3,5-Dibromo-4-carbamoylbenzoic acid 2-propanol monosolvate

Molecules of the title compound are linked by hydrogen-bond dimerization of the amido group, and a chain of hydrogen bonds between 2-propanol and the carboxyl and amido groups that propagates parallel to [100].


Structure description
Although the structure of 2-bromobenzamide is reported twice (Izumi & Okamoto, 1972;Gulyá s et al., 2015) in the current version of the Cambridge Structural Database (version 5.42, Nov 2020;Groom et al., 2016), no 2,6-dibromo-or 4-carboxylbenzamides were found. The title compound (I) is an example of both classes, and was accidentally prepared in an attempt to selectively hydrolyze the ester group of a cyano ester (II) (Fig. 1). The target was cyano acid (III), for a study in our laboratory involving co-crystals of (III) with anthracene (Noland et al., 2017).

Figure 1
The synthesis of (I).

Figure 3
Hydrogen bonding in the crystal of (I), viewed along [010]. For clarity, the minor component and the lower-left molecule of 2-propanol are omitted from the unit cell. The dashed green lines represent amide dimerization. The dashed magenta lines represent the hydrogen bonds that form chains along [100]. The dashed orange line and its magenta counterpart (O2Á Á ÁN1) illustrate head-to-tail dimerization.

Figure 4
Substituted benzamides, in their crystals, viewed along carbamoyl group ipso bonds. The listed dihedral angles (!) are between the best-fit planes of the respective benzene rings and carbamoyl groups.

Figure 2
The molecular structure of (I), with atomic numbering and displacement ellipsoids at the 50% probability level. For clarity, only the major disorder component of 2-propanol is shown.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2.   Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Angle of C2/C3/C4/C5/C6/C7 vs. N1/C1/O1 below Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.9373 (