In the crystal of the title compound, the molecules are linked via C—H⋯O hydrogen bonds, giving rise to centrosymmetric inversion dimers. On one side of the molecule, C—H⋯O interactions generate R22(16)ring motifs, while on the opposite side, C—H⋯O hydrogen bonds form R22(14) ring motifs.
Keywords: crystal structure, Hirshfeld surface, two-dimensional fingerprint, 2H-chromene-3-carboxamide
Abstract
In the title compound, C15H10N2O3, the dihedral angle between the heterocyclic 2H-chromene and the pyridine moieties is 2.09 (9)°. The molecule exhibits an almost planar conformation (r.m.s. deviation = 0.048 Å). The torsion angle associated with the amide linkage between the 2H-chromene and pyridine moieties is −179.17 (18)ο and found to be anti-periplanar. In the crystal, C—H⋯O hydrogen bonds form two sets of inversion dimers, generating R22(14) and R22(16) synthons that propagate along the [010] direction. The molecular packing in the crystal is further consolidated by C= O⋯π interactions and π–π stacking with centroid–centroid separations of 3.732 (2), 3.815 (2) and 3.947 (2) Å. The two-dimensional fingerprint plots indicate that the major contributions to the crystal packing arise from H⋯O/O⋯H (19.5%), H⋯C/C⋯H (14.1%), H⋯N/N⋯H (8.0%) and O⋯C/C⋯O (5.0%) interactions.
1. Chemical context
The 2-oxo-2H-chromene (coumarin) scaffold is of considerable interest due to its diverse biological and physicochemical properties. Coumarin derivatives, both natural and synthetic, exhibit a broad range of pharmacological activities, including antioxidant, anti-inflammatory and anticoagulant effects (Annunziata et al., 2020 ▸; Ivanov et al., 2025 ▸). They have also been reported to show significant anticancer activity through inhibition of cell proliferation and modulation of signalling pathways (Emami & Dadashpour, 2015 ▸), as well as antimicrobial activity against pathogens such as Staphylococcus aureus and Escherichia coli (Tang et al., 2025 ▸; Baaiu et al., 2025 ▸). In addition to pharmaceutical relevance, coumarin derivatives find applications in other fields owing to their characteristic odour, fluorescence properties and agrochemical activity (Anywar & Muhumuza, 2024 ▸). In particular, chromene-3-carboxamide derivatives have attracted attention due to their cytotoxic activity and their ability to inhibit cancer-related enzymes such as carbonic anhydrase IX (Supuran et al., 2017 ▸). These compounds also exhibit antibacterial activity against both Gram-positive and Gram-negative bacteria (Khan et al., 2020 ▸).
Furthermore, the presence of amide and heterocyclic donor groups, such as pyridin-4-yl moieties, enhances their ability to coordinate with metal ions, making them useful in coordination chemistry and crystal engineering (El-Sayed et al., 2023 ▸; Kaur et al., 2015 ▸). Such coordination behaviour facilitates the formation of supramolecular assemblies and functional materials. On the basis of these considerations, coumarin–pyridine hybrid systems are of particular interest, and we report herein the synthesis and crystal structure of a new derivative.
2. Structural commentary
In the title compound (Fig. 1 ▸), the fused 2H-chromene ring system (C8–C11/O1/C12–C16) and the pyridine ring (C1–C3/N2/C5/C6) are nearly coplanar, forming a dihedral angle of 2.09 (9)°, with an r.m.s. deviation of 0.048 Å, indicating an essentially planar conformation. The amide linkage between the 2H-chromene and pyridine moieties adopts an anti-periplanar conformation, as evidenced by the C8—C7(=O2)—N1—C1 torsion angle of −179.17 (18)°. Bond lengths and angles are within normal ranges. Intramolecular N1—H1⋯O3, C6—H6⋯O2 and C9—H9⋯O2 hydrogen bonds are observed (see Table 1 ▸ for details), contributing to the stabilization of the molecular conformation.
Figure 1.
