Crystal structure and Hirshfeld surface analysis of N′-[(1E)-1-(3-oxo-3,4-di­hydro-2H-1,4-benzoxazin-6-yl)ethyl­idene]benzohydrazide monohydrate

Janarthanan, S.; Meenambigai, G.; Mahalakshmi, V.; Kavitha, M.; Selvan, R.A.; Pazhamalai, S.; Selvanayagam, S.

doi:10.1107/S2056989025007819

research communications

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ISSN: 2056-9890

Volume 81| Part 10| October 2025| Pages 924-927

https://doi.org/10.1107/S2056989025007819

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Crystal structure and Hirshfeld surface analysis of N′-[(1E)-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethylidene]benzohydrazide monohydrate

Sekar Janarthanan,^a Ganesan Meenambigai,^a Velayutham Mahalakshmi,^a Manivel Kavitha,^a Rajendran Arivu Selvan,^a Srinivasan Pazhamalai ^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 August 2025; accepted 2 September 2025; online 5 September 2025)

The title compound, C₁₇H₁₅N₃O₃·H₂O, a hydrazone derivative, crystallizes with one molecule of water. The morpholine ring adopts a twist-boat conformation. Intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds are responsible for the consolidation of the crystal packing. The intermolecular interactions were quantified using Hirshfeld surface analysis, revealing that H⋯H interactions contribute most (40.6%) to the crystal packing.

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

CCDC reference: 2480218

1. Chemical context

Hydrazones, characterized by the —HN—N=C— linkage, are an important class of organic compounds with wide-ranging applications. They are employed as catalysts, bioactive molecules, organic dyes, and liquid crystals, as well as in agriculture as insecticides, sterilants, and herbicides (Meenatchi et al., 2021 ; Costa et al., 2025 ; Fuh et al., 2012 ). Their ability to form hydrogen bonds and coordinate to metal ions enhances their versatility, making them valuable scaffolds in drug design (Karthiga et al., 2025 ). Hydrazone derivatives also display a wide range of pharmacological activities, including antimicrobial, anticancer, antimalarial, anticonvulsant, and cardioprotective effects, with several already in clinical use. Examples include isoniazid, an essential antitubercular drug, and related analogs such as isocarboxazid, iproniazid, furazolidone, nifuroxazide, nitrofurantoin, and nitrofurazone, which are employed against various diseases. These cases highlight the therapeutic importance of hydrazide/hydrazone derivatives and their relevance in drug discovery (Teneva et al., 2023 ).

In the context given above, we synthesized a new hydrazone derivative, N′-[(1E)-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethylidene]benzohydrazide monohydrate, (I), and report here its molecular and crystal structure, and the results of a Hirshfeld surface analysis.

2. Structural commentary

The molecular structure of (I) is displayed in Fig. 1. The O2—C2 [1.235 (3) Å], C9—N2 [1.285 (3) Å] and O3—C11 [1.228 (3) Å] bond lengths confirm double-bond character. The morpholine ring adopts a twist-boat conformation with puckering parameters (Cremer & Pople, 1975 ) q₂ = 0.322 (2) Å, q₃ = 0.141 (2) Å, Q_T = 0.352 (2) Å and φ = 30.8 (3)°. Atom C1 deviates by 0.460 (3) Å from the least-squares plane through the remaining five atoms (O1/C2/N1/C3/C8) of the morpholine ring. The mean-plane calculation of the N′-[(1Z)-ethyliden]formohydrazide moiety (C9–C10/N2/N3/C11/O3) reveals that the atoms C10 and O3 deviate by 0.1836 (12) and 2.081 (14) Å, respectively, from the plane. This moiety makes a dihedral angle of 2.81 (13)° with respect to the phenyl ring (C12–C17). This phenyl ring and the phenyl ring (C3–C8) fused to the morpholine ring are oriented at a dihedral angle of 5.67 (10)°.

