Methyl 2,4-dihy­droxy-5-(4-nitro­benzamido)­benzoate

Naz, S.S.; Islam, N.U.; Tahir, M.N.; Shah, M.R.

doi:10.1107/S160053681300024X

Volume 69
Part 2
Page o207
February 2013

Received 3 January 2013
Accepted 3 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.052
wR = 0.134
Data-to-parameter ratio = 13.1
Details

Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)benzoate

Syeda Sohaila Naz,^a Nazar Ul Islam,^a M. Nawaz Tahir ^b ^* and Muhammad Raza Shah ^c

^aUniversity of Peshawar, Institute of Chemical Sciences, Peshawar, Pakistan,^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C₁₅H₁₂N₂O₇, the dihedral angle between the aromatic rings is 4.58 (13)° and the nitro group is rotated from its attached ring by 18.07 (17)°. Intramolecular N-HO and O-HO hydrogen bonds generate S(5) and S(6) rings, respectively. In the crystal, molecules are linked by O-HO hydrogen bonds, generating [001] C(7) chains. The chains are linked by C-HO interactions, forming a three-dimensional network, which incorporates R₂²(7) and R₂²(10) loops.

Related literature

For a related structure, see: Gorelik et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₂N₂O₇
M_r = 332.27
Monoclinic, C 2/c
a = 30.412 (6) Å
b = 6.9325 (15) Å
c = 14.936 (3) Å
= 111.737 (8)°
V = 2925.0 (11) Å³
Z = 8
Mo K radiation
= 0.12 mm^-1
T = 296 K
0.28 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.970, T_max = 0.980
10681 measured reflections
2885 independent reflections
1519 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.134
S = 0.98
2885 reflections
220 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O4	0.86	2.16	2.595 (3)	111
O3-H3AO2	0.82	1.91	2.619 (3)	144
O4-H4O5ⁱ	0.82	1.86	2.670 (2)	170
C8-H8AO3ⁱⁱ	0.96	2.51	3.274 (4)	137
C12-H12O7ⁱⁱⁱ	0.93	2.38	3.297 (4)	171
C15-H15O4ⁱⁱ	0.93	2.46	3.370 (3)	165
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7022 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gorelik, T., Matveeva, G., Kolb, U., Schleuss, T., Kilbinger, A. F. M., van de Streek, J., Bohle, A. & Brunklaus, G. (2010). CrystEngComm, 12, 1824-1832.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds