Synthesis and structure of 5-[(4-fluoro­benz­yl)amino]­isophthalic acid featuring O—H⋯O and N—H⋯π inter­actions

Gurbanov, A.V.; Akkurt, M.; Karmakar, A.; Manahelohe, G.M.

doi:10.1107/S205698902600959X

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ISSN: 2056-9890

Volume 82| Part 10| October 2026| Pages 1201-1204

https://doi.org/10.1107/S205698902600959X

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Synthesis and structure of 5-[(4-fluorobenzyl)amino]isophthalic acid featuring O—H⋯O and N—H⋯π interactions

Atash V. Gurbanov,^a Mehmet Akkurt,^b Anirban Karmakar ^c and Gizachew Mulugeta Manahelohe ^d ^*

^aExcellence Center, Baku State University, Z. Khalilov Str. 33, AZ 1148, Baku, Azerbaijan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^cCentro de Estudos de Engenharia Química, Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, 1959-007 Lisboa, Portugal, and ^dDepartment of Chemistry, University of Gondar, PO Box 196, Gondar, Ethiopia
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 1 September 2026; accepted 14 September 2026; online 25 September 2026)

In the title compound, C₁₅H₁₂FNO₄, the dihedral angle between the aromatic rings is 77.78 (8)°. In the crystal, the molecules are linked into zigzag ribbons propagating along the [210] direction by pairwise O—H⋯O hydrogen bonds through their two carboxylic acid groups to generate centrosymmetric R²₂(8) dimers in each case. In addition, molecules are connected via pairwise N—H⋯π interactions between the NH groups and the fluorobenzene rings. Aromatic π–π stacking interactions and weak C—H⋯F and C—H⋯O interactions also contribute to the packing. A Hirshfeld surface analysis shows that the most important contributions to the crystal packing are from H⋯H (30.7%), O⋯H/H⋯O (26.1%) and C⋯H/H⋯C (20.3%) contacts.

Keywords: crystal structure; carboxylic acid homodimers; Hirshfeld surface analysis.

CCDC reference: 2587990

1. Chemical context

Metal–organic frameworks (MOFs) are highly porous crystalline materials built from metal ions connected by organic ligands (Chughtai et al., 2015 ; Liu et al., 2014 ). The functional properties of MOFs can be improved by the design of organic ligands (carboxylates, sulfonates, phosphonates, etc.) and the variation of metal centres. 5-Aminoisophthalic acid and its derivatives have already been used in the synthesis and design of MOFs (Karmakar et al., 2024 ). In order to generate an additional coordination centre and a non-covalent bond donor or acceptor site, 5-aminoisophthalic acid has been functionalized by introducing hydrazone, amide, azo, etc. onto its backbone (Aliyeva et al., 2026 ). For example, halogen-bonded hydrazones of 5-amino-2,4,6-tribromoisophthalic acid were employed in the construction of new MOFs and applied in the Henry reaction of aldehydes with nitroalkanes (Gurbanov et al., 2022 ) as well as in the coupling of CO₂ with epoxides (Aliyeva et al., 2023 ). As a continuation of our research work in this direction, we now describe the synthesis and structure of the title compound, C₁₅H₁₂FNO₄ (I).

2. Structural commentary

Compound (I) crystallizes in the triclinic space group P $[\overline{1}]$ with one molecule in the asymmetric unit (Fig. 1). The dihedral angle between the planes of the benzene-1,3-dicarboxylic acid (C1–C6) and fluorophenyl (C8–C13) rings is 77.78 (8)°. The sum of the bond angles around N1 is 358.7°, implying sp² hybridization; the unhybridized 2p orbital is well aligned to interact with the π system of the C1–C6 ring, which may result in partial double-bond character for the C1—N1 bond [1.3728 (19) Å]. The C14/O1/O2 and C15/O3/O4 carboxylic acid groups are almost coplanar with their attached ring [dihedral angles = 3.83 (19) and 6.7 (3)°, respectively].

Figure 1
The molecular structure of (I)

with displacement ellipsoids drawn at the 50% probability level.