The title compound with the atom-numbering scheme and 50% probability ellipsoids.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O3 | 0.86 | 1.97 | 2.698 (2) | 141 |
| C6—H6⋯O2 | 0.93 | 2.29 | 2.869 (3) | 120 |
| C9—H9⋯O2 | 0.93 | 2.44 | 2.758 (3) | 100 |
| C2—H2⋯O3i | 0.93 | 2.58 | 3.480 (3) | 162 |
| C13—H13⋯O2ii | 0.93 | 2.59 | 3.422 (3) | 149 |
Symmetry codes: (i) 
; (ii) 
.
3. Supramolecular features
In the crystal, the molecules are linked via C—H⋯O hydrogen bonds, giving rise to centrosymmetric inversion dimers (Table 1 ▸). On one side of the molecule, C2—H2⋯O3 interactions generate 
(16) ring motifs, while on the opposite side, C13—H13⋯O2 hydrogen bonds form (14) ring motifs. These discrete supramolecular synthons propagate along the [010] direction (Fig. 2 ▸). The crystal packing is further consolidated by C=O⋯π interactions involving the carbonyl group C7=O2 and the π-system of the 2H-chromene ring [Fig. 3 ▸; O2⋯Cg1(1 − x, 1 − y, 1 − z) = 3.279 (2) Å, Cg1 is the centroid of the O1/C8–C12 ring]. In addition, significant π–π stacking interactions are observed between adjacent aromatic systems (Fig. 4 ▸). The centroid–centroid separations are Cg1⋯Cg2(1 − x, −y, 1 − z) = 3.815 (2) Å, Cg2⋯Cg3(1 − x, 1 − y, 1 − z) = 3.732 (2) Å and Cg2⋯Cg3(1 − x, 2 − y, 1 − z) = 3.947 (2) Å, where Cg2 and Cg3 are the centroids of the pyridine (N2/C1–C3/C5–C6) and 2H-chromene benzene (C10/C11/C13–C16) rings, respectively. These non-covalent interactions collectively contribute to the cohesion of the three-dimensional crystal architecture.
Figure 2.
The packing of the title compound. Intermolecular C—H⋯O hydrogen bonds are shown as blue dashed lines.
Figure 3.
Partial crystal packing of the title compound showing the C—O⋯π interactions as blue dashed lines.
Figure 4.
Crystal packing of the title compound showing the π–π interactions as blue dashed lines.
4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.43, 2025 update; Groom et al., 2016 ▸) for structures containing the 2-oxo-2H-chromene-3-carboxamide moiety yielded more than 30 hits. Among these, closely related structures include 7-(diethylamino)-N-(4-nitrophenyl)-2-oxo-2H-chromene-3-carboxamide (refcode DISYIP; Maldonado-Domínguez et al., 2014 ▸), 7-(diethylamino)-N-(4-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide (DISXUA; Maldonado-Domínguez et al., 2014 ▸), and 7-(diethylamino)-N-(3-methyl-1,3-benzothiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (DUBHOZ; Wang et al., 2015 ▸), which exhibit dihedral angles of 0.28, 0.79 and 2.85°, respectively, indicating a strong tendency toward planarity in this class of compounds similar to the title molecule.
The torsional angle associated with the amide linkage in representative examples N-(3-(imidazo[1,2-a]pyridin-2-yl)phenyl)-8-methoxy-2-oxo-2H-chromene-3-carboxamide (BONKAS; Julien et al., 2014 ▸), 7-(diethylamino)-N-(4-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide, N-(4-cyanophenyl)-7-(diethylamino)-2-oxo-2H-chromene-3-carboxamide and 7-(diethylamino)-N-(4-nitrophenyl)-2-oxo-2H-chromene-3-carboxamide (DISXUA, DISYEL and DISYIP, respectively; Maldonado-Domínguez et al., 2014 ▸) are 179.96, 177.26, −179.17 and −177.43°, respectively, reflecting an anti-periplanar conformation. In the representative examples 7-(diethylamino)-N-(3-methyl-1,3-benzothiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (DUBHOZ; Wang et al., 2015 ▸) and 6-methoxy-N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide (ECEBIA; Gomes et al., 2016 ▸) the torsion angles are −177.73 and −179.06°, respectively, reflecting the same anti-periplanar conformation as comparable to the title molecule.
