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_7710177
_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         'C33 H34 Cl N2 P Pd'
_chemical_formula_sum            'C33 H34 Cl N2 P Pd'
_chemical_formula_weight         631.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
;
2022-02-23 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.540(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2862(5)
_cell_length_b                   12.1285(4)
_cell_length_c                   12.6954(5)
_cell_measurement_reflns_used    2812
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.5510
_cell_measurement_theta_min      3.4400
_cell_volume                     1473.22(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -3.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000  -90.0000 27

  2 omega  -49.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000  150.0000 90

  3 omega   -6.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   37.0000  120.0000 98

  4 omega  -49.00  -24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0240306000
_diffrn_orient_matrix_UB_12      0.0096238000
_diffrn_orient_matrix_UB_13      0.0448867000
_diffrn_orient_matrix_UB_21      0.0700952000
_diffrn_orient_matrix_UB_22      0.0008178000
_diffrn_orient_matrix_UB_23      0.0390922000
_diffrn_orient_matrix_UB_31      0.0030307000
_diffrn_orient_matrix_UB_32      0.0576696000
_diffrn_orient_matrix_UB_33      -0.0080298000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6698
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         3.195
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.423
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1605 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0203P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                4584
_reflns_number_total             5022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01078j2.cif
_cod_data_source_block           20140490
_cod_original_cell_volume        1473.22(11)
_cod_database_code               7710177
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4Pd1
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.844
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C16(H16), C17(H17), C18(H18), C24(H24), C25(H25), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_res_checksum              51512
_shelx_hkl_checksum              11996
_olex2_submission_special_instructions 'No special instructions were received'