organic compounds
2,2,2-Trifluoro-N-(4-methyl-2-oxo-2H-chromen-7-yl)acetamide
aKey Laboratory of Natural Resources of Changbai Mountain & Functional Molecules (Yanbian University), Ministry of Eduction, Yanji 133002, People's Republic of China
*Correspondence e-mail: zqcong@ybu.edu.cn
In the title molecule, C12H8F3NO3, the trifluoromethyl group is rotationally disordered over three orientations in a 0.5:0.3:0.2 ratio. In the crystal, N—H⋯O hydrogen bonds link the molecules related by translation into chains along the c axis. The crystal packing exhibits π–π interactions between the pyran rings of neighboring molecules [centroid–centroid distance = 3.462 (4) Å] and short C⋯O contacts of 3.149 (4) Å.
Related literature
For applications of coumarin derivatives, see: Li et al. (2012). For potential applications of the title compound as a fluorescent probe for cyanide, see: Li et al. (2011).
Experimental
Crystal data
|
Refinement
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812009634/cv5256sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812009634/cv5256Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812009634/cv5256Isup3.cml
A solution of 7-amino-4-methylcoumarin (100 mg, 0.57 mmol) and trifluoroacetic anhydride (360 mg, 1.70 mmol) was stirred in THF (5 ml) at room temperature for 1 h under N2. Then the mixture was concentrated and the solid was recrystallized from THF to give the title compound (113.4 mg), yield 73.3%. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a mixture of tetrahydrofuran and petroleum (60–90 °C) at room temperature.
C-bound H-atoms were placed in calculated positions (C—H 0.93 and 0.96 Å) and were included in the
in the riding model with Uiso(H) = 1.5 or 1.2 Ueq(C). N-bound atom H1 was placed in calculated position with N-H = 0.86 Å and refined with Uiso(H) = 1.2 Ueq(N). Trifluoromethyl group was treated as rotationally disordered over three orientations with the occupancies refined in the initial cycles, but in the final cycle they were fixed to 0.5, 0.3 and 0.2, respectively.Coumarins, with the structure of benzopyrone, have many advantages including high fluorescence
large excellent light stability, and low toxicity. Therefore, coumarin derivatives have been used as fluorescent probes of pH, for detection of nitric oxide, nitroxide, and hydrogen peroxide so far. Moreover, coumarin derivatives have served as good chemosensors of anions including cyanide, fluoride, pyrophosphate, acetate, benzoate, and dihydrogenphosphate as well as various metal ions comprised of Hg (II), Cu(II), Zn(II), Ni(II), Ca(II), Pb(II), Mg(II), Fe(III), Al (III), Cr(III), and Ag(I) (Li et al., 2012). Herein, we report the of the title compound (I), a potential fluorescent probe for cyanide (Li et al., 2011).In (I) (Fig. 1), all bond lengths and angles are normal. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis c into chains. The crystal packing exhibits π···π interactions between the pyran rings from the neighboring molecules [centroid-centroid distance of 3.462 (4) Å] and short C···O contacts of 3.149 (4) Å.
For applications of coumarin derivatives, see: Li et al. (2012). For potential applications of the title compound as fluorescent probe for cyanide, see: Li et al. (2011).
