Aqua-{4,4'-dibromo-6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}copper(II).

The title complex, [Cu(C(18)H(16)Br(2)N(2)O(4))(H(2)O)], lies on a crystallographic mirror plane with the Cu(II) ion coordinated by two N atoms and two O atoms of a tetra-dentate Schiff base ligand and one O atom from a water ligand in a slightly distorted square-pyramidal environment. The mirror plane, which coincides with the Cu-O(water) bond, imposes disorder of the atoms of the ethyl-ene group. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link complex mol-ecules into extended chains along [100].

Related literature

For related structures, see: Nathan et al. (2003 ▶); Saha et al. (2007 ▶); Xing (2009 ▶). For general background to Schiff base compounds, see: Yu et al. (2007 ▶); Ghosh et al. (2006 ▶); Singh et al. (2007 ▶); Nayka et al. (2006 ▶).

Experimental

Crystal data

[Cu(C18H16Br2N2O4)(H2O)]

M = 565.70

Orthorhombic,

a = 8.7299 (13) Å

b = 27.968 (4) Å

c = 7.9900 (12) Å

V = 1950.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.25 mm−1

T = 293 K

0.23 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.378, T max = 0.452

8970 measured reflections

1759 independent reflections

1498 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.138

S = 1.13

1759 reflections

140 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.48 e Å−3

Δρmin = −1.02 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809046212/lh2938sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046212/lh2938Isup2.hkl

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

[Cu(C18H16Br2N2O4)(H2O)]	F(000) = 1116
Mr = 565.70	Dx = 1.926 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2580 reflections
a = 8.7299 (13) Å	θ = 2.9–26.7°
b = 27.968 (4) Å	µ = 5.25 mm−1
c = 7.9900 (12) Å	T = 293 K
V = 1950.8 (5) Å3	Block, blue
Z = 4	0.23 × 0.20 × 0.18 mm

Bruker APEXII CCD diffractometer	1759 independent reflections
Radiation source: fine-focus sealed tube	1498 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
Tmin = 0.378, Tmax = 0.452	k = −33→27
8970 measured reflections	l = −8→9

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0394P)2 + 13.8845P] where P = (Fo2 + 2Fc2)/3
1759 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 1.48 e Å−3
1 restraint	Δρmin = −1.01 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Br1	0.28985 (13)	0.50680 (3)	−0.14560 (14)	0.0802 (4)
Cu1	0.43677 (12)	0.2500	0.01791 (14)	0.0336 (3)
O1	0.2831 (5)	0.29928 (14)	0.0459 (6)	0.0394 (11)
O2	0.0393 (5)	0.35017 (16)	0.0910 (7)	0.0492 (12)
O3	0.5275 (7)	0.2500	0.2889 (8)	0.0446 (16)
H3A	0.5656	0.2746	0.3257	0.067*
N1	0.5856 (6)	0.2962 (2)	−0.0675 (8)	0.0515 (16)
C1	0.4226 (7)	0.3656 (2)	−0.0697 (8)	0.0385 (15)
C2	0.2929 (7)	0.3439 (2)	0.0005 (8)	0.0334 (13)
C3	0.1626 (7)	0.3736 (2)	0.0235 (8)	0.0387 (15)
C4	0.1622 (8)	0.4211 (2)	−0.0169 (9)	0.0436 (16)
H4	0.0754	0.4397	0.0006	0.052*
C5	0.2941 (9)	0.4410 (2)	−0.0848 (9)	0.0472 (17)
C6	0.4200 (9)	0.4150 (2)	−0.1124 (9)	0.0484 (18)
H6	0.5062	0.4291	−0.1596	0.058*
C7	0.5621 (8)	0.3402 (2)	−0.1013 (9)	0.0460 (17)
H7	0.6421	0.3571	−0.1505	0.055*
C8	−0.0958 (9)	0.3769 (3)	0.1200 (10)	0.058 (2)
H8A	−0.0753	0.4015	0.2011	0.087*
H8B	−0.1746	0.3561	0.1615	0.087*
H8C	−0.1290	0.3913	0.0172	0.087*
C9	0.7175 (16)	0.2701 (7)	−0.147 (2)	0.054 (5)	0.50
H9A	0.6948	0.2643	−0.2645	0.065*	0.50
H9B	0.8089	0.2897	−0.1413	0.065*	0.50
C9A	0.7457 (13)	0.2236 (7)	−0.061 (3)	0.052 (5)	0.50
H9A1	0.7812	0.2280	0.0527	0.063*	0.50
H9A2	0.8177	0.2037	−0.1222	0.063*	0.50

