2-Cyano-N′-[(1E)-1-(3,4-di­meth­oxy­phen­yl)ethylidene]acetohydrazide

Manvizhi, M.; Senthilkumar, S.; Selvanayagam, S.

doi:10.1107/S2414314626000891

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 2| February 2026| x260089

https://doi.org/10.1107/S2414314626000891

Open

access

2-Cyano-N′-[(1E)-1-(3,4-dimethoxyphenyl)ethylidene]acetohydrazide

Meiyazhagan Manvizhi,^a Srinivasan Senthilkumar ^a ^* and Sivashanmugam Selvanayagam ^b ‡

^aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and ^bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 18 December 2025; accepted 28 January 2026; online 5 February 2026)

The non-H part of the molecule of the title compound, C₁₃H₁₅N₃O₃, is nearly planar, with the 2-cyano-N′-[(1E)-ethylidene]acetohydrazide moiety and the dimethoxy phenol ring forming a dihedral angle of 2.5 (1)°. Intermolecular N—H⋯O, C—H⋯O and C—H⋯π interactions are mainly responsible for the cohesion within the crystal structure. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, revealing that H⋯H interactions contribute most to the crystal packing (36.9%). The volume of the crystal voids was calculated to be 167.8 Å³ (13% of the unit-cell volume).

Keywords: benzohydrazine; intermolecular hydrogen bonds; Hirshfeld surface analysis; crystal structure.

CCDC reference: 2501701

Structure description

Hydrazone derivatives have long been valued in medicinal and organic chemistry because they are easy to prepare, structurally flexible, and capable of exhibiting a wide range of biological activities. Within this class, acyl hydrazones and heterocycle-linked hydrazones are especially notable, as many of them display antidiabetic, anticancer, antimicrobial, antioxidant, and anti-inflammatory properties (Punitha et al., 2020 ). In the present work, the title compound, (I), was chosen due to the particular ombination of functional groups that are known to enhance biological effectiveness. The hydrazone unit (–C=N–NH–) provides an extended- conjugated system that supports strong intermolecular interactions and can promote favourable binding within enzyme active sites. The 3,4-dimethoxyphenyl ring adds lipophilicity, encouraging π–π stacking and improving membrane permeability, which together may enhance pharmacological performance. The cyano (–C≡N) group, being a strong electron-withdrawing substituent, fine-tunes the electronic character of the molecule, increases hydrogen-bond acceptor strength, and is often associated with improved antimicrobial and anticancer effects (Senthilkumar et al., 2021 ; Maheswari et al., 2025 ). The coexistence of electron-donating methoxy groups and an electron-withdrawing cyano group creates an internal charge-transfer environment, a feature commonly linked to stronger biological responses in hydrazone frameworks. Because of this combination of structural and electronic attributes, the selected compound offers enhanced biological activity, making it a promising candidate for further pharmacological development (Senthilkumar et al., 2020 ).

The molecular structure of (I) is displayed in Fig. 1. The phenyl ring (C6–C11) is planar with a maximum deviation of 0.010 (3) Å for atom C9, and its attached methoxy atoms O2, C12, O3 and C13 deviate by −0.015 (2), 0.075 (4), 0.036 (2) and 0.218 (4) Å, respectively. The 2-cyano-N′-[(1E)-ethylidene]acetohydrazide moiety (N1/C1/C2/C3/O1/N2/N3/C4/C5) is nearly planar with a maximum deviation of 0.120 (4) Å for atom C5. This moiety forms a dihedral angle of 2.5 (1)° with the dimethoxy phenyl ring. Weak intramolecular C5—H5A⋯N2 and C7—H7⋯N3 contacts, forming two S(5) ring motifs (Bernstein et al., 1995 ) may help to establish the solid-state conformation (Table 1, Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring (C6–C11).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N2	0.96	2.38	2.796 (4)	105
C7—H7⋯N3	0.93	2.44	2.749 (3)	100
N2—H2⋯O1ⁱ	0.86	2.14	2.982 (3)	166
C5—H5A⋯O1ⁱ	0.96	2.33	3.252 (4)	160
C5—H5E⋯O2ⁱⁱ	0.96	2.59	3.436 (4)	147
C13—H13B⋯Cgⁱⁱⁱ	0.97	2.86	3.569 (4)	132
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
Molecular structure of (I) showing the atom-labelling scheme and the intramolecular hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 50% probability level. Only one part of the disordered methyl group at C5 is shown.

