Centrosymmetric π-stacked dimers in 5-(2-acetyl­oxy­phenyl)-3-phenyl-1,2,4-oxa­diazo­le

In mol­ecules of the title compound, C₁₆H₁₂N₂O₃, the three independent rings are nearly coplanar; the mol­ecules are linked into centrosymmetric dimers by a π–π stacking interaction.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.055
• wR factor = 0.126
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.115
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

5-(2-Acetyloxyphenyl)-3-phenyl-1,2,4-oxadiazole

Crystal data

C16H12N2O3	F(000) = 584
Mr = 280.28	Dx = 1.418 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2875 reflections
a = 14.5489 (8) Å	θ = 3.3–27.5°
b = 5.4293 (3) Å	µ = 0.10 mm^−1
c = 17.2806 (13) Å	T = 120 K
β = 105.955 (2)°	Plate, colourless
V = 1312.42 (14) Å^3	0.20 × 0.08 × 0.01 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2875 independent reflections
Radiation source: rotating anode	1649 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.115
φ scans, and ω scans with κ offsets	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −16→18
Tmin = 0.951, Tmax = 0.999	k = −6→5
8160 measured reflections	l = −18→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0465P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2875 reflections	Δρmax = 0.26 e Å^−3
192 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.36315 (9)	0.1997 (3)	0.47966 (8)	0.0263 (4)
O52	0.40604 (9)	0.8256 (2)	0.63287 (8)	0.0239 (4)
O521	0.32320 (10)	0.5874 (3)	0.69702 (8)	0.0270 (4)
N2	0.26830 (12)	0.1909 (3)	0.42934 (10)	0.0280 (5)
N4	0.28702 (12)	0.5148 (3)	0.51459 (10)	0.0227 (4)
C3	0.22805 (14)	0.3803 (4)	0.45294 (12)	0.0230 (5)
C31	0.12611 (14)	0.4404 (4)	0.41766 (12)	0.0218 (5)
C32	0.08606 (15)	0.6498 (4)	0.44173 (14)	0.0314 (6)
C33	−0.01027 (16)	0.6980 (4)	0.41092 (14)	0.0355 (6)
C34	−0.06761 (16)	0.5400 (4)	0.35593 (13)	0.0313 (6)
C35	−0.02829 (15)	0.3340 (4)	0.33032 (13)	0.0314 (6)
C36	0.06807 (6)	0.28393 (16)	0.36106 (6)	0.0282 (5)
C5	0.36779 (6)	0.39670 (16)	0.52839 (6)	0.0215 (5)
C51	0.45964 (6)	0.44165 (16)	0.58771 (6)	0.0205 (5)
C52	0.47561 (6)	0.64254 (16)	0.63986 (6)	0.0226 (5)
C53	0.56304 (6)	0.68026 (16)	0.69527 (6)	0.0244 (5)
C54	0.63707 (16)	0.5166 (4)	0.69884 (13)	0.0283 (5)
