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Volume 69 
Part 9 
Pages o1445-o1446  
September 2013  

Received 10 August 2013
Accepted 12 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.003 Å
R = 0.062
wR = 0.148
Data-to-parameter ratio = 15.4
Details
Open access

Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4-dicarboxylate-2,9-dimethyl-1,10-phenanthroline-benzene-1,2,4,5-tetracarboxylic acid (1/2/1)

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The asymmetric unit of the title co-crystal, 2C14H13N2+·C10H4O82-·2C14H12N2·C10H6O8, comprises a 2,9-dimethyl-1,10-phenanthrolin-1-ium cation (Me2PhenH+) and a 2,9-dimethyl-1,10-phenanthroline molecule (Me2Phen), each in a general position, and half each of a 2,5-dicarboxybenzene-1,4-dicarboxylate dianion (LH22-) and a benzene-1,2,4,5-tetracarboxylic acid molecule (LH4), each being disposed about a centre of inversion. Small twists are evident in the dianion [the C-C-C-O torsion angles are 168.41 (18) and 16.2 (3)°], whereas a major twist is found for one carboxylic acid group in the neutral molecule [C-C-C-O = 66.3 (2) and 18.2 (3)°]. The most prominent feature of the crystal packing is the formation of linear supramolecular chains along [001] mediated by charge-assisted O-H...O- hydrogen bonding between alternating LH4 and LH22-. These are connected to the Me2PhenH+ and Me2Phen species by N-H...O and O-H...N hydrogen bonds, respectively. A three-dimensional architecture is formed by C-H...O and [pi]-[pi] interactions [inter-centroid distance = 3.5337 (17) Å].

Related literature

For salt formation with benzene-1,2,4,5-tetracarboxylic acid, see: Arman & Tiekink (2013[Arman, H. D. & Tiekink, E. R. T. (2013). Z. Kristallogr. Cryst. Mat. 228, 289-294.]). For a co-crystal involving 2,9-dimethyl-1,10-phenanthroline, see: Arman et al. (2010[Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2602.]). For the structure of a 2,9-dimethyl-1,10-phenanthrolin-1-ium carboxylate salt, see: Derikvand & Olmstead (2011[Derikvand, Z. & Olmstead, M. M. (2011). Acta Cryst. E67, o87-o88.]).

[Scheme 1]

Experimental

Crystal data
  • 2C14H13N2+·C10H4O82-·2C14H12N2·C10H6O8

  • Mr = 1341.32

  • Monoclinic, P 21 /n

  • a = 11.798 (4) Å

  • b = 13.893 (4) Å

  • c = 19.163 (6) Å

  • [beta] = 92.216 (5)°

  • V = 3138.8 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 98 K

  • 0.48 × 0.37 × 0.09 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.723, Tmax = 1.000

  • 22006 measured reflections

  • 7181 independent reflections

  • 6007 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.148

  • S = 1.11

  • 7181 reflections

  • 467 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H1o...O1 0.85 (2) 1.55 (2) 2.403 (2) 176 (3)
O6-H2o...O2i 0.85 (1) 1.74 (1) 2.577 (2) 168 (2)
O8-H3o...N4ii 0.85 (2) 1.79 (2) 2.636 (2) 173 (2)
N1-H1n...O3iii 0.89 (2) 2.41 (2) 3.257 (2) 161 (2)
N1-H1n...O4iii 0.89 (2) 2.35 (2) 2.957 (2) 126 (2)
C13-H13...O7iv 0.95 2.28 3.225 (3) 171
C28-H28...O5v 0.95 2.40 3.320 (3) 162
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5731 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2602.  [CSD] [CrossRef] [details]
Arman, H. D. & Tiekink, E. R. T. (2013). Z. Kristallogr. Cryst. Mat. 228, 289-294.  [CrossRef] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Derikvand, Z. & Olmstead, M. M. (2011). Acta Cryst. E67, o87-o88.  [CrossRef] [ChemPort] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1445-o1446   [ doi:10.1107/S1600536813022691 ]

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