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In 3-methyl­thio-4-(propargyl­thio)­quinolinium chloride monohydrate, C13H12NS2+·Cl·H2O, and 3-methyl­thio-4-(propargyl­thio)­quinolinium tri­chloro­acetate, C13H12­NS2+·­C2Cl3O2, the terminal alkyne group forms C[triple bond]C—H...O hydrogen bonds of favourable geometry. The conformation of the flexible propargyl­thio group is different in the two structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008271/de1147sup1.cif
Contains datablocks global, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008271/de1147IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008271/de1147IIIsup3.hkl
Contains datablock III

CCDC references: 150851; 150852

Computing details top

For both compounds, data collection: please provide details; cell refinement: please provide details; data reduction: please provide details; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(II) 3-Methylthio-4-propargylthioquinolinium chloride monohydrate top
Crystal data top
C13H12NS2+·Cl·H2OZ = 2
Mr = 299.85F(000) = 312
Triclinic, P1Dx = 1.428 Mg m3
a = 7.571 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.486 (6) ÅCell parameters from 39 reflections
c = 10.528 (4) Åθ = 5.1–16.2°
α = 85.72 (4)°µ = 0.56 mm1
β = 71.16 (4)°T = 293 K
γ = 76.94 (5)°Needle, yellow
V = 697.1 (6) Å30.65 × 0.10 × 0.05 mm
Data collection top
STOE four-circle
diffractometer
Rint = 0.035
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.0°
Graphite monochromatorh = 69
ω scansk = 1212
3330 measured reflectionsl = 913
3149 independent reflections3 standard reflections every 90 min
2429 reflections with I > 2σ(I) intensity decay: 4%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0789P)2 + 0.2963P]
where P = (Fo2 + 2Fc2)/3
3149 reflections(Δ/σ)max = 0.001
179 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.51162 (15)1.17671 (9)0.59063 (8)0.0671 (3)
OW10.1414 (6)0.0961 (4)1.5305 (3)0.1142 (12)
S10.22133 (11)0.57394 (7)0.84116 (7)0.0489 (2)
S20.10128 (11)0.67154 (9)1.13383 (7)0.0505 (2)
N10.3469 (3)0.9640 (2)0.7999 (2)0.0388 (5)
H10.389 (5)1.019 (4)0.730 (4)0.059 (9)*
C20.3278 (4)0.8362 (3)0.7718 (3)0.0404 (5)
H20.36500.80740.68280.068 (10)*
C30.2524 (3)0.7437 (3)0.8740 (3)0.0365 (5)
C40.1989 (3)0.7888 (3)1.0061 (2)0.0355 (5)
C50.2159 (3)0.9282 (3)1.0348 (2)0.0357 (5)
C60.1564 (4)0.9872 (3)1.1653 (3)0.0442 (6)
H60.10200.93341.23930.043 (7)*
C70.1781 (4)1.1217 (3)1.1832 (3)0.0518 (7)
