#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008254.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_2008254
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  434
_journal_page_last  436
_publ_section_title
;
Fromm's methylphenyldithiodimethylketuret
;
loop_
_publ_author_name
  'John S. Davidson'
  'Steven J. Rettig'
  'James Trotter'
_chemical_formula_sum  'C12 H15 N3 S2'
_chemical_formula_weight  265.39
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '  -x,  -y,  -z'
_cell_length_a  9.871(2)
_cell_length_b  11.044(2)
_cell_length_c  13.117(3)
_cell_angle_alpha  87.403(8)
_cell_angle_beta  89.625(4)
_cell_angle_gamma  67.3872(11)
_cell_volume  1318.6(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  180
_exptl_crystal_density_diffrn  1.337
_diffrn_ambient_temperature  180
_refine_ls_wR_factor_obs  0.077
loop_
_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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
  S1 0.60003(11) 0.11796(8) 0.07864(7) 0.0255(3) Uani d ? . 1.000
  S2 1.01898(10) -0.27403(8) 0.04655(7) 0.0220(3) Uani d ? . 1.000
  S3 0.34569(10) 0.35706(8) 0.33310(7) 0.0246(3) Uani d ? . 1.000
  S4 -0.05623(11) 0.75278(8) 0.37940(7) 0.0258(3) Uani d ? . 1.000
  N1 0.8317(3) -0.0891(2) 0.1522(2) 0.0179(9) Uani d ? . 1.000
  N2 0.8432(3) -0.0371(2) -0.0241(2) 0.0178(9) Uani d ? . 1.000
  N3 0.6800(3) 0.1434(2) -0.1120(2) 0.0172(8) Uani d ? . 1.000
  N4 0.0822(3) 0.5410(2) 0.2798(2) 0.0191(9) Uani d ? . 1.000
  N5 0.1450(3) 0.5321(2) 0.4553(2) 0.0167(8) Uani d ? . 1.000
  N6 0.3542(3) 0.3833(2) 0.5319(2) 0.0164(8) Uani d ? . 1.000
  C1 0.8868(4) -0.1207(3) 0.0602(3) 0.0147(10) Uani d ? . 1.000
  C2 0.7220(4) 0.0679(3) -0.0253(3) 0.0170(10) Uani d ? . 1.000
  C3 0.7369(4) 0.0442(3) 0.1795(3) 0.0224(10) Uani d ? . 1.000
  C4 0.6505(4) 0.0344(3) 0.2741(3) 0.0319(12) Uani d ? . 1.000
  C5 0.8287(4) 0.1270(3) 0.1963(3) 0.0302(12) Uani d ? . 1.000
  C6 0.7752(4) 0.1118(3) -0.2014(3) 0.0273(11) Uani d ? . 1.000
  C7 0.5511(4) 0.2651(3) -0.1154(2) 0.0185(10) Uani d ? . 1.000
  C8 0.5730(4) 0.3813(3) -0.1280(3) 0.0217(11) Uani d ? . 1.000
  C9 0.4495(4) 0.4997(3) -0.1269(3) 0.0262(12) Uani d ? . 1.000
  C10 0.3115(4) 0.5003(3) -0.1148(3) 0.0294(12) Uani d ? . 1.000
  C11 0.2927(4) 0.3815(4) -0.1042(3) 0.0258(11) Uani d ? . 1.000
  C12 0.4132(4) 0.2632(3) -0.1062(3) 0.0223(11) Uani d ? . 1.000
  C13 0.0670(4) 0.5972(3) 0.3708(3) 0.0173(10) Uani d ? . 1.000
  C14 0.2699(4) 0.4322(3) 0.4483(3) 0.0163(10) Uani d ? . 1.000
  C15 0.1685(4) 0.4000(3) 0.2666(3) 0.0212(10) Uani d ? . 1.000
  C16 0.1997(4) 0.3779(3) 0.1531(3) 0.0262(11) Uani d ? . 1.000
  C17 0.0886(4) 0.3166(3) 0.3101(3) 0.0273(11) Uani d ? . 1.000
  C18 0.3022(4) 0.4342(3) 0.6313(3) 0.0255(11) Uani d ? . 1.000
  C19 0.4934(4) 0.2727(3) 0.5288(2) 0.0177(10) Uani d ? . 1.000
