Crystal structure, Hirshfeld surface analysis and crystal voids of 4-nitro­benzo[c][1,2,5]selena­diazole

Gurbanov, A.V.; Hökelek, T.; Mammadova, G.Z.; Hasanov, K.I.; Javadzade, T.A.; Belay, A.N.

doi:10.1107/S2056989024012398

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 81| Part 2| February 2025|

https://doi.org/10.1107/S2056989024012398

Open

access

Crystal structure, Hirshfeld surface analysis and crystal voids of 4-nitrobenzo[c][1,2,5]selenadiazole

Atash V. Gurbanov,^a,^b Tuncer Hökelek,^c Gunay Z. Mammadova,^d Khudayar I. Hasanov,^e,^f Tahir A. Javadzade ^g and Alebel N. Belay ^h ^*

^aExcellence Center, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^bCentro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, ^cHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^dDepartment of Chemistry, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan, ^eWestern Caspian University, Istiglaliyyat Str. 31, AZ 1001 Baku, Azerbaijan, ^fAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, Azerbaijan, ^gDepartment of Chemistry and Chemical Engineering, Khazar University, Mahzati Str. 41, AZ 1096 Baku, Azerbaijan, and ^hDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: alebel.nibret@bdu.edu.et

Edited by F. Di Salvo, University of Buenos Aires, Argentina (Received 24 October 2024; accepted 23 December 2024; online 7 January 2025)

The title molecule, C₆H₃N₃O₂Se, is almost planar. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a network structure, enclosing R²₂(7) and R³₃(8) ring motifs, parallel to the bc plane. There are π–π interactions present with centroid-to-centroid distances of 3.746 (3) and 3.697 (3) Å. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯O/O⋯H (19.6%), H⋯N/N⋯H (11.0%), H⋯Se/Se⋯H (8.5%), O⋯Se/Se⋯O (8.2%), H⋯H (7.4%), C⋯N/N⋯C (7.3%) and N⋯Se/Se⋯N (7.2%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 25.60 Å³ and 3.73%, showing that there is no large cavity in the crystal.

Keywords: crystal structure; non-covalent interactions; chalcogen bond.

CCDC reference: 2412565

1. Chemical context

Like other weak interactions, the chalcogen bond (ChB) has attracted considerable attention due to its various applications in synthesis, catalysis, crystal engineering, biochemical processes, molecular recognition, functional materials, etc. (Mahmudov et al., 2017 ; Mahmudov et al., 2022 ; Scilabra et al., 2019 ). Both bond parameters, strength and directionality of ChB can be improved by variation of substituents, ChB atom (tunability), nucleophile, resonance and cooperation of weak interactions (Aliyeva et al., 2024 ; Gurbanov et al., 2020 ). For instance, due to cooperation of the ChB, the common four-membered Se₂N₂ aggregate of [1,2,5]selenadiazoles is well employed in materials chemistry (Hua et al., 2020 ; Ho et al., 2020 ; Tiekink, 2022 ). In this regard, we studied the ortho-NO₂ effect on the Se₂N₂ synthon of 4-nitrobenzo[c][1,2,5]selenadiazole aggregates. We provided herein a detailed synthesis and an examination of the molecular and crystal structures together with the Hirshfeld surface analysis and crystal voids of the title compound, (I).

2. Structural commentary

The title compound (Fig. 1) is almost planar, with the planar A (C1–C6) and B (Se/N1/N2/C1/C6) rings oriented at a dihedral angle of A/B = 0.94 (15)°. Atoms N3, O1 and O2 are displaced by −0.004 (6), −0.024 (6) and 0.022 (6) Å, respectively, from the best least-squares plane of ring A. Hence, they are almost coplanar. There are no unusual bond distances or interbond angles in the molecule.

Figure 1
The title molecule with the atom-numbering scheme and 50% probability ellipsoids.

