Chiral (phosphine)-(imidazoline) PCN pincer palladium(II) complexes: synthesis and application in asymmetric hydrophosphination of 2-alkenoylpyridines with diphenylphosphine
Huang, Jun-Jian; Zhang, Xiao-Qi; Yang, Jing-Jing; Gong, Jun-Fang; Song, Mao-Ping; Dalton Transactions  (2022) –; doi:10.1039/D2DT01078J

data_7710179
_publ_section_title
;
 Chiral (phosphine)-(imidazoline) PCN pincer palladium(II) complexes:
 synthesis and application in asymmetric hydrophosphination of
 2-alkenoylpyridines with diphenylphosphine
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01078J
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H32 Cl N2 O P Pd'
_chemical_formula_sum            'C41 H32 Cl N2 O P Pd'
_chemical_formula_weight         741.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.34262(12)
_cell_length_b                   14.76131(19)
_cell_length_c                   24.6818(3)
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0460
_cell_measurement_theta_min      4.6620
_cell_volume                     3403.85(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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    -54.00 -28.00   1.00    1.25    --  -33.50 -57.00-180.00   26
  2  \w    -87.00 -45.00   1.00    1.25    --  -33.50 178.00 -60.00   42
  3  \w     30.00  58.00   1.00    1.25    --   36.47 -37.00-120.00   28
  4  \w    -34.00  11.00   1.00    1.25    --   36.47 -37.00  60.00   45
  5  \w     57.00  85.00   1.00    1.25    --   36.47 178.00-120.00   28
  6  \w     -1.00  28.00   1.00    1.25    --   36.47 -99.00 -90.00   29
  7  \w     29.00  93.00   1.00    1.25    --   36.47  77.00 -90.00   64
  8  \w     45.00  77.00   1.00    1.25    --   36.47 -99.00 -90.00   32
  9  \w     57.00 109.00   1.00    1.25    --   36.47 178.00-180.00   52
 10  \w     80.00 110.00   1.00    1.25    --   36.47 178.00 -30.00   30
 11  \w    -32.00  23.00   1.00    1.25    --   36.47 -37.00-120.00   55
 12  \w     63.00 106.00   1.00    5.00    --  108.00 -94.00   0.00   43
 13  \w     88.00 130.00   1.00    5.00    --  108.00  45.00 -30.00   42
 14  \w    102.00 178.00   1.00    5.00    --  108.00  45.00  60.00   76
 15  \w     39.00  88.00   1.00    5.00    --  108.00 -94.00-150.00   49
 16  \w     37.00  81.00   1.00    5.00    --  108.00-111.00 -90.00   44
 17  \w     88.00 178.00   1.00    5.00    --  108.00  45.00  30.00   90
 18  \w     39.00 109.00   1.00    5.00    --  108.00 -94.00 -90.00   70
 19  \w     39.00  69.00   1.00    5.00    --  108.00 -94.00 -60.00   30
 20  \w     80.00 126.00   1.00    5.00    --  108.00 -61.00-120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1067567000
_diffrn_orient_matrix_UB_12      -0.0418795000
_diffrn_orient_matrix_UB_13      0.0404067000
_diffrn_orient_matrix_UB_21      0.1221593000
_diffrn_orient_matrix_UB_22      -0.0136146000
_diffrn_orient_matrix_UB_23      0.0411919000
_diffrn_orient_matrix_UB_31      -0.0297829000
_diffrn_orient_matrix_UB_32      0.0945548000
_diffrn_orient_matrix_UB_33      0.0238426000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13142
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.582
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.838
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0320
_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^)+(0.0255P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5503
_reflns_number_total             6055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01078j2.cif
_cod_data_source_block           202105139a
_cod_original_cell_volume        3403.85(8)
_cod_database_code               7710179
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C41H32O1N2Pd1Cl1P1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.543
_shelx_estimated_absorpt_t_min   0.347
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C35(H35),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41)
;
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.860