Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds.
Wu, Hui-Chun; Wang, Chen; Chen, Ying-Han; Liu, Yan-Kai; Chemical communications (Cambridge, England) 57 (2021) 1762–1765; doi:10.1039/d0cc07761e

data_7127781
_publ_section_title
;
 Asymmetric organocatalytic vinylogous Michael addition triggered
 triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous
 nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane
 scaffolds.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1762
_journal_page_last               1765
_journal_paper_doi               10.1039/d0cc07761e
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H15 Br N2 O2'
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-07-08 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   8.3888(11)
_cell_length_b                   9.2869(12)
_cell_length_c                   23.322(4)
_cell_measurement_reflns_used    659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.7990
_cell_measurement_theta_min      5.6140
_cell_volume                     1816.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
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_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.1562
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4537
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        67.233
_diffrn_reflns_theta_max         67.233
_diffrn_reflns_theta_min         3.791
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 193 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.0831
_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^)+(0.0463P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.2058
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.725
_reflns_Friedel_fraction_max     0.725
_reflns_number_gt                1254
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07761e2.cif
_cod_data_source_block           exp_10294
_cod_depositor_comments          'Adding full bibliography for 7127781.cif.'
_cod_database_code               7127781
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.681
_shelx_estimated_absorpt_t_max   0.719
_shelx_res_checksum              82059