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Volume 69 
Part 12 
Pages o1782-o1783  
December 2013  

Received 11 October 2013
Accepted 10 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.005 Å
R = 0.088
wR = 0.272
Data-to-parameter ratio = 13.8
Details
Open access

2,9-Dimethyl-1,10-phenanthrolin-1-ium 2,4,5-tri­carb­oxy­benzoate monohydrate

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
Correspondence e-mail: zklong76@163.com

In the preparation of the title hydrated salt, C14H13N2+·C10H5O8-·H2O, a proton has been transfered to the 2,9-dimethyl-1,10-phenanthrolinium cation, forming a 2,4,5-tri­carb­oxy­benzoate anion. In the anion, the mean planes of the protonated carboxyl­ate groups form dihedral angles of 11.0 (5), 4.4 (5) and 80.3 (4)° with the benzene ring to which they are attached. The mean plane of the deprotonated carboxyl­ate group forms a dihedral angle of 10.6 (5)° with the benzene ring. In the crystal, the anions are involved in carb­oxy­lic acid O-H...Ocarbox­yl hydrogen bonds, generating a two-dimensional network parallel to (001) containing R44(28) and R44(32) motifs. The 2,9-dimethyl-1,10-phenanthrolinium cations and water mol­ecules reside between the anion layers and are connected to the anions via N-H...Owater and Owater-H...Ocarbox­yl hydrogen bonds. An intra­molecular O-H...O hydrogen bond is also observed in the anion.

Related literature

For related structures, see: Adams & Ramdas (1978[Adams, J. M. & Ramdas, V. (1978). Acta Cryst. B34, 2781-2785.]); Mrvos-Sermek et al. (1996)[Mrvos-Sermek, D., Popovic, Z. & Matkovic-Calogovic, D. (1996). Acta Cryst. C52, 2538-2541.]; Sun et al. (2002a[Sun, Y.-Q., Zhang, J. & Yang, G.-Y. (2002a). Acta Cryst. E58, o904-o906.],b[Sun, Y.-Q., Zhang, J. & Yang, G.-Y. (2002b). Acta Cryst. E58, o1100-o1102.]); Zhu et al. (2002[Zhu, L.-G., Ellern, A. M. & Kostic, N. M. (2002). Acta Cryst. C58, o129-o130.]); Li et al. (2003[Li, Y., Hao, N., Lu, Y. & Wang, E.-B. (2003). Inorg. Chem. 42, 3119-3124.]; 2006[Li, X.-F., Liu, D.-S., Luo, Q.-Y. & Huang, C.-C. (2006). Acta Cryst. E62, o460-o462.]); Oscar et al. (2008[Oscar, F., Jorge, P., Francesc, L., Miguel, J. & Catalina, R.-P. (2008). Inorg. Chem. 47, 3568-3576.]). For background to mol­ecular recognition and supra­molecular chemistry, see: Batten & Robson (1998[Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460-1494.]); Juan et al. (2002[Juan, C. N., Myoung, S. L., Rico, E. D. S., Atta, M. A., Joel, S. M. & Peter, J. S. (2002). J. Am. Chem. Soc. 124, 6613-6625.]); Qiu et al. (2008[Qiu, Y., Liu, Z., Li, Y., Deng, H., Zeng, R. & Zeller, M. (2008). Inorg. Chem. 47, 5122-5128.]). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N2+·C10H5O8-·H2O

  • Mr = 480.42

  • Orthorhombic, P b c a

  • a = 7.1135 (8) Å

  • b = 19.4512 (11) Å

  • c = 30.800 (2) Å

  • V = 4261.7 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 223 K

  • 0.35 × 0.20 × 0.15 mm

Data collection
  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.468, Tmax = 1.000

  • 19580 measured reflections

  • 4346 independent reflections

  • 2278 reflections with I > 2[sigma](I)

  • Rint = 0.173

Refinement
  • R[F2 > 2[sigma](F2)] = 0.088

  • wR(F2) = 0.272

  • S = 1.00

  • 4346 reflections

  • 316 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.82 1.58 2.395 (4) 171
O5-H5...O1i 0.82 1.86 2.671 (3) 172
O8-H8...O3ii 0.82 1.82 2.645 (4) 178
N1-H1A...O1Wiii 0.86 1.92 2.738 (4) 160
O1W-H1WA...O4ii 0.82 1.92 2.735 (4) 171
O1W-H1WB...O7iv 0.82 2.11 2.873 (4) 155
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iv) x+1, y, z.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5664 ).


Acknowledgements

This work was supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2013-10).

References

Adams, J. M. & Ramdas, V. (1978). Acta Cryst. B34, 2781-2785.  [CSD] [CrossRef] [IUCr Journals]
Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460-1494.  [Web of Science] [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.
Juan, C. N., Myoung, S. L., Rico, E. D. S., Atta, M. A., Joel, S. M. & Peter, J. S. (2002). J. Am. Chem. Soc. 124, 6613-6625.  [Web of Science] [CSD] [CrossRef] [PubMed]
Li, Y., Hao, N., Lu, Y. & Wang, E.-B. (2003). Inorg. Chem. 42, 3119-3124.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Li, X.-F., Liu, D.-S., Luo, Q.-Y. & Huang, C.-C. (2006). Acta Cryst. E62, o460-o462.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mrvos-Sermek, D., Popovic, Z. & Matkovic-Calogovic, D. (1996). Acta Cryst. C52, 2538-2541.  [CSD] [CrossRef] [IUCr Journals]
Oscar, F., Jorge, P., Francesc, L., Miguel, J. & Catalina, R.-P. (2008). Inorg. Chem. 47, 3568-3576.  [Web of Science] [PubMed]
Qiu, Y., Liu, Z., Li, Y., Deng, H., Zeng, R. & Zeller, M. (2008). Inorg. Chem. 47, 5122-5128.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
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]
Sun, Y.-Q., Zhang, J. & Yang, G.-Y. (2002a). Acta Cryst. E58, o904-o906.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sun, Y.-Q., Zhang, J. & Yang, G.-Y. (2002b). Acta Cryst. E58, o1100-o1102.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Zhu, L.-G., Ellern, A. M. & Kostic, N. M. (2002). Acta Cryst. C58, o129-o130.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1782-o1783   [ doi:10.1107/S1600536813030857 ]

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