Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/ Acid Anhydride: Reversal of Stereoselectivity
Chai Ling Fan; Wei-Der Lee; Nai-Wei Teng; Ying-Chieh Sun; Kwunmin Chen; Journal of Organic Chemistry 68 (2003) 9816–9818; doi:10.1021/jo034807w

data_4022527
_publ_section_title
;
 Epoxidation of Chiral Camphor N-Enoylpyrazolidinones with
 Methyl(trifluoromethyl)dioxirane and Urea Hydrogen Peroxide/
 Acid Anhydride: Reversal of Stereoselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9816
_journal_page_last               9818
_journal_paper_doi               10.1021/jo034807w
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C21 H28 N2 O4 '
_chemical_formula_sum            'C21 H28 N2 O4'
_chemical_formula_weight         372.465
_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           maXus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6118(3)
_cell_length_b                   10.6555(3)
_cell_length_c                   17.8821(7)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.395
_cell_volume                     2022.00(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.00354
_diffrn_orient_matrix_UB_12      0.09416
_diffrn_orient_matrix_UB_13      -0.00118
_diffrn_orient_matrix_UB_21      -0.00303
_diffrn_orient_matrix_UB_22      0.00106
_diffrn_orient_matrix_UB_23      0.09379
_diffrn_orient_matrix_UB_31      0.05585
_diffrn_orient_matrix_UB_32      0.00212
_diffrn_orient_matrix_UB_33      0.00178
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3890
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cube
_exptl_crystal_F_000             736
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.05
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_coef       50E4(19)
_refine_ls_extinction_expression
;
  equation(22) p292 'Crystallographic Computing' (1970)
  coefficient is multiplied by 10^4
;
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.721
_refine_ls_goodness_of_fit_gt    1.620
_refine_ls_goodness_of_fit_ref   1.616
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.096
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.091
_reflns_d_resolution_high        0.64
_reflns_d_resolution_low         1.63
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                1700
_reflns_number_total             2340
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            jo034807wsi20030626_040925.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value
27 times.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21    '
_cod_original_formula_sum        'C21 H28 N2 O4 '
_cod_database_code               4022527