4-Nitro­phenyl 4-bromo­benzoate

Rodolfo Moreno-Fuquen

doi:10.1107/S1600536811043923

. 2011 Oct 29;67(Pt 11):o3114. doi: 10.1107/S1600536811043923

4-Nitrophenyl 4-bromobenzoate

Rodolfo Moreno-Fuquen ^a,^*

PMCID: PMC3247499 PMID: 22220117

Abstract

In the crystal structure of the title compound, C₁₃H₈BrNO₄, molecules are linked into chains along [101] by weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.140 (4) Å]. The planes of the nitrated and brominated aryl rings form a dihedral angle of 64.98 (10)°, indicating a twist in the molecule.

Related literature

For background to the applications of aromatic esters containing nitro groups, see: Jefford & Zaslona (1985 ▶). For molecular and supramolecular structures of nitroaryl compounds, see: Wardell et al. (2005 ▶); Jefford et al., (1986 ▶). For halogen bonding, see: Politzer et al. (2010 ▶); Ritter (2009 ▶). For hydrogen bonding, see: Nardelli (1995 ▶) and for hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C₁₃H₈BrNO₄
M _r = 322.11
Monoclinic,
a = 8.8177 (4) Å
b = 9.5279 (5) Å
c = 14.9394 (5) Å
β = 99.024 (3)°
V = 1239.59 (10) Å³
Z = 4
Mo Kα radiation
μ = 3.33 mm⁻¹
T = 293 K
0.55 × 0.31 × 0.23 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.250, T _max = 0.361
9341 measured reflections
2648 independent reflections
1918 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.02
2648 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043923/hg5114sup1.cif

e-67-o3114-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043923/hg5114Isup2.hkl

e-67-o3114-Isup2.hkl^{(130.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043923/hg5114Isup3.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
C10—H10⋯O4ⁱ	0.93	2.69	3.543 (6)	153
C3—H3⋯O3ⁱⁱ	0.93	2.60	3.335 (5)	136
C13—H13⋯O3ⁱⁱⁱ	0.93	2.67	3.460 (5)	143
C12—H12⋯O1^iv	0.93	2.50	3.237 (5)	137

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

Acknowledgments

Thanks are given to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a license for the use of the Cambridge Crystallographic Database (CSD; Allen, 2002 ▶). The author also thanks the Universidad del Valle, Colombia, for partial financial support.

supplementary crystallographic information

Comment

Aromatic esters containing nitro groups in their aromatic rings can be used as precursors for the preparation of compounds with potential analgesic and anti-inflammatory properties (Jefford & Zaslona, 1985). Molecular and supramolecular structures of a wide range of nitroaryl compounds have been reported (Wardell et al., 2005 and Jefford et al., 1986).

In order to complement the structural information on nitroaryl compounds the title ester, 4-nitrophenyl bromobenzoate (I) was synthesized. A perspective view of the molecule of the title compound, showing the atomic numbering scheme, is given in Fig. 1. The central ester fragment between atoms C4 and C8 is effectively planar. The nitrated and brominated aryl rings form a dihedral angle of 64.98 (10)°, indicating a twist in the molecule. The nitro group forms a dihedral angle of 2.7 (5)° with the adjacent aryl ring. Halogen bonding, an electrostatically driven higly directional noncovalent interaction, that can be important for its potential in the development of new materials and pharmaceutical compounds (Politzer et al., 2010 and Ritter, 2009) can be observed in the present structure. Indeed, the Br···O contacts along [101] with a Br1···O3ⁱⁱⁱ, (iii: x - 1,+y,+z + 1) distance of 3.140 (4) Å, showing the formation of an infinite chain is detected (see Fig. 2). Other C—H···O weak hydrogen bonds (see Table 1, Nardelli, 1995) that complement the crystal packing can also be seen in this figure. The propagation of these interactions forms R³₃(30), R⁴₄(24) and R²₂(14) rings (Etter, 1990) along this direction.

Experimental

Solution containing equimolar quantities (3.2 mmol) of 4-bromobenzoyl chloride and 4-nitrophenol in acetonitrile (60 ml) was gradually heated under reflux for 2 h. At room temperature, triethylamine was added, to get a solid which was poured in cold water. The solid was recrystallized in dichlorometane to yield excellent yellow crystals suitable for single-crystal X-ray diffraction. M.p. 431 (1) K.