1-Naphthamide

Bensegueni, M.A.; Ghallab, R.; Gheries, D.; Seghiri, A.; Nouail, L.

doi:10.1107/S2414314626009892

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 9| September 2026| x260989

https://doi.org/10.1107/S2414314626009892

Open

access

1-Naphthamide

Mohamed Abdellatif Bensegueni,^a Rochdi Ghallab,^b ^* Dorsaf Gheries,^a,^c Asma Seghiri ^a and Lamis Nouail ^a

^aEnvironmental, Molecular and Structural Chemistry Research Unit, University of Constantine-1, 25000, Constantine, Algeria, ^bLaboratoire de Technologie des Matériaux Avancés, Ecole Nationale, Polytechnique, de Constantine, Algeria, and ^cCRM2, UMR CNRS 7036, Faculté des Sciences et Technologies, Université de Lorraine, Institut Jean Barriol, BP 70239, 54506 Vandoeuvre-lès-Nancy Cedex, France
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 2 September 2026; accepted 23 September 2026; online 30 September 2026)

In the title compound, C₁₁H₉NO, the dihedral angle between the naphthalene fused-ring system and the amide group is 42.18 (9)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into (100) sheets. No significant aromatic π–π stacking is observed.

Keywords: crystal structure; naphthalene ring; hydrogen bonds.

CCDC reference: 2590330

Structure description

The title compound (I), with molecular formula C₁₁H₉NO, crystallizes in the monoclinic space group P2₁/c. The asymmetric unit contains one molecule in which the dihedral angle between the C2–C11 fused ring system (r.m.s. deviation = 0.008 Å) and the C1/N1/O1 amide moiety is 42.18 (9)° (Fig. 1). The significant twist probably arises to minimize steric crowding. The geometrical parameters for the amide group [C1—N1 = 1.3249 (19) Å, C1—O1 = 1.245 (2) Å and angles O1—C1—N1, O1—C1—C2 and N1—C1—C2 close to 120°) support a conjugated amide system, as expected. A short intramolecular C4—H4⋯O1 contact occurs.

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

In the extended structure of (I), the crystal cohesion is dominated by N11—H1A⋯O1 and N1—H1B⋯O1 hydrogen bonds (Table 1). The former generate inversion dimers and the latter link the dimers into (100) sheets (Fig. 2 and Table 1). The separations between the aromatic ring planes [shortest centroid–centroid separation = 4.799 (4) Å] are too large to support significant aromatic π–π stacking interactions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.38	2.969 (3)	121
N1—H1A⋯O1ⁱ	0.86	2.10	2.951 (3)	170
N1—H1B⋯O1ⁱⁱ	0.86	2.06	2.889 (3)	163
Symmetry codes: (i) ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The packing in (I) with hydrogen bonds shown as black dashed lines.

Hirshfeld surface analysis and the associated two-dimensional fingerprint plots were used to quantify the intermolecular contacts in the crystal of (I) (Fig. 3). The fingerprint plots show that H⋯H contacts make the largest contribution (42.2%), followed closely by C⋯H/H⋯C contacts (40.2%). The O⋯H/H⋯O contacts account for 14.20%, while all other contributions are less than 2.0%. These results show that the cohesion of the crystal is primarily governed by van der Waals contacts, with aromatic π–π stacking interactions not playing a significant role in establishing the supramolecular architecture.

Figure 3
Hirshfeld surfaces of (I) mapped over d_norm, shown as front and back views.

For the related structure of 9-anthramide, see Heller & Schmidt (1971 ).

Synthesis and crystallization

1-Naphthamide was obtained by aqueous hydrolysis of 1-naphthonitrile under heating. The starting nitrile was suspended in water and the mixture was heated until complete conversion to the amide was achieved. Colourless blocks of (I) were grown by slow evaporation of an aqueous solution of the compound at room temperature.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₉NO
M_r	171.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.787 (5), 6.053 (5), 9.954 (5)
β (°)	90.448 (5)
V (Å³)	890.9 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.14 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 )
T_min, T_max	0.753, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5594, 2584, 1535
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.207, 1.05
No. of reflections	2584
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.27
Computer programs: CrysAlis PRO (Rigaku OD, 2015), OLEX2.solve 1.5 (Bourhis et al., 2015 ), SHELXL (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2590330