3. Supramolecular features

In the crystal, intermolecular C—H⋯O hydrogen bonds (Table 1) link the molecules into a network structure, enclosing R₂²(7) and R₃³(8) ring motifs (Fig. 2), parallel to the bc plane (Fig. 3). No C—H⋯π(ring) interactions are observed but there are two π–π interactions between the almost parallel A and B rings and also between the parallel B rings with centroid-to-centroid distances of 3.746 (3) and 3.697 (3) Å, respectively [Cg1⋯Cg2ⁱ = 3.746 (3) Å with α = 0.91° and Cg2⋯Cg2ⁱ = 3.697 (3) Å with α = 0.00° where Cg1 and Cg2 are the centroids of rings A and B, respectively; symmetry code: (i) −x, −y, 1 − z].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2^iv	0.95	2.52	3.269 (7)	135
C5—H5⋯O1ⁱⁱⁱ	0.95	2.33	3.240 (7)	161
Symmetry codes: (iii) ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A partial packing diagram. Intermolecular C—H⋯O hydrogen bonds are shown by dashed lines.

Figure 3
A partial packing diagram, viewed down the b-axis direction. Intermolecular C—H⋯O hydrogen bonds are shown by dashed lines.

4. Hirshfeld surface analysis

In order to visualize the intermolecular interactions, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ). In the HS plotted over d_norm (Fig. 4), the white areas indicate contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter (in close contact) or longer (distinct contact) than the van der Waals radii, respectively (Venkatesan et al., 2016 ). The bright-red spots indicate their roles as the respective donors and/or acceptors. The shape-index surface can be used to identify characteristic packing modes, in particular, planar stacking arrangements and the presence of aromatic stacking interactions such as C—H⋯π and π–π interactions. C—H⋯π interactions are represented as red p-holes, which are related to the electron ring interactions between the CH groups and the centroid of the aromatic rings of neighbouring molecules. Fig. 5 clearly suggests that there are no C—H⋯π interactions in (I). The shape-index is a tool for visualizing π–π stacking by the presence of adjacent red and blue triangles; if there are no adjacent red and/or blue triangles, then there are no π–π interactions. Fig. 5 clearly suggests that there are π–π interactions in (I). The overall two-dimensional fingerprint plot, Fig. 6a, and those delineated into H⋯O/O⋯H, H⋯N/N⋯H, H⋯Se/Se⋯H, O⋯Se/Se⋯O, H⋯H, C⋯N/N⋯C, N⋯Se/Se⋯N, N⋯O/O⋯N, C⋯O/O⋯C, H⋯C/C⋯H, C⋯C, N⋯N, O⋯O and C⋯Se/Se⋯C (McKinnon et al., 2007 ) are illustrated in Fig. 6b–o, respectively, together with their relative contributions to the Hirshfeld surface. The most important interaction is H⋯O/O⋯H (Table 2) contributing 19.6% to the overall crystal packing, which is reflected in Fig. 6b as a pair of spikes with the tips at d_e + d_i = 2.20 Å. The H⋯N/N⋯H contacts (Fig. 6c) make an 11.0% contribution to the HS and have the tips at d_e + d_i = 3.46 Å. The H⋯Se/Se⋯H contacts (Fig. 6d; 8.5% contribution to the HS) have a pair of wings with the tips at d_e + d_i = 3.34 Å. The pair of spikes for the O⋯Se/Se⋯O contacts (Table 2 and Fig. 6e), contributing 8.2% to the HS, have the tips at d_e + d_i = 3.14 Å. The H⋯H interactions (Fig. 6f) contribute 7.4% to the HS with the tip at d_e = d_i = 1.12 Å. The C⋯N/N⋯C (Fig. 6g), N⋯Se/Se⋯N (Table 2 and Fig. 6h) and N⋯O/O ⋯N (Table 2 and Fig. 6i) contacts contribute 7.3%, 7.2% and 6.9%, respectively, to the HS and are viewed as pairs of spikes with the tips at d_e + d_i = 3.26, 3.08 and 3.04 Å, respectively. The C⋯O/ O⋯C contacts (Fig. 6j) make 6.4% contribution to the HS with the central point at d_e = d_i = 1.72 Å. In the absence of C—H⋯π interactions, the H⋯C/C⋯H contacts, contributing 5.9% to the overall crystal packing, are reflected in Fig. 6k with the tips at d_e + d_i = 3.46 Å. The C⋯C contacts (Fig. 6l) contributing 5.1% to the HS have a bullet-shaped distribution of points with the tip at d_e = d_i = 1.69Å. Finally, the N⋯N (Table 2 and Fig. 6m), O⋯O (Fig. 6n) and C⋯Se/Se⋯C (Fig. 6o) contacts with 3.3%, 2.1% and 1.1% contributions, respectively, to the HS have very low densities.