The C8—C7—N1 bond angle of 115.64 (13)° for the bridging methylene group deviates significantly from the nominal tetrahedral value of 109.5° possibly due to steric crowding. The torsion angles of the C2—C1—N1—C7, C1—N1—C7—C8 and N1—C7—C8—C13 groupings are 164.21 (15), 89.38 (19) and 173.68 (14)°, respectively. A short intramolecular C—H⋯N contact (Table 1) is observed. Otherwise, all geometric parameters for (I) are normal and consistent with those of related compounds listed in the Database survey.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1	0.96 (1)	2.52 (1)	2.890 (2)	103 (1)
O1—H1O⋯O2ⁱ	0.86 (1)	1.77 (1)	2.6326 (16)	177 (2)
O4—H4O⋯O3ⁱⁱ	0.87 (1)	1.79 (1)	2.6518 (15)	176 (2)
N1—H1N⋯Cg2ⁱⁱⁱ	0.87 (1)	2.71 (2)	3.4071 (17)	139 (2)
C12—H12⋯F1^iv	0.96 (1)	2.46 (1)	3.2661 (19)	142 (1)
C12—H12⋯O3^v	0.96 (1)	2.65 (2)	3.298 (2)	126 (1)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

3. Supramolecular features and Hirshfeld surface analysis

In the extended structure of (I), the molecules are connected into zigzag ribbons propagating along the [210] direction by two centrosymmetric R₂²(8) dimers formed from pairwise O—H⋯O hydrogen bonds involving both their carboxylic acid groups (Fig. 2, Table 1). Furthermore, molecules are linked by pairwise N—H⋯π interactions between the NH groups and fluorobenzene rings (Fig. 3, Table 1). Simultaneously, the molecules are linked by weak π–π stacking interactions [Cg1⋯Cg1^a = 3.9798 (10) Å, shift = 2.081 Å; symmetry code (a) 1 − x, 1 − y, −z; Cg1 is the centroid of the C1–C6 benzene ring], generating ribbons propagating along the [011] direction (Fig. 3, Table 1). Finally, weak C—H⋯F and C—H⋯O interactions between these ribbons may help to consolidate the packing.

Figure 2
A partial view of the R₂²(8) motif dimers formed by pairwise O—H⋯O hydrogen bonds in the extended structure. Symmetry codes: (a) −x, −y, −z; (b) −x + 2, −y + 1, −z.

Figure 3
A partial view of the N—H⋯π and π–π interactions in the extended structure. Symmetry codes: (c) −x + 1, −y + 1, −z; (d) −x + 1, −y + 2, −z + 1.

A Hirshfeld surface analysis was carried out to further investigate the intermolecular interactions using Crystal Explorer 21 (Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm is illustrated in Fig. 4. The red spots on the Hirshfeld surface plot indicate the directional interactions noted above. The two-dimensional fingerprint plots are shown in Fig. 5: H⋯H (30.7%), O⋯H/H⋯O (26.1%) and C⋯H/H⋯C (20.3%) contacts are the main contributors to the crystal packing. Minor contributions are from F⋯H/H⋯F (7.5%), O⋯C/C⋯O (4.4%), C⋯C (4.0%), F⋯C/C⋯F (2.7%), F⋯O/O⋯F (2.3%), O⋯O (1.1%), N⋯C/C⋯N (0.6%) and F⋯F (0.3%) contacts.

Figure 4
Three-dimensional Hirshfeld surface of (I)

mapped over d_norm.

Figure 5
The two-dimensional fingerprint plots for (I)

showing (a) all interactions, and (b)–(d) the different contact types.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 6.00, update of April 2025; Groom et al., 2016 ) found that the most closely related structures to the title compound are N-benzylaniline (CSD refcode UREJOR: Betz et al., 2011 ), N-benzyl-3-nitroaniline (YAHDIW: Stilinović & Portada, 2011 ) and N-[3,5-bis(trifluoromethyl)phenyl]-1-(2-bromophenyl)methanimine (AKISIA: Kingsley et al., 2025 ).

In UREJOR, the N atom is present in a nearly planar molecular geometry (angle sums at the N atom are 358 and 359° in the two molecules of the asymmetric unit). The planes defined by the aromatic rings intersect at angles of 80.76 (4) and 81.40 (4)° in the two molecules. In the crystal, N—H⋯π interactions connect the two molecules of the asymmetric unit to form infinite homodromic chains propagating along the b axis direction [N⋯π = 3.4782 (12) and 3.4642 (13) Å].

