Crystal structure and Hirshfeld surface analysis, crystal voids, inter­action energy calculations and energy frameworks of C-anthracen-9-yl-N-methyl aldo­nitrone

Lasri, J.; Zayed, M.M.; Almehmadi, Y.A.; Eltayeb, N.E.; Hökelek, T.; McKay, A.P.

doi:10.1107/S2056989026000599

research communications

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ISSN: 2056-9890

Volume 82| Part 2| February 2026| Pages 221-226

https://doi.org/10.1107/S2056989026000599

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Crystal structure and Hirshfeld surface analysis, crystal voids, interaction energy calculations and energy frameworks of C-anthracen-9-yl-N-methyl aldonitrone

Jamal Lasri,^a ^* Mohamed M. Zayed,^a,^b Yaseen A. Almehmadi,^a,^c Naser E. Eltayeb,^a,^d Tuncer Hökelek ^e and Aidan P. McKay ^f

^aDepartment of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, Jeddah 21589, Saudi Arabia, ^bEnvironmental and Occupational Medicine Department, National Research Centre, Giza 12622, Egypt, ^cKing Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia, ^dDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Khartoum 2469, Sudan, ^eDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye, and ^fEaStCHEM School of Chemistry, University of St Andrews, Fife KY16 9ST, United Kingdom
^*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 6 January 2026; accepted 21 January 2026; online 29 January 2026)

The title compound (systematic name: 1-anthracen-9-yl-N-methylmethanimine oxide), C₁₆H₁₃NO, contains an almost planar anthracene ring system [r.m.s. deviation = 0.021 (1) Å]. In the crystal, intermolecular bifurcated C—H⋯O hydrogen bonds link the molecules into infinite chains along the a-axis direction. The π–π stacking interactions between the benzene rings of adjacent molecules help to consolidate the three-dimensional architecture. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (54.5%), H⋯C/C⋯H (23.7%), H⋯O/O⋯H (10.6%) and C⋯C (9.8%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 76.07 Å³ and 6.57%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization largely depends on dispersion energy contributions. Hydrogen bonding, π–π and van der Waals interactions, together with the dispersion energy contributions, are the dominant interactions in the crystal packing.

Keywords: C-anthracen-9-yl-N-methyl aldonitrone; crystal structure; hydrogen bond; π-stacking; Hirshfeld surface; energy framework analysis.

CCDC reference: 2524759

1. Chemical context

Nitrones have interesting applications as buiding blocks in the synthesis of natural products (Padwa & Pearson, 2002 ) and have found usage as both modifiers in radical polymerization and regulators of molecular weight (Feuer, 2007 ; Hamer & Macaluso, 1964 ). Nitrones have been broadly used in metal-mediated [2 + 3]-cycloaddition reactions to furnish N-heterocyclic compounds which have shown to be excellent catalysts for Suzuki-Miyaura C—C cross-couplings (Fernandes et al., 2011 ). Nitrones have also been used for therapeutic applications as they are components of the molecular structure of several drugs (Floyd et al., 2008 ). Currently, our research program focuses on the synthesis, X-ray structure analysis, Hirshfeld surface analysis and density functional theory (DFT) calculations and molecular docking studies of aldonitrone-type compounds (Lasri et al., 2024 ). Herein, we report the synthesis, molecular and crystal structures, Hirshfeld surface analysis, crystal voids, interaction energies and energy frameworks of the title compound C-anthracen-9-yl-N-methyl aldonitrone, (I).

