1-(4-Chloro-phen-yl)-1H-1,2,4-triazol-5(4H)-one.

In the title compound, C8H6ClN3O, the dihedral angle between the 1,2,4-triazole and benzene rings is 4.60 (9)° and an intra-molecular C-H⋯O inter-action closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops and C-H⋯O inter-actions link the dimers into [100] chains. Weak π-π stacking inter-actions [centroid-centroid distance = 3.644 (1) Å] are also observed.

Related literature

For a related structure and background to 1,2,4-triazoles, see: Devarajegowda et al.(2012 ▶).

Experimental

Crystal data

C8H6ClN3O

M = 195.61

Triclinic,

a = 6.5791 (4) Å

b = 7.2663 (4) Å

c = 9.3342 (5) Å

α = 80.121 (4)°

β = 85.042 (4)°

γ = 70.235 (4)°

V = 413.52 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ▶) T min = 0.770, T max = 1.000

5938 measured reflections

1438 independent reflections

1270 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.06

1438 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006412/hb7211sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006412/hb7211Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006412/hb7211Isup3.cml

CCDC reference: 993126

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H6ClN3O	Z = 2
Mr = 195.61	F(000) = 200
Triclinic, P1	Dx = 1.571 Mg m−3
Hall symbol: -P 1	Melting point: 528 K
a = 6.5791 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2663 (4) Å	Cell parameters from 1438 reflections
c = 9.3342 (5) Å	θ = 2.2–25.0°
α = 80.121 (4)°	µ = 0.42 mm−1
β = 85.042 (4)°	T = 296 K
γ = 70.235 (4)°	Plate, colourless
V = 413.52 (4) Å3	0.24 × 0.20 × 0.12 mm

Bruker SMART CCD diffractometer	1438 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −7→7
Tmin = 0.770, Tmax = 1.000	k = −8→8
5938 measured reflections	l = −11→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.1038P] where P = (Fo2 + 2Fc2)/3
1438 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. IR (KBr): 1686 (C=O), 3433 (NH); 1H-NMR (400 MHz, DMSO-D6, δ p.p.m.): 7.46–7.50 (d, 2H, ArH, J = 16 Hz), 7.90–7.94 (d, 2H, ArH, J = 16 Hz), 8.12 (s, 1H, C5H), 12.00 (s, 1H, NH); 13C-NMR (100 MHz, DMSO-D6, δ p.p.m.): 119.26, 128.77, 128.84, 136.66, 136.72, 152.17; MS (m/z, 70 eV): 197 (M2+), 195 (M+), 127, 125, 113, 111.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	−0.31296 (10)	0.62029 (8)	1.39673 (5)	0.0705 (2)
O2	−0.1420 (2)	0.9297 (2)	0.66886 (13)	0.0595 (4)
N3	0.1322 (2)	0.79679 (19)	0.83947 (14)	0.0385 (3)
N4	0.3528 (2)	0.7607 (2)	0.83651 (15)	0.0488 (4)
N5	0.2213 (2)	0.8940 (2)	0.62018 (15)	0.0457 (4)
H5	0.2196	0.9413	0.5291	0.055*
C11	−0.1807 (3)	0.6731 (2)	1.23269 (18)	0.0462 (4)
C10	−0.2983 (3)	0.7604 (3)	1.1128 (2)	0.0600 (5)
H10	−0.4479	0.7927	1.1186	0.072*
C9	−0.1960 (3)	0.8017 (3)	0.9812 (2)	0.0557 (5)
H9	−0.2767	0.8615	0.8986	0.067*
C8	0.0241 (2)	0.7544 (2)	0.97287 (16)	0.0369 (3)
C7	0.0477 (3)	0.8791 (2)	0.70550 (17)	0.0414 (4)
C12	0.0388 (3)	0.6240 (3)	1.2260 (2)	0.0600 (5)
H12	0.1183	0.5645	1.3092	0.072*
C13	0.1426 (3)	0.6632 (3)	1.0949 (2)	0.0563 (5)
H13	0.2924	0.6278	1.0894	0.068*
C6	0.3967 (3)	0.8216 (3)	0.70340 (19)	0.0500 (4)
H6	0.5350	0.8162	0.6684	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.0853 (4)	0.0835 (4)	0.0407 (3)	−0.0336 (3)	0.0192 (2)	−0.0029 (2)
O2	0.0439 (7)	0.0937 (10)	0.0378 (6)	−0.0286 (7)	−0.0083 (5)	0.0143 (6)
N3	0.0342 (7)	0.0481 (7)	0.0320 (7)	−0.0137 (5)	−0.0030 (5)	−0.0012 (5)
N4	0.0351 (8)	0.0675 (9)	0.0393 (8)	−0.0140 (6)	−0.0019 (6)	−0.0020 (6)
N5	0.0429 (8)	0.0615 (8)	0.0319 (7)	−0.0210 (6)	0.0008 (6)	0.0018 (6)
C11	0.0586 (11)	0.0470 (9)	0.0333 (8)	−0.0202 (8)	0.0072 (7)	−0.0046 (7)
C10	0.0396 (9)	0.0893 (14)	0.0466 (10)	−0.0202 (9)	0.0037 (8)	−0.0030 (9)
C9	0.0403 (9)	0.0861 (13)	0.0344 (9)	−0.0181 (9)	−0.0046 (7)	0.0041 (8)
C8	0.0399 (8)	0.0389 (8)	0.0313 (8)	−0.0132 (6)	−0.0013 (6)	−0.0029 (6)
C7	0.0411 (9)	0.0499 (9)	0.0337 (8)	−0.0187 (7)	−0.0030 (7)	0.0011 (6)
C12	0.0579 (12)	0.0775 (13)	0.0346 (9)	−0.0167 (10)	−0.0070 (8)	0.0096 (8)
C13	0.0399 (9)	0.0786 (12)	0.0412 (10)	−0.0149 (8)	−0.0072 (8)	0.0087 (8)
C6	0.0377 (9)	0.0696 (11)	0.0405 (9)	−0.0180 (8)	0.0025 (7)	−0.0041 (8)

