3-[5-(Pyridin-4-yl)-1,3,4-oxa­diazol-2-yl]-4H-chromen-4-one

In the title mol­ecule, C₁₆H₉N₃O₃, the plane of oxa­diazole ring is almost coplanar with attached pyridine ring and chromenyl ring system, forming dihedral angles of 2.37 (3) and 6.71 (2)°, respectively. In the crystal, a pair of C—H...O and C—H...N hydrogen-bond inter­actions lead to the formation of dimers, which are linked together into [100] chains.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.112
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.107 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          16 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-4H-chromen-4-one

Crystal data

C16H9N3O3	F(000) = 600
Mr = 291.26	Dx = 1.518 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9683 reflections
a = 6.7439 (2) Å	θ = 2.2–28.3°
b = 10.8441 (3) Å	µ = 0.11 mm^−1
c = 17.7415 (6) Å	T = 223 K
β = 100.7317 (13)°	Block, yellow
V = 1274.77 (7) Å^3	0.13 × 0.12 × 0.09 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	3188 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.986, Tmax = 0.990	k = −14→14
38727 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.5495P] where P = (Fo^2 + 2Fc^2)/3
3188 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	Uiso*/Ueq
C1	−0.1618 (2)	0.24444 (14)	0.01388 (8)	0.0301 (3)
O1	−0.31711 (18)	0.22005 (13)	0.03664 (8)	0.0540 (4)
C2	−0.1492 (2)	0.34564 (14)	−0.04011 (8)	0.0282 (3)
C3	−0.3161 (2)	0.42116 (15)	−0.06691 (9)	0.0361 (4)
H3	−0.4382	0.4078	−0.0498	0.043*
C4	−0.3024 (3)	0.51438 (16)	−0.11791 (10)	0.0421 (4)
H4	−0.4145	0.5652	−0.1353	0.050*
C5	−0.1229 (3)	0.53389 (16)	−0.14399 (10)	0.0417 (4)
H5	−0.1156	0.5972	−0.1796	0.050*
C6	0.0439 (3)	0.46201 (15)	−0.11854 (9)	0.0373 (4)
H6	0.1654	0.4756	−0.1360	0.045*
C7	0.0282 (2)	0.36883 (13)	−0.06637 (8)	0.0287 (3)
O2	0.19977 (16)	0.29944 (10)	−0.04199 (6)	0.0342 (3)
C8	0.1928 (2)	0.20816 (14)	0.00834 (9)	0.0299 (3)
H8	0.3118	0.1630	0.0251	0.036*
C9	0.0281 (2)	0.17627 (13)	0.03673 (8)	0.0254 (3)
C10	0.0427 (2)	0.07610 (13)	0.09176 (8)	0.0266 (3)
O3	0.21616 (14)	0.00778 (9)	0.10556 (5)	0.0247 (2)
C11	0.1816 (2)	−0.07098 (13)	0.16119 (8)	0.0265 (3)