5. Hirshfeld surface analysis
A Hirshfeld surface analysis of the title compound was carried out using CrystalExplorer (Spackman et al., 2021 ▸) to investigate and visualize the intermolecular interactions governing the crystal packing. The Hirshfeld surface mapped over dnorm together with two neighbouring molecules is shown in Fig. 5 ▸, On one side of the molecule, the oxygen atom of the amide linkage takes part in C2—H2⋯O3 interactions generating (16) ring motifs, while on the opposite side, the oxygen of the 2-oxo-2H-chromene moiety takes part in C13—H13⋯O2 hydrogen bonds forming (14) ring motifs, where red spots correspond to regions of these close intermolecular contacts. The two-dimensional fingerprint plots provide a quantitative description of the various intermolecular interactions. The most significant contributions arise from H⋯H contacts (35.1%), followed by H⋯O/O⋯H (19.5%), H⋯C/C⋯H (14.1%), H⋯N/N⋯H (8.2%) and O⋯C/C⋯O (5.7%) interactions (Fig. 6 ▸). These results indicate that van der Waals interactions (H⋯H) dominate the crystal packing, while directional hydrogen-bonding and heteroatom contacts make notable secondary contributions.
Figure 5.
View of the three-dimensional Hirshfeld surface mapped over dnorm and the C—H⋯O interactions forming (16) and (14) ring motifs with neighboring molecules
Figure 6.
The two-dimensional fingerprint plots showing all (100%), H⋯H (31.5%), H⋯O/O⋯H (19.5%), H⋯C/C⋯H (14.1%), H⋯N/N⋯H (8.0%), and O⋯C/C⋯O (5.0%) contacts.
6. Synthesis and crystallization
A mixture of 2-oxo-2H-chromene-3-carboxylic acid (1.00 mmol), 4-aminopyridine (2.00 mmol) and triethyl amine (TEA; 4.2 mmol) in acetonitrile (15 ml) was stirred at room temperature for 15 min. Then, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU; 5 mmol) was added in one portion, and the reaction was covered with a rubber septum. After 24 h, the acetonitrile was removed in vacuo, and the residue was dissolved in dichloromethane (25 ml). The organic layer was washed with water (25 ml) and separated; the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude residue was purified by 60–120 mesh silica gel column chromatography (1:4 ethyl acetate:hexane). The scheme for the reaction is presented in Fig. 7 ▸.
Figure 7.
Reaction scheme for the synthesis of the title compound.
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were positioned with idealized geometry (N—H = 0.83 Å, C—H = 0.93 Å) and refined using a riding model with Uiso(H) = 1.2Ueq(C/N).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C15H10N2O3 |
| M r | 266.25 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 299 |
| a, b, c (Å) | 5.731 (2), 7.668 (3), 13.911 (5) |
| α, β, γ (°) | 103.199 (14), 93.059 (11), 94.332 (10) |
| V (Å3) | 591.8 (4) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.11 |
| Crystal size (mm) | 0.32 × 0.27 × 0.24 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.964, 0.973 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 8155, 3181, 2263 |
| R int | 0.034 |
| (sin θ/λ)max (Å−1) | 0.697 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.184, 1.02 |
| No. of reflections | 3181 |
| No. of parameters | 181 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.35, −0.22 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026003798/vm2329sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026003798/vm2329Isup3.hkl
Supporting information file. DOI: 10.1107/S2056989026003798/vm2329Isup3.cml
CCDC reference: 2545176
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Solid State and Structural Chemistry Unit (SSCU), Indian Institute of Science (IISc) and iSTEM facilities for their help with the single-crystal data collection. MSK thanks the BSPM lab, Centre of Innovative Science, Engineering and Education (CISEE) for extending their help in carrying out experiments and use of software facilities to complete the research work at University College of Science (UCS), Tumkur University Tumkur.
