Construction of cyclobutane-fused tetracyclic skeletons <i>via</i> substrate-dependent EnT-enabled dearomative [2+2] cycloaddition of benzofurans (benzothiophenes)/maleimides.
Liao, Zhi-Yu; Gao, Fan; Ye, Yu-Hang; Yu, Qian-Hui; Yang, Cui; Luo, Qing-Yu; Du, Fei; Pan, Bin; Zhong, Wen-Wu; Liang, Wu; Chemical communications (Cambridge, England) 60 (2024) 4455–4458; doi:10.1039/d4cc00690a

data_7132884
_publ_section_title
;
 Construction of cyclobutane-fused tetracyclic skeletons <i>via</i>
 substrate-dependent EnT-enabled dearomative [2+2] cycloaddition of
 benzofurans (benzothiophenes)/maleimides.
;
_journal_issue                   33
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4455
_journal_page_last               4458
_journal_paper_doi               10.1039/d4cc00690a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H13 N O3'
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29
_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             2023-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.24800(10)
_cell_length_b                   11.9893(2)
_cell_length_c                   21.1722(2)
_cell_measurement_reflns_used    7792
_cell_measurement_temperature    292.37(10)
_cell_measurement_theta_max      71.5520
_cell_measurement_theta_min      4.2320
_cell_volume                     2855.19(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.37(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_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   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00-150.00   84
  2  \w    -33.00  55.00   1.00    1.00    --   35.97 -38.00 -90.00   88
  3  \w     28.00  90.00   1.00    1.00    --   35.97-126.00-180.00   62
  4  \w     38.00 109.00   1.00    1.77    --  107.97-112.00 -90.00   71
  5  \w     38.00 109.00   1.00    1.77    --  107.97-112.00-180.00   71
  6  \w    103.00 176.00   1.00    1.77    --  107.97  77.00 -60.00   73
  7  \w     90.00 175.00   1.00    1.77    --  107.97  61.00-180.00   85
  8  \w    103.00 176.00   1.00    1.77    --  107.97  77.00-150.00   73
  9  \w    103.00 176.00   1.00    1.77    --  107.97  77.00 -90.00   73
 10  \w    104.00 178.00   1.00    1.77    --  107.97 112.00  30.00   74
 11  \w   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00 -60.00   88
 12  \w    -55.00  33.00   1.00    1.00    --  -35.97  38.00 120.00   88
 13  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  60.00   84
 14  \w     87.00 147.00   1.00    1.77    --  107.97  30.00  30.00   60
 15  \w     90.00 175.00   1.00    1.77    --  107.97  61.00 120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0807523000
_diffrn_orient_matrix_UB_12      0.0052290000
_diffrn_orient_matrix_UB_13      -0.0586992000
_diffrn_orient_matrix_UB_21      0.1105617000
_diffrn_orient_matrix_UB_22      -0.0021790000
_diffrn_orient_matrix_UB_23      0.0428867000
_diffrn_orient_matrix_UB_31      0.0013656000
_diffrn_orient_matrix_UB_32      -0.1284070000
_diffrn_orient_matrix_UB_33      -0.0031584000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14004
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.819
_diffrn_reflns_theta_min         5.739
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0855P)^2^+1.4358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2592
_reflns_number_total             2758
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00690a2.cif
_cod_data_source_block           bo3zb-acctone
_cod_depositor_comments          'Adding full bibliography for 7132884.cif.'
_cod_database_code               7132884
_shelxl_version_number           2014-1
_chemical_oxdiff_usercomment     'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.799
_shelx_estimated_absorpt_t_min   0.736
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
;
_olex2_date_sample_data_collection 2023-10-16
_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 2.856
_oxdiff_exptl_absorpt_empirical_full_min 0.441