600 https://doi.org/10.1107/S2056989021004655 Acta Cryst. (2021). E77, 600–604 research communications Received 21 April 2021 Accepted 2 May 2021 Edited by L. Van Meervelt, Katholieke Universi- teit Leuven, Belgium Keywords: crystal structure; imidazolidine ring; pyridine ring; hydrogen bond; Hirshfeld surface analysis. CCDC reference: 2081515 Supporting information: this article has supporting information at journals.iucr.org/e Crystal structure and Hirshfeld surface analysis of 5,7-diphenyl-1,2,3,5,6,7-hexahydroimidazo[1,2-a]- pyridine-6,6,8-tricarbonitrile methanol mono- solvate Farid N. Naghiyev, a Gunay Z. Mammadova, a Ali N. Khalilov, a,b Zeliha Atiog ˘lu, c Mehmet Akkurt, d Anzurat A. Akobirshoeva e * and ¤brahim G. Mamedov a a Department of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, Azerbaijan, b "Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, c Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapas ¸a, 50420 U ¨ rgu ¨ p, Nevs ¸ehir, Turkey, d Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and e Acad. Sci. Republ. Tadzhikistan, Kh. Yu. Yusufbekov Pamir Biol. Inst., 1 Kholdorova St, Khorog 736002, Gbao, Tajikistan. *Correspondence e-mail: anzurat2003@mail.ru In the title compound, C 22 H 17 N 5 CH 4 O, the imidazolidine ring of the 1,2,3,5,6,7- hexahydroimidazo[1,2-a]pyridine ring system is a twisted envelope, while the 1,2,3,4-tetrahydropyridine ring adopts a twisted boat conformation. In the crystal, pairs of molecules are linked by O—HN and N—HO hydrogen bonds via two methanol molecules, forming a centrosymmetric R 4 4 (16) ring motif. These motifs are connected to each other by C—HN hydrogen bonds and form columns along the a axis. The columns form a stable molecular packing, being connected to each other by van der Waals interactions. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from HH (43.8%), NH/HN (31.7%) and CH/ HC (18.4%) contacts. 1. Chemical context Having a great methodological diversity, C—C and C—X (where X is a heteroatom) bond-forming reactions lie at the heart of synthetic organic chemistry (Khalilov et al. , 2018a,b; Maharramov et al. , 2019; Cheng & Mankad, 2020). They allow the construction of complex molecular structures and the introduction of various substituents. Nowadays, researchers are constantly trying to develop new methods in these direc- tions for the syntheses of structurally diverse valuable mol- ecular entities. These approaches have successfully found application in the building of carbo- and heterocyclic ring systems (Naghiyev et al. , 2020; Mamedov et al. , 2019). In heterocyclic ring systems, the use of nitrogen as a bridgehead atom is being assessed widely. Bridgehead nitrogen hetero- cycles incorporating an imidazole ring are widespread struc- tural motifs in a diverse range of compounds having application in medicinal chemistry, coordination chemistry, catalysis and materials science (Asadov et al. , 2016; Ma et al., 2017a,b, 2020, 2021; Maharramov et al. , 2010, 2018; Mahmoudi et al., 2017, 2019; Mahmudov et al. , 2019, 2020). Various synthetic drugs, such as soraprazan, alpidem, olprinone, sari- pidem, necopidem, minodronic acid, zolimidine and zolpidem containing the imidazo[1,2-a]pyridine moiety (Fig. 1) have already been used in medical practice (Hosseini & Bayat, 2018). ISSN 2056-9890