C55	0.62340 (15)	0.3155 (4)	0.64745 (13)	0.0272 (5)
C56	0.53525 (14)	0.2775 (4)	0.59298 (12)	0.0245 (5)
C521	0.32925 (15)	0.7744 (4)	0.66144 (12)	0.0226 (5)
C522	0.25979 (15)	0.9807 (4)	0.64235 (13)	0.0270 (5)
H32	0.1252	0.7598	0.4795	0.038*
H33	−0.0372	0.8410	0.4277	0.043*
H34	−0.1341	0.5724	0.3356	0.038*
H35	−0.0675	0.2269	0.2916	0.038*
H36	0.0948	0.1420	0.3435	0.034*
H53	0.5723	0.8175	0.7307	0.029*
H54	0.6975	0.5422	0.7366	0.034*
H55	0.6745	0.2043	0.6497	0.033*
H56	0.5258	0.1377	0.5586	0.029*
H52A	0.2064	0.9463	0.6651	0.040*
H52B	0.2356	0.9984	0.5838	0.040*
H52C	0.2915	1.1336	0.6655	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0203 (8)	0.0266 (8)	0.0284 (9)	0.0028 (6)	0.0006 (7)	−0.0066 (6)
O52	0.0210 (8)	0.0198 (8)	0.0316 (9)	0.0006 (6)	0.0082 (7)	0.0013 (6)
O521	0.0284 (9)	0.0248 (9)	0.0268 (9)	−0.0014 (7)	0.0062 (7)	0.0024 (6)
N2	0.0197 (10)	0.0299 (11)	0.0300 (11)	0.0008 (8)	−0.0005 (8)	−0.0056 (8)
N4	0.0202 (10)	0.0228 (9)	0.0241 (10)	0.0008 (7)	0.0045 (8)	−0.0006 (7)
C3	0.0226 (12)	0.0226 (11)	0.0218 (12)	−0.0036 (9)	0.0030 (9)	0.0022 (9)
C31	0.0198 (11)	0.0225 (11)	0.0219 (12)	0.0002 (9)	0.0037 (9)	0.0024 (8)
C32	0.0244 (13)	0.0265 (13)	0.0375 (14)	−0.0010 (9)	−0.0013 (11)	−0.0017 (9)
C33	0.0257 (13)	0.0297 (14)	0.0465 (16)	0.0057 (10)	0.0020 (11)	−0.0004 (10)
C34	0.0201 (12)	0.0332 (13)	0.0348 (14)	0.0005 (10)	−0.0022 (10)	0.0087 (10)
C35	0.0239 (13)	0.0366 (14)	0.0285 (14)	−0.0059 (10)	−0.0013 (10)	−0.0007 (10)
C36	0.0265 (13)	0.0281 (12)	0.0288 (13)	−0.0013 (10)	0.0053 (10)	−0.0020 (9)
C5	0.0220 (12)	0.0203 (11)	0.0223 (12)	0.0007 (9)	0.0063 (9)	0.0026 (9)
C51	0.0171 (11)	0.0220 (11)	0.0214 (11)	−0.0015 (9)	0.0033 (9)	0.0040 (8)
C52	0.0179 (12)	0.0229 (11)	0.0270 (12)	0.0011 (8)	0.0063 (10)	0.0036 (9)
C53	0.0218 (12)	0.0250 (12)	0.0250 (12)	−0.0051 (9)	0.0041 (10)	−0.0017 (9)
C54	0.0189 (12)	0.0344 (13)	0.0279 (13)	−0.0011 (10)	0.0005 (10)	0.0024 (10)
C55	0.0208 (12)	0.0296 (12)	0.0305 (13)	0.0043 (9)	0.0055 (10)	0.0056 (9)
C56	0.0230 (12)	0.0240 (12)	0.0259 (12)	0.0016 (9)	0.0057 (10)	0.0024 (9)
C521	0.0233 (12)	0.0232 (11)	0.0191 (11)	−0.0017 (9)	0.0023 (9)	−0.0040 (9)
C522	0.0259 (13)	0.0233 (12)	0.0312 (13)	0.0015 (9)	0.0069 (10)	−0.0012 (9)

