4-[(3-Nitro-benzyl-idene)amino]-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(14)H(10)N(6)O(2)S, the dihedral angle between the pyridine and triazole rings is 3.21 (10)°. The mol-ecule is significantly twisted about the N(t)-N(b) (t = triazole and b = benzyl-idene) bond [C-N(t)-N(b)=C = 151.64 (17)°]. In the crystal, mol-ecules are linked by weak N-H⋯N hydrogen bonds, generating C(8) chains propagating in [10[Formula: see text]].

Related literature

For further details of the synthesis, see: Wang et al. (2010 ▶). For the biological activity of related compounds, see: Liu et al. (2011 ▶).

Experimental

Crystal data

C14H10N6O2S

M = 326.34

Monoclinic,

a = 3.7989 (13) Å

b = 24.334 (9) Å

c = 15.208 (6) Å

β = 93.035 (5)°

V = 1403.9 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.952, T max = 0.975

14478 measured reflections

3317 independent reflections

2807 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.103

S = 1.07

3317 reflections

212 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) gllobal, I. DOI: 10.1107/S1600536811054444/hb6570sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054444/hb6570Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054444/hb6570Isup3.cml

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

C14H10N6O2S	F(000) = 672
Mr = 326.34	Dx = 1.544 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.7989 (13) Å	Cell parameters from 4572 reflections
b = 24.334 (9) Å	θ = 1.6–28.0°
c = 15.208 (6) Å	µ = 0.25 mm−1
β = 93.035 (5)°	T = 113 K
V = 1403.9 (9) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.10 mm

Rigaku Saturn724 CCD diffractometer	3317 independent reflections
Radiation source: rotating anode	2807 reflections with I > 2σ(I)
multilayer	Rint = 0.056
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.6°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −32→32
Tmin = 0.952, Tmax = 0.975	l = −19→20
14478 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0391P)2 + 0.3217P] where P = (Fo2 + 2Fc2)/3
3317 reflections	(Δ/σ)max = 0.002
212 parameters	Δρmax = 0.30 e Å−3
7 restraints	Δρmin = −0.28 e Å−3

