Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethyl-idene]ethanamine-κN,N',N''}copper(II) monohydrate.

In the title compound, [CuCl(2)(C(13)H(19)N(3)O)]·H(2)O, the tridentate Schiff base ligand and the two Cl atoms complete a distorted square-pyramidal coordination geometry around the Cu(II) ion in which the three N atoms and one Cl atom are located in the basal plane and the other Cl atom is at the apical position. In the crystal, O-H⋯Cl hydrogen bonds link the complex mol-ecules and the uncoordinated water mol-ecules into infinite chains along the a axis. The chains are further connected into a three-dimensional network via C-H⋯O and C-H⋯Cl inter-actions.

Related literature

For the structures of CuCl2 complexes with similar ligands, see: Saleh Salga et al. (2010 ▶); Wang et al. (2009 ▶). For the structure of a CdCl2 complex with the same Schiff base ligand, see: Ikmal Hisham et al. (2010 ▶). For a description of the geometry of complexes with a five-coordinate metal atom, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CuCl2(C13H19N3O)]·H2O

M = 385.77

Monoclinic,

a = 7.9194 (8) Å

b = 8.5793 (8) Å

c = 22.925 (2) Å

β = 91.981 (1)°

V = 1556.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.75 mm−1

T = 100 K

0.18 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.743, T max = 0.858

9634 measured reflections

3348 independent reflections

2948 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.060

S = 1.05

3348 reflections

197 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001) ▶; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004892/is2674sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004892/is2674Isup2.hkl

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

[CuCl2(C13H19N3O)]·H2O	F(000) = 796
Mr = 385.77	Dx = 1.646 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4229 reflections
a = 7.9194 (8) Å	θ = 2.5–28.2°
b = 8.5793 (8) Å	µ = 1.75 mm−1
c = 22.925 (2) Å	T = 100 K
β = 91.981 (1)°	Block, green
V = 1556.6 (3) Å3	0.18 × 0.16 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	2948 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.743, Tmax = 0.858	k = −10→10
9634 measured reflections	l = −29→28

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0258P)2 + 0.893P] where P = (Fo2 + 2Fc2)/3
3348 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.37 e Å−3
2 restraints	Δρmin = −0.34 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	0.60251 (3)	0.86379 (2)	0.122328 (9)	0.01099 (7)
Cl1	0.49087 (6)	0.62132 (5)	0.11931 (2)	0.01873 (11)
Cl2	0.90458 (6)	0.85029 (5)	0.15951 (2)	0.01773 (11)
O1	0.32231 (17)	0.82636 (16)	0.30317 (6)	0.0183 (3)
N1	0.68558 (19)	0.86674 (17)	0.03959 (7)	0.0129 (3)
N2	0.60269 (19)	1.09006 (17)	0.10733 (7)	0.0119 (3)
N3	0.51025 (18)	0.92685 (17)	0.20213 (6)	0.0114 (3)
C1	0.7350 (2)	0.7448 (2)	0.00826 (8)	0.0159 (4)
H1	0.7128	0.6427	0.0221	0.019*
C2	0.8177 (2)	0.7617 (2)	−0.04381 (8)	0.0167 (4)
H2	0.8513	0.6729	−0.0653	0.020*
C3	0.8501 (2)	0.9106 (2)	−0.06373 (8)	0.0156 (4)
H3	0.9077	0.9254	−0.0990	0.019*
C4	0.7975 (2)	1.0386 (2)	−0.03157 (8)	0.0147 (4)
H4	0.8168	1.1417	−0.0449	0.018*
C5	0.7169 (2)	1.0126 (2)	0.01989 (8)	0.0121 (4)
C6	0.6645 (2)	1.1396 (2)	0.05987 (8)	0.0127 (4)
C7	0.6910 (2)	1.3055 (2)	0.04320 (8)	0.0172 (4)
H7A	0.6395	1.3737	0.0719	0.026*
H7B	0.6385	1.3247	0.0045	0.026*
H7C	0.8124	1.3271	0.0422	0.026*
C8	0.5483 (2)	1.1856 (2)	0.15617 (8)	0.0127 (4)
H8A	0.4272	1.2127	0.1510	0.015*
H8B	0.6148	1.2832	0.1587	0.015*
C9	0.5779 (2)	1.0881 (2)	0.21117 (8)	0.0132 (4)
H9A	0.7005	1.0830	0.2210	0.016*
H9B	0.5212	1.1379	0.2442	0.016*
C10	0.5778 (2)	0.8179 (2)	0.24813 (8)	0.0139 (4)
H10A	0.7017	0.8316	0.2522	0.017*
H10B	0.5557	0.7094	0.2353	0.017*
C11	0.5017 (2)	0.8419 (2)	0.30720 (8)	0.0174 (4)
H11A	0.5492	0.7642	0.3352	0.021*
H11B	0.5316	0.9471	0.3221	0.021*
C12	0.2547 (2)	0.9419 (2)	0.26393 (8)	0.0171 (4)
H12A	0.2853	1.0468	0.2789	0.021*
H12B	0.1299	0.9340	0.2620	0.021*
C13	0.3217 (2)	0.9220 (2)	0.20293 (8)	0.0130 (4)
H13A	0.2818	0.8210	0.1867	0.016*
H13B	0.2749	1.0057	0.1774	0.016*
O2	0.0878 (2)	0.59912 (18)	0.08146 (7)	0.0273 (3)
H2A	0.035 (3)	0.659 (3)	0.1032 (10)	0.033*
H2B	0.183 (2)	0.602 (3)	0.0978 (11)	0.033*

