Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of (2Z)-4-benzyl-2-(2,4-di­chloro­benzyl­idene)-2H-1,4-benzo­thia­zin-3(4H)-one

Sebbar, N.K.; Hni, B.; Hökelek, T.; Labd Taha, M.; Mague, J.T.; El Ghayati, L.; Essassi, E.M.

doi:10.1107/S2056989019013586

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (2Z)-4-benzyl-2-(2,4-dichlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one

N. K. Sebbar, B. Hni, T. Hökelek, M. Labd Taha, J. T. Mague, L. El Ghayati and E. M. Essassi

The title compound contains 1,4-benzothiazine and 2,4-dichlorobenzylidene units, where the dihydrothiazine ring adopts a screw-boat conformation. In the crystal, intermolecular C—H_Bnz

O_Thz (Bnz = benzene and Thz = thiazine) hydrogen bonds form corrugated chains extending along the b-axis direction which are tied into layers parallel to the bc plane by intermolecular C—H_Methy

S_Thz (Methy = methylene) hydrogen bonds, enclosing $R_{4}^{4}$ (22) ring motifs.

Keywords: crystal structure; dihydrothiazine; hydrogen bond; π-stacking; Hirshfeld surface.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013586/lh5925sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013586/lh5925Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S2056989019013586/lh5925Isup3.cdx Supplementary material

CCDC reference: 1957875

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.026
wR factor = 0.070
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level G
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1      ..Cl1              3.24 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         21 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2016).

(2Z)-4-Benzyl-2-(2,4-dichlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one top

Crystal data top

C₂₂H₁₅Cl₂NOS	F(000) = 848
M_r = 412.31	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.0373 (7) Å	Cell parameters from 9943 reflections
b = 16.6798 (13) Å	θ = 4.4–43.5°
c = 12.511 (1) Å	µ = 4.25 mm⁻¹
β = 95.982 (2)°	T = 150 K
V = 1875.6 (3) Å³	Block, colourless
Z = 4	0.14 × 0.13 × 0.09 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3847 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3650 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.6°, θ_min = 4.4°
ω scans	h = −11→11
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −20→20
T_min = 0.59, T_max = 0.70	l = −15→15
48886 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	All H-atom parameters refined
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0379P)² + 0.6937P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3847 reflections	Δρ_max = 0.22 e Å⁻³
304 parameters	Δρ_min = −0.26 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.