2. Structural commentary

The title compound, (I), contains an almost planar [r.m.s. deviation = 0.021 (1) Å] anthracene ring system, consisting of three fused benzene rings, denoted A (C1/C2/C7–C9/C14), B (C2–C7) and C (C9–C14) (Fig. 1). Atom C3 deviates by −0.0419 (14) Å from the least-squares plane through the ring system. The planes of benzene rings A, B and C are oriented at dihedral angles of A/B = 1.95 (4)°, A/C = 1.99 (5)° and B/C = 0.51 (3)°. In the substituent, the C1—C15—N16, C15—N16—C17, C15—N16—O16 and C17—N16—O16 bond angles are 125.01 (13), 119.73 (12), 125.30 (12) and 114.96 (11)°, respectively. On the other hand, the N16—C15—C1—C2, N16—C15—C1—C14, C15—C1—C2—C3 and C15—C1—C14—C13 torsion angles are 56.39 (19), −128.50 (14), −1.4 (2) and 4.96 (19)°, respectively. The dihedral angle between the plane of the anthracene ring and the least-squares plane through its substituent is 54.42 (5)°.

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

3. Supramolecular features

In the crystal, intermolecular bifurcated C—H⋯O hydrogen bonds (Table 1) link the molecules into infinite chains along the a-axis direction (Fig. 2). The π–π stacking interactions between the benzene rings (A, B and C) of adjacent molecules, with inter-centroid distances of 3.8445 (8) [between rings A and B, α = 1.96 (6)° and slippage = 1.592 Å] and 3.8497 (8) Å [between rings A and C, α = 0.51 (7)° and slippage = 1.636 Å] may help to consolidate the three-dimensional architecture, together with C—H⋯O contacts. 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
C15—H15⋯O16ⁱ	0.95	2.24	3.1267 (18)	154
C17—H17B⋯O16ⁱ	0.98	2.28	3.2037 (18)	157
Symmetry code: (i) .

Figure 2
A partial packing diagram viewed down the c-axis direction. Intermolecular C—H⋯O hydrogen bonds are shown as dashed lines. Nonbonding H atoms have been omitted for clarity.

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 [Figs. 3(a), 3(b) and 3(c)] and the percentage of free space in the unit cell are calculated as 76.07 Å³ and 6.57%, respectively, indicating that the crystal packing is compact.

Figure 3
Graphical views of voids in the crystal packing of the title compound (a) along the a-axis, (b) along the b-axis and (c) along the c-axis direction.

4. Hirshfeld surface analysis

A Hirshfeld surface (HS) analysis was carried out using CrystalExplorer (Version 17.5; Spackman et al., 2021 ) for clarifying the intermolecular interactions in the crystal of (I). The HS plotted over d_norm is shown in Fig. 4, where the bright-red spots correspond to donor and/or acceptor sites; they also appear as blue and red regions in Fig. 5, corresponding to positive and negative potentials (Spackman et al., 2008 ). The shape-index surface can be used for identifying the characteristic packing modes, particularly, the presence of aromatic stacking interactions like C—H⋯π(ring) and π–π interactions, with the former represented as red π-holes, which are related to the electron–ring interactions between the C—H groups with the centroids of the aromatic rings of neighbouring molecules. Fig. 6 clearly suggests that there are no C—H⋯π(ring) interactions. A π–π stacking is indicated by the presence of adjacent red and blue triangles, as clearly indicated by Fig. 6. According to the 2D fingerprint plots (McKinnon et al., 2007 ), intermolecular H⋯H, H⋯C/C⋯H, H⋯O/O⋯H and C⋯C contacts make important contributions to the HS, with values of 54.5, 23.7, 10.6 and 9.8%, respectively (Fig. 7).

Figure 4
View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm in the range from −0.3681 to 1.4279 a.u.

Figure 5
View of the Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range from −0.0500 to 0.0500 a.u. using the STO-3G 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 6
Hirshfeld surface of the title compound plotted over shape-index.

Figure 7
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) H⋯O/O⋯H, (e) C⋯C, (f) H⋯N/N⋯H and (g) N⋯O/O⋯N 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.

