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Volume 69 
Part 10 
Pages o1594-o1595  
October 2013  

Received 7 June 2013
Accepted 24 September 2013
Online 28 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.137
Data-to-parameter ratio = 12.0
Details
Open access

2-Benzyl-5-methoxyisoindoline-1,3-dione

aDepartment of Organic Chemistry, University of Vigo, E-36310 Vigo, Spain
Correspondence e-mail: mcteran@uvigo.es

The title N-benzylphthalimide derivative, C16H13NO3, consists of two planar moieties, viz. the phthalimide system (r.m.s. deviation = 0.007 Å) and the phenyl ring, which make a dihedral angle of 84.7 (6)°. The methoxy group is almost coplanar with the phathalimide ring, as shown by the C-C-O-C torsion angle of -171.5 (2)°. In the crystal, the molecules are self-assembled via non-classical C-H...O hydrogen bonds, forming a tape motif along [110].

Related literature

For background to the applications of phthalimide derivatives, see: Luzzio (2005[Luzzio, F. A. (2005). Science of Synthesis, Vol. 21, edited by S. Veinreb, pp. 259-324. Stuttgart: Thieme Chemistry.]); Barooah & Baruah (2007[Barooah, N. & Baruah, J. B. (2007). Mini-Rev. Org. Chem. 4, 292-309.]); Sharma et al. (2010[Sharma, U., Kumar, P., Kumar, N. & Singh, B. (2010). Mini Rev. Med. Chem. 10, 678-704.]); Warzecha et al. (2006[Warzecha, K.-D., Görner, H. & Griesbeck, A. G. (2006). J. Phys. Chem. A, 110, 3356-3363.]). For different approaches to synthesize N-benzylphthalimides, see: Luzzio (2005[Luzzio, F. A. (2005). Science of Synthesis, Vol. 21, edited by S. Veinreb, pp. 259-324. Stuttgart: Thieme Chemistry.]); Cao & Alper (2010[Cao, H. & Alper, H. (2010). Org. Lett. 12, 4126-4129.]); Vidal et al. (2000[Vidal, T., Petit, A., Loupy, A. & Gedye, R. N. (2000). Tetrahedron, 56, 5473-5478.]). For the synthesis of the title compound, see: Favor et al. (2008[Favor, D., Powers, J. J., Repine, J. T. & White, A. D. (2008). PCT Int. Appl. WO 020306.]); Haj-Yehia & Khan (2004[Haj-Yehia, A. I. & Khan, M. A. (2004). PCT Int. Appl. WO 047837.]). For related structures, see: Warzecha et al. (2006a[Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006a). Acta Cryst. E62, o2367-o2368.],b[Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006b). Acta Cryst. E62, o5271-o5273.],c[Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006c). Acta Cryst. E62, o5450-o5452.]); Jiang et al. (2008[Jiang, Z., Wang, J.-D., Chen, N.-S. & Huang, J.-L. (2008). Acta Cryst. E64, o324.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13NO3

  • Mr = 267.27

  • Monoclinic, P 21 /n

  • a = 8.476 (4) Å

  • b = 5.264 (3) Å

  • c = 28.295 (13) Å

  • [beta] = 93.589 (9)°

  • V = 1260.0 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.49 × 0.13 × 0.07 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.993

  • 5768 measured reflections

  • 2204 independent reflections

  • 1433 reflections with I > 2[sigma](I)

  • Rint = 0.083

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.137

  • S = 1.00

  • 2204 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O5i 0.95 2.57 3.505 (3) 168
C7-H7...O1ii 0.95 2.40 3.247 (3) 149
C8-H8B...O3i 0.98 2.59 3.432 (4) 144
Symmetry codes: (i) -x, -y+3, -z+2; (ii) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2100 ).


Acknowledgements

This work was supported financially by the Xunta de Galicia (CN 2012/184). The authors gratefully acknowledge Dr Berta Covelo, X-ray service of the University of Vigo, for her valuable assistance. NV thanks the University of Vigo for a PhD fellowship.

References

Barooah, N. & Baruah, J. B. (2007). Mini-Rev. Org. Chem. 4, 292-309.  [CrossRef] [ChemPort]
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.
Cao, H. & Alper, H. (2010). Org. Lett. 12, 4126-4129.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Favor, D., Powers, J. J., Repine, J. T. & White, A. D. (2008). PCT Int. Appl. WO 020306.
Haj-Yehia, A. I. & Khan, M. A. (2004). PCT Int. Appl. WO 047837.
Jiang, Z., Wang, J.-D., Chen, N.-S. & Huang, J.-L. (2008). Acta Cryst. E64, o324.  [CSD] [CrossRef] [IUCr Journals]
Luzzio, F. A. (2005). Science of Synthesis, Vol. 21, edited by S. Veinreb, pp. 259-324. Stuttgart: Thieme Chemistry.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sharma, U., Kumar, P., Kumar, N. & Singh, B. (2010). Mini Rev. Med. Chem. 10, 678-704.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vidal, T., Petit, A., Loupy, A. & Gedye, R. N. (2000). Tetrahedron, 56, 5473-5478.  [Web of Science] [CrossRef] [ChemPort]
Warzecha, K.-D., Görner, H. & Griesbeck, A. G. (2006). J. Phys. Chem. A, 110, 3356-3363.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006a). Acta Cryst. E62, o2367-o2368.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006b). Acta Cryst. E62, o5271-o5273.  [CrossRef] [IUCr Journals]
Warzecha, K.-D., Lex, J. & Griesbeck, A. G. (2006c). Acta Cryst. E62, o5450-o5452.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1594-o1595   [ doi:10.1107/S160053681302638X ]

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