2,9-Dimethyl-1,10-phenanthrolin-1-ium (6-carb­oxy-4-hy­droxy­pyridine-2-carboxyl­ato-κ3O2,N,O6)(4-hy­droxy­pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)zincate(II) 2.35-hydrate: a proton-transfer compound

Derikvand, Z.; Stoeckli-Evans, H.; Nemati, A.

doi:10.1107/S1600536811052445

Volume 68
Part 1
Pages m31-m32
January 2012

Received 20 November 2011
Accepted 5 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.039
wR = 0.081
Data-to-parameter ratio = 12.5
Details

2,9-Dimethyl-1,10-phenanthrolin-1-ium (6-carboxy-4-hydroxypyridine-2-carboxylato-³O²,N,O⁶)(4-hydroxypyridine-2,6-dicarboxylato-³O²,N,O⁶)zincate(II) 2.35-hydrate: a proton-transfer compound

Zohreh Derikvand,^a ^* Helen Stoeckli-Evans ^b and Andya Nemati ^c

^aFaculty of Science, Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Iran,^bInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland, and ^cIran Compiling Encyclopedia Foundation, Tajrish, Tehran, Iran
Correspondence e-mail: zderik@yahoo.com

In the title compound, (C₁₄H₁₃N₂)[Zn(C₇H₃NO₅)(C₇H₄NO₅)]·2.35H₂O, the Zn^II atom is coordinated by two N atoms and four O atoms from the carboxylate groups of the 4-hydroxypyridine-2,6-dicarboxylate and 6-carboxy-4-hydroxypyridine-2-carboxylate ligands, forming a distored octahedral geometry. In the anion, the two pyridine rings are inclined to one another by 87.75 (13)°. Two types of robust O-HO hydrogen bond synthons, viz. R₂²(16) and R₆⁶(42), link the anions to form a two-dimensional network parallel to the bc plane. Furthermore, O-HO, N-HO, N-HN and weak C-HO hydrogen bonds connect the two dimensional networks, forming a three-dimensional structure. In the crystal, there are also C-H [pi] and [pi] - [pi] interactions [centroid-centroid distances of 3.5554 (18) and 3.7681 (18) Å], and C=O [pi] interactions [Ocentroid distance = 3.117 (2) Å] present. One of the three crystal water molecules shows an occupancy of 0.35.

Related literature

For related structures, see: Aghabozorg et al. (2007a,b,c, 2008a,b,c); Derakhshandeh et al. (2010); Moghimi et al. (2005a,b).

Experimental

Crystal data

(C₁₄H₁₃N₂)[Zn(C₇H₃NO₅)(C₇H₄NO₅)]·2.35H₂O
M_r = 680.19
Monoclinic, P 2₁ /c
a = 11.0687 (18) Å
b = 9.7888 (14) Å
c = 25.776 (4) Å
= 94.160 (19)°
V = 2785.4 (7) Å³
Z = 4
Mo K radiation
= 0.96 mm^-1
T = 223 K
0.38 × 0.15 × 0.15 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009) T_min = 0.972, T_max = 1.000
20517 measured reflections
5464 independent reflections
3242 reflections with I > 2(I)
R_int = 0.079

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.081
S = 0.82
5464 reflections
437 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.82 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1-C5 ring.

D-HA	D-H	HA	DA	D-HA
N3-H3N4	0.87	2.37	2.721 (3)	105
N3-H3O1W	0.87	2.01	2.848 (4)	161
O5-H5O2W	0.83	1.76	2.570 (4)	166
O7-H7O2ⁱ	0.83	1.66	2.402 (3)	147
O10-H10O3ⁱⁱ	0.83	1.75	2.562 (3)	166
O1W-H1WAO9ⁱⁱⁱ	0.83 (3)	2.02 (4)	2.833 (4)	169 (4)
O1W-H1WBO4^iv	0.84 (4)	2.18 (4)	2.960 (4)	156 (3)
O2W-H2WAO8^v	0.82 (4)	1.98 (4)	2.738 (4)	155 (4)
O2W-H2WBO4^vi	0.81 (2)	2.25 (3)	3.046 (4)	171 (4)
O3W-H3WAO4	0.83 (2)	1.75 (5)	2.530 (7)	157 (13)
O3W-H3WBO2W^v	0.82 (2)	2.21 (4)	2.750 (9)	123 (3)
C27-H27CO3^vii	0.97	2.58	3.504 (4)	160
C22-H22Cg1^viii	0.94	2.76	3.634 (4)	155
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z; (iii) -x+1, -y+2, -z; (iv) -x+1, -y+1, -z; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) x+1, y, z; (viii) x, y-1, z.

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5386 ).

Acknowledgements

HSE thanks the XRD Application Lab. of the CSEM, Neuchâtel, for access to the X-ray diffraction equipment.

References

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