NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenones <i>via</i> α,β-unsaturated acyl azoliums.
Dzieszkowski, Krzysztof; Słotwiński, Michał; Rafińska, Katarzyna; Muzioł, Tadeusz M; Rafiński, Zbigniew; Chemical communications (Cambridge, England) 57 (2021) 9999–10002; doi:10.1039/d1cc03708k

data_7128944
_publ_section_title
;
 NHC-catalyzed enantioselective C2-functionalization of
 3-hydroxychromenones <i>via</i> \a,\b-unsaturated acyl azoliums.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9999
_journal_page_last               10002
_journal_paper_doi               10.1039/d1cc03708k
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 Br O5'
_chemical_formula_sum            'C19 H15 Br O5'
_chemical_formula_weight         403.22
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.06(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   5.9984(13)
_cell_length_c                   18.889(6)
_cell_measurement_reflns_used    2406
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2770
_cell_measurement_theta_min      2.1760
_cell_volume                     1786.0(13)
_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_publication_material  ciftab
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_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11460
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.095
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.34a (2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       needle
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_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6739
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.844
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3655
_reflns_number_total             6739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03708k2.cif
_cod_data_source_block           kd2shape
_cod_depositor_comments          'Adding full bibliography for 7128944.cif.'
_cod_original_cell_volume        1786.1(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7128944
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.361
_shelx_estimated_absorpt_t_max   0.893
_shelx_res_checksum              83969