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_7719086
_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 H31 Cl N O P Pd'
_chemical_formula_sum            'C31 H31 Cl N O P Pd'
_chemical_formula_weight         606.39
_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
_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                 96.442(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7141(6)
_cell_length_b                   14.3721(9)
_cell_length_c                   19.5667(11)
_cell_measurement_reflns_used    6585
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.25
_cell_volume                     2714.5(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47197
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.762
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.6929.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       needle
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0515P)^2^+7.5265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3638
_reflns_number_total             4781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01353d2.cif
_cod_data_source_block           complex_1
_cod_depositor_comments
'Adding full bibliography for 7719085--7719094.cif.'
_cod_database_code               7719086
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.917
_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 Ternary CH refined with riding coordinates:
 C17(H17), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C5(H5), C4(H4), C3(H3), C2(H2), C25(H25),
 C24(H24), C23(H23), C22(H22), C21(H21), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_shelx_res_checksum              71739
_shelx_hkl_checksum              86857
_olex2_submission_special_instructions 'No special instructions were received'