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_7719094
_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         'C66 H68 N2 O6 P2 Pd2'
_chemical_formula_sum            'C66 H68 N2 O6 P2 Pd2'
_chemical_formula_weight         1259.96
_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     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                 91.964(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1836(3)
_cell_length_b                   14.8154(2)
_cell_length_c                   19.1770(3)
_cell_measurement_reflns_used    17825
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      25.9170
_cell_measurement_theta_min      1.7010
_cell_volume                     5731.09(15)
_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  \f    -38.27 161.23   0.50    1.00  77.88 -12.98  31.50    --   399
  2  \w   -108.63  15.87   0.50    1.00    --  -12.98 -59.25 122.08  249
  3  \f   -108.21 123.79   0.50    1.00  16.12 -12.98 -59.25    --   464
  4  \w   -108.63  15.87   0.50    1.00    --  -12.98 -59.25  20.08  249
  5  \w   -108.63  15.87   0.50    1.00    --  -12.98 -59.25 173.08  249
  6  \f    -97.73  86.77   0.50    1.00   9.41 -12.98 -31.50    --   369
;
_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      -0.0066418000
_diffrn_orient_matrix_UB_12      -0.0412936000
_diffrn_orient_matrix_UB_13      -0.0175748000
_diffrn_orient_matrix_UB_21      0.0169008000
_diffrn_orient_matrix_UB_22      0.0160539000
_diffrn_orient_matrix_UB_23      -0.0293411000
_diffrn_orient_matrix_UB_31      0.0301339000
_diffrn_orient_matrix_UB_32      -0.0181433000
_diffrn_orient_matrix_UB_33      0.0140869000
_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  0.0952
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            142637
_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         1.705
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72079
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     713
_refine_ls_number_reflns         10087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0310P)^2^+4.4368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8070
_reflns_number_total             10087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01353d2.cif
_cod_data_source_block           Complex_2
_cod_depositor_comments
'Adding full bibliography for 7719085--7719094.cif.'
_cod_database_code               7719094
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C17(H17), C14(H14), C48(H48), C45(H45)
1.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C3(H3), C2(H2), C5(H5), C10(H10), C25(H25), C12(H12), C11(H11),
 C33(H33), C36(H36), C4(H4), C31(H31), C58(H58), C28(H28), C24(H24), C21(H21),
 C34(H34), C52(H52), C43(H43), C35(H35), C41(H41), C62(H62), C22(H22), C56(H56),
  C23(H23), C53(H53), C30(H30), C29(H29), C59(H59), C54(H54), C42(H42),
 C55(H55), C61(H61), C60(H60)
1.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C64(H64A,H64B,H64C), C18(H18A,H18B,H18C), C16(H16A,H16B,
 H16C), C15(H15A,H15B,H15C), C66(H66A,H66B,H66C), C50(H50A,H50B,H50C), C49(H49A,
 H49B,H49C), C47(H47A,H47B,H47C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              16315
_shelx_hkl_checksum              80527
_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 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.639