Crystal structure and Hirshfeld surface analyses, crystal voids, inter­action energy calculations and energy frameworks of (E)-2-[(pyren-1-yl­methylidene)amino]­ethanol

Eltayeb, N.E.; Hökelek, T.; Lasri, J.

doi:10.1107/S2056989025004451

research communications

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ISSN: 2056-9890

Volume 81| Part 7| July 2025| Pages 595-599

https://doi.org/10.1107/S2056989025004451

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Crystal structure and Hirshfeld surface analyses, crystal voids, interaction energy calculations and energy frameworks of (E)-2-[(pyren-1-ylmethylidene)amino]ethanol

Naser E. Eltayeb,^a,^b ^* Tuncer Hökelek ^c and Jamal Lasri ^a

^aDepartment of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, Jeddah 21589, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Khartoum 2469, Sudan, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye
^*Correspondence e-mail: [email protected]

Edited by F. F. Ferreira, Universidade Federal do ABC, Brazil (Received 23 April 2025; accepted 16 May 2025; online 10 June 2025)

The title compound, C₁₉H₁₅NO, contains a pyrene ring system, consisting of four fused benzene rings arranged in a planar configuration. In the crystal, intermolecular O—H⋯N hydrogen bonds link the molecules into infinite chains along the c-axis direction. π–π stacking interactions between the benzene rings of adjacent molecules help to consolidate the three-dimensional architecture. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (56.4%), H⋯C/C⋯H (16.6%) and C⋯C (15.8%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 76.07 Å³ and 5.79%, showing that there is no large cavity in the crystal packing. An evaluation of the electrostatic, dispersion and total energy frameworks indicates that the dispersion energy contribution is dominant while hydrogen bonding, π⋯π and van der Waals interactions are the dominant interactions in the crystal packing.

Keywords: pyrene Schiff base; Hirshfeld surface; energy framework analysis; hydrogen bond; π-stacking; crystal structure.

CCDC reference: 2452369

1. Chemical context

Schiff bases have garnered significant attention in coordination and medicinal chemistry and in materials science due to their structural versatilities, ease of syntheses, and diverse applications (Gupta & Sutar, 2008 ). The abilities of Schiff bases to act as chelating ligands by coordinating various transition-metal ions make them valuable in catalysis, bioorganic chemistry, and in the development of metallodrugs (da Silva et al., 2011 ). Additionally, their biological activities including antimicrobial (Malik et al., 2018 ) and antioxidant properties (Kumar et al., 2017 ) have made them promising candidates for pharmaceutical applications. Schiff bases also find utility in industrial processes such as corrosion inhibition (Omar et al., 1986 ), polymer stabilization (Sabaa et al., 2009 ), and as sensors for metal ion detection (Alam et al., 2023 ). Currently, our research program focuses on the syntheses and evaluations of anticancer activities of Schiff base type compounds (Lasri et al., 2018 , 2023a ,b , 2024 ; Eltayeb et al., 2020a ,b ). Herein, we report the synthesis, molecular and crystal structures, Hirshfeld surface analysis, crystal voids, interaction energies and energy frameworks of the title compound (I).

2. Structural commentary

The title compound contains a planar pyrene ring system, consisting of four fused benzene rings [A (C4–C17/C18), B (C7–C10/C18/C19), C (C10–C14/C19) and D (C14–C19)] arranged in a planar configuration (Fig. 1), where atom C3 is 0.0255 (13) Å away from the best least-squares plane of the ring system. The C2—N1—C3—C4, N1—C3—C4—C5, N1—C3—C4—C17 and O1—C1—C2—N1 torsion angles are −178.71 (11), −9.67 (19), 171.23 (12) and −61.54 (14)°, respectively. There are no unusual bond distances or inter-bond angles in the molecule.

