1-[2-(4-Chloro-phen-yl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone.

In the title compound, C(16)H(14)ClN(3)O(2), the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π-π [centroid-centroid distance = 3.7311 (6) Å] and C-H⋯π inter-actions are observed.

Related literature

For the biological activity of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazo­line ring systems, see: Rakesh & Prabhakar (2009 ▶); Priya et al. (2007 ▶); Bhatia & Gupta (2011 ▶); Vijesh et al. (2011 ▶); Galil & Amr (2000 ▶). For related structures, see: Yehye et al. (2010 ▶); Ono et al. (2009 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14ClN3O2

M = 315.75

Triclinic,

a = 5.8623 (2) Å

b = 10.9912 (5) Å

c = 12.2815 (5) Å

α = 68.214 (1)°

β = 84.707 (1)°

γ = 87.623 (1)°

V = 731.67 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.40 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.899, T max = 0.962

19562 measured reflections

5301 independent reflections

4768 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.116

S = 1.02

5301 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023100/hb6803sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023100/hb6803Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023100/hb6803Isup3.cml

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

C16H14ClN3O2	Z = 2
Mr = 315.75	F(000) = 328
Triclinic, P1	Dx = 1.433 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8623 (2) Å	Cell parameters from 9976 reflections
b = 10.9912 (5) Å	θ = 3.1–32.6°
c = 12.2815 (5) Å	µ = 0.27 mm−1
α = 68.214 (1)°	T = 100 K
β = 84.707 (1)°	Block, yellow
γ = 87.623 (1)°	0.40 × 0.22 × 0.14 mm
V = 731.67 (5) Å3

