Synthesis and structure of 9-(di­methyl­amino)-1,10-phenanthrolin-1-ium nitrate

Torambetov, B.; Allaniyazov, M.; Ashurov, J.; Hökelek, T.; Belay, A.N.; Hasanov, K.I.; Guliyeva, N.A.

doi:10.1107/S2056989026006882

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ISSN: 2056-9890

Volume 82| Part 8| August 2026|

https://doi.org/10.1107/S2056989026006882

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Synthesis and structure of 9-(dimethylamino)-1,10-phenanthrolin-1-ium nitrate

Batirbay Torambetov,^a Mukhammedaliy Allaniyazov,^a Jamshid Ashurov,^b Tuncer Hökelek,^c Alebel N. Belay,^d ^* Khudayar I. Hasanov ^e and Narmina A. Guliyeva ^f

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St., Tashkent 100174, Uzbekistan, ^bInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek St. 83, Tashkent 100125, Uzbekistan, ^cHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^dDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia, ^eAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14, AZ 1022, Baku, Azerbaijan, and ^fDepartment of Chemical Engineering, Baku Engineering University, Hasan Aliyev Str. 120, AZ0101, Khirdalan, Absheron, Azerbaijan
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 2 June 2026; accepted 1 July 2026; online 10 July 2026)

In the title salt, C₁₄H₁₄N₃⁺·NO₃⁻, the cation is almost planar (r.m.s. deviation = 0.015 Å), implying significant conjugation of the lone pair of the tertiary amino group N atom with the aromatic ring system. In the extended structure, N—H⋯O and C—H⋯O hydrogen bonds link the components into infinite chains of alternating cations and anions propagating along the b-axis direction. Aromatic π–π stacking interactions with centroid–centroid distances of 3.5773 (12) and 3.5889 (12) Å may help to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H⋯H (39.2%), H⋯O/O⋯H (31.6%), H⋯C/C⋯H (10.3%) and C⋯C (9.1%) interactions.

Keywords: 1,10-phenanthroline; crystal structure; noncovalent interactions.

CCDC reference: 2566614

1. Chemical context

1,10-Phenanthroline and its derivatives are widely used in medicinal, catalysis, materials and coordination chemistry (e.g., Queffelec et al., 2024 ; Krawiec et al., 2005 ; Kumar et al., 2022 ). Polyaromatic rings in this class of organic compounds possess rigidity and robustness, which may be significant in the design of functional materials such as catalysts, luminescent coordination scaffolds, supramolecular aggregates, sensors and theranostics. 1,10-Phenanthroline derivatives are popular ligands in coordination chemistry due to their strong affinities for a wide range of metals with various oxidation states (Naithani et al., 2023 ). Substitution of the aromatic ring of 1,10-phenanthroline can be used as an important synthetic strategy towards new materials (Figueiredo et al., 2022 ; Tsvetkov et al., 2025 ).

As part of our studies in this area, we now report the synthesis and structure of the title salt, C₁₄H₁₄N₃⁺·NO₃⁻ (I).

