Structural, Hirshfeld surface and three-dimensional inter­action energy studies of 2-(6-iodo-4-oxo-3,4-di­hydro­quinazolin-3-yl)ethane­sulfonyl fluoride

Ganesha, D.P.; Sreenatha, N.R.; Shankara, S.R.; Lakshminarayana, B.N.

doi:10.1107/S205698902201221X

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ISSN: 2056-9890

Volume 79| Part 2| February 2023| Pages 65-69

https://doi.org/10.1107/S205698902201221X

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Structural, Hirshfeld surface and three-dimensional interaction energy studies of 2-(6-iodo-4-oxo-3,4-dihydroquinazolin-3-yl)ethanesulfonyl fluoride

D. P. Ganesha,^a N. R. Sreenatha,^b S. R. Shankara ^c and B. N. Lakshminarayana ^a ^*

^aDepartment of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru - 577102, Karnataka, India, ^bDepartment of Physics, Government Engineering College, B M Road, Dairy Circle, Hassan - 573 201, Karnataka, India, and ^cDepartment of Engineering Physics, BGS Institute of Technology, Adichunchanagiri University, B G Nagara, Karnataka, India
^*Correspondence e-mail: bnlphysics@gmail.com

Edited by A. S. Batsanov, University of Durham, United Kingdom (Received 17 October 2022; accepted 28 December 2022; online 6 January 2023)

In the crystal, molecules of the title compound, C₁₀H₈FIN₂O₃S, are connected through C—H⋯N and C—H⋯O hydrogen bonds, I⋯O halogen bonds, π–π stacking interactions between the benzene and pyrimidine rings, and edge-to-edge electrostatic interactions, as shown by the analysis of the Hirshfeld surface and two-dimensional fingerprint plots, as well as intermolecular interaction energies calculated using the electron-density model at the HF/3–21 G level of theory.

Keywords: Single-crystal structure; C—H⋯N and C—H⋯O hydrogen bonds; I⋯O halogen bond; Hirshfeld surface; intermolecular energies.

CCDC reference: 1987361

1. Chemical context

Quinazoline is an aromatic heterocycle consisting of a benzene ring fused with a pyrimidine ring. Its derivatives are well known for their biological activities such as anti-analgesic, anti-inflammatory, anti-hypertensive, sedative, hypnotic, anti-histaminic, anti-tumor, anti-microbial, anti-convulsant, anti-bacterial, anti-fungal, enzyme inhibition, and anti-HIV activities (Kumar et al., 1981 ; Baker et al., 1952 ; Rewcastle et al., 1995 ; Hitkari et al., 1995 ; Bertelli et al., 2000 ; Yang et al., 2009 ; Cao et al., 2009 ; De Clercq, 2001 ). Compounds bearing the quinazoline moiety also are potent cytotoxic agents (Ibrahim et al., 1988 ; Riou et al., 1991 ; Braña et al., 1994 ; Helissey et al., 1994 ), show anti-oxidant (Al-Amiery et al., 2014 ) and insecticidal (Yang et al., 2021 ) activities. In view of their therapeutic importance, we report herein the crystal structure, Hirshfeld surface and three-dimensional interaction energy studies of 2-(6-iodo-4-oxo-3,4-dihydroquinazolin-3-yl)ethanesulfonyl fluoride, (I).

2. Structural commentary

The molecular structure of (I) (Fig. 1) shows an out-of-plane conformation of the (CH₂)₂SO₂F side chain, the C9/C10/S1 fragment forming a dihedral angle of 76.1 (5)° with the quinazoline (N1/N2/C1–C8) system mean plane, whereas the I1 and O1 substituents do not deviate appreciably from the latter plane. The molecule is stabilized by a weak intramolecular C10—H10B⋯O1 hydrogen bond, forming an S(6) ring motif. The S1 atom has a slightly distorted tetrahedral geometry. In the heterocycle, the N1=C1 bond [1.271 (8) Å] is essentially double, while those at the three-coordinate N2 atom are nominally single [C1—N2 = 1.359 (7), N2—C2 = 1.384 (6) Å].

Figure 1
Molecular structure of (I)

. The atomic displacement ellipsoids are drawn at the 50% probability level.

The bond lengths and angles are in agreement with those in related structures (El-Hiti et al., 2014 ; Al-Salahi et al., 2012 ; Utayeva et al., 2013 ; Priya et al., 2011 ; Lakshminarayana et al., 2009 , 2022 ; Sreenatha et al., 2018a ,b , 2020 , 2022 ).

