#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228965.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228965
loop_
_publ_author_name
'Gordillo, Paola G.'
'Terán, Joel L.'
'Juárez, Jorge R.'
'Mendoza, Angel'
_publ_section_title
;
 (R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]sulfonium
;
_journal_coeditor_code           BT5438
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o239
_journal_paper_doi               10.1107/S1600536810052955
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H19 N O2 S'
_chemical_formula_moiety         'C15 H19 N O2 S'
_chemical_formula_sum            'C15 H19 N O2 S'
_chemical_formula_weight         277.37
_chemical_name_systematic
;
(R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-
tetrahydropyridin-3-yl]sulfonium
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9860(17)
_cell_length_b                   7.4050(14)
_cell_length_c                   31.589(5)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.071
_cell_measurement_theta_min      21.269
_cell_volume                     1400.2(5)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'XSCANS (Siemens, 1994)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            3016
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North et al., 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.385
_refine_ls_abs_structure_details 'Flack (1983), 532 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+1.1965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                1928
_reflns_number_total             2683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5438.cif
_cod_data_source_block           I
_cod_database_code               2228965
_cod_database_fobs_code          2228965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.10027(19) 0.87732(14) 0.03372(3) 0.0323(2) Uani d . 1 . .
O O1 0.8859(6) 0.5383(4) 0.05505(8) 0.0393(7) Uani d . 1 . .
N N1 0.7630(6) 0.6122(4) 0.12114(10) 0.0300(7) Uani d . 1 . .
O O2 1.0851(7) 1.1013(4) 0.11356(10) 0.0511(9) Uani d . 1 . .
C C9 0.8558(7) 0.3759(6) 0.19114(12) 0.0351(9) Uani d . 1 . .
H H9 0.9723 0.4434 0.1798 0.042 Uiso calc R 1 . .
C C1 0.8724(7) 0.6511(5) 0.08437(10) 0.0278(8) Uani d . 1 . .
C C6 0.6341(8) 0.4423(5) 0.12418(12) 0.0345(10) Uani d . 1 . .
H H6 0.7011 0.3572 0.1041 0.041 Uiso calc R 1 . .
C C4 0.8971(9) 0.8843(6) 0.15731(11) 0.0373(9) Uani d . 1 . .
H H4A 1.0124 0.8199 0.1727 0.045 Uiso calc R 1 . .
H H4B 0.8501 0.9863 0.1744 0.045 Uiso calc R 1 . .
C C3 0.9911(8) 0.9518(6) 0.11576(12) 0.0340(9) Uani d . 1 . .
C C8 0.6557(7) 0.3579(5) 0.16847(12) 0.0305(9) Uani d . 1 . .
C C10 0.8816(9) 0.2937(6) 0.23044(13) 0.0404(10) Uani d . 1 . .
H H10 1.0143 0.3077 0.2454 0.049 Uiso calc R 1 . .
C C15 1.3821(8) 0.9447(7) 0.04512(13) 0.0427(11) Uani d . 1 . .
H H15A 1.4586 0.9711 0.0191 0.064 Uiso calc R 1 . .
H H15B 1.4578 0.8487 0.0596 0.064 Uiso calc R 1 . .
H H15C 1.3805 1.0505 0.0627 0.064 Uiso calc R 1 . .
C C2 0.9708(7) 0.8304(5) 0.08140(11) 0.0285(9) Uani d . 1 . .
C C5 0.7006(8) 0.7604(6) 0.14990(12) 0.0345(10) Uani d . 1 . .
H H5A 0.6507 0.7108 0.1767 0.041 Uiso calc R 1 . .
H H5B 0.578 0.8286 0.1377 0.041 Uiso calc R 1 . .
C C13 0.4867(8) 0.2558(6) 0.18589(14) 0.0396(10) Uani d . 1 . .
H H13 0.3523 0.2426 0.1714 0.048 Uiso calc R 1 . .
C C12 0.5156(9) 0.1720(6) 0.22507(14) 0.0445(11) Uani d . 1 . .
H H12 0.401 0.1021 0.2363 0.053 Uiso calc R 1 . .
C C11 0.7107(9) 0.1916(6) 0.24725(14) 0.0443(12) Uani d . 1 . .
H H11 0.7278 0.1363 0.2735 0.053 Uiso calc R 1 . .
C C14 0.9890(9) 1.0887(7) 0.01517(15) 0.0544(13) Uani d . 1 . .
H H14A 1.0569 1.1193 -0.0114 0.082 Uiso calc R 1 . .
H H14B 1.0205 1.1817 0.0355 0.082 Uiso calc R 1 . .
H H14C 0.8304 1.078 0.0115 0.082 Uiso calc R 1 . .
C C7 0.3927(9) 0.4733(7) 0.10987(16) 0.0524(13) Uani d . 1 . .
H H7A 0.3922 0.5252 0.082 0.079 Uiso calc R 1 . .
H H7B 0.3199 0.5539 0.1293 0.079 Uiso calc R 1 . .
H H7C 0.3147 0.36 0.1094 0.079 Uiso calc R 1 . .
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 S1 C15 . . 107.6(2) ?
C2 S1 C14 . . 107.0(2) ?
C15 S1 C14 . . 99.9(2) ?
C1 N1 C5 . . 119.4(3) ?