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	0.79238 (13)	0.064958 (19)	−0.05911 (3)	0.01910 (14)
O1	1.3928 (4)	0.08135 (6)	0.49993 (9)	0.0325 (4)
O2	1.2099 (6)	0.14915 (7)	0.41988 (12)	0.0631 (7)
N1	0.0656 (4)	0.30533 (6)	0.24207 (10)	0.0201 (4)
N2	0.3124 (4)	0.20542 (6)	−0.04085 (10)	0.0176 (3)
N3	0.4482 (4)	0.16171 (6)	−0.08450 (10)	0.0169 (3)
N4	0.5138 (4)	0.14148 (6)	0.05152 (9)	0.0144 (3)
N5	0.6482 (4)	0.12137 (6)	0.13193 (10)	0.0163 (3)
N6	1.2412 (5)	0.10008 (7)	0.43334 (11)	0.0270 (4)
C1	0.2990 (5)	0.21757 (8)	0.20265 (12)	0.0203 (4)
H1	0.3918	0.1830	0.2216	0.024*
C2	0.2005 (5)	0.25621 (8)	0.26337 (12)	0.0221 (4)
H2	0.2308	0.2472	0.3241	0.027*
C3	0.0267 (5)	0.31683 (8)	0.15567 (12)	0.0217 (4)
H3	−0.0704	0.3515	0.1387	0.026*
C4	0.1197 (5)	0.28122 (8)	0.09009 (12)	0.0198 (4)
H4	0.0884	0.2915	0.0299	0.024*
C5	0.2600 (5)	0.23011 (7)	0.11340 (12)	0.0153 (4)
C6	0.3606 (5)	0.19291 (7)	0.04253 (11)	0.0152 (4)
C7	0.5807 (5)	0.12176 (7)	−0.03166 (12)	0.0152 (4)
C8	0.6464 (5)	0.06903 (7)	0.14201 (12)	0.0160 (4)
H8	0.5481	0.0453	0.0976	0.019*
C9	0.8035 (5)	0.04757 (8)	0.22553 (11)	0.0158 (4)
C10	0.8222 (5)	−0.00903 (8)	0.24024 (12)	0.0176 (4)
H10	0.7268	−0.0337	0.1968	0.021*
C11	0.9793 (5)	−0.02948 (8)	0.31800 (12)	0.0205 (4)
H11	0.9920	−0.0681	0.3271	0.025*
C12	1.1176 (5)	0.00569 (8)	0.38243 (12)	0.0197 (4)
H12	1.2262	−0.0081	0.4356	0.024*
C13	1.0928 (5)	0.06162 (8)	0.36685 (12)	0.0189 (4)
C14	0.9407 (5)	0.08343 (8)	0.29021 (12)	0.0186 (4)
H14	0.9297	0.1221	0.2816	0.022*
H3A	0.461 (5)	0.1634 (9)	−0.1431 (7)	0.025 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0194 (3)	0.0182 (2)	0.0198 (3)	0.00006 (19)	0.00267 (19)	−0.00447 (18)
O1	0.0432 (10)	0.0331 (8)	0.0195 (8)	0.0039 (7)	−0.0132 (7)	0.0013 (6)
O2	0.1174 (18)	0.0204 (8)	0.0460 (11)	−0.0044 (10)	−0.0482 (11)	−0.0003 (7)
N1	0.0243 (10)	0.0202 (8)	0.0160 (8)	0.0027 (7)	0.0030 (7)	−0.0009 (6)
N2	0.0213 (9)	0.0165 (8)	0.0150 (8)	0.0000 (7)	0.0015 (6)	−0.0010 (6)
N3	0.0231 (9)	0.0172 (8)	0.0108 (7)	−0.0001 (7)	0.0029 (7)	−0.0004 (6)
N4	0.0163 (8)	0.0149 (7)	0.0118 (7)	0.0001 (6)	−0.0009 (6)	0.0009 (6)
N5	0.0183 (8)	0.0190 (8)	0.0114 (7)	0.0024 (6)	−0.0017 (6)	0.0005 (6)
N6	0.0354 (11)	0.0249 (9)	0.0196 (9)	0.0001 (8)	−0.0082 (8)	0.0013 (7)
C1	0.0266 (11)	0.0173 (9)	0.0171 (9)	0.0038 (8)	0.0016 (8)	0.0023 (7)
C2	0.0312 (12)	0.0219 (10)	0.0135 (9)	0.0044 (9)	0.0030 (8)	0.0008 (7)
C3	0.0241 (11)	0.0206 (10)	0.0204 (10)	0.0050 (8)	0.0003 (8)	0.0006 (7)
C4	0.0239 (11)	0.0194 (9)	0.0162 (9)	0.0024 (8)	0.0014 (8)	0.0022 (7)
C5	0.0135 (9)	0.0164 (8)	0.0158 (9)	−0.0015 (7)	0.0002 (7)	−0.0003 (7)
C6	0.0155 (10)	0.0153 (8)	0.0144 (9)	−0.0010 (7)	−0.0011 (7)	0.0008 (7)
C7	0.0132 (9)	0.0184 (9)	0.0140 (9)	−0.0054 (7)	0.0012 (7)	−0.0020 (7)
C8	0.0144 (10)	0.0180 (9)	0.0155 (9)	−0.0003 (7)	0.0006 (7)	−0.0003 (7)
C9	0.0143 (10)	0.0187 (9)	0.0146 (9)	0.0008 (7)	0.0020 (7)	0.0010 (7)
C10	0.0168 (10)	0.0182 (9)	0.0180 (9)	0.0014 (8)	0.0037 (7)	−0.0021 (7)
C11	0.0224 (11)	0.0171 (9)	0.0221 (10)	0.0029 (8)	0.0027 (8)	0.0023 (7)
C12	0.0177 (10)	0.0247 (10)	0.0166 (9)	0.0027 (8)	0.0001 (8)	0.0056 (7)
C13	0.0188 (10)	0.0216 (9)	0.0161 (9)	0.0008 (8)	−0.0010 (8)	−0.0007 (7)
C14	0.0213 (11)	0.0170 (9)	0.0174 (9)	0.0006 (8)	−0.0001 (8)	0.0012 (7)

