4-Bromo-N-(4-methoxy-2-nitrophenyl)benzamide

In the title compound, C14H11BrN2O4, the amide segment makes dihedral angles of 23.4 (2) and 20.5 (2)° with the benzene rings, while the dihedral angle between the bezene rings is 2.90 (8)°. The nitro and methoxy groups are almost coplanar with their bound benzene ring, with the r.m.s. deviation for the 11 non-H atoms being 0.0265 (1) Å. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into [2-10] chains by weak C—H⋯O and C—H⋯Br interactions, which form an R 2 2(8) motif between pairs of molecules in the chain. A Br⋯O [3.2018 (12) Å] short contact also occurs.

In the title compound, C 14 H 11 BrN 2 O 4 , the amide segment makes dihedral angles of 23.4 (2) and 20.5 (2) with the benzene rings, while the dihedral angle between the bezene rings is 2.90 (8) . The nitro and methoxy groups are almost coplanar with their bound benzene ring, with the r.m.s. deviation for the 11 non-H atoms being 0.0265 (1) Å . An intramolecular N-HÁ Á ÁO hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked into [210] chains by weak C-HÁ Á ÁO and C-HÁ Á ÁBr interactions, which form an R 2 2 (8) motif between pairs of molecules in the chain. A BrÁ Á ÁO [3.2018 (12) Å ] short contact also occurs.

Comment
As part of our research in medicinal chemistry, the title benzamide derivative (I) was synthesized with a hope that it may exhibit anticancer and/or anti-alzheimer activities. Herein, its crystal structure was reported.
Orange blocks of the title compound were recrystallized from ethylacetate by slow evaporation of the solvent at room temperature after a week, Mp. 434-436 K.

Refinement
Amide H atom was located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.95 Å for aromatic and CH and 0.98 Å for CH 3 atoms. The U iso values were constrained to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.75 Å from Br1 and the deepest hole is located at 0.85 Å from Br1.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009   The crystal packing of the title compound viewed along the c axis. Hydrogen bonds were drawn as dashed lines.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. 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. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.