In the crystal, molecules associate pairwise through N2—H2⋯O1ⁱ and C5—H5A⋯O1ⁱ hydrogen bonds (Table 1) into inversion dimers with R₂²(8) and R₂²(14) graph-set motifs (Etter et al., 1990 ; Bernstein et al., 1995), as shown in Fig. 2. The molecules are linked into a C(7) chain motif by C5—H5E⋯O2ⁱⁱ hydrogen bonds running parallel to [001] (Table 1, Fig. 3). Moreover, molecules are further linked along the same direction into a C(5) chain motif by C—H⋯π interactions, C13—H13B⋯Cg, where Cg is the centroid of the symmetry-related C6–C11 benzene ring at (x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ) (Table 1, Fig. 4).

Figure 2
The formation of a centrosymmetric dimer in the crystal structure of (I) through N—H⋯O and C—H⋯O hydrogen bonds. [Symmetry code: (a) −x + 1, −y + 1, −z].

Figure 3
The crystal packing of compound (I) viewed along the b axis. The C—H⋯O hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds have been omitted.

Figure 4
The crystal packing of (I). C—H⋯π interactions are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

In order to further characterize and quantify the intermolecular interactions in the title compound, a Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ) was carried out using CrystalExplorer (Spackman et al., 2021 ). The HS mapped over d_norm is illustrated in Fig. 5 where the deep-red spots indicative of strong interactions occur at O1, H2 and H5A, and these atoms are responsible for intermolecular N—H⋯O and C—H⋯O hydrogen bonds discussed above.

Figure 5
A view of the Hirshfeld surface mapped over d_norm for compound (I).

The associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) provide quantitative information about the non-covalent interactions in the crystal packing in terms of the percentage contribution of the interatomic contacts (Spackman & McKinnon, 2002 ). As shown in Fig. 6, the overall two-dimensional fingerprint plot for compound (I) is delineated into the different contact types, revealing that H⋯H (36.9%) and H⋯O/O⋯H (22.2%) are the main contributors to the crystal packing.

Figure 6
Two-dimensional fingerprint plots for compound (I), showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e) H⋯N/N⋯H, (f) N⋯C/C⋯N, (g) N⋯N and (h) O⋯C/C⋯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.

A void analysis was performed by adding up the electron densities of the spherically symmetric atoms contained in the asymmetric unit (Turner et al., 2011 ). The void surface is defined as an isosurface of the procrystal electron density and is calculated for the whole unit cell where the void surface meets the boundary of the unit cell and capping faces are generated to create an enclosed volume. The volume of the crystal voids (Fig. 7) was calculated to be 168 Å³ (13% of the unit-cell volume). Fig. 7(b) also reveals that individual molecules are arranged in layers parallel to (10 $[\overline{1}]$ ).

Figure 7
Graphical views of voids in the crystal packing of compound (I) viewed down the (a) a-axis and (b) b-axis directions.

Synthesis and crystallization

Compound (I) was prepared through a condensation reaction involving an equimolar ratio of 2-cyanoacetohydrazide (0.05 mol) and 3,4-dimethoxyacetophenone (0.05 mol). The reagents were placed into a clean reaction flask where methanol served as the reaction medium. A few drops of glacial acetic acid were added to promote the formation of the hydrazone bond. The mixture was then heated under reflux for about 6–8 h. Throughout this period, the progress of the reaction was checked at intervals using thin-layer chromatography (TLC) to confirm that the starting materials were being fully consumed. Once the reaction reached completion, the mixture was allowed to cool gradually to room temperature, during which a solid product began to separate out. The resulting precipitate was collected by filtration, thoroughly washed to remove any remaining impurities, and dried under reduced pressure to eliminate traces of solvent. Final purification was achieved by recrystallizing the crude product from warm ethanol solution, affording the desired hydrazone derivative with 75% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl hydrogen atoms at C5 were refined as equally disordered (using an AFIX 127 instruction with SHELXL; Sheldrick, 2015b ) with C—H = 0.98 Å.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₅N₃O₃
M_r	261.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	11.2308 (13), 11.7792 (13), 10.3668 (12)
β (°)	102.692 (4)
V (Å³)	1337.9 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.46 × 0.12 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.672, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	25559, 3317, 1510
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.239, 1.04
No. of reflections	3317
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2017 ), SHELXT (Sheldrick, 2015a ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2020 ) and SHELXL (Sheldrick, 2015b).

