The Reaction of 2-Aroylvinylcinnamaldehydes with Aromatic Aldehydes by Dual Catalysis with a Chiral N-Heterocyclic Carbene and a Lewis Acid: Enantioselective Construction of Tetrahydroindeno[1,2-c]furan-1-ones.
Wang, Gang; Wang, Zhan-Yong; Niu, Shuang-Shuo; Rao, Yin; Cheng, Ying; The Journal of organic chemistry  (2016) –; doi:10.1021/acs.joc.6b01362

data_4032051
_publ_section_title
;
 The Reaction of 2-Aroylvinylcinnamaldehydes with Aromatic Aldehydes by
 Dual Catalysis with a Chiral N-Heterocyclic Carbene and a Lewis Acid:
 Enantioselective Construction of Tetrahydroindeno[1,2-c]furan-1-ones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b01362
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C33 H25 Br O3'
_chemical_formula_weight         549.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.987(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.515(18)
_cell_length_b                   7.530(5)
_cell_length_c                   15.194(10)
_cell_measurement_reflns_used    2841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.61
_cell_volume                     2933(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
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_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9785
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.568
_diffrn_reflns_theta_min         1.589
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.382
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5892
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+3.8033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1922
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4170
_reflns_number_total             5892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01362_si_002.cif
_cod_data_source_block           151223b_0m_sq_s
_cod_database_code               4032051
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.634
_shelx_estimated_absorpt_t_max   0.870
_shelx_res_checksum              295
_shelx_hkl_checksum              19191
_shelx_fab_checksum              85116