Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[4-(2-methyl­prop­yl)phen­yl]-N′-[(1Z)-1-(thio­phen-2-yl)ethyl­idene]propane­hydrazide

Jayadevan, S.; Sujith, K.V.; Biju, A.R.

doi:10.1107/S2056989025003329

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ISSN: 2056-9890

Volume 81| Part 5| May 2025| Pages 417-419

https://doi.org/10.1107/S2056989025003329

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Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[4-(2-methylpropyl)phenyl]-N′-[(1Z)-1-(thiophen-2-yl)ethylidene]propanehydrazide

Sarayu Jayadevan,^a,^b K. V. Sujith ^c and A. R. Biju ^b ^*

^aDepartment of Chemistry, Sir Syed College, Taliparamba, Kannur, 670 142, India, ^bDepartment of Chemistry, Kannur University, Swami Anandatheertha Campus, Edat PO, Payyanur, 670 327, Kerala, India, and ^cDepartment of Chemistry, Payyanur College, Edat PO, Payyanur, 670 327, Kerala, India
^*Correspondence e-mail: [email protected]

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 26 February 2025; accepted 13 April 2025; online 24 April 2025)

In the title compound C₁₉H₂₄N₂OS, intermolecular N—H⋯O hydrogen bonds generate R₂²(8) ring motifs, forming dimers with an interaction energy of −70.5 kJ mol⁻¹. A short S⋯C interaction produces another dimer with an interaction energy of −30.6 kJ mol⁻¹. The intermolecular interactions were quantified using Hirshfeld surface analysis. The two-dimensional fingerprint plots indicate that the major contributions to the crystal packing are from H⋯H (67.9%), C⋯H (13.7%), O⋯H (7.3%) and S⋯H (4.3%) interactions.

Keywords: crystal structure; Hirshfeld surface analysis; single crystal X-ray diffraction; interaction energy; ibuprofen hydrazide.

CCDC reference: 2443395

1. Chemical context

Derivatives of ibuprofen have been synthesized to enhance the efficacy and reduce the side effects commonly associated with traditional NSAIDs (Ahmadi et al., 2017 ). These derivatives have shown promising results in preliminary studies, particularly regarding anti-inflammatory, analgesic, and antimicrobial activities (Sujith et al., 2009 ; Dhakane et al., 2014 ). Compared to other derivatives of NSAIDs, ibuprofen hydrazides may offer distinct advantages, although comprehensive clinical comparisons are still limited (Kamms & Hadi, 2023 ). Based on the above studies, we herein report the crystal structure of the ibuprofen hydrazide derivative 2-[4-(2-methylpropyl)phenyl]-N′-[(1Z)-1-(thiophen-2-yl)ethylidene]propanehydrazide (1).

2. Structural commentary

The title compound crystallizes in the triclinic space group Pī with one molecule in the asymmetric unit (Fig. 1) The lengths of the C—S bonds C16—S1 and C19—S1 are 1.7225 (14) and 1.7115 (18) Å, respectively, while the carbonyl bond distance C13—O1 is 1.2297 (15) Å. The torsion angle N1—N2—C14—C16 is 176.95 (10)°, while C8—C11—C13—O1 is 103.88 (14)°. The benzene (A, C5–C10; r.m.s.d. = 0.004 Å) and thiophene (B, C16–C19/S1; r.m.s.d. = 0.004 Å) rings are not coplanar, subtending a dihedral angle of 86.69 (4)°.

Figure 1
The molecular structure of 1 with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the crystal, N1—H1⋯O1 hydrogen bonds [2.119 (18) Å; Table 1] lead to the formation of dimers with an R₂²(8) motif. Energy calculations at the B3LYP/6-31G(d, p) level were performed using Crystal Explorer 21.5 (Mackenzie et al., 2017 ; Spackman et al., 2021 ) software with the CIF as the input file. The dimer energy was found to be −70.5 kJ mol⁻¹. In the crystal, each molecule in the dimer also forms an S1⋯C14 short interaction [3.5214 (14) Å; symmetry operation −x, 2 − y, 2 − z], forming another dimer with an R₂²(6) motif and thereby forming a chain running in the b-axis direction (Fig. 2). The energy of the dimer formed by this short interaction was calculated to be −30.6 kJ mol⁻¹.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.859 (18)	2.119 (18)	2.9537 (15)	163.6 (16)
Symmetry code: (i) .

