Crystal structure and Hirshfeld surface analyses, inter­action energy calculations and energy frameworks of (Z)-4-benzyl-2-(4-methyl­benzylidene)-2H-[1,4]benzo­thia­zin-3(4H)-one

Hni, B.; Hamou Ahabchane, N.; Ballo, D.; Hökelek, T.; Mague, J.T.; Essassi, E.M.; Sebbar, N.K.

doi:10.1107/S2056989026004664

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ISSN: 2056-9890

Volume 82| Part 6| June 2026| Pages 665-669

https://doi.org/10.1107/S2056989026004664

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Crystal structure and Hirshfeld surface analyses, interaction energy calculations and energy frameworks of (Z)-4-benzyl-2-(4-methylbenzylidene)-2H-[1,4]benzothiazin-3(4H)-one

Brahim Hni,^a Noureddine Hamou Ahabchane,^a Daouda Ballo,^b Tuncer Hökelek,^c Joel T. Mague,^d El Mokhtar Essassi ^a and Nada Kheira Sebbar ^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, ^bLaboratory of Constitution and Reaction of Matter (LCRM), UFR SSMT, Félix Houphouët Boigny University, 22 BP 582 Abidjan 22, Republic of Côte d'Ivoire, ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 12 April 2026; accepted 5 May 2026; online 15 May 2026)

The thiazine ring in the title molecule, C₂₃H₁₉NOS, exhibits a screw-boat conformation and is significantly folded along the S⋯N axis. In the extended structure, aided by C—H⋯π(ring) interactions, the molecules pack in wave-like layers parallel to the bc plane. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (50.3%) and H⋯C/C⋯H (35.9%) interactions. An evaluation of the electrostatic, dispersion and total energy frameworks in the crystal structure indicates that dispersion energy contribution dominates.

Keywords: crystal structure; 1,4-benzothiazin-3-one; C—H⋯π(ring); weak hydrogen-bonding.

CCDC reference: 2551702

1. Chemical context

Heterocyclic compounds containing both nitrogen and sulfur atoms occupy a prominent position in organic chemistry due to their structural diversities and the wide range of biological activities they display (Sebbar et al., 2020 ). Among these systems, 1,4-benzothiazine derivatives represent an important class of fused heterocycles that have been extensively investigated in medicinal chemistry (Sebbar et al., 2016a ,b ; Tawada et al., 1990 ; Zia-ur-Rehman et al., 2009 ). The interest in these compounds mainly arises from the diversities of their pharmacological properties, which make the 1,4-benzothiazine core a valuable structural unit for the development of new therapeutic agents. Previous studies have indicated that molecules containing this scaffold exhibit anti-inflammatory (Park et al., 2002 ), antimicrobial (Rathore et al., 2006 ), antipyretic (Warren et al., 1987 ), antiviral (Malagu et al., 1998 ), or anticancer activities (Gupta et al., 1986 ). Beyond pharmaceutical applications, 1,4-benzothiazine derivatives have also gained attention as functional agents in agrochemical applications, especially as herbicides (Takemoto et al., 1994 ), and as corrosion inhibitors for metallic materials (Ellouz et al., 2016 ).

The sustained interest in the family of 1,4-benzothiazines and its derivatives is largely attributed to the ease with which their molecular structures can be modified, enabling the design of new compounds with enhanced physicochemical, biological or medicinal properties (Hni et al., 2019 ). As part of our ongoing studies of N-substituted 1,4-benzothiazine derivatives and the investigations of their potential pharmacological properties, we report herein the synthesis and crystal structure determination of (Z)-4-benzyl-2-(4-methylbenzylidene)-2H-1,4-benzothiazin-3(4H)-one, I. A Hirshfeld surface analysis and evaluation of intermolecular interaction energies and energy frameworks complement the crystallographic study.

2. Structural commentary

In the title molecule (Fig. 1), the benzothiazine moiety is folded along the S1⋯N1 axis by 23.3 (1)°, which puts it in the upper third of fold angles found for these types of molecules (Sebbar et al., 2014 ). The thiazine ring is in a screw-boat conformation (Fig. 2) with puckering parameters (Cremer & Pople, 1975 ) Q_T = 0.3565 (16) Å, θ = 75.4 (3)° and φ = 341.4 (3)°. The C10–C15 and C17–C22 benzene rings are inclined to the C1–C6 benzene ring by 84.22 (9) and 39.48 (8)°, respectively. This gives the molecule an overall convex shape with atom H15 of the benzyl group pointing towards the concave underside (Fig. 1).

