4-n-Butyl-3-(3-methyl-phen-yl)-1H-1,2,4-triazol-5(4H)-one.

In the mol-ecule of the title compound, C(13)H(17)N(3)O, the two rings make a dihedral angle of 56.63 (13)°. Mol-ecules are linked by strong N-H⋯O inter-molecular hydrogen bonds into chains running along the c axis.

Related literature

For related literature, see: Akhtar et al. (2006 ▶, 2007 ▶, 2008 ▶); Aoyama et al. (1984 ▶); Al-Masoudi et al. (2006 ▶); Demirbas et al. (2002 ▶); Lin et al. (2005 ▶); Torres et al. (2005 ▶); Witkowski et al. (1972 ▶).

Experimental

Crystal data

C13H17N3O

M = 231.30

Orthorhombic,

a = 16.905 (5) Å

b = 18.139 (5) Å

c = 8.145 (2) Å

V = 2497.5 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 (2) K

0.26 × 0.19 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

8129 measured reflections

1791 independent reflections

1118 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 1.07

1791 reflections

160 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019661/bt2734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019661/bt2734Isup2.hkl

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

C13H17N3O	F000 = 992
Mr = 231.30	Dx = 1.230 Mg m−3
Orthorhombic, Ccc2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2 -2c	Cell parameters from 1751 reflections
a = 16.905 (5) Å	θ = 3.0–22.2º
b = 18.139 (5) Å	µ = 0.08 mm−1
c = 8.145 (2) Å	T = 296 (2) K
V = 2497.5 (11) Å3	Orthorhombic, white
Z = 8	0.26 × 0.19 × 0.12 mm

Bruker APEXII CCD area-detector diffractometer	1791 independent reflections
Radiation source: fine-focus sealed tube	1118 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.066
Detector resolution: 7.40 pixels mm-1	θmax = 29.2º
T = 296(2) K	θmin = 2.4º
φ and ω scans	h = −20→23
Absorption correction: none	k = −23→24
8129 measured reflections	l = −11→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1791 reflections	Δρmax = 0.15 e Å−3
160 parameters	Δρmin = −0.25 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
N1	0.09066 (14)	0.37056 (10)	0.2364 (3)	0.0349 (5)
N2	0.08503 (15)	0.41720 (12)	−0.0051 (3)	0.0407 (6)
N3	0.08408 (14)	0.34149 (11)	−0.0273 (3)	0.0412 (6)
O1	0.09681 (11)	0.49894 (11)	0.2110 (2)	0.0500 (6)
C1	0.08634 (17)	0.23582 (14)	0.1565 (3)	0.0350 (6)
C2	0.02844 (17)	0.20574 (14)	0.2574 (4)	0.0449 (8)
H2	−0.0090	0.2359	0.3072	0.054*
C3	0.0272 (2)	0.13041 (15)	0.2829 (4)	0.0531 (9)
H3	−0.0111	0.1100	0.3510	0.064*
C4	0.08179 (19)	0.08554 (16)	0.2092 (4)	0.0501 (8)
H4	0.0791	0.0349	0.2257	0.060*
C5	0.14059 (18)	0.11403 (14)	0.1111 (4)	0.0423 (7)
C6	0.14204 (17)	0.18975 (14)	0.0851 (3)	0.0389 (7)
H6	0.1811	0.2099	0.0185	0.047*
C7	0.08757 (16)	0.31523 (14)	0.1205 (3)	0.0355 (6)
C8	0.09113 (17)	0.43677 (14)	0.1525 (3)	0.0360 (6)
C9	0.11284 (18)	0.36397 (14)	0.4094 (3)	0.0385 (7)
H9A	0.0902	0.3192	0.4546	0.046*
H9B	0.0916	0.4055	0.4701	0.046*
C10	0.20182 (18)	0.36205 (16)	0.4290 (4)	0.0475 (7)
H10A	0.2223	0.3202	0.3683	0.057*
H10B	0.2239	0.4063	0.3803	0.057*
C11	0.22993 (18)	0.35668 (17)	0.6045 (4)	0.0499 (8)
H11A	0.2064	0.3137	0.6557	0.060*
H11B	0.2125	0.3999	0.6646	0.060*
C12	0.2024 (2)	0.06501 (17)	0.0313 (5)	0.0615 (10)
H13A	0.2245	0.0325	0.1123	0.092*
H13B	0.2436	0.0951	−0.0145	0.092*
H13C	0.1782	0.0364	−0.0543	0.092*
H22	0.0837 (17)	0.4487 (16)	−0.097 (4)	0.060 (10)*
C13	0.31893 (19)	0.35095 (19)	0.6144 (5)	0.0622 (9)
H13D	0.3366	0.3098	0.5500	0.093*
H13E	0.3345	0.3440	0.7267	0.093*
H13F	0.3423	0.3955	0.5730	0.093*