Figure 1
A view of the molecular structure of (I)

, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

3. Supramolecular features

In the crystal of (I), the oxygen atom (O1W) of the water molecule plays a major role in the crystal packing, acting both as a donor and an acceptor group in intermolecular O—H⋯O, N—H⋯O, and C—H⋯O hydrogen bonds (Table 1). The water molecule O1W acts as a trifold acceptor for two C—H⋯O (C10—H10B⋯O1Wⁱⁱ and C17—H17⋯O1Wⁱⁱ) and one N3—H3⋯O1Wⁱⁱ hydrogen bond (Fig. 2). It is a donor for two O—H⋯O hydrogen bonds (O1W—H1W⋯O2^v and O1W—H2W⋯O3^vi; Fig. 3). Molecules associate further into C(4) chains by N1—H1⋯O2ⁱ hydrogen bonds running parallel to [100]. In addition, C16—H16⋯O3^iv hydrogen bonds form C(6) chains running parallel to [110] (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	1.99	2.847 (3)	173
N3—H3⋯O1Wⁱⁱ	0.86	2.25	3.037 (3)	152
O1W—H1W⋯O2ⁱⁱⁱ	0.83 (1)	2.10 (2)	2.925 (3)	169 (5)
O1W—H2W⋯O3^iv	0.83 (1)	2.05 (2)	2.847 (3)	162 (3)
C10—H10B⋯O1Wⁱⁱ	0.96	2.34	3.200 (3)	150
C17—H17⋯O1Wⁱⁱ	0.93	2.52	3.228 (3)	133
C1—H1B⋯O3^v	0.97	2.57	3.286 (3)	131
C16—H16⋯O3^vi	0.93	2.58	3.447 (3)	155
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iv) ; (v) ; (vi) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
The crystal packing of (I)

with N—H⋯O and C—H⋯O hydrogen bonds to the solvent water molecule as an acceptor shown as dashed lines. For clarity, H atoms not involved in these hydrogen bonds have been omitted.

Figure 3
The crystal packing of (I)

with O—H⋯O hydrogen bonds involving the water solvent molecule as a donor shown as dashed lines. For clarity, H atoms not involved in these hydrogen bonds have been omitted.

Figure 4
The crystal packing of (I)

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

4. Hirshfeld surface analysis

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 at O2, O3, O1W and H1 are indicative of the intermolecular N—H⋯O, O—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 ) are displayed in Fig. 6. They 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 ). The HS analysis revealed that H⋯H and H⋯O/O⋯H contacts are the main contributors to the crystal packing, followed by H⋯C/C⋯H, H⋯N/N⋯H, C⋯C, N⋯C/C⋯N and O⋯C/C⋯O contacts.

Figure 6
Two-dimensional fingerprint plots for (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)C⋯C, (g) N⋯C/C⋯N and (h) O⋯C/C⋯O interactions with the corresponding percentages contribution. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Synthesis and crystallization

A mixture of 4-benzohydrazide (2 mmol) and 6-acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one (2 mmol) was dissolved in methanol (25 ml) containing a few drops of glacial acetic acid to obtain a clear solution. The reaction mixture was transferred to a round-bottom flask and refluxed for 3 h with continuous stirring. The progress of the reaction was monitored by thin-layer chromatography (TLC). Upon completion, the solvent was removed under reduced pressure, affording a solid residue. The crude product was collected, washed with cold methanol to remove impurities, and subsequently recrystallized from hot methanol to yield a pure product of (I).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms H1W and H2W were located in a difference-Fourier map and freely refined. Other 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-methyl) and 1.2U_eq(C or N) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₃·H₂O
M_r	327.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	299
a, b, c (Å)	7.4104 (3), 12.2781 (5), 17.3257 (7)
V (Å³)	1576.39 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.13 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.974, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	15825, 3894, 2868
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.111, 1.05
No. of reflections	3894
No. of parameters	226
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25
Absolute structure	Refined as an inversion twin
Absolute structure parameter	−0.4 (15)
Computer programs: APEX3 and SAINT (Bruker, 2017 ), SHELXT (Sheldrick, 2015a ), ORTEP-3 for Windows (Farrugia, 2012 ), SHELXL (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2480218