In YAHDIW, the N–methyl–3–nitroaniline system is almost planar and the dihedral angle between the ring planes is 86.0 (6)°. In the crystal, the molecules are connected via strong N—H⋯O and weak C—H⋯O hydrogen bonds into chains propagating along [101].

In AKISIA, the imine grouping is nearly coplanar with the 2-bromophenyl group, while the N-[3,5-bis(trifluoromethyl)phenyl] moiety is significantly twisted from the imine group [49.61 (5)°]. The imine bond length C7—N1 [1.280 (4) Å] and C7—N1—C8 bond angle [119.1 (2)°] are consistent with atom N1 being sp² hybridized as in (I). The angle between the least-squares planes formed by C1–C8/N1/Br1 and C8–C15/N1 of 49.61 (5)° is consistent with steric effects involving H7 and H9. The crystal packing involves short C—H⋯Br contacts generating zigzag ribbons flanked by fluorine-rich layers.

5. Synthesis and crystallization

A mixture of 5-aminoisophthalic acid (1.08 g, 6 mmol) and 4-fluorobenzaldehyde (0.992 mg, 8.0 mmol), in ethanol (95%, 30 ml) was stirred at room temperature. Triethylamine (4.16 ml, 30 mmol) was added to the mixture and stirred for 1 h. The mixture became viscous, then an excess of NaBH₄ (2 equivalents relative to the imine) was slowly added at 273 K. After 4 h at 273 K, the solvent was removed under vacuum. The residue was dissolved in water (50 ml) and acidified with glacial acetic acid (AcOH) to pH 3–5. After filtration, the product was obtained as a pale-yellowish crystalline solid. Single crystals of (I) were recrystallized from a methanol solution at room temperature. Yield: 71%. Analysis calculated for C₁₅H₁₂FNO₄: C 62.28; H 4.18; N 4.84; found: C 62.26; H 4.15; N 4.81%. ¹H NMR (DMSO-d₆) δ 13.20 (br s, 2H, –COOH), 7.81 (s, 1H, Ar), 7.76 (s, 2H, Ar), 7.33 and 7.30 (m, 2H, J = 12.0 Hz, Ar), 6.96 and 6.93 (m, 2H, J = 12.0 Hz, Ar), 6.75 (s, 1H, NH), 4.62 (d, 2H, CH₂). ¹³C NMR (DMSO-d₆) δ 161.2, 161.1, 156.7, 144.1, 139.0, 129.2, 127.2, 127.1, 115.3, 113.4, 46.7.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All hydrogen atoms were found from difference-Fourier maps. Hydroxyl group H atoms wererefined with U_iso(H) = 1.5U_eq(O), while other H atoms were refined freely. The restraints O—H = 0.85 (1) Å for the OH group, N—H = 0.86 (1) Å for the NH group, C—H = 0.99 Å for the CH₂ group, and C—H = 0.95 Å for the CH group were applied using the DFIX command.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₂FNO₄
M_r	289.26
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	8.4674 (9), 9.2193 (11), 9.2749 (11)
α, β, γ (°)	102.838 (4), 96.181 (4), 108.027 (4)
V (Å³)	659.01 (13)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.35 × 0.30 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.954, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	8198, 2722, 2050
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.05
No. of reflections	2722
No. of parameters	236
No. of restraints	12
H-atom treatment	Only H-atom coordinates refined
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26
Computer programs: APEX4 and SAINT (Bruker, 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2587990

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902600959X/hb8253sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902600959X/hb8253Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902600959X/hb8253Isup3.cml

checkCIF report

Computing details top

5-{[(4-Fluorophenyl)methyl]amino}benzene-1,3-dicarboxylic acid top

Crystal data top

C₁₅H₁₂FNO₄	Z = 2
M_r = 289.26	F(000) = 300
Triclinic, P1	D_x = 1.458 Mg m⁻³
a = 8.4674 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2193 (11) Å	Cell parameters from 2691 reflections
c = 9.2749 (11) Å	θ = 2.3–26.4°
α = 102.838 (4)°	µ = 0.12 mm⁻¹
β = 96.181 (4)°	T = 150 K
γ = 108.027 (4)°	Prism, yellow
V = 659.01 (13) Å³	0.35 × 0.30 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	2050 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.036
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.5°, θ_min = 2.3°
T_min = 0.954, T_max = 0.966	h = −10→9
8198 measured reflections	k = −10→11
2722 independent reflections	l = −9→11

