C~2~ Symmetric Chiral NHC Ligand for Asymmetric Quaternary Carbon Constructing Copper-Catalyzed Conjugate Addition of Grignard Reagents to 3-Substituted Cyclohexenones
Yasumasa Matsumoto; Ken-ichi Yamada; Kiyoshi Tomioka; Journal of Organic Chemistry 73 (2008) 4578–4581; doi:10.1021/jo800613h

data_4023485
_publ_contact_author_address
;Graduate School of Pharmaceutical Sciences
Kyoto University
Yoshida, Sakyo, Kyoto 606-8501
Japan
;
_publ_contact_author_email       tomioka@pharm.kyoto-u.ac.jp
_publ_contact_author_fax         +81-75-753-4604
_publ_contact_author_name        'Kiyoshi Tomioka'
_publ_contact_author_phone       +81-75-753-4553
_publ_section_title
;
 C~2~ Symmetric Chiral NHC Ligand for Asymmetric Quaternary Carbon
 Constructing Copper-Catalyzed Conjugate Addition of Grignard
 Reagents to 3-Substituted Cyclohexenones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4578
_journal_page_last               4581
_journal_paper_doi               10.1021/jo800613h
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C35 H38 Au Cl N2'
_chemical_formula_sum            'C35 H38 Au Cl N2'
_chemical_formula_weight         719.09
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-04-14T19:16:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1526(9)
_cell_length_b                   13.1526(9)
_cell_length_c                   18.2549(12)
_cell_measurement_reflns_used    28921
_cell_measurement_temperature    98.1
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     3157.9(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_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
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36093
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         3.1
_exptl_absorpt_coefficient_mu    4.768
_exptl_absorpt_correction_T_max  0.715
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.291
_refine_diff_density_min         -0.31
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0178P)^2^+0.5998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0421
_reflns_number_gt                4382
_reflns_number_total             4611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800613h-File004.cif
_cod_data_source_block           061117ym
_cod_database_code               4023485