{4,4'-Dimethyl-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(2))]·H(2)O, comprises half of a Schiff base complex and half of a water mol-ecule. The whole compound is generated by crystallographic twofold rotation symmetry. The geometry around the Cu(II) atom, located on a twofold axis, is distorted square-planar, which is supported by the N(2)O(2) donor atoms of the coordinating Schiff base ligand. The dihedral angle between the symmetry-related benzene rings is 47.5 (4)°. In the crystal, the water mol-ecule that is hydrogen bonded to the coordinated O atoms links the mol-ecules via O-H⋯O inter-actions into chains parallel to [001]. The crystal structure is further stabilized by C-H⋯π inter-actions, and by π-π inter-actions involving inversion-related chelate rings [centroid-centroid distance = 3.480 (4) Å].

Related literature

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

Experimental

Crystal data

[Cu(C21H24N2O2)]·H2O

M = 417.98

Monoclinic,

a = 13.353 (5) Å

b = 15.986 (5) Å

c = 10.023 (5) Å

β = 104.696 (5)°

V = 2069.5 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.08 mm−1

T = 296 K

0.11 × 0.08 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.891, T max = 0.948

4967 measured reflections

1779 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.209

S = 0.95

1779 reflections

125 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.96 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034502/su2488sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034502/su2488Isup2.hkl

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

[Cu(C21H24N2O2)]·H2O	F(000) = 876
Mr = 417.98	Dx = 1.342 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 512 reflections
a = 13.353 (5) Å	θ = 2.5–27.4°
b = 15.986 (5) Å	µ = 1.08 mm−1
c = 10.023 (5) Å	T = 296 K
β = 104.696 (5)°	Block, dark-green
V = 2069.5 (14) Å3	0.11 × 0.08 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1779 independent reflections
Radiation source: fine-focus sealed tube	1053 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.101
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→11
Tmin = 0.891, Tmax = 0.948	k = −18→18
4967 measured reflections	l = −10→11

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0775P)2] where P = (Fo2 + 2Fc2)/3
1779 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 1.03 e Å−3
0 restraints	Δρmin = −0.96 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
Cu1	0.5000	0.01026 (6)	−0.2500	0.0266 (5)
O1	0.4089 (4)	−0.0737 (2)	−0.3499 (6)	0.0312 (14)
N1	0.4554 (5)	0.0944 (3)	−0.3912 (7)	0.0305 (16)
C1	0.3331 (6)	−0.0612 (4)	−0.4620 (9)	0.0293 (19)
C2	0.2617 (6)	−0.1276 (4)	−0.5073 (10)	0.042 (3)
H2	0.2662	−0.1758	−0.4541	0.050*
C3	0.1860 (7)	−0.1214 (5)	−0.6291 (11)	0.046 (3)
H3	0.1375	−0.1642	−0.6530	0.055*
C4	0.1790 (6)	−0.0526 (5)	−0.7191 (10)	0.045 (2)
C6	0.3222 (6)	0.0109 (4)	−0.5441 (9)	0.0311 (19)
C7	0.3854 (6)	0.0845 (4)	−0.5067 (10)	0.032 (2)
H7	0.3753	0.1282	−0.5699	0.038*
C8	0.5166 (6)	0.1727 (4)	−0.3691 (9)	0.036 (2)
H8A	0.4984	0.2056	−0.4531	0.043*
H8B	0.5894	0.1587	−0.3512	0.043*
C9	0.5000	0.2260 (6)	−0.2500	0.048 (4)
C5	0.2449 (6)	0.0134 (5)	−0.6699 (10)	0.042 (2)
H5	0.2380	0.0621	−0.7224	0.051*
C11	0.1004 (8)	−0.0471 (7)	−0.8564 (12)	0.069 (3)
H11B	0.1206	−0.0042	−0.9113	0.104*
H11A	0.0338	−0.0338	−0.8421	0.104*
H11C	0.0968	−0.0999	−0.9032	0.104*
C10	0.4033 (10)	0.2806 (6)	−0.2988 (13)	0.087 (5)
H10B	0.3947	0.3149	−0.2238	0.130*
H10A	0.3436	0.2455	−0.3299	0.130*
H10C	0.4110	0.3157	−0.3733	0.130*
O1W	0.5000	−0.2254 (4)	−0.2500	0.091 (5)
H1W1	0.5281	−0.1936	−0.2981	0.137*

