{4,4'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methanylyl-idene)]diphenolato}copper(II) monohydrate.

The asymmetric unit of the title compound, [Cu(C(21)H(24)N(2)O(4))]·H(2)O, comprises half of a Schiff base complex and a water mol-ecule. The Cu(II) atom, water mol-ecule and one C atom of the central propyl-ene segment are located on a twofold rotation axis. The geometry around the Cu(II) atom is distorted square-planar, supported by the N(2)O(2) donor atoms of the coordinating ligand. The dihedral angle between the symmetry-related benzene rings is 42.56 (19)°. In the crystal, O-H⋯O hydrogen bonds involving the water mol-ecule make an R(2) (1)(6) ring motif. Complex mol-ecules are linked into a chain along the c axis via C-H⋯O inter-actions.

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993 ▶); Blower et al. (1998 ▶). For related structures, see, for example: Ghaemi et al. (2011 ▶); Kargar et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

[Cu(C21H24N2O4)]·H2O

M = 449.98

Orthorhombic,

a = 20.567 (2) Å

b = 12.2647 (14) Å

c = 8.4287 (7) Å

V = 2126.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.06 mm−1

T = 291 K

0.21 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.256, T max = 0.535

17546 measured reflections

2620 independent reflections

1113 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 0.98

2620 reflections

134 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038135/kp2436sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038135/kp2436Isup2.hkl

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

[Cu(C21H24N2O4)]·H2O	F(000) = 940
Mr = 449.98	Dx = 1.406 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2169 reflections
a = 20.567 (2) Å	θ = 2.5–27.4°
b = 12.2647 (14) Å	µ = 1.06 mm−1
c = 8.4287 (7) Å	T = 291 K
V = 2126.1 (4) Å3	Block, dark-green
Z = 4	0.21 × 0.14 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	2620 independent reflections
Radiation source: fine-focus sealed tube	1113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.115
φ and ω scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
Tmin = 0.256, Tmax = 0.535	k = −16→16
17546 measured reflections	l = −10→8

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1009P] where P = (Fo2 + 2Fc2)/3
2620 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.36 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
O1W	0.5000	0.1449 (4)	−0.2500	0.136 (2)
H1W	0.5199	0.1907	−0.1831	0.205*
N1	0.44802 (15)	0.5832 (3)	−0.1447 (3)	0.0486 (8)
C1	0.37450 (19)	0.3777 (3)	−0.1853 (4)	0.0476 (10)
C2	0.3307 (2)	0.2908 (3)	−0.2041 (5)	0.0616 (12)
H1	0.3448	0.2271	−0.2531	0.074*
C3	0.2675 (2)	0.2974 (3)	−0.1520 (5)	0.0642 (12)
H3	0.2395	0.2389	−0.1682	0.077*
C4	0.24498 (19)	0.3899 (3)	−0.0757 (5)	0.0547 (11)
C5	0.28556 (19)	0.4760 (3)	−0.0581 (5)	0.0516 (10)
H5	0.2703	0.5388	−0.0087	0.062*
C6	0.35058 (18)	0.4730 (3)	−0.1130 (4)	0.0459 (9)
C7	0.1550 (2)	0.4783 (4)	0.0455 (6)	0.0796 (15)
H7A	0.1793	0.4947	0.1399	0.119*
H7B	0.1104	0.4650	0.0730	0.119*
H7C	0.1575	0.5389	−0.0264	0.119*
C8	0.38928 (18)	0.5688 (3)	−0.0937 (4)	0.0480 (10)
H8	0.3704	0.6265	−0.0390	0.058*
C9	0.4810 (2)	0.6853 (4)	−0.1061 (5)	0.0596 (12)
H9A	0.5197	0.6691	−0.0450	0.072*
H9B	0.4525	0.7290	−0.0400	0.072*
C10	0.5000	0.7548 (5)	−0.2500	0.0626 (16)
C11	0.4427 (3)	0.8223 (5)	−0.3009 (7)	0.139 (3)
H11A	0.4546	0.8661	−0.3906	0.209*
H11B	0.4295	0.8688	−0.2150	0.209*
H11C	0.4073	0.7751	−0.3294	0.209*
Cu1	0.5000	0.47397 (6)	−0.2500	0.0496 (3)
O1	0.43439 (12)	0.3654 (2)	−0.2370 (3)	0.0530 (7)
O3	0.18104 (14)	0.3856 (3)	−0.0270 (4)	0.0734 (9)