Bruker SMART APEXII DUO CCD diffractometer	5301 independent reflections
Radiation source: fine-focus sealed tube	4768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 32.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.899, Tmax = 0.962	k = −16→16
19562 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.3111P] where P = (Fo2 + 2Fc2)/3
5301 reflections	(Δ/σ)max = 0.003
195 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.93968 (5)	0.44230 (2)	1.24269 (2)	0.02345 (8)
O1	0.75357 (12)	0.84198 (7)	0.70235 (6)	0.01543 (13)
O2	0.71195 (14)	1.07742 (8)	0.89561 (7)	0.02114 (16)
N1	0.14662 (17)	0.82200 (10)	0.47108 (8)	0.02164 (14)
N2	0.42483 (14)	0.94931 (8)	0.72117 (7)	0.01425 (14)
N3	0.57912 (14)	0.96760 (8)	0.79406 (7)	0.01478 (15)
C1	0.56078 (19)	0.72732 (11)	0.56195 (10)	0.0218 (2)
H1A	0.7044	0.6960	0.5920	0.026*
C2	0.4694 (2)	0.67544 (11)	0.49036 (10)	0.0221 (2)
H2A	0.5479	0.6079	0.4709	0.026*
C3	0.26192 (19)	0.72257 (11)	0.44693 (9)	0.02164 (14)
C4	0.23766 (16)	0.87227 (10)	0.54253 (9)	0.01640 (17)
H4A	0.1587	0.9408	0.5601	0.020*
C5	0.44533 (16)	0.82564 (9)	0.59111 (8)	0.01382 (16)
C6	0.53469 (15)	0.87669 (9)	0.67240 (8)	0.01324 (15)
C7	0.79357 (15)	0.89356 (9)	0.79165 (8)	0.01384 (16)
H7A	0.9281	0.9536	0.7659	0.017*
C8	0.82979 (15)	0.78264 (9)	0.90601 (8)	0.01289 (15)
C9	1.02946 (15)	0.77444 (10)	0.96167 (8)	0.01520 (16)
H9A	1.1425	0.8404	0.9281	0.018*
C10	1.06480 (16)	0.67008 (10)	1.06622 (9)	0.01629 (17)
H10A	1.2006	0.6646	1.1045	0.020*
C11	0.89815 (16)	0.57433 (9)	1.11339 (8)	0.01493 (16)
C12	0.69506 (17)	0.58158 (10)	1.06022 (9)	0.01712 (17)
H12A	0.5814	0.5160	1.0944	0.021*
C13	0.66228 (16)	0.68659 (10)	0.95626 (9)	0.01628 (17)
H13A	0.5248	0.6931	0.9191	0.020*
C14	0.1547 (3)	0.66352 (15)	0.37211 (12)	0.0388 (3)
H14A	0.0095	0.6224	0.4122	0.058*
H14B	0.2585	0.5973	0.3588	0.058*
H14C	0.1261	0.7322	0.2964	0.058*
C15	0.55511 (17)	1.06142 (9)	0.84241 (8)	0.01540 (16)
C16	0.33496 (18)	1.13830 (10)	0.82619 (10)	0.02050 (19)
H16A	0.3508	1.2156	0.8465	0.031*
H16B	0.2109	1.0833	0.8775	0.031*
H16C	0.2994	1.1662	0.7440	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.02985 (14)	0.01791 (12)	0.01908 (12)	0.00100 (9)	−0.00754 (9)	−0.00162 (9)
O1	0.0136 (3)	0.0209 (3)	0.0149 (3)	0.0038 (2)	−0.0041 (2)	−0.0101 (3)
O2	0.0226 (3)	0.0219 (4)	0.0229 (4)	−0.0025 (3)	−0.0045 (3)	−0.0119 (3)
N1	0.0243 (3)	0.0241 (3)	0.0164 (3)	−0.0039 (2)	−0.0053 (2)	−0.0062 (2)
N2	0.0145 (3)	0.0157 (3)	0.0139 (3)	0.0009 (3)	−0.0034 (2)	−0.0065 (3)
N3	0.0151 (3)	0.0162 (3)	0.0158 (3)	0.0032 (3)	−0.0046 (3)	−0.0087 (3)
C1	0.0233 (5)	0.0244 (5)	0.0237 (5)	0.0070 (4)	−0.0089 (4)	−0.0151 (4)
C2	0.0275 (5)	0.0232 (5)	0.0224 (5)	0.0061 (4)	−0.0094 (4)	−0.0153 (4)
C3	0.0243 (3)	0.0241 (3)	0.0164 (3)	−0.0039 (2)	−0.0053 (2)	−0.0062 (2)
C4	0.0162 (4)	0.0185 (4)	0.0146 (4)	0.0005 (3)	−0.0031 (3)	−0.0059 (3)
C5	0.0153 (4)	0.0147 (4)	0.0117 (4)	−0.0003 (3)	−0.0019 (3)	−0.0051 (3)
C6	0.0127 (3)	0.0143 (4)	0.0121 (4)	0.0008 (3)	−0.0021 (3)	−0.0040 (3)
C7	0.0133 (3)	0.0160 (4)	0.0136 (4)	0.0010 (3)	−0.0027 (3)	−0.0068 (3)
C8	0.0123 (3)	0.0144 (4)	0.0133 (4)	0.0008 (3)	−0.0023 (3)	−0.0066 (3)
C9	0.0121 (3)	0.0190 (4)	0.0151 (4)	−0.0012 (3)	−0.0017 (3)	−0.0067 (3)
C10	0.0133 (4)	0.0200 (4)	0.0159 (4)	0.0006 (3)	−0.0034 (3)	−0.0065 (3)
C11	0.0174 (4)	0.0140 (4)	0.0141 (4)	0.0022 (3)	−0.0030 (3)	−0.0058 (3)
C12	0.0183 (4)	0.0147 (4)	0.0186 (4)	−0.0027 (3)	−0.0037 (3)	−0.0057 (3)
C13	0.0147 (4)	0.0166 (4)	0.0180 (4)	−0.0020 (3)	−0.0046 (3)	−0.0059 (3)
C14	0.0595 (9)	0.0387 (7)	0.0213 (5)	−0.0216 (7)	−0.0116 (5)	−0.0106 (5)
C15	0.0191 (4)	0.0131 (4)	0.0144 (4)	−0.0012 (3)	0.0001 (3)	−0.0059 (3)
C16	0.0223 (4)	0.0185 (4)	0.0235 (5)	0.0051 (3)	−0.0026 (4)	−0.0114 (4)