H70.14021.15801.26980.065 (10)*
C80.2563 (4)1.2073 (3)1.0742 (3)0.0501 (7)
H80.26991.29911.08890.062 (10)*
C90.3123 (4)1.1559 (3)0.9471 (3)0.0431 (6)
H90.36301.21270.87450.062 (10)*
C100.2930 (3)1.0161 (3)0.9261 (2)0.0356 (5)
C110.2826 (5)0.5702 (4)0.6626 (3)0.0581 (8)
H11A0.19660.64660.63390.060 (10)*
H11B0.27300.47870.63520.082 (12)*
H11C0.41110.58340.62270.082 (12)*
C120.2750 (7)0.6326 (5)1.2213 (5)0.0879 (15)
H12A0.40300.61101.15780.19 (3)*
H12B0.26340.71551.27440.21 (4)*
C130.2397 (5)0.5092 (3)1.3075 (3)0.0572 (8)
C140.2087 (5)0.4110 (4)1.3768 (3)0.0629 (8)
H140.18380.33221.43250.090 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.1072 (7)0.0542 (4)0.0441 (4)0.0416 (4)0.0150 (4)0.0088 (3)
OW10.119 (3)0.132 (3)0.072 (2)0.020 (2)0.0117 (18)0.0213 (19)
S10.0609 (4)0.0384 (3)0.0516 (4)0.0217 (3)0.0159 (3)0.0002 (3)
S20.0549 (4)0.0644 (5)0.0449 (4)0.0363 (4)0.0214 (3)0.0205 (3)
N10.0435 (11)0.0392 (11)0.0360 (11)0.0177 (9)0.0111 (9)0.0069 (9)
C20.0472 (14)0.0424 (13)0.0345 (12)0.0183 (11)0.0111 (10)0.0020 (10)
C30.0365 (12)0.0356 (11)0.0410 (13)0.0130 (9)0.0139 (10)0.0026 (9)
C40.0339 (11)0.0403 (12)0.0349 (12)0.0144 (10)0.0113 (9)0.0065 (9)
C50.0314 (11)0.0390 (12)0.0375 (12)0.0093 (9)0.0112 (9)0.0010 (9)
C60.0440 (14)0.0487 (14)0.0373 (13)0.0094 (11)0.0095 (10)0.0001 (11)
C70.0547 (16)0.0527 (16)0.0462 (15)0.0047 (13)0.0149 (13)0.0143 (12)
C80.0513 (16)0.0407 (14)0.0629 (18)0.0109 (12)0.0214 (13)0.0095 (12)
C90.0428 (13)0.0390 (13)0.0508 (15)0.0154 (11)0.0157 (11)0.0042 (11)
C100.0312 (11)0.0387 (12)0.0393 (12)0.0107 (9)0.0124 (9)0.0018 (9)
C110.070 (2)0.0536 (17)0.0553 (18)0.0206 (15)0.0182 (15)0.0129 (14)
C120.100 (3)0.079 (3)0.127 (4)0.055 (2)0.083 (3)0.060 (3)
C130.0674 (19)0.0542 (17)0.0619 (19)0.0211 (15)0.0337 (16)0.0134 (14)
C140.085 (2)0.0581 (18)0.0550 (18)0.0252 (17)0.0309 (17)0.0136 (15)
Geometric parameters (Å, º) top
S1—C31.753 (3)C7—C81.402 (5)
S1—C111.786 (3)C7—H70.9300
S2—C41.760 (3)C8—C91.358 (4)
S2—C121.796 (4)C8—H80.9300
N1—C21.319 (3)C9—C101.408 (4)
N1—C101.355 (3)C9—H90.9300
N1—H10.88 (4)C11—H11A0.9600
C2—C31.394 (4)C11—H11B0.9600
C2—H20.9300C11—H11C0.9600
C3—C41.388 (4)C12—C131.446 (5)
C4—C51.421 (3)C12—H12A0.9700
C5—C101.411 (3)C12—H12B0.9700
C5—C61.416 (4)C13—C141.159 (4)
C6—C71.357 (4)C14—H140.9300
C6—H60.9300
C3—S1—C11103.84 (14)C9—C8—C7120.0 (3)
C4—S2—C12101.79 (16)C9—C8—H8120.0
C2—N1—C10123.7 (2)C7—C8—H8120.0
C2—N1—H1116 (2)C8—C9—C10119.5 (3)
C10—N1—H1120 (2)C8—C9—H9120.2
