#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/21/1502179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1502179
loop_
_publ_author_name
'Glass, Richard S.'
'Schöneich, Christian'
'Wilson, George S.'
'Nauser, Thomas'
'Yamamoto, Takuhei'
'Lorance, Edward'
'Nichol, Gary S.'
'Ammam, Malika'
_publ_section_title
;
 Neighboring pyrrolidine amide participation in thioether oxidation.
 Methionine as a "hopping" 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
_chemical_name_systematic
;
 ?
;
_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       'φ and ω 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/[σ²(Fo²)+(0.0458P)²+0.1752P] where P=(Fo²+2Fc²)/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>2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
S S 0.12926(3) 0.383308(14) 0.345168(13) 0.02094(5) Uani 1 1 d
O O -0.13297(9) 0.53641(4) 0.18581(4) 0.01900(11) Uani 1 1 d
N N 0.13249(10) 0.45653(4) 0.12389(4) 0.01521(10) Uani 1 1 d
C1 C 0.30606(12) 0.48381(5) 0.37841(5) 0.01597(12) Uani 1 1 d
H1 H 0.425(2) 0.4615(8) 0.4268(8) 0.020(3) Uiso 1 1 d
C2 C 0.17160(13) 0.56382(6) 0.41574(5) 0.01888(13) Uani 1 1 d
H2A H 0.006(2) 0.5612(8) 0.3930(8) 0.025(3) Uiso 1 1 d
H2B H 0.189(2) 0.5613(9) 0.4830(9) 0.033(3) Uiso 1 1 d
C3 C 0.28139(13) 0.65075(5) 0.37973(5) 0.01791(13) Uani 1 1 d
H3 H 0.274(2) 0.7054(8) 0.4178(9) 0.028(3) Uiso 1 1 d
C4 C 0.17127(14) 0.66471(5) 0.28051(5) 0.01953(13) Uani 1 1 d
H4A H 0.001(2) 0.6626(9) 0.2716(8) 0.026(3) Uiso 1 1 d
H4B H 0.219(2) 0.7217(9) 0.2562(9) 0.029(3) Uiso 1 1 d
C5 C 0.26509(12) 0.58111(5) 0.23131(5) 0.01529(11) Uani 1 1 d
H5A H 0.3603(19) 0.6038(7) 0.1859(8) 0.016(2) Uiso 1 1 d
C6 C 0.43323(11) 0.53272(5) 0.30834(5) 0.01465(11) Uani 1 1 d
H6 H 0.5488(19) 0.4954(8) 0.2871(7) 0.016(2) Uiso 1 1 d
C7 C 0.52295(12) 0.61708(5) 0.36649(5) 0.01770(12) Uani 1 1 d
H7A H 0.6066(19) 0.6598(8) 0.3336(8) 0.019(3) Uiso 1 1 d
H7B H 0.626(2) 0.6005(8) 0.4251(8) 0.018(3) Uiso 1 1 d
C8 C 0.35496(18) 0.29827(6) 0.34904(7) 0.02837(17) Uani 1 1 d
H8A H 0.282(2) 0.2388(11) 0.3367(10) 0.041(4) Uiso 1 1 d
H8B H 0.452(3) 0.3009(10) 0.4091(11) 0.041(4) Uiso 1 1 d
H8C H 0.456(3) 0.3102(11) 0.3043(11) 0.051(4) Uiso 1 1 d
C9 C 0.07245(12) 0.52238(5) 0.17986(5) 0.01438(11) Uani 1 1 d
C10 C 0.36607(12) 0.42885(6) 0.11136(5) 0.01834(13) Uani 1 1 d
H10A H 0.441(2) 0.3910(9) 0.1627(9) 0.033(3) Uiso 1 1 d
H10B H 0.460(2) 0.4818(9) 0.1048(9) 0.031(3) Uiso 1 1 d
C11 C 0.32304(13) 0.36952(5) 0.02602(5) 0.01803(13) Uani 1 1 d
H11A H 0.454(2) 0.3258(9) 0.0224(9) 0.030(3) Uiso 1 1 d
H11B H 0.300(2) 0.4091(8) -0.0269(8) 0.023(3) Uiso 1 1 d
C12 C 0.09696(14) 0.32018(6) 0.03589(6) 0.02171(14) Uani 1 1 d
H12A H 0.014(2) 0.2960(9) -0.0223(9) 0.036(3) Uiso 1 1 d
H12B H 0.129(2) 0.2681(9) 0.0771(9) 0.033(3) Uiso 1 1 d
C13 C -0.04269(12) 0.39343(5) 0.07761(5) 0.01655(12) Uani 1 1 d
H13A H -0.133(2) 0.3679(8) 0.1218(8) 0.021(3) Uiso 1 1 d
H13B H -0.145(2) 0.4259(9) 0.0316(9) 0.028(3) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S C8 98.74(4)
C9 N C10 127.44(6)
C9 N C13 120.08(6)
C10 N C13 111.87(6)
