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_1552949
_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         'C15 H10 N O5, 0.35(C3 H7)'
_chemical_formula_sum            'C16.05 H12.45 N O5'
_chemical_formula_weight         299.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-26 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0405(2)
_cell_length_b                   8.47920(10)
_cell_length_c                   13.84310(10)
_cell_measurement_reflns_used    10111
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.8850
_cell_measurement_theta_min      5.1270
_cell_volume                     1691.83(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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    -69.00  32.00   1.00    1.00    --  -41.07  57.00 -30.00  101
  2  \w   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00 -60.00   98
  3  \w   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00-180.00   98
  4  \w   -121.00   0.00   1.00    1.00    --  -41.07 -19.00  30.00  121
  5  \w     23.00  97.00   1.00    1.00    --   41.07-125.00  60.00   74
  6  \w     19.00 109.00   1.00    5.00    --  101.41 -94.00 -30.00   90
  7  \w     20.00 154.00   1.00    5.00    --  101.41 -15.00-180.00  134
  8  \w    100.00 178.00   1.00    5.00    --  101.41 109.00  14.00   78
  9  \w     19.00 109.00   1.00    5.00    --  101.41 -94.00  60.00   90
 10  \w     19.00 109.00   1.00    5.00    --  101.41 -94.00-150.00   90
 11  \w     28.00 117.00   1.00    5.00    --  101.41-125.00-150.00   89
 12  \w     29.00 130.00   1.00    5.00    --  101.41 -61.00-120.00  101
 13  \w     28.00 127.00   1.00    5.00    --  101.41 -45.00  60.00   99
 14  \w     49.00 178.00   1.00    5.00    --  101.41  15.00-120.00  129
 15  \w     28.00 127.00   1.00    5.00    --  101.41 -45.00   0.00   99
 16  \w     25.00 130.00   1.00    5.00    --  101.41 -30.00-120.00  105
 17  \w   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00  30.00  109
 18  \w   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00 -90.00  109
 19  \w   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00 120.00  109
 20  \w     23.00  97.00   1.00    1.00    --   41.07-125.00-150.00   74
 21  \w     72.00 174.00   1.00    5.00    --  101.41  61.00 -90.00  102
 22  \w     72.00 174.00   1.00    5.00    --  101.41  61.00  60.00  102
 23  \w     73.00 178.00   1.00    5.00    --  101.41  30.00   0.00  105
 24  \w     72.00 123.00   1.00    5.00    --  101.41  61.00 120.00   51
;
_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      -0.0575488000
_diffrn_orient_matrix_UB_12      0.1472876000
_diffrn_orient_matrix_UB_13      -0.0434195000
_diffrn_orient_matrix_UB_21      -0.0585063000
_diffrn_orient_matrix_UB_22      -0.0988249000
_diffrn_orient_matrix_UB_23      -0.0889693000
_diffrn_orient_matrix_UB_31      -0.0684783000
_diffrn_orient_matrix_UB_32      -0.0393378000
_diffrn_orient_matrix_UB_33      0.0607128000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12262
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.857
_diffrn_reflns_theta_min         3.830
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76479
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       prism
_exptl_crystal_F_000             623
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3195
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1544P)^2^+0.2026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2005
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3155
_reflns_number_total             3195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04378k2.cif
_cod_data_source_block           b9302162
_cod_depositor_comments
;Adding full bibliography for 1552948--1552949.cif.

 Adding full bibliography for 1552948--1552949.cif.
;
_cod_database_code               1552949
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c30 h22 n2 o10'
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.755
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C16
 1.45 with sigma of 0.02
 C20-C21
 1.45 with sigma of 0.01
 C17-C18
 1.54 with sigma of 0.02
 C20-C19
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C16 \\sim C17: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.02
C17 \\sim C18: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.02
Uanis(C17) = Uanis(C20)
Uanis(C21) = Uanis(C16)
Uanis(C19) = Uanis(C18)
4. Rigid body (RIGU) restrains
 C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C19, C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: C16(0.2) H16A(0.2) H16B(0.2) C17(0.2) H17A(0.2) H17B(0.2) C18(0.2)
 H18A(0.2) H18B(0.2) H18C(0.2) C19(0.15) H19A(0.15) H19B(0.15) H19C(0.15)
 C20(0.15) H20A(0.15) H20B(0.15) C21(0.15) H21A(0.15) H21B(0.15)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B), C21(H21A,H21B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C13(H13), C14(H14)
6.d Idealised Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
6.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.717