Enolization Regioselectivity Involving Stereoisomeric 4a-Methyl-5-methoxyperhydrobenzo[7]annulen-2-ones
Wang, Xiaozhao; Butler, Sean C.; Gallucci, Judith C.; Paquette, Leo A.; The Journal of Organic Chemistry 74 (2009) 6825–6830; doi:10.1021/jo901391d

data_4028960
_publ_section_title
;
 Enolization Regioselectivity Involving Stereoisomeric
 4a-Methyl-5-methoxyperhydrobenzo[7]annulen-2-ones
;
_journal_issue                   17
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              6825
_journal_page_last               6830
_journal_paper_doi               10.1021/jo901391d
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H22 N2 O7'
_chemical_formula_sum            'C19 H22 N2 O7'
_chemical_formula_weight         390.39
_chemical_name_common            'Paquette 1523'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2009-06-05T11:02:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.385(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6110(4)
_cell_length_b                   11.5186(3)
_cell_length_c                   9.8507(2)
_cell_measurement_reflns_used    3435
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     1859.56(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1998)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.331705E-1
_diffrn_orient_matrix_UB_12      -0.613989E-1
_diffrn_orient_matrix_UB_13      0.756098E-1
_diffrn_orient_matrix_UB_21      0.82068E-1
_diffrn_orient_matrix_UB_22      -0.140846E-1
_diffrn_orient_matrix_UB_23      0.245664E-1
_diffrn_orient_matrix_UB_31      -0.6196E-2
_diffrn_orient_matrix_UB_32      0.41373E-1
_diffrn_orient_matrix_UB_33      0.444191E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24467
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rhombus-shaped block'
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0721P)^2^+0.5435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1349
_reflns_number_gt                2469
_reflns_number_total             3259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901391dsup1.cif
_cod_data_source_block           Paquette1523
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028960