Top PDF Methyl 3-[(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)formamido]propanoate: crystal structure, Hirshfeld surface analysis and computational chemistry

Methyl 3-[(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)formamido]propanoate: crystal structure, Hirshfeld surface analysis and computational chemistry

Methyl 3-[(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)formamido]propanoate: crystal structure, Hirshfeld surface analysis and computational chemistry

The title compound, C 20 H 20 N 4 O 3 , is constructed about a tri-substituted 1,2,3- triazole ring, with the substituent at one C atom flanked by the C and N atoms being a substituted amide group, and with the adjacent C and N atoms bearing phenyl and benzyl groups, respectively; the dihedral angle between the pendant phenyl rings is 81.17 (12)  , indicative of an almost orthogonal disposition. In the crystal, pairwise amide-N—H   O(carbonyl) hydrogen bonds lead to a centrosymmetric dimer incorporating methylene-C—H  (benzene) inter- actions. The dimers are linked into a supramolecular layer in the ab plane via methylene-C—H  N(azo) and benzene-C—H  O(amide) interactions; the layers stack along the c-axis direction without directional interactions between them. The above-mentioned intermolecular contacts are apparent in the analysis of the calculated Hirshfeld surface, which also provides evidence for short inter- layer H   C contacts with a significant dispersion energy contribution.
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2 Methyl 4 (4 nitro­phen­yl)but 3 yn 2 ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

2 Methyl 4 (4 nitro­phen­yl)but 3 yn 2 ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

is the second eigenvalue of the Hessian matrix of . Crucially, through a three-colour scheme, a specific interaction can be identified as being attractive or otherwise. Thus, a green isosurface indicates a weakly attrac- tive interaction whereas a blue isosurface indicates an attractive interaction; a repulsive interaction appears red. The isosurfaces for three identified intermolecular interactions are given in the upper view of Fig. 10. Thus, in Fig. 10(a), a green isosurface is apparent for the conventional hydroxy-O— H O(hydroxy) hydrogen bond. Similarly, green isosurfaces are seen between the interacting atoms involved in the phenyl- C—H O(nitro), Fig. 10(b), and the methyl-C—H (C11– C16), Fig. 10(c), interactions.
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Crystal structure, computational study and Hirshfeld surface analysis of ethyl (2S,3R) 3 (3 amino 1H 1,2,4 triazol 1 yl) 2 hy­dr­oxy 3 phenyl­propano­ate

Crystal structure, computational study and Hirshfeld surface analysis of ethyl (2S,3R) 3 (3 amino 1H 1,2,4 triazol 1 yl) 2 hy­dr­oxy 3 phenyl­propano­ate

Searches of the CSD (Version 5.40, updated to September 2019; Groom et al., 2016) with two different search fragments were performed. The first, with 3-amino-1H-1,2,4-triazole as the search fragment, found three structures in which a side chain is bound to the nitrogen atom in the 1-position of the triazole ring (N2 in 1), namely 4-(3-amino-1H-1,2,4-triazol-1- yl)-4-methylpentan-2-one (QISROC; Zemlyanaya et al., 2018), 1-(3-amino-1H-1,2,4-triazol-1-yl)-3,3-dimethylbutan-2- one (VATPEO; Cai et al., 2017) and 3-amino-1-guanyl-1,2,4- triazole dinitramide (YOPDAJ; Zeng et al., 2008). The triazole ring in each of these is essentially planar and the distances of the corresponding C and N substituent atoms from the mean plane of the triazole ring are comparable to those observed for 1.
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Crystal structure and Hirshfeld surface analysis of 5 [(5 nitro 1H indazol 1 yl)meth­yl] 3 phenyl 4,5 di­hydro­isoxazole

Crystal structure and Hirshfeld surface analysis of 5 [(5 nitro 1H indazol 1 yl)meth­yl] 3 phenyl 4,5 di­hydro­isoxazole

A search of the Cambridge Structural Database (CSD, version 5.39, updates August 2018; Groom et al., 2016) for the 1- methyl-5-nitro-1H-indazole skeleton yielded six hits. In all of these compounds, the indazole rings are planar as in the title compound. In the crystals of all six compounds, molecules are linked by C—H O hydrogen bonds, similar to what is observed in the crystal of the title compound. The N—O bond lengths vary from ca 1.213–1.236 A ˚ and the C aromatic —NO 2