	U11	U22	U33	U12	U13	U23
Cu1	0.01348 (12)	0.00927 (11)	0.01044 (12)	0.00023 (8)	0.00364 (8)	0.00007 (8)
Cl1	0.0256 (3)	0.0112 (2)	0.0200 (2)	−0.00334 (17)	0.00966 (19)	−0.00245 (17)
Cl2	0.0123 (2)	0.0245 (2)	0.0165 (2)	0.00191 (17)	0.00273 (17)	0.00437 (18)
O1	0.0157 (7)	0.0231 (7)	0.0165 (7)	−0.0002 (5)	0.0050 (5)	0.0047 (6)
N1	0.0131 (7)	0.0133 (7)	0.0124 (8)	0.0007 (6)	0.0013 (6)	0.0005 (6)
N2	0.0124 (7)	0.0112 (7)	0.0120 (8)	0.0006 (6)	0.0008 (6)	−0.0010 (6)
N3	0.0109 (7)	0.0114 (7)	0.0120 (8)	−0.0005 (6)	0.0013 (6)	−0.0006 (6)
C1	0.0190 (10)	0.0125 (9)	0.0162 (10)	0.0001 (7)	0.0019 (8)	−0.0010 (7)
C2	0.0175 (9)	0.0177 (9)	0.0151 (10)	0.0032 (7)	0.0029 (7)	−0.0031 (7)
C3	0.0142 (9)	0.0215 (10)	0.0113 (9)	0.0014 (7)	0.0017 (7)	0.0002 (7)
C4	0.0145 (9)	0.0155 (9)	0.0142 (9)	0.0001 (7)	0.0004 (7)	0.0017 (7)
C5	0.0127 (9)	0.0130 (8)	0.0107 (9)	0.0010 (7)	0.0003 (7)	−0.0004 (7)
C6	0.0108 (8)	0.0141 (9)	0.0130 (9)	0.0002 (7)	0.0003 (7)	0.0008 (7)
C7	0.0229 (10)	0.0124 (9)	0.0169 (10)	0.0016 (7)	0.0070 (8)	0.0016 (7)
C8	0.0150 (9)	0.0109 (8)	0.0124 (9)	−0.0008 (7)	0.0031 (7)	−0.0010 (7)
C9	0.0145 (9)	0.0126 (9)	0.0126 (9)	−0.0025 (7)	0.0007 (7)	−0.0029 (7)
C10	0.0127 (9)	0.0155 (9)	0.0134 (9)	0.0024 (7)	0.0007 (7)	0.0033 (7)
C11	0.0160 (9)	0.0228 (10)	0.0134 (9)	0.0002 (8)	0.0021 (7)	0.0025 (8)
C12	0.0152 (9)	0.0194 (9)	0.0171 (10)	0.0013 (7)	0.0056 (8)	−0.0004 (8)
C13	0.0099 (8)	0.0144 (9)	0.0148 (9)	−0.0005 (7)	0.0009 (7)	0.0000 (7)
O2	0.0307 (9)	0.0231 (8)	0.0285 (9)	0.0035 (7)	0.0053 (7)	−0.0013 (7)

