
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0410
_cell_measurement_theta_min      2.0970
_cell_volume                     1485.17(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.827
_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    -31.00  66.00   0.50    1.21    --   -8.66  57.00  30.00  194
  2  \w     -1.00  24.00   0.50    1.21    --    9.13 -57.00  90.00   50
  3  \w    -25.00   6.00   0.50    1.21    --   -8.66 -81.00 -26.00   62
  4  \w    -29.00  41.00   0.50    1.21    --   -8.66  81.00  95.00  140
  5  \w    -33.00   2.00   0.50    1.21    --    9.13 109.00 -20.11   70
  6  \w    -41.00 -15.00   0.50    1.21    --    9.13 -57.00  90.00   52
  7  \w    -83.00 -45.00   0.50    1.21    --   -8.66 -81.00 -26.00   76
  8  \w    -26.00  49.00   0.50    1.21    --    9.13 -99.00 -30.00  150
  9  \w    -26.00  25.00   0.50    1.21    --   -8.66 -99.00-180.00  102
 10  \w    -16.00   9.00   0.50    1.21    --    9.13 -99.00-180.00   50
 11  \w    -25.00  46.00   0.50    1.21    --    9.13 -99.00-120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442975000
_diffrn_orient_matrix_UB_12      0.0008159000
_diffrn_orient_matrix_UB_13      0.0344042000
_diffrn_orient_matrix_UB_21      0.0014522000
_diffrn_orient_matrix_UB_22      -0.0694306000
_diffrn_orient_matrix_UB_23      0.0232892000
_diffrn_orient_matrix_UB_31      0.0583641000
_diffrn_orient_matrix_UB_32      -0.0248980000
_diffrn_orient_matrix_UB_33      -0.0244778000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23449
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.050
_diffrn_reflns_theta_min         2.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.431
_exptl_crystal_description       prism
_exptl_crystal_F_000             650
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.219
_refine_diff_density_max         1.395
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0797P)^2^+1.0362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5103
_reflns_number_total             7207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04311d1.cif
_cod_data_source_block           xu_220307
_cod_database_code               1567590
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C60 H40 O2 P2 Cl12'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C36(H36), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C29(H29), C26(H26), C17(H17), C8(H8), C5(H5), C18(H18),
 C21(H21), C6(H6), C7(H7), C20(H20), C19(H19), C15(H15), C11(H11), C13(H13),
 C14(H14), C12(H12)
;
_shelx_res_checksum              87323
_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 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.769