5-(4-Methyl-phen-yl)-1,3,4-oxadiazol-2-amine.

In the crystal structure of the title compound, C(9)H(9)N(3)O, adjacent mol-ecules are linked through N-H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For background to 1,3,4-oxadiazole derivatives, see: Lv et al. (2010 ▶); Bachwani & Sharma (2011 ▶); Padmavathi et al. (2009 ▶); Tang et al. (2007 ▶); Xue et al. (2007 ▶).

Experimental

Crystal data

C9H9N3O

M = 175.19

Monoclinic,

a = 12.161 (2) Å

b = 5.9374 (3) Å

c = 12.8282 (15) Å

β = 108.012 (19)°

V = 880.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.38 × 0.35 × 0.30 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.966, T max = 0.973

3809 measured reflections

1800 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.03

1800 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019617/zj2066sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019617/zj2066Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019617/zj2066Isup3.cml

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

C9H9N3O	F(000) = 368
Mr = 175.19	Dx = 1.321 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.161 (2) Å	Cell parameters from 1122 reflections
b = 5.9374 (3) Å	θ = 3.3–26.3°
c = 12.8282 (15) Å	µ = 0.09 mm−1
β = 108.012 (19)°	T = 291 K
V = 880.9 (2) Å3	Prism, yellow
Z = 4	0.38 × 0.35 × 0.30 mm

Rigaku Saturn diffractometer	1800 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 28.5714 pixels mm-1	θmax = 26.4°, θmin = 3.3°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −7→6
Tmin = 0.966, Tmax = 0.973	l = −16→15
3809 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0612P)2 + 0.0867P] where P = (Fo2 + 2Fc2)/3
1800 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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	0.00011 (9)	0.21279 (17)	0.19008 (10)	0.0417 (3)
N1	−0.06440 (12)	−0.1327 (2)	0.19144 (13)	0.0516 (4)
N2	−0.13933 (12)	0.0146 (2)	0.22353 (14)	0.0497 (4)
N3	−0.13387 (15)	0.4123 (3)	0.24629 (15)	0.0572 (5)
C1	0.29096 (15)	−0.2138 (3)	0.05483 (15)	0.0515 (5)
C2	0.19911 (16)	−0.3566 (3)	0.04961 (15)	0.0537 (5)
H2	0.1975	−0.4991	0.0191	0.064*
C3	0.11020 (16)	−0.2923 (3)	0.08861 (15)	0.0485 (5)
H3	0.0500	−0.3917	0.0847	0.058*
C4	0.11017 (13)	−0.0803 (3)	0.13353 (14)	0.0395 (4)
C5	0.20195 (15)	0.0649 (3)	0.14061 (16)	0.0497 (5)
H5	0.2036	0.2073	0.1712	0.060*
C6	0.29100 (15)	−0.0041 (3)	0.10172 (17)	0.0568 (5)
H6	0.3524	0.0933	0.1073	0.068*
C7	0.01433 (13)	−0.0122 (3)	0.17222 (14)	0.0388 (4)
C8	−0.09732 (14)	0.2145 (3)	0.22099 (15)	0.0411 (4)
C9	0.38709 (18)	−0.2859 (4)	0.0109 (2)	0.0749 (7)
H9A	0.4075	−0.4395	0.0312	0.112*
H9B	0.4533	−0.1910	0.0410	0.112*
H9C	0.3617	−0.2730	−0.0676	0.112*
H3A	−0.1032 (18)	0.535 (4)	0.2273 (17)	0.068 (6)*
H3B	−0.2065 (17)	0.421 (3)	0.2559 (16)	0.062 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0408 (6)	0.0300 (6)	0.0602 (8)	−0.0006 (5)	0.0243 (6)	0.0001 (5)
N1	0.0544 (9)	0.0322 (8)	0.0790 (11)	−0.0021 (6)	0.0363 (8)	−0.0008 (7)
N2	0.0521 (8)	0.0319 (8)	0.0768 (11)	−0.0014 (6)	0.0372 (8)	0.0020 (7)
N3	0.0563 (10)	0.0337 (9)	0.0968 (14)	0.0003 (7)	0.0460 (10)	−0.0007 (8)
C1	0.0468 (10)	0.0584 (12)	0.0530 (11)	0.0107 (9)	0.0209 (9)	0.0035 (9)
C2	0.0652 (12)	0.0437 (10)	0.0584 (12)	0.0078 (9)	0.0279 (10)	−0.0056 (9)
C3	0.0538 (10)	0.0393 (9)	0.0573 (11)	−0.0033 (8)	0.0244 (9)	−0.0043 (8)
C4	0.0400 (8)	0.0351 (9)	0.0447 (10)	0.0027 (7)	0.0148 (7)	0.0025 (7)
C5	0.0478 (9)	0.0390 (10)	0.0654 (12)	−0.0004 (8)	0.0222 (9)	−0.0041 (9)
C6	0.0439 (10)	0.0566 (12)	0.0758 (14)	−0.0018 (9)	0.0269 (10)	0.0005 (10)
C7	0.0431 (9)	0.0279 (8)	0.0472 (10)	0.0011 (7)	0.0165 (8)	0.0016 (7)
C8	0.0394 (8)	0.0348 (9)	0.0544 (11)	−0.0004 (7)	0.0223 (8)	0.0020 (8)
C9	0.0596 (12)	0.0929 (17)	0.0811 (16)	0.0168 (11)	0.0350 (12)	−0.0082 (13)