	U11	U22	U33	U12	U13	U23
Cu1	0.0194 (7)	0.0263 (6)	0.0300 (9)	0.000	−0.0015 (6)	0.000
O1	0.026 (3)	0.026 (2)	0.031 (4)	−0.0008 (18)	−0.012 (3)	−0.005 (2)
N1	0.033 (4)	0.032 (3)	0.030 (5)	−0.005 (2)	0.016 (4)	0.003 (3)
C1	0.018 (4)	0.038 (4)	0.030 (5)	0.001 (3)	0.003 (4)	−0.005 (3)
C2	0.031 (5)	0.037 (4)	0.049 (7)	0.000 (3)	−0.007 (5)	0.000 (4)
C3	0.020 (5)	0.060 (5)	0.052 (7)	−0.007 (3)	0.001 (5)	−0.014 (5)
C4	0.017 (4)	0.068 (5)	0.046 (7)	−0.005 (4)	−0.003 (5)	−0.003 (5)
C6	0.022 (4)	0.036 (3)	0.032 (5)	0.007 (3)	0.001 (4)	0.001 (3)
C7	0.030 (5)	0.029 (3)	0.036 (6)	0.007 (3)	0.006 (5)	0.011 (3)
C8	0.026 (5)	0.032 (4)	0.044 (6)	−0.007 (3)	−0.002 (5)	0.004 (3)
C9	0.046 (9)	0.025 (5)	0.073 (12)	0.000	0.018 (8)	0.000
C5	0.026 (5)	0.052 (4)	0.043 (6)	0.005 (3)	−0.002 (4)	0.007 (4)
C11	0.036 (6)	0.113 (8)	0.049 (8)	−0.013 (5)	−0.007 (6)	0.000 (6)
C10	0.123 (12)	0.058 (6)	0.089 (11)	0.050 (6)	0.045 (9)	0.034 (6)
O1W	0.106 (10)	0.033 (5)	0.106 (11)	0.000	−0.026 (8)	0.000

