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Volume 69 
Part 1 
Page o83  
January 2013  

Received 9 November 2012
Accepted 7 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.002 Å
R = 0.018
wR = 0.047
Data-to-parameter ratio = 18.9
Details
Open access

4-(4-Iodoanilino)-2-methylene-4-oxobutanoic acid

aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C11H10INO3, an addition product of itaconic acid anhydride and 4-iodoaniline, the least-squares planes defined by the atoms of the aromatic moiety and the non-H atoms of the carboxylic acid group enclose an angle of 74.82 (11)°. In the crystal, classical O-H...O hydrogen bonds formed by carboxylic groups, as well as N-H...O hydrogen bonds formed by amide groups, are present along with C-H...O contacts. Together, these connect the molecules into dimeric chains along the b-axis direction.

Related literature

For applications of itaconic acid anhydride, see: Oishi (1980[Oishi, T. (1980). Polym. J. 12, 719-727.]); Urzua et al. (1998[Urzua, M., Opazo, A., Gargallo, L. & Radic, D. (1998). Polym. Bull. 40, 63-67.]); Shetgiri & Nayak (2005[Shetgiri, N. P. & Nayak, B. K. (2005). Indian J. Chem. Sect. B, 44, 1933-1936.]); Katla et al. (2011[Katla, S., Pothana, P., Gubba, B. & Manda, S. (2011). Der Chem. Sin. 2, 47-53.]); Hanoon (2011[Hanoon, H. D. (2011). Nat. J. Chem. 41, 77-89.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10INO3

  • Mr = 331.10

  • Monoclinic, P 21 /c

  • a = 23.1111 (6) Å

  • b = 4.7863 (1) Å

  • c = 10.4262 (2) Å

  • [beta] = 97.071 (1)°

  • V = 1144.54 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.79 mm-1

  • T = 200 K

  • 0.29 × 0.16 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.503, Tmax = 0.776

  • 12435 measured reflections

  • 2839 independent reflections

  • 2612 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.018

  • wR(F2) = 0.047

  • S = 1.06

  • 2839 reflections

  • 150 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.83 2.6597 (19) 170
N1-H71...O3ii 0.83 (2) 2.10 (2) 2.8963 (18) 161 (2)
C3-H3B...O3ii 0.99 2.51 3.266 (2) 134
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2533 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE for financial assistance.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hanoon, H. D. (2011). Nat. J. Chem. 41, 77-89.
Katla, S., Pothana, P., Gubba, B. & Manda, S. (2011). Der Chem. Sin. 2, 47-53.  [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oishi, T. (1980). Polym. J. 12, 719-727.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shetgiri, N. P. & Nayak, B. K. (2005). Indian J. Chem. Sect. B, 44, 1933-1936.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Urzua, M., Opazo, A., Gargallo, L. & Radic, D. (1998). Polym. Bull. 40, 63-67.  [ChemPort]


Acta Cryst (2013). E69, o83  [ doi:10.1107/S160053681205012X ]

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