Syntheses and structures of N-(2-fluoro­phen­yl)-2-oxo-2H-chromene-3-carboxamide and N-[4-(methyl­sulfon­yl)phen­yl]-2-oxo-2H-chromene-3-carboxamide

Sunithakumari, M.; Devarajegowda, H.C.; Gagan, M.U.; Dwarakanath, V.; Srinivasa, H.T.; Palakshamurthy, B.S.

doi:10.1107/S2056989026001180

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ISSN: 2056-9890

Volume 82| Part 3| March 2026| Pages 264-270

https://doi.org/10.1107/S2056989026001180

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Syntheses and structures of N-(2-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide and N-[4-(methylsulfonyl)phenyl]-2-oxo-2H-chromene-3-carboxamide

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

^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, ^cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, Karnataka-560080, India, and ^dDepartment of PG Studies and Research in Physics, Albert Einstein Block, UCS, Tumkur University, Tumkur, Karnataka-572103, India
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 27 January 2026; accepted 4 February 2026; online 10 February 2026)

In the first title compound, C₁₆H₁₀FNO₃ (I), the dihedral angle between the 2-oxo-2H-chromene ring system and the 2-fluorophenyl ring is 0.73 (16)°. In the second title compound, C₁₇H₁₃NO₅S (II), the corresponding angle is 12.44 (2)°. Compound (I) features a bifurcated intramolecular N—H⋯(O,F) hydrogen bond, whereas (II) displays an N—H⋯O hydrogen bond. In the crystal of (I), the molecules are connected through pairwise C—H⋯O hydrogen bonds forming an inversion dimer generating an R₂²(14) motif, whereas in (II), C—H⋯O hydrogen bonds generate an R₂²(8) motif. The packing for (I) also features a C—H⋯F contact, generating an S(6) chain along [001]. The major contributions to the Hirshfeld surface of (I) are from H⋯H (30.0%), O⋯H/H⋯O (21.0%), C⋯H/H⋯C (15.9%), C⋯C (12.5%), F⋯H/H⋯F (10.8%) and O⋯C/C⋯O (5.0%) contacts while those in (II) are from H⋯H (28.0%), O⋯H/H⋯O (36.7%), C⋯H/H⋯C (19.8%), C⋯C (5.6%), and O⋯C/C⋯O (6.9%) contacts. Compound (II) demonstrated moderate to good anti-bacterial activity with MIC values of 25 µg ml⁻¹ against S. aureus and 15 µg ml⁻¹ against E. coli.

Keywords: crystal structure; 2-oxo-2H-chromene; Hirshfeld surface analysis; anti-bacterial studies.

CCDC references: 2528508; 2528509

1. Chemical context

The 2-oxo-2H-chromene scaffold is associated with a wide range of biological activities, including anticancer (Phutdhawong et al., 2021 ; Sunitha Kumari et al., 2025 ), anti-inflammatory (Melagraki et al., 2009 ), antitubercular (Rana et al., 2025 ) and antimicrobial properties (Sangani et al., 2013 ). Recent studies have demonstrated that conjugated 2-oxo-2H-chromene derivatives exhibit considerable antimicrobial potential (Lata et al., 2024 ). Efficient synthetic approaches, such as one-pot and multicomponent reactions, have enabled the development of structurally diverse coumarin derivatives (Eshghi et al., 2021 ). Several investigations have reported the effectiveness of these compounds against pathogenic microorganisms associated with wound infections, often displaying advantages over conventional antibiotics due to their distinct modes of action (Latha Rani et al., 2016 ). Among these derivatives, 2-oxo-2H-chromene-3-carboxamides have attracted particular attention owing to their potential as anti-Helicobacter pylori agents (Chimenti et al., 2007 ). Carboxamide frameworks are widely employed in pharmaceutical design and are known to exhibit antibacterial and antioxidant properties, highlighting their importance in drug-discovery programmes (Gadhave et al., 2022 ). In addition, phenyl-substituted coumarins have been reported to display antimicrobial activity comparable to that of kanamycin (Nayak et al., 2015 ).

The incorporation of halogen and sulfonyl substituents has been shown to enhance biological activity in some cases, including notable anticancer effects against breast cancer cell lines (Althobaiti et al., 2025 ). Sulfonyl-containing heterocycles, such as quinazoline analogues, have also exhibited promising anticancer and anti-inflammatory activities, underscoring the therapeutic relevance of sulfonyl-functionalized scaffolds (Venkatesan et al., 2024 ). Amide bond formation mediated by 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) in the presence of triethylamine (TEA) is a reliable and widely used synthetic method. Coupling halogenated phenylaniline and other rigid aromatic moieties with the 2-oxo-2H-chromene core has yielded derivatives with enhanced antibacterial activity. In continuation of our ongoing studies on these systems, we report herein the synthesis and crystal structures of the title compounds C₁₆H₁₀FNO₃ (I) and C₁₇H₁₃NO₅S (II). Hirshfeld surfaces are computed for both compounds and preliminary anti-bacterial data are reported for (II).

2. Structural commentary

In compound (I), the dihedral angle between the C1–C9/O1/O2 2-oxo-2H-chromene ring system and the C11–C16 aromatic ring of the 2-fluorophenyl moiety is 0.73 (16)°: the molecule is approximately planar with an r.m.s deviation of twenty fitted non-H atoms of 0.020 Å. In (II), the dihedral angle between the C1–C9/O1/O2 2-oxo-2H-chromene fused rings and the C11–C16 ring of the methylsulfonyl phenyl moiety is 12.44 (2)°. The C1—C10(O)—N1(H)—C11 torsion angles associated with the amide moiety of (I) and (II) are 179.9 (4) and −172.1 (3)°, respectively, indicating the expected trans conformation in each case. The bond angle for the linking C14(Ar)—S1—C17 bond in (II) of 104.63 (19)° correlates with a near perpendicular arrangement of the terminal methyl group with the aromatic ring phenyl moiety. Compound (I) features a bifurcated intramolecular N—H⋯(O,F) hydrogen bond (Table 1), whereas (II) displays an intramolecular N—H⋯O hydrogen bond (Table 2). Both (I) and (II) feature the same two short intramolecular C—H⋯O contacts associated with atoms C9, C16 and O3 (Fig. 1). All in all, the solid-state conformations of (I) and (II) are very similar, with the same intramolecular non-covalent interactions.

