Bis(4,4′′-difluoro-1,1′:3′,1′′-terphenyl-2′-carboxyl­ato-κO)tetra­kis­(methanol-κO)calcium methanol tetra­solvate

Kim, N.; Noh, H.; Yoon, S.; Park, C.R.

doi:10.1107/S1600536813000044

Volume 69
Part 2
Pages m122-m123
February 2013

Received 21 November 2012
Accepted 2 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
R = 0.064
wR = 0.165
Data-to-parameter ratio = 19.0
Details

Bis(4,4''-difluoro-1,1':3',1''-terphenyl-2'-carboxylato-O)tetrakis(methanol-O)calcium methanol tetrasolvate

Namseok Kim,^a Heeso Noh,^b Sungho Yoon ^a ^* and Chan Ryang Park ^a ^*

^aDepartment of Bio & Nano Chemistry, College of Natural Sciences, Kookmin University, 861-1 Jeongneung-dong, Seongbuk-gu, Seoul 136-702, Republic of Korea, and ^bDepartment of Physics, College of Natural Sciences, Kookmin University, 861-1 Jeongneung-dong, Seongbuk-gu, Seoul 136-702, Republic of Korea.
Correspondence e-mail: yoona@kookmin.ac.kr, crpark@kookmin.ac.kr

In the title compound, [Ca(C₁₉H₁₁F₂O₂)₂(CH₃OH)₄]·4CH₃OH, the Ca²⁺ ion is located on an inversion centre and is hexacoordinated by two O atoms of two 4,4''-difluoro-1,1':3',1''-terphenyl-2'-carboxylate ligands and four O atoms of four methanol ligands, forming a CaO₆ polyhedron with a slightly distorted octahedral coordination geometry. The Ca-O-C angle between the carboxylate group and the calcium ion is 171.8 (2)°. Two types of intermolecular hydrogen-bond interactions (C=OH and O-HO) between the carboxylate ligand, the methanol solvent molecules and the coordinating methanol ligands generate a two-dimensional network parallel to (001).

Related literature

For background to metal complexes with 4,4''-difluoro-1,1':3',1''-terphenyl-2'-carboxylate ligands, see: Kannan et al. (2011); Chavez et al. (2001). For mononuclear calcium complexes with carboxylate ligands, see: Perrin et al. (2009); Godino Salido et al. (2004); Huang et al. (2010). For their polymerization behavior, see: Jisha et al. (2010); Murugavel & Banerjee (2003); Yang et al. (2004).

Experimental

Crystal data

[Ca(C₁₉H₁₁F₂O₂)₂(CH₄O)₄]·4CH₄O
M_r = 914.97
Orthorhombic, P b c a
a = 15.4611 (19) Å
b = 14.2436 (18) Å
c = 20.886 (3) Å
V = 4599.5 (10) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 200 K
0.32 × 0.23 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.521, T_max = 1.00
32627 measured reflections
5709 independent reflections
2624 reflections with I > 2(I)
R_int = 0.143

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.165
S = 0.98
5709 reflections
300 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.45 e Å^-3

Table 1
Selected bond lengths (Å)

Ca1-O1	2.2693 (19)
Ca1-O4	2.325 (2)
Ca1-O3	2.346 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O6ⁱⁱ	0.89 (4)	1.78 (4)	2.636 (3)	162 (4)
O4-H2O5ⁱⁱⁱ	0.91 (4)	1.76 (4)	2.660 (3)	172 (4)
O6-H6AO2^iv	0.84	1.96	2.804 (3)	177
O5-H5AO2^v	0.84	1.92	2.755 (3)	170
Symmetry codes: (ii) x, y-1, z; (iii) x+1, y-1, z; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RU2047 ).

Acknowledgements

This work was supported by the International Collaborative R&D Program of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant funded by Korea Government Ministry of Knowledge Economy (20118520010020).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chavez, F. A., Que, L. & Tolman, W. B. (2001). Chem. Commun. pp. 111-112.
Godino Salido, M. L., Arranz Mascarós, P., López Garzón, R., Gutiérrez Valero, M. D., Low, J. N., Gallagher, J. F. & Glidewell, C. (2004). Acta Cryst. B60, 46-64.
Huang, L., Zhong, A. G., Chen, D. B., Qiu, D. & Liang, H. D. (2010). J. Mol. Struct. 984, 39-50.
Jisha, K. R., Suma, S. & Sudarsanakumar, M. R. (2010). Polyhedron, 29, 3164-3169.
Kannan, S., Venkatachalam, G., Lee, H.-J., Kim, W., Koo, E., Do, Y. R. & Yoon, S. (2011). Polyhedron, 30, 340-346.
Murugavel, R. & Banerjee, S. (2003). Inorg. Chem. Commun. 6, 810-814.
Perrin, C. L., Lau, J. S., Kim, Y.-J., Karri, P., Moore, C. & Rheingold, A. L. (2009). J. Am. Chem. Soc. 131, 13548-13554.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, Y.-Y., Huang, Z.-Q., Szeto, L. & Wong, W. T. (2004). Appl. Organomet. Chem. 18, 97-98.

metal-organic compounds