2017
DOI: 10.1107/s2056989017014815
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A 2:1 co-crystal of 3,5-dibromo-4-cyanobenzoic acid and anthracene

Abstract: The title co-crystal, C 8 H 3 Br 2 NO 2 Á0.5C 14 H 10 , was self-assembled from a 2:1 mixture of the components in slowly evaporating dichloromethane. The molecules adopt a sheet structure parallel to (112) in which carboxy hydrogen-bonded dimers and anthracene molecules stagger in both dimensions. Within the sheets, six individual cyano acid molecules surround each anthracene molecule. Cyano acid molecules form one of the two possible R 2 2 (10) rings between neighboring cyano and bromo groups. Compared to th… Show more

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Cited by 4 publications
(5 citation statements)
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“…Crystals of (VII) contain C(6) chains of C OÁ Á ÁBr contacts (Saeed et al, 2010), and crystals of (VIII) contain C(5) chains of BrÁ Á ÁBr contacts (Reinhold & Rosati, 1994). A co-crystal of cyano acid (IXa) with anthracene was recently reported by our group (Noland et al 2017a). The corresponding isocyano acid (IXb) was not observed, probably because of the acid sensitivity of isocyanides (Ugi et al, 1965), preventing crystallographic comparison of (IXa) and (IXb).…”
Section: Figurementioning
confidence: 81%
See 1 more Smart Citation
“…Crystals of (VII) contain C(6) chains of C OÁ Á ÁBr contacts (Saeed et al, 2010), and crystals of (VIII) contain C(5) chains of BrÁ Á ÁBr contacts (Reinhold & Rosati, 1994). A co-crystal of cyano acid (IXa) with anthracene was recently reported by our group (Noland et al 2017a). The corresponding isocyano acid (IXb) was not observed, probably because of the acid sensitivity of isocyanides (Ugi et al, 1965), preventing crystallographic comparison of (IXa) and (IXb).…”
Section: Figurementioning
confidence: 81%
“…Methyl 4-amino-3,5-dibromobenzoate (RNH2) and methyl 3,5-dibromo-4-cyanobenzoate (RCN) were taken from material prepared in our recent study (Noland et al 2017a; Fig. 7).…”
Section: Synthesis and Crystallizationmentioning
confidence: 99%
“…1). The target was cyano acid (III), for a study in our laboratory involving co-crystals of (III) with anthracene (Noland et al, 2017).…”
Section: Structure Descriptionmentioning
confidence: 99%
“…3,5-Dibromo-4-carbamoylbenzoic acid (I): a portion of compound (II) (589 mg, Fig. 1) taken from our prior study (Noland et al, 2017) was placed in a round-bottomed flask with water (5 ml), 2-propanol (5 ml) and NaOH (186 mg). The resulting mixture was refluxed for 1 h, and then cooled to 290 K. Hydrochloric acid (6 M) was added dropwise until the pH of the mixture was less than 4.…”
Section: Synthesis and Crystallizationmentioning
confidence: 99%
“…The chlorinated and brominated entries are either bis(carbonitriles) [(I), Fig. 1; Britton, 1981;Hirshfeld, 1984;van Rij & Britton, 1981] or 4-carboxy analogs [(II); Britton, 2012;Noland et al, 2017]. All of these 4-substituents have stronger interactions than a methyl group, and exhibit different packing motifs than RCN.…”
Section: Chemical Contextmentioning
confidence: 99%