organic compounds
5-(2-Hydroxybenzoyl)-1-methyl-3-nitropyridin-2(1H)-one
aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and bOrganic Chemistry, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: aspandian59@gmail.com
In the title compound, C13H10N2O5, the dihedral angle between the pyridine and phenyl ring is 50.47 (2)°. The hydroxyl H and ketone O atoms form an intramolecular O—H⋯O hydrogen bond with the hydroxyl group almost coplanar with the phenyl ring. In the crystal, molecules are linked by two C—H⋯O hydrogen bonds, forming dimers. The dimers are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional architecture.
Keywords: crystal structure; pyridine derivative; hydrogen bonding.
CCDC reference: 1471050
Structure description
The title compound is an important nitropyridine compound which is widely used in organic synthesis, especially in the synthesis of heterocyclic drugs and cytokine inhibitors (Hu et al., 2011). Studies of pyridine and pyrimidine derivatives related to the title compound are also of interest owing to their putative fluorescence properties (Kawai et al. 2001; Abdullah, 2005). For related crystal structures, see: Aznan et al., (2011).
In the title compound the dihedral angle between the pyridine and phenyl ring is 50.47 (2)°. The hydroxyl H and ketone O atoms form an intramolecular O—H⋯O hydrogen bond with the hydroxyl group almost coplanar with the phenyl ring (Fig. 1). In the crystal, molecules are linked into dimers via two C—H⋯O hydrogen bonds (Table 1), resulting in an (10) graph-set motif (Fig. 2). The dimers are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional architecture.
Synthesis and crystallization
A mixture of 3-formylchromone (1 mmol), (Z)-N-methyl-1-(methyl-thio)-2-nitroethenamine (1 mmol), and indium trifluoromethanesulfonate (0.020 mmol) in ethanol (3 ml) were charged in a 25 ml round-bottomed flask and the mixture was heated at reflux. The resulting solution was stirred for 1.5 h. The consumption of the starting material was monitored by TLC. After completion of the reaction, the compound was purified by to obtain pure product. The purified compound was recrystallized from ethanol and DMSO-D6 by slow evaporation. The yield of the isolated product was 88%, giving block-like crystals suitable for X-ray diffraction.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1471050
10.1107/S2414314616005277/ff4005sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005277/ff4005Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005277/ff4005Isup3.cml
A mixture of 3-formylchromone (1 mmol), (Z)-N-methyl-1-(methyl-thio)-2-nitroethenamine (1 mmol), and indium trifluoromethanesulfonate (0.020 mmol) in ethanol (3 ml) were charged in a 25 ml round-bottomed flask and the mixture was heated at reflux. The resulting solution was stirred for 1.5 h. The consumption of the starting material was monitored by TLC. After completion of the reaction, the compound was purified by
to obtain pure product. The purified compound was recrystallized from ethanol and DMSO-D6 by slow evaporation. The yield of the isolated product was 88%, giving block-like crystals suitable for X-ray diffraction.The title compound is an important nitropyridine compound which is widely used in organic synthesis, especially in the synthesis of heterocyclic drugs and cytokine inhibitors (Hu et al., 2011). Studies of pyridine and pyrimidine derivatives related to the title compound are also of interest owing to their putative fluorescence properties (Kawai et al. 2001; Abdullah, 2005). For related crystal structures, see: Aznan et al., (2011).
In the title compound the dihedral angle between the pyridine and phenyl ring is 50.47 (2)°. The hydroxyl H and ketone O atoms form an intramolecular O—H···O hydrogen bond with the hydroxyl group almost coplanar with the phenyl ring (Fig. 1). In the crystal, molecules are linked into dimers via two C—H···O hydrogen bonds (Table 1), resulting in an R22(10) graph-set motif (Fig. 2).
