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

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ISSN: 2414-3146

(E)-2-({[3-Benzyl­sulfan­yl-5-(p-tol­yl)-4H-1,2,4-triazol-4-yl]imino}­meth­yl)phenol

aCollege of Chemical Engineering, Huanggang Normal University, Huanggang 438000, People's Republic of China
*Correspondence e-mail: qqhrchemistry@aliyun.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 19 December 2016; accepted 9 February 2017; online 14 February 2017)

In the title compound, C23H20N4OS, the 1,2,4-triazole ring (r.m.s. deviation = 0.014 Å) forms dihedral angles of 88.66 (8), 24.48 (8) and 17.97 (7)° with the benzyl, p-tolyl and phenol rings, respectively. The conformation about the C=N bond is E. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming chains along [010].

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Recently, we have reported the synthesis and crystal structures of some Mannich base derivatives (Wang et al., 2011a[Wang, W., Gao, Y., Xiao, Z., Yao, H. & Zhang, J. (2011a). Acta Cryst. E67, o269.],b[Wang, W., Liu, Q., Xu, C., Wu, W. & Gao, Y. (2011b). Acta Cryst. E67, o2236.]). We report herein, on the crystal structure of the title 1,2,4-triazole–thione derivative.

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. The 1,2,4-triazole ring (N1–N3/C8/C9) is almost planar with an r.m.s. deviation of 0.014 Å, and a maximum deviation of 0.012 (1) Å for atoms N3 and C9. Atom C9 shows a distorted Csp2 hybrid­ization state with bond angles of 108.51 (12)° (N2—C9—N3), 124.13 (11)° (N2—C9—C10) and 127.36 (12)° (N3—C9—C10), which are similar to the same bond angles reported for other triazole derivatives (Zhao et al., 2010[Zhao, B., Liu, Z., Gao, Y., Song, B. & Deng, Q. (2010). Acta Cryst. E66, o2814.]; Gao et al., 2011[Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.]). The 1,2,4-triazole ring forms dihedral angles of by 88.66 (8), 24.48 (8) and 17.97 (7) ° with the benzyl ring (C1–C6), the p-toluene ring (C10–C15), and the phenol ring (C18–C23), respectively. Hence, the benzyl ring (C1–C6) is almost normal to the 1,2,4-triazole ring. The conformation about the C7=N4 bond is E. As a result of ππ conjugation, the Csp2—S bond [S1—C8 = 1.7462 (14) Å] is significantly shorter than the Csp3—S bond [S1—C7 = 1.8091 (14) Å]. These values compare well with those of 1.744 (2) and 1.812 (2) Å, respectively, reported for the very similar compound (E)-2-{[(3-(propyl­thio)-5-(p-tol­yl)-4H-1,2,4-triazol-4-yl)imino]­meth­yl}phenol (Wang et al., 2011b[Wang, W., Liu, Q., Xu, C., Wu, W. & Gao, Y. (2011b). Acta Cryst. E67, o2236.]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 75% probability level.

In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming chains propagating along the b-axis direction (Fig. 2[link] and Table 1[link]). There are no other significant inter­molecular inter­actions present.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2i 0.95 (2) 1.72 (2) 2.6555 (15) 167.6 (19)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 2]
Figure 2
A partial view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as pale-blue lines (see Table 1[link]). For clarity, only one H atom, H1, has been included.

Synthesis and crystallization

The title compound was synthesized by refluxing 3-(benzyl­sulfan­yl)-5-(p-tol­yl)-4p-1,2,4-triazol-4-amine (2.0 mmol) with 2-hy­droxy­benzaldehyde (2.0 mmol) in ethanol for 5 h. The resulting precipitate was filtered, washed with cold ethanol, and dried. The target product was purified by recrystallization from chloro­form-ethanol (1:2) to give a colourless solid (yield 75%). Colourless prismatic crystals of the title compound, suitable for X-ray diffraction analysis, were grown by slow evaporation of a solution in chloro­form–ethanol (1:2).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C23H20N4OS
Mr 400.49
Crystal system, space group Monoclinic, P21/c
Temperature (K) 113
a, b, c (Å) 11.8003 (12), 17.9297 (16), 9.8723 (8)
β (°) 110.279 (5)
V3) 1959.3 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.19
Crystal size (mm) 0.20 × 0.18 × 0.12
 
