data_2011305
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1139
_journal_page_last  1141
_publ_section_title
;
Hydrogen bonding in two salts of 3-methylthio-4-propargylthioquinoline
;
loop_
_publ_author_name
  'Boryczka, Stanis\/law'
  'Steiner, Thomas'
_chemical_formula_moiety  'C13 H12 N S2 + , C2 Cl3 O2 -'
_chemical_formula_sum  'C15 H12 Cl3 N O2 S2'
_chemical_formula_weight  408.73
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  19.430(11)
_cell_length_b  5.338(3)
_cell_length_c  36.66(3)
_cell_angle_alpha  90.00
_cell_angle_beta  111.67(5)
_cell_angle_gamma  90.00
_cell_volume  3533(4)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.537
_diffrn_ambient_temperature  293
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
  S1  .14430(6)  .3416(2)  .03462(3)  .0626(3) Uani d . 1 . . S
  S2  .05253(5)  -.00203(18)  .07042(3)  .0556(3) Uani d . 1 . . S
  N1  .19773(15)  .6183(5)  .14213(8)  .0412(6) Uani d . 1 . . N
  H1  .230(2)  .741(9)  .1550(12)  .066(13) Uiso d . 1 . . H
  C2  .19199(18)  .5839(7)  .10568(10)  .0440(8) Uani d . 1 . . C
  H2  .2172  .6907  .0949  .053(11) Uiso calc R 1 . . H
  C3  .14879(18)  .3902(7)  .08256(9)  .0422(7) Uani d . 1 . . C
  C4  .10912(16)  .2401(6)  .09870(9)  .0393(7) Uani d . 1 . . C
  C5  .11634(16)  .2755(6)  .13815(9)  .0385(7) Uani d . 1 . . C
  C6  .08055(19)  .1282(7)  .15765(11)  .0487(8) Uani d . 1 . . C
  H6  .0490  .0004  .1441  .041(9) Uiso calc R 1 . . H
  C7  .0912(2)  .1687(8)  .19567(12)  .0555(9) Uani d . 1 . . C
  H7  .0672  .0673  .2079  .047(10) Uiso calc R 1 . . H
  C8  .1381(2)  .3624(8)  .21719(11)  .0560(10) Uani d . 1 . . C
  H8  .1450  .3878  .2434  .044(9) Uiso calc R 1 . . H
  C9  .1730(2)  .5116(7)  .19942(10)  .0485(8) Uani d . 1 . . C
  H9  .2036  .6407  .2134  .064(12) Uiso calc R 1 . . H
  C10  .16300(17)  .4708(6)  .15992(9)  .0391(7) Uani d . 1 . . C
  C11  .2164(3)  .5331(15)  .03144(14)  .093(2) Uani d . 1 . . C
  H11A  .2043  .7061  .0330  .12(3) Uiso calc R 1 . . H
  H11B  .2222  .5030  .0069  .085(15) Uiso calc R 1 . . H
  H11C  .2619  .4940  .0527  .089(17) Uiso calc R 1 . . H
  C12  -.0253(2)  .1809(10)  .03786(11)  .0626(11) Uani d . 1 . . C
  H12A  -.0070  .3007  .0237  .103(19) Uiso calc R 1 . . H
  H12B  -.0593  .0694  .0187  .078(14) Uiso calc R 1 . . H
  C13  -.0650(2)  .3139(9)  .05824(11)  .0587(10) Uani d . 1 . . C
  C14  -.0958(3)  .4239(12)  .07467(14)  .0821(15) Uani d . 1 . . C
  H14  -.1206  .5125  .0879  .12(2) Uiso calc R 1 . . H
  Cl1  .45966(6) 1.0717(2)  .18929(4)  .0824(4) Uani d . 1 . . Cl
  Cl2  .38600(6) 1.48057(19)  .14004(3)  .0650(3) Uani d . 1 . . Cl
  Cl3  .37079(7) 1.4117(2)  .21391(3)  .0720(3) Uani d . 1 . . Cl