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.97	2.706 (4)	143
N1—H1⋯F1	0.86	2.25	2.647 (4)	108
C9—H9⋯O3	0.93	2.43	2.757 (5)	101
C16—H16⋯O3	0.93	2.34	2.918 (5)	120
C7—H7⋯O3ⁱ	0.93	2.47	3.326 (5)	154
C15—H15⋯F1ⁱⁱ	0.93	2.53	3.255 (5)	135
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

Cg1 and Cg2 are the centroids of the O2/C2/C1/C9/C8/C3 and C3/C4/C5/C6/C7/C8 rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86 (4)	1.91 (4)	2.685 (4)	149 (3)
C9—H9⋯O3	0.93	2.45	2.771 (4)	100
C16—H16⋯O3	0.93	2.34	2.916 (4)	119
C13—H13⋯O4	0.93	2.51	2.890 (4)	105
C7—H7⋯O1ⁱ	0.93	2.82	3.624 (4)	146
C17—H17A⋯O5ⁱⁱ	0.96	2.53	3.163 (5)	123
C17—H17B⋯O4ⁱⁱⁱ	0.96	2.47	3.293 (5)	144
C12—H12⋯Cg1^iv	0.93	2.97	3.509 (4)	118
C13—H13⋯Cg2^iv	0.93	2.86	3.522 (4)	129
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structures of (I) and (II) showing 50% probability ellipsoids with intramolecular hydrogen bonds and short contacts shown as blue dashed lines.

3. Supramolecular features

In the extended structure of (I), intermolecular C—H⋯O and C—H⋯F hydrogen bonds are observed (Table 1). The molecules are connected through pairwise C7—H7⋯O3 hydrogen bonds, forming an inversion dimer generating an R₂²(14) motif (Fig. 2). In addition, weak C15—H15⋯F1 interactions generate S(6) chains propagating along [001]. In (II), C7—H7⋯O1, C17—H17A⋯O5 and C17—H17B⋯O4 intermolecular interactions are observed (Table 2). Among these, C7—H7⋯O1 forms an S(5) chain propagating along the [001] direction and C17—H17B⋯O4 generates an R₂²(8) motif by connecting two molecules into an inversion dimer (Fig. 3).

Figure 2
The packing diagram for (I): C—H⋯O hydrogen bonds generating an R₂²(14) motif and weak C—H⋯F interactions generating an S(6) chain along [001] are shown as dashed lines.

Figure 3
The packing diagram for (II): C—H⋯O hydrogen bonds generating R₂²(8) motifs and S(5) chains along [001] are shown as dashed lines.

Both structures feature a C10=O3⋯Cg1 close contact between the carbonyl group and the heterocyclic ring of the coumarin moiety (Fig. 4) with an O⋯π separation of 3.383 (3) Å for (I) and 3.465 (3) Å for (II) compared to a van der Waals separation of 3.32 Å. Furthermore, the packing of (II) is consolidated by two C12—H12⋯Cg2, C13—H13⋯Cg1 interactions as shown in Fig. 5. In addition to these, the packing for (I) and (II) is consolidated by aromatic π⋯π stacking with a centroid–centroid distance, Cg1⋯Cg2 = 3.662 (2) Å in (I) and Cg2⋯Cg3 = 3.917 (2) Å in (II) (Fig. 6) where Cg1 and Cg2 are the centroids of the O2/C2/C1/C9/C8/C3 and C3–C8 coumarin rings in (I) or (II) and Cg3 is centroid of the C11–C16 ring in (II).

Figure 4
The partial packing of (I) and (II) showing the C=O⋯π short contacts.

Figure 5
The partial packing of (II) indicating the C—H⋯π interactions.

Figure 6
The partial packing of (I) and (II) indicating π–π stacking.

4. Database survey

A search of the Cambridge Structural Database (CSD, updated to July 2025; Groom et al., 2016 ) for structures containing a 2-oxo-2H-chromene-3-carboxamide fragment yielded more than thirty entries, of which four are closely related to compounds (I) and (II). In the structures with refcodes DISYIP (Maldonado-Domínguez et al., 2014 ), IPODIC (Gomes et al., 2016 ) and IPODOI (Gomes et al., 2016 ), the dihedral angles between the 2-oxo-2H-chromene core and the substituted phenyl rings are less than 2°, indicating near coplanarity, comparable with that observed in (I) and (II). In these structures, the amide linkage adopts a trans conformation, with torsion angles close to 180°, consistent with those found in the title compounds. By contrast, in N-(2,6-dimethylphenyl)-2-oxo-2H-chromene-3-carboxamide (KEVGUQ; Yu et al., 2018 ), the dihedral angle between the chromene system and the dimethyl-substituted phenyl ring deviates significantly from planarity, approaching orthogonality, which can be attributed to steric effects arising from the two methyl substituents. In addition, three structures containing an N-(4-methylsulfonyl)phenyl fragment [FUGKIB (Ghosh et al., 2000 ), HIZMIP (Tian et al., 2019 ) and MOTJEK (Daszkiewicz et al., 2002 )] were identified. In these compounds, the geometry around the C(aryl)—S—C bond indicates a perpendicular orientation of the methylsulfonyl group relative to the phenyl ring, closely resembling that observed in compound (II). Overall, these observations indicate that molecules incorporating the 2-oxo-2H-chromene-3-carboxamide moiety preferentially adopt a trans-amide geometry, consistent with the conformations observed in (I) and (II).