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025007819/wm5768sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025007819/wm5768Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025007819/wm5768Isup3.cml

checkCIF report

Computing details top

N'-[(1E)-1-(3-Oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethylidene]benzohydrazide monohydrate top

Crystal data top

C₁₇H₁₅N₃O₃·H₂O	D_x = 1.379 Mg m⁻³
M_r = 327.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 5917 reflections
a = 7.4104 (3) Å	θ = 3.0–23.2°
b = 12.2781 (5) Å	µ = 0.10 mm⁻¹
c = 17.3257 (7) Å	T = 299 K
V = 1576.39 (11) Å³	Block, colourless
Z = 4	0.27 × 0.13 × 0.12 mm
F(000) = 688

Data collection top

Bruker APEXII CCD diffractometer	2868 reflections with I > 2σ(I)
Radiation source: i-mu-s microfocus source	R_int = 0.036
ω and φ scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→7
T_min = 0.974, T_max = 0.988	k = −16→16
15825 measured reflections	l = −23→22
3894 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0632P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.111	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.19 e Å⁻³
3894 reflections	Δρ_min = −0.25 e Å⁻³
226 parameters	Absolute structure: Refined as an inversion twin
2 restraints	Absolute structure parameter: −0.4 (15)

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
H1W	0.377 (7)	0.224 (4)	0.8703 (13)	0.17 (2)*
H2W	0.486 (4)	0.1690 (19)	0.822 (2)	0.080 (11)*
O1	−0.2896 (2)	0.95271 (12)	1.00996 (10)	0.0477 (5)
O2	−0.2428 (2)	1.24134 (13)	1.02249 (10)	0.0469 (5)
O3	0.7149 (2)	1.07637 (13)	0.81266 (10)	0.0495 (5)
N1	−0.0451 (3)	1.11560 (15)	0.98123 (11)	0.0371 (5)
H1	0.041324	1.162300	0.982514	0.044*
N2	0.4543 (3)	0.93097 (16)	0.83363 (11)	0.0398 (5)
N3	0.6079 (3)	0.90671 (16)	0.79078 (12)	0.0408 (5)
H3	0.623173	0.843446	0.770503	0.049*
C1	−0.3546 (3)	1.06120 (19)	0.99967 (15)	0.0414 (6)
H1A	−0.443263	1.076619	1.039357	0.050*
H1B	−0.414913	1.065928	0.950101	0.050*
C2	−0.2091 (3)	1.14674 (18)	1.00297 (12)	0.0347 (5)
C3	−0.0077 (3)	1.00879 (18)	0.95616 (13)	0.0318 (5)
C4	0.1523 (3)	0.98296 (18)	0.91927 (13)	0.0347 (5)
H4	0.235910	1.037560	0.909001	0.042*
C5	0.1897 (3)	0.87617 (17)	0.89736 (12)	0.0327 (5)
C6	0.0621 (4)	0.79616 (19)	0.91380 (14)	0.0397 (6)
H6	0.085751	0.724151	0.900581	0.048*
C7	−0.1005 (4)	0.82224 (19)	0.94971 (14)	0.0413 (6)
H7	−0.185698	0.768344	0.959433	0.050*
C8	−0.1339 (3)	0.92836 (19)	0.97067 (13)	0.0350 (5)
C9	0.3590 (3)	0.84945 (18)	0.85609 (12)	0.0334 (5)
C10	0.4065 (4)	0.73195 (19)	0.84311 (15)	0.0502 (7)
H10A	0.314605	0.686455	0.865158	0.075*
H10B	0.414957	0.718030	0.788712	0.075*
H10C	0.520253	0.716270	0.867180	0.075*
C11	0.7324 (3)	0.98662 (18)	0.78224 (13)	0.0369 (5)
C12	0.8963 (3)	0.95828 (19)	0.73614 (13)	0.0353 (5)
C13	1.0105 (4)	1.0435 (2)	0.71613 (18)	0.0551 (7)
H13	0.980509	1.114507	0.729847	0.066*
C14	1.1677 (4)	1.0237 (3)	0.6761 (2)	0.0665 (9)
H14	1.242362	1.081437	0.662510	0.080*
C15	1.2150 (4)	0.9196 (3)	0.65617 (15)	0.0544 (7)
H15	1.321087	0.906665	0.628974	0.065*
C16	1.1054 (3)	0.8348 (2)	0.67653 (15)	0.0477 (7)
H16	1.137637	0.763970	0.663540	0.057*
C17	0.9464 (3)	0.85385 (19)	0.71639 (14)	0.0405 (6)
H17	0.872727	0.795578	0.729944	0.049*
O1W	0.4179 (3)	0.22231 (19)	0.82551 (14)	0.0727 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0415 (10)	0.0359 (9)	0.0657 (11)	−0.0009 (8)	0.0243 (9)	0.0007 (8)
O2	0.0432 (11)	0.0365 (9)	0.0609 (11)	0.0090 (8)	0.0028 (9)	−0.0107 (8)
O3	0.0499 (11)	0.0332 (9)	0.0655 (11)	0.0002 (9)	0.0116 (10)	−0.0081 (8)
N1	0.0282 (11)	0.0305 (10)	0.0525 (12)	−0.0007 (8)	0.0022 (9)	−0.0086 (9)
N2	0.0338 (11)	0.0396 (11)	0.0459 (11)	0.0059 (10)	0.0052 (10)	−0.0066 (9)
N3	0.0353 (11)	0.0340 (10)	0.0530 (12)	0.0025 (9)	0.0080 (10)	−0.0084 (9)
C1	0.0320 (12)	0.0417 (13)	0.0505 (14)	0.0008 (11)	0.0068 (12)	−0.0059 (12)
C2	0.0331 (12)	0.0365 (12)	0.0346 (11)	0.0048 (10)	0.0010 (11)	−0.0033 (10)
C3	0.0330 (13)	0.0270 (11)	0.0353 (12)	−0.0004 (10)	−0.0015 (10)	−0.0031 (10)
C4	0.0294 (12)	0.0310 (12)	0.0436 (12)	−0.0006 (10)	0.0015 (11)	−0.0026 (10)
C5	0.0346 (13)	0.0326 (11)	0.0309 (11)	0.0035 (10)	0.0005 (10)	0.0001 (9)
C6	0.0487 (15)	0.0281 (11)	0.0424 (13)	0.0019 (11)	0.0061 (13)	−0.0024 (10)
C7	0.0443 (15)	0.0320 (12)	0.0478 (14)	−0.0075 (12)	0.0078 (12)	0.0027 (10)
C8	0.0339 (13)	0.0364 (12)	0.0347 (11)	0.0008 (11)	0.0056 (10)	0.0005 (10)
C9	0.0359 (12)	0.0348 (12)	0.0294 (11)	0.0058 (11)	0.0008 (10)	−0.0014 (9)
C10	0.0559 (17)	0.0370 (14)	0.0577 (16)	0.0071 (13)	0.0198 (14)	0.0021 (12)
C11	0.0373 (13)	0.0322 (12)	0.0412 (12)	0.0016 (11)	0.0013 (11)	0.0020 (11)
C12	0.0336 (13)	0.0372 (13)	0.0350 (12)	0.0021 (11)	−0.0008 (10)	0.0020 (10)
C13	0.0529 (17)	0.0391 (15)	0.0731 (19)	−0.0037 (13)	0.0170 (16)	−0.0023 (14)
C14	0.0474 (18)	0.0582 (19)	0.094 (2)	−0.0145 (15)	0.0197 (17)	0.0046 (17)
C15	0.0351 (14)	0.073 (2)	0.0551 (16)	0.0064 (15)	0.0101 (13)	0.0020 (15)
C16	0.0444 (15)	0.0497 (15)	0.0492 (15)	0.0128 (14)	0.0014 (13)	−0.0043 (12)
C17	0.0373 (14)	0.0368 (13)	0.0476 (14)	0.0018 (12)	0.0029 (12)	0.0026 (11)
O1W	0.0842 (16)	0.0697 (15)	0.0643 (13)	0.0362 (14)	0.0257 (13)	0.0160 (12)

