Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029212/at2330sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029212/at2330Isup2.hkl |
CCDC reference: 654991
10 mmol of 3,4-Dimethylbenzaldehyde was added to a solution of nicotinic acid hydrazine (10 mmol) in 10 ml of ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 68%). Clear blocks of (I) were obtained by evaporation from a methanol solution after five days.
The H atoms were placed geometrically (C—H = 0.93 - 0.96 Å, O—H = 0.85 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(Cmethyl or Owater).
As part of our ongoing studies of the coordination chemistry of aroylhydrazones ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
In the molecule of (I), both C7—N3 [1.269 (3) Å] and C6—O1 [1.216 (2) Å] are close to double-bond separations, indicating that the Lewis structure shown in the scheme is only an approximation to the electron distribution in the molecule. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the pyridine and benzene ring mean planes is 10.69 (10)°, indicating that the molecule is non-planar, which perhaps correlates with the intramolecular O—H···O hydrogen bond (Table 1). An intermolecular N—H···O link also occurs.
For related literature, see: Tai et al. (2003).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C15H15N3O·H2O | F(000) = 576 |
Mr = 271.32 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2 y b c | Cell parameters from 1686 reflections |
a = 13.4762 (19) Å | θ = 2.7–26.9° |
b = 6.5174 (14) Å | µ = 0.09 mm−1 |
c = 16.497 (2) Å | T = 298 K |
β = 101.629 (2)° | Block, colourless |
V = 1419.2 (4) Å3 | 0.56 × 0.53 × 0.49 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2475 independent reflections |
Radiation source: fine-focus sealed tube | 1583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −15→15 |
Tmin = 0.953, Tmax = 0.959 | k = −7→7 |
6293 measured reflections | l = −13→19 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.2072P] where P = (Fo2 + 2Fc2)/3 |
2475 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C15H15N3O·H2O | V = 1419.2 (4) Å3 |
Mr = 271.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4762 (19) Å | µ = 0.09 mm−1 |
b = 6.5174 (14) Å | T = 298 K |
c = 16.497 (2) Å | 0.56 × 0.53 × 0.49 mm |
β = 101.629 (2)° |
Bruker SMART CCD area-detector diffractometer | 2475 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1583 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.959 | Rint = 0.038 |
6293 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2475 reflections | Δρmin = −0.18 e Å−3 |
183 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.32848 (12) | 0.7209 (2) | −0.01437 (8) | 0.0570 (6) | |
