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_1571474
_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 H18 Cl N O4'
_chemical_formula_sum            'C27 H18 Cl N O4'
_chemical_formula_weight         455.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-28
_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                90
_cell_angle_beta                 112.958(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3160(5)
_cell_length_b                   9.2552(2)
_cell_length_c                   16.7635(5)
_cell_measurement_reflns_used    6371
_cell_measurement_temperature    295
_cell_measurement_theta_max      71.2690
_cell_measurement_theta_min      3.1110
_cell_volume                     2188.05(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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 0.994
_diffrn_measured_fraction_theta_max 0.978
_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    -80.00  17.00   1.00    5.00    --  -35.88  92.00  63.00   97
  2  \w   -126.00-101.00   1.00    5.00    --  -35.88 -92.00 -49.00   25
  3  \w     26.00  63.00   1.00    5.00    --   35.88 -92.00 -49.00   37
  4  \w    101.00 162.00   1.00   20.00    --  107.97  92.00  63.00   61
  5  \w     48.00 108.00   1.00   20.00    --  107.97 -92.00 -49.00   60
  6  \w   -125.00-100.00   1.00    5.00    --  -35.88 -99.00 -90.00   25
  7  \w   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00-180.00   43
  8  \w   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00  90.00   43
  9  \w   -105.00 -20.00   1.00    5.00    --  -35.88 -38.00-150.00   85
 10  \w   -119.00 -84.00   1.00    5.00    --  -35.88 -99.00-150.00   35
 11  \w   -121.00 -81.00   1.00    5.00    --  -35.88 -99.00-120.00   40
 12  \w   -124.00 -81.00   1.00    5.00    --  -35.88 -99.00 150.00   43
 13  \w     17.00  72.00   1.00    5.00    --   35.88 -77.00-120.00   55
 14  \w    -51.00 -26.00   1.00    5.00    --   35.88 -19.00   0.00   25
 15  \w     57.00 121.00   1.00    5.00    --   35.88 178.00 -60.00   64
 16  \w     90.00 115.00   1.00    5.00    --   35.88 -19.00   0.00   25
 17  \w    -55.00  -5.00   1.00    5.00    --   35.88 -77.00-120.00   50
 18  \w     59.00  95.00   1.00    5.00    --   35.88 178.00  60.00   36
 19  \w      5.00  43.00   1.00    5.00    --   35.88 -19.00   0.00   38
 20  \w     24.00 144.00   1.00   20.00    --  107.97 -61.00 -30.00  120
 21  \w    101.00 171.00   1.00   20.00    --  107.97 111.00  30.00   70
 22  \w     66.00 106.00   1.00   20.00    --  107.97 -94.00  60.00   40
 23  \w     72.00 177.00   1.00   20.00    --  107.97  45.00-150.00  105
 24  \w     22.00  50.00   1.00   20.00    --  107.97-111.00  60.00   28
 25  \w     22.00  47.00   1.00   20.00    --  107.97 -94.00  60.00   25
 26  \w    101.00 159.00   1.00   20.00    --  107.97  61.00 150.00   58
 27  \w     22.00  80.00   1.00   20.00    --  107.97-111.00-150.00   58
 28  \w     95.00 142.00   1.00   20.00    --  107.97  45.00  60.00   47
 29  \w     83.00 151.00   1.00   20.00    --  107.97  61.00 120.00   68
 30  \w     83.00 113.00   1.00   20.00    --  107.97-111.00  60.00   30
 31  \w    117.00 151.00   1.00   20.00    --  107.97 111.00  90.00   34
 32  \w     82.00 177.00   1.00   20.00    --  107.97  77.00   0.00   95
 33  \w     92.00 117.00   1.00   20.00    --  107.97 -45.00  30.00   25
 34  \w     60.00 110.00   1.00   20.00    --  107.97-111.00-120.00   50
 35  \w     64.00  89.00   1.00   20.00    --  107.97 -45.00  30.00   25
;
_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      0.0459521000
_diffrn_orient_matrix_UB_12      -0.1509585000
_diffrn_orient_matrix_UB_13      0.0141140000
_diffrn_orient_matrix_UB_21      -0.0324112000
_diffrn_orient_matrix_UB_22      -0.0187943000
_diffrn_orient_matrix_UB_23      -0.0987240000
_diffrn_orient_matrix_UB_31      0.0936031000
_diffrn_orient_matrix_UB_32      0.0676182000
_diffrn_orient_matrix_UB_33      0.0042769000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14184
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.517
_diffrn_reflns_theta_min         3.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (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    1.384
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_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     299
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0845P)^2^+0.6558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             4174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           ag2153f2
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_original_cell_volume        2188.05(12)
_cod_database_code               1571474
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.710
_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:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              9835
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.798