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

Derikvand, Z.; Olmstead, M.M.

doi:10.1107/S160053681005110X

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 (C-C) = 0.006 Å
R = 0.090
wR = 0.173
Data-to-parameter ratio = 11.5
Details

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

Zohreh Derikvand ^a ^* and Marilyn M. Olmstead ^b

^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-HO, N-HO and C-HO 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); Derikvand & Olmstead (2010); Paixão et al. (1999); Ryttersgaard & Larsen (2003); Smith et al. (2006); Su et al. (2009); Suresh et al. (2006); Wang et al. (2008); Zhang et al. (2006).

Experimental

Crystal data

2C₁₄H₁₃N₂⁺·2C₄H₅O₆^-·9H₂O
M_r = 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 radiation
= 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) T_min = 0.975, T_max = 0.994
49446 measured reflections
7023 independent reflections
6177 reflections with I > 2(I)
R_int = 0.097

Refinement

R[F² > 2(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
_max = 0.47 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO1W	0.88	1.97	2.820 (5)	162
N4-H4CO7W	0.88	1.98	2.814 (5)	159
O4-H4O6W	0.84	1.80	2.633 (5)	175
O9-H9CO5W	0.84	1.83	2.673 (4)	177
O10-H10AO4W	0.84	1.79	2.627 (5)	172
O2W-H2CO11	0.86 (4)	1.97 (2)	2.783 (4)	157 (4)
O3W-H3CO5	0.87 (4)	1.95 (2)	2.798 (5)	168 (5)
O2W-H2DO8W	0.88	2.42	2.903 (5)	115
O5W-H5AO3	0.87 (4)	2.04 (3)	2.827 (4)	151 (5)
O5W-H5AO2	0.87 (4)	2.35 (4)	3.020 (4)	135 (5)
O8W-H8BO2W	0.87 (2)	2.03 (2)	2.903 (5)	178 (5)
O9W-H9AO2	0.86 (4)	1.89 (2)	2.744 (4)	175 (5)
O9W-H9BO9	0.87 (4)	2.08 (4)	2.849 (4)	147 (5)
O9W-H9BO8	0.87 (4)	2.26 (4)	2.958 (4)	137 (5)
O1-H1O5ⁱ	0.99 (6)	1.49 (6)	2.473 (4)	172 (5)
O7-H7O11ⁱ	0.91 (6)	1.60 (6)	2.496 (4)	167 (5)
O4W-H4BO12ⁱ	0.87 (2)	1.85 (2)	2.720 (5)	178 (6)
O6W-H6BO6ⁱ	0.86 (3)	1.93 (2)	2.776 (5)	167 (5)
O3-H3BO9Wⁱⁱ	0.84	1.81	2.647 (5)	173
O5W-H5BO8ⁱⁱ	0.87 (4)	1.91 (2)	2.761 (4)	168 (5)
O1W-H1AO2Wⁱⁱⁱ	0.87 (4)	2.22 (3)	3.062 (5)	161 (5)
O1W-H1BO5Wⁱⁱⁱ	0.87 (4)	1.96 (2)	2.811 (5)	168 (6)
O3W-H3DO8Wⁱⁱⁱ	0.87 (4)	2.02 (2)	2.876 (5)	168 (5)
O4W-H4AO10^iv	0.87 (4)	1.99 (3)	2.815 (4)	160 (5)
O4W-H4AO12^iv	0.87 (4)	2.40 (4)	2.998 (4)	127 (4)
O6W-H6AO4^v	0.87 (4)	2.15 (4)	2.892 (4)	143 (5)
O6W-H6AO6^v	0.87 (4)	2.19 (4)	2.909 (5)	140 (5)
O7W-H7AO3W^vi	0.87 (4)	2.17 (3)	2.988 (5)	156 (5)
O7W-H7BO9W^vii	0.87 (4)	2.02 (2)	2.869 (5)	165 (5)
O8W-H8AO1^vii	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Derikvand, Z. & Olmstead, M. M. (2010). Acta Cryst. E66, o185.
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, C. & Larsen, S. (2003). Acta Cryst. E59, o1715-o1716.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Wermuth, U. D. & White, J. M. (2006). Acta Cryst. C62, o694-o698.
Su, H., Lv, Y.-K. & Feng, Y.-L. (2009). Acta Cryst. E65, o933.
Suresh, J., Krishnakumar, R. V., Rajagopal, K. & Natarajan, S. (2006). Acta Cryst. E62, o3220-o3222.
Wang, X.-H., Chao, B. & Qiu, Z.-B. (2008). Acta Cryst. E64, o784.
Zhang, Y.-C., Bai, G.-Y., Zeng, T., Li, J.-S. & Yan, X.-L. (2006). Acta Cryst. E62, o1511-o1512.

organic compounds