N-Phenyl-[1,1′-biphen­yl]-2-carboxamide

Guerah, N.E.H.; Tarek, A.; Mounib, A.M.; Daran, J.-C.; Manoury, E.

doi:10.1107/S2414314626005754

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 6| June 2026| x260575

https://doi.org/10.1107/S2414314626005754

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N-Phenyl-[1,1′-biphenyl]-2-carboxamide

Nour El Houda Guerah,^a ^* Attia Tarek,^b Allaoui Mahfoud Mounib,^b Jean-Claude Daran ^c and Eric Manoury ^c

^aLaboratoire des sciences analytiques, materiaux et environnement (LSAME), Université Oum El Bouaghi, Oum El Bouaghi, 04000, Algeria, ^bDépartement des Sciences de la Matière, Université d'Oum El Bouaghi, 04000, Algeria, and ^cLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205, route de Narbonne, 31077 Toulouse cedex, France
^*Correspondence e-mail: [email protected]

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 27 May 2026; accepted 29 May 2026; online 5 June 2026)

The title molecule, C₁₉H₁₅NO, contains a carboxamide fragment in which the amide N atom is bonded to a phenyl group, while the carbonyl C atom is attached to a biphenyl unit. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains running parallel to the a axis. These chains are further connected by C—H⋯π interactions, resulting in a three-dimensional supramolecular network.

Keywords: crystal structure; carboxamide; biphenyl derivative; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 2558356

Structure description

Biphenyl derivatives represent an important class of aromatic compounds owing to their conformational flexibility and structural diversity (Jain et al., 2017 ; Landeros-Rivera & Hernańdez-Trujillo, 2022 ). Functionalized biphenyl systems bearing carboxylic acid or amide groups have attracted considerable interest for their structural and coordination properties (Sienkiewicz-Gromiuk et al., 2014 ; Wang et al., 2004 ; Yu et al., 2006 ), as well as for their biological relevance (Sharma et al., 2010 ; van 't Hof et al., 2004 ; Mukherjee et al., 2016 ; Zhao et al., 2017 ). The amide functional group is well known for its strong hydrogen-bonding ability and its role in directing supramolecular organization in the solid state. The combination of a biphenyl scaffold with an amide linkage provides a versatile structural platform capable of promoting intermolecular hydrogen bonding and π–π stacking interactions, which are key factors in supramolecular self-assembly processes (Gao et al., 2022 ; Yao et al., 2025 ). Recent crystallographic studies of substituted biphenyl derivatives further highlight the influence of these interactions on molecular conformation and crystal packing (Nodera et al., 2025 ). In this context, we report herein the synthesis and crystal structure of the title comnpound, C₁₉H₁₅NO.

The title compound 1 crystallizes in the triclinic space group P $[\overline{1}]$ with one molecule in the asymmetric unit (Fig. 1). The molecular structure consists of a carboxamide fragment, C—N(H)—C(=O)—C, in which the amide N atom is bonded to a phenyl group and the carbonyl C atom is bonded to a biphenyl unit. The C—N, N—C and C=O bond lengths are in agreement with those observed in related compounds (see below). The amide fragment C—N(H)—C(=O)—C is essentially planar, with the largest deviation from the mean plane being 0.0413 (5) Å for atom C2. The phenyl ring C2—C7 is twisted by 24.70 (4)° with respect to the amide mean plane, while the phenyl ring attached to the carbonyl group is inclined by 55.67 (4)°. The phenyl and biphenyl groups are in the trans position with respect to the C1—N1 bond. The dihedral angle between the biphenyl rings is 40.67 (6)°.