N1	0.0061 (2)	−0.05671 (13)	0.17827 (9)	0.0408 (3)
N2	−0.0862 (2)	0.04037 (13)	0.13246 (9)	0.0411 (4)
C12	0.3365 (2)	−0.15833 (13)	0.19546 (8)	0.0257 (3)
C13	0.5241 (2)	−0.16371 (13)	0.17404 (8)	0.0285 (3)
H13	0.5565	−0.1107	0.1362	0.034*
C14	0.6622 (2)	−0.24943 (14)	0.21005 (9)	0.0319 (3)
H14	0.7887	−0.2532	0.1951	0.038*
N3	0.6283 (2)	−0.32645 (12)	0.26410 (8)	0.0350 (3)
C15	0.4466 (2)	−0.31961 (15)	0.28450 (9)	0.0363 (4)
H15	0.4194	−0.3732	0.3230	0.044*
C16	0.2980 (2)	−0.23835 (14)	0.25208 (9)	0.0320 (3)
H16	0.1727	−0.2371	0.2680	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0233 (7)	0.0345 (8)	0.0325 (7)	0.0026 (6)	0.0051 (6)	0.0007 (6)
O1	0.0276 (6)	0.0684 (9)	0.0695 (9)	0.0109 (6)	0.0183 (6)	0.0293 (7)
C2	0.0285 (7)	0.0289 (7)	0.0260 (7)	0.0024 (6)	0.0014 (5)	−0.0017 (6)
C3	0.0293 (8)	0.0385 (9)	0.0381 (8)	0.0055 (6)	0.0002 (6)	−0.0002 (7)
C4	0.0415 (9)	0.0385 (9)	0.0411 (9)	0.0092 (7)	−0.0056 (7)	0.0044 (7)
C5	0.0524 (10)	0.0362 (9)	0.0337 (8)	0.0030 (8)	0.0007 (7)	0.0089 (7)
C6	0.0413 (9)	0.0365 (8)	0.0343 (8)	−0.0002 (7)	0.0079 (7)	0.0042 (7)
C7	0.0295 (7)	0.0287 (7)	0.0268 (7)	0.0024 (6)	0.0027 (6)	−0.0012 (6)
O2	0.0285 (5)	0.0367 (6)	0.0390 (6)	0.0048 (4)	0.0109 (4)	0.0109 (5)
C8	0.0260 (7)	0.0306 (7)	0.0332 (7)	0.0042 (6)	0.0060 (6)	0.0041 (6)
C9	0.0243 (7)	0.0245 (7)	0.0269 (7)	0.0002 (5)	0.0036 (5)	−0.0011 (5)
C10	0.0219 (7)	0.0262 (7)	0.0318 (7)	0.0015 (5)	0.0057 (6)	−0.0016 (6)
O3	0.0234 (5)	0.0253 (5)	0.0257 (5)	0.0014 (4)	0.0050 (4)	0.0013 (4)
C11	0.0275 (7)	0.0241 (7)	0.0285 (7)	−0.0029 (5)	0.0066 (6)	0.0007 (6)
N1	0.0312 (7)	0.0402 (8)	0.0542 (9)	0.0060 (6)	0.0163 (6)	0.0192 (7)
N2	0.0323 (7)	0.0403 (8)	0.0543 (9)	0.0080 (6)	0.0171 (6)	0.0183 (7)
C12	0.0268 (7)	0.0235 (7)	0.0261 (7)	−0.0020 (5)	0.0027 (5)	−0.0020 (5)
C13	0.0290 (7)	0.0269 (7)	0.0305 (7)	−0.0017 (6)	0.0073 (6)	0.0013 (6)
C14	0.0261 (7)	0.0327 (8)	0.0367 (8)	−0.0013 (6)	0.0055 (6)	−0.0023 (6)
N3	0.0305 (7)	0.0331 (7)	0.0402 (7)	0.0027 (5)	0.0037 (6)	0.0049 (6)
C15	0.0360 (8)	0.0352 (8)	0.0377 (8)	0.0000 (7)	0.0071 (7)	0.0105 (7)
C16	0.0287 (8)	0.0327 (8)	0.0357 (8)	−0.0013 (6)	0.0088 (6)	0.0050 (6)

