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Volume 69 
Part 7 
Page o1108  
July 2013  

Received 24 May 2013
Accepted 11 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.113
Data-to-parameter ratio = 14.9
Details
Open access

1,4,10,13-Tetraoxa-7,16-diazoniacyclooctadecane bis(1H-pyrrole-2-carboxylate)

aTianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China
Correspondence e-mail: tjyinzm@aliyun.com

In the title salt, C12H28N2O42+·2C5H4NO2-, the 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane dication possesses inversion symmetry. In the crystal, the pyrrole-carboxylate anions are linked via pairs of N-H...O hydrogen bonds, forming inversion dimers. These dimers are linked by the dications, via N-H...O hydrogen bonds, forming chains propagating along [110].

Related literature

For background to hydrogen-bonded supramolecular assemblies, see: Burrows (2004[Burrows, A. D. (2004). Struct. Bond. 108, 55-96.]). For the hydrogen-bonded assemblies of pyrrole-based structures, see: Wang & Yin (2007[Wang, W.-Y. & Yin, Z.-M. (2007). Acta Cryst. E63, o2737-o2738.]); Yin & Li (2006[Yin, Z. & Li, Z. (2006). Tetrahedron Lett. 47, 7875-7879.]); Cui et al. (2009[Cui, Y., Yin, Z., Dong, L. & He, J. (2009). J. Mol. Struct. 938, 322-327.]); Li et al. (2012[Li, C., Zhang, G. & Yin, Z. (2012). Acta Cryst. E68, m323.]).

[Scheme 1]

Experimental

Crystal data
  • C12H28N2O42+·2C5H4NO2-

  • Mr = 484.55

  • Triclinic, [P \overline 1]

  • a = 7.8963 (19) Å

  • b = 9.164 (2) Å

  • c = 9.244 (2) Å

  • [alpha] = 73.028 (4)°

  • [beta] = 76.547 (4)°

  • [gamma] = 77.824 (4)°

  • V = 614.8 (3) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 294 K

  • 0.24 × 0.22 × 0.18 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.982

  • 3484 measured reflections

  • 2471 independent reflections

  • 1695 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.03

  • 2471 reflections

  • 166 parameters

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

  • [Delta][rho]max = 0.14 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
N2-H2...O4i 0.877 (19) 1.94 (2) 2.7741 (19) 158.0 (17)
N1-H1B...O3ii 0.91 (2) 2.01 (2) 2.8167 (19) 147.4 (16)
N1-H1A...O4 0.94 (2) 2.489 (19) 3.137 (2) 125.9 (14)
N1-H1A...O3 0.94 (2) 1.81 (2) 2.7452 (19) 171.1 (17)
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, 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.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2108 ).


Acknowledgements

We sincerely thank the Natural Science Foundation of China for financial support (NSFC No. 21172174).

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burrows, A. D. (2004). Struct. Bond. 108, 55-96.  [CrossRef] [ChemPort]
Cui, Y., Yin, Z., Dong, L. & He, J. (2009). J. Mol. Struct. 938, 322-327.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Li, C., Zhang, G. & Yin, Z. (2012). Acta Cryst. E68, m323.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, W.-Y. & Yin, Z.-M. (2007). Acta Cryst. E63, o2737-o2738.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Yin, Z. & Li, Z. (2006). Tetrahedron Lett. 47, 7875-7879.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1108  [ doi:10.1107/S1600536813016176 ]

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