Figure 2
A chain of molecules in the crystal structure of 1.

4. Hirshfeld surface analysis

Hirshfeld surface analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was conducted using Crystal Explorer (Spackman et al., 2021) to visualize and quantify the intermolecular interactions in the title molecule. The Hirshfeld surface for the title compound mapped over d_norm is shown in Fig. 3. The red region is attributed to the N1—H1⋯O1 interaction. The two-dimensional fingerprint plots in Fig. 4 indicate that the major contributions to the crystal packing are from H⋯H (67.9%), C⋯H (13.7%), O⋯H (7.3%) and S⋯H (4.3%) interactions.

Figure 3
The Hirshfeld surface of the title compound mapped over d_norm with dashed lines indicating the N—H⋯·O hydrogen bonds that lead to the formation of dimers.

Figure 4
The two-dimensional fingerprint plots of the title molecule, showing all interactions and those delineated into H⋯H, O⋯H/H⋯O and S⋯H/ S⋯H.

5. Database Survey

A search of the Cambridge Structural Database (CSD, updated to January 2025; Groom et al., 2016 ) for the 2-(4-isobutylphenyl)-N′-methylpropanehydrazide moiety yielded two closely related structures: 1-[2-(4-isobutylphenyl)propanoyl]thiosemicarbazide (2; CSD refcode HOLQIJ; Fun & Kia et al., 2009 ) and N-(2,4-dioxo-1,3-thiazolidin-3-yl)-2-(4-isobutylphenyl)propenamide (3; CSD refcode HUCTUV; Fun & Goh et al., 2009 ). In compound 2, the crystal structure features N—H⋯O and N—H⋯S hydrogen bonds, with donor–acceptor distances of 2.09 (15) and 2.495 (13) Å, respectively, leading to a supramolecular architecture. In compound 3, the supramolecular structure is governed by N—H⋯O hydrogen bonding [1.94 (3) Å], along with several C—H⋯O interactions.

6. Synthesis and crystallization

The title compound was obtained by refluxing 2-[4-(2-methylpropyl)phenyl]propanehydrazide (0.01 mol) and 2-acetyl thiophene (0.01 mol) in ethanol (20 ml) by adding a catalytic amount of concentrated sulfuric acid for 1 h. The excess solvent was removed under reduced pressure. The solid product obtained was filtered, washed with ethanol, and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation from an ethanol solution with 80% yield and melting point 340–342 K.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were refined using a DFIX restraint to ensure chemically reasonable bond lengths and angles, with their U_iso(H) values constrained to 1.5 times the U_eq of their pivot atoms for terminal sp³ carbon atoms and 1.2 times for all other carbon atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂OS
M_r	328.46
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	7.9057 (3), 10.1929 (3), 12.2794 (3)
α, β, γ (°)	83.238 (1), 89.201 (1), 71.122 (1)
V (Å³)	929.45 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.18
Crystal size (mm)	0.77 × 0.66 × 0.55

Data collection
Diffractometer	Bruker D8 Quest Eco
Absorption correction	Multi-scan (SADABS, Krause et al., 2015 )
T_min, T_max	0.874, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	27745, 4620, 4098
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.03
No. of reflections	4620
No. of parameters	304
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.33
Computer programs: APEX2 and SAINT (Bruker 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL(Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2443395

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989025003329/dx2065sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025003329/dx2065Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025003329/dx2065Isup3.cml

checkCIF report

Computing details top

2-[4-(2-Methylpropyl)phenyl]-N'-[(1Z)-1-(thiophen-2-yl)ethylidene]propanehydrazide top

Crystal data top

C₁₉H₂₄N₂OS	Z = 2
M_r = 328.46	F(000) = 352
Triclinic, P1	D_x = 1.174 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9057 (3) Å	Cell parameters from 27745 reflections
b = 10.1929 (3) Å	θ = 2.7–28.3°
c = 12.2794 (3) Å	µ = 0.18 mm⁻¹
α = 83.238 (1)°	T = 293 K
β = 89.201 (1)°	BLOCK, white
γ = 71.122 (1)°	0.77 × 0.66 × 0.55 mm
V = 929.45 (5) Å³