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Crystal structure and Hirshfeld surface analysis of 3 (4 meth­­oxy­phen­yl) 1 methyl 4 phenyl 1H pyrazolo­[3,4 d]pyrimidine

Crystal structure and Hirshfeld surface analysis of 3 (4 meth­­oxy­phen­yl) 1 methyl 4 phenyl 1H pyrazolo­[3,4 d]pyrimidine

fingerprint outlined in gray. Individual fingerprint plots (Fig. 7b) reveal that the H H contacts clearly give the most significant contribution to the Hirshfeld surface (48.2%). In addition, C H/H C, N H/H N, O H/H O and C N/N C contacts contribute 23.9%, 17.4%, 5.3% and 2.6%, respectively, to the Hirshfeld surface. In particular, the N H/H N and O H/H O contacts indicate the presence of intermolecular C—H N and C—H O inter- actions, respectively. Much weaker C C (2.2%) and C O/ O C (0.5%) contacts also occur.

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Co crystallization of a neutral mol­ecule and its zwitterionic tautomer: structure and Hirshfeld surface analysis of 5 methyl 4 (5 methyl 1H pyrazol 3 yl) 2 phenyl 2,3 di­hydro 1H pyrazol 3 one 5 methyl 4 (5 methyl 1H pyrazol 2 ium 3 yl) 3 oxo 2 phenyl 2,

Co crystallization of a neutral mol­ecule and its zwitterionic tautomer: structure and Hirshfeld surface analysis of 5 methyl 4 (5 methyl 1H pyrazol 3 yl) 2 phenyl 2,3 di­hydro 1H pyrazol 3 one 5 methyl 4 (5 methyl 1H pyrazol 2 ium 3 yl) 3 oxo 2 phenyl 2,3 di­hydro 1H pyrazol 1 ide monohydrate

Tautomerism relates to a phenomenon whereby isomeric structures undergo inter-conversion by the migration of, typically, an atom, often a proton, or small group within the molecule. While different tautomers can co-exist in solution, in crystals usually only one form is found (Rubcˇic´ et al., 2012). Notable examples of tautomers crystallizing in the same crystal begin with biologically relevant isocytosine (Sharma & McConnell, 1965) and the histidine residue in the structure of l -His-Gly hemihydrate (Steiner & Koellner, 1997). Such behaviour has also been observed, for example, in a synthetic compound, namely, N-(3-hydroxysalicylidene)-4-methoxy- aniline (Pizzala et al., 2000). Herein, the crystal and molecular structures of the title compound, (I), are described along with an analysis of the calculated Hirshfeld surfaces.
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Crystal structure, Hirshfeld surface analysis and DFT studies of 1 benzyl 3 [(1 benzyl 1H 1,2,3 triazol 5 yl)meth­yl] 2,3 di­hydro 1H 1,3 benzo­diazol 2 one monohydrate

Crystal structure, Hirshfeld surface analysis and DFT studies of 1 benzyl 3 [(1 benzyl 1H 1,2,3 triazol 5 yl)meth­yl] 2,3 di­hydro 1H 1,3 benzo­diazol 2 one monohydrate

Lakhrissi et al., 2008). As a continuation of our research devoted to the study of the cycloaddition reactions involving benzimidazolone derivatives (Sebbar et al., 2016; Saber et al., 2020), we report herein the synthesis, the molecular and crystal structures of the title compound along with the results of the Hirshfeld surface analysis and the density functional theory (DFT) computational calculations carried out at the B3LYP/6–311 G(d,p) level in order to compare the theoretical and experimentally determined molecular structures in the solid state.

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A Hirshfeld Surface Analysis and Crystal Structure of 2’ [1 (2 Fluoro Phenyl) 1H tetrazol 5 Yl] 4 Methoxy Biphenyl 2 Carbaldehyde

A Hirshfeld Surface Analysis and Crystal Structure of 2’ [1 (2 Fluoro Phenyl) 1H tetrazol 5 Yl] 4 Methoxy Biphenyl 2 Carbaldehyde