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

3. Supramolecular features

In the crystal, intermolecular O—H⋯N hydrogen bonds (Table 1) link the molecules into infinite chains along the c-axis direction (Fig. 2). π–π stacking interactions occur between the benzene rings of adjacent molecules with the inter-centroid distances of 4.3657 (18) Å [between A rings, α = 0.02 (6)° and slippage = 2.632], 3.6343 (16) Å [between A and B rings, α = 0.05 (6)° and slippage = 1.079], 3.7953 (16) Å [between A and C rings, α = 1.90 (6)° and slippage = 1.663], 3.6538 (16) Å [between A and D rings, α = 1.10 (6)° and slippage = 1.418], 4.4161 (18) Å [between B rings, α = 0.00 (6)° and slippage = 2.727], 3.8279 (16) Å [between B and D rings, α = 0.14 (6)° and slippage = 1.609], 4.1054 (17) Å [between D rings, α = 0.00 (6)° and slippage = 2.367] and may help to consolidate the three-dimensional architecture. No C—H⋯π(ring) interactions are identified.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.853 (17)	1.997 (16)	2.8440 (18)	171.6 (14)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
A partial packing diagram viewed down the a-axis direction. Intermolecular O—H⋯N hydrogen bonds are shown as dashed lines. H atoms not involved in these interactions have been omitted for clarity.

4. Hirshfeld surface analysis

A Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ) to clarify the intermolecular interactions (Table 2) in the crystal of the title compound (I). The contact distances (Table 2) (Venkatesan et al., 2016 ) are shown in Fig. 3, where the bright-red spots correspond to the respective donors and/or acceptors; they also appear as blue and red regions in Fig. 4 corresponding to positive and negative potentials (Spackman et al., 2008 ; Jayatilaka et al., 2005 ). Fig. 5 shows only the presence of the π–π interactions in (I). According to the 2D fingerprint plots (McKinnon et al., 2007 ), the intermolecular H⋯H (Table 2), H⋯C/C⋯H and C⋯C (Table 2) contacts make important contributions to the HS of 56.4%, 16.6% and 15.8%, respectively (Fig. 6). Their contact patches are also plotted onto the surface as shown in Fig. 7, suggesting that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

Table 2
Selected interatomic distances (Å)

O1⋯N1	2.9300 (19)	H1⋯C2ⁱ	2.841 (16)
O1⋯N1ⁱ	2.8440 (18)	C3⋯H16	2.65
N1⋯H5	2.62	C16⋯H3	2.63
H1⋯N1ⁱ	1.997 (16)	H1⋯H5ⁱ	2.33
C3⋯C19ⁱⁱ	3.386 (2)	H2A⋯H3	2.07
C17⋯C17ⁱⁱ	3.396 (2)	H3⋯H16	2.06
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) .

Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm.

Figure 4
View of the Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range of −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms corresponding to positive and negative potentials, respectively.

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⋯H, (c) H⋯C/C⋯H, (d) C⋯C, (e) H⋯O/O⋯H, (f) H⋯N/N⋯H and (g) C⋯N/N⋯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 contacts.

Figure 7
The Hirshfeld surface representations of contact patches plotted onto the surface for (a) H⋯H, (b) H⋯C/C⋯H and (c) C⋯C interactions.

5. Crystal voids

If the molecules are tightly packed and an applied external mechanical force does not easily break the crystal, then the crystal packing does not result in significant voids. 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 volume of the crystal voids (Fig. 8) and the percentage of free space in the unit cell are calculated as 76.07 Å³ and 5.79%, respectively, indicating that the crystal packing is compact.

Figure 8
Graphical views of voids in the crystal packing of the title compound along the (a) a-axis and (b) c-axis directions.>

6. Interaction energy calculations and energy frameworks

The CE–B3LYP/6–31G(d,p) energy model available in Crystal Explorer 17.5 (Spackman et al., 2021) was used to calculate the intermolecular interaction energies. Hydrogen-bonding interaction energies (in kJ mol⁻¹) were calculated to be −9.8 (E_ele), −14.2 (E_pol), −103.3 (E_dis), 52.1 (E_rep) and −70.0 (E_tot) for O1—H1⋯N1. Energy frameworks combine the calculation of intermolecular interaction energies with a graphical representation of their magnitude (Turner et al., 2015 ). Energy frameworks were constructed for E_ele (red cylinders), E_dis (green cylinders) and E_tot (blue cylinders) (Fig. 9a, b and c), and their evaluation indicates that the stabilization is dominated via the dispersion energy contributions in the crystal structure of (I).

