4-[(E)-2-Furylmethyl-eneamino]-3-phenyl-1H-1,2,4-triazole-5(4H)-thione.

In the title mol-ecule, C(13)H(10)N(4)OS, the triazole ring makes dihedral angles of 16.14 (9) and 58.51 (11)°, respectively, with the phenyl and furan rings. Intra-molecular C-H⋯N hydrogen bonds generate S(5) and S(6) ring motifs. In the crystal structure, centrosymmetrically related mol-ecules are linked via N-H⋯S hydrogen bonds to form dimeric pairs, which are inter-linked via C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activities of triazole derivatives, see: Clemons et al. (2004 ▶); Glerman et al. (1997 ▶); Holla et al. (2003 ▶); Johnston (2002 ▶); Kane et al. (1990 ▶); Kkgzel et al. (2004 ▶); Modzelewska & Kalabun (1999 ▶); Rollas et al. (1993 ▶); Shujuan et al. (2004 ▶); For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10N4OS

M = 270.31

Orthorhombic,

a = 27.4006 (6) Å

b = 11.4940 (3) Å

c = 7.7886 (2) Å

V = 2452.96 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 100.0 (1) K

0.40 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.829, T max = 0.974

40042 measured reflections

3627 independent reflections

2573 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.05

3627 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021806/ci2631sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021806/ci2631Isup2.hkl

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

C13H10N4OS	F000 = 1120
Mr = 270.31	Dx = 1.464 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5448 reflections
a = 27.4006 (6) Å	θ = 2.9–27.9º
b = 11.4940 (3) Å	µ = 0.26 mm−1
c = 7.7886 (2) Å	T = 100.0 (1) K
V = 2452.96 (10) Å3	Block, orange
Z = 8	0.40 × 0.13 × 0.10 mm

