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The title compound, C9H11N3S2, crystallizes with two mol­ecules in the asymmetric unit, which differ mainly in the degree of planarity. The C=N double bonds are trans configured. Geometric parameters are in the usual ranges. The crystal structure is characterized by N—H...N and N—H...S hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050793/sg2105sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050793/sg2105Isup2.hkl
Contains datablock I

CCDC reference: 630464

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.084
  • Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - C1 .. 7.28 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1A - C1A .. 5.68 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

4-(Methylsulfanyl)benzaldehyde thiosemicarbazone top
Crystal data top
C9H11N3S2Z = 4
Mr = 225.33F(000) = 472
Triclinic, P1Dx = 1.373 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2052 (4) ÅCell parameters from 35812 reflections
b = 9.1947 (5) Åθ = 2.6–30.3°
c = 15.5994 (8) ŵ = 0.45 mm1
α = 106.558 (5)°T = 173 K
β = 97.573 (3)°Block, light orange
γ = 100.110 (4)°0.38 × 0.36 × 0.33 mm
V = 1089.76 (10) Å3
Data collection top
Stoe IPDS-II two-circle
diffractometer
6421 independent reflections
Radiation source: fine-focus sealed tube6026 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 30.2°, θmin = 2.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1111
Tmin = 0.847, Tmax = 0.865k = 1212
36432 measured reflectionsl = 2219
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.3428P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
6421 reflectionsΔρmax = 0.38 e Å3
280 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.048 (3)
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
S10.67198 (3)0.07742 (3)0.631875 (17)0.02549 (7)
S20.25814 (4)0.65923 (4)0.88918 (2)0.03788 (9)
N10.39725 (14)0.17237 (13)0.57770 (7)0.0312 (2)
H1A0.390 (2)0.109 (2)0.5230 (12)0.038 (4)*
H1B0.310 (2)0.2118 (19)0.5896 (11)0.038 (4)*
N20.48514 (12)0.23271 (11)0.73196 (6)0.02565 (18)
H20.547 (2)0.222 (2)0.7774 (12)0.041 (4)*
N30.34361 (12)0.29195 (11)0.74363 (6)0.02462 (17)
C10.50545 (13)0.16371 (12)0.64601 (7)0.02302 (18)
C20.33505 (13)0.36393 (12)0.82623 (7)0.02456 (19)
H2B0.42320.37390.87500.029*
C30.19202 (19)0.81155 (15)0.99705 (10)0.0397 (3)
H3A0.16060.76671.04510.059*
H3B0.28480.86311.01040.059*