supplementary crystallographic information
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Crystal data
| C15H10N2O3 | Z = 2 |
| Mr = 266.25 | F(000) = 276 |
| Triclinic, P1 | Dx = 1.494 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 410 K |
| a = 5.731 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 7.668 (3) Å | Cell parameters from 2253 reflections |
| c = 13.911 (5) Å | θ = 0.2–29.0° |
| α = 103.199 (14)° | µ = 0.11 mm−1 |
| β = 93.059 (11)° | T = 299 K |
| γ = 94.332 (10)° | Prism, colourless |
| V = 591.8 (4) Å3 | 0.32 × 0.27 × 0.24 mm |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Data collection
| Bruker SMART APEXII CCD diffractometer | 3181 independent reflections |
| Radiation source: fine-focus sealed tube | 2263 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.034 |
| Detector resolution: 1.7 pixels mm-1 | θmax = 29.7°, θmin = 2.7° |
| φ and Ω scans | h = −7→7 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −10→8 |
| Tmin = 0.964, Tmax = 0.973 | l = −19→19 |
| 8155 measured reflections |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Refinement
| 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)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.184 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0775P)2 + 0.3022P] where P = (Fo2 + 2Fc2)/3 |
| 3181 reflections | (Δ/σ)max < 0.001 |
| 181 parameters | Δρmax = 0.35 e Å−3 |
| 0 restraints | Δρmin = −0.22 e Å−3 |
| 0 constraints |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . 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. |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.6621 (2) | 0.66045 (19) | 0.30075 (10) | 0.0408 (4) | |
| N1 | 0.5999 (3) | 0.8748 (2) | 0.60639 (12) | 0.0391 (4) | |
| H1 | 0.709158 | 0.903908 | 0.571403 | 0.047* | |
| C1 | 0.6267 (3) | 0.9567 (2) | 0.70744 (14) | 0.0343 (4) | |
| O2 | 0.2543 (3) | 0.7009 (2) | 0.59463 (11) | 0.0530 (5) | |
| C2 | 0.8347 (4) | 1.0609 (3) | 0.74418 (16) | 0.0429 (5) | |
| H2 | 0.951919 | 1.076508 | 0.702375 | 0.051* | |
| O3 | 0.8239 (3) | 0.8350 (2) | 0.43803 (12) | 0.0546 (5) | |
| C3 | 0.8642 (4) | 1.1408 (3) | 0.84403 (17) | 0.0489 (6) | |
| H3 | 1.003647 | 1.211559 | 0.867377 | 0.059* | |
| N2 | 0.7074 (4) | 1.1241 (3) | 0.90939 (14) | 0.0500 (5) | |
| C5 | 0.5084 (4) | 1.0255 (3) | 0.87212 (16) | 0.0463 (5) | |
