Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.
Liao, Xuebin; Weng, Zhiqiang; Hartwig, John F.; Journal of the American Chemical Society 130 (2008) 195–200; doi:10.1021/ja074453g

data_4101736
_publ_contact_author
; 
Scott R. Wilson 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_contact_author_email       srwilson@uiuc.edu
_publ_contact_author_fax         '1  217 244 8068'
_publ_contact_author_phone       '1  217 244 1708'
_publ_section_title
;
 Enantioselective alpha-arylation of ketones with aryl triflates catalyzed
 by difluorphos complexes of palladium and nickel.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              195
_journal_page_last               200
_journal_paper_doi               10.1021/ja074453g
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 I O3'
_chemical_formula_sum            'C18 H17 I O3'
_chemical_formula_weight         408.22
_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
_audit_update_record
; 
2007-09-20   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.098(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.698(7)
_cell_length_b                   7.153(5)
_cell_length_c                   11.571(7)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.69
_cell_volume                     802.1(9)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  g64vas
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_sigmaI/netI    0.1529
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4333
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        5.1
_diffrn_standards_interval_time  609
_diffrn_standards_number         70
_exptl_absorpt_coefficient_mu    2.006
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             404
_exptl_crystal_id                g64vas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 0 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.732
_refine_diff_density_rms         0.179
_refine_ls_abs_structure_details 'Flack (1983),  701 Friedels'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0774P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                1287
_reflns_number_total             2289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja074453gsi20071014_062742.cif
_cod_data_source_block           iodocompoundB
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_cell_volume        802.2(9)
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21   '
_cod_database_code               4101736