catena-Poly[copper(II)-bis-(μ-3-cyano-2-hydroxy-propionato)-κN:O,O;κO,O:N-copper(II)].

The title compound, [Cu(C(4)H(4)NO(3))(2)](n), exhibits a double-chain structure extending along [100]. The Cu(II) atom, lying on an inversion center, is coordinated by two cyano N atoms from two 3-cyano-2-hydroxy-propionate ligands and two hydr-oxy O atoms and two carboxyl-ate O atom from two other two ligands in a distorted octa-hedral geometry. Inter-molecular C-H⋯O and O-H⋯O hydrogen bonds connect the chains into a three-dimensional structure.

Related literature

For the synthesis and studies of β-hydroxy­nitriles, see: Conti et al. (2003 ▶); Seo et al. (1994 ▶). For related structures, see: Klein et al. (1982 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

[Cu(C4H4NO3)2]

M = 291.71

Monoclinic,

a = 6.3704 (7) Å

b = 8.4382 (10) Å

c = 10.0412 (12) Å

β = 104.492 (2)°

V = 522.59 (11) Å3

Z = 2

Mo Kα radiation

μ = 2.11 mm−1

T = 293 K

0.28 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.624, T max = 0.776

2803 measured reflections

1031 independent reflections

973 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.064

S = 1.11

1031 reflections

83 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007129/hy2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007129/hy2278Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C4H4NO3)2]	F(000) = 294
Mr = 291.71	Dx = 1.854 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2150 reflections
a = 6.3704 (7) Å	θ = 3.2–26.0°
b = 8.4382 (10) Å	µ = 2.11 mm−1
c = 10.0412 (12) Å	T = 293 K
β = 104.492 (2)°	Block, blue
V = 522.59 (11) Å3	0.28 × 0.19 × 0.12 mm
Z = 2

Bruker SMART APEX CCD diffractometer	1031 independent reflections
Radiation source: sealed tube	973 reflections with I > 2σ(I)
graphite	Rint = 0.017
φ and ω scans	θmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→7
Tmin = 0.624, Tmax = 0.776	k = −9→10
2803 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.2506P] where P = (Fo2 + 2Fc2)/3
1031 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.0000	0.0000	0.03130 (14)
N1	1.1980 (3)	0.1558 (3)	0.0646 (2)	0.0635 (6)
O1	0.69000 (19)	0.11889 (14)	0.15024 (11)	0.0264 (3)
H1W	0.671 (4)	0.117 (3)	0.2292 (14)	0.057 (7)*
O2	0.5444 (2)	0.17730 (15)	−0.10898 (11)	0.0364 (3)
O3	0.6908 (2)	0.41604 (15)	−0.09635 (12)	0.0384 (3)
C1	0.7140 (3)	0.28079 (19)	0.11473 (16)	0.0256 (3)
H1	0.6192	0.3473	0.1545	0.031*
C2	0.6441 (3)	0.2934 (2)	−0.04252 (16)	0.0274 (4)
C3	0.9491 (3)	0.3336 (2)	0.17056 (18)	0.0345 (4)
H3A	0.9641	0.4433	0.1454	0.041*
H3B	0.9880	0.3266	0.2701	0.041*
C4	1.0950 (3)	0.2340 (3)	0.1150 (2)	0.0419 (5)

	U11	U22	U33	U12	U13	U23
Cu1	0.0435 (2)	0.0282 (2)	0.02069 (19)	−0.01409 (12)	0.00516 (14)	0.00079 (10)
N1	0.0422 (10)	0.0728 (14)	0.0791 (14)	−0.0038 (10)	0.0222 (10)	−0.0190 (12)
O1	0.0346 (6)	0.0251 (6)	0.0203 (5)	−0.0059 (5)	0.0080 (5)	−0.0001 (4)
O2	0.0537 (8)	0.0323 (7)	0.0217 (6)	−0.0152 (6)	0.0065 (5)	0.0008 (5)
O3	0.0626 (9)	0.0272 (7)	0.0284 (6)	−0.0107 (6)	0.0170 (6)	0.0016 (5)
C1	0.0333 (9)	0.0228 (8)	0.0232 (7)	−0.0030 (6)	0.0116 (6)	−0.0017 (6)
C2	0.0327 (8)	0.0276 (8)	0.0244 (8)	−0.0008 (7)	0.0120 (7)	0.0001 (6)
C3	0.0385 (10)	0.0351 (9)	0.0306 (8)	−0.0119 (8)	0.0099 (7)	−0.0069 (7)
C4	0.0307 (9)	0.0476 (11)	0.0465 (11)	−0.0109 (9)	0.0081 (8)	−0.0063 (9)

Cu1—O2	1.9159 (12)	O3—C2	1.238 (2)
Cu1—O1	1.9579 (11)	C1—C3	1.528 (2)
Cu1—N1i	2.545 (2)	C1—C2	1.533 (2)
N1—C4	1.135 (3)	C1—H1	0.9800
O1—C1	1.4298 (19)	C3—C4	1.464 (3)
O1—H1W	0.832 (10)	C3—H3A	0.9700
O2—C2	1.264 (2)	C3—H3B	0.9700
O2ii—Cu1—O2	180.0	C3—C1—C2	111.28 (14)
O2ii—Cu1—O1	96.39 (5)	O1—C1—H1	109.3
O2—Cu1—O1	83.62 (5)	C3—C1—H1	109.3
O2—Cu1—O1ii	96.38 (5)	C2—C1—H1	109.3
O1—Cu1—O1ii	179.999 (1)	O3—C2—O2	124.17 (15)
O1—Cu1—N1i	84.25 (6)	O3—C2—C1	117.92 (14)
O2—Cu1—N1i	88.35 (6)	O2—C2—C1	117.90 (14)
O1ii—Cu1—N1i	95.74 (6)	C4—C3—C1	110.51 (15)
O2ii—Cu1—N1i	91.65 (6)	C4—C3—H3A	109.5
C1—O1—Cu1	112.43 (9)	C1—C3—H3A	109.5
C1—O1—H1W	108.0 (19)	C4—C3—H3B	109.5
Cu1—O1—H1W	120.9 (19)	C1—C3—H3B	109.5
C2—O2—Cu1	115.49 (10)	H3A—C3—H3B	108.1
O1—C1—C3	110.09 (14)	N1—C4—C3	175.7 (2)
O1—C1—C2	107.56 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2iii	0.98	2.54	3.240 (2)	128
O1—H1W···O3iii	0.83 (2)	1.75 (2)	2.560 (2)	165 (4)

Table 1

Selected bond lengths (Å)

Cu1—O2	1.9159 (12)
Cu1—O1	1.9579 (11)
Cu1—N1i	2.545 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ii	0.98	2.54	3.240 (2)	128
O1—H1W⋯O3ii	0.83 (2)	1.75 (2)	2.560 (2)	165 (4)

Symmetry code: (ii) .