5. Database survey

A survey of the Cambridge Structural Database (CSD, Version 6.01, November 2025 update; Groom et al., 2016 ) revealed 3581 C9-substituted anthracene derivatives. Herein, we present 20 of them with structural similarity to the target compound C-anthracen-9-yl-N-methyl aldonitrone, namely, I (AWUZOI; Kraicheva et al., 2011 ), II (AXODAS; Wong et al., 2004 ), III (AZORUD; Geetha et al., 2011 ), IV (CEJLOT; Horiguchi & Ito, 2006 ), V (CUBMOC; Jaworska et al., 2009 ), VI (EDOHIS; Monika et al., 2022 ), VII (FAXVIK; Howie et al., 2005 ), VIII (FIBQIT; Spinelli et al., 2018 ), IX (FOHLOE; Howie & Wardell, 2005 ), X (GUMLAD; Lohar et al., 2015 ), XI (KEYJAD; Kakimoto et al., 2023 ), XII (KOBWAC; Ghosh et al., 2017 ), XIII (NIJWEK; Banerjee et al., 2013 ), XIV (NOKMIN; Zheng et al., 2024 ), XV (OCOLUQ; Faizi et al., 2017 ), XVI (PIGWOR; Subramanian et al., 1993 ), XVII (QARBUG; Ihmels et al., 2000 ), XVIII (TITNES; Junor et al., 2019 ), XIX (TUPGIV; Villalpando et al., 2010 ) and XX (YIVQAY; Barwiolek et al., 2019 ).

6. Interaction energy calculations and energy frameworks

The CE-B3LYP/6-31G(d,p) energy model available in CrystalExplorer (Version 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 −33.9 (E_ele), −10.9 (E_pol), −62.7 (E_dis), 65.8 (E_rep) and −57.9 (E_tot) for the C15—H15⋯O16, and −23.9 (E_ele), −6.4 (E_pol), −32.8 (E_dis), 18.5 (E_rep) and −47.1 (E_tot) for the C17—H17B⋯O16 hydrogen-bond interaction. 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) [Figs. 8(a), 8(b) and 8(c)], and their evaluation indicates that the stabilization largely depends on dispersion energy contributions in the crystal structure of (I).

Figure 8
The energy frameworks for a cluster of molecules of the title compound viewed down the b axis, showing the (a) electrostatic energy E_ele, (b) dispersion energy E_dis and (c) total energy E_tot 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 a cut-off value of 5 kJ mol⁻¹ within 2×2×2 unit cells.

7. Synthesis and crystallization

To a solution of N-methylhydroxylamine (99.9 mg, 1.20 mmol) in MeOH (50 ml) was added sodium carbonate (63.4 mg, 0.60 mmol) and the reaction mixture was stirred for 10 min followed by the addition of anthracene-9-carbaldehyde (224.4 mg, 1.09 mmol). The mixture was then stirred for 12 h at room temperature. The precipitate which formed was filtered off and MeOH was eliminated in vacuo. In order to remove the NaCl produced, the obtained solid was dissolved in CH₂Cl₂ and filtered, the filtrate was then evaporated in vacuo. The solid product was ultimately washed with Et₂O to give pure C-anthracen-9-yl-N-methyl aldonitrone, (I). Yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a CH₂Cl₂ solution (yield 90%). FT–IR (cm⁻¹): 1637 (C=N), 1566 (C=C). Analysis calculated (%) for C₁₆H₁₃NO: C 81.68, H 5.57, N 5.95; found: C 81.73, H 5.60, N 5.93.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H-atom positions were calculated geometrically at distances of 0.95 (for aromatic and methine CH) and 0.98 Å (for CH₃), and refined using a riding model by applying the constraints U_iso(H) = kU_eq(C), where k = 1.5 for CH₃ and 1.2 for the other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO
M_r	235.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	4.89615 (14), 16.6590 (5), 14.2008 (4)
β (°)	91.240 (3)
V (Å³)	1158.02 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.02 × 0.01

Data collection
Diffractometer	Rigaku XtaLAB P200K
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2024 )
T_min, T_max	0.714, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24788, 2788, 1992
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.05
No. of reflections	2788
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2024), SHELXT2018 (Sheldrick, 2015a ), SHELXL2019 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2524759