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.32725 (3)	0.51603 (2)	0.51778 (3)	0.03318 (9)
Cl2	−0.08376 (4)	0.45362 (2)	0.78449 (3)	0.03443 (10)
S1	0.15102 (3)	0.21109 (2)	0.37534 (2)	0.02451 (9)
O1	0.29675 (11)	0.36735 (6)	0.18264 (8)	0.0318 (2)
N1	0.36671 (11)	0.23777 (6)	0.20360 (8)	0.0231 (2)
C1	0.29233 (13)	0.14621 (7)	0.34225 (10)	0.0235 (2)
C2	0.30706 (15)	0.07308 (8)	0.39669 (11)	0.0287 (3)
H2	0.2413 (19)	0.0621 (10)	0.4526 (14)	0.033 (4)*
C3	0.41257 (16)	0.01777 (8)	0.37140 (12)	0.0327 (3)
H3	0.4187 (18)	−0.0323 (10)	0.4058 (13)	0.030 (4)*
C4	0.50780 (16)	0.03719 (8)	0.29531 (13)	0.0330 (3)
H4	0.579 (2)	−0.0001 (12)	0.2780 (15)	0.042 (5)*
C5	0.49570 (15)	0.11045 (8)	0.24245 (11)	0.0285 (3)
H5	0.5655 (19)	0.1230 (11)	0.1921 (13)	0.035 (4)*
C6	0.38507 (13)	0.16533 (7)	0.26301 (10)	0.0233 (2)
C7	0.29726 (13)	0.30575 (7)	0.23567 (10)	0.0237 (2)
C8	0.22305 (13)	0.30312 (7)	0.33731 (10)	0.0223 (2)
C9	0.20587 (14)	0.37330 (7)	0.38765 (10)	0.0241 (2)
H9	0.2472 (18)	0.4183 (10)	0.3553 (13)	0.031 (4)*
C10	0.13615 (13)	0.38965 (7)	0.48567 (10)	0.0232 (2)
C11	0.18203 (13)	0.45583 (7)	0.55067 (10)	0.0239 (2)
C12	0.11763 (15)	0.47512 (8)	0.64272 (11)	0.0266 (3)
H12	0.152 (2)	0.5194 (11)	0.6845 (14)	0.040 (5)*
C13	0.00202 (14)	0.42783 (8)	0.67128 (10)	0.0261 (3)
C14	−0.04785 (15)	0.36229 (8)	0.61082 (11)	0.0283 (3)
H14	−0.130 (2)	0.3302 (11)	0.6306 (14)	0.038 (4)*
C15	0.01925 (15)	0.34384 (8)	0.51908 (11)	0.0271 (3)
H15	−0.019 (2)	0.3021 (11)	0.4758 (15)	0.042 (5)*
C16	0.43514 (15)	0.24544 (8)	0.10287 (10)	0.0261 (3)
H16A	0.4342 (18)	0.1915 (10)	0.0694 (13)	0.029 (4)*
H16B	0.3717 (18)	0.2771 (10)	0.0550 (13)	0.027 (4)*
C17	0.59004 (14)	0.28115 (7)	0.11411 (10)	0.0235 (2)
C18	0.65243 (16)	0.30239 (9)	0.02058 (11)	0.0311 (3)
H18	0.593 (2)	0.2943 (11)	−0.0487 (15)	0.039 (5)*
C19	0.79411 (17)	0.33523 (9)	0.02566 (13)	0.0384 (3)
H19	0.835 (2)	0.3503 (12)	−0.0383 (16)	0.050 (5)*
C20	0.87604 (17)	0.34739 (9)	0.12401 (14)	0.0382 (3)
H20	0.973 (2)	0.3695 (12)	0.1271 (15)	0.046 (5)*
C21	0.81497 (16)	0.32701 (8)	0.21707 (13)	0.0334 (3)
H21	0.874 (2)	0.3354 (11)	0.2875 (14)	0.040 (5)*
C22	0.67257 (15)	0.29448 (8)	0.21258 (11)	0.0273 (3)
H22	0.6283 (17)	0.2799 (9)	0.2793 (12)	0.024 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02604 (16)	0.03290 (17)	0.04160 (19)	−0.00735 (12)	0.00829 (13)	−0.00211 (13)
Cl2	0.03839 (18)	0.03495 (18)	0.03231 (17)	0.00967 (13)	0.01489 (13)	0.00164 (12)
S1	0.02266 (15)	0.02109 (15)	0.03075 (17)	−0.00207 (11)	0.00738 (12)	0.00098 (11)
O1	0.0405 (5)	0.0264 (5)	0.0303 (5)	0.0018 (4)	0.0116 (4)	0.0066 (4)
N1	0.0226 (5)	0.0248 (5)	0.0224 (5)	−0.0006 (4)	0.0050 (4)	0.0000 (4)
C1	0.0225 (6)	0.0217 (6)	0.0261 (6)	−0.0018 (5)	0.0009 (5)	−0.0017 (5)
C2	0.0297 (7)	0.0241 (6)	0.0321 (7)	−0.0029 (5)	0.0017 (5)	0.0022 (5)
C3	0.0349 (7)	0.0215 (6)	0.0406 (8)	0.0005 (5)	−0.0015 (6)	0.0025 (5)
C4	0.0295 (7)	0.0245 (6)	0.0446 (8)	0.0037 (5)	0.0022 (6)	−0.0047 (6)
C5	0.0253 (6)	0.0267 (6)	0.0337 (7)	−0.0007 (5)	0.0044 (5)	−0.0047 (5)
C6	0.0225 (6)	0.0214 (6)	0.0255 (6)	−0.0026 (5)	0.0004 (5)	−0.0020 (5)
C7	0.0223 (6)	0.0241 (6)	0.0247 (6)	−0.0015 (5)	0.0025 (5)	0.0010 (5)
C8	0.0194 (5)	0.0231 (6)	0.0246 (6)	0.0002 (4)	0.0034 (4)	0.0033 (4)
C9	0.0229 (6)	0.0224 (6)	0.0276 (6)	0.0000 (5)	0.0051 (5)	0.0036 (5)
C10	0.0228 (6)	0.0207 (6)	0.0265 (6)	0.0038 (5)	0.0041 (5)	0.0034 (4)
C11	0.0201 (6)	0.0224 (6)	0.0293 (6)	0.0025 (4)	0.0034 (5)	0.0033 (5)
C12	0.0259 (6)	0.0242 (6)	0.0293 (6)	0.0039 (5)	0.0015 (5)	−0.0006 (5)
C13	0.0265 (6)	0.0260 (6)	0.0267 (6)	0.0083 (5)	0.0069 (5)	0.0042 (5)
C14	0.0279 (6)	0.0238 (6)	0.0350 (7)	0.0014 (5)	0.0111 (5)	0.0048 (5)
C15	0.0281 (6)	0.0222 (6)	0.0318 (7)	−0.0001 (5)	0.0075 (5)	0.0002 (5)
C16	0.0273 (6)	0.0315 (7)	0.0196 (6)	−0.0010 (5)	0.0033 (5)	−0.0020 (5)
C17	0.0256 (6)	0.0215 (6)	0.0240 (6)	0.0032 (5)	0.0062 (5)	0.0002 (4)
C18	0.0344 (7)	0.0333 (7)	0.0271 (7)	0.0065 (6)	0.0104 (5)	0.0039 (5)
C19	0.0385 (8)	0.0330 (7)	0.0476 (9)	0.0061 (6)	0.0232 (7)	0.0101 (6)
C20	0.0270 (7)	0.0262 (7)	0.0630 (10)	−0.0002 (5)	0.0123 (6)	0.0026 (6)
C21	0.0290 (7)	0.0262 (7)	0.0442 (8)	−0.0002 (5)	−0.0002 (6)	−0.0042 (6)
C22	0.0294 (6)	0.0261 (6)	0.0265 (6)	−0.0009 (5)	0.0042 (5)	−0.0013 (5)

