##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-09-25
_journal_date_accepted     2009-10-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2741
_journal_page_last     o2741
_journal_paper_category     QO
_journal_coeditor_code     PV2212
_publ_contact_author_name     'Harms, Klaus'
_publ_contact_author_address
;
Philipps-Universität Marburg
Fachbereich Chemie
Hans-Meerwein-Strasse
D-35032 Marburg
Germany
;
_publ_contact_author_email     klaus.harms@chemie.uni-marburg.de
_publ_contact_author_fax     '00(06421)2825762'
_publ_contact_author_phone     '00(06421)2827029'
_publ_section_title
;\
(SS,2S,3R)-2-(2-Methylpropane-2-sulfinamido)-3-\
phenylbutyronitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Harms, Klaus'
; ?
;
;Philipps-Universität Marburg
Fachbereich Chemie
Hans-Meerwein-Strasse
D-35032 Marburg
Germany
;
    'Marsch, Michael'
; ?
;
;Philipps-Universität Marburg
Fachbereich Chemie
Hans-Meerwein-Strasse
D-35032 Marburg
Germany
;
    'Oberthür, Markus'
; ?
;
;Philipps-Universität Marburg
Fachbereich Chemie
Hans-Meerwein-Strasse
D-35032 Marburg
Germany
;
    'Schüler, Peter'
; ?
;
;Philipps-Universität Marburg
Fachbereich Chemie
Hans-Meerwein-Strasse
D-35032 Marburg
Germany
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
(SS,2S,3R)-2-(2-Methylpropane-2-sulfinamido)-
3-phenylbutyronitrile
;
_chemical_formula_moiety     'C14 H20 N2 O1 S1'
_chemical_formula_sum     'C14 H20 N2 O S'
_chemical_formula_iupac     'C14 H20 N2 O1 S1'
_chemical_formula_weight     264.38
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_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'
_cell_length_a     8.7892(3)
_cell_length_b     8.7967(4)
_cell_length_c     18.5217(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1432.02(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     22507
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     25
_cell_measurement_temperature     100(2)
_cell_measurement_pressure     ?
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.226
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.217
_exptl_absorpt_correction_type     none
_exptl_special_details
;
δH(300 MHz;
DMSO) 1.13 (s, 9H, tBu), 1.28 (d, 3H, ³J~Me,CH ~= 7.0 Hz,
CH₃), 3.14 (dq, 1H, ³J~CH,CHN ~= 9.9, J~CH,Me ~= 7.0 Hz,
CH), 4.48 (pt, 1H, ³J~CHN,CH ~= 9.9 Hz, CHN), 6.37 (d, 1H,
³J~NH,CHN ~= 9.9 Hz, NH), 7.22 -- 7.38 (m, 5H, CHarom); δC(75
MHz; DMSO-d₆) 18.3 (CH₃), 22.5 (C(CH₃)₃), 43.6 (CH), 52.4 (CHN), 56.4
(C(CH₃)₃), 119.8 (CN), 127.2 (p-CHarom), 127.8 (CHarom),128.5
(CHarom), 141.7 (i-Carom).
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'STOE IPDS II'
_diffrn_measurement_method     'area detetor, ω scans'
_diffrn_reflns_number     22029
_diffrn_reflns_av_R_equivalents     0.0699
_diffrn_reflns_theta_min     2.2
_diffrn_reflns_theta_max     26.76
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     3031
_reflns_number_gt     2624
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0346
_refine_ls_R_factor_gt     0.0286
_refine_ls_wR_factor_ref     0.0642
_refine_ls_goodness_of_fit_ref     0.924
_refine_ls_restrained_S_all     0.924
_refine_ls_number_reflns     3031
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0378P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.178
_refine_diff_density_min     -0.231
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0113(13)
_refine_ls_abs_structure_details     'Flack (1983), 1272 Friedel pairs'
_refine_ls_abs_structure_Flack     0.02(6)
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-AREA (Stoe & Cie, 2002)'
_computing_structure_solution     'SIR2004 (Burla et al, 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 1999)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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
    C C1 0.43208(18) 0.5330(2) -0.00956(9) 0.0303(4) Uani d . 1 . .
    C C2 0.56755(17) 0.6458(2) -0.00597(9) 0.0311(4) Uani d . 1 . .
    C C3 0.40206(16) 0.4817(2) -0.08405(11) 0.0337(4) Uani d . 1 . .
    C C4 0.57924(19) 0.7071(2) 0.07072(10) 0.0343(4) Uani d . 1 . .
