2-Phenyl-5-(p-tol-yl)-1,3,4-oxadiazole.

The title compound, C(15)H(12)N(2)O, adopts the expected near-planar geometry, the phenyl and tolyl rings being inclined relative to the oxadiazole ring by 3.8 (3) and 8.3 (2)°, respectively. This allows adjacent mol-ecules to pack in a parallel fashion and form stacking along [010] via π-π inter-actions [centroid-centroid distances = 3.629 (2) and 3.723 (2) Å]. Further inter-molecular inter-actions include C-H⋯π inter-actions and weak C-H⋯N hydrogen bonds, giving rise to a crossed herringbone packing motif.

Related literature

For synthesis of the starting material N′-benzoyl-4-methyl­benzohydrazide, see: Hua et al. (2009 ▶). For a review of synthetic routes to the title compound, see: Weaver (2004 ▶). For related structures, see: Kuznetsov et al. (1998 ▶); Franco et al. (2003 ▶); Reck et al. (2003 ▶).

Experimental

Crystal data

C15H12N2O

M = 236.27

Monoclinic,

a = 19.733 (5) Å

b = 5.1441 (12) Å

c = 12.436 (3) Å

β = 107.477 (6)°

V = 1204.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.20 × 0.04 × 0.02 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2010 ▶) T min = 0.984, T max = 0.998

7407 measured reflections

2256 independent reflections

1293 reflections with I > 2σ(I)

R int = 0.207

Refinement

R[F 2 > 2σ(F 2)] = 0.109

wR(F 2) = 0.307

S = 1.02

2256 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrystalClear (Rigaku, 2010 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023579/su2281sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023579/su2281Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023579/su2281Isup3.cml

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

C15H12N2O	F(000) = 496
Mr = 236.27	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2748 reflections
a = 19.733 (5) Å	θ = 3.3–28.2°
b = 5.1441 (12) Å	µ = 0.08 mm−1
c = 12.436 (3) Å	T = 93 K
β = 107.477 (6)°	Chip, colourless
V = 1204.1 (5) Å3	0.20 × 0.04 × 0.02 mm
Z = 4

