catena-Poly[[{2-[(2-hy-droxy-eth-yl)imino-meth-yl]-6-meth-oxy-phenolato}copper(II)]-μ-thio-cyanato].

In the title thio-cyanate-bridged polynuclear copper(II) complex, [Cu(C(10)H(12)NO(3))(NCS)](n), the Cu atom is five-coordinated in a square-pyramidal geometry, with one phenolato O, one imino N and one hy-droxy O atom of a Schiff base ligand and one thio-cyanato N atom defining the basal plane, and with one thio-cyanato S atom occupying the apical position. In the crystal structure, pairs of adjacent complex mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds into dimers. The dimers are further linked via Cu⋯S inter-actions, forming two-dimensional layers parallel to the bc plane.

Related literature

For the biological properties of Schiff bases, see: Bhandari et al. (2008 ▶); Sinha et al. (2008 ▶); Sondhi et al. (2006 ▶); Singh et al. (2006 ▶). For metal complexes with Schiff bases, see: Assey et al. (2010 ▶); Thiam et al. (2010 ▶); Montazerozohori et al. (2009 ▶); Eltayeb et al. (2009 ▶).

Experimental

Crystal data

[Cu(C10H12NO3)(NCS)]

M = 315.83

Monoclinic,

a = 10.123 (2) Å

b = 11.812 (2) Å

c = 10.264 (2) Å

β = 94.122 (2)°

V = 1224.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.96 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.662, T max = 0.696

6414 measured reflections

2602 independent reflections

1875 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.097

S = 1.04

2602 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034021/om2356sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034021/om2356Isup2.hkl

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

[Cu(C10H12NO3)(NCS)]	F(000) = 644
Mr = 315.83	Dx = 1.714 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.123 (2) Å	Cell parameters from 1160 reflections
b = 11.812 (2) Å	θ = 2.5–24.5°
c = 10.264 (2) Å	µ = 1.96 mm−1
β = 94.122 (2)°	T = 298 K
V = 1224.1 (4) Å3	Block, blue
Z = 4	0.23 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	1875 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.662, Tmax = 0.696	k = −15→9
6414 measured reflections	l = −10→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.2873P] where P = (Fo2 + 2Fc2)/3
2602 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.39 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cu1	0.53293 (4)	0.44688 (4)	0.14711 (4)	0.03113 (16)
N1	0.5018 (3)	0.5378 (2)	0.2957 (3)	0.0287 (7)
N2	0.5887 (3)	0.3555 (3)	0.0048 (3)	0.0347 (8)
O1	0.3542 (2)	0.3978 (2)	0.1187 (2)	0.0313 (6)
O2	0.6958 (2)	0.5474 (2)	0.1426 (3)	0.0369 (7)
O3	0.1241 (2)	0.3292 (2)	0.0317 (3)	0.0502 (8)
S1	0.69266 (9)	0.20646 (9)	−0.17233 (10)	0.0367 (3)
C1	0.2666 (3)	0.5001 (3)	0.2971 (4)	0.0299 (9)
C2	0.2552 (3)	0.4302 (3)	0.1865 (4)	0.0282 (8)
C3	0.1256 (4)	0.3941 (3)	0.1410 (4)	0.0356 (9)
C4	0.0163 (4)	0.4253 (4)	0.2056 (4)	0.0467 (11)
H4	−0.0676	0.4013	0.1746	0.056*
C5	0.0312 (4)	0.4923 (4)	0.3164 (5)	0.0512 (12)
H5	−0.0428	0.5120	0.3602	0.061*
C6	0.1528 (4)	0.5294 (4)	0.3616 (4)	0.0423 (11)
H6	0.1613	0.5747	0.4358	0.051*
C7	0.3894 (4)	0.5518 (3)	0.3442 (3)	0.0308 (9)
H7	0.3874	0.5995	0.4161	0.037*
C8	0.6186 (4)	0.6025 (3)	0.3450 (4)	0.0353 (10)
H8A	0.6777	0.5550	0.3997	0.042*
H8B	0.5922	0.6665	0.3964	0.042*
C9	0.6868 (4)	0.6430 (3)	0.2283 (4)	0.0394 (10)
H9A	0.6362	0.7034	0.1844	0.047*
H9B	0.7744	0.6714	0.2551	0.047*
C10	−0.0026 (4)	0.2961 (4)	−0.0268 (5)	0.0643 (15)
H10A	−0.0477	0.2509	0.0338	0.096*
H10B	0.0091	0.2528	−0.1043	0.096*
H10C	−0.0542	0.3624	−0.0492	0.096*
C11	0.6318 (3)	0.2926 (3)	−0.0683 (4)	0.0265 (8)
H2	0.701 (5)	0.568 (4)	0.0643 (18)	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.0286 (2)	0.0349 (3)	0.0305 (3)	−0.0015 (2)	0.00595 (18)	−0.0093 (2)
N1	0.0324 (16)	0.0280 (19)	0.0260 (17)	0.0028 (13)	0.0036 (13)	−0.0012 (14)
N2	0.0380 (17)	0.038 (2)	0.0291 (19)	0.0019 (15)	0.0067 (14)	−0.0066 (16)
O1	0.0285 (13)	0.0328 (15)	0.0335 (16)	−0.0030 (11)	0.0085 (11)	−0.0096 (12)
O2	0.0373 (14)	0.0396 (18)	0.0348 (16)	−0.0047 (12)	0.0100 (13)	−0.0066 (15)
O3	0.0379 (15)	0.060 (2)	0.052 (2)	−0.0168 (14)	0.0020 (13)	−0.0150 (17)
S1	0.0390 (5)	0.0337 (6)	0.0376 (6)	0.0032 (4)	0.0050 (4)	−0.0110 (5)
C1	0.0325 (19)	0.030 (2)	0.028 (2)	0.0055 (16)	0.0064 (16)	0.0026 (18)
C2	0.0301 (18)	0.024 (2)	0.032 (2)	−0.0017 (16)	0.0092 (16)	0.0061 (17)
C3	0.038 (2)	0.033 (2)	0.035 (2)	−0.0047 (18)	0.0054 (18)	0.005 (2)
C4	0.031 (2)	0.060 (3)	0.050 (3)	−0.004 (2)	0.0109 (19)	0.008 (2)
C5	0.039 (2)	0.067 (3)	0.051 (3)	0.008 (2)	0.026 (2)	0.008 (3)
C6	0.045 (2)	0.048 (3)	0.036 (2)	0.011 (2)	0.0183 (19)	0.002 (2)
C7	0.043 (2)	0.028 (2)	0.022 (2)	0.0052 (17)	0.0034 (16)	−0.0042 (18)
C8	0.037 (2)	0.034 (2)	0.035 (2)	−0.0026 (17)	−0.0045 (17)	−0.0041 (19)
C9	0.038 (2)	0.037 (3)	0.042 (3)	−0.0071 (18)	−0.0020 (18)	0.000 (2)
C10	0.050 (3)	0.067 (3)	0.075 (4)	−0.029 (2)	−0.008 (2)	−0.005 (3)
C11	0.0287 (18)	0.028 (2)	0.022 (2)	−0.0040 (16)	−0.0017 (15)	0.0055 (18)

