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Volume 69 
Part 6 
Page o963  
June 2013  

Received 16 April 2013
Accepted 18 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.104
Data-to-parameter ratio = 12.3
Details
Open access

2-(9H-Fluoren-9-yl)-4-(4-fluoroanilino)-4-oxobutanoic acid

aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kyiv, Ukraine,bLaboratoire de Synthese et Physico-Chimie de Molecules d'Interet Biologique, Paul Sabatier University, 118 route de Narbonne, 31062, Toulouse, France, and cUniversité de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, LSPCMIB, 118 route de Narbonne, F-31062 Toulouse Cedex 9, France
Correspondence e-mail: 417lab@gmail.com

In the title compound, C23H18FNO3, the tricyclic 9-fluorenyl system is approximately planar (r.m.s. deviation = 0.0279 Å). The N-C(=O) bond length is comparatively short [1.359 (3) Å], which is typical for such conjugated systems. The N atom has a planar configuration [sum of bond angles= 359.8°] due to conjugation of its lone pair with the [pi]-system of the carbonyl group. In the crystal, a three-dimensional network is formed through N-H...O and O-H...O hydrogen bonds between the amide and carboxylic acid groups and carbonyl O-atom acceptors.

Related literature

For the synthesis of various succinic anhydrides, see: Clar (1942[Clar, E. (1942). Reichsamt Wirtschaftsausbau Chem. Ber., Pruf-Nr. 015(PB52017), pp. 859-878.]). For biological studies on substituted succinimides, see: Carroll et al. (2007[Carroll, I. F., Ma, W., Navarro, H. A., Abraham, P., Wolckenhauer, S. A., Damaj, M. I. & Martin, B. R. (2007). Bioorg. Med. Chem. 15, 678-685.]); Miller & Johns (1951[Miller, C. A. & Johns, I. B. (1951). J. Am. Chem. Soc. 73, 4895-4898.]); Patsalos (2005[Patsalos, P. N. (2005). Epilepsia, 46(Suppl. 9), 140-148.]); Rankin et al. (1986[Rankin, G., Cressey-Venezia, K., Wang, R. & Brown, P. J. (1986). J. Appl. Toxicol. 6, 349-356.]). For the synthesis of substituted phenysuccinamic acids, see: Galustyan et al. (2000[Galustyan, G. G., Levkovich, M. G. & Abdullaev, N. D. (2000). Chem. Heterocycl. Compd, 36, 1402-1408.]); Stephani et al. (2002[Stephani, R., Cesare, V., Sadarangani, I. & Lengyel, I. (2002). Synthesis, pp. 47-52.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18FNO3

  • Mr = 375.38

  • Monoclinic, P 21 /c

  • a = 10.2048 (6) Å

  • b = 18.5170 (11) Å

  • c = 9.6164 (6) Å

  • [beta] = 90.494 (4)°

  • V = 1817.07 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.45 × 0.10 × 0.03 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.997

  • 8408 measured reflections

  • 3205 independent reflections

  • 1744 reflections with I > 2[sigma](I)

  • Rint = 0.081

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.104

  • S = 1.00

  • 3205 reflections

  • 261 parameters

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O2i 0.98 (4) 1.71 (4) 2.682 (3) 175 (3)
N1-H1N...O3ii 0.88 (2) 2.02 (3) 2.891 (3) 172 (2)
Symmetry codes: (i) -x, -y, -z+2; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2107 ).


References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carroll, I. F., Ma, W., Navarro, H. A., Abraham, P., Wolckenhauer, S. A., Damaj, M. I. & Martin, B. R. (2007). Bioorg. Med. Chem. 15, 678-685.  [PubMed] [ChemPort]
Clar, E. (1942). Reichsamt Wirtschaftsausbau Chem. Ber., Pruf-Nr. 015(PB52017), pp. 859-878.
Galustyan, G. G., Levkovich, M. G. & Abdullaev, N. D. (2000). Chem. Heterocycl. Compd, 36, 1402-1408.  [ChemPort]
Miller, C. A. & Johns, I. B. (1951). J. Am. Chem. Soc. 73, 4895-4898.  [CrossRef] [ChemPort] [ISI]
Patsalos, P. N. (2005). Epilepsia, 46(Suppl. 9), 140-148.
Rankin, G., Cressey-Venezia, K., Wang, R. & Brown, P. J. (1986). J. Appl. Toxicol. 6, 349-356.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Stephani, R., Cesare, V., Sadarangani, I. & Lengyel, I. (2002). Synthesis, pp. 47-52.  [CrossRef]


Acta Cryst (2013). E69, o963  [ doi:10.1107/S1600536813013779 ]

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