4-Nitro­phenyl 2-chloro­benzoate

Iqbal, A.; Akhter, T.; Masood Siddiqi, H.; Akhter, Z.; Bolte, M.

doi:10.1107/S1600536812050362

Volume 69
Part 1
Page o96
January 2013

Received 3 December 2012
Accepted 11 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.105
Data-to-parameter ratio = 18.9
Details

4-Nitrophenyl 2-chlorobenzoate

Asma Iqbal,^a Toheed Akhter,^a Humaira Masood Siddiqi,^a ^* Zareen Akhter ^a and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bInstitut fur Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: humaira_siddiqi@yahoo.com

The aromatic rings in the title compound, C₁₃H₈ClNO₄, enclose a dihedral angle of 39.53 (3)°. The nitro group is almost coplanar with the ring to which it is attached [dihedral angle = 4.31 (1)°]. In the crystal, molecules are connected by C-HO hydrogen bonds into chains running along [001].

Related literature

For the use of 4-nitrophenyl-2-chlorobenzoate as a starting material for the synthesis of pain-relieving and anti-inflammatory drugs, see: Selvakumar et al. (2002); Jefford & Zaslona (1985). For a similar hydrogen-bonding pattern in a related structure, see: Akhter et al. (2012).

Experimental

Crystal data

C₁₃H₈ClNO₄
M_r = 277.65
Orthorhombic, P b c a
a = 11.4790 (4) Å
b = 14.0461 (5) Å
c = 14.3702 (7) Å
V = 2316.98 (16) Å³
Z = 8
Mo K radiation
= 0.34 mm^-1
T = 173 K
0.36 × 0.15 × 0.15 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) T_min = 0.888, T_max = 0.951
54293 measured reflections
3251 independent reflections
3071 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.105
S = 1.14
3251 reflections
172 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O1ⁱ	0.95	2.48	3.3368 (19)	150
Symmetry code: (i) x, y, z-1.

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2092 ).

Acknowledgements

The authors acknowledge the Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, for providing necessary research facilities.

References

Akhter, T., Masood Siddiqi, H., Akhter, Z. & McKee, V. (2012). Acta Cryst. E68, o1912.
Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.
Selvakumar, N., Malar Azhagan, A., Seinivas, D. & Gopi Krishna, G. (2002). Tetrahedron Lett. 43, 9175-9178.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.

organic compounds