N1—C2—C3120.8 (2)C10—C9—H9120.2
N1—C2—H2119.6N1—C10—C9120.1 (2)
C3—C2—H2119.6N1—C10—C5118.7 (2)
C4—C3—C2118.5 (2)C9—C10—C5121.2 (2)
C4—C3—S1119.23 (19)S1—C11—H11A109.5
C2—C3—S1122.3 (2)S1—C11—H11B109.5
C3—C4—C5120.1 (2)H11A—C11—H11B109.5
C3—C4—S2117.91 (19)S1—C11—H11C109.5
C5—C4—S2121.89 (19)H11A—C11—H11C109.5
C10—C5—C6117.3 (2)H11B—C11—H11C109.5
C10—C5—C4118.2 (2)C13—C12—S2107.7 (2)
C6—C5—C4124.5 (2)C13—C12—H12A110.2
C7—C6—C5120.5 (3)S2—C12—H12A110.2
C7—C6—H6119.8C13—C12—H12B110.2
C5—C6—H6119.8S2—C12—H12B110.2
C6—C7—C8121.5 (3)H12A—C12—H12B108.5
C6—C7—H7119.2C14—C13—C12179.0 (4)
C8—C7—H7119.2C13—C14—H14180.0
C10—N1—C2—C31.4 (4)C10—C5—C6—C71.6 (4)
N1—C2—C3—C40.3 (4)C4—C5—C6—C7179.9 (3)
N1—C2—C3—S1179.1 (2)C5—C6—C7—C81.1 (4)
C11—S1—C3—C4173.8 (2)C6—C7—C8—C90.0 (5)
C11—S1—C3—C25.6 (3)C7—C8—C9—C100.7 (4)
C2—C3—C4—C51.9 (4)C2—N1—C10—C9177.8 (2)
S1—C3—C4—C5177.52 (18)C2—N1—C10—C51.5 (4)
C2—C3—C4—S2179.21 (19)C8—C9—C10—N1179.5 (2)
S1—C3—C4—S20.2 (3)C8—C9—C10—C50.2 (4)
C12—S2—C4—C3116.8 (3)C6—C5—C10—N1178.4 (2)
C12—S2—C4—C565.9 (3)C4—C5—C10—N10.1 (3)
C3—C4—C5—C101.8 (3)C6—C5—C10—C90.9 (4)
S2—C4—C5—C10178.97 (18)C4—C5—C10—C9179.4 (2)
C3—C4—C5—C6176.6 (2)C4—S2—C12—C13165.5 (3)
S2—C4—C5—C60.6 (4)
(III) 4-Methylthio-3-propargylthioquinolinium trichloroacetate top
Crystal data top
C13H12NS2+·C2Cl3O2F(000) = 1664
Mr = 408.73Dx = 1.537 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.430 (11) ÅCell parameters from 26 reflections
b = 5.338 (3) Åθ = 5.0–15.1°
c = 36.66 (3) ŵ = 0.76 mm1
β = 111.67 (5)°T = 293 K
V = 3533 (4) Å3Needle, yellow
Z = 81.2 × 0.1 × 0.05 mm
Data collection top
STOE four-circle
diffractometer
Rint = 0.032
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.1°
Graphite monochromatorh = 2424
ω scansk = 62
4098 measured reflectionsl = 4247
4031 independent reflections3 standard reflections every 90 min
2781 reflections with I > 2σ(I) intensity decay: 6%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0764P)2 + 5.2477P]
where P = (Fo2 + 2Fc2)/3
4031 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.14430 (6)0.3416 (2)0.03462 (3)0.0626 (3)
S20.05253 (5)0.00203 (18)0.07042 (3)0.0556 (3)
N10.19773 (15)0.6183 (5)0.14213 (8)0.0412 (6)
H10.230 (2)0.741 (9)0.1550 (12)0.066 (13)*
C20.19199 (18)0.5839 (7)0.10568 (10)0.0440 (8)
H20.21720.69070.09490.053 (11)*
C30.14879 (18)0.3902 (7)0.08256 (9)0.0422 (7)
C40.10912 (16)0.2401 (6)0.09870 (9)0.0393 (7)
C50.11634 (16)0.2755 (6)0.13815 (9)0.0385 (7)
