2,6-Dichloro-4-nitrotoluene

Abstract

The title compound, C7H5Cl2NO2[systematic name: 1,3-dichloro-2-methyl-5-nitrobenzene], crystallizes in the chiral space groupP212121with a Flack parameter of −0.03 (5). The methyl C atom, the Cl atoms and the N atom of the nitro substituent all lie extremely close to the plane of the benzene ring; the deviations are 0.028 (3) Å for the methyl C atom, −0.016 (1) and 0.007 (1) Å for the two Cl atoms, and −0.017 (3) Å for the nitro N atom. Hence, no significant steric hindrance of the methyl group by theorthohalogen atoms is observed. The nitro group is inclined to the benzene ring by 9.8 (3)°. In the crystal, molecules are linked by weak C—H...O and C—H...Cl hydrogen bonds, forming layers parallel to theabplane.

Crystal structure and Hirshfeld surface analysis of 2,6-diiodo-4-nitrotoluene and 2,4,6-tribromotoluene

“…In DBNT (Medjroubi et al, 2016), there are two independent molecules per asymmetric unit and the methyl group H atoms are positionally disordered, as found for DBM (Hernandez et al, 2003). While in the compounds DINT and DCNT (Medjroubi et al, 2017), there is only one molecule in the asymmetric unit and no disorder is observed for the methyl group H atoms. In the molecule of DINT, a C m -H (m = methyl) bond is perpendicular to the mean plane of the molecule, as found for triiodomesitylene (TIM; Boudjada et al, 2001).…”

“…2. The structures of the title compounds are ISSN 2056-9890 compared with those of the dichloronitrotoluene (DCNT; Medjroubi et al, 2017) and dibromonitrotoluene (DBNT; Medjroubi et al, 2016) analogues, illustrated in Fig. 3.…”

“…In the crystal of DCNT, molecules are linked by weak C-HÁ Á ÁO and C-HÁ Á ÁCl hydrogen bonds, forming layers parallel to the ab plane Fig. 5 (Medjroubi et al, 2017).…”

“…A difference of 2 is found between the exocyclic angles C ar -C ar -C me , which explains the importance of the interaction of this eclipsed bond with atom Br3. The endocyclic angle in front of the methyl group is equal to 116.6 (3) for DINT, 115.7 (2) for DCNT (Medjroubi et al, 2017), 114.7 (3) for DBNT (Medjroubi et al, 2016) and 114.5 (3) for TBT. The variation of this angle is very sensitive to the substitution of the halogen atoms surrounding the methyl groups of these different compounds.…”

“…calculated using TONTO (Spackman & Jayatilaka, 2009) integrated into CrystalExplorer, using the crystal structure as the starting geometry. Short contacts and contributions to the Hirshfeld surface for DINT, DCNT (Medjroubi et al, 2017) and TBT are given in Table 2. The Hirshfeld surface (HS) mapped over the electrostatic potential for DINT in the range [À0.071 to +0.041], is shown in Fig.…”