    C C5 0.55157(17) 0.7666(2) -0.06356(9) 0.0322(4) Uani d . 1 . .
    C C6 0.46159(19) 0.8950(2) -0.05357(10) 0.0362(4) Uani d . 1 . .
    C C7 0.4397(2) 0.9986(2) -0.10900(12) 0.0451(5) Uani d . 1 . .
    C C8 0.5075(2) 0.9750(3) -0.17589(12) 0.0480(5) Uani d . 1 . .
    C C9 0.5996(2) 0.8499(3) -0.18570(11) 0.0467(5) Uani d . 1 . .
    C C10 0.6223(2) 0.7472(2) -0.13039(10) 0.0394(4) Uani d . 1 . .
    C C11 0.39529(17) 0.2377(2) 0.15401(9) 0.0321(4) Uani d . 1 . .
    C C12 0.4864(3) 0.3546(3) 0.19584(12) 0.0498(5) Uani d . 1 . .
    C C13 0.2643(2) 0.1791(3) 0.20040(12) 0.0447(5) Uani d . 1 . .
    C C14 0.4918(2) 0.1082(3) 0.12683(12) 0.0459(5) Uani d . 1 . .
    N N1 0.45589(15) 0.40435(17) 0.03876(8) 0.0302(3) Uani d . 1 . .
    N N2 0.37703(17) 0.4385(2) -0.14134(9) 0.0449(4) Uani d . 1 . .
    O O1 0.23286(12) 0.20929(14) 0.03335(7) 0.0376(3) Uani d . 1 . .
    S S1 0.30144(4) 0.33362(5) 0.07741(2) 0.03041(11) Uani d . 1 . .
    H H2 0.6626(19) 0.578(2) -0.0175(9) 0.034(5) Uiso d . 1 . .
    H H4A 0.655(2) 0.795(2) 0.0753(11) 0.042(5) Uiso d . 1 . .
    H H8 0.495(2) 1.053(3) -0.2164(11) 0.059(6) Uiso d . 1 . .
    H H01 0.521(2) 0.334(2) 0.0226(10) 0.038(5) Uiso d . 1 . .
    H H4B 0.486(2) 0.751(2) 0.0859(10) 0.041(5) Uiso d . 1 . .
    H H10 0.689(2) 0.649(2) -0.1366(10) 0.049(5) Uiso d . 1 . .
    H H1 0.3383(18) 0.586(2) 0.0075(9) 0.030(4) Uiso d . 1 . .
    H H13A 0.307(3) 0.113(3) 0.2399(12) 0.064(7) Uiso d . 1 . .
    H H6 0.417(2) 0.910(2) -0.0079(10) 0.040(5) Uiso d . 1 . .
    H H14C 0.570(2) 0.146(2) 0.0968(11) 0.053(6) Uiso d . 1 . .
    H H12A 0.509(3) 0.315(3) 0.2468(13) 0.063(6) Uiso d . 1 . .
    H H14B 0.425(2) 0.024(3) 0.0969(13) 0.059(7) Uiso d . 1 . .
    H H4C 0.604(2) 0.621(2) 0.1034(11) 0.051(6) Uiso d . 1 . .
    H H13B 0.205(3) 0.270(3) 0.2212(12) 0.067(7) Uiso d . 1 . .
    H H12C 0.576(3) 0.393(3) 0.1711(14) 0.080(8) Uiso d . 1 . .
    H H7 0.379(2) 1.088(3) -0.0992(12) 0.053(6) Uiso d . 1 . .
    H H12B 0.424(3) 0.447(3) 0.2040(12) 0.060(7) Uiso d . 1 . .
    H H9 0.650(2) 0.827(3) -0.2315(12) 0.060(6) Uiso d . 1 . .
    H H14A 0.539(3) 0.049(3) 0.1672(12) 0.061(7) Uiso d . 1 . .
