Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric oligoarenes featuring two distal C-C stereogenic axes.
Bao, Xiaoze; Rodriguez, Jean; Bonne, Damien; Chemical science 11 (2020) 403–408; doi:10.1039/c9sc04378k

data_1552948
_publ_section_title
;
 Bidirectional enantioselective synthesis of bis-benzofuran atropisomeric
 oligoarenes featuring two distal C-C stereogenic axes.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              403
_journal_page_last               408
_journal_paper_doi               10.1039/c9sc04378k
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H12 Br2 N2 O6'
_chemical_formula_sum            'C26 H12 Br2 N2 O6'
_chemical_formula_weight         608.20
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-06 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3550(4)
_cell_length_b                   12.9923(7)
_cell_length_c                   24.5807(14)
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    295
_cell_measurement_theta_max      23.8200
_cell_measurement_theta_min      3.1950
_cell_volume                     2348.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -80.00  96.00   1.00   30.00    --    8.25   0.00-120.00  176
  2  \w    -68.00  41.00   1.00   30.00    --    8.25 -77.00  60.00  109
  3  \w    -20.00  19.00   1.00   30.00    --   -8.02 -99.00-120.00   39
  4  \w    -66.00  33.00   1.00   30.00    --    8.25 -38.00 150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001592000
_diffrn_orient_matrix_UB_12      0.0182098000
_diffrn_orient_matrix_UB_13      0.0272019000
_diffrn_orient_matrix_UB_21      0.0544532000
_diffrn_orient_matrix_UB_22      -0.0425306000
_diffrn_orient_matrix_UB_23      0.0079588000
_diffrn_orient_matrix_UB_31      0.0796021000
_diffrn_orient_matrix_UB_32      0.0289929000
_diffrn_orient_matrix_UB_33      -0.0054004000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26618
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.626
_diffrn_reflns_theta_min         2.891
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.498
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0377P)^2^+1.0885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                3930
_reflns_number_total             5216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04378k2.cif
_cod_data_source_block           bob0320
_cod_depositor_comments
;Adding full bibliography for 1552948--1552949.cif.

 Adding full bibliography for 1552948--1552949.cif.
;
_cod_database_code               1552948
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c26 h12 Br2 n2 o6'
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.487
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C17(H17), C18(H18),
 C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.746