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme and displacement ellipsoids drawn at 30% probability level. | |
Fig. 2. The crystal packing of the title compound is viewed along the b axis, showing intramolecular O—H···O hydrogen bonds and molecules linked by C—H···O intermolecular interactions along the b axis. |
C13H10N2O5 | F(000) = 568 |
Mr = 274.23 | Dx = 1.505 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1288 reflections |
a = 7.4998 (8) Å | θ = 2.3–25.0° |
b = 13.8350 (14) Å | µ = 0.12 mm−1 |
c = 12.2324 (12) Å | T = 293 K |
β = 107.474 (4)° | Block, colourless |
V = 1210.7 (2) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 2126 independent reflections |
Radiation source: fine-focus sealed tube | 1288 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω and φ scan | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.974, Tmax = 0.979 | k = −16→16 |
18309 measured reflections | l = −14→14 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.083P)2 + 0.9837P] where P = (Fo2 + 2Fc2)/3 |
2091 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C13H10N2O5 | V = 1210.7 (2) Å3 |
Mr = 274.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4998 (8) Å | µ = 0.12 mm−1 |
b = 13.8350 (14) Å | T = 293 K |
c = 12.2324 (12) Å | 0.22 × 0.20 × 0.18 mm |
β = 107.474 (4)° |
Bruker Kappa APEXII CCD diffractometer | 2126 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1288 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.979 | Rint = 0.057 |
18309 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.42 e Å−3 |
2091 reflections | Δρmin = −0.30 e Å−3 |
181 parameters |
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 | ||
O2 | 0.8511 (3) | −0.05625 (17) | 1.07410 (18) | 0.0501 (6) | |
N2 | 0.4933 (3) | 0.21890 (17) | 0.95459 (19) | 0.0352 (6) | |
O5 | 0.2617 (3) | 0.22615 (17) | 0.78498 (18) | 0.0523 (7) | |
O1 | 1.0686 (4) | −0.0637 (2) | 1.2845 (2) | 0.0662 (8) | |
H1 | 0.9808 | −0.0823 | 1.2307 | 0.099* | |
C8 | 0.7065 (4) | 0.0878 (2) | 1.0007 (2) | 0.0338 (7) | |
C12 | 0.6121 (4) | 0.0460 (2) | 0.8948 (2) | 0.0361 (7) | |
H12 | 0.6469 | −0.0148 | 0.8759 | 0.043* | |
N1 | 0.3812 (4) | 0.0517 (2) | 0.7088 (2) | 0.0511 (8) | |
C9 | 0.6406 (4) | 0.1738 (2) | 1.0272 (2) | 0.0357 (7) | |
H9 | 0.6993 | 0.2022 | 1.0978 | 0.043* | |
C11 | 0.4714 (4) | 0.0938 (2) | 0.8206 (2) | 0.0372 (8) | |
C6 | 1.0100 (4) | 0.0801 (2) | 1.1684 (2) | 0.0378 (8) | |
O3 | 0.3589 (5) | 0.1021 (2) | 0.6255 (2) | 0.0864 (10) | |
C7 | 0.8572 (4) | 0.0327 (2) | 1.0816 (2) | 0.0369 (7) | |
C10 | 0.3981 (4) | 0.1837 (2) | 0.8458 (2) | 0.0373 (8) | |