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I) with the atomic numbering. Displacement ellipsoids are drawn at the 30% probalility level. |
C12H8F3NO3 | Z = 2 |
Mr = 271.19 | F(000) = 276 |
Triclinic, P1 | Dx = 1.590 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4897 (17) Å | Cell parameters from 4341 reflections |
b = 8.5777 (17) Å | θ = 3.3–27.7° |
c = 9.3677 (19) Å | µ = 0.15 mm−1 |
α = 89.36 (3)° | T = 293 K |
β = 68.27 (3)° | Block, colourless |
γ = 65.12 (3)° | 0.33 × 0.25 × 0.22 mm |
V = 566.3 (2) Å3 |
Rigaku R-AXIS RAPID diffractometer | 2558 independent reflections |
Radiation source: fine-focus sealed tube | 1660 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→11 |
Tmin = 0.954, Tmax = 0.968 | k = −9→11 |
5577 measured reflections | l = −12→12 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0898P)2] where P = (Fo2 + 2Fc2)/3 |
2558 reflections | (Δ/σ)max = 0.043 |
227 parameters | Δρmax = 0.32 e Å−3 |
84 restraints | Δρmin = −0.29 e Å−3 |
C12H8F3NO3 | γ = 65.12 (3)° |
Mr = 271.19 | V = 566.3 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4897 (17) Å | Mo Kα radiation |
b = 8.5777 (17) Å | µ = 0.15 mm−1 |
c = 9.3677 (19) Å | T = 293 K |
α = 89.36 (3)° | 0.33 × 0.25 × 0.22 mm |
β = 68.27 (3)° |
Rigaku R-AXIS RAPID diffractometer | 2558 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1660 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.968 | Rint = 0.025 |
5577 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 84 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.32 e Å−3 |
2558 reflections | Δρmin = −0.29 e Å−3 |
227 parameters |
Experimental. (See detailed section in the paper) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | Occ. (<1) | |
C1 | 0.2553 (3) | 0.1720 (2) | 0.69632 (18) | 0.0411 (4) | |
C2 | 0.2740 (3) | 0.0012 (2) | 0.66094 (19) | 0.0428 (5) | |
H2 | 0.2863 | −0.0729 | 0.7336 | 0.051* | |
C3 | 0.2746 (3) | −0.0569 (2) | 0.52793 (19) | 0.0378 (4) | |
C4 | 0.2947 (4) | −0.2365 (3) | 0.4954 (2) | 0.0558 (6) | |
H4A | 0.3023 | −0.2943 | 0.5827 | 0.084* | |
H4B | 0.4080 | −0.3019 | 0.4038 | 0.084* | |
H4C | 0.1866 | −0.2284 | 0.4789 | 0.084* | |
C5 | 0.2568 (3) | 0.0591 (2) | 0.41442 (17) | 0.0340 (4) | |
C6 | 0.2416 (2) | 0.2238 (2) | 0.44841 (17) | 0.0317 (4) | |
C7 | 0.2285 (3) | 0.3436 (2) | 0.34783 (17) | 0.0345 (4) | |
H7 | 0.2167 | 0.4531 | 0.3753 | 0.041* | |
C8 | 0.2336 (3) | 0.2953 (2) | 0.20462 (17) | 0.0326 (4) | |
C9 | 0.2482 (3) | 0.1313 (2) | 0.16628 (18) | 0.0411 (5) | |
H9 | 0.2504 | 0.1001 | 0.0706 | 0.049* | |
C10 | 0.2595 (3) | 0.0160 (2) | 0.26924 (19) | 0.0406 (4) | |
H10 | 0.2690 | −0.0927 | 0.2423 | 0.049* | |
C11 | 0.2084 (3) | 0.5682 (2) | 0.10611 (19) | 0.0367 (4) | |
C12 | 0.2258 (3) | 0.6488 (3) | −0.0436 (2) | 0.0470 (5) | |
