Crystal structure, Hirshfeld surface and crystal void analysis of (1Z)-1-[(E)-2-(2H-1,3-benzodioxol-5-yl­methyl­idene)hydrazin-1-yl­idene]-1,2-di­hydro­phthalazine

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

doi:10.1107/S2056989026000538

research communications

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ISSN: 2056-9890

Volume 82| Part 2| February 2026| Pages 208-211

https://doi.org/10.1107/S2056989026000538

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Crystal structure, Hirshfeld surface and crystal void analysis of (1Z)-1-[(E)-2-(2H-1,3-benzodioxol-5-ylmethylidene)hydrazin-1-ylidene]-1,2-dihydrophthalazine

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], [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 19 December 2025; accepted 20 January 2026; online 23 January 2026)

The title compound, C₁₆H₁₂N₄O₂, crystallizes in the tetragonal space group I4₁/a with one molecule in the asymmetric unit. The 2H-1,3-benzodioxole ring is almost planar [maximum deviation of −0.039 (3) Å] and makes a dihedral angle of 11.25 (5)° with the 1,2-dihydrophthalazine moiety. An intramolecular N—H⋯N hydrogen bond stabilizes the molecular conformation. Intermolecular N—H⋯N hydrogen bonds, as well as C—H⋯N hydrogen bonds, lead to the formation of supramolecular chains extending parallel to [001]. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, revealing that H⋯H interactions contribute most to the crystal packing (37.4%). The volume of the crystal voids and the percentage of free space were calculated to be 614.55 Å³ and 11.5%, respectively.

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

CCDC reference: 2512372

1. Chemical context

Hydrazone derivatives have remained important molecules in medicinal and organic chemistry for decades, largely because they are easy to synthesize, adaptable in structure and capable of exhibiting a wide range of biological activities. Within this class, hydrazones linked to heterocyclic systems have received particular attention. The presence of fused aromatic rings often strengthens pharmacological effects, and many such derivatives have been reported to show antidiabetic, anticancer, antimicrobial, antioxidant and anti-inflammatory properties. The hydrazone unit (–C=N—NH–; Punitha et al., 2020 ; Senthilkumar et al., 2021 ) provides a conjugated pathway that allows for efficient electron delocalization and supports intermolecular hydrogen bonding, both of which can improve interactions with biological receptors. The 1,2-dihydroisoquinoline core is a widely recognized pharmacophore and often contributes to molecular rigidity, planarity and the possibility of π–π stacking, characteristics associated with notable anticancer and neuroactive potential. The benzo[d][1,3]dioxole ring is a structural motif commonly encountered in naturally occurring bioactive compounds, such as safrole derivatives and piperine analogues. Its electron-rich O atoms, compact ring system and moderate lipophilicity help to enhance membrane permeability and to enable additional hydrogen-bonding or π-based interactions. The combined influence of the electron-donating dioxole group and the electron-withdrawing hydrazone segment generates an internal charge-transfer environment, a feature often linked with stronger biological responses, improved antioxidant behaviour and distinctive electronic transitions. Overall, the thoughtful assembly of these functional groups results in a molecular scaffold with promising physicochemical and biological attributes (Maheswari et al., 2025 ; Senthilkumar et al., 2020 ).

In the present work, we report on the crystal structure, Hirshfeld surface analysis and crystal void studies of (1Z)-1-[(E)-2-(2H-1,3-benzodioxol-5-ylmethylidene)hydrazin-1-ylidene]-1,2-dihydrophthalazine, (I), which brings together several structural features discussed above.

2. Structural commentary

The molecular structure of (I) is displayed in Fig. 1. The C8—N1 [1.282 (2) Å], C9—N2 [1.308 (2) Å] and C10—N4 [1.289 (3) Å] bond lengths confirm their double-bond character. The 2H-1,3-benzodioxole ring (C1–C3/O1/C4/O2/C5–C7) is essentialy planar, with a maximum deviation of −0.039 (3) Å for atom C4. The planes of the fused five- and six-membered rings of this moiety make a dihedral angle of 0.41 (1)°. The 1,2-dihydrophthalazine moiety (C9/N3/N4/C10–C16) is also planar, exhibiting a maximum devation of 0.006 (2) Å for atom C15. The planes of the two fused six-membered rings of this moiety make a dihedral angle of 0.31 (1)°. The benzodioxole and dihydrophthalazine moieties are oriented with respect to each other at a dihedral angle of 11.25 (5)°. An intramolecular N3—H3⋯N1 hydrogen bond contributes to the stabilization of the molecular conformation (Table 1) and generates an S(5) ring motif (Bernstein et al., 1995 ), as shown in Fig. 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1	0.86	2.24	2.596 (2)	105
N3—H3⋯N2ⁱ	0.86	2.28	3.013 (2)	143
C8—H8⋯N1ⁱⁱ	0.93	2.62	3.517 (2)	162
Symmetry codes: (i) $[y-{\script{1\over 4}}, -x+{\script{3\over 4}}, z-{\script{1\over 4}}]$ ; (ii) $[-y+{\script{3\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Figure 1
The molecular structure of compound (I)

, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular hydrogen bond is shown as a dashed line.

3. Supramolecular features

In the crystal structure of (I), the molecules are interconnected through N3—H3⋯N2ⁱ hydrogen bonds, generating a C(4) chain motif that propagates parallel to [001] (Table 1 and Fig. 2). In addition, non-classical C8—H8⋯N1ⁱⁱ hydrogen bonds link adjacent molecules to form C(3) chain motifs that extend in a helical fashion parallel to [001]. Together with the intramolecular N3—H3⋯N2 hydrogen bond, these interactions combine into an S(7) ring motif, which further reinforces the overall crystal packing, as illustrated in Fig. 2.

Figure 2
The crystal packing of (I)

, with N—H⋯N and C—H⋯N intermolecular interactions shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

4. Hirshfeld surface and void analysis

In order to characterize and quantify the intermolecular interactions of (I), 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. 3, where deep-red spots indicative of strong interactions occur at N1, N2, H3 and H8, and these atoms are responsible for the intra- and intermolecular hydrogen bonds discussed above. 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. 4, the overall two-dimensional fingerprint plot for compound (I) is delineated into H⋯H, H⋯C/C⋯H, H⋯N/N⋯H, H⋯O/O⋯H, C⋯C, N⋯C/C⋯N and C⋯O/O⋯C contacts, revealing that H⋯H and H⋯C/C⋯H interactions are the main contributors to the crystal packing.

Figure 3
A view of the Hirshfeld surface mapped over d_norm for compound (I)

Figure 4
Two-dimensional fingerprint plots for compound (I)

, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯N/N⋯H, (e) H⋯O/O⋯H, (f) C⋯C, (g) N⋯C/C⋯N and (h) C⋯O/O⋯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.

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 volumes of the crystal voids (Fig. 5) and the percentages of free space in the unit cells were calculated to be 614.55 Å³ and 11.15%, respectively.

Figure 5
Graphical views of voids in the crystal packing of compound view down the (a) a axis and (b) b axis.

5. Synthesis and crystallization

Compound (I) was prepared by condensation of hydralazine hydrochloride (0.98 g, 0.005 mol) with piperonal (0.75 g, 0.005 mol) in methanol (30 ml). Sodium acetate (0.41 g, 0.005 mol) was added to neutralize the hydralazine hydrochloride in situ, generating free hydralazine; the resulting acetic acid acted as a mild catalyst to promote the reaction. The reaction progress was monitored by thin-layer chromatography (TLC) with ethyl acetate–hexane (5 ml; 1:4 v/v), confirming the disappearance of the starting materials. On cooling to room temperature, the crystallized product was collected by vacuum filtration and washed with cold methanol to remove inorganic salts. Single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane–methanol (1:1 v/v) by slow evaporation at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in idealized positions and allowed to ride on their parent atoms, with N—H = 0.86 Å and C—H = 0.93–0.97 Å, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms and U_iso(H) = 1.2U_eq(C,N) for all other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₄O₂
M_r	292.30
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	300
a, c (Å)	20.721 (5), 12.835 (3)
V (Å³)	5511 (3)
Z	16
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.13 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.968, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	40086, 3416, 2231
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.166, 1.17
No. of reflections	3416
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19
Computer programs: APEX3 (Bruker, 2017 ), SAINT (Bruker, 2017), SHELXT (Sheldrick, 2015a ), ORTEP-3 for Windows (Farrugia, 2012 ), SHELXL (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2512372

Crystal structure: contains datablocks I, shelx. DOI: https://doi.org/10.1107/S2056989026000538/wm5785sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000538/wm5785Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026000538/wm5785Isup3.cml

checkCIF report

Computing details top

(1Z)-1-[(E)-2-(2H-1,3-Benzodioxol-5-ylmethylidene)hydrazin-1-ylidene]-1,2-dihydrophthalazine top

