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The title compound, C17H16ClN3OS, is an important biologically active heterocyclic compound. The triazole ring is oriented with respect to the 4-chloro­phenyl and 2-(3-methoxy­phen­yl)ethyl rings at dihedral angles of 89.5 (1) and 56.9 (1)°, respectively. The dihedral angle between the benzene rings is 78.5 (1)°. In the crystal structure, inter­molecular N—H...S hydrogen bonds link the mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053329/hk2353sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053329/hk2353Isup2.hkl
Contains datablock I

CCDC reference: 672788

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.111
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C17 H16 Cl N3 O S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Substituted triazole derivatives display significant biological activities including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to the structure, possibly being due to the presence of the —N—C S unit (Omar et al., 1986). We are interested in the synthesis and biological activities of aryloxyacetyl hydrazide derivatives and report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are comparable with those observed in related structures (Öztürk et al., 2004a,b). The C1S1 [1.680 (2) Å] bond agrees with the corresponding values [1.6773 (19) Å] in 4-(4-chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione (Öztürk et al., 2004a) and [1.668 (5) Å] in 4-amino-3-(1,2,3,4,5-pentahydroxypentyl)-1H-1,2,4-triazole-5(4H)-thione (Zhang et al., 2004). In the triazole ring, the N2 C2 [1.347 (3) Å] bond has double-bond character. The planar triazole ring A (N1–N3/C7/C8) is oriented with respect to planar 4-chlorophenyl and 2-(3-methoxyphenyl)ethyl rings; B (C1–C6) and C (C11–C16), at dihedral angles of 89.5 (1) and 56.9 (1)°, respectively. The dihedral angle between rings B and C is B/C = 78.5 (1)°.

In the crystal structure, intermolecular N—H···S hydrogen bonds (Table 1, Fig. 2) link the molecules, in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Holla et al. (1998); Turan-Zitouni et al. (1999); Demirbas et al. (2002); Paulvannan et al. (2000); Kritsanida et al. (2002); Omar et al. (1986); Öztürk et al. (2004a,b); Zhang et al. (2004).

Experimental top

The synthesis of the title compound was carried out by refluxing a solution of 1-(3-(3-methoxyphenyl)propanoyl)-4-(4-chlorophenyl)thiosemicarbazide (3.63 g, 10 mmol) in NaOH (2 M) for 5 h. Single crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield; 72%, m.p. 461–462 K).