2. Structural commentary

The asymmetric unit of (I), which crystallizes in space group P2₁/n, consists of one dimethylaminophenanthroline cation and one nitrate counter ion (Fig. 1). The phenanthroline ring system is almost planar with an r.m.s. deviation of 0.0125 Å. Atoms N3, C13 and C14 are displaced by −0.035 (2), −0.001 (3) and −0.011 (3) Å, respectively, away from the best least-squares plane of the phenanthroline ring system. Evidence of their near co-planarity with the ring system is further supported by the C13—N3—C10—N2 [–178.5 (2)°] and C14—N3—C10—N2 [–2.6 (3)°] torsion angles. The C1—N1—C12 [123.41 (18)°] bond angle at the protonated N1 atom of the ring system is significantly enlarged compared to the unprotonated C10—N2—C11 [117.80 (17)°] bond angle, which is consistent with previous studies, e.g., Hensen et al. (2000 ) and Büyükekşi et al. (2019 ). The N1—C1 [1.322 (3) Å] and N1—C12 [1.353 (2) Å] bond lengths of the protonated N1 atom are similar to the N2—C10 [1.336 (2) Å] and N2—C11 [1.345 (2) Å] bonds of the non-protonated N2 atom. In the pendant dimethylamino group, the N3—C10 [1.357 (3) Å] bond length is significantly shorter than N3—C13 [1.453 (3) Å] and N3—C14 [1.444 (3) Å] bonds, presumably because of resonance-assisted π-conjugation, where the N atom of the dimethylamino group acts as a strong electron donor to the aromatic ring system. On the other hand, the C10—N3—C13 [123.3 (2)°] and C14—N3—C13 [115.69 (19)°] bond angles are significantly enlarged and narrowed according to the bond angle of C10—N3—C14 [120.86 (18)°], respectively. In the nitrate counter-ion, the N4—O3 [1.204 (3) Å] bond is significantly shorter than N4—O1 [1.251 (3) Å] and N4—O2 [1.245 (3) Å], possibly due to hydrogen bonding and crystal packing effects, where O1 acts as hydrogen-bond acceptor interacting with the protonated N1 atom of the phenanthroline ring system. The O2—N4—O1 [117.5 (2)°] bond angle is significantly narrower than O3—N4—O1 [120.6 (3)°] and O3—N4—O2 [121.8 (3)°].

Figure 1
The molecular structure of (I) with 50% probability ellipsoids. The N—H⋯O hydrogen bond is shown as a dashed line.

3. Supramolecular features

In the extended structure, the N1—H1⋯O1 hydrogen bond (Table 1) links the cation to the anion (Fig. 2) and a C5—H5⋯O3 hydrogen bond (Table 2) links the ion pairs into infinite chains propagating along the b-axis direction (Fig. 2). Further, π–π stacking interactions between the A (N1/C1–C4/C12) and B (N2/C7–C11) rings and also between the B and C (C4–C12) rings of the phenanthroline ring system with centroid–to–centroid distances of 3.5773 (12) Å [α = 1.34 (10)° and slippage = 1.212 Å] and 3.5889 (12) Å [α = 0.84 (9)° and slippage = 1.198 Å], respectively, help to consolidate the packing. No C—H⋯π(ring) interactions are observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86 (1)	2.04 (2)	2.819 (3)	150 (3)
C5—H5⋯O3ⁱ	0.93	2.55	3.407 (3)	154
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₃⁺·NO₃⁻
M_r	286.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.7438 (3), 19.8224 (7), 9.8185 (4)
β (°)	94.762 (3)
V (Å³)	1307.99 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.88
Crystal size (mm)	0.2 × 0.16 × 0.14

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix-Bantam
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2026 )
T_min, T_max	0.243, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12223, 2527, 1881
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.184, 1.07
No. of reflections	2527
No. of parameters	196
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2026), SHELXT (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Figure 2
Packing diagram of (I) showing N—H⋯O and C—H⋯O hydrogen bonds as dashed lines with the infinite chains propagating along the b-axis direction.

The intermolecular interactions in the crystal were visualized by carrying out the Hirshfeld surface (HS) analysis using CrystalExplorer 17.5 (Spackman et al., 2021 ). Fig. 3 shows the Hirshfeld surface with the red spots corresponding to the hydrogen-bond donors and acceptors noted above. The overall two-dimensional fingerprint plot is shown in Fig. 4a and those delineated into the different contact types are illustrated in Fig. 4 (b)–(h), respectively. According to the two-dimensional fingerprint plots the H⋯H, H⋯O/O⋯H, H⋯C/C⋯H and C⋯C contacts make the most significant contributions to the HS, at 39.2%, 31.6%, 10.3% and 9.1%, respectively.

Figure 3
View of the three-dimensional Hirshfeld surface for (I) plotted over d_norm in the range −0.54 to 1.08 a.u.

