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_7129852
_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         'C40 H40 O4 S'
_chemical_formula_sum            'C40 H40 O4 S'
_chemical_formula_weight         616.78
_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     iterative
_audit_creation_date             2020-12-04
_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                 101.2817(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6560(2)
_cell_length_b                   12.29932(13)
_cell_length_c                   17.8070(2)
_cell_measurement_reflns_used    5657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9130
_cell_measurement_theta_min      4.3890
_cell_volume                     3792.19(7)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -60.00 -34.00   0.50    2.00    --  -33.50 -57.00   0.00   52
  2  \w    -99.00 -42.00   0.50    2.00    --  -33.50 178.00  60.00  114
  3  \w   -101.00 -72.00   0.50    2.00    --  -33.50 -57.00   0.00   58
  4  \w    -32.00  14.00   0.50    2.00    --   36.47 -19.00 120.00   92
  5  \w     58.00  98.00   0.50    2.00    --   36.47 178.00-180.00   80
  6  \w     69.00  95.00   0.50    2.00    --   36.47 178.00 -90.00   52
  7  \w     47.00  73.00   0.50    2.00    --   36.47 -19.00 120.00   52
  8  \w     57.00 105.00   0.50    2.00    --   36.47 178.00   0.00   96
  9  \w     61.00 110.00   0.50    2.00    --   36.47 178.00  60.00   98
 10  \w     22.00  66.00   0.50    2.00    --   36.47  57.00-180.00   88
 11  \w      9.00  40.00   0.50    2.00    --   36.47  77.00  60.00   62
 12  \w     58.00 102.00   0.50    2.00    --   36.47  77.00  60.00   88
 13  \w     38.00  90.00   0.50   12.50    --  108.00 -94.00-150.00  104
 14  \w     90.00 170.00   0.50   12.50    --  108.00  45.00 120.00  160
 15  \w    112.00 167.00   0.50   12.50    --  108.00  61.00 -30.00  110
 16  \w     48.00 110.00   0.50   12.50    --  108.00 -94.00 -90.00  124
 17  \w     42.00 123.00   0.50   12.50    --  108.00 -61.00  60.00  162
 18  \w     43.00 128.00   0.50   12.50    --  108.00 -61.00 -60.00  170
 19  \w    133.00 176.00   0.50   12.50    --  108.00  61.00  90.00   86
 20  \w    116.00 168.00   0.50   12.50    --  108.00 111.00-150.00  104
 21  \w     96.00 152.00   0.50   12.50    --  108.00  77.00  30.00  112
;
_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      -0.0377420000
_diffrn_orient_matrix_UB_12      0.0606353000
_diffrn_orient_matrix_UB_13      0.0588974000
_diffrn_orient_matrix_UB_21      -0.0456105000
_diffrn_orient_matrix_UB_22      0.0711998000
_diffrn_orient_matrix_UB_23      -0.0645347000
_diffrn_orient_matrix_UB_31      -0.0664139000
_diffrn_orient_matrix_UB_32      -0.0833122000
_diffrn_orient_matrix_UB_33      -0.0122618000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16124
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.397
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86820
_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    1.080
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.043
_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     415
_refine_ls_number_reflns         6753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0709P)^2^+0.3573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5440
_reflns_number_total             6753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00183g2.cif
_cod_data_source_block           202012289a
_cod_original_cell_volume        3792.21(8)
_cod_database_code               7129852
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 99.83
_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), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C34(H34), C36(H36)
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), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              33405
_shelx_hkl_checksum              39798
_shelx_fab_checksum              19759
_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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.879