##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     2013-03-18
_journal_date_accepted     2013-03-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     o643
_journal_page_last     o643
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813008337
_journal_coeditor_code     CV5395
_publ_contact_author_name     'Castro, Rosane de P.'
_publ_contact_author_address
;
Instituto de Física, Universidade Federal de Goiás
PObox 131, 74001-970 Goiânia, GO
Brazil
;
_publ_contact_author_email     rosanepc@posgrad.ufg.br
_publ_contact_author_fax     '55(62)35211014 ext. 228'
_publ_contact_author_phone     '55(62)35211014 ext. 247'
_publ_section_title
;
rac-5-(1-Methylethyl)-2-sulfanylideneimidazolidin-4-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Castro, Rosane de P.' ?
;
Instituto de Física -- UFG
Caixa Postal 131, 74001-970 Goiânia, GO
Brazil
;
    'Macedo Jr, Fernando C.' ?
;
Departamento de Química -- UEL
Caixa Postal 6001, 86051-990 Londrina, PR
Brazil
;
    'Brito, Tiago O.' ?
;
Departamento de Química -- UEL
Caixa Postal 6001, 86051-990 Londrina, PR
Brazil
;
    'de Fátima, Angelo' ?
;
Departamento de Química -- UFMG,
31270-901 - Belo Horizonte, MG
Brazil
;
    'Sabino, José R.' .
;
Instituto de Física -- UFG
Caixa Postal 131, 74001-970 Goiânia, GO
Brazil
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
rac-5-(1-Methylethyl)-2-sulfanylideneimidazolidin-4-one
;
_chemical_formula_moiety     'C6 H10 N2 O S'
_chemical_formula_sum     'C6 H10 N2 O S'
_chemical_formula_iupac     'C6 H10 N2 O S'
_chemical_formula_weight     158.23
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     5.71610(10)
_cell_length_b     17.4091(4)
_cell_length_c     8.2505(2)
_cell_angle_alpha     90
_cell_angle_beta     103.5130(10)
_cell_angle_gamma     90
_cell_volume     798.30(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     637
_cell_measurement_theta_min     7.041
_cell_measurement_theta_max     60.80
_cell_measurement_temperature     308(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.93
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.3
_exptl_crystal_density_diffrn     1.316
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     336
_exptl_absorpt_coefficient_mu     0.34
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_absorpt_correction_T_min     0.9362
_exptl_absorpt_correction_T_max     0.9788
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Multilayer optics'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     18741
_diffrn_reflns_av_R_equivalents     0.0195
_diffrn_reflns_theta_min     2.34
_diffrn_reflns_theta_max     34.26
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.926
_diffrn_measured_fraction_theta_full     1
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     13
_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     3064
_reflns_number_gt     2544
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0446
_refine_ls_R_factor_gt     0.0365
_refine_ls_wR_factor_ref     0.1138
_refine_ls_goodness_of_fit_ref     1.023
_refine_ls_restrained_S_all     1.023
_refine_ls_number_reflns     3064
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0671P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0
_refine_diff_density_max     0.332
_refine_diff_density_min     -0.198
_refine_ls_extinction_method     none
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'
    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'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2010)'
_computing_cell_refinement     'SAINT (Bruker, 2010)'
_computing_data_reduction     'SAINT (Bruker, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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 0.50440(6) 0.579973(16) 0.22144(4) 0.04944(11) Uani d . 1 . .
    C C1 0.31293(17) 0.50804(5) 0.22060(11) 0.03529(18) Uani d . 1 . .
    N N1 0.25674(18) 0.45108(5) 0.11098(10) 0.0431(2) Uani d . 1 . .
    H H1 0.3188 0.446 0.0262 0.052 Uiso calc R 1 . .
    C C3 0.07920(18) 0.39803(6) 0.14899(11) 0.03667(18) Uani d . 1 . .
    H H3 -0.0682 0.4005 0.0602 0.044 Uiso calc R 1 . .
    C C4 0.16814(19) 0.31474(5) 0.16973(13) 0.0415(2) Uani d . 1 . .
    H H4 0.2276 0.3015 0.0711 0.05 Uiso calc R 1 . .
    C C5 -0.0352(2) 0.25955(7) 0.17693(18) 0.0568(3) Uani d . 1 . .
    H H5A -0.0905 0.2689 0.2764 0.085 Uiso calc R 1 . .
    H H5B 0.0219 0.2077 0.1778 0.085 Uiso calc R 1 . .
    H H5C -0.1655 0.2672 0.0811 0.085 Uiso calc R 1 . .
    C C6 0.3773(2) 0.30522(7) 0.3219(2) 0.0595(3) Uani d . 1 . .
    H H6C 0.5011 0.3417 0.3163 0.089 Uiso calc R 1 . .
    H H6B 0.4408 0.2541 0.3236 0.089 Uiso calc R 1 . .
    H H6A 0.3215 0.3139 0.4214 0.089 Uiso calc R 1 . .
