Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate.

In the title compound, C(13)H(15)N(3)O(3), the dihedral angle between the two aromatic ring is 51.06 (1)°. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For the pharmacological activity of 1,2,4-triazole compounds, see: Chiu & Huskey (1998 ▶); Eliott et al. (1986 ▶, 1987 ▶); Griffin & Mannion (1986 ▶, 1987, 1987 ▶); Heubach et al. (1975 ▶, 1979 ▶); Husain & Amir (1986 ▶, 1987 ▶,); Tanaka (1974 ▶, 1975 ▶); Tsukuda et al. (1998 ▶); Witkoaski et al. (1972 ▶). For the biological activity of the triazole family, see: Unver et al. (2008 ▶, 2009 ▶). For a related structure, see: Tanak et al. (2010 ▶).

Experimental

Crystal data

C13H15N3O3

M = 261.28

Monoclinic,

a = 13.6111 (11) Å

b = 4.0970 (2) Å

c = 24.172 (2) Å

β = 100.063 (7)°

V = 1327.20 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.80 × 0.41 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer

8189 measured reflections

2581 independent reflections

1606 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.095

S = 0.93

2581 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001603X/bt5258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001603X/bt5258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H15N3O3	F(000) = 552
Mr = 261.28	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.6111 (11) Å	Cell parameters from 10833 reflections
b = 4.0970 (2) Å	θ = 1.5–27.2°
c = 24.172 (2) Å	µ = 0.10 mm−1
β = 100.063 (7)°	T = 293 K
V = 1327.20 (17) Å3	Prism, colourless
Z = 4	0.80 × 0.41 × 0.13 mm

Stoe IPDS 2 diffractometer	1606 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 26.0°, θmin = 1.6°
Detector resolution: 6.67 pixels mm-1	h = −16→15
rotation method scans	k = −4→5
8189 measured reflections	l = −29→29
2581 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0488P)2] where P = (Fo2 + 2Fc2)/3
2581 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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 > 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.