	U11	U22	U33	U12	U13	U23
O1W	0.216 (7)	0.081 (4)	0.113 (5)	0.000	−0.022 (4)	0.000
N1	0.045 (2)	0.060 (2)	0.041 (2)	−0.0107 (18)	0.0028 (15)	−0.0045 (16)
C1	0.048 (3)	0.052 (3)	0.043 (2)	−0.001 (2)	0.0030 (19)	0.0007 (19)
C2	0.058 (3)	0.049 (3)	0.078 (3)	−0.002 (2)	0.010 (2)	−0.009 (2)
C3	0.054 (3)	0.054 (3)	0.085 (3)	−0.011 (2)	0.010 (2)	−0.005 (2)
C4	0.040 (2)	0.059 (3)	0.065 (3)	−0.001 (2)	0.003 (2)	0.004 (2)
C5	0.046 (2)	0.054 (3)	0.054 (2)	0.003 (2)	0.005 (2)	−0.003 (2)
C6	0.043 (2)	0.048 (2)	0.046 (2)	0.000 (2)	−0.0001 (18)	0.000 (2)
C7	0.053 (3)	0.091 (4)	0.095 (4)	−0.008 (3)	0.019 (3)	−0.006 (3)
C8	0.048 (2)	0.050 (3)	0.046 (2)	0.002 (2)	0.002 (2)	−0.0086 (19)
C9	0.056 (3)	0.068 (3)	0.054 (3)	−0.015 (2)	0.003 (2)	−0.008 (2)
C10	0.072 (4)	0.054 (4)	0.062 (4)	0.000	0.006 (4)	0.000
C11	0.178 (7)	0.137 (5)	0.102 (4)	0.106 (5)	0.047 (4)	0.041 (4)
Cu1	0.0406 (4)	0.0587 (5)	0.0494 (4)	0.000	0.0029 (3)	0.000
O1	0.0433 (15)	0.0533 (17)	0.0624 (18)	0.0010 (12)	0.0043 (15)	−0.0051 (14)
O3	0.0435 (17)	0.073 (2)	0.104 (3)	−0.0068 (16)	0.0141 (16)	−0.0039 (18)