Geometric parameters (Å, º) top

O1—C8	1.373 (3)	C6—H6	0.9300
O1—C1	1.427 (3)	C7—C8	1.375 (3)
O2—C2	1.235 (3)	C7—H7	0.9300
O3—C11	1.228 (3)	C9—C10	1.502 (3)
N1—C2	1.329 (3)	C10—H10A	0.9600
N1—C3	1.409 (3)	C10—H10B	0.9600
N1—H1	0.8600	C10—H10C	0.9600
N2—C9	1.285 (3)	C11—C12	1.495 (3)
N2—N3	1.391 (3)	C12—C17	1.378 (3)
N3—C11	1.355 (3)	C12—C13	1.390 (3)
N3—H3	0.8600	C13—C14	1.378 (4)
C1—C2	1.506 (3)	C13—H13	0.9300
C1—H1A	0.9700	C14—C15	1.369 (4)
C1—H1B	0.9700	C14—H14	0.9300
C3—C8	1.383 (3)	C15—C16	1.367 (4)
C3—C4	1.384 (3)	C15—H15	0.9300
C4—C5	1.393 (3)	C16—C17	1.385 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.393 (3)	C17—H17	0.9300
C5—C9	1.481 (3)	O1W—H1W	0.834 (13)
C6—C7	1.393 (4)	O1W—H2W	0.831 (13)

C8—O1—C1	115.12 (17)	O1—C8—C3	120.2 (2)
C2—N1—C3	122.4 (2)	C7—C8—C3	120.5 (2)
C2—N1—H1	118.8	N2—C9—C5	116.0 (2)
C3—N1—H1	118.8	N2—C9—C10	125.1 (2)
C9—N2—N3	116.36 (18)	C5—C9—C10	118.9 (2)
C11—N3—N2	117.42 (19)	C9—C10—H10A	109.5
C11—N3—H3	121.3	C9—C10—H10B	109.5
N2—N3—H3	121.3	H10A—C10—H10B	109.5
O1—C1—C2	113.9 (2)	C9—C10—H10C	109.5
O1—C1—H1A	108.8	H10A—C10—H10C	109.5
C2—C1—H1A	108.8	H10B—C10—H10C	109.5
O1—C1—H1B	108.8	O3—C11—N3	122.0 (2)
C2—C1—H1B	108.8	O3—C11—C12	121.6 (2)
H1A—C1—H1B	107.7	N3—C11—C12	116.3 (2)
O2—C2—N1	122.2 (2)	C17—C12—C13	118.4 (2)
O2—C2—C1	121.4 (2)	C17—C12—C11	124.6 (2)
N1—C2—C1	116.31 (19)	C13—C12—C11	116.9 (2)
C8—C3—C4	120.0 (2)	C14—C13—C12	120.4 (3)
C8—C3—N1	118.4 (2)	C14—C13—H13	119.8
C4—C3—N1	121.6 (2)	C12—C13—H13	119.8
C3—C4—C5	120.8 (2)	C15—C14—C13	120.6 (3)
C3—C4—H4	119.6	C15—C14—H14	119.7
C5—C4—H4	119.6	C13—C14—H14	119.7
C4—C5—C6	118.2 (2)	C16—C15—C14	119.5 (3)
C4—C5—C9	120.6 (2)	C16—C15—H15	120.2
C6—C5—C9	121.2 (2)	C14—C15—H15	120.2
C7—C6—C5	121.1 (2)	C15—C16—C17	120.4 (2)
C7—C6—H6	119.5	C15—C16—H16	119.8
C5—C6—H6	119.5	C17—C16—H16	119.8
C8—C7—C6	119.4 (2)	C12—C17—C16	120.6 (2)
C8—C7—H7	120.3	C12—C17—H17	119.7
C6—C7—H7	120.3	C16—C17—H17	119.7
O1—C8—C7	119.2 (2)	H1W—O1W—H2W	108 (4)

