(2E)-2-[(4-Eth­oxy­phen­yl)imino]-1,2-di­phenylethanone

Chiter, C.; Boudinar, Y.; Akkache, H.E.M.; Djedouani, A.; Tabti, S.; Jeanneau, E.

doi:10.1107/S2414314626007406

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 7| July 2026| x260740

https://doi.org/10.1107/S2414314626007406

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(2E)-2-[(4-Ethoxyphenyl)imino]-1,2-diphenylethanone

Chaabane Chiter,^a Yamina Boudinar,^b,^c Hibet Errahmane Meroua Akkache,^d ^* Amel Djedouani,^e,^f Salima Tabti ^g,^h and Erwann Jeanneau ⁱ

^aLaboratoire de Chimie, Ingénierie Moléculaire et Nanostructures, Université Ferhat Abbas Sétif 1, Sétif, 19000, Algeria, ^bDepartment of Chemistry, Faculty of Sciences, University of 20 August 1955, Skikda 21000, Algeria, ^cLaboratory of Physico-Chemistry Research on Surfaces and Interfaces, University of Skikda 21000, Algeria, ^dCrystallography Laboratory, Department of Physics, University of Constantine-1, 25000 Constantine, Algeria, ^eEcole normale supérieure de Constantine-Assia Djebar-Université, Ali Mendjeli, Constantine 3, Constantine 25000, Algeria, ^fLaboratoire de produits d'origine végétale et de synthése organique 'PHYSYNOR', Université Mentouri-Constantine 1, Constantine 25000, Algeria, ^gDepartment of Ecology and Environment, Faculty of Life and Natural Sciences of Earth and Universe Sciences, Mohamed El Bachir El Ibrahimi University, El Anasser, Bordj BouArreridj 34000, Algeria, ^hLaboratory of Electrochemistry and Environment, Mohamed El Bachir El Ibrahimi University, El Anasser, Bordj BouArreridj 34000, Algeria, and ⁱCentre de Diffractométrie Henri Longchambon, Université Claude Bernard Lyon 1, 5 rue de la Doua, 69100 Villeurbanne, France
^*Correspondence e-mail: [email protected]

Edited by M. Zeller, Purdue University, USA (Received 25 June 2026; accepted 18 July 2026; online 28 July 2026)

The title compound, C₂₂H₁₉NO₂, is an imino-ketone Schiff base. The configuration about the azomethine bond is E. The aromatic rings of the 1,2-diphenylethanone moiety are inclined to each other by 80.43 (7)°. The 4-ethoxyphenyl ring is inclined to the phenylethanone ring by 81.91 (7)° and to the phenyl ring to which it is trans by 68.56 (7)°. In the crystal, four symmetry-related molecules are linked by C—H⋯O hydrogen bonds to form square-like units with an R³₄(36) ring motif, which are linked through bifurcated C—H⋯O hydrogen bonds to form sheets parallel to the (101) plane.

Keywords: crystal structure; imino-ketone; Schiff base; hydrogen bonding.

CCDC reference: 2574557

Structure description

As part of our ongoing studies of Schiff bases (Ziani et al., 2023 ; Bouchama et al., 2007 ), we describe herein the synthesis and crystal structure of the title imino-ketone compound, (I). The molecular structure of (I) is illustrated in Fig. 1. The configuration about the azomethine bond, C1=N1, is E, with a bond length of 1.278 (2) Å. This value is essentially identical to that observed for the 4-methoxyphenyl analogue (II), viz. 1.277 (2) Å (Wang et al., 2021 ). In the 1,2-diphenylethan-1-one unit, the aromatic rings A (C2–C7) and B (C9–C14) are inclined to each other by 80.43 (7)°. The 4-ethoxyphenyl ring C (C15–C20) is inclined to rings A and B by 68.56 (7) and 81.91 (7)°, respectively. In the 4-methoxyphenyl analogue (II), these dihedral angles are similar; A/B is 79.85 (6)°, A/C is 70.06 (6)° and B/C is 77.26 (6)°. The 4-ethoxyphenyl moiety is almost co-planar with the ethoxy unit (O2/C21/C22), being inclined to aromatic ring C by only 1.33 (15)°. There is a short intramolecular C16—H16⋯O1 contact in the molecule (Fig. 1 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1	0.95	2.56	3.068 (2)	114
C12—H12⋯O1ⁱ	0.95	2.41	3.279 (2)	151
C22—H22A⋯O1ⁱⁱ	0.98	2.55	3.462 (2)	155
Symmetry codes: (i) ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
A view of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. The intramolecular C—H⋯O hydrogen bond (Table 1

) is shown as a dashed blue line.