Data collection top

Bruker D8 Quest Eco diffractometer	4098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 28.3°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS, Krause et al., 2015)	h = −10→10
T_min = 0.874, T_max = 0.907	k = −13→13
27745 measured reflections	l = −16→16
4620 independent 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0654P)² + 0.1712P] where P = (F_o² + 2F_c²)/3
4620 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³
0 constraints

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
H7	0.214 (2)	1.0985 (18)	0.6861 (13)	0.061 (4)*
H11	−0.014 (2)	1.2611 (16)	0.7709 (12)	0.051 (4)*
H3	0.7134 (19)	1.3440 (16)	0.4536 (12)	0.050 (4)*
H10	0.538 (2)	1.4079 (17)	0.6116 (13)	0.061 (4)*
H4B	0.744 (2)	1.0670 (19)	0.5259 (14)	0.064 (4)*
H12B	−0.225 (3)	1.480 (2)	0.7002 (18)	0.093 (6)*
H6	0.487 (2)	1.0259 (18)	0.6006 (14)	0.064 (4)*
H9	0.267 (2)	1.4757 (18)	0.6996 (14)	0.066 (5)*
H4A	0.816 (2)	1.1609 (18)	0.5930 (15)	0.066 (5)*
H1A	0.603 (2)	1.173 (2)	0.3246 (15)	0.073 (5)*
H1C	0.468 (3)	1.291 (2)	0.3788 (16)	0.081 (6)*
H2B	0.929 (3)	1.263 (2)	0.3186 (18)	0.085 (6)*
H2C	1.001 (3)	1.205 (2)	0.438 (2)	0.102 (8)*
H12A	−0.118 (3)	1.413 (2)	0.6042 (19)	0.090 (6)*
H1B	0.591 (3)	1.327 (2)	0.2852 (18)	0.085 (6)*
H1	0.107 (2)	1.3514 (19)	1.0060 (15)	0.068 (5)*
H19	0.276 (3)	0.649 (2)	0.9227 (19)	0.099 (7)*
H12C	−0.080 (3)	1.536 (2)	0.6532 (18)	0.093 (7)*
H2A	0.940 (3)	1.108 (2)	0.3691 (17)	0.089 (6)*
H17	0.426 (3)	0.840 (2)	1.1552 (19)	0.087 (6)*
H15A	0.198 (4)	1.177 (3)	1.166 (2)	0.134 (10)*
H15B	0.342 (4)	1.212 (3)	1.113 (3)	0.140 (10)*
H15C	0.371 (4)	1.072 (3)	1.171 (2)	0.121 (9)*
H18	0.433 (3)	0.615 (2)	1.1025 (19)	0.100 (7)*
S1	0.20178 (5)	0.88866 (4)	0.90928 (3)	0.05992 (13)
N2	0.16268 (14)	1.17435 (11)	0.94142 (8)	0.0464 (2)
C8	0.20740 (16)	1.29536 (11)	0.69966 (9)	0.0410 (2)
N1	0.11506 (16)	1.31606 (11)	0.94519 (9)	0.0499 (2)
C6	0.4414 (2)	1.11989 (12)	0.61919 (10)	0.0515 (3)
O1	−0.01124 (18)	1.53227 (10)	0.86090 (8)	0.0697 (3)
C11	0.02513 (17)	1.34485 (13)	0.75071 (10)	0.0464 (3)
C9	0.30698 (17)	1.38476 (12)	0.67826 (11)	0.0481 (3)
C10	0.46957 (18)	1.34333 (12)	0.62781 (11)	0.0509 (3)
C5	0.54019 (17)	1.20942 (11)	0.59659 (9)	0.0452 (3)
C7	0.2783 (2)	1.16138 (13)	0.67006 (10)	0.0508 (3)
C16	0.27929 (17)	0.94374 (13)	1.02006 (10)	0.0493 (3)
