Neighboring pyrrolidine amide participation in thioether oxidation. Methionine as a "hopping" site.
Glass, Richard S.; Schöneich, Christian; Wilson, George S.; Nauser, Thomas; Yamamoto, Takuhei; Lorance, Edward; Nichol, Gary S.; Ammam, Malika; Organic letters 13 (2011) 2837–2839; doi:10.1021/ol200793z

data_1502179
_publ_section_title
;
 Neighboring pyrrolidine amide participation in thioether oxidation.
 Methionine as a &quot;hopping&quot; site.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2837
_journal_page_last               2839
_journal_paper_doi               10.1021/ol200793z
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C13 H21 N O S'
_chemical_formula_sum            'C13 H21 N O S'
_chemical_formula_weight         239.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.613(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8625(3)
_cell_length_b                   14.4664(7)
_cell_length_c                   14.8726(7)
_cell_measurement_reflns_used    7409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.24
_cell_measurement_theta_min      2.77
_cell_volume                     1247.11(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29268
_diffrn_reflns_theta_full        36.43
_diffrn_reflns_theta_max         36.43
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_correction_T_min  0.9094
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0458P)^2^+0.1752P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                4861
_reflns_number_total             6053
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol200793z_si_002.cif
_cod_data_source_block           1b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1502179