Figure 9
The energy frameworks for a cluster of molecules of the title compound viewed down the c-axis showing the (a) electrostatic energy, (b) dispersion energy and (c) total energy diagrams. The cylindrical radius is proportional to the relative strength of the corresponding energies and they were adjusted to the same scale factor of 80 with cut-off value of 5 kJ mol⁻¹ within 2 × 2 X 2 unit cells.

7. Synthesis and crystallization

To a solution of 1-pyrenecarboxaldehyde (0.230 g, 1.0 mmol) in ethanol (25 ml) was added 2-aminoethanol (0.073 g, 1.2 mmol) and the reaction mixture was refluxed for 4 h. The reaction mixture was cooled down to room temperature for precipitation, and then filtered. The precipitate was washed with cold ethanol and dried in air. Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution. Yield: 80%. FT–IR (cm⁻¹): 3440 (OH), 1631 (C=N), 1594 (C=C). ¹H NMR (CDCl₃): 9.34 (s, 1H, N=CH), 9.12 (d, 1H, J_H–H = 9.6 Hz, pyrenyl), 8.56 (d, 1H, J_H–H = 7.8 Hz, pyrenyl), 8.36 (m, 7H, pyrenyl), 4.73 (t, J_H–H = 5.4 Hz, OH), 3.87 (dd, 4H, J_H–H = 4.8 and 5.4 Hz, CH₂). ¹³C NMR (CDCl₃): 161.83, 131.23, 128.75, 128.68, 127.41, 126.21, 125.97, 125.70, 124.92, 122.38, 64.20, 62.70; HRMS: m/z: 273.11 [M]⁺. Analysis calculated (%) for C₁₉H₁₅NO: C 83.49, H 5.53, N 5.12; found C 83.47, H 5.51, N 5.10.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The OH hydrogen atom was located in a difference-Fourier map, and refined isotropically. The C-bound hydrogen-atom positions were calculated geometrically at distances of 0.93 Å (for aromatic CH) and 0.97 Å (for CH₂) and refined using a riding model by applying the constraint U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO
M_r	273.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.447 (2), 20.916 (8), 8.446 (3)
β (°)	93.347 (9)
V (Å³)	1313.3 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.35 × 0.28

Data collection
Diffractometer	Bruker D8 Quest
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
No. of measured, independent and observed [I > 2σ(I)] reflections	14470, 2362, 1980
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.04
No. of reflections	2362
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2021 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2452369

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004451/ee2014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004451/ee2014Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025004451/ee2014Isup3.cml

checkCIF report

Computing details top

(E)-2-[(Pyren-1-ylmethylidene)amino]ethanol top

Crystal data top

C₁₉H₁₅NO	F(000) = 576
M_r = 273.32	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.447 (2) Å	Cell parameters from 7593 reflections
b = 20.916 (8) Å	θ = 2.6–25.4°
c = 8.446 (3) Å	µ = 0.09 mm⁻¹
β = 93.347 (9)°	T = 100 K
V = 1313.3 (8) Å³	Block, colourless
Z = 4	0.37 × 0.35 × 0.28 mm

Data collection top

Bruker D8 Quest diffractometer	1980 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.044
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.3°, θ_min = 2.7°
	h = −8→8
14470 measured reflections	k = −25→25
2362 independent reflections	l = −10→10