  O1  .28681(14)  .9747(5)  .17708(7)  .0529(6) Uani d . 1 . . O
  O2  .29272(14) 1.0461(5)  .11853(7)  .0526(6) Uani d . 1 . . O
  C15  .37879(18) 1.2549(6)  .17346(11)  .0450(8) Uani d . 1 . . C
  C16  .31214(17) 1.0752(6)  .15390(10)  .0401(7) Uani d . 1 . . C
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  .0676(6)  .0760(7)  .0439(5)  -.0172(6)  .0204(4)  -.0110(5)
  S2  .0545(5)  .0417(5)  .0617(6)  -.0104(4)  .0109(4)  -.0133(4)
  N1  .0384(14)  .0362(15)  .0450(15)  -.0057(12)  .0107(12)  -.0053(12)
  C2  .0412(16)  .0423(18)  .0448(18)  -.0067(15)  .0114(14)  -.0011(15)
  C3  .0392(16)  .0425(18)  .0389(16)  -.0012(14)  .0074(13)  -.0010(14)
  C4  .0350(15)  .0309(16)  .0443(17)  .0000(13)  .0057(13)  -.0027(13)
  C5  .0329(15)  .0319(16)  .0451(17)  .0009(12)  .0076(13)  .0021(13)
  C6  .0449(18)  .042(2)  .053(2)  -.0041(15)  .0120(16)  .0064(16)
  C7  .058(2)  .051(2)  .058(2)  -.0021(19)  .0221(18)  .0125(18)
  C8  .060(2)  .063(3)  .0437(19)  .009(2)  .0181(17)  .0079(18)
  C9  .0476(18)  .047(2)  .0462(18)  .0001(16)  .0118(15)  -.0052(16)
  C10  .0372(15)  .0324(16)  .0430(17)  .0016(13)  .0093(13)  .0004(13)
  C11  .084(3)  .146(6)  .056(3)  -.049(4)  .034(3)  -.014(3)
  C12  .048(2)  .084(3)  .045(2)  -.001(2)  .0040(17)  -.015(2)
  C13  .056(2)  .068(3)  .047(2)  .001(2)  .0125(18)  -.0025(19)
  C14  .088(3)  .099(4)  .063(3)  .021(3)  .032(3)  .000(3)
  Cl1  .0443(5)  .0486(6)  .1277(11)  .0074(4)  .0008(6)  -.0085(6)
  Cl2  .0676(6)  .0463(5)  .0811(7)  -.0163(5)  .0277(5)  .0020(5)
  Cl3  .0928(8)  .0537(6)  .0637(6)  -.0126(6)  .0223(6)  -.0244(5)
  O1  .0593(15)  .0478(15)  .0528(14)  -.0168(12)  .0221(12)  -.0088(12)
  O2  .0579(15)  .0476(15)  .0467(14)  -.0133(12)  .0128(12)  -.0049(11)
  C15  .0406(17)  .0313(16)  .056(2)  -.0007(14)  .0092(15)  -.0054(14)
  C16  .0362(15)  .0278(15)  .0512(19)  -.0001(13)  .0102(14)  -.0056(14)
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 C3 . 1.747(4) y
  S1 C11 . 1.773(5) y
  S2 C4 . 1.764(3) y
  S2 C12 . 1.825(4) y
  N1 C2 . 1.312(5) y
  N1 C10 . 1.351(4) y
  N1 H1 .  .91(5) y
  C2 C3 . 1.402(5) ?
  C2 H2 .  .9300 ?
  C3 C4 . 1.387(5) ?
  C4 C5 . 1.413(5) ?
  C5 C6 . 1.407(5) ?
  C5 C10 . 1.419(4) ?
  C6 C7 . 1.349(5) ?
  C6 H6 .  .9300 ?
  C7 C8 . 1.411(6) ?
  C7 H7 .  .9300 ?
  C8 C9 . 1.359(5) ?
  C8 H8 .  .9300 ?
  C9 C10 . 1.405(5) ?
  C9 H9 .  .9300 ?
  C11 H11A .  .9600 ?
  C11 H11B .  .9600 ?
  C11 H11C .  .9600 ?
  C12 C13 . 1.444(6) ?
  C12 H12A .  .9700 ?
  C12 H12B .  .9700 ?
  C13 C14 . 1.154(6) y
  C14 H14 .  .9300 ?
  Cl1 C15 . 1.757(4) ?
  Cl2 C15 . 1.760(4) ?
  Cl3 C15 . 1.759(4) ?
  O1 C16 . 1.249(4) y
  O2 C16 . 1.219(4) y
  C15 C16 . 1.557(5) ?