F1 | 0.1414 (13) | 0.6068 (13) | −0.1225 (11) | 0.0525 (18) | 0.50 |
F2 | 0.1399 (19) | 0.8175 (10) | −0.0063 (12) | 0.065 (3) | 0.50 |
F3 | 0.4003 (12) | 0.5937 (15) | −0.1389 (9) | 0.068 (3) | 0.50 |
F1' | 0.215 (4) | 0.570 (3) | −0.150 (3) | 0.115 (8) | 0.30 |
F2' | 0.087 (3) | 0.821 (3) | −0.016 (2) | 0.078 (6) | 0.30 |
F3' | 0.383 (2) | 0.669 (3) | −0.096 (3) | 0.098 (6) | 0.30 |
F1'' | 0.102 (3) | 0.685 (4) | −0.094 (3) | 0.108 (10) | 0.20 |
F2'' | 0.273 (6) | 0.776 (3) | −0.0344 (18) | 0.090 (6) | 0.20 |
F3'' | 0.394 (5) | 0.524 (2) | −0.166 (2) | 0.104 (9) | 0.20 |
N1 | 0.2276 (2) | 0.40564 (18) | 0.09096 (15) | 0.0368 (4) | |
H1 | 0.2373 | 0.3638 | 0.0034 | 0.044* | |
O1 | 0.2404 (2) | 0.27853 (15) | 0.58734 (12) | 0.0395 (3) | |
O2 | 0.2518 (3) | 0.23117 (19) | 0.81527 (14) | 0.0599 (5) | |
O3 | 0.1836 (3) | 0.65505 (17) | 0.22024 (15) | 0.0554 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0547 (12) | 0.0453 (10) | 0.0236 (7) | −0.0192 (9) | −0.0200 (8) | 0.0085 (6) |
C2 | 0.0605 (13) | 0.0417 (10) | 0.0304 (8) | −0.0229 (9) | −0.0231 (8) | 0.0157 (7) |
C3 | 0.0504 (12) | 0.0351 (9) | 0.0319 (8) | −0.0214 (8) | −0.0184 (8) | 0.0117 (7) |
C4 | 0.0946 (19) | 0.0414 (11) | 0.0499 (10) | −0.0384 (12) | −0.0391 (12) | 0.0206 (8) |
C5 | 0.0453 (11) | 0.0336 (8) | 0.0280 (7) | −0.0194 (8) | −0.0179 (7) | 0.0090 (6) |
C6 | 0.0415 (10) | 0.0343 (8) | 0.0222 (7) | −0.0165 (7) | −0.0162 (7) | 0.0043 (6) |
C7 | 0.0512 (11) | 0.0293 (8) | 0.0292 (7) | −0.0202 (8) | −0.0200 (7) | 0.0070 (6) |
C8 | 0.0444 (10) | 0.0330 (8) | 0.0267 (7) | −0.0192 (7) | −0.0188 (7) | 0.0096 (6) |
C9 | 0.0690 (14) | 0.0402 (9) | 0.0301 (8) | −0.0298 (9) | −0.0302 (9) | 0.0096 (7) |
C10 | 0.0655 (13) | 0.0327 (8) | 0.0356 (8) | −0.0264 (9) | −0.0278 (9) | 0.0088 (7) |
C11 | 0.0477 (11) | 0.0370 (9) | 0.0359 (8) | −0.0234 (8) | −0.0227 (8) | 0.0146 (7) |
C12 | 0.0608 (15) | 0.0455 (11) | 0.0448 (10) | −0.0288 (10) | −0.0262 (11) | 0.0207 (8) |
F1 | 0.078 (5) | 0.055 (4) | 0.056 (3) | −0.038 (4) | −0.052 (3) | 0.037 (3) |
F2 | 0.102 (8) | 0.032 (3) | 0.066 (3) | −0.026 (4) | −0.043 (5) | 0.028 (2) |
F3 | 0.049 (3) | 0.093 (8) | 0.056 (4) | −0.035 (5) | −0.011 (3) | 0.032 (5) |
F1' | 0.23 (2) | 0.080 (10) | 0.067 (9) | −0.075 (15) | −0.088 (15) | 0.039 (7) |
F2' | 0.067 (7) | 0.073 (8) | 0.070 (6) | −0.007 (4) | −0.030 (4) | 0.040 (5) |
F3' | 0.056 (7) | 0.112 (15) | 0.127 (15) | −0.047 (10) | −0.030 (9) | 0.076 (11) |
F1'' | 0.078 (10) | 0.14 (2) | 0.119 (15) | −0.043 (14) | −0.058 (10) | 0.089 (16) |
F2'' | 0.175 (18) | 0.073 (11) | 0.063 (7) | −0.083 (12) | −0.057 (12) | 0.038 (7) |
F3'' | 0.135 (16) | 0.072 (9) | 0.044 (5) | −0.035 (10) | 0.012 (7) | 0.007 (6) |
N1 | 0.0603 (11) | 0.0358 (7) | 0.0268 (6) | −0.0268 (7) | −0.0245 (7) | 0.0120 (5) |
O1 | 0.0628 (9) | 0.0376 (6) | 0.0253 (5) | −0.0235 (6) | −0.0240 (6) | 0.0071 (4) |
