4-Phenyl-1-(1H-1,2,4-triazol-3-yl­carbonyl)­thio­semicarbazide

The title compound, C₁₀H₁₀N₆OS, was synthesized by the reaction of 1H-1,2,4-triazol-3-yl­hydrazine with phenyl isocyanate in benzene. The mol­ecule is non-planar, the dihedral angle between the two aromatic rings being 62.07 (7)°. N—H...O, N—H...N and N—H...S hydrogen bonds are observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.077
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Phenyl-1-(1H-1,2,4-triazol-3-ylcarbonyl)thiosemicarbazide

Crystal data

C10H10N6OS	F(000) = 1088
Mr = 262.30	Dx = 1.419 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1478 reflections
a = 12.1981 (10) Å	θ = 5.2–42.9°
b = 10.1097 (8) Å	µ = 0.26 mm^−1
c = 19.9112 (16) Å	T = 293 K
V = 2455.4 (3) Å^3	Block, colourless
Z = 8	0.38 × 0.25 × 0.09 mm

Data collection

Bruker APEX area-detector diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	1653 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→12
Tmin = 0.908, Tmax = 0.977	k = −12→12
13557 measured reflections	l = −25→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0246P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.85	(Δ/σ)max = 0.001
2684 reflections	Δρmax = 0.26 e Å^−3
203 parameters	Δρmin = −0.31 e Å^−3
2 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.36987 (5)	1.03361 (6)	0.57497 (2)	0.03934 (17)
N1	0.36349 (16)	1.02177 (17)	0.44388 (7)	0.0329 (4)
N2	0.31876 (15)	0.97948 (18)	0.38313 (8)	0.0324 (4)
N3	0.29471 (15)	0.88794 (16)	0.25111 (8)	0.0377 (5)
N4	0.25263 (16)	0.81516 (19)	0.20040 (9)	0.0427 (5)
N5	0.22539 (15)	0.69518 (17)	0.28896 (7)	0.0384 (5)
N6	0.19538 (15)	1.02416 (18)	0.49447 (8)	0.0367 (5)
O1	0.32144 (14)	0.76525 (14)	0.41589 (6)	0.0512 (5)
C1	0.30337 (17)	1.02426 (18)	0.50070 (9)	0.0289 (5)
C2	0.30769 (17)	0.8486 (2)	0.37264 (9)	0.0318 (5)
C3	0.27521 (17)	0.8111 (2)	0.30301 (9)	0.0294 (5)
C4	0.2126 (2)	0.7021 (2)	0.22316 (11)	0.0426 (6)
C5	0.12087 (17)	1.0323 (2)	0.54984 (9)	0.0318 (5)
C6	0.1021 (2)	0.9218 (2)	0.58824 (11)	0.0467 (6)
C7	0.0303 (2)	0.9297 (3)	0.64178 (13)	0.0586 (8)
C8	−0.0223 (2)	1.0450 (3)	0.65562 (13)	0.0595 (8)
C9	−0.0057 (2)	1.1540 (3)	0.61621 (13)	0.0576 (8)
C10	0.0672 (2)	1.1481 (3)	0.56297 (11)	0.0443 (6)
H1	0.4352 (13)	1.008 (2)	0.4485 (9)	0.054 (7)*
H2	0.3134 (18)	1.041 (2)	0.3538 (10)	0.057 (8)*
H4	0.1835 (17)	0.640 (2)	0.1961 (9)	0.049 (7)*
H6	0.1330 (17)	0.840 (2)	0.5756 (9)	0.051 (7)*
H7	0.0171 (19)	0.8533 (17)	0.6649 (10)	0.062 (8)*
H8	−0.0704 (18)	1.055 (2)	0.6920 (10)	0.063 (8)*
H9	−0.040 (2)	1.233 (2)	0.6255 (11)	0.085 (10)*
H10	0.0811 (17)	1.222 (2)	0.5374 (9)	0.049 (7)*
H4A	0.266 (2)	0.840 (2)	0.1587 (11)	0.082 (9)*
H6A	0.1703 (17)	1.038 (2)	0.4574 (9)	0.046 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0373 (3)	0.0595 (4)	0.0212 (3)	0.0019 (3)	−0.0021 (2)	−0.0072 (2)
N1	0.0345 (11)	0.0445 (11)	0.0197 (9)	0.0036 (10)	−0.0008 (8)	−0.0028 (7)
N2	0.0479 (12)	0.0326 (11)	0.0166 (9)	0.0037 (9)	−0.0038 (8)	0.0004 (8)
N3	0.0554 (13)	0.0352 (11)	0.0226 (9)	−0.0026 (9)	0.0012 (9)	−0.0011 (8)
N4	0.0651 (14)	0.0415 (12)	0.0215 (10)	−0.0043 (10)	0.0008 (9)	0.0004 (9)
N5	0.0591 (14)	0.0344 (11)	0.0217 (9)	−0.0050 (9)	0.0016 (9)	−0.0007 (8)
N6	0.0353 (11)	0.0555 (12)	0.0193 (9)	0.0053 (9)	−0.0035 (8)	−0.0002 (9)
O1	0.0844 (13)	0.0389 (9)	0.0303 (8)	0.0035 (9)	−0.0106 (8)	0.0104 (7)
C1	0.0359 (12)	0.0282 (11)	0.0225 (10)	0.0027 (10)	0.0012 (9)	0.0003 (9)
C2	0.0359 (14)	0.0355 (13)	0.0241 (11)	0.0038 (10)	0.0024 (10)	0.0022 (9)
C3	0.0392 (14)	0.0283 (12)	0.0207 (10)	0.0048 (10)	0.0047 (9)	0.0027 (9)
C4	0.0644 (19)	0.0347 (14)	0.0288 (13)	−0.0065 (13)	−0.0019 (12)	−0.0030 (10)
C5	0.0290 (12)	0.0426 (13)	0.0238 (10)	0.0001 (11)	−0.0019 (9)	−0.0014 (10)
C6	0.0501 (17)	0.0450 (17)	0.0449 (15)	0.0053 (13)	0.0033 (12)	0.0065 (12)
C7	0.0501 (18)	0.074 (2)	0.0513 (17)	−0.0083 (16)	0.0019 (13)	0.0253 (15)
C8	0.0358 (15)	0.105 (3)	0.0375 (15)	0.0086 (17)	0.0092 (12)	0.0069 (16)
C9	0.0494 (18)	0.072 (2)	0.0512 (16)	0.0178 (16)	0.0093 (14)	−0.0026 (15)
C10	0.0466 (16)	0.0455 (17)	0.0408 (14)	0.0029 (13)	0.0053 (12)	0.0017 (12)

