catena-Poly[[[(2,2′-bipyridine-κ2N,N′)manganese(II)]-μ-(2,5-dichloro-3,6-dioxocyclo­hexa-1,4-diene-1,4-diolato)-κ4O1,O6:O3,O4] ethanol disolvate]

Nishimura, Y.; Himegi, A.; Fuyuhiro, A.; Hayami, S.; Kawata, S.

doi:10.1107/S1600536813001438

Volume 69
Part 2
Pages m119-m120
February 2013

Received 22 December 2012
Accepted 15 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.089
Data-to-parameter ratio = 17.3
Details

catena-Poly[[[(2,2'-bipyridine-²N,N')manganese(II)]--(2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolato)-⁴O¹,O⁶:O³,O⁴] ethanol disolvate]

Yuji Nishimura,^a Akiko Himegi,^a Akira Fuyuhiro,^b Shinya Hayami ^c and Satoshi Kawata ^a ^*

^aDepartment of Chemistry, Faculty of Science, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan,^bDepartment of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan, and ^cDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami, Kumamoto 860-8555, Japan
Correspondence e-mail: kawata@fukuoka-u.ac.jp

The asymmetric unit of the title coordination polymer, {[Mn(C₆Cl₂O₄)(C₁₀H₈N₂)]·2C₂H₅OH}_n, consists of one Mn^II ion, one 2,2'-bipyridine (bpy) ligand, one chloranilate (CA^2-) ligand and two ethanol solvent molecules. The Mn^II ion is octahedrally coordinated by two N atoms of one bpy ligand and four O atoms of two chloranilate ions. The chloranilate ion serves as a bridging ligand between the Mn^II ions, leading to an infinite zigzag chain along [101]. [pi] - [pi] stacking interactions [centroid-centroid distance = 4.098 (2) Å] is observed between the pyridine rings of adjacent chains. The ethanol molecules act as accepters as well as donors for O-HO hydrogen bonds, and form a hydrogen-bonded chain along the a axis. The H atoms of the hydroxy groups of the two independent ethanol molecules are each disordered over two sites with equal occupancies.

Related literature

For related structures, see: Nagayoshi et al. (2003); Decurtins et al. (1996); Deguenon et al. (1990); Kabir et al. (2001); Zheng et al. (1996).

Experimental

Crystal data

[Mn(C₆Cl₂O₄)(C₁₀H₈N₂)]·2C₂H₆O
M_r = 510.22
Monoclinic, P 2₁ /n
a = 8.3130 (15) Å
b = 20.866 (4) Å
c = 12.513 (2) Å
= 97.665 (2)°
V = 2151.2 (7) Å³
Z = 4
Mo K radiation
= 0.90 mm^-1
T = 100 K
0.40 × 0.10 × 0.05 mm

Data collection

Rigaku Saturn724 diffractometer
Absorption correction: multi-scan (REQAB; Rigaku, 1998) T_min = 0.897, T_max = 0.956
24503 measured reflections
4903 independent reflections
4526 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.089
S = 1.10
4903 reflections
284 parameters
H-atom parameters constrained
_max = 0.99 e Å^-3
_min = -0.57 e Å^-3

Table 1
Selected bond lengths (Å)

Mn1-O1	2.1796 (14)
Mn1-O2	2.1546 (14)
Mn1-O3ⁱ	2.1511 (14)
Mn1-O4ⁱ	2.1782 (14)
Mn1-N1	2.2473 (16)
Mn1-N2	2.2398 (16)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H1O6	0.84	1.91	2.716 (4)	160
O5-H4O5ⁱⁱ	0.84	2.00	2.715 (4)	142
O6-H2O6ⁱⁱⁱ	0.84	1.83	2.661 (3)	170
O6-H3O5	0.84	1.90	2.716 (4)	162
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5235 ).

Acknowledgements

This work was supported by funds (No. 101501) from the Central Research Institute of Fukuoka University and Grant-in-Aids for Science Research (No. 22550067) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.
Decurtins, S., Schmalle, H. W., Zheng, L.-M. & Ensling, J. (1996). Inorg. Chim. Acta, 244, 165-170.
Deguenon, D., Bernardinelli, G., Tuchagues, J.-P. & Castan, J.-P. (1990). Inorg. Chem. 29, 3031-3037.
Kabir, M. K., Kawahara, M., Kumagai, H., Adachi, K., Kawata, S., Ishii, T. & Kitagawa, S. (2001). Polyhedron, 20, 1417-1422.
Nagayoshi, K., Kabir, M. K., Tobita, H., Honda, K., Kawahara, M., Katada, M., Adachi, K., Nishikawa, H., Ikemoto, I., Kumagai, H., Hosokoshi, Y., Inoue, K., Kitagawa, S. & Kawata, S. (2003). J. Am. Chem. Soc. 125, 221-232.
Rigaku (1998). REQAB. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). Crystal Structure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zheng, L.-M., Schmalle, H. W., Huber, R. & Decurtins, S. (1996). Polyhedron, 15, 4399-4405.

metal-organic compounds

catena-Poly[[[(2,2'-bipyridine-2N,N')manganese(II)]--(2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolato)-4O1,O6:O3,O4] ethanol disolvate]