	U11	U22	U33	U12	U13	U23
Br1	0.1002 (8)	0.0319 (4)	0.1084 (8)	0.0054 (4)	0.0121 (6)	0.0259 (4)
Cu1	0.0301 (5)	0.0275 (5)	0.0433 (6)	0.000	0.0040 (5)	0.000
O1	0.038 (2)	0.024 (2)	0.056 (3)	0.0025 (18)	0.006 (2)	0.010 (2)
O2	0.038 (3)	0.034 (2)	0.076 (3)	0.006 (2)	0.014 (2)	0.007 (2)
O3	0.053 (4)	0.032 (3)	0.049 (4)	0.000	−0.011 (3)	0.000
N1	0.035 (3)	0.044 (3)	0.076 (4)	0.000 (3)	0.013 (3)	0.020 (3)
C1	0.041 (4)	0.037 (4)	0.038 (3)	−0.002 (3)	0.001 (3)	0.008 (3)
C2	0.039 (3)	0.026 (3)	0.035 (3)	0.000 (3)	0.000 (3)	0.002 (3)
C3	0.041 (3)	0.035 (3)	0.040 (3)	−0.002 (3)	−0.001 (3)	0.002 (3)
C4	0.049 (4)	0.030 (3)	0.051 (4)	0.005 (3)	−0.004 (3)	0.007 (3)
C5	0.065 (5)	0.029 (3)	0.048 (4)	−0.001 (3)	−0.005 (4)	0.005 (3)
C6	0.054 (4)	0.039 (4)	0.052 (4)	−0.004 (3)	0.000 (4)	0.009 (3)
C7	0.038 (4)	0.043 (4)	0.057 (4)	−0.005 (3)	0.008 (3)	0.013 (3)
C8	0.052 (5)	0.053 (5)	0.069 (5)	0.015 (4)	0.011 (4)	0.009 (4)
C9	0.031 (8)	0.053 (9)	0.078 (14)	−0.001 (7)	0.009 (9)	0.021 (10)
C9A	0.023 (8)	0.067 (11)	0.066 (13)	0.004 (7)	−0.006 (8)	−0.011 (11)

Br1—C5	1.903 (7)	C2—C3	1.420 (9)
Cu1—O1i	1.937 (4)	C3—C4	1.367 (9)
Cu1—O1	1.937 (4)	C4—C5	1.389 (10)
Cu1—N1	1.954 (5)	C4—H4	0.9300
Cu1—N1i	1.954 (5)	C5—C6	1.338 (10)
Cu1—O3	2.305 (6)	C6—H6	0.9300
O1—C2	1.303 (7)	C7—H7	0.9300
O2—C3	1.371 (8)	C8—H8A	0.9600
O2—C8	1.416 (8)	C8—H8B	0.9600
O3—H3A	0.8188	C8—H8C	0.9600
N1—C7	1.277 (9)	C9—C9A	1.491 (19)
N1—C9Ai	1.504 (10)	C9—H9A	0.9700
N1—C9	1.505 (10)	C9—H9B	0.9700
C1—C2	1.402 (9)	C9A—N1i	1.504 (10)
C1—C6	1.421 (9)	C9A—H9A1	0.9700
C1—C7	1.433 (10)	C9A—H9A2	0.9700
O1i—Cu1—O1	90.8 (2)	C5—C4—H4	120.6
O1i—Cu1—N1	166.2 (3)	C6—C5—C4	121.8 (6)
O1—Cu1—N1	91.8 (2)	C6—C5—Br1	120.1 (6)
O1i—Cu1—N1i	91.8 (2)	C4—C5—Br1	118.1 (5)
O1—Cu1—N1i	166.2 (3)	C5—C6—C1	120.2 (7)
N1—Cu1—N1i	82.7 (4)	C5—C6—H6	119.9
O1i—Cu1—O3	97.45 (18)	C1—C6—H6	119.9
O1—Cu1—O3	97.45 (18)	N1—C7—C1	125.3 (6)
N1—Cu1—O3	95.7 (2)	N1—C7—H7	117.4
N1i—Cu1—O3	95.7 (2)	C1—C7—H7	117.4
C2—O1—Cu1	127.2 (4)	O2—C8—H8A	109.5
C3—O2—C8	117.8 (5)	O2—C8—H8B	109.5
Cu1—O3—H3A	118.5	H8A—C8—H8B	109.5
C7—N1—C9Ai	120.7 (10)	O2—C8—H8C	109.5
C7—N1—C9	120.0 (9)	H8A—C8—H8C	109.5
C7—N1—Cu1	127.2 (5)	H8B—C8—H8C	109.5
C9Ai—N1—Cu1	111.3 (9)	C9A—C9—N1	110.7 (14)
C9—N1—Cu1	109.7 (8)	C9A—C9—H9A	109.5
C2—C1—C6	120.2 (6)	N1—C9—H9A	109.5
C2—C1—C7	122.8 (6)	C9A—C9—H9B	109.5
C6—C1—C7	117.0 (6)	N1—C9—H9B	109.5
O1—C2—C1	125.4 (6)	H9A—C9—H9B	108.1
O1—C2—C3	118.1 (6)	C9—C9A—N1i	98.7 (12)
C1—C2—C3	116.5 (6)	C9—C9A—H9A1	112.0
C4—C3—O2	123.7 (6)	N1i—C9A—H9A1	112.0
C4—C3—C2	122.6 (6)	C9—C9A—H9A2	112.0
O2—C3—C2	113.7 (5)	N1i—C9A—H9A2	112.0
C3—C4—C5	118.7 (7)	H9A1—C9A—H9A2	109.7
C3—C4—H4	120.6

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ii	0.82	2.23	2.963 (5)	150
O3—H3A···O1ii	0.82	2.27	2.936 (7)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2i	0.82	2.23	2.963 (5)	150
O3—H3A⋯O1i	0.82	2.27	2.936 (7)	139

Symmetry code: (i) .