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_7719090
_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         'C52 H42 N O2 P, C2 H3 N'
_chemical_formula_sum            'C54 H45 N2 O2 P'
_chemical_formula_weight         784.89
_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   mixed
_atom_sites_solution_primary     dual
_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                71.863(3)
_cell_angle_beta                 78.627(3)
_cell_angle_gamma                77.250(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3353(3)
_cell_length_b                   16.5259(6)
_cell_length_c                   16.8581(6)
_cell_measurement_reflns_used    8511
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      24.5910
_cell_measurement_theta_min      2.0620
_cell_volume                     2131.60(14)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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  \f    -10.27 349.73   0.50    4.00  72.47 -18.39  31.50    --   720
  2  \w    -83.02  -0.02   0.50    4.00    --  -27.59  94.56 -34.84  166
  3  \w    -73.83   0.17   0.50    4.00    --  -18.39  94.56 145.16  148
  4  \w   -119.86  16.64   0.50    4.00    --  -18.39 -59.25 173.08  273
  5  \w   -119.86  16.64   0.50    4.00    --  -18.39 -59.25 -33.92  273
  6  \w    -73.83   0.17   0.50    4.00    --  -18.39  94.56  73.16  148
  7  \f   -349.73  10.27   0.50    4.00  16.75 -18.39 -31.50    --   720
  8  \w    -73.83   0.17   0.50    4.00    --  -18.39  94.56   1.16  148
  9  \w   -119.86  16.64   0.50    4.00    --  -18.39 -59.25  20.08  273
;
_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      -0.0865573000
_diffrn_orient_matrix_UB_12      0.0042502000
_diffrn_orient_matrix_UB_13      -0.0000020000
_diffrn_orient_matrix_UB_21      -0.0073495000
_diffrn_orient_matrix_UB_22      -0.0280113000
_diffrn_orient_matrix_UB_23      0.0415889000
_diffrn_orient_matrix_UB_31      -0.0146661000
_diffrn_orient_matrix_UB_32      0.0360359000
_diffrn_orient_matrix_UB_33      0.0164021000
_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  0.0832
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61958
_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         1.560
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60874
_exptl_absorpt_correction_type   multi-scan
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.058
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0771P)^2^+1.2942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6079
_reflns_number_total             7487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01353d2.cif
_cod_data_source_block           Compound_7
_cod_depositor_comments
'Adding full bibliography for 7719085--7719094.cif.'
_cod_database_code               7719090
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C26(H26), C39(H39)
1.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C34(H34), C38(H38), C41(H41), C32(H32), C35(H35),
 C47(H47), C37(H37), C36(H36), C28(H28), C3(H3), C6(H6), C31(H31), C4(H4),
 C19(H19), C15(H15), C42(H42), C45(H45), C5(H5), C51(H51), C13(H13), C30(H30),
 C48(H48), C9(H9), C17(H17), C43(H43), C18(H18), C29(H29), C16(H16), C50(H50),
 C49(H49), C12(H12), C11(H11), C44(H44), C10(H10)
1.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C53(H53A,H53B,H53C)
;
_shelx_res_checksum              8912
_shelx_hkl_checksum              98075
_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 3.076
_oxdiff_exptl_absorpt_empirical_full_min 0.477