Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O.
Qi, Chao; Xiong, Yuan; Eschenbrenner-Lux, Vincent; Cong, Huan; Porco, Jr, John A; Journal of the American Chemical Society 138 (2016) 798–801; doi:10.1021/jacs.5b12778

data_4124874
_publ_section_title
;
 Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products
 Sanggenons C and O.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              798
_journal_page_last               801
_journal_paper_doi               10.1021/jacs.5b12778
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C35 H21 B Br2 O4, C6 H6 O'
_chemical_formula_sum            'C41 H27 B Br2 O5'
_chemical_formula_weight         770.25
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-08-21 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 95.976(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2781(4)
_cell_length_b                   12.6985(4)
_cell_length_c                   15.9497(5)
_cell_measurement_temperature    100(2)
_cell_volume                     2070.39(12)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'OLEX2 (Dolmanov, et al. 2006)'
_computing_publication_material  'publCIF v1.9.9_c (IUCr)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41052
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.614
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_min         2.785
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_T_max  0.8976
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 3243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.042(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         7236
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0460P)^2^+1.7520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                7052
_reflns_number_total             7236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12778_si_003.cif
_cod_data_source_block           chao8_face_indexed_sqd
_cod_depositor_comments
'Adding full bibliography for 4124874--4124875.cif.'
_cod_database_code               4124874
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.678
_shelx_estimated_absorpt_t_max   0.880
_shelx_res_checksum              97471
_shelx_hkl_checksum              18299
_platon_squeeze_void_probe_radius 1.20