Sterically hindered P,N-type amidophosphines {{(<i>o</i>-PPh<sub>2</sub>)C<sub>6</sub>H<sub>4</sub>}C(O)NH(R)}: synthesis, transition metal chemistry, and catalytic activity in stereoselective Heck coupling of aryl chlorides.
Sabharwal, Gazal; Dwivedi, Khilesh C.; Balakrishna, Maravanji S.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 11551–11562; doi:10.1039/d5dt01353d

data_7719085
_publ_section_title
;
 Sterically hindered P,N-type amidophosphines
 {{(<i>o</i>-PPh<sub>2</sub>)C<sub>6</sub>H<sub>4</sub>}C(O)NH(R)}:
 synthesis, transition metal chemistry, and catalytic activity in
 stereoselective Heck coupling of aryl chlorides.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11551
_journal_page_last               11562
_journal_paper_doi               10.1039/d5dt01353d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C31 H32 N O P'
_chemical_formula_sum            'C31 H32 N O P'
_chemical_formula_weight         465.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-06-04
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-04 deposited with the CCDC.	2025-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1282(8)
_cell_length_b                   11.1151(5)
_cell_length_c                   39.4454(16)
_cell_measurement_reflns_used    3727
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      22.1070
_cell_measurement_theta_min      2.0010
_cell_volume                     5317.5(5)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -115.72  16.28   0.50    2.00    --  -15.82 -59.25  20.08  264
  2  \f    107.79 252.29   0.50    2.00  16.40 -15.82 -59.25    --   289
;
_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      0.0129545000
_diffrn_orient_matrix_UB_12      0.0235727000
_diffrn_orient_matrix_UB_13      -0.0162275000
_diffrn_orient_matrix_UB_21      -0.0495332000
_diffrn_orient_matrix_UB_22      -0.0244509000
_diffrn_orient_matrix_UB_23      -0.0065941000
_diffrn_orient_matrix_UB_31      -0.0281119000
_diffrn_orient_matrix_UB_32      0.0540898000
_diffrn_orient_matrix_UB_33      0.0040991000
_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  0.0854
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            32661
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.971
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62121
_exptl_absorpt_correction_type   empirical
_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            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0464P)^2^+2.0932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3335
_reflns_number_total             4684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01353d2.cif
_cod_data_source_block           Ligand_L1
_cod_depositor_comments
'Adding full bibliography for 7719085--7719094.cif.'
_cod_database_code               7719085
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C26(H26), C29(H29)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C24(H24), C22(H22), C23(H23), C4(H4), C9(H9), C3(H3),
 C13(H13), C10(H10), C11(H11), C19(H19), C12(H12), C18(H18), C15(H15), C17(H17),
  C16(H16)
1.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C27(H27A,H27B,H27C), C31(H31A,H31B,
 H31C)
;
_shelx_res_checksum              35738
_shelx_hkl_checksum              97083
_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 1.585
_oxdiff_exptl_absorpt_empirical_full_min 0.671