In the crystal, four symmetry-related molecules are linked by C—H⋯O hydrogen bonds, forming a square-like unit with an R₄³(36) ring motif (Table 1 and Fig. 2). These units are linked by bifurcated C—H⋯O hydrogen bonds, forming sheets lying parallel to the (10 $[\overline{1}]$ ) plane (Fig. 3).

Figure 2
A view of four symmetry-related molecules of (I) that are linked by C—H⋯O hydrogen bonds (Table 1

) to form a square-like unit with an R₄³(36) ring motif. (The acceptor O atoms are red, the donor H atoms are grey and the ring atoms are green.)

Figure 3
A view of the sheet-like hydrogen-bonded arrangement of symmetry-related molecules in the crystal of (I), lying parallel to the (10 $[\overline{1}]$ ) plane.

Synthesis and crystallization

Equimolar amounts of benzil (0.210 g, 0.01 mmol) and 4-ethoxyaniline (0.137 g, 0.01 mmol) were mixed in absolute ethanol (30 ml) and refluxed under stirring for 3 h. After cooling to room temperature, the solvent was allowed to evaporate slowly, yielding yellow needle-like crystals (yield 0.249 g, 76%, m.p. 529.5 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₉NO₂
M_r	329.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.0674 (4), 8.0633 (2), 16.4309 (5)
β (°)	101.412 (3)
V (Å³)	1697.04 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.17 × 0.05

Data collection
Diffractometer	Xcalibur, Eos, Nova
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 )
T_min, T_max	0.568, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	22651, 4240, 3037
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.117, 1.04
No. of reflections	4240
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26
Computer programs: CrysAlis PRO (Rigaku OD, 2022), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2025/1 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ), OLEX2 (Dolomanov et al., 2009 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2574557

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314626007406/zl4101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626007406/zl4101Isup2.hkl

checkCIF report

Computing details top

(2E)-2-[(4-Ethoxyphenyl)imino]-1,2-diphenylethanone top

Crystal data top

C₂₂H₁₉NO₂	F(000) = 696
M_r = 329.38	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.0674 (4) Å	Cell parameters from 7263 reflections
b = 8.0633 (2) Å	θ = 4.0–28.9°
c = 16.4309 (5) Å	µ = 0.08 mm⁻¹
β = 101.412 (3)°	T = 100 K
V = 1697.04 (9) Å³	Plate, yellow
Z = 4	0.32 × 0.17 × 0.05 mm

Data collection top

Xcalibur, Eos, Nova diffractometer	3037 reflections with I > 2σ(I)
Detector resolution: 15.9897 pixels mm^-1	R_int = 0.050
ω scans	θ_max = 29.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	h = −17→17
T_min = 0.568, T_max = 1.000	k = −11→10
22651 measured reflections	l = −22→22
4240 independent 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0451P)² + 0.5117P] where P = (F_o² + 2F_c²)/3
4240 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.27 e Å⁻³
0 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.