Table 2
Selected interatomic distances (Å)

Se1⋯O1ⁱ	3.140 (4)	O2⋯H3	2.37
Se1⋯N1ⁱ	3.132 (5)	H4⋯O2^iv	2.52
Se1⋯N2ⁱⁱ	3.079 (5)	N1⋯N3	3.012 (6)
O1⋯N1	2.709 (6)	N1⋯N2ⁱⁱ	3.017 (6)
H5⋯O1ⁱⁱⁱ	2.33
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 4
View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm.

Figure 5
Hirshfeld surface of the title compound plotted over shape-index.

Figure 6
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯O/O⋯H, (c) H⋯N/N⋯H, (d) H⋯Se/Se⋯H, (e) O⋯Se/Se⋯O, (f) H⋯H, (g) C⋯N/N⋯C, (h) N⋯Se/Se⋯N, (i) N⋯O/O⋯N, (j) C⋯O/O⋯C, (k) H⋯C/C ⋯H, (l) C⋯C, (m) N⋯N, (n) O⋯O and (o) C⋯Se/Se⋯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.

The nearest neighbour coordination environment of a molecule can be determined from the colour patches on the HS based on how close to other molecules they are. The Hirshfeld surface representations with the function d_norm plotted onto the surface are shown for the H⋯O/O⋯H, H⋯N/N⋯H and H⋯Se/Se⋯H interactions in Fig. 7a–c, respectively.

Figure 7
The Hirshfeld surface representations with the function d_norm plotted onto the surface for (a) H⋯O/O⋯H, (b) H⋯N/N⋯H and (c) H⋯Se/Se⋯H interactions.

The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯O/O⋯H, H⋯N/N⋯H and H⋯Se/Se⋯H interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

5. Crystal voids

The strength of the crystal packing is important for determining the response to an applied mechanical force. If the crystal packing results in significant voids, the molecules are not tightly packed and a small amount of applied external mechanical force may easily break the crystal. To check the mechanical stability of the crystal, 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. 8a–c) and the percentage of free space in the unit cell are calculated as 25.60 Å³ and 3.73%, respectively. Thus, the crystal packing appears compact and the mechanical stability should be substantial.

Figure 8
Graphical views of voids in the crystal packing of (I)

(a) along the a-axis direction, (b) along the b-axis direction and (c) along the c-axis direction.

6. Database survey

A survey conducted of the Cambridge Structural Database (CSD, Version 5.45, last updated September 2024; Groom et al., 2016 ) indicates that two molecules are similar to the title compound (I): (rac)-4-methyl-4-nitro-2,1,3-benzoselena-diazol-5(4H)-one, C₇H₅N₃O₃Se (CSD refcode JURLAJ; Tian et al., 1993 ) and 5-nitro-2,1,3-benzoselenadiazole, C₆H₃N₃O₂Se (CSD refcode DOBWUQ; Aliyeva et al., 2023).