Geometric parameters (Å, º)

C1—O1	1.2198 (19)	C9—C10	1.452 (2)
C1—C9	1.4687 (19)	C10—N2	1.2886 (19)
C1—C2	1.470 (2)	C10—O3	1.3677 (16)
C2—C7	1.385 (2)	O3—C11	1.3579 (16)
C2—C3	1.402 (2)	C11—N1	1.2844 (19)
C3—C4	1.371 (2)	C11—C12	1.4566 (19)
C3—H3	0.9400	N1—N2	1.4026 (19)
C4—C5	1.390 (3)	C12—C16	1.388 (2)
C4—H4	0.9400	C12—C13	1.389 (2)
C5—C6	1.374 (2)	C13—C14	1.385 (2)
C5—H5	0.9400	C13—H13	0.9400
C6—C7	1.388 (2)	C14—N3	1.323 (2)
C6—H6	0.9400	C14—H14	0.9400
C7—O2	1.3804 (17)	N3—C15	1.343 (2)
O2—C8	1.3398 (17)	C15—C16	1.377 (2)
C8—C9	1.347 (2)	C15—H15	0.9400
C8—H8	0.9400	C16—H16	0.9400
O1—C1—C9	123.91 (14)	C10—C9—C1	120.58 (12)
O1—C1—C2	122.36 (14)	N2—C10—O3	112.35 (13)
C9—C1—C2	113.73 (12)	N2—C10—C9	129.32 (13)
C7—C2—C3	117.99 (14)	O3—C10—C9	118.32 (12)
C7—C2—C1	120.88 (13)	C11—O3—C10	102.35 (11)
C3—C2—C1	121.13 (14)	N1—C11—O3	112.72 (13)
C4—C3—C2	120.38 (16)	N1—C11—C12	126.91 (13)
C4—C3—H3	119.8	O3—C11—C12	120.36 (12)
C2—C3—H3	119.8	C11—N1—N2	106.41 (12)
C3—C4—C5	120.12 (15)	C10—N2—N1	106.13 (12)
C3—C4—H4	119.9	C16—C12—C13	118.32 (13)
C5—C4—H4	119.9	C16—C12—C11	119.51 (13)
C6—C5—C4	120.97 (16)	C13—C12—C11	122.17 (13)
C6—C5—H5	119.5	C14—C13—C12	118.09 (13)
C4—C5—H5	119.5	C14—C13—H13	121.0
C5—C6—C7	118.22 (16)	C12—C13—H13	121.0
C5—C6—H6	120.9	N3—C14—C13	124.45 (14)
C7—C6—H6	120.9	N3—C14—H14	117.8
O2—C7—C2	121.44 (13)	C13—C14—H14	117.8
O2—C7—C6	116.25 (14)	C14—N3—C15	116.74 (13)
C2—C7—C6	122.30 (14)	N3—C15—C16	123.53 (14)
C8—O2—C7	118.70 (12)	N3—C15—H15	118.2
O2—C8—C9	124.91 (13)	C16—C15—H15	118.2
O2—C8—H8	117.5	C15—C16—C12	118.86 (14)
C9—C8—H8	117.5	C15—C16—H16	120.6
C8—C9—C10	119.08 (13)	C12—C16—H16	120.6
C8—C9—C1	120.32 (13)
O1—C1—C2—C7	−178.30 (15)	C1—C9—C10—N2	−7.4 (2)
C9—C1—C2—C7	1.2 (2)	C8—C9—C10—O3	−8.0 (2)
O1—C1—C2—C3	1.4 (2)	C1—C9—C10—O3	173.75 (12)
C9—C1—C2—C3	−179.09 (13)	N2—C10—O3—C11	−2.00 (16)
C7—C2—C3—C4	0.4 (2)	C9—C10—O3—C11	177.07 (12)
C1—C2—C3—C4	−179.31 (14)	C10—O3—C11—N1	1.97 (16)
C2—C3—C4—C5	0.6 (3)	C10—O3—C11—C12	−177.28 (12)
C3—C4—C5—C6	−1.0 (3)	O3—C11—N1—N2	−1.26 (18)
C4—C5—C6—C7	0.4 (3)	C12—C11—N1—N2	177.93 (14)
C3—C2—C7—O2	179.26 (13)	O3—C10—N2—N1	1.33 (18)
C1—C2—C7—O2	−1.1 (2)	C9—C10—N2—N1	−177.61 (14)
C3—C2—C7—C6	−1.0 (2)	C11—N1—N2—C10	−0.05 (18)
C1—C2—C7—C6	178.66 (14)	N1—C11—C12—C16	1.1 (2)
C5—C6—C7—O2	−179.60 (14)	O3—C11—C12—C16	−179.80 (13)
C5—C6—C7—C2	0.7 (2)	N1—C11—C12—C13	−178.16 (15)
C2—C7—O2—C8	−0.2 (2)	O3—C11—C12—C13	1.0 (2)
C6—C7—O2—C8	−179.93 (13)	C16—C12—C13—C14	0.5 (2)
C7—O2—C8—C9	1.3 (2)	C11—C12—C13—C14	179.71 (13)
O2—C8—C9—C10	−179.26 (13)	C12—C13—C14—N3	−0.5 (2)
O2—C8—C9—C1	−1.0 (2)	C13—C14—N3—C15	0.1 (2)
O1—C1—C9—C8	179.27 (16)	C14—N3—C15—C16	0.3 (2)
C2—C1—C9—C8	−0.3 (2)	N3—C15—C16—C12	−0.3 (2)
O1—C1—C9—C10	−2.5 (2)	C13—C12—C16—C15	−0.1 (2)
C2—C1—C9—C10	177.96 (12)	C11—C12—C16—C15	−179.37 (14)
C8—C9—C10—N2	170.89 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1^i	0.94	2.55	3.2517 (19)	132
C14—H14···N1^i	0.94	2.63	3.248 (2)	123

Symmetry code: (i) x+1, y, z.