O4 | 0.3364 (4) | −0.0328 (2) | 0.7060 (2) | 0.0750 (9) | |
C5 | 1.0684 (4) | 0.1731 (3) | 1.1538 (3) | 0.0493 (9) | |
H5 | 1.0048 | 0.2080 | 1.0888 | 0.059* | |
C1 | 1.1098 (4) | 0.0286 (3) | 1.2664 (3) | 0.0477 (9) | |
C13 | 0.4218 (5) | 0.3087 (2) | 0.9891 (3) | 0.0538 (10) | |
H13A | 0.3173 | 0.3312 | 0.9277 | 0.081* | |
H13B | 0.5185 | 0.3568 | 1.0063 | 0.081* | |
H13C | 0.3827 | 0.2970 | 1.0558 | 0.081* | |
C2 | 1.2540 (5) | 0.0719 (4) | 1.3476 (3) | 0.0640 (11) | |
H2 | 1.3150 | 0.0388 | 1.4145 | 0.077* | |
C4 | 1.2182 (5) | 0.2144 (3) | 1.2333 (3) | 0.0646 (11) | |
H4 | 1.2582 | 0.2761 | 1.2216 | 0.078* | |
C3 | 1.3088 (5) | 0.1631 (4) | 1.3310 (4) | 0.0726 (13) | |
H3 | 1.4086 | 0.1913 | 1.3863 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0543 (14) | 0.0430 (15) | 0.0478 (14) | 0.0061 (11) | 0.0074 (11) | 0.0055 (11) |
N2 | 0.0360 (14) | 0.0363 (15) | 0.0288 (13) | 0.0027 (11) | 0.0028 (11) | −0.0011 (11) |
O5 | 0.0506 (14) | 0.0564 (15) | 0.0388 (13) | 0.0125 (11) | −0.0036 (11) | 0.0050 (11) |
O1 | 0.0713 (17) | 0.0667 (19) | 0.0514 (15) | 0.0189 (14) | 0.0047 (13) | 0.0210 (13) |
C8 | 0.0338 (16) | 0.0388 (18) | 0.0273 (16) | −0.0004 (13) | 0.0070 (13) | 0.0012 (13) |
C12 | 0.0378 (17) | 0.0374 (18) | 0.0327 (17) | −0.0006 (13) | 0.0099 (14) | −0.0022 (13) |
N1 | 0.0454 (16) | 0.065 (2) | 0.0345 (17) | 0.0050 (15) | −0.0004 (13) | −0.0135 (16) |
C9 | 0.0355 (16) | 0.0421 (19) | 0.0247 (15) | −0.0037 (14) | 0.0018 (13) | −0.0010 (13) |
C11 | 0.0394 (17) | 0.0409 (19) | 0.0275 (16) | −0.0027 (14) | 0.0042 (14) | −0.0044 (13) |
C6 | 0.0337 (16) | 0.049 (2) | 0.0291 (17) | 0.0064 (14) | 0.0073 (13) | 0.0012 (14) |
O3 | 0.121 (3) | 0.096 (2) | 0.0275 (14) | 0.0062 (19) | 0.0009 (15) | −0.0046 (15) |
C7 | 0.0381 (17) | 0.044 (2) | 0.0299 (16) | 0.0054 (14) | 0.0117 (13) | 0.0053 (14) |
C10 | 0.0391 (17) | 0.0402 (18) | 0.0285 (16) | −0.0015 (14) | 0.0042 (14) | 0.0036 (14) |
O4 | 0.0760 (19) | 0.067 (2) | 0.0690 (19) | −0.0128 (15) | 0.0019 (14) | −0.0323 (15) |
C5 | 0.0418 (19) | 0.056 (2) | 0.048 (2) | −0.0010 (16) | 0.0095 (16) | −0.0015 (16) |
C1 | 0.0411 (19) | 0.065 (2) | 0.0346 (18) | 0.0132 (17) | 0.0078 (15) | −0.0002 (17) |
C13 | 0.060 (2) | 0.048 (2) | 0.047 (2) | 0.0135 (17) | 0.0068 (17) | −0.0123 (16) |
C2 | 0.052 (2) | 0.096 (3) | 0.036 (2) | 0.020 (2) | 0.0003 (18) | −0.008 (2) |
C4 | 0.045 (2) | 0.072 (3) | 0.072 (3) | −0.0133 (19) | 0.010 (2) | −0.018 (2) |
C3 | 0.043 (2) | 0.105 (4) | 0.058 (3) | 0.001 (2) | −0.0036 (19) | −0.035 (3) |
O2—C7 | 1.234 (4) | C11—C10 | 1.431 (4) |
N2—C9 | 1.345 (4) | C6—C5 | 1.388 (5) |