Data collection
Diffractometer Rigaku Saturn CCD area detector
Absorption correction Multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.963, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections 22129, 4677, 4023
Rint 0.044
(sin θ/λ)max−1) 0.658
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.099, 1.07
No. of reflections 4677
No. of parameters 267
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.35, −0.21
Computer programs: CrystalClear and CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data


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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

(E)-2-({[3-Benzylsulfanyl-5-(p-tolyl)-4H-1,2,4-triazol-4-yl]imino}methyl)phenol top
Crystal data top
C23H20N4OSF(000) = 840
Mr = 400.49Dx = 1.358 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6546 reflections
a = 11.8003 (12) Åθ = 1.8–27.9°
b = 17.9297 (16) ŵ = 0.19 mm1
c = 9.8723 (8) ÅT = 113 K
β = 110.279 (5)°Prism, colourless
V = 1959.3 (3) Å30.20 × 0.18 × 0.12 mm
Z = 4
Data collection top
Rigaku Saturn CCD area detector
diffractometer
4677 independent reflections
Radiation source: rotating anode4023 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.044
Detector resolution: 14.22 pixels mm-1θmax = 27.9°, θmin = 1.8°
φ and ω scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2320
Tmin = 0.963, Tmax = 0.978l = 1212
22129 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0691P]
where P = (Fo2 + 2Fc2)/3
4677 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S10.05368 (3)0.073331 (19)0.84276 (4)0.02198 (11)
O10.04559 (9)0.07904 (5)0.64668 (11)0.0235 (2)
H10.0323 (17)0.1309 (12)0.657 (2)0.053 (6)*
N10.05660 (10)0.22483 (6)0.83583 (13)0.0211 (3)
N20.00556 (10)0.28249 (6)0.79821 (13)0.0201 (3)
N30.07357 (10)0.17775 (6)0.74342 (12)0.0170 (2)
N40.15716 (10)0.12969 (6)0.71510 (12)0.0182 (2)
C10.32364 (13)0.12819 (8)0.76880 (16)0.0225 (3)
H1A0.29460.10520.70050.027*
C20.44007 (13)0.15724 (8)0.72435 (17)0.0271 (3)
H20.49020.15400.62570.032*
C30.48351 (13)0.19083 (9)0.82265 (18)0.0297 (4)
H30.56350.21000.79210.036*
C40.40971 (14)0.19621 (9)0.96563 (18)0.0292 (4)
H40.43880.21941.03370.035*
C50.29371 (13)0.16795 (8)1.00994 (16)0.0243 (3)
H50.24310.17261.10820.029*
C60.25002 (12)0.13271 (7)0.91230 (15)0.0182 (3)