C60.08055 (19)0.1282 (7)0.15765 (11)0.0487 (8)
H60.04900.00040.14410.041 (9)*
C70.0912 (2)0.1687 (8)0.19567 (12)0.0555 (9)
H70.06720.06730.20790.047 (10)*
C80.1381 (2)0.3624 (8)0.21719 (11)0.0560 (10)
H80.14500.38780.24340.044 (9)*
C90.1730 (2)0.5116 (7)0.19942 (10)0.0485 (8)
H90.20360.64070.21340.064 (12)*
C100.16300 (17)0.4708 (6)0.15992 (9)0.0391 (7)
C110.2164 (3)0.5331 (15)0.03144 (14)0.093 (2)
H11A0.20430.70610.03300.12 (3)*
H11B0.22220.50300.00690.085 (15)*
H11C0.26190.49400.05270.089 (17)*
C120.0253 (2)0.1809 (10)0.03786 (11)0.0626 (11)
H12A0.00700.30070.02370.103 (19)*
H12B0.05930.06940.01870.078 (14)*
C130.0650 (2)0.3139 (9)0.05824 (11)0.0587 (10)
C140.0958 (3)0.4239 (12)0.07467 (14)0.0821 (15)
H140.12060.51250.08790.12 (2)*
Cl10.45966 (6)1.0717 (2)0.18929 (4)0.0824 (4)
Cl20.38600 (6)1.48057 (19)0.14004 (3)0.0650 (3)
Cl30.37079 (7)1.4117 (2)0.21391 (3)0.0720 (3)
O10.28681 (14)0.9747 (5)0.17708 (7)0.0529 (6)
O20.29272 (14)1.0461 (5)0.11853 (7)0.0526 (6)
C150.37879 (18)1.2549 (6)0.17346 (11)0.0450 (8)
C160.31214 (17)1.0752 (6)0.15390 (10)0.0401 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0676 (6)0.0760 (7)0.0439 (5)0.0172 (6)0.0204 (4)0.0110 (5)
S20.0545 (5)0.0417 (5)0.0617 (6)0.0104 (4)0.0109 (4)0.0133 (4)
N10.0384 (14)0.0362 (15)0.0450 (15)0.0057 (12)0.0107 (12)0.0053 (12)
C20.0412 (16)0.0423 (18)0.0448 (18)0.0067 (15)0.0114 (14)0.0011 (15)
C30.0392 (16)0.0425 (18)0.0389 (16)0.0012 (14)0.0074 (13)0.0010 (14)
C40.0350 (15)0.0309 (16)0.0443 (17)0.0000 (13)0.0057 (13)0.0027 (13)
C50.0329 (15)0.0319 (16)0.0451 (17)0.0009 (12)0.0076 (13)0.0021 (13)
C60.0449 (18)0.042 (2)0.053 (2)0.0041 (15)0.0120 (16)0.0064 (16)
C70.058 (2)0.051 (2)0.058 (2)0.0021 (19)0.0221 (18)0.0125 (18)
C80.060 (2)0.063 (3)0.0437 (19)0.009 (2)0.0181 (17)0.0079 (18)
C90.0476 (18)0.047 (2)0.0462 (18)0.0001 (16)0.0118 (15)0.0052 (16)
C100.0372 (15)0.0324 (16)0.0430 (17)0.0016 (13)0.0093 (13)0.0004 (13)
C110.084 (3)0.146 (6)0.056 (3)0.049 (4)0.034 (3)0.014 (3)
C120.048 (2)0.084 (3)0.045 (2)0.001 (2)0.0040 (17)0.015 (2)
C130.056 (2)0.068 (3)0.047 (2)0.001 (2)0.0125 (18)0.0025 (19)
C140.088 (3)0.099 (4)0.063 (3)0.021 (3)0.032 (3)0.000 (3)
Cl10.0443 (5)0.0486 (6)0.1277 (11)0.0074 (4)0.0008 (6)0.0085 (6)
Cl20.0676 (6)0.0463 (5)0.0811 (7)0.0163 (5)0.0277 (5)0.0020 (5)
Cl30.0928 (8)0.0537 (6)0.0637 (6)0.0126 (6)0.0223 (6)0.0244 (5)
O10.0593 (15)0.0478 (15)0.0528 (14)0.0168 (12)0.0221 (12)0.0088 (12)
O20.0579 (15)0.0476 (15)0.0467 (14)0.0133 (12)0.0128 (12)0.0049 (11)
