An Enantioselective Organocatalytic Oxidative Dearomatization Strategy
Ngoc T. Vo; Robert D. M. Pace; Fionn O'Har; Matthew J. Gaunt; Journal of the American Chemical Society 130 (2008) 404–405; doi:10.1021/ja077457u

data_4107292
_publ_section_title
;
 An Enantioselective Organocatalytic Oxidative Dearomatization Strategy
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              404
_journal_page_last               405
_journal_paper_doi               10.1021/ja077457u
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration
;
 1234 Friedel pairs were averaged for the refinement.
;
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6822(2)
_cell_length_b                   8.5740(3)
_cell_length_c                   19.7420(7)
_cell_measurement_reflns_used    11512
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.00
_cell_volume                     1300.35(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7121
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.4206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1842
_reflns_number_total             2129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja077457u-file003.cif
_cod_data_source_block           mg0602
_cod_database_code               4107292