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Volume 69 
Part 12 
Page o1752  
December 2013  

Received 5 October 2013
Accepted 1 November 2013
Online 9 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.081
wR = 0.221
Data-to-parameter ratio = 22.1
Details
Open access

4-(3-Fluoro-4-methyl­anilino)-2-methyl­idene-4-oxo­butanoic acid

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

The title compound, C12H12FNO3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 3-fluoro-4-methyl­phenyl ring and the oxo­amine group is 25.7 (7)° in mol­ecule A and 71.3 (7)° in mol­ecule B, while the mean plane of the 2-methyl­idene-4-oxo­butanoic acid group is twisted by 76.2 (1)° from that of the oxo­amine group in mol­ecule A and by 76.2 (4)° in mol­ecule B. In the crystal, N-H...O and O-H...O hydrogen bonds [the latter forming an R22(8) graph-set motif] link the mol­ecules into a two-dimensional network parallel to the ac plane.

Related literature

For properties of itaconic anhydride polymers, 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.]). For derivatives of itaconic anhydride, see: Katla et al. (2011[Katla, S., Pothana, P., Gubba, B. & Manda, S. (2011). Chem. Sin. 2, 47-53.]); Shetgiri & Nayak (2005[Shetgiri, N. P. & Nayak, B. K. (2005). Indian J. Chem. Sect. B, 44, 1933-1936.]); Hanoon (2011[Hanoon, H. D. (2011). Nat. J. Chem. 41, 77-89.]); Nayak et al. (2013[Nayak, P. S., Narayana, B., Yathirajan, H. S., Gerber, T., Brecht, B. van & Betz, R. (2013). Acta Cryst. E69, o83.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12FNO3

  • Mr = 237.23

  • Triclinic, [P \overline 1]

  • a = 6.3368 (3) Å

  • b = 8.2642 (4) Å

  • c = 21.0277 (11) Å

  • [alpha] = 84.057 (4)°

  • [beta] = 89.798 (4)°

  • [gamma] = 86.062 (4)°

  • V = 1092.69 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 173 K

  • 0.38 × 0.32 × 0.16 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.673, Tmax = 1.000

  • 13094 measured reflections

  • 7221 independent reflections

  • 4872 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.081

  • wR(F2) = 0.221

  • S = 1.06

  • 7221 reflections

  • 327 parameters

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

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2A-H2A...O3Ai 0.82 1.84 2.658 (2) 174
O2B-H2B...O3Bii 0.82 1.85 2.667 (2) 176
N1A-H1A...O1Biii 0.86 2.10 2.948 (2) 168
N1B-H1B...O1Aiv 0.86 2.10 2.884 (2) 151
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y-1, z; (iv) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2227 ).


Acknowledgements

BN thanks the UGC for a BSR one-time grant for the purchase of chemicals and the DST-PURSE for financial assistance. HSY thanks the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hanoon, H. D. (2011). Nat. J. Chem. 41, 77-89.
Katla, S., Pothana, P., Gubba, B. & Manda, S. (2011). Chem. Sin. 2, 47-53.  [ChemPort]
Nayak, P. S., Narayana, B., Yathirajan, H. S., Gerber, T., Brecht, B. van & Betz, R. (2013). Acta Cryst. E69, o83.  [CSD] [CrossRef] [IUCr Journals]
Oishi, T. (1980). Polym. J. 12, 719-727.  [CrossRef] [ChemPort] [Web of Science]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shetgiri, N. P. & Nayak, B. K. (2005). Indian J. Chem. Sect. B, 44, 1933-1936.
Urzua, M., Opazo, A., Gargallo, L. & Radic, D. (1998). Polym. Bull. 40, 63-67.  [ChemPort]


Acta Cryst (2013). E69, o1752  [ doi:10.1107/S160053681302998X ]

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