(E)-4-{[(4-Meth­oxy­naphthalen-1-yl)methyl­idene]amino}­phenol

Ghames, A.; Ziani, N.; Djedouani, A.; Hannachi, D.; Crochet, A.; Stoeckli-Evans, H.

doi:10.1107/S2414314626008552

organic compounds

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ISSN: 2414-3146

Volume 11| Part 8| August 2026| x260855

https://doi.org/10.1107/S2414314626008552

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(E)-4-{[(4-Methoxynaphthalen-1-yl)methylidene]amino}phenol

Amel Ghames,^a Nouara Ziani,^a,^b Amel Djedouani,^c,^d ^* Douniazed Hannachi,^e Aurelian Crochet ^f and Helen Stoeckli-Evans ^g ^*‡

^aLaboratoire d'électrochimie des matériaux moléculaires et des complexes, (LEMMC), Département de génie des procédés, Université Ferhat Abbas, Sétif 19000, Algeria, ^bDépartement de chimie, Faculté des sciences, Université Ferhat Abbas, Sétif 19000, Algeria, ^cEcole Normale Supérieure de Constantine-Assia Djebar, Université Constantine 3, 25000, Ali Mendjli, Algeria, ^dLaboratoire des Produits Naturels d'Origine Végétale et de Synthése Organique, Faculté des Sciences Exactes, Université des Fréres Mentouri-Constantine 1, Algeria, ^eLaboratoire d'électrochimie, d'ingénierie moléculaire et de catalyse redox, Département de génie des procédés, Faculté de technologie, Universite Ferhat Abbas, Sétif 19000, Algeria, ^fChemistry Department, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland, and ^gInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: [email protected], [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 17 August 2026; accepted 18 August 2026; online 28 August 2026)

The title Schiff base compound, C₁₈H₁₅NO₂, was synthesized via the condensation reaction of 4-hydroxy aniline and 4-methoxy-1-naphthaldehyde in ethanol. The dihedral angle between the phenol ring and the mean plane of the naphthalene ring system is 75.81 (6)°. In the crystal, the molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds, enclosing R³₃(18) ring motifs and forming zigzag chains propagating along the c-axis direction. The chains are linked via C—H⋯π interactions forming slabs lying parallel to the ac plane.

Keywords: crystal structure; naphthalene; Schiff base; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 2582009

Structure description

Schiff bases exhibit a wide range of biological activities (Djabbour et al., 2025 ; Villar et al., 2004 ). They have applications in the field of water treatment as they have a great capacity for complexation of transition metals (Boudraa et al., 2023 ; Kalcher et al., 1995 ). Their use as corrosion inhibitors (e.g., Boudraa et al., 2023) reveal their importance in this field too. Herein, we report on the synthesis and crystal structure of the title compound, C₁₈H₁₅NO₂ (I).

The molecular structure of compound (I) is illustrated in Fig. 1. The configuration about the N1=C12 azomethine bond is E. The –C=N– bond length [1.282 (2) Å] is a little longer than the bond lengths observed in related compounds, such as (E)-1-(4-methoxynaphthalen-1-yl)-N-phenylmethanimine (II) [1.264 (4) Å; Linden et al., 1989 ] and (E)-2-{[(4-methoxynaphthalen-1-yl)methylene]amino}-4-methylphenol (III) [1.274 (2) Å; Yahiaoui et al., 2023 ]. A search of the Cambridge Structural Database (CSD, Version 6.01; last update May 2026; Groom et al., 2016 ) for the length of the azomethine bond of structures with the benzylideneaniline substructure gave 1601 hits (Filters: R ≤ 0.05, no disorder, no ions, no polymers, single crystals and organics only). An analysis using Mercury (Macrae et al., 2020 ) gave an average value for the –C=N– bond length of 1.277 (15) Å, with a median value of 1.278 Å. Hence, the N1=C12 bond length in (I) is normal.

Figure 1
A view of the molecular structure of compound (I). The displacement ellipsoids are drawn at the 50% probability level.

The dihedral angle between the phenol ring (C13–C18) and the mean plane of the naphthalene ring system (C1–C10; r.m.s. deviation 0.013 Å) in (I) is 75.81 (6)°. In compound (II) the corresponding dihedral angle is 64.33 (12)°, while in compound (III) the same dihedral angle is smaller, at 33.41 (4)° probably due to the presence of an intramolecular O—H⋯N hydrogen bond.

