PCN Pincer Palladium(II) Complex Catalyzed Enantioselective Hydrophosphination of Enones: Synthesis of Pyridine-Functionalized Chiral Phosphine Oxides as NCsp(3)O Pincer Preligands.
Hao, Xin-Qi; Huang, Juan-Juan; Wang, Tao; Lv, Jing; Gong, Jun-Fang; Song, Mao-Ping; The Journal of organic chemistry 79 (2014) 9512–9530; doi:10.1021/jo5015307

data_4029973
_publ_section_title
;
 PCN Pincer Palladium(II) Complex Catalyzed Enantioselective
 Hydrophosphination of Enones: Synthesis of Pyridine-Functionalized Chiral
 Phosphine Oxides as NCsp(3)O Pincer Preligands.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9512
_journal_page_last               9530
_journal_paper_doi               10.1021/jo5015307
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H23 Cl N O3 P Pd'
_chemical_formula_sum            'C27 H23 Cl N O3 P Pd'
_chemical_formula_weight         582.28
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-03
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_length_a                   7.9822(2)
_cell_length_b                   17.3280(5)
_cell_length_c                   17.6516(7)
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.1140
_cell_measurement_theta_min      3.4810
_cell_volume                     2441.49(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
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_diffrn_ambient_temperature      291.15
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0127489000
_diffrn_orient_matrix_UB_12      0.0353032000
_diffrn_orient_matrix_UB_13      -0.0194577000
_diffrn_orient_matrix_UB_21      -0.0247422000
_diffrn_orient_matrix_UB_22      0.0178377000
_diffrn_orient_matrix_UB_23      0.0343596000
_diffrn_orient_matrix_UB_31      0.0844614000
_diffrn_orient_matrix_UB_32      0.0105813000
_diffrn_orient_matrix_UB_33      0.0072209000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7202
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour
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_exptl_crystal_density_diffrn    1.584
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_exptl_crystal_description
;
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_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.18
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_refine_diff_density_max         0.283
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'calc w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0630
_reflns_number_gt                4391
_reflns_number_total             4850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5015307_si_002.cif
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'Adding full bibliography for 4029972--4029973.cif.'
_cod_original_cell_volume        2441.47(14)
_cod_database_code               4029973
_chemical_oxdiff_formula         C1H1O1N1Pd1P1Cl1
_reflns_odcompleteness_completeness 99.65
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_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;