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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 [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.105
Data-to-parameter ratio = 18.9
Details
Open access

4-Nitrophenyl 2-chlorobenzoate

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-H...O 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[Selvakumar, N., Malar Azhagan, A., Seinivas, D. & Gopi Krishna, G. (2002). Tetrahedron Lett. 43, 9175-9178.]); Jefford & Zaslona (1985[Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.]). For a similar hydrogen-bonding pattern in a related structure, see: Akhter et al. (2012[Akhter, T., Masood Siddiqi, H., Akhter, Z. & McKee, V. (2012). Acta Cryst. E68, o1912.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8ClNO4

  • Mr = 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[alpha] radiation

  • [mu] = 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[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.888, Tmax = 0.951

  • 54293 measured reflections

  • 3251 independent reflections

  • 3071 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.105

  • S = 1.14

  • 3251 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O1i 0.95 2.48 3.3368 (19) 150
Symmetry code: (i) x, y, z-1.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CSD] [CrossRef] [details]
Jefford, C. W. & Zaslona, A. (1985). Tetrahedron Lett. 26, 6035-6038.  [CrossRef] [ChemPort] [ISI]
Selvakumar, N., Malar Azhagan, A., Seinivas, D. & Gopi Krishna, G. (2002). Tetrahedron Lett. 43, 9175-9178.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.


Acta Cryst (2013). E69, o96  [ doi:10.1107/S1600536812050362 ]

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