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_4082563
_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         'C21 H17 Cl N2 O Pd'
_chemical_formula_sum            'C21 H17 Cl N2 O Pd'
_chemical_formula_weight         455.22
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-04-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.495(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1915(2)
_cell_length_b                   21.4390(7)
_cell_length_c                   12.2763(3)
_cell_measurement_reflns_used    4117
_cell_measurement_temperature    291.0
_cell_measurement_theta_max      26.3149
_cell_measurement_theta_min      3.0352
_cell_volume                     1854.78(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      291.0
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -89.00  -42.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  -37.0000  -90.0000 94

  2 omega  -32.00   -6.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323   77.0000 -120.0000 52

  3 omega   19.00   91.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   37.0000   30.0000 144

  4 omega  -45.00   50.00   0.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -77.0000  -90.0000 190
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0324963000
_diffrn_orient_matrix_UB_12      0.0092071000
_diffrn_orient_matrix_UB_13      -0.0560105000
_diffrn_orient_matrix_UB_21      0.0158115000
_diffrn_orient_matrix_UB_22      -0.0306668000
_diffrn_orient_matrix_UB_23      -0.0177865000
_diffrn_orient_matrix_UB_31      -0.0939891000
_diffrn_orient_matrix_UB_32      -0.0083767000
_diffrn_orient_matrix_UB_33      0.0036786000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8473
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.064
_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   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6363
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                5614
_reflns_number_total             6363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400945d_si_002.cif
_cod_data_source_block           complex-3d
_cod_original_cell_volume        1854.79(9)
_cod_database_code               4082563
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 84.18
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     26.32