Bruker SMART APEXII CCD area-detector diffractometer	3627 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.072
T = 100.0(1) K	θmax = 30.2º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −38→38
Tmin = 0.829, Tmax = 0.974	k = −16→16
40042 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.3858P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3627 reflections	Δρmax = 0.26 e Å−3
176 parameters	Δρmin = −0.32 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
S1	0.494570 (15)	0.69781 (4)	0.50297 (6)	0.02259 (13)
O1	0.36669 (4)	1.02453 (10)	0.58350 (18)	0.0258 (3)
N1	0.44316 (5)	0.52097 (12)	0.6503 (2)	0.0225 (3)
N2	0.39895 (5)	0.49428 (12)	0.7222 (2)	0.0228 (3)
N3	0.40473 (5)	0.68093 (11)	0.66047 (19)	0.0190 (3)
N4	0.38912 (5)	0.79579 (12)	0.6319 (2)	0.0206 (3)
C1	0.44803 (6)	0.63262 (15)	0.6058 (2)	0.0203 (3)
C2	0.37554 (6)	0.59359 (14)	0.7269 (2)	0.0204 (4)
C3	0.32509 (6)	0.60514 (14)	0.7901 (2)	0.0198 (3)
C4	0.30539 (6)	0.51246 (15)	0.8824 (2)	0.0244 (4)
H4A	0.3247	0.4484	0.9086	0.029*
C5	0.25719 (6)	0.51543 (16)	0.9351 (3)	0.0267 (4)
H5A	0.2444	0.4533	0.9971	0.032*
C6	0.22781 (6)	0.60973 (16)	0.8967 (2)	0.0259 (4)
H6A	0.1954	0.6111	0.9320	0.031*
C7	0.24716 (6)	0.70213 (16)	0.8051 (3)	0.0255 (4)
H7A	0.2275	0.7656	0.7783	0.031*
C8	0.29558 (6)	0.70074 (15)	0.7530 (2)	0.0229 (4)
H8A	0.3084	0.7637	0.6931	0.028*
C9	0.41795 (6)	0.87250 (15)	0.6957 (2)	0.0212 (4)
H9A	0.4458	0.8494	0.7548	0.025*
C10	0.40718 (6)	0.99364 (15)	0.6757 (2)	0.0214 (4)
C11	0.42966 (7)	1.08948 (16)	0.7401 (3)	0.0268 (4)
H11A	0.4578	1.0913	0.8067	0.032*
C12	0.40148 (7)	1.18664 (15)	0.6854 (3)	0.0282 (4)
H12A	0.4075	1.2646	0.7095	0.034*
C13	0.36459 (7)	1.14332 (15)	0.5921 (3)	0.0289 (4)
H13A	0.3406	1.1883	0.5399	0.035*
H1N1	0.4628 (6)	0.4674 (14)	0.619 (3)	0.034 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0170 (2)	0.0210 (2)	0.0298 (3)	0.00050 (15)	0.00408 (17)	0.00147 (18)
O1	0.0210 (6)	0.0219 (6)	0.0344 (8)	0.0019 (5)	−0.0013 (5)	0.0001 (6)
N1	0.0169 (7)	0.0191 (7)	0.0316 (9)	0.0034 (5)	0.0022 (6)	0.0014 (6)
N2	0.0161 (7)	0.0206 (7)	0.0317 (9)	0.0010 (5)	0.0025 (6)	0.0013 (6)
N3	0.0153 (6)	0.0172 (7)	0.0244 (8)	0.0004 (5)	−0.0002 (6)	0.0008 (6)
N4	0.0185 (6)	0.0173 (7)	0.0260 (8)	0.0016 (5)	0.0010 (6)	0.0015 (6)
C1	0.0170 (7)	0.0208 (8)	0.0232 (9)	0.0014 (6)	−0.0020 (6)	−0.0018 (7)
C2	0.0182 (8)	0.0182 (8)	0.0247 (9)	−0.0013 (6)	−0.0014 (7)	0.0010 (7)
C3	0.0167 (7)	0.0215 (8)	0.0212 (8)	−0.0018 (6)	−0.0011 (6)	−0.0011 (7)
C4	0.0214 (8)	0.0256 (9)	0.0262 (9)	0.0001 (7)	0.0001 (7)	0.0040 (7)
C5	0.0240 (8)	0.0306 (10)	0.0255 (9)	−0.0038 (7)	0.0025 (7)	0.0058 (8)
C6	0.0199 (8)	0.0320 (10)	0.0259 (9)	−0.0012 (7)	0.0031 (7)	−0.0031 (8)
C7	0.0180 (8)	0.0231 (9)	0.0353 (10)	0.0026 (7)	0.0003 (7)	−0.0044 (8)
C8	0.0206 (8)	0.0204 (8)	0.0279 (10)	−0.0013 (6)	0.0008 (7)	0.0008 (7)
C9	0.0161 (7)	0.0240 (8)	0.0236 (9)	0.0006 (6)	0.0024 (7)	0.0003 (7)
C10	0.0169 (7)	0.0235 (9)	0.0238 (9)	−0.0008 (6)	0.0028 (7)	−0.0001 (7)
C11	0.0214 (8)	0.0254 (9)	0.0334 (10)	−0.0042 (7)	0.0033 (7)	−0.0027 (8)
C12	0.0280 (9)	0.0199 (9)	0.0366 (11)	−0.0031 (7)	0.0106 (8)	−0.0019 (8)
C13	0.0280 (9)	0.0216 (9)	0.0372 (11)	0.0054 (7)	0.0072 (8)	0.0050 (8)