Refinement top

The H atom (for SH) was located in difference syntheses, and constrained to ride on its parent atom, with S—H = 0.9972 Å and Uiso = 1.5Ueq(S). The remaining H atoms were positioned geometrically, with C—H = 0.95, 0.99 and 0.98 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: COLLECT (Bruker, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. The formation of the title compound.
4-(4-Chlorophenyl)-3-(3-methoxyphenethyl)-1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C17H16ClN3OSZ = 2
Mr = 345.84F(000) = 360
Triclinic, P1Dx = 1.399 Mg m3
Hall symbol: -P 1Melting point: 461(1) K
a = 7.1697 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1376 (4) ÅCell parameters from 9213 reflections
c = 11.7574 (5) Åθ = 1.0–27.5°
α = 67.070 (2)°µ = 0.37 mm1
β = 77.421 (2)°T = 120 K
γ = 72.948 (3)°Block, colorless
V = 820.93 (6) Å30.26 × 0.18 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
3752 independent reflections
Radiation source: fine-focus sealed tube2725 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.048
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ scans and ω scans with κ offseth = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1414
Tmin = 0.912, Tmax = 0.953l = 1515
15238 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)] = 0.043Hydrogen site location: mixed
wR(F2) = 0.111H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.5947P]
where P = (Fo2 + 2Fc2)/3
3752 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.77 e Å3
Crystal data top
C17H16ClN3OSγ = 72.948 (3)°
Mr = 345.84V = 820.93 (6) Å3
Triclinic, P1Z = 2
a = 7.1697 (3) ÅMo Kα radiation
b = 11.1376 (4) ŵ = 0.37 mm1
c = 11.7574 (5) ÅT = 120 K
α = 67.070 (2)°0.26 × 0.18 × 0.13 mm
β = 77.421 (2)°
Data collection top
Nonius KappaCCD
diffractometer
3752 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2725 reflections with I > 2σ(I)
Tmin = 0.912, Tmax = 0.953Rint = 0.048
15238 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.04Δρmax = 0.74 e Å3
3752 reflectionsΔρmin = 0.77 e Å3
209 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
Cl10.76936 (8)0.01723 (5)0.38434 (5)0.02439 (16)
S11.42541 (8)0.32374 (5)0.81974 (5)0.02415 (16)
H1S1.48390.32130.88820.036*
O10.3991 (2)0.62525 (16)0.62402 (16)0.0305 (4)
N11.1468 (2)0.43495 (17)0.79786 (15)0.0162 (4)
N21.3112 (3)0.55857 (17)0.95049 (16)0.0186 (4)
N31.1823 (3)0.63067 (17)0.95225 (16)0.0192 (4)
C10.8828 (3)0.1146 (2)0.5053 (2)0.0182 (5)
C21.0559 (3)0.1999 (2)0.4786 (2)0.0201 (5)
H21.11300.18590.39490.024*
C31.1453 (3)0.3063 (2)0.5751 (2)0.0193 (5)
H31.26300.36670.55830.023*
C41.0604 (3)0.3228 (2)0.69584 (19)0.0162 (4)
C50.8906 (3)0.2357 (2)0.7231 (2)0.0203 (5)
H50.83710.24750.80710.024*
C60.7986 (3)0.1308 (2)0.6265 (2)0.0211 (5)
H60.68000.07100.64340.025*
C71.2942 (3)0.4394 (2)0.85785 (19)0.0180 (5)
C81.0843 (3)0.5532 (2)0.85786 (19)0.0175 (4)
C90.9291 (3)0.5843 (2)0.8159 (2)0.0203 (5)
H9A0.96080.56990.72600.024*
H9B0.80210.52190.82780.024*
C100.9083 (3)0.7281 (2)0.8865 (2)0.0226 (5)
H10A1.03850.78950.88020.027*
H10B0.86760.73980.97550.027*
C110.7628 (3)0.7685 (2)0.8412 (2)0.0209 (5)
C120.6384 (3)0.6796 (2)0.7539 (2)0.0211 (5)
H120.64050.58740.72140.025*
C130.5102 (3)0.7227 (2)0.7129 (2)0.0224 (5)
C140.5016 (3)0.8572 (2)0.7609 (2)0.0258 (5)
H140.41410.88720.73360.031*
C150.6245 (4)0.9462 (2)0.8498 (2)0.0301 (6)
H150.61971.03800.88400.036*
C160.7531 (4)0.9040 (2)0.8892 (2)0.0283 (5)
H160.83630.96710.94950.034*
C170.2965 (4)0.6684 (3)0.5611 (3)0.0376 (6)
H17A0.39010.73010.52300.056*
H17B0.23030.59050.49630.056*
H17C0.19880.71430.62080.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0265 (3)0.0187 (3)0.0252 (3)0.0051 (2)0.0144 (2)0.0011 (2)
S10.0245 (3)0.0206 (3)0.0261 (3)0.0096 (2)0.0142 (2)0.0023 (2)
O10.0293 (9)0.0269 (9)0.0428 (10)0.0037 (7)0.0177 (8)0.0150 (8)
N10.0168 (9)0.0155 (9)0.0157 (9)0.0046 (7)0.0057 (7)0.0021 (7)
N20.0191 (9)0.0168 (9)0.0203 (9)0.0069 (7)0.0059 (7)0.0029 (7)
