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_4082562
_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         'C20 H15 Cl N2 O Pd'
_chemical_formula_sum            'C20 H15 Cl N2 O Pd'
_chemical_formula_weight         441.19
_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             2011-06-21
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.100(2)
_cell_length_b                   11.2001(12)
_cell_length_c                   15.725(2)
_cell_measurement_reflns_used    4253
_cell_measurement_temperature    291.15
_cell_measurement_theta_max      29.1104
_cell_measurement_theta_min      3.0060
_cell_volume                     1778.8(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      291.15
_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  -66.00  -40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  143.0000 -133.0000 26

  2 omega  -50.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104    0.0000 -150.0000 117

  3 omega   48.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104   70.0000  172.0000 29

  4 omega    0.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104   70.0000  172.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0664114000
_diffrn_orient_matrix_UB_12      0.0152914000
_diffrn_orient_matrix_UB_13      -0.0103575000
_diffrn_orient_matrix_UB_21      0.0232304000
_diffrn_orient_matrix_UB_22      0.0357052000
_diffrn_orient_matrix_UB_23      -0.0340859000
_diffrn_orient_matrix_UB_31      -0.0037230000
_diffrn_orient_matrix_UB_32      -0.0500142000
_diffrn_orient_matrix_UB_33      -0.0275230000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7100
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.01
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0268
_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^)+(0.0169P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0504
_reflns_number_gt                3339
_reflns_number_total             3625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400945d_si_002.cif
_cod_data_source_block           complex-3c
_cod_original_cell_volume        1778.9(5)
_cod_database_code               4082562
_chemical_oxdiff_formula         'C11 H10 S O2'
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32