In the crystal of (I), the molecules are linked by O—H⋯N hydrogen bonds to form zigzag chains propagating along the c-axis direction (Fig. 2). The chains are consolidated by C—H⋯O hydrogen bonds, so enclosing R₃³(18) ring motifs (Fig. 2, Table 1). The chains are linked by C—H⋯π interactions forming slabs lying parallel to the ac plane (Fig. 3, Table 1). The slabs stack along the b-axis direction and there are no significant inter-planar interactions present.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the naphthalene ring system (C1–C10) and the phenol ring (C13–C18), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯N1ⁱ	0.91 (3)	1.97 (3)	2.849 (2)	160 (3)
C11—H11A⋯O2ⁱⁱ	0.97	2.53	3.409 (2)	150
C14—H14⋯Cg2ⁱⁱⁱ	0.94	2.90	3.627 (2)	135
C18—H18⋯Cg1^iv	0.94	2.82	3.745 (2)	170
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Figure 2
A partial view along the a-axis of the crystal structure of compound I, illustrating the formation of the zigzag chain via O—H⋯N and C—H⋯O hydrogen bonds and the formation of the R₃³(18) ring motifs (Table 1

). The various hydrogen bonds are shown as cyan dashed lines.

Figure 3
A view along the c-axis of the crystal packing of compound I. The C—H⋯π interactions are shown as dashed double arrows (see Table 1

; naphthalene ring system is pale green and the phenol ring is pale blue).

Synthesis and crystallization

Equimolar amounts of 4-hydroxy aniline (0.109 g, 0.01 mmol) and 4-methoxy naphthaldehyde (0.186 g, 0.01 mmol) were mixed in absolute ethanol (30 ml) and refluxed under stirring for 4 h. After cooling to room temperature, the solvent was allowed to evaporate slowly, yielding yellow needle-like crystals of (I).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₅NO₂
M_r	277.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	250
a, b, c (Å)	7.8365 (3), 27.460 (1), 13.0741 (5)
V (Å³)	2813.43 (18)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.69
Crystal size (mm)	0.54 × 0.24 × 0.09

Data collection
Diffractometer	Stoe Stadivari
Absorption correction	Analytical (X-RED32 and LANA; Stoe, 2025 )
T_min, T_max	0.682, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	17634, 2477, 2243
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 1.01
No. of reflections	2477
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25
Computer programs: X-AREA Pilatus3_SV, X-AREA and LANA (Stoe, 2025), SHELXT2019/3 (Sheldrick, 2015a ), Mercury (Macrae et al., 2020), SHELXL2019/3 (Sheldrick, 2015b ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2582009

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626008552/hb4570sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626008552/hb4570Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626008552/hb4570Isup3.cml

checkCIF report

Computing details top

(E)-4-{[(4-Methoxynaphthalen-1-yl)methylidene]amino}phenol top

Crystal data top

C₁₈H₁₅NO₂	D_x = 1.309 Mg m⁻³
M_r = 277.31	Cu Kα radiation, λ = 1.54186 Å
Orthorhombic, Pbca	Cell parameters from 30029 reflections
a = 7.8365 (3) Å	θ = 4.7–67.1°
b = 27.460 (1) Å	µ = 0.69 mm⁻¹
c = 13.0741 (5) Å	T = 250 K
V = 2813.43 (18) Å³	Needle, yellow
Z = 8	0.54 × 0.24 × 0.09 mm
F(000) = 1168

Data collection top

Stoe Stadivari diffractometer	2477 independent reflections
Radiation source: Primux 100 micro	2243 reflections with I > 2σ(I)
Graded multilayer mirror monochromator	R_int = 0.057
Detector resolution: 5.81 pixels mm^-1	θ_max = 66.9°, θ_min = 4.7°
rotation method, ω scans	h = −3→9
Absorption correction: analytical (X-Red32 and LANA; Stoe, 2025)	k = −32→27
T_min = 0.682, T_max = 0.938	l = −14→15
17634 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: mixed
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0836P)² + 0.6531P] where P = (F_o² + 2F_c²)/3
2477 reflections	(Δ/σ)_max = 0.004
195 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	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.