Structural data

CCDC reference: 2501701

Crystal structure: contains datablocks I, shelx. DOI: https://doi.org/10.1107/S2414314626000891/wm4242sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626000891/wm4242Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626000891/wm4242Isup3.cml

checkCIF report

Computing details top

2-Cyano-N'-[(1E)-1-(3,4-dimethoxyphenyl)ethylidene]acetohydrazide top

Crystal data top

C₁₃H₁₅N₃O₃	F(000) = 552
M_r = 261.28	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2308 (13) Å	Cell parameters from 5190 reflections
b = 11.7792 (13) Å	θ = 2.5–24.4°
c = 10.3668 (12) Å	µ = 0.09 mm⁻¹
β = 102.692 (4)°	T = 300 K
V = 1337.9 (3) Å³	Plate, colourless
Z = 4	0.46 × 0.12 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	1510 reflections with I > 2σ(I)
Radiation source: i-mu-s microfocus source	R_int = 0.064
φ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
T_min = 0.672, T_max = 0.746	k = −15→15
25559 measured reflections	l = −13→13
3317 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.067	w = 1/[σ²(F_o²) + (0.1011P)² + 0.4583P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.239	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.34 e Å⁻³
3317 reflections	Δρ_min = −0.18 e Å⁻³
174 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.008 (3)

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	Occ. (<1)
O1	0.4532 (2)	0.63384 (18)	−0.0687 (2)	0.0873 (8)
O2	0.87019 (19)	0.96378 (15)	0.55091 (18)	0.0716 (6)
O3	1.00787 (18)	0.85504 (16)	0.74705 (17)	0.0680 (6)
N1	0.3940 (3)	0.9169 (3)	−0.1399 (4)	0.1051 (11)
N2	0.5860 (2)	0.61306 (19)	0.1263 (2)	0.0626 (7)
H2	0.585827	0.540243	0.120280	0.075*
N3	0.65690 (19)	0.66651 (18)	0.2344 (2)	0.0590 (6)
C1	0.4510 (3)	0.8648 (3)	−0.0567 (3)	0.0750 (9)
C2	0.5239 (3)	0.8034 (2)	0.0532 (3)	0.0680 (8)
H2A	0.495556	0.820980	0.132830	0.082*
H2B	0.608161	0.827932	0.066527	0.082*
C3	0.5174 (2)	0.6761 (2)	0.0306 (3)	0.0629 (7)
C4	0.7271 (2)	0.6060 (2)	0.3220 (3)	0.0554 (7)
C5	0.7404 (3)	0.4793 (2)	0.3148 (3)	0.0791 (9)
H5A	0.696800	0.452706	0.229983	0.119*	0.5
H5B	0.707704	0.444113	0.383042	0.119*	0.5
H5C	0.825218	0.460173	0.326694	0.119*	0.5
H5D	0.789682	0.451955	0.396497	0.119*	0.5
H5E	0.778777	0.460548	0.243437	0.119*	0.5