Cl1—C11	1.7373 (10)	C7—C8	1.5055 (13)
O1—C6	1.3673 (11)	C7—H7A	1.0000
O1—C7	1.4489 (11)	C8—C9	1.3923 (12)
O2—C15	1.2300 (12)	C8—C13	1.3966 (13)
N1—C4	1.3531 (13)	C9—C10	1.3941 (14)
N1—C3	1.3716 (16)	C9—H9A	0.9500
N2—C6	1.2851 (12)	C10—C11	1.3878 (14)
N2—N3	1.3993 (11)	C10—H10A	0.9500
N3—C15	1.3648 (12)	C11—C12	1.3954 (13)
N3—C7	1.4730 (12)	C12—C13	1.3900 (14)
C1—C2	1.3674 (14)	C12—H12A	0.9500
C1—C5	1.3914 (14)	C13—H13A	0.9500
C1—H1A	0.9500	C14—H14A	0.9800
C2—C3	1.3764 (15)	C14—H14B	0.9800
C2—H2A	0.9500	C14—H14C	0.9800
C3—C14	1.4979 (16)	C15—C16	1.5005 (14)
C4—C5	1.3986 (13)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.4569 (13)	C16—H16C	0.9800
C6—O1—C7	106.85 (7)	C13—C8—C7	119.68 (8)
C4—N1—C3	118.61 (9)	C8—C9—C10	120.49 (9)
C6—N2—N3	104.34 (8)	C8—C9—H9A	119.8
C15—N3—N2	124.21 (8)	C10—C9—H9A	119.8
C15—N3—C7	123.06 (8)	C11—C10—C9	118.84 (9)
N2—N3—C7	111.51 (7)	C11—C10—H10A	120.6
C2—C1—C5	120.58 (10)	C9—C10—H10A	120.6
C2—C1—H1A	119.7	C10—C11—C12	121.68 (9)
C5—C1—H1A	119.7	C10—C11—Cl1	119.71 (7)
C1—C2—C3	118.95 (10)	C12—C11—Cl1	118.60 (7)
C1—C2—H2A	120.5	C13—C12—C11	118.69 (9)
C3—C2—H2A	120.5	C13—C12—H12A	120.7
N1—C3—C2	122.02 (10)	C11—C12—H12A	120.7
N1—C3—C14	118.22 (11)	C12—C13—C8	120.56 (9)
C2—C3—C14	119.75 (12)	C12—C13—H13A	119.7
N1—C4—C5	121.54 (9)	C8—C13—H13A	119.7
N1—C4—H4A	119.2	C3—C14—H14A	109.5
C5—C4—H4A	119.2	C3—C14—H14B	109.5
C1—C5—C4	118.25 (9)	H14A—C14—H14B	109.5
C1—C5—C6	121.10 (9)	C3—C14—H14C	109.5
C4—C5—C6	120.63 (8)	H14A—C14—H14C	109.5
N2—C6—O1	116.52 (8)	H14B—C14—H14C	109.5
N2—C6—C5	126.02 (8)	O2—C15—N3	118.81 (9)
O1—C6—C5	117.44 (8)	O2—C15—C16	124.60 (9)
O1—C7—N3	100.48 (7)	N3—C15—C16	116.59 (9)
O1—C7—C8	109.92 (7)	C15—C16—H16A	109.5
N3—C7—C8	113.89 (8)	C15—C16—H16B	109.5
O1—C7—H7A	110.7	H16A—C16—H16B	109.5
N3—C7—H7A	110.7	C15—C16—H16C	109.5
C8—C7—H7A	110.7	H16A—C16—H16C	109.5
C9—C8—C13	119.71 (9)	H16B—C16—H16C	109.5
C9—C8—C7	120.61 (8)
C6—N2—N3—C15	164.62 (9)	C15—N3—C7—O1	−162.77 (8)
C6—N2—N3—C7	−3.06 (10)	N2—N3—C7—O1	5.08 (10)
C5—C1—C2—C3	0.40 (18)	C15—N3—C7—C8	79.78 (11)
C4—N1—C3—C2	−1.88 (16)	N2—N3—C7—C8	−112.37 (9)
C4—N1—C3—C14	177.33 (10)	O1—C7—C8—C9	123.04 (9)
C1—C2—C3—N1	1.52 (18)	N3—C7—C8—C9	−125.11 (9)
C1—C2—C3—C14	−177.68 (11)	O1—C7—C8—C13	−56.48 (11)
C3—N1—C4—C5	0.33 (15)	N3—C7—C8—C13	55.37 (11)
C2—C1—C5—C4	−1.86 (16)	C13—C8—C9—C10	0.93 (14)
C2—C1—C5—C6	176.61 (10)	C7—C8—C9—C10	−178.58 (8)
N1—C4—C5—C1	1.50 (15)	C8—C9—C10—C11	0.34 (14)
N1—C4—C5—C6	−176.97 (9)	C9—C10—C11—C12	−1.41 (15)
N3—N2—C6—O1	−0.56 (11)	C9—C10—C11—Cl1	179.25 (7)
N3—N2—C6—C5	177.71 (9)	C10—C11—C12—C13	1.16 (15)
C7—O1—C6—N2	3.92 (11)	Cl1—C11—C12—C13	−179.50 (8)
C7—O1—C6—C5	−174.50 (8)	C11—C12—C13—C8	0.16 (15)
C1—C5—C6—N2	−166.88 (10)	C9—C8—C13—C12	−1.19 (15)
C4—C5—C6—N2	11.55 (15)	C7—C8—C13—C12	178.33 (9)
C1—C5—C6—O1	11.37 (14)	N2—N3—C15—O2	−172.90 (9)
C4—C5—C6—O1	−170.20 (8)	C7—N3—C15—O2	−6.60 (14)
C6—O1—C7—N3	−5.07 (9)	N2—N3—C15—C16	7.16 (14)
C6—O1—C7—C8	115.27 (8)	C7—N3—C15—C16	173.46 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···Cg3i	0.98	2.65	3.4360 (13)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg3i	0.98	2.65	3.4360 (13)	138

Symmetry code: (i) .