Figure 1
Molecular structure of the title compound with the labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

In the crystal, molecules are linked by N1—H1⋯O1 hydrogen bonds, generating chains running parallel to the a axis (Table 1, Fig. 2). A weak C7—H7⋯O1 contact also contributes to the crystal packing. In addition, weak C—H⋯π interactions (Table 1) involving atoms C13 and C24 and the centroid of the C2—C7 phenyl ring further consolidate the packing. These interactions connect the N—H⋯O hydrogen-bonded chains into a three-dimensional supramolecular network.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.877 (16)	2.307 (16)	3.0790 (12)	146.9 (13)
C3—H3⋯O1	0.95	2.38	2.9035 (15)	114
C7—H7⋯O1ⁱ	0.95	2.64	3.2433 (13)	122
C13—H13⋯Cg1ⁱⁱ	0.95	2.78	3.5815 (13)	142
C24—H24⋯Cg1ⁱⁱⁱ	0.95	2.94	3.8444 (13)	160
Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2
Partial packing view showing the formation of N—H⋯O hydrogen-bonded chains running parallel to the a axis. Symmetry code as in Table 1

A search of the Cambridge Structural Database (CSD, version 5.36; Groom et al., 2016 ), based on the Ph—NH—C(=O)—C(R) fragment, revealed ten related structures containing a phenyl group attached to the amide N atom and different substituents attached to the carbonyl C atom. A comparison of selected bond lengths and angles is given in Table 2.

Table 2
Comparison of selected distances and angles (Å, °) in related compounds having a similar C(Ph)—NH—C(O)—C(R) fragment

Compound	N—C(O)	N—C(Ph)	C=O	C(O)—C(R)	C—N—C	N—C—C
1	1.3626 (14)	1.4198 (14)	1.2283 (13)	1.5001 (15)	126.70 (9)	114.07 (9)
CIBPIM	1.332	1.400	1.234	1.508	127.1	114.0
CIBPIM01	1.340	1.421	1.232	1.505	128.2	114.9
LASHEU	1.335	1.431	1.236	1.495	122.1	118.5
MANDIP	1.354	1.409	1.232	1.487	128.4	115.0
MANDIP01	1.350	1.416	1.237	1.497	127.3	115.3
MANDIP02	1.352	1.410	1.233	1.500	127.8	114.3
MANDIP03	1.353	1.412	1.233	1.499	127.9	114.1
NUKVOH	1.355	1.420	1.226	1.595	125.4	115.8
YEGJID	1.353	1.424	1.225	1.493	124.8	115.4
YEGJID01	1.352	1.418	1.237	1.492	126.3	114.5
References: CIBPIM: Smith et al. (1983 ); CIBPIM01: Bocelli et al. (1989 ); LASHEU: Panini et al. (2012 ); MANDIP: Goswami et al. (2005 ); MANDIP01: Fellowes (2020 ); MANDIP02: Romito & Bonifazi (2023 ); MANDIP03: Clarke et al. (2024 ); NUKVOH: McKay et al. (2020 ); YEGJID: Azumaya et al. (1994 ); YEGJID01: Gowda et al. (2008 ).

Synthesis and crystallization

2-Biphenylcarboxylic acid (1.63 g, 10 mmol) was dissolved in toluene (50 ml) and treated dropwise with thionyl chloride SOCl₂ (1.67 ml, 15 mmol) under stirring at 323–333 K. The reaction mixture was maintained at this temperature to allow formation of the corresponding acyl chloride. Aniline (1.03 g, 10 mmol) was then added dropwise, and the mixture was heated under reflux for 3 h. After completion of the reaction, the solvent was removed under reduced pressure. The crude solid was purified by recrystallization from ethanol solution to afford the title amide as a white solid (yield = 80%). Crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation of a solution of the compound in ethanol at room temperature. The reaction scheme is shown in Fig. 3.

Figure 3
Synthesis of N-phenyl-[1,1′-biphenyl]-2-carboxamide.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO
M_r	273.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	5.2935 (1), 12.0493 (2), 12.3713 (3)
α, β, γ (°)	65.411 (2), 80.417 (2), 80.644 (1)
V (Å³)	703.67 (3)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.62
Crystal size (mm)	0.18 × 0.06 × 0.04

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 )
T_min, T_max	0.84, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	20896, 2252, 2084
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.581

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.05
No. of reflections	2252
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2021), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEPIII (Burnett & Johnson, 1996 ); ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2558356

Crystal structure: contains datablocks shelx, I. DOI: https://doi.org/10.1107/S2414314626005754/vm4077sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626005754/vm4077Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626005754/vm4077Isup3.cml

checkCIF report

Computing details top

N-Phenyl-[1,1'-biphenyl]-2-carboxamide top

Crystal data top

C₁₉H₁₅NO	Z = 2
M_r = 273.32	F(000) = 288
Triclinic, P1	D_x = 1.290 Mg m⁻³
a = 5.2935 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 12.0493 (2) Å	Cell parameters from 15231 reflections
c = 12.3713 (3) Å	θ = 4.0–63.5°
α = 65.411 (2)°	µ = 0.62 mm⁻¹
β = 80.417 (2)°	T = 100 K
γ = 80.644 (1)°	Needle, colorless
V = 703.67 (3) Å³	0.18 × 0.06 × 0.04 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2252 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2084 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.0000 pixels mm^-1	θ_max = 63.7°, θ_min = 4.0°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	k = −13→13
T_min = 0.84, T_max = 1.0	l = −14→13
20896 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: mixed
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0444P)² + 0.1624P] where P = (F_o² + 2F_c²)/3
2252 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.20 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. Hydrogen atoms bonded to carbon atoms were placed at geometrically idealized positions and refined using a riding model, with Uiso(H) = 1.2Ueq(C). The amide H atom was located in a difference-Fourier map and freely refined.