5. Hirshfeld surface analysis

A Hirshfeld surface analysis was carried out for (I) and (II) using Crystal Explorer 17.5 (Spackman et al., 2021 ) to further quantify the intermolecular interactions listed in Tables 1 and 2. The three-dimensional Hirshfeld surfaces plotted over d_norm are shown in Fig. 7. The two-dimensional fingerprint plots for (I) indicate that the most important contributions for the Hirshfeld surface are from H⋯H (30.0%), H⋯O/O⋯H (21.0%), H⋯C/C⋯H (15.9%), C⋯C (12.5%), H⋯F/C⋯F (10.8%), and C⋯O/ O⋯C (5%) contacts as shown in Fig. 8. Similarly the fingerprint plots for (II) show the important contributions for the Hirshfeld surface are from H⋯H (28.0%), O⋯H/H⋯O (36.7%), C⋯H/H⋯C (19.8%), C⋯C (5.6%) and O⋯C/C⋯O (6.9%) contacts are shown in Fig. 9. Thus, the percentage of O⋯H/H⋯O contacts for (II) is substantially higher than for (I), which possibly correlates with the ‘extra' O atoms in the methylsulfonate group in the former and their role as intermolecular hydrogen-bond acceptors (Table 2).

Figure 7
View of the three-dimensional Hirshfeld surfaces of (I) and (II) plotted over d_norm.

Figure 8
The two-dimensional fingerprint plots for compound (I), showing the different contact types.

Figure 9
The two-dimensional fingerprint plots for compound (II), showing the different contact types.

6. Anti-bacterial activities

The anti-bacterial efficacy of compound (II) was evaluated against gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacterial strains by determining the minimum inhibitory concentration (MIC) (Boyanova et al., 2005 ). Compound (II) exhibited moderate to good anti-bacterial activity, with MIC values of 25 µg ml⁻¹ against S. aureus and 15 µg ml⁻¹ against E. coli, indicating slightly enhanced activity towards the gram-negative strain. The estimated error for these measurements is ±1 µg ml⁻¹. Compared with the standard antibiotic ciprofloxacin, which exhibited potent activity against both tested organisms with MIC values of 15 µg ml⁻¹, compound (II) showed approximately 1.7-fold lower potency against S. aureus; however, against E. coli, compound (II) demonstrated comparable efficacy, exhibiting an identical MIC value of 15 µg ml⁻¹. These findings suggest that compound (II) possesses a promising antibacterial profile and might serve as a potential lead compound for further structure–activity relationship and mechanistic studies.

7. Synthesis and crystallization

A mixture of 2-oxo-2H-chromene-3-carboxylic acid (1.00 mmol), 2-fluoroaniline (2.00 mmol) [for (I)] and 4-(methylsulfonyl)aniline (2.00 mmol) [for (II)] and triethyl amine (TEA) (4.2 mmol) in acetonitrile (15 ml) was stirred at room temperature for 5 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 (Fig. 10). 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). Colourless prisms of (I) and (II) were recrystallized from ethyl acetate solution in each case. For (I): ¹H NMR (500 MHz, CDCl₃): δ (ppm) 10.83 (s, 1H, –CO—NH–), 8.45 (s, 1H, vinyl-H), 8.10–7.86 (m, 3H, Ar-H), 7.42–7.38 (m, 3H, Ar-H), 7.33–6.95 (m, 2H, Ar-H). M.p. 432 K; elemental analysis (%) calculated: C, 72.34; H, 3.93; F, 6.73; O 17.00; found C, 72.39; H, 3.95; F, 6.77%. For (II): ¹H NMR (500 MHz, CDCl₃: δ (ppm) 10.83 (s, 1H, –CO—NH–), 8.45 (s, 1H, vinyl-H), 7.86–7.66 (m, 4H, Ar-H), 7.42 (m, 2H, Ar-H), 6.86 (m, 2H, Ar-H), 3.41 (s, 3H, –CH₃). M.p 458 K, elemental analysis (%) calculated: C, 59.47; H, 3.82; N, 4.08; O, 23.30; S, 9.34.; found C, 59.50; H, 3.87; N, 4.13; S, 9.39%.

Figure 10
Synthesis schemes for (I) and (II).

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen-atom positions were calculated geometrically (N—H = 0.86 Å; C—H = 0.93–0.96 Å) and refined using a riding model by applying the constraint U_iso(H) = 1.2U_eq(C, N) or 1.5U_eq(methyl C).

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₆H₁₀FNO₃	C₁₇H₁₃NO₅S
M_r	283.25	343.36
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/c
Temperature (K)	296	289
a, b, c (Å)	3.7966 (2), 24.8289 (11), 12.9470 (7)	17.2099 (18), 7.0495 (7), 12.6535 (12)
β (°)	92.870 (2)	98.022 (3)
V (Å³)	1218.92 (11)	1520.1 (3)
Z	4	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.12	0.24
Crystal size (mm)	0.32 × 0.25 × 0.21	0.38 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.963, 0.974	0.915, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	22396, 2154, 1976	19137, 3042, 2177
R_int	0.076	0.090
(sin θ/λ)_max (Å⁻¹)	0.594	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.149, 1.28	0.064, 0.156, 1.05
No. of reflections	2154	3042
No. of parameters	190	221
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35	0.26, −0.42
Computer programs: APEX2 and SAINT (Bruker, 2017 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010).

