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_4125539
_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         'C22 H13 N O6, C2 H3 N'
_chemical_formula_sum            'C24 H16 N2 O6'
_chemical_formula_weight         428.39
_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     direct
_audit_creation_date             2016-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.75939(9)
_cell_length_b                   10.99247(11)
_cell_length_c                   27.3555(3)
_cell_measurement_reflns_used    11262
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.8000
_cell_measurement_theta_min      3.8170
_cell_volume                     2032.58(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -133.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -77.0000  120.0000 138

  2 omega -128.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -99.0000   90.0000 49

  3 omega -124.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014 -125.0000 -120.0000 51

  4 omega   23.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.6014 -125.0000   90.0000 78

  5 omega   15.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -63.0000   30.0000 131

  6 omega   17.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -38.0000  120.0000 76

  7 omega   15.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -25.0000  150.0000 78

  8 omega   15.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -25.0000   30.0000 78

  9 omega   16.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667 -111.0000   60.0000 99

 10 omega   17.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -38.0000  -90.0000 76

 11 omega  100.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  111.0000   90.0000 78

 12 omega   15.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667  -63.0000  -30.0000 131

 13 omega -124.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -38.0000  -90.0000 130

 14 omega -125.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014  -57.0000 -180.0000 128

 15 omega -124.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -36.6014 -125.0000   30.0000 51

 16 omega   36.00  137.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   25.0000   60.0000 101

 17 omega   23.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7667   22.0000 -121.0000 155
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0585144000
_diffrn_orient_matrix_UB_12      0.0996384000
_diffrn_orient_matrix_UB_13      -0.0368590000
_diffrn_orient_matrix_UB_21      0.0271168000
_diffrn_orient_matrix_UB_22      -0.0909157000
_diffrn_orient_matrix_UB_23      -0.0423233000
_diffrn_orient_matrix_UB_31      -0.2186650000
_diffrn_orient_matrix_UB_32      -0.0379111000
_diffrn_orient_matrix_UB_33      0.0046491000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14402
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.877
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0460P)^2^+0.2377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3642
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11079_si_005.cif
_cod_data_source_block           vsr2-134
_cod_depositor_comments
'Adding full bibliography for 4125539--4125541.cif.'
_cod_database_code               4125539
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.90
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'