Geometric parameters (Å, º) top

Cl1—C11	1.7357 (13)	C10—C11	1.4076 (18)
Cl2—C13	1.7382 (13)	C11—C12	1.3814 (18)
S1—C8	1.7525 (12)	C12—C13	1.3854 (19)
S1—C1	1.7561 (13)	C12—H12	0.940 (19)
O1—C7	1.2228 (16)	C13—C14	1.3781 (19)
N1—C7	1.3759 (16)	C14—C15	1.3874 (19)
N1—C6	1.4192 (16)	C14—H14	0.971 (19)
N1—C16	1.4661 (16)	C15—H15	0.928 (19)
C1—C2	1.3967 (18)	C16—C17	1.5143 (18)
C1—C6	1.4000 (18)	C16—H16A	0.993 (17)
C2—C3	1.387 (2)	C16—H16B	0.945 (16)
C2—H2	0.981 (18)	C17—C22	1.3899 (18)
C3—C4	1.387 (2)	C17—C18	1.3965 (18)
C3—H3	0.938 (17)	C18—C19	1.388 (2)
C4—C5	1.388 (2)	C18—H18	0.979 (18)
C4—H4	0.94 (2)	C19—C20	1.383 (2)
C5—C6	1.3990 (18)	C19—H19	0.95 (2)
C5—H5	0.960 (18)	C20—C21	1.382 (2)
C7—C8	1.4988 (17)	C20—H20	0.95 (2)
C8—C9	1.3458 (18)	C21—C22	1.392 (2)
C9—C10	1.4616 (17)	C21—H21	0.993 (18)
C9—H9	0.948 (17)	C22—H22	0.992 (16)
C10—C15	1.4024 (18)

Cl1···Cl1ⁱ	3.2439 (5)	C6···C22	3.4830 (18)
Cl1···C14ⁱⁱ	3.4981 (14)	C6···C12^v	3.5828 (18)
Cl1···H9	2.647 (16)	C7···C22	3.4391 (18)
Cl2···H19ⁱⁱⁱ	2.96 (2)	C10···C12ⁱⁱ	3.4871 (18)
Cl2···H9ⁱⁱ	3.044 (16)	C14···C20^iv	3.572 (2)
Cl2···H4^iv	3.138 (18)	C5···H16A	2.563 (16)
S1···Cl2^v	3.5832 (5)	C6···H22	2.904 (15)
S1···Cl2^v	3.5832 (5)	C8···H15	2.929 (18)
S1···N1	3.0801 (11)	C16···H5	2.556 (18)
S1···C15	3.1625 (14)	C17···H5	2.829 (18)
S1···C13^v	3.6033 (13)	C18···H3^vi	2.998 (17)
S1···H15	2.578 (18)	C21···H12ⁱ	2.845 (18)
O1···C17	3.2096 (16)	H14···C20^iv	2.964 (18)
O1···C4^vi	3.3346 (17)	H14···C21^iv	2.899 (18)
O1···H9	2.406 (16)	H14···C22^iv	2.990 (18)
O1···H16B	2.345 (16)	H15···C19^iv	2.951 (18)
O1···H4^vi	2.51 (2)	H16B···S1^v	2.852 (16)
N1···S1	3.0801 (11)	H16B···C1^v	2.973 (16)
N1···H22	2.552 (15)	H18···C6^v	2.934 (19)
C1···C12^v	3.4639 (18)	H5···H16A	2.16 (2)
C1···C13^v	3.4372 (18)	H12···H21ⁱ	2.46 (3)
C2···C12^v	3.541 (2)	H15···H21^viii	2.51 (3)
C3···C3^vii	3.485 (2)	H16B···H18	2.51 (2)
C5···C22	3.4988 (19)	H18···H22^v	2.53 (2)
C5···C17	3.4201 (18)

