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

Nayak, P.S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Brecht, B. van; Betz, R.

doi:10.1107/S160053681205012X

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 (C-C) = 0.002 Å
R = 0.018
wR = 0.047
Data-to-parameter ratio = 18.9
Details

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

Prakash S. Nayak,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Benjamin van Brecht ^c and Richard Betz ^c ^*

^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-HO hydrogen bonds formed by carboxylic groups, as well as N-HO hydrogen bonds formed by amide groups, are present along with C-HO 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); Urzua et al. (1998); Shetgiri & Nayak (2005); Katla et al. (2011); Hanoon (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₀INO₃
M_r = 331.10
Monoclinic, P 2₁ /c
a = 23.1111 (6) Å
b = 4.7863 (1) Å
c = 10.4262 (2) Å
= 97.071 (1)°
V = 1144.54 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.503, T_max = 0.776
12435 measured reflections
2839 independent reflections
2612 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(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
_max = 0.73 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.84	1.83	2.6597 (19)	170
N1-H71O3ⁱⁱ	0.83 (2)	2.10 (2)	2.8963 (18)	161 (2)
C3-H3BO3ⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

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

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Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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organic compounds