H5F	0.661263	0.444489	0.299785	0.119*	0.5
C6	0.8006 (2)	0.6688 (2)	0.4357 (2)	0.0544 (7)
C7	0.7997 (2)	0.7877 (2)	0.4374 (3)	0.0557 (7)
H7	0.752355	0.826757	0.366329	0.067*
C8	0.8673 (2)	0.8482 (2)	0.5422 (2)	0.0544 (7)
C9	0.9413 (2)	0.7895 (2)	0.6492 (2)	0.0548 (7)
C10	0.9413 (3)	0.6734 (2)	0.6487 (3)	0.0627 (7)
H10	0.987959	0.634148	0.720009	0.075*
C11	0.8724 (3)	0.6137 (2)	0.5426 (3)	0.0646 (8)
H11	0.874624	0.534744	0.543617	0.078*
C12	0.8042 (3)	1.0254 (2)	0.4392 (3)	0.0795 (9)
H12A	0.812865	1.105355	0.456610	0.119*
H12B	0.836055	1.007186	0.363009	0.119*
H12C	0.719483	1.005024	0.422915	0.119*
C13	1.0939 (3)	0.7968 (3)	0.8472 (3)	0.0808 (10)
H13A	1.135675	0.850615	0.910895	0.121*
H13B	1.051878	0.742740	0.890291	0.121*
H13C	1.152076	0.758002	0.807590	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0962 (16)	0.0556 (12)	0.0888 (15)	−0.0086 (11)	−0.0261 (13)	−0.0013 (11)
O2	0.0960 (14)	0.0461 (11)	0.0650 (12)	0.0002 (10)	0.0014 (10)	−0.0039 (9)
O3	0.0821 (13)	0.0586 (11)	0.0568 (11)	−0.0016 (10)	0.0011 (10)	−0.0062 (9)
N1	0.102 (2)	0.081 (2)	0.118 (3)	0.0087 (18)	−0.006 (2)	0.0182 (19)
N2	0.0645 (14)	0.0452 (12)	0.0703 (15)	−0.0035 (10)	−0.0021 (12)	−0.0056 (11)
N3	0.0589 (13)	0.0472 (12)	0.0648 (14)	−0.0062 (10)	0.0006 (11)	−0.0067 (11)
C1	0.0699 (19)	0.0540 (17)	0.095 (2)	0.0030 (15)	0.0049 (18)	0.0030 (17)
C2	0.0673 (17)	0.0479 (15)	0.082 (2)	−0.0003 (13)	0.0028 (15)	−0.0026 (14)
C3	0.0587 (16)	0.0524 (15)	0.0709 (18)	−0.0058 (13)	−0.0004 (14)	−0.0005 (14)
C4	0.0586 (15)	0.0477 (14)	0.0603 (16)	−0.0027 (12)	0.0136 (13)	−0.0004 (12)
C5	0.100 (2)	0.0519 (17)	0.075 (2)	−0.0004 (16)	−0.0025 (17)	−0.0036 (15)
C6	0.0588 (15)	0.0478 (14)	0.0558 (15)	−0.0019 (12)	0.0108 (12)	0.0000 (12)
C7	0.0621 (16)	0.0491 (14)	0.0553 (15)	−0.0007 (12)	0.0113 (13)	0.0010 (12)
C8	0.0614 (15)	0.0480 (14)	0.0534 (15)	−0.0002 (12)	0.0115 (12)	−0.0005 (12)
C9	0.0592 (15)	0.0549 (15)	0.0494 (14)	−0.0010 (12)	0.0103 (12)	−0.0049 (12)
C10	0.0705 (17)	0.0559 (16)	0.0566 (16)	0.0007 (13)	0.0032 (13)	0.0063 (13)
C11	0.0753 (18)	0.0454 (14)	0.0697 (18)	−0.0022 (13)	0.0083 (15)	0.0039 (13)
C12	0.106 (2)	0.0497 (16)	0.073 (2)	−0.0010 (16)	0.0002 (17)	0.0056 (15)
C13	0.085 (2)	0.076 (2)	0.0684 (19)	0.0057 (17)	−0.0101 (16)	−0.0089 (16)