S C1 H1 104.6(7)
S C1 C2 113.36(5)
S C1 C6 119.93(5)
H1 C1 C2 109.2(7)
H1 C1 C6 106.5(7)
C2 C1 C6 102.89(6)
C1 C2 H2A 112.3(7)
C1 C2 H2B 110.7(8)
C1 C2 C3 102.89(6)
H2A C2 H2B 107.1(11)
H2A C2 C3 110.8(7)
H2B C2 C3 113.3(8)
C2 C3 H3 113.7(8)
C2 C3 C4 107.69(6)
C2 C3 C7 103.07(6)
H3 C3 C4 113.7(7)
H3 C3 C7 116.9(8)
C4 C3 C7 100.46(6)
C3 C4 H4A 113.3(7)
C3 C4 H4B 111.8(8)
C3 C4 C5 102.87(6)
H4A C4 H4B 108.9(10)
H4A C4 C5 109.5(7)
H4B C4 C5 110.3(8)
C4 C5 H5A 109.7(6)
C4 C5 C6 103.43(6)
C4 C5 C9 112.44(6)
H5A C5 C6 106.8(6)
H5A C5 C9 107.0(6)
C6 C5 C9 117.22(6)
C1 C6 C5 112.70(6)
C1 C6 H6 113.7(7)
C1 C6 C7 98.22(5)
C5 C6 H6 114.3(6)
C5 C6 C7 100.46(6)
H6 C6 C7 115.7(7)
C3 C7 C6 94.54(5)
C3 C7 H7A 114.1(7)
C3 C7 H7B 114.1(7)
C6 C7 H7A 112.3(7)
C6 C7 H7B 113.9(6)
H7A C7 H7B 107.7(9)
S C8 H8A 107.4(9)
S C8 H8B 109.0(9)
S C8 H8C 112.2(10)
H8A C8 H8B 112.8(12)
H8A C8 H8C 109.1(13)
H8B C8 H8C 106.5(13)
O C9 N 120.50(6)
O C9 C5 121.91(6)
N C9 C5 117.53(6)
N C10 H10A 111.7(8)
N C10 H10B 110.9(8)
N C10 C11 102.64(6)
H10A C10 H10B 109.1(11)
H10A C10 C11 109.3(8)
H10B C10 C11 113.1(8)
C10 C11 H11A 111.6(7)
C10 C11 H11B 109.4(7)
C10 C11 C12 102.75(6)
H11A C11 H11B 110.2(10)
H11A C11 C12 113.0(7)
H11B C11 C12 109.6(7)
C11 C12 H12A 113.7(8)
C11 C12 H12B 109.5(8)
C11 C12 C13 103.88(6)
H12A C12 H12B 107.4(10)
H12A C12 C13 112.0(8)
H12B C12 C13 110.3(8)
N C13 C12 104.02(6)
N C13 H13A 109.4(7)
N C13 H13B 110.4(7)
C12 C13 H13A 112.9(7)
C12 C13 H13B 111.5(7)
H13A C13 H13B 108.5(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C1 1.8109(8)
S C8 1.8013(10)
O C9 1.2374(8)
N C9 1.3462(9)
N C10 1.4651(9)
N C13 1.4662(9)
C1 H1 0.979(12)
C1 C2 1.5493(10)
C1 C6 1.5412(10)
C2 H2A 0.982(12)
C2 H2B 0.990(14)
C2 C3 1.5446(11)
C3 H3 0.977(13)
C3 C4 1.5329(11)
C3 C7 1.5378(10)
C4 H4A 0.990(13)
C4 H4B 0.959(13)
C4 C5 1.5560(11)
C5 H5A 0.994(11)
C5 C6 1.5608(10)
C5 C9 1.5244(10)
C6 H6 0.956(11)
C6 C7 1.5420(10)
C7 H7A 0.966(12)
C7 H7B 1.012(12)
C8 H8A 0.966(15)
C8 H8B 0.985(15)
C8 H8C 0.969(17)
C10 H10A 0.988(14)
C10 H10B 0.957(13)
C10 C11 1.5216(11)
C11 H11A 1.001(13)
C11 H11B 0.967(12)
C11 C12 1.5316(11)
C12 H12A 0.992(14)
C12 H12B 0.971(14)
C12 C13 1.5265(11)
C13 H13A 0.977(12)
C13 H13B 0.963(13)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 S C1 C2 -159.38(6)
C8 S C1 C6 78.68(6)
S C1 C2 C3 -143.76(5)
C6 C1 C2 C3 -12.73(7)
C1 C2 C3 C4 80.66(7)
C1 C2 C3 C7 -24.99(7)
C2 C3 C4 C5 -68.37(7)
C7 C3 C4 C5 39.10(7)
C3 C4 C5 C6 -3.84(7)
C3 C4 C5 C9 123.57(6)
S C1 C6 C5 67.52(7)
S C1 C6 C7 172.56(5)
C2 C1 C6 C5 -59.43(7)
C2 C1 C6 C7 45.60(7)
C4 C5 C6 C1 71.03(7)
C4 C5 C6 C7 -32.56(6)
C9 C5 C6 C1 -53.32(8)
C9 C5 C6 C7 -156.90(6)
C2 C3 C7 C6 52.39(7)
C4 C3 C7 C6 -58.71(6)
C1 C6 C7 C3 -59.52(6)
C5 C6 C7 C3 55.52(6)
C10 N C9 O -177.55(7)
C10 N C9 C5 5.31(10)
C13 N C9 O -7.27(10)
C13 N C9 C5 175.58(6)
C4 C5 C9 O -6.77(9)
C4 C5 C9 N 170.33(6)
C6 C5 C9 O 112.90(8)
C6 C5 C9 N -69.99(8)
C9 N C10 C11 -167.33(7)
C13 N C10 C11 21.73(8)
N C10 C11 C12 -35.80(8)
C10 C11 C12 C13 37.46(8)
C9 N C13 C12 -170.07(6)
C10 N C13 C12 1.62(8)
C11 C12 C13 N -24.27(8)