Figure 4
Two-dimensional fingerprint plots for (I), showing (a) all interactions, and delineated (b)–(f) into different contact types. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.45, updated September 2024; Groom et al., 2016 ) identified eight compounds with close structural similarity to (I). These include: 1,10-phenanthrolin-1-ium-6-sulfonate hydrogen peroxide, C₁₂H₈N₂O₃S·H₂O₂ (CSD refcode BIPZUZ; Bezzubov et al., 2023 ), 1,10-phenanthrolin-1-ium chloride, C₁₂H₉N₂⁺·Cl⁻ (CUZDIK; Hensen et al., 2000), 2,9-dimethyl-1,10-phenanthrolin-1-ium picrate, C₆H₂N₃O₇⁻·C₁₄H₁₃N₂⁺ (CIYPIL; Chan et al., 2014 ), 6-ethynyl-1,10-phenanthrolin-1-ium trifluoromethanesulfonate, CF₃O₃S⁻·C₁₄H₉N₂⁺ (DILPIA; Doistau et al., 2018 ), 2-amino-1,10-phenanthrolin-1-ium chloride, C₁₂H₁₀N₃⁺·Cl⁻ (LUZZAL; Büyükekşi et al., 2019), 9-phenyl-1,10-phenanthrolin-1-ium trifluoromethanesulfonate, C₁₈H₁₃N₂⁺·CF₃SO₃⁻ (NIYSUL; Krause et al., 2014 ), 9-phenyl-1,10-phenanthrolin-1-ium tetrachlorogold(III), C₁₈H₁₃N₂·AuCl₄ (NIYTAS; Krause et al., 2014) and 1,10-phenanthrolin-1-ium tetrafluoroborate, C₁₂H₉N₂⁺·BF₄⁻ (WUJWUX; Ghorai et al., 2024 ).

5. Synthesis and crystallization

2-Bromo-1,10-phenanthroline (2.59 g, 10 mmol) and Cs₂CO₃ (3.25 g, 10 mmol) were dissolved in N,N-dimethylformide (DMF) (75 ml), and the resulting mixture was heated with stirring at 413 K for 6 h (Fig. 5). After completion of the reaction, the solvent was removed under reduced pressure. The residue was washed with ethyl acetate and water. The neutral molecule was isolated from the ethyl acetate fraction after concentration, giving a yield of 60%. An equimolar amount of 1 M aqueous HNO₃ was added dropwise, with stirring, to an ethanolic solution and the resulting solution was left to crystallize at room temperature. Colorless crystals of (I) were obtained after 6 days. Yield: 65%. Analysis (%) for C₁₄H₁₄N₄O₃, calculated (obtained): C 58.74 (58.70), H 4.93 (4.89), N 19.57 (19.52). ¹H NMR (400 MHz, DMSO-d₆, ppm): δ 3.19 (6H, NMe₂), 7.57–9.20 (7H). ¹³C{¹H} NMR (100 MHz, DMSO-d₆, ppm): δ 42.3, 111.7, 122.7, 123.8, 125.5, 126.9, 128.4, 138.2, 143.5, 144.9, 146.1, 150.4, 157.3.

Figure 5
Synthesis of (I).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N-bound H atom was located from a difference-Fourier map and refined isotropically. The C-bound H-atom positions were calculated geometrically at distances of 0.93–0.96 Å and refined using a riding model by applying the constraint U_iso(H) = k × U_eq (C), where k = 1.2 for aromatic CH hydrogen atoms and k = 1.5 for methyl hydrogen atoms.

Supporting information

CCDC reference: 2566614

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989026006882/hb8230sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026006882/hb8230Isup2.hkl