C70.12538 (12)0.09818 (8)0.97144 (15)0.0221 (3)
H7A0.13090.05261.02540.027*
H7B0.07170.13351.04180.027*
C80.01388 (12)0.16245 (7)0.80360 (15)0.0191 (3)
C90.08464 (12)0.25386 (7)0.74565 (15)0.0174 (3)
C100.16945 (12)0.29819 (7)0.70022 (15)0.0176 (3)
C110.21798 (12)0.27415 (8)0.59754 (15)0.0192 (3)
H110.20100.22520.55890.023*
C120.29062 (12)0.32083 (8)0.55128 (16)0.0215 (3)
H120.32240.30330.48090.026*
C130.31820 (12)0.39299 (8)0.60553 (16)0.0215 (3)
C140.27198 (13)0.41596 (8)0.71107 (17)0.0239 (3)
H140.29130.46430.75180.029*
C150.19875 (13)0.37003 (8)0.75794 (16)0.0225 (3)
H150.16820.38730.82960.027*
C160.39281 (14)0.44438 (8)0.54910 (18)0.0281 (3)
H16A0.47610.42590.57930.042*
H16B0.39220.49460.58790.042*
H16C0.35860.44600.44340.042*
C170.11524 (12)0.06527 (7)0.66711 (15)0.0184 (3)
H170.03230.05470.64870.022*
C180.19257 (12)0.00785 (7)0.64025 (14)0.0177 (3)
C190.30414 (12)0.02410 (8)0.62744 (16)0.0227 (3)
H190.33100.07430.63370.027*
C200.37576 (13)0.03235 (8)0.60577 (16)0.0259 (3)
H200.45150.02110.59680.031*
C210.33616 (14)0.10567 (8)0.59720 (16)0.0257 (3)
H210.38590.14440.58340.031*
C220.22584 (13)0.12335 (8)0.60829 (15)0.0217 (3)
H220.19940.17370.60060.026*
C230.15335 (12)0.06653 (7)0.63100 (15)0.0185 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02314 (19)0.01440 (19)0.0331 (2)0.00067 (14)0.01575 (16)0.00221 (14)
O10.0241 (5)0.0149 (5)0.0357 (6)0.0020 (4)0.0160 (5)0.0011 (4)
N10.0196 (6)0.0157 (6)0.0301 (7)0.0003 (5)0.0114 (5)0.0013 (5)
N20.0202 (6)0.0147 (6)0.0270 (6)0.0003 (5)0.0102 (5)0.0012 (5)
N30.0164 (5)0.0128 (6)0.0230 (6)0.0013 (4)0.0086 (5)0.0001 (5)
N40.0183 (6)0.0149 (6)0.0231 (6)0.0046 (5)0.0095 (5)0.0007 (5)
C10.0259 (7)0.0204 (7)0.0241 (8)0.0021 (6)0.0122 (6)0.0011 (6)
C20.0216 (7)0.0301 (8)0.0269 (8)0.0035 (6)0.0049 (6)0.0070 (6)
C30.0193 (7)0.0289 (8)0.0425 (10)0.0037 (6)0.0126 (7)0.0086 (7)
C40.0285 (8)0.0276 (8)0.0382 (9)0.0022 (7)0.0200 (7)0.0013 (7)
C50.0254 (7)0.0248 (8)0.0244 (8)0.0014 (6)0.0108 (6)0.0005 (6)
C60.0188 (7)0.0133 (7)0.0244 (7)0.0037 (5)0.0099 (6)0.0025 (5)
C70.0221 (7)0.0228 (7)0.0232 (7)0.0022 (6)0.0100 (6)0.0038 (6)
C80.0156 (6)0.0174 (7)0.0245 (7)0.0011 (5)0.0072 (6)0.0011 (6)
C90.0161 (6)0.0141 (7)0.0211 (7)0.0019 (5)0.0054 (6)0.0003 (5)
C100.0162 (6)0.0154 (7)0.0204 (7)0.0012 (5)0.0055 (6)0.0028 (5)
C110.0202 (7)0.0161 (7)0.0201 (7)0.0012 (6)0.0054 (6)0.0001 (5)
