Synthesis and structure of N-(perfluoro­phen­yl)isonicotinamide

Saha, A.; Hanan, G.S.; Cibian, M.

doi:10.1107/S2056989025010679

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Volume 82| Part 1| January 2026| Pages 19-23

https://doi.org/10.1107/S2056989025010679

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Synthesis and structure of N-(perfluorophenyl)isonicotinamide

Arindam Saha,^a ^* Garry S Hanan ^a and Mihaela Cibian ^b

^aDépartement de chimie, Université de Montréal, Complexe des sciences, 1375, Avenue Thérèse-Lavoie-Roux, Montréal, Québec, H2V 0B3, Canada, and ^bDépartement de biochimie, chimie, physique et science forensique and l'Institut de recherche sur l'hydrogène, Université du Québec à Trois-Rivières, 3351, boul. des Forges, CP 500, Trois-Rivières, Québec, G9A 5H7, Canada
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 10 September 2025; accepted 29 November 2025; online 1 January 2026)

The title compound [systematic name: N-(2,3,4,5,6-pentafluorophenyl)pyridine-4-carboxamide], C₁₂H₅F₅N₂O, crystallizes with two independent molecules (A and B) in the asymmetric unit in space group P1. The molecules adopt a conformation where the planes of the pentafluorophenyl and pyridyl rings have twist angles of 5.3 (1) and 14.5 (1)°. In the crystal, the molecules are connected by N—H⋯N hydrogen bonds between the amide H atom and the pyridyl nitrogen atom of an adjacent molecule to generate [110] chains of alternating A and B molecules. The packing is consolidated by C—H⋯π interactions, π–π stacking and C—H⋯O interactions and a short F⋯F contact of 2.7270 (13) Å occurs. The structures of related isonicotinamides are surveyed.

Keywords: crystal structure; arylamide; hydrogen bonding.

CCDC reference: 2512078

1. Chemical context

There is ongoing interest in the synthesis of amides for academic and industrial research (Pattabiraman & Bode, 2011 ) owing to their applications in peptide synthesis (Seward & Jakubke, 2002 ), drug discovery (Masse et al., 1998 ), organometallic (Leitch et al., 2011 ), and coordination chemistry (Hasegawa et al., 2007 ). Herein, we report on the synthesis and solid state structure of the title compound, C₁₂H₅F₅N₂O (1). It was sythesized as the first-step product of a total three-step method for preparing amidine-N-oxide ligands (Cibian et al., 2009 , 2011 ; Saha et al., 2024 ). Although there are specific examples in the literature corresponding to unsymmetrical amides, this is the first report of pyridyl-containing N—H pentafluroaryl analogue.

2. Structural commentary

Each of the two molecules in the asymmetric unit of 1 consists of three near planar sub-units: the 4-pyridyl ring (py), the amide linkage (NCO), and the pentafluorophenyl ring (pfp) (Fig. 1). Tilt angles exist between the py and pfp planes. In molecule A (atoms labelled with the suffix A), this twist angle has a value of 5.3 (1)° whereas in molecule B (atoms labelled with the suffix B) this value is 14.5 (1)°. In molecule A, the angles between the amide plane (consisting of atoms N1A, C1A, and O1A) and the py and pfp planes are 47.8 (1) and 49.7 (1)°, respectively. Regarding molecule B, these values (plane of amide consisting of atoms N1B, C1B, and O1B with the py and pfp rings) are 38.5 (1) and 52.8 (1)°. The N1A—C1A and N1B—C1B bond lengths [indistinguishable within 3σ, average of 1.360 (1) Å] are characteristic of the partial double-bond found in amides. This intermediate length, falling between that of a typical N—C single bond (∼1.45) Å and an N=C double bond (∼1.25 Å), results from resonance across the amide group (Pattabiraman & Bode, 2011). The amide N—C bond length herein is statistically similar (within 3σ) to those found in other N-(pentafluorophenyl)arylamides with the aryl group being phenyl, 4-nitrophenyl, or 4-dimethylaminophenyl [1.369 (4), 1.369 (5), and 1.366 (4) Å, respectively, Adams et al., 2001 ], but it is different when the aryl substituent is another pentafluorophenyl ring [1.332 (5) Å; Pagliari et al., 2022 ]. The amide N—C bond length in 1 is also similar to those found in N-aryl-substituted isonicotinamides bearing N-substituents such as phenyl [1.359 (2) Å; Mondal et al., 2007 ] or 4-fluorophenyl [1.355 (2) Å; Mocilac et al., 2011 ]. However, it is quite different when a bulky N-aryl-substituent is present, e.g., 2,6-diiPrPh [1.337 (1) Å; Laramée et al., 2012 ]. The amide C=O bond length in 1 is similar to that in N-(phenyl)pentafluorobenzamide [1.232 (4) Å; Adams et al., 2001], but it is longer in N-(pentafluorophenyl)pentafluorobenzamide [1.271 (4) Å; Pagliari et al., 2022], as expected due to the electron-withdrawing effect of the pentafluorophenyl substituent. The amide C=O bond length in 1 is also shorter than those observed in N-aryl-substituted isonicotinamides bearing N-substituents such as phenyl [1.232 (2) Å; Mondal et al., 2007], 4-fluorophenyl [1.230 (2) Å; Mocilac et al., 2011], and 2,6-diiPrPh [1.333 (1) Å; Laramée et al., 2012].

Figure 1
The molecular structure of 1, with displacement ellipsoids drawn at the 50% probability level. The short F⋯F intermolecular contact is also shown.

3. Supramolecular features

In the crystal, the molecules are linked by N1A—H1A⋯N2B and N1B—H1B⋯N2A hydrogen bonds (Table 1 and Fig. 2) between the amide (donor) and py subunits (acceptor), generating [ $[\overline{1}]$ 10] chains of alternating A and B molecules. Given the short distance between the donor and acceptor units with a high hydrogen-bond angle, these interactions are likely to be strong (Desiraju & Steiner, 2001 ). Hydrogen-bonding interactions also exist between the o-Csp²–H (C3A—H3A in A) and the carbonyl-O atom (O1A in A) located in two adjacent unit cells. These interactions are assigned as moderately weak hydrogen bonds. In contrast, the hydrogen bond between m-Csp²–H (C5A—H5A in A) and carbonyl-O (O1B in B) is stronger, given a C5A—H5A⋯O1B distance of 2.54 (1) Å and angle of 169.8 (1)°. Interestingly, the fluorine atom in molecule B (F4B in the pfp ring) is also engaged as a double acceptor with two sp²C—H atoms (H5B and H6B in molecule B) in the adjacent molecule. The bond parameters for C5B—H5B⋯F4B are 2.65 (1) Å and 117 (1)° and those for C6B—H6B⋯F4B are 2.43 (1) Å and 124 (1)°. This observation could also explain the higher twist angle between the py and pfp planes in molecule B where the F atom is involved in the above-mentioned interactions, which are absent in molecule A. The packing in 1 (Fig. 3) is further consolidated by C—H ⋯π interactions and π–π stacking interactions, as well as by a short F4A⋯F2B contact (shown in Fig. 1) of 2.7270 (13) Å (van der Waals sum = 2.94 Å). This C—F⋯F—C interaction is identified as quasi type I/II (Singla et al., 2023 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N2Bⁱ	0.872 (18)	2.004 (19)	2.8261 (16)	156.9 (16)
N1B—H1B⋯N2Aⁱⁱ	0.844 (18)	2.047 (19)	2.8643 (16)	163.1 (17)
C3A—H3A⋯O1Aⁱⁱⁱ	0.95	2.44	3.2075 (17)	138
C5A—H5A⋯O1B^iv	0.95	2.54	3.4785 (17)	170
C6B—H6B⋯F4B^v	0.95	2.43	3.0669 (16)	124
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

Figure 2
Hydrogen-bonding pattern in 1.

Figure 3
Packing of 1 in the unit cell. H atoms are omitted for clarity.

4. Database survey

Table 2 presents the results of the Cambridge Structural Database survey with respect to other reported molecular structures of N-(aryl)isonicotinamides and N-(perfluorophenyl)arylamides (CSD, Version 5.46, update of November 2024; Groom et al., 2016 ). The space groups and the values of tilt angle between the aromatic rings (θ) are presented for each of the structures. All the compounds in Table 2 are free amides [N-(aryl)isonicotinamides (entries 1–14) and N-(perfluorophenyl)arylamides (entries 20–27) or pyridinium chloride salts (entries 15–19)], non-coordinated to metal ions. Coordination complexes of related amide ligands containing 4-py subunit exist with transition-metal ions Cu^II (CSD refcodes FOPZAM, FOPZEQ, FOPZIU; Ge et al., 2005 and JEQMEY, JESXUB; Ge et al., 2006 ), Cd^II (IKEQIY; Li et al., 2003 ), and Zn^II (IKEQOE; Li et al., 2003 and QINJEF, QINJIJ; Kwiatek et al., 2019 ). Mono- and bimetallic 4-py amide-based coordination polymers are reported with Cu^II (IDUTIN; Chen et al., 2018 , and ISISUZ; Deng et al., 2011 ) and Co^III (IPURIV; Chen et al., 2011a ), Cu^II/Tb^III (NETWOA; Deng et al., 2013 ), Cu^II/Gd^III (IZAYIS; Chen et al., 2011b ), Mn^II/Gd^III (NASMIF; Chen et al., 2012 ), and Mn^II/Eu^III (NASMEB; Chen et al., 2012).

Table 2
CSD reported molecular structures of N-(aryl)isonicotinamides and N-(perfluorophenyl)arylamides (free base, non-coordinated and salts forms)

py = pyridyl; pfp = pentafluorophenyl; Ar1 = 3-(methoxycarbonyl)-2-methylphenyl; Ar2 = 3-(methoxycarbonyl)-6-methylphenyl; Ar3 = 5-(methoxycarbonyl)-2-methylphenyl; Ar4 = 2-(methoxycarbonyl)-4-methylphenyl; Ar5 = 4-(methoxycarbonyl)-2-methylphenyl; Ar6 = 9-anthracene; Ar7 = 4-dimethylaminophenyl; Ar8 = 4-nitrophenyl; Ar9 = 5′-methyl, 2′-methoxy-biphenyl-4-carboxylate; Ar10 = 4-fluoro-2-methyl-6-(morpholin-4-yl); θ = tilt angle between the aromatic rings.

Entry No.	R1—(C=O)	R2—(N—C=O)	Space group	θ (°)	CSD refcode	Reference
1	4-py	Ph	P $[\overline{1}]$	63	PEDDIM	Kumar et al. (2004 )
2	4-py	Ph	P $[\overline{1}]$	61	PEDDIM01	Mondal et al. (2007)
3	4-py	Ph	P $[\overline{1}]$	61	PEDDIM02	Mondal et al. (2020 )
4	4-py	4-F—Ph	P $[\overline{1}]$	58	AMUDES	Mocilac et al. (2011)
5	4-py	3-F—Ph	Cc	66	AMUDIW	Mocilac et al. (2011)
6	4-py	3-F—Ph	P21/c	69	KODGES	Mocilac et al. (2018 )
7	4-py	2-F—Ph	Cc	77	AMUDOC	Mocilac et al. (2011)
8	4-py	2,6-diiPr-Ph	P21/c	80	CEGMOS	Laramée et al. (2012)
9	4-py	4-Cl—Ph	Pbca	48	KEHTOK	Gallagher et al. (2022 )
10	4-py	3-Cl—Ph	P21/n	2	KEHTUQ	Gallagher et al. (2022)
11	4-py	2-Cl—Ph	Cc	83	KEHVAY	Gallagher et al. (2022)
12	4-py	4-MePh	P2/c	67	UXEXAX	Mocilac et al. (2011)
13	4-py	3-MePh	P21/n	5	UXEXEB	Mocilac et al. (2011)
14	4-py	2-MePh	Cc	84	UXEXIF	Mocilac et al. (2011)
15	4-pyH⁺	Ar1	P21/c	10	DAZGAP	Kwiatek et al. (2017 )
16	4-pyH⁺	Ar2	P21/c	88	DAZFOC	Kwiatek et al. (2017)
17	4-pyH⁺	Ar3	P41	88	DAZGET	Kwiatek et al. (2017)
18	4-pyH⁺	Ar4	P21/c	13	QINKEG	Kwiatek et al. (2019)
19	4-pyH⁺	Ar5	P21/c	4	QINKIK	Kwiatek et al. (2019)
20	Ar6	pfp	P21/n	2, 58	CABGAO	Adams et al. (2001)
21	Ar7	pfp	P21/n	22	UCOVAJ	Adams et al. (2001)
22	Ar8	pfp	Cc	81	UCOVEN	Adams et al. (2001)
23	Ar9	pfp	P21/c	3	AKUDIV	Wang et al. (2016 )
24	Ar10	pfp	C2/c	38	VODGEE	Xing et al. (2023 )
25	pfp	pfp	P1	86	RENPAF	Pagliari et al. (2022)
26	pfp	pfp	P21/c	90	QUKVUN	Sopkova et al. (2001 )
27	pfp	pfp	P $[\overline{1}]$	89	QUKVUN01	Adams et al. (2001)

Several coordination polymers based on discrete units containing 4-py O-/S- linked bisamides are also reported with transition-metal ions such as Mn^II (JEMMOG, JEMPOJ, JEMQOK), Ni^II (JEMQAW, JEMQIE), and Co^II (JEMQEA, JEMPUP) (Tzeng et al., 2016 ). Interestingly, 2,3,4,5,6-pentafluoro-N-(pentafluorophenyl)benzamide and N-phenylbenzamide are also reported as co-crystallized structures (RENPEJ; Pagliari et al., 2022).

Other N-(R)isonicotinamides exists, with R = Me (PAPROP; Mukherjee et al., 2011 ), as well as N-(perfluorophenyl)-R-amides, with R = Me (WALPIL; Babailov et al., 2015 ), CF₃ (TEKQOP; Mahoui et al., 1996 ), dimethoxyphosphinoyl (XIPNEQ and XIPPOC; Song et al., 2007 ), and other more exotic groups [DORKUR (Moorthy et al., 2009 ), DIJGAF, DIJJAI, DIJJEM (Basheer et al., 2007 )]. N-(Perfluorophenyl)-R-bisamides (AMEKAG, AMEKAG01, NIPXUG; Light et al., 2016 , Picci et al., 2020 , and Light et al., 2008 ) are also reported.

5. Synthesis and crystallization

The synthesis of compound 1 was realized by reacting isonicotinic acid (0.30 g, 2.44 mmol, 1 equiv.) and pentafluoroaniline (1.12 g, 6.10 mmol, 2.5 equiv.) in polyphosphoric acid trimethylsilyl ester (PPSE) at 453 K, overnight. The reaction was brought to room temperature and quenched with aqueous NaOH 1 M. A beige solid was obtained, which was further recrystallized from 95% aqueous EtOH solution and dried under vacuum to give the pure compound, as colorless crystals. Yield 0.49 g, 70%. The final product was characterized by ¹H and ¹⁹F NMR, as well as by C/H/N elemental analysis. Note: The PPSE (a condensing and dehydrating agent) was obtained as a colorless viscous liquid by refluxing P₂O₅ with hexamethyldisiloxane (HMDS) (stoichiometry 1 to 1.5) in dry DCM for 30 min (under N₂), followed by solvent evaporation.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms were included in calculated positions and treated as riding atoms: aromatic C—H = 0.95 Å, methyl C—H = 0.98 Å, with U_iso(H) = k × U_eq(parent C atom), where k = 1.2 for the aromatic H atoms and 1.5 for the methyl H atoms. The amide H atoms (H1A and H1B) were located in a difference-Fourier map and refined freely.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₂H₅F₅N₂O
M_r	288.18
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.6987 (1), 10.5767 (1), 14.9123 (2)
α, β, γ (°)	76.250 (1), 86.487 (1), 71.941 (1)
V (Å³)	1121.26 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.51
Crystal size (mm)	0.11 × 0.08 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII area detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015
T_min, T_max	0.642, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	31582, 4197, 3961
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.04
No. of reflections	4197
No. of parameters	369
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.25
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), OLEX2 (Dolomanov et al., 2009), ORTEP-3 for Windows (Farrugia, 2012 ), publCIF (Westrip, 2010 ), POVRAY (POVRAY, 2013 ), PLATON (Spek, 2020 ) and Mercury (Macrae et al., 2020 ).

Supporting information

CCDC reference: 2512078

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025010679/hb8158sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989025010679/hb8158Isup3.cml

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025010679/hb8158Isup3.hkl

checkCIF report

Computing details top

N-(2,3,4,5,6-Pentafluorophenyl)pyridine-4-carboxamide top

Crystal data top

C₁₂H₅F₅N₂O	Z = 4
M_r = 288.18	F(000) = 576
Triclinic, P1	D_x = 1.707 Mg m⁻³
a = 7.6987 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.5767 (1) Å	Cell parameters from 9964 reflections
c = 14.9123 (2) Å	θ = 3.1–70.7°
α = 76.250 (1)°	µ = 1.51 mm⁻¹
β = 86.487 (1)°	T = 100 K
γ = 71.941 (1)°	Plate, colourless
V = 1121.26 (2) Å³	0.11 × 0.08 × 0.02 mm

Data collection top

Bruker SMART APEXII area detector diffractometer	4197 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	3961 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.020
Detector resolution: 7.9 pixels mm^-1	θ_max = 71.1°, θ_min = 3.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Krause et al., 2015	k = −12→12
T_min = 0.642, T_max = 0.753	l = −18→18
31582 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0443P)² + 0.555P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4197 reflections	Δρ_max = 0.29 e Å⁻³
369 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

Experimental. X-ray crystallographic data for 1 were collected from a crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker smart diffractometer equipped with an APEX II CCD Detector, a Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 180.0 degree scan in 180 frames over three different parts of the reciprocal space.

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.

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

	x	y	z	U_iso*/U_eq
F1A	0.83834 (11)	0.85339 (9)	0.35948 (6)	0.02830 (19)
F2A	1.13400 (12)	0.69644 (10)	0.46658 (7)	0.0403 (2)
F3A	1.08948 (13)	0.53557 (10)	0.63288 (8)	0.0430 (3)
F4A	0.74626 (14)	0.53090 (9)	0.68912 (7)	0.0415 (2)
F5A	0.45820 (11)	0.67183 (8)	0.57895 (6)	0.0291 (2)
O1A	0.31847 (12)	0.95308 (9)	0.51675 (6)	0.0193 (2)
N1A	0.49224 (15)	0.85415 (11)	0.40764 (8)	0.0186 (2)
H1A	0.501 (2)	0.8540 (18)	0.3491 (13)	0.029 (4)*
N2A	−0.00745 (16)	1.24405 (11)	0.22270 (8)	0.0224 (2)
C1A	0.34768 (17)	0.94707 (12)	0.43635 (8)	0.0166 (2)
C2A	0.22535 (17)	1.04700 (12)	0.35925 (8)	0.0170 (3)
C3A	0.03689 (18)	1.07807 (13)	0.36737 (9)	0.0192 (3)
H3A	−0.015799	1.033733	0.419899	0.023*
C4A	−0.07252 (19)	1.17503 (13)	0.29726 (9)	0.0216 (3)
H4A	−0.201170	1.193663	0.302356	0.026*
C5A	0.1744 (2)	1.21472 (13)	0.21610 (9)	0.0228 (3)
H5A	0.223073	1.263552	0.164086	0.027*
C6A	0.29529 (18)	1.11650 (13)	0.28150 (9)	0.0206 (3)
H6A	0.423490	1.097053	0.273364	0.025*
C7A	0.63972 (18)	0.76998 (13)	0.46636 (9)	0.0191 (3)
C8A	0.81592 (19)	0.77125 (14)	0.43946 (10)	0.0227 (3)
C9A	0.96634 (19)	0.69236 (15)	0.49431 (11)	0.0283 (3)
C10A	0.9442 (2)	0.61128 (14)	0.57893 (11)	0.0301 (3)
C11A	0.7709 (2)	0.60855 (14)	0.60733 (10)	0.0283 (3)
C12A	0.62167 (19)	0.68509 (13)	0.55052 (10)	0.0228 (3)
F1B	0.95005 (10)	0.46098 (7)	0.88679 (5)	0.02124 (17)
F2B	1.00723 (11)	0.29582 (8)	0.76949 (5)	0.02752 (19)
F3B	0.91262 (13)	0.06125 (8)	0.81644 (6)	0.0329 (2)
F4B	0.76213 (12)	−0.00665 (8)	0.98328 (6)	0.0304 (2)
F5B	0.70539 (11)	0.15694 (8)	1.10273 (5)	0.02535 (18)
O1B	0.62254 (12)	0.59168 (9)	0.95399 (6)	0.01814 (19)
N1B	0.78444 (15)	0.40335 (11)	1.05917 (8)	0.0166 (2)
H1B	0.831 (2)	0.3691 (18)	1.1126 (12)	0.027 (4)*
N2B	0.54695 (15)	0.77346 (12)	1.23789 (8)	0.0217 (2)
C1B	0.68065 (16)	0.53613 (12)	1.03250 (8)	0.0158 (2)
C2B	0.63837 (17)	0.61433 (13)	1.10735 (9)	0.0169 (2)
C3B	0.59647 (18)	0.55864 (13)	1.19689 (9)	0.0212 (3)
H3B	0.599283	0.465630	1.215172	0.025*
C4B	0.55028 (19)	0.64262 (14)	1.25911 (9)	0.0233 (3)
H4B	0.519354	0.604944	1.320089	0.028*
C5B	0.58856 (18)	0.82555 (14)	1.15148 (9)	0.0216 (3)
H5B	0.588384	0.918061	1.135634	0.026*
C6B	0.63189 (18)	0.75108 (13)	1.08398 (9)	0.0197 (3)
H6B	0.656748	0.792679	1.022806	0.024*
C7B	0.82003 (17)	0.31678 (12)	0.99738 (9)	0.0163 (2)
C8B	0.89747 (17)	0.34855 (12)	0.91135 (9)	0.0171 (2)
C9B	0.92841 (18)	0.26397 (13)	0.85043 (9)	0.0200 (3)
C10B	0.88256 (19)	0.14414 (13)	0.87468 (10)	0.0223 (3)
C11B	0.80777 (18)	0.10951 (13)	0.95990 (10)	0.0221 (3)
C12B	0.77824 (17)	0.19421 (13)	1.02067 (9)	0.0190 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0260 (4)	0.0348 (5)	0.0271 (4)	−0.0100 (4)	0.0082 (3)	−0.0137 (4)
F2A	0.0162 (4)	0.0473 (6)	0.0607 (6)	−0.0058 (4)	0.0007 (4)	−0.0239 (5)
F3A	0.0292 (5)	0.0324 (5)	0.0603 (6)	0.0031 (4)	−0.0240 (5)	−0.0077 (4)
F4A	0.0435 (6)	0.0309 (5)	0.0389 (5)	−0.0074 (4)	−0.0159 (4)	0.0116 (4)
F5A	0.0234 (4)	0.0264 (4)	0.0325 (4)	−0.0075 (3)	−0.0027 (3)	0.0031 (3)
O1A	0.0196 (5)	0.0208 (4)	0.0161 (4)	−0.0039 (4)	0.0009 (4)	−0.0047 (3)
N1A	0.0182 (5)	0.0189 (5)	0.0165 (5)	−0.0010 (4)	−0.0017 (4)	−0.0059 (4)
N2A	0.0275 (6)	0.0183 (5)	0.0190 (5)	−0.0035 (5)	−0.0036 (5)	−0.0035 (4)
C1A	0.0167 (6)	0.0159 (6)	0.0180 (6)	−0.0059 (5)	0.0005 (5)	−0.0041 (5)
C2A	0.0199 (6)	0.0150 (6)	0.0164 (6)	−0.0038 (5)	−0.0008 (5)	−0.0059 (5)
C3A	0.0207 (6)	0.0195 (6)	0.0169 (6)	−0.0055 (5)	0.0013 (5)	−0.0044 (5)
C4A	0.0196 (6)	0.0222 (6)	0.0216 (6)	−0.0032 (5)	−0.0012 (5)	−0.0063 (5)
C5A	0.0294 (7)	0.0192 (6)	0.0185 (6)	−0.0075 (5)	0.0017 (5)	−0.0021 (5)
C6A	0.0198 (6)	0.0197 (6)	0.0217 (6)	−0.0055 (5)	0.0019 (5)	−0.0048 (5)
C7A	0.0185 (6)	0.0161 (6)	0.0227 (6)	−0.0011 (5)	−0.0029 (5)	−0.0092 (5)
C8A	0.0221 (7)	0.0209 (6)	0.0266 (7)	−0.0037 (5)	0.0012 (6)	−0.0124 (5)
C9A	0.0165 (7)	0.0273 (7)	0.0446 (9)	−0.0025 (6)	−0.0012 (6)	−0.0201 (6)
C10A	0.0246 (7)	0.0197 (7)	0.0429 (9)	0.0029 (6)	−0.0154 (7)	−0.0101 (6)
C11A	0.0313 (8)	0.0180 (6)	0.0320 (8)	−0.0033 (6)	−0.0098 (6)	−0.0023 (6)
C12A	0.0213 (7)	0.0179 (6)	0.0282 (7)	−0.0033 (5)	−0.0041 (6)	−0.0055 (5)
F1B	0.0208 (4)	0.0165 (4)	0.0267 (4)	−0.0073 (3)	0.0038 (3)	−0.0043 (3)
F2B	0.0306 (5)	0.0267 (4)	0.0200 (4)	−0.0015 (3)	0.0053 (3)	−0.0063 (3)
F3B	0.0402 (5)	0.0251 (4)	0.0367 (5)	−0.0040 (4)	−0.0032 (4)	−0.0201 (4)
F4B	0.0339 (5)	0.0154 (4)	0.0445 (5)	−0.0108 (3)	−0.0024 (4)	−0.0065 (3)
F5B	0.0279 (4)	0.0195 (4)	0.0253 (4)	−0.0076 (3)	0.0034 (3)	0.0008 (3)
O1B	0.0188 (5)	0.0168 (4)	0.0168 (4)	−0.0034 (3)	−0.0016 (4)	−0.0025 (3)
N1B	0.0177 (5)	0.0153 (5)	0.0155 (5)	−0.0026 (4)	−0.0035 (4)	−0.0032 (4)
N2B	0.0185 (6)	0.0239 (6)	0.0226 (6)	−0.0027 (4)	−0.0012 (4)	−0.0098 (4)
C1B	0.0135 (6)	0.0161 (6)	0.0182 (6)	−0.0054 (5)	0.0010 (5)	−0.0039 (5)
C2B	0.0128 (6)	0.0178 (6)	0.0194 (6)	−0.0024 (5)	−0.0022 (5)	−0.0053 (5)
C3B	0.0227 (7)	0.0181 (6)	0.0211 (6)	−0.0046 (5)	0.0005 (5)	−0.0034 (5)
C4B	0.0238 (7)	0.0256 (7)	0.0181 (6)	−0.0044 (5)	0.0012 (5)	−0.0049 (5)
C5B	0.0214 (7)	0.0189 (6)	0.0255 (7)	−0.0056 (5)	−0.0009 (5)	−0.0073 (5)
C6B	0.0201 (6)	0.0188 (6)	0.0194 (6)	−0.0054 (5)	−0.0002 (5)	−0.0036 (5)
C7B	0.0133 (6)	0.0150 (6)	0.0187 (6)	−0.0012 (5)	−0.0037 (5)	−0.0038 (5)
C8B	0.0137 (6)	0.0134 (5)	0.0222 (6)	−0.0022 (5)	−0.0029 (5)	−0.0022 (5)
C9B	0.0175 (6)	0.0199 (6)	0.0187 (6)	0.0001 (5)	−0.0020 (5)	−0.0045 (5)
C10B	0.0215 (7)	0.0184 (6)	0.0264 (7)	0.0000 (5)	−0.0051 (5)	−0.0105 (5)
C11B	0.0201 (7)	0.0127 (6)	0.0326 (7)	−0.0035 (5)	−0.0059 (6)	−0.0041 (5)
C12B	0.0163 (6)	0.0164 (6)	0.0210 (6)	−0.0026 (5)	−0.0024 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

F1A—C8A	1.3351 (16)	F1B—C8B	1.3361 (14)
F2A—C9A	1.3415 (17)	F2B—C9B	1.3351 (15)
F3A—C10A	1.3374 (17)	F3B—C10B	1.3371 (15)
F4A—C11A	1.3381 (18)	F4B—C11B	1.3429 (15)
F5A—C12A	1.3413 (16)	F5B—C12B	1.3382 (15)
O1A—C1A	1.2193 (15)	O1B—C1B	1.2208 (15)
N1A—H1A	0.872 (18)	N1B—H1B	0.844 (18)
N1A—C1A	1.3606 (16)	N1B—C1B	1.3589 (16)
N1A—C7A	1.4047 (17)	N1B—C7B	1.4060 (16)
N2A—C4A	1.3390 (18)	N2B—C4B	1.3367 (18)
N2A—C5A	1.3397 (19)	N2B—C5B	1.3372 (18)
C1A—C2A	1.5046 (18)	C1B—C2B	1.5044 (17)
C2A—C3A	1.3891 (18)	C2B—C3B	1.3875 (18)
C2A—C6A	1.3922 (18)	C2B—C6B	1.3905 (18)
C3A—H3A	0.9500	C3B—H3B	0.9500
C3A—C4A	1.3845 (19)	C3B—C4B	1.3899 (19)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—H5A	0.9500	C5B—H5B	0.9500
C5A—C6A	1.3880 (19)	C5B—C6B	1.3847 (18)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.3940 (19)	C7B—C8B	1.3928 (18)
C7A—C12A	1.3859 (19)	C7B—C12B	1.3913 (17)
C8A—C9A	1.378 (2)	C8B—C9B	1.3820 (18)
C9A—C10A	1.381 (2)	C9B—C10B	1.3804 (19)
C10A—C11A	1.381 (2)	C10B—C11B	1.379 (2)
C11A—C12A	1.382 (2)	C11B—C12B	1.3821 (19)

C1A—N1A—H1A	118.8 (12)	C1B—N1B—H1B	122.4 (12)
C1A—N1A—C7A	122.49 (11)	C1B—N1B—C7B	120.68 (11)
C7A—N1A—H1A	118.2 (12)	C7B—N1B—H1B	116.9 (12)
C4A—N2A—C5A	117.18 (11)	C4B—N2B—C5B	117.51 (11)
O1A—C1A—N1A	124.29 (12)	O1B—C1B—N1B	124.09 (11)
O1A—C1A—C2A	121.61 (11)	O1B—C1B—C2B	120.45 (11)
N1A—C1A—C2A	114.09 (11)	N1B—C1B—C2B	115.46 (11)
C3A—C2A—C1A	119.81 (11)	C3B—C2B—C1B	123.18 (11)
C3A—C2A—C6A	118.34 (12)	C3B—C2B—C6B	118.68 (12)
C6A—C2A—C1A	121.72 (11)	C6B—C2B—C1B	118.05 (11)
C2A—C3A—H3A	120.7	C2B—C3B—H3B	120.9
C4A—C3A—C2A	118.58 (12)	C2B—C3B—C4B	118.19 (12)
C4A—C3A—H3A	120.7	C4B—C3B—H3B	120.9
N2A—C4A—C3A	123.78 (12)	N2B—C4B—C3B	123.63 (12)
N2A—C4A—H4A	118.1	N2B—C4B—H4B	118.2
C3A—C4A—H4A	118.1	C3B—C4B—H4B	118.2
N2A—C5A—H5A	118.4	N2B—C5B—H5B	118.4
N2A—C5A—C6A	123.24 (12)	N2B—C5B—C6B	123.13 (12)
C6A—C5A—H5A	118.4	C6B—C5B—H5B	118.4
C2A—C6A—H6A	120.6	C2B—C6B—H6B	120.6
C5A—C6A—C2A	118.84 (12)	C5B—C6B—C2B	118.82 (12)
C5A—C6A—H6A	120.6	C5B—C6B—H6B	120.6
C8A—C7A—N1A	118.68 (12)	C8B—C7B—N1B	122.34 (11)
C12A—C7A—N1A	124.06 (12)	C12B—C7B—N1B	120.48 (11)
C12A—C7A—C8A	117.26 (13)	C12B—C7B—C8B	117.17 (11)
F1A—C8A—C7A	118.93 (12)	F1B—C8B—C7B	120.18 (11)
F1A—C8A—C9A	119.43 (13)	F1B—C8B—C9B	117.96 (11)
C9A—C8A—C7A	121.63 (13)	C9B—C8B—C7B	121.82 (12)
F2A—C9A—C8A	120.13 (14)	F2B—C9B—C8B	120.22 (12)
F2A—C9A—C10A	119.90 (14)	F2B—C9B—C10B	119.98 (12)
C8A—C9A—C10A	119.96 (13)	C10B—C9B—C8B	119.77 (12)
F3A—C10A—C9A	120.22 (14)	F3B—C10B—C9B	120.28 (12)
F3A—C10A—C11A	120.24 (15)	F3B—C10B—C11B	120.16 (12)
C9A—C10A—C11A	119.54 (14)	C11B—C10B—C9B	119.55 (12)
F4A—C11A—C10A	120.54 (13)	F4B—C11B—C10B	119.57 (12)
F4A—C11A—C12A	119.51 (14)	F4B—C11B—C12B	120.09 (12)
C10A—C11A—C12A	119.94 (14)	C10B—C11B—C12B	120.34 (12)
F5A—C12A—C7A	120.97 (12)	F5B—C12B—C7B	120.16 (11)
F5A—C12A—C11A	117.39 (13)	F5B—C12B—C11B	118.51 (11)
C11A—C12A—C7A	121.62 (13)	C11B—C12B—C7B	121.32 (12)