Tetrazoles and its derivatives are the most important in the field of medicinal chemistry and found wide spec- trum of applications in coordination chemistry because of their multiple coordination status, acting as ligands to metal ions and for the construction of novel metal-or- ganic frameworks [1-3]. And they exhibit biological ac- tivities like antibacterial [4,5], antifungal and anticon- vulsant [6], analgesic [7], antitubercular activity [8] and anti-cancer activity [9]. Also, 1,5-disubstituted tetrazoles used as anti-inflammatory and anti-hypertensive agents [10,11], such as Losartan [12,13]. Biphenyl tetrazoles have also demonstrated activities as stimulators of growth hormone release [14], metallo-protease inhibitors [15,16] and chloride channel blockers [17]. And, the 5-substituted 1H-tetrazole moiety has been used in the drug discovery as a bioisotere for the corboxylic acid group [18]. In addition, tetrazole compounds are used as new energetic materials because of their good thermal stability due to the presence of aromatic ring system (5-Azido-1H-tetrazole) [19]. Synthesizing the organic
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S Benzyl 3 [1 (6 methyl­pyridin 2 yl)ethyl­­idene]di­thio­carbazate: crystal structure and Hirshfeld surface analysis

S Benzyl 3 [1 (6 methyl­pyridin 2 yl)ethyl­­idene]di­thio­carbazate: crystal structure and Hirshfeld surface analysis

1’). The presence of the weak intermolecular C—H S contact involving the phenyl-C8 and thione-S2 atoms is evident from the diminutive red spots near these atoms in Fig. 3 (labelled as ‘2’). The faint-red spots near the phenyl-H7 and -C8 atoms in Fig. 3b (labelled as ‘3’) characterize the short surface C H/H C contacts and indicate the relative importance of this particular C—H contact compared with the other two C—H contacts summarized in Table 1. The most prominent interlayer contact appears to be a weak methyl-C16—H S1(ester) interaction (Table 2). The donors and acceptors of intermolecular interactions are also repre- sented with blue and red regions, respectively, corresponding to positive and negative electrostatic potentials on the Hirshfeld surface mapped over electrostatic potential in Fig. 4. The intermolecular C—H contacts, involving donor atoms, and their reciprocal contacts, i.e. H—C, containing -bond acceptors, on the Hirshfeld surface mapped with the shape-index property are illustrated in Fig. 5.
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4 [(1 Benzyl 1H 1,2,3 triazol 4 yl)meth­­oxy]benzene 1,2 dicarbo­nitrile: crystal structure, Hirshfeld surface analysis and energy minimization calculations

4 [(1 Benzyl 1H 1,2,3 triazol 4 yl)meth­­oxy]benzene 1,2 dicarbo­nitrile: crystal structure, Hirshfeld surface analysis and energy minimization calculations

There are four closely related structures to (I) in the crystal- lographic literature (Groom & Allen, 2014). The chemical structures of (II)–(V) are shown in Scheme 2, salient dihedral angles are given in Table 3 and a comparison between mol- ecules is shown in Fig. 8. The similarity in the structures is seen in the relationship between the central triazolyl ring and pendent phenyl rings. By contrast to the conformation observed in (I), which was described above as anti with respect to the relative orientation of the N- and C-bound residues to the central ring, a syn disposition is observed in each of (II) (Rostovtsev et al., 2002), (III) (Garcia et al., 2011) and (IV) (Lo´pez-Ruiz et al., 2013). A similar but somewhat flattened syn relationship is observed in (V) (Lo´pez-Ruiz et al., 2013) for which an intramolecular O N contact of 2.745 (3) A ˚ is noted between the ether-O and benzoxazole-N atoms. The difference in structures prompted energy-minimization calculations.
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Crystal structure and Hirshfeld surface analysis of ethyl 2 [5 (3 chloro­benz­yl) 6 oxo 3 phenyl 1,6 di­hydro­pyridazin 1 yl]acetate

Crystal structure and Hirshfeld surface analysis of ethyl 2 [5 (3 chloro­benz­yl) 6 oxo 3 phenyl 1,6 di­hydro­pyridazin 1 yl]acetate

A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016) revealed two structures containing a similar pyridazinone moiety as in the title structure but with different substituents, viz. 4-benzyl-6-p- tolylpyridazin-3(2H)-one (YOTVIN; Oubair et al., 2009) and ethyl 3-methyl-6-oxo-5-(3-(trifluoromethyl)phenyl)-1,6-di- hydro-1-pyridazineacetate (QANVOR; Xu et al., 2005). In the crystal structure of YOTVIN, the molecules are connected two-by-two through N—H O hydrogen bonds with an R 2
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Crystal structure and Hirshfeld surface analysis of 1 (4 bromo­phen­yl) 2 {[5 (pyridin 3 yl) 1,3,4 oxa­diazol 2 yl]sulfan­yl}ethan 1 one

