3-(2-Chloro­phen­yl)-4-(4-nitro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione

Nikoo, A.; Akbari Dilmaghani, K.; Hassanzadeh, A.; Notash, B.

doi:10.1107/S1600536811020459

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1612

doi:10.1107/S1600536811020459

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3-(2-Chlorophenyl)-4-(4-nitrophenyl)-1H-1,2,4-triazole-5(4H)-thione

Abbas Nikoo,^a Karim Akbari Dilmaghani,^a ^* Ali Hassanzadeh ^a and Behrouz Notash ^b

^aDepartment of Chemistry, Faculty of Science, Urmia University, 57159 Urmia, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C. Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: kadilmaghani@yahoo.com

(Received 15 May 2011; accepted 28 May 2011; online 11 June 2011)

In the crystal structure of the title triazole compound, C₁₄H₉ClN₄O₂S, molecules are connected into centrosymmetric dimers by pairs of N—H⋯S hydrogen bonds. In addition, there are weak C—H⋯N hydrogen bonds stabilizing the crystal structure. The dihedral angles between the triazole ring and the two benzene rings are 73.0 (4) and 72.9 (4)°.

Related literature

For related structures, see: Genç et al. (2004 ); Kumaran et al. (1999 ). For the synthesis of triazoles, see: Zamani et al. (2003 ).

Experimental

Crystal data

C₁₄H₉ClN₄O₂S
M_r = 332.77
Monoclinic, P 2₁ /n
a = 6.7262 (13) Å
b = 17.109 (3) Å
c = 13.101 (3) Å
β = 95.89 (3)°
V = 1499.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 298 K
0.35 × 0.3 × 0.3 mm

Data collection

Stoe IPDS 2T diffractometer
16462 measured reflections
4038 independent reflections
2850 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.174
S = 1.18
4038 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯S1ⁱ	0.86 (3)	2.48 (3)	3.328 (3)	172 (3)
C2—H2⋯N1ⁱⁱ	0.93	2.54	3.454 (5)	170
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020459/bt5548sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020459/bt5548Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020459/bt5548Isup3.cml

checkCIF report

Comment top

In the medicinal chemistry, 1,2,4-triazoles are widely used. Cyclization of 1,4-disubstituted thiosemicarbazides produced 4,5-disubstituted 1,2,4-triazoles (Zamani et al., 2003). 4-nitro phenylisothiocyanate reacted with 2-chlorophenylcarboxylic acid hydrazide to yield the corresponding 1-(2-chlorobenzoyl)-4-(4-nitrophenyl)thiosemicarbazide (1), whereas cyclization of (1) with NaHCO₃ 10% solution gave the 3-(2-Chlorophenyl)-4-(4-nitrophenyl)-1H-1,2,4-triazole-5(4H)-thione (2) (Fig. 1).The structures of the compounds were assigned on the basis of IR, ¹H-NMR and ¹³C-NMR spectra.

The molecular structure of the title compound is shown in Fig. 2. In the crystal structure of the title compound, there are intermolecular N—H···S and weak C—H···N hydrogen bonding which play important role in the stabilization of the crystal structure (Table 1 and Fig. 3).

Related literature top

For related structures, see: Genç et al. (2004); Kumaran et al. (1999). For the synthesis of triazoles, see: Zamani et al. (2003).