Rigaku Mercury CCD diffractometer	2256 independent reflections
Radiation source: rotating anode	1293 reflections with I > 2σ(I)
confocal	Rint = 0.207
Detector resolution: 14.7059 pixels mm-1	θmax = 27.5°, θmin = 3.3°
ω and φ scans	h = −24→24
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010)	k = −3→6
Tmin = 0.984, Tmax = 0.998	l = −11→14
7407 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)] = 0.109	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.307	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1532P)2] where P = (Fo2 + 2Fc2)/3
2256 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.48 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	0.26886 (13)	0.5359 (5)	0.70037 (19)	0.0337 (8)
N1	0.24323 (17)	0.4502 (6)	0.5190 (3)	0.0374 (9)
N2	0.29187 (16)	0.6544 (6)	0.5435 (2)	0.0334 (9)
C1	0.2307 (2)	0.3862 (7)	0.6126 (3)	0.0322 (10)
C2	0.30560 (19)	0.6981 (7)	0.6502 (3)	0.0299 (10)
C3	0.18313 (19)	0.1875 (8)	0.6309 (3)	0.0306 (10)
C4	0.1822 (2)	0.1219 (7)	0.7391 (3)	0.0330 (10)
H4	0.2132	0.2077	0.8027	0.040*
C5	0.1364 (2)	−0.0672 (8)	0.7541 (3)	0.0354 (10)
H5	0.1369	−0.1109	0.8285	0.042*
C6	0.0898 (2)	−0.1957 (8)	0.6643 (3)	0.0344 (10)
C7	0.0919 (2)	−0.1274 (8)	0.5552 (3)	0.0413 (11)
H7	0.0606	−0.2120	0.4917	0.050*
C8	0.1378 (2)	0.0573 (8)	0.5385 (3)	0.0374 (11)
H8	0.1388	0.0967	0.4643	0.045*
C9	0.0394 (2)	−0.3978 (8)	0.6791 (3)	0.0421 (11)
H9A	0.0416	−0.4078	0.7588	0.063*
H9B	0.0524	−0.5665	0.6544	0.063*
H9C	−0.0090	−0.3520	0.6339	0.063*
C10	0.35306 (19)	0.8918 (7)	0.7193 (3)	0.0307 (10)
C11	0.3641 (2)	0.9055 (7)	0.8354 (3)	0.0368 (11)
H11	0.3400	0.7895	0.8708	0.044*
C12	0.4102 (2)	1.0888 (8)	0.8982 (3)	0.0400 (11)
H12	0.4191	1.0945	0.9776	0.048*
C13	0.4437 (2)	1.2640 (8)	0.8470 (3)	0.0392 (11)
H13	0.4743	1.3924	0.8910	0.047*
C14	0.4327 (2)	1.2533 (7)	0.7316 (3)	0.0347 (10)
H14	0.4565	1.3710	0.6964	0.042*
C15	0.3871 (2)	1.0705 (7)	0.6692 (3)	0.0344 (10)
H15	0.3785	1.0657	0.5898	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0369 (16)	0.0242 (16)	0.0432 (18)	−0.0030 (12)	0.0167 (13)	−0.0033 (11)
N1	0.041 (2)	0.032 (2)	0.042 (2)	0.0020 (17)	0.0165 (16)	0.0037 (14)
N2	0.042 (2)	0.035 (2)	0.0250 (19)	−0.0011 (16)	0.0129 (14)	−0.0061 (13)
C1	0.034 (2)	0.023 (2)	0.040 (2)	0.0001 (18)	0.0135 (17)	0.0024 (17)
C2	0.034 (2)	0.019 (2)	0.044 (2)	0.0064 (17)	0.0223 (18)	0.0073 (16)
C3	0.032 (2)	0.027 (2)	0.036 (2)	0.0054 (17)	0.0139 (16)	−0.0013 (16)
C4	0.035 (2)	0.032 (2)	0.035 (2)	0.0026 (18)	0.0156 (17)	0.0019 (16)
C5	0.039 (2)	0.032 (2)	0.036 (2)	0.0031 (19)	0.0132 (18)	−0.0024 (17)
C6	0.037 (2)	0.026 (2)	0.045 (3)	0.0041 (18)	0.0200 (18)	0.0008 (17)
C7	0.040 (3)	0.031 (3)	0.050 (3)	−0.002 (2)	0.0088 (19)	−0.0091 (18)
C8	0.043 (3)	0.035 (3)	0.033 (2)	0.001 (2)	0.0103 (18)	−0.0036 (17)
C9	0.039 (2)	0.035 (3)	0.052 (3)	0.003 (2)	0.013 (2)	−0.0038 (18)
C10	0.035 (2)	0.022 (2)	0.040 (2)	0.0086 (17)	0.0188 (18)	−0.0012 (16)
C11	0.046 (3)	0.027 (2)	0.043 (3)	0.005 (2)	0.0228 (19)	0.0003 (17)
C12	0.051 (3)	0.033 (3)	0.040 (3)	0.005 (2)	0.017 (2)	−0.0025 (18)
C13	0.042 (3)	0.032 (3)	0.044 (3)	0.000 (2)	0.0139 (19)	−0.0099 (18)
C14	0.038 (2)	0.030 (2)	0.035 (2)	−0.0008 (19)	0.0098 (17)	0.0056 (17)
C15	0.040 (2)	0.033 (2)	0.030 (2)	0.0092 (19)	0.0103 (17)	0.0068 (17)