	U11	U22	U33	U12	U13	U23
N1	0.0461 (15)	0.0309 (11)	0.0277 (12)	−0.0011 (10)	−0.0020 (12)	−0.0027 (9)
N2	0.0577 (17)	0.0319 (12)	0.0325 (14)	−0.0033 (11)	−0.0061 (12)	0.0009 (10)
N3	0.0553 (15)	0.0328 (12)	0.0356 (14)	−0.0028 (10)	−0.0050 (12)	−0.0019 (11)
O1	0.0770 (15)	0.0307 (9)	0.0422 (12)	−0.0055 (11)	−0.0009 (11)	−0.0052 (9)
C1	0.0398 (16)	0.0312 (13)	0.0341 (15)	−0.0004 (12)	−0.0074 (13)	−0.0035 (12)
C2	0.047 (2)	0.0412 (15)	0.0464 (18)	−0.0008 (12)	0.0070 (15)	−0.0014 (14)
C3	0.056 (2)	0.0449 (16)	0.058 (2)	−0.0091 (15)	0.0099 (16)	0.0072 (15)
C4	0.063 (2)	0.0333 (14)	0.054 (2)	−0.0028 (14)	−0.0098 (18)	0.0041 (15)
C5	0.0478 (18)	0.0347 (14)	0.0444 (17)	0.0043 (13)	−0.0105 (16)	−0.0025 (14)
C6	0.0432 (17)	0.0385 (15)	0.0350 (16)	−0.0024 (12)	−0.0011 (13)	−0.0017 (13)
C7	0.0373 (16)	0.0332 (13)	0.0361 (16)	−0.0021 (11)	−0.0073 (14)	−0.0013 (11)
C8	0.0434 (17)	0.0343 (14)	0.0303 (15)	−0.0015 (12)	−0.0013 (13)	−0.0029 (12)
C9	0.0486 (19)	0.0365 (14)	0.0303 (15)	−0.0052 (12)	0.0002 (13)	−0.0013 (12)
C10	0.052 (2)	0.0548 (17)	0.0358 (16)	−0.0006 (14)	−0.0003 (15)	−0.0009 (13)
C11	0.057 (2)	0.0537 (18)	0.0393 (17)	0.0043 (15)	−0.0044 (16)	0.0027 (14)
C12	0.068 (3)	0.0503 (18)	0.066 (2)	0.0181 (17)	−0.0004 (19)	−0.0076 (17)
C13	0.059 (2)	0.069 (2)	0.059 (2)	0.0085 (17)	−0.012 (2)	−0.0021 (18)