checkCIF report

Computing details top

9-(Dimethylamino)-1,10-phenanthrolin-1-ium nitrate top

Crystal data top

C₁₄H₁₄N₃⁺·NO₃⁻	F(000) = 600
M_r = 286.29	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.7438 (3) Å	Cell parameters from 4514 reflections
b = 19.8224 (7) Å	θ = 4.5–71.4°
c = 9.8185 (4) Å	µ = 0.88 mm⁻¹
β = 94.762 (3)°	T = 293 K
V = 1307.99 (9) Å³	Block, colorless
Z = 4	0.2 × 0.16 × 0.14 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix-Bantam diffractometer	2527 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1881 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.6°, θ_min = 4.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2026)	k = −22→24
T_min = 0.243, T_max = 1.000	l = −12→12
12223 measured reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.1045P)² + 0.2504P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2527 reflections	Δρ_max = 0.25 e Å⁻³
196 parameters	Δρ_min = −0.20 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
O1	0.5907 (4)	0.61057 (11)	0.1377 (2)	0.0922 (7)
O2	0.8825 (4)	0.60068 (15)	0.0709 (3)	0.1135 (8)
O3	0.7228 (5)	0.69350 (10)	0.0406 (3)	0.1222 (10)
N4	0.7340 (4)	0.63673 (11)	0.0841 (2)	0.0707 (6)
N1	0.7044 (3)	0.48753 (9)	0.26544 (17)	0.0469 (4)
N2	0.7379 (2)	0.57058 (8)	0.48756 (17)	0.0441 (4)
N3	0.7401 (3)	0.67846 (9)	0.5727 (2)	0.0595 (5)
C1	0.6868 (4)	0.45120 (12)	0.1522 (2)	0.0575 (6)
H1A	0.668242	0.472441	0.067649	0.069*
C2	0.6959 (4)	0.38109 (12)	0.1595 (3)	0.0637 (6)
H2	0.683511	0.355146	0.080373	0.076*
C3	0.7233 (3)	0.35116 (11)	0.2844 (3)	0.0574 (6)
H3	0.729509	0.304362	0.289935	0.069*
C4	0.7424 (3)	0.38943 (10)	0.4051 (2)	0.0469 (5)
C5	0.7720 (3)	0.36087 (11)	0.5380 (3)	0.0556 (6)
H5	0.778823	0.314270	0.548464	0.067*
C6	0.7903 (3)	0.40108 (11)	0.6490 (2)	0.0553 (6)
H6	0.809475	0.381530	0.735149	0.066*
C7	0.7810 (3)	0.47261 (10)	0.6381 (2)	0.0459 (5)
C8	0.8034 (3)	0.51706 (11)	0.7505 (2)	0.0509 (5)
H8	0.826659	0.499836	0.838442	0.061*
C9	0.7912 (3)	0.58476 (11)	0.7312 (2)	0.0518 (5)
H9	0.805535	0.613818	0.805706	0.062*
C10	0.7564 (3)	0.61119 (10)	0.5964 (2)	0.0444 (5)