O1—C1	1.363 (4)	C7—H7	0.9500
O1—C2	1.372 (4)	C8—H8	0.9500
N1—C1	1.304 (4)	C9—H9A	0.9800
N1—N2	1.393 (4)	C9—H9B	0.9800
N2—C2	1.293 (4)	C9—H9C	0.9800
C1—C3	1.451 (5)	C10—C15	1.391 (5)
C2—C10	1.458 (5)	C10—C11	1.396 (5)
C3—C4	1.394 (5)	C11—C12	1.379 (6)
C3—C8	1.397 (5)	C11—H11	0.9500
C4—C5	1.378 (5)	C12—C13	1.381 (5)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.383 (5)	C13—C14	1.386 (5)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.414 (5)	C14—C15	1.371 (5)
C6—C9	1.488 (5)	C14—H14	0.9500
C7—C8	1.371 (5)	C15—H15	0.9500
C1—O1—C2	102.7 (3)	C3—C8—H8	120.1
C1—N1—N2	107.3 (3)	C6—C9—H9A	109.5
C2—N2—N1	105.9 (3)	C6—C9—H9B	109.5
N1—C1—O1	111.4 (3)	H9A—C9—H9B	109.5
N1—C1—C3	128.5 (4)	C6—C9—H9C	109.5
O1—C1—C3	120.1 (3)	H9A—C9—H9C	109.5
N2—C2—O1	112.6 (3)	H9B—C9—H9C	109.5
N2—C2—C10	128.6 (3)	C15—C10—C11	118.9 (4)
O1—C2—C10	118.8 (3)	C15—C10—C2	119.9 (3)
C4—C3—C8	119.2 (4)	C11—C10—C2	121.1 (3)
C4—C3—C1	121.2 (4)	C12—C11—C10	119.5 (4)
C8—C3—C1	119.6 (3)	C12—C11—H11	120.3
C5—C4—C3	120.0 (4)	C10—C11—H11	120.3
C5—C4—H4	120.0	C11—C12—C13	120.7 (4)
C3—C4—H4	120.0	C11—C12—H12	119.6
C4—C5—C6	122.2 (3)	C13—C12—H12	119.6
C4—C5—H5	118.9	C12—C13—C14	120.3 (4)
C6—C5—H5	118.9	C12—C13—H13	119.9
C5—C6—C7	116.9 (4)	C14—C13—H13	119.9
C5—C6—C9	122.8 (3)	C15—C14—C13	119.0 (3)
C7—C6—C9	120.4 (4)	C15—C14—H14	120.5
C8—C7—C6	121.9 (4)	C13—C14—H14	120.5
C8—C7—H7	119.0	C14—C15—C10	121.5 (3)
C6—C7—H7	119.0	C14—C15—H15	119.2
C7—C8—C3	119.7 (3)	C10—C15—H15	119.2
C7—C8—H8	120.1
C1—N1—N2—C2	0.4 (4)	C5—C6—C7—C8	0.0 (6)
N2—N1—C1—O1	−0.4 (4)	C9—C6—C7—C8	−179.8 (4)
N2—N1—C1—C3	179.0 (4)	C6—C7—C8—C3	−1.4 (6)
C2—O1—C1—N1	0.3 (4)	C4—C3—C8—C7	1.7 (6)
C2—O1—C1—C3	−179.3 (3)	C1—C3—C8—C7	−178.9 (3)
N1—N2—C2—O1	−0.2 (4)	N2—C2—C10—C15	4.1 (6)
N1—N2—C2—C10	−179.9 (4)	O1—C2—C10—C15	−175.5 (3)
C1—O1—C2—N2	0.0 (4)	N2—C2—C10—C11	−177.2 (4)
C1—O1—C2—C10	179.7 (3)	O1—C2—C10—C11	3.2 (5)
N1—C1—C3—C4	172.1 (4)	C15—C10—C11—C12	−2.3 (5)
O1—C1—C3—C4	−8.5 (5)	C2—C10—C11—C12	179.0 (3)
N1—C1—C3—C8	−7.3 (6)	C10—C11—C12—C13	2.2 (6)
O1—C1—C3—C8	172.1 (3)	C11—C12—C13—C14	−1.8 (6)
C8—C3—C4—C5	−0.7 (5)	C12—C13—C14—C15	1.5 (6)
C1—C3—C4—C5	179.9 (3)	C13—C14—C15—C10	−1.7 (6)
C3—C4—C5—C6	−0.7 (6)	C11—C10—C15—C14	2.1 (5)
C4—C5—C6—C7	1.1 (6)	C2—C10—C15—C14	−179.2 (3)
C4—C5—C6—C9	−179.1 (3)

Cg1 and Cg2 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N2i	0.95	2.61	3.322 (4)	132.
C9—H9B···Cg1ii	0.98	2.80	3.731 (4)	158.
C14—H14···Cg2iii	0.95	2.99	3.783 (4)	141.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N2i	0.95	2.61	3.322 (4)	132
C9—H9B⋯Cg1ii	0.98	2.80	3.731 (4)	158
C14—H14⋯Cg2iii	0.95	2.99	3.783 (4)	141

Symmetry codes: (i) ; (ii) ; (iii) .