Crystal structure and Hirshfeld surface analysis of 1 (4 bromo­phen­yl) 2 {[5 (pyridin 3 yl) 1,3,4 oxa­diazol 2 yl]sulfan­yl}ethan 1 one

derivatives were found, viz. 1,3-bis{[5-(pyridin-2-yl)-1,3,4- oxadiazol-2-yl]sulfanyl}propan-2-one (II) (Xia et al., 2011) and 2-{5-[(1H-1,2,4-triazol-1-yl)-methyl]-1,3,4-oxadiazol-2-ylthio}- 1-(2,4-dichlorophenyl)ethanone (III) (Xu et al., 2005). H N interactions were found to be the most relevant inter- molecular interactions to form hydrogen bonds with neigh- boring molecules. Therefore, D—H N interactions were considered in a comparison with reported structures. In the crystal of (II), the molecules are linked into a three-dimen- sional network via weak C—H N hydrogen bonds (H N distances = 2.51 and 2.54 A ˚ ) In (III), the C—H N hydrogen bonds are found to be slightly weaker in comparison with the first structure (H N distances = 2.41 A ˚ ). The change in substituents also changes the packing pattern towards zigzag chains extending along the b-axis direction. In addition, both (II) and (III) feature aromatic – stacking interactions, which are not observed in (I).
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Crystal structure and Hirshfeld surface analysis of ethyl 2 {4 [(3 methyl 2 oxo 1,2 di­hydro­quinoxalin 1 yl)meth­yl] 1H 1,2,3 triazol 1 yl}acetate

Crystal structure and Hirshfeld surface analysis of ethyl 2 {4 [(3 methyl 2 oxo 1,2 di­hydro­quinoxalin 1 yl)meth­yl] 1H 1,2,3 triazol 1 yl}acetate

Quinoxaline derivatives, especially quinoxalinone, are of great importance in medicinal chemistry (Ramli & Essassi, 2015; Ramli et al., 2017) and can be used for the synthesis of numerous heterocyclic compounds with various biological activities such as antibacterial (Griffith et al., 1992), HIV (Loriga et al., 1997), antimicrobial (Badran et al., 2003), anti- inflammatory (Wagle et al., 2008), antiprotozoal (Hui et al., 2006), and anticancer (Carta et al., 2006). In a continuation of our research work devoted to the study of cycloaddition reactions involving quinoxaline derivatives (Ramli et al., 2011, 2013; Abad et al., 2018; Sebbar et al., 2016), we report in this work the synthesis, using 3-methyl-1-(prop-2-ynyl)-3,4-di- hydroquinoxalin-2(1H)-one as dipolarophile and ethyl azido acetate as 1,3-dipole, and crystal structure of ethyl 2-{4-[(3- methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)methyl]-1H-1,2,3- triazol-1-yl}acetate, C 16 H 17 N 5 O 3 (Fig. 1).
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4 (4 Acetyl 5 methyl 1H 1,2,3 triazol 1 yl)benzo­nitrile: crystal structure and Hirshfeld surface analysis

4 (4 Acetyl 5 methyl 1H 1,2,3 triazol 1 yl)benzo­nitrile: crystal structure and Hirshfeld surface analysis

The Hirshfeld surface calculations for (I) were performed in accord with related studies (Caracelli et al., 2018) and provide information on the influence of other weak intermolecular interactions instrumental in the molecular packing. In addition to the presence of carbonyl-C O (triazolyl) and cyano- C N (triazolyl) interactions (Table 1) in the formation of three-dimensional architecture as discussed above, the mol- ecular packing also features weak C—H N interactions. On the Hirshfeld surface mapped over d norm in Fig. 3, these

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Crystal structure and Hirshfeld surface analysis of 1 [(1 butyl 1H 1,2,3 triazol 4 yl)meth­yl] 3 methyl­quinoxalin 2(1H) one

Crystal structure and Hirshfeld surface analysis of 1 [(1 butyl 1H 1,2,3 triazol 4 yl)meth­yl] 3 methyl­quinoxalin 2(1H) one

