 
data_shelxl 
 
_audit_creation_method            SHELXL-97
_journal_coden_Cambridge ?
_journal_volume ?
_journal_year ?
_journal_page_first ?
_journal_name_full 'Eur.J.Chem. '
loop_
_publ_author_name
"M.Ichitani"
"S.Kitoh"
"K.Tanaka"
"S.Fujinami"
"M.Suda"
"M.Honda"
"A.Kuwae"
"K.Hanai"
"K.-K.Kunimoto" 
_chemical_name_systematic 
; 
(S)-5-Isopropyl-5-methyl-2-sulfanylideneimidazolidin-4-one
; 
_chemical_name_common
; 
(S)-5-Isopropyl-5-methyl-2-thiohydantoin
; 
_chemical_melting_point           413.15 
_chemical_formula_moiety
 'C7 H12 N2 O S'  
_chemical_formula_sum 
 'C7 H12 N2 O S' 
_chemical_formula_weight          172.26 
 
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' 
 
_symmetry_cell_setting            orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21'
_symmetry_Int_Tables_number 19 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x+1/2, -y, z+1/2' 
 
_cell_length_a                    8.2798(12) 
_cell_length_b                    8.6024(13) 
_cell_length_c                    12.826(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      913.6(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     4431
_cell_measurement_theta_min       3.18
_cell_measurement_theta_max       27.50
 
_exptl_crystal_description        'plate' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_max           0.45 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.252 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              368 
_exptl_absorpt_coefficient_mu     0.303 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.8758 
_exptl_absorpt_correction_T_max   0.9281 
_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71070 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method        ω
_diffrn_detector_area_resol_mean  7.314 
_diffrn_standards_number          0
_diffrn_standards_interval_count  .
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9366 
_diffrn_reflns_av_R_equivalents   0.0222 
_diffrn_reflns_av_sigmaI/netI     0.0170 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          3.18 
_diffrn_reflns_theta_max          27.49 
_reflns_number_total              2050 
_reflns_number_gt                 1972 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection             'CrystalClear (Rigaku, 2006)'
_computing_cell_refinement              CrystalClear
_computing_data_reduction               CrystalClear
_computing_structure_solution  
;
SIR2008 in Il Milione (Burla et al., 2007)
;
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure (Rigaku, 2010)'
_computing_molecular_graphics          
;
ORTEP-3 for Windows (Farrugia, 2012) 
and Mercury (Macrae et al., 2006)
;
 