N2—C10 | 1.395 (4) | C6—C1 | 1.402 (4) |
N2—C13 | 1.465 (4) | C6—C7 | 1.463 (4) |
O5—C10 | 1.219 (3) | C5—C4 | 1.370 (5) |
O1—C1 | 1.348 (4) | C5—H5 | 0.9300 |
O1—H1 | 0.8200 | C1—C2 | 1.367 (5) |
C8—C9 | 1.364 (4) | C13—H13A | 0.9600 |
C8—C12 | 1.402 (4) | C13—H13B | 0.9600 |
C8—C7 | 1.472 (4) | C13—H13C | 0.9600 |
C12—C11 | 1.342 (4) | C2—C3 | 1.361 (6) |
C12—H12 | 0.9300 | C2—H2 | 0.9300 |
N1—O3 | 1.205 (4) | C4—C3 | 1.381 (6) |
N1—O4 | 1.214 (4) | C4—H4 | 0.9300 |
N1—C11 | 1.453 (4) | C3—H3 | 0.9300 |
C9—H9 | 0.9300 | ||
C9—N2—C10 | 123.5 (3) | O5—C10—N2 | 120.6 (3) |
C9—N2—C13 | 120.2 (2) | O5—C10—C11 | 126.4 (3) |
C10—N2—C13 | 116.3 (2) | N2—C10—C11 | 112.9 (2) |
C1—O1—H1 | 109.5 | C4—C5—C6 | 121.2 (3) |
C9—C8—C12 | 117.5 (3) | C4—C5—H5 | 119.4 |
C9—C8—C7 | 123.5 (3) | C6—C5—H5 | 119.4 |
C12—C8—C7 | 118.7 (3) | O1—C1—C2 | 117.8 (3) |
C11—C12—C8 | 119.8 (3) | O1—C1—C6 | 122.2 (3) |
C11—C12—H12 | 120.1 | C2—C1—C6 | 120.0 (4) |
C8—C12—H12 | 120.1 | N2—C13—H13A | 109.5 |
O3—N1—O4 | 124.5 (3) | N2—C13—H13B | 109.5 |
O3—N1—C11 | 118.2 (3) | H13A—C13—H13B | 109.5 |
O4—N1—C11 | 117.3 (3) | N2—C13—H13C | 109.5 |
N2—C9—C8 | 122.1 (3) | H13A—C13—H13C | 109.5 |
N2—C9—H9 | 118.9 | H13B—C13—H13C | 109.5 |
C8—C9—H9 | 118.9 | C3—C2—C1 | 120.5 (4) |
C12—C11—C10 | 123.9 (3) | C3—C2—H2 | 119.8 |
C12—C11—N1 | 119.2 (3) | C1—C2—H2 | 119.8 |
C10—C11—N1 | 116.8 (3) | C5—C4—C3 | 119.1 (4) |
C5—C6—C1 | 118.3 (3) | C5—C4—H4 | 120.5 |
C5—C6—C7 | 122.0 (3) | C3—C4—H4 | 120.5 |
C1—C6—C7 | 119.6 (3) | C2—C3—C4 | 120.8 (3) |
O2—C7—C6 | 120.3 (3) | C2—C3—H3 | 119.6 |
O2—C7—C8 | 117.6 (3) | C4—C3—H3 | 119.6 |
C6—C7—C8 | 122.1 (3) | ||
C9—C8—C12—C11 | 4.7 (4) | C9—N2—C10—O5 | 177.7 (3) |
C7—C8—C12—C11 | 178.5 (3) | C13—N2—C10—O5 | −0.9 (4) |
C10—N2—C9—C8 | −1.5 (5) | C9—N2—C10—C11 | 1.1 (4) |
C13—N2—C9—C8 | 177.0 (3) | C13—N2—C10—C11 | −177.5 (3) |
C12—C8—C9—N2 | −1.4 (4) | C12—C11—C10—O5 | −173.9 (3) |
C7—C8—C9—N2 | −174.9 (3) | N1—C11—C10—O5 | 3.9 (5) |
C8—C12—C11—C10 | −5.4 (5) | C12—C11—C10—N2 | 2.4 (4) |
C8—C12—C11—N1 | 176.9 (3) | N1—C11—C10—N2 | −179.8 (3) |
O3—N1—C11—C12 | −131.4 (3) | C1—C6—C5—C4 | −0.8 (5) |
O4—N1—C11—C12 | 47.3 (4) | C7—C6—C5—C4 | −176.5 (3) |
O3—N1—C11—C10 | 50.7 (4) | C5—C6—C1—O1 | −176.5 (3) |
O4—N1—C11—C10 | −130.6 (3) | C7—C6—C1—O1 | −0.7 (5) |
C5—C6—C7—O2 | 153.2 (3) | C5—C6—C1—C2 | 3.5 (5) |
C1—C6—C7—O2 | −22.5 (4) | C7—C6—C1—C2 | 179.4 (3) |
C5—C6—C7—C8 | −26.8 (4) | O1—C1—C2—C3 | 176.3 (3) |
C1—C6—C7—C8 | 157.5 (3) | C6—C1—C2—C3 | −3.7 (5) |
C9—C8—C7—O2 | 147.5 (3) | C6—C5—C4—C3 | −1.7 (6) |
C12—C8—C7—O2 | −25.8 (4) | C1—C2—C3—C4 | 1.2 (6) |
