Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

El Haddad, S.; Blacque, O.; Hökelek, T.; Mazzah, A.; Labd, T.M.; El Ghayati, L.; Sebbar, N.K.

doi:10.1107/S2056989025007686

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ISSN: 2056-9890

Volume 81| Part 10| October 2025| Pages 920-923

https://doi.org/10.1107/S2056989025007686

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Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Soukaina El Haddad,^a Olivier Blacque,^b Tuncer Hökelek,^c Ahmed Mazzah,^d Taha Mohamed Labd,^e Lhoussaine El Ghayati ^a ^* and Nada Kheira Sebbar ^e,^a

^aLaboratory of Heterocyclic Organic Chemistry, Medicines Science Research, Center, Pharmacochemistry Competence Center, Mohammed V University in Rabat, Faculté des Sciences, Av. Ibn Battouta, BP 1014, Rabat, Morocco, ^bUniversity of Zurich, Department of Chemistry, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland, ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye, ^dScience and Technology of Lille USR 3290, Villeneuve d'ascq cedex, France, and ^eLaboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 July 2025; accepted 28 August 2025; online 5 September 2025)

The molecule of the title compound, C₁₅H₁₃NO₂, comprises a non-planar oxazine ring (twisted–boat conformation) fused to a benzene ring, and a benzyl moiety. In the crystal, C—H⋯O hydrogen bonds link the molecules into [010] supramolecular chains, enclosing R₂²(9) ring motifs. C—H⋯π interactions and very weak π–π stacking between the benzene rings of adjacent molecules help to consolidate the packing. A Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (48.8%), H⋯ C/C⋯H (29.3%) and H⋯O/O⋯H (18.9%) interactions.

Keywords: crystal structure; heterocycles; 1,4-benzoxazin-3-ones; C—H⋯π interaction..

CCDC reference: 2483523

1. Chemical context

1,4-Benzoxazine and its derivatives are heterocycles, resulting from the fusion of a benzene ring with an oxazine ring, containing O and N heteroatoms in positions 1 and 4, respectively. These structural elements give these compounds high chemical reactivity and are of particular interest for the development of bioactive molecules. Among them, 1,4-benzoxazin-3-ones constitute a subclass with a wide range of pharmacological properties, including antitumor, antibacterial, antifungal, anticancer, antiviral and antidepressant activities (Hlimi et al., 2018 ; Oksuzoglu et al., 2023 ; Tang et al., 2023 ; Fringuelli et al., 2002 ; Benarjee & Saritha, 2022 ; Rao et al., 2022 ; Zhou et al., 2006 ). As part of our research on benzoxazines (Sebbar et al., 2025 ), we developed a selective alkylation strategy aimed at introducing a benzyl group, 2, onto the 1,4-benzoxazin-3-one nucleus, 1. This transformation was carried out in a polar aprotic solvent (dimethylformamide, DMF), in the presence of potassium carbonate (K₂CO₃) as a base, allowing for an efficient reaction with a halogenated derivative (Fig. 1). This methodology enables the targeted production of new functionalized derivatives for future structural and biological evaluations and led to the synthesis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one (C₁₅H₁₃NO₂), 3, in 90% yield. We report here on the molecular and crystal structures of this compound and also present the results of its Hirshfeld surface analysis.

Figure 1
Reaction scheme for obtaining the title compound, 3.

2. Structural commentary

Compound 3 contains a non-planar oxazine ring fused to a benzene ring, and a benzyl moiety (Fig. 2). The oxazine ring A (O1/N1/C1–C4) has a twisted-boat conformation (Fig. 3) with puckering parameters (Cremer & Pople, 1975 ) Q_T = 0.4286 (10) Å, θ = 112.77 (13)° and φ = 213.01 (15)°. The benzene rings B (C3–C8) and C (C10–C15) are oriented at a dihedral angle of 87.27 (3)°, and atom C9 is displaced by −0.1060 (11) Å from the mean plane of ring C. Bond lengths and angles appear to be in normal ranges.

Figure 2
The molecular structure of 3 showing displacement ellipsoids at the 50% probability level.

Figure 3
Conformation of the oxazine ring atoms.