    H H13C 0.192(3) 0.115(3) 0.1726(12) 0.061(6) Uiso d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0237(8) 0.0324(9) 0.0348(9) 0.0004(7) -0.0002(7) -0.0003(7)
    C2 0.0230(7) 0.0334(10) 0.0368(9) -0.0003(7) 0.0000(6) 0.0008(8)
    C3 0.0232(7) 0.0387(9) 0.0394(10) -0.0018(6) 0.0012(7) -0.0008(9)
    C4 0.0303(8) 0.0346(10) 0.0381(10) -0.0040(7) -0.0005(7) -0.0012(8)
    C5 0.0242(7) 0.0346(9) 0.0378(9) -0.0056(7) -0.0021(6) -0.0003(8)
    C6 0.0240(8) 0.0381(10) 0.0465(10) -0.0054(7) -0.0032(7) 0.0046(8)
    C7 0.0304(9) 0.0389(11) 0.0661(14) -0.0059(8) -0.0134(9) 0.0087(10)
    C8 0.0445(10) 0.0477(13) 0.0518(12) -0.0203(9) -0.0177(9) 0.0157(10)
    C9 0.0468(10) 0.0524(13) 0.0408(11) -0.0187(10) -0.0043(8) 0.0025(11)
    C10 0.0368(9) 0.0407(11) 0.0408(10) -0.0094(8) 0.0004(7) 0.0008(9)
    C11 0.0264(8) 0.0318(9) 0.0380(9) -0.0014(7) 0.0002(6) -0.0011(8)
    C12 0.0603(12) 0.0454(13) 0.0436(11) -0.0135(11) -0.0102(10) 0.0023(11)
    C13 0.0351(9) 0.0486(12) 0.0505(11) 0.0009(10) 0.0047(8) 0.0134(11)
    C14 0.0428(10) 0.0481(12) 0.0466(11) 0.0145(9) 0.0039(9) 0.0072(10)
    N1 0.0235(6) 0.0296(8) 0.0375(8) 0.0017(6) 0.0030(6) 0.0012(7)
    N2 0.0350(8) 0.0575(11) 0.0421(10) -0.0049(8) 0.0003(7) -0.0064(8)
    O1 0.0311(6) 0.0367(7) 0.0451(7) -0.0088(5) -0.0069(5) -0.0010(6)
    S1 0.02191(15) 0.0315(2) 0.0378(2) -0.00129(16) 0.00057(16) 0.0009(2)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    C1 N1 . 1.458(2) ?
    C1 C3 . 1.476(3) ?
    C1 C2 . 1.551(2) ?
    C1 H1 . 0.998(17) ?
    C2 C5 . 1.512(2) ?
    C2 C4 . 1.523(2) ?
    C2 H2 . 1.046(18) ?
    C3 N2 . 1.148(2) ?
    C4 H4A . 1.019(19) ?
    C4 H4B . 0.95(2) ?
    C4 H4C . 0.99(2) ?
    C5 C6 . 1.391(3) ?
    C5 C10 . 1.395(2) ?
    C6 C7 . 1.386(3) ?
    C6 H6 . 0.943(19) ?
    C7 C8 . 1.390(3) ?
    C7 H7 . 0.96(2) ?
    C8 C9 . 1.378(3) ?
    C8 H8 . 1.02(2) ?
    C9 C10 . 1.380(3) ?
    C9 H9 . 0.98(2) ?
    C10 H10 . 1.05(2) ?
    C11 C14 . 1.507(3) ?
    C11 C12 . 1.517(3) ?
    C11 C13 . 1.526(2) ?
    C11 S1 . 1.8454(17) ?
    C12 H12A . 1.02(2) ?
    C12 H12C . 0.97(3) ?
    C12 H12B . 0.99(3) ?
    C13 H13A . 1.01(2) ?
    C13 H13B . 1.03(2) ?
    C13 H13C . 0.99(2) ?
    C14 H14C . 0.94(2) ?
    C14 H14B . 1.10(2) ?
    C14 H14A . 1.00(2) ?
    N1 S1 . 1.6560(14) ?
    N1 H01 . 0.89(2) ?
    O1 S1 . 1.4918(12) ?
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
    N1 C1 C3 . . 111.21(15) ?
    N1 C1 C2 . . 111.10(13) ?
    C3 C1 C2 . . 111.90(13) ?
    N1 C1 H1 . . 106.6(10) ?
    C3 C1 H1 . . 106.9(9) ?
    C2 C1 H1 . . 108.8(10) ?
    C5 C2 C4 . . 114.53(15) ?
    C5 C2 C1 . . 110.36(13) ?
    C4 C2 C1 . . 108.55(13) ?
    C5 C2 H2 . . 109.2(10) ?
    C4 C2 H2 . . 109.7(9) ?
    C1 C2 H2 . . 104.0(10) ?
    N2 C3 C1 . . 178.3(2) ?
    C2 C4 H4A . . 112.9(11) ?
    C2 C4 H4B . . 111.2(11) ?
    H4A C4 H4B . . 103.3(15) ?
    C2 C4 H4C . . 108.2(12) ?
    H4A C4 H4C . . 112.6(15) ?
    H4B C4 H4C . . 108.6(16) ?
    C6 C5 C10 . . 118.05(17) ?
    C6 C5 C2 . . 121.98(15) ?
