Chiral CNN Pincer Palladium(II) Complexes with 2-Aryl-6-(oxazolinyl)pyridine Ligands: Synthesis, Characterization, and Application to Enantioselective Allylation of Isatins and Suzuki‒Miyaura Coupling Reaction
Wang, Tao; Hao, Xin-Qi; Huang, Juan-Juan; Wang, Kai; Gong, Jun-Fang; Song, Mao-Ping; Organometallics 33 (2014) 194–; doi:10.1021/om400945d

data_4082565
_publ_section_title
;
 Chiral CNN Pincer Palladium(II) Complexes with
 2-Aryl-6-(oxazolinyl)pyridine Ligands: Synthesis, Characterization, and
 Application to Enantioselective Allylation of Isatins and Suzuki--Miyaura
 Coupling Reaction
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              194
_journal_paper_doi               10.1021/om400945d
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H17 Cl N2 O Pd, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C24.5 H18 Cl2 N2 O Pd'
_chemical_formula_weight         538.71
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-09-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8040(4)
_cell_length_b                   13.5812(4)
_cell_length_c                   24.3928(5)
_cell_measurement_reflns_used    6136
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.3125
_cell_measurement_theta_min      2.9937
_cell_volume                     4241.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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  -46.00   47.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1383   77.0000  150.0000 93

  2 omega   65.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8726   77.0000  -60.0000 25

  3 omega   -7.00   84.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8726   77.0000 -150.0000 91

  4 omega   32.00   57.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8726 -178.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0464102000
_diffrn_orient_matrix_UB_12      -0.0001478000
_diffrn_orient_matrix_UB_13      -0.0158887000
_diffrn_orient_matrix_UB_21      -0.0300806000
_diffrn_orient_matrix_UB_22      -0.0046038000
_diffrn_orient_matrix_UB_23      0.0242897000
_diffrn_orient_matrix_UB_31      -0.0027175000
_diffrn_orient_matrix_UB_32      0.0520003000
_diffrn_orient_matrix_UB_33      0.0021279000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18581
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         8666
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0135P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0633
_reflns_number_gt                6583
_reflns_number_total             8666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400945d_si_002.cif
_cod_data_source_block           complex-3f
_cod_original_cell_volume        4241.75(19)
_cod_database_code               4082565
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32