C9—N2—N3—C11	−164.5 (2)	N1—C3—C8—C7	−177.7 (2)
C8—O1—C1—C2	−43.3 (3)	N3—N2—C9—C5	−176.25 (18)
C3—N1—C2—O2	−177.5 (2)	N3—N2—C9—C10	3.4 (3)
C3—N1—C2—C1	0.2 (3)	C4—C5—C9—N2	−8.7 (3)
O1—C1—C2—O2	−153.8 (2)	C6—C5—C9—N2	169.9 (2)
O1—C1—C2—N1	28.4 (3)	C4—C5—C9—C10	171.7 (2)
C2—N1—C3—C8	−14.6 (3)	C6—C5—C9—C10	−9.7 (3)
C2—N1—C3—C4	166.7 (2)	N2—N3—C11—O3	2.1 (3)
C8—C3—C4—C5	−0.9 (3)	N2—N3—C11—C12	179.84 (18)
N1—C3—C4—C5	177.7 (2)	O3—C11—C12—C17	163.5 (2)
C3—C4—C5—C6	−0.2 (3)	N3—C11—C12—C17	−14.2 (3)
C3—C4—C5—C9	178.4 (2)	O3—C11—C12—C13	−12.5 (3)
C4—C5—C6—C7	1.3 (3)	N3—C11—C12—C13	169.7 (2)
C9—C5—C6—C7	−177.3 (2)	C17—C12—C13—C14	1.3 (4)
C5—C6—C7—C8	−1.3 (4)	C11—C12—C13—C14	177.6 (3)
C1—O1—C8—C7	−153.1 (2)	C12—C13—C14—C15	−0.7 (5)
C1—O1—C8—C3	30.4 (3)	C13—C14—C15—C16	−0.3 (5)
C6—C7—C8—O1	−176.3 (2)	C14—C15—C16—C17	0.6 (4)
C6—C7—C8—C3	0.1 (4)	C13—C12—C17—C16	−1.0 (4)
C4—C3—C8—O1	177.4 (2)	C11—C12—C17—C16	−176.9 (2)
N1—C3—C8—O1	−1.3 (3)	C15—C16—C17—C12	0.0 (4)
C4—C3—C8—C7	1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	1.99	2.847 (3)	173
N3—H3···O1Wⁱⁱ	0.86	2.25	3.037 (3)	152
O1W—H1W···O2ⁱⁱⁱ	0.83 (1)	2.10 (2)	2.925 (3)	169 (5)
O1W—H2W···O3^iv	0.83 (1)	2.05 (2)	2.847 (3)	162 (3)
C10—H10B···O1Wⁱⁱ	0.96	2.34	3.200 (3)	150
C17—H17···O1Wⁱⁱ	0.93	2.52	3.228 (3)	133
C1—H1B···O3^v	0.97	2.57	3.286 (3)	131
C16—H16···O3^vi	0.93	2.58	3.447 (3)	155

Symmetry codes: (i) x+1/2, −y+5/2, −z+2; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+2; (iv) x, y−1, z; (v) x−1, y, z; (vi) −x+2, y−1/2, −z+3/2.

Footnotes

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

Acknowledgements

The authors are very thankful to 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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