3. Supramolecular features

In the crystal of 3, C1—H1A⋯O2ⁱ and C11—H11⋯O2ⁱ hydrogen bonds (Table 1) link adjacent molecules into [010] supramolecular chains, enclosing R₂²(9) ring motifs (Etter et al., 1990 ), Fig. 4. An additional C—H⋯π(ring) interaction (Table 1) and a very weak π–π stacking interaction between the B rings of adjacent molecules with a centroid-to-centroid distance of 4.0255 (6) Å, a dihedral angle α of 0.02 (5)° and a slippage of 2.291 Å help to consolidate the packing within the crystal.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.99	2.50	3.2592 (12)	133
C11—H11⋯O2ⁱ	0.95	2.56	3.3765 (13)	146
C1—H1B⋯Cg3ⁱ	0.99	2.78	3.5952 (10)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
Partial packing diagram of 3 with intermolecular C—H⋯O hydrogen bonds shown as dashed lines; only those hydrogen atoms involved in these interactions are shown.

4. Hirshfeld surface analysis

To quantify and visualize the intermolecular interactions in the crystal of 3, a Hirshfeld surface (HS) analysis was carried out with CrystalExplorer (Spackman et al., 2021 ). Fig. 5 shows the contact distances on the HS where the bright-red spots correspond to the respective donors and/or acceptor sites noted above. According to the two-dimensional fingerprint plots (McKinnon et al., 2007 ), H⋯H, H⋯C/C⋯H and H⋯O/O⋯H contacts make the most significant contributions to the HS, at 48.8%, 29.3% and 18.9%, respectively (Fig. 6).

Figure 5
View of the three-dimensional HS of 3 plotted over d_norm.

Figure 6
The two-dimensional fingerprint plots of 3, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯O/O⋯H, (e) C⋯C, (f) H⋯N/N⋯H, (g) C⋯O/O⋯C and (h) O⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, updated July 2025; Groom et al., 2016 ) for compounds with the benzo[b][1,4]oxazin-3(4H)-one moiety substituted in the 2-, 4-, 5-, or 7-positions revealed numerous entries. The compounds most closely related to 3 are schematically displayed in Fig. 7 and include: Structures I (CSD refcode DAMYOJ; Shaikh et al., 2021 ); II (BUHROO, with R₁ = 4-(3-(2,4-dimethylphenylamino)propan-2-olyl), R₂ to R₅ = H; Rao et al., 2020 ); III (DUFKEX; Yang et al., 2019 ); IV (HAHCEC, with R₁ = CH₃, R₂ = 2-(2-methylprop-1-enyl), R₃ = 2-(4- methylbenzyl), R₄ = R₅ = H; Mohanta et al., 2023 ); V (INICIU; Nie et al., 2021 ) and VI (KOQSES; Winter et al., 2024 ). In comparison, the title compound 3 is N-benzylated and unsubstituted on the ring (R₂ – R₅ = H) and thus is distinguished by a moderate bulky group at the nitrogen atom and greater rotational freedom of the –CH₂–Ph arm, conditions favorable to (weak) π–π stacking and C—H⋯O contacts. Conversely, II and VI carry polar functions (e.g., alcohol/amine or hydroxyl groups) to establish O—H⋯O / N—H⋯O networks influencing the local conformation. III introduces a strongly electron-withdrawing group (trifluoromethyl sulfonyl), which strengthens the C—H⋯O contacts and modifies the electron density of oxazinone. I, IV, and V present bulky/aromatic substituents (N-alkyls, aryls), inducing more pronounced shifts (slippage) in the π stacks and higher N—C torsion angles, which result in distinct packing modes. The conformation of the oxazine ring in these structures is similar to that observed in the title compound.

Figure 7
Results of the database search with the closest structures identified.

