(IUCr) Bis(chloroacetato)-[kappa]2O,O';[kappa]O-methanol-[kappa]O-bis(2-methylfuro[3,2-c]pyridine-[kappa]N)copper(II)

Volume 64
Part 5
Pages m610-m611
May 2008

Received 17 March 2008
Accepted 28 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R = 0.044
wR = 0.104
Data-to-parameter ratio = 13.4
Details

Bis(chloroacetato)-²O,O';O-methanol-O-bis(2-methylfuro[3,2-c]pyridine-N)copper(II)

Dusan Miklos,^a Jozef Miklovic,^b Viera Mrázová,^b Jan Moncol ^a ^* and Peter Segla ^a

^aDepartment of Inorganic Chemistry, Slovak Technical University, Radlinského 9, SK-812 37, Bratislava, Slovakia, and ^bDepartment of Chemistry, Faculty of Natural Science, University of St. Cyril and Methodius, SK-91701 Trnava, Slovakia
Correspondence e-mail: jan.moncol@stuba.sk

In the title compound, [Cu(C₂H₂ClO₂)₂(C₈H₇NO)₂(CH₄O)], the Cu²⁺ ion has a highly distorted square-bipyramidal (4 + 1 + 1) coordination environment and is bonded to three carboxylate O atoms of two chloroacetate anions (monodentate and asymmetrically bidentate), two pyridine N atoms of 2-methylfuro[3,2-c]pyridine and one methanol O atom. There is an intramolecular O-HO hydrogen bond. Intermolecular C-HO hydrogen bonds result in the formation of a three-dimensional network and [pi] - [pi] stacking interactions [3.44-3.83 Å] are observed between symmetry-related rings of 2-methylfuro[3,2-c]pyridine. Further interactions in the crystal structure are a short ClCl interaction [3.384 (2)Å] and C-H [pi] interactions between 2-methylfuro[3,2-c]pyridine rings.

Related literature

For general background, see: Desiraju (1995); Janiak (2000); Suezawa et al. (2002). For related literature, see: Baran et al. (2005); Eloy & Deryckere (1971); Ivaniková et al. (2006); Miklos et al. (2005); Miklovic et al. (2004); New et al. (1989); Segla et al. (2005); Titis et al. (2007); Vrábel et al. (2007a,b). For similar structures, see: Borel et al. (1978); Moncol et al. (2007); Wang et al. (2005).

Experimental

Crystal data

[Cu(C₂H₂ClO₂)₂(C₈H₇NO)₂(CH₄O)]
M_r = 548.86
Monoclinic, C 2/c
a = 19.860 (3) Å
b = 15.576 (3) Å
c = 15.017 (3) Å
= 97.917 (3)°
V = 4600.9 (15) Å³
Z = 8
Mo K radiation
= 1.23 mm^-1
T = 173 (2) K
0.26 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.776, T_max = 0.891 (expected range = 0.716-0.822)
16690 measured reflections
4021 independent reflections
3093 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.103
S = 1.02
4021 reflections
300 parameters
H-atom parameters constrained
_max = 1.08 e Å^-3
_min = -0.53 e Å^-3

Table 1
Selected bond lengths (Å)

Cu1-O8	1.956 (2)
Cu1-O4	1.964 (2)
Cu1-N21	2.031 (3)
Cu1-N11	2.046 (3)
Cu1-O1	2.311 (2)
Cu1-O5	2.833 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OO9	0.84	1.86	2.664 (3)	159
C12-H12O4	0.95	2.44	2.944 (4)	113
C20-H20O8	0.95	2.40	2.915 (4)	114
C22-H22O8	0.95	2.41	2.886 (4)	111
C30-H30O4	0.95	2.53	3.000 (4)	111
C6-H6AO5ⁱ	0.99	2.60	3.510 (4)	154
C16-H16CO1ⁱⁱ	0.98	2.63	3.413 (4)	137
C14-H14O9ⁱⁱ	0.95	2.55	3.450 (4)	159
C20-H20O5ⁱ	0.95	2.57	3.221 (4)	126
C29-H29O5ⁱⁱⁱ	0.95	2.69	3.451 (4)	138
C19-H19O5ⁱ	0.95	2.65	3.235 (4)	120
C16-H16AO9^iv	0.98	2.65	3.610 (4)	167
C24-H24O9^v	0.95	2.67	3.408 (4)	135
C1-H1BC14^vi	0.98	2.87	3.834 (4)	168
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2220 ).

Acknowledgements

We thank Professor R. Sillanpää for measuring the diffraction data and the Scientific Grant Agency of the Ministry of Education of the Slovak Republic and the Slovak Academy of Sciences (1/4454/07 and 1/0353/08) for financial support.

References

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metal-organic compounds

Bis(chloroacetato)-2O,O';O-methanol-O-bis(2-methylfuro[3,2-c]pyridine-N)copper(II)