C9—C8—C7—C6 | −32.4 (4) | C5—C4—C3—C2 | 1.6 (6) |
C12—C8—C7—C6 | 154.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.90 | 2.603 (3) | 142 |
C4—H4···O1i | 0.93 | 2.58 | 3.498 (5) | 169 |
C9—H9···O5ii | 0.93 | 2.41 | 3.311 (3) | 164 |
C13—H13A···O4iii | 0.96 | 2.53 | 3.388 (4) | 148 |
C13—H13B···O3ii | 0.96 | 2.59 | 3.431 (5) | 146 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+5/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.90 | 2.603 (3) | 142 |
C4—H4···O1i | 0.93 | 2.58 | 3.498 (5) | 169 |
C9—H9···O5ii | 0.93 | 2.41 | 3.311 (3) | 164 |
C13—H13A···O4iii | 0.96 | 2.53 | 3.388 (4) | 148 |
C13—H13B···O3ii | 0.96 | 2.59 | 3.431 (5) | 146 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+5/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H10N2O5 |
Mr | 274.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.4998 (8), 13.8350 (14), 12.2324 (12) |
β (°) | 107.474 (4) |
V (Å3) | 1210.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.974, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18309, 2126, 1288 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.176, 1.01 |
No. of reflections | 2091 |
No. of parameters | 181 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.30 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).
Acknowledgements
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.
References
Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9–15. CAS Google Scholar
Aznan, A. M. A., Abdullah, Z., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o3076. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hu, Y., Jin, Y. Z., Xiong, Y. P. & Li, Z. C. (2011). Sci. Technol. Eng. 11, 1841–1843. Google Scholar
Kawai, M., Lee, M. J., Evans, K. O. & Nordlund, T. M. (2001). J. Fluoresc. 11, 23–32. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The title compound is an important nitropyridine compound which is widely used in organic synthesis, especially in the synthesis of heterocyclic drugs and cytokine inhibitors (Hu et al., 2011). Studies of pyridine and pyrimidine derivatives related to the title compound are of also of interest owing to their putative fluorescence properties (Kawai et al. 2001; Abdullah, 2005).
In the title compound the dihedral angle between the pyridine and phenyl ring is 50.47 (2)°. The hydroxyl H and ketone O atoms form an intra-molecular O-H···O hydrogen bond with the hydroxyl group almost coplanar with the phenyl ring (Figure 1). The molecules are linked into inversion dimers via C-H···O hydrogen bonds resulting in an R22(10) graph-set motif (Bernstein et al., 1995) (Figure 2).