| H5 | 0.394600 | 1.012612 | 0.915832 | 0.056* | |
| C6 | 0.4575 (4) | 0.9411 (3) | 0.77383 (15) | 0.0407 (5) | |
| H6 | 0.313624 | 0.875356 | 0.752407 | 0.049* | |
| C7 | 0.4221 (3) | 0.7544 (3) | 0.55616 (15) | 0.0368 (4) | |
| C8 | 0.4456 (3) | 0.6886 (3) | 0.44736 (14) | 0.0339 (4) | |
| C9 | 0.2666 (3) | 0.5796 (3) | 0.39258 (14) | 0.0357 (4) | |
| H9 | 0.133815 | 0.550586 | 0.423391 | 0.043* | |
| C10 | 0.2754 (3) | 0.5076 (3) | 0.28884 (14) | 0.0343 (4) | |
| C11 | 0.4783 (3) | 0.5494 (3) | 0.24507 (14) | 0.0354 (4) | |
| C12 | 0.6545 (4) | 0.7357 (3) | 0.39968 (14) | 0.0374 (4) | |
| C13 | 0.0925 (4) | 0.3980 (3) | 0.22872 (16) | 0.0430 (5) | |
| H13 | −0.045401 | 0.368823 | 0.256137 | 0.052* | |
| C14 | 0.1153 (4) | 0.3332 (3) | 0.12939 (16) | 0.0471 (5) | |
| H14 | −0.007513 | 0.261687 | 0.089546 | 0.056* | |
| C15 | 0.3218 (4) | 0.3747 (3) | 0.08887 (16) | 0.0486 (6) | |
| H15 | 0.337020 | 0.328822 | 0.021821 | 0.058* | |
| C16 | 0.5058 (4) | 0.4830 (3) | 0.14592 (15) | 0.0443 (5) | |
| H16 | 0.644142 | 0.510211 | 0.118265 | 0.053* |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0374 (8) | 0.0506 (9) | 0.0319 (7) | −0.0050 (6) | 0.0080 (6) | 0.0060 (6) |
| N1 | 0.0397 (9) | 0.0443 (10) | 0.0312 (8) | −0.0038 (7) | 0.0077 (7) | 0.0060 (7) |
| C1 | 0.0399 (10) | 0.0314 (9) | 0.0316 (9) | 0.0028 (8) | 0.0029 (8) | 0.0071 (7) |
| O2 | 0.0484 (9) | 0.0697 (11) | 0.0352 (8) | −0.0153 (8) | 0.0113 (7) | 0.0051 (7) |
| C2 | 0.0406 (11) | 0.0458 (12) | 0.0414 (11) | −0.0025 (9) | 0.0062 (9) | 0.0099 (9) |
| O3 | 0.0417 (9) | 0.0716 (11) | 0.0425 (9) | −0.0166 (8) | 0.0091 (7) | 0.0029 (8) |
| C3 | 0.0470 (12) | 0.0492 (13) | 0.0440 (12) | −0.0108 (10) | −0.0022 (10) | 0.0034 (10) |
| N2 | 0.0584 (12) | 0.0505 (11) | 0.0364 (10) | −0.0014 (9) | 0.0012 (8) | 0.0026 (8) |
| C5 | 0.0511 (13) | 0.0494 (12) | 0.0361 (11) | 0.0007 (10) | 0.0094 (9) | 0.0051 (9) |
| C6 | 0.0395 (11) | 0.0416 (11) | 0.0371 (11) | −0.0039 (8) | 0.0042 (8) | 0.0035 (8) |
| C7 | 0.0386 (10) | 0.0386 (10) | 0.0326 (10) | 0.0012 (8) | 0.0043 (8) | 0.0073 (8) |
| C8 | 0.0344 (10) | 0.0371 (10) | 0.0306 (9) | 0.0011 (8) | 0.0053 (7) | 0.0088 (7) |
| C9 | 0.0353 (10) | 0.0386 (10) | 0.0337 (10) | 0.0011 (8) | 0.0059 (8) | 0.0093 (8) |
| C10 | 0.0372 (10) | 0.0338 (10) | 0.0313 (10) | 0.0033 (8) | 0.0031 (8) | 0.0065 (7) |
| C11 | 0.0384 (10) | 0.0342 (10) | 0.0339 (10) | 0.0025 (8) | 0.0044 (8) | 0.0084 (8) |
