Synthesis, crystal structure and Hirshfeld surface analysis of 2-oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide

Sunithakumari, M.; Harish Kumar, M.; Devarajegowda, H.C.; Gagan, M.U.; Dwarakanath, V.; Palakshamurthy, B.S.

doi:10.1107/S2056989026003798

research communications

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ISSN: 2056-9890

Volume 82| Part 5| May 2026| Pages 516-520

https://doi.org/10.1107/S2056989026003798

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Synthesis, crystal structure and Hirshfeld surface analysis of 2-oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide

M. Sunithakumari,^a M. Harish Kumar,^a H. C. Devarajegowda,^a M. U. Gagan,^b V. Dwarakanath ^b and B. S. Palakshamurthy ^c ^*

^aDepartment of Physics, Yuvaraja's College, University of Mysore, Mysore-570005, Karnataka, India, ^bDepartment of Biotechnology, U.C.S, Tumkur University, Tumkur, Karnataka-572103, India, and ^cDepartment of PG Studies and Research in Physics, Albert Einstein Block, UCS, Tumkur University, Tumkur, Karnataka-572103, India
^*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 7 April 2026; accepted 10 April 2026; online 29 April 2026)

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.

Keywords: crystal structure; Hirshfeld surface; two-dimensional fingerprint; 2H-chromene-3-carboxamide.

CCDC reference: 2545176

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.

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) .

Figure 1
The title compound with the atom-numbering scheme and 50% probability ellipsoids.

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 R₂²(16) ring motifs, while on the opposite side, C13—H13⋯O2 hydrogen bonds form R₂²(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 d_norm 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 R₂²(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 R₂²(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 d_norm and the C—H⋯O interactions forming R₂²(16) and R₂²(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 U_iso(H) = 1.2U_eq(C/N).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₂O₃
M_r	266.25
Crystal system, space group	Triclinic, P $[\overline{1}]$
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 )
T_min, T_max	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
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2017 ), SHELXT2018/3 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2545176

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003798/vm2329sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003798/vm2329Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026003798/vm2329Isup3.cml

checkCIF report

Computing details top

2-Oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide top

Crystal data top

C₁₅H₁₀N₂O₃	Z = 2
M_r = 266.25	F(000) = 276
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEXII CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 1.7 pixels mm^-1	θ_max = 29.7°, θ_min = 2.7°
φ and Ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −10→8
T_min = 0.964, T_max = 0.973	l = −19→19
8155 measured reflections

Refinement top

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(F_o²) + (0.0775P)² + 0.3022P] where P = (F_o² + 2F_c²)/3
3181 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³
0 constraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

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.

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Volume 82| Part 5| May 2026| Pages 516-520

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Synthesis, crystal structure and Hirshfeld surface analysis of 2-oxo-N-(pyridin-4-yl)-2H-chromene-3-carboxamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

3. Supramolecular features