Synthesis of Novel Enantiopure Biphenyl P,N-Ligands and Application in Palladium-Catalyzed Asymmetric Addition of Arylboronic Acids to N-Benzylisatin
Hongshan Lai; Zhiyan Huang; Qiong Wu; Yong Qin; Journal of Organic Chemistry 74 (2009) 283–288; doi:10.1021/jo802036m

data_4024230
_publ_section_title
;
Synthesis of Novel Enantiopure Biphenyl P,N-Ligands and Application in
Palladium-Catalyzed Asymmetric Addition of Arylboronic Acids
to N-Benzylisatin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              283
_journal_page_last               288
_journal_paper_doi               10.1021/jo802036m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C34 H37 F6 N O P Pd S Sb'
_chemical_formula_weight         880.83
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.089(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5696(3)
_cell_length_b                   19.2499(5)
_cell_length_c                   9.8027(2)
_cell_measurement_reflns_used    16568
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.01
_cell_volume                     1751.47(8)
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17159
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.450
_exptl_absorpt_correction_T_max  0.7409
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         7986
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0256P)^2^+0.4360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0584
_reflns_number_gt                7633
_reflns_number_total             7986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802036m_si_001.cif
_cod_data_source_block           y2494
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024230