organic compounds
3-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-4H-chromen-4-one
aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr
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.
Keywords: crystal structure; oxadiazole; hydrogen bonding.
CCDC reference: 1509623
Structure description
Heterocycles possessing five-membered rings have attracted lots of interest due to their versatile pharmacological and biological activities. Oxadiazole is a furan-type five-membered ring heterocycle in which two nitrogen atoms substitute two carbons. Depending on the positions of the replacing nitrogen atoms, several types of oxadiazole isomers are formed. Examples of oxadiazole structures have been published (dos Santos et al., 2014; Sharma et al., 2014). In particular, 1,3,4-oxadiazoles have been extensively investigated in medicinal chemistry. They have been found to show anti-fungal (Wani et al. 2015), anti-inflammatory (Banerjee et al. 2015), anti-microbial (Li et al. 2015), and anticancer activities (Mochona et al. 2016).
We have focused our research on et al. 2014, Lee et al. 2016), which have a central conjugated enone system connecting two aromatic rings. In a continuation of this research program, the central enone of chalcone was modified to an oxadiazole ring. Herein, the of title oxadiazole compound is reported.
(ShinThe molecular structure is shown in Fig. 1. The plane of the oxadiazole ring is almost co-planar with attached pyridine ring and chromenyl ring system, making 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 bonds (Table 1) lead to the formation of dimers, which are linked together into [100] chains (Fig. 2).
Synthesis and crystallization
The synthetic procedure is shown in Fig. 3. To a solution of 4-oxo-4H-chromene-3-carbaldehyde (348 mg, 2 mmol) in 20 ml of anhydrous ethanol was added isonicotinohydrazide (274 mg, 2 mmol) and a catalytic amount of glacial acetic acid. The temperature of the mixture was adjusted to around 358 K in an oil-bath and the mixture was refluxed for 5 h. Then the reaction mixture was cooled down to the room temperature to give a precipitate. Filtration and washing with ethanol afforded a solid of the intermediate compound (I, 88%) which was used in the next step without further purification. The intermediate compound (I, 196 mg, 0.5 mmol) was dissolved in 10 ml of dichloromethane and iodobenzenediacetate (276 mg, 0.8 mmol) was added. The reaction mixture was stirred at room temperature for 12 h and the solvent was evaporated under vacuum to produce a solid. Recrystallization of the solid from methanol solution gave yellow block-shaped crystals for this study (m.p. 513–514 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1509623
https://doi.org/10.1107/S2414314616016254/ff4010sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016254/ff4010Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616016254/ff4010Isup3.cml
Data collection: APEX2 (Bruker, 2000); cell
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).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) Å3 | 0.13 × 0.12 × 0.09 mm |
Z = 4 |
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 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.045P)2 + 0.5495P] where P = (Fo2 + 2Fc2)/3 |
3188 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.94 | 2.55 | 3.2517 (19) | 132 |
C14—H14···N1i | 0.94 | 2.63 | 3.248 (2) | 123 |
Symmetry code: (i) x+1, y, z. |
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