Refinement. The hydroxyl H atom (H1) was located in a difference Fourier map and freely refined. The C-bound hydrogen atoms were placed geometrically (C—H = 0.94–0.97 Å) and allowed to ride on their parent atoms with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.54483 (17)	0.42260 (4)	−0.11052 (8)	0.0607 (3)
O2	0.50176 (18)	0.27526 (4)	0.74559 (9)	0.0631 (4)
H1	0.535 (4)	0.2440 (11)	0.759 (2)	0.112 (9)*
N1	0.56304 (15)	0.31870 (4)	0.33044 (9)	0.0431 (3)
C1	0.57080 (17)	0.37828 (5)	0.19453 (11)	0.0408 (3)
C2	0.48289 (18)	0.35110 (5)	0.12373 (11)	0.0438 (3)
H2	0.429306	0.322240	0.145278	0.053*
C3	0.46995 (19)	0.36462 (5)	0.02107 (11)	0.0456 (3)
H3	0.408485	0.345058	−0.025015	0.055*
C4	0.54710 (19)	0.40648 (5)	−0.01231 (11)	0.0448 (4)
C5	0.7243 (2)	0.47925 (5)	0.02372 (13)	0.0544 (4)
H5	0.717067	0.488614	−0.045305	0.065*
C6	0.8157 (2)	0.50699 (6)	0.09119 (14)	0.0611 (5)
H6	0.871221	0.535300	0.068213	0.073*
C7	0.8272 (2)	0.49353 (5)	0.19402 (14)	0.0566 (4)
H7	0.890171	0.512896	0.239741	0.068*
C8	0.74786 (19)	0.45251 (5)	0.22859 (12)	0.0477 (4)
H8	0.756775	0.444017	0.298037	0.057*
C9	0.65200 (17)	0.42243 (4)	0.16155 (11)	0.0404 (3)
C10	0.64038 (18)	0.43649 (4)	0.05746 (11)	0.0423 (3)
C11	0.4544 (3)	0.39390 (7)	−0.18289 (14)	0.0765 (6)
H11C	0.462324	0.408915	−0.249878	0.115*
H11B	0.335501	0.391672	−0.162765	0.115*
H11A	0.503581	0.361505	−0.185446	0.115*
C12	0.57358 (18)	0.36320 (5)	0.30148 (11)	0.0433 (3)
H12	0.583650	0.387430	0.351919	0.052*
C13	0.55024 (17)	0.30924 (5)	0.43688 (10)	0.0404 (3)
C14	0.64259 (18)	0.27075 (5)	0.47837 (11)	0.0457 (4)
H14	0.712289	0.251745	0.435586	0.055*
C15	0.63350 (19)	0.26002 (5)	0.58132 (12)	0.0461 (4)
H15	0.701496	0.234978	0.608536	0.055*
C16	0.52446 (19)	0.28599 (5)	0.64513 (11)	0.0453 (4)
C17	0.4292 (2)	0.32384 (5)	0.60349 (11)	0.0486 (4)
H17	0.353863	0.341496	0.645387	0.058*
C18	0.44399 (19)	0.33576 (5)	0.50134 (11)	0.0448 (3)
H18	0.381461	0.362145	0.474999	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0941 (9)	0.0422 (6)	0.0456 (6)	−0.0098 (5)	−0.0054 (5)	0.0026 (4)
O2	0.0974 (9)	0.0459 (6)	0.0459 (6)	0.0143 (6)	0.0037 (5)	0.0037 (5)
N1	0.0487 (7)	0.0341 (6)	0.0465 (7)	−0.0005 (5)	0.0025 (5)	0.0007 (5)
C1	0.0435 (7)	0.0305 (6)	0.0484 (8)	0.0030 (5)	0.0021 (5)	0.0000 (5)
C2	0.0469 (7)	0.0312 (6)	0.0534 (8)	−0.0015 (6)	0.0022 (6)	0.0008 (6)
C3	0.0521 (8)	0.0352 (7)	0.0496 (8)	−0.0023 (6)	−0.0043 (6)	−0.0032 (6)
C4	0.0550 (8)	0.0337 (7)	0.0459 (8)	0.0037 (6)	0.0005 (6)	−0.0003 (6)
C5	0.0684 (10)	0.0363 (7)	0.0585 (9)	−0.0048 (7)	0.0056 (7)	0.0038 (6)
C6	0.0711 (11)	0.0369 (8)	0.0752 (11)	−0.0145 (7)	0.0048 (8)	0.0013 (7)
C7	0.0594 (10)	0.0381 (7)	0.0723 (11)	−0.0078 (7)	−0.0045 (7)	−0.0074 (7)
C8	0.0522 (8)	0.0368 (7)	0.0541 (8)	0.0003 (6)	−0.0037 (6)	−0.0028 (6)
C9	0.0418 (7)	0.0293 (6)	0.0501 (8)	0.0045 (5)	0.0020 (6)	−0.0018 (5)
C10	0.0470 (8)	0.0300 (6)	0.0500 (8)	0.0026 (5)	0.0034 (6)	−0.0014 (5)
C11	0.1276 (18)	0.0512 (10)	0.0508 (10)	−0.0136 (10)	−0.0176 (10)	0.0001 (7)
C12	0.0464 (8)	0.0342 (7)	0.0493 (8)	−0.0001 (6)	−0.0001 (6)	−0.0012 (6)
C13	0.0452 (7)	0.0315 (6)	0.0446 (7)	−0.0036 (5)	−0.0014 (5)	−0.0010 (5)
C14	0.0477 (8)	0.0330 (7)	0.0563 (9)	0.0034 (5)	0.0086 (6)	0.0022 (6)
C15	0.0499 (8)	0.0330 (7)	0.0553 (8)	0.0031 (6)	0.0001 (6)	0.0070 (6)
C16	0.0583 (8)	0.0339 (7)	0.0437 (8)	−0.0025 (6)	−0.0039 (6)	−0.0011 (5)
C17	0.0601 (9)	0.0389 (7)	0.0467 (8)	0.0083 (6)	−0.0005 (7)	−0.0064 (6)
C18	0.0519 (8)	0.0346 (7)	0.0480 (8)	0.0077 (6)	−0.0045 (6)	−0.0010 (6)