Geometric parameters (Å, º) top

O1—C3	1.225 (3)	C5—H5D	0.9600
O2—C8	1.364 (3)	C5—H5E	0.9600
O2—C12	1.428 (3)	C5—H5F	0.9600
O3—C9	1.360 (3)	C6—C11	1.382 (4)
O3—C13	1.429 (3)	C6—C7	1.401 (4)
N1—C1	1.135 (4)	C7—C8	1.379 (3)
N2—C3	1.339 (3)	C7—H7	0.9300
N2—N3	1.376 (3)	C8—C9	1.412 (3)
N2—H2	0.8600	C9—C10	1.367 (4)
N3—C4	1.280 (3)	C10—C11	1.390 (4)
C1—C2	1.443 (4)	C10—H10	0.9300
C2—C3	1.517 (4)	C11—H11	0.9300
C2—H2A	0.9700	C12—H12A	0.9600
C2—H2B	0.9700	C12—H12B	0.9600
C4—C6	1.480 (3)	C12—H12C	0.9600
C4—C5	1.504 (4)	C13—H13A	0.9600
C5—H5A	0.9600	C13—H13B	0.9600
C5—H5B	0.9600	C13—H13C	0.9600
C5—H5C	0.9600

C8—O2—C12	116.9 (2)	H5A—C5—H5F	56.3
C9—O3—C13	116.3 (2)	H5B—C5—H5F	56.3
C3—N2—N3	119.0 (2)	H5C—C5—H5F	141.1
C3—N2—H2	120.5	H5D—C5—H5F	109.5
N3—N2—H2	120.5	H5E—C5—H5F	109.5
C4—N3—N2	118.6 (2)	C11—C6—C7	117.7 (2)
N1—C1—C2	177.2 (4)	C11—C6—C4	121.9 (2)
C1—C2—C3	112.0 (2)	C7—C6—C4	120.4 (2)
C1—C2—H2A	109.2	C8—C7—C6	121.5 (2)
C3—C2—H2A	109.2	C8—C7—H7	119.2
C1—C2—H2B	109.2	C6—C7—H7	119.2
C3—C2—H2B	109.2	O2—C8—C7	124.7 (2)
H2A—C2—H2B	107.9	O2—C8—C9	115.8 (2)
O1—C3—N2	122.3 (3)	C7—C8—C9	119.5 (2)
O1—C3—C2	122.0 (2)	O3—C9—C10	124.7 (2)
N2—C3—C2	115.7 (2)	O3—C9—C8	116.1 (2)
N3—C4—C6	115.8 (2)	C10—C9—C8	119.2 (2)
N3—C4—C5	124.7 (2)	C9—C10—C11	120.6 (2)
C6—C4—C5	119.5 (2)	C9—C10—H10	119.7
C4—C5—H5A	109.5	C11—C10—H10	119.7
C4—C5—H5B	109.5	C6—C11—C10	121.5 (2)
H5A—C5—H5B	109.5	C6—C11—H11	119.3
C4—C5—H5C	109.5	C10—C11—H11	119.3
H5A—C5—H5C	109.5	O2—C12—H12A	109.5
H5B—C5—H5C	109.5	O2—C12—H12B	109.5
C4—C5—H5D	109.5	H12A—C12—H12B	109.5
H5A—C5—H5D	141.1	O2—C12—H12C	109.5
H5B—C5—H5D	56.3	H12A—C12—H12C	109.5
H5C—C5—H5D	56.3	H12B—C12—H12C	109.5
C4—C5—H5E	109.5	O3—C13—H13A	109.5
H5A—C5—H5E	56.3	O3—C13—H13B	109.5
H5B—C5—H5E	141.1	H13A—C13—H13B	109.5
H5C—C5—H5E	56.3	O3—C13—H13C	109.5
H5D—C5—H5E	109.5	H13A—C13—H13C	109.5
C4—C5—H5F	109.5	H13B—C13—H13C	109.5

C3—N2—N3—C4	−176.4 (2)	C12—O2—C8—C9	174.9 (2)
N3—N2—C3—O1	179.3 (3)	C6—C7—C8—O2	−179.6 (3)
N3—N2—C3—C2	−0.9 (4)	C6—C7—C8—C9	1.3 (4)
C1—C2—C3—O1	−2.4 (4)	C13—O3—C9—C10	7.8 (4)
C1—C2—C3—N2	177.8 (2)	C13—O3—C9—C8	−172.6 (2)
N2—N3—C4—C6	−179.9 (2)	O2—C8—C9—O3	−0.9 (3)
N2—N3—C4—C5	1.3 (4)	C7—C8—C9—O3	178.2 (2)
N3—C4—C6—C11	174.5 (3)	O2—C8—C9—C10	178.7 (2)
C5—C4—C6—C11	−6.7 (4)	C7—C8—C9—C10	−2.1 (4)
N3—C4—C6—C7	−5.8 (4)	O3—C9—C10—C11	−178.5 (2)
C5—C4—C6—C7	173.0 (3)	C8—C9—C10—C11	1.9 (4)
C11—C6—C7—C8	−0.4 (4)	C7—C6—C11—C10	0.1 (4)
C4—C6—C7—C8	180.0 (2)	C4—C6—C11—C10	179.8 (2)
C12—O2—C8—C7	−4.2 (4)	C9—C10—C11—C6	−0.9 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the benzene ring (C6–C11).

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2	0.96	2.38	2.796 (4)	105
C7—H7···N3	0.93	2.44	2.749 (3)	100
N2—H2···O1ⁱ	0.86	2.14	2.982 (3)	166
C5—H5A···O1ⁱ	0.96	2.33	3.252 (4)	160
C5—H5E···O2ⁱⁱ	0.96	2.59	3.436 (4)	147
C13—H13B···Cgⁱⁱⁱ	0.97	2.86	3.569 (4)	132

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: [email protected].

Acknowledgements

The authors thank the Single Crystal XRD Facility at VIT, Vellore, Tamil Nadu, India, for providing the instrumentation and support necessary for this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2017). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef ICSD CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Maheswari, S. U., Senthilkumar, S. & Selvanayagam, S. (2025). Acta Cryst. E81, 473–475. Web of Science CSD CrossRef IUCr Journals Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Punitha, P., Senthilkumar, S. & Muthukumaran, G. (2020). Chem. Data Coll. 28, 100373. Google Scholar
Senthilkumar, S., Seralathan, J. & Muthukumaran, G. (2020). Chem. Data Coll. 29, 100514. Google Scholar
Senthilkumar, S., Seralathan, J. & Muthukumaran, G. (2021). J. Mol. Struct. 1226, 129354. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm 4, 378–392. Web of Science CrossRef CAS Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2011). CrystEngComm 13, 1804–1813. Web of Science CrossRef CAS Google Scholar