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_1571478
_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 H16 O3'
_chemical_formula_sum            'C27 H16 O3'
_chemical_formula_weight         388.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8746(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.93381(14)
_cell_length_b                   15.53317(18)
_cell_length_c                   11.17806(14)
_cell_measurement_reflns_used    8351
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.1980
_cell_measurement_theta_min      4.9340
_cell_volume                     1896.06(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3045
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -56.00  33.00   1.00    1.00    --  -40.57  60.00 -29.00   89
  2  \w   -108.00 -15.00   1.00    1.00    --  -40.57 -60.00-169.00   93
  3  \w     38.00 118.00   1.00    5.00    --  103.49 -60.00-169.00   80
  4  \w     75.00 172.00   1.00    5.00    --  103.49  60.00 -29.00   97
  5  \w     15.00  58.00   1.00    1.00    --   40.57 -99.00  30.00   43
  6  \w     16.00 106.00   1.00    1.00    --   40.57  38.00 120.00   90
  7  \w     39.00  87.00   1.00    1.00    --   40.57-125.00-180.00   48
  8  \w     80.00 177.00   1.00    5.00    --  103.49  30.00 -60.00   97
  9  \w    114.00 175.00   1.00    5.00    --  103.49 111.00-180.00   61
 10  \w     75.00 103.00   1.00    5.00    --  103.49  61.00  30.00   28
 11  \w    140.00 166.00   1.00    5.00    --  103.49  61.00  60.00   26
 12  \w     74.00 157.00   1.00    5.00    --  103.49  61.00  90.00   83
 13  \w     33.00 107.00   1.00    5.00    --  103.49-111.00-150.00   74
 14  \w     87.00 113.00   1.00    5.00    --  103.49  45.00  60.00   26
 15  \w     83.00 133.00   1.00    5.00    --  103.49  30.00 150.00   50
 16  \w    116.00 150.00   1.00    5.00    --  103.49 111.00-150.00   34
 17  \w    106.00 157.00   1.00    5.00    --  103.49  77.00   0.00   51
 18  \w     79.00 131.00   1.00    5.00    --  103.49  45.00  90.00   52
 19  \w    123.00 172.00   1.00    5.00    --  103.49  61.00  30.00   49
 20  \w     80.00 106.00   1.00    5.00    --  103.49  61.00  60.00   26
 21  \w     35.00 100.00   1.00    5.00    --  103.49-111.00  60.00   65
;
_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      -0.0224222000
_diffrn_orient_matrix_UB_12      0.0125591000
_diffrn_orient_matrix_UB_13      0.1338245000
_diffrn_orient_matrix_UB_21      0.1006924000
_diffrn_orient_matrix_UB_22      0.0693886000
_diffrn_orient_matrix_UB_23      0.0084164000
_diffrn_orient_matrix_UB_31      -0.0962254000
_diffrn_orient_matrix_UB_32      0.0697671000
_diffrn_orient_matrix_UB_33      -0.0325144000
_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14711
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.341
_diffrn_reflns_theta_min         4.878
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0530P)^2^+0.2575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3365
_reflns_number_total             3710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00745j2.cif
_cod_data_source_block           eyp2-163
_cod_depositor_comments
'Adding full bibliography for 1571472--1571478.cif.'
_cod_database_code               1571478
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'c27 h16 o3'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              96486
_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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.756