Supporting information

CCDC references: 2528508; 2528509

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989026001180/hb8193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026001180/hb8193Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989026001180/hb8193IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026001180/hb8193Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989026001180/hb8193IIsup5.cml

checkCIF report

Computing details top

N-(2-Fluorophenyl)-2-oxo-2H-chromene-3-carboxamide (I) top

Crystal data top

C₁₆H₁₀FNO₃	D_x = 1.543 Mg m⁻³
M_r = 283.25	Melting point: 432 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.7966 (2) Å	Cell parameters from 1976 reflections
b = 24.8289 (11) Å	θ = 2.0–26.0°
c = 12.9470 (7) Å	µ = 0.12 mm⁻¹
β = 92.870 (2)°	T = 296 K
V = 1218.92 (11) Å³	Prism, colorless
Z = 4	0.32 × 0.25 × 0.21 mm
F(000) = 584

Data collection top

Bruker SMART APEXII CCD diffractometer	2154 independent reflections
Radiation source: fine-focus sealed tube	1976 reflections with I > 2σ(I)
Detector resolution: 1.09 pixels mm^-1	R_int = 0.076
φ and Ω scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −4→4
T_min = 0.963, T_max = 0.974	k = −29→29
22396 measured reflections	l = −15→15

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.28	w = 1/[σ²(F_o²) + 3.8827P] where P = (F_o² + 2F_c²)/3
2154 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

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	0.1241 (8)	0.90012 (11)	0.6794 (2)	0.0246 (7)
O2	−0.1271 (7)	0.97653 (10)	0.63588 (19)	0.0186 (6)
F1	0.4305 (7)	0.78279 (10)	0.79180 (18)	0.0333 (7)
O3	−0.1113 (8)	0.92419 (11)	0.9918 (2)	0.0231 (7)
C4	−0.3668 (11)	1.05905 (16)	0.5771 (3)	0.0194 (9)
H4	−0.308278	1.050165	0.510313	0.023*
N1	0.1219 (9)	0.86595 (12)	0.8778 (2)	0.0182 (7)
H1	0.159091	0.862348	0.813205	0.022*
C3	−0.2944 (10)	1.02407 (16)	0.6582 (3)	0.0190 (9)
C8	−0.3803 (10)	1.03577 (15)	0.7596 (3)	0.0157 (8)
C2	−0.0334 (11)	0.93910 (16)	0.7095 (3)	0.0190 (9)
C6	−0.6140 (11)	1.12069 (16)	0.6980 (3)	0.0226 (9)
H6	−0.718705	1.153697	0.710989	0.027*
C9	−0.2900 (10)	0.99706 (16)	0.8372 (3)	0.0168 (8)
H9	−0.346070	1.004073	0.905013	0.020*
C12	0.3930 (11)	0.77959 (17)	0.8957 (3)	0.0218 (9)
C10	−0.0380 (11)	0.91219 (16)	0.9044 (3)	0.0190 (9)
C11	0.2356 (10)	0.82297 (16)	0.9418 (3)	0.0176 (9)
C7	−0.5444 (10)	1.08505 (16)	0.7777 (3)	0.0203 (9)
H7	−0.606932	1.093797	0.844139	0.024*
C15	0.3174 (11)	0.77538 (16)	1.1028 (3)	0.0227 (9)
H15	0.291815	0.773906	1.173785	0.027*
C1	−0.1257 (11)	0.95043 (15)	0.8160 (3)	0.0169 (8)
C16	0.1984 (10)	0.82015 (16)	1.0487 (3)	0.0184 (9)
H16	0.093706	0.848377	1.083041	0.022*
C5	−0.5277 (11)	1.10740 (16)	0.5972 (3)	0.0215 (9)
H5	−0.579398	1.131395	0.543369	0.026*
C13	0.5118 (11)	0.73507 (17)	0.9487 (3)	0.0266 (10)
H13	0.616607	0.706863	0.914296	0.032*
C14	0.4739 (11)	0.73258 (17)	1.0543 (3)	0.0254 (10)
H14	0.552215	0.702649	1.092051	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0380 (18)	0.0246 (16)	0.0119 (14)	0.0102 (14)	0.0068 (12)	−0.0017 (12)
O2	0.0253 (16)	0.0207 (14)	0.0100 (13)	0.0006 (12)	0.0032 (11)	−0.0003 (11)
F1	0.0473 (17)	0.0349 (15)	0.0178 (13)	0.0155 (13)	0.0019 (11)	−0.0038 (11)
O3	0.0350 (18)	0.0233 (15)	0.0117 (14)	0.0047 (13)	0.0070 (12)	−0.0004 (12)
C4	0.023 (2)	0.024 (2)	0.0112 (19)	−0.0067 (18)	−0.0020 (16)	−0.0005 (16)
N1	0.0257 (19)	0.0216 (18)	0.0075 (16)	0.0017 (15)	0.0013 (14)	0.0013 (13)
C3	0.016 (2)	0.021 (2)	0.020 (2)	−0.0024 (16)	0.0017 (17)	−0.0027 (17)
C8	0.016 (2)	0.019 (2)	0.0120 (19)	−0.0060 (16)	−0.0010 (15)	−0.0041 (15)
C2	0.022 (2)	0.020 (2)	0.014 (2)	−0.0042 (18)	−0.0001 (17)	0.0000 (17)
C6	0.024 (2)	0.018 (2)	0.025 (2)	0.0008 (18)	0.0008 (18)	−0.0001 (17)
C9	0.015 (2)	0.024 (2)	0.0118 (18)	−0.0064 (17)	0.0041 (15)	−0.0009 (16)
C12	0.023 (2)	0.027 (2)	0.015 (2)	−0.0007 (18)	−0.0014 (17)	−0.0060 (17)
C10	0.022 (2)	0.023 (2)	0.013 (2)	−0.0030 (17)	0.0037 (16)	−0.0015 (16)
C11	0.015 (2)	0.021 (2)	0.016 (2)	−0.0035 (16)	−0.0016 (16)	−0.0006 (16)
C7	0.019 (2)	0.025 (2)	0.017 (2)	−0.0042 (17)	0.0021 (16)	−0.0046 (17)
C15	0.022 (2)	0.028 (2)	0.018 (2)	−0.0017 (18)	0.0039 (17)	0.0043 (17)
C1	0.018 (2)	0.019 (2)	0.0135 (19)	−0.0034 (16)	0.0004 (16)	−0.0016 (15)
C16	0.017 (2)	0.021 (2)	0.017 (2)	−0.0014 (17)	0.0018 (16)	−0.0019 (16)
C5	0.022 (2)	0.023 (2)	0.020 (2)	−0.0014 (17)	0.0006 (17)	0.0043 (17)
C13	0.029 (2)	0.018 (2)	0.032 (3)	0.0028 (18)	−0.004 (2)	−0.0064 (19)
C14	0.025 (2)	0.022 (2)	0.029 (2)	−0.0048 (18)	−0.0096 (19)	0.0069 (18)