    C10 C5 C2 . . 119.90(16) ?
    C7 C6 C5 . . 120.94(19) ?
    C7 C6 H6 . . 120.9(12) ?
    C5 C6 H6 . . 118.2(12) ?
    C6 C7 C8 . . 120.2(2) ?
    C6 C7 H7 . . 118.1(14) ?
    C8 C7 H7 . . 121.7(14) ?
    C9 C8 C7 . . 119.2(2) ?
    C9 C8 H8 . . 120.2(12) ?
    C7 C8 H8 . . 120.4(12) ?
    C8 C9 C10 . . 120.6(2) ?
    C8 C9 H9 . . 122.8(14) ?
    C10 C9 H9 . . 116.6(14) ?
    C9 C10 C5 . . 120.9(2) ?
    C9 C10 H10 . . 122.5(11) ?
    C5 C10 H10 . . 116.5(11) ?
    C14 C11 C12 . . 112.71(17) ?
    C14 C11 C13 . . 110.95(17) ?
    C12 C11 C13 . . 109.88(17) ?
    C14 C11 S1 . . 109.91(13) ?
    C12 C11 S1 . . 108.57(14) ?
    C13 C11 S1 . . 104.48(11) ?
    C11 C12 H12A . . 110.1(15) ?
    C11 C12 H12C . . 115.1(16) ?
    H12A C12 H12C . . 113(2) ?
    C11 C12 H12B . . 109.8(13) ?
    H12A C12 H12B . . 104(2) ?
    H12C C12 H12B . . 104(2) ?
    C11 C13 H13A . . 108.8(13) ?
    C11 C13 H13B . . 109.2(12) ?
    H13A C13 H13B . . 111.5(17) ?
    C11 C13 H13C . . 112.4(13) ?
    H13A C13 H13C . . 106.7(17) ?
    H13B C13 H13C . . 108.3(18) ?
    C11 C14 H14C . . 109.8(13) ?
    C11 C14 H14B . . 112.1(11) ?
    H14C C14 H14B . . 109.4(17) ?
    C11 C14 H14A . . 112.4(13) ?
    H14C C14 H14A . . 108.6(17) ?
    H14B C14 H14A . . 104.4(18) ?
    C1 N1 S1 . . 116.06(11) ?
    C1 N1 H01 . . 115.0(12) ?
    S1 N1 H01 . . 114.2(13) ?
    O1 S1 N1 . . 111.73(7) ?
    O1 S1 C11 . . 105.41(7) ?
    N1 S1 C11 . . 97.92(7) ?
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
    N1 C1 C2 C5 . . . . 172.20(13) ?
    C3 C1 C2 C5 . . . . 47.23(18) ?
    N1 C1 C2 C4 . . . . -61.53(18) ?
    C3 C1 C2 C4 . . . . 173.50(14) ?
    N1 C1 C3 N2 . . . . 31(6) ?
    C2 C1 C3 N2 . . . . 156(6) ?
    C4 C2 C5 C6 . . . . -39.8(2) ?
    C1 C2 C5 C6 . . . . 83.09(19) ?
    C4 C2 C5 C10 . . . . 143.46(15) ?
    C1 C2 C5 C10 . . . . -93.69(17) ?
    C10 C5 C6 C7 . . . . 1.6(2) ?
    C2 C5 C6 C7 . . . . -175.21(15) ?
    C5 C6 C7 C8 . . . . 0.2(3) ?
    C6 C7 C8 C9 . . . . -1.7(3) ?
    C7 C8 C9 C10 . . . . 1.3(3) ?
    C8 C9 C10 C5 . . . . 0.6(3) ?
    C6 C5 C10 C9 . . . . -2.1(3) ?
    C2 C5 C10 C9 . . . . 174.84(15) ?
    C3 C1 N1 S1 . . . . -88.88(15) ?
    C2 C1 N1 S1 . . . . 145.76(12) ?
    C1 N1 S1 O1 . . . . 90.88(13) ?
    C1 N1 S1 C11 . . . . -158.98(12) ?
    C14 C11 S1 O1 . . . . 48.56(14) ?
    C12 C11 S1 O1 . . . . 172.26(13) ?
    C13 C11 S1 O1 . . . . -70.54(14) ?
    C14 C11 S1 N1 . . . . -66.65(14) ?
    C12 C11 S1 N1 . . . . 57.04(15) ?
    C13 C11 S1 N1 . . . . 174.25(13) ?
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
    N1 H01 O1 3 0.89(2) 2.167(19) 2.9511(18) 146.5(18)
