Ruthenium-NHC complex-catalyzed P(III)-directed C-H borylation of arylphosphines.
Thongpaen, Jompol; Manguin, Romane; Kittikool, Tanakorn; Camy, Aurèle; Roisnel, Thierry; Dorcet, Vincent; Yotphan, Sirilata; Canac, Yves; Mauduit, Marc; Baslé, Olivier; Chemical communications (Cambridge, England) 58 (2022) 12082–12085; doi:10.1039/d2cc03909e

data_7130811
_publ_section_title
;
 Ruthenium-NHC complex-catalyzed P(III)-directed C-H borylation of
 arylphosphines.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12082
_journal_page_last               12085
_journal_paper_doi               10.1039/d2cc03909e
_journal_volume                  58
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H29 Cl N2 O2 Ru'
_chemical_formula_sum            'C24 H29 Cl N2 O2 Ru'
_chemical_formula_weight         514.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-07-11 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.016(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1024(18)
_cell_length_b                   21.259(4)
_cell_length_c                   10.8649(19)
_cell_measurement_reflns_used    6662
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      2.27
_cell_measurement_wavelength     0.71073
_cell_volume                     2282.3(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0572793
_diffrn_orient_matrix_UB_12      -0.0376858
_diffrn_orient_matrix_UB_13      0.0289857
_diffrn_orient_matrix_UB_21      -0.0525800
_diffrn_orient_matrix_UB_22      -0.0249194
_diffrn_orient_matrix_UB_23      -0.0718810
_diffrn_orient_matrix_UB_31      0.0647808
_diffrn_orient_matrix_UB_32      0.0130958
_diffrn_orient_matrix_UB_33      -0.0533667
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1374
_diffrn_reflns_av_unetI/netI     0.1152
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43748
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.094
_diffrn_source_current           1.0
_diffrn_source_power             50.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.241
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         10425
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+16.3811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                7677
_reflns_number_total             10425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03909e2.cif
_cod_data_source_block           JT240Z
_cod_depositor_comments
'Adding full bibliography for 7130810--7130811.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130811
_shelx_res_checksum              56411
_shelx_hkl_checksum              84150