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The title compound, C6H9N3OS, was obtained by cyclization of ethyl 2-methyl­aceto­acetate thio­semicarbazone with sodium methanolate in methanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation of the mother liquor. The pyrazolone moiety is essentially planar. The S atom is cis with respect to the protonated endocyclic N2 atom, probably because the intramolecular hydrogen bonds allowed by this arrangement afford greater stability than those allowed when S is trans to N-2. Intermolecular hydrogen bonds link the mol­ecules in interlocking pleated sheets, stacked along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201098X/cm6010sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201098X/cm6010Isup2.hkl
Contains datablock I

CCDC reference: 189914

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.132
  • Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and SCHAKAL (Keller, 1988).

2,5-dihydro-3,4-dimethyl-5-oxo-1H-pyrazole-1-carbothioamide top
Crystal data top
C6H9N3OSF(000) = 720
Mr = 171.22Dx = 1.429 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 n 2 a bCell parameters from 4044 reflections
a = 7.9246 (13) Åθ = 2.5–28.0°
b = 12.543 (2) ŵ = 0.35 mm1
c = 16.015 (3) ÅT = 293 K
V = 1591.9 (4) Å3Prism, colourless
Z = 80.37 × 0.27 × 0.20 mm
Data collection top
Bruker SMART-CCD 1000
diffractometer
1904 independent reflections
Radiation source: fine-focus sealed tube1559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
φ and ω scansθmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.875, Tmax = 0.932k = 916
8987 measured reflectionsl = 2120
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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0809P)2 + 0.2527P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1904 reflectionsΔρmax = 0.37 e Å3
105 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0133 (18)
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
S0.09270 (7)0.13621 (4)0.41542 (3)0.0492 (2)
N10.1054 (2)0.07459 (13)0.39897 (10)0.0530 (5)
H1A0.13210.13060.37090.064*
H1B0.05850.08090.44710.064*
N20.21228 (18)0.01946 (10)0.29012 (8)0.0369 (3)
N30.2586 (2)0.11183 (11)0.24929 (9)0.0404 (4)
H30.221 (3)0.168 (2)0.2680 (17)0.072 (8)*
O0.24333 (19)0.16257 (9)0.26406 (9)0.0542 (4)
C10.1365 (2)0.02105 (12)0.36803 (11)0.0368 (4)
C20.3316 (2)0.08462 (12)0.17618 (9)0.0355 (4)
C30.3405 (2)0.02382 (12)0.16908 (10)0.0361 (4)
C40.2656 (2)0.06864 (12)0.24109 (10)0.0375 (4)
C120.3893 (3)0.16841 (16)0.11721 (12)0.0498 (5)
H12A0.50760.15950.10640.075*
H12B0.36990.23740.14130.075*
H12C0.32770.16240.06580.075*
C130.4165 (3)0.08722 (16)0.09951 (12)0.0507 (5)
H13A0.33200.10140.05800.076*
H13B0.45900.15340.12110.076*
H13C0.50730.04760.07480.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0694 (4)0.0349 (3)0.0432 (3)0.0052 (2)0.0150 (2)0.00179 (17)
N10.0788 (12)0.0334 (8)0.0468 (9)0.0052 (7)0.0195 (8)0.0023 (7)
N20.0517 (8)0.0246 (7)0.0344 (7)0.0008 (5)0.0034 (6)0.0003 (5)
N30.0584 (10)0.0245 (7)0.0383 (7)0.0006 (6)0.0090 (6)0.0014 (6)
O0.0891 (11)0.0245 (6)0.0490 (8)0.0025 (6)0.0072 (7)0.0019 (5)
C10.0411 (9)0.0338 (8)0.0357 (8)0.0009 (6)0.0007 (6)0.0012 (6)
C20.0428 (9)0.0319 (8)0.0317 (8)0.0021 (7)0.0017 (6)0.0007 (6)
C30.0449 (9)0.0300 (8)0.0334 (8)0.0018 (6)0.0037 (7)0.0037 (6)
C40.0506 (10)0.0268 (8)0.0351 (8)0.0004 (7)0.0043 (7)0.0039 (6)
C120.0656 (12)0.0395 (9)0.0443 (10)0.0002 (8)0.0110 (8)0.0075 (8)
C130.0697 (13)0.0429 (10)0.0396 (9)0.0039 (9)0.0048 (8)0.0092 (8)
Geometric parameters (Å, º) top
S—C11.6682 (17)C2—C31.367 (2)
N1—C11.321 (2)C2—C121.485 (2)
N1—H1A0.8600C3—C41.414 (2)
N1—H1B0.8600C3—C131.495 (2)
N2—N31.3801 (18)C12—H12A0.9600
N2—C11.385 (2)C12—H12B0.9600
N2—C41.420 (2)C12—H12C0.9600
N3—C21.350 (2)C13—H13A0.9600
N3—H30.82 (3)C13—H13B0.9600
O—C41.2468 (19)C13—H13C0.9600
C1—N1—H1A120.0C4—C3—C13124.43 (15)
C1—N1—H1B120.0O—C4—C3132.52 (15)
H1A—N1—H1B120.0O—C4—N2122.01 (16)
N3—N2—C1122.01 (12)C3—C4—N2105.47 (13)
N3—N2—C4108.19 (13)C2—C12—H12A109.5
C1—N2—C4129.68 (13)C2—C12—H12B109.5
C2—N3—N2108.22 (13)H12A—C12—H12B109.5
C2—N3—H3133.7 (18)C2—C12—H12C109.5
N2—N3—H3116.6 (18)H12A—C12—H12C109.5
N1—C1—N2113.93 (15)H12B—C12—H12C109.5
N1—C1—S125.23 (14)C3—C13—H13A109.5
N2—C1—S120.84 (11)C3—C13—H13B109.5
N3—C2—C3110.24 (14)H13A—C13—H13B109.5
N3—C2—C12120.31 (15)C3—C13—H13C109.5
C3—C2—C12129.45 (15)H13A—C13—H13C109.5
C2—C3—C4107.83 (13)H13B—C13—H13C109.5
C2—C3—C13127.73 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O0.861.972.661 (2)137
N3—H3···S0.82 (3)2.60 (3)2.9834 (16)110 (2)
N1—H1B···Si0.862.603.4495 (17)169
N3—H3···Oii0.82 (3)2.15 (3)2.840 (2)142 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1/2, y+1/2, z.
 

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