Geometric parameters (Å, º) top

O1—C4	1.3583 (18)	C7—C8	1.364 (2)
O1—C11	1.421 (2)	C7—H7	0.9400
O2—C16	1.3578 (18)	C8—C9	1.420 (2)
O2—H1	0.91 (3)	C8—H8	0.9400
N1—C12	1.2820 (18)	C9—C10	1.417 (2)
N1—C13	1.4192 (18)	C11—H11C	0.9700
C1—C2	1.374 (2)	C11—H11B	0.9700
C1—C9	1.4354 (18)	C11—H11A	0.9700
C1—C12	1.4585 (19)	C12—H12	0.9400
C2—C3	1.396 (2)	C13—C18	1.391 (2)
C2—H2	0.9400	C13—C14	1.3911 (19)
C3—C4	1.370 (2)	C14—C15	1.380 (2)
C3—H3	0.9400	C14—H14	0.9400
C4—C10	1.430 (2)	C15—C16	1.391 (2)
C5—C6	1.368 (2)	C15—H15	0.9400
C5—C10	1.416 (2)	C16—C17	1.391 (2)
C5—H5	0.9400	C17—C18	1.380 (2)
C6—C7	1.397 (2)	C17—H17	0.9400
C6—H6	0.9400	C18—H18	0.9400