Crystal data top

C₁₆H₁₂N₄O₂	D_x = 1.409 Mg m⁻³
M_r = 292.30	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 9881 reflections
a = 20.721 (5) Å	θ = 2.7–24.9°
c = 12.835 (3) Å	µ = 0.10 mm⁻¹
V = 5511 (3) Å³	T = 300 K
Z = 16	Block, yellow
F(000) = 2432	0.33 × 0.13 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	2231 reflections with I > 2σ(I)
Radiation source: i-mu-s microfocus source	R_int = 0.044
φ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −27→25
T_min = 0.968, T_max = 0.988	k = −25→26
40086 measured reflections	l = −17→17
3416 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)] = 0.048	w = 1/[σ²(F_o²) + (0.0632P)² + 3.5875P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max < 0.001
S = 1.17	Δρ_max = 0.18 e Å⁻³
3416 reflections	Δρ_min = −0.19 e Å⁻³
200 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00061 (18)

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
O1	0.39195 (9)	0.77008 (9)	0.29979 (16)	0.0864 (6)
O2	0.35150 (8)	0.76292 (8)	0.13220 (14)	0.0724 (5)
N1	0.18949 (7)	0.56513 (7)	0.13410 (12)	0.0454 (4)
N2	0.14478 (7)	0.51426 (7)	0.13390 (12)	0.0450 (4)
N3	0.14684 (8)	0.53064 (8)	−0.04779 (12)	0.0490 (4)
H3	0.176482	0.559169	−0.038998	0.059*
N4	0.12757 (9)	0.51996 (9)	−0.14794 (13)	0.0566 (5)
C1	0.28885 (10)	0.62896 (10)	0.34250 (15)	0.0522 (5)
H1	0.276323	0.599118	0.392705	0.063*
C2	0.33250 (11)	0.67694 (11)	0.36977 (17)	0.0609 (6)
H2	0.349117	0.680115	0.436885	0.073*
C3	0.34972 (10)	0.71904 (10)	0.29344 (17)	0.0556 (5)
C4	0.39145 (13)	0.79955 (12)	0.2006 (2)	0.0777 (7)
H4A	0.435018	0.801540	0.173126	0.093*
H4B	0.375045	0.843254	0.206206	0.093*
C5	0.32496 (9)	0.71475 (9)	0.19346 (16)	0.0489 (5)
C6	0.28210 (9)	0.66826 (9)	0.16482 (15)	0.0466 (4)
H6	0.266030	0.665787	0.097279	0.056*
C7	0.26323 (9)	0.62402 (9)	0.24257 (13)	0.0431 (4)
C8	0.21674 (9)	0.57300 (9)	0.22285 (14)	0.0450 (4)
H8	0.206329	0.544907	0.276803	0.054*
C9	0.12438 (8)	0.50119 (9)	0.03975 (14)	0.0419 (4)
C10	0.08325 (11)	0.47696 (11)	−0.16024 (16)	0.0583 (5)
H10	0.069081	0.468964	−0.227764	0.070*
C11	0.05416 (9)	0.44053 (9)	−0.07770 (15)	0.0495 (5)