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

	x	y	z	U_iso*/U_eq
O1	0.56138 (14)	0.48552 (7)	0.15047 (7)	0.0233 (2)
N1	0.12096 (18)	0.51216 (8)	0.16680 (8)	0.0204 (2)
H1	−0.016 (3)	0.4735 (12)	0.1824 (11)	0.026 (3)*
C1	0.3539 (2)	0.44452 (10)	0.16721 (9)	0.0191 (3)
C2	0.0753 (2)	0.63423 (10)	0.15990 (10)	0.0198 (3)
C3	0.2518 (2)	0.72007 (10)	0.10018 (10)	0.0227 (3)
H3	0.411682	0.698081	0.062454	0.027*
C4	0.1921 (2)	0.83811 (10)	0.09629 (11)	0.0246 (3)
H4	0.312790	0.896678	0.055944	0.029*
C5	−0.0406 (2)	0.87187 (10)	0.15028 (10)	0.0243 (3)
H5	−0.079582	0.952895	0.147088	0.029*
C6	−0.2159 (2)	0.78608 (10)	0.20900 (10)	0.0239 (3)
H6	−0.376344	0.808549	0.245972	0.029*
C7	−0.1588 (2)	0.66771 (10)	0.21413 (10)	0.0220 (3)
H7	−0.279691	0.609315	0.254787	0.026*
C11	0.33708 (19)	0.31320 (10)	0.19073 (10)	0.0194 (3)
C12	0.2034 (2)	0.28790 (10)	0.11718 (10)	0.0222 (3)
H12	0.112167	0.353274	0.058094	0.027*
C13	0.2018 (2)	0.16830 (10)	0.12918 (11)	0.0246 (3)
H13	0.112241	0.151757	0.077916	0.029*
C14	0.3319 (2)	0.07337 (10)	0.21654 (11)	0.0253 (3)
H14	0.333382	−0.008692	0.224702	0.030*
C15	0.4600 (2)	0.09738 (10)	0.29225 (11)	0.0239 (3)
H15	0.545952	0.030985	0.352639	0.029*
C16	0.4657 (2)	0.21702 (10)	0.28175 (10)	0.0204 (3)
C21	0.5881 (2)	0.23759 (10)	0.37111 (10)	0.0210 (3)
C22	0.8175 (2)	0.16885 (10)	0.41265 (10)	0.0251 (3)
H22	0.901319	0.111695	0.380268	0.030*
C23	0.9242 (2)	0.18298 (11)	0.50042 (11)	0.0303 (3)
H23	1.079857	0.135190	0.527985	0.036*
C24	0.8061 (2)	0.26608 (12)	0.54823 (11)	0.0327 (3)
H24	0.880431	0.276035	0.608025	0.039*
C25	0.5781 (2)	0.33477 (11)	0.50809 (11)	0.0296 (3)
H25	0.495631	0.391962	0.540670	0.035*
C26	0.4698 (2)	0.32056 (10)	0.42091 (10)	0.0239 (3)
H26	0.312917	0.367838	0.394535	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0196 (4)	0.0220 (4)	0.0287 (5)	−0.0038 (3)	−0.0038 (3)	−0.0094 (3)
N1	0.0181 (5)	0.0181 (5)	0.0260 (5)	−0.0042 (4)	−0.0032 (4)	−0.0088 (4)
C1	0.0205 (6)	0.0205 (5)	0.0167 (6)	−0.0028 (4)	−0.0033 (4)	−0.0071 (4)
C2	0.0219 (6)	0.0187 (5)	0.0207 (6)	−0.0005 (4)	−0.0086 (4)	−0.0081 (5)
C3	0.0204 (6)	0.0222 (6)	0.0248 (6)	−0.0020 (4)	−0.0048 (5)	−0.0079 (5)
C4	0.0259 (6)	0.0203 (6)	0.0268 (6)	−0.0056 (5)	−0.0081 (5)	−0.0056 (5)
C5	0.0290 (6)	0.0194 (6)	0.0273 (6)	0.0005 (5)	−0.0114 (5)	−0.0101 (5)
C6	0.0232 (6)	0.0256 (6)	0.0257 (6)	0.0007 (5)	−0.0059 (5)	−0.0129 (5)
C7	0.0215 (6)	0.0228 (6)	0.0231 (6)	−0.0041 (4)	−0.0045 (5)	−0.0091 (5)
C11	0.0170 (5)	0.0205 (6)	0.0208 (6)	−0.0030 (4)	0.0011 (4)	−0.0090 (5)
C12	0.0222 (6)	0.0228 (6)	0.0212 (6)	−0.0032 (4)	−0.0028 (5)	−0.0081 (5)
C13	0.0264 (6)	0.0266 (6)	0.0258 (6)	−0.0062 (5)	−0.0023 (5)	−0.0143 (5)
C14	0.0266 (6)	0.0207 (6)	0.0314 (7)	−0.0029 (5)	−0.0010 (5)	−0.0139 (5)
C15	0.0217 (6)	0.0205 (6)	0.0278 (6)	0.0001 (4)	−0.0034 (5)	−0.0086 (5)
C16	0.0160 (5)	0.0224 (6)	0.0228 (6)	−0.0023 (4)	0.0006 (4)	−0.0099 (5)
C21	0.0206 (5)	0.0202 (5)	0.0201 (6)	−0.0059 (4)	−0.0010 (4)	−0.0052 (4)
C22	0.0214 (6)	0.0245 (6)	0.0255 (6)	−0.0051 (5)	−0.0026 (5)	−0.0053 (5)
C23	0.0250 (6)	0.0325 (7)	0.0271 (7)	−0.0087 (5)	−0.0077 (5)	−0.0020 (5)
C24	0.0379 (7)	0.0376 (7)	0.0235 (7)	−0.0158 (6)	−0.0076 (5)	−0.0072 (6)
C25	0.0377 (7)	0.0301 (6)	0.0229 (6)	−0.0112 (5)	−0.0011 (5)	−0.0107 (5)
C26	0.0242 (6)	0.0239 (6)	0.0228 (6)	−0.0048 (5)	−0.0019 (5)	−0.0078 (5)