C150.0406 (17)0.0313 (16)0.056 (2)0.0007 (14)0.0092 (15)0.0054 (14)
C160.0362 (15)0.0278 (15)0.0512 (19)0.0001 (13)0.0102 (14)0.0056 (14)
Geometric parameters (Å, º) top
S1—C31.747 (4)C8—H80.9300
S1—C111.773 (5)C9—C101.405 (5)
S2—C41.764 (3)C9—H90.9300
S2—C121.825 (4)C11—H11A0.9600
N1—C21.312 (5)C11—H11B0.9600
N1—C101.351 (4)C11—H11C0.9600
N1—H10.91 (5)C12—C131.444 (6)
C2—C31.402 (5)C12—H12A0.9700
C2—H20.9300C12—H12B0.9700
C3—C41.387 (5)C13—C141.154 (6)
C4—C51.413 (5)C14—H140.9300
C5—C61.407 (5)Cl1—C151.757 (4)
C5—C101.419 (4)Cl2—C151.760 (4)
C6—C71.349 (5)Cl3—C151.759 (4)
C6—H60.9300O1—C161.249 (4)
C7—C81.411 (6)O2—C161.219 (4)
C7—H70.9300C15—C161.557 (5)
C8—C91.359 (5)
C3—S1—C11103.5 (2)C10—C9—H9120.0
C4—S2—C12100.27 (19)N1—C10—C9120.2 (3)
C2—N1—C10122.7 (3)N1—C10—C5119.1 (3)
C2—N1—H1115 (3)C9—C10—C5120.7 (3)
C10—N1—H1123 (3)S1—C11—H11A109.5
N1—C2—C3121.7 (3)S1—C11—H11B109.5
N1—C2—H2119.1H11A—C11—H11B109.5
C3—C2—H2119.1S1—C11—H11C109.5
C4—C3—C2118.1 (3)H11A—C11—H11C109.5
C4—C3—S1120.9 (3)H11B—C11—H11C109.5
C2—C3—S1120.9 (3)C13—C12—S2113.4 (3)
C3—C4—C5119.9 (3)C13—C12—H12A108.9
C3—C4—S2119.8 (3)S2—C12—H12A108.9
C5—C4—S2120.3 (3)C13—C12—H12B108.9
C6—C5—C4124.4 (3)S2—C12—H12B108.9
C6—C5—C10117.3 (3)H12A—C12—H12B107.7
C4—C5—C10118.4 (3)C14—C13—C12178.7 (5)
C7—C6—C5121.3 (4)C13—C14—H14180.0
C7—C6—H6119.3C16—C15—Cl1107.4 (2)
C5—C6—H6119.3C16—C15—Cl3111.3 (2)
C6—C7—C8121.0 (4)Cl1—C15—Cl3109.4 (2)
C6—C7—H7119.5C16—C15—Cl2111.6 (2)
C8—C7—H7119.5Cl1—C15—Cl2108.6 (2)
C9—C8—C7119.7 (4)Cl3—C15—Cl2108.39 (19)
C9—C8—H8120.1O2—C16—O1128.6 (3)
C7—C8—H8120.1O2—C16—C15116.5 (3)
C8—C9—C10120.0 (3)O1—C16—C15114.9 (3)
C8—C9—H9120.0
C10—N1—C2—C30.2 (5)C6—C7—C8—C90.2 (6)
N1—C2—C3—C42.7 (5)C7—C8—C9—C100.7 (6)
N1—C2—C3—S1177.9 (3)C2—N1—C10—C9178.0 (3)
C11—S1—C3—C4169.0 (4)C2—N1—C10—C52.2 (5)
C11—S1—C3—C211.7 (4)C8—C9—C10—N1179.9 (3)
C2—C3—C4—C53.7 (5)C8—C9—C10—C50.3 (5)
S1—C3—C4—C5177.0 (2)C6—C5—C10—N1179.3 (3)
C2—C3—C4—S2178.7 (3)C4—C5—C10—N11.1 (5)
S1—C3—C4—S20.6 (4)C6—C5—C10—C90.6 (5)
C12—S2—C4—C375.1 (3)C4—C5—C10—C9179.0 (3)
C12—S2—C4—C5107.3 (3)C4—S2—C12—C1363.8 (4)
C3—C4—C5—C6177.8 (3)S2—C12—C13—C1484 (22)
S2—C4—C5—C60.2 (5)Cl1—C15—C16—O292.3 (3)
C3—C4—C5—C101.8 (5)Cl3—C15—C16—O2147.8 (3)
S2—C4—C5—C10179.4 (2)Cl2—C15—C16—O226.6 (4)
C4—C5—C6—C7178.5 (3)Cl1—C15—C16—O186.0 (3)
C10—C5—C6—C71.1 (5)Cl3—C15—C16—O133.8 (4)
C5—C6—C7—C80.7 (6)Cl2—C15—C16—O1155.1 (3)
 

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