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Volume 67 
Part 1 
Pages o87-o88  
January 2011  

Received 1 December 2010
Accepted 6 December 2010
Online 11 December 2010

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.006 Å
R = 0.090
wR = 0.173
Data-to-parameter ratio = 11.5
Details
Open access

Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) hydrogen (S,S)-tartrate nonahydrate

aYoung Researchers Club, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, and bDepartment of Chemistry, University of California, One Shields Avenue, Davis, CA 95616-5292, USA
Correspondence e-mail: zderik@yahoo.com

The asymmetric unit of the title compound, 2C14H13N2+·2C4H5O6-·9H2O, contains two cations and two anions in addition to nine molecules of water. Each of the hydrogen tartrate anions is hydrogen bonded to itself by translation along [100] in a head-to-tail fashion via a short hydrogen bond with donor-acceptor distances of 2.473 (4) and 2.496 (4) Å. A large number of intermolecular O-H...O, N-H...O and C-H...O hydrogen-bonding interactions, as well as [pi]-[pi] stacking [centroid-centroid distances in the range 3.642 (3) to 3.866 (3) Å], play an important role in the crystal structure.

Related literature

For proton-transfer structures of tartaric acid, see: Bai et al. (2005[Bai, G.-Y., Chen, L.-G., Li, Y., Yan, X.-L., Xing, P., Dong, C.-M., Duan, X.-M., Zhang, Y.-C. & Ge, F.-Y. (2005). Acta Cryst. E61, o1125-o1126.]); Derikvand & Olmstead (2010[Derikvand, Z. & Olmstead, M. M. (2010). Acta Cryst. E66, o185.]); Paixão et al. (1999[Paixão, J. A., Pereira Silva, P. S., Matos Beja, A., Ramos Silva, M., de Matos Gomes, E. & Belsley, M. (1999). Acta Cryst. C55, 1287-1290.]); Ryttersgaard & Larsen (2003[Ryttersgaard, C. & Larsen, S. (2003). Acta Cryst. E59, o1715-o1716.]); Smith et al. (2006[Smith, G., Wermuth, U. D. & White, J. M. (2006). Acta Cryst. C62, o694-o698.]); Su et al. (2009[Su, H., Lv, Y.-K. & Feng, Y.-L. (2009). Acta Cryst. E65, o933.]); Suresh et al. (2006[Suresh, J., Krishnakumar, R. V., Rajagopal, K. & Natarajan, S. (2006). Acta Cryst. E62, o3220-o3222.]); Wang et al. (2008[Wang, X.-H., Chao, B. & Qiu, Z.-B. (2008). Acta Cryst. E64, o784.]); Zhang et al. (2006[Zhang, Y.-C., Bai, G.-Y., Zeng, T., Li, J.-S. & Yan, X.-L. (2006). Acta Cryst. E62, o1511-o1512.]).

[Scheme 1]

Experimental

Crystal data
  • 2C14H13N2+·2C4H5O6-·9H2O

  • Mr = 878.83

  • Orthorhombic, P 21 21 21

  • a = 7.0927 (5) Å

  • b = 23.3998 (15) Å

  • c = 24.9335 (16) Å

  • V = 4138.2 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 90 K

  • 0.53 × 0.06 × 0.05 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.994

  • 49446 measured reflections

  • 7023 independent reflections

  • 6177 reflections with I > 2[sigma](I)

