4-{[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl-idene]amino}-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(12)H(10)N(6)S, a weak intra-molecular C-H⋯S hydrogen bond stabilizes the mol-ecular conformation. The pyrazole and triazole rings form a dihedral angle of 17.82 (8)°. The mol-ecule adopts an E configuration with respect to the central C=N double bond. In the crystal, inter-molecular N-H⋯N and N-H⋯S hydrogen bonds link mol-ecules into chains propagating in [20[Formula: see text]].

Related literature

For applications of Schiff bases, see: Kahveci et al. (2005 ▶); Bekircan et al. (2006 ▶); Singh & Dash (1988 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C12H10N6S

M = 270.32

Monoclinic,

a = 4.1180 (4) Å

b = 17.9237 (16) Å

c = 17.0787 (15) Å

β = 97.352 (3)°

V = 1250.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.55 × 0.26 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.872, T max = 0.954

14262 measured reflections

4361 independent reflections

3204 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 1.03

4361 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024834/cv5118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024834/cv5118Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024834/cv5118Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H10N6S	F(000) = 560
Mr = 270.32	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4488 reflections
a = 4.1180 (4) Å	θ = 2.7–32.1°
b = 17.9237 (16) Å	µ = 0.25 mm−1
c = 17.0787 (15) Å	T = 296 K
β = 97.352 (3)°	Block, colourless
V = 1250.2 (2) Å3	0.55 × 0.26 × 0.19 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4361 independent reflections
Radiation source: fine-focus sealed tube	3204 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→6
Tmin = 0.872, Tmax = 0.954	k = −23→26
14262 measured reflections	l = −24→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.2417P] where P = (Fo2 + 2Fc2)/3
4361 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
S1	0.40558 (10)	0.78578 (2)	0.54047 (2)	0.04665 (12)
N1	0.9965 (3)	0.79730 (6)	0.20882 (6)	0.0407 (3)
N2	1.0317 (3)	0.72254 (7)	0.20392 (7)	0.0420 (3)
N3	0.5720 (3)	0.66043 (6)	0.39821 (6)	0.0384 (2)
N4	0.3925 (3)	0.64999 (5)	0.46129 (6)	0.0348 (2)
N5	0.1337 (4)	0.57751 (7)	0.53767 (7)	0.0488 (3)
N6	0.1665 (3)	0.64885 (6)	0.56639 (7)	0.0413 (3)
