#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202455.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_2202455
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1938
_journal_page_last  o1940
_publ_section_title
;
4,5-Dicyano-1,2-bis(2-dimethylaminoethylsulfanyl)benzene
;
loop_
_publ_author_name
  "\,Coruh, Ufuk"
  'Ustaba\,s, Re\,sat'
  'Y\?ilmaz, \.Ismail'
  'Yavuz, Metin'
_chemical_formula_moiety  'C16 H22 N4 S2'
_chemical_formula_sum  'C16 H22 N4 S2'
_chemical_formula_iupac  'C16 H22 N4 S2'
_chemical_formula_weight  334.50
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
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'
  '-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  9.5897(6)
_cell_length_b  27.024(2)
_cell_length_c  14.3392(14)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3716.1(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.196
_diffrn_ambient_temperature  293(2)
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C11 0.3186(4) 0.80482(13) 0.9447(2) 0.0911(12) Uani d . 1 . . C
  H11A 0.4145 0.8148 0.9405 0.137 Uiso calc R 1 . . H
  H11B 0.3099 0.7783 0.9889 0.137 Uiso calc R 1 . . H
  H11C 0.2629 0.8324 0.9647 0.137 Uiso calc R 1 . . H
  C12 0.2940(4) 0.82653(12) 0.7845(3) 0.0960(12) Uani d . 1 . . C
  H12A 0.3908 0.8356 0.7843 0.144 Uiso calc R 1 . . H
  H12B 0.2384 0.8550 0.7996 0.144 Uiso calc R 1 . . H
  H12C 0.2681 0.8144 0.7240 0.144 Uiso calc R 1 . . H
  S1 0.20135(7) 0.69814(3) 0.74335(6) 0.0584(2) Uani d . 1 . . S
  S2 0.34219(8) 0.60427(3) 0.68672(6) 0.0618(2) Uani d . 1 . . S
  C5 0.1821(2) 0.61723(9) 0.63474(18) 0.0425(6) Uani d . 1 . . C
  C7 -0.0070(3) 0.67568(9) 0.61607(19) 0.0466(7) Uani d . 1 . . C
  H7 -0.0482 0.7058 0.6308 0.056 Uiso calc R 1 . . H
  C6 0.1154(2) 0.66256(9) 0.65893(18) 0.0413(6) Uani d . 1 . . C
  C3 -0.0076(3) 0.59941(10) 0.52946(19) 0.0467(7) Uani d . 1 . . C
  C8 -0.0710(3) 0.64504(10) 0.55123(19) 0.0458(7) Uani d . 1 . . C
  C4 0.1152(3) 0.58654(9) 0.5711(2) 0.0479(7) Uani d . 1 . . C
  H4 0.1555 0.5562 0.5563 0.057 Uiso calc R 1 . . H
  C2 -0.0721(3) 0.56667(11) 0.4639(2) 0.0597(8) Uani d . 1 . . C
  C14 0.5352(3) 0.53291(11) 0.6702(2) 0.0665(9) Uani d . 1 . . C
  H14A 0.5998 0.5604 0.6656 0.080 Uiso calc R 1 . . H
  H14B 0.5229 0.5251 0.7357 0.080 Uiso calc R 1 . . H
  N3 0.2706(2) 0.78811(8) 0.85361(18) 0.0585(7) Uani d . 1 . . N
  N4 0.5934(3) 0.48997(10) 0.62194(17) 0.0669(7) Uani d . 1 . . N
  C1 -0.1962(3) 0.65976(11) 0.5059(2) 0.0619(8) Uani d . 1 . . C
  C10 0.1271(3) 0.77267(11) 0.8570(2) 0.0672(9) Uani d . 1 . . C
  H10A 0.0687 0.8014 0.8684 0.081 Uiso calc R 1 . . H
  H10B 0.1147 0.7500 0.9087 0.081 Uiso calc R 1 . . H
  C9 0.0794(3) 0.74742(11) 0.7672(2) 0.0673(9) Uani d . 1 . . C
  H9A 0.0783 0.7709 0.7162 0.081 Uiso calc R 1 . . H
  H9B -0.0139 0.7342 0.7749 0.081 Uiso calc R 1 . . H
  N2 -0.1223(3) 0.54044(10) 0.4114(2) 0.0855(9) Uani d . 1 . . N
  C13 0.3970(3) 0.54765(10) 0.6288(2) 0.0610(8) Uani d . 1 . . C
  H13A 0.3287 0.5217 0.6387 0.073 Uiso calc R 1 . . H
  H13B 0.4064 0.5532 0.5623 0.073 Uiso calc R 1 . . H