Geometric parameters (Å, º) top

O1—C2	1.212 (5)	C6—H6	0.9300
O2—C2	1.365 (5)	C9—C1	1.350 (5)
O2—C3	1.378 (5)	C9—H9	0.9300
F1—C12	1.363 (5)	C12—C13	1.366 (6)
O3—C10	1.215 (5)	C12—C11	1.382 (5)
C4—C5	1.378 (6)	C10—C1	1.512 (5)
C4—C3	1.380 (5)	C11—C16	1.399 (5)
C4—H4	0.9300	C7—H7	0.9300
N1—C10	1.352 (5)	C15—C16	1.378 (6)
N1—C11	1.406 (5)	C15—C14	1.383 (6)
N1—H1	0.8600	C15—H15	0.9300
C3—C8	1.398 (5)	C16—H16	0.9300
C8—C7	1.398 (6)	C5—H5	0.9300
C8—C9	1.420 (5)	C13—C14	1.383 (6)
C2—C1	1.467 (5)	C13—H13	0.9300
C6—C7	1.375 (6)	C14—H14	0.9300
C6—C5	1.401 (6)

C2—O2—C3	122.9 (3)	O3—C10—N1	124.9 (4)
C5—C4—C3	118.6 (4)	O3—C10—N1	124.9 (4)
C5—C4—H4	120.7	O3—C10—C1	119.9 (4)
C3—C4—H4	120.7	O3—C10—C1	119.9 (4)
C10—N1—C11	128.5 (3)	O3—C10—C1	119.9 (4)
C10—N1—H1	115.7	N1—C10—C1	115.2 (3)
C11—N1—H1	115.7	C12—C11—C16	117.1 (4)
O2—C3—C4	117.1 (3)	C12—C11—N1	117.6 (3)
O2—C3—C8	120.4 (3)	C16—C11—N1	125.3 (4)
C4—C3—C8	122.5 (4)	C6—C7—C8	120.5 (4)
C7—C8—C3	117.8 (4)	C6—C7—H7	119.7
C7—C8—C9	124.6 (3)	C8—C7—H7	119.7
C3—C8—C9	117.7 (4)	C16—C15—C14	121.8 (4)
O1—C2—O1	0.0 (3)	C16—C15—H15	119.1
O1—C2—O2	115.8 (3)	C14—C15—H15	119.1
O1—C2—O2	115.8 (3)	C9—C1—C2	119.4 (4)
O1—C2—C1	126.9 (4)	C9—C1—C10	118.1 (3)
O1—C2—C1	126.9 (4)	C2—C1—C10	122.5 (3)
O2—C2—C1	117.3 (3)	C15—C16—C11	119.8 (4)
C7—C6—C5	120.2 (4)	C15—C16—H16	120.1
C7—C6—H6	119.9	C11—C16—H16	120.1
C5—C6—H6	119.9	C4—C5—C6	120.5 (4)
C1—C9—C8	122.3 (3)	C4—C5—H5	119.7
C1—C9—H9	118.9	C6—C5—H5	119.7
C8—C9—H9	118.9	C12—C13—C14	119.0 (4)
F1—C12—C13	119.7 (4)	C12—C13—H13	120.5
F1—C12—C13	119.7 (4)	C14—C13—H13	120.5
F1—C12—C11	116.7 (4)	C15—C14—C13	118.8 (4)
F1—C12—C11	116.7 (4)	C15—C14—H14	120.6
C13—C12—C11	123.6 (4)	C13—C14—H14	120.6
O3—C10—N1	124.9 (4)

C2—O2—C3—C4	178.5 (4)	C8—C9—C1—C2	0.5 (6)
C2—O2—C3—C8	−0.8 (5)	C8—C9—C1—C10	179.4 (4)
C5—C4—C3—O2	−178.8 (4)	O1—C2—C1—C9	177.3 (4)
C5—C4—C3—C8	0.4 (6)	O1—C2—C1—C9	177.3 (4)
O2—C3—C8—C7	178.9 (3)	O2—C2—C1—C9	−1.3 (6)
C4—C3—C8—C7	−0.2 (6)	O1—C2—C1—C10	−1.6 (7)
O2—C3—C8—C9	−0.2 (6)	O1—C2—C1—C10	−1.6 (7)
C4—C3—C8—C9	−179.4 (4)	O2—C2—C1—C10	179.8 (3)
C3—O2—C2—O1	−177.3 (4)	O3—C10—C1—C9	−1.0 (6)
C3—O2—C2—O1	−177.3 (4)	O3—C10—C1—C9	−1.0 (6)
C3—O2—C2—C1	1.5 (5)	O3—C10—C1—C9	−1.0 (6)
C7—C8—C9—C1	−178.8 (4)	N1—C10—C1—C9	179.1 (4)
C3—C8—C9—C1	0.3 (6)	O3—C10—C1—C2	177.9 (4)
F1—F1—C12—C13	0.0 (16)	O3—C10—C1—C2	177.9 (4)
C11—N1—C10—C1	179.9 (4)	O3—C10—C1—C2	177.9 (4)
F1—C12—C11—C16	−179.6 (4)	N1—C10—C1—C2	−2.0 (6)
F1—C12—C11—C16	−179.6 (4)	C14—C15—C16—C11	−0.1 (6)
C13—C12—C11—C16	−0.1 (6)	C12—C11—C16—C15	0.1 (6)
F1—C12—C11—N1	1.2 (5)	N1—C11—C16—C15	179.2 (4)
F1—C12—C11—N1	1.2 (5)	C3—C4—C5—C6	0.3 (6)
C13—C12—C11—N1	−179.3 (4)	C7—C6—C5—C4	−1.2 (6)
C10—N1—C11—C12	179.8 (4)	F1—C12—C13—C14	179.6 (4)
C10—N1—C11—C16	0.7 (7)	F1—C12—C13—C14	179.6 (4)
C5—C6—C7—C8	1.4 (6)	C11—C12—C13—C14	0.1 (7)
C3—C8—C7—C6	−0.7 (6)	C16—C15—C14—C13	0.1 (6)
C9—C8—C7—C6	178.4 (4)	C12—C13—C14—C15	−0.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.97	2.706 (4)	143
N1—H1···F1	0.86	2.25	2.647 (4)	108
C9—H9···O3	0.93	2.43	2.757 (5)	101
C16—H16···O3	0.93	2.34	2.918 (5)	120
C7—H7···O3ⁱ	0.93	2.47	3.326 (5)	154
C15—H15···F1ⁱⁱ	0.93	2.53	3.255 (5)	135