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.102	Only H-atom coordinates refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0457P)² + 0.1305P] where P = (F_o² + 2F_c²)/3
2722 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.24 e Å⁻³
12 restraints	Δρ_min = −0.26 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
F1	0.90425 (13)	1.37822 (11)	0.33763 (12)	0.0396 (3)
O1	0.06367 (14)	0.18670 (14)	0.13695 (15)	0.0393 (3)
H1O	−0.021 (2)	0.1019 (17)	0.093 (2)	0.059*
O2	0.20181 (15)	0.07050 (14)	−0.01296 (16)	0.0469 (4)
O3	0.92015 (12)	0.60399 (12)	0.11820 (12)	0.0242 (3)
O4	0.79097 (13)	0.35250 (12)	−0.01900 (13)	0.0272 (3)
H4O	0.8879 (15)	0.370 (2)	−0.048 (2)	0.041*
N1	0.49379 (17)	0.70687 (15)	0.43757 (16)	0.0280 (3)
H1N	0.4006 (16)	0.700 (2)	0.470 (2)	0.043 (6)*
C1	0.49554 (18)	0.58645 (17)	0.32082 (17)	0.0210 (3)
C2	0.34918 (19)	0.45235 (17)	0.25993 (18)	0.0213 (3)
H2	0.2474 (14)	0.4463 (18)	0.2968 (17)	0.024 (4)*
C3	0.35070 (18)	0.32787 (17)	0.14517 (17)	0.0201 (3)
C4	0.49641 (18)	0.33361 (17)	0.08617 (17)	0.0195 (3)
H4	0.4986 (18)	0.2491 (14)	0.0081 (14)	0.021 (4)*
C5	0.63955 (17)	0.46746 (16)	0.14245 (16)	0.0182 (3)
C6	0.63946 (18)	0.59342 (17)	0.25752 (17)	0.0200 (3)
H6	0.7376 (14)	0.6865 (13)	0.2898 (16)	0.017 (4)*
C7	0.6451 (2)	0.82871 (18)	0.53084 (18)	0.0255 (4)
H7A	0.7382 (16)	0.7843 (17)	0.5426 (18)	0.027 (4)*
H7B	0.623 (2)	0.8617 (19)	0.6336 (12)	0.029 (4)*
C8	0.71148 (19)	0.97471 (17)	0.47556 (17)	0.0227 (4)
C9	0.6414 (2)	0.98566 (18)	0.33749 (18)	0.0269 (4)
H9	0.5464 (16)	0.8975 (15)	0.2762 (17)	0.034 (5)*
C10	0.7055 (2)	1.12091 (19)	0.28966 (19)	0.0294 (4)
H10	0.660 (2)	1.128 (2)	0.1941 (14)	0.039 (5)*
C11	0.8393 (2)	1.24435 (18)	0.38301 (19)	0.0271 (4)
C12	0.9112 (2)	1.23975 (19)	0.5208 (2)	0.0306 (4)
