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Volume 69 
Part 10 
Page o1535  
October 2013  

Received 31 August 2013
Accepted 3 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.098
Data-to-parameter ratio = 11.7
Details
Open access

3,22-Dioxa-11,14-diazapentacyclo[12.8.0.02,11.05,10.015,20]docosa-5(10),6,8,15(20),16,18-hexaene-4,21-dione

aInstitute of Molecular Science, Chemical Biology and Molecular Engineering Laboratory of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China, and bDepartment of Chemistry, Changzhi University, Changzhi, Shanxi 046011, People's Republic of China
Correspondence e-mail: yangbs@sxu.edu.cn

In the title compound, C18H14N2O4, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.09 (9)°. In the crystal, molecules are linked along the c axis by C-H...[pi] and N...[pi] [H(N)-centroid distances = 2.8030 (2) and 3.376 (2) Å] interactions between neighbouring molecules.

Related literature

For applications of [pi]-[pi] interactions, see: Janiak (2000[Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]). For C-H...[pi] interactions, see: Ciunik & Desiraju (2001[Ciunik, Z. & Desiraju, G. R. (2001). Chem. Commun. pp. 703-704.]) and for N...[pi] interactions, see: Lindeman et al. (1998[Lindeman, S. V., Kosynkin, D. & Kochi, J. K. (1998). J. Am. Chem. Soc. 120, 13268-13269.]). For the synthesis of the 2,2'-(ethane-1,2-diylbis(azanediyl))dibenzoic acid precursor, see: Berger & Telford (2002[Berger, D. J. & Telford, J. R. (2002). Inorg. Chim. Acta, 341, 132-134.]).

[Scheme 1]

Experimental

Crystal data
  • C18H14N2O4

  • Mr = 322.31

  • Triclinic, [P \overline 1]

  • a = 8.058 (1) Å

  • b = 8.2629 (11) Å

  • c = 12.0972 (14) Å

  • [alpha] = 74.956 (2)°

  • [beta] = 73.868 (1)°

  • [gamma] = 72.311 (1)°

  • V = 723.54 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.23 × 0.20 × 0.13 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.986

  • 3858 measured reflections

  • 2533 independent reflections

  • 1301 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.098

  • S = 1.01

  • 2533 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6-C11 ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg1i 0.98 2.80 3.7337 (3) 159
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART 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.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: FF2118 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21271122 and 20901048) and Shanxi Scholarship Council of China (2013-018).

References

Berger, D. J. & Telford, J. R. (2002). Inorg. Chim. Acta, 341, 132-134.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ciunik, Z. & Desiraju, G. R. (2001). Chem. Commun. pp. 703-704.  [CrossRef]
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.  [CrossRef]
Lindeman, S. V., Kosynkin, D. & Kochi, J. K. (1998). J. Am. Chem. Soc. 120, 13268-13269.  [Web of Science] [CSD] [CrossRef] [ChemPort]
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, o1535  [ doi:10.1107/S1600536813024537 ]

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