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_1567591
_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         'C22 H19 O P'
_chemical_formula_sum            'C22 H19 O P'
_chemical_formula_weight         330.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-21 deposited with the CCDC.	2022-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.369(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5743(3)
_cell_length_b                   11.3680(2)
_cell_length_c                   11.7601(2)
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.4350
_cell_measurement_theta_min      3.4870
_cell_volume                     1678.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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    -47.00 -22.00   0.50    0.05    --  -42.93  89.00 118.00   50
  2  \w    -96.00 -23.00   0.50    0.05    --  -42.93 125.00  90.00  146
  3  \w    -76.00 -35.00   0.50    0.05    -- -106.00 125.00 -30.00   82
  4  \w    -85.00 -59.00   0.50    0.05    -- -106.00 125.00-120.00   52
  5  \w   -128.00 -28.00   0.50    0.05    -- -106.00  37.00-180.00  200
  6  \w    -85.00 -26.00   0.50    0.05    -- -106.00  19.00-150.00  118
  7  \w    -63.00 -26.00   0.50    0.05    -- -106.00  19.00 -60.00   74
  8  \w   -108.00 -83.00   0.50    0.05    -- -106.00 -57.00  30.00   50
  9  \w   -127.00-102.00   0.50    0.05    -- -106.00 -89.00   2.00   50
 10  \w   -130.00 -84.00   0.50    0.05    -- -106.00 -99.00  60.00   92
 11  \w   -115.00 -70.00   0.50    0.05    --  -42.93-125.00  60.00   90
 12  \w   -115.00 -84.00   0.50    0.05    --  -42.93-125.00 -30.00   62
 13  \w    -30.00  58.00   0.50    0.05    --   42.93 -89.00   2.00  176
 14  \w     32.00  57.00   0.50    0.05    --   76.50 -89.00   2.00   50
 15  \w     89.00 114.00   0.50    0.05    --   76.50  89.00 118.00   50
 16  \w     72.00 117.00   0.50    0.05    --   42.93 125.00  30.00   90
 17  \w     80.00 115.00   0.50    0.05    --   42.93 125.00-150.00   70
 18  \w    -95.00 -69.00   0.50    0.05    -- -106.00  77.00 150.00   52
 19  \w   -118.00 -61.00   0.50    0.05    -- -106.00  89.00 118.00  114
 20  \w   -126.00 -28.00   0.50    0.05    -- -106.00  37.00  30.00  196
 21  \w   -131.00-106.00   0.50    0.05    -- -106.00  77.00 150.00   50
 22  \w   -129.00 -50.00   0.50    0.05    -- -106.00  77.00  90.00  158
 23  \w   -132.00-107.00   0.50    0.05    -- -106.00  19.00 -60.00   50
 24  \w   -114.00 -40.00   0.50    0.05    -- -106.00  77.00-120.00  148
 25  \w   -135.00-106.00   0.50    0.05    -- -106.00  19.00-150.00   58
 26  \w   -170.00-144.00   0.50    0.05    -- -106.00 -57.00  30.00   52
 27  \w   -170.00-135.00   0.50    0.05    -- -106.00 -37.00  60.00   70
 28  \w   -173.00-133.00   0.50    0.05    -- -106.00 -99.00  60.00   80
;
_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      0.0622882000
_diffrn_orient_matrix_UB_12      -0.0600299000
_diffrn_orient_matrix_UB_13      -0.0929116000
_diffrn_orient_matrix_UB_21      -0.0747269000
_diffrn_orient_matrix_UB_22      -0.1072222000
_diffrn_orient_matrix_UB_23      0.0026264000
_diffrn_orient_matrix_UB_31      -0.0747993000
_diffrn_orient_matrix_UB_32      0.0571935000
_diffrn_orient_matrix_UB_33      -0.0926215000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13235
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.194
_diffrn_reflns_theta_min         3.521
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0543P)^2^+0.7919P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3075
_reflns_number_total             3366
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04311d1.cif
_cod_data_source_block           201205_saito_1
_cod_database_code               1567591
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C22 H19 P O'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C8(H8), C11(H11), C15(H15), C18(H18), C17(H17), C20(H20), C5(H5), C2(H2),
 C6(H6), C13(H13), C21(H21), C14(H14), C12(H12)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              60032
_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 1.518
_oxdiff_exptl_absorpt_empirical_full_min 0.633