C11	0.7504 (3)	0.50365 (9)	0.50939 (19)	0.0395 (4)
C12	0.7314 (3)	0.46029 (9)	0.39193 (19)	0.0423 (5)
C13	0.7615 (5)	0.72889 (12)	0.6803 (3)	0.0765 (8)
H13A	0.758735	0.707236	0.767585	0.115*
H13B	0.654123	0.760685	0.668229	0.115*
H13C	0.885878	0.752077	0.676224	0.115*
C14	0.7127 (4)	0.70437 (12)	0.4350 (3)	0.0714 (7)
H14A	0.838078	0.719632	0.406935	0.107*
H14B	0.620567	0.741374	0.431959	0.107*
H14C	0.661062	0.669325	0.374545	0.107*
H1	0.693 (4)	0.5304 (6)	0.254 (3)	0.074 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1127 (17)	0.0782 (13)	0.0871 (14)	0.0041 (12)	0.0165 (13)	0.0218 (11)
O2	0.1078 (18)	0.129 (2)	0.1037 (18)	0.0283 (16)	0.0054 (14)	0.0172 (15)
O3	0.195 (3)	0.0546 (12)	0.1178 (19)	−0.0092 (14)	0.0194 (18)	0.0274 (12)
N4	0.1038 (18)	0.0568 (12)	0.0496 (11)	0.0007 (12)	−0.0039 (11)	0.0033 (9)
N1	0.0551 (10)	0.0411 (9)	0.0444 (9)	0.0024 (8)	0.0039 (7)	−0.0003 (7)
N2	0.0478 (9)	0.0373 (9)	0.0474 (9)	−0.0018 (7)	0.0061 (7)	0.0013 (7)
N3	0.0833 (14)	0.0369 (9)	0.0583 (11)	−0.0038 (9)	0.0051 (9)	−0.0057 (8)
C1	0.0674 (14)	0.0557 (13)	0.0488 (12)	0.0032 (11)	0.0023 (10)	−0.0064 (9)
C2	0.0729 (16)	0.0556 (13)	0.0621 (14)	0.0023 (11)	0.0029 (11)	−0.0181 (11)
C3	0.0615 (14)	0.0402 (11)	0.0711 (15)	0.0010 (9)	0.0082 (11)	−0.0092 (10)
C4	0.0445 (11)	0.0392 (10)	0.0581 (12)	−0.0008 (8)	0.0101 (9)	−0.0009 (9)
C5	0.0624 (13)	0.0371 (10)	0.0684 (14)	0.0015 (9)	0.0120 (11)	0.0092 (10)
C6	0.0651 (14)	0.0461 (11)	0.0553 (12)	0.0026 (10)	0.0094 (10)	0.0135 (10)
C7	0.0466 (11)	0.0448 (11)	0.0472 (11)	0.0005 (8)	0.0099 (8)	0.0060 (8)
C8	0.0570 (12)	0.0553 (12)	0.0408 (10)	0.0021 (10)	0.0074 (8)	0.0055 (9)
C9	0.0561 (13)	0.0545 (12)	0.0454 (11)	−0.0035 (10)	0.0082 (9)	−0.0097 (9)
C10	0.0439 (10)	0.0402 (10)	0.0495 (11)	−0.0039 (8)	0.0068 (8)	−0.0029 (8)
C11	0.0378 (10)	0.0360 (9)	0.0451 (10)	−0.0011 (7)	0.0063 (7)	0.0020 (8)
C12	0.0399 (10)	0.0399 (11)	0.0477 (11)	0.0000 (8)	0.0073 (8)	0.0007 (8)
C13	0.102 (2)	0.0454 (13)	0.0827 (18)	−0.0057 (13)	0.0089 (15)	−0.0187 (12)
C14	0.0960 (19)	0.0424 (12)	0.0753 (16)	0.0012 (12)	0.0042 (14)	0.0082 (11)