C12	0.00633 (11)	0.39398 (11)	−0.09611 (18)	0.0618 (6)
H12	−0.007580	0.385954	−0.163766	0.074*
C13	−0.01994 (11)	0.36030 (12)	−0.0145 (2)	0.0653 (6)
H13	−0.051715	0.329541	−0.026824	0.078*
C14	0.00088 (11)	0.37211 (11)	0.08663 (19)	0.0613 (6)
H14	−0.017249	0.349151	0.141587	0.074*
C15	0.04801 (9)	0.41737 (10)	0.10665 (16)	0.0518 (5)
H15	0.061712	0.424791	0.174600	0.062*
C16	0.07506 (8)	0.45203 (9)	0.02410 (14)	0.0436 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0875 (12)	0.0756 (11)	0.0959 (14)	−0.0334 (9)	−0.0192 (11)	−0.0034 (10)
O2	0.0792 (11)	0.0616 (9)	0.0763 (11)	−0.0167 (8)	0.0059 (9)	0.0119 (8)
N1	0.0493 (9)	0.0468 (8)	0.0401 (8)	−0.0052 (7)	0.0012 (7)	−0.0015 (6)
N2	0.0484 (8)	0.0478 (8)	0.0389 (8)	−0.0049 (7)	−0.0014 (6)	0.0001 (6)
N3	0.0545 (9)	0.0555 (9)	0.0370 (8)	−0.0073 (7)	−0.0045 (7)	0.0026 (7)
N4	0.0643 (11)	0.0672 (11)	0.0384 (9)	−0.0059 (9)	−0.0072 (7)	0.0029 (7)
C1	0.0645 (12)	0.0530 (11)	0.0390 (10)	−0.0027 (9)	−0.0028 (9)	0.0000 (8)
C2	0.0677 (13)	0.0683 (13)	0.0468 (11)	−0.0069 (11)	−0.0130 (10)	−0.0077 (10)
C3	0.0524 (11)	0.0526 (11)	0.0618 (13)	−0.0053 (9)	−0.0043 (9)	−0.0070 (10)
C4	0.0721 (16)	0.0586 (14)	0.102 (2)	−0.0146 (12)	0.0114 (14)	−0.0070 (14)
C5	0.0494 (10)	0.0438 (10)	0.0536 (11)	0.0002 (8)	0.0060 (8)	0.0025 (8)
C6	0.0502 (10)	0.0493 (10)	0.0403 (9)	−0.0006 (8)	−0.0005 (8)	0.0002 (8)
C7	0.0467 (10)	0.0458 (9)	0.0367 (9)	0.0010 (7)	0.0009 (7)	−0.0037 (7)
C8	0.0525 (10)	0.0474 (10)	0.0350 (9)	−0.0031 (8)	0.0020 (7)	−0.0007 (7)
C9	0.0436 (9)	0.0447 (9)	0.0373 (9)	0.0029 (7)	−0.0008 (7)	0.0002 (7)
C10	0.0649 (13)	0.0685 (13)	0.0415 (10)	−0.0071 (11)	−0.0099 (9)	−0.0010 (9)
C11	0.0471 (10)	0.0550 (11)	0.0465 (10)	0.0004 (8)	−0.0040 (8)	−0.0026 (9)
C12	0.0569 (12)	0.0717 (14)	0.0567 (13)	−0.0090 (10)	−0.0100 (10)	−0.0075 (10)
C13	0.0556 (12)	0.0673 (14)	0.0729 (15)	−0.0142 (11)	−0.0042 (11)	−0.0060 (11)
C14	0.0557 (12)	0.0623 (13)	0.0660 (14)	−0.0090 (10)	0.0052 (10)	0.0041 (11)
C15	0.0529 (11)	0.0546 (11)	0.0480 (11)	−0.0040 (9)	−0.0013 (9)	0.0014 (9)
C16	0.0411 (9)	0.0457 (10)	0.0441 (10)	0.0028 (7)	−0.0018 (7)	0.0000 (7)

