Highly enantioselective copper(I)-catalyzed conjugate addition of 1,3-diynes to alpha,beta-unsaturated trifluoromethyl ketones
Amparo Sanz-Marco; Gonzalo Blay; M. Carmen Munoz; Jose R. Pedro; Chem.Commun. 51 (2015) 8958–; doi:10.1039/C5cc01676B

data_7117176
_publ_section_title
;
 Highly enantioselective copper(I)-catalyzed conjugate addition of
 1,3-diynes to alpha,beta-unsaturated trifluoromethyl ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              8958
_journal_paper_doi               10.1039/C5cc01676B
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H11 F3 O S'
_chemical_formula_weight         332.33
_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
_audit_update_record
;
2015-01-30 deposited with the CCDC.
2015-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.029(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.59300(10)
_cell_length_b                   8.1070(3)
_cell_length_c                   17.5700(5)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      12
_cell_volume                     793.60(4)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7127
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1726P)^2^+0.1097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2313
_reflns_number_gt                2709
_reflns_number_total             3610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01676b2.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7117176