Refinement. The hydrogen atoms were fixed geometrically (C—H = 0.95–0.99 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	0.37863 (9)	0.72732 (14)	0.72318 (7)	0.0230 (3)
O2	−0.00143 (8)	0.65400 (14)	0.42270 (7)	0.0233 (3)
N1	0.42408 (10)	0.75710 (16)	0.54025 (8)	0.0177 (3)
C1	0.47276 (12)	0.72080 (18)	0.61342 (9)	0.0159 (3)
C2	0.58625 (11)	0.75382 (18)	0.63777 (9)	0.0150 (3)
C3	0.63793 (12)	0.84505 (19)	0.58563 (9)	0.0187 (3)
H3	0.599688	0.888983	0.535014	0.022*
C4	0.74416 (12)	0.8714 (2)	0.60744 (10)	0.0210 (3)
H4	0.778474	0.934724	0.572067	0.025*
C5	0.80129 (12)	0.8062 (2)	0.68071 (10)	0.0220 (4)
H5	0.874683	0.822321	0.694735	0.026*
C6	0.75096 (12)	0.7176 (2)	0.73313 (10)	0.0221 (4)
H6	0.789725	0.673329	0.783465	0.026*
C7	0.64419 (12)	0.6935 (2)	0.71241 (10)	0.0208 (4)
H7	0.609858	0.634988	0.749469	0.025*
C8	0.42051 (11)	0.64005 (19)	0.67898 (9)	0.0164 (3)
C9	0.42599 (11)	0.45736 (18)	0.68773 (9)	0.0150 (3)
C10	0.39198 (12)	0.3842 (2)	0.75483 (9)	0.0195 (3)
H10	0.362780	0.450853	0.792138	0.023*
C11	0.40093 (13)	0.2151 (2)	0.76670 (10)	0.0232 (4)
H11	0.377345	0.165044	0.812001	0.028*
C12	0.44422 (12)	0.1181 (2)	0.71271 (10)	0.0229 (4)
H12	0.451685	0.002030	0.721944	0.027*
C13	0.47678 (12)	0.1891 (2)	0.64523 (10)	0.0199 (3)
H13	0.505542	0.121833	0.607927	0.024*
C14	0.46712 (11)	0.35854 (19)	0.63259 (9)	0.0166 (3)
H14	0.488628	0.407542	0.586138	0.020*
C15	0.31464 (12)	0.73071 (19)	0.51553 (9)	0.0175 (3)
C16	0.24190 (12)	0.80883 (19)	0.55370 (9)	0.0189 (3)
H16	0.265110	0.877720	0.600625	0.023*
C17	0.13555 (12)	0.78732 (19)	0.52400 (10)	0.0195 (3)
H17	0.086599	0.841725	0.550558	0.023*
C18	0.10068 (12)	0.6867 (2)	0.45574 (9)	0.0188 (3)
C19	0.17346 (12)	0.6111 (2)	0.41623 (10)	0.0212 (4)
H19	0.150243	0.543058	0.368988	0.025*
C20	0.27838 (12)	0.6342 (2)	0.44505 (9)	0.0213 (4)
H20	0.327052	0.583954	0.416726	0.026*
C21	−0.07850 (12)	0.7274 (2)	0.46183 (11)	0.0232 (4)
H21A	−0.071613	0.849674	0.462343	0.028*
H21B	−0.069898	0.688132	0.519880	0.028*
C22	−0.18352 (12)	0.6770 (2)	0.41299 (10)	0.0250 (4)
H22A	−0.189758	0.711703	0.355052	0.038*
H22B	−0.238460	0.730179	0.436621	0.038*
H22C	−0.190857	0.556242	0.415420	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0319 (7)	0.0175 (6)	0.0236 (6)	0.0029 (5)	0.0153 (5)	−0.0003 (5)
O2	0.0178 (6)	0.0292 (7)	0.0237 (6)	0.0011 (5)	0.0058 (5)	−0.0046 (5)
N1	0.0174 (7)	0.0182 (7)	0.0183 (6)	0.0001 (5)	0.0057 (5)	0.0024 (5)
C1	0.0205 (8)	0.0118 (7)	0.0174 (7)	0.0008 (6)	0.0086 (6)	−0.0011 (6)
C2	0.0179 (8)	0.0110 (7)	0.0177 (7)	0.0005 (6)	0.0072 (6)	−0.0023 (6)
C3	0.0223 (8)	0.0173 (8)	0.0178 (7)	0.0014 (6)	0.0073 (6)	0.0013 (6)
C4	0.0226 (8)	0.0185 (8)	0.0244 (8)	−0.0015 (7)	0.0109 (7)	0.0000 (7)
C5	0.0188 (8)	0.0201 (8)	0.0273 (9)	−0.0017 (7)	0.0052 (7)	−0.0045 (7)
C6	0.0229 (9)	0.0219 (9)	0.0201 (8)	−0.0017 (7)	0.0011 (7)	0.0012 (7)
C7	0.0258 (9)	0.0189 (8)	0.0191 (8)	−0.0042 (7)	0.0079 (7)	0.0007 (6)
C8	0.0173 (8)	0.0167 (8)	0.0158 (7)	−0.0006 (6)	0.0049 (6)	0.0003 (6)
C9	0.0138 (7)	0.0142 (7)	0.0169 (7)	−0.0012 (6)	0.0029 (6)	0.0008 (6)
C10	0.0235 (8)	0.0184 (8)	0.0183 (8)	−0.0014 (7)	0.0081 (6)	−0.0015 (6)
C11	0.0289 (9)	0.0210 (9)	0.0210 (8)	−0.0048 (7)	0.0078 (7)	0.0033 (7)
C12	0.0283 (9)	0.0135 (8)	0.0261 (8)	−0.0011 (7)	0.0037 (7)	0.0008 (7)
C13	0.0207 (8)	0.0172 (8)	0.0215 (8)	0.0017 (6)	0.0034 (6)	−0.0043 (7)
C14	0.0156 (7)	0.0185 (8)	0.0162 (7)	−0.0013 (6)	0.0046 (6)	−0.0002 (6)
C15	0.0180 (8)	0.0180 (8)	0.0178 (7)	−0.0004 (6)	0.0066 (6)	0.0054 (6)
C16	0.0233 (8)	0.0156 (8)	0.0185 (8)	−0.0015 (6)	0.0060 (6)	0.0007 (6)
C17	0.0211 (8)	0.0179 (8)	0.0217 (8)	0.0029 (6)	0.0097 (6)	0.0022 (7)
C18	0.0183 (8)	0.0199 (8)	0.0189 (8)	0.0000 (6)	0.0056 (6)	0.0042 (6)
C19	0.0233 (8)	0.0241 (9)	0.0169 (7)	−0.0003 (7)	0.0058 (6)	−0.0018 (7)
C20	0.0215 (8)	0.0259 (9)	0.0187 (8)	0.0029 (7)	0.0094 (6)	0.0010 (7)
C21	0.0213 (8)	0.0228 (9)	0.0277 (9)	0.0025 (7)	0.0103 (7)	−0.0003 (7)
C22	0.0216 (9)	0.0285 (9)	0.0262 (9)	0.0027 (7)	0.0078 (7)	0.0021 (7)