| C12 | 0.0395 (10) | 0.0386 (10) | 0.0334 (10) | 0.0006 (8) | 0.0056 (8) | 0.0073 (8) |
| C13 | 0.0411 (11) | 0.0443 (12) | 0.0412 (12) | −0.0013 (9) | 0.0039 (9) | 0.0062 (9) |
| C14 | 0.0520 (13) | 0.0454 (12) | 0.0389 (11) | −0.0011 (10) | −0.0027 (10) | 0.0028 (9) |
| C15 | 0.0678 (15) | 0.0482 (13) | 0.0284 (10) | 0.0098 (11) | 0.0049 (10) | 0.0045 (9) |
| C16 | 0.0479 (12) | 0.0509 (13) | 0.0356 (11) | 0.0037 (10) | 0.0118 (9) | 0.0116 (9) |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Geometric parameters (Å, º)
| O1—C12 | 1.370 (2) | C5—H5 | 0.9300 |
| O1—C11 | 1.382 (2) | C6—H6 | 0.9300 |
| N1—C7 | 1.366 (3) | C7—C8 | 1.499 (3) |
| N1—C1 | 1.398 (2) | C8—C9 | 1.352 (3) |
| N1—H1 | 0.8600 | C8—C12 | 1.461 (3) |
| C1—C2 | 1.388 (3) | C9—C10 | 1.428 (3) |
| C1—C6 | 1.391 (3) | C9—H9 | 0.9300 |
| O2—O2 | 0.000 (5) | C10—C11 | 1.391 (3) |
| O2—O2 | 0.000 (5) | C10—C13 | 1.399 (3) |
| O2—C7 | 1.215 (2) | C11—C16 | 1.379 (3) |
| C2—C3 | 1.380 (3) | C13—C14 | 1.374 (3) |
| C2—H2 | 0.9300 | C13—H13 | 0.9300 |
| O3—O3 | 0.000 (5) | C14—C15 | 1.384 (3) |
| O3—C12 | 1.206 (2) | C14—H14 | 0.9300 |
| C3—N2 | 1.332 (3) | C15—C16 | 1.381 (3) |
| C3—H3 | 0.9300 | C15—H15 | 0.9300 |
| N2—C5 | 1.330 (3) | C16—H16 | 0.9300 |
| C5—C6 | 1.378 (3) | ||
| C12—O1—C11 | 122.70 (15) | C9—C8—C7 | 118.04 (17) |
| C7—N1—C1 | 128.19 (17) | C12—C8—C7 | 122.45 (17) |
| C7—N1—H1 | 115.9 | C8—C9—C10 | 121.95 (18) |
| C1—N1—H1 | 115.9 | C8—C9—H9 | 119.0 |
| C2—C1—C6 | 117.69 (18) | C10—C9—H9 | 119.0 |
| C2—C1—N1 | 118.11 (18) | C11—C10—C13 | 118.14 (18) |
| C6—C1—N1 | 124.20 (18) | C11—C10—C9 | 117.87 (18) |
| C3—C2—C1 | 118.6 (2) | C13—C10—C9 | 123.99 (18) |
| C3—C2—H2 | 120.7 | C16—C11—O1 | 117.38 (17) |
| C1—C2—H2 | 120.7 | C16—C11—C10 | 122.19 (19) |
| N2—C3—C2 | 124.8 (2) | O1—C11—C10 | 120.43 (17) |
| N2—C3—H3 | 117.6 | O3—C12—O1 | 115.52 (17) |
| C2—C3—H3 | 117.6 | O3—C12—O1 | 115.52 (17) |
| C5—N2—C3 | 115.42 (19) | O3—C12—C8 | 127.00 (19) |
| N2—C5—C6 | 125.1 (2) | O3—C12—C8 | 127.00 (19) |
| N2—C5—H5 | 117.4 | O1—C12—C8 | 117.48 (17) |
| C6—C5—H5 | 117.4 | C14—C13—C10 | 120.4 (2) |
| C5—C6—C1 | 118.3 (2) | C14—C13—H13 | 119.8 |
| C5—C6—H6 | 120.8 | C10—C13—H13 | 119.8 |
| C1—C6—H6 | 120.8 | C13—C14—C15 | 119.8 (2) |
| O2—C7—N1 | 123.95 (19) | C13—C14—H14 | 120.1 |
| O2—C7—N1 | 123.95 (19) | C15—C14—H14 | 120.1 |
