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_1571476
_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 H17 N O5'
_chemical_formula_sum            'C27 H17 N O5'
_chemical_formula_weight         435.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-30
_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            8
_cell_length_a                   10.9082(6)
_cell_length_b                   13.4620(7)
_cell_length_c                   28.2100(13)
_cell_measurement_reflns_used    6592
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.3350
_cell_measurement_theta_min      5.1240
_cell_volume                     4142.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (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 0.995
_diffrn_measured_fraction_theta_max 0.917
_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      0.00  51.00   1.00    1.00    --    0.00 -96.00 103.00   51
  2  \w    -95.00  16.00   1.00    5.00    --  -55.48  58.00 -17.00  111
  3  \w   -146.00-120.00   1.00    5.00    --  -55.48 -72.00 -12.00   26
  4  \w     -1.00  41.00   1.00    5.00    --   55.48 -96.00 103.00   42
  5  \w     66.00 146.00   1.00   20.00    --  110.96  72.00 117.00   80
  6  \w    115.00 140.00   1.00   20.00    --  110.96  96.00-147.00   25
  7  \w     36.00  66.00   1.00   20.00    --  110.96 -96.00 103.00   30
  8  \w     30.00 145.00   1.00   20.00    --  110.96 -58.00-158.00  115
  9  \w     57.00  82.00   1.00    1.00    --    0.00 178.00 -60.00   25
 10  \w     13.00  48.00   1.00    1.00    --    0.00 -99.00 -60.00   35
 11  \w      3.00  48.00   1.00    1.00    --    0.00 -99.00-150.00   45
 12  \w    -92.00  -2.00   1.00    5.00    --  -55.48 125.00 -30.00   90
 13  \w     33.00 102.00   1.00    5.00    --   55.48-125.00-150.00   69
 14  \w    149.00 176.00   1.00   20.00    --  110.96  50.00  30.00   27
 15  \w    143.00 169.00   1.00   20.00    --  110.96 111.00 -30.00   26
 16  \w     71.00 144.00   1.00   20.00    --  110.96  50.00  30.00   73
 17  \w    126.00 152.00   1.00   20.00    --  110.96 111.00-180.00   26
 18  \w     60.00 178.00   1.00   20.00    --  110.96  38.00  90.00  118
 19  \w     67.00  93.00   1.00   20.00    --  110.96  77.00 -90.00   26
 20  \w     34.00 106.00   1.00   20.00    --  110.96-111.00-150.00   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      -0.0783580000
_diffrn_orient_matrix_UB_12      -0.0016541000
_diffrn_orient_matrix_UB_13      0.0453456000
_diffrn_orient_matrix_UB_21      -0.0838137000
_diffrn_orient_matrix_UB_22      -0.0794355000
_diffrn_orient_matrix_UB_23      -0.0223482000
_diffrn_orient_matrix_UB_31      0.0823653000
_diffrn_orient_matrix_UB_32      -0.0824014000
_diffrn_orient_matrix_UB_33      0.0206044000
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.591
_diffrn_reflns_theta_min         5.126
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (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    1.396
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0661
_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^)+(0.1531P)^2^+4.1543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2310
_refine_ls_wR_factor_ref         0.2934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             3947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           eyp291
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_database_code               1571476
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c27 h17 n1 o5'
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.784
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15)
2.b 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              80195
_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 2.283
_oxdiff_exptl_absorpt_empirical_full_min 0.630