S1—C7	1.6634 (19)	C3—C4	1.381 (3)
O1—N6	1.226 (2)	C3—H3	0.9500
O2—N6	1.216 (2)	C4—C5	1.392 (2)
N1—C2	1.334 (2)	C4—H4	0.9500
N1—C3	1.344 (2)	C5—C6	1.473 (2)
N2—C6	1.308 (2)	C8—C9	1.470 (2)
N2—N3	1.369 (2)	C8—H8	0.9500
N3—C7	1.342 (2)	C9—C14	1.395 (2)
N3—H3A	0.896 (9)	C9—C10	1.396 (3)
N4—C6	1.384 (2)	C10—C11	1.388 (3)
N4—N5	1.389 (2)	C10—H10	0.9500
N4—C7	1.389 (2)	C11—C12	1.383 (3)
N5—C8	1.283 (2)	C11—H11	0.9500
N6—C13	1.468 (2)	C12—C13	1.384 (3)
C1—C2	1.383 (3)	C12—H12	0.9500
C1—C5	1.391 (3)	C13—C14	1.379 (3)
C1—H1	0.9500	C14—H14	0.9500
C2—H2	0.9500
C2—N1—C3	116.43 (16)	N2—C6—N4	110.06 (16)
C6—N2—N3	104.61 (15)	N2—C6—C5	122.55 (16)
C7—N3—N2	114.30 (15)	N4—C6—C5	127.40 (16)
C7—N3—H3A	126.1 (14)	N3—C7—N4	102.37 (15)
N2—N3—H3A	119.3 (13)	N3—C7—S1	128.51 (14)
C6—N4—N5	122.59 (14)	N4—C7—S1	129.03 (14)
C6—N4—C7	108.58 (15)	N5—C8—C9	116.82 (16)
N5—N4—C7	127.12 (15)	N5—C8—H8	121.6
C8—N5—N4	116.80 (15)	C9—C8—H8	121.6
O2—N6—O1	122.78 (18)	C14—C9—C10	119.34 (17)
O2—N6—C13	118.63 (16)	C14—C9—C8	120.42 (17)
O1—N6—C13	118.58 (17)	C10—C9—C8	120.23 (16)
C2—C1—C5	118.91 (18)	C11—C10—C9	120.39 (17)
C2—C1—H1	120.5	C11—C10—H10	119.8
C5—C1—H1	120.5	C9—C10—H10	119.8
N1—C2—C1	124.13 (18)	C12—C11—C10	120.77 (17)
N1—C2—H2	117.9	C12—C11—H11	119.6
C1—C2—H2	117.9	C10—C11—H11	119.6
N1—C3—C4	123.79 (18)	C11—C12—C13	117.85 (17)
N1—C3—H3	118.1	C11—C12—H12	121.1
C4—C3—H3	118.1	C13—C12—H12	121.1
C3—C4—C5	119.07 (17)	C14—C13—C12	123.01 (18)
C3—C4—H4	120.5	C14—C13—N6	117.72 (17)
C5—C4—H4	120.5	C12—C13—N6	119.25 (16)
C1—C5—C4	117.65 (17)	C13—C14—C9	118.64 (17)
C1—C5—C6	124.09 (17)	C13—C14—H14	120.7
C4—C5—C6	118.25 (16)	C9—C14—H14	120.7
C6—N2—N3—C7	0.1 (2)	N2—N3—C7—S1	−175.14 (13)
C6—N4—N5—C8	151.64 (17)	C6—N4—C7—N3	−2.68 (19)
C7—N4—N5—C8	−44.9 (2)	N5—N4—C7—N3	−167.98 (16)
C3—N1—C2—C1	−0.1 (3)	C6—N4—C7—S1	174.07 (14)
C5—C1—C2—N1	0.6 (3)	N5—N4—C7—S1	8.8 (3)
C2—N1—C3—C4	−0.4 (3)	N4—N5—C8—C9	177.27 (15)
N1—C3—C4—C5	0.5 (3)	N5—C8—C9—C14	1.1 (3)
C2—C1—C5—C4	−0.5 (3)	N5—C8—C9—C10	−177.83 (17)
C2—C1—C5—C6	178.91 (18)	C14—C9—C10—C11	−0.7 (3)
C3—C4—C5—C1	0.0 (3)	C8—C9—C10—C11	178.18 (17)
C3—C4—C5—C6	−179.44 (17)	C9—C10—C11—C12	0.5 (3)
N3—N2—C6—N4	−1.9 (2)	C10—C11—C12—C13	0.2 (3)
N3—N2—C6—C5	178.17 (16)	C11—C12—C13—C14	−0.7 (3)
N5—N4—C6—N2	169.09 (15)	C11—C12—C13—N6	−179.16 (17)
C7—N4—C6—N2	3.0 (2)	O2—N6—C13—C14	3.3 (3)
N5—N4—C6—C5	−10.9 (3)	O1—N6—C13—C14	−176.44 (19)
C7—N4—C6—C5	−177.05 (17)	O2—N6—C13—C12	−178.2 (2)
C1—C5—C6—N2	178.28 (18)	O1—N6—C13—C12	2.1 (3)
C4—C5—C6—N2	−2.3 (3)	C12—C13—C14—C9	0.4 (3)
C1—C5—C6—N4	−1.7 (3)	N6—C13—C14—C9	178.92 (17)
C4—C5—C6—N4	177.75 (18)	C10—C9—C14—C13	0.3 (3)
N2—N3—C7—N4	1.6 (2)	C8—C9—C14—C13	−178.61 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.90 (1)	1.96 (1)	2.815 (2)	158.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.90 (1)	1.96 (1)	2.815 (2)	158 (2)

Symmetry code: (i) .