Experimental top

Starting materials were obtained from Merck. For the synthesis of 1-(2-chlorobenzoyl)-4-(4-nitrophenyl)thiosemicarbazide (1), a mixture of 2-chlorophenylcarboxylic acid hydrazide (0.01 mol, 1.7 g) and 4-nitrophenyl isothiocynate (0.01 mol, 1.8 g) in absolute ethanol was refluxed for 6 h. The solid material obtained on cooling was filtered, washed with diethyl ether, dried and crystallized from ethanol (yield 82%; m.p. 170–172°C). IR (KBr, cm^-1): 3315, 3184 (N—H), 1643 (C═O), 1457, 1330 (NO₂), 1273 (C═S); ¹H NMR (300 MHz, DMSO-d₆): 7.42–7.53 (3H, m, 2-chlorophenyl), 7.74 (1H, s, 2-chlorophenyl), 7.90 (2H, d, J = 8.7, Ar—H), 8.21 (2H, d, J = 8.7, Ar—H), 9.99 (1H, br, –NH—Ar), 10.30 (1H, s, –CS—NH–), 10.56 (1H, br, –CO—NH–); ¹³C NMR (75 MHz, DMSO-d₆): 121.59, 124.66, 125.11, 127.43, 130.39, 131.22, 132.19, 146.25, 165.93 and 181.58. For the synthesis of (2), a stirred mixture of (1) (1 mmol, 0.35 g) and NaHCO₃ 10% (10 ml) was refluxed for 6 h. After cooling, the solution was acidified with hydrochloric acid and the precipitate was filtered. The precipitate was then crystallized from ethanol (yield 57%; m.p. 223–225°C). IR (KBr, cm^-1): 3286 (N—H), 1608 (C═N), 1465, 1336 (NO₂), 1529, 1177, 1071, 963 (N—═S, amide I, II, III and IV bands); ¹H NMR (300 MHz, CDCl₃): 7.37–7.53 (6H, m, Ar—H), 7.91 (1H, s, 2-chlorophenyl), 8.23 (2H, d, J = 8.7, Ar—H), 12.24 (1H, s, SH); ¹³C NMR (75 MHz, CDCl₃): 124.43, 127.26, 127.48, 128.74, 130.30, 130.50, 131.58, 132.23, 133, 133.07.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The reaction scheme for synthesis of the title compound.
	Fig. 2. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 3. The packing diagram of the title compound down the a axis. The intermolecular N—H···S, C—H···N hydrogen bonds are shown as blue dashed lines.

3-(2-Chlorophenyl)-4-(4-nitrophenyl)-1H-1,2,4-triazole-5(4H)- thione top

Crystal data top

C₁₄H₉ClN₄O₂S	F(000) = 680.0
M_r = 332.77	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4038 reflections
a = 6.7262 (13) Å	θ = 2.4–29.2°
b = 17.109 (3) Å	µ = 0.41 mm⁻¹
c = 13.101 (3) Å	T = 298 K
β = 95.89 (3)°	Block, brown
V = 1499.7 (5) Å³	0.35 × 0.3 × 0.3 mm
Z = 4

Data collection top

Stoe IPDS 2T diffractometer	2850 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 29.2°, θ_min = 2.4°
Detector resolution: 0.15 pixels mm^-1	h = −9→9
rotation method scans	k = −23→22
16462 measured reflections	l = −16→17
4038 independent reflections

Refinement top

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ²(F_o²) + (0.0706P)² + 0.4737P] where P = (F_o² + 2F_c²)/3
4038 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₉ClN₄O₂S	V = 1499.7 (5) Å³
M_r = 332.77	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7262 (13) Å	µ = 0.41 mm⁻¹
b = 17.109 (3) Å	T = 298 K
c = 13.101 (3) Å	0.35 × 0.3 × 0.3 mm
β = 95.89 (3)°

Data collection top

Stoe IPDS 2T diffractometer	2850 reflections with I > 2σ(I)
16462 measured reflections	R_int = 0.060
4038 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	Δρ_max = 0.26 e Å⁻³
4038 reflections	Δρ_min = −0.23 e Å⁻³
203 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

