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_4124875
_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 ad
_chemical_formula_moiety         'C26 H23 Br O2'
_chemical_formula_sum            'C26 H23 Br O2'
_chemical_formula_weight         447.35
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-08-17 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8799(10)
_cell_length_b                   12.0496(12)
_cell_length_c                   14.8783(13)
_cell_measurement_temperature    100(2)
_cell_volume                     2129.8(3)
_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, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker D8 Venture MX'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  MX
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7795
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.394
_diffrn_reflns_theta_min         4.722
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.772
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0245
_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^+0.1865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0569
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.787
_reflns_Friedel_fraction_max     0.740
_reflns_number_gt                3569
_reflns_number_total             3738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12778_si_002.cif
_cod_data_source_block           chao1_0m_a
_cod_depositor_comments
'Adding full bibliography for 4124874--4124875.cif.'
_cod_database_code               4124875
_shelxl_version_number           2014-3
_shelx_res_checksum              13036
_shelx_hkl_checksum              18753