Geometric parameters (Å, º) top

O1—C8	1.2162 (18)	C11—H11	0.9500
O2—C18	1.3630 (19)	C11—C12	1.385 (2)
O2—C21	1.4263 (18)	C12—H12	0.9500
N1—C1	1.2779 (19)	C12—C13	1.387 (2)
N1—C15	1.423 (2)	C13—H13	0.9500
C1—C2	1.482 (2)	C13—C14	1.384 (2)
C1—C8	1.530 (2)	C14—H14	0.9500
C2—C3	1.400 (2)	C15—C16	1.389 (2)
C2—C7	1.395 (2)	C15—C20	1.398 (2)
C3—H3	0.9500	C16—H16	0.9500
C3—C4	1.380 (2)	C16—C17	1.390 (2)
C4—H4	0.9500	C17—H17	0.9500
C4—C5	1.388 (2)	C17—C18	1.386 (2)
C5—H5	0.9500	C18—C19	1.394 (2)
C5—C6	1.381 (2)	C19—H19	0.9500
C6—H6	0.9500	C19—C20	1.372 (2)
C6—C7	1.383 (2)	C20—H20	0.9500
C7—H7	0.9500	C21—H21A	0.9900
C8—C9	1.481 (2)	C21—H21B	0.9900
C9—C10	1.398 (2)	C21—C22	1.502 (2)
C9—C14	1.392 (2)	C22—H22A	0.9800
C10—H10	0.9500	C22—H22B	0.9800
C10—C11	1.380 (2)	C22—H22C	0.9800