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000599/vm2323sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026000599/vm2323Isup2.hkl

checkcif. DOI: https://doi.org/10.1107/S2056989026000599/vm2323sup3.pdf

checkcif. DOI: https://doi.org/10.1107/S2056989026000599/vm2323sup4.pdf

Supporting information file. DOI: https://doi.org/10.1107/S2056989026000599/vm2323Isup5.cml

checkCIF report

Computing details top

1-Anthracen-9-yl-N-methylmethanimine oxide top

Crystal data top

C₁₆H₁₃NO	F(000) = 496
M_r = 235.27	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.89615 (14) Å	Cell parameters from 8143 reflections
b = 16.6590 (5) Å	θ = 2.8–29.1°
c = 14.2008 (4) Å	µ = 0.08 mm⁻¹
β = 91.240 (3)°	T = 100 K
V = 1158.02 (6) Å³	Platy-needle, yellow
Z = 4	0.26 × 0.02 × 0.01 mm

Data collection top

Rigaku XtaLAB P200K diffractometer	2788 independent reflections
Radiation source: Rotating Anode, Rigaku FR-X	1992 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.055
Detector resolution: 5.8140 pixels mm^-1	θ_max = 29.0°, θ_min = 1.9°
shutterless scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2024)	k = −21→21
T_min = 0.714, T_max = 1.000	l = −19→19
24788 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0587P)² + 0.3266P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2788 reflections	Δρ_max = 0.30 e Å⁻³
164 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

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
O16	0.2639 (2)	0.47437 (6)	0.60736 (7)	0.0281 (3)
N16	0.5270 (2)	0.47324 (7)	0.61726 (8)	0.0205 (3)
C1	0.5642 (3)	0.60243 (8)	0.70066 (9)	0.0178 (3)
C2	0.3685 (3)	0.60047 (8)	0.77210 (9)	0.0175 (3)
C3	0.2557 (3)	0.52728 (8)	0.80734 (9)	0.0204 (3)
H3	0.315933	0.477410	0.782852	0.025*
C4	0.0635 (3)	0.52796 (8)	0.87536 (9)	0.0229 (3)
H4	−0.009682	0.478649	0.897013	0.028*
C5	−0.0289 (3)	0.60146 (9)	0.91436 (9)	0.0232 (3)
H5	−0.166736	0.601175	0.960406	0.028*
C6	0.0801 (3)	0.67197 (8)	0.88573 (9)	0.0215 (3)
H6	0.021220	0.720677	0.913543	0.026*
C7	0.2818 (3)	0.67444 (8)	0.81452 (9)	0.0183 (3)
C8	0.3977 (3)	0.74681 (8)	0.78584 (9)	0.0192 (3)
