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_1571475
_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_formula_moiety         'C27 H19 N O4'
_chemical_formula_sum            'C27 H19 N O4'
_chemical_formula_weight         421.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-28
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                78.591(2)
_cell_angle_beta                 74.221(2)
_cell_angle_gamma                66.162(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7947(2)
_cell_length_b                   9.7683(2)
_cell_length_c                   13.6750(3)
_cell_measurement_reflns_used    11441
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.6090
_cell_measurement_theta_min      3.3430
_cell_volume                     1028.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.984
_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   -110.00 -65.00   1.00    5.00    --  -40.79 -52.00 -32.00   45
  2  \w     19.00  46.00   1.00    5.00    --   40.79  52.00 113.00   27
  3  \w     66.00  99.00   1.00    5.00    --   40.79  52.00 113.00   33
  4  \w     37.00  63.00   1.00   20.00    --  105.59 -52.00 -32.00   26
  5  \w    117.00 143.00   1.00   20.00    --  105.59  52.00 113.00   26
  6  \w     81.00 111.00   1.00   20.00    --  105.59  52.00 113.00   30
  7  \w    -56.00 -16.00   1.00    5.00    --  -40.79 -52.00 -32.00   40
  8  \w     -9.00  19.00   1.00    5.00    --  -40.79  52.00 113.00   28
  9  \w    -55.00 -19.00   1.00    5.00    --  -40.79  52.00 113.00   36
 10  \w     19.00  45.00   1.00    5.00    --   40.79  38.00  60.00   26
 11  \w    -29.00  67.00   1.00    5.00    --   40.79 -52.00 -32.00   96
 12  \w     48.00 113.00   1.00    5.00    --   40.79  38.00  60.00   65
 13  \w     25.00  97.00   1.00    5.00    --   40.79-125.00-120.00   72
 14  \w     17.00  42.00   1.00    5.00    --   46.00  67.00 174.16   25
 15  \w     55.00  82.00   1.00    5.00    --   46.00  67.00 174.16   27
 16  \w     11.00  36.00   1.00    5.00    --   46.00  84.00-172.15   25
 17  \w     11.00  37.00   1.00    5.00    --   46.00  84.00 -90.36   26
 18  \w     11.00  36.00   1.00    5.00    --   46.00  84.00 -31.27   25
 19  \w     16.00  42.00   1.00    5.00    --   50.00  81.00 150.93   26
 20  \w     17.00  43.00   1.00    5.00    --   50.00  80.00  62.62   26
 21  \w     17.00  42.00   1.00    5.00    --   50.00  79.00 119.94   25
 22  \w     71.00  97.00   1.00    5.00    --   58.00  75.00-110.93   26
 23  \w     25.00  54.00   1.00    5.00    --   58.00  77.00  22.90   29
 24  \w     27.00  65.00   1.00    5.00    --   58.00  75.00-110.93   38
 25  \w     26.00  62.00   1.00    5.00    --   58.00  75.00 -41.14   36
 26  \w     32.00  60.00   1.00    5.00    --   62.00  75.00 121.98   28
 27  \w     31.00  56.00   1.00    5.00    --   62.00  76.00-165.31   25
 28  \w     35.00  69.00   1.00    5.00    --   66.00  76.00  64.36   34
 29  \w     98.00 124.00   1.00    5.00    --   66.00  76.00 -27.22   26
 30  \w     34.00  66.00   1.00    5.00    --   66.00  76.00 -27.22   32
 31  \w     92.00 142.00   1.00    5.00    --   66.00  76.00  64.36   50
 32  \w     39.00 142.00   1.00    5.00    --   70.00  76.00-107.36  103
 33  \w     43.00  69.00   1.00    5.00    --   70.00  61.00  67.04   26
 34  \w     45.00  71.00   1.00   20.00    --   74.00  65.00  19.17   26
 35  \w     42.00  70.00   1.00   20.00    --   74.00  75.00 141.27   28
 36  \w     46.00  75.00   1.00   20.00    --   78.00  77.00 166.85   29