H3C0.09460.88770.99440.059*
C110.18868 (13)0.43033 (12)0.84461 (7)0.02277 (18)
C120.03851 (14)0.38485 (13)0.77929 (7)0.0264 (2)
H120.02760.30370.72380.032*
C130.09340 (14)0.45763 (14)0.79535 (8)0.0289 (2)
H130.19370.42700.75040.035*
C140.08065 (13)0.57645 (13)0.87757 (8)0.0262 (2)
C150.06585 (14)0.61834 (12)0.94438 (7)0.0268 (2)
H150.07480.69651.00090.032*
C160.19843 (13)0.54492 (12)0.92766 (7)0.02488 (19)
H160.29730.57310.97340.030*
S1A0.38986 (4)0.08951 (3)0.102549 (17)0.02913 (8)
S2A1.06187 (4)0.93546 (3)0.64566 (2)0.03645 (9)
N1A0.61386 (14)0.17483 (12)0.12934 (7)0.0318 (2)
H1C0.609 (2)0.147 (2)0.0708 (13)0.048 (5)*
H1D0.677 (2)0.262 (2)0.1625 (11)0.039 (4)*
N2A0.52121 (13)0.14129 (11)0.25613 (6)0.02653 (18)
H2A0.456 (2)0.0849 (19)0.2834 (11)0.035 (4)*
N3A0.62678 (12)0.28349 (10)0.30691 (6)0.02564 (18)
C1A0.51689 (14)0.08655 (12)0.16569 (7)0.02419 (19)
C2A0.62789 (14)0.32367 (12)0.39316 (7)0.0256 (2)
H2A10.55850.25670.41690.031*
C3A1.0228 (2)0.94995 (18)0.75830 (10)0.0495 (4)
H3A10.90630.95990.76070.074*
H3A21.10071.04170.80260.074*
H3A31.04000.85620.77290.074*
C11A0.73408 (13)0.47062 (12)0.45536 (7)0.02366 (19)
C12A0.85520 (14)0.56411 (12)0.42608 (7)0.0258 (2)
H12A0.87020.53120.36470.031*
C13A0.95270 (14)0.70357 (13)0.48588 (8)0.0280 (2)
H13A1.03430.76540.46520.034*
C14A0.93201 (13)0.75450 (12)0.57704 (8)0.0272 (2)
C15A0.81326 (15)0.66133 (14)0.60712 (8)0.0296 (2)
H15A0.79870.69390.66860.036*
C16A0.71637 (14)0.52038 (13)0.54644 (7)0.0282 (2)
H16A0.63690.45710.56740.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02376 (12)0.02918 (13)0.02258 (12)0.00799 (9)0.00616 (9)0.00470 (9)
S20.03053 (15)0.04077 (17)0.03995 (17)0.01490 (12)0.00683 (12)0.00491 (13)
N10.0350 (5)0.0402 (5)0.0211 (4)0.0189 (4)0.0066 (4)0.0072 (4)
N20.0260 (4)0.0306 (4)0.0204 (4)0.0103 (3)0.0052 (3)0.0053 (3)
N30.0252 (4)0.0254 (4)0.0234 (4)0.0073 (3)0.0074 (3)0.0057 (3)
C10.0248 (4)0.0222 (4)0.0213 (4)0.0040 (3)0.0064 (4)0.0057 (3)
C20.0250 (5)0.0244 (4)0.0221 (4)0.0040 (4)0.0050 (4)0.0047 (4)
C30.0463 (7)0.0324 (6)0.0421 (7)0.0164 (5)0.0146 (6)0.0073 (5)
C110.0245 (4)0.0213 (4)0.0210 (4)0.0029 (3)0.0062 (3)0.0050 (3)
C120.0265 (5)0.0263 (5)0.0216 (4)0.0025 (4)0.0050 (4)0.0019 (4)
C130.0245 (5)0.0317 (5)0.0253 (5)0.0036 (4)0.0027 (4)0.0036 (4)
C140.0242 (5)0.0255 (5)0.0280 (5)0.0046 (4)0.0077 (4)0.0066 (4)
C150.0267 (5)0.0249 (5)0.0240 (5)0.0031 (4)0.0065 (4)0.0013 (4)