Symmetry codes: (i) −x−1, −y+2, −z+2; (ii) x−1/2, −y+3/2, z+1/2.

N-[4-(Methylsulfonyl)phenyl]-2-oxo-2H-chromene-3-carboxamide (II) top

Crystal data top

C₁₇H₁₃NO₅S	F(000) = 712
M_r = 343.36	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 458 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.2099 (18) Å	Cell parameters from 2177 reflections
b = 7.0495 (7) Å	θ = 3.0–26.0°
c = 12.6535 (12) Å	µ = 0.24 mm⁻¹
β = 98.022 (3)°	T = 289 K
V = 1520.1 (3) Å³	Prism, colourless
Z = 4	0.38 × 0.30 × 0.25 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3042 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
Detector resolution: 1.09 pixels mm^-1	θ_max = 26.2°, θ_min = 3.1°
φ and Ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −8→8
T_min = 0.915, T_max = 0.941	l = −15→15
19137 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)] = 0.064	Hydrogen site location: mixed
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0533P)² + 1.6684P] where P = (F_o² + 2F_c²)/3
3042 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³
0 constraints

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.40542 (5)	0.18990 (15)	0.37569 (8)	0.0515 (3)
O2	−0.17185 (13)	0.0829 (3)	0.13403 (17)	0.0435 (6)
O1	−0.06266 (14)	0.0440 (4)	0.24183 (18)	0.0537 (7)
O3	0.06755 (14)	0.2706 (4)	0.01234 (19)	0.0552 (7)
O4	0.40545 (16)	0.1716 (5)	0.4883 (2)	0.0679 (8)
N1	0.07441 (17)	0.1345 (4)	0.1762 (2)	0.0393 (7)
C2	−0.09242 (19)	0.1004 (5)	0.1545 (3)	0.0406 (8)
C9	−0.09491 (19)	0.2534 (5)	−0.0178 (2)	0.0377 (7)
H9	−0.069180	0.310057	−0.069533	0.045*
C10	0.03591 (19)	0.2021 (4)	0.0840 (2)	0.0370 (7)
C14	0.30808 (19)	0.1684 (5)	0.3125 (3)	0.0397 (8)
C12	0.17416 (19)	0.1029 (5)	0.3246 (2)	0.0399 (8)
H12	0.135220	0.066486	0.364521	0.048*
C8	−0.17861 (19)	0.2407 (4)	−0.0351 (2)	0.0373 (7)
C3	−0.21538 (19)	0.1513 (5)	0.0418 (3)	0.0385 (7)
C15	0.2889 (2)	0.2111 (5)	0.2049 (3)	0.0441 (8)
H15	0.328076	0.247507	0.165326	0.053*
C5	−0.3410 (2)	0.1977 (6)	−0.0567 (3)	0.0547 (10)
H5	−0.395167	0.182412	−0.065105	0.066*
C1	−0.05228 (18)	0.1853 (4)	0.0718 (2)	0.0342 (7)
C4	−0.2957 (2)	0.1282 (5)	0.0328 (3)	0.0476 (9)
H4	−0.318471	0.067130	0.085906	0.057*
O5	0.43786 (17)	0.3599 (5)	0.3370 (3)	0.0790 (10)
C16	0.21218 (19)	0.1998 (5)	0.1565 (3)	0.0414 (8)
H16	0.199419	0.226799	0.084194	0.050*
C6	−0.3062 (2)	0.2909 (6)	−0.1347 (3)	0.0544 (10)
H6	−0.337561	0.340156	−0.194251	0.065*
C11	0.15400 (18)	0.1474 (4)	0.2169 (2)	0.0347 (7)
C13	0.25051 (19)	0.1120 (5)	0.3723 (3)	0.0408 (8)
H13	0.263593	0.080650	0.443957	0.049*
C7	−0.2264 (2)	0.3113 (5)	−0.1252 (3)	0.0473 (9)
H7	−0.203869	0.372142	−0.178679	0.057*
C17	0.4539 (3)	−0.0076 (8)	0.3316 (4)	0.0875 (16)
H17A	0.454577	0.001883	0.256090	0.131*
H17B	0.506822	−0.011464	0.367707	0.131*
H17C	0.426947	−0.121333	0.347035	0.131*
H1	0.043 (2)	0.093 (5)	0.217 (3)	0.046 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0364 (5)	0.0667 (6)	0.0521 (6)	−0.0024 (4)	0.0093 (4)	−0.0055 (5)
O2	0.0400 (13)	0.0528 (14)	0.0387 (12)	−0.0058 (11)	0.0090 (10)	0.0089 (11)
O1	0.0497 (15)	0.0725 (18)	0.0387 (13)	−0.0077 (13)	0.0054 (11)	0.0189 (13)
O3	0.0475 (14)	0.0728 (18)	0.0483 (14)	0.0010 (13)	0.0171 (12)	0.0199 (13)
O4	0.0531 (16)	0.102 (2)	0.0483 (15)	0.0026 (16)	0.0050 (12)	−0.0052 (16)
N1	0.0397 (15)	0.0412 (16)	0.0381 (15)	−0.0028 (13)	0.0097 (12)	0.0061 (13)
C2	0.0439 (19)	0.0399 (18)	0.0390 (18)	−0.0052 (15)	0.0101 (15)	−0.0012 (16)
C9	0.0453 (18)	0.0365 (17)	0.0336 (16)	−0.0019 (14)	0.0131 (14)	−0.0010 (14)
C10	0.0474 (19)	0.0305 (16)	0.0354 (17)	0.0017 (15)	0.0138 (14)	−0.0012 (14)
C14	0.0363 (17)	0.0390 (18)	0.0454 (18)	0.0021 (14)	0.0112 (14)	−0.0008 (15)
C12	0.0411 (18)	0.0428 (18)	0.0383 (17)	−0.0020 (15)	0.0152 (14)	0.0025 (15)
C8	0.0450 (18)	0.0300 (16)	0.0376 (17)	0.0015 (14)	0.0082 (14)	−0.0030 (14)
C3	0.0405 (18)	0.0366 (17)	0.0375 (17)	−0.0010 (14)	0.0027 (14)	−0.0006 (14)
C15	0.0437 (19)	0.047 (2)	0.0453 (19)	0.0012 (16)	0.0200 (15)	0.0069 (16)
C5	0.041 (2)	0.057 (2)	0.065 (2)	−0.0015 (18)	0.0013 (18)	−0.002 (2)
C1	0.0400 (17)	0.0309 (16)	0.0334 (16)	−0.0007 (14)	0.0111 (13)	−0.0015 (13)
C4	0.045 (2)	0.047 (2)	0.052 (2)	−0.0032 (16)	0.0116 (16)	0.0039 (17)
O5	0.0609 (18)	0.090 (2)	0.087 (2)	−0.0316 (17)	0.0160 (16)	0.0050 (18)
C16	0.0447 (19)	0.0444 (19)	0.0374 (17)	0.0036 (16)	0.0140 (14)	0.0048 (16)
C6	0.053 (2)	0.057 (2)	0.050 (2)	0.0068 (19)	−0.0047 (17)	0.0033 (19)
C11	0.0389 (17)	0.0288 (16)	0.0371 (17)	0.0024 (13)	0.0083 (13)	−0.0014 (13)
C13	0.0422 (18)	0.0462 (19)	0.0353 (17)	0.0046 (15)	0.0102 (14)	0.0020 (15)
C7	0.055 (2)	0.048 (2)	0.0394 (18)	0.0050 (18)	0.0085 (16)	0.0050 (16)
C17	0.050 (3)	0.121 (4)	0.089 (3)	0.027 (3)	0.001 (2)	−0.031 (3)

