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

Saeed, S.; Rashid, N.; Jasinski, J.P.; Butcher, R.J.

doi:10.1107/S1600536811002236

Volume 67
Part 2
Page o465
February 2011

Received 13 December 2010
Accepted 14 January 2011
Online 22 January 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.001 Å
Disorder in main residue
R = 0.053
wR = 0.157
Data-to-parameter ratio = 47.8
Details

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

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

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan,^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: sohail262001@yahoo.com

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-HO hydrogen bond occurs. The crystal packing is stabilized by weak intermolecular C-HO 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, $[P \overline 1]$
a = 6.9802 (3) Å
b = 9.3570 (4) Å
c = 12.5779 (5) Å
= 102.833 (4)°
= 94.296 (4)°
= 107.567 (4)°
V = 754.68 (6) Å³
Z = 2
Cu K radiation
= 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 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.825, T_max = 1.000
10410 measured reflections
10410 independent reflections
9282 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.157
S = 1.04
10410 reflections
218 parameters
25 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O4	0.86	1.95	2.6638 (9)	139
C2-H2AO3ⁱ	0.93	2.50	3.4069 (11)	166
C10-H10AO2ⁱⁱ	0.93	2.56	3.3716 (14)	146
C12-H12AO1ⁱⁱⁱ	0.93	2.50	3.2554 (12)	138
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z+1; (iii) x+1, y+1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: HG2769 ).

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Banihashemi, A. & Firoozifar, H. (2003). Eur. Polym. J. 39, 281-289.
Mallakpour, S. & Kowsari, E. (2005). Polym. Adv. Technol. 16, 732-737.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Saxena, A., Rao, V. L., Prabhakaran, P. V. & Ninan, K. N. (2003). Eur. Polym. J. 39, 401-405.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, X.-J., Yang, Q., Liu, F. & You, Q.-D. (2008). Synth. Commun. 38, 1028-1035.

organic compounds