    C C2 0.03374(17) 0.43453(5) 0.30588(12) 0.03636(18) Uani d . 1 . .
    O O1 -0.10205(16) 0.41213(5) 0.38922(12) 0.0516(2) Uani d . 1 . .
    N N2 0.17754(15) 0.49851(5) 0.33699(11) 0.03987(18) Uani d . 1 . .
    H H2 0.1825 0.5291 0.4196 0.048 Uiso calc R 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
    S1 0.0669(2) 0.04239(16) 0.04620(17) -0.02026(11) 0.02773(13) -0.00744(10)
    C1 0.0445(4) 0.0311(4) 0.0333(4) -0.0024(3) 0.0153(3) 0.0008(3)
    N1 0.0626(5) 0.0386(4) 0.0348(4) -0.0127(4) 0.0248(4) -0.0050(3)
    C3 0.0431(4) 0.0368(4) 0.0320(4) -0.0061(3) 0.0126(3) -0.0032(3)
    C4 0.0497(5) 0.0335(4) 0.0486(5) -0.0080(4) 0.0263(4) -0.0118(4)
    C5 0.0625(7) 0.0448(6) 0.0676(7) -0.0212(5) 0.0242(6) -0.0143(5)
    C6 0.0440(5) 0.0419(5) 0.0917(10) 0.0023(4) 0.0142(6) 0.0060(6)
    C2 0.0379(4) 0.0328(4) 0.0431(4) -0.0009(3) 0.0190(3) -0.0048(3)
    O1 0.0562(5) 0.0449(4) 0.0667(5) -0.0122(3) 0.0406(4) -0.0155(4)
    N2 0.0486(4) 0.0345(4) 0.0431(4) -0.0074(3) 0.0239(3) -0.0096(3)
_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
    S1 C1 . 1.6621(9) ?
    C1 N1 . 1.3300(12) ?
    C1 N2 . 1.3769(12) ?
    N1 C3 . 1.4595(12) ?
    N1 H1 . 0.86 ?
    C3 C2 . 1.5179(13) ?
    C3 C4 . 1.5328(14) ?
    C3 H3 . 0.98 ?
    C4 C5 . 1.5200(14) ?
    C4 C6 . 1.5269(18) ?
    C4 H4 . 0.98 ?
    C5 H5A . 0.96 ?
    C5 H5B . 0.96 ?
    C5 H5C . 0.96 ?
    C6 H6C . 0.96 ?
    C6 H6B . 0.96 ?
    C6 H6A . 0.96 ?
    C2 O1 . 1.2152(12) ?
    C2 N2 . 1.3724(12) ?
    N2 H2 . 0.86 ?
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 N2 . . 107.37(8) ?
    N1 C1 S1 . . 128.23(7) ?
    N2 C1 S1 . . 124.39(7) ?
    C1 N1 C3 . . 113.28(8) ?
    C1 N1 H1 . . 123.4 ?
    C3 N1 H1 . . 123.4 ?
    N1 C3 C2 . . 100.63(7) ?
    N1 C3 C4 . . 113.17(8) ?
    C2 C3 C4 . . 114.79(8) ?
    N1 C3 H3 . . 109.3 ?
    C2 C3 H3 . . 109.3 ?
    C4 C3 H3 . . 109.3 ?
    C5 C4 C6 . . 111.00(10) ?
    C5 C4 C3 . . 111.44(9) ?
    C6 C4 C3 . . 111.72(8) ?
    C5 C4 H4 . . 107.5 ?
    C6 C4 H4 . . 107.5 ?
    C3 C4 H4 . . 107.5 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    C4 C6 H6C . . 109.5 ?
    C4 C6 H6B . . 109.5 ?
    H6C C6 H6B . . 109.5 ?
    C4 C6 H6A . . 109.5 ?
    H6C C6 H6A . . 109.5 ?
    H6B C6 H6A . . 109.5 ?
    O1 C2 N2 . . 126.04(9) ?
    O1 C2 C3 . . 127.40(9) ?
    N2 C2 C3 . . 106.55(8) ?
    C2 N2 C1 . . 112.15(8) ?
    C2 N2 H2 . . 123.9 ?
    C1 N2 H2 . . 123.9 ?
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
    N2 C1 N1 C3 . . . . -0.87(12) ?
    S1 C1 N1 C3 . . . . -179.62(7) ?
    C1 N1 C3 C2 . . . . 0.55(11) ?
    C1 N1 C3 C4 . . . . -122.43(10) ?
    N1 C3 C4 C5 . . . . -169.42(9) ?
    C2 C3 C4 C5 . . . . 75.83(11) ?
    N1 C3 C4 C6 . . . . 65.78(11) ?
    C2 C3 C4 C6 . . . . -48.97(12) ?
    N1 C3 C2 O1 . . . . -179.83(11) ?
    C4 C3 C2 O1 . . . . -57.99(15) ?
