Neighboring Amide Participation in Thioether Oxidation: Relevance to Biological Oxidation
Richard S. Glass; Gordon L. Hug; Christian Schöneich; George S. Wilson; Larisa Kuznetsova; Tang-man Lee; Malika Ammam; Edward Lorance; Thomas Nauser; Gary S. Nichol; Takuhei Yamamoto; Journal of the American Chemical Society 131 (2009) 13791–13805; doi:10.1021/ja904895u

data_4105069
_publ_section_title
;
 Neighboring Amide Participation in Thioether Oxidation: Relevance to
 Biological Oxidation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13791
_journal_page_last               13805
_journal_paper_doi               10.1021/ja904895u
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C13 H20 N2 O2 S'
_chemical_formula_sum            'C13 H20 N2 O2 S'
_chemical_formula_weight         268.37
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.4120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.211(2)
_cell_length_b                   7.9924(8)
_cell_length_c                   16.8189(16)
_cell_measurement_reflns_used    7222
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.55
_cell_volume                     2798.2(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
Bruker SHELXTL and Mercury 1.4 (Bruno et al, 2002)
;
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12188
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9389
_exptl_absorpt_correction_T_min  0.9264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0522P)^2^+4.1902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                2835
_reflns_number_total             3409
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja904895u_si_002.cif
_cod_data_source_block           rsg101
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4105069