C4	0.71791 (18)	1.16349 (13)	0.54132 (12)	0.0532 (3)
C14	0.24044 (16)	1.09260 (13)	1.02689 (10)	0.0471 (3)
C13	0.03963 (17)	1.40564 (13)	0.85616 (10)	0.0483 (3)
C3	0.73007 (17)	1.25536 (12)	0.43557 (11)	0.0504 (3)
C19	0.2924 (3)	0.71716 (17)	0.96246 (16)	0.0715 (4)
C15	0.2901 (3)	1.1379 (2)	1.13036 (14)	0.0667 (4)
C17	0.3711 (2)	0.83168 (17)	1.09363 (14)	0.0662 (4)
C1	0.5877 (2)	1.26297 (17)	0.35180 (13)	0.0626 (4)
C12	−0.1107 (2)	1.4535 (2)	0.67142 (15)	0.0662 (4)
C2	0.9153 (2)	1.20371 (19)	0.38798 (19)	0.0730 (5)
C18	0.3772 (3)	0.70272 (18)	1.05916 (17)	0.0793 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0657 (2)	0.0562 (2)	0.0589 (2)	−0.01866 (16)	0.00501 (16)	−0.01461 (15)
N2	0.0515 (5)	0.0443 (5)	0.0446 (5)	−0.0157 (4)	0.0091 (4)	−0.0100 (4)
C8	0.0512 (6)	0.0374 (5)	0.0349 (5)	−0.0146 (4)	0.0009 (4)	−0.0062 (4)
N1	0.0637 (6)	0.0459 (5)	0.0423 (5)	−0.0181 (5)	0.0081 (4)	−0.0131 (4)
C6	0.0726 (8)	0.0343 (5)	0.0478 (6)	−0.0158 (5)	0.0117 (6)	−0.0113 (4)
O1	0.1087 (9)	0.0434 (5)	0.0536 (5)	−0.0177 (5)	0.0126 (5)	−0.0136 (4)
C11	0.0506 (6)	0.0452 (6)	0.0464 (6)	−0.0183 (5)	0.0035 (5)	−0.0101 (5)
C9	0.0554 (7)	0.0323 (5)	0.0572 (7)	−0.0135 (5)	0.0081 (5)	−0.0107 (5)
C10	0.0545 (7)	0.0363 (5)	0.0632 (7)	−0.0163 (5)	0.0087 (6)	−0.0077 (5)
C5	0.0543 (6)	0.0348 (5)	0.0413 (5)	−0.0081 (4)	0.0028 (5)	−0.0019 (4)
C7	0.0706 (8)	0.0403 (6)	0.0494 (6)	−0.0263 (6)	0.0123 (6)	−0.0134 (5)
C16	0.0489 (6)	0.0508 (6)	0.0459 (6)	−0.0128 (5)	0.0103 (5)	−0.0078 (5)
C4	0.0526 (7)	0.0384 (6)	0.0581 (7)	−0.0022 (5)	0.0054 (5)	−0.0006 (5)
C14	0.0454 (6)	0.0516 (6)	0.0437 (6)	−0.0141 (5)	0.0089 (4)	−0.0098 (5)
C13	0.0564 (7)	0.0447 (6)	0.0460 (6)	−0.0176 (5)	0.0111 (5)	−0.0116 (5)
C3	0.0542 (7)	0.0345 (5)	0.0573 (7)	−0.0073 (5)	0.0124 (5)	−0.0062 (5)
C19	0.0836 (11)	0.0522 (8)	0.0815 (11)	−0.0230 (7)	0.0200 (9)	−0.0180 (7)
C15	0.0766 (10)	0.0660 (9)	0.0523 (8)	−0.0127 (8)	−0.0068 (7)	−0.0152 (7)
C17	0.0760 (10)	0.0569 (8)	0.0569 (8)	−0.0110 (7)	0.0005 (7)	−0.0022 (6)
C1	0.0711 (9)	0.0559 (8)	0.0540 (8)	−0.0124 (7)	0.0055 (7)	−0.0043 (6)
C12	0.0561 (8)	0.0679 (9)	0.0691 (9)	−0.0121 (7)	−0.0106 (7)	−0.0087 (8)
C2	0.0617 (9)	0.0606 (9)	0.0887 (12)	−0.0100 (7)	0.0251 (9)	−0.0085 (8)
C18	0.0958 (13)	0.0514 (8)	0.0786 (11)	−0.0105 (8)	0.0100 (9)	0.0008 (8)

