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_4125540
_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 H14 Br N O4'
_chemical_formula_sum            'C19 H14 Br N O4'
_chemical_formula_weight         400.22
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-17
_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                120
_cell_formula_units_Z            9
_cell_length_a                   18.09886(14)
_cell_length_b                   18.09886(14)
_cell_length_c                   13.84162(14)
_cell_measurement_reflns_used    20199
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.7030
_cell_measurement_theta_min      4.2280
_cell_volume                     3926.63(6)
_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    'ShelXT (Sheldrick, 2015)'
_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 0.999
_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   -133.00   4.00   1.00    1.00    --  -37.23 -77.00-180.00  137
  2  \w    -96.00  -2.00   1.00    1.00    --  -37.23 125.00 -90.00   94
  3  \w   -125.00   2.00   1.00    1.00    --  -37.23 -57.00 120.00  127
  4  \w   -125.00   2.00   1.00    1.00    --  -37.23 -57.00-120.00  127
  5  \w   -125.00   5.00   1.00    1.00    --  -37.23 -38.00 -60.00  130
  6  \w   -129.00 -79.00   1.00    1.00    --  -37.23 -99.00  30.00   50
  7  \w     77.00 129.00   1.00    1.00    --   37.23 153.00 155.00   52
  8  \w    -18.00  11.00   1.00    1.00    --   37.23 110.00  15.58   29
  9  \w    -21.00   6.00   1.00    1.00    --   37.23 115.00-169.36   27
 10  \w    -17.00  11.00   1.00    1.00    --   37.23 109.00 -55.66   28
 11  \w      1.00  86.00   1.00    1.00    --   37.23 -99.00 150.00   85
 12  \w    100.00 178.00   1.00   10.00    --  105.39 111.00  60.00   78
 13  \w     66.00 178.00   1.00   10.00    --  105.39  50.00  30.00  112
 14  \w     64.00 178.00   1.00   10.00    --  105.39  63.00   0.00  114
 15  \w     64.00 178.00   1.00   10.00    --  105.39  63.00  30.00  114
 16  \w     66.00 178.00   1.00   10.00    --  105.39  58.00 -41.22  112
 17  \w     64.00 178.00   1.00   10.00    --  105.39  77.00 -60.00  114
 18  \w     64.00  90.00   1.00   10.00    --  105.39  77.00   0.00   26
 19  \w     64.00  91.00   1.00   10.00    --  105.39  77.00  30.00   27
 20  \w     64.00  91.00   1.00   10.00    --  105.39  77.00 -30.00   27
 21  \w     65.00  92.00   1.00   10.00    --  105.39  63.00  60.00   27
 22  \w     64.00  95.00   1.00   10.00    --  105.39  63.00 -60.00   31
 23  \w     64.00  91.00   1.00   10.00    --  105.39  63.00 -30.00   27
 24  \w     67.00  94.00   1.00   10.00    --  105.39  53.00  49.69   27
 25  \w     66.00  92.00   1.00   10.00    --  105.39  50.00   0.00   26
 26  \w    100.00 172.00   1.00   10.00    --  105.39 111.00-150.00   72
 27  \w     12.00 120.00   1.00   10.00    --  105.39 -91.00 -90.00  108
 28  \w    130.00 166.00   1.00   10.00    --  105.39  53.00  49.69   36
 29  \w     64.00  96.00   1.00   10.00    --  105.39  77.00  60.00   32
 30  \w     64.00 141.00   1.00   10.00    --  105.39  38.00   0.00   77
 31  \w     64.00  89.00   1.00   10.00    --  105.39  38.00  30.00   25
 32  \w     64.00 133.00   1.00   10.00    --  105.39  36.00 -11.94   69
;
_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      0.0690068000
_diffrn_orient_matrix_UB_12      0.0941286000
_diffrn_orient_matrix_UB_13      0.0142964000
_diffrn_orient_matrix_UB_21      -0.0691520000
_diffrn_orient_matrix_UB_22      0.0258734000
_diffrn_orient_matrix_UB_23      -0.0029923000
_diffrn_orient_matrix_UB_31      -0.0107964000
_diffrn_orient_matrix_UB_32      -0.0114647000
_diffrn_orient_matrix_UB_33      0.1103300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.162
_diffrn_reflns_theta_min         4.261
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54246
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       plate
_exptl_crystal_F_000             1818
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         9135
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0544P)^2^+0.8532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                8880
_reflns_number_total             9135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b11079_si_002.cif
_cod_data_source_block           vsr21691
_cod_depositor_comments
;
Adding full bibliography for 4125539--4125541.cif.

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C57 H42 Br3 N3 O12'
_cod_original_formula_weight         1200.66
_cod_original_formula_moiety         '3(C19 H14 Br N O4)'
_cod_original_formula_units_Z            3
_cod_original_cell_volume        3926.63(7)
_cod_database_code               4125540
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7987(11) 0.2013(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12), C20(H20), C31(H31), C39(H39), C50(H50)
4.b 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), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C34(H34), C35(H35),
  C36(H36), C37(H37), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48),
 C53(H53), C54(H54), C55(H55), C56(H56)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C), C57(H57A,H57B,H57C)
;
_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 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.743