  C20 0.6176(4) 0.2937(3) 0.5003(3) 0.0256(11) Uani d ? . 1.000
  C21 0.7533(4) 0.1890(4) 0.5016(3) 0.0342(13) Uani d ? . 1.000
  C22 0.7631(5) 0.0642(3) 0.5330(3) 0.0346(13) Uani d ? . 1.000
  C23 0.6395(5) 0.0447(3) 0.5622(3) 0.0345(13) Uani d ? . 1.000
  C24 0.5019(4) 0.1499(3) 0.5618(3) 0.0287(12) Uani d ? . 1.000
  H1 0.879(3) -0.159(3) 0.209(2) 0.027(9) Uiso d ? . 1.000
  H2 0.7188 -0.0100 0.3305 0.038 Uiso c ? . 1.000
  H3 0.5866 0.1228 0.2934 0.038 Uiso c ? . 1.000
  H4 0.5905 -0.0159 0.2594 0.038 Uiso c ? . 1.000
  H5 0.8999 0.0859 0.2518 0.036 Uiso c ? . 1.000
  H6 0.7639 0.2155 0.2144 0.036 Uiso c ? . 1.000
  H7 0.8809 0.1322 0.1335 0.036 Uiso c ? . 1.000
  H8 0.8490 0.0222 -0.1922 0.033 Uiso c ? . 1.000
  H9 0.7159 0.1184 -0.2626 0.033 Uiso c ? . 1.000
  H10 0.8244 0.1736 -0.2091 0.033 Uiso c ? . 1.000
  H11 0.6717 0.3810 -0.1375 0.026 Uiso c ? . 1.000
  H12 0.4624 0.5832 -0.1348 0.031 Uiso c ? . 1.000
  H13 0.2264 0.5837 -0.1136 0.035 Uiso c ? . 1.000
  H14 0.1940 0.3815 -0.0952 0.031 Uiso c ? . 1.000
  H15 0.4000 0.1796 -0.1012 0.027 Uiso c ? . 1.000
  H16 0.031(4) 0.604(3) 0.227(3) 0.049(10) Uiso d ? . 1.000
  H17 0.1068 0.4062 0.1150 0.031 Uiso c ? . 1.000
  H18 0.2563 0.2845 0.1436 0.031 Uiso c ? . 1.000
  H19 0.2562 0.4290 0.1280 0.031 Uiso c ? . 1.000
  H20 -0.0061 0.3413 0.2749 0.033 Uiso c ? . 1.000
  H21 0.1480 0.2237 0.3005 0.033 Uiso c ? . 1.000
  H22 0.0724 0.3309 0.3831 0.033 Uiso c ? . 1.000
  H23 0.3774 0.4562 0.6650 0.031 Uiso c ? . 1.000
  H24 0.2121 0.5131 0.6225 0.031 Uiso c ? . 1.000
  H25 0.2819 0.3675 0.6732 0.031 Uiso c ? . 1.000
  H26 0.6104 0.3822 0.4790 0.031 Uiso c ? . 1.000
  H27 0.8415 0.2035 0.4805 0.041 Uiso c ? . 1.000
  H28 0.8584 -0.0098 0.5343 0.042 Uiso c ? . 1.000
  H29 0.6468 -0.0438 0.5837 0.041 Uiso c ? . 1.000
  H30 0.4140 0.1360 0.5846 0.034 Uiso c ? . 1.000
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 0.0200(6) 0.0265(5) 0.0167(5) 0.0051(5) 0.0032(5) 0.0050(4)
  S2 0.0185(6) 0.0169(5) 0.0231(6) 0.0018(4) 0.0017(5) -0.0022(4)
  S3 0.0192(6) 0.0276(6) 0.0171(5) 0.0025(5) -0.0001(5) -0.0048(4)
  S4 0.0254(7) 0.0172(5) 0.0233(6) 0.0047(5) -0.0027(5) -0.0019(4)
  N1 0.022(2) 0.012(2) 0.011(2) 0.0037(14) 0.0047(14) 0.0008(13)
  N2 0.019(2) 0.0142(15) 0.015(2) -0.0013(14) 0.0008(14) -0.0006(13)
  N3 0.018(2) 0.0169(15) 0.012(2) -0.0018(13) -0.0007(13) 0.0034(12)
  N4 0.017(2) 0.0145(15) 0.015(2) 0.0064(13) -0.0058(14) 0.0013(13)
  N5 0.015(2) 0.0155(15) 0.011(2) 0.0033(13) -0.0016(14) 0.0002(12)
  N6 0.014(2) 0.0198(15) 0.009(2) 0.0007(13) -0.0009(13) 0.0014(12)
  C1 0.013(2) 0.012(2) 0.016(2) -0.0004(15) -0.003(2) 0.0006(15)
  C2 0.019(2) 0.016(2) 0.013(2) -0.003(2) 0.000(2) -0.0001(15)
  C3 0.021(2) 0.018(2) 0.017(2) 0.004(2) 0.003(2) 0.0004(15)
  C4 0.034(3) 0.025(2) 0.022(2) 0.005(2) 0.007(2) 0.006(2)
  C5 0.031(3) 0.024(2) 0.033(2) -0.008(2) 0.001(2) -0.003(2)
