Vanadium-catalyzed selenide oxidation with in situ[2,3] sigmatropic rearrangement (SOS reaction): scope and asymmetric applications.
Bourland, T. Campbell; Carter, Rich G.; Yokochi, Alexandre F. T.; Organic & biomolecular chemistry 2 (2004) 1315–1329; doi:10.1039/b316502g

data_7151609
_publ_section_title
;
 Vanadium-catalyzed selenide oxidation with in situ[2,3] sigmatropic
 rearrangement (SOS reaction): scope and asymmetric applications.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1315
_journal_page_last               1329
_journal_paper_doi               10.1039/b316502g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C22 H25 N O2 Se'
_chemical_formula_weight         414.39
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.049(9)
_cell_angle_beta                 98.288(15)
_cell_angle_gamma                99.018(15)
_cell_formula_units_Z            2
_cell_length_a                   5.2672(14)
_cell_length_b                   12.0311(14)
_cell_length_c                   17.196(2)
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      47.27
_cell_measurement_theta_min      2.68
_cell_volume                     1025.0(3)
_computing_cell_refinement       TwinSolve
_computing_data_collection       CrystalClear
_computing_data_reduction        TwinSolve
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.701
_diffrn_measured_fraction_theta_max 0.701
_diffrn_measurement_device_type  '  R-AXIS-CS3 6.X, c++'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_sigmaI/netI    0.006
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10804
_diffrn_reflns_theta_full        71.90
_diffrn_reflns_theta_max         71.59
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    2.590
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
Shape function based on spherical harmonics.
Highest even and odd order for spherical harmonics:  4  and  1
Laue group:  -1
Friedel opposites are equivalent.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         4857
_refine_ls_number_restraints     293
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0274P)^2^+0.6397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0735
_reflns_number_gt                4512
_reflns_number_total             4859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b316502g.txt
_cod_data_source_block           rc113003
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7151609