	x	y	z	Uiso*/Ueq
C1	0.44143 (13)	0.7739 (5)	0.05726 (6)	0.0485 (5)
C2	0.51671 (12)	0.5332 (4)	0.13682 (6)	0.0440 (4)
C3	0.53173 (14)	0.3581 (6)	0.19150 (8)	0.0525 (5)
C4	0.63819 (16)	0.2621 (7)	0.21203 (9)	0.0631 (6)
C5	0.32736 (11)	0.5585 (5)	0.11912 (6)	0.0432 (4)
C6	0.30553 (12)	0.6504 (5)	0.17095 (6)	0.0466 (5)
H6	0.3534	0.7542	0.1973	0.056*
C7	0.21229 (12)	0.5858 (5)	0.18282 (6)	0.0473 (4)
H7	0.1975	0.6437	0.2177	0.057*
C8	0.14040 (12)	0.4365 (5)	0.14379 (6)	0.0450 (4)
C9	0.16301 (13)	0.3535 (5)	0.09164 (7)	0.0533 (5)
H9	0.1146	0.2559	0.0648	0.064*
C10	0.25609 (12)	0.4141 (5)	0.07938 (6)	0.0515 (5)
H10	0.2708	0.3579	0.0445	0.062*
C11	0.04218 (13)	0.3608 (5)	0.15961 (7)	0.0512 (5)
C12	−0.11800 (16)	0.1271 (8)	0.13044 (10)	0.0724 (7)
C13	−0.1753 (2)	−0.0096 (12)	0.07756 (15)	0.1015 (11)
N1	0.54074 (11)	0.7686 (5)	0.06243 (6)	0.0562 (5)
N2	0.58809 (10)	0.6223 (4)	0.11107 (5)	0.0519 (4)
N3	0.42458 (9)	0.6181 (4)	0.10615 (5)	0.0447 (4)
O1	0.37870 (9)	0.8859 (4)	0.01948 (5)	0.0624 (4)
O2	0.02253 (9)	0.4134 (4)	0.20563 (5)	0.0726 (5)
O3	−0.02131 (9)	0.2283 (4)	0.11801 (5)	0.0660 (4)
H1	0.5731 (14)	0.864 (5)	0.0382 (8)	0.062 (6)*
H3A	0.4910 (15)	0.170 (5)	0.1871 (8)	0.069 (6)*
H3B	0.5059 (14)	0.489 (5)	0.2178 (8)	0.065 (6)*
H4A	0.6436 (14)	0.140 (5)	0.2481 (9)	0.074 (6)*
H4B	0.6795 (18)	0.443 (6)	0.2188 (9)	0.090 (8)*
H4C	0.6648 (16)	0.115 (6)	0.1853 (10)	0.086 (7)*
H12A	−0.1044 (16)	−0.029 (6)	0.1621 (9)	0.085 (7)*
H12B	−0.1459 (17)	0.324 (6)	0.1422 (9)	0.083 (8)*
H13A	−0.234 (2)	−0.096 (8)	0.0840 (12)	0.126 (10)*
H13B	−0.138 (3)	−0.175 (9)	0.0604 (14)	0.153 (16)*
H13C	−0.189 (2)	0.174 (8)	0.0528 (12)	0.120 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.0429 (10)	0.0675 (13)	0.0373 (8)	−0.0030 (9)	0.0133 (7)	0.0024 (9)
C2	0.0395 (9)	0.0531 (12)	0.0399 (8)	−0.0052 (8)	0.0087 (7)	−0.0039 (8)
C3	0.0470 (11)	0.0639 (15)	0.0468 (10)	0.0000 (11)	0.0083 (8)	0.0064 (10)
C4	0.0521 (12)	0.0768 (17)	0.0572 (12)	0.0002 (13)	0.0006 (10)	0.0093 (12)
C5	0.0374 (9)	0.0534 (12)	0.0404 (8)	−0.0005 (8)	0.0111 (7)	0.0043 (8)
C6	0.0433 (9)	0.0591 (13)	0.0377 (8)	−0.0077 (9)	0.0083 (7)	−0.0033 (8)
C7	0.0462 (9)	0.0612 (12)	0.0364 (8)	−0.0028 (9)	0.0127 (7)	−0.0011 (8)
C8	0.0377 (9)	0.0572 (12)	0.0409 (8)	0.0010 (8)	0.0095 (7)	0.0033 (8)
C9	0.0431 (10)	0.0739 (14)	0.0428 (9)	−0.0079 (9)	0.0074 (7)	−0.0078 (9)
C10	0.0449 (10)	0.0743 (13)	0.0370 (8)	−0.0026 (10)	0.0118 (7)	−0.0052 (9)
C11	0.0417 (10)	0.0646 (14)	0.0481 (9)	−0.0004 (9)	0.0095 (8)	0.0047 (9)
C12	0.0435 (12)	0.096 (2)	0.0784 (15)	−0.0156 (13)	0.0131 (11)	0.0078 (15)
C13	0.0636 (17)	0.135 (3)	0.098 (2)	−0.039 (2)	−0.0063 (16)	0.010 (2)
N1	0.0414 (9)	0.0862 (13)	0.0438 (8)	−0.0034 (8)	0.0151 (6)	0.0120 (8)
N2	0.0424 (8)	0.0710 (11)	0.0430 (7)	−0.0024 (8)	0.0095 (6)	0.0047 (7)
N3	0.0375 (8)	0.0609 (10)	0.0370 (7)	−0.0037 (7)	0.0102 (6)	0.0038 (7)
O1	0.0463 (7)	0.0976 (11)	0.0452 (6)	0.0052 (7)	0.0137 (6)	0.0196 (7)
O2	0.0552 (8)	0.1122 (13)	0.0562 (7)	−0.0142 (8)	0.0256 (6)	−0.0088 (8)
O3	0.0414 (7)	0.1015 (12)	0.0556 (7)	−0.0182 (7)	0.0100 (6)	−0.0041 (7)