N1 | 0.40161 (16) | 1.0572 (3) | −0.20590 (10) | 0.0613 (7) | |
N2 | 0.30314 (13) | 1.0062 (3) | 0.05661 (9) | 0.0478 (6) | |
N3 | 0.26026 (13) | 0.8926 (3) | 0.11142 (10) | 0.0472 (6) | |
C1 | 0.37042 (16) | 0.9576 (3) | −0.14497 (12) | 0.0508 (8) | |
C2 | 0.37106 (14) | 1.0398 (3) | −0.06760 (11) | 0.0374 (6) | |
C3 | 0.40561 (17) | 1.2374 (3) | −0.05342 (12) | 0.0499 (8) | |
C4 | 0.44022 (17) | 1.3419 (4) | −0.11451 (13) | 0.0565 (8) | |
C5 | 0.43719 (17) | 1.2463 (4) | −0.18867 (13) | 0.0571 (9) | |
C6 | 0.33334 (15) | 0.9064 (3) | −0.00641 (11) | 0.0411 (7) | |
C7 | 0.23315 (15) | 0.9945 (3) | 0.16883 (12) | 0.0468 (7) | |
C8 | 0.18329 (15) | 0.8997 (3) | 0.22987 (11) | 0.0424 (7) | |
C9 | 0.17182 (15) | 1.0139 (3) | 0.29861 (12) | 0.0467 (7) | |
C10 | 0.12531 (15) | 0.9365 (4) | 0.35975 (12) | 0.0469 (8) | |
C11 | 0.08658 (15) | 0.7372 (4) | 0.35100 (12) | 0.0477 (8) | |
C12 | 0.09697 (16) | 0.6241 (4) | 0.28210 (12) | 0.0505 (8) | |
C13 | 0.14457 (16) | 0.7015 (3) | 0.22211 (12) | 0.0491 (8) | |
C14 | 0.11591 (19) | 1.0666 (4) | 0.43276 (14) | 0.0676 (10) | |
C15 | 0.03416 (19) | 0.6467 (4) | 0.41503 (14) | 0.0705 (10) | |
O2 | 0.32861 (13) | 0.4266 (2) | 0.11411 (8) | 0.0642 (6) | |
H1 | 0.34670 | 0.82420 | −0.15520 | 0.0610* | |
H2 | 0.31050 | 1.13680 | 0.06230 | 0.0570* | |
H3 | 0.40560 | 1.30010 | −0.00280 | 0.0600* | |
H4 | 0.46520 | 1.47480 | −0.10560 | 0.0680* | |
H5 | 0.46140 | 1.31750 | −0.22950 | 0.0690* | |
H7 | 0.24560 | 1.13490 | 0.17200 | 0.0560* | |
H9 | 0.19640 | 1.14760 | 0.30370 | 0.0560* | |
H12 | 0.07100 | 0.49160 | 0.27610 | 0.0610* | |
H13 | 0.15070 | 0.62150 | 0.17670 | 0.0590* | |
H14A | 0.15010 | 1.19480 | 0.42990 | 0.1010* | |
H14B | 0.14600 | 0.99650 | 0.48290 | 0.1010* | |
H14C | 0.04560 | 1.09170 | 0.43230 | 0.1010* | |
H15A | 0.01530 | 0.50740 | 0.40050 | 0.1060* | |
H15B | −0.02540 | 0.72530 | 0.41740 | 0.1060* | |
H15C | 0.07920 | 0.64950 | 0.46810 | 0.1060* | |
H2A | 0.33440 | 0.53020 | 0.08410 | 0.0770* | |
H2B | 0.35320 | 0.45640 | 0.16430 | 0.0770* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0900 (12) | 0.0355 (10) | 0.0492 (9) | −0.0060 (8) | 0.0226 (8) | −0.0005 (7) |
N1 | 0.0875 (14) | 0.0591 (14) | 0.0439 (10) | −0.0084 (11) | 0.0289 (10) | −0.0033 (10) |
N2 | 0.0710 (12) | 0.0351 (11) | 0.0436 (9) | −0.0046 (9) | 0.0266 (9) | 0.0025 (8) |
N3 | 0.0601 (11) | 0.0424 (11) | 0.0436 (10) | −0.0037 (9) | 0.0215 (8) | 0.0064 (8) |
C1 | 0.0706 (15) | 0.0408 (14) | 0.0438 (12) | −0.0054 (11) | 0.0179 (11) | −0.0053 (10) |
C2 | 0.0438 (11) | 0.0353 (12) | 0.0338 (10) | −0.0004 (9) | 0.0092 (8) | 0.0001 (9) |
C3 | 0.0635 (14) | 0.0491 (15) | 0.0400 (11) | −0.0101 (11) | 0.0171 (10) | −0.0062 (10) |