Geometric parameters (Å, º) top

O1—N4	1.251 (3)	C4—C12	1.412 (3)
O2—N4	1.245 (3)	C5—H5	0.9300
O3—N4	1.204 (3)	C5—C6	1.347 (3)
N1—C1	1.322 (3)	C6—H6	0.9300
N1—C12	1.353 (2)	C6—C7	1.423 (3)
N1—H1	0.861 (10)	C7—C8	1.410 (3)
N2—C10	1.336 (2)	C7—C11	1.405 (3)
N2—C11	1.345 (2)	C8—H8	0.9300
N3—C10	1.357 (3)	C8—C9	1.357 (3)
N3—C13	1.453 (3)	C9—H9	0.9300
N3—C14	1.444 (3)	C9—C10	1.424 (3)
C1—H1A	0.9300	C11—C12	1.435 (3)
C1—C2	1.393 (3)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C2—C3	1.361 (4)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C3—C4	1.404 (3)	C14—H14B	0.9600
C4—C5	1.421 (3)	C14—H14C	0.9600

O2—N4—O1	117.5 (2)	C11—C7—C6	120.40 (19)
O3—N4—O1	120.6 (3)	C11—C7—C8	115.35 (18)
O3—N4—O2	121.8 (3)	C7—C8—H8	119.8
C1—N1—C12	123.41 (18)	C9—C8—C7	120.49 (19)
C1—N1—H1	115.1 (19)	C9—C8—H8	119.8
C12—N1—H1	121.4 (19)	C8—C9—H9	120.1
C10—N2—C11	117.80 (17)	C8—C9—C10	119.80 (19)
C10—N3—C13	123.3 (2)	C10—C9—H9	120.1
C10—N3—C14	120.86 (18)	N2—C10—N3	117.00 (18)
C14—N3—C13	115.69 (19)	N2—C10—C9	121.26 (18)
N1—C1—H1A	120.0	N3—C10—C9	121.74 (18)
N1—C1—C2	120.0 (2)	N2—C11—C7	125.28 (17)
C2—C1—H1A	120.0	N2—C11—C12	117.53 (16)
C1—C2—H2	120.5	C7—C11—C12	117.19 (17)
C3—C2—C1	118.9 (2)	N1—C12—C4	118.91 (17)
C3—C2—H2	120.5	N1—C12—C11	119.66 (17)
C2—C3—H3	119.3	C4—C12—C11	121.42 (17)
C2—C3—C4	121.4 (2)	N3—C13—H13A	109.5
C4—C3—H3	119.3	N3—C13—H13B	109.5
C3—C4—C5	123.77 (19)	N3—C13—H13C	109.5
C3—C4—C12	117.35 (19)	H13A—C13—H13B	109.5
C12—C4—C5	118.88 (19)	H13A—C13—H13C	109.5
C4—C5—H5	119.9	H13B—C13—H13C	109.5
C6—C5—C4	120.20 (19)	N3—C14—H14A	109.5
C6—C5—H5	119.9	N3—C14—H14B	109.5
C5—C6—H6	119.0	N3—C14—H14C	109.5
C5—C6—C7	121.9 (2)	H14A—C14—H14B	109.5
C7—C6—H6	119.0	H14A—C14—H14C	109.5
C8—C7—C6	124.24 (19)	H14B—C14—H14C	109.5

N1—C1—C2—C3	−0.1 (4)	C7—C8—C9—C10	−0.3 (3)
N2—C11—C12—N1	0.7 (3)	C7—C11—C12—N1	−179.14 (17)
N2—C11—C12—C4	−179.94 (17)	C7—C11—C12—C4	0.2 (3)
C1—N1—C12—C4	0.2 (3)	C8—C7—C11—N2	−1.2 (3)
C1—N1—C12—C11	179.61 (19)	C8—C7—C11—C12	178.60 (17)
C1—C2—C3—C4	0.0 (4)	C8—C9—C10—N2	−0.9 (3)
C2—C3—C4—C5	−179.7 (2)	C8—C9—C10—N3	179.0 (2)
C2—C3—C4—C12	0.2 (3)	C10—N2—C11—C7	0.1 (3)
C3—C4—C5—C6	179.6 (2)	C10—N2—C11—C12	−179.69 (16)
C3—C4—C12—N1	−0.3 (3)	C11—N2—C10—N3	−178.92 (18)
C3—C4—C12—C11	−179.66 (18)	C11—N2—C10—C9	1.0 (3)
C4—C5—C6—C7	0.0 (3)	C11—C7—C8—C9	1.2 (3)
C5—C4—C12—N1	179.62 (18)	C12—N1—C1—C2	−0.1 (3)
C5—C4—C12—C11	0.3 (3)	C12—C4—C5—C6	−0.4 (3)
C5—C6—C7—C8	−178.6 (2)	C13—N3—C10—N2	−178.5 (2)
C5—C6—C7—C11	0.5 (3)	C13—N3—C10—C9	1.6 (3)
C6—C7—C8—C9	−179.6 (2)	C14—N3—C10—N2	−2.6 (3)
C6—C7—C11—N2	179.55 (18)	C14—N3—C10—C9	177.5 (2)
C6—C7—C11—C12	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (1)	2.04 (2)	2.819 (3)	150 (3)
C5—H5···O3ⁱ	0.93	2.55	3.407 (3)	154

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

This work has been supported by the Azerbaijan Medical University and Baku Engineering University. TH is also grateful to Hacettepe University Scientific Research Project Unit. This research was conducted at the Laboratory of Complex Compounds, Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan. It was financially supported by government funding from the Republic of Uzbekistan. The authors' contributions are as follows. Conceptualization, TH and ANB; synthesis, MA and JA; X-ray analysis, BT, JA and TH; Hirshfeld surface analysis, TH; writing (review and editing of the manuscript) TH, NAG and KIH; supervision, TH and ANB.

Funding information

The following funding is acknowledged: Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004 to Tuncer Hökelek).

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