Geometric parameters (Å, º) top

S1—C19	1.7115 (18)	C4—C3	1.5300 (18)
S1—C16	1.7225 (14)	C4—H4B	0.978 (18)
N2—C14	1.2862 (16)	C4—H4A	1.003 (18)
N2—N1	1.3761 (14)	C14—C15	1.5005 (19)
C8—C9	1.3860 (17)	C3—C1	1.512 (2)
C8—C7	1.3881 (15)	C3—C2	1.521 (2)
C8—C11	1.5175 (17)	C3—H3	0.923 (15)
N1—C13	1.3473 (17)	C19—C18	1.341 (3)
N1—H1	0.859 (19)	C19—H19	0.93 (2)
C6—C5	1.3841 (18)	C15—H15A	0.85 (3)
C6—C7	1.3853 (19)	C15—H15B	0.97 (4)
C6—H6	0.962 (17)	C15—H15C	0.87 (3)
O1—C13	1.2297 (15)	C17—C18	1.414 (3)
C11—C13	1.5208 (17)	C17—H17	0.90 (2)
C11—C12	1.527 (2)	C1—H1A	0.98 (2)
C11—H11	1.002 (16)	C1—H1C	0.96 (2)
C9—C10	1.3793 (18)	C1—H1B	0.99 (2)
C9—H9	0.945 (17)	C12—H12B	0.93 (2)
C10—C5	1.3949 (16)	C12—H12A	0.98 (2)
C10—H10	0.979 (17)	C12—H12C	0.95 (2)
C5—C4	1.5087 (18)	C2—H2B	1.01 (2)
C7—H7	0.942 (18)	C2—H2C	0.92 (3)
C16—C17	1.373 (2)	C2—H2A	0.99 (2)
C16—C14	1.4599 (18)	C18—H18	0.96 (2)

C19—S1—C16	91.71 (8)	O1—C13—C11	121.97 (12)
C14—N2—N1	117.92 (10)	N1—C13—C11	117.84 (11)
C9—C8—C7	117.67 (11)	C1—C3—C2	110.69 (14)
C9—C8—C11	120.64 (10)	C1—C3—C4	111.69 (12)
C7—C8—C11	121.67 (11)	C2—C3—C4	110.71 (12)
C13—N1—N2	120.01 (10)	C1—C3—H3	108.8 (9)
C13—N1—H1	116.0 (12)	C2—C3—H3	107.3 (9)
N2—N1—H1	122.2 (12)	C4—C3—H3	107.4 (9)
C5—C6—C7	121.56 (11)	C18—C19—S1	112.06 (14)
C5—C6—H6	119.9 (10)	C18—C19—H19	130.0 (14)
C7—C6—H6	118.5 (10)	S1—C19—H19	118.0 (14)
C8—C11—C13	109.93 (10)	C14—C15—H15A	112 (2)
C8—C11—C12	111.19 (12)	C14—C15—H15B	110.5 (19)
C13—C11—C12	110.02 (11)	H15A—C15—H15B	102 (3)
C8—C11—H11	107.7 (8)	C14—C15—H15C	113.9 (18)
C13—C11—H11	107.3 (9)	H15A—C15—H15C	113 (3)
C12—C11—H11	110.6 (9)	H15B—C15—H15C	105 (2)
C10—C9—C8	121.41 (10)	C16—C17—C18	112.44 (16)
C10—C9—H9	117.7 (11)	C16—C17—H17	123.3 (14)
C8—C9—H9	120.9 (11)	C18—C17—H17	124.2 (14)
C9—C10—C5	121.13 (11)	C3—C1—H1A	113.0 (11)
C9—C10—H10	120.7 (9)	C3—C1—H1C	114.2 (12)
C5—C10—H10	118.1 (10)	H1A—C1—H1C	104.8 (16)
C6—C5—C10	117.32 (11)	C3—C1—H1B	111.6 (12)
C6—C5—C4	121.29 (11)	H1A—C1—H1B	104.6 (16)
C10—C5—C4	121.38 (11)	H1C—C1—H1B	108.0 (16)
C6—C7—C8	120.91 (11)	C11—C12—H12B	111.8 (14)
C6—C7—H7	120.5 (10)	C11—C12—H12A	108.8 (13)
C8—C7—H7	118.6 (10)	H12B—C12—H12A	107.1 (18)
C17—C16—C14	129.06 (13)	C11—C12—H12C	112.5 (14)
C17—C16—S1	110.69 (11)	H12B—C12—H12C	107.5 (18)
C14—C16—S1	120.23 (10)	H12A—C12—H12C	109.0 (19)
C5—C4—C3	114.56 (10)	C3—C2—H2B	112.8 (11)
C5—C4—H4B	109.1 (10)	C3—C2—H2C	110.4 (15)
C3—C4—H4B	109.4 (10)	H2B—C2—H2C	106.9 (19)
C5—C4—H4A	110.0 (10)	C3—C2—H2A	109.9 (12)
C3—C4—H4A	108.2 (10)	H2B—C2—H2A	107.1 (17)
H4B—C4—H4A	105.1 (13)	H2C—C2—H2A	109.6 (19)
N2—C14—C16	115.38 (11)	C19—C18—C17	113.10 (16)
N2—C14—C15	125.65 (13)	C19—C18—H18	124.1 (14)
C16—C14—C15	118.95 (12)	C17—C18—H18	122.7 (14)
O1—C13—N1	120.17 (12)