C4 | 0.0690 (15) | 0.0501 (15) | 0.0541 (13) | −0.0172 (12) | 0.0212 (11) | −0.0038 (11) |
C5 | 0.0675 (15) | 0.0621 (18) | 0.0476 (13) | −0.0086 (13) | 0.0254 (11) | 0.0073 (12) |
C6 | 0.0480 (12) | 0.0398 (14) | 0.0358 (11) | −0.0027 (10) | 0.0090 (9) | 0.0014 (9) |
C7 | 0.0574 (13) | 0.0394 (13) | 0.0472 (12) | −0.0044 (11) | 0.0189 (10) | 0.0020 (10) |
C8 | 0.0445 (12) | 0.0422 (14) | 0.0429 (11) | −0.0020 (10) | 0.0145 (9) | 0.0031 (9) |
C9 | 0.0497 (13) | 0.0406 (13) | 0.0525 (12) | −0.0036 (10) | 0.0168 (10) | −0.0026 (10) |
C10 | 0.0455 (12) | 0.0555 (15) | 0.0413 (12) | 0.0025 (11) | 0.0126 (9) | −0.0002 (10) |
C11 | 0.0442 (12) | 0.0571 (16) | 0.0441 (12) | 0.0003 (11) | 0.0143 (9) | 0.0074 (11) |
C12 | 0.0510 (13) | 0.0455 (14) | 0.0566 (14) | −0.0101 (11) | 0.0150 (11) | 0.0029 (11) |
C13 | 0.0551 (13) | 0.0490 (15) | 0.0463 (12) | −0.0040 (11) | 0.0175 (10) | −0.0030 (10) |
C14 | 0.0730 (16) | 0.0771 (19) | 0.0589 (14) | −0.0036 (14) | 0.0279 (12) | −0.0122 (13) |
C15 | 0.0730 (17) | 0.082 (2) | 0.0650 (15) | −0.0105 (14) | 0.0343 (13) | 0.0083 (14) |
O2 | 0.1121 (13) | 0.0394 (10) | 0.0449 (8) | −0.0104 (9) | 0.0250 (9) | 0.0012 (7) |
O1—C6 | 1.216 (2) | C10—C14 | 1.499 (3) |
O2—H2A | 0.8500 | C11—C12 | 1.385 (3) |
O2—H2B | 0.8500 | C11—C15 | 1.505 (3) |
N1—C1 | 1.334 (3) | C12—C13 | 1.379 (3) |
N1—C5 | 1.332 (3) | C1—H1 | 0.9300 |
N2—N3 | 1.382 (2) | C3—H3 | 0.9300 |
N2—C6 | 1.357 (3) | C4—H4 | 0.9300 |
N3—C7 | 1.269 (3) | C5—H5 | 0.9300 |
N2—H2 | 0.8600 | C7—H7 | 0.9300 |
C1—C2 | 1.383 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.373 (3) | C12—H12 | 0.9300 |
C2—C6 | 1.497 (3) | C13—H13 | 0.9300 |
C3—C4 | 1.374 (3) | C14—H14B | 0.9600 |
C4—C5 | 1.366 (3) | C14—H14C | 0.9600 |
C7—C8 | 1.456 (3) | C14—H14A | 0.9600 |
C8—C9 | 1.391 (3) | C15—H15C | 0.9600 |
C8—C13 | 1.389 (3) | C15—H15A | 0.9600 |
C9—C10 | 1.386 (3) | C15—H15B | 0.9600 |
C10—C11 | 1.396 (4) | ||
O1···O2 | 2.858 (2) | C14···H15B | 2.9100 |
O1···N3 | 2.678 (2) | C15···H14B | 2.8400 |
O1···C3i | 3.420 (3) | C15···H14C | 2.9200 |
O1···C14ii | 3.387 (3) | H1···O1 | 2.4800 |
O1···C10ii | 3.251 (3) | H1···C13ii | 3.0500 |
O2···N3 | 3.171 (2) | H1···C8ii | 2.9800 |
O2···C7i | 3.297 (3) | H2···O2v | 2.0700 |
O2···N2i | 2.897 (2) | H2···C3 | 2.5900 |
O2···C3i | 3.375 (3) | H2···H7 | 2.1600 |
O2···O1 | 2.858 (2) | H2···H3 | 2.1200 |
O2···N1iii | 2.936 (2) | H2A···N3 | 2.6400 |
O1···H2A | 2.0300 | H2A···O1 | 2.0300 |
O1···H1 | 2.4800 | H2A···C4iv | 3.0900 |
O1···H14Bii | 2.8300 | H2A···C6 | 2.8700 |
O2···H3i | 2.5100 | H2A···H3i | 2.4000 |
O2···H7i | 2.4900 | H2B···H7i | 2.5700 |
O2···H4iv | 2.8800 | H2B···C5iii | 2.7900 |
O2···H2i | 2.0700 | H2B···N1iii | 2.1100 |
