Monodentate Non-C2-symmetric Chiral N-Heterocyclic Carbene Complexes for Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and Alkenylsilylfluorides to Cyclic Enones
Kang-sang Lee; Amir H. Hoveyda; Journal of Organic Chemistry 74 (2009) 4455–4462; doi:10.1021/jo900589x

data_4024595
_publ_section_title
;
Monodentate Non-C2-symmetric Chiral N-Heterocyclic Carbene Complexes for
Enantioselective Synthesis. Cu-Catalyzed Conjugate Additions of Aryl- and
Alkenylsilylfluorides to Cyclic Enones
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4455
_journal_page_last               4462
_journal_paper_doi               10.1021/jo900589x
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         '(C36 H33 N2)+ (B F4)-'
_chemical_formula_sum            'C36 H33 B F4 N2'
_chemical_formula_weight         580.45
_chemical_melting_point          ?
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.358(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.466(4)
_cell_length_b                   17.876(8)
_cell_length_c                   10.669(5)
_cell_measurement_reflns_used    7661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.27
_cell_volume                     1756.4(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6912
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
;
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(18)
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6912
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0769
_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^)+(0.0990P)^2^+1.5345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2133
_reflns_number_gt                5629
_reflns_number_total             6912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900589x_si_003.cif
_cod_data_source_block           C36H33N2BF4
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
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_cod_database_code               4024595