N1—C7	1.379 (3)	C5—C12	1.518 (4)
N1—C8	1.382 (3)	C6—H6	0.9300
N1—C9	1.463 (3)	C9—C10	1.513 (4)
N2—C8	1.336 (4)	C9—H9A	0.9700
N2—N3	1.385 (3)	C9—H9B	0.9700
N2—H22	0.94 (3)	C10—C11	1.509 (4)
N3—C7	1.296 (3)	C10—H10A	0.9700
O1—C8	1.228 (3)	C10—H10B	0.9700
C1—C6	1.387 (4)	C11—C13	1.510 (4)
C1—C2	1.390 (4)	C11—H11A	0.9700
C1—C7	1.470 (4)	C11—H11B	0.9700
C2—C3	1.382 (3)	C12—H13A	0.9600
C2—H2	0.9300	C12—H13B	0.9600
C3—C4	1.369 (4)	C12—H13C	0.9600
C3—H3	0.9300	C13—H13D	0.9600
C4—C5	1.376 (4)	C13—H13E	0.9600
C4—H4	0.9300	C13—H13F	0.9600
C5—C6	1.390 (4)
C7—N1—C8	107.1 (2)	N1—C9—C10	111.0 (2)
C7—N1—C9	127.6 (2)	N1—C9—H9A	109.4
C8—N1—C9	123.1 (2)	C10—C9—H9A	109.4
C8—N2—N3	113.0 (2)	N1—C9—H9B	109.4
C8—N2—H22	127.2 (19)	C10—C9—H9B	109.4
N3—N2—H22	119.8 (19)	H9A—C9—H9B	108.0
C7—N3—N2	104.0 (2)	C11—C10—C9	114.5 (3)
C6—C1—C2	119.3 (2)	C11—C10—H10A	108.6
C6—C1—C7	119.8 (3)	C9—C10—H10A	108.6
C2—C1—C7	120.8 (3)	C11—C10—H10B	108.6
C3—C2—C1	119.2 (3)	C9—C10—H10B	108.6
C3—C2—H2	120.4	H10A—C10—H10B	107.6
C1—C2—H2	120.4	C10—C11—C13	111.7 (3)
C4—C3—C2	120.8 (3)	C10—C11—H11A	109.3
C4—C3—H3	119.6	C13—C11—H11A	109.3
C2—C3—H3	119.6	C10—C11—H11B	109.3
C3—C4—C5	121.2 (3)	C13—C11—H11B	109.3
C3—C4—H4	119.4	H11A—C11—H11B	108.0
C5—C4—H4	119.4	C5—C12—H13A	109.5
C4—C5—C6	118.2 (3)	C5—C12—H13B	109.5
C4—C5—C12	121.7 (3)	H13A—C12—H13B	109.5
C6—C5—C12	120.1 (3)	C5—C12—H13C	109.5
C5—C6—C1	121.3 (3)	H13A—C12—H13C	109.5
C5—C6—H6	119.3	H13B—C12—H13C	109.5
C1—C6—H6	119.3	C11—C13—H13D	109.5
N3—C7—N1	111.7 (2)	C11—C13—H13E	109.5
N3—C7—C1	123.0 (2)	H13D—C13—H13E	109.5
N1—C7—C1	125.2 (2)	C11—C13—H13F	109.5
O1—C8—N2	128.5 (3)	H13D—C13—H13F	109.5
O1—C8—N1	127.4 (2)	H13E—C13—H13F	109.5
N2—C8—N1	104.1 (2)
C8—N2—N3—C7	1.7 (3)	C9—N1—C7—C1	16.6 (4)
C6—C1—C2—C3	−0.6 (4)	C6—C1—C7—N3	55.9 (4)
C7—C1—C2—C3	177.3 (3)	C2—C1—C7—N3	−122.1 (3)
C1—C2—C3—C4	−0.5 (5)	C6—C1—C7—N1	−125.7 (3)
C2—C3—C4—C5	1.7 (5)	C2—C1—C7—N1	56.4 (4)
C3—C4—C5—C6	−1.6 (5)	N3—N2—C8—O1	176.6 (3)
C3—C4—C5—C12	178.8 (3)	N3—N2—C8—N1	−2.6 (3)
C4—C5—C6—C1	0.5 (4)	C7—N1—C8—O1	−176.8 (3)
C12—C5—C6—C1	−179.9 (3)	C9—N1—C8—O1	−12.7 (5)
C2—C1—C6—C5	0.7 (4)	C7—N1—C8—N2	2.5 (3)
C7—C1—C6—C5	−177.3 (3)	C9—N1—C8—N2	166.6 (3)
N2—N3—C7—N1	0.0 (3)	C7—N1—C9—C10	80.2 (3)
N2—N3—C7—C1	178.7 (3)	C8—N1—C9—C10	−80.5 (3)
C8—N1—C7—N3	−1.6 (3)	N1—C9—C10—C11	178.9 (2)
C9—N1—C7—N3	−164.8 (3)	C9—C10—C11—C13	177.0 (2)
C8—N1—C7—C1	179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O1i	0.94 (3)	1.84 (3)	2.775 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H22⋯O1i	0.94 (3)	1.84 (3)	2.775 (3)	170 (3)

Symmetry code: (i) .