3. Supramolecular features

In the crystal, each molecule donates three and accepts three intermolecular hydrogen bonds, viz. C1—H1⋯N1, C10—H10B⋯O1, C10—H10A⋯O1 (Table 1) and their inversion equivalents. Thus, each molecule participates in three centrosymmetric dimers with R₂²(6), R₂²(12) and R₂²(12) ring motifs, respectively (Fig. 2). Molecules related by the a translation, form a continuous stack via π–π interactions between the benzene and the pyrimidine rings (which are parallel within 1.5°), with a mean interplanar separation of 3.503 (4) Å (Fig. 3). The I1⋯O2(x − 1, y + 1, z) contact of 3.152 (6) Å is considerably shorter than the sum of the van der Waals radii of 3.61 Å (Batsanov, 1995 ; Rowland & Taylor, 1996 ) and can be described as a halogen bond (Metrangolo & Resnati, 2001 ), the nearly linear angle C6—I1⋯O2 = 175.9 (3)° being typical of such bonds.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1ⁱ	0.93	2.46	3.284 (8)	148
C10—H10B⋯O1ⁱⁱ	0.97	2.56	3.493 (7)	160
C10—H10A⋯O1ⁱⁱⁱ	0.97	2.45	3.151 (7)	129
C9—H9A⋯O3^iv	0.97	2.33	3.150 (8)	141
C10—H10B⋯O1	0.97	2.59	3.121 (7)	115
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) x+1, y, z.

Figure 2
Intermolecular hydrogen (see Table 1

) and halogen bonds in the structure of (I)

Figure 3
π–π stacking in the structure of (I)

4. Database survey

A survey of the Cambridge Structural Database (CSD version 5.41, update of October 2022; Groom et al., 2016 ) revealed only one structure, namely (Z)-ethyl-2-cyano-2-(3H-quinazoline-4-ylidene)acetate (ACEZUE; Tulyasheva et al., 2005 ), which shares such features of (I) as one two-coordinate (N1) and one three-coordinate (N2) nitrogen atom of the quinazoline ring system, as well as an exocyclic double bond at C2, although in this case the H atom at N2 is not substituted. Of the other comparable quinazoline derivatives, in 3-amino-6-bromo-1-methyl-2, 4-(1H,3H)-quinazolinedione (ABMQZD; Ardebili & While, 1978 ) both N atoms are three-coordinate, while in N-(5-methyl-1,2-oxazol-3-yl)-4-[(quinazolin-4-yl) level of theoryamino]benzene-1-sulfonamide and N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide (GEYYOB, GEYYUH; Sunil Kumar et al., 2018 ) both are two-coordinate.

5. Hirshfeld surfaces and 2D fingerprint calculations

The Hirshfeld surfaces and two-dimensional fingerprint plots were calculated using CrystalExplorer17.5 (Spackman et al., 2009 ) to analyse the intermolecular interactions. The three-dimensional Hirshfeld surface mapped over the normalized contact distance (d_norm) is shown in Fig. 4. The eight bright-red spots, indicating shortened contacts, correspond to the three pairs of intermolecular hydrogen bonds and one pair of halogen bonds discussed in Section 3. The two-dimensional fingerprint plots show the H⋯O contacts to be the most common (23.0%), followed by H⋯H (13.5%), H⋯C (11.5%), H⋯I (9.9%), I⋯O (7.8%), H⋯F (6.7%), H⋯N (6.4%), I⋯F (4.0%), I⋯C (3.2%), O⋯O (2.2%) and C⋯N (1.9%) (including the reverse ones for all heteronuclear contacts). The characteristic spikes in the plots of the H⋯O and H⋯N contacts indicate intermolecular hydrogen bonds, those in the I⋯O plot indicate halogen bonds (Fig. 5).

Figure 4
Different aspects of the three-dimensional Hirshfeld surface of (I)

mapped over d_norm. Red spots indicate shortened contacts, revealing intermolecular hydrogen and halogen bonds

Figure 5
Selected two-dimensional fingerprint plots of structure (I)

; d_i and d_e are the distances from the Hirshfeld surface to the nearest internal and external atoms. Arrows indicate the `spikes' characteristic of hydrogen and halogen bonds

