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

Weerawat Sripet; Suchada Chantrapromma; Pumsak Ruanwas; Hoong-Kun Fun

doi:10.1107/S1600536812010963

. 2012 Mar 31;68(Pt 4):o1234. doi: 10.1107/S1600536812010963

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

Weerawat Sripet ^a, Suchada Chantrapromma ^a,^*,^‡, Pumsak Ruanwas ^a, Hoong-Kun Fun ^b,^§

PMCID: PMC3344164 PMID: 22606167

Abstract

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.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Johnston & Taylor (2011 ▶); Li & Cui (2011 ▶); Saeed et al. (2008) ▶. For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₄
M _r = 351.15
Triclinic,
a = 6.1219 (2) Å
b = 7.6519 (3) Å
c = 14.3504 (6) Å
α = 89.197 (1)°
β = 84.795 (1)°
γ = 77.983 (1)°
V = 654.78 (4) Å³
Z = 2
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 100 K
0.54 × 0.27 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.281, T _max = 0.616
14195 measured reflections
3725 independent reflections
3558 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.080
S = 1.12
3725 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010963/hb6654sup1.cif

e-68-o1234-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010963/hb6654Isup2.hkl

e-68-o1234-Isup2.hkl^{(182.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010963/hb6654Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2	0.84 (3)	1.99 (3)	2.6318 (19)	132 (2)
C3—H3A⋯O4ⁱ	0.95	2.57	3.475 (2)	160
C12—H12A⋯O1ⁱⁱ	0.95	2.41	3.358 (2)	172
C10—H10A⋯Br1ⁱⁱⁱ	0.95	2.93	3.863 (2)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

WS thanks the Crystal Materials Research Unit, Prince of Songkla University, for financial support. The authors thank Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

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.

The molecule of the title benzamide derivative (Fig. 1), C₁₄H₁₁BrN₂O₄, is not planar as the plane of the middle N-C=O segment makes the dihedral angles of 23.4 (2) and 20.5 (2) ° with the C1–C6 and C8–C13 benzene rings, respectively whereas the dihedral angle between the two benzene rings is 2.90 (8)°. In the 4-methoxy-2-nitrophenyl moiety, the nitro and methoxy groups are co-planar with the bound benzene ring with the r.m.s. deviation of 0.0265 (1) Å for the eleven non-H atoms [C8–C14/N2/O2–O4] and the torsion angles O2–N2–C9–C8 = -3.8 (2)°, O3–N2–C9–C8 = 175.88 (15)° and C14–O4–C11–C12 = 3.5 (2)°. An intramolecular N1—H1N1···O2 hydrogen bond generates a S(6) ring motif (Bernstein et al., 1995). Bond distances are comparable with those in related structures (Johnston & Taylor, 2011; Li & Cui, 2011 and Saeed et al., 2008).

In the crystal (Fig. 2), the molecules are linked into [210] chains by weak C—H···O and C—H···Br interactions forming R₂²(8) motifs. Br1···O2ⁱⁱⁱ[3.2018 (12) Å; (iii) = -x, 2-y, -z] short contact is presented.

Experimental

A mixture of 4-bromobenzoyl chloride (0.20 g, 0.91 mmol) and 4-metoxy-2-nitroaniline (0.23 g, 1.40 mmol) in anhydrous acetone (20 ml) was refluxed for 4 h. An orange solid was formed, which was filtered and washed with water. 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.