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0576P)² + 0.4126P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.019
2362 reflections	Δρ_max = 0.18 e Å⁻³
193 parameters	Δρ_min = −0.25 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	0.20414 (13)	0.21597 (5)	0.52257 (12)	0.0216 (3)
H1	0.248 (2)	0.2057 (8)	0.616 (2)	0.032*
N1	0.37839 (14)	0.30976 (5)	0.32442 (13)	0.0152 (3)
C1	0.32460 (18)	0.19901 (6)	0.40609 (16)	0.0171 (3)
H1A	0.256590	0.191054	0.306579	0.020*
H1B	0.385335	0.159619	0.437830	0.020*
C2	0.46484 (18)	0.25029 (6)	0.38038 (16)	0.0164 (3)
H2A	0.534355	0.258221	0.479141	0.020*
H2B	0.546544	0.235486	0.302886	0.020*
C3	0.38451 (17)	0.35642 (6)	0.42167 (15)	0.0146 (3)
H3	0.444841	0.350163	0.519987	0.017*
C4	0.30263 (16)	0.41963 (6)	0.38920 (15)	0.0130 (3)
C5	0.23407 (17)	0.43504 (6)	0.23570 (15)	0.0145 (3)
H5	0.237547	0.404567	0.155754	0.017*
C6	0.16132 (16)	0.49467 (6)	0.20070 (15)	0.0143 (3)
H6	0.117589	0.503528	0.097642	0.017*
C7	0.15235 (16)	0.54192 (6)	0.31769 (15)	0.0128 (3)
C8	0.07710 (17)	0.60437 (6)	0.28453 (15)	0.0154 (3)
H8	0.035518	0.614331	0.181508	0.019*
C9	0.06565 (17)	0.64883 (6)	0.40009 (16)	0.0167 (3)
H9	0.016214	0.688652	0.375061	0.020*
C10	0.12884 (16)	0.63543 (6)	0.56126 (15)	0.0140 (3)
C11	0.11339 (17)	0.68037 (6)	0.68337 (17)	0.0174 (3)
H11	0.060084	0.719801	0.660935	0.021*
C12	0.17704 (17)	0.66639 (6)	0.83720 (16)	0.0179 (3)
H12	0.166897	0.696676	0.916797	0.021*
C13	0.25590 (17)	0.60745 (6)	0.87342 (15)	0.0167 (3)
H13	0.299764	0.599066	0.976686	0.020*
C14	0.27000 (16)	0.56069 (6)	0.75641 (15)	0.0138 (3)
C15	0.34525 (17)	0.49843 (6)	0.78892 (15)	0.0149 (3)
H15	0.386896	0.488566	0.891982	0.018*
C16	0.35730 (17)	0.45384 (6)	0.67445 (15)	0.0146 (3)
H16	0.407480	0.414277	0.701019	0.018*
C17	0.29455 (16)	0.46569 (6)	0.51163 (15)	0.0125 (3)
C18	0.21810 (16)	0.52728 (6)	0.47568 (15)	0.0122 (3)
C19	0.20622 (16)	0.57444 (6)	0.59733 (15)	0.0126 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0190 (5)	0.0258 (6)	0.0203 (5)	0.0037 (4)	0.0046 (4)	0.0078 (4)
N1	0.0156 (6)	0.0122 (6)	0.0180 (6)	−0.0018 (4)	0.0029 (4)	0.0010 (4)
C1	0.0208 (7)	0.0129 (7)	0.0173 (7)	0.0002 (5)	−0.0013 (5)	0.0012 (5)
C2	0.0168 (7)	0.0151 (7)	0.0175 (7)	0.0025 (5)	0.0021 (5)	−0.0003 (5)
C3	0.0127 (6)	0.0167 (7)	0.0145 (6)	−0.0029 (5)	0.0020 (5)	0.0011 (5)
C4	0.0098 (6)	0.0138 (7)	0.0156 (7)	−0.0029 (5)	0.0022 (5)	0.0017 (5)
C5	0.0141 (7)	0.0148 (7)	0.0150 (7)	−0.0027 (5)	0.0028 (5)	−0.0022 (5)
C6	0.0119 (6)	0.0191 (7)	0.0118 (6)	−0.0016 (5)	−0.0009 (5)	0.0029 (5)
C7	0.0086 (6)	0.0162 (6)	0.0139 (6)	−0.0028 (5)	0.0020 (5)	0.0024 (5)
C8	0.0129 (6)	0.0187 (7)	0.0146 (6)	−0.0001 (5)	0.0001 (5)	0.0049 (5)
C9	0.0131 (6)	0.0135 (6)	0.0235 (7)	0.0007 (5)	0.0020 (5)	0.0054 (5)
C10	0.0099 (6)	0.0143 (7)	0.0181 (7)	−0.0030 (5)	0.0030 (5)	0.0001 (5)
C11	0.0129 (6)	0.0146 (7)	0.0248 (8)	−0.0007 (5)	0.0031 (5)	−0.0008 (5)
C12	0.0156 (7)	0.0174 (7)	0.0209 (7)	−0.0036 (5)	0.0039 (5)	−0.0063 (6)
C13	0.0142 (7)	0.0227 (7)	0.0134 (7)	−0.0049 (5)	0.0015 (5)	−0.0014 (5)
C14	0.0093 (6)	0.0160 (7)	0.0162 (7)	−0.0039 (5)	0.0023 (5)	0.0004 (5)
C15	0.0127 (6)	0.0198 (7)	0.0119 (6)	−0.0026 (5)	−0.0006 (5)	0.0022 (5)
C16	0.0135 (6)	0.0129 (6)	0.0173 (7)	−0.0003 (5)	0.0001 (5)	0.0043 (5)
C17	0.0093 (6)	0.0138 (7)	0.0144 (6)	−0.0036 (5)	0.0021 (5)	0.0018 (5)
C18	0.0079 (6)	0.0144 (7)	0.0146 (7)	−0.0034 (5)	0.0023 (5)	0.0014 (5)
C19	0.0082 (6)	0.0155 (7)	0.0143 (7)	−0.0036 (5)	0.0031 (5)	0.0002 (5)