Geometric parameters (Å, º) top

S1—O4	1.431 (3)	C12—C11	1.394 (4)
S1—O4	1.431 (3)	C12—H12	0.9300
S1—O5	1.437 (3)	C8—C3	1.385 (4)
S1—C17	1.754 (5)	C8—C7	1.401 (5)
S1—C14	1.759 (3)	C3—C4	1.380 (5)
O2—C2	1.361 (4)	C15—C16	1.379 (5)
O2—C3	1.382 (4)	C15—H15	0.9300
O1—C2	1.218 (4)	C5—C4	1.372 (5)
O3—C10	1.221 (4)	C5—C6	1.389 (5)
N1—C10	1.345 (4)	C5—H5	0.9300
N1—C11	1.397 (4)	C4—H4	0.9300
N1—H1	0.86 (4)	C16—C11	1.392 (4)
C2—C1	1.460 (4)	C16—H16	0.9300
C9—C1	1.350 (4)	C6—C7	1.370 (5)
C9—C8	1.429 (4)	C6—H6	0.9300
C9—H9	0.9300	C13—H13	0.9300
C10—C1	1.509 (4)	C7—H7	0.9300
C14—C13	1.386 (4)	C17—H17A	0.9600
C14—C15	1.389 (5)	C17—H17B	0.9600
C12—C13	1.369 (4)	C17—H17C	0.9600

O4—S1—O5	117.9 (2)	C4—C3—O2	116.6 (3)
O4—S1—O5	117.9 (2)	C4—C3—C8	123.1 (3)
O4—S1—C17	108.1 (2)	O2—C3—C8	120.3 (3)
O4—S1—C17	108.1 (2)	C16—C15—C14	120.3 (3)
O5—S1—C17	109.2 (2)	C16—C15—H15	119.8
O4—S1—C14	108.22 (16)	C14—C15—H15	119.8
O4—S1—C14	108.22 (16)	C4—C5—C6	120.3 (3)
O5—S1—C14	107.94 (17)	C4—C5—H5	119.9
C17—S1—C14	104.63 (19)	C6—C5—H5	119.9
C2—O2—C3	122.7 (3)	C9—C1—C2	119.5 (3)
C10—N1—C11	129.5 (3)	C9—C1—C10	118.6 (3)
C10—N1—H1	112 (2)	C2—C1—C10	121.9 (3)
C11—N1—H1	118 (2)	C5—C4—C3	118.2 (3)
O1—C2—O2	115.3 (3)	C5—C4—H4	120.9
O1—C2—O2	115.3 (3)	C3—C4—H4	120.9
O1—C2—C1	127.1 (3)	C15—C16—C11	119.3 (3)
O1—C2—C1	127.1 (3)	C15—C16—H16	120.4
O2—C2—C1	117.6 (3)	C11—C16—H16	120.4
C1—C9—C8	121.6 (3)	C7—C6—C5	120.9 (3)
C1—C9—H9	119.2	C7—C6—H6	119.6
C8—C9—H9	119.2	C5—C6—H6	119.6
O3—C10—N1	124.6 (3)	C16—C11—C12	119.8 (3)
O3—C10—N1	124.6 (3)	C16—C11—N1	123.9 (3)
O3—C10—N1	124.6 (3)	C12—C11—N1	116.3 (3)
O3—C10—C1	120.1 (3)	C12—C13—C14	119.2 (3)
O3—C10—C1	120.1 (3)	C12—C13—H13	120.4
O3—C10—C1	120.1 (3)	C14—C13—H13	120.4
N1—C10—C1	115.3 (3)	C6—C7—C8	120.1 (3)
C13—C14—C15	120.5 (3)	C6—C7—H7	119.9
C13—C14—S1	119.0 (3)	C8—C7—H7	119.9
C15—C14—S1	120.5 (2)	S1—C17—H17A	109.5
C13—C12—C11	120.9 (3)	S1—C17—H17B	109.5
C13—C12—H12	119.6	H17A—C17—H17B	109.5
C11—C12—H12	119.6	S1—C17—H17C	109.5
C3—C8—C7	117.4 (3)	H17A—C17—H17C	109.5
C3—C8—C9	118.1 (3)	H17B—C17—H17C	109.5
C7—C8—C9	124.5 (3)