Cu1—O1	1.902 (2)	C2—C3	1.426 (5)
Cu1—N1	1.910 (3)	C3—C4	1.380 (5)
Cu1—N2	1.933 (3)	C4—C5	1.385 (6)
Cu1—O2	2.035 (3)	C4—H4	0.9300
Cu1—S1i	2.983 (3)	C5—C6	1.357 (6)
N1—C7	1.285 (4)	C5—H5	0.9300
N1—C8	1.467 (4)	C6—H6	0.9300
N2—C11	1.164 (4)	C7—H7	0.9300
O1—C2	1.317 (4)	C8—C9	1.502 (5)
O2—C9	1.439 (5)	C8—H8A	0.9700
O2—H2	0.846 (10)	C8—H8B	0.9700
O3—C3	1.357 (5)	C9—H9A	0.9700
O3—C10	1.431 (4)	C9—H9B	0.9700
S1—C11	1.627 (4)	C10—H10A	0.9600
C1—C2	1.401 (5)	C10—H10B	0.9600
C1—C6	1.413 (5)	C10—H10C	0.9600
C1—C7	1.438 (5)
O1—Cu1—N1	94.82 (11)	C5—C4—H4	119.9
O1—Cu1—N2	92.31 (11)	C6—C5—C4	120.5 (4)
N1—Cu1—N2	172.47 (12)	C6—C5—H5	119.7
O1—Cu1—O2	159.63 (11)	C4—C5—H5	119.7
N1—Cu1—O2	82.55 (12)	C5—C6—C1	120.7 (4)
N2—Cu1—O2	91.59 (12)	C5—C6—H6	119.6
O1—Cu1—S1i	112.18 (12)	C1—C6—H6	119.6
O2—Cu1—S1i	87.96 (12)	N1—C7—C1	125.7 (3)
N1—Cu1—S1i	87.62 (12)	N1—C7—H7	117.1
N2—Cu1—S1i	87.45 (12)	C1—C7—H7	117.1
C7—N1—C8	120.9 (3)	N1—C8—C9	107.2 (3)
C7—N1—Cu1	125.7 (3)	N1—C8—H8A	110.3
C8—N1—Cu1	113.2 (2)	C9—C8—H8A	110.3
C11—N2—Cu1	171.1 (3)	N1—C8—H8B	110.3
C2—O1—Cu1	125.6 (2)	C9—C8—H8B	110.3
C9—O2—Cu1	110.9 (2)	H8A—C8—H8B	108.5
C9—O2—H2	111 (3)	O2—C9—C8	106.9 (3)
Cu1—O2—H2	107 (3)	O2—C9—H9A	110.3
C3—O3—C10	117.2 (3)	C8—C9—H9A	110.3
C2—C1—C6	120.1 (3)	O2—C9—H9B	110.3
C2—C1—C7	122.8 (3)	C8—C9—H9B	110.3
C6—C1—C7	116.9 (4)	H9A—C9—H9B	108.6
O1—C2—C1	125.3 (3)	O3—C10—H10A	109.5
O1—C2—C3	117.2 (3)	O3—C10—H10B	109.5
C1—C2—C3	117.5 (3)	H10A—C10—H10B	109.5
O3—C3—C4	125.9 (4)	O3—C10—H10C	109.5
O3—C3—C2	113.3 (3)	H10A—C10—H10C	109.5
C4—C3—C2	120.9 (4)	H10B—C10—H10C	109.5
C3—C4—C5	120.2 (4)	N2—C11—S1	179.0 (4)
C3—C4—H4	119.9

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ii	0.85 (1)	1.96 (2)	2.770 (4)	160 (5)
O2—H2···O3ii	0.85 (1)	2.41 (4)	3.020 (4)	129 (4)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.902 (2)
Cu1—N1	1.910 (3)
Cu1—N2	1.933 (3)
Cu1—O2	2.035 (3)
Cu1—S1i	2.983 (3)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ii	0.85 (1)	1.96 (2)	2.770 (4)	160 (5)
O2—H2⋯O3ii	0.85 (1)	2.41 (4)	3.020 (4)	129 (4)

Symmetry code: (ii) .