7. Synthesis and crystallization

3-Nitrobenzene-1,2-diamine (10 mmol) and selenium dioxide (10 mmol) were dissolved in 25 ml of dichloromethane and stirred for 1 h at ambient temperature, and further refluxed for 1 h (Georges et al., 2024 ). After cooling to room temperature, the solvent was evaporated under reduced pressure to give the reaction product. Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution. Yield 82% (based on SeO₂), yellow powder soluble in methanol, ethanol and DMSO. Analysis calculated for C₆H₃N₃O₂Se (M_r = 228.07): C, 31.60; H, 1.33; N, 18.42. Found: C, 31.58, H, 1.30; N, 18.40. ESI–MS (positive ion mode), m/z: 229.10 [M_r + H]^{+. 1}H NMR (DMSO-d⁶), δ: 7.72–8.46 (3H, Ar-H). ¹³C NMR (DMSO-d⁶), 126.4, 126.8, 129.4, 140.5, 149.9 and 159.9.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The C-bond H atoms were positioned geometrically (C—H = 0.95 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₆H₃N₃O₂Se
M_r	228.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	7.0105 (4), 13.2765 (8), 8.1311 (5)
β (°)	114.808 (3)
V (Å³)	686.96 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	5.42
Crystal size (mm)	0.28 × 0.21 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.284, 0.473
No. of measured, independent and observed [I > 2σ(I)] reflections	5894, 1475, 1297
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.636

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.17
No. of reflections	1475
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.24, −1.27
Computer programs: APEX4 and SAINT (Bruker, 2014), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2412565

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024012398/vu2008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024012398/vu2008Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024012398/vu2008Isup3.cml

checkCIF report

Computing details top

4-Nitrobenzo[c][1,2,5]selenadiazole top

Crystal data top

C₆H₃N₃O₂Se	F(000) = 440
M_r = 228.07	D_x = 2.205 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.0105 (4) Å	Cell parameters from 2556 reflections
b = 13.2765 (8) Å	θ = 3.1–26.7°
c = 8.1311 (5) Å	µ = 5.42 mm⁻¹
β = 114.808 (3)°	T = 150 K
V = 686.96 (7) Å³	Prism, yellow
Z = 4	0.28 × 0.21 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	1297 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.9°, θ_min = 3.1°
T_min = 0.284, T_max = 0.473	h = −8→8
5894 measured reflections	k = −16→16
1475 independent reflections	l = −10→10

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + 6.1884P] where P = (F_o² + 2F_c²)/3
1475 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 1.24 e Å⁻³
0 restraints	Δρ_min = −1.27 e Å⁻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
Se1	0.77441 (9)	0.25835 (4)	0.82143 (8)	0.01947 (18)
O1	0.7737 (8)	0.4739 (3)	0.3944 (6)	0.0372 (11)
O2	0.7408 (8)	0.6348 (3)	0.4079 (6)	0.0324 (11)
N1	0.7713 (7)	0.3520 (3)	0.6607 (6)	0.0179 (10)
N2	0.7564 (7)	0.3476 (3)	0.9783 (6)	0.0198 (10)
N3	0.7548 (8)	0.5496 (3)	0.4731 (6)	0.0219 (10)
C1	0.7570 (8)	0.4405 (4)	0.7304 (7)	0.0152 (10)
C2	0.7477 (8)	0.5380 (4)	0.6503 (7)	0.0155 (10)
C3	0.7288 (8)	0.6233 (4)	0.7359 (7)	0.0175 (11)
H3	0.720824	0.686805	0.679574	0.021*
C4	0.7207 (8)	0.6192 (4)	0.9056 (7)	0.0174 (11)
H4	0.707675	0.680103	0.961342	0.021*
C5	0.7310 (8)	0.5300 (4)	0.9926 (7)	0.0164 (10)
H5	0.726556	0.528392	1.107708	0.020*
C6	0.7487 (8)	0.4387 (4)	0.9056 (7)	0.0161 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0249 (3)	0.0107 (2)	0.0233 (3)	0.0001 (2)	0.0106 (2)	0.0017 (2)
O1	0.066 (3)	0.019 (2)	0.034 (3)	0.001 (2)	0.029 (2)	−0.0030 (18)
O2	0.054 (3)	0.019 (2)	0.029 (2)	0.0017 (19)	0.022 (2)	0.0081 (17)
N1	0.023 (3)	0.012 (2)	0.020 (2)	0.0017 (17)	0.009 (2)	−0.0001 (17)
N2	0.022 (2)	0.014 (2)	0.024 (3)	0.0000 (17)	0.011 (2)	0.0018 (18)
N3	0.028 (3)	0.020 (2)	0.020 (3)	0.0003 (19)	0.012 (2)	0.0011 (19)
C1	0.013 (2)	0.014 (2)	0.018 (3)	−0.0010 (18)	0.006 (2)	0.0004 (19)
C2	0.017 (3)	0.015 (2)	0.017 (3)	0.0001 (19)	0.008 (2)	0.0010 (19)
C3	0.019 (3)	0.015 (2)	0.017 (3)	0.001 (2)	0.006 (2)	0.003 (2)
C4	0.022 (3)	0.014 (2)	0.019 (3)	0.001 (2)	0.012 (2)	−0.0055 (19)
C5	0.019 (3)	0.018 (2)	0.015 (3)	0.001 (2)	0.010 (2)	−0.002 (2)
C6	0.016 (3)	0.015 (2)	0.018 (3)	0.0005 (19)	0.009 (2)	0.0011 (19)

