5-Phenyl-1,3,4-oxadiazol-2-amine.

In the title complex, C(8)H(7)N(3)O, the C-O [1.369 (2) and 1.364 (3) Å] and C=N [1.285 (3) and 1.289 (3) Å] bond lengths in the oxadiazole ring are each almost identical within systematic errors, although different substituents are attached to the ring. The phenyl ring is inclined to the planar oxadiazole ring [r.m.s. deviation 0.002 Å] by 13.42 (18)°. In the crystal, molecules are linked via N-H⋯N hydrogen bonds, forming double-stranded chains propagating along [010].

Related literature

For background to 5-phenyl-1,3,4-oxadiazol-2-amines and the synthesis of the title compound, see: Bachwani et al. (2011 ▶); Lv et al. (2010 ▶); Tang et al. (2007 ▶).

Experimental

Crystal data

C8H7N3O

M = 161.17

Monoclinic,

a = 11.194 (3) Å

b = 5.8990 (5) Å

c = 15.034 (5) Å

β = 130.193 (18)°

V = 758.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 291 K

0.26 × 0.24 × 0.22 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.851, T max = 1.000

2912 measured reflections

1551 independent reflections

877 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.137

S = 1.02

1551 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040640/im2386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040640/im2386Isup2.hkl

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

C8H7N3O	F(000) = 336
Mr = 161.17	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 11.194 (3) Å	Cell parameters from 656 reflections
b = 5.8990 (5) Å	θ = 3.5–26.3°
c = 15.034 (5) Å	µ = 0.10 mm−1
β = 130.193 (18)°	T = 291 K
V = 758.3 (3) Å3	Prism, colourless
Z = 4	0.26 × 0.24 × 0.22 mm

Agilent Xcalibur Eos Gemini diffractometer	1551 independent reflections
Radiation source: Enhance (Mo) X-ray Source	877 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 16.2312 pixels mm-1	θmax = 26.4°, θmin = 3.6°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −4→7
Tmin = 0.851, Tmax = 1.000	l = −18→17
2912 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
1551 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.15541 (17)	0.6145 (2)	0.02276 (13)	0.0495 (5)
N1	−0.2177 (2)	0.2637 (3)	−0.04164 (18)	0.0617 (7)
N2	−0.3435 (2)	0.4062 (3)	−0.12624 (17)	0.0594 (7)
N3	−0.3795 (2)	0.8025 (3)	−0.12550 (17)	0.0622 (7)
H3A	−0.4628	0.8128	−0.2012	0.075*
H3B	−0.3161	0.9341	−0.0922	0.075*
C1	0.1056 (3)	0.1191 (4)	0.1680 (2)	0.0624 (8)
H1	0.0506	0.0125	0.1084	0.075*
C2	0.2512 (3)	0.0674 (4)	0.2723 (3)	0.0683 (9)
H2	0.2942	−0.0749	0.2825	0.082*
C3	0.3329 (3)	0.2221 (5)	0.3606 (2)	0.0714 (9)
H3	0.4308	0.1850	0.4303	0.086*
C4	0.2704 (3)	0.4311 (5)	0.3463 (2)	0.0720 (9)
H4	0.3259	0.5365	0.4065	0.086*
C5	0.1250 (3)	0.4866 (4)	0.2428 (2)	0.0578 (8)
H5	0.0828	0.6292	0.2336	0.069*
C6	0.0423 (3)	0.3320 (4)	0.1532 (2)	0.0457 (6)
C7	−0.1115 (3)	0.3912 (4)	0.0434 (2)	0.0450 (6)
C8	−0.3014 (3)	0.6083 (4)	−0.0839 (2)	0.0477 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0394 (10)	0.0366 (9)	0.0426 (9)	−0.0023 (7)	0.0129 (8)	−0.0024 (7)
N1	0.0457 (13)	0.0409 (11)	0.0551 (13)	−0.0007 (10)	0.0129 (11)	−0.0039 (10)
N2	0.0413 (12)	0.0417 (12)	0.0529 (13)	−0.0017 (10)	0.0112 (11)	−0.0038 (10)
N3	0.0462 (13)	0.0409 (12)	0.0514 (13)	0.0025 (10)	0.0097 (11)	0.0036 (10)
C1	0.0511 (17)	0.0476 (15)	0.0623 (17)	−0.0008 (13)	0.0247 (15)	−0.0049 (13)
C2	0.0508 (17)	0.0531 (16)	0.0730 (19)	0.0128 (14)	0.0273 (16)	0.0128 (14)
C3	0.0463 (16)	0.075 (2)	0.0537 (18)	0.0022 (15)	0.0143 (14)	0.0111 (15)
C4	0.0611 (19)	0.067 (2)	0.0468 (16)	−0.0069 (16)	0.0164 (15)	−0.0053 (14)
C5	0.0522 (17)	0.0457 (14)	0.0529 (16)	0.0005 (12)	0.0236 (15)	−0.0019 (12)
C6	0.0391 (14)	0.0415 (13)	0.0467 (14)	0.0012 (11)	0.0232 (12)	0.0037 (11)
C7	0.0404 (14)	0.0330 (12)	0.0487 (14)	−0.0002 (11)	0.0229 (12)	0.0003 (11)
C8	0.0365 (14)	0.0447 (14)	0.0422 (13)	−0.0044 (12)	0.0164 (12)	−0.0025 (12)