6. Synthesis and crystallization

A dry mixture was prepared by combining 100 mg (0.6 mmol) of 2H-benzo[b][1,4]oxazin-3(4H)-one (previously dried under vacuum in a desiccator) with 92.1 mg (0.66 mmol) of potassium carbonate (K₂CO₃) in 15 ml of anhydrous DMF. To this mixture, 0.66 mmol of benzyl bromide were added. The reaction mixture was stirred at room temperature, and the reaction progress was monitored using thin-layer chromatography (TLC). Once the reaction was complete, the mixture was filtered to remove inorganic salts, and the solvent was evaporated under reduced pressure. The crude product was then purified using silica gel column chromatography, employing a mixture of hexane and ethyl acetate as the eluent. The target compound 3 was obtained as colorless crystals with an overall yield of 90%.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound hydrogen atoms were calculated geometrically at CH = 0.95 Å and CH₂ = 0.99 Å and refined using a riding model with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₂
M_r	239.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	160
a, b, c (Å)	9.49281 (8), 5.79368 (5), 21.45658 (18)
β (°)	91.3621 (8)
V (Å³)	1179.74 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.73
Crystal size (mm)	0.30 × 0.13 × 0.11

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Analytical (CrysAlis PRO; Rigaku OD, 2024 )
T_min, T_max	0.859, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	15357, 2477, 2412
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.04
No. of reflections	2477
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19
Computer programs: CrysAlis PRO (Rigaku OD, 2024), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2483523

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007686/wm5767sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007686/wm5767Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025007686/wm5767Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989025007686/wm5767Isup4.cml

checkCIF report

Computing details top

4-Benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one top

Crystal data top

C₁₅H₁₃NO₂	F(000) = 504
M_r = 239.26	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 9.49281 (8) Å	Cell parameters from 12385 reflections
b = 5.79368 (5) Å	θ = 4.1–79.3°
c = 21.45658 (18) Å	µ = 0.73 mm⁻¹
β = 91.3621 (8)°	T = 160 K
V = 1179.74 (2) Å³	Block, colourless
Z = 4	0.30 × 0.13 × 0.11 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2477 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2412 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.013
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.3°, θ_min = 4.1°
ω scans	h = −11→11
Absorption correction: analytical (CrysAlisPro; Rigaku OD, 2024)	k = −6→7
T_min = 0.859, T_max = 0.929	l = −27→25
15357 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.045P)² + 0.3423P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2477 reflections	Δρ_max = 0.17 e Å⁻³
163 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints

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	−0.00508 (7)	0.54481 (13)	0.36181 (3)	0.02998 (18)
O2	0.15569 (8)	0.13347 (15)	0.26572 (4)	0.0379 (2)
N1	0.22040 (8)	0.24375 (14)	0.36413 (4)	0.02528 (19)
C1	0.05704 (10)	0.48342 (19)	0.30398 (4)	0.0284 (2)
H1A	0.115402	0.613732	0.289607	0.034*
H1B	−0.018786	0.457366	0.272281	0.034*
C2	0.14752 (10)	0.26962 (18)	0.30884 (5)	0.0268 (2)
C3	0.20721 (10)	0.40933 (17)	0.41222 (4)	0.0242 (2)
C4	0.09204 (10)	0.55889 (17)	0.41010 (4)	0.0251 (2)
C5	0.06932 (11)	0.71387 (19)	0.45779 (5)	0.0319 (2)
H5	−0.010120	0.813576	0.455994	0.038*
C6	0.16316 (12)	0.7230 (2)	0.50828 (5)	0.0357 (3)
H6	0.147692	0.828356	0.541354	0.043*
C7	0.27928 (12)	0.5787 (2)	0.51046 (5)	0.0356 (3)
H7	0.344034	0.586946	0.544835	0.043*
C8	0.30189 (11)	0.42197 (19)	0.46287 (5)	0.0308 (2)
H8	0.381803	0.323285	0.464743	0.037*
C9	0.30952 (10)	0.04000 (17)	0.37316 (5)	0.0289 (2)
H9A	0.272671	−0.084600	0.345729	0.035*
H9B	0.300835	−0.012997	0.416763	0.035*
C10	0.46435 (10)	0.07306 (16)	0.36029 (4)	0.0239 (2)
C11	0.51780 (10)	0.26787 (17)	0.33164 (4)	0.0264 (2)
H11	0.457398	0.393858	0.321551	0.032*
C12	0.66043 (11)	0.2784 (2)	0.31765 (5)	0.0323 (2)
H12	0.697103	0.412364	0.298315	0.039*
C13	0.74884 (11)	0.0947 (2)	0.33182 (5)	0.0359 (3)
H13	0.845560	0.101544	0.321565	0.043*
C14	0.69600 (12)	−0.0988 (2)	0.36092 (6)	0.0370 (3)
H14	0.756507	−0.224714	0.370939	0.044*
C15	0.55472 (11)	−0.10865 (18)	0.37543 (5)	0.0317 (2)
H15	0.519116	−0.240940	0.395942	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0217 (3)	0.0411 (4)	0.0271 (4)	0.0047 (3)	0.0009 (3)	−0.0012 (3)
O2	0.0347 (4)	0.0444 (5)	0.0346 (4)	−0.0014 (3)	−0.0012 (3)	−0.0142 (3)
N1	0.0218 (4)	0.0267 (4)	0.0274 (4)	0.0008 (3)	0.0003 (3)	−0.0016 (3)
C1	0.0239 (5)	0.0378 (6)	0.0236 (5)	0.0006 (4)	−0.0001 (3)	0.0005 (4)
C2	0.0206 (4)	0.0331 (5)	0.0269 (5)	−0.0043 (4)	0.0019 (3)	−0.0028 (4)
C3	0.0231 (4)	0.0266 (5)	0.0232 (4)	−0.0032 (4)	0.0031 (3)	0.0015 (4)
C4	0.0226 (4)	0.0286 (5)	0.0242 (5)	−0.0026 (4)	0.0031 (3)	0.0025 (4)
C5	0.0322 (5)	0.0316 (5)	0.0324 (5)	0.0007 (4)	0.0081 (4)	−0.0013 (4)
C6	0.0433 (6)	0.0366 (6)	0.0276 (5)	−0.0062 (5)	0.0075 (4)	−0.0061 (4)
C7	0.0365 (5)	0.0453 (6)	0.0249 (5)	−0.0078 (5)	−0.0019 (4)	−0.0005 (4)
C8	0.0269 (5)	0.0377 (6)	0.0276 (5)	−0.0009 (4)	−0.0013 (4)	0.0020 (4)
C9	0.0266 (5)	0.0234 (5)	0.0366 (5)	−0.0011 (4)	0.0024 (4)	0.0018 (4)
C10	0.0247 (5)	0.0236 (4)	0.0235 (4)	−0.0007 (4)	−0.0009 (3)	−0.0025 (3)
C11	0.0287 (5)	0.0256 (5)	0.0248 (4)	−0.0015 (4)	−0.0014 (4)	−0.0005 (4)
C12	0.0330 (5)	0.0356 (6)	0.0283 (5)	−0.0093 (4)	0.0034 (4)	−0.0024 (4)
C13	0.0239 (5)	0.0450 (6)	0.0389 (6)	−0.0031 (4)	0.0028 (4)	−0.0126 (5)
C14	0.0290 (5)	0.0333 (6)	0.0483 (6)	0.0067 (4)	−0.0043 (4)	−0.0074 (5)
C15	0.0314 (5)	0.0244 (5)	0.0391 (6)	0.0012 (4)	−0.0011 (4)	0.0008 (4)

Geometric parameters (Å, º) top

O1—C1	1.4313 (12)	C7—C8	1.3869 (16)
O1—C4	1.3729 (12)	C8—H8	0.9500
O2—C2	1.2197 (13)	C9—H9A	0.9900
N1—C2	1.3671 (13)	C9—H9B	0.9900
N1—C3	1.4167 (12)	C9—C10	1.5140 (13)
N1—C9	1.4626 (12)	C10—C11	1.3871 (14)
C1—H1A	0.9900	C10—C15	1.3916 (14)
C1—H1B	0.9900	C11—H11	0.9500
C1—C2	1.5096 (14)	C11—C12	1.3951 (14)
C3—C4	1.3949 (14)	C12—H12	0.9500
C3—C8	1.3957 (14)	C12—C13	1.3847 (16)
C4—C5	1.3822 (14)	C13—H13	0.9500
C5—H5	0.9500	C13—C14	1.3831 (17)
C5—C6	1.3872 (16)	C14—H14	0.9500
C6—H6	0.9500	C14—C15	1.3852 (15)
C6—C7	1.3836 (17)	C15—H15	0.9500
C7—H7	0.9500

