The title compound contains an almost planar anthracene ring system. In the crystal, intermolecular bifurcated C—H⋯O hydrogen bonds link the molecules into infinite chains along the a-axis direction and π–π stacking interactions between the benzene rings of adjacent molecules help to consolidate the three-dimensional architecture.
Keywords: C-anthracen-9-yl-N-methyl aldonitrone, crystal structure, hydrogen bond, π-stacking, Hirshfeld surface, energy framework analysis
Abstract
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.
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 dnorm 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 dnorm 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 di and de 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 (Eele), −10.9 (Epol), −62.7 (Edis), 65.8 (Erep) and −57.9 (Etot) for the C15—H15⋯O16, and −23.9 (Eele), −6.4 (Epol), −32.8 (Edis), 18.5 (Erep) and −47.1 (Etot) 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 Eele (red cylinders), Edis (green cylinders) and Etot (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 Eele, (b) dispersion energy Edis and (c) total energy Etot 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 Uiso(H) = kUeq(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 ▸) |
| Tmin, Tmax | 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 |
| Δρmax, Δρmin (e Å−3) | 0.30, −0.20 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026000599/vm2323sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000599/vm2323Isup2.hkl
checkcif. DOI: 10.1107/S2056989026000599/vm2323sup3.pdf
checkcif. DOI: 10.1107/S2056989026000599/vm2323sup4.pdf
Supporting information file. DOI: 10.1107/S2056989026000599/vm2323Isup5.cml
CCDC reference: 2524759
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors would like to thank D. B. Cordes for his fruitful discussion. TH is grateful to Hacettepe University Scientific Research Project Unit.
supplementary crystallographic information
1-Anthracen-9-yl-N-methylmethanimine oxide . Crystal data
| C16H13NO | F(000) = 496 |
| Mr = 235.27 | Dx = 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 |
1-Anthracen-9-yl-N-methylmethanimine oxide . Data collection
| 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 | Rint = 0.055 |
| Detector resolution: 5.8140 pixels mm-1 | θmax = 29.0°, θmin = 1.9° |
| shutterless scans | h = −6→6 |
| Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2024) | k = −21→21 |
| Tmin = 0.714, Tmax = 1.000 | l = −19→19 |
| 24788 measured reflections |
1-Anthracen-9-yl-N-methylmethanimine oxide . Refinement
| 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(Fo2) + (0.0587P)2 + 0.3266P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2788 reflections | Δρmax = 0.30 e Å−3 |
| 164 parameters | Δρmin = −0.20 e Å−3 |
| 0 restraints |
1-Anthracen-9-yl-N-methylmethanimine oxide . Special details
| 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. |
1-Anthracen-9-yl-N-methylmethanimine oxide . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| 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* |
1-Anthracen-9-yl-N-methylmethanimine oxide . Atomic displacement parameters (Å2)
| 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) |
1-Anthracen-9-yl-N-methylmethanimine oxide . Geometric parameters (Å, º)
| 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) |
1-Anthracen-9-yl-N-methylmethanimine oxide . Hydrogen-bond geometry (Å, º)
| 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.
Funding Statement
Funding for this research was provided by: Hacettepe Üniversitesi (grant No. 013 D04 602 004).
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989026000599/vm2323sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026000599/vm2323Isup2.hkl
checkcif. DOI: 10.1107/S2056989026000599/vm2323sup3.pdf
checkcif. DOI: 10.1107/S2056989026000599/vm2323sup4.pdf
Supporting information file. DOI: 10.1107/S2056989026000599/vm2323Isup5.cml
CCDC reference: 2524759
Additional supporting information: crystallographic information; 3D view; checkCIF report