organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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4-[(3-Nitro­benzyl­­idene)amino]-3-(pyridin-4-yl)-1H-1,2,4-triazole-5(4H)-thione

aCollege of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, People's Republic of China
*Correspondence e-mail: yinbangshao@yahoo.cn

(Received 16 December 2011; accepted 18 December 2011; online 7 January 2012)

In the title compound, C14H10N6O2S, the dihedral angle between the pyridine and triazole rings is 3.21 (10)°. The mol­ecule is significantly twisted about the Nt—Nb (t = triazole and b = benzyl­idene) bond [C—Nt—Nb=C = 151.64 (17)°]. In the crystal, mol­ecules are linked by weak N—H⋯N hydrogen bonds, generating C(8) chains propagating in [10[\overline{1}]].

Related literature

For further details of the synthesis, see: Wang et al. (2010[Wang, B. L., Shi, Y. X., Ma, Y., Liu, X. H., Li, Y. H., Song, H. B., Li, B. J. & Li, Z. M. (2010). J. Agric. Food Chem. 58, 5515-5520.]). For the biological activity of related compounds, see: Liu et al. (2011[Liu, X. H., Tan, C. X. & Jian, Q. W. (2011). Phosphorus Sulfur Silicon Relat. Elem. 186, 558-564.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N6O2S

  • Mr = 326.34

  • Monoclinic, P 21 /n

  • 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]) Tmin = 0.952, Tmax = 0.975

  • 14478 measured reflections

  • 3317 independent reflections

  • 2807 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯N1i 0.90 (1) 1.96 (1) 2.815 (2) 158 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Related literature top

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

Experimental top

The title complex was prepared according to the literature procedures (Wang et al. (2010)). Colourless prisms were recrystallised from dimethylformamide solution at room temperature.