	x	y	z	U_iso*/U_eq
S1	0.23357 (11)	1.07003 (4)	0.08833 (6)	0.0535 (2)
Cl1	0.4224 (2)	0.80997 (7)	0.35611 (8)	0.0955 (4)
N3	0.4499 (3)	0.94203 (12)	0.15936 (15)	0.0400 (5)
C8	0.2956 (4)	0.97505 (15)	0.09792 (19)	0.0417 (6)
C7	0.4517 (4)	0.86289 (16)	0.13680 (19)	0.0433 (6)
C9	0.5843 (4)	0.98312 (15)	0.23334 (19)	0.0403 (5)
N2	0.2132 (4)	0.91476 (14)	0.04511 (19)	0.0512 (6)
C14	0.7779 (4)	0.99626 (19)	0.2123 (2)	0.0538 (7)
H14	0.8207	0.9795	0.1506	0.065*
C12	0.8404 (4)	1.05784 (17)	0.3744 (2)	0.0512 (7)
N1	0.3080 (4)	0.84485 (14)	0.06799 (19)	0.0523 (6)
C6	0.6088 (4)	0.80956 (16)	0.1831 (2)	0.0479 (6)
C11	0.6475 (5)	1.04638 (19)	0.3956 (2)	0.0555 (7)
H11	0.6049	1.0640	0.4569	0.067*
C5	0.7588 (5)	0.78584 (19)	0.1248 (3)	0.0644 (9)
H5	0.7544	0.8011	0.0565	0.077*
N4	0.9821 (5)	1.09731 (19)	0.4514 (2)	0.0732 (8)
C1	0.6151 (5)	0.78478 (19)	0.2838 (2)	0.0612 (8)
C13	0.9084 (4)	1.0349 (2)	0.2844 (2)	0.0598 (8)
H13	1.0395	1.0449	0.2716	0.072*
C10	0.5174 (4)	1.00804 (19)	0.3240 (2)	0.0508 (7)
H10	0.3858	0.9991	0.3367	0.061*
O2	1.1498 (5)	1.1103 (2)	0.4306 (3)	0.1210 (13)
C2	0.7732 (8)	0.7390 (2)	0.3270 (3)	0.0859 (13)
H2	0.7789	0.7230	0.3951	0.103*
O1	0.9257 (5)	1.1125 (2)	0.5332 (2)	0.1153 (12)
C3	0.9209 (7)	0.7181 (2)	0.2669 (5)	0.0946 (15)
H3	1.0281	0.6883	0.2954	0.114*
C4	0.9137 (6)	0.7400 (2)	0.1668 (4)	0.0852 (13)
H4	1.0131	0.7240	0.1270	0.102*
H1	0.104 (5)	0.9176 (17)	0.006 (2)	0.048 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0494 (4)	0.0469 (4)	0.0592 (4)	0.0006 (3)	−0.0187 (3)	0.0028 (3)
Cl1	0.1317 (10)	0.1029 (8)	0.0554 (5)	−0.0121 (7)	0.0263 (6)	0.0092 (5)
N3	0.0405 (11)	0.0458 (12)	0.0315 (10)	0.0015 (9)	−0.0071 (8)	0.0005 (8)
C8	0.0380 (12)	0.0494 (14)	0.0360 (12)	−0.0011 (10)	−0.0041 (10)	0.0027 (10)
C7	0.0465 (14)	0.0479 (14)	0.0341 (12)	0.0028 (11)	−0.0024 (10)	0.0026 (10)
C9	0.0384 (12)	0.0472 (14)	0.0328 (12)	0.0008 (10)	−0.0081 (10)	0.0017 (10)
N2	0.0500 (13)	0.0513 (14)	0.0476 (13)	0.0014 (10)	−0.0187 (11)	−0.0010 (10)
C14	0.0428 (15)	0.077 (2)	0.0415 (15)	0.0000 (13)	0.0016 (12)	−0.0100 (13)
C12	0.0479 (15)	0.0567 (17)	0.0453 (15)	0.0043 (12)	−0.0134 (12)	−0.0085 (12)
N1	0.0579 (14)	0.0506 (13)	0.0450 (13)	0.0029 (11)	−0.0112 (11)	−0.0022 (10)
C6	0.0503 (15)	0.0420 (14)	0.0485 (15)	−0.0010 (11)	−0.0094 (12)	0.0050 (11)
C11	0.0558 (17)	0.0692 (19)	0.0408 (15)	0.0009 (14)	0.0015 (13)	−0.0119 (13)
C5	0.065 (2)	0.0530 (18)	0.075 (2)	0.0103 (15)	0.0080 (17)	0.0146 (15)
N4	0.0633 (18)	0.085 (2)	0.0659 (19)	0.0037 (15)	−0.0195 (15)	−0.0246 (15)
C1	0.082 (2)	0.0535 (17)	0.0446 (16)	−0.0095 (15)	−0.0103 (15)	0.0079 (13)
C13	0.0355 (14)	0.084 (2)	0.0592 (18)	−0.0052 (14)	−0.0003 (12)	−0.0125 (16)
C10	0.0401 (14)	0.0705 (19)	0.0415 (14)	−0.0031 (12)	0.0038 (11)	−0.0056 (13)
O2	0.0646 (18)	0.172 (3)	0.122 (3)	−0.030 (2)	−0.0108 (17)	−0.065 (2)
C2	0.116 (3)	0.063 (2)	0.069 (2)	−0.007 (2)	−0.039 (2)	0.0228 (18)
O1	0.100 (2)	0.168 (3)	0.074 (2)	−0.015 (2)	−0.0115 (17)	−0.061 (2)
C3	0.082 (3)	0.057 (2)	0.134 (4)	0.0075 (19)	−0.043 (3)	0.018 (2)
C4	0.064 (2)	0.056 (2)	0.135 (4)	0.0139 (17)	0.008 (2)	0.018 (2)

