1,10-Phenanthrolin-1-ium hydrogen d,l-tartrate dihydrate

Cheng, S.F.; Ng, S.W.

doi:10.1107/S1600536811015972

Volume 67
Part 6
Page o1306
June 2011

Received 27 April 2011
Accepted 27 April 2011
Online 7 May 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.160
Data-to-parameter ratio = 13.6
Details

1,10-Phenanthrolin-1-ium hydrogen D,L-tartrate dihydrate

Sit Foon Cheng ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title hydrated molecular salt, C₁₂H₉N₂⁺·C₄H₅O₆^-·2H₂O, the cation is almost planar (r.m.s. deviation = 0.014 Å); the carbon skeleton of the anion assumes a trans conformation [C-C-C-C torsion angle = -179.86 (14)°]. The carboxyl end of one hydrogen tartrate anion forms a short hydrogen bond to the carboxylate end of another anion [OO = 2.508 (2) Å] in a head-to-tail manner, forming a chain; the chains and water molecules interact, generating an O-HO hydrogen-bonded layer. The cation binds to the layer by an N-HO hydrogen bond.

Related literature

For the trihydrated 1,10-phenanthrolin-1-ium salts of D- and L-tartaric acid, see: Derikvand & Olmstead (2010); Wang et al. (2006).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₄H₅O₆^-·2H₂O
M_r = 366.32
Triclinic, $[P \overline 1]$
a = 7.0933 (7) Å
b = 10.5849 (11) Å
c = 11.4694 (11) Å
= 98.081 (1)°
= 100.350 (1)°
= 103.903 (1)°
V = 806.95 (14) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 100 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
7610 measured reflections
3635 independent reflections
2880 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.160
S = 1.04
3635 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O1wⁱ	0.89 (3)	1.82 (3)	2.709 (2)	175 (3)
O4-H4O2wⁱⁱ	0.90 (3)	1.84 (3)	2.739 (2)	172 (3)
O5-H5O2ⁱⁱⁱ	0.99 (3)	1.52 (3)	2.508 (2)	169 (3)
O1w-H12O1	0.93 (3)	1.97 (3)	2.846 (2)	157 (3)
O1w-H11O1^iv	0.90 (4)	1.86 (4)	2.753 (2)	173 (4)
O2w-H21O2	0.84 (4)	1.93 (4)	2.764 (2)	168 (3)
O2w-H22O6^v	0.87 (3)	1.97 (3)	2.835 (2)	176 (3)
N1-H1O1w	0.93 (3)	1.89 (3)	2.753 (2)	153 (3)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z; (iii) x+1, y, z; (iv) -x, -y+2, -z+1; (v) -x+1, -y+2, -z.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5536 ).

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Derikvand, Z. & Olmstead, M. M. (2010). Acta Cryst. E66, o185.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Z.-L., Li, M.-X., Wei, L.-H. & Wang, J.-P. (2006). Acta Cryst. E62, o2508-o2509.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds