Enantioselective Syntheses of Furan Atropisomers by an Oxidative Central-to-Axial Chirality Conversion Strategy.
Raut, Vivek S.; Jean, Marion; Vanthuyne, Nicolas; Roussel, Christian; Constantieux, Thierry; Bressy, Cyril; Bugaut, Xavier; Bonne, Damien; Rodriguez, Jean; Journal of the American Chemical Society 139 (2017) 2140–2143; doi:10.1021/jacs.6b11079

data_4125541
_publ_section_title
;
 Enantioselective Syntheses of Furan Atropisomers by an Oxidative
 Central-to-Axial Chirality Conversion Strategy.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2140
_journal_page_last               2143
_journal_paper_doi               10.1021/jacs.6b11079
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H12 Br N O4'
_chemical_formula_sum            'C19 H12 Br N O4'
_chemical_formula_weight         398.21
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2701(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.95597(12)
_cell_length_b                   7.08249(9)
_cell_length_c                   11.73782(13)
_cell_measurement_reflns_used    10105
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.1440
_cell_measurement_theta_min      4.4260
_cell_volume                     825.372(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -125.00 -73.00   1.00    1.00    --  -37.23-125.00-180.00   52
  2  \w   -129.00 -79.00   1.00    1.00    --  -37.23 -99.00 150.00   50
  3  \w   -129.00 -79.00   1.00    1.00    --  -37.23 -99.00  60.00   50
  4  \w    -79.00  59.00   1.00    1.00    --  -37.23  77.00 120.00  138
  5  \w   -133.00   4.00   1.00    1.00    --  -37.23 -77.00 -30.00  137
  6  \w    -81.00  35.00   1.00    1.00    --  -37.23  86.00-125.00  116
  7  \w    -96.00  -2.00   1.00    1.00    --  -37.23 125.00 -60.00   94
  8  \w     57.00 150.00   1.00    2.00    --  105.39 178.00-180.00   93
  9  \w     63.00 178.00   1.00    2.00    --  105.39  38.00  30.00  115
 10  \w      9.00 149.00   1.00    2.00    --  105.39 -86.00 116.00  140
 11  \w     15.00 174.00   1.00    2.00    --  105.39 -25.00 -60.00  159
 12  \w     17.00 115.00   1.00    2.00    --  105.39-111.00-180.00   98
 13  \w     57.00 150.00   1.00    2.00    --  105.39 178.00   0.00   93
 14  \w    101.00 178.00   1.00    2.00    --  105.39  94.00 -27.00   77
 15  \w     18.00 144.00   1.00    2.00    --  105.39 -50.00  90.00  126
 16  \w     11.00 151.00   1.00    2.00    --  105.39 -91.00 -60.00  140
 17  \w     64.00 178.00   1.00    2.00    --  105.39  77.00 -60.00  114
 18  \w   -125.00   2.00   1.00    1.00    --  -37.23 -57.00-180.00  127
 19  \w   -125.00   2.00   1.00    1.00    --  -37.23 -57.00  60.00  127
 20  \w   -129.00 -79.00   1.00    1.00    --  -37.23 -99.00 -90.00   50
 21  \w     -4.00 133.00   1.00    1.00    --   37.23  77.00 120.00  137
 22  \w     -4.00 133.00   1.00    1.00    --   37.23  77.00 -30.00  137
 23  \w     -4.00 133.00   1.00    1.00    --   37.23  77.00-120.00  137
 24  \w     63.00 178.00   1.00    2.00    --  105.39  38.00 120.00  115
 25  \w     64.00 178.00   1.00    2.00    --  105.39  63.00-150.00  114
 26  \w     64.00 178.00   1.00    2.00    --  105.39  77.00 -90.00  114
 27  \w     64.00 178.00   1.00    2.00    --  105.39  63.00  60.00  114
 28  \w     64.00 178.00   1.00    2.00    --  105.39  77.00-120.00  114
 29  \w     64.00 178.00   1.00    2.00    --  105.39  77.00 120.00  114
 30  \w     64.00 115.00   1.00    2.00    --  105.39  63.00  30.00   51
 31  \w     37.00 178.00   1.00    2.00    --  105.39  25.00-120.00  141
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0716052000
_diffrn_orient_matrix_UB_12      -0.1907981000
_diffrn_orient_matrix_UB_13      0.0129463000
_diffrn_orient_matrix_UB_21      -0.0734627000
_diffrn_orient_matrix_UB_22      0.0251095000
_diffrn_orient_matrix_UB_23      -0.1193801000
_diffrn_orient_matrix_UB_31      0.1163999000
_diffrn_orient_matrix_UB_32      -0.1013458000
_diffrn_orient_matrix_UB_33      -0.0539958000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.043
_diffrn_reflns_theta_min         3.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.2786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3024
_reflns_number_total             3058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11079_si_004.cif
_cod_data_source_block           vsr21831
_cod_depositor_comments
'Adding full bibliography for 4125539--4125541.cif.'
_cod_database_code               4125541
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.701