C160.0236 (5)0.0252 (5)0.0217 (4)0.0027 (4)0.0038 (4)0.0030 (4)
S1A0.03812 (15)0.02424 (13)0.01908 (12)0.00001 (10)0.00147 (10)0.00366 (9)
S2A0.03119 (15)0.02522 (14)0.04128 (17)0.00205 (11)0.00131 (12)0.00120 (11)
N1A0.0401 (5)0.0288 (5)0.0220 (4)0.0014 (4)0.0068 (4)0.0061 (4)
N2A0.0329 (5)0.0224 (4)0.0194 (4)0.0003 (3)0.0039 (3)0.0033 (3)
N3A0.0289 (4)0.0211 (4)0.0227 (4)0.0025 (3)0.0023 (3)0.0035 (3)
C1A0.0282 (5)0.0235 (4)0.0201 (4)0.0062 (4)0.0033 (4)0.0061 (3)
C2A0.0279 (5)0.0231 (4)0.0229 (5)0.0036 (4)0.0043 (4)0.0041 (4)
C3A0.0577 (9)0.0387 (7)0.0343 (7)0.0024 (6)0.0097 (6)0.0026 (5)
C11A0.0239 (4)0.0224 (4)0.0224 (4)0.0058 (3)0.0026 (4)0.0042 (3)
C12A0.0273 (5)0.0259 (5)0.0241 (5)0.0073 (4)0.0050 (4)0.0070 (4)
C13A0.0252 (5)0.0254 (5)0.0323 (5)0.0050 (4)0.0044 (4)0.0085 (4)
C14A0.0232 (5)0.0227 (4)0.0301 (5)0.0063 (4)0.0008 (4)0.0018 (4)
C15A0.0291 (5)0.0295 (5)0.0244 (5)0.0054 (4)0.0041 (4)0.0007 (4)
C16A0.0274 (5)0.0281 (5)0.0244 (5)0.0026 (4)0.0052 (4)0.0032 (4)
Geometric parameters (Å, º) top
S1—C11.7045 (11)S1A—C1A1.7045 (11)
S2—C141.7645 (11)S2A—C14A1.7640 (11)
S2—C31.7991 (14)S2A—C3A1.7995 (17)
N1—C11.3244 (14)N1A—C1A1.3297 (14)
N1—H1A0.873 (17)N1A—H1C0.869 (19)
N1—H1B0.875 (17)N1A—H1D0.852 (17)
N2—C11.3561 (13)N2A—C1A1.3493 (13)
N2—N31.3783 (12)N2A—N3A1.3851 (12)
N2—H20.854 (17)N2A—H2A0.906 (17)
N3—C21.2874 (13)N3A—C2A1.2880 (14)
C2—C111.4649 (15)C2A—C11A1.4639 (14)
C2—H2B0.9500C2A—H2A10.9500
C3—H3A0.9800C3A—H3A10.9800
C3—H3B0.9800C3A—H3A20.9800
C3—H3C0.9800C3A—H3A30.9800
C11—C161.3999 (14)C11A—C16A1.3987 (15)
C11—C121.4060 (15)C11A—C12A1.4067 (15)
C12—C131.3829 (16)C12A—C13A1.3842 (15)
C12—H120.9500C12A—H12A0.9500
C13—C141.4055 (15)C13A—C14A1.4079 (16)
C13—H130.9500C13A—H13A0.9500
C14—C151.3992 (15)C14A—C15A1.4000 (17)
C15—C161.3926 (15)C15A—C16A1.3958 (15)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C14—S2—C3103.46 (6)C14A—S2A—C3A103.74 (7)
C1—N1—H1A118.9 (11)C1A—N1A—H1C120.3 (13)
C1—N1—H1B118.9 (11)C1A—N1A—H1D120.6 (11)
H1A—N1—H1B117.9 (15)H1C—N1A—H1D118.9 (17)
C1—N2—N3118.67 (9)C1A—N2A—N3A119.41 (9)
C1—N2—H2120.0 (11)C1A—N2A—H2A120.2 (10)
N3—N2—H2119.9 (11)N3A—N2A—H2A120.4 (10)
C2—N3—N2116.18 (9)C2A—N3A—N2A115.19 (9)
N1—C1—N2117.64 (10)N1A—C1A—N2A117.52 (10)
N1—C1—S1123.74 (8)N1A—C1A—S1A122.52 (8)
N2—C1—S1118.57 (8)N2A—C1A—S1A119.96 (8)
N3—C2—C11119.66 (10)N3A—C2A—C11A121.25 (10)
N3—C2—H2B120.2N3A—C2A—H2A1119.4