C18—O2—C21	117.58 (12)	C13—C12—H12	119.7
C1—N1—C15	121.28 (13)	C12—C13—H13	120.2
N1—C1—C2	119.89 (13)	C14—C13—C12	119.62 (14)
N1—C1—C8	123.46 (13)	C14—C13—H13	120.2
C2—C1—C8	116.64 (13)	C9—C14—H14	119.9
C3—C2—C1	120.48 (13)	C13—C14—C9	120.19 (14)
C7—C2—C1	120.99 (13)	C13—C14—H14	119.9
C7—C2—C3	118.53 (14)	C16—C15—N1	122.83 (14)
C2—C3—H3	119.9	C16—C15—C20	118.45 (14)
C4—C3—C2	120.29 (14)	C20—C15—N1	118.45 (14)
C4—C3—H3	119.9	C15—C16—H16	119.6
C3—C4—H4	119.8	C15—C16—C17	120.73 (15)
C3—C4—C5	120.49 (15)	C17—C16—H16	119.6
C5—C4—H4	119.8	C16—C17—H17	119.9
C4—C5—H5	120.1	C18—C17—C16	120.20 (14)
C6—C5—C4	119.73 (15)	C18—C17—H17	119.9
C6—C5—H5	120.1	O2—C18—C17	125.09 (14)
C5—C6—H6	120.0	O2—C18—C19	115.73 (14)
C5—C6—C7	120.06 (15)	C17—C18—C19	119.18 (14)
C7—C6—H6	120.0	C18—C19—H19	119.8
C2—C7—H7	119.6	C20—C19—C18	120.49 (15)
C6—C7—C2	120.85 (15)	C20—C19—H19	119.8
C6—C7—H7	119.6	C15—C20—H20	119.6
O1—C8—C1	119.36 (14)	C19—C20—C15	120.89 (15)
O1—C8—C9	122.45 (13)	C19—C20—H20	119.6
C9—C8—C1	118.16 (12)	O2—C21—H21A	110.2
C10—C9—C8	118.64 (13)	O2—C21—H21B	110.2
C14—C9—C8	121.59 (13)	O2—C21—C22	107.39 (13)
C14—C9—C10	119.73 (14)	H21A—C21—H21B	108.5
C9—C10—H10	120.1	C22—C21—H21A	110.2
C11—C10—C9	119.81 (14)	C22—C21—H21B	110.2
C11—C10—H10	120.1	C21—C22—H22A	109.5
C10—C11—H11	119.9	C21—C22—H22B	109.5
C10—C11—C12	120.12 (15)	C21—C22—H22C	109.5
C12—C11—H11	119.9	H22A—C22—H22B	109.5
C11—C12—H12	119.7	H22A—C22—H22C	109.5
C11—C12—C13	120.51 (15)	H22B—C22—H22C	109.5

O1—C8—C9—C10	−7.1 (2)	C8—C1—C2—C3	−172.28 (13)
O1—C8—C9—C14	175.02 (14)	C8—C1—C2—C7	8.5 (2)
O2—C18—C19—C20	−179.23 (14)	C8—C9—C10—C11	−176.86 (14)
N1—C1—C2—C3	8.9 (2)	C8—C9—C14—C13	176.21 (14)
N1—C1—C2—C7	−170.37 (14)	C9—C10—C11—C12	0.5 (2)
N1—C1—C8—O1	−86.83 (19)	C10—C9—C14—C13	−1.6 (2)
N1—C1—C8—C9	95.03 (18)	C10—C11—C12—C13	−1.5 (2)
N1—C15—C16—C17	175.87 (14)	C11—C12—C13—C14	0.9 (2)
N1—C15—C20—C19	−176.97 (14)	C12—C13—C14—C9	0.7 (2)
C1—N1—C15—C16	61.3 (2)	C14—C9—C10—C11	1.0 (2)
C1—N1—C15—C20	−124.78 (16)	C15—N1—C1—C2	−178.45 (13)
C1—C2—C3—C4	−178.13 (14)	C15—N1—C1—C8	2.8 (2)
C1—C2—C7—C6	176.87 (14)	C15—C16—C17—C18	0.2 (2)
C1—C8—C9—C10	170.95 (13)	C16—C15—C20—C19	−2.8 (2)
C1—C8—C9—C14	−6.9 (2)	C16—C17—C18—O2	178.41 (14)
C2—C1—C8—O1	94.38 (17)	C16—C17—C18—C19	−1.6 (2)
C2—C1—C8—C9	−83.76 (17)	C17—C18—C19—C20	0.8 (2)
C2—C3—C4—C5	0.8 (2)	C18—O2—C21—C22	178.44 (13)
C3—C2—C7—C6	−2.4 (2)	C18—C19—C20—C15	1.4 (2)
C3—C4—C5—C6	−1.6 (2)	C20—C15—C16—C17	2.0 (2)
C4—C5—C6—C7	0.4 (2)	C21—O2—C18—C17	−0.7 (2)
C5—C6—C7—C2	1.7 (2)	C21—O2—C18—C19	179.29 (14)
C7—C2—C3—C4	1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1	0.95	2.56	3.068 (2)	114
C12—H12···O1ⁱ	0.95	2.41	3.279 (2)	151
C22—H22A···O1ⁱⁱ	0.98	2.55	3.462 (2)	155

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

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