Figure 1
The title molecule with the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level.

Figure 2
The conformation of the thiazine ring.

3. Supramolecular features

In the crystal, the molecules pack in wave-like layers parallel to the bc plane with the only directed interactions between them being the C18—H18⋯Cg3 interaction (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg3ⁱ	0.95	3.00	3.898 (2)	158
Symmetry code: (i) $[x+{\script{1\over 4}}, -y+{\script{3\over 4}}, z-{\script{1\over 4}}]$ .

Figure 3
Packing of molecules as viewed along the c axis, with C—H⋯π(ring) interactions depicted by dashed lines.

4. Hirshfeld surface analysis and energy calculations

The intermolecular interactions in the crystal were quantified by a Hirshfeld surface (HS) analysis using CrystalExplorer (Spackman et al., 2021 ). Fig. 4 shows the HS mapped over d_norm. The white surface indicates contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter (in close contact) or longer (distinct contacts) than the van der Waals radii, respectively. Hence, the red spots indicate their roles as the respective donors and/or acceptors atoms; they also appear as the blue and red regions corresponding to positive and negative potentials on the HS mapped over electrostatic potential as shown in Fig. 5. The blue and red regions indicate positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials. The overall two-dimensional fingerprint plot is shown in Fig. 6a and those delineated into various contact types are illustrated in Fig. 6b–h. According to the fingerprint plots, H⋯H and H⋯C/C⋯H contacts make the most significant contributions to the HS, at 50.3% and 35.9%, respectively.

Figure 4
View of the HS of the title molecule plotted over d_norm.

Figure 5
View of the HS of the title molecule plotted over electrostatic potential using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen-bonding donors and acceptors are shown as blue and red regions around the atoms, corresponding to positive and negative potentials, respectively.

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

The intermolecular interaction energies were calculated using the CE–B3LYP/6–31G(d,p) energy model available in CrystalExplorer, where a cluster of molecules is generated by applying crystallographic symmetry operations with respect to a selected central molecule within a radius of 3.8 Å by default. The maximum interaction energy occurring at 6.14 Å with an E_total value of −56.1 kJ mol⁻¹ is dominated by the dispersion component of E_dis = −67.4 kJ mol⁻¹ that is significantly larger than the electrostatic component of E_ele = −20.4 kJ mol⁻¹. Energy frameworks combine the calculation of intermolecular interaction energies with a graphical representation of their magnitudes, in which they were constructed for E_ele (red cylinders), E_dis (green cylinders) and E_tot (blue cylinders), as shown in Fig. 7a, b and c, respectively. The evaluation of these frameworks indicates that the stabilization is dominated via the dispersion energy contributions.

Figure 7
The energy frameworks for a cluster of molecules of the title compound viewed down the c axis showing the (a) electrostatic energy, (b) dispersion energy and (c) total energy diagrams. The cylindrical radius is proportional to the relative strength of the corresponding energies and they were adjusted to the same scale factor of 80 with cut-off value of 5 kJ mol⁻¹ within the unit cell.

5. Database survey

A survey of the Cambridge Structural Database (CSD; Groom et al., 2016 ; update of March 2026) for structures incorporating fragment II (R1 = Ph, R2 = C; Fig. 8) identified 14 related entries. Among these, compounds IIa correspond to derivatives bearing R1 = 4-ClC₆H₄ or 2,4-ClC₆H₄ and R2 = CH₂Ph₂ (Sebbar et al., 2019 ). Compound IIb has been reported with R1 = 4-ClC₆H₄ and R2 = CH₂COOH (Sebbar et al., 2016a), whereas compounds IIc include examples with R1 = Ph, 4-FC₆H₄, or 2-ClC₆H₄ and R2 = CH₂C≡CH (Hni et al., 2019). Additional related structures correspond to types IId and IIe (Sebbar et al., 2016b). In every case, the benzylidene C=CHC₆H₅ double bond leads to a Z configuration. Furthermore, most of these structures display a markedly non-planar heterocyclic ring. The dihedral angle between the plane formed by the benzene ring together with the nitrogen and sulfur atoms, and the plane defined by the nitrogen and sulfur atoms and the two intervening carbon atoms, varies from approximately 29° in IIc to 36° in IId.

Figure 8
Schematic representation of candidates for the search in the CSD.