  N1 -0.2961(3) 0.67096(12) 0.4685(2) 0.1016(11) Uani d . 1 . . N
  C16 0.7342(3) 0.48091(14) 0.6532(3) 0.0896(12) Uani d . 1 . . C
  H16A 0.7715 0.4528 0.6208 0.134 Uiso calc R 1 . . H
  H16B 0.7339 0.4745 0.7190 0.134 Uiso calc R 1 . . H
  H16C 0.7907 0.5094 0.6405 0.134 Uiso calc R 1 . . H
  C15 0.5080(4) 0.44650(12) 0.6367(3) 0.0959(12) Uani d . 1 . . C
  H15A 0.5480 0.4189 0.6041 0.144 Uiso calc R 1 . . H
  H15B 0.4156 0.4526 0.6136 0.144 Uiso calc R 1 . . H
  H15C 0.5038 0.4392 0.7022 0.144 Uiso calc R 1 . . H
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
  C11 0.087(3) 0.094(3) 0.093(3) 0.003(2) -0.018(2) -0.044(2)
  C12 0.116(3) 0.067(2) 0.105(3) -0.010(2) 0.007(3) -0.012(2)
  S1 0.0484(4) 0.0530(4) 0.0738(5) 0.0067(3) -0.0146(4) -0.0246(4)
  S2 0.0572(4) 0.0491(4) 0.0790(6) 0.0095(4) -0.0210(4) -0.0179(4)
  C5 0.0432(16) 0.0427(14) 0.0417(16) -0.0045(12) -0.0015(13) -0.0007(12)
  C7 0.0470(16) 0.0407(14) 0.0520(18) 0.0023(13) -0.0001(15) -0.0066(13)
  C6 0.0395(15) 0.0377(14) 0.0466(17) -0.0019(12) 0.0016(13) -0.0044(12)
  C3 0.0449(16) 0.0491(16) 0.0462(18) -0.0085(13) -0.0038(14) -0.0060(14)
  C8 0.0409(16) 0.0540(17) 0.0425(17) 0.0003(13) -0.0024(14) -0.0029(14)
  C4 0.0501(17) 0.0372(14) 0.0562(19) -0.0027(13) -0.0070(15) -0.0045(13)
  C2 0.062(2) 0.0568(18) 0.061(2) -0.0018(16) -0.0130(18) -0.0067(17)
  C14 0.0578(18) 0.0698(19) 0.072(2) 0.0142(16) -0.0101(17) -0.0128(18)
  N3 0.0551(15) 0.0529(15) 0.0674(17) -0.0011(12) -0.0007(14) -0.0246(13)
  N4 0.0623(17) 0.0722(17) 0.0661(18) 0.0257(14) -0.0036(14) -0.0108(15)
  C1 0.055(2) 0.071(2) 0.059(2) 0.0067(16) -0.0059(19) -0.0175(16)
  C10 0.058(2) 0.0602(18) 0.084(2) 0.0060(15) 0.0020(18) -0.0284(18)
  C9 0.0489(17) 0.0608(17) 0.092(3) 0.0092(14) -0.0112(18) -0.0334(18)
  N2 0.086(2) 0.0751(19) 0.095(2) -0.0048(16) -0.0312(18) -0.0239(18)
  C13 0.0640(19) 0.0525(16) 0.067(2) 0.0141(15) -0.0089(17) -0.0160(16)
  N1 0.078(2) 0.124(3) 0.103(3) 0.0290(19) -0.036(2) -0.032(2)
  C16 0.070(2) 0.109(3) 0.090(3) 0.034(2) -0.001(2) -0.014(2)
  C15 0.096(3) 0.066(2) 0.125(3) 0.021(2) 0.001(3) -0.017(2)
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
  C11 N3 . 1.457(4) yes
  C11 H11A . 0.960 ?
  C11 H11B . 0.960 ?
  C11 H11C . 0.960 ?
  C12 N3 . 1.452(4) yes
  C12 H12A . 0.960 ?
  C12 H12B . 0.960 ?
  C12 H12C . 0.960 ?
  S1 C6 . 1.752(3) yes
  S1 C9 . 1.806(3) yes
  S2 C5 . 1.742(3) yes
  S2 C13 . 1.818(3) yes
  C5 C4 . 1.390(3) ?
  C5 C6 . 1.425(3) ?
  C7 C6 . 1.372(3) ?
  C7 C8 . 1.388(3) ?
  C7 H7 . 0.930 ?
  C3 C4 . 1.365(3) ?
  C3 C8 . 1.410(3) ?
  C3 C2 . 1.431(4) yes
  C8 C1 . 1.423(4) yes
  C4 H4 . 0.930 ?
  C2 N2 . 1.141(3) yes
  C14 N4 . 1.462(3) yes
  C14 C13 . 1.505(3) yes
  C14 H14A . 0.970 ?
  C14 H14B . 0.970 ?
  N3 C10 . 1.439(3) yes
  N4 C16 . 1.444(4) yes
  N4 C15 . 1.447(4) yes
  C1 N1 . 1.138(4) yes
  C10 C9 . 1.527(4) yes
  C10 H10A . 0.970 ?
  C10 H10B . 0.970 ?
  C9 H9A . 0.970 ?
  C9 H9B . 0.970 ?
  C13 H13A . 0.970 ?
  C13 H13B . 0.970 ?
  C16 H16A . 0.960 ?
  C16 H16B . 0.960 ?
  C16 H16C . 0.960 ?
  C15 H15A . 0.960 ?
  C15 H15B . 0.960 ?
  C15 H15C . 0.960 ?
_cod_database_code 2202455