C4—O1—C11	117.08 (12)	C9—C10—C5	119.68 (13)
C16—O2—H1	110.3 (19)	C9—C10—C4	119.23 (12)
C12—N1—C13	117.95 (12)	C5—C10—C4	121.08 (14)
C2—C1—C9	118.59 (13)	O1—C11—H11C	109.5
C2—C1—C12	119.94 (12)	O1—C11—H11B	109.5
C9—C1—C12	121.41 (12)	H11C—C11—H11B	109.5
C1—C2—C3	122.64 (13)	O1—C11—H11A	109.5
C1—C2—H2	118.7	H11C—C11—H11A	109.5
C3—C2—H2	118.7	H11B—C11—H11A	109.5
C4—C3—C2	119.82 (13)	N1—C12—C1	123.56 (13)
C4—C3—H3	120.1	N1—C12—H12	118.2
C2—C3—H3	120.1	C1—C12—H12	118.2
O1—C4—C3	124.66 (13)	C18—C13—C14	118.23 (13)
O1—C4—C10	114.96 (12)	C18—C13—N1	122.73 (12)
C3—C4—C10	120.38 (13)	C14—C13—N1	118.99 (12)
C6—C5—C10	120.26 (15)	C15—C14—C13	121.05 (13)
C6—C5—H5	119.9	C15—C14—H14	119.5
C10—C5—H5	119.9	C13—C14—H14	119.5
C5—C6—C7	120.45 (14)	C14—C15—C16	120.49 (13)
C5—C6—H6	119.8	C14—C15—H15	119.8
C7—C6—H6	119.8	C16—C15—H15	119.8
C8—C7—C6	120.54 (15)	O2—C16—C17	118.07 (13)
C8—C7—H7	119.7	O2—C16—C15	123.33 (13)
C6—C7—H7	119.7	C17—C16—C15	118.56 (13)
C7—C8—C9	121.15 (15)	C18—C17—C16	120.74 (13)
C7—C8—H8	119.4	C18—C17—H17	119.6
C9—C8—H8	119.4	C16—C17—H17	119.6
C10—C9—C8	117.92 (12)	C17—C18—C13	120.84 (13)
C10—C9—C1	119.34 (12)	C17—C18—H18	119.6
C8—C9—C1	122.72 (13)	C13—C18—H18	119.6

C9—C1—C2—C3	0.2 (2)	C6—C5—C10—C4	−178.70 (15)
C12—C1—C2—C3	177.47 (13)	O1—C4—C10—C9	−179.24 (12)
C1—C2—C3—C4	0.1 (2)	C3—C4—C10—C9	0.0 (2)
C11—O1—C4—C3	0.6 (2)	O1—C4—C10—C5	−0.7 (2)
C11—O1—C4—C10	179.71 (16)	C3—C4—C10—C5	178.48 (14)
C2—C3—C4—O1	178.93 (13)	C13—N1—C12—C1	−173.88 (12)
C2—C3—C4—C10	−0.2 (2)	C2—C1—C12—N1	29.7 (2)
C10—C5—C6—C7	−0.1 (3)	C9—C1—C12—N1	−153.10 (13)
C5—C6—C7—C8	0.2 (3)	C12—N1—C13—C18	43.94 (19)
C6—C7—C8—C9	0.1 (2)	C12—N1—C13—C14	−138.50 (14)
C7—C8—C9—C10	−0.4 (2)	C18—C13—C14—C15	−2.0 (2)
C7—C8—C9—C1	178.18 (14)	N1—C13—C14—C15	−179.68 (12)
C2—C1—C9—C10	−0.44 (19)	C13—C14—C15—C16	3.4 (2)
C12—C1—C9—C10	−177.64 (12)	C14—C15—C16—O2	175.76 (14)
C2—C1—C9—C8	−178.98 (13)	C14—C15—C16—C17	−1.9 (2)
C12—C1—C9—C8	3.8 (2)	O2—C16—C17—C18	−178.60 (13)
C8—C9—C10—C5	0.42 (19)	C15—C16—C17—C18	−0.8 (2)
C1—C9—C10—C5	−178.19 (13)	C16—C17—C18—C13	2.1 (2)
C8—C9—C10—C4	178.96 (12)	C14—C13—C18—C17	−0.7 (2)
C1—C9—C10—C4	0.35 (19)	N1—C13—C18—C17	176.85 (13)
C6—C5—C10—C9	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the naphthalene ring system (C1–C10) and the phenol ring (C13–C18), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···N1ⁱ	0.91 (3)	1.97 (3)	2.849 (2)	160 (3)
C11—H11A···O2ⁱⁱ	0.97	2.53	3.409 (2)	150
C14—H14···Cg2ⁱⁱⁱ	0.94	2.90	3.627 (2)	135
C18—H18···Cg1^iv	0.94	2.82	3.745 (2)	170

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

Footnotes

‡Prof. Emerita.

Acknowledgements

The authors are grateful to the University of Setif 1 and to the Algerian DGRSDT (Directorate General for Scientific Research and Technological Development) for supporting this research. HSE is grateful to the University of Neuchâtel for their support over the years.

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