  • Rint = 0.097

Refinement
  • R[F2 > 2[sigma](F2)] = 0.090

  • wR(F2) = 0.173

  • S = 1.25

  • 7023 reflections

  • 611 parameters

  • 111 restraints

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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O1W 0.88 1.97 2.820 (5) 162
N4-H4C...O7W 0.88 1.98 2.814 (5) 159
O4-H4...O6W 0.84 1.80 2.633 (5) 175
O9-H9C...O5W 0.84 1.83 2.673 (4) 177
O10-H10A...O4W 0.84 1.79 2.627 (5) 172
O2W-H2C...O11 0.86 (4) 1.97 (2) 2.783 (4) 157 (4)
O3W-H3C...O5 0.87 (4) 1.95 (2) 2.798 (5) 168 (5)
O2W-H2D...O8W 0.88 2.42 2.903 (5) 115
O5W-H5A...O3 0.87 (4) 2.04 (3) 2.827 (4) 151 (5)
O5W-H5A...O2 0.87 (4) 2.35 (4) 3.020 (4) 135 (5)
O8W-H8B...O2W 0.87 (2) 2.03 (2) 2.903 (5) 178 (5)
O9W-H9A...O2 0.86 (4) 1.89 (2) 2.744 (4) 175 (5)
O9W-H9B...O9 0.87 (4) 2.08 (4) 2.849 (4) 147 (5)
O9W-H9B...O8 0.87 (4) 2.26 (4) 2.958 (4) 137 (5)
O1-H1...O5i 0.99 (6) 1.49 (6) 2.473 (4) 172 (5)
O7-H7...O11i 0.91 (6) 1.60 (6) 2.496 (4) 167 (5)
O4W-H4B...O12i 0.87 (2) 1.85 (2) 2.720 (5) 178 (6)
O6W-H6B...O6i 0.86 (3) 1.93 (2) 2.776 (5) 167 (5)
O3-H3B...O9Wii 0.84 1.81 2.647 (5) 173
O5W-H5B...O8ii 0.87 (4) 1.91 (2) 2.761 (4) 168 (5)
O1W-H1A...O2Wiii 0.87 (4) 2.22 (3) 3.062 (5) 161 (5)
O1W-H1B...O5Wiii 0.87 (4) 1.96 (2) 2.811 (5) 168 (6)
O3W-H3D...O8Wiii 0.87 (4) 2.02 (2) 2.876 (5) 168 (5)
O4W-H4A...O10iv 0.87 (4) 1.99 (3) 2.815 (4) 160 (5)
O4W-H4A...O12iv 0.87 (4) 2.40 (4) 2.998 (4) 127 (4)
O6W-H6A...O4v 0.87 (4) 2.15 (4) 2.892 (4) 143 (5)
O6W-H6A...O6v 0.87 (4) 2.19 (4) 2.909 (5) 140 (5)
O7W-H7A...O3Wvi 0.87 (4) 2.17 (3) 2.988 (5) 156 (5)
O7W-H7B...O9Wvii 0.87 (4) 2.02 (2) 2.869 (5) 165 (5)
O8W-H8A...O1vii 0.87 (4) 2.06 (2) 2.926 (5) 170 (5)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (vi) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2765 ).


References

Bai, G.-Y., Chen, L.-G., Li, Y., Yan, X.-L., Xing, P., Dong, C.-M., Duan, X.-M., Zhang, Y.-C. & Ge, F.-Y. (2005). Acta Cryst. E61, o1125-o1126.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Derikvand, Z. & Olmstead, M. M. (2010). Acta Cryst. E66, o185.  [CSD] [CrossRef] [details]
Paixão, J. A., Pereira Silva, P. S., Matos Beja, A., Ramos Silva, M., de Matos Gomes, E. & Belsley, M. (1999). Acta Cryst. C55, 1287-1290.  [CrossRef] [details]
Ryttersgaard, C. & Larsen, S. (2003). Acta Cryst. E59, o1715-o1716.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Wermuth, U. D. & White, J. M. (2006). Acta Cryst. C62, o694-o698.  [CrossRef] [details]
Su, H., Lv, Y.-K. & Feng, Y.-L. (2009). Acta Cryst. E65, o933.  [CSD] [CrossRef] [details]
Suresh, J., Krishnakumar, R. V., Rajagopal, K. & Natarajan, S. (2006). Acta Cryst. E62, o3220-o3222.  [CSD] [CrossRef] [details]
Wang, X.-H., Chao, B. & Qiu, Z.-B. (2008). Acta Cryst. E64, o784.  [CSD] [CrossRef] [details]
Zhang, Y.-C., Bai, G.-Y., Zeng, T., Li, J.-S. & Yan, X.-L. (2006). Acta Cryst. E62, o1511-o1512.  [CSD] [CrossRef] [details]


Acta Cryst (2011). E67, o87-o88   [ doi:10.1107/S160053681005110X ]

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