6. Synthesis and crystallization

To a solution of (Z)-2-(4-methylbenzylidene)-2H-1,4-benzothiazin-3(4H)-one (3.21 mmol), benzyl chloride (6.52 mmol) and potassium carbonate (6.51 mmol) in dimethylformamide (DMF; 20ml), a catalytic amount of tetra-n-butyl ammonium bromide (0.33 mmol) was added. The mixture was then stirred for 24 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol to afford colourless crystals in 86% yield.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and were included as riding contributions with isotropic displacement parameters 1.2–1.5 times those of the attached atoms. The phenyl group (C10–C15) of the benzyl moiety suffers from minor disorder as evidenced by the elongated displacement ellipsoids for most of the atoms. Attempts to model the disorder with two rigid groups led to an unstable refinement and were not pursued.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₁₉NOS
M_r	357.45
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	150
a, b, c (Å)	18.7286 (11), 43.903 (2), 8.9154 (5)
V (Å³)	7330.5 (7)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	0.19
Crystal size (mm)	0.36 × 0.32 × 0.27

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.85, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	34831, 4941, 4700
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.093, 1.06
No. of reflections	4941
No. of parameters	236
No. of restraints	31
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22
Absolute structure	Flack x determined using 2075 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.010 (13)
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2551702

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989026004664/wm5798sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026004664/wm5798Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004664/wm5798Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004664/wm5798Isup4.cml

checkCIF report

Computing details top

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

Crystal data top

C₂₃H₁₉NOS	D_x = 1.296 Mg m⁻³
M_r = 357.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 9879 reflections
a = 18.7286 (11) Å	θ = 2.4–29.2°
b = 43.903 (2) Å	µ = 0.19 mm⁻¹
c = 8.9154 (5) Å	T = 150 K
V = 7330.5 (7) Å³	Block, colourless
Z = 16	0.36 × 0.32 × 0.27 mm
F(000) = 3008

Data collection top

Bruker SMART APEX CCD diffractometer	4941 independent reflections
Radiation source: fine-focus sealed tube	4700 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.3°, θ_min = 1.9°
φ and ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −60→60
T_min = 0.85, T_max = 0.95	l = −12→12
34831 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0567P)² + 3.7343P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4941 reflections	Δρ_max = 0.32 e Å⁻³
236 parameters	Δρ_min = −0.22 e Å⁻³
31 restraints	Absolute structure: Flack x determined using 2075 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.010 (13)

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The phenyl group C10···C15 suffers from minor disorder as evidenced by the elongated displacement ellipsoids for most of the atoms. Attempts to model the disorder with two rigid hexagon sites led to an unstable refinement and so were not pursued.