C1	0.6630 (4)	0.93695 (8)	0.23797 (9)	0.0472 (3)
H1A	0.6471	0.9232	0.1851	0.057*
C2	0.5789 (5)	1.00854 (9)	0.25766 (11)	0.0598 (4)
H2A	0.5067	1.0426	0.2181	0.072*
C3	0.6017 (5)	1.02944 (9)	0.33542 (12)	0.0641 (5)
H3A	0.5426	1.0774	0.3487	0.077*
C4	0.7125 (5)	0.97907 (10)	0.39391 (11)	0.0629 (5)
H4A	0.7289	0.9935	0.4466	0.075*
C5	0.7998 (4)	0.90706 (9)	0.37484 (9)	0.0491 (3)
H5A	0.8769	0.8736	0.4145	0.059*
C6	0.7714 (3)	0.88523 (7)	0.29628 (7)	0.0370 (3)
C7	0.8527 (3)	0.80877 (7)	0.27359 (7)	0.0341 (2)
C8	0.9156 (3)	0.68630 (7)	0.26224 (8)	0.0388 (3)
H8A	0.9153	0.6349	0.2698	0.047*
C9	0.7949 (3)	0.73971 (7)	0.30963 (7)	0.0337 (2)
C10	0.6185 (3)	0.72707 (7)	0.37639 (7)	0.0358 (2)
H10A	0.5400	0.7671	0.4030	0.043*
C11	0.2728 (4)	0.58040 (7)	0.47418 (8)	0.0450 (3)
H11A	0.2897	0.5399	0.4410	0.054*
C12	0.3230 (3)	0.69554 (7)	0.52237 (7)	0.0335 (2)
H1N2	1.114 (5)	0.7046 (11)	0.1654 (12)	0.064 (6)*
H1N6	0.095 (5)	0.6601 (12)	0.6124 (12)	0.067 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0665 (2)	0.03563 (18)	0.04225 (19)	−0.01109 (15)	0.02386 (16)	−0.00666 (13)
N1	0.0537 (7)	0.0369 (6)	0.0350 (5)	−0.0016 (4)	0.0193 (5)	0.0000 (4)
N2	0.0546 (7)	0.0397 (6)	0.0357 (5)	0.0009 (5)	0.0210 (5)	−0.0030 (4)
N3	0.0492 (6)	0.0373 (5)	0.0323 (5)	0.0024 (4)	0.0192 (4)	0.0020 (4)
N4	0.0459 (6)	0.0294 (5)	0.0322 (5)	0.0016 (4)	0.0167 (4)	0.0020 (4)
N5	0.0741 (8)	0.0330 (6)	0.0443 (6)	−0.0067 (5)	0.0264 (6)	−0.0002 (4)
N6	0.0590 (7)	0.0339 (5)	0.0354 (5)	−0.0037 (5)	0.0225 (5)	−0.0012 (4)
C1	0.0609 (9)	0.0393 (7)	0.0429 (7)	0.0019 (6)	0.0128 (6)	0.0037 (5)
C2	0.0743 (11)	0.0391 (8)	0.0677 (10)	0.0064 (7)	0.0150 (9)	0.0070 (7)
C3	0.0760 (12)	0.0395 (8)	0.0797 (12)	0.0054 (8)	0.0213 (9)	−0.0107 (8)
C4	0.0801 (12)	0.0566 (10)	0.0543 (9)	−0.0021 (9)	0.0172 (8)	−0.0203 (8)
C5	0.0625 (9)	0.0468 (8)	0.0391 (7)	0.0006 (7)	0.0110 (6)	−0.0035 (6)
C6	0.0414 (6)	0.0348 (6)	0.0368 (6)	−0.0027 (5)	0.0134 (5)	−0.0009 (5)
C7	0.0393 (6)	0.0353 (6)	0.0294 (5)	−0.0010 (5)	0.0113 (4)	0.0006 (4)
C8	0.0462 (7)	0.0358 (6)	0.0366 (6)	−0.0001 (5)	0.0140 (5)	0.0002 (5)
C9	0.0375 (6)	0.0348 (6)	0.0306 (5)	0.0003 (4)	0.0115 (4)	0.0012 (4)
C10	0.0411 (6)	0.0366 (6)	0.0321 (5)	0.0030 (5)	0.0139 (5)	0.0021 (4)
C11	0.0695 (9)	0.0288 (6)	0.0409 (6)	−0.0015 (6)	0.0231 (6)	−0.0010 (5)
C12	0.0381 (6)	0.0336 (5)	0.0307 (5)	0.0010 (4)	0.0121 (4)	0.0003 (4)

