Enantioselective Michael Addition of Photogenerated o-Quinodimethanes to Enones Catalyzed by Chiral Amino Acid Esters.
Yuan, Xiaoqian; Dong, Shupeng; Liu, Zhen; Wu, Guibing; Zou, Chuncheng; Ye, Jinxing; Organic letters 19 (2017) 2322–2325; doi:10.1021/acs.orglett.7b00862

data_1546222
_publ_section_title
;
 Enantioselective Michael Addition of Photogenerated o-Quinodimethanes to
 Enones Catalyzed by Chiral Amino Acid Esters.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2322
_journal_page_last               2325
_journal_paper_doi               10.1021/acs.orglett.7b00862
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H17 Br O'
_chemical_formula_weight         353.24
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.296(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4386(11)
_cell_length_b                   11.6291(13)
_cell_length_c                   14.6798(17)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.711
_cell_measurement_theta_min      4.471
_cell_volume                     1608.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9292
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.161
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
; 
 Flack x determined using 937 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.027(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0102P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.652
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                3123
_reflns_number_total             4979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00862_si_004.cif
_cod_data_source_block           cd16426
_cod_database_code               1546222
_shelx_estimated_absorpt_t_min   0.603
_shelx_estimated_absorpt_t_max   0.749
_shelxl_version_number           2013-4
_shelx_res_checksum              85294
_shelx_hkl_checksum              31106