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_7719092
_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 Ag N O P, Cl O4, C H2 Cl2, C H2 Cl'
_chemical_formula_sum            'C33 H36 Ag Cl4 N O5 P'
_chemical_formula_weight         807.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 91.8180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1281(2)
_cell_length_b                   21.3078(3)
_cell_length_c                   24.5213(4)
_cell_measurement_reflns_used    16954
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.6040
_cell_measurement_theta_min      1.8480
_cell_volume                     6855.91(18)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    1.00    --  -15.82 -59.25-135.92  264
  2  \w   -115.73  16.27   0.50    1.00    --  -15.82 -59.25  20.08  264
  3  \f   -130.56  94.44   0.50    1.00  75.04 -15.82  31.50    --   450
  4  \f    174.27 357.77   0.50    1.00  13.01 -15.82 -31.50    --   367
  5  \w   -115.72  16.28   0.50    1.00    --  -15.82 -59.25 -84.92  264
;
_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      0.0436317000
_diffrn_orient_matrix_UB_12      0.0080303000
_diffrn_orient_matrix_UB_13      0.0163011000
_diffrn_orient_matrix_UB_21      -0.0032594000
_diffrn_orient_matrix_UB_22      0.0313297000
_diffrn_orient_matrix_UB_23      -0.0096449000
_diffrn_orient_matrix_UB_31      -0.0317435000
_diffrn_orient_matrix_UB_32      0.0078469000
_diffrn_orient_matrix_UB_33      0.0218890000
_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  0.0565
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            60327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.983
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61930
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             3288
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.041
_refine_diff_density_max         1.929
_refine_diff_density_min         -1.985
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0879P)^2^+64.8194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5355
_reflns_number_total             6036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01353d2.cif
_cod_data_source_block           Complex_6
_cod_depositor_comments
'Adding full bibliography for 7719085--7719094.cif.'
_cod_database_code               7719092
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 92.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.36
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(C33) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
2.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C30(H30), C24(H24), C31(H31), C23(H23), C2(H2), C12(H12), C4(H4),
 C5(H5), C10(H10), C3(H3), C11(H11), C29(H29), C21(H21), C22(H22), C27(H27),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              63118
_shelx_hkl_checksum              62157
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.627