O2 | 0.0991 (13) | 0.0576 (9) | 0.0330 (6) | −0.0343 (9) | −0.0380 (8) | 0.0094 (6) |
O3 | 0.0959 (13) | 0.0392 (7) | 0.0502 (8) | −0.0366 (8) | −0.0420 (8) | 0.0136 (6) |
C1—O2 | 1.215 (2) | C8—N1 | 1.417 (2) |
C1—O1 | 1.367 (2) | C9—C10 | 1.373 (2) |
C1—C2 | 1.434 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.345 (2) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—O3 | 1.209 (2) |
C3—C5 | 1.454 (2) | C11—N1 | 1.337 (2) |
C3—C4 | 1.499 (2) | C11—C12 | 1.542 (2) |
C4—H4A | 0.9600 | C12—F1'' | 1.23 (2) |
C4—H4B | 0.9600 | C12—F1' | 1.259 (19) |
C4—H4C | 0.9600 | C12—F3 | 1.287 (8) |
C5—C6 | 1.393 (2) | C12—F2 | 1.297 (8) |
C5—C10 | 1.403 (2) | C12—F3' | 1.327 (15) |
C6—O1 | 1.3835 (17) | C12—F2'' | 1.327 (14) |
C6—C7 | 1.384 (2) | C12—F1 | 1.343 (7) |
C7—C8 | 1.388 (2) | C12—F2' | 1.400 (18) |
C7—H7 | 0.9300 | C12—F3'' | 1.42 (2) |
C8—C9 | 1.398 (2) | N1—H1 | 0.8600 |
O2—C1—O1 | 116.61 (16) | F1'—C12—F3' | 111.2 (12) |
O2—C1—C2 | 125.67 (16) | F3—C12—F3' | 30.8 (9) |
O1—C1—C2 | 117.72 (13) | F2—C12—F3' | 84.4 (9) |
C3—C2—C1 | 123.21 (15) | F1''—C12—F2'' | 114.2 (12) |
C3—C2—H2 | 118.4 | F1'—C12—F2'' | 134.9 (11) |
C1—C2—H2 | 118.4 | F3—C12—F2'' | 72.7 (13) |
C2—C3—C5 | 118.12 (15) | F2—C12—F2'' | 42.9 (14) |
C2—C3—C4 | 121.53 (15) | F3'—C12—F2'' | 42.7 (10) |
C5—C3—C4 | 120.35 (14) | F1''—C12—F1 | 27.2 (16) |
C3—C4—H4A | 109.5 | F1'—C12—F1 | 22.9 (14) |
C3—C4—H4B | 109.5 | F3—C12—F1 | 105.9 (5) |
H4A—C4—H4B | 109.5 | F2—C12—F1 | 106.3 (5) |
C3—C4—H4C | 109.5 | F3'—C12—F1 | 129.8 (11) |
H4A—C4—H4C | 109.5 | F2''—C12—F1 | 135.9 (10) |
H4B—C4—H4C | 109.5 | F1''—C12—F2' | 59.8 (14) |
C6—C5—C10 | 116.77 (14) | F1'—C12—F2' | 105.0 (11) |
C6—C5—C3 | 118.39 (13) | F3—C12—F2' | 123.9 (9) |
C10—C5—C3 | 124.81 (14) | F2—C12—F2' | 20.2 (10) |
O1—C6—C7 | 115.01 (13) | F3'—C12—F2' | 101.2 (11) |
O1—C6—C5 | 121.47 (13) | F2''—C12—F2' | 62.0 (14) |
C7—C6—C5 | 123.52 (13) | F1—C12—F2' | 87.0 (9) |
C6—C7—C8 | 117.96 (14) | F1''—C12—F3'' | 104.1 (14) |
C6—C7—H7 | 121.0 | F1'—C12—F3'' | 59.8 (11) |
C8—C7—H7 | 121.0 | F3—C12—F3'' | 28.5 (10) |
C7—C8—C9 | 120.26 (14) | F2—C12—F3'' | 135.5 (9) |
C7—C8—N1 | 122.56 (14) | F3'—C12—F3'' | 59.3 (10) |
C9—C8—N1 | 117.18 (12) | F2''—C12—F3'' | 100.8 (12) |
C10—C9—C8 | 120.32 (13) | F1—C12—F3'' | 82.7 (15) |
C10—C9—H9 | 119.8 | F2'—C12—F3'' | 139.8 (12) |
C8—C9—H9 | 119.8 | F1''—C12—C11 | 120.0 (10) |
C9—C10—C5 | 121.17 (14) | F1'—C12—C11 | 115.8 (9) |
C9—C10—H10 | 119.4 | F3—C12—C11 | 111.5 (4) |
C5—C10—H10 | 119.4 | F2—C12—C11 | 109.2 (4) |
O3—C11—N1 | 127.88 (15) | F3'—C12—C11 | 109.6 (8) |
O3—C11—C12 | 117.70 (15) | F2''—C12—C11 | 108.7 (5) |
N1—C11—C12 | 114.40 (14) | F1—C12—C11 | 112.2 (4) |
F1''—C12—F1' | 47.4 (13) | F2'—C12—C11 | 113.0 (8) |
F1''—C12—F3 | 119.8 (13) | F3''—C12—C11 | 106.8 (10) |