S1—C12	1.6735 (13)	C2—C3	1.372 (3)
N1—C7	1.3358 (15)	C2—H2A	0.9300
N1—N2	1.3516 (16)	C3—C4	1.380 (3)
N2—C8	1.3283 (17)	C3—H3A	0.9300
N2—H1N2	0.84 (2)	C4—C5	1.390 (2)
N3—C10	1.2731 (17)	C4—H4A	0.9300
N3—N4	1.3950 (14)	C5—C6	1.3880 (19)
N4—C11	1.3693 (16)	C5—H5A	0.9300
N4—C12	1.3830 (15)	C6—C7	1.4744 (17)
N5—C11	1.2905 (18)	C7—C9	1.4160 (17)
N5—N6	1.3700 (16)	C8—C9	1.3862 (17)
N6—C12	1.3433 (16)	C8—H8A	0.9300
N6—H1N6	0.90 (2)	C9—C10	1.4460 (16)
C1—C2	1.382 (2)	C10—H10A	0.9300
C1—C6	1.3916 (19)	C11—H11A	0.9300
C1—H1A	0.9300
C7—N1—N2	105.45 (10)	C6—C5—C4	119.74 (15)
C8—N2—N1	112.74 (11)	C6—C5—H5A	120.1
C8—N2—H1N2	128.2 (13)	C4—C5—H5A	120.1
N1—N2—H1N2	119.0 (13)	C5—C6—C1	118.92 (13)
C10—N3—N4	117.80 (11)	C5—C6—C7	121.48 (12)
C11—N4—C12	107.64 (10)	C1—C6—C7	119.60 (12)
C11—N4—N3	118.92 (10)	N1—C7—C9	110.02 (11)
C12—N4—N3	133.20 (10)	N1—C7—C6	120.03 (11)
C11—N5—N6	103.26 (11)	C9—C7—C6	129.93 (11)
C12—N6—N5	114.42 (11)	N2—C8—C9	106.89 (11)
C12—N6—H1N6	125.9 (14)	N2—C8—H8A	126.6
N5—N6—H1N6	119.6 (14)	C9—C8—H8A	126.6
C2—C1—C6	120.79 (15)	C8—C9—C7	104.90 (11)
C2—C1—H1A	119.6	C8—C9—C10	127.30 (12)
C6—C1—H1A	119.6	C7—C9—C10	127.52 (11)
C3—C2—C1	120.07 (16)	N3—C10—C9	119.17 (12)
C3—C2—H2A	120.0	N3—C10—H10A	120.4
C1—C2—H2A	120.0	C9—C10—H10A	120.4
C2—C3—C4	119.84 (15)	N5—C11—N4	112.28 (12)
C2—C3—H3A	120.1	N5—C11—H11A	123.9
C4—C3—H3A	120.1	N4—C11—H11A	123.9
C3—C4—C5	120.62 (16)	N6—C12—N4	102.40 (10)
C3—C4—H4A	119.7	N6—C12—S1	126.82 (9)
C5—C4—H4A	119.7	N4—C12—S1	130.77 (9)
C7—N1—N2—C8	0.32 (16)	N2—C8—C9—C7	−0.12 (15)
C10—N3—N4—C11	164.74 (13)	N2—C8—C9—C10	174.12 (13)
C10—N3—N4—C12	−21.8 (2)	N1—C7—C9—C8	0.33 (15)
C11—N5—N6—C12	−0.19 (18)	C6—C7—C9—C8	178.66 (13)
C6—C1—C2—C3	0.0 (3)	N1—C7—C9—C10	−173.91 (13)
C1—C2—C3—C4	0.8 (3)	C6—C7—C9—C10	4.4 (2)
C2—C3—C4—C5	−0.4 (3)	N4—N3—C10—C9	−178.11 (11)
C3—C4—C5—C6	−0.8 (3)	C8—C9—C10—N3	2.6 (2)
C4—C5—C6—C1	1.6 (2)	C7—C9—C10—N3	175.63 (13)
C4—C5—C6—C7	−178.29 (14)	N6—N5—C11—N4	0.09 (18)
C2—C1—C6—C5	−1.2 (2)	C12—N4—C11—N5	0.03 (18)
C2—C1—C6—C7	178.68 (15)	N3—N4—C11—N5	175.07 (12)
N2—N1—C7—C9	−0.39 (15)	N5—N6—C12—N4	0.20 (16)
N2—N1—C7—C6	−178.91 (12)	N5—N6—C12—S1	−179.73 (11)
C5—C6—C7—N1	−143.18 (14)	C11—N4—C12—N6	−0.14 (15)
C1—C6—C7—N1	36.93 (19)	N3—N4—C12—N6	−174.18 (13)
C5—C6—C7—C9	38.6 (2)	C11—N4—C12—S1	179.79 (12)
C1—C6—C7—C9	−141.26 (15)	N3—N4—C12—S1	5.8 (2)
N1—N2—C8—C9	−0.12 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.84 (2)	2.59 (2)	3.3593 (15)	153.6 (17)
N6—H1N6···N1ii	0.90 (2)	1.91 (2)	2.7884 (15)	168.0 (2)
C10—H10A···S1	0.93	2.50	3.2183 (13)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.84 (2)	2.59 (2)	3.3593 (15)	153.6 (17)
N6—H1N6⋯N1ii	0.90 (2)	1.91 (2)	2.7884 (15)	168.0 (2)
C10—H10A⋯S1	0.93	2.50	3.2183 (13)	134

Symmetry codes: (i) ; (ii) .