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

In the title compound, C(10)H(11)N(3)O(2), the triazole ring has a dihedral angle of 11.55 (2)° relative to the benzene ring. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, and by weak π-π stacking inter-actions [centroid-to-centroid distance = 3.545 (3) Å].

Related literature

For related literature on the biological activity of the title compound, see: Kitazaki et al. (1996 ▶); John (1996 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H11N3O2

M = 205.22

Orthorhombic,

a = 13.244 (3) Å

b = 8.4865 (17) Å

c = 17.518 (4) Å

V = 1968.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 113 (2) K

0.16 × 0.14 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.973, T max = 0.988

12523 measured reflections

2163 independent reflections

1923 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 1.09

2163 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031784/sg2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031784/sg2268Isup2.hkl

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

C10H11N3O2	F(000) = 864
Mr = 205.22	Dx = 1.385 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4443 reflections
a = 13.244 (3) Å	θ = 1.5–27.1°
b = 8.4865 (17) Å	µ = 0.10 mm−1
c = 17.518 (4) Å	T = 113 K
V = 1968.9 (7) Å3	Block, colorless
Z = 8	0.16 × 0.14 × 0.12 mm

Rigaku Saturn diffractometer	2163 independent reflections
Radiation source: rotating anode	1923 reflections with I > 2σ(I)
confocal	Rint = 0.046
Detector resolution: 7.31 pixels mm-1	θmax = 27.1°, θmin = 2.8°
ω scans	h = −16→16
Absorption correction: multi-scan (Crystalclear; Rigaku, 2005)	k = −10→10
Tmin = 0.973, Tmax = 0.988	l = −19→22
12523 measured reflections

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.2559P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2163 reflections	Δρmax = 0.19 e Å−3
143 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

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
O1	0.50756 (8)	0.83446 (11)	0.57225 (5)	0.0310 (3)
O2	0.39300 (8)	0.14256 (11)	0.72040 (6)	0.0292 (3)
N1	0.41360 (9)	0.87270 (14)	0.46051 (6)	0.0263 (3)
N2	0.33167 (9)	0.64616 (13)	0.45502 (6)	0.0252 (3)
N3	0.39458 (9)	0.65123 (13)	0.51918 (6)	0.0229 (3)
C1	0.44607 (11)	0.79085 (16)	0.52321 (7)	0.0249 (3)
C2	0.34610 (11)	0.78137 (16)	0.42171 (7)	0.0249 (3)
C3	0.29407 (12)	0.83520 (17)	0.35153 (8)	0.0328 (4)
H3A	0.2456	0.7574	0.3361	0.049*
H3B	0.3427	0.8500	0.3115	0.049*
H3C	0.2602	0.9331	0.3615	0.049*
C4	0.39649 (10)	0.52033 (15)	0.56989 (7)	0.0219 (3)
C5	0.44275 (11)	0.53031 (16)	0.64158 (7)	0.0253 (3)
H5	0.4753	0.6224	0.6566	0.030*
C6	0.43944 (11)	0.40130 (17)	0.68989 (7)	0.0264 (3)
H6	0.4695	0.4077	0.7378	0.032*
C7	0.39175 (10)	0.26195 (15)	0.66796 (7)	0.0234 (3)
C8	0.34760 (10)	0.25219 (16)	0.59617 (7)	0.0248 (3)
H8	0.3163	0.1594	0.5807	0.030*
C9	0.35032 (10)	0.38157 (16)	0.54756 (7)	0.0242 (3)
H9	0.3208	0.3748	0.4995	0.029*
C10	0.33849 (11)	0.00276 (17)	0.70166 (8)	0.0292 (3)
H10A	0.2699	0.0295	0.6894	0.044*
H10B	0.3393	−0.0679	0.7445	0.044*
H10C	0.3695	−0.0474	0.6585	0.044*
H1	0.4346 (14)	0.975 (2)	0.4473 (9)	0.041 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0328 (6)	0.0288 (6)	0.0313 (5)	−0.0098 (4)	−0.0025 (4)	0.0006 (4)
O2	0.0286 (6)	0.0272 (5)	0.0317 (5)	−0.0030 (4)	−0.0064 (4)	0.0062 (4)
N1	0.0305 (7)	0.0222 (6)	0.0263 (6)	−0.0032 (5)	0.0027 (5)	0.0011 (5)
N2	0.0273 (7)	0.0236 (6)	0.0246 (6)	0.0019 (5)	−0.0012 (4)	−0.0018 (4)
N3	0.0231 (6)	0.0224 (6)	0.0233 (6)	−0.0019 (5)	−0.0001 (4)	−0.0014 (4)
C1	0.0267 (8)	0.0232 (7)	0.0248 (6)	−0.0018 (6)	0.0055 (5)	−0.0013 (5)
C2	0.0273 (8)	0.0226 (7)	0.0247 (6)	0.0026 (5)	0.0043 (5)	−0.0033 (5)
C3	0.0466 (10)	0.0244 (7)	0.0273 (7)	0.0038 (7)	−0.0018 (6)	−0.0007 (5)
C4	0.0192 (7)	0.0219 (7)	0.0247 (6)	0.0014 (5)	0.0039 (5)	0.0003 (5)
C5	0.0219 (7)	0.0243 (7)	0.0297 (7)	−0.0028 (5)	−0.0010 (5)	−0.0030 (5)
C6	0.0222 (7)	0.0310 (7)	0.0260 (7)	−0.0009 (6)	−0.0036 (5)	−0.0009 (6)
C7	0.0186 (7)	0.0243 (7)	0.0272 (7)	0.0025 (5)	0.0005 (5)	0.0019 (5)
C8	0.0241 (7)	0.0220 (7)	0.0283 (7)	−0.0004 (5)	−0.0018 (5)	−0.0022 (5)
C9	0.0235 (7)	0.0249 (7)	0.0242 (6)	0.0006 (5)	−0.0013 (5)	−0.0018 (5)
C10	0.0278 (8)	0.0254 (8)	0.0344 (7)	−0.0007 (6)	0.0007 (6)	0.0045 (6)