Quinoxaline groups are well known, important nitrogen- containing heterocyclic compounds comprising a benzene and a pyrazine ring fused together. Diversely substituted quinox- alines and their derivatives embedded with variety of func- tional groups are important biological agents and a significant amount of research activity has been directed towards this class of compounds. These molecules exhibit a wide range of biological applications and are potentially useful in medicinal chemistry research and have therapeutic applications such as antimicrobial (Attia et al., 2013; Vieira et al., 2014; Teja et al., 2016), anti-inflammatory (Guirado et al., 2012), anticancer (Abbas et al., 2015), antidiabetic (Kulkarni et al., 2012) and antihistaminic activities (Sridevi et al., 2010). As a continua- tion of our research works on the synthesis, spectroscopic and biological properties of quinoxaline derivatives (Ramli et al., 2013, 2017; Ramli & Essassi, 2015; Abad et al., 2018a,b,c; Ellouz et al., 2015; Sebbar et al., 2014), we report herein the molecular and crystal structures along with the Hirshfeld surface analysis of the title compound, 1-[(1-butyl-1H-1,2,3- triazol-5-yl)methyl]-3-methyl-1,2-dihydroquinoxalin-2-one.
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4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal structure and Hirshfeld surface analysis

4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal structure and Hirshfeld surface analysis

The title compound, C 12 H 10 N 4 O, comprises a central 1,2,3-triazole ring (r.m.s. deviation = 0.0030 A ˚ ) flanked by N-bound 4-cyanophenyl and C-bound acetyl groups, which make dihedral angles of 54.64 (5) and 6.8 (3)  with the five- membered ring, indicating a twisted molecule. In the crystal, the three- dimensional architecture is sustained by carbonyl-C O   (triazoyl), cyano- C N   (triazoyl) (these interactions are shown to be attractive based on non- covalent interaction plots) and – stacking interactions [intercentroid separation = 3.9242 (9) A ˚ ]. An analysis of the Hirshfeld surface shows the important contributions made by H  H (35.9%) and N  H (26.2%) contacts to the overall surface, as well as notable contributions by O  H (9.9%), C  H (8.7%), C   C (7.3%) and C  N (7.2%) contacts.
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Crystal structure of (E) 4 {[2 (2,4 di­nitro­phen­yl)hydrazin 1 yl­­idene]meth­yl} 3 methyl 1 phenyl 5 (1H pyrrol 1 yl) 1H pyrazole

Crystal structure of (E) 4 {[2 (2,4 di­nitro­phen­yl)hydrazin 1 yl­­idene]meth­yl} 3 methyl 1 phenyl 5 (1H pyrrol 1 yl) 1H pyrazole

In 20 ml of ethanol, a mixture of 5.06 g m (0.02 mol) of 3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-4,5-dihydro-1H- pyrazole-4-carbaldehyde and 3.96 g m (0.02 mol) of (2,4-dinitrophenyl)hydrazine was heated under reflux for 8 h. The resulting solid product was filtered off, dried under vacuum and crystallized from dioxane to furnish red-orange crystals in a sufficient quality for X-ray diffraction. M.p 491–493 K, yield 71%.

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1 Benzyl 2 [1 (5 methyl 1H pyrazol 3 yl) 2 phenyl­ethyl]benzimidazole

1 Benzyl 2 [1 (5 methyl 1H pyrazol 3 yl) 2 phenyl­ethyl]benzimidazole

Hydrazine hydrate (0.29 cc, 0.006 mol) was added to a solution of (4Z)-(2-oxopropylidene)-1,3-dibenzyl-1,2,4,5-tetrahydro-2H-1,5- benzodiazepin-2-one (1.17 g, 0.003 mol) in ethanol (30 ml). The reaction mixture was heated at reflux for 8 h; after cooling, a solid was isolated and dried under vacuum (yield 82%). 1 H NMR (CDCl

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(±) 3 (5 Amino 3 methyl 1 phenyl 1H pyrazol 4 yl) 2 benzo­furan 1(3H) one

(±) 3 (5 Amino 3 methyl 1 phenyl 1H pyrazol 4 yl) 2 benzo­furan 1(3H) one

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

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Crystal structure and Hirshfeld analysis of 2 [bis­­(1 methyl 1H indol 3 yl)meth­yl]benzoic acid

Crystal structure and Hirshfeld analysis of 2 [bis­­(1 methyl 1H indol 3 yl)meth­yl]benzoic acid

Equimolar amounts of 2-carboxybenzaldehyde (3.0 mmol) and 1-methylindole (3.0 mmol) was mixed in a reaction vessel. A few drops of anhydrous acetic acid was added and the mixture was then irradiated in a domestic microwave oven at 100 W for 5 min. The crude product obtained was purified by recrystallization from an acetone–EtOH solvent mixture (v:v = 1:2) to give the pure product in 13.3% yield. IR (ATR, max /

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