O1—C7	1.369 (2)	C1—C6	1.387 (3)
O1—C8	1.364 (3)	C2—H2	0.9300
N1—N2	1.413 (3)	C2—C3	1.366 (4)
N1—C7	1.285 (3)	C3—H3	0.9300
N2—C8	1.289 (3)	C3—C4	1.364 (4)
N3—H3A	0.8936	C4—H4	0.9300
N3—H3B	0.9476	C4—C5	1.382 (3)
N3—C8	1.328 (3)	C5—H5	0.9300
C1—H1	0.9300	C5—C6	1.376 (3)
C1—C2	1.382 (3)	C6—C7	1.464 (3)
C8—O1—C7	102.89 (16)	C3—C4—H4	119.9
C7—N1—N2	106.97 (18)	C3—C4—C5	120.2 (2)
C8—N2—N1	105.75 (18)	C5—C4—H4	119.9
H3A—N3—H3B	115.3	C4—C5—H5	119.8
C8—N3—H3A	119.2	C6—C5—C4	120.3 (2)
C8—N3—H3B	114.6	C6—C5—H5	119.8
C2—C1—H1	120.4	C1—C6—C7	120.3 (2)
C2—C1—C6	119.2 (2)	C5—C6—C1	119.5 (2)
C6—C1—H1	120.4	C5—C6—C7	120.3 (2)
C1—C2—H2	119.5	O1—C7—C6	118.30 (19)
C3—C2—C1	121.0 (2)	N1—C7—O1	111.77 (19)
C3—C2—H2	119.5	N1—C7—C6	129.9 (2)
C2—C3—H3	120.1	N2—C8—O1	112.6 (2)
C4—C3—C2	119.8 (3)	N2—C8—N3	130.2 (2)
C4—C3—H3	120.1	N3—C8—O1	117.12 (19)
N1—N2—C8—O1	0.7 (3)	C4—C5—C6—C1	0.5 (4)
N1—N2—C8—N3	−176.1 (3)	C4—C5—C6—C7	−179.8 (2)
N2—N1—C7—O1	−0.4 (3)	C5—C6—C7—O1	13.9 (3)
N2—N1—C7—C6	−180.0 (2)	C5—C6—C7—N1	−166.5 (3)
C1—C2—C3—C4	0.1 (5)	C6—C1—C2—C3	0.3 (4)
C1—C6—C7—O1	−166.5 (2)	C7—O1—C8—N2	−0.9 (3)
C1—C6—C7—N1	13.1 (4)	C7—O1—C8—N3	176.4 (2)
C2—C1—C6—C5	−0.5 (4)	C7—N1—N2—C8	−0.2 (3)
C2—C1—C6—C7	179.8 (3)	C8—O1—C7—N1	0.8 (3)
C2—C3—C4—C5	−0.1 (5)	C8—O1—C7—C6	−179.6 (2)
C3—C4—C5—C6	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2i	0.89	2.12	2.997 (3)	169
N3—H3B···N1ii	0.95	2.12	3.054 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2i	0.89	2.12	2.997 (3)	169
N3—H3B⋯N1ii	0.95	2.12	3.054 (3)	168

Symmetry codes: (i) ; (ii) .