Geometric parameters (Å, º) top

S1—C8	1.679 (3)	C6—C1	1.382 (4)
Cl1—C1	1.736 (4)	C6—C5	1.387 (5)
N3—C8	1.369 (3)	C11—C10	1.382 (4)
N3—C7	1.386 (3)	C11—H11	0.9300
N3—C9	1.439 (3)	C5—C4	1.373 (5)
C8—N2	1.331 (3)	C5—H5	0.9300
C7—N1	1.290 (3)	N4—O1	1.203 (4)
C7—C6	1.479 (4)	N4—O2	1.208 (4)
C9—C14	1.377 (4)	C1—C2	1.393 (5)
C9—C10	1.380 (4)	C13—H13	0.9300
N2—N1	1.374 (3)	C10—H10	0.9300
N2—H1	0.86 (3)	C2—C3	1.377 (7)
C14—C13	1.389 (4)	C2—H2	0.9300
C14—H14	0.9300	C3—C4	1.360 (7)
C12—C13	1.366 (4)	C3—H3	0.9300
C12—C11	1.369 (4)	C4—H4	0.9300
C12—N4	1.478 (4)

C8—N3—C7	107.5 (2)	C12—C11—H11	120.7
C8—N3—C9	125.5 (2)	C10—C11—H11	120.7
C7—N3—C9	127.0 (2)	C4—C5—C6	120.7 (4)
N2—C8—N3	103.6 (2)	C4—C5—H5	119.7
N2—C8—S1	128.6 (2)	C6—C5—H5	119.7
N3—C8—S1	127.68 (19)	O1—N4—O2	123.3 (3)
N1—C7—N3	111.1 (2)	O1—N4—C12	117.8 (3)
N1—C7—C6	126.3 (2)	O2—N4—C12	118.9 (3)
N3—C7—C6	122.4 (2)	C6—C1—C2	120.5 (4)
C14—C9—C10	121.4 (2)	C6—C1—Cl1	119.5 (3)
C14—C9—N3	119.1 (2)	C2—C1—Cl1	120.0 (3)
C10—C9—N3	119.5 (2)	C12—C13—C14	118.7 (3)
C8—N2—N1	113.7 (2)	C12—C13—H13	120.6
C8—N2—H1	124 (2)	C14—C13—H13	120.6
N1—N2—H1	122 (2)	C9—C10—C11	119.4 (3)
C9—C14—C13	119.1 (3)	C9—C10—H10	120.3
C9—C14—H14	120.5	C11—C10—H10	120.3
C13—C14—H14	120.5	C3—C2—C1	118.6 (4)
C13—C12—C11	122.8 (3)	C3—C2—H2	120.7
C13—C12—N4	118.1 (3)	C1—C2—H2	120.7
C11—C12—N4	119.1 (3)	C4—C3—C2	121.6 (4)
C7—N1—N2	104.0 (2)	C4—C3—H3	119.2
C1—C6—C5	118.9 (3)	C2—C3—H3	119.2
C1—C6—C7	122.1 (3)	C3—C4—C5	119.7 (4)
C5—C6—C7	118.9 (3)	C3—C4—H4	120.2
C12—C11—C10	118.6 (3)	C5—C4—H4	120.2