C1—O1	1.2251 (19)	C7—H7	0.9300
C1—N1	1.336 (2)	C8—C9	1.391 (2)
C1—N3	1.397 (2)	C8—C11	1.486 (2)
C2—N2	1.295 (2)	C9—C10	1.373 (2)
C2—N3	1.385 (2)	C9—H9	0.9300
C2—C3	1.486 (2)	C10—H10	0.9300
C3—C4	1.500 (3)	C11—O2	1.2080 (19)
C3—H3A	0.94 (2)	C11—O3	1.322 (2)
C3—H3B	0.95 (2)	C12—O3	1.460 (2)
C4—H4A	1.00 (2)	C12—C13	1.486 (4)
C4—H4B	0.93 (3)	C12—H12A	0.99 (2)
C4—H4C	1.00 (2)	C12—H12B	0.96 (2)
C5—C10	1.374 (2)	C13—H13A	0.92 (3)
C5—C6	1.389 (2)	C13—H13B	0.98 (4)
C5—N3	1.433 (2)	C13—H13C	0.96 (3)
C6—C7	1.375 (2)	N1—N2	1.376 (2)
C6—H6	0.9300	N1—H1	0.883 (19)
C7—C8	1.378 (2)
O1—C1—N1	129.64 (15)	C10—C9—C8	120.66 (16)
O1—C1—N3	127.27 (15)	C10—C9—H9	119.7
N1—C1—N3	103.09 (14)	C8—C9—H9	119.7
N2—C2—N3	110.93 (14)	C9—C10—C5	119.49 (15)
N2—C2—C3	124.44 (15)	C9—C10—H10	120.3
N3—C2—C3	124.63 (14)	C5—C10—H10	120.3
C2—C3—C4	113.30 (17)	O2—C11—O3	123.57 (16)
C2—C3—H3A	107.9 (12)	O2—C11—C8	123.62 (16)
C4—C3—H3A	109.7 (12)	O3—C11—C8	112.81 (14)
C2—C3—H3B	108.3 (12)	O3—C12—C13	106.6 (2)
C4—C3—H3B	112.2 (11)	O3—C12—H12A	106.8 (13)
H3A—C3—H3B	105.0 (17)	C13—C12—H12A	114.8 (13)
C3—C4—H4A	109.9 (12)	O3—C12—H12B	103.8 (14)
C3—C4—H4B	111.7 (15)	C13—C12—H12B	113.4 (14)
H4A—C4—H4B	107.3 (17)	H12A—C12—H12B	110 (2)
C3—C4—H4C	112.6 (13)	C12—C13—H13A	110.1 (18)
H4A—C4—H4C	106.5 (18)	C12—C13—H13B	113 (2)
H4B—C4—H4C	109 (2)	H13A—C13—H13B	110 (3)
C10—C5—C6	120.72 (15)	C12—C13—H13C	104.8 (18)
C10—C5—N3	119.11 (14)	H13A—C13—H13C	109 (2)
C6—C5—N3	120.16 (14)	H13B—C13—H13C	110 (3)
C7—C6—C5	119.14 (15)	C1—N1—N2	113.73 (14)
C7—C6—H6	120.4	C1—N1—H1	123.0 (12)
C5—C6—H6	120.4	N2—N1—H1	123.1 (12)
C6—C7—C8	120.88 (15)	C2—N2—N1	104.77 (13)
C6—C7—H7	119.6	C2—N3—C1	107.48 (13)
C8—C7—H7	119.6	C2—N3—C5	128.63 (13)
C7—C8—C9	119.07 (15)	C1—N3—C5	123.87 (13)
C7—C8—C11	118.65 (14)	C11—O3—C12	116.92 (15)
C9—C8—C11	122.26 (15)
N2—C2—C3—C4	−5.8 (3)	N3—C2—N2—N1	0.0 (2)
N3—C2—C3—C4	173.1 (2)	C3—C2—N2—N1	178.99 (19)
C10—C5—C6—C7	2.0 (3)	C1—N1—N2—C2	0.2 (2)
N3—C5—C6—C7	−178.93 (17)	N2—C2—N3—C1	−0.1 (2)
C5—C6—C7—C8	−1.0 (3)	C3—C2—N3—C1	−179.15 (19)
C6—C7—C8—C9	−0.6 (3)	N2—C2—N3—C5	178.63 (17)
C6—C7—C8—C11	177.66 (18)	C3—C2—N3—C5	−0.4 (3)
C7—C8—C9—C10	1.1 (3)	O1—C1—N3—C2	−179.77 (19)
C11—C8—C9—C10	−177.07 (19)	N1—C1—N3—C2	0.23 (19)
C8—C9—C10—C5	−0.1 (3)	O1—C1—N3—C5	1.4 (3)
C6—C5—C10—C9	−1.5 (3)	N1—C1—N3—C5	−178.60 (16)
N3—C5—C10—C9	179.42 (17)	C10—C5—N3—C2	−128.50 (19)
C7—C8—C11—O2	−2.5 (3)	C6—C5—N3—C2	52.4 (3)
C9—C8—C11—O2	175.7 (2)	C10—C5—N3—C1	50.1 (3)
C7—C8—C11—O3	177.81 (17)	C6—C5—N3—C1	−129.01 (19)
C9—C8—C11—O3	−4.0 (3)	O2—C11—O3—C12	−3.3 (3)
O1—C1—N1—N2	179.7 (2)	C8—C11—O3—C12	176.4 (2)
N3—C1—N1—N2	−0.3 (2)	C13—C12—O3—C11	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.883 (19)	1.94 (2)	2.808 (2)	169.5 (18)

Symmetry code: (i) .