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009892/hb4572sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009892/hb4572Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626009892/hb4572Isup3.cml

checkCIF report

Computing details top

Naphthalene-1-carboxamide top

Crystal data top

C₁₁H₉NO	F(000) = 360
M_r = 171.19	D_x = 1.276 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.787 (5) Å	Cell parameters from 2494 reflections
b = 6.053 (5) Å	θ = 2.5–35.6°
c = 9.954 (5) Å	µ = 0.08 mm⁻¹
β = 90.448 (5)°	T = 293 K
V = 890.9 (9) Å³	Block, colourless
Z = 4	0.14 × 0.13 × 0.11 mm

Data collection top

Saxi-CrysAlisPro-abstract goniometer imported SAXI images diffractometer	2584 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1535 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 30.0°, θ_min = 3.6°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	h = −9→20
T_min = 0.753, T_max = 1.000	k = −8→5
5594 measured reflections	l = −13→13

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)] = 0.071	H-atom parameters constrained
wR(F²) = 0.207	w = 1/[σ²(F_o²) + (0.106P)² + 0.0779P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2584 reflections	Δρ_max = 0.22 e Å⁻³
118 parameters	Δρ_min = −0.27 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.

Refinement. The H atoms were placed geometrically (N—H = 0.86 Å, C—H = 0.93 Å) and refined as riding atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.92484 (9)	0.3228 (2)	0.10353 (11)	0.0589 (4)
C11	0.84713 (15)	−0.1053 (3)	−0.10734 (18)	0.0600 (5)
H11	0.9018	−0.1167	−0.1524	0.072*
C2	0.83223 (12)	0.0721 (3)	−0.02377 (15)	0.0456 (4)
C1	0.90457 (11)	0.2427 (3)	−0.00788 (15)	0.0472 (4)
C3	0.74867 (11)	0.0887 (3)	0.04678 (15)	0.0439 (4)
C4	0.72663 (12)	0.2652 (3)	0.13314 (17)	0.0509 (4)
H4	0.7684	0.3780	0.1470	0.061*
C8	0.68255 (13)	−0.0809 (3)	0.02734 (19)	0.0550 (5)
C7	0.59888 (15)	−0.0640 (4)	0.0951 (2)	0.0721 (6)
H7	0.5555	−0.1735	0.0827	0.086*
C9	0.70104 (17)	−0.2580 (3)	−0.0600 (2)	0.0681 (6)
H9	0.6579	−0.3681	−0.0725	0.082*
C5	0.64530 (15)	0.2736 (4)	0.1967 (2)	0.0659 (6)
H5	0.6326	0.3912	0.2537	0.079*
C10	0.78034 (18)	−0.2706 (3)	−0.1257 (2)	0.0701 (6)
H10	0.7912	−0.3884	−0.1833	0.084*
C6	0.58088 (15)	0.1078 (5)	0.1774 (2)	0.0772 (7)
H6	0.5256	0.1156	0.2210	0.093*
N1	0.94732 (11)	0.3035 (3)	−0.11836 (13)	0.0605 (5)
H1A	0.9900	0.3999	−0.1139	0.073*
H1B	0.9324	0.2465	−0.1945	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0605 (8)	0.0885 (10)	0.0276 (6)	−0.0165 (7)	0.0030 (5)	−0.0033 (6)
C11	0.0731 (13)	0.0653 (12)	0.0416 (9)	0.0114 (10)	0.0017 (8)	−0.0031 (8)
C2	0.0543 (10)	0.0526 (10)	0.0299 (7)	0.0032 (7)	−0.0019 (6)	0.0028 (7)
C1	0.0478 (9)	0.0653 (11)	0.0285 (7)	0.0027 (7)	0.0025 (6)	0.0008 (7)
C3	0.0499 (9)	0.0482 (9)	0.0335 (7)	−0.0009 (7)	−0.0040 (6)	0.0066 (6)
C4	0.0527 (10)	0.0581 (10)	0.0418 (9)	−0.0015 (8)	0.0036 (7)	0.0006 (7)
C8	0.0630 (11)	0.0545 (10)	0.0472 (9)	−0.0073 (8)	−0.0089 (8)	0.0095 (8)
C7	0.0613 (13)	0.0844 (15)	0.0703 (14)	−0.0239 (11)	−0.0050 (10)	0.0150 (12)
C9	0.0880 (16)	0.0549 (12)	0.0612 (13)	−0.0146 (10)	−0.0138 (11)	0.0033 (9)
C5	0.0580 (11)	0.0825 (14)	0.0572 (12)	0.0048 (10)	0.0090 (9)	−0.0071 (10)
C10	0.1031 (18)	0.0500 (11)	0.0572 (12)	0.0029 (11)	−0.0113 (12)	−0.0088 (9)
C6	0.0538 (12)	0.1050 (18)	0.0730 (15)	−0.0059 (12)	0.0124 (10)	0.0030 (13)
N1	0.0655 (10)	0.0879 (11)	0.0281 (7)	−0.0179 (8)	0.0101 (6)	−0.0073 (7)