| O2—C7—N1 | 123.95 (19) | C16—C15—C14 | 121.4 (2) |
| O2—C7—C8 | 120.60 (18) | C16—C15—H15 | 119.3 |
| O2—C7—C8 | 120.60 (18) | C14—C15—H15 | 119.3 |
| O2—C7—C8 | 120.60 (18) | C11—C16—C15 | 118.08 (19) |
| N1—C7—C8 | 115.45 (16) | C11—C16—H16 | 121.0 |
| C9—C8—C12 | 119.50 (18) | C15—C16—H16 | 121.0 |
| C7—N1—C1—C2 | 173.33 (19) | C8—C9—C10—C11 | 1.6 (3) |
| C7—N1—C1—C6 | −6.9 (3) | C8—C9—C10—C13 | −178.3 (2) |
| C6—C1—C2—C3 | 0.9 (3) | C12—O1—C11—C16 | 179.46 (18) |
| N1—C1—C2—C3 | −179.3 (2) | C12—O1—C11—C10 | −0.7 (3) |
| C1—C2—C3—N2 | 0.8 (4) | C13—C10—C11—C16 | −1.7 (3) |
| C2—C3—N2—C5 | −1.7 (4) | C9—C10—C11—C16 | 178.44 (19) |
| C3—N2—C5—C6 | 0.8 (4) | C13—C10—C11—O1 | 178.54 (18) |
| N2—C5—C6—C1 | 0.9 (4) | C9—C10—C11—O1 | −1.4 (3) |
| C2—C1—C6—C5 | −1.7 (3) | C11—O1—C12—O3 | −177.37 (18) |
| N1—C1—C6—C5 | 178.55 (19) | C11—O1—C12—O3 | −177.37 (18) |
| C1—N1—C7—O2 | 0.6 (3) | C11—O1—C12—C8 | 2.5 (3) |
| C1—N1—C7—O2 | 0.6 (3) | C9—C8—C12—O3 | 177.6 (2) |
| C1—N1—C7—O2 | 0.6 (3) | C7—C8—C12—O3 | −3.4 (3) |
| C1—N1—C7—C8 | −179.17 (18) | C9—C8—C12—O3 | 177.6 (2) |
| O2—C7—C8—C9 | 5.0 (3) | C7—C8—C12—O3 | −3.4 (3) |
| O2—C7—C8—C9 | 5.0 (3) | C9—C8—C12—O1 | −2.3 (3) |
| O2—C7—C8—C9 | 5.0 (3) | C7—C8—C12—O1 | 176.68 (17) |
| N1—C7—C8—C9 | −175.21 (18) | C11—C10—C13—C14 | 0.5 (3) |
| O2—C7—C8—C12 | −174.0 (2) | C9—C10—C13—C14 | −179.6 (2) |
| O2—C7—C8—C12 | −174.0 (2) | C10—C13—C14—C15 | 0.8 (3) |
| O2—C7—C8—C12 | −174.0 (2) | C13—C14—C15—C16 | −1.0 (4) |
| N1—C7—C8—C12 | 5.8 (3) | O1—C11—C16—C15 | −178.72 (18) |
| C12—C8—C9—C10 | 0.3 (3) | C10—C11—C16—C15 | 1.5 (3) |
| C7—C8—C9—C10 | −178.74 (17) | C14—C15—C16—C11 | −0.1 (3) |
2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.86 | 1.97 | 2.698 (2) | 141 |
| C6—H6···O2 | 0.93 | 2.29 | 2.869 (3) | 120 |
| C9—H9···O2 | 0.93 | 2.44 | 2.758 (3) | 100 |
| C2—H2···O3i | 0.93 | 2.58 | 3.480 (3) | 162 |
| C13—H13···O2ii | 0.93 | 2.59 | 3.422 (3) | 149 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x, −y+1, −z+1.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026003798/vm2329sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026003798/vm2329Isup3.hkl
Supporting information file. DOI: 10.1107/S2056989026003798/vm2329Isup3.cml
CCDC reference: 2545176
Additional supporting information: crystallographic information; 3D view; checkCIF report