F1'—C12—F3 | 84.0 (13) | C11—N1—C8 | 126.56 (12) |
F1''—C12—F2 | 79.3 (15) | C11—N1—H1 | 116.7 |
F1'—C12—F2 | 122.1 (9) | C8—N1—H1 | 116.7 |
F3—C12—F2 | 111.5 (6) | C1—O1—C6 | 121.07 (13) |
F1''—C12—F3' | 130.4 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.05 | 2.8960 (19) | 170 |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C12H8F3NO3 |
Mr | 271.19 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.4897 (17), 8.5777 (17), 9.3677 (19) |
α, β, γ (°) | 89.36 (3), 68.27 (3), 65.12 (3) |
V (Å3) | 566.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.33 × 0.25 × 0.22 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.954, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5577, 2558, 1660 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.143, 1.01 |
No. of reflections | 2558 |
No. of parameters | 227 |
No. of restraints | 84 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.29 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC and Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.05 | 2.8960 (19) | 170.0 |
Symmetry code: (i) x, y, z−1. |
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21062022) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin Universty.
References
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, H. Q., Cai, L. & Chen, Z. (2012). Advances in Chemical Sensors, Coumarin-Derived Flurescent Chemosensors, p. 121. Rijeka, Croatia: Intech. Google Scholar
Li, H. D., Li, B., Jin, L. Y., Kan, Y. H. & Yin, B. Z. (2011). Tetrahedron, 67, 7348–7353. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC & Rigaku (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
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Coumarins, with the structure of benzopyrone, have many advantages including high fluorescence quantum yield, large Stokes shift, excellent light stability, and low toxicity. Therefore, coumarin derivatives have been used as fluorescent probes of pH, for detection of nitric oxide, nitroxide, and hydrogen peroxide so far. Moreover, coumarin derivatives have served as good chemosensors of anions including cyanide, fluoride, pyrophosphate, acetate, benzoate, and dihydrogenphosphate as well as various metal ions comprised of Hg (II), Cu(II), Zn(II), Ni(II), Ca(II), Pb(II), Mg(II), Fe(III), Al (III), Cr(III), and Ag(I) (Li et al., 2012). Herein, we report the crystal structure of the title compound (I), a potential fluorescent probe for cyanide (Li et al., 2011).
In (I) (Fig. 1), all bond lengths and angles are normal. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis c into chains. The crystal packing exhibits π···π interactions between the pyran rings from the neighboring molecules [centroid-centroid distance of 3.462 (4) Å] and short C···O contacts of 3.149 (4) Å.