Geometric parameters (Å, º)

O1—N2	1.415 (2)	C35—H35	0.95
N2—C3	1.303 (3)	C36—H36	0.95
C3—N4	1.379 (3)	C5—C51	1.4639 (14)
N4—C5	1.302 (2)	C51—C52	1.3931 (13)
C5—O1	1.351 (2)	C51—C56	1.399 (2)
O52—C521	1.368 (2)	C52—C53	1.3811 (14)
O52—C52	1.400 (2)	C53—C54	1.384 (2)
O521—C521	1.203 (2)	C53—H53	0.95
C3—C31	1.477 (3)	C54—C55	1.387 (3)
C31—C36	1.392 (2)	C54—H54	0.95
C31—C32	1.392 (3)	C55—C56	1.382 (3)
C32—C33	1.381 (3)	C55—H55	0.95
C32—H32	0.95	C56—H56	0.95
C33—C34	1.378 (3)	C521—C522	1.484 (3)
C33—H33	0.95	C522—H52A	0.98
C34—C35	1.383 (3)	C522—H52B	0.98
C34—H34	0.95	C522—H52C	0.98
C35—C36	1.383 (2)
C5—O1—N2	106.44 (12)	C52—C51—C56	117.93 (10)
O1—N2—C3	103.13 (15)	C52—C51—C5	122.78 (8)
N2—C3—N4	114.97 (18)	C56—C51—C5	119.29 (10)
C3—N4—C5	102.65 (14)	C53—C52—C51	121.51 (8)
N4—C5—O1	112.81 (11)	C53—C52—O52	117.44 (7)
C521—O52—C52	117.87 (13)	C51—C52—O52	120.80 (7)
N2—C3—C31	122.14 (18)	C52—C53—C54	119.52 (10)
N4—C3—C31	122.86 (18)	C52—C53—H53	120.2
C36—C31—C32	119.04 (17)	C54—C53—H53	120.2
C36—C31—C3	120.10 (17)	C53—C54—C55	120.26 (19)
C32—C31—C3	120.84 (18)	C53—C54—H54	119.9
C33—C32—C31	120.3 (2)	C55—C54—H54	119.9
C33—C32—H32	119.9	C56—C55—C54	119.8 (2)
C31—C32—H32	119.9	C56—C55—H55	120.1
C34—C33—C32	120.4 (2)	C54—C55—H55	120.1
C34—C33—H33	119.8	C55—C56—C51	120.99 (18)
C32—C33—H33	119.8	C55—C56—H56	119.5
C33—C34—C35	119.9 (2)	C51—C56—H56	119.5
C33—C34—H34	120.0	O521—C521—O52	122.53 (18)
C35—C34—H34	120.0	O521—C521—C522	127.57 (19)
C34—C35—C36	120.07 (19)	O52—C521—C522	109.90 (17)
C34—C35—H35	120.0	C521—C522—H52A	109.5
C36—C35—H35	120.0	C521—C522—H52B	109.5
C35—C36—C31	120.33 (14)	H52A—C522—H52B	109.5
C35—C36—H36	119.8	C521—C522—H52C	109.5
C31—C36—H36	119.8	H52A—C522—H52C	109.5
N4—C5—C51	130.57 (8)	H52B—C522—H52C	109.5
O1—C5—C51	116.61 (7)
C5—O1—N2—C3	0.30 (19)	N2—O1—C5—C51	178.82 (9)
O1—N2—C3—N4	−0.2 (2)	N4—C5—C51—C52	−3.31 (11)
O1—N2—C3—C31	−178.40 (17)	O1—C5—C51—C52	177.72 (8)
C5—N4—C3—N2	0.0 (2)	N4—C5—C51—C56	176.68 (16)
C5—N4—C3—C31	178.20 (16)	O1—C5—C51—C56	−2.29 (12)
N2—C3—C31—C36	4.3 (3)	C56—C51—C52—C53	−0.02 (10)
N4—C3—C31—C36	−173.74 (17)	C5—C51—C52—C53	180.0
N2—C3—C31—C32	−177.3 (2)	C56—C51—C52—O52	174.13 (14)
N4—C3—C31—C32	4.6 (3)	C5—C51—C52—O52	−5.88 (8)
C36—C31—C32—C33	1.3 (3)	C521—O52—C52—C53	−108.76 (13)
C3—C31—C32—C33	−177.1 (2)	C521—O52—C52—C51	76.87 (15)
C31—C32—C33—C34	−0.2 (3)	C51—C52—C53—C54	0.64 (11)
C32—C33—C34—C35	−1.1 (3)	O52—C52—C53—C54	−173.69 (15)
C33—C34—C35—C36	1.3 (3)	C52—C53—C54—C55	−0.4 (2)
C34—C35—C36—C31	−0.2 (3)	C53—C54—C55—C56	−0.6 (3)
C32—C31—C36—C35	−1.1 (3)	C54—C55—C56—C51	1.2 (3)
C3—C31—C36—C35	177.32 (17)	C52—C51—C56—C55	−0.9 (2)
C3—N4—C5—O1	0.22 (17)	C5—C51—C56—C55	179.10 (14)
C3—N4—C5—C51	−178.79 (9)	C52—O52—C521—O521	5.5 (3)
N2—O1—C5—N4	−0.34 (17)	C52—O52—C521—C522	−175.09 (14)