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

	x	y	z	U_iso*/U_eq
S1	0.19870 (3)	0.44442 (2)	0.60481 (6)	0.04254 (16)
O1	0.18669 (9)	0.41154 (3)	0.19620 (17)	0.0356 (3)
N1	0.14611 (9)	0.39080 (4)	0.41107 (19)	0.0284 (3)
C1	0.17135 (11)	0.40843 (5)	0.6666 (2)	0.0335 (4)
C2	0.17002 (12)	0.40339 (6)	0.8212 (3)	0.0416 (5)
H2	0.183487	0.419267	0.887892	0.050*
C3	0.14930 (13)	0.37555 (6)	0.8777 (3)	0.0430 (5)
H3	0.148292	0.372284	0.983053	0.052*
C4	0.12992 (13)	0.35231 (5)	0.7805 (3)	0.0389 (5)
H4	0.116288	0.333005	0.819175	0.047*
C5	0.13045 (11)	0.35728 (5)	0.6267 (2)	0.0333 (4)
H5	0.117455	0.341240	0.560583	0.040*
C6	0.14986 (10)	0.38557 (4)	0.5680 (2)	0.0291 (4)
C7	0.18423 (10)	0.41240 (4)	0.3334 (2)	0.0280 (4)
C8	0.22171 (10)	0.43711 (4)	0.4178 (2)	0.0282 (4)
C9	0.10298 (10)	0.37004 (4)	0.3195 (2)	0.0284 (4)
H9A	0.085046	0.381357	0.231188	0.034*
H9B	0.061013	0.363559	0.379031	0.034*
C10	0.14167 (11)	0.34193 (4)	0.2652 (2)	0.0293 (4)
C11	0.10357 (19)	0.32103 (6)	0.1796 (3)	0.0575 (8)
H11	0.054201	0.324269	0.160976	0.069*
C12	0.1371 (3)	0.29553 (7)	0.1213 (4)	0.0831 (12)
H12	0.110860	0.281341	0.062798	0.100*
C13	0.2088 (3)	0.29079 (7)	0.1484 (4)	0.0809 (12)
H13	0.232125	0.273554	0.106422	0.097*
C14	0.24653 (18)	0.31078 (7)	0.2353 (4)	0.0647 (9)
H14	0.295524	0.307112	0.256186	0.078*
C15	0.21316 (12)	0.33643 (5)	0.2931 (3)	0.0413 (5)
H15	0.239716	0.350386	0.352412	0.050*
C16	0.26745 (10)	0.45466 (4)	0.3393 (2)	0.0290 (4)
H16	0.270036	0.449685	0.235720	0.035*
C17	0.31382 (10)	0.47992 (4)	0.3834 (2)	0.0300 (4)
C18	0.36728 (11)	0.48828 (5)	0.2807 (2)	0.0336 (4)
H18	0.370584	0.477985	0.187258	0.040*
C19	0.41524 (11)	0.51136 (5)	0.3141 (3)	0.0378 (5)
H19	0.450342	0.516830	0.241997	0.045*
C20	0.41322 (11)	0.52667 (5)	0.4501 (3)	0.0383 (5)
C21	0.35937 (13)	0.51898 (5)	0.5500 (3)	0.0443 (5)
H21	0.356185	0.529493	0.642919	0.053*
C22	0.30992 (12)	0.49626 (5)	0.5176 (3)	0.0403 (5)
H22	0.273081	0.491817	0.587471	0.048*
C23	0.46743 (14)	0.55090 (6)	0.4877 (4)	0.0526 (6)
H23A	0.477091	0.563235	0.398377	0.079*
H23B	0.511753	0.541230	0.521572	0.079*
H23C	0.448664	0.563967	0.567616	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0539 (3)	0.0364 (2)	0.0374 (3)	−0.0173 (2)	0.0175 (2)	−0.0148 (2)
O1	0.0468 (8)	0.0324 (7)	0.0275 (7)	−0.0058 (6)	−0.0001 (6)	0.0008 (5)
N1	0.0282 (7)	0.0302 (7)	0.0266 (8)	−0.0048 (6)	0.0010 (6)	−0.0049 (6)
C1	0.0332 (10)	0.0375 (9)	0.0298 (10)	−0.0110 (8)	0.0090 (8)	−0.0076 (8)
C2	0.0418 (11)	0.0550 (13)	0.0281 (10)	−0.0174 (10)	0.0069 (9)	−0.0131 (9)
C3	0.0455 (12)	0.0602 (13)	0.0231 (9)	−0.0143 (10)	0.0049 (9)	−0.0047 (9)
C4	0.0421 (11)	0.0454 (11)	0.0294 (10)	−0.0107 (9)	0.0061 (8)	0.0010 (8)
C5	0.0350 (9)	0.0363 (9)	0.0285 (10)	−0.0076 (8)	0.0032 (7)	−0.0028 (7)
C6	0.0263 (8)	0.0350 (9)	0.0260 (9)	−0.0052 (7)	0.0044 (7)	−0.0044 (7)
C7	0.0286 (8)	0.0257 (8)	0.0296 (10)	0.0006 (6)	0.0009 (7)	−0.0022 (7)
C8	0.0292 (8)	0.0267 (7)	0.0288 (8)	0.0005 (6)	0.0022 (7)	−0.0040 (7)
C9	0.0250 (8)	0.0317 (8)	0.0284 (9)	−0.0012 (6)	−0.0019 (7)	−0.0038 (7)
C10	0.0376 (10)	0.0293 (8)	0.0211 (8)	−0.0001 (7)	−0.0003 (7)	0.0009 (6)
C11	0.0805 (19)	0.0377 (11)	0.0542 (16)	0.0039 (12)	−0.0337 (15)	−0.0116 (11)
C12	0.152 (4)	0.0405 (13)	0.0570 (18)	0.0161 (18)	−0.034 (2)	−0.0204 (13)
C13	0.137 (3)	0.0443 (14)	0.0610 (19)	0.0365 (19)	0.017 (2)	−0.0041 (13)
C14	0.0648 (17)	0.0496 (14)	0.080 (2)	0.0246 (13)	0.0290 (16)	0.0164 (14)
C15	0.0356 (10)	0.0374 (10)	0.0510 (13)	0.0040 (8)	0.0091 (9)	0.0057 (9)
C16	0.0281 (8)	0.0259 (8)	0.0330 (10)	0.0021 (6)	0.0023 (7)	0.0016 (7)
C17	0.0273 (8)	0.0240 (7)	0.0387 (11)	0.0039 (6)	−0.0003 (7)	0.0042 (7)
C18	0.0311 (9)	0.0341 (9)	0.0355 (11)	0.0005 (7)	−0.0006 (8)	0.0060 (8)
C19	0.0273 (9)	0.0387 (10)	0.0474 (12)	−0.0022 (8)	0.0013 (9)	0.0108 (9)
C20	0.0292 (9)	0.0296 (9)	0.0562 (13)	−0.0002 (7)	−0.0014 (9)	0.0030 (9)
C21	0.0457 (12)	0.0315 (10)	0.0556 (14)	−0.0057 (9)	0.0097 (10)	−0.0115 (9)
C22	0.0400 (11)	0.0310 (9)	0.0498 (13)	−0.0055 (8)	0.0154 (10)	−0.0071 (9)
C23	0.0397 (12)	0.0440 (12)	0.0742 (18)	−0.0118 (10)	−0.0014 (12)	−0.0043 (12)

