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Volume 67 
Part 1 
Pages o98-o99  
January 2011  

Received 25 November 2010
Accepted 2 December 2010
Online 11 December 2010

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.065
wR = 0.171
Data-to-parameter ratio = 9.3
Details
Open access

Ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)benzoate

Yi Chen Chan,a Abdussalam Salhin,a+ Melati Khairuddean,a Madhukar Hemamalinib and Hoong-Kun Funb*++

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The title compound, C21H15NO4, was synthesized by reducing the Schiff base obtained from acenaphthenequinone and ethyl-4-aminobenzoate. The dihedral angle between the essentially planar 1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline ring system [maximum deviation = 0.061 (2) Å] and the benzene ring is 75.08 (10)°. In the crystal, molecules are connected via weak intermolecular C-H...O hydrogen bonds, forming a two-dimensional network. The ethyl group is disordered over two sets of sites with a refined occupancy ratio of 0.502 (12):0.498 (12).

Related literature

For details and applications of acenaphthenquinone-based Schiff bases, see: Maldanis et al. (2002[Maldanis, R. J., Wood, J. S., Chandrasekaran, A., Rausch, M. D. & Chien, J. C. W. (2002). J. Organomet. Chem. 645, 158-167.]); Son et al. (2006[Son, G. W., Bijal, K. B., Park, D. W., Ha, C. S. & Kim, I. I. (2006). Catal. Today, 111, 412-416.]); Mhaidat et al. (2009[Mhaidat, I., Mergos, J. A., Hamilakis, S., Kollia, C., Loizos, Z., Tsolomitis, A. & Dervos, C. T. (2009). Mater. Lett. 63, 2587-2590.]); Rodriguez-Argüelles et al. (1997[Rodriguez-Argüelles, M. C., Ferrari, M. B., Fava, G. G., Pelizzi, C., Pelosi, G., Albertini, R., Botani, A., DallÁnglio, P. P., Lunghi, P. & Pinelli, S. (1997). J. Inorg. Biochem. 66, 7-17.]); McDavid et al. (1951[McDavid, J. E. & Daniels, T. C. (1951). J. Am. Pharm. Assoc. 40: 325, 8594.]); Salhin et al. (2007[Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.], 2008[Salhin, A., Abdul Razak, N. & Rahman, I. A. (2008). Acta Cryst. E64, o2353.], 2009[Salhin, A., Abdul Razak, N. & Rahman, I. A. (2009). Acta Cryst. E65, o1221-o1222.]); Tameem et al. (2006[Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o5686-o5688.], 2007[Tameem, A. A., Salhin, A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2502.], 2008[Tameem, A. A., Saad, B., Salhin, A., Jebas, S. R. & Fun, H. K. (2008). Acta Cryst. E64, o679-o680.]); Shalash et al. (2010[Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C21H15NO4

  • Mr = 345.34

  • Monoclinic, C c

  • a = 5.2025 (7) Å

  • b = 18.066 (3) Å

  • c = 17.560 (2) Å

  • [beta] = 98.365 (2)°

  • V = 1632.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.49 × 0.21 × 0.08 mm
Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.992

  • 15726 measured reflections

  • 2393 independent reflections

  • 2157 reflections with I > 2[sigma](I)

  • Rint = 0.040
Refinement

  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.171

  • S = 1.07

  • 2393 reflections

  • 256 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...O3i 0.93 2.60 3.249 (4) 127
C14-H14A...O1ii 0.93 2.41 3.312 (3) 165
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: LH5180 ).

Acknowledgements

YCC, AS and MK acknowledge financial support by the Universiti Sains Malaysia (USM) under the Science Fund Grant No. 1001/PKIMIA/823003. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Maldanis, R. J., Wood, J. S., Chandrasekaran, A., Rausch, M. D. & Chien, J. C. W. (2002). J. Organomet. Chem. 645, 158-167.  [CSD] [CrossRef] [ChemPort]
McDavid, J. E. & Daniels, T. C. (1951). J. Am. Pharm. Assoc. 40: 325, 8594.
Mhaidat, I., Mergos, J. A., Hamilakis, S., Kollia, C., Loizos, Z., Tsolomitis, A. & Dervos, C. T. (2009). Mater. Lett. 63, 2587-2590.  [CrossRef] [ChemPort]
Rodriguez-Argüelles, M. C., Ferrari, M. B., Fava, G. G., Pelizzi, C., Pelosi, G., Albertini, R., Botani, A., DallÁnglio, P. P., Lunghi, P. & Pinelli, S. (1997). J. Inorg. Biochem. 66, 7-17.  [CrossRef] [PubMed] [ISI]
Salhin, A., Abdul Razak, N. & Rahman, I. A. (2008). Acta Cryst. E64, o2353.  [CSD] [CrossRef] [details]
Salhin, A., Abdul Razak, N. & Rahman, I. A. (2009). Acta Cryst. E65, o1221-o1222.  [CSD] [CrossRef] [details]
Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880.  [CSD] [CrossRef] [details]
Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Son, G. W., Bijal, K. B., Park, D. W., Ha, C. S. & Kim, I. I. (2006). Catal. Today, 111, 412-416.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tameem, A. A., Saad, B., Salhin, A., Jebas, S. R. & Fun, H. K. (2008). Acta Cryst. E64, o679-o680.  [CrossRef] [details]
Tameem, A. A., Salhin, A., Saad, B., Rahman, I. A., Saleh, M. I., Ng, S.-L. & Fun, H.-K. (2006). Acta Cryst. E62, o5686-o5688.  [CSD] [CrossRef] [details]
Tameem, A. A., Salhin, A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2502.  [CSD] [CrossRef] [details]

Acta Cryst (2011). E67, o98-o99   [ doi:10.1107/S160053681005049X ]

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