Asymmetric desymmetrization of 4,5-epoxycyclohex-1-ene by enantioselective allylic oxidation.
Tan, Qitao; Hayashi, Masahiko; Organic letters 11 (2009) 3314–3317; doi:10.1021/ol901284v

data_1504044
_publ_section_title
;
 Asymmetric desymmetrization of 4,5-epoxycyclohex-1-ene by
 enantioselective allylic oxidation.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3314
_journal_page_last               3317
_journal_paper_doi               10.1021/ol901284v
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C13 H11 N O5'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.23
_chemical_name_common
(3S,4S,5S)-3-(4-Nitro)benzoyloxy-4,5-epoxycyclohex-1-ene
_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
_audit_update_record
;
2009-05-12 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3632(16)
_cell_length_b                   11.501(3)
_cell_length_c                   16.661(4)
_cell_measurement_reflns_used    2727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.15
_cell_volume                     1219.3(5)
_computing_cell_refinement       'Bruker AXS SAINT'
_computing_data_collection       'Bruker AXS SAINT'
_computing_data_reduction        'Bruker AXS SAINT'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6176
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'program SADABS ver. 2.03(Sheldrick)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0314P)^2^+0.0699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                1541
_reflns_number_total             2727
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901284v_si_002.cif
_cod_data_source_block           ol_Hayashi_compound_6
_cod_database_code               1504044