 37  \w    104.00 153.00   1.00   20.00    --   78.00  74.00 104.22   49
 38  \w     46.00  74.00   1.00   20.00    --   78.00  74.00 104.22   28
 39  \w     51.00  83.00   1.00   20.00    --   82.00  72.00-141.98   32
 40  \w     53.00  93.00   1.00   20.00    --   82.00  67.00 -62.72   40
 41  \w     57.00  83.00   1.00   20.00    --   86.00  71.00-178.38   26
 42  \w     56.00  95.00   1.00   20.00    --   86.00  65.00 -85.40   39
 43  \w    124.00 157.00   1.00   20.00    --   90.00  75.00 -54.61   33
 44  \w     62.00 112.00   1.00   20.00    --   90.00  75.00 -54.61   50
 45  \w     69.00 104.00   1.00   20.00    --  105.59 -94.00  60.00   35
 46  \w    115.00 147.00   1.00   20.00    --  105.59  77.00  60.00   32
 47  \w     33.00  63.00   1.00   20.00    --  105.59 -94.00  60.00   30
 48  \w     77.00 105.00   1.00   20.00    --  105.59  77.00  60.00   28
 49  \w     73.00 173.00   1.00   20.00    --  105.59  77.00   0.00  100
 50  \w     24.00 108.00   1.00   20.00    --  105.59 -94.00   0.00   84
 51  \w     73.00 101.00   1.00   20.00    --  105.59  77.00 120.00   28
 52  \w     81.00 128.00   1.00   20.00    --  105.59  61.00   0.00   47
 53  \w    112.00 177.00   1.00   20.00    --  105.59  77.00  90.00   65
 54  \w     73.00 177.00   1.00   20.00    --  105.59  77.00  30.00  104
 55  \w     75.00 102.00   1.00   20.00    --  105.59  77.00  90.00   27
 56  \w     75.00 143.00   1.00   20.00    --  105.59  77.00-180.00   68
 57  \w     74.00 178.00   1.00   20.00    --  105.59  77.00-120.00  104
 58  \w    109.00 148.00   1.00   20.00    --  105.59  77.00 -90.00   39
 59  \w     75.00 101.00   1.00   20.00    --  105.59  77.00 -90.00   26
 60  \w     73.00 177.00   1.00   20.00    --  105.59  77.00 -60.00  104
 61  \w     44.00 111.00   1.00   20.00    --  105.59-125.00 -30.00   67
 62  \w     74.00 177.00   1.00   20.00    --  105.59  77.00-150.00  103
 63  \w     36.00  98.00   1.00   20.00    --  105.59 -94.00-150.00   62
 64  \w     77.00 178.00   1.00   20.00    --  105.59  61.00 150.00  101
 65  \w    125.00 151.00   1.00   20.00    --  105.59  77.00 -30.00   26
 66  \w     73.00  99.00   1.00   20.00    --  105.59  77.00 -30.00   26
 67  \w     44.00 116.00   1.00   20.00    --  105.59-125.00-180.00   72
;
_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      -0.1770995000
_diffrn_orient_matrix_UB_12      -0.0028858000
_diffrn_orient_matrix_UB_13      0.0539478000
_diffrn_orient_matrix_UB_21      -0.0409968000
_diffrn_orient_matrix_UB_22      0.1417147000
_diffrn_orient_matrix_UB_23      0.0509523000
_diffrn_orient_matrix_UB_31      -0.0734263000
_diffrn_orient_matrix_UB_32      0.0996821000
_diffrn_orient_matrix_UB_33      -0.0913027000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.747
_diffrn_reflns_theta_min         3.375
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.360
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0032(6)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0687P)^2^+0.2186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3629
_reflns_number_total             4028
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           eyp1-12
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_original_cell_volume        1028.93(5)
_cod_database_code               1571475
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C1, N1, O3, O4
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              94657
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.807