C4—O1—C1	112.70 (7)	C3—C8—H8	120.0
C2—N1—C3	120.41 (8)	C7—C8—C3	119.97 (10)
C2—N1—C9	118.86 (8)	C7—C8—H8	120.0
C3—N1—C9	120.72 (8)	N1—C9—H9A	108.3
O1—C1—H1A	109.0	N1—C9—H9B	108.3
O1—C1—H1B	109.0	N1—C9—C10	115.77 (8)
O1—C1—C2	112.92 (8)	H9A—C9—H9B	107.4
H1A—C1—H1B	107.8	C10—C9—H9A	108.3
C2—C1—H1A	109.0	C10—C9—H9B	108.3
C2—C1—H1B	109.0	C11—C10—C9	123.41 (9)
O2—C2—N1	123.18 (10)	C11—C10—C15	119.28 (9)
O2—C2—C1	121.64 (9)	C15—C10—C9	117.22 (9)
N1—C2—C1	115.17 (8)	C10—C11—H11	120.1
C4—C3—N1	118.66 (9)	C10—C11—C12	119.87 (9)
C4—C3—C8	118.86 (9)	C12—C11—H11	120.1
C8—C3—N1	122.43 (9)	C11—C12—H12	119.8
O1—C4—C3	119.97 (9)	C13—C12—C11	120.36 (10)
O1—C4—C5	118.92 (9)	C13—C12—H12	119.8
C5—C4—C3	121.02 (9)	C12—C13—H13	120.1
C4—C5—H5	120.2	C14—C13—C12	119.84 (10)
C4—C5—C6	119.63 (10)	C14—C13—H13	120.1
C6—C5—H5	120.2	C13—C14—H14	120.1
C5—C6—H6	120.0	C13—C14—C15	119.89 (10)
C7—C6—C5	119.97 (10)	C15—C14—H14	120.1
C7—C6—H6	120.0	C10—C15—H15	119.6
C6—C7—H7	119.7	C14—C15—C10	120.74 (10)
C6—C7—C8	120.52 (10)	C14—C15—H15	119.6
C8—C7—H7	119.7

O1—C1—C2—O2	145.86 (9)	C4—C3—C8—C7	1.08 (15)
O1—C1—C2—N1	−35.32 (12)	C4—C5—C6—C7	0.48 (16)
O1—C4—C5—C6	177.15 (9)	C5—C6—C7—C8	−0.89 (17)
N1—C3—C4—O1	−0.48 (13)	C6—C7—C8—C3	0.10 (16)
N1—C3—C4—C5	175.91 (9)	C8—C3—C4—O1	−177.89 (8)
N1—C3—C8—C7	−176.23 (9)	C8—C3—C4—C5	−1.50 (14)
N1—C9—C10—C11	−10.84 (14)	C9—N1—C2—O2	−1.88 (14)
N1—C9—C10—C15	172.60 (9)	C9—N1—C2—C1	179.31 (8)
C1—O1—C4—C3	−34.64 (12)	C9—N1—C3—C4	−160.52 (9)
C1—O1—C4—C5	148.89 (9)	C9—N1—C3—C8	16.79 (13)
C2—N1—C3—C4	18.13 (13)	C9—C10—C11—C12	−175.70 (9)
C2—N1—C3—C8	−164.55 (9)	C9—C10—C15—C14	175.23 (10)
C2—N1—C9—C10	96.66 (11)	C10—C11—C12—C13	0.47 (15)
C3—N1—C2—O2	179.44 (9)	C11—C10—C15—C14	−1.48 (15)
C3—N1—C2—C1	0.63 (13)	C11—C12—C13—C14	−1.08 (16)
C3—N1—C9—C10	−84.67 (11)	C12—C13—C14—C15	0.41 (16)
C3—C4—C5—C6	0.72 (15)	C13—C14—C15—C10	0.88 (17)
C4—O1—C1—C2	51.88 (11)	C15—C10—C11—C12	0.80 (14)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.99	2.50	3.2592 (12)	133
C11—H11···O2ⁱ	0.95	2.56	3.3765 (13)	146
C1—H1B···Cg3ⁱ	0.99	2.78	3.5952 (10)	143

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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Volume 81| Part 10| October 2025| Pages 920-923

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

Crystal structure and Hirshfeld surface analysis of 4-benzyl-2H-benzo[b][1,4]oxazin-3(4H)-one

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

3. Supramolecular features