Geometric parameters (Å, º) top

S1—C1	1.750 (2)	C11—H11	0.9500
S1—C8	1.751 (2)	C12—C13	1.380 (7)
O1—C7	1.225 (3)	C12—H12	0.9500
N1—C7	1.375 (2)	C13—C14	1.367 (6)
N1—C6	1.419 (3)	C13—H13	0.9500
N1—C9	1.466 (2)	C14—C15	1.387 (3)
C1—C6	1.393 (3)	C14—H14	0.9500
C1—C2	1.397 (3)	C15—H15	0.9500
C2—C3	1.378 (3)	C16—C17	1.463 (3)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.387 (3)	C17—C22	1.396 (3)
C3—H3	0.9500	C17—C18	1.406 (3)
C4—C5	1.389 (3)	C18—C19	1.386 (3)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.396 (3)	C19—C20	1.387 (3)
C5—H5	0.9500	C19—H19	0.9500
C7—C8	1.495 (3)	C20—C21	1.387 (3)
C8—C16	1.348 (3)	C20—C23	1.508 (3)
C9—C10	1.511 (3)	C21—C22	1.392 (3)
C9—H9A	0.9900	C21—H21	0.9500
C9—H9B	0.9900	C22—H22	0.9500
C10—C15	1.383 (3)	C23—H23A	0.9800
C10—C11	1.390 (3)	C23—H23B	0.9800
C11—C12	1.385 (4)	C23—H23C	0.9800

C1—S1—C8	101.89 (9)	C13—C12—C11	119.9 (3)
C7—N1—C6	125.62 (16)	C13—C12—H12	120.1
C7—N1—C9	115.77 (15)	C11—C12—H12	120.1
C6—N1—C9	118.39 (15)	C14—C13—C12	120.3 (3)
C6—C1—C2	120.24 (19)	C14—C13—H13	119.9
C6—C1—S1	122.43 (16)	C12—C13—H13	119.9
C2—C1—S1	117.31 (16)	C13—C14—C15	119.9 (3)
C3—C2—C1	120.4 (2)	C13—C14—H14	120.0
C3—C2—H2	119.8	C15—C14—H14	120.0
C1—C2—H2	119.8	C10—C15—C14	120.7 (3)
C2—C3—C4	119.9 (2)	C10—C15—H15	119.6
C2—C3—H3	120.1	C14—C15—H15	119.6
C4—C3—H3	120.1	C8—C16—C17	132.1 (2)
C3—C4—C5	120.0 (2)	C8—C16—H16	113.9
C3—C4—H4	120.0	C17—C16—H16	113.9
C5—C4—H4	120.0	C22—C17—C18	117.45 (18)
C4—C5—C6	120.78 (19)	C22—C17—C16	126.09 (18)
C4—C5—H5	119.6	C18—C17—C16	116.46 (19)
C6—C5—H5	119.6	C19—C18—C17	120.8 (2)
C1—C6—C5	118.66 (18)	C19—C18—H18	119.6
C1—C6—N1	121.31 (18)	C17—C18—H18	119.6
C5—C6—N1	120.02 (17)	C18—C19—C20	121.6 (2)
O1—C7—N1	120.08 (17)	C18—C19—H19	119.2
O1—C7—C8	120.52 (18)	C20—C19—H19	119.2
N1—C7—C8	119.39 (17)	C19—C20—C21	117.6 (2)
C16—C8—C7	116.82 (18)	C19—C20—C23	121.2 (2)
C16—C8—S1	123.09 (15)	C21—C20—C23	121.2 (2)
C7—C8—S1	119.77 (14)	C20—C21—C22	121.6 (2)
N1—C9—C10	114.96 (15)	C20—C21—H21	119.2
N1—C9—H9A	108.5	C22—C21—H21	119.2
C10—C9—H9A	108.5	C21—C22—C17	120.8 (2)
N1—C9—H9B	108.5	C21—C22—H22	119.6
C10—C9—H9B	108.5	C17—C22—H22	119.6
H9A—C9—H9B	107.5	C20—C23—H23A	109.5
C15—C10—C11	118.7 (2)	C20—C23—H23B	109.5
C15—C10—C9	123.32 (18)	H23A—C23—H23B	109.5
C11—C10—C9	117.9 (2)	C20—C23—H23C	109.5
C12—C11—C10	120.4 (3)	H23A—C23—H23C	109.5
C12—C11—H11	119.8	H23B—C23—H23C	109.5
C10—C11—H11	119.8