Geometric parameters (Å, º) top

O1—C1	1.4148 (17)	C8—H8	0.9300
O1—H1	0.862 (19)	C9—C10	1.4415 (19)
N1—C3	1.2745 (17)	C9—H9	0.9300
N1—C2	1.4662 (17)	C10—C11	1.4051 (19)
C1—C2	1.5215 (19)	C10—C19	1.4254 (19)
C1—H1A	0.9700	C11—C12	1.388 (2)
C1—H1B	0.9700	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.3918 (19)
C2—H2B	0.9700	C12—H12	0.9300
C3—C4	1.4750 (18)	C13—C14	1.3988 (19)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.4029 (19)	C14—C19	1.4279 (19)
C4—C17	1.4171 (19)	C14—C15	1.4378 (19)
C5—C6	1.3847 (19)	C15—C16	1.3500 (19)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.4019 (19)	C16—C17	1.4476 (18)
C6—H6	0.9300	C16—H16	0.9300
C7—C18	1.4275 (18)	C17—C18	1.4337 (19)
C7—C8	1.4424 (18)	C18—C19	1.4307 (19)
C8—C9	1.3543 (19)

O1···N1	2.9300 (19)	H1···C2ⁱ	2.841 (16)
O1···N1ⁱ	2.8440 (18)	C3···H16	2.65
N1···H5	2.62	C16···H3	2.63
H1···N1ⁱ	1.997 (16)	H1···H5ⁱ	2.33
C3···C19ⁱⁱ	3.386 (2)	H2A···H3	2.07
C17···C17ⁱⁱ	3.396 (2)	H3···H16	2.06