C14—N2—N1—C13	177.41 (11)	N1—N2—C14—C16	176.95 (10)
C9—C8—C11—C13	−53.84 (15)	N1—N2—C14—C15	−2.2 (2)
C7—C8—C11—C13	127.93 (12)	C17—C16—C14—N2	175.00 (14)
C9—C8—C11—C12	68.24 (15)	S1—C16—C14—N2	−6.57 (15)
C7—C8—C11—C12	−109.99 (14)	C17—C16—C14—C15	−5.8 (2)
C7—C8—C9—C10	0.99 (19)	S1—C16—C14—C15	172.59 (12)
C11—C8—C9—C10	−177.31 (12)	N2—N1—C13—O1	176.36 (12)
C8—C9—C10—C5	−0.2 (2)	N2—N1—C13—C11	−5.30 (17)
C7—C6—C5—C10	0.43 (19)	C8—C11—C13—O1	103.88 (14)
C7—C6—C5—C4	179.90 (12)	C12—C11—C13—O1	−18.90 (18)
C9—C10—C5—C6	−0.56 (19)	C8—C11—C13—N1	−74.43 (14)
C9—C10—C5—C4	179.97 (12)	C12—C11—C13—N1	162.80 (13)
C5—C6—C7—C8	0.4 (2)	C5—C4—C3—C1	−57.96 (16)
C9—C8—C7—C6	−1.11 (19)	C5—C4—C3—C2	178.20 (14)
C11—C8—C7—C6	177.17 (12)	C16—S1—C19—C18	−0.08 (15)
C19—S1—C16—C17	0.06 (12)	C14—C16—C17—C18	178.51 (14)
C19—S1—C16—C14	−178.63 (11)	S1—C16—C17—C18	−0.04 (19)
C6—C5—C4—C3	123.70 (14)	S1—C19—C18—C17	0.1 (2)
C10—C5—C4—C3	−56.85 (18)	C16—C17—C18—C19	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.859 (18)	2.119 (18)	2.9537 (15)	163.6 (16)

Symmetry code: (i) −x, −y+3, −z+2.

Table 2. The energy values (eV) of global reactivity descriptors for the title compound. top

Global reactivity Descriptors	Calculated values (eV)
E(HOMO)	-6.0826
E(LUMO)	-1.7796
Energy gap	4.303
Electron affinity (A)	1.7796
Ionisation energy (I)	6.0826
Electronegativity (χ)	3.9311
Chemical hardness (η)	2.1515
Chemical potential (µ)	-3.9311
Chemical hardness (S)	0.2324
Electrophilicity index (ω)	3.5913

Acknowledgements

The authors thank the Department of Chemistry, Sir Syed College, Taliparamba for providing the computational lab facility. The authors thank the Laboratory of X-ray Crystallography, Department of Physics, Periyar University, Salem, for assistance with data collection for single-crystal XRD studies.

Funding information

Funding for this research was provided by: This research received no specific grant from any funding agency in the public, commercial, or not-for-profit sectors.

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