Enantioselective Hydrophosphination of Enones with Diphenylphosphine Catalyzed by Bis(imidazoline) NCN Pincer Palladium(II) Complexes
Hao, Xin-Qi; Zhao, Yong-Wei; Yang, Jing-Jing; Niu, Jun-Long; Gong, Jun-Fang; Song, Mao-Ping; Organometallics 33 (2014) 1801–; doi:10.1021/om500144b

data_4082884
_publ_section_title
;
 Enantioselective Hydrophosphination of Enones with Diphenylphosphine
 Catalyzed by Bis(imidazoline) NCN Pincer Palladium(II) Complexes
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1801
_journal_paper_doi               10.1021/om500144b
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H37 Br N4 Pd'
_chemical_formula_sum            'C32 H37 Br N4 Pd'
_chemical_formula_weight         663.97
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-16
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7799(3)
_cell_length_b                   11.7799(3)
_cell_length_c                   21.5302(8)
_cell_measurement_reflns_used    2926
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.3980
_cell_measurement_theta_min      3.4620
_cell_volume                     2987.66(15)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   54.00   85.00   1.0000   10.9300
omega____ theta____ kappa____ phi______ frames
    -       19.7885 -178.0000  -30.0000 31

  2 omega  -36.00   50.00   1.0000   10.9300
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -19.0000  -90.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0576151000
_diffrn_orient_matrix_UB_12      0.0158763000
_diffrn_orient_matrix_UB_13      0.0040585000
_diffrn_orient_matrix_UB_21      0.0099234000
_diffrn_orient_matrix_UB_22      -0.0506290000
_diffrn_orient_matrix_UB_23      0.0169411000
_diffrn_orient_matrix_UB_31      0.0143755000
_diffrn_orient_matrix_UB_32      -0.0283877000
_diffrn_orient_matrix_UB_33      -0.0279782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6687
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96958
_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
;
;
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.081(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+0.7951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                2636
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500144b_si_002.cif
_cod_data_source_block           complex-5b
_cod_depositor_comments          'Adding full bibliography for 4082884.cif.'
_cod_original_cell_volume        2987.68(16)
_cod_database_code               4082884
_chemical_oxdiff_formula         'C32 H37 Br N4 Pd'
_reflns_odcompleteness_completeness 99.57
_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:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;