Geometric parameters (Å, º) top

O1—C1	1.245 (2)	C8—C9	1.408 (3)
C11—H11	0.9300	C7—H7	0.9300
C11—C2	1.377 (3)	C7—C6	1.352 (3)
C11—C10	1.417 (3)	C9—H9	0.9300
C2—C1	1.495 (3)	C9—C10	1.349 (3)
C2—C3	1.430 (2)	C5—H5	0.9300
C1—N1	1.3249 (19)	C5—C6	1.396 (3)
C3—C4	1.411 (2)	C10—H10	0.9300
C3—C8	1.430 (3)	C6—H6	0.9300
C4—H4	0.9300	N1—H1A	0.8600
C4—C5	1.364 (3)	N1—H1B	0.8600
C8—C7	1.417 (3)

C2—C11—H11	119.5	C8—C7—H7	119.3
C2—C11—C10	120.9 (2)	C6—C7—C8	121.37 (19)
C10—C11—H11	119.5	C6—C7—H7	119.3
C11—C2—C1	119.01 (17)	C8—C9—H9	119.5
C11—C2—C3	119.67 (17)	C10—C9—C8	121.05 (19)
C3—C2—C1	121.32 (15)	C10—C9—H9	119.5
O1—C1—C2	122.04 (14)	C4—C5—H5	119.6
O1—C1—N1	121.23 (17)	C4—C5—C6	120.8 (2)
N1—C1—C2	116.73 (14)	C6—C5—H5	119.6
C2—C3—C8	118.39 (16)	C11—C10—H10	119.8
C4—C3—C2	123.88 (15)	C9—C10—C11	120.35 (19)
C4—C3—C8	117.72 (17)	C9—C10—H10	119.8
C3—C4—H4	119.3	C7—C6—C5	120.0 (2)
C5—C4—C3	121.30 (18)	C7—C6—H6	120.0
C5—C4—H4	119.3	C5—C6—H6	120.0
C7—C8—C3	118.83 (18)	C1—N1—H1A	120.0
C9—C8—C3	119.63 (19)	C1—N1—H1B	120.0
C9—C8—C7	121.54 (19)	H1A—N1—H1B	120.0

C11—C2—C1—O1	−137.42 (18)	C3—C8—C7—C6	−0.2 (3)
C11—C2—C1—N1	41.7 (2)	C3—C8—C9—C10	0.1 (3)
C11—C2—C3—C4	−179.15 (16)	C4—C3—C8—C7	0.0 (2)
C11—C2—C3—C8	−0.3 (2)	C4—C3—C8—C9	178.83 (16)
C2—C11—C10—C9	−0.7 (3)	C4—C5—C6—C7	0.2 (4)
C2—C3—C4—C5	179.25 (17)	C8—C3—C4—C5	0.4 (3)
C2—C3—C8—C7	−178.98 (16)	C8—C7—C6—C5	0.1 (4)
C2—C3—C8—C9	−0.1 (2)	C8—C9—C10—C11	0.3 (3)
C1—C2—C3—C4	1.4 (2)	C7—C8—C9—C10	178.9 (2)
C1—C2—C3—C8	−179.74 (15)	C9—C8—C7—C6	−179.1 (2)
C3—C2—C1—O1	42.0 (2)	C10—C11—C2—C1	−179.83 (17)
C3—C2—C1—N1	−138.82 (17)	C10—C11—C2—C3	0.7 (3)
C3—C4—C5—C6	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.38	2.969 (3)	121
N1—H1A···O1ⁱ	0.86	2.10	2.951 (3)	170
N1—H1B···O1ⁱⁱ	0.86	2.06	2.889 (3)	163

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

Acknowledgements

The authors thank the Cambridge Crystallographic Data Center (CCDC) for access to the Cambridge Structural Database (CSD) through the FAIRE program.

Funding information

Funding for this research was provided by: Unité de recherche de chimie de l'environnement, moléculaire et structurale UR.CHEMS; DRSDT-Algeria; Laboratoire de technologie des matériaux avancés, Ecole Nationale Polytechnique de Constantine, Algeria.

References

Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Heller, E. & Schmidt, G. M. J. (1971). Isr. J. Chem. 9, 449–462. CSD CrossRef CAS Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 9| September 2026| x260989

https://doi.org/10.1107/S2414314626009892

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Naphthamide

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

Funding information

References

organic compounds