Ethyl 2-(4-nitro­benzamido)­benzoate, a non-merohedral twin

Sohail Saeed; Naghmana Rashid; Jerry P Jasinski; Ray J Butcher

doi:10.1107/S1600536811002236

. 2011 Jan 22;67(Pt 2):o465. doi: 10.1107/S1600536811002236

Ethyl 2-(4-nitrobenzamido)benzoate, a non-merohedral twin

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Jerry P Jasinski ^b, Ray J Butcher ^c

PMCID: PMC3051796 PMID: 21523125

Abstract

In the title compound, C₁₆H₁₄N₂O₅, a non-merohedral twin, the dihedral angle between the mean planes of the two benzene rings is 4.0 (9)°. The ethyl group is disordered [0.643 (14) and 0.357 (14) occupancy]. The nitro group is twisted by 16.4 (4)° from the mean plane of the benzene ring and the mean plane of the carbonyl group is twisted from the mean planes of the two benzene rings by 4.5 (0) and 4.7 (9)°. An intramolecular N—H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions.

Related literature

For applications of amides and amide derivatives in the pharmaceutical industry, see: Banihashemi & Firoozifar (2003 ▶); Mallakpour & Kowsari (2005 ▶); Saxena et al. (2003 ▶); Wang et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₅
M _r = 314.29
Triclinic,
a = 6.9802 (3) Å
b = 9.3570 (4) Å
c = 12.5779 (5) Å
α = 102.833 (4)°
β = 94.296 (4)°
γ = 107.567 (4)°
V = 754.68 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.88 mm⁻¹
T = 295 K
0.52 × 0.48 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.825, T _max = 1.000
10410 measured reflections
10410 independent reflections
9282 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.157
S = 1.04
10410 reflections
218 parameters
25 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002236/hg2769sup1.cif

e-67-0o465-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002236/hg2769Isup2.hkl

e-67-0o465-Isup2.hkl^{(509KB, hkl)}

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
N2—H2⋯O4	0.86	1.95	2.6638 (9)	139
C2—H2A⋯O3ⁱ	0.93	2.50	3.4069 (11)	166
C10—H10A⋯O2ⁱⁱ	0.93	2.56	3.3716 (14)	146
C12—H12A⋯O1ⁱⁱⁱ	0.93	2.50	3.2554 (12)	138

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

Acknowledgments

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

The development of heat-resistant, high performance polymers in the past decades has been quite dramatic and has drawn the attention of many polymer scientists all over the world. Wholly aromatic polymers such as polyamides and polyimides have already been noted for high temperature resistance and excellent physico-mechanical properties. Amides and amide derivatives have extensive applications in the pharmaceutical industry (Wang et al., 2008) and in polymer chemistry (Saxena et al., 2003; Banihashemi & Firoozifar, 2003; Mallakpour et al., 2005).

In the title compound, C₁₆H₁₄N₂O₅, a nonmerohedral twin, the dihedral angle between the mean planes of the two benzene rings is 4.0 (9)° (Fig. 1). The ethyl group is disordered (0.643 (14) & 0.357 (14) occupancy). The nitro group is twisted by 16.4 (4)° from the mean plane of the benzene ring and the mean plane of the carbonyl group is twisted from the mean planes of the two benzene rings by 4.5 (0)° and 4.7 (9)°, respectively. Bond distances and angles are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by intramolecular N—H···O, and weak C—H···O intermolecular hydrogen bond interactions (Fig. 2).

Experimental

A mixture of 4-nitrobenzoyl chloride (0.01 mol) and ethyl-p-aminobenzoate (0.01 mol) was refluxed in anhydrous acetone (70 ml) for three hours. After cooling to room temperature, the mixture was poured into acidified cold water. The resulting yellow solid product was filtered and washed with cold acetone. Single crystals of the title compound suitable for single-crystal x-ray analysis were obtained by recrystallization of the yellow solid from ethyl acetate.