C8—S1—C1	100.14 (6)	C11—C12—C13	118.49 (12)
C7—N1—C6	125.51 (10)	C11—C12—H12	120.1 (11)
C7—N1—C16	115.14 (10)	C13—C12—H12	121.4 (11)
C6—N1—C16	119.20 (10)	C14—C13—C12	121.49 (12)
C2—C1—C6	120.71 (12)	C14—C13—Cl2	119.70 (10)
C2—C1—S1	117.26 (10)	C12—C13—Cl2	118.79 (10)
C6—C1—S1	122.02 (10)	C13—C14—C15	118.94 (12)
C3—C2—C1	120.17 (13)	C13—C14—H14	120.9 (10)
C3—C2—H2	121.4 (10)	C15—C14—H14	120.1 (10)
C1—C2—H2	118.5 (10)	C14—C15—C10	122.24 (12)
C4—C3—C2	119.47 (13)	C14—C15—H15	118.7 (12)
C4—C3—H3	120.7 (10)	C10—C15—H15	118.9 (12)
C2—C3—H3	119.8 (10)	N1—C16—C17	115.04 (10)
C3—C4—C5	120.59 (13)	N1—C16—H16A	107.3 (9)
C3—C4—H4	119.6 (12)	C17—C16—H16A	111.3 (9)
C5—C4—H4	119.7 (12)	N1—C16—H16B	108.1 (10)
C4—C5—C6	120.71 (13)	C17—C16—H16B	109.4 (10)
C4—C5—H5	118.7 (10)	H16A—C16—H16B	105.2 (13)
C6—C5—H5	120.6 (11)	C22—C17—C18	118.42 (12)
C5—C6—C1	118.24 (12)	C22—C17—C16	123.41 (11)
C5—C6—N1	120.50 (11)	C18—C17—C16	118.16 (12)
C1—C6—N1	121.26 (11)	C19—C18—C17	120.85 (14)
O1—C7—N1	120.68 (11)	C19—C18—H18	120.7 (11)
O1—C7—C8	120.54 (11)	C17—C18—H18	118.5 (11)
N1—C7—C8	118.78 (10)	C20—C19—C18	120.29 (14)
C9—C8—C7	117.09 (11)	C20—C19—H19	119.3 (12)
C9—C8—S1	124.79 (10)	C18—C19—H19	120.4 (12)
C7—C8—S1	117.88 (9)	C21—C20—C19	119.32 (14)
C8—C9—C10	129.48 (12)	C21—C20—H20	120.6 (11)
C8—C9—H9	114.8 (10)	C19—C20—H20	120.1 (11)
C10—C9—H9	115.7 (10)	C20—C21—C22	120.69 (14)
C15—C10—C11	116.15 (11)	C20—C21—H21	119.2 (11)
C15—C10—C9	123.53 (12)	C22—C21—H21	120.1 (11)
C11—C10—C9	120.29 (11)	C17—C22—C21	120.43 (13)
C12—C11—C10	122.68 (12)	C17—C22—H22	118.7 (9)
C12—C11—Cl1	117.23 (10)	C21—C22—H22	120.9 (9)
C10—C11—Cl1	120.08 (10)

