Convenient synthesis of perhydrobenz[<i>e</i>]indene triketone, a key intermediate for the total synthesis of stelletins.
Cao, Yang; Liu, Xiaoyu; Wang, Zhe; Wang, Yuan; Jiao, Xiaozhen; Xie, Ping; Organic & biomolecular chemistry 21 (2023) 3850–3857; doi:10.1039/d3ob00319a

data_7159316
_publ_section_title
;
 Convenient synthesis of perhydrobenz[<i>e</i>]indene triketone, a key
 intermediate for the total synthesis of stelletins.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3850
_journal_page_last               3857
_journal_paper_doi               10.1039/d3ob00319a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H31 N O2'
_chemical_formula_sum            'C19 H31 N O2'
_chemical_formula_weight         305.45
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-02-08
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2023-02-27 deposited with the CCDC.	2023-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.115(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3053(3)
_cell_length_b                   12.1351(4)
_cell_length_c                   18.2588(9)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    113.70(14)
_cell_measurement_theta_max      28.1090
_cell_measurement_theta_min      3.8830
_cell_volume                     1617.55(12)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.70(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8568
_diffrn_measurement_details
;
  1 omega   24.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000   60.0000 59

  2 omega   10.00   83.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000  150.0000 73

  3 omega   -1.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000   30.0000 48

  4 omega   -5.00   21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508   57.0000 -120.0000 26

  5 omega    7.00   56.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852   57.0000 -120.0000 49

  6 omega  -47.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -77.0000  -90.0000 90

  7 omega  -51.00  -26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000 -180.0000 25

  8 omega   -7.00   18.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0085489000
_diffrn_orient_matrix_UB_12      -0.0582383000
_diffrn_orient_matrix_UB_13      0.0004715000
_diffrn_orient_matrix_UB_21      0.0236061000
_diffrn_orient_matrix_UB_22      0.0007404000
_diffrn_orient_matrix_UB_23      -0.0373504000
_diffrn_orient_matrix_UB_31      0.0938252000
_diffrn_orient_matrix_UB_32      0.0051073000
_diffrn_orient_matrix_UB_33      0.0108152000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12610
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98616
_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_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+0.7471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2503
_reflns_number_total             3144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ob00319a2.cif
_cod_data_source_block           exp_8288
_cod_depositor_comments          'Adding full bibliography for 7159316.cif.'
_cod_original_cell_volume        1617.56(12)
_cod_database_code               7159316
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07