_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 > 2sigma(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. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0353P)²+0.1248P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.01(6) 
_refine_ls_number_reflns          2050 
_refine_ls_number_parameters      111 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0231 
_refine_ls_R_factor_gt            0.0223 
_refine_ls_wR_factor_ref          0.0597 
_refine_ls_wR_factor_gt           0.0593 
_refine_ls_goodness_of_fit_ref    1.079 
_refine_ls_restrained_S_all       1.079 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S -0.05126(3) 0.33886(3) 0.79306(2) 0.01932(9) Uani 1 1 d . . . 
O1 O 0.31309(10) 0.15428(11) 0.50997(6) 0.02303(18) Uani 1 1 d . . . 
N1 N 0.14418(12) 0.46383(12) 0.64734(8) 0.0172(2) Uani 1 1 d . . . 
N2 N 0.14163(13) 0.20969(12) 0.64712(8) 0.0175(2) Uani 1 1 d . . . 
C1 C 0.08016(12) 0.34085(13) 0.69397(8) 0.0156(2) Uani 1 1 d . . . 
C2 C 0.24479(14) 0.24574(13) 0.56632(9) 0.0168(2) Uani 1 1 d . . . 
C3 C 0.25513(14) 0.42290(13) 0.56195(9) 0.0157(2) Uani 1 1 d . . . 
C4 C 0.19272(15) 0.47908(15) 0.45643(9) 0.0237(3) Uani 1 1 d . . . 
H4A H 0.0803 0.4461 0.4475 0.028 Uiso 1 1 calc R . . 
H4B H 0.2590 0.4344 0.4007 0.028 Uiso 1 1 calc R . . 
H4C H 0.1988 0.5928 0.4534 0.028 Uiso 1 1 calc R . . 
C5 C 0.43038(14) 0.47513(14) 0.58422(9) 0.0195(2) Uani 1 1 d . . . 
H5 H 0.4988 0.4374 0.5252 0.023 Uiso 1 1 calc R . . 
C6 C 0.49725(16) 0.40275(16) 0.68411(10) 0.0289(3) Uani 1 1 d . . . 
H6A H 0.6106 0.4330 0.6928 0.035 Uiso 1 1 calc R . . 
H6B H 0.4896 0.2893 0.6796 0.035 Uiso 1 1 calc R . . 
H6C H 0.4345 0.4395 0.7440 0.035 Uiso 1 1 calc R . . 
C7 C 0.44630(16) 0.65179(16) 0.58783(10) 0.0300(3) Uani 1 1 d . . . 
H7A H 0.5588 0.6799 0.6024 0.036 Uiso 1 1 calc R . . 
H7B H 0.3765 0.6932 0.6429 0.036 Uiso 1 1 calc R . . 
H7C H 0.4138 0.6957 0.5205 0.036 Uiso 1 1 calc R . . 
H1 H 0.1171(19) 0.555(2) 0.6626(12) 0.025(4) Uiso 1 1 d . . . 
H2 H 0.119(2) 0.126(2) 0.6620(13) 0.025(4) Uiso 1 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
S1 0.02243(14) 0.01316(13) 0.02236(14) -0.00038(11) 0.00868(10) -0.00119(12) 
O1 0.0250(4) 0.0200(4) 0.0241(4) -0.0053(4) 0.0055(3) 0.0019(4) 
N1 0.0181(5) 0.0115(5) 0.0220(5) -0.0008(4) 0.0069(4) 0.0018(4) 
N2 0.0214(5) 0.0106(4) 0.0204(5) -0.0002(4) 0.0031(4) -0.0004(4) 
C1 0.0153(4) 0.0130(4) 0.0186(5) -0.0017(5) 0.0005(4) -0.0004(4) 
C2 0.0164(6) 0.0164(5) 0.0176(6) -0.0012(4) -0.0020(5) 0.0001(4) 
C3 0.0150(5) 0.0149(5) 0.0172(5) -0.0007(4) 0.0038(4) 0.0005(4) 
C4 0.0211(6) 0.0259(6) 0.0241(6) 0.0061(5) -0.0033(4) -0.0001(5) 
C5 0.0159(5) 0.0240(6) 0.0187(5) -0.0033(4) 0.0023(4) -0.0031(4) 
C6 0.0224(6) 0.0367(7) 0.0276(7) -0.0010(5) -0.0045(5) 0.0002(5) 
C7 0.0325(6) 0.0266(6) 0.0308(6) -0.0025(5) 0.0022(5) -0.0132(7) 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
S1 C1 1.6732(10) . ? 
O1 C2 1.2088(14) . ? 
N1 C1 1.3258(15) . ? 
N1 C3 1.4722(14) . ? 
N1 H1 0.837(17) . ? 
N2 C1 1.3759(15) . ? 
N2 C2 1.3783(16) . ? 
N2 H2 0.767(17) . ? 
C2 C3 1.5274(14) . ? 
C3 C4 1.5272(16) . ? 
C3 C5 1.5457(16) . ? 
C4 H4A 0.9800 . ? 
C4 H4B 0.9800 . ? 
C4 H4C 0.9800 . ? 
C5 C7 1.5260(18) . ? 
C5 C6 1.5284(17) . ? 
C5 H5 1.0000 . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C6 H6C 0.9800 . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C1 N1 C3 113.22(9) . . ? 
C1 N1 H1 122.2(11) . . ? 
C3 N1 H1 124.4(11) . . ? 
C1 N2 C2 111.91(10) . . ? 
C1 N2 H2 124.7(12) . . ? 
C2 N2 H2 123.3(12) . . ? 
N1 C1 N2 108.02(9) . . ? 
N1 C1 S1 127.65(9) . . ? 
N2 C1 S1 124.33(9) . . ? 
O1 C2 N2 126.37(11) . . ? 
O1 C2 C3 126.96(11) . . ? 
N2 C2 C3 106.67(10) . . ? 
N1 C3 C4 111.87(9) . . ? 
N1 C3 C2 100.16(9) . . ? 
C4 C3 C2 109.23(10) . . ? 
N1 C3 C5 112.26(9) . . ? 
C4 C3 C5 112.92(10) . . ? 
C2 C3 C5 109.63(10) . . ? 
C3 C4 H4A 109.5 . . ? 
C3 C4 H4B 109.5 . . ? 
H4A C4 H4B 109.5 . . ? 
C3 C4 H4C 109.5 . . ? 
H4A C4 H4C 109.5 . . ? 
H4B C4 H4C 109.5 . . ? 
C7 C5 C6 110.42(10) . . ? 
C7 C5 C3 112.10(10) . . ? 
C6 C5 C3 112.12(10) . . ? 
C7 C5 H5 107.3 . . ? 
C6 C5 H5 107.3 . . ? 
C3 C5 H5 107.3 . . ? 
C5 C6 H6A 109.5 . . ? 
C5 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C5 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
C5 C7 H7A 109.5 . . ? 
C5 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
C5 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
 
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 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C3 N1 C1 N2 0.88(12) . . . . ? 
C3 N1 C1 S1 -179.59(8) . . . . ? 
C2 N2 C1 N1 -1.62(13) . . . . ? 
C2 N2 C1 S1 178.83(8) . . . . ? 
C1 N2 C2 O1 -178.16(11) . . . . ? 
C1 N2 C2 C3 1.66(14) . . . . ? 
C1 N1 C3 C4 115.72(11) . . . . ? 
C1 N1 C3 C2 0.10(13) . . . . ? 
C1 N1 C3 C5 -116.13(11) . . . . ? 
O1 C2 C3 N1 178.79(11) . . . . ? 
N2 C2 C3 N1 -1.03(13) . . . . ? 
O1 C2 C3 C4 61.19(17) . . . . ? 
N2 C2 C3 C4 -118.62(10) . . . . ? 
O1 C2 C3 C5 -63.02(16) . . . . ? 
N2 C2 C3 C5 117.16(10) . . . . ? 
N1 C3 C5 C7 -65.96(12) . . . . ? 
C4 C3 C5 C7 61.63(13) . . . . ? 
C2 C3 C5 C7 -176.34(9) . . . . ? 
N1 C3 C5 C6 58.90(13) . . . . ? 
C4 C3 C5 C6 -173.51(10) . . . . ? 
C2 C3 C5 C6 -51.48(13) . . . . ? 

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 S1 . . 3_556 3.4036(12) 0.837(17) 2.566(17) 176.7(15) no
N2 H2 S1 . . 3_546 3.3652(12) 0.767(17) 2.598(17) 177.7(15) no

_diffrn_measured_fraction_theta_max    0.976 
_diffrn_reflns_theta_full              27.49 
_diffrn_measured_fraction_theta_full   0.976 
_refine_diff_density_max    0.255 
_refine_diff_density_min   -0.180 
_refine_diff_density_rms    0.033