#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/76/2227669.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_2227669
loop_
_publ_author_name
'Li, Kaozhen'
'Feng, Qiu'
'Lu, Ze-Hua'
_publ_section_title
;
 1-Acetyl-5-isobutyl-2-sulfanylideneimidazolidin-4-one
;
_journal_coeditor_code           IS2592
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2655
_journal_paper_doi               10.1107/S1600536810037256
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H14 N2 O2 S'
_chemical_formula_moiety         'C9 H14 N2 O2 S'
_chemical_formula_sum            'C9 H14 N2 O2 S'
_chemical_formula_weight         214.28
_chemical_name_systematic
;
1-Acetyl-5-isobutyl-2-sulfanylideneimidazolidin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.231(2)
_cell_angle_beta                 93.9650(10)
_cell_angle_gamma                90.4910(10)
_cell_formula_units_Z            4
_cell_length_a                   7.1856(8)
_cell_length_b                   9.7567(11)
_cell_length_c                   16.4226(15)
_cell_measurement_reflns_used    1409
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.488
_cell_measurement_theta_min      2.536
_cell_volume                     1126.3(2)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5877
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.8966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0539
_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)+(0.0539P)²+0.2948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                2199
_reflns_number_total             3916
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2592.cif
_cod_data_source_block           I
_cod_database_code               2227669
_cod_database_fobs_code          2227669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.3760(3) 0.2881(3) 0.16750(16) 0.0404(7) Uani d . 1 . .
N N2 0.0770(3) 0.2612(3) 0.18054(17) 0.0523(8) Uani d . 1 . .
H H2 -0.0417 0.2710 0.1746 0.063 Uiso calc R 1 . .
N N3 0.0219(3) 0.7835(3) 0.17203(16) 0.0429(7) Uani d . 1 . .
N N4 0.3235(4) 0.7558(3) 0.18537(17) 0.0518(8) Uani d . 1 . .
H H4 0.4406 0.7664 0.1800 0.062 Uiso calc R 1 . .
O O1 0.0752(3) 0.1110(3) 0.27212(17) 0.0746(8) Uani d . 1 . .
O O2 0.6815(3) 0.2536(3) 0.16880(16) 0.0638(7) Uani d . 1 . .
O O3 0.3503(3) 0.6072(3) 0.27747(17) 0.0748(8) Uani d . 1 . .
O O4 -0.2837(3) 0.7469(3) 0.17042(16) 0.0649(7) Uani d . 1 . .
S S1 0.13550(12) 0.41653(10) 0.06933(6) 0.0563(3) Uani d . 1 . .
S S2 0.23535(13) 0.90538(11) 0.07109(6) 0.0626(3) Uani d . 1 . .
C C1 0.2002(4) 0.3238(3) 0.13812(19) 0.0403(8) Uani d . 1 . .
C C2 0.1575(4) 0.1820(4) 0.2329(2) 0.0520(9) Uani d . 1 . .
C C3 0.3646(4) 0.2041(4) 0.2328(2) 0.0466(9) Uani d . 1 . .
H H3 0.4243 0.1141 0.2158 0.056 Uiso calc R 1 . .
C C4 0.4495(5) 0.2774(4) 0.3174(2) 0.0569(10) Uani d . 1 . .
H H4A 0.5733 0.3121 0.3106 0.068 Uiso calc R 1 . .
H H4B 0.3747 0.3576 0.3373 0.068 Uiso calc R 1 . .
C C5 0.4652(6) 0.1881(4) 0.3833(2) 0.0698(11) Uani d . 1 . .
H H5 0.3394 0.1543 0.3900 0.084 Uiso calc R 1 . .
C C6 0.5376(7) 0.2777(5) 0.4657(3) 0.1015(16) Uani d . 1 . .
H H6A 0.6642 0.3068 0.4621 0.152 Uiso calc R 1 . .
H H6B 0.5328 0.2245 0.5089 0.152 Uiso calc R 1 . .