H8	0.341342	0.795398	0.814553	0.023*
C9	0.5936 (3)	0.74962 (8)	0.71628 (9)	0.0186 (3)
C10	0.7105 (3)	0.82395 (8)	0.68640 (10)	0.0222 (3)
H10	0.655215	0.872636	0.715162	0.027*
C11	0.8991 (3)	0.82603 (8)	0.61756 (10)	0.0244 (3)
H11	0.973665	0.875937	0.598406	0.029*
C12	0.9852 (3)	0.75359 (9)	0.57416 (10)	0.0243 (3)
H12	1.118288	0.755476	0.526533	0.029*
C13	0.8788 (3)	0.68159 (8)	0.60015 (9)	0.0211 (3)
H13	0.937397	0.633996	0.569781	0.025*
C14	0.6800 (3)	0.67635 (8)	0.67244 (9)	0.0178 (3)
C15	0.6736 (3)	0.52877 (8)	0.65776 (9)	0.0196 (3)
H15	0.866041	0.521447	0.659962	0.024*
C17	0.6620 (3)	0.40225 (8)	0.57657 (10)	0.0228 (3)
H17A	0.608897	0.354042	0.611222	0.034*
H17B	0.860711	0.408976	0.581280	0.034*
H17C	0.606005	0.396676	0.510219	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O16	0.0163 (6)	0.0333 (6)	0.0348 (6)	0.0009 (4)	0.0017 (4)	−0.0111 (5)
N16	0.0171 (6)	0.0207 (6)	0.0237 (6)	0.0009 (5)	0.0036 (5)	−0.0040 (5)
C1	0.0172 (7)	0.0170 (7)	0.0191 (6)	0.0021 (5)	−0.0013 (5)	−0.0019 (5)
C2	0.0184 (7)	0.0162 (6)	0.0178 (6)	0.0020 (5)	−0.0011 (5)	−0.0002 (5)
C3	0.0243 (8)	0.0153 (6)	0.0216 (7)	0.0028 (5)	−0.0002 (6)	−0.0013 (5)
C4	0.0286 (8)	0.0201 (7)	0.0202 (7)	−0.0024 (6)	0.0030 (6)	0.0020 (5)
C5	0.0246 (8)	0.0259 (7)	0.0194 (6)	0.0013 (6)	0.0055 (6)	0.0008 (6)
C6	0.0245 (8)	0.0194 (7)	0.0208 (6)	0.0052 (6)	0.0032 (6)	−0.0023 (5)
C7	0.0182 (7)	0.0179 (7)	0.0188 (6)	0.0029 (5)	−0.0006 (5)	−0.0013 (5)
C8	0.0209 (7)	0.0156 (7)	0.0211 (7)	0.0039 (5)	0.0000 (5)	−0.0026 (5)
C9	0.0193 (7)	0.0168 (7)	0.0196 (6)	0.0019 (5)	−0.0013 (5)	−0.0003 (5)
C10	0.0271 (8)	0.0153 (7)	0.0241 (7)	0.0006 (5)	−0.0006 (6)	−0.0016 (5)
C11	0.0293 (8)	0.0190 (7)	0.0249 (7)	−0.0038 (6)	0.0007 (6)	0.0018 (6)
C12	0.0228 (8)	0.0263 (8)	0.0238 (7)	−0.0020 (6)	0.0045 (6)	−0.0004 (6)
C13	0.0207 (7)	0.0198 (7)	0.0229 (7)	0.0005 (5)	0.0023 (5)	−0.0039 (5)
C14	0.0178 (7)	0.0172 (7)	0.0182 (6)	0.0008 (5)	−0.0003 (5)	−0.0017 (5)
C15	0.0197 (7)	0.0173 (7)	0.0220 (7)	0.0012 (5)	0.0033 (5)	−0.0005 (5)
C17	0.0243 (8)	0.0173 (7)	0.0269 (7)	0.0010 (6)	0.0047 (6)	−0.0062 (6)