Geometric parameters (Å, º) top

Se1—N2	1.784 (5)	C1—C6	1.450 (7)
Se1—N1	1.797 (4)	C2—C3	1.364 (7)
O1—N3	1.228 (6)	C3—C4	1.406 (7)
O2—N3	1.235 (6)	C3—H3	0.9500
N1—C1	1.327 (6)	C4—C5	1.366 (7)
N2—C6	1.338 (7)	C4—H4	0.9500
N3—C2	1.471 (7)	C5—C6	1.434 (7)
C1—C2	1.439 (7)	C5—H5	0.9500

Se1···O1ⁱ	3.140 (4)	O2···H3	2.37
Se1···N1ⁱ	3.132 (5)	H4···O2^iv	2.52
Se1···N2ⁱⁱ	3.079 (5)	N1···N3	3.012 (6)
O1···N1	2.709 (6)	N1···N2ⁱⁱ	3.017 (6)
H5···O1ⁱⁱⁱ	2.33

N2—Se1—N1	94.46 (19)	C2—C3—C4	121.4 (5)
C1—N1—Se1	106.4 (3)	C2—C3—H3	119.3
C6—N2—Se1	106.7 (4)	C4—C3—H3	119.3
O1—N3—O2	122.2 (5)	C5—C4—C3	121.8 (5)
O1—N3—C2	118.7 (4)	C5—C4—H4	119.1
O2—N3—C2	119.1 (4)	C3—C4—H4	119.1
N1—C1—C2	126.9 (5)	C4—C5—C6	118.3 (5)
N1—C1—C6	116.5 (5)	C4—C5—H5	120.8
C2—C1—C6	116.5 (4)	C6—C5—H5	120.8
C3—C2—C1	120.7 (5)	N2—C6—C5	122.8 (5)
C3—C2—N3	117.6 (4)	N2—C6—C1	116.0 (5)
C1—C2—N3	121.6 (4)	C5—C6—C1	121.2 (5)