H H6C 0.4616 0.3585 0.4782 0.152 Uiso calc R 1 . .
C C7 0.5853(8) 0.0619(5) 0.3603(3) 0.121(2) Uani d . 1 . .
H H7A 0.7066 0.0916 0.3486 0.182 Uiso calc R 1 . .
H H7B 0.5283 0.0007 0.3119 0.182 Uiso calc R 1 . .
H H7C 0.5972 0.0131 0.4058 0.182 Uiso calc R 1 . .
C C8 0.5509(4) 0.3120(3) 0.1399(2) 0.0453(8) Uani d . 1 . .
C C9 0.5730(5) 0.4020(4) 0.0785(2) 0.0639(11) Uani d . 1 . .
H H9A 0.7025 0.4090 0.0686 0.096 Uiso calc R 1 . .
H H9B 0.5277 0.4934 0.0996 0.096 Uiso calc R 1 . .
H H9C 0.5030 0.3621 0.0273 0.096 Uiso calc R 1 . .
C C10 0.1898(4) 0.8166(3) 0.1424(2) 0.0427(8) Uani d . 1 . .
C C11 0.2580(5) 0.6769(4) 0.2376(2) 0.0502(9) Uani d . 1 . .
C C12 0.0504(4) 0.6996(3) 0.2371(2) 0.0461(9) Uani d . 1 . .
H H12 -0.0175 0.6099 0.2202 0.055 Uiso calc R 1 . .
C C13 -0.0073(5) 0.7752(4) 0.3214(2) 0.0573(10) Uani d . 1 . .
H H13A 0.0745 0.8564 0.3406 0.069 Uiso calc R 1 . .
H H13B -0.1329 0.8086 0.3142 0.069 Uiso calc R 1 . .
C C14 -0.0024(6) 0.6886(4) 0.3882(2) 0.0724(12) Uani d . 1 . .
H H14 0.1255 0.6567 0.3955 0.087 Uiso calc R 1 . .
C C15 -0.1284(9) 0.5618(6) 0.3658(3) 0.126(2) Uani d . 1 . .
H H15A -0.1293 0.5155 0.4122 0.190 Uiso calc R 1 . .
H H15B -0.0840 0.4992 0.3189 0.190 Uiso calc R 1 . .
H H15C -0.2526 0.5894 0.3518 0.190 Uiso calc R 1 . .
C C16 -0.0487(7) 0.7818(6) 0.4705(3) 0.1089(17) Uani d . 1 . .
H H16A -0.1747 0.8127 0.4655 0.163 Uiso calc R 1 . .
H H16B 0.0352 0.8614 0.4831 0.163 Uiso calc R 1 . .
H H16C -0.0355 0.7296 0.5143 0.163 Uiso calc R 1 . .
C C17 -0.1606(4) 0.8094(4) 0.1444(2) 0.0471(9) Uani d . 1 . .
C C18 -0.2005(5) 0.9099(4) 0.0897(2) 0.0630(10) Uani d . 1 . .
H H18A -0.3330 0.9169 0.0800 0.094 Uiso calc R 1 . .
H H18B -0.1466 0.8784 0.0376 0.094 Uiso calc R 1 . .
H H18C -0.1478 0.9998 0.1157 0.094 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 0.0000 0.0000 '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'
N N 0.0061 0.0033 '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
C1 N1 C8 . . 129.4(3) ?
C1 N1 C3 . . 111.9(2) ?
C8 N1 C3 . . 118.6(3) ?
C2 N2 C1 . . 114.9(3) ?
C2 N2 H2 . . 122.6 ?
C1 N2 H2 . . 122.6 ?
C10 N3 C17 . . 129.3(3) ?
C10 N3 C12 . . 111.7(2) ?
C17 N3 C12 . . 118.8(3) ?
C10 N4 C11 . . 115.1(3) ?
C10 N4 H4 . . 122.5 ?
C11 N4 H4 . . 122.5 ?
N2 C1 N1 . . 104.9(3) ?