    N1 C3 C2 N2 . . . . -0.03(10) ?
    C4 C3 C2 N2 . . . . 121.82(9) ?
    O1 C2 N2 C1 . . . . 179.33(11) ?
    C3 C2 N2 C1 . . . . -0.49(11) ?
    N1 C1 N2 C2 . . . . 0.84(12) ?
    S1 C1 N2 C2 . . . . 179.65(7) ?
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
    N2 H2 O1 3_566 0.86 2.02 2.8573(11) 163.8
    N1 H1 S1 3_665 0.86 2.52 3.3806(9) 175.5
    C6 H6C O1 1_655 0.96 2.52 3.4434(14) 160.3
_iucr_refine_instructions_details
;
TITL mo_RTB76_FERNANDO_UEL_0m in P2(1)/c
CELL  0.71073   5.7161  17.4091   8.2505   90.000  103.513   90.000
ZERR     4.00   0.0001   0.0004   0.0002    0.000    0.001    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O    S    N
UNIT  24   40   4    4    8
MERG   2
MPLA   5  N1 C1 N2 C2 C3 O1 S1
FMAP   2
PLAN   5
SIZE     0.30   0.40   0.93
ACTA   50.00
EQIV  $1  -x, 1-y, 1-z
EQIV  $2  1-x, 1-y, -z
HTAB  N2 O1_$1
HTAB  N1 S1_$2
BOND   $H
CONF
L.S.   4
TEMP    23.00
WGHT    0.067100    0.086900
FVAR       0.28531
S1    4    0.504396    0.579973    0.221440    11.00000    0.06690    0.04239 =
         0.04620   -0.00744    0.02773   -0.02026
C1    1    0.312929    0.508043    0.220601    11.00000    0.04451    0.03113 =
         0.03329    0.00076    0.01530   -0.00239
N1    5    0.256741    0.451077    0.110979    11.00000    0.06260    0.03856 =
         0.03477   -0.00504    0.02478   -0.01270
AFIX  43
H1    2    0.318833    0.446008    0.026156    11.00000   -1.20000
AFIX   0
C3    1    0.079196    0.398025    0.148995    11.00000    0.04312    0.03678 =
         0.03200   -0.00320    0.01259   -0.00609
AFIX  13
H3    2   -0.068203    0.400539    0.060160    11.00000   -1.20000
AFIX   0
C4    1    0.168141    0.314741    0.169732    11.00000    0.04973    0.03355 =
         0.04860   -0.01180    0.02632   -0.00801
AFIX  13
H4    2    0.227586    0.301485    0.071083    11.00000   -1.20000
AFIX   0
C5    1   -0.035231    0.259550    0.176932    11.00000    0.06249    0.04475 =
         0.06762   -0.01430    0.02423   -0.02120
AFIX 137
H5A   2   -0.090515    0.268941    0.276423    11.00000   -1.50000
H5B   2    0.021861    0.207658    0.177774    11.00000   -1.50000
H5C   2   -0.165484    0.267193    0.081148    11.00000   -1.50000
AFIX   0
C6    1    0.377311    0.305219    0.321886    11.00000    0.04399    0.04189 =
         0.09168    0.00600    0.01421    0.00232
AFIX 137
H6C   2    0.501131    0.341703    0.316332    11.00000   -1.50000
H6B   2    0.440842    0.254103    0.323554    11.00000   -1.50000
H6A   2    0.321471    0.313864    0.421433    11.00000   -1.50000
AFIX   0
C2    1    0.033743    0.434531    0.305882    11.00000    0.03787    0.03282 =
         0.04310   -0.00485    0.01896   -0.00090
O1    3   -0.102054    0.412135    0.389224    11.00000    0.05620    0.04493 =
         0.06668   -0.01551    0.04060   -0.01222
N2    5    0.177540    0.498509    0.336994    11.00000    0.04856    0.03445 =
         0.04312   -0.00961    0.02392   -0.00738
AFIX  43
H2    2    0.182511    0.529092    0.419588    11.00000   -1.20000
HKLF 4  1.0  1.00  0.00  0.00  0.00  1.00  0.00  0.00  0.00  1.00
REM  mo_RTB76_FERNANDO_UEL_0m in P2(1)/c
REM R1 =  0.0365 for   2544 Fo > 4sig(Fo)  and  0.0446 for all   3064 data
REM     93 parameters refined using      0 restraints
END
WGHT      0.0631      0.0902
REM Highest difference peak  0.332,  deepest hole -0.198,  1-sigma level  0.045
Q1    1   0.1130  0.4687  0.3285  11.00000  0.05    0.33
Q2    1   0.0394  0.4176  0.2243  11.00000  0.05    0.32
Q3    1   0.4066  0.5428  0.2200  11.00000  0.05    0.30
Q4    1   0.1215  0.3539  0.1600  11.00000  0.05    0.28
Q5    1   0.2786  0.4801  0.1674  11.00000  0.05    0.27
;