C120.0210 (7)0.0228 (8)0.0221 (7)0.0025 (6)0.0091 (6)0.0019 (6)
C130.0176 (7)0.0207 (7)0.0249 (8)0.0001 (6)0.0060 (6)0.0038 (6)
C140.0243 (8)0.0156 (7)0.0343 (9)0.0026 (6)0.0134 (7)0.0019 (6)
C150.0243 (7)0.0183 (7)0.0284 (8)0.0001 (6)0.0136 (6)0.0027 (6)
C160.0291 (8)0.0265 (8)0.0328 (9)0.0047 (7)0.0157 (7)0.0007 (7)
C170.0180 (7)0.0189 (7)0.0185 (7)0.0003 (5)0.0068 (6)0.0022 (5)
C180.0199 (7)0.0157 (7)0.0181 (7)0.0010 (5)0.0073 (6)0.0006 (5)
C190.0232 (7)0.0214 (7)0.0251 (8)0.0012 (6)0.0104 (6)0.0003 (6)
C200.0228 (7)0.0294 (8)0.0302 (8)0.0023 (6)0.0153 (7)0.0004 (7)
C210.0302 (8)0.0246 (8)0.0262 (8)0.0092 (6)0.0148 (7)0.0000 (6)
C220.0299 (8)0.0161 (7)0.0208 (7)0.0009 (6)0.0110 (6)0.0003 (6)
C230.0210 (7)0.0190 (7)0.0166 (7)0.0000 (6)0.0078 (6)0.0009 (5)
Geometric parameters (Å, º) top
S1—C81.7462 (14)C10—C111.3941 (19)
S1—C71.8091 (14)C10—C151.4025 (19)
O1—C231.3519 (16)C11—C121.3839 (19)
O1—H10.95 (2)C11—H110.9500
N1—C81.3106 (17)C12—C131.395 (2)
N1—N21.3904 (16)C12—H120.9500
N2—C91.3187 (17)C13—C141.395 (2)
N3—C91.3704 (17)C13—C161.508 (2)
N3—C81.3849 (17)C14—C151.3842 (19)
N3—N41.4088 (15)C14—H140.9500
N4—C171.2810 (17)C15—H150.9500
C1—C61.3838 (19)C16—H16A0.9800
C1—C21.391 (2)C16—H16B0.9800
C1—H1A0.9500C16—H16C0.9800
C2—C31.383 (2)C17—C181.4597 (19)
C2—H20.9500C17—H170.9500
C3—C41.381 (2)C18—C191.3963 (18)
C3—H30.9500C18—C231.4042 (19)
C4—C51.381 (2)C19—C201.382 (2)
C4—H40.9500C19—H190.9500
C5—C61.3923 (19)C20—C211.388 (2)
C5—H50.9500C20—H200.9500
C6—C71.5141 (19)C21—C221.381 (2)
C7—H7A0.9900C21—H210.9500
C7—H7B0.9900C22—C231.3974 (19)
C9—C101.4648 (18)C22—H220.9500
C8—S1—C799.05 (7)C12—C11—H11119.7
C23—O1—H1111.8 (12)C10—C11—H11119.7
C8—N1—N2106.67 (11)C11—C12—C13121.53 (13)
C9—N2—N1109.05 (11)C11—C12—H12119.2
C9—N3—C8105.75 (11)C13—C12—H12119.2
C9—N3—N4122.88 (11)C12—C13—C14117.45 (13)
C8—N3—N4129.87 (11)C12—C13—C16120.88 (13)
C17—N4—N3114.69 (11)C14—C13—C16121.66 (13)
C6—C1—C2120.14 (14)C15—C14—C13121.66 (13)
C6—C1—H1A119.9C15—C14—H14119.2
C2—C1—H1A119.9C13—C14—H14119.2
C3—C2—C1120.51 (14)C14—C15—C10120.34 (13)
C3—C2—H2119.7C14—C15—H15119.8
C1—C2—H2119.7C10—C15—H15119.8
C4—C3—C2119.46 (14)C13—C16—H16A109.5
C4—C3—H3120.3C13—C16—H16B109.5
C2—C3—H3120.3H16A—C16—H16B109.5
C5—C4—C3120.18 (15)C13—C16—H16C109.5
C5—C4—H4119.9H16A—C16—H16C109.5