S1—C1	1.6820 (17)	C5—C6	1.383 (3)
O1—C13	1.368 (2)	C5—H5A	0.93
O1—C10	1.368 (2)	C6—C7	1.385 (3)
N1—C1	1.336 (2)	C6—H6A	0.93
N1—N2	1.369 (2)	C7—C8	1.388 (2)
N1—H1N1	0.853 (9)	C7—H7A	0.93
N2—C2	1.310 (2)	C8—H8A	0.93
N3—C1	1.377 (2)	C9—C10	1.432 (2)
N3—C2	1.384 (2)	C9—H9A	0.93
N3—N4	1.4054 (18)	C10—C11	1.358 (2)
N4—C9	1.284 (2)	C11—C12	1.423 (3)
C2—C3	1.474 (2)	C11—H11A	0.93
C3—C4	1.394 (2)	C12—C13	1.341 (3)
C3—C8	1.395 (2)	C12—H12A	0.93
C4—C5	1.384 (2)	C13—H13A	0.93
C4—H4A	0.93
C13—O1—C10	105.50 (14)	C5—C6—C7	119.33 (16)
C1—N1—N2	114.19 (14)	C5—C6—H6A	120.3
C1—N1—H1N1	123.8 (15)	C7—C6—H6A	120.3
N2—N1—H1N1	120.9 (15)	C6—C7—C8	120.52 (17)
C2—N2—N1	104.44 (13)	C6—C7—H7A	119.7
C1—N3—C2	108.72 (13)	C8—C7—H7A	119.7
C1—N3—N4	126.29 (13)	C7—C8—C3	120.18 (16)
C2—N3—N4	124.37 (13)	C7—C8—H8A	119.9
C9—N4—N3	113.36 (14)	C3—C8—H8A	119.9
N1—C1—N3	102.77 (14)	N4—C9—C10	119.92 (16)
N1—C1—S1	128.84 (13)	N4—C9—H9A	120.0
N3—C1—S1	128.36 (13)	C10—C9—H9A	120.0
N2—C2—N3	109.79 (14)	C11—C10—O1	110.56 (15)
N2—C2—C3	123.18 (15)	C11—C10—C9	130.92 (17)
N3—C2—C3	127.01 (15)	O1—C10—C9	118.46 (15)
C4—C3—C8	119.00 (15)	C10—C11—C12	106.24 (17)
C4—C3—C2	117.83 (15)	C10—C11—H11A	126.9
C8—C3—C2	123.05 (15)	C12—C11—H11A	126.9
C5—C4—C3	120.26 (16)	C13—C12—C11	106.25 (16)
C5—C4—H4A	119.9	C13—C12—H12A	126.9
C3—C4—H4A	119.9	C11—C12—H12A	126.9
C6—C5—C4	120.71 (17)	C12—C13—O1	111.45 (16)
C6—C5—H5A	119.6	C12—C13—H13A	124.3
C4—C5—H5A	119.6	O1—C13—H13A	124.3
C1—N1—N2—C2	−1.5 (2)	C8—C3—C4—C5	0.4 (3)
C1—N3—N4—C9	−60.1 (2)	C2—C3—C4—C5	−175.78 (17)
C2—N3—N4—C9	129.83 (18)	C3—C4—C5—C6	0.3 (3)
N2—N1—C1—N3	2.8 (2)	C4—C5—C6—C7	−0.3 (3)
N2—N1—C1—S1	−175.45 (13)	C5—C6—C7—C8	−0.3 (3)
C2—N3—C1—N1	−2.91 (19)	C6—C7—C8—C3	1.0 (3)
N4—N3—C1—N1	−174.24 (15)	C4—C3—C8—C7	−1.0 (3)
C2—N3—C1—S1	175.32 (14)	C2—C3—C8—C7	174.91 (17)
N4—N3—C1—S1	4.0 (3)	N3—N4—C9—C10	179.42 (14)
N1—N2—C2—N3	−0.50 (19)	C13—O1—C10—C11	0.1 (2)
N1—N2—C2—C3	177.88 (17)	C13—O1—C10—C9	177.54 (16)
C1—N3—C2—N2	2.2 (2)	N4—C9—C10—C11	174.88 (19)
N4—N3—C2—N2	173.76 (15)	N4—C9—C10—O1	−2.0 (3)
C1—N3—C2—C3	−176.07 (17)	O1—C10—C11—C12	0.1 (2)
N4—N3—C2—C3	−4.5 (3)	C9—C10—C11—C12	−176.88 (18)
N2—C2—C3—C4	14.2 (3)	C10—C11—C12—C13	−0.3 (2)
N3—C2—C3—C4	−167.70 (17)	C11—C12—C13—O1	0.4 (2)
N2—C2—C3—C8	−161.76 (17)	C10—O1—C13—C12	−0.3 (2)
N3—C2—C3—C8	16.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1i	0.85 (2)	2.42 (2)	3.265 (2)	169 (2)
C4—H4A···N2	0.93	2.55	2.859 (2)	100
C6—H6A···O1ii	0.93	2.59	3.347 (2)	139
C8—H8A···N4	0.93	2.29	2.942 (2)	126
C5—H5A···Cg1iii	0.93	2.92	3.522 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1i	0.85 (2)	2.42 (2)	3.265 (2)	169 (2)
C4—H4A⋯N2	0.93	2.55	2.859 (2)	100
C6—H6A⋯O1ii	0.93	2.59	3.347 (2)	139
C8—H8A⋯N4	0.93	2.29	2.942 (2)	126
C5—H5A⋯Cg1iii	0.93	2.92	3.522 (2)	123

Symmetry codes: (i) ; (ii) ; (iii) .