N2—Se1—N1—C1	−0.2 (4)	C1—C2—C3—C4	0.9 (8)
N1—Se1—N2—C6	0.2 (4)	N3—C2—C3—C4	180.0 (5)
Se1—N1—C1—C2	−179.5 (4)	C2—C3—C4—C5	−0.1 (9)
Se1—N1—C1—C6	0.2 (6)	C3—C4—C5—C6	−0.5 (8)
N1—C1—C2—C3	178.7 (5)	Se1—N2—C6—C5	179.2 (4)
C6—C1—C2—C3	−1.0 (7)	Se1—N2—C6—C1	−0.1 (6)
N1—C1—C2—N3	−0.3 (8)	C4—C5—C6—N2	−178.9 (5)
C6—C1—C2—N3	180.0 (5)	C4—C5—C6—C1	0.4 (8)
O1—N3—C2—C3	179.4 (5)	N1—C1—C6—N2	0.0 (7)
O2—N3—C2—C3	−0.9 (8)	C2—C1—C6—N2	179.7 (5)
O1—N3—C2—C1	−1.6 (8)	N1—C1—C6—C5	−179.4 (5)
O2—N3—C2—C1	178.1 (5)	C2—C1—C6—C5	0.4 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^iv	0.95	2.52	3.269 (7)	135
C5—H5···O1ⁱⁱⁱ	0.95	2.33	3.240 (7)	161

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

Acknowledgements

The authors' contributions are as follows. Conceptualization, AVG, TH and ANB; synthesis, AVG and GZM; X-ray analysis, AVG; writing (review and editing of the manuscript) AVG and TH; funding acquisition, AVG, GZM, KIH and TAJ; supervision, AVG, TH and ANB.

Funding information

This work was supported by the Fundaçao para a Ciencia e a Tecnologia (FCT, Portugal) , projects UIDB/00100/2020 (https://doi.org/10.54499/UIDB/00100/2020) and UIDP/00100/2020 (https://doi.org/10.54499/UIDP/00100/2020) of the Centro de Quimica Estrutural, and LA/P/0056/2020 (https://doi.org/10.54499/LA/P/0056/2020) of the Institute of Molecular Sciences, as well as Baku State University, Azerbaijan Medical University, Western Caspian University and Khazar University in Azerbaijan. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

References

Aliyeva, V. A., Gurbanov, A. V., Guedes da Silva, M. F. C., Gomila, R. M., Frontera, A., Mahmudov, K. T. & Pombeiro, A. J. L. (2024). Cryst. Growth Des. 24, 781–791. Web of Science CSD CrossRef CAS Google Scholar
Georges, T., Ovens, J. S. & Bryce, D. L. (2024). Chem. A Eur. J. e202402254. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Mahmudov, K. T., Pombeiro, A. J. L. & Resnati, G. (2020). Chem. A Eur. J. 26, 14833–14837. Web of Science CSD CrossRef CAS Google Scholar
Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ, 2, 563–574. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Hirshfeld, H. L. (1977). Theor. Chim. Acta, 44, 129–138. CrossRef CAS Web of Science Google Scholar
Ho, P. C., Wang, J. Z., Meloni, F. & Vargas-Baca, I. (2020). Coord. Chem. Rev. 422, 213464. Web of Science CrossRef Google Scholar
Hua, B., Zhang, C., Zhou, W., Shao, L., Wang, Z., Wang, L., Zhu, H. & Huang, F. (2020). J. Am. Chem. Soc. 142, 16557–16561. CrossRef PubMed 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
Mahmudov, K. T., Gurbanov, A. V., Aliyeva, V. A., Guedes da Silva, M. F. C., Resnati, G. & Pombeiro, A. J. L. (2022). Coord. Chem. Rev. 464, 214556. Web of Science CrossRef Google Scholar
Mahmudov, K. T., Kopylovich, M. N., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2017). Dalton Trans. 46, 10121–10138. Web of Science CrossRef CAS PubMed Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814. Google Scholar
Scilabra, P., Terraneo, G. & Resnati, G. (2019). Acc. Chem. Res. 52, 1313–1324. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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, 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
Tian, W., Grivas, S. & Olsson, K. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 257. Google Scholar
Tiekink, E. R. T. (2022). CrystEngComm, 25, 9–39. CrossRef 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
Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H. & Sundius, T. (2016). Spectrochim. Acta A Mol. Biomol. Spectrosc. 153, 625–636. Web of Science CSD CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.