C8—S1—C1—C6	−20.9 (2)	C7—N1—C9—C10	87.9 (2)
C8—S1—C1—C2	160.67 (18)	C6—N1—C9—C10	−87.1 (2)
C6—C1—C2—C3	1.7 (4)	N1—C9—C10—C15	−2.7 (3)
S1—C1—C2—C3	−179.75 (19)	N1—C9—C10—C11	179.1 (2)
C1—C2—C3—C4	0.3 (4)	C15—C10—C11—C12	−1.2 (4)
C2—C3—C4—C5	−0.9 (4)	C9—C10—C11—C12	177.1 (3)
C3—C4—C5—C6	−0.4 (4)	C10—C11—C12—C13	0.1 (6)
C2—C1—C6—C5	−3.0 (3)	C11—C12—C13—C14	1.5 (6)
S1—C1—C6—C5	178.52 (16)	C12—C13—C14—C15	−1.9 (5)
C2—C1—C6—N1	175.7 (2)	C11—C10—C15—C14	0.8 (4)
S1—C1—C6—N1	−2.8 (3)	C9—C10—C15—C14	−177.5 (2)
C4—C5—C6—C1	2.4 (3)	C13—C14—C15—C10	0.8 (4)
C4—C5—C6—N1	−176.3 (2)	C7—C8—C16—C17	−178.35 (18)
C7—N1—C6—C1	24.5 (3)	S1—C8—C16—C17	8.1 (3)
C9—N1—C6—C1	−161.06 (18)	C8—C16—C17—C22	−14.8 (3)
C7—N1—C6—C5	−156.78 (18)	C8—C16—C17—C18	165.0 (2)
C9—N1—C6—C5	17.6 (3)	C22—C17—C18—C19	1.7 (3)
C6—N1—C7—O1	167.09 (18)	C16—C17—C18—C19	−178.12 (18)
C9—N1—C7—O1	−7.5 (3)	C17—C18—C19—C20	1.1 (3)
C6—N1—C7—C8	−13.7 (3)	C18—C19—C20—C21	−2.7 (3)
C9—N1—C7—C8	171.75 (16)	C18—C19—C20—C23	177.6 (2)
O1—C7—C8—C16	−11.2 (3)	C19—C20—C21—C22	1.5 (4)
N1—C7—C8—C16	169.57 (17)	C23—C20—C21—C22	−178.8 (2)
O1—C7—C8—S1	162.57 (16)	C20—C21—C22—C17	1.3 (4)
N1—C7—C8—S1	−16.6 (2)	C18—C17—C22—C21	−2.8 (3)
C1—S1—C8—C16	−156.70 (17)	C16—C17—C22—C21	176.9 (2)
C1—S1—C8—C7	29.91 (18)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg3ⁱ	0.95	3.00	3.898 (2)	158

Symmetry code: (i) x+1/4, −y+3/4, z−1/4.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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Volume 82| Part 6| June 2026| Pages 665-669

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

Crystal structure and Hirshfeld surface analyses, inter­action energy calculations and energy frameworks of (Z)-4-benzyl-2-(4-methyl­benzyl­idene)-2H-[1,4]benzo­thia­zin-3(4H)-one

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis and energy calculations

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure and Hirshfeld surface analyses, interaction energy calculations and energy frameworks of (Z)-4-benzyl-2-(4-methylbenzylidene)-2H-[1,4]benzothiazin-3(4H)-one

3. Supramolecular features