C1—O1—H1	110.7 (12)	C8—C9—H9	119.5
C3—N1—C2	116.32 (11)	C10—C9—H9	119.5
O1—C1—C2	113.01 (11)	C11—C10—C19	119.43 (12)
O1—C1—H1A	109.0	C11—C10—C9	121.79 (12)
C2—C1—H1A	109.0	C19—C10—C9	118.78 (12)
O1—C1—H1B	109.0	C12—C11—C10	120.53 (13)
C2—C1—H1B	109.0	C12—C11—H11	119.7
H1A—C1—H1B	107.8	C10—C11—H11	119.7
N1—C2—C1	110.61 (11)	C11—C12—C13	120.60 (12)
N1—C2—H2A	109.5	C11—C12—H12	119.7
C1—C2—H2A	109.5	C13—C12—H12	119.7
N1—C2—H2B	109.5	C12—C13—C14	120.81 (12)
C1—C2—H2B	109.5	C12—C13—H13	119.6
H2A—C2—H2B	108.1	C14—C13—H13	119.6
N1—C3—C4	124.59 (12)	C13—C14—C19	119.30 (12)
N1—C3—H3	117.7	C13—C14—C15	122.89 (12)
C4—C3—H3	117.7	C19—C14—C15	117.82 (12)
C5—C4—C17	119.30 (12)	C16—C15—C14	122.03 (12)
C5—C4—C3	120.13 (12)	C16—C15—H15	119.0
C17—C4—C3	120.56 (12)	C14—C15—H15	119.0
C6—C5—C4	121.40 (12)	C15—C16—C17	122.05 (12)
C6—C5—H5	119.3	C15—C16—H16	119.0
C4—C5—H5	119.3	C17—C16—H16	119.0
C5—C6—C7	121.24 (12)	C4—C17—C18	119.31 (12)
C5—C6—H6	119.4	C4—C17—C16	123.47 (12)
C7—C6—H6	119.4	C18—C17—C16	117.21 (12)
C6—C7—C18	118.67 (12)	C7—C18—C19	119.41 (12)
C6—C7—C8	122.39 (12)	C7—C18—C17	120.07 (12)
C18—C7—C8	118.94 (12)	C19—C18—C17	120.52 (12)
C9—C8—C7	121.47 (12)	C10—C19—C14	119.31 (12)
C9—C8—H8	119.3	C10—C19—C18	120.32 (12)
C7—C8—H8	119.3	C14—C19—C18	120.38 (12)
C8—C9—C10	121.07 (12)

C3—N1—C2—C1	110.27 (13)	C3—C4—C17—C18	178.50 (10)
O1—C1—C2—N1	−61.54 (14)	C5—C4—C17—C16	178.35 (11)
C2—N1—C3—C4	−178.71 (11)	C3—C4—C17—C16	−2.55 (19)
N1—C3—C4—C5	−9.67 (19)	C15—C16—C17—C4	−178.97 (12)
N1—C3—C4—C17	171.23 (12)	C15—C16—C17—C18	0.00 (18)
C17—C4—C5—C6	1.06 (19)	C6—C7—C18—C19	−178.58 (11)
C3—C4—C5—C6	−178.05 (11)	C8—C7—C18—C19	0.64 (17)
C4—C5—C6—C7	−0.38 (19)	C6—C7—C18—C17	1.17 (17)
C5—C6—C7—C18	−0.74 (18)	C8—C7—C18—C17	−179.62 (11)
C5—C6—C7—C8	−179.92 (11)	C4—C17—C18—C7	−0.50 (18)
C6—C7—C8—C9	178.35 (12)	C16—C17—C18—C7	−179.52 (10)
C18—C7—C8—C9	−0.83 (18)	C4—C17—C18—C19	179.24 (10)
C7—C8—C9—C10	0.13 (19)	C16—C17—C18—C19	0.23 (18)
C8—C9—C10—C11	−178.20 (12)	C11—C10—C19—C14	−1.30 (18)
C8—C9—C10—C19	0.74 (18)	C9—C10—C19—C14	179.74 (11)
C19—C10—C11—C12	1.71 (19)	C11—C10—C19—C18	178.05 (11)
C9—C10—C11—C12	−179.36 (12)	C9—C10—C19—C18	−0.91 (18)
C10—C11—C12—C13	−0.53 (19)	C13—C14—C19—C10	−0.27 (18)
C11—C12—C13—C14	−1.1 (2)	C15—C14—C19—C10	179.26 (11)
C12—C13—C14—C19	1.47 (19)	C13—C14—C19—C18	−179.61 (11)
C12—C13—C14—C15	−178.03 (11)	C15—C14—C19—C18	−0.09 (17)
C13—C14—C15—C16	179.82 (12)	C7—C18—C19—C10	0.23 (18)
C19—C14—C15—C16	0.32 (18)	C17—C18—C19—C10	−179.52 (11)
C14—C15—C16—C17	−0.28 (19)	C7—C18—C19—C14	179.57 (11)
C5—C4—C17—C18	−0.61 (18)	C17—C18—C19—C14	−0.18 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.853 (17)	1.997 (16)	2.8440 (18)	171.6 (14)

Symmetry code: (i) x, −y+1/2, z+1/2.

Funding information

TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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