Facile construction of dibenzodioxo[3.3.1]nonanes bearing spirocyclohexadienones via domino [4 + 2] cycloaddition/C(sp3)–H oxidative dehydrogenation coupling reactions
Chen, Genhui; Li, Hongjiao; Liang, Guojuan; Pu, Qian; Bai, Lijuan; Zhang, Dexin; Ye, Ying; Li, Yong; Zhou, Jing; Zhou, Hui; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01860H

data_7159009
_publ_section_title
;
 Facile construction of dibenzodioxo[3.3.1]nonanes bearing
 spirocyclohexadienones via domino [4 + 2] cycloaddition/C(sp3)--H
 oxidative dehydrogenation coupling reactions
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01860H
_journal_year                    2022
_chemical_formula_moiety         'C28 H40 O2'
_chemical_formula_sum            'C28 H40 O2'
_chemical_formula_weight         408.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-18 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                81.508(7)
_cell_angle_beta                 75.932(8)
_cell_angle_gamma                81.583(8)
_cell_formula_units_Z            1
_cell_length_a                   6.1016(6)
_cell_length_b                   10.4244(9)
_cell_length_c                   10.5390(8)
_cell_measurement_reflns_used    1192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4690
_cell_measurement_theta_min      4.2860
_cell_volume                     638.83(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -52.00  35.00   1.00    1.50    --  -33.50  57.00  90.00   87
  2  \w   -102.00 -15.00   1.00    1.50    --  -33.50 -57.00 -60.00   87
  3  \w   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 150.00   93
  4  \w      3.00  81.00   1.00    1.50    --   36.47-106.00 -78.00   78
  5  \w     -4.00  77.00   1.00    1.50    --   36.47 -99.00  60.00   81
  6  \w     57.00 110.00   1.00    1.50    --   36.47 178.00-120.00   53
  7  \w    -34.00  59.00   1.00    1.50    --   36.47 -37.00 -60.00   93
  8  \w    -32.00  55.00   1.00    1.50    --   36.47 -57.00-150.00   87
  9  \w     57.00 110.00   1.00    1.50    --   36.47 178.00 -60.00   53
 10  \w      8.00 106.00   1.00    1.50    --   36.47  77.00  90.00   98
 11  \w     37.00 134.00   1.00    5.00    --  108.00 -30.00 -60.00   97
 12  \w     38.00 110.00   1.00    5.00    --  108.00 -94.00   0.00   72
 13  \w     38.00 110.00   1.00    5.00    --  108.00 -94.00  90.00   72
 14  \w     79.00 177.00   1.00    5.00    --  108.00  77.00-120.00   98
 15  \w     50.00 134.00   1.00    5.00    --  108.00 -30.00  60.00   84
 16  \w     77.00 110.00   1.00    5.00    --  108.00 -61.00  90.00   33
 17  \w     47.00  73.00   1.00    5.00    --  108.00 -61.00  90.00   26
 18  \w    101.00 127.00   1.00    5.00    --  108.00 -77.00 -60.00   26
 19  \w     76.00 108.00   1.00    5.00    --  108.00-111.00 -60.00   32
 20  \w     40.00 124.00   1.00    5.00    --  108.00 -61.00-180.00   84
 21  \w     46.00  72.00   1.00    5.00    --  108.00-111.00 -60.00   26
 22  \w     37.00 136.00   1.00    5.00    --  108.00 -15.00 150.00   99
 23  \w     42.00  80.00   1.00    5.00    --  108.00 -77.00 -60.00   38
 24  \w     75.00 105.00   1.00    5.00    --  108.00-111.00-150.00   30
 25  \w     42.00 124.00   1.00    5.00    --  108.00 -15.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1618771000
_diffrn_orient_matrix_UB_12      0.1232028000
_diffrn_orient_matrix_UB_13      0.0379561000
_diffrn_orient_matrix_UB_21      -0.2058009000
_diffrn_orient_matrix_UB_22      -0.0725330000
_diffrn_orient_matrix_UB_23      0.0065998000
_diffrn_orient_matrix_UB_31      -0.0102025000
_diffrn_orient_matrix_UB_32      -0.0467678000
_diffrn_orient_matrix_UB_33      0.1467635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4594
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.317
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_description       prism
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0757P)^2^+0.0711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1616
_reflns_number_total             2279
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01860h2.cif
_cod_data_source_block           201910273
_cod_database_code               7159009
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4Cl4
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.930
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.859