Cu1—O1i	1.914 (4)	C6—C7	1.441 (10)
Cu1—O1	1.914 (4)	C7—H7	0.9300
Cu1—N1i	1.934 (6)	C8—C9	1.527 (10)
Cu1—N1	1.934 (6)	C8—H8A	0.9700
O1—C1	1.322 (9)	C8—H8B	0.9700
N1—C7	1.300 (10)	C9—C8i	1.527 (10)
N1—C8	1.480 (8)	C9—C10	1.533 (10)
C1—C6	1.403 (10)	C9—C10i	1.533 (10)
C1—C2	1.423 (10)	C5—H5	0.9300
C2—C3	1.377 (12)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.411 (13)	C11—H11C	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.382 (11)	C10—H10A	0.9600
C4—C11	1.507 (12)	C10—H10C	0.9600
C6—C5	1.413 (11)	O1W—H1W1	0.8513
O1i—Cu1—O1	91.0 (3)	N1—C8—C9	113.9 (7)
O1i—Cu1—N1i	93.9 (2)	N1—C8—H8A	108.8
O1—Cu1—N1i	155.2 (3)	C9—C8—H8A	108.8
O1i—Cu1—N1	155.1 (3)	N1—C8—H8B	108.8
O1—Cu1—N1	93.9 (2)	C9—C8—H8B	108.8
N1i—Cu1—N1	91.9 (4)	H8A—C8—H8B	107.7
C1—O1—Cu1	125.9 (4)	C8—C9—C8i	112.2 (8)
C7—N1—C8	118.8 (6)	C8—C9—C10	110.2 (6)
C7—N1—Cu1	125.8 (4)	C8i—C9—C10	106.9 (6)
C8—N1—Cu1	115.0 (5)	C8—C9—C10i	106.9 (6)
O1—C1—C6	124.5 (6)	C8i—C9—C10i	110.2 (6)
O1—C1—C2	117.8 (7)	C10—C9—C10i	110.5 (11)
C6—C1—C2	117.6 (8)	C4—C5—C6	123.4 (8)
C3—C2—C1	120.8 (8)	C4—C5—H5	118.3
C3—C2—H2	119.6	C6—C5—H5	118.3
C1—C2—H2	119.6	C4—C11—H11B	109.5
C2—C3—C4	122.5 (7)	C4—C11—H11A	109.5
C2—C3—H3	118.8	H11B—C11—H11A	109.5
C4—C3—H3	118.8	C4—C11—H11C	109.5
C5—C4—C3	115.8 (8)	H11B—C11—H11C	109.5
C5—C4—C11	121.0 (9)	H11A—C11—H11C	109.5
C3—C4—C11	123.1 (8)	C9—C10—H10B	109.5
C1—C6—C5	119.4 (7)	C9—C10—H10A	109.5
C1—C6—C7	123.4 (7)	H10B—C10—H10A	109.5
C5—C6—C7	117.1 (7)	C9—C10—H10C	109.5
N1—C7—C6	124.9 (7)	H10B—C10—H10C	109.5
N1—C7—H7	117.5	H10A—C10—H10C	109.5
C6—C7—H7	117.5
O1i—Cu1—O1—C1	−166.5 (8)	C2—C1—C6—C5	−2.8 (12)
N1i—Cu1—O1—C1	92.1 (9)	O1—C1—C6—C7	−7.9 (13)
N1—Cu1—O1—C1	−10.9 (7)	C2—C1—C6—C7	176.4 (8)
O1i—Cu1—N1—C7	101.3 (8)	C8—N1—C7—C6	178.2 (8)
O1—Cu1—N1—C7	0.5 (8)	Cu1—N1—C7—C6	5.8 (13)
N1i—Cu1—N1—C7	−155.3 (9)	C1—C6—C7—N1	−3.6 (14)
O1i—Cu1—N1—C8	−71.3 (8)	C5—C6—C7—N1	175.7 (8)
O1—Cu1—N1—C8	−172.1 (6)	C7—N1—C8—C9	116.3 (8)
N1i—Cu1—N1—C8	32.1 (4)	Cu1—N1—C8—C9	−70.5 (7)
Cu1—O1—C1—C6	15.7 (11)	N1—C8—C9—C8i	35.3 (4)
Cu1—O1—C1—C2	−168.6 (6)	N1—C8—C9—C10	−83.7 (9)
O1—C1—C2—C3	−174.8 (8)	N1—C8—C9—C10i	156.2 (8)
C6—C1—C2—C3	1.2 (14)	C3—C4—C5—C6	6.1 (15)
C1—C2—C3—C4	4.2 (15)	C11—C4—C5—C6	−177.9 (9)
C2—C3—C4—C5	−7.7 (15)	C1—C6—C5—C4	−1.0 (14)
C2—C3—C4—C11	176.4 (10)	C7—C6—C5—C4	179.7 (9)
O1—C1—C6—C5	172.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.85	2.46	2.783 (7)	103
O1W—H1W1···O1i	0.85	2.44	2.783 (7)	105
C3—H3···O1Wii	0.93	2.55	3.48 (1)	173
C8—H8B···Cg1iii	0.97	2.83	3.693 (9)	148
C11—H11B···Cg1iv	0.96	2.98	3.850 (12)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1	0.85	2.46	2.783 (7)	103
O1W—H1W1⋯O1i	0.85	2.44	2.783 (7)	105
C3—H3⋯O1W ii	0.93	2.55	3.48 (1)	173
C8—H8B⋯Cg1iii	0.97	2.83	3.693 (9)	148
C11—H11B⋯Cg1iv	0.96	2.98	3.850 (12)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .