Home Physical Sciences The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
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The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3

  • Lindelwa N. Maziya ORCID logo , Hlobsile Kgomo ORCID logo and Mark G. Smith ORCID logo EMAIL logo
Published/Copyright: October 23, 2025

Abstract

C6H6N2O·C7H7NO3, monoclinic, P21/n (no. 14), a = 3.7957(3) Å, b = 7.4395(5) Å, c = 43.878(3) Å, β = 91.181(3)°, V = 1238.77(16) Å3, Z = 4, R gt (F) = 0.0514, wRref(F2) = 0.1138, T = 173 K.

CCDC no.: 2451500

The molecular structure is shown in the figure. Table 1 contains the crystallographic data. The list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Colorless needle
Size: 0.76 × 0.15 × 0.12 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.11 mm−1
Diffractometer, scan mode: Bruker APEX3, φ and ω scans
θmax, completeness: 27.6°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 25907, 2837, 0.101
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2107
N(param)refined: 193
Programs: Bruker, 1 SHELX, 2 , 3 WinGX, 4 , 5 Platon 6

1 Discussion

Isonicotinamide, a pyridine-based compound with an amide group at the gamma-position, holds pharmaceutical significance due to its anti-tubercular, antipyretic, and antibacterial activities. 7 It readily forms co-crystals because of its ability to act as both a hydrogen bond donor and acceptor, and the robust heterosynthon formed between the pyridine nitrogen heteroatom and carboxylic acids and alcohols is well known in crystal engineering. 8 It is therefore often used in the formation of hydrogen-bonded networks with a wide range of pharmaceutical and functional molecules. 9 The 2-(nitrophenyl)methanol has the possibility to be a good co-former in co-crystallization since it is able to engage in both hydrogen bonding through the hydroxyl group and ππ stacking interactions via the aromatic ring, which can significantly influence crystal packing and stability. In this study, we report the synthesis and characterization of a co-crystal formed between isonicotinamide and 2-(nitrophenyl)methanol.

The asymmetric unit contains one molecule of isonicotinamide and one molecule of 2-(nitrophenyl)methanol, which crystallizes in the monoclinic P21/n space group. There is a single hydrogen bond between the two molecules formed between the pyridine nitrogen acceptor of isonicotinamide and the hydroxyl hydrogen donor of 2-(nitrophenyl)methanol, thus forming a discrete hydrogen bond via N1⋯H2a–O2.

With regard to packing, each isonicotinamide molecule is hydrogen bonded to an adjacent isonicotinamide via O5⋯H1A–N1 homosynthons, with a centre of inversion between the two molecules. The packing is further stabilized by ππ stacking interactions via the aromatic rings of 2-(nitrophenyl)methanol with a distance of 3.796 Å between the rings.

2 Source of materials

Analytical grade chemicals were purchased and used without further purification. The general one pot method for the synthesis of co-crystals described by Smith et al. 10 was followed for the synthesis of the co-crystal isonicotinamide·2-(nitrophenyl)methanol. The reaction followed a 1:1 mol ratio between isonicotinamide and 2-(nitrophenyl)methanol, by weighing 0.0800 g isonicotinamide (0.655 mmol) and 0.100 g 2-(nitrophenyl)methanol (0.655 mmol) in the same reaction vial. The mixture was subsequently dissolved in 3 mL AP-grade methanol. The mixture was stirred to ensure complete dissolution and placed at room temperature with the lid slightly opened to allow slow evaporation. Clear colourless needle crystals were afforded after 2 days.

3 Experimental details

C-bound hydrogen atoms were located in the difference map then positioned geometrically and were allowed to ride on their respective parent atoms with thermal displacement parameters 1.2 times of the parent C atom. The coordinates and isotropic displacement parameters of the N-bound and O-bound H atoms involved in hydrogen bonding interactions were allowed to refine freely. Diagrams and publication material were generated using ORTEP-3, 4 WinGX 5 and PLATON. 6


Corresponding author: Mark G. Smith, Department of Chemistry, University of South Africa, Unisa Science Campus, 28 Pioneer Avenue, Florida, Roodepoort Gauteng, South Africa, E-mail:

Funding source: National Research Foundation (South Africa)

Award Identifier / Grant number: CSUR23042597072

Funding source: University of South Africa (Dr H Kgomo)

Funding source: UNISA College of Science, Engineering and Technology bursary (Ms LN Maziya)

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Conflict of interest: The authors declare no conflicts of interest regarding this article.

  3. Research funding: This work was supported by the National Research Foundation (NRF) “Competitive Support for Unrated Researchers” grant Number CSUR23042597072 (Dr MG Smith), the University of South Africa (Dr H Kgomo) and the UNISA College of Science, Engineering and Technology bursary (Ms LN Maziya).

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Received: 2025-07-17
Accepted: 2025-10-02
Published Online: 2025-10-23
Published in Print: 2025-12-17

© 2025 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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