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Volume 69 
Part 10 
Page o1569  
October 2013  

Received 1 August 2013
Accepted 7 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 13.4
Details
Open access

Methyl 9-hydroxy-15-methyl-2-oxo-11-(pyren-1-yl)-10-oxa-15-azatetracyclo[7.6.0.01,12.03,8]pentadeca-3(8),4,6-triene-12-carboxylate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C32H25NO5, the furan and pyrrole rings each adopt an envelope conformation, the respective flap atoms being the C atom bearing the pyrene substituent and the CH2 atom adjacent to the N atom. The molecular conformation is stabilized by an intramolecular O-H...N hydrogen bond. In the crystal, C-H...O contacts link the molecules, forming a two-dimensional network parallel to (001).

Related literature

For the solid-state structures of pyrenes, see: Robertson & White (1947[Robertson, J. M. & White, J. G. (1947). J. Chem. Soc. pp. 358-368.]); Camerman & Trotter (1965[Camerman, A. & Trotter, J. (1965). Acta Cryst. 18, 636-643.]); Allmann (1970[Allmann, R. (1970). Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem. 132, 129-151.]); Hazell et al. (1972[Hazell, A. C., Larsen, F. K. & Lehmann, M. S. (1972). Acta Cryst. B28, 2977-2984.]); Kai et al. (1978[Kai, Y., Hama, F., Yasuoka, N. & Kasai, N. (1978). Acta Cryst. B34, 1263-1270.]). For a related structure, see: Gruber et al. (2010[Gruber, T., Seichter, W. & Weber, E. (2010). Acta Cryst. E66, o443.]). For the use of pyrenes in fluorescence sensors, see: Bren (2001[Bren, V. A. (2001). Russ. Chem. Rev. 70, 1017-1036.]).

[Scheme 1]

Experimental

Crystal data
  • C32H25NO5

  • Mr = 503.53

  • Monoclinic, C 2/c

  • a = 31.6964 (6) Å

  • b = 11.0325 (2) Å

  • c = 14.1965 (3) Å

  • [beta] = 96.503 (1)°

  • V = 4932.44 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.983

  • 20953 measured reflections

  • 4661 independent reflections

  • 3280 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.04

  • 4661 reflections

  • 347 parameters

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C27-H27...O3i 0.93 2.43 3.299 (2) 155
O2-H2...N 0.87 (2) 1.95 (2) 2.6217 (19) 133 (2)
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: 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: BT6925 ).


References

Allmann, R. (1970). Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem. 132, 129-151.  [CrossRef] [ChemPort]
Bren, V. A. (2001). Russ. Chem. Rev. 70, 1017-1036.  [CrossRef] [ChemPort]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Camerman, A. & Trotter, J. (1965). Acta Cryst. 18, 636-643.  [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gruber, T., Seichter, W. & Weber, E. (2010). Acta Cryst. E66, o443.  [CSD] [CrossRef] [IUCr Journals]
Hazell, A. C., Larsen, F. K. & Lehmann, M. S. (1972). Acta Cryst. B28, 2977-2984.  [CrossRef] [ChemPort] [IUCr Journals]
Kai, Y., Hama, F., Yasuoka, N. & Kasai, N. (1978). Acta Cryst. B34, 1263-1270.  [CrossRef] [IUCr Journals]
Robertson, J. M. & White, J. G. (1947). J. Chem. Soc. pp. 358-368.  [CrossRef]
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]


Acta Cryst (2013). E69, o1569  [ doi:10.1107/S1600536813024951 ]

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