F1A—C8A—C9A—F2A	−1.21 (19)	F1B—C8B—C9B—F2B	−0.54 (18)
F1A—C8A—C9A—C10A	177.32 (12)	F1B—C8B—C9B—C10B	177.51 (11)
F2A—C9A—C10A—F3A	−0.8 (2)	F2B—C9B—C10B—F3B	−1.66 (19)
F2A—C9A—C10A—C11A	179.44 (13)	F2B—C9B—C10B—C11B	177.47 (12)
F3A—C10A—C11A—F4A	0.3 (2)	F3B—C10B—C11B—F4B	−1.27 (19)
F3A—C10A—C11A—C12A	−178.82 (13)	F3B—C10B—C11B—C12B	179.32 (12)
F4A—C11A—C12A—F5A	−3.3 (2)	F4B—C11B—C12B—F5B	0.60 (18)
F4A—C11A—C12A—C7A	178.16 (12)	F4B—C11B—C12B—C7B	−178.40 (11)
O1A—C1A—C2A—C3A	−46.00 (17)	O1B—C1B—C2B—C3B	139.95 (13)
O1A—C1A—C2A—C6A	129.96 (13)	O1B—C1B—C2B—C6B	−36.60 (17)
N1A—C1A—C2A—C3A	135.40 (12)	N1B—C1B—C2B—C3B	−39.79 (17)
N1A—C1A—C2A—C6A	−48.63 (16)	N1B—C1B—C2B—C6B	143.66 (12)
N1A—C7A—C8A—F1A	0.75 (17)	N1B—C7B—C8B—F1B	3.66 (18)
N1A—C7A—C8A—C9A	179.24 (12)	N1B—C7B—C8B—C9B	−178.66 (12)
N1A—C7A—C12A—F5A	4.3 (2)	N1B—C7B—C12B—F5B	−0.70 (18)
N1A—C7A—C12A—C11A	−177.30 (12)	N1B—C7B—C12B—C11B	178.28 (12)
N2A—C5A—C6A—C2A	−1.7 (2)	N2B—C5B—C6B—C2B	−2.1 (2)
C1A—N1A—C7A—C8A	−124.75 (13)	C1B—N1B—C7B—C8B	55.10 (17)
C1A—N1A—C7A—C12A	54.95 (18)	C1B—N1B—C7B—C12B	−124.91 (13)
C1A—C2A—C3A—C4A	177.07 (11)	C1B—C2B—C3B—C4B	−176.66 (12)
C1A—C2A—C6A—C5A	−175.27 (11)	C1B—C2B—C6B—C5B	178.36 (12)
C2A—C3A—C4A—N2A	−2.0 (2)	C2B—C3B—C4B—N2B	−1.2 (2)
C3A—C2A—C6A—C5A	0.75 (18)	C3B—C2B—C6B—C5B	1.66 (19)
C4A—N2A—C5A—C6A	0.85 (19)	C4B—N2B—C5B—C6B	0.8 (2)
C5A—N2A—C4A—C3A	1.03 (19)	C5B—N2B—C4B—C3B	0.8 (2)
C6A—C2A—C3A—C4A	0.97 (18)	C6B—C2B—C3B—C4B	−0.14 (19)
C7A—N1A—C1A—O1A	−11.0 (2)	C7B—N1B—C1B—O1B	−5.13 (18)
C7A—N1A—C1A—C2A	167.53 (11)	C7B—N1B—C1B—C2B	174.60 (11)
C7A—C8A—C9A—F2A	−179.69 (12)	C7B—C8B—C9B—F2B	−178.26 (11)
C7A—C8A—C9A—C10A	−1.2 (2)	C7B—C8B—C9B—C10B	−0.2 (2)
C8A—C7A—C12A—F5A	−176.05 (11)	C8B—C7B—C12B—F5B	179.28 (11)
C8A—C7A—C12A—C11A	2.40 (19)	C8B—C7B—C12B—C11B	−1.74 (19)
C8A—C9A—C10A—F3A	−179.31 (12)	C8B—C9B—C10B—F3B	−179.71 (12)
C8A—C9A—C10A—C11A	0.9 (2)	C8B—C9B—C10B—C11B	−0.6 (2)
C9A—C10A—C11A—F4A	−179.88 (13)	C9B—C10B—C11B—F4B	179.60 (12)
C9A—C10A—C11A—C12A	1.0 (2)	C9B—C10B—C11B—C12B	0.2 (2)
C10A—C11A—C12A—F5A	175.82 (12)	C10B—C11B—C12B—F5B	180.00 (12)
C10A—C11A—C12A—C7A	−2.7 (2)	C10B—C11B—C12B—C7B	1.0 (2)
C12A—C7A—C8A—F1A	−178.96 (11)	C12B—C7B—C8B—F1B	−176.33 (11)
C12A—C7A—C8A—C9A	−0.48 (19)	C12B—C7B—C8B—C9B	1.35 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N2Bⁱ	0.872 (18)	2.004 (19)	2.8261 (16)	156.9 (16)
N1B—H1B···N2Aⁱⁱ	0.844 (18)	2.047 (19)	2.8643 (16)	163.1 (17)
C3A—H3A···O1Aⁱⁱⁱ	0.95	2.44	3.2075 (17)	138
C5A—H5A···O1B^iv	0.95	2.54	3.4785 (17)	170
C6B—H6B···F4B^v	0.95	2.43	3.0669 (16)	124