O1W—H1W	0.8940	C7—H7A	0.9600
N1—C8	1.295 (4)	C7—H7B	0.9600
N1—C9	1.460 (5)	C7—H7C	0.9600
N1—Cu1	1.930 (3)	C8—H8	0.9300
C1—O1	1.315 (4)	C9—C10	1.533 (5)
C1—C2	1.405 (5)	C9—H9A	0.9691
C1—C6	1.407 (5)	C9—H9B	0.9699
C2—C3	1.374 (5)	C10—C11i	1.503 (6)
C2—H1	0.9300	C10—C11	1.503 (6)
C3—C4	1.384 (5)	C10—C9i	1.533 (5)
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.354 (5)	C11—H11B	0.9600
C4—O3	1.379 (4)	C11—H11C	0.9600
C5—C6	1.415 (5)	Cu1—O1	1.899 (3)
C5—H5	0.9300	Cu1—O1i	1.899 (3)
C6—C8	1.429 (5)	Cu1—N1i	1.930 (3)
C7—O3	1.398 (5)
C8—N1—C9	118.5 (3)	N1—C8—H8	116.8
C8—N1—Cu1	125.1 (3)	C6—C8—H8	116.8
C9—N1—Cu1	116.1 (3)	N1—C9—C10	114.7 (3)
O1—C1—C2	118.5 (4)	N1—C9—H9A	108.9
O1—C1—C6	124.5 (4)	C10—C9—H9A	108.9
C2—C1—C6	117.0 (4)	N1—C9—H9B	108.8
C3—C2—C1	121.8 (4)	C10—C9—H9B	107.6
C3—C2—H1	119.1	H9A—C9—H9B	107.7
C1—C2—H1	119.1	C11i—C10—C11	113.1 (7)
C2—C3—C4	120.8 (4)	C11i—C10—C9i	109.4 (3)
C2—C3—H3	119.6	C11—C10—C9i	106.3 (3)
C4—C3—H3	119.6	C11i—C10—C9	106.3 (3)
C5—C4—O3	125.9 (4)	C11—C10—C9	109.4 (3)
C5—C4—C3	119.0 (4)	C9i—C10—C9	112.5 (5)
O3—C4—C3	115.2 (4)	C10—C11—H11A	109.5
C4—C5—C6	121.7 (4)	C10—C11—H11B	109.5
C4—C5—H5	119.1	H11A—C11—H11B	109.5
C6—C5—H5	119.1	C10—C11—H11C	109.5
C1—C6—C5	119.6 (4)	H11A—C11—H11C	109.5
C1—C6—C8	122.5 (4)	H11B—C11—H11C	109.5
C5—C6—C8	117.9 (4)	O1—Cu1—O1i	90.97 (15)
O3—C7—H7A	109.5	O1—Cu1—N1i	155.08 (11)
O3—C7—H7B	109.5	O1i—Cu1—N1i	93.83 (12)
H7A—C7—H7B	109.5	O1—Cu1—N1	93.83 (12)
O3—C7—H7C	109.5	O1i—Cu1—N1	155.08 (11)
H7A—C7—H7C	109.5	N1i—Cu1—N1	92.05 (18)
H7B—C7—H7C	109.5	C1—O1—Cu1	127.2 (2)
N1—C8—C6	126.5 (4)	C4—O3—C7	117.6 (3)
O1—C1—C2—C3	179.5 (4)	Cu1—N1—C9—C10	68.1 (4)
C6—C1—C2—C3	−1.1 (6)	N1—C9—C10—C11i	−153.9 (4)
C1—C2—C3—C4	−1.3 (7)	N1—C9—C10—C11	83.7 (5)
C2—C3—C4—C5	2.4 (7)	N1—C9—C10—C9i	−34.2 (2)
C2—C3—C4—O3	−179.0 (4)	C8—N1—Cu1—O1	−0.3 (3)
O3—C4—C5—C6	−179.6 (4)	C9—N1—Cu1—O1	172.8 (3)
C3—C4—C5—C6	−1.2 (6)	C8—N1—Cu1—O1i	−100.9 (4)
O1—C1—C6—C5	−178.4 (3)	C9—N1—Cu1—O1i	72.2 (4)
C2—C1—C6—C5	2.2 (6)	C8—N1—Cu1—N1i	155.4 (4)
O1—C1—C6—C8	2.4 (6)	C9—N1—Cu1—N1i	−31.4 (2)
C2—C1—C6—C8	−177.0 (3)	C2—C1—O1—Cu1	171.9 (3)
C4—C5—C6—C1	−1.1 (6)	C6—C1—O1—Cu1	−7.5 (5)
C4—C5—C6—C8	178.1 (3)	O1i—Cu1—O1—C1	161.4 (3)
C9—N1—C8—C6	−176.9 (3)	N1i—Cu1—O1—C1	−97.4 (4)
Cu1—N1—C8—C6	−3.9 (5)	N1—Cu1—O1—C1	5.9 (3)
C1—C6—C8—N1	3.7 (6)	C5—C4—O3—C7	0.8 (6)
C5—C6—C8—N1	−175.6 (4)	C3—C4—O3—C7	−177.7 (4)
C8—N1—C9—C10	−118.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1i	0.89	2.43	3.024 (5)	124
C9—H9A···O1ii	0.97	2.59	3.432 (5)	145

Table 1

Selected bond lengths (Å)

N1—Cu1	1.930 (3)
Cu1—O1	1.899 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1i	0.89	2.43	3.024 (5)	124
C9—H9A⋯O1ii	0.97	2.59	3.432 (5)	145

Symmetry codes: (i) ; (ii) .