Geometric parameters (Å, º) top

O1—C1	1.2283 (13)	C12—C13	1.3872 (16)
N1—C1	1.3626 (14)	C13—C14	1.3833 (17)
N1—C2	1.4198 (14)	C14—C15	1.3864 (16)
C1—C11	1.5001 (15)	C15—C16	1.3975 (15)
C2—C7	1.3905 (16)	C16—C21	1.4906 (16)
C2—C3	1.3920 (16)	C21—C22	1.3969 (15)
C3—C4	1.3882 (16)	C21—C26	1.3970 (16)
C4—C5	1.3851 (17)	C22—C23	1.3844 (17)
C5—C6	1.3857 (16)	C23—C24	1.3820 (19)
C6—C7	1.3859 (15)	C24—C25	1.3862 (18)
C11—C12	1.3919 (16)	C25—C26	1.3828 (17)
C11—C16	1.4098 (16)

C1—N1—C2	126.70 (9)	C13—C12—C11	120.74 (10)
O1—C1—N1	123.91 (10)	C14—C13—C12	119.33 (11)
O1—C1—C11	122.02 (9)	C13—C14—C15	120.33 (10)
N1—C1—C11	114.07 (9)	C14—C15—C16	121.51 (10)
C7—C2—C3	119.80 (10)	C15—C16—C11	117.62 (10)
C7—C2—N1	117.46 (10)	C15—C16—C21	119.56 (10)
C3—C2—N1	122.73 (10)	C11—C16—C21	122.66 (10)
C4—C3—C2	119.36 (10)	C22—C21—C26	118.06 (10)
C5—C4—C3	121.06 (10)	C22—C21—C16	120.66 (10)
C4—C5—C6	119.23 (10)	C26—C21—C16	121.17 (10)
C5—C6—C7	120.42 (11)	C23—C22—C21	120.80 (11)
C6—C7—C2	120.13 (10)	C24—C23—C22	120.51 (11)
C12—C11—C16	120.43 (10)	C23—C24—C25	119.35 (11)
C12—C11—C1	118.88 (9)	C26—C25—C24	120.40 (12)
C16—C11—C1	120.61 (10)	C25—C26—C21	120.88 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.38	2.9035 (15)	114
C7—H7···O1ⁱ	0.95	2.64	3.2433 (13)	122
N1—H1···O1ⁱ	0.877 (16)	2.307 (16)	3.0790 (12)	146.9 (13)
C13—H13···Cg1ⁱⁱ	0.95	2.78	3.5815 (13)	142
C24—H24···Cg1ⁱⁱⁱ	0.95	2.94	3.8444 (13)	160

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

Comparison of selected distances and angles (Å, °) in related compounds having a similar C(Ph)—NH—C(O)—C(R) fragment top

Compound	N—C(O)	N—C(Ph)	C═O	C(O)—C(R)	C—N—C	N—C—C
1	1.3626 (14)	1.4198 (14)	1.2283 (13)	1.5001 (15)	126.70 (9)	114.07 (9)
CIBPIM	1.332	1.400	1.234	1.508	127.134	114.036
CIBPIM01	1.340	1.421	1.232	1.505	128.207	114.945
LASHEU	1.335	1.431	1.236	1.495	122.136	118.483
MANDIP	1.354	1.409	1.232	1.487	128.379	114.957
MANDIP01	1.350	1.416	1.237	1.497	127.314	115.315
MANDIP02	1.352	1.410	1.233	1.500	127.814	114.296
MANDIP03	1.353	1.412	1.233	1.499	127.862	114.135
NUKVOH	1.355	1.420	1.226	1.595	125.394	115.806
YEGJID	1.353	1.424	1.225	1.493	124.813	115.419
YEGJID01	1.352	1.418	1.237	1.492	126.319	114.538

References: CIBPIM: Smith et al. (1983); CIBPIM01: Bocelli et al. (1989); LASHEU: Panini et al. (2012); MANDIP: Goswami et al. (2005); MANDIP01: Fellowes (2020); MANDIP02: Romito & Bonifazi (2023); MANDIP03: Clarke et al. (2024); NUKVOH: McKay et al. (2020); YEGJID: Azumaya et al. (1994); YEGJID01: Gowda et al. (2008).

Acknowledgements

The authors thank the Laboratoire de Chimie de Coordination (LCC), Toulouse, for access to crystallographic facilities. The technical staff is gratefully acknowledged for assistance with crystal mounting and data collection.

References

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