Refinement top

All the H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing for (I).
4-[(3-Nitrobenzylidene)amino]-3-(pyridin-4-yl)-1H-1,2,4-triazole- 5(4H)-thione top
Crystal data top
C14H10N6O2SF(000) = 672
Mr = 326.34Dx = 1.544 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.7989 (13) ÅCell parameters from 4572 reflections
b = 24.334 (9) Åθ = 1.6–28.0°
c = 15.208 (6) ŵ = 0.25 mm1
β = 93.035 (5)°T = 113 K
V = 1403.9 (9) Å3Prism, colorless
Z = 40.20 × 0.18 × 0.10 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer
3317 independent reflections
Radiation source: rotating anode2807 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.056
Detector resolution: 14.22 pixels mm-1θmax = 27.9°, θmin = 1.6°
ω and ϕ scansh = 44
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 3232
Tmin = 0.952, Tmax = 0.975l = 1920
14478 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H 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 parametersΔρmax = 0.30 e Å3
7 restraintsΔρmin = 0.28 e Å3
Crystal data top
C14H10N6O2SV = 1403.9 (9) Å3
Mr = 326.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 3.7989 (13) ŵ = 0.25 mm1
b = 24.334 (9) ÅT = 113 K
c = 15.208 (6) Å0.20 × 0.18 × 0.10 mm
β = 93.035 (5)°
Data collection top
Rigaku Saturn724 CCD
diffractometer
3317 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2807 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.975Rint = 0.056
14478 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0497 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.30 e Å3
3317 reflectionsΔρmin = 0.28 e Å3
212 parameters
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
S10.79238 (13)0.064958 (19)0.05911 (3)0.01910 (14)
O11.3928 (4)0.08135 (6)0.49993 (9)0.0325 (4)
O21.2099 (6)0.14915 (7)0.41988 (12)0.0631 (7)
N10.0656 (4)0.30533 (6)0.24207 (10)0.0201 (4)
N20.3124 (4)0.20542 (6)0.04085 (10)0.0176 (3)
N30.4482 (4)0.16171 (6)0.08450 (10)0.0169 (3)
N40.5138 (4)0.14148 (6)0.05152 (9)0.0144 (3)
N50.6482 (4)0.12137 (6)0.13193 (10)0.0163 (3)
N61.2412 (5)0.10008 (7)0.43334 (11)0.0270 (4)
C10.2990 (5)0.21757 (8)0.20265 (12)0.0203 (4)
H10.39180.18300.22160.024*
C20.2005 (5)0.25621 (8)0.26337 (12)0.0221 (4)
H20.23080.24720.32410.027*
C30.0267 (5)0.31683 (8)0.15567 (12)0.0217 (4)
H30.07040.35150.13870.026*
C40.1197 (5)0.28122 (8)0.09009 (12)0.0198 (4)
H40.08840.29150.02990.024*
C50.2600 (5)0.23011 (7)0.11340 (12)0.0153 (4)
C60.3606 (5)0.19291 (7)0.04253 (11)0.0152 (4)
C70.5807 (5)0.12176 (7)0.03166 (12)0.0152 (4)
C80.6464 (5)0.06903 (7)0.14201 (12)0.0160 (4)
H80.54810.04530.09760.019*
C90.8035 (5)0.04757 (8)0.22553 (11)0.0158 (4)
C100.8222 (5)0.00903 (8)0.24024 (12)0.0176 (4)
H100.72680.03370.19680.021*
C110.9793 (5)0.02948 (8)0.31800 (12)0.0205 (4)
H110.99200.06810.32710.025*
C121.1176 (5)0.00569 (8)0.38243 (12)0.0197 (4)
H121.22620.00810.43560.024*
C131.0928 (5)0.06162 (8)0.36685 (12)0.0189 (4)
C140.9407 (5)0.08343 (8)0.29021 (12)0.0186 (4)
H140.92970.12210.28160.022*
H3A0.461 (5)0.1634 (9)0.1431 (7)0.025 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0194 (3)0.0182 (2)0.0198 (3)0.00006 (19)0.00267 (19)0.00447 (18)
O10.0432 (10)0.0331 (8)0.0195 (8)0.0039 (7)0.0132 (7)0.0013 (6)
O20.1174 (18)0.0204 (8)0.0460 (11)0.0044 (10)0.0482 (11)0.0003 (7)
N10.0243 (10)0.0202 (8)0.0160 (8)0.0027 (7)0.0030 (7)0.0009 (6)
N20.0213 (9)0.0165 (8)0.0150 (8)0.0000 (7)0.0015 (6)0.0010 (6)
N30.0231 (9)0.0172 (8)0.0108 (7)0.0001 (7)0.0029 (7)0.0004 (6)
N40.0163 (8)0.0149 (7)0.0118 (7)0.0001 (6)0.0009 (6)0.0009 (6)
N50.0183 (8)0.0190 (8)0.0114 (7)0.0024 (6)0.0017 (6)0.0005 (6)
N60.0354 (11)0.0249 (9)0.0196 (9)0.0001 (8)0.0082 (8)0.0013 (7)
C10.0266 (11)0.0173 (9)0.0171 (9)0.0038 (8)0.0016 (8)0.0023 (7)
C20.0312 (12)0.0219 (10)0.0135 (9)0.0044 (9)0.0030 (8)0.0008 (7)
C30.0241 (11)0.0206 (10)0.0204 (10)0.0050 (8)0.0003 (8)0.0006 (7)
C40.0239 (11)0.0194 (9)0.0162 (9)0.0024 (8)0.0014 (8)0.0022 (7)
C50.0135 (9)0.0164 (8)0.0158 (9)0.0015 (7)0.0002 (7)0.0003 (7)
C60.0155 (10)0.0153 (8)0.0144 (9)0.0010 (7)0.0011 (7)0.0008 (7)
C70.0132 (9)0.0184 (9)0.0140 (9)0.0054 (7)0.0012 (7)0.0020 (7)
C80.0144 (10)0.0180 (9)0.0155 (9)0.0003 (7)0.0006 (7)0.0003 (7)
C90.0143 (10)0.0187 (9)0.0146 (9)0.0008 (7)0.0020 (7)0.0010 (7)