O1—C1	1.2402 (17)	C4—C9	1.3833 (19)
O2—C7	1.3677 (16)	C4—C5	1.3999 (18)
O2—C10	1.4270 (17)	C5—C6	1.3845 (19)
N1—C2	1.3644 (18)	C5—H5	0.9300
N1—C1	1.3689 (18)	C6—C7	1.3946 (19)
N1—H1	0.938 (18)	C6—H6	0.9300
N2—C2	1.3014 (18)	C7—C8	1.3894 (18)
N2—N3	1.3997 (16)	C8—C9	1.3900 (19)
N3—C1	1.3689 (18)	C8—H8	0.9300
N3—C4	1.4226 (17)	C9—H9	0.9300
C2—C3	1.4816 (19)	C10—H10A	0.9600
C3—H3A	0.9600	C10—H10B	0.9600
C3—H3B	0.9600	C10—H10C	0.9600
C3—H3C	0.9600
C7—O2—C10	117.08 (10)	C5—C4—N3	121.38 (12)
C2—N1—C1	108.50 (12)	C6—C5—C4	119.12 (12)
C2—N1—H1	126.5 (10)	C6—C5—H5	120.4
C1—N1—H1	125.0 (10)	C4—C5—H5	120.4
C2—N2—N3	104.21 (11)	C5—C6—C7	121.10 (12)
C1—N3—N2	111.38 (11)	C5—C6—H6	119.4
C1—N3—C4	129.40 (11)	C7—C6—H6	119.4
N2—N3—C4	119.21 (10)	O2—C7—C8	124.67 (12)
O1—C1—N3	128.40 (13)	O2—C7—C6	115.96 (11)
O1—C1—N1	127.64 (13)	C8—C7—C6	119.37 (12)
N3—C1—N1	103.96 (12)	C7—C8—C9	119.77 (12)
N2—C2—N1	111.95 (12)	C7—C8—H8	120.1
N2—C2—C3	125.14 (13)	C9—C8—H8	120.1
N1—C2—C3	122.88 (12)	C4—C9—C8	120.71 (12)
C2—C3—H3A	109.5	C4—C9—H9	119.6
C2—C3—H3B	109.5	C8—C9—H9	119.6
H3A—C3—H3B	109.5	O2—C10—H10A	109.5
C2—C3—H3C	109.5	O2—C10—H10B	109.5
H3A—C3—H3C	109.5	H10A—C10—H10B	109.5
H3B—C3—H3C	109.5	O2—C10—H10C	109.5
C9—C4—C5	119.91 (12)	H10A—C10—H10C	109.5
C9—C4—N3	118.71 (12)	H10B—C10—H10C	109.5
C2—N2—N3—C1	0.01 (14)	C1—N3—C4—C5	11.1 (2)
C2—N2—N3—C4	179.21 (11)	N2—N3—C4—C5	−167.89 (12)
N2—N3—C1—O1	179.91 (13)	C9—C4—C5—C6	−1.45 (19)
C4—N3—C1—O1	0.8 (2)	N3—C4—C5—C6	177.74 (12)
N2—N3—C1—N1	0.27 (14)	C4—C5—C6—C7	0.6 (2)
C4—N3—C1—N1	−178.83 (12)	C10—O2—C7—C8	−4.83 (19)
C2—N1—C1—O1	179.92 (14)	C10—O2—C7—C6	175.59 (12)
C2—N1—C1—N3	−0.44 (14)	C5—C6—C7—O2	−179.84 (12)
N3—N2—C2—N1	−0.31 (14)	C5—C6—C7—C8	0.6 (2)
N3—N2—C2—C3	−178.37 (13)	O2—C7—C8—C9	179.62 (12)
C1—N1—C2—N2	0.49 (16)	C6—C7—C8—C9	−0.8 (2)
C1—N1—C2—C3	178.61 (12)	C5—C4—C9—C8	1.2 (2)
C1—N3—C4—C9	−169.66 (13)	N3—C4—C9—C8	−178.00 (12)
N2—N3—C4—C9	11.31 (18)	C7—C8—C9—C4	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O1i	0.96	2.57	3.4918 (18)	160
N1—H1···O1ii	0.938 (18)	1.825 (19)	2.7561 (16)	171.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O1i	0.96	2.57	3.4918 (18)	160
N1—H1⋯O1ii	0.938 (18)	1.825 (19)	2.7561 (16)	171.9 (16)

Symmetry codes: (i) ; (ii) .