Geometric parameters (Å, º)

S1—C1	1.6894 (19)	O1—C2	1.216 (2)
N1—C1	1.348 (2)	C2—C3	1.491 (2)
N1—N2	1.394 (2)	C4—H4	0.903 (19)
N1—H1	0.890 (15)	C5—C10	1.367 (3)
N2—C2	1.346 (2)	C5—C6	1.373 (3)
N2—H2	0.85 (2)	C6—C7	1.382 (3)
N3—C3	1.314 (2)	C6—H6	0.94 (2)
N3—N4	1.351 (2)	C7—C8	1.359 (3)
N4—C4	1.323 (3)	C7—H7	0.913 (15)
N4—H4A	0.88 (2)	C8—C9	1.368 (3)
N5—C4	1.321 (2)	C8—H8	0.94 (2)
N5—C3	1.350 (2)	C9—C10	1.385 (3)
N6—C1	1.323 (2)	C9—H9	0.93 (2)
N6—C5	1.431 (2)	C10—H10	0.924 (19)
N6—H6A	0.812 (18)
C1—N1—N2	121.39 (18)	N5—C3—C2	122.21 (17)
C1—N1—H1	116.8 (13)	N5—C4—N4	110.0 (2)
N2—N1—H1	115.3 (13)	N5—C4—H4	126.9 (13)
C2—N2—N1	118.38 (17)	N4—C4—H4	123.1 (13)
C2—N2—H2	126.9 (14)	C10—C5—C6	120.7 (2)
N1—N2—H2	113.5 (15)	C10—C5—N6	120.07 (19)
C3—N3—N4	101.36 (17)	C6—C5—N6	119.2 (2)
C4—N4—N3	110.79 (18)	C5—C6—C7	119.2 (2)
C4—N4—H4A	129.7 (16)	C5—C6—H6	119.8 (12)
N3—N4—H4A	118.4 (17)	C7—C6—H6	120.7 (13)
C4—N5—C3	102.28 (17)	C8—C7—C6	120.3 (3)
C1—N6—C5	124.06 (17)	C8—C7—H7	122.7 (15)
C1—N6—H6A	117.4 (15)	C6—C7—H7	116.8 (15)
C5—N6—H6A	116.8 (15)	C7—C8—C9	120.3 (3)
N6—C1—N1	117.57 (17)	C7—C8—H8	123.1 (14)
N6—C1—S1	124.06 (15)	C9—C8—H8	116.6 (14)
N1—C1—S1	118.32 (16)	C8—C9—C10	120.0 (3)
O1—C2—N2	123.86 (18)	C8—C9—H9	121.0 (15)
O1—C2—C3	121.27 (19)	C10—C9—H9	118.9 (16)
N2—C2—C3	114.87 (17)	C5—C10—C9	119.4 (2)
N3—C3—N5	115.58 (16)	C5—C10—H10	120.2 (13)
N3—C3—C2	122.20 (18)	C9—C10—H10	120.3 (13)
C1—N1—N2—C2	−78.2 (2)	O1—C2—C3—N5	22.2 (3)
C3—N3—N4—C4	−0.7 (2)	N2—C2—C3—N5	−157.0 (2)
C5—N6—C1—N1	−177.22 (18)	C3—N5—C4—N4	0.1 (3)
C5—N6—C1—S1	0.2 (3)	N3—N4—C4—N5	0.4 (3)
N2—N1—C1—N6	−19.8 (3)	C1—N6—C5—C10	104.4 (2)
N2—N1—C1—S1	162.71 (15)	C1—N6—C5—C6	−77.3 (3)
N1—N2—C2—O1	9.5 (3)	C10—C5—C6—C7	−1.8 (3)
N1—N2—C2—C3	−171.23 (16)	N6—C5—C6—C7	179.9 (2)
N4—N3—C3—N5	0.7 (2)	C5—C6—C7—C8	1.0 (4)
N4—N3—C3—C2	179.74 (18)	C6—C7—C8—C9	0.8 (4)
C4—N5—C3—N3	−0.5 (3)	C7—C8—C9—C10	−1.7 (4)
C4—N5—C3—C2	−179.53 (19)	C6—C5—C10—C9	0.9 (3)
O1—C2—C3—N3	−156.7 (2)	N6—C5—C10—C9	179.2 (2)
N2—C2—C3—N3	24.0 (3)	C8—C9—C10—C5	0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1^i	0.812 (18)	2.44 (2)	2.904 (2)	116.9 (17)
N4—H4A···S1^ii	0.88 (2)	2.45 (2)	3.259 (2)	152 (2)
N2—H2···N5^i	0.85 (2)	2.08 (2)	2.926 (2)	171 (2)
N1—H1···S1^iii	0.89 (2)	2.46 (2)	3.322 (2)	163 (2)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, −y+2, z−1/2; (iii) −x+1, −y+2, −z+1.