O1—C8	1.3608 (19)	C2—H2	0.9300
O1—C7	1.3754 (18)	C3—C4	1.385 (2)
N1—C7	1.279 (2)	C3—H3	0.9300
N1—N2	1.4129 (19)	C4—C5	1.391 (2)
N2—C8	1.296 (2)	C4—C7	1.458 (2)
N3—C8	1.331 (2)	C5—C6	1.387 (2)
N3—H3A	0.88 (2)	C5—H5	0.9300
N3—H3B	0.93 (2)	C6—H6	0.9300
C1—C6	1.382 (3)	C9—H9A	0.9600
C1—C2	1.388 (3)	C9—H9B	0.9600
C1—C9	1.509 (3)	C9—H9C	0.9600
C2—C3	1.378 (2)
C8—O1—C7	102.79 (11)	C6—C5—C4	119.58 (16)
C7—N1—N2	107.39 (13)	C6—C5—H5	120.2
C8—N2—N1	105.34 (13)	C4—C5—H5	120.2
C8—N3—H3A	117.2 (13)	C1—C6—C5	121.82 (17)
C8—N3—H3B	119.0 (11)	C1—C6—H6	119.1
H3A—N3—H3B	119.1 (17)	C5—C6—H6	119.1
C6—C1—C2	117.61 (16)	N1—C7—O1	111.77 (14)
C6—C1—C9	121.48 (18)	N1—C7—C4	129.48 (15)
C2—C1—C9	120.92 (18)	O1—C7—C4	118.74 (13)
C3—C2—C1	121.55 (17)	N2—C8—N3	129.62 (16)
C3—C2—H2	119.2	N2—C8—O1	112.70 (14)
C1—C2—H2	119.2	N3—C8—O1	117.65 (14)
C2—C3—C4	120.28 (17)	C1—C9—H9A	109.5
C2—C3—H3	119.9	C1—C9—H9B	109.5
C4—C3—H3	119.9	H9A—C9—H9B	109.5
C3—C4—C5	119.15 (16)	C1—C9—H9C	109.5
C3—C4—C7	119.79 (15)	H9A—C9—H9C	109.5
C5—C4—C7	121.06 (15)	H9B—C9—H9C	109.5
C7—N1—N2—C8	−0.3 (2)	N2—N1—C7—C4	−177.86 (16)
C6—C1—C2—C3	0.6 (3)	C8—O1—C7—N1	−0.76 (19)
C9—C1—C2—C3	−179.45 (18)	C8—O1—C7—C4	177.94 (14)
C1—C2—C3—C4	0.6 (3)	C3—C4—C7—N1	14.9 (3)
C2—C3—C4—C5	−1.2 (3)	C5—C4—C7—N1	−165.33 (19)
C2—C3—C4—C7	178.60 (16)	C3—C4—C7—O1	−163.57 (15)
C3—C4—C5—C6	0.6 (3)	C5—C4—C7—O1	16.2 (2)
C7—C4—C5—C6	−179.16 (17)	N1—N2—C8—N3	−178.37 (19)
C2—C1—C6—C5	−1.2 (3)	N1—N2—C8—O1	−0.2 (2)
C9—C1—C6—C5	178.88 (19)	C7—O1—C8—N2	0.58 (19)
C4—C5—C6—C1	0.6 (3)	C7—O1—C8—N3	178.98 (16)
N2—N1—C7—O1	0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.88 (2)	2.11 (2)	2.979 (2)	165.7 (19)
N3—H3B···N2ii	0.93 (2)	2.05 (2)	2.964 (2)	167.6 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.88 (2)	2.11 (2)	2.979 (2)	165.7 (19)
N3—H3B⋯N2ii	0.93 (2)	2.05 (2)	2.964 (2)	167.6 (16)

Symmetry codes: (i) ; (ii) .