C3—O2—C2—O1	175.6 (3)	O2—C2—C1—C9	4.1 (5)
C3—O2—C2—O1	175.6 (3)	O1—C2—C1—C10	4.0 (5)
C3—O2—C2—C1	−3.6 (5)	O1—C2—C1—C10	4.0 (5)
C11—N1—C10—O3	9.0 (6)	O2—C2—C1—C10	−176.9 (3)
C11—N1—C10—O3	9.0 (6)	O3—C10—C1—C9	−2.4 (5)
C11—N1—C10—O3	9.0 (6)	O3—C10—C1—C9	−2.4 (5)
C11—N1—C10—C1	−172.1 (3)	O3—C10—C1—C9	−2.4 (5)
O4—S1—C14—C13	−9.2 (3)	N1—C10—C1—C9	178.7 (3)
O4—S1—C14—C13	−9.2 (3)	O3—C10—C1—C2	178.6 (3)
O5—S1—C14—C13	−137.9 (3)	O3—C10—C1—C2	178.6 (3)
C17—S1—C14—C13	105.9 (3)	O3—C10—C1—C2	178.6 (3)
O4—S1—C14—C15	169.4 (3)	N1—C10—C1—C2	−0.3 (4)
O4—S1—C14—C15	169.4 (3)	C6—C5—C4—C3	−0.9 (6)
O5—S1—C14—C15	40.8 (3)	O2—C3—C4—C5	178.7 (3)
C17—S1—C14—C15	−75.5 (3)	C8—C3—C4—C5	−0.1 (5)
C1—C9—C8—C3	−1.7 (5)	C14—C15—C16—C11	0.8 (5)
C1—C9—C8—C7	178.8 (3)	C4—C5—C6—C7	1.5 (6)
C2—O2—C3—C4	−178.4 (3)	C15—C16—C11—C12	−1.5 (5)
C2—O2—C3—C8	0.5 (5)	C15—C16—C11—N1	179.0 (3)
C7—C8—C3—C4	0.5 (5)	C13—C12—C11—C16	0.8 (5)
C9—C8—C3—C4	−179.0 (3)	C13—C12—C11—N1	−179.7 (3)
C7—C8—C3—O2	−178.2 (3)	C10—N1—C11—C16	−14.9 (5)
C9—C8—C3—O2	2.3 (5)	C10—N1—C11—C12	165.6 (3)
C13—C14—C15—C16	0.7 (5)	C11—C12—C13—C14	0.7 (5)
S1—C14—C15—C16	−178.0 (3)	C15—C14—C13—C12	−1.4 (5)
C8—C9—C1—C2	−1.5 (5)	S1—C14—C13—C12	177.2 (3)
C8—C9—C1—C10	179.4 (3)	C5—C6—C7—C8	−1.1 (6)
O1—C2—C1—C9	−175.0 (3)	C3—C8—C7—C6	0.1 (5)
O1—C2—C1—C9	−175.0 (3)	C9—C8—C7—C6	179.6 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the O2/C2/C1/C9/C8/C3 and C3/C4/C5/C6/C7/C8 rings.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (4)	1.91 (4)	2.685 (4)	149 (3)
C9—H9···O3	0.93	2.45	2.771 (4)	100
C16—H16···O3	0.93	2.34	2.916 (4)	119
C13—H13···O4	0.93	2.51	2.890 (4)	105
C7—H7···O1ⁱ	0.93	2.82	3.624 (4)	146
C17—H17A···O5ⁱⁱ	0.96	2.53	3.163 (5)	123
C17—H17B···O4ⁱⁱⁱ	0.96	2.47	3.293 (5)	144
C12—H12···Cg1^iv	0.93	2.97	3.509 (4)	118
C13—H13···Cg2^iv	0.93	2.86	3.522 (4)	129

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x, y−1/2, −z+1/2.

Acknowledgements

The authors thank iSTEM and IISc for their help with the single-crystal data collection. MSK thanks CISEE and the BSPM lab for extending their help in carry out experiments and for usage of software facilities to complete the research work at University College of Science, Tumkur University Tumkur.

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Volume 82| Part 3| March 2026| Pages 264-270

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

Syntheses and structures of N-(2-fluoro­phen­yl)-2-oxo-2H-chromene-3-carboxamide and N-[4-(methyl­sulfon­yl)phen­yl]-2-oxo-2H-chromene-3-carboxamide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Hirshfeld surface analysis

6. Anti-bacterial activities

7. Synthesis and crystallization

8. Refinement

Supporting information

Acknowledgements

References

research communications

Syntheses and structures of N-(2-fluorophenyl)-2-oxo-2H-chromene-3-carboxamide and N-[4-(methylsulfonyl)phenyl]-2-oxo-2H-chromene-3-carboxamide

3. Supramolecular features