N1···O2ii | 2.936 (2) | H3···N2 | 2.6600 |
N2···O2v | 2.897 (2) | H3···O2v | 2.5100 |
N3···O1 | 2.678 (2) | H3···H2Av | 2.4000 |
N3···O2 | 3.171 (2) | H3···H2 | 2.1200 |
N1···H5vi | 2.7900 | H4···O2iv | 2.8800 |
N1···H2Bii | 2.1100 | H5···N1vii | 2.7900 |
N2···H3 | 2.6600 | H7···H2Bv | 2.5700 |
N3···H2A | 2.6400 | H7···O2v | 2.4900 |
N3···H13 | 2.6700 | H7···H2 | 2.1600 |
C1···C13ii | 3.529 (3) | H7···H9 | 2.4000 |
C3···O1v | 3.420 (3) | H9···H7 | 2.4000 |
C3···O2v | 3.375 (3) | H9···H14A | 2.3100 |
C3···C6iv | 3.582 (3) | H12···H15A | 2.3300 |
C6···C3iv | 3.582 (3) | H13···N3 | 2.6700 |
C7···O2v | 3.297 (3) | H14A···H9 | 2.3100 |
C10···O1iii | 3.251 (3) | H14B···C15 | 2.8400 |
C13···C1iii | 3.529 (3) | H14B···H15C | 2.4300 |
C14···O1iii | 3.387 (3) | H14B···O1iii | 2.8300 |
C3···H2 | 2.5900 | H14C···C15 | 2.9200 |
C4···H2Aiv | 3.0900 | H14C···H15B | 2.5700 |
C5···H2Bii | 2.7900 | H15A···H12 | 2.3300 |
C6···H2A | 2.8700 | H15B···C14 | 2.9100 |
C8···H1iii | 2.9800 | H15B···H14C | 2.5700 |
C13···H1iii | 3.0500 | H15C···C14 | 2.8400 |
C14···H15C | 2.8400 | H15C···H14B | 2.4300 |
H2A—O2—H2B | 109.00 | C2—C1—H1 | 118.00 |
C1—N1—C5 | 116.36 (18) | N1—C1—H1 | 118.00 |
N3—N2—C6 | 118.30 (18) | C2—C3—H3 | 120.00 |
N2—N3—C7 | 115.41 (18) | C4—C3—H3 | 120.00 |
N3—N2—H2 | 121.00 | C3—C4—H4 | 121.00 |
C6—N2—H2 | 121.00 | C5—C4—H4 | 121.00 |
N1—C1—C2 | 124.26 (19) | C4—C5—H5 | 118.00 |
C3—C2—C6 | 125.41 (17) | N1—C5—H5 | 118.00 |
C1—C2—C3 | 117.35 (18) | N3—C7—H7 | 119.00 |
C1—C2—C6 | 117.24 (17) | C8—C7—H7 | 119.00 |
C2—C3—C4 | 119.58 (19) | C10—C9—H9 | 119.00 |
C3—C4—C5 | 118.5 (2) | C8—C9—H9 | 119.00 |
N1—C5—C4 | 123.9 (2) | C11—C12—H12 | 119.00 |
N2—C6—C2 | 115.69 (17) | C13—C12—H12 | 119.00 |
O1—C6—N2 | 122.78 (18) | C12—C13—H13 | 120.00 |
O1—C6—C2 | 121.52 (17) | C8—C13—H13 | 120.00 |
N3—C7—C8 | 122.44 (18) | C10—C14—H14A | 109.00 |
C7—C8—C9 | 118.65 (18) | C10—C14—H14B | 109.00 |
C7—C8—C13 | 123.22 (17) | H14A—C14—H14B | 109.00 |
C9—C8—C13 | 118.12 (18) | H14A—C14—H14C | 110.00 |
C8—C9—C10 | 122.66 (19) | C10—C14—H14C | 109.00 |
C11—C10—C14 | 121.25 (19) | H14B—C14—H14C | 109.00 |
C9—C10—C11 | 118.55 (19) | C11—C15—H15B | 110.00 |
C9—C10—C14 | 120.2 (2) | C11—C15—H15C | 109.00 |
C10—C11—C12 | 118.8 (2) | C11—C15—H15A | 109.00 |
C10—C11—C15 | 120.71 (19) | H15A—C15—H15C | 109.00 |
C12—C11—C15 | 120.5 (2) | H15B—C15—H15C | 109.00 |
C11—C12—C13 | 122.2 (2) | H15A—C15—H15B | 109.00 |
C8—C13—C12 | 119.63 (19) | ||
C5—N1—C1—C2 | 1.4 (3) | N3—C7—C8—C9 | 169.1 (2) |
C1—N1—C5—C4 | −2.0 (4) | N3—C7—C8—C13 | −12.3 (3) |
C6—N2—N3—C7 | −179.72 (18) | C7—C8—C9—C10 | 179.93 (19) |
N3—N2—C6—O1 | −3.4 (3) | C13—C8—C9—C10 | 1.2 (3) |
N3—N2—C6—C2 | 175.06 (16) | C7—C8—C13—C12 | −179.0 (2) |