6. Three-dimensional framework analysis of interaction energies

Quantification of intermolecular interactions energies is important for molecular recognition, protein modelling and drug design (Volkov & Coppens, 2004 ). We computed these energies for (I) with the HF/3-21G(d,p) electron-density model (Grimme, 2006 ), using CrystalExplorer17.5 software. Eleven molecules surrounding the original one with shortest intermolecular atom–atom distances of 3.8 Å or less were included in the calculations. The total interaction energy (E_tot) between each pair of molecules comprises coloumbic (E_ele), dispersion (E_dis), polarization (E_pol) and exchange-repulsion interaction energies (E_rep) (Turner et al., 2015 , 2017 ). The E_ele, E_dis and E_tot intermolecular energy frameworks for (I) are shown graphically in Fig. 6 and numerically in Fig. 7. The molecular stacks (Fig. 3, top line in the Fig. 7 table) are held together mostly by dispersion (van der Waals) interactions, supported by the shortest C—H⋯O hydrogen bonds, while edge-to-edge intermolecular contacts (lines 5 to 8) have larger contributions of electrostatic interactions. The interaction between halogen-bonded molecules (line 3) is smaller than the above in absolute terms (10.8 kJ mol⁻¹), but is remarkable given that only one pair of atoms is actually in contact.

Figure 6
Intermolecular energy frameworks of (a) E_ele, (b) E_dis and (c) E_tot in the structure of (I)

, viewed down the b axis.

Figure 7
Intermolecular energies (in kJ mol⁻¹) and their components in the structure of (I)

. N is the number of molecules in a group, Symop is the symmetry operator, R is the distance between molecular centroids in Å.

7. Synthesis and crystallization

To an ice-cooled stirred suspension of NaH (60% suspension in mineral oil; 125 mg, 2.0 mmol, 2.0 equiv) and 6-iodoquinazolin-4(3H)-one (1.0 mmol, 1.0 equiv) in DMF (2 mL), a solution of 2-bromoethanesulfonyl fluoride (350 mg, 1.0 mmol, 1.0 equiv) in DMF (1 mL) was added, under an N₂ atmosphere. The reaction was heated at 353 K for 4 h under an N₂ atmosphere (monitored by TLC). After the complete conversion of the reactants as confirmed from TLC analysis, the reaction mixture was quenched with saturated NH₄Cl solution (25 mL), extracted with EtOAc (25 mL) and the collected organic layer was further washed with water (25 mL) and brine (25 mL), then dried over anhydrous Na₂SO₄ and concentrated under vacuum. Compound (I) was isolated by silica gel chromatography (using chloroform and methanol as mobile phase) and recrystallized from DMF.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were placed in idealized positions and refined using a riding model with C—H 0.93 Å for sp² and 0.97 Å for sp³ C atoms, with U_iso(H) = 1.2U_eq(C) for both.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₈FIN₂O₃S
M_r	382.14
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	5.0230 (5), 11.3241 (11), 11.5509 (11)
α, β, γ (°)	103.081 (2), 96.742 (1), 97.860 (1)
V (Å³)	626.43 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	2.74
Crystal size (mm)	0.34 × 0.30 × 0.27

Data collection
Diffractometer	Bruker APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4073, 3207, 2315
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.166, 1.11
No. of reflections	3207
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −1.39
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 1987361

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902201221X/zv2021sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902201221X/zv2021Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902201221X/zv2021Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: PLATON (Spek, 2020).

2-(6-Iodo-4-oxo-3,4-dihydroquinazolin-3-yl)ethanesulfonyl fluoride top

Crystal data top

C₁₀H₈FIN₂O₃S	Z = 2
M_r = 382.14	F(000) = 368
Triclinic, P1	D_x = 2.026 Mg m⁻³
a = 5.0230 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3241 (11) Å	Cell parameters from 3207 reflections
c = 11.5509 (11) Å	θ = 2.9–28.6°
α = 103.081 (2)°	µ = 2.74 mm⁻¹
β = 96.742 (1)°	T = 293 K
γ = 97.860 (1)°	Block, colourless
V = 626.43 (11) Å³	0.34 × 0.30 × 0.27 mm

Data collection top

Bruker APEXII diffractometer	2315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 28.6°, θ_min = 2.9°
SAINT (Bruker, 2009) scans	h = −6→6
4073 measured reflections	k = −15→15
3207 independent reflections	l = −15→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max = 0.027
S = 1.11	Δρ_max = 0.88 e Å⁻³
3207 reflections	Δρ_min = −1.39 e Å⁻³
164 parameters	Extinction correction: SHELXL2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.075 (6)

