Enantioselective Epoxidation of Alkenes Catalyzed by 2-Fluoro-N-Carbethoxytropinone and Related Tropinone Derivatives
Alan Armstrong; Ghafoor Ahmed; Belén Domínguez-Fernández; Barry R. Hayter; J. Steven Wailes; Journal of Organic Chemistry 67 (2002) 8610–8617; doi:10.1021/jo026322y

data_4022268
_publ_section_title
;
 Enantioselective Epoxidation of Alkenes Catalyzed by
 2-Fluoro-N-Carbethoxytropinone and Related Tropinone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8610
_journal_page_last               8617
_journal_paper_doi               10.1021/jo026322y
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         'C10 H14 F N O3'
_chemical_formula_sum            'C10 H14 F N O3'
_chemical_formula_weight         215.22
_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
_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                   6.439(2)
_cell_length_b                   7.680(2)
_cell_length_c                   20.619(5)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      17.20
_cell_measurement_theta_min      12.65
_cell_volume                     1019.7(4)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997b)'
_computing_molecular_graphics    'SHELXTL/PC version 5.03 (Sheldrick, 1995)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       \w-\q
_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  0.018
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2190
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        'variation +/-3.8'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0296
_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^)+(0.043P)^2^+0.257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                1702
_reflns_number_total             1795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026322y_s2.cif
_cod_data_source_block           DICYNF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geometrically placed' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4022268