Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear alpha,beta,gamma,delta-unsaturated ketones
Zhenni Ma; Fang Xie; Han Yu; Yiren Zhang; Xiaoting Wu; Wanbin Zhang; Chem.Commun. 49 (2013) 5292–; doi:10.1039/c3cc42088d

data_7109359
_publ_section_title
;
 Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents
 to linear alpha,beta,gamma,delta-unsaturated ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              5292
_journal_paper_doi               10.1039/c3cc42088d
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H18 O'
_chemical_formula_sum            'C18 H18 O'
_chemical_formula_weight         250.32
_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                 106.817(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3820(9)
_cell_length_b                   5.6425(6)
_cell_length_c                   11.8926(10)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4110
_cell_measurement_theta_min      2.9323
_cell_volume                     731.11(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3015
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0245P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                986
_reflns_number_total             1479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42088d.txt
_cod_data_source_block           121212_mzn
_cod_original_cell_volume        731.11(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7109359