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_1571472
_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         'C28 H21 N O4'
_chemical_formula_sum            'C28 H21 N O4'
_chemical_formula_weight         435.46
_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             2021-09-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_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                   12.28419(14)
_cell_length_b                   13.47791(17)
_cell_length_c                   13.83030(17)
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.8220
_cell_measurement_theta_min      3.1370
_cell_volume                     2289.82(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.988
_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  32.00   1.00    1.50    --  -40.79  65.00 -12.00  103
  2  \w     27.00 140.00   1.00   12.50    --  105.59 -83.00 100.00  113
  3  \w     74.00 178.00   1.00   12.50    --  105.59  73.00 112.00  104
  4  \w     23.00  97.00   1.00    1.50    --   40.79-125.00-120.00   74
  5  \w     23.00  97.00   1.00    1.50    --   40.79-125.00 120.00   74
  6  \w     23.00  97.00   1.00    1.50    --   40.79-125.00-150.00   74
  7  \w     80.00 178.00   1.00   12.50    --  105.59  45.00-180.00   98
  8  \w     32.00 118.00   1.00   12.50    --  105.59-125.00-150.00   86
  9  \w     80.00 178.00   1.00   12.50    --  105.59  45.00 -90.00   98
 10  \w     94.00 178.00   1.00   12.50    --  105.59 125.00 -60.00   84
 11  \w     33.00 135.00   1.00   12.50    --  105.59 -65.00-148.00  102
 12  \w   -113.00 -13.00   1.00    1.50    --  -40.79 -57.00-120.00  100
 13  \w   -117.00 -26.00   1.00    1.50    --  -40.79 -77.00 120.00   91
 14  \w   -113.00 -13.00   1.00    1.50    --  -40.79 -57.00   0.00  100
;
_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      0.1056739000
_diffrn_orient_matrix_UB_12      -0.0599867000
_diffrn_orient_matrix_UB_13      0.0138252000
_diffrn_orient_matrix_UB_21      -0.0353503000
_diffrn_orient_matrix_UB_22      -0.0714525000
_diffrn_orient_matrix_UB_23      -0.0811630000
_diffrn_orient_matrix_UB_31      0.0576519000
_diffrn_orient_matrix_UB_32      0.0661336000
_diffrn_orient_matrix_UB_33      -0.0750913000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.917
_diffrn_reflns_theta_min         4.581
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (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    1.263
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0641P)^2^+0.1170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4184
_reflns_number_total             4475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           ag2018
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_database_code               1571472
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c28 h21 n1 o4'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.864
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(3)
 0.0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              51471
_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 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.812