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
I1	0.12293 (8)	0.97164 (3)	0.27666 (4)	0.0627 (3)
S1	0.6688 (3)	0.23549 (14)	0.14355 (16)	0.0558 (4)
C4	0.6072 (11)	0.6675 (5)	0.4017 (4)	0.0400 (10)
O1	0.7389 (9)	0.6113 (4)	0.0952 (3)	0.0492 (9)
C6	0.3202 (11)	0.8380 (5)	0.3281 (5)	0.0452 (12)
N1	0.7570 (11)	0.5853 (5)	0.4409 (4)	0.0502 (11)
C3	0.5977 (10)	0.6826 (5)	0.2840 (4)	0.0374 (10)
C2	0.7379 (10)	0.6082 (4)	0.2009 (4)	0.0370 (10)
C1	0.8777 (12)	0.5224 (5)	0.3644 (5)	0.0473 (12)
H1	0.976779	0.467243	0.390691	0.057*
C10	0.8383 (12)	0.3422 (5)	0.0775 (5)	0.0466 (12)
H10A	0.946662	0.300744	0.022171	0.056*
H10B	0.705250	0.375036	0.031537	0.056*
C9	1.0223 (10)	0.4478 (5)	0.1700 (5)	0.0424 (11)
H9A	1.146034	0.414079	0.219643	0.051*
H9B	1.130812	0.496966	0.128183	0.051*
C5	0.4554 (11)	0.7690 (5)	0.2498 (5)	0.0416 (11)
H5	0.452220	0.780100	0.172336	0.050*
C7	0.3249 (13)	0.8216 (6)	0.4448 (6)	0.0554 (14)
H7	0.231139	0.867697	0.498211	0.066*
O3	0.4727 (11)	0.2855 (6)	0.2052 (7)	0.0900 (19)
O2	0.8528 (12)	0.1889 (8)	0.2130 (10)	0.139 (4)
N2	0.8762 (8)	0.5277 (4)	0.2479 (4)	0.0393 (9)
F1	0.532 (2)	0.1389 (6)	0.0379 (6)	0.167 (4)
C8	0.4670 (14)	0.7380 (6)	0.4805 (5)	0.0534 (14)
H8	0.470010	0.728088	0.558397	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0622 (3)	0.0401 (3)	0.0873 (4)	0.01597 (19)	0.0067 (2)	0.0166 (2)
S1	0.0624 (8)	0.0382 (7)	0.0754 (11)	0.0114 (6)	0.0258 (8)	0.0219 (7)
C4	0.049 (2)	0.038 (3)	0.031 (2)	0.001 (2)	0.005 (2)	0.0078 (19)
O1	0.069 (2)	0.049 (2)	0.038 (2)	0.0201 (19)	0.0135 (17)	0.0178 (16)
C6	0.046 (3)	0.033 (3)	0.055 (3)	0.007 (2)	0.006 (2)	0.007 (2)
N1	0.072 (3)	0.048 (3)	0.034 (2)	0.017 (2)	0.003 (2)	0.0161 (19)
C3	0.042 (2)	0.034 (2)	0.036 (2)	0.0027 (19)	0.0040 (19)	0.0112 (19)
C2	0.045 (2)	0.031 (2)	0.036 (3)	0.0049 (19)	0.0046 (19)	0.0147 (19)
C1	0.062 (3)	0.040 (3)	0.039 (3)	0.011 (2)	−0.007 (2)	0.014 (2)
C10	0.064 (3)	0.038 (3)	0.042 (3)	0.010 (2)	0.018 (2)	0.012 (2)
C9	0.044 (2)	0.040 (3)	0.050 (3)	0.014 (2)	0.012 (2)	0.017 (2)
C5	0.050 (3)	0.038 (3)	0.037 (3)	0.006 (2)	0.005 (2)	0.012 (2)
C7	0.067 (4)	0.045 (3)	0.056 (3)	0.012 (3)	0.021 (3)	0.009 (3)
O3	0.078 (3)	0.079 (4)	0.142 (5)	0.028 (3)	0.065 (4)	0.053 (4)
O2	0.073 (4)	0.141 (7)	0.265 (11)	0.040 (4)	0.031 (5)	0.160 (8)
N2	0.044 (2)	0.036 (2)	0.040 (2)	0.0097 (18)	0.0016 (17)	0.0129 (17)
F1	0.280 (10)	0.083 (4)	0.098 (4)	−0.080 (5)	0.054 (5)	−0.009 (3)
C8	0.076 (4)	0.048 (3)	0.041 (3)	0.010 (3)	0.017 (3)	0.015 (2)

Geometric parameters (Å, º) top

I1—C6	2.075 (5)	C2—N2	1.384 (6)
S1—O3	1.390 (6)	C1—N2	1.359 (7)
S1—O2	1.389 (6)	C1—H1	0.9300
S1—F1	1.467 (6)	C10—C9	1.521 (8)
S1—C10	1.748 (5)	C10—H10A	0.9700
C4—C3	1.404 (7)	C10—H10B	0.9700
C4—N1	1.393 (7)	C9—N2	1.462 (6)
C4—C8	1.392 (8)	C9—H9A	0.9700
O1—C2	1.230 (6)	C9—H9B	0.9700
C6—C5	1.363 (8)	C5—H5	0.9300
C6—C7	1.400 (9)	C7—C8	1.367 (9)
N1—C1	1.271 (8)	C7—H7	0.9300
C3—C5	1.387 (7)	C8—H8	0.9300
C3—C2	1.443 (7)

