Substrate-Controlled Michael Additions of Chiral Ketones to Enones.
Fàbregas, Mireia; Gómez-Palomino, Alejandro; Pellicena, Miquel; Reina, Daniel F.; Romea, Pedro; Urpí, Fèlix; Font-Bardia, Mercè; Organic letters 16 (2014) 6220–; doi:10.1021/ol503133j

data_1518698
_publ_section_title
;
 Substrate-Controlled Michael Additions of Chiral Ketones to Enones.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6220
_journal_paper_doi               10.1021/ol503133j
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H26 O3'
_chemical_formula_sum            'C22 H26 O3'
_chemical_formula_weight         338.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7161(3)
_cell_length_b                   13.5777(6)
_cell_length_c                   24.2590(12)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      3.64
_cell_volume                     1882.78(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.836
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.836
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22363
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        113.000
_diffrn_reflns_theta_max         66.554
_diffrn_reflns_theta_min         3.644
_diffrn_source                   Microfocus
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.2787P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.849
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                2642
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503133j_si_002.cif
_cod_data_source_block           cu_o31rb93_0m
_cod_database_code               1518698