H12	0.9998 (18)	1.3310 (15)	0.5851 (18)	0.042 (5)*
C13	0.8465 (2)	1.10370 (19)	0.5663 (2)	0.0295 (4)
H13	0.8931 (19)	1.0945 (19)	0.6609 (13)	0.029 (4)*
C14	0.19642 (19)	0.18422 (18)	0.08348 (18)	0.0242 (4)
C15	0.79660 (18)	0.48153 (17)	0.08001 (17)	0.0199 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0492 (6)	0.0294 (5)	0.0471 (7)	0.0152 (5)	0.0171 (5)	0.0177 (5)
O1	0.0181 (6)	0.0352 (7)	0.0475 (8)	−0.0046 (5)	0.0140 (6)	−0.0065 (6)
O2	0.0265 (7)	0.0311 (7)	0.0608 (9)	−0.0037 (5)	0.0170 (6)	−0.0162 (6)
O3	0.0163 (5)	0.0229 (5)	0.0279 (6)	0.0021 (4)	0.0077 (5)	0.0014 (5)
O4	0.0176 (6)	0.0246 (6)	0.0345 (7)	0.0044 (5)	0.0115 (5)	−0.0007 (5)
N1	0.0193 (7)	0.0247 (7)	0.0337 (8)	0.0037 (6)	0.0118 (6)	−0.0019 (6)
C1	0.0198 (8)	0.0203 (7)	0.0237 (8)	0.0071 (6)	0.0070 (6)	0.0062 (6)
C2	0.0158 (8)	0.0234 (8)	0.0263 (8)	0.0059 (6)	0.0096 (6)	0.0082 (6)
C3	0.0158 (7)	0.0199 (7)	0.0235 (8)	0.0034 (6)	0.0041 (6)	0.0077 (6)
C4	0.0189 (8)	0.0188 (7)	0.0204 (8)	0.0062 (6)	0.0048 (6)	0.0041 (6)
C5	0.0152 (7)	0.0211 (7)	0.0203 (8)	0.0068 (6)	0.0044 (6)	0.0083 (6)
C6	0.0152 (7)	0.0189 (7)	0.0235 (8)	0.0028 (6)	0.0035 (6)	0.0052 (6)
C7	0.0259 (9)	0.0250 (8)	0.0222 (8)	0.0072 (7)	0.0059 (7)	0.0012 (7)
C8	0.0219 (8)	0.0244 (8)	0.0225 (8)	0.0099 (6)	0.0076 (6)	0.0031 (6)
C9	0.0281 (9)	0.0257 (8)	0.0229 (9)	0.0095 (7)	0.0026 (7)	−0.0010 (7)
C10	0.0382 (10)	0.0307 (9)	0.0219 (9)	0.0178 (8)	0.0051 (7)	0.0043 (7)
C11	0.0317 (9)	0.0237 (8)	0.0330 (9)	0.0140 (7)	0.0148 (8)	0.0109 (7)
C12	0.0235 (9)	0.0245 (8)	0.0382 (10)	0.0046 (7)	0.0004 (7)	0.0051 (7)
C13	0.0283 (9)	0.0292 (9)	0.0287 (9)	0.0090 (7)	−0.0007 (7)	0.0079 (7)
C14	0.0172 (8)	0.0250 (8)	0.0273 (9)	0.0038 (6)	0.0074 (7)	0.0043 (7)
C15	0.0176 (8)	0.0226 (8)	0.0193 (8)	0.0067 (6)	0.0034 (6)	0.0057 (6)