Geometric parameters (Å, º) top

O1—C3	1.375 (3)	C5—C6	1.361 (3)
O1—C4	1.412 (3)	C6—C7	1.410 (3)
O2—C5	1.385 (2)	C6—H6	0.9300
O2—C4	1.425 (3)	C7—C8	1.452 (3)
N1—C8	1.282 (2)	C8—H8	0.9300
N1—N2	1.403 (2)	C9—C16	1.457 (3)
N2—C9	1.308 (2)	C10—C11	1.434 (3)
N3—C9	1.361 (2)	C10—H10	0.9300
N3—N4	1.364 (2)	C11—C16	1.397 (3)
N3—H3	0.8600	C11—C12	1.403 (3)
N4—C10	1.289 (3)	C12—C13	1.371 (3)
C1—C2	1.389 (3)	C12—H12	0.9300
C1—C7	1.392 (3)	C13—C14	1.389 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.359 (3)	C14—C15	1.378 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C5	1.385 (3)	C15—C16	1.397 (3)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700

C3—O1—C4	105.94 (18)	C1—C7—C8	117.84 (17)
C5—O2—C4	105.36 (18)	C6—C7—C8	122.25 (16)
C8—N1—N2	112.83 (15)	N1—C8—C7	122.66 (17)
C9—N2—N1	111.74 (15)	N1—C8—H8	118.7
C9—N3—N4	127.26 (16)	C7—C8—H8	118.7
C9—N3—H3	116.4	N2—C9—N3	124.01 (17)
N4—N3—H3	116.4	N2—C9—C16	119.91 (16)
C10—N4—N3	115.84 (17)	N3—C9—C16	116.08 (16)
C2—C1—C7	122.22 (19)	N4—C10—C11	124.95 (18)
C2—C1—H1	118.9	N4—C10—H10	117.5
C7—C1—H1	118.9	C11—C10—H10	117.5
C3—C2—C1	116.66 (19)	C16—C11—C12	119.59 (19)
C3—C2—H2	121.7	C16—C11—C10	118.10 (18)
C1—C2—H2	121.7	C12—C11—C10	122.31 (19)
C2—C3—O1	128.2 (2)	C13—C12—C11	120.1 (2)
C2—C3—C5	121.96 (19)	C13—C12—H12	119.9
O1—C3—C5	109.88 (19)	C11—C12—H12	119.9
O1—C4—O2	109.22 (19)	C12—C13—C14	120.0 (2)
O1—C4—H4A	109.8	C12—C13—H13	120.0
O2—C4—H4A	109.8	C14—C13—H13	120.0
O1—C4—H4B	109.8	C15—C14—C13	120.9 (2)
O2—C4—H4B	109.8	C15—C14—H14	119.5
H4A—C4—H4B	108.3	C13—C14—H14	119.5
C6—C5—O2	128.04 (19)	C14—C15—C16	119.52 (19)
C6—C5—C3	122.52 (18)	C14—C15—H15	120.2
O2—C5—C3	109.43 (18)	C16—C15—H15	120.2
C5—C6—C7	116.73 (17)	C11—C16—C15	119.81 (17)
C5—C6—H6	121.6	C11—C16—C9	117.76 (17)
C7—C6—H6	121.6	C15—C16—C9	122.43 (17)
C1—C7—C6	119.91 (17)

C8—N1—N2—C9	−171.01 (16)	C6—C7—C8—N1	−0.6 (3)
C9—N3—N4—C10	−0.2 (3)	N1—N2—C9—N3	3.8 (3)
C7—C1—C2—C3	−0.5 (3)	N1—N2—C9—C16	−176.73 (14)
C1—C2—C3—O1	−179.5 (2)	N4—N3—C9—N2	−179.39 (18)
C1—C2—C3—C5	0.3 (3)	N4—N3—C9—C16	1.1 (3)
C4—O1—C3—C2	−178.2 (2)	N3—N4—C10—C11	−0.4 (3)
C4—O1—C3—C5	1.9 (3)	N4—C10—C11—C16	−0.1 (3)
C3—O1—C4—O2	−3.8 (3)	N4—C10—C11—C12	−179.6 (2)
C5—O2—C4—O1	4.2 (3)	C16—C11—C12—C13	0.4 (3)
C4—O2—C5—C6	178.1 (2)	C10—C11—C12—C13	179.9 (2)
C4—O2—C5—C3	−3.0 (2)	C11—C12—C13—C14	−0.2 (4)
C2—C3—C5—C6	−0.2 (3)	C12—C13—C14—C15	−0.2 (4)
O1—C3—C5—C6	179.64 (18)	C13—C14—C15—C16	0.2 (3)
C2—C3—C5—O2	−179.1 (2)	C12—C11—C16—C15	−0.3 (3)
O1—C3—C5—O2	0.7 (2)	C10—C11—C16—C15	−179.82 (18)
O2—C5—C6—C7	179.09 (18)	C12—C11—C16—C9	−179.46 (18)
C3—C5—C6—C7	0.4 (3)	C10—C11—C16—C9	1.0 (3)
C2—C1—C7—C6	0.7 (3)	C14—C15—C16—C11	0.0 (3)
C2—C1—C7—C8	−178.53 (19)	C14—C15—C16—C9	179.12 (18)
C5—C6—C7—C1	−0.6 (3)	N2—C9—C16—C11	179.03 (17)
C5—C6—C7—C8	178.62 (17)	N3—C9—C16—C11	−1.5 (2)
N2—N1—C8—C7	−178.01 (16)	N2—C9—C16—C15	−0.1 (3)
C1—C7—C8—N1	178.68 (18)	N3—C9—C16—C15	179.37 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.86	2.24	2.596 (2)	105
N3—H3···N2ⁱ	0.86	2.28	3.013 (2)	143
C8—H8···N1ⁱⁱ	0.93	2.62	3.517 (2)	162

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

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.

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