C7—N3—C8—N2	1.3 (3)	C13—C12—C11—C10	1.8 (5)
C9—N3—C8—N2	−178.7 (2)	N4—C12—C11—C10	−178.7 (3)
C7—N3—C8—S1	−176.1 (2)	C1—C6—C5—C4	−1.5 (5)
C9—N3—C8—S1	3.8 (4)	C7—C6—C5—C4	176.2 (3)
C8—N3—C7—N1	−1.3 (3)	C13—C12—N4—O1	−174.9 (4)
C9—N3—C7—N1	178.7 (3)	C11—C12—N4—O1	5.6 (5)
C8—N3—C7—C6	175.2 (2)	C13—C12—N4—O2	2.6 (5)
C9—N3—C7—C6	−4.8 (4)	C11—C12—N4—O2	−176.9 (4)
C8—N3—C9—C14	−107.0 (3)	C5—C6—C1—C2	2.2 (5)
C7—N3—C9—C14	72.9 (4)	C7—C6—C1—C2	−175.4 (3)
C8—N3—C9—C10	73.4 (3)	C5—C6—C1—Cl1	−176.9 (2)
C7—N3—C9—C10	−106.6 (3)	C7—C6—C1—Cl1	5.4 (4)
N3—C8—N2—N1	−1.0 (3)	C11—C12—C13—C14	−1.9 (5)
S1—C8—N2—N1	176.4 (2)	N4—C12—C13—C14	178.7 (3)
C10—C9—C14—C13	0.5 (5)	C9—C14—C13—C12	0.7 (5)
N3—C9—C14—C13	−179.0 (3)	C14—C9—C10—C11	−0.6 (5)
N3—C7—N1—N2	0.7 (3)	N3—C9—C10—C11	179.0 (3)
C6—C7—N1—N2	−175.6 (3)	C12—C11—C10—C9	−0.6 (5)
C8—N2—N1—C7	0.2 (3)	C6—C1—C2—C3	−1.0 (5)
N1—C7—C6—C1	−109.4 (4)	Cl1—C1—C2—C3	178.1 (3)
N3—C7—C6—C1	74.7 (4)	C1—C2—C3—C4	−1.0 (6)
N1—C7—C6—C5	73.0 (4)	C2—C3—C4—C5	1.8 (6)
N3—C7—C6—C5	−103.0 (3)	C6—C5—C4—C3	−0.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···S1ⁱ	0.86 (3)	2.48 (3)	3.328 (3)	172 (3)
C2—H2···N1ⁱⁱ	0.93	2.54	3.454 (5)	170

Symmetry codes: (i) −x, −y+2, −z; (ii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₉ClN₄O₂S
M_r	332.77
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.7262 (13), 17.109 (3), 13.101 (3)
β (°)	95.89 (3)
V (Å³)	1499.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.35 × 0.3 × 0.3

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16462, 4038, 2850
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.174, 1.18
No. of reflections	4038
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···S1ⁱ	0.86 (3)	2.48 (3)	3.328 (3)	172 (3)
C2—H2···N1ⁱⁱ	0.93	2.54	3.454 (5)	169.7

Symmetry codes: (i) −x, −y+2, −z; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

The authors are grateful to Urmia University for financial support.

References

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