  C6 0.031(3) 0.029(2) 0.012(2) -0.001(2) 0.006(2) -0.001(2)
  C7 0.022(3) 0.018(2) 0.009(2) -0.002(2) -0.003(2) 0.0024(15)
  C8 0.015(2) 0.022(2) 0.026(2) -0.007(2) -0.001(2) 0.003(2)
  C9 0.027(3) 0.018(2) 0.031(2) -0.004(2) -0.003(2) -0.002(2)
  C10 0.030(3) 0.029(2) 0.014(2) 0.005(2) 0.000(2) 0.003(2)
  C11 0.015(2) 0.045(2) 0.014(2) -0.008(2) -0.001(2) 0.006(2)
  C12 0.019(3) 0.030(2) 0.017(2) -0.010(2) -0.004(2) 0.006(2)
  C13 0.014(2) 0.020(2) 0.016(2) -0.004(2) 0.006(2) -0.0043(15)
  C14 0.020(2) 0.017(2) 0.013(2) -0.008(2) 0.005(2) -0.0020(15)
  C15 0.017(2) 0.019(2) 0.018(2) 0.003(2) -0.005(2) 0.001(2)
  C16 0.028(3) 0.027(2) 0.018(2) -0.003(2) -0.003(2) -0.004(2)
  C17 0.027(3) 0.024(2) 0.031(2) -0.009(2) -0.001(2) -0.003(2)
  C18 0.024(3) 0.027(2) 0.018(2) -0.002(2) -0.001(2) -0.003(2)
  C19 0.015(2) 0.022(2) 0.011(2) -0.001(2) -0.009(2) 0.0033(15)
  C20 0.019(3) 0.026(2) 0.031(2) -0.008(2) 0.000(2) -0.001(2)
  C21 0.013(3) 0.048(3) 0.039(3) -0.008(2) 0.000(2) -0.014(2)
  C22 0.032(3) 0.025(2) 0.029(2) 0.010(2) -0.016(2) -0.011(2)
  C23 0.040(3) 0.017(2) 0.036(3) 0.001(2) -0.014(2) 0.004(2)
  C24 0.029(3) 0.031(2) 0.027(2) -0.013(2) -0.007(2) 0.010(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  S1 C2 . . 1.774(3) yes
  S1 C3 . . 1.822(4) yes
  S2 C1 . . 1.711(3) yes
  S3 C14 . . 1.775(3) yes
  S3 C15 . . 1.842(3) yes
  S4 C13 . . 1.689(3) yes
  N1 C1 . . 1.324(4) yes
  N1 C3 . . 1.469(4) no
  N1 H1 . . 1.02(3) no
  N2 C1 . . 1.367(4) no
  N2 C2 . . 1.307(4) yes
  N3 C2 . . 1.347(4) no
  N3 C6 . . 1.467(4) no
  N3 C7 . . 1.452(4) no
  N4 C13 . . 1.350(4) yes
  N4 C15 . . 1.478(4) no
  N4 H16 . . 0.96(4) no
  N5 C13 . . 1.361(4) no
  N5 C14 . . 1.307(4) yes
  N6 C14 . . 1.342(4) no
  N6 C18 . . 1.453(4) no
  N6 C19 . . 1.447(4) no
  C3 C4 . . 1.525(5) no
  C3 C5 . . 1.537(5) no
  C4 H2 . . 0.98 no
  C4 H3 . . 0.98 no
  C4 H4 . . 0.98 no
  C5 H5 . . 0.98 no
  C5 H6 . . 0.98 no
  C5 H7 . . 0.98 no
  C6 H8 . . 0.98 no
  C6 H9 . . 0.98 no
  C6 H10 . . 0.98 no
  C7 C8 . . 1.384(4) no
  C7 C12 . . 1.375(5) no
  C8 C9 . . 1.404(4) no
  C8 H11 . . 0.98 no
  C9 C10 . . 1.368(5) no
  C9 H12 . . 0.98 no
  C10 C11 . . 1.395(5) no
  C10 H13 . . 0.98 no
  C11 C12 . . 1.389(5) no
  C11 H14 . . 0.98 no
  C12 H15 . . 0.98 no
  C15 C16 . . 1.530(5) no
  C15 C17 . . 1.517(5) no
  C16 H17 . . 0.98 no
  C16 H18 . . 0.98 no
  C16 H19 . . 0.98 no
  C17 H20 . . 0.98 no
  C17 H21 . . 0.98 no
  C17 H22 . . 0.98 no
  C18 H23 . . 0.98 no
  C18 H24 . . 0.98 no
  C18 H25 . . 0.98 no
  C19 C20 . . 1.379(5) no
  C19 C24 . . 1.376(4) no
  C20 C21 . . 1.392(5) no
  C20 H26 . . 0.98 no
  C21 C22 . . 1.388(5) no
  C21 H27 . . 0.98 no
  C22 C23 . . 1.368(5) no
  C22 H28 . . 0.98 no
  C23 C24 . . 1.408(5) no
  C23 H29 . . 0.98 no
  C24 H30 . . 0.98 no
_cod_database_code 2008254