C3—C4—H4119.9H16B—C16—H16C109.5
C4—C5—C6120.76 (14)N4—C17—C18121.17 (12)
C4—C5—H5119.6N4—C17—H17119.4
C6—C5—H5119.6C18—C17—H17119.4
C1—C6—C5118.92 (13)C19—C18—C23119.48 (13)
C1—C6—C7123.51 (13)C19—C18—C17122.53 (12)
C5—C6—C7117.51 (13)C23—C18—C17117.97 (12)
C6—C7—S1117.27 (10)C20—C19—C18120.51 (13)
C6—C7—H7A108.0C20—C19—H19119.7
S1—C7—H7A108.0C18—C19—H19119.7
C6—C7—H7B108.0C19—C20—C21119.47 (13)
S1—C7—H7B108.0C19—C20—H20120.3
H7A—C7—H7B107.2C21—C20—H20120.3
N1—C8—N3109.97 (12)C22—C21—C20121.30 (13)
N1—C8—S1124.86 (11)C22—C21—H21119.3
N3—C8—S1125.02 (10)C20—C21—H21119.3
N2—C9—N3108.51 (12)C21—C22—C23119.45 (13)
N2—C9—C10124.13 (11)C21—C22—H22120.3
N3—C9—C10127.36 (12)C23—C22—H22120.3
C11—C10—C15118.29 (13)O1—C23—C22123.35 (12)
C11—C10—C9123.45 (12)O1—C23—C18116.87 (12)
C15—C10—C9118.19 (12)C22—C23—C18119.77 (13)
C12—C11—C10120.69 (13)
C8—N1—N2—C90.55 (15)N2—C9—C10—C11154.26 (14)
C9—N3—N4—C17156.47 (13)N3—C9—C10—C1126.5 (2)
C8—N3—N4—C1739.60 (19)N2—C9—C10—C1522.5 (2)
C6—C1—C2—C30.0 (2)N3—C9—C10—C15156.66 (14)
C1—C2—C3—C40.8 (2)C15—C10—C11—C121.6 (2)
C2—C3—C4—C50.3 (2)C9—C10—C11—C12175.15 (12)
C3—C4—C5—C61.0 (2)C10—C11—C12—C130.2 (2)
C2—C1—C6—C51.2 (2)C11—C12—C13—C141.4 (2)
C2—C1—C6—C7175.89 (13)C11—C12—C13—C16177.20 (13)
C4—C5—C6—C11.8 (2)C12—C13—C14—C151.7 (2)
C4—C5—C6—C7175.54 (13)C16—C13—C14—C15176.88 (13)
C1—C6—C7—S117.78 (18)C13—C14—C15—C100.4 (2)
C5—C6—C7—S1165.06 (11)C11—C10—C15—C141.3 (2)
C8—S1—C7—C674.69 (11)C9—C10—C15—C14175.62 (13)
N2—N1—C8—N30.98 (15)N3—N4—C17—C18176.57 (12)
N2—N1—C8—S1174.78 (10)N4—C17—C18—C1917.4 (2)
C9—N3—C8—N12.08 (16)N4—C17—C18—C23160.89 (13)
N4—N3—C8—N1168.11 (12)C23—C18—C19—C200.0 (2)
C9—N3—C8—S1173.67 (10)C17—C18—C19—C20178.29 (13)
N4—N3—C8—S17.6 (2)C18—C19—C20—C210.2 (2)
C7—S1—C8—N114.82 (14)C19—C20—C21—C220.7 (2)
C7—S1—C8—N3160.31 (12)C20—C21—C22—C231.1 (2)
N1—N2—C9—N31.86 (15)C21—C22—C23—O1178.32 (13)
N1—N2—C9—C10177.46 (12)C21—C22—C23—C180.9 (2)
C8—N3—C9—N22.39 (15)C19—C18—C23—O1178.88 (12)
N4—N3—C9—N2169.64 (11)C17—C18—C23—O10.53 (19)
C8—N3—C9—C10176.91 (13)C19—C18—C23—C220.4 (2)
N4—N3—C9—C109.7 (2)C17—C18—C23—C22178.72 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.95 (2)1.72 (2)2.6555 (15)167.6 (19)
Symmetry code: (i) x, y1/2, z+3/2.
 

References

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