C100.0168 (10)0.0182 (9)0.0180 (9)0.0014 (8)0.0037 (7)0.0021 (7)
C110.0224 (11)0.0171 (9)0.0221 (10)0.0029 (8)0.0027 (8)0.0023 (7)
C120.0177 (10)0.0247 (10)0.0166 (9)0.0027 (8)0.0001 (8)0.0056 (7)
C130.0188 (10)0.0216 (9)0.0161 (9)0.0008 (8)0.0010 (8)0.0007 (7)
C140.0213 (11)0.0170 (9)0.0174 (9)0.0006 (8)0.0001 (8)0.0012 (7)
Geometric parameters (Å, º) top
S1—C71.6634 (19)C3—C41.381 (3)
O1—N61.226 (2)C3—H30.9500
O2—N61.216 (2)C4—C51.392 (2)
N1—C21.334 (2)C4—H40.9500
N1—C31.344 (2)C5—C61.473 (2)
N2—C61.308 (2)C8—C91.470 (2)
N2—N31.369 (2)C8—H80.9500
N3—C71.342 (2)C9—C141.395 (2)
N3—H3A0.896 (9)C9—C101.396 (3)
N4—C61.384 (2)C10—C111.388 (3)
N4—N51.389 (2)C10—H100.9500
N4—C71.389 (2)C11—C121.383 (3)
N5—C81.283 (2)C11—H110.9500
N6—C131.468 (2)C12—C131.384 (3)
C1—C21.383 (3)C12—H120.9500
C1—C51.391 (3)C13—C141.379 (3)
C1—H10.9500C14—H140.9500
C2—H20.9500
C2—N1—C3116.43 (16)N2—C6—N4110.06 (16)
C6—N2—N3104.61 (15)N2—C6—C5122.55 (16)
C7—N3—N2114.30 (15)N4—C6—C5127.40 (16)
C7—N3—H3A126.1 (14)N3—C7—N4102.37 (15)
N2—N3—H3A119.3 (13)N3—C7—S1128.51 (14)
C6—N4—N5122.59 (14)N4—C7—S1129.03 (14)
C6—N4—C7108.58 (15)N5—C8—C9116.82 (16)
N5—N4—C7127.12 (15)N5—C8—H8121.6
C8—N5—N4116.80 (15)C9—C8—H8121.6
O2—N6—O1122.78 (18)C14—C9—C10119.34 (17)
O2—N6—C13118.63 (16)C14—C9—C8120.42 (17)
O1—N6—C13118.58 (17)C10—C9—C8120.23 (16)
C2—C1—C5118.91 (18)C11—C10—C9120.39 (17)
C2—C1—H1120.5C11—C10—H10119.8
C5—C1—H1120.5C9—C10—H10119.8
N1—C2—C1124.13 (18)C12—C11—C10120.77 (17)
N1—C2—H2117.9C12—C11—H11119.6
C1—C2—H2117.9C10—C11—H11119.6
N1—C3—C4123.79 (18)C11—C12—C13117.85 (17)
N1—C3—H3118.1C11—C12—H12121.1
C4—C3—H3118.1C13—C12—H12121.1
C3—C4—C5119.07 (17)C14—C13—C12123.01 (18)
C3—C4—H4120.5C14—C13—N6117.72 (17)
C5—C4—H4120.5C12—C13—N6119.25 (16)
C1—C5—C4117.65 (17)C13—C14—C9118.64 (17)
C1—C5—C6124.09 (17)C13—C14—H14120.7
C4—C5—C6118.25 (16)C9—C14—H14120.7
C6—N2—N3—C70.1 (2)N2—N3—C7—S1175.14 (13)
C6—N4—N5—C8151.64 (17)C6—N4—C7—N32.68 (19)
C7—N4—N5—C844.9 (2)N5—N4—C7—N3167.98 (16)
C3—N1—C2—C10.1 (3)C6—N4—C7—S1174.07 (14)
C5—C1—C2—N10.6 (3)N5—N4—C7—S18.8 (3)
C2—N1—C3—C40.4 (3)N4—N5—C8—C9177.27 (15)
N1—C3—C4—C50.5 (3)N5—C8—C9—C141.1 (3)
C2—C1—C5—C40.5 (3)N5—C8—C9—C10177.83 (17)
C2—C1—C5—C6178.91 (18)C14—C9—C10—C110.7 (3)
C3—C4—C5—C10.0 (3)C8—C9—C10—C11178.18 (17)
C3—C4—C5—C6179.44 (17)C9—C10—C11—C120.5 (3)
N3—N2—C6—N41.9 (2)C10—C11—C12—C130.2 (3)
N3—N2—C6—C5178.17 (16)C11—C12—C13—C140.7 (3)
N5—N4—C6—N2169.09 (15)C11—C12—C13—N6179.16 (17)
C7—N4—C6—N23.0 (2)O2—N6—C13—C143.3 (3)
N5—N4—C6—C510.9 (3)O1—N6—C13—C14176.44 (19)
C7—N4—C6—C5177.05 (17)O2—N6—C13—C12178.2 (2)
C1—C5—C6—N2178.28 (18)O1—N6—C13—C122.1 (3)
C4—C5—C6—N22.3 (3)C12—C13—C14—C90.4 (3)
C1—C5—C6—N41.7 (3)N6—C13—C14—C9178.92 (17)
C4—C5—C6—N4177.75 (18)C10—C9—C14—C130.3 (3)
N2—N3—C7—N41.6 (2)C8—C9—C14—C13178.61 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N1i0.90 (1)1.96 (1)2.815 (2)158 (2)
Symmetry code: (i) x+1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H10N6O2S
Mr326.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)113
a, b, c (Å)3.7989 (13), 24.334 (9), 15.208 (6)
β (°) 93.035 (5)
V3)1403.9 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn724 CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.952, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
14478, 3317, 2807
Rint0.056
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.103, 1.07
No. of reflections3317
No. of parameters212
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.28

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···N1i0.896 (9)1.964 (12)2.815 (2)157.9 (19)
Symmetry code: (i) x+1/2, y+1/2, z1/2.
 

Acknowledgements

This work was supported by the start-up foundation of Hunan Normal University.

References

First citationLiu, X. H., Tan, C. X. & Jian, Q. W. (2011). Phosphorus Sulfur Silicon Relat. Elem. 186, 558–564.  Web of Science CSD CrossRef CAS Google Scholar
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, B. L., Shi, Y. X., Ma, Y., Liu, X. H., Li, Y. H., Song, H. B., Li, B. J. & Li, Z. M. (2010). J. Agric. Food Chem. 58, 5515–5520.  Web of Science CrossRef CAS PubMed Google Scholar

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