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_7159008
_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         'C42 H50 O4'
_chemical_formula_sum            'C42 H50 O4'
_chemical_formula_weight         618.82
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-17 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.929(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9497(5)
_cell_length_b                   13.0829(4)
_cell_length_c                   17.7686(6)
_cell_measurement_reflns_used    4247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6370
_cell_measurement_theta_min      3.5710
_cell_volume                     3694.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    5.00   34.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -90.0000 29

  2 omega  -77.00  -10.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -90.0000 67

  3 omega  -24.00   35.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -60.0000 59

  4 omega   79.00  106.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -180.0000 27

  5 omega   59.00   85.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

  6 omega  -31.00   49.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   30.0000 80

  7 omega   17.00   59.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 42

  8 omega    3.00   82.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -180.0000 79

  9 omega   84.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

 10 omega   64.00   97.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 33

 11 omega   67.00   97.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 30

 12 omega   41.00   79.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 38

 13 omega   37.00   83.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 46

 14 omega   40.00   66.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 26

 15 omega   63.00  177.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 114

 16 omega   85.00  178.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 93

 17 omega   41.00   99.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 18 omega   42.00   68.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

 19 omega   37.00   89.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

 20 omega   38.00   91.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 21 omega   43.00   72.00   1.0000    5.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0750900000
_diffrn_orient_matrix_UB_12      0.0674661000
_diffrn_orient_matrix_UB_13      0.0173975000
_diffrn_orient_matrix_UB_21      -0.0360424000
_diffrn_orient_matrix_UB_22      -0.0082965000
_diffrn_orient_matrix_UB_23      -0.0830259000
_diffrn_orient_matrix_UB_31      -0.0496109000
_diffrn_orient_matrix_UB_32      -0.0961425000
_diffrn_orient_matrix_UB_33      0.0194335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.113
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0735P)^2^+0.7628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4903
_reflns_number_total             6598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01860h2.cif
_cod_data_source_block           20190488a
_cod_database_code               7159008
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.918
_reflns_odcompleteness_completeness 99.93
_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, All O(H) groups
2.a Riding coordinates:
 O4(H4A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C30(H30), C34(H34)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C37(H37A,
 H37B,H37C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'