Cl1—C11	1.7444 (16)	C11—C12	1.364 (3)
O2—C7	1.237 (2)	C10—C9	1.385 (3)
N3—C7	1.367 (2)	C10—H10	0.9300
N3—N4	1.3833 (19)	C9—C8	1.369 (2)
N3—C8	1.419 (2)	C9—H9	0.9300
N4—C6	1.288 (2)	C8—C13	1.375 (2)
N5—C6	1.348 (2)	C12—C13	1.383 (3)
N5—C7	1.359 (2)	C12—H12	0.9300
N5—H5	0.8600	C13—H13	0.9300
C11—C10	1.352 (3)	C6—H6	0.9300
C7—N3—N4	111.34 (13)	C9—C8—C13	119.67 (15)
C7—N3—C8	128.99 (13)	C9—C8—N3	120.90 (14)
N4—N3—C8	119.63 (12)	C13—C8—N3	119.43 (15)
C6—N4—N3	103.86 (13)	O2—C7—N5	127.42 (15)
C6—N5—C7	107.98 (14)	O2—C7—N3	128.69 (15)
C6—N5—H5	126.0	N5—C7—N3	103.89 (13)
C7—N5—H5	126.0	C11—C12—C13	119.63 (17)
C10—C11—C12	120.83 (16)	C11—C12—H12	120.2
C10—C11—Cl1	119.12 (14)	C13—C12—H12	120.2
C12—C11—Cl1	120.04 (14)	C8—C13—C12	119.95 (17)
C11—C10—C9	119.95 (17)	C8—C13—H13	120.0
C11—C10—H10	120.0	C12—C13—H13	120.0
C9—C10—H10	120.0	N4—C6—N5	112.93 (15)
C8—C9—C10	119.94 (17)	N4—C6—H6	123.5
C8—C9—H9	120.0	N5—C6—H6	123.5
C10—C9—H9	120.0
C7—N3—N4—C6	0.28 (18)	C6—N5—C7—N3	0.31 (18)
C8—N3—N4—C6	−177.50 (14)	N4—N3—C7—O2	179.93 (18)
C12—C11—C10—C9	−0.3 (3)	C8—N3—C7—O2	−2.6 (3)
Cl1—C11—C10—C9	−179.35 (16)	N4—N3—C7—N5	−0.37 (18)
C11—C10—C9—C8	−0.1 (3)	C8—N3—C7—N5	177.14 (14)
C10—C9—C8—C13	1.1 (3)	C10—C11—C12—C13	−0.3 (3)
C10—C9—C8—N3	−179.50 (17)	Cl1—C11—C12—C13	178.82 (16)
C7—N3—C8—C9	−2.1 (3)	C9—C8—C13—C12	−1.6 (3)
N4—N3—C8—C9	175.26 (15)	N3—C8—C13—C12	178.97 (17)
C7—N3—C8—C13	177.37 (16)	C11—C12—C13—C8	1.2 (3)
N4—N3—C8—C13	−5.3 (2)	N3—N4—C6—N5	−0.1 (2)
C6—N5—C7—O2	−179.98 (18)	C7—N5—C6—N4	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2i	0.86	1.95	2.7924 (18)	166
C6—H6···O2ii	0.93	2.53	3.360 (3)	149
C9—H9···O2	0.93	2.29	2.933 (2)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O2i	0.86	1.95	2.7924 (18)	166
C6—H6⋯O2ii	0.93	2.53	3.360 (3)	149
C9—H9⋯O2	0.93	2.29	2.933 (2)	126

Symmetry codes: (i) ; (ii) .