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_1571473
_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 unk
_chemical_formula_moiety         'C27 H19 N O5'
_chemical_formula_sum            'C27 H19 N O5'
_chemical_formula_weight         437.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_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            8
_cell_length_a                   15.4716(8)
_cell_length_b                   10.1507(8)
_cell_length_c                   27.2357(19)
_cell_measurement_reflns_used    7753
_cell_measurement_temperature    295
_cell_measurement_theta_max      75.9970
_cell_measurement_theta_min      4.7020
_cell_volume                     4277.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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 0.964
_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    -71.00 -35.00   1.00    2.00    --  -22.88 123.00-102.00   36
  2  \w    -58.00  63.00   1.00    2.00    --  -22.88   8.00 147.00  121
  3  \w   -140.00-115.00   1.00    5.00    --  -70.50-129.00 -89.00   25
  4  \w   -161.00 -52.00   1.00    5.00    --  -70.50   8.00 147.00  109
  5  \w     79.00 113.00   1.00    5.00    --   71.94-141.00  97.00   34
  6  \w     95.00 161.00   1.00    5.00    --   71.94 123.00-102.00   66
  7  \w     37.00  73.00   1.00    5.00    --   71.94-141.00  97.00   36
  8  \w    136.00 162.00   1.00   12.00    --  121.00  -8.00 -27.00   26
  9  \w     27.00  53.00   1.00   12.00    --  121.00  -8.00 -27.00   26
 10  \w     94.00 135.00   1.00   12.00    --  121.00 129.00 -16.00   41
 11  \w     56.00  81.00   1.00   12.00    --  121.00-141.00  97.00   25
 12  \w     49.00  74.00   1.00   12.00    --  121.00-123.00 176.00   25
 13  \w     51.00  76.00   1.00   12.00    --  121.00-129.00 -89.00   25
 14  \w    102.00 128.00   1.00   12.00    --  121.00   8.00 147.00   26
 15  \w    112.00 137.00   1.00   12.00    --  121.00 123.00-102.00   25
 16  \w    101.00 161.00   1.00    5.00    --   71.94 111.00-150.00   60
 17  \w     51.00  76.00   1.00    5.00    --   71.94  -8.00 -27.00   25
 18  \w    107.00 162.00   1.00    5.00    --   71.94 111.00 -60.00   55
 19  \w     52.00  78.00   1.00   12.00    --  121.00 -63.00  60.00   26
 20  \w    108.00 175.00   1.00   12.00    --  121.00 111.00 -60.00   67
 21  \w     66.00  92.00   1.00   12.00    --  121.00 -91.00 -90.00   26
 22  \w     43.00  94.00   1.00   12.00    --  121.00-111.00  90.00   51
 23  \w    101.00 154.00   1.00   12.00    --  121.00 111.00-120.00   53
 24  \w     32.00 109.00   1.00   12.00    --  121.00-111.00 120.00   77
 25  \w    127.00 176.00   1.00   12.00    --  121.00 111.00 -30.00   49
 26  \w     56.00  91.00   1.00   12.00    --  121.00-111.00  30.00   35
 27  \w     24.00  60.00   1.00   12.00    --  121.00 -91.00 -90.00   36
 28  \w     61.00  86.00   1.00   12.00    --  121.00 178.00-120.00   25
 29  \w     98.00 124.00   1.00   12.00    --  121.00 -91.00 -90.00   26
 30  \w     42.00  67.00   1.00   12.00    --  121.00-111.00 -30.00   25
 31  \w     75.00 131.00   1.00   12.00    --  121.00  38.00  90.00   56
 32  \w     87.00 112.00   1.00   12.00    --  121.00-111.00 -30.00   25
 33  \w     60.00 112.00   1.00   12.00    --  121.00-111.00   0.00   52
 34  \w     86.00 124.00   1.00   12.00    --  121.00 178.00 -90.00   38
 35  \w     99.00 132.00   1.00   12.00    --  121.00-145.00 -32.30   33
 36  \w     82.00 111.00   1.00   12.00    --  121.00  50.00   0.00   29
 37  \w     88.00 161.00   1.00   12.00    --  121.00  77.00-150.00   73
 38  \w     35.00  60.00   1.00   12.00    --  121.00 -91.00-120.00   25
 39  \w    100.00 125.00   1.00   12.00    --  121.00 -91.00-120.00   25
 40  \w    102.00 176.00   1.00   12.00    --  121.00 111.00 -90.00   74
 41  \w     75.00 110.00   1.00   12.00    --  121.00-111.00  60.00   35
 42  \w    126.00 151.00   1.00   12.00    --  121.00 -63.00  60.00   25
 43  \w     98.00 123.00   1.00   12.00    --  121.00-132.00 -75.85   25
 44  \w     91.00 135.00   1.00   12.00    --  121.00-150.00  13.00   44
;
_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      -0.0002232000
_diffrn_orient_matrix_UB_12      -0.0349527000
_diffrn_orient_matrix_UB_13      0.1187985000
_diffrn_orient_matrix_UB_21      0.0057381000
_diffrn_orient_matrix_UB_22      0.0444585000
_diffrn_orient_matrix_UB_23      0.0939643000
_diffrn_orient_matrix_UB_31      -0.0995198000
_diffrn_orient_matrix_UB_32      0.0025908000
_diffrn_orient_matrix_UB_33      0.0051500000
_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  0.0482
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29242
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.530
_diffrn_reflns_theta_min         4.649
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     598
_refine_ls_number_reflns         7959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1336P)^2^+0.1614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.1946
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                6706
_reflns_number_total             7959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           ag3-166
_cod_depositor_comments
;
Adding full bibliography for 1571472--1571478.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C54 H38 N2 O10'
_cod_original_formula_weight         874.86
_cod_original_formula_moiety         '2(C27 H19 N O5)'
_cod_original_formula_units_Z            4
_cod_database_code               1571473
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c27 h19 n1 o5'
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.801
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(4)
 0.2(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C14(H14), C28(H28), C29(H29)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C34(H34), C36(H36),
  C37(H37), C39(H39), C40(H40), C43(H43), C44(H44), C45(H45), C46(H46),
 C47(H47), C49(H49), C50(H50), C51(H51), C52(H52)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              30441
_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 2.304
_oxdiff_exptl_absorpt_empirical_full_min 0.700