Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol.
Trost, Barry M.; Gnanamani, Elumalai; Kalnmals, Christopher A.; Hung, Chao-I Joey; Tracy, Jacob S.; Journal of the American Chemical Society 141 (2019) 1489–1493; doi:10.1021/jacs.8b13367

data_4128098
_publ_section_title
;
 Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides
 to Chromones Catalyzed by Zn-ProPhenol.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1489
_journal_page_last               1493
_journal_paper_doi               10.1021/jacs.8b13367
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H11 Br O4'
_chemical_formula_sum            'C14 H11 Br O4'
_chemical_formula_weight         323.14
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6127(5)
_cell_length_b                   8.2896(5)
_cell_length_c                   24.1826(16)
_cell_measurement_reflns_used    9537
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.578
_cell_measurement_theta_min      2.598
_cell_volume                     1325.61(16)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 Photon100
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            41499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.641
_diffrn_reflns_theta_min         2.597
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.107
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1283 before and 0.0638 after correction. 
The Ratio of minimum to maximum transmission is 0.8014. 
The \l/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       plank
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1432 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0195P)^2^+1.1175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0627
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3612
_reflns_number_total             3735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13367_si_002.cif
_cod_data_source_block           eg_i_2298_br_a_0m_a
_cod_database_code               4128098
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.477
_shelx_res_checksum              99275
_shelx_hkl_checksum              56770