N2 C1 S1 . . 123.4(2) ?
N1 C1 S1 . . 131.7(2) ?
O1 C2 N2 . . 125.9(3) ?
O1 C2 C3 . . 127.8(3) ?
N2 C2 C3 . . 106.3(3) ?
N1 C3 C2 . . 101.6(2) ?
N1 C3 C4 . . 113.5(3) ?
C2 C3 C4 . . 111.9(3) ?
N1 C3 H3 . . 109.9 ?
C2 C3 H3 . . 109.9 ?
C4 C3 H3 . . 109.9 ?
C5 C4 C3 . . 115.3(3) ?
C5 C4 H4A . . 108.5 ?
C3 C4 H4A . . 108.5 ?
C5 C4 H4B . . 108.5 ?
C3 C4 H4B . . 108.5 ?
H4A C4 H4B . . 107.5 ?
C7 C5 C4 . . 113.2(4) ?
C7 C5 C6 . . 110.9(4) ?
C4 C5 C6 . . 109.3(3) ?
C7 C5 H5 . . 107.7 ?
C4 C5 H5 . . 107.7 ?
C6 C5 H5 . . 107.7 ?
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 ?
O2 C8 N1 . . 116.2(3) ?
O2 C8 C9 . . 122.6(3) ?
N1 C8 C9 . . 121.1(3) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N4 C10 N3 . . 105.3(3) ?
N4 C10 S2 . . 123.4(2) ?
N3 C10 S2 . . 131.3(3) ?
O3 C11 N4 . . 126.2(3) ?
O3 C11 C12 . . 127.9(3) ?
N4 C11 C12 . . 105.9(3) ?
N3 C12 C11 . . 101.5(3) ?
N3 C12 C13 . . 112.7(3) ?
C11 C12 C13 . . 112.0(3) ?
N3 C12 H12 . . 110.1 ?
C11 C12 H12 . . 110.1 ?
C13 C12 H12 . . 110.1 ?
C14 C13 C12 . . 115.1(3) ?
C14 C13 H13A . . 108.5 ?
C12 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
C12 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C15 C14 C13 . . 112.9(4) ?
C15 C14 C16 . . 111.7(4) ?
C13 C14 C16 . . 108.9(4) ?
C15 C14 H14 . . 107.7 ?
C13 C14 H14 . . 107.7 ?
C16 C14 H14 . . 107.7 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O4 C17 N3 . . 115.9(3) ?
O4 C17 C18 . . 122.3(3) ?
N3 C17 C18 . . 121.7(3) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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
N1 C1 . 1.393(4) ?
N1 C8 . 1.398(4) ?
N1 C3 . 1.478(4) ?
N2 C2 . 1.368(4) ?
N2 C1 . 1.372(4) ?
N2 H2 . 0.8600 ?
N3 C10 . 1.390(4) ?
N3 C17 . 1.399(4) ?
N3 C12 . 1.472(4) ?
N4 C10 . 1.361(4) ?
N4 C11 . 1.363(4) ?
N4 H4 . 0.8600 ?
O1 C2 . 1.209(4) ?
O2 C8 . 1.218(4) ?
O3 C11 . 1.205(4) ?
O4 C17 . 1.217(4) ?
S1 C1 . 1.626(3) ?
S2 C10 . 1.635(3) ?
C2 C3 . 1.502(4) ?
C3 C4 . 1.517(5) ?
C3 H3 . 0.9800 ?
C4 C5 . 1.515(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C7 . 1.512(6) ?
C5 C6 . 1.517(5) ?
C5 H5 . 0.9800 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.476(5) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C11 C12 . 1.510(4) ?
C12 C13 . 1.524(4) ?
C12 H12 . 0.9800 ?
C13 C14 . 1.508(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.497(6) ?
C14 C16 . 1.534(5) ?
C14 H14 . 0.9800 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.471(5) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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 O2 1_455 0.86 1.99 2.834(3) 167
N4 H4 O4 1_655 0.86 2.01 2.850(3) 167