N30.0207 (9)0.0184 (9)0.0190 (9)0.0060 (7)0.0052 (7)0.0045 (7)
C10.0217 (11)0.0132 (10)0.0212 (11)0.0070 (8)0.0105 (9)0.0011 (8)
C20.0223 (11)0.0201 (11)0.0182 (11)0.0045 (9)0.0053 (9)0.0059 (9)
C30.0181 (11)0.0185 (11)0.0210 (11)0.0029 (8)0.0049 (9)0.0062 (9)
C40.0162 (10)0.0143 (10)0.0187 (10)0.0057 (8)0.0076 (8)0.0019 (8)
C50.0198 (11)0.0204 (11)0.0186 (11)0.0054 (9)0.0019 (9)0.0043 (9)
C60.0165 (11)0.0199 (11)0.0255 (12)0.0035 (8)0.0036 (9)0.0062 (9)
C70.0157 (10)0.0190 (11)0.0175 (10)0.0021 (8)0.0041 (8)0.0046 (9)
C80.0186 (11)0.0162 (10)0.0164 (10)0.0054 (8)0.0025 (8)0.0032 (8)
C90.0214 (11)0.0198 (11)0.0211 (11)0.0071 (9)0.0074 (9)0.0044 (9)
C100.0265 (12)0.0213 (11)0.0211 (11)0.0086 (9)0.0065 (9)0.0045 (9)
C110.0219 (11)0.0212 (11)0.0212 (11)0.0087 (9)0.0012 (9)0.0084 (9)
C120.0226 (11)0.0198 (11)0.0237 (11)0.0073 (9)0.0023 (9)0.0091 (9)
C130.0189 (11)0.0255 (12)0.0250 (12)0.0040 (9)0.0010 (9)0.0128 (10)
C140.0257 (12)0.0286 (13)0.0310 (13)0.0120 (10)0.0002 (10)0.0162 (10)
C150.0362 (14)0.0234 (12)0.0333 (14)0.0146 (11)0.0014 (11)0.0084 (11)
C160.0331 (13)0.0231 (12)0.0281 (13)0.0109 (10)0.0077 (11)0.0030 (10)
C170.0365 (15)0.0410 (15)0.0469 (16)0.0090 (12)0.0200 (13)0.0197 (13)
Geometric parameters (Å, º) top
Cl1—C11.737 (2)C8—C91.483 (3)
S1—C71.680 (2)C9—C101.525 (3)
S1—H1S0.9972C9—H9A0.9900
O1—C131.370 (3)C9—H9B0.9900
O1—C171.429 (3)C10—C111.509 (3)
N1—C71.372 (3)C10—H10A0.9900
N1—C81.385 (3)C10—H10B0.9900
N1—C41.444 (2)C11—C121.384 (3)
N2—C71.341 (3)C11—C161.408 (3)
N2—N31.384 (2)C12—C131.393 (3)
N3—C81.307 (3)C12—H120.9500
C1—C21.383 (3)C13—C141.396 (3)
C1—C61.384 (3)C14—C151.390 (3)
C2—C31.387 (3)C14—H140.9500
C2—H20.9500C15—C161.377 (3)
C3—C41.380 (3)C15—H150.9500
C3—H30.9500C16—H160.9500
C4—C51.381 (3)C17—H17A0.9800
C5—C61.390 (3)C17—H17B0.9800
C5—H50.9500C17—H17C0.9800
C6—H60.9500
C7—S1—H1S116.9C8—C9—H9B109.1
C13—O1—C17117.19 (18)C10—C9—H9B109.1
C7—N1—C8108.24 (16)H9A—C9—H9B107.9
C7—N1—C4126.25 (17)C11—C10—C9114.60 (18)
C8—N1—C4125.36 (17)C11—C10—H10A108.6
C7—N2—N3113.38 (17)C9—C10—H10A108.6
C8—N3—N2104.10 (16)C11—C10—H10B108.6
C2—C1—C6121.58 (19)C9—C10—H10B108.6
C2—C1—Cl1119.36 (17)H10A—C10—H10B107.6
C6—C1—Cl1119.05 (17)C12—C11—C16117.8 (2)
C1—C2—C3119.4 (2)C12—C11—C10123.64 (19)
C1—C2—H2120.3C16—C11—C10118.5 (2)
C3—C2—H2120.3C11—C12—C13121.4 (2)
C4—C3—C2119.0 (2)C11—C12—H12119.3
C4—C3—H3120.5C13—C12—H12119.3
C2—C3—H3120.5O1—C13—C12115.4 (2)
C3—C4—C5121.81 (19)O1—C13—C14124.1 (2)
C3—C4—N1120.17 (18)C12—C13—C14120.5 (2)
C5—C4—N1118.01 (19)C15—C14—C13118.2 (2)
C4—C5—C6119.3 (2)C15—C14—H14120.9
C4—C5—H5120.3C13—C14—H14120.9
C6—C5—H5120.3C16—C15—C14121.3 (2)
C1—C6—C5118.9 (2)C16—C15—H15119.3
C1—C6—H6120.6C14—C15—H15119.3
C5—C6—H6120.6C15—C16—C11120.8 (2)
N2—C7—N1103.63 (18)C15—C16—H16119.6
N2—C7—S1128.85 (16)C11—C16—H16119.6
N1—C7—S1127.50 (15)O1—C17—H17A109.5
N3—C8—N1110.66 (18)O1—C17—H17B109.5
N3—C8—C9126.37 (18)H17A—C17—H17B109.5
N1—C8—C9122.96 (18)O1—C17—H17C109.5
C8—C9—C10112.31 (17)H17A—C17—H17C109.5
C8—C9—H9A109.1H17B—C17—H17C109.5
C10—C9—H9A109.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
S1—H1S···N2i1.002.373.2546 (18)147
Symmetry code: (i) x+3, y1, z+2.

Experimental details

Crystal data
Chemical formulaC17H16ClN3OS
Mr345.84
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)7.1697 (3), 11.1376 (4), 11.7574 (5)
α, β, γ (°)67.070 (2), 77.421 (2), 72.948 (3)
V3)820.93 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.26 × 0.18 × 0.13
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.912, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
15238, 3752, 2725
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.111, 1.04
No. of reflections3752
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.77

Computer programs: COLLECT (Bruker, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
S1—H1S···N2i1.002.373.2546 (18)147.0
Symmetry code: (i) x+3, y1, z+2.
 

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