C11—C2—H2B120.2C11A—C2A—H2A1119.4
S2—C3—H3A109.5S2A—C3A—H3A1109.5
S2—C3—H3B109.5S2A—C3A—H3A2109.5
H3A—C3—H3B109.5H3A1—C3A—H3A2109.5
S2—C3—H3C109.5S2A—C3A—H3A3109.5
H3A—C3—H3C109.5H3A1—C3A—H3A3109.5
H3B—C3—H3C109.5H3A2—C3A—H3A3109.5
C16—C11—C12118.67 (10)C16A—C11A—C12A118.58 (10)
C16—C11—C2119.91 (9)C16A—C11A—C2A119.77 (10)
C12—C11—C2121.39 (9)C12A—C11A—C2A121.65 (9)
C13—C12—C11120.38 (10)C13A—C12A—C11A120.60 (10)
C13—C12—H12119.8C13A—C12A—H12A119.7
C11—C12—H12119.8C11A—C12A—H12A119.7
C12—C13—C14120.67 (10)C12A—C13A—C14A120.55 (10)
C12—C13—H13119.7C12A—C13A—H13A119.7
C14—C13—H13119.7C14A—C13A—H13A119.7
C15—C14—C13119.32 (10)C15A—C14A—C13A119.27 (10)
C15—C14—S2124.70 (8)C15A—C14A—S2A124.71 (9)
C13—C14—S2115.97 (8)C13A—C14A—S2A116.02 (9)
C16—C15—C14119.71 (10)C16A—C15A—C14A119.74 (10)
C16—C15—H15120.1C16A—C15A—H15A120.1
C14—C15—H15120.1C14A—C15A—H15A120.1
C15—C16—C11121.17 (10)C15A—C16A—C11A121.24 (10)
C15—C16—H16119.4C15A—C16A—H16A119.4
C11—C16—H16119.4C11A—C16A—H16A119.4
C1—N2—N3—C2176.22 (10)C1A—N2A—N3A—C2A177.30 (10)
N3—N2—C1—N17.31 (15)N3A—N2A—C1A—N1A1.10 (16)
N3—N2—C1—S1175.05 (8)N3A—N2A—C1A—S1A179.07 (8)
N2—N3—C2—C11179.95 (9)N2A—N3A—C2A—C11A179.70 (9)
N3—C2—C11—C16161.46 (10)N3A—C2A—C11A—C16A171.71 (11)
N3—C2—C11—C1216.63 (16)N3A—C2A—C11A—C12A8.53 (16)
C16—C11—C12—C133.11 (16)C16A—C11A—C12A—C13A1.04 (16)
C2—C11—C12—C13175.00 (10)C2A—C11A—C12A—C13A179.19 (10)
C11—C12—C13—C140.92 (17)C11A—C12A—C13A—C14A0.17 (16)
C12—C13—C14—C151.51 (17)C12A—C13A—C14A—C15A0.96 (17)
C12—C13—C14—S2179.97 (9)C12A—C13A—C14A—S2A179.10 (8)
C3—S2—C14—C155.08 (12)C3A—S2A—C14A—C15A7.41 (12)
C3—S2—C14—C13176.55 (9)C3A—S2A—C14A—C13A172.52 (9)
C13—C14—C15—C161.69 (17)C13A—C14A—C15A—C16A0.52 (17)
S2—C14—C15—C16179.99 (9)S2A—C14A—C15A—C16A179.55 (9)
C14—C15—C16—C110.54 (17)C14A—C15A—C16A—C11A0.72 (18)
C12—C11—C16—C152.94 (16)C12A—C11A—C16A—C15A1.50 (17)
C2—C11—C16—C15175.20 (10)C2A—C11A—C16A—C15A178.74 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.873 (17)2.459 (17)3.3254 (11)172.1 (15)
N1—H1B···N30.875 (17)2.266 (16)2.6364 (13)105.4 (12)
N2—H2···S1Ai0.854 (17)2.555 (18)3.3412 (10)153.5 (15)
N1A—H1C···S1Aii0.869 (19)2.604 (19)3.4707 (11)174.7 (17)
N2A—H2A···S1i0.906 (17)2.454 (17)3.3499 (10)169.8 (14)
N1A—H1D···N3A0.852 (17)2.302 (16)2.6440 (14)104.2 (13)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
 

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