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_7129851
_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 H31 Br O2'
_chemical_formula_sum            'C31 H31 Br O2'
_chemical_formula_weight         515.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-07-03
_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                 105.181(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8373(4)
_cell_length_b                   11.7899(3)
_cell_length_c                   27.1076(7)
_cell_measurement_reflns_used    5381
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9330
_cell_measurement_theta_min      4.4660
_cell_volume                     5810.2(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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   -108.00 -32.00   0.50    3.50    --  -33.50 178.00-150.00  152
  2  \w    -83.00 -57.00   0.50    3.50    --  -33.50 -57.00 -60.00   52
  3  \w    -90.00 -55.00   0.50    3.50    --  -33.50-155.00-111.00   70
  4  \w    -54.00 -28.00   0.50    3.50    --  -33.50 -57.00 -60.00   52
  5  \w     19.00 102.00   0.50    3.50    --   36.47  57.00  90.00  166
  6  \w     57.00  87.00   0.50    3.50    --   36.47 178.00   0.00   60
  7  \w     34.00 101.00   0.50    3.50    --   36.47  57.00-180.00  134
  8  \w     17.00  54.00   0.50    3.50    --   36.47 -57.00-180.00   74
  9  \w     57.00  82.00   0.50    3.50    --   36.47 178.00  30.00   50
 10  \w    124.00 162.00   0.50   21.00    --  108.00  61.00  30.00   76
 11  \w     39.00 153.00   0.50   21.00    --  108.00 -15.00-120.00  228
 12  \w     55.00 124.00   0.50   21.00    --  108.00 -45.00 -90.00  138
 13  \w     55.00 112.00   0.50   21.00    --  108.00-111.00-150.00  114
 14  \w     38.00 134.00   0.50   21.00    --  108.00 -30.00  90.00  192
 15  \w    118.00 159.00   0.50   21.00    --  108.00  45.00  90.00   82
 16  \w     59.00 131.00   0.50   21.00    --  108.00 178.00-150.00  144
;
_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      0.0720748000
_diffrn_orient_matrix_UB_12      -0.0579995000
_diffrn_orient_matrix_UB_13      -0.0029967000
_diffrn_orient_matrix_UB_21      -0.0207593000
_diffrn_orient_matrix_UB_22      0.0190297000
_diffrn_orient_matrix_UB_23      -0.0582938000
_diffrn_orient_matrix_UB_31      0.0394274000
_diffrn_orient_matrix_UB_32      0.1156576000
_diffrn_orient_matrix_UB_33      0.0079943000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10467
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.379
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85670
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0716P)^2^+2.7739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4540
_reflns_number_total             5147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00183g2.cif
_cod_data_source_block           20200770
_cod_original_cell_volume        5810.3(2)
_cod_database_code               7129851
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4Br1
_shelx_estimated_absorpt_t_max   0.818
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.27
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.c 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              53946
_shelx_hkl_checksum              51934
_shelx_fab_checksum              3544
_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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.872