Geometric parameters (Å, º) top

F1—C11	1.3651 (18)	C4—H4	0.945 (9)
O1—C14	1.2809 (19)	C5—C6	1.392 (2)
O1—H1O	0.861 (10)	C5—C15	1.488 (2)
O2—C14	1.2341 (19)	C6—H6	0.953 (9)
O3—C15	1.2273 (17)	C7—C8	1.514 (2)
O4—C15	1.3156 (17)	C7—H7A	1.001 (9)
O4—H4O	0.868 (9)	C7—H7B	0.990 (9)
N1—C1	1.3728 (19)	C8—C9	1.390 (2)
N1—C7	1.4460 (19)	C8—C13	1.391 (2)
N1—H1N	0.866 (9)	C9—C10	1.387 (2)
C1—C6	1.399 (2)	C9—H9	0.961 (9)
C1—C2	1.405 (2)	C10—C11	1.371 (2)
C2—C3	1.385 (2)	C10—H10	0.952 (9)
C2—H2	0.952 (9)	C11—C12	1.371 (2)
C3—C4	1.394 (2)	C12—C13	1.382 (2)
C3—C14	1.490 (2)	C12—H12	0.958 (9)
C4—C5	1.384 (2)	C13—H13	0.955 (9)

C14—O1—H1O	111.3 (15)	C8—C7—H7B	108.6 (10)
C15—O4—H4O	108.2 (12)	H7A—C7—H7B	105.5 (14)
C1—N1—C7	123.58 (13)	C9—C8—C13	118.46 (15)
C1—N1—H1N	119.1 (13)	C9—C8—C7	122.41 (14)
C7—N1—H1N	116.0 (13)	C13—C8—C7	119.12 (14)
N1—C1—C6	121.89 (13)	C10—C9—C8	121.07 (15)
N1—C1—C2	120.03 (13)	C10—C9—H9	120.6 (10)
C6—C1—C2	118.07 (14)	C8—C9—H9	118.3 (10)
C3—C2—C1	120.61 (14)	C11—C10—C9	118.13 (15)
C3—C2—H2	119.2 (9)	C11—C10—H10	120.4 (11)
C1—C2—H2	120.2 (9)	C9—C10—H10	121.5 (11)
C2—C3—C4	120.87 (13)	F1—C11—C12	118.15 (15)
C2—C3—C14	120.43 (13)	F1—C11—C10	118.95 (15)
C4—C3—C14	118.69 (13)	C12—C11—C10	122.90 (16)
C5—C4—C3	118.82 (13)	C11—C12—C13	118.20 (15)
C5—C4—H4	119.8 (9)	C11—C12—H12	120.2 (11)
C3—C4—H4	121.4 (9)	C13—C12—H12	121.5 (11)
C4—C5—C6	120.82 (13)	C12—C13—C8	121.23 (16)
C4—C5—C15	120.91 (13)	C12—C13—H13	121.3 (10)
C6—C5—C15	118.26 (13)	C8—C13—H13	117.5 (10)
C5—C6—C1	120.73 (13)	O2—C14—O1	123.59 (14)
C5—C6—H6	118.9 (9)	O2—C14—C3	119.88 (14)
C1—C6—H6	120.3 (9)	O1—C14—C3	116.53 (13)
N1—C7—C8	115.64 (13)	O3—C15—O4	123.33 (13)
N1—C7—H7A	110.0 (9)	O3—C15—C5	122.30 (13)
C8—C7—H7A	107.8 (9)	O4—C15—C5	114.37 (12)
N1—C7—H7B	108.8 (10)

C7—N1—C1—C6	−16.8 (2)	C7—C8—C9—C10	−179.75 (14)
C7—N1—C1—C2	164.21 (15)	C8—C9—C10—C11	−0.5 (2)
N1—C1—C2—C3	−178.04 (14)	C9—C10—C11—F1	179.82 (14)
C6—C1—C2—C3	2.9 (2)	C9—C10—C11—C12	−0.3 (2)
C1—C2—C3—C4	−0.9 (2)	F1—C11—C12—C13	−179.42 (14)
C1—C2—C3—C14	178.51 (14)	C10—C11—C12—C13	0.7 (3)
C2—C3—C4—C5	−1.1 (2)	C11—C12—C13—C8	−0.3 (3)
C14—C3—C4—C5	179.50 (14)	C9—C8—C13—C12	−0.4 (2)
C3—C4—C5—C6	1.0 (2)	C7—C8—C13—C12	−179.85 (15)
C3—C4—C5—C15	−178.08 (13)	C2—C3—C14—O2	−176.06 (16)
C4—C5—C6—C1	1.1 (2)	C4—C3—C14—O2	3.3 (2)
C15—C5—C6—C1	−179.77 (13)	C2—C3—C14—O1	3.2 (2)
N1—C1—C6—C5	177.92 (14)	C4—C3—C14—O1	−177.37 (14)
C2—C1—C6—C5	−3.1 (2)	C4—C5—C15—O3	173.38 (14)
C1—N1—C7—C8	89.38 (19)	C6—C5—C15—O3	−5.7 (2)
N1—C7—C8—C9	−5.7 (2)	C4—C5—C15—O4	−6.4 (2)
N1—C7—C8—C13	173.68 (14)	C6—C5—C15—O4	174.48 (13)
C13—C8—C9—C10	0.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1	0.96 (1)	2.52 (1)	2.890 (2)	103 (1)
O1—H1O···O2ⁱ	0.86 (1)	1.77 (1)	2.6326 (16)	177 (2)
O4—H4O···O3ⁱⁱ	0.87 (1)	1.79 (1)	2.6518 (15)	176 (2)
N1—H1N···Cg2ⁱⁱⁱ	0.87 (1)	2.71 (2)	3.4071 (17)	139 (2)
C12—H12···F1^iv	0.96 (1)	2.46 (1)	3.2661 (19)	142 (1)
C12—H12···O3^v	0.96 (1)	2.65 (2)	3.298 (2)	126 (1)

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

Acknowledgements

The author's contributions are as follows. Conceptualization, AVG, MA and GMM; synthesis and X-ray analysis, AVG; writing (review and editing of the manuscript) AVG, AK and MA; funding acquisition, AVG; supervision, MA.

Funding information

This work has been supported by the Baku State University (Azerbaijan).

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