Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core.
Gaucherand, Arthur; Yen-Pon, Expédite; García-López, Diego; Naubron, Jean-Valère; Chentouf, Sara; Giorgi, Michel; Humbel, Stéphane; Jean, Marion; Rodriguez, Jean; Bonne, Damien; Chemical science 15 (2024) 7300–7307; doi:10.1039/d4sc00745j

data_1571477
_publ_section_title
;
 Padlocking dihydrofurannulation for the control of small degree of
 helicity built on a fused-tetracyclic core.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              7300
_journal_page_last               7307
_journal_paper_doi               10.1039/d4sc00745j
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H20 N2 O3'
_chemical_formula_sum            'C27 H20 N2 O3'
_chemical_formula_weight         420.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.18760(10)
_cell_length_b                   11.14520(10)
_cell_length_c                   20.9565(2)
_cell_measurement_reflns_used    15399
_cell_measurement_temperature    295
_cell_measurement_theta_max      75.9430
_cell_measurement_theta_min      4.1930
_cell_volume                     2145.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -118.00 -10.00   1.00    1.00    --  -40.91 -27.00  94.00  108
  2  \w    -87.00   7.00   1.00    1.00    --  -40.91 114.00 102.00   94
  3  \w      4.00  83.00   1.00    1.00    --   40.91-101.00 -88.00   79
  4  \w     10.00 118.00   1.00    1.00    --   40.91  27.00-103.00  108
  5  \w    100.00 178.00   1.00   10.00    --  112.00 114.00 102.00   78
  6  \w     32.00 111.00   1.00   10.00    --  112.00-101.00 -88.00   79
  7  \w     35.00 143.00   1.00   10.00    --  112.00 -27.00  94.00  108
  8  \w    101.00 178.00   1.00   10.00    --  112.00 101.00  15.00   77
  9  \w     36.00 112.00   1.00   10.00    --  112.00-114.00  11.00   76
 10  \w     23.00  97.00   1.00    1.00    --   40.91-125.00-150.00   74
 11  \w     39.00 138.00   1.00   10.00    --  112.00 -45.00-120.00   99
 12  \w     56.00 107.00   1.00   10.00    --  112.00-111.00 -60.00   51
 13  \w    115.00 147.00   1.00   10.00    --  112.00  15.00   0.00   32
 14  \w     60.00  86.00   1.00   10.00    --  112.00-111.00-120.00   26
 15  \w     97.00 126.00   1.00   10.00    --  112.00 -61.00-150.00   29
 16  \w     60.00  87.00   1.00   10.00    --  112.00  15.00   0.00   27
 17  \w    103.00 177.00   1.00   10.00    --  112.00 111.00 -60.00   74
 18  \w     41.00  92.00   1.00   10.00    --  112.00-111.00  30.00   51
 19  \w     37.00 107.00   1.00   10.00    --  112.00-111.00 -90.00   70
 20  \w     37.00 139.00   1.00   10.00    --  112.00 -30.00-150.00  102
 21  \w    129.00 168.00   1.00   10.00    --  112.00  27.00-103.00   39
 22  \w     31.00  56.00   1.00   10.00    --  112.00 -94.00  30.00   25
 23  \w     76.00 106.00   1.00   10.00    --  112.00 -94.00  30.00   30
 24  \w     66.00  92.00   1.00   10.00    --  112.00 178.00 120.00   26
 25  \w    125.00 150.00   1.00   10.00    --  112.00 178.00 120.00   25
 26  \w    108.00 134.00   1.00   10.00    --  112.00  56.00 -10.39   26
 27  \w    136.00 162.00   1.00   10.00    --  112.00  56.00 -10.39   26
 28  \w     84.00 116.00   1.00   10.00    --  112.00  61.00 -25.89   32
 29  \w     85.00 111.00   1.00   10.00    --  112.00 -77.00 -90.00   26
 30  \w    109.00 135.00   1.00   10.00    --  112.00 111.00 -90.00   26
 31  \w     97.00 123.00   1.00   10.00    --  112.00  45.00-120.00   26
 32  \w     85.00 111.00   1.00   10.00    --  112.00  27.00-103.00   26
;
_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      -0.0617727000
_diffrn_orient_matrix_UB_12      -0.1065619000
_diffrn_orient_matrix_UB_13      0.0382010000
_diffrn_orient_matrix_UB_21      0.0066172000
_diffrn_orient_matrix_UB_22      0.0754436000
_diffrn_orient_matrix_UB_23      0.0615336000
_diffrn_orient_matrix_UB_31      -0.1557187000
_diffrn_orient_matrix_UB_32      0.0454564000
_diffrn_orient_matrix_UB_33      -0.0125718000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.183
_diffrn_reflns_theta_min         4.219
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
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    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0769P)^2^+0.1124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4332
_reflns_number_total             4452
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           ag3021
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_database_code               1571477
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c27 h20 n2 o3'
_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 Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              63182
_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 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.771