Geometric parameters (Å, º) top

O16—N16	1.2932 (15)	C8—H8	0.9500
N16—C15	1.2975 (18)	C8—C9	1.3924 (19)
N16—C17	1.4785 (16)	C9—C10	1.4324 (19)
C1—C2	1.4108 (19)	C9—C14	1.4381 (18)
C1—C14	1.4172 (18)	C10—H10	0.9500
C1—C15	1.4757 (18)	C10—C11	1.360 (2)
C2—C3	1.4332 (18)	C11—H11	0.9500
C2—C7	1.4396 (18)	C11—C12	1.4229 (19)
C3—H3	0.9500	C12—H12	0.9500
C3—C4	1.3631 (19)	C12—C13	1.3618 (19)
C4—H4	0.9500	C13—H13	0.9500
C4—C5	1.4217 (19)	C13—C14	1.4323 (19)
C5—H5	0.9500	C15—H15	0.9500
C5—C6	1.356 (2)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C6—C7	1.4293 (19)	C17—H17C	0.9800
C7—C8	1.3968 (18)

O16—N16—C15	125.30 (12)	C8—C9—C10	121.67 (12)
O16—N16—C17	114.96 (11)	C8—C9—C14	119.50 (12)
C15—N16—C17	119.73 (12)	C10—C9—C14	118.84 (12)
C2—C1—C14	120.37 (11)	C9—C10—H10	119.4
C2—C1—C15	122.40 (12)	C11—C10—C9	121.13 (13)
C14—C1—C15	117.05 (11)	C11—C10—H10	119.4
C1—C2—C3	122.93 (11)	C10—C11—H11	119.9
C1—C2—C7	119.48 (12)	C10—C11—C12	120.11 (13)
C3—C2—C7	117.57 (12)	C12—C11—H11	119.9
C2—C3—H3	119.4	C11—C12—H12	119.6
C4—C3—C2	121.17 (12)	C13—C12—C11	120.74 (13)
C4—C3—H3	119.4	C13—C12—H12	119.6
C3—C4—H4	119.6	C12—C13—H13	119.4
C3—C4—C5	120.90 (13)	C12—C13—C14	121.18 (13)
C5—C4—H4	119.6	C14—C13—H13	119.4
C4—C5—H5	120.0	C1—C14—C9	119.45 (12)
C6—C5—C4	119.91 (13)	C1—C14—C13	122.54 (12)
C6—C5—H5	120.0	C13—C14—C9	118.00 (12)
C5—C6—H6	119.4	N16—C15—C1	125.01 (13)
C5—C6—C7	121.29 (12)	N16—C15—H15	117.5
C7—C6—H6	119.4	C1—C15—H15	117.5
C6—C7—C2	119.07 (12)	N16—C17—H17A	109.5
C8—C7—C2	119.44 (12)	N16—C17—H17B	109.5
C8—C7—C6	121.49 (12)	N16—C17—H17C	109.5
C7—C8—H8	119.1	H17A—C17—H17B	109.5
C9—C8—C7	121.75 (12)	H17A—C17—H17C	109.5
C9—C8—H8	119.1	H17B—C17—H17C	109.5

O16—N16—C15—C1	0.9 (2)	C8—C9—C10—C11	−179.17 (13)
C1—C2—C3—C4	−178.89 (12)	C8—C9—C14—C1	0.08 (19)
C1—C2—C7—C6	178.96 (12)	C8—C9—C14—C13	179.06 (12)
C1—C2—C7—C8	−1.51 (19)	C9—C10—C11—C12	−0.4 (2)
C2—C1—C14—C9	−0.90 (19)	C10—C9—C14—C1	−179.40 (12)
C2—C1—C14—C13	−179.83 (12)	C10—C9—C14—C13	−0.42 (19)
C2—C1—C15—N16	56.39 (19)	C10—C11—C12—C13	0.6 (2)
C2—C3—C4—C5	−0.7 (2)	C11—C12—C13—C14	−0.7 (2)
C2—C7—C8—C9	0.7 (2)	C12—C13—C14—C1	179.59 (13)
C3—C2—C7—C6	−2.96 (19)	C12—C13—C14—C9	0.6 (2)
C3—C2—C7—C8	176.56 (12)	C14—C1—C2—C3	−176.36 (12)
C3—C4—C5—C6	−1.8 (2)	C14—C1—C2—C7	1.61 (19)
C4—C5—C6—C7	1.9 (2)	C14—C1—C15—N16	−128.50 (14)
C5—C6—C7—C2	0.5 (2)	C14—C9—C10—C11	0.3 (2)
C5—C6—C7—C8	−179.00 (13)	C15—C1—C2—C3	−1.4 (2)
C6—C7—C8—C9	−179.77 (12)	C15—C1—C2—C7	176.56 (12)
C7—C2—C3—C4	3.1 (2)	C15—C1—C14—C9	−176.11 (11)
C7—C8—C9—C10	179.46 (12)	C15—C1—C14—C13	4.96 (19)
C7—C8—C9—C14	0.0 (2)	C17—N16—C15—C1	179.78 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O16ⁱ	0.95	2.24	3.1267 (18)	154
C17—H17B···O16ⁱ	0.98	2.28	3.2037 (18)	157

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors would like to thank D. B. Cordes for his fruitful discussion. TH is grateful to Hacettepe University Scientific Research Project Unit.

Funding information

Funding for this research was provided by: Hacettepe Üniversitesi (grant No. 013 D04 602 004).

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