C8—S1—C1—C2	155.71 (10)	S1—C8—C9—C10	4.6 (2)
C8—S1—C1—C6	−25.73 (11)	C8—C9—C10—C15	−29.8 (2)
C6—C1—C2—C3	−1.12 (19)	C8—C9—C10—C11	152.34 (13)
S1—C1—C2—C3	177.47 (10)	C15—C10—C11—C12	0.42 (18)
C1—C2—C3—C4	3.0 (2)	C9—C10—C11—C12	178.46 (11)
C2—C3—C4—C5	−1.7 (2)	C15—C10—C11—Cl1	179.25 (9)
C3—C4—C5—C6	−1.5 (2)	C9—C10—C11—Cl1	−2.71 (16)
C4—C5—C6—C1	3.35 (19)	C10—C11—C12—C13	−0.78 (19)
C4—C5—C6—N1	−175.72 (12)	Cl1—C11—C12—C13	−179.64 (9)
C2—C1—C6—C5	−2.05 (18)	C11—C12—C13—C14	0.72 (19)
S1—C1—C6—C5	179.43 (9)	C11—C12—C13—Cl2	−177.88 (9)
C2—C1—C6—N1	177.02 (11)	C12—C13—C14—C15	−0.33 (19)
S1—C1—C6—N1	−1.50 (17)	Cl2—C13—C14—C15	178.27 (10)
C7—N1—C6—C5	−158.93 (12)	C13—C14—C15—C10	0.0 (2)
C16—N1—C6—C5	16.29 (17)	C11—C10—C15—C14	0.00 (19)
C7—N1—C6—C1	22.03 (18)	C9—C10—C15—C14	−177.97 (12)
C16—N1—C6—C1	−162.76 (11)	C7—N1—C16—C17	84.01 (14)
C6—N1—C7—O1	174.42 (12)	C6—N1—C16—C17	−91.69 (14)
C16—N1—C7—O1	−0.96 (17)	N1—C16—C17—C22	9.68 (18)
C6—N1—C7—C8	−5.15 (18)	N1—C16—C17—C18	−169.73 (11)
C16—N1—C7—C8	179.46 (10)	C22—C17—C18—C19	0.7 (2)
O1—C7—C8—C9	−23.67 (18)	C16—C17—C18—C19	−179.87 (13)
N1—C7—C8—C9	155.91 (11)	C17—C18—C19—C20	0.1 (2)
O1—C7—C8—S1	150.91 (10)	C18—C19—C20—C21	−0.4 (2)
N1—C7—C8—S1	−29.52 (15)	C19—C20—C21—C22	0.1 (2)
C1—S1—C8—C9	−145.73 (11)	C18—C17—C22—C21	−1.06 (19)
C1—S1—C8—C7	40.15 (10)	C16—C17—C22—C21	179.53 (12)
C7—C8—C9—C10	178.71 (12)	C20—C21—C22—C17	0.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^ix	0.936 (19)	2.51 (2)	3.3346 (17)	147.7 (15)
C16—H16B···S1^v	0.945 (16)	2.852 (16)	3.7011 (13)	149.9 (12)
C3—H3···Cg4^ix	0.938 (17)	2.901 (17)	3.6428 (15)	136.8 (13)
C14—H14···Cg4^x	0.971 (19)	2.710 (18)	3.5593 (15)	146.8 (14)
C18—H18···Cg1^xi	0.979 (18)	2.969 (18)	3.6759 (16)	130.0 (13)

Symmetry codes: (v) x, −y+1/2, z−1/2; (ix) −x+1, y−1/2, −z+1/2; (x) x−1, −y−1/2, z−1/2; (xi) x, −y−1/2, z−3/2.

Table 4. Comparison of the selected (X-ray and DFT) geometric data (Å, °) top

Bonds/angles	X-ray	B3LYP/6-311G(d,p)
Cl1—C11	1.7357 (13)	1.80981
Cl2—C13	1.7382 (13)	1.80489
S1—C8	1.7525 (12)	1.80120
S1—C1	1.7561 (13)	1.82629
O1—C7	1.2228 (16)	1.23968
N1—C7	1.3759 (16)	1.38157
N1—C6	1.4192 (16)	1.41776
N1—C16	1.4661 (16)	1.47048
C8—S1—C1	100.14 (6)	98.69028
C7—N1—C6	125.51 (10)	124.58623
C7—N1—C16	115.14 (10)	116.12685
C6—N1—C16	119.20 (10)	119.26679
C2—C1—C6	120.71 (12)	121.24260
C2—C1—S1	117.26 (10)	117.48822
C6—C1—S1	122.02 (10)	121.26667

Table 5. Calculated energies. top

Molecular Energy (a.u.) (eV)	Compound (I)
Total Energy TE (eV)	-62249, 6662
E_HOMO (eV)	-8.2479
E_LUMO (eV)	-2.9115
Gap ΔE (eV)	5.3364
Dipole moment, µ (Debye)	3.4723
Ionisation potential, I (eV)	8.2479
Electron affinity, A	2.9115
Electro negativity, χ	5.3364
Hardness, η	2.6682
Electrophilicity index, ω	5.8340
Softness, σ	0.3748
Fraction of electron transferred, ΔN	0.2662

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Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of (2Z)-4-benzyl-2-(2,4-di­chloro­benzyl­idene)-2H-1,4-benzo­thia­zin-3(4H)-one

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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (2Z)-4-benzyl-2-(2,4-dichlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one