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

CSD reported molecular structures of N-(aryl)isonicotinamides and N-(perfluorophenyl)arylamides (free base, non-coordinated and salts forms) top

py = pyridyl; pfp = pentafluorophenyl; Ar1 = 3-(methoxycarbonyl)-2-methylphenyl; Ar2 = 3-(methoxycarbonyl)-6-methylphenyl; Ar3 = 5-(methoxycarbonyl)-2-methylphenyl; Ar4 = 2-(methoxycarbonyl)-4-methylphenyl; Ar5 = 4-(methoxycarbonyl)-2-methylphenyl; Ar6 = 9-anthracene; Ar7 = 4-dimethylaminophenyl; Ar8 = 4-nitrophenyl; Ar9 = 5'-methyl, 2'-methoxy-biphenyl-4-carboxylate; Ar10 = 4-fluoro-2-methyl-6-(morpholin-4-yl); θ = tilt angle between the aromatic rings.

Entry No.	R1—(C═O)	R2—(N—C═O)	Space group	θ (°)	CSD refcode	Reference
1	4-py	Ph	P1	63	PEDDIM	Kumar et al. (2004)
2	4-py	Ph	P1	61	PEDDIM01	Mondal et al. (2007)
3	4-py	Ph	P1	61	PEDDIM02	Mondal et al. (2020)
4	4-py	4-F-Ph	P1	58	AMUDES	Mocilac et al. (2011)
5	4-py	3-F-Ph	Cc	66	AMUDIW	Mocilac et al. (2011)
6	4-py	3-F-Ph	P21/c	69	KODGES	Mocilac et al. (2018)
7	4-py	2-F-Ph	Cc	77	AMUDOC	Mocilac et al. (2011)
8	4-py	2,6-diiPr-Ph	P21/c	80	CEGMOS	Laramée et al. (2012)
9	4-py	4-Cl-Ph	Pbca	48	KEHTOK	Gallagher et al. (2022)
10	4-py	3-Cl-Ph	P21/n	2	KEHTUQ	Gallagher et al. (2022)
11	4-py	2-Cl-Ph	Cc	83	KEHVAY	Gallagher et al. (2022)
12	4-py	4-MePh	P2/c	67	UXEXAX	Mocilac et al. (2011)
13	4-py	3-MePh	P21/n	5	UXEXEB	Mocilac et al. (2011)
14	4-py	2-MePh	Cc	84	UXEXIF	Mocilac et al. (2011)
15	4-pyH⁺	Ar1	P21/c	10	DAZGAP	Kwiatek et al. (2017)
16	4-pyH⁺	Ar2	P21/c	88	DAZFOC	Kwiatek et al. (2017)
17	4-pyH⁺	Ar3	P41	88	DAZGET	Kwiatek et al. (2017)
18	4-pyH⁺	Ar4	P21/c	13	QINKEG	Kwiatek et al. (2019)
19	4-pyH⁺	Ar5	P21/c	4	QINKIK	Kwiatek et al. (2019)
20	Ar6	pfp	P21/n	2, 58	CABGAO	Adams et al. (2001)
21	Ar7	pfp	P21/n	22	UCOVAJ	Adams et al. (2001)
22	Ar8	pfp	Cc	81	UCOVEN	Adams et al. (2001)
23	Ar9	pfp	P21/c	3	AKUDIV	Wang et al. (2016)
24	Ar10	pfp	C2/c	38	VODGEE	Xing et al. (2023)
25	pfp	pfp	P1	86	RENPAF	Pagliari et al. (2022)
26	pfp	pfp	P21/c	90	QUKVUN	Sopkova et al. (2001)
27	pfp	pfp	P1	89	QUKVUN01	Adams et al. (2001)

Acknowledgements

We gratefully acknowledge all the personnel from the XRD facilities of Université de Montréal. Professor Frank Schaper, Dr Daniel Chartrand and Dr Thierry Maris are acknowledged for the crystallographic course and training of A. Saha.

Funding information

Funding for this research was provided by: Natural Sciences and Engineering Research Council of Canada (NSERC); Fonds de recherche du Québec – Nature et technologies (FRQ-NT); Centre in Green Chemistry and Catalysis (CGCC); Quebec Centre for Advanced Materials (CQMF); Université de Montréal (UdeM); Université du Québec à Trois-Rivières (UQTR); l'Institut de recherche sur l'hydrogène (IRH).

References

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