N2—N3—C7—C8 | 177.64 (17) | C9—C8—C13—C12 | −0.3 (3) |
N1—C1—C2—C3 | 0.4 (3) | C8—C9—C10—C11 | −1.4 (3) |
N1—C1—C2—C6 | −180.0 (2) | C8—C9—C10—C14 | 179.5 (2) |
C1—C2—C3—C4 | −1.8 (3) | C9—C10—C11—C12 | 0.6 (3) |
C6—C2—C3—C4 | 178.6 (2) | C9—C10—C11—C15 | −179.2 (2) |
C1—C2—C6—O1 | 19.6 (3) | C14—C10—C11—C12 | 179.7 (2) |
C1—C2—C6—N2 | −158.97 (18) | C14—C10—C11—C15 | −0.1 (3) |
C3—C2—C6—O1 | −160.9 (2) | C10—C11—C12—C13 | 0.2 (3) |
C3—C2—C6—N2 | 20.6 (3) | C15—C11—C12—C13 | −180.0 (2) |
C2—C3—C4—C5 | 1.3 (3) | C11—C12—C13—C8 | −0.4 (3) |
C3—C4—C5—N1 | 0.7 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+2, −z; (v) x, y+1, z; (vi) −x+1, y−1/2, −z−1/2; (vii) −x+1, y+1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2v | 0.86 | 2.07 | 2.897 (2) | 162 |
O2—H2A···O1 | 0.85 | 2.03 | 2.858 (2) | 163 |
O2—H2B···N1iii | 0.85 | 2.11 | 2.936 (2) | 163 |
C1—H1···O1 | 0.93 | 2.48 | 2.799 (2) | 100 |
C3—H3···O2v | 0.93 | 2.51 | 3.375 (3) | 156 |
C7—H7···O2v | 0.93 | 2.49 | 3.297 (3) | 145 |
Symmetry codes: (iii) x, −y+3/2, z+1/2; (v) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H15N3O·H2O |
Mr | 271.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.4762 (19), 6.5174 (14), 16.497 (2) |
β (°) | 101.629 (2) |
V (Å3) | 1419.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.56 × 0.53 × 0.49 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.953, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6293, 2475, 1583 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.132, 1.03 |
No. of reflections | 2475 |
No. of parameters | 183 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.18 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.07 | 2.897 (2) | 162 |
O2—H2A···O1 | 0.85 | 2.03 | 2.858 (2) | 163 |
O2—H2B···N1ii | 0.85 | 2.11 | 2.936 (2) | 163 |
C1—H1···O1 | 0.93 | 2.48 | 2.799 (2) | 100 |
C3—H3···O2i | 0.93 | 2.51 | 3.375 (3) | 156 |
C7—H7···O2i | 0.93 | 2.49 | 3.297 (3) | 145 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y+3/2, z+1/2. |
As part of our ongoing studies of the coordination chemistry of aroylhydrazones ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
In the molecule of (I), both C7—N3 [1.269 (3) Å] and C6—O1 [1.216 (2) Å] are close to double-bond separations, indicating that the Lewis structure shown in the scheme is only an approximation to the electron distribution in the molecule. Otherwise, the geometrical parameters for (I) are normal. The dihedral angle between the pyridine and benzene ring mean planes is 10.69 (10)°, indicating that the molecule is non-planar, which perhaps correlates with the intramolecular O—H···O hydrogen bond (Table 1). An intermolecular N—H···O link also occurs.