Divergent oxidative dearomatization coupling reactions to construct polycyclic cyclohexadienones
Pu, Qian; Huo, Mingming; Liang, Guojuan; Bai, Lijuan; Chen, Genhui; Li, Hongjiao; Xiang, Peng; Zhou, Hui; Zhou, Jing; Chemical Communications  (2022) –; doi:10.1039/D2CC00183G

data_7129850
_publ_section_title
;
 Divergent oxidative dearomatization coupling reactions to construct
 polycyclic cyclohexadienones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00183G
_journal_year                    2022
_chemical_formula_moiety         'C31 H30 O2'
_chemical_formula_sum            'C31 H30 O2'
_chemical_formula_weight         434.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-19 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.279(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8263(3)
_cell_length_b                   21.7654(4)
_cell_length_c                   11.6633(4)
_cell_measurement_reflns_used    5369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6500
_cell_measurement_theta_min      4.0530
_cell_volume                     2442.67(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -89.00 -58.00   1.00    1.00    --  -33.50 178.00-180.00   31
  2  \w    -88.00  -5.00   1.00    1.00    --  -33.50 -77.00-150.00   83
  3  \w    -34.00  69.00   1.00    1.00    --   36.47 -19.00  60.00  103
  4  \w     71.00 107.00   1.00    1.00    --   36.47 178.00 150.00   36
  5  \w     24.00 103.00   1.00    1.00    --   36.47  57.00  30.00   79
  6  \w     64.00  98.00   1.00    1.00    --   36.47  37.00 150.00   34
  7  \w    -22.00  13.00   1.00    1.00    --   36.47 -77.00 -90.00   35
  8  \w     64.00 100.00   1.00    1.00    --   36.47  57.00-120.00   36
  9  \w     57.00 109.00   1.00    1.00    --   36.47 178.00  60.00   52
 10  \w    -28.00   9.00   1.00    1.00    --   36.47 -57.00-150.00   37
 11  \w    -31.00   4.00   1.00    1.00    --   36.47 -77.00-180.00   35
 12  \w     -4.00  64.00   1.00    1.00    --   36.47 -99.00 -90.00   68
 13  \w     59.00 102.00   1.00    1.00    --   36.47 178.00-150.00   43
 14  \w     14.00  46.00   1.00    1.00    --   36.47  37.00 150.00   32
 15  \w     74.00 100.00   1.00    1.00    --   36.47 178.00-180.00   26
 16  \w     37.00  63.00   1.00    1.00    --   36.47 -77.00 -90.00   26
 17  \w     14.00  50.00   1.00    1.00    --   36.47 -77.00-180.00   36
 18  \w     89.00 135.00   1.00    6.00    --  108.00  30.00 120.00   46
 19  \w     91.00 136.00   1.00    6.00    --  108.00  61.00-150.00   45
 20  \w     49.00 107.00   1.00    6.00    --  108.00 -94.00  90.00   58
 21  \w     45.00 109.00   1.00    6.00    --  108.00 -94.00-162.00   64
 22  \w     89.00 178.00   1.00    6.00    --  108.00  45.00 -60.00   89
 23  \w     67.00 154.00   1.00    6.00    --  108.00  15.00  60.00   87
 24  \w     43.00 134.00   1.00    6.00    --  108.00 -30.00-180.00   91
 25  \w     84.00 110.00   1.00    6.00    --  108.00-111.00 -60.00   26
 26  \w     90.00 151.00   1.00    6.00    --  108.00  61.00  60.00   61
 27  \w    101.00 150.00   1.00    6.00    --  108.00 111.00 -30.00   49
 28  \w    142.00 168.00   1.00    6.00    --  108.00  61.00-150.00   26
 29  \w    112.00 170.00   1.00    6.00    --  108.00 111.00   0.00   58
 30  \w     46.00 119.00   1.00    6.00    --  108.00 -61.00-120.00   73
 31  \w     40.00  70.00   1.00    6.00    --  108.00 -61.00  30.00   30
 32  \w    148.00 176.00   1.00    6.00    --  108.00  30.00 120.00   28
 33  \w     53.00 109.00   1.00    6.00    --  108.00-111.00  30.00   56
 34  \w    121.00 175.00   1.00    6.00    --  108.00  61.00-180.00   54
 35  \w     89.00 116.00   1.00    6.00    --  108.00  61.00-180.00   27
;
_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      0.0670055000
_diffrn_orient_matrix_UB_12      0.0203430000
_diffrn_orient_matrix_UB_13      0.1422399000
_diffrn_orient_matrix_UB_21      0.0369388000
_diffrn_orient_matrix_UB_22      0.0625724000
_diffrn_orient_matrix_UB_23      -0.0380419000
_diffrn_orient_matrix_UB_31      -0.1406335000
_diffrn_orient_matrix_UB_32      0.0261711000
_diffrn_orient_matrix_UB_33      -0.0197313000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17345
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.062
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54867
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+0.3013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3487
_reflns_number_total             4339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00183g2.cif
_cod_data_source_block           20200101
_cod_original_cell_volume        2442.67(13)
_cod_database_code               7129850
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N1
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.892
_reflns_odcompleteness_completeness 99.73
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C23(H23)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              194
_shelx_hkl_checksum              85928
_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 2.707
_oxdiff_exptl_absorpt_empirical_full_min 0.840