O3—S1—O2	113.9 (5)	C9—C10—H10A	109.1
O3—S1—F1	108.8 (5)	S1—C10—H10A	109.1
O2—S1—F1	110.1 (6)	C9—C10—H10B	109.1
O3—S1—C10	110.6 (3)	S1—C10—H10B	109.1
O2—S1—C10	110.8 (3)	H10A—C10—H10B	107.8
F1—S1—C10	101.9 (3)	N2—C9—C10	114.0 (4)
C3—C4—N1	121.3 (5)	N2—C9—H9A	108.8
C3—C4—C8	118.8 (5)	C10—C9—H9A	108.8
N1—C4—C8	119.8 (5)	N2—C9—H9B	108.8
C5—C6—C7	119.6 (5)	C10—C9—H9B	108.8
C5—C6—I1	120.1 (4)	H9A—C9—H9B	107.7
C7—C6—I1	120.3 (4)	C6—C5—C3	121.0 (5)
C1—N1—C4	116.9 (4)	C6—C5—H5	119.5
C4—C3—C5	119.6 (5)	C3—C5—H5	119.5
C4—C3—C2	119.2 (4)	C8—C7—C6	120.2 (6)
C5—C3—C2	121.2 (4)	C8—C7—H7	119.9
O1—C2—N2	120.0 (5)	C6—C7—H7	119.9
O1—C2—C3	125.0 (4)	C1—N2—C2	121.1 (4)
N2—C2—C3	115.0 (4)	C1—N2—C9	120.1 (4)
N1—C1—N2	126.4 (5)	C2—N2—C9	118.8 (4)
N1—C1—H1	116.8	C7—C8—C4	120.8 (5)
N2—C1—H1	116.8	C7—C8—H8	119.6
C9—C10—S1	112.5 (4)	C4—C8—H8	119.6

C3—C4—N1—C1	−2.0 (8)	I1—C6—C5—C3	177.4 (4)
C8—C4—N1—C1	179.1 (6)	C4—C3—C5—C6	−1.2 (8)
N1—C4—C3—C5	−177.4 (5)	C2—C3—C5—C6	179.1 (5)
C8—C4—C3—C5	1.6 (8)	C5—C6—C7—C8	0.8 (9)
N1—C4—C3—C2	2.3 (7)	I1—C6—C7—C8	−176.6 (5)
C8—C4—C3—C2	−178.8 (5)	N1—C1—N2—C2	1.0 (9)
C4—C3—C2—O1	178.3 (5)	N1—C1—N2—C9	−179.1 (6)
C5—C3—C2—O1	−2.1 (8)	O1—C2—N2—C1	−179.9 (5)
C4—C3—C2—N2	−1.0 (7)	C3—C2—N2—C1	−0.6 (7)
C5—C3—C2—N2	178.7 (4)	O1—C2—N2—C9	0.2 (7)
C4—N1—C1—N2	0.3 (9)	C3—C2—N2—C9	179.5 (4)
O3—S1—C10—C9	70.2 (5)	C10—C9—N2—C1	106.4 (6)
O2—S1—C10—C9	−57.1 (7)	C10—C9—N2—C2	−73.7 (6)
F1—S1—C10—C9	−174.2 (6)	C6—C7—C8—C4	−0.4 (10)
S1—C10—C9—N2	−67.0 (5)	C3—C4—C8—C7	−0.7 (9)
C7—C6—C5—C3	0.0 (8)	N1—C4—C8—C7	178.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ⁱ	0.93	2.46	3.284 (8)	148
C10—H10B···O1ⁱⁱ	0.97	2.56	3.493 (7)	160
C10—H10A···O1ⁱⁱⁱ	0.97	2.45	3.151 (7)	129
C9—H9A···O3^iv	0.97	2.33	3.150 (8)	141
C10—H10B···O1	0.97	2.59	3.121 (7)	115

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

Acknowledgements

The authors are thankful to Dr A. S. Jeevan Chakravarthy, C/O Professor H. ILA, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research, Jakkur Post, Amruthahalli, Bengaluru − 560064, Karnataka, and to the Department of Engineering Physics, Adichunchanagiri Institute of Technology, Chikkamagaluru, Karnataka, India, for support.

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