C1 N1 C6 . . 119.0(3) ?
C5 N1 C6 . . 117.5(3) ?
C10 C9 C8 . . 120.6(4) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
O1 C1 N1 . . 121.4(3) ?
O1 C1 C2 . . 122.4(3) ?
N1 C1 C2 . . 116.2(3) ?
N1 C6 C7 . . 110.2(4) ?
N1 C6 C8 . . 111.2(3) ?
C7 C6 C8 . . 114.1(4) ?
N1 C6 H6 . . 107 ?
C7 C6 H6 . . 107 ?
C8 C6 H6 . . 107 ?
C5 C4 C3 . . 110.8(3) ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
O2 C3 C2 . . 124.2(4) ?
O2 C3 C4 . . 120.7(4) ?
C2 C3 C4 . . 115.1(3) ?
C13 C8 C9 . . 118.4(4) ?
C13 C8 C6 . . 121.6(4) ?
C9 C8 C6 . . 119.9(4) ?
C11 C10 C9 . . 120.1(5) ?
C11 C10 H10 . . 120 ?
C9 C10 H10 . . 120 ?
S1 C15 H15A . . 109.5 ?
S1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
S1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C3 C2 C1 . . 124.4(3) ?
C3 C2 S1 . . 120.1(3) ?
C1 C2 S1 . . 114.9(3) ?
N1 C5 C4 . . 110.5(3) ?
N1 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C8 C13 C12 . . 120.5(4) ?
C8 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C11 C12 C13 . . 120.9(4) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C12 C11 C10 . . 119.6(4) ?
C12 C11 H11 . . 120.2 ?
C10 C11 H11 . . 120.2 ?
S1 C14 H14A . . 109.5 ?
S1 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
S1 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.729(4) ?
S1 C15 . 1.796(5) ?
S1 C14 . 1.799(5) ?
O1 C1 . 1.250(4) ?
N1 C1 . 1.364(5) ?
N1 C5 . 1.473(5) ?
N1 C6 . 1.479(5) ?
O2 C3 . 1.244(5) ?
C9 C10 . 1.391(6) ?
C9 C8 . 1.402(6) ?
C9 H9 . 0.93 ?
C1 C2 . 1.455(5) ?
C6 C7 . 1.531(7) ?
C6 C8 . 1.538(5) ?
C6 H6 . 0.98 ?
C4 C5 . 1.510(6) ?
C4 C3 . 1.513(5) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C3 C2 . 1.415(5) ?
C8 C13 . 1.378(6) ?
C10 C11 . 1.379(7) ?
C10 H10 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C13 C12 . 1.395(6) ?
C13 H13 . 0.93 ?
C12 C11 . 1.369(7) ?
C12 H12 . 0.93 ?
C11 H11 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7C O2 1_445 0.96 2.36 3.315(6) 172
C15 H15A O1 3_565 0.96 2.38 3.167(5) 138
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 O1 . . . . -164.3(4) ?
C6 N1 C1 O1 . . . . -7.7(6) ?
C5 N1 C1 C2 . . . . 15.5(5) ?
C6 N1 C1 C2 . . . . 172.0(3) ?
C1 N1 C6 C7 . . . . -90.2(5) ?
C5 N1 C6 C7 . . . . 66.8(5) ?
C1 N1 C6 C8 . . . . 142.2(4) ?
C5 N1 C6 C8 . . . . -60.8(5) ?
C5 C4 C3 O2 . . . . 151.0(4) ?
C5 C4 C3 C2 . . . . -31.4(6) ?
C10 C9 C8 C13 . . . . -0.6(6) ?
C10 C9 C8 C6 . . . . -177.2(4) ?
N1 C6 C8 C13 . . . . 149.8(4) ?
C7 C6 C8 C13 . . . . 24.4(6) ?
N1 C6 C8 C9 . . . . -33.6(5) ?
C7 C6 C8 C9 . . . . -159.1(4) ?
C8 C9 C10 C11 . . . . 0.8(6) ?
O2 C3 C2 C1 . . . . 176.3(4) ?
C4 C3 C2 C1 . . . . -1.2(6) ?
O2 C3 C2 S1 . . . . 5.4(7) ?
C4 C3 C2 S1 . . . . -172.1(3) ?
O1 C1 C2 C3 . . . . -169.5(4) ?
N1 C1 C2 C3 . . . . 10.7(6) ?
O1 C1 C2 S1 . . . . 1.8(5) ?
N1 C1 C2 S1 . . . . -178.0(3) ?
C15 S1 C2 C3 . . . . 46.9(4) ?
C14 S1 C2 C3 . . . . -59.6(4) ?
C15 S1 C2 C1 . . . . -124.8(3) ?
C14 S1 C2 C1 . . . . 128.7(3) ?
C1 N1 C5 C4 . . . . -48.4(5) ?
C6 N1 C5 C4 . . . . 154.7(3) ?
C3 C4 C5 N1 . . . . 54.5(5) ?
C9 C8 C13 C12 . . . . -0.3(6) ?
C6 C8 C13 C12 . . . . 176.3(4) ?
C8 C13 C12 C11 . . . . 0.9(7) ?
C13 C12 C11 C10 . . . . -0.7(7) ?
C9 C10 C11 C12 . . . . -0.2(7) ?