Cu1—N2	1.9715 (15)	C5—C6	1.491 (2)
Cu1—N1	2.0290 (15)	C6—C7	1.490 (2)
Cu1—N3	2.0654 (15)	C7—H7A	0.9800
Cu1—Cl1	2.2604 (5)	C7—H7B	0.9800
Cu1—Cl2	2.5143 (5)	C7—H7C	0.9800
O1—C11	1.427 (2)	C8—C9	1.524 (2)
O1—C12	1.430 (2)	C8—H8A	0.9900
N1—C1	1.336 (2)	C8—H8B	0.9900
N1—C5	1.356 (2)	C9—H9A	0.9900
N2—C6	1.281 (2)	C9—H9B	0.9900
N2—C8	1.464 (2)	C10—C11	1.515 (3)
N3—C10	1.494 (2)	C10—H10A	0.9900
N3—C13	1.495 (2)	C10—H10B	0.9900
N3—C9	1.495 (2)	C11—H11A	0.9900
C1—C2	1.389 (3)	C11—H11B	0.9900
C1—H1	0.9500	C12—C13	1.522 (3)
C2—C3	1.383 (3)	C12—H12A	0.9900
C2—H2	0.9500	C12—H12B	0.9900
C3—C4	1.395 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.379 (3)	O2—H2A	0.837 (16)
C4—H4	0.9500	O2—H2B	0.831 (16)
N2—Cu1—N1	79.77 (6)	C6—C7—H7B	109.5
N2—Cu1—N3	84.20 (6)	H7A—C7—H7B	109.5
N1—Cu1—N3	163.90 (6)	C6—C7—H7C	109.5
N2—Cu1—Cl1	154.62 (5)	H7A—C7—H7C	109.5
N1—Cu1—Cl1	97.01 (4)	H7B—C7—H7C	109.5
N3—Cu1—Cl1	96.79 (4)	N2—C8—C9	106.53 (14)
N2—Cu1—Cl2	95.63 (5)	N2—C8—H8A	110.4
N1—Cu1—Cl2	88.97 (5)	C9—C8—H8A	110.4
N3—Cu1—Cl2	94.20 (4)	N2—C8—H8B	110.4
Cl1—Cu1—Cl2	109.544 (19)	C9—C8—H8B	110.4
C11—O1—C12	109.02 (14)	H8A—C8—H8B	108.6
C1—N1—C5	118.92 (16)	N3—C9—C8	110.42 (14)
C1—N1—Cu1	127.12 (12)	N3—C9—H9A	109.6
C5—N1—Cu1	113.06 (12)	C8—C9—H9A	109.6
C6—N2—C8	126.51 (15)	N3—C9—H9B	109.6
C6—N2—Cu1	118.51 (13)	C8—C9—H9B	109.6
C8—N2—Cu1	114.57 (11)	H9A—C9—H9B	108.1
C10—N3—C13	107.88 (14)	N3—C10—C11	113.72 (15)
C10—N3—C9	111.29 (14)	N3—C10—H10A	108.8
C13—N3—C9	112.19 (14)	C11—C10—H10A	108.8
C10—N3—Cu1	109.42 (11)	N3—C10—H10B	108.8
C13—N3—Cu1	112.81 (11)	C11—C10—H10B	108.8
C9—N3—Cu1	103.24 (10)	H10A—C10—H10B	107.7
N1—C1—C2	122.40 (17)	O1—C11—C10	110.79 (15)
N1—C1—H1	118.8	O1—C11—H11A	109.5
C2—C1—H1	118.8	C10—C11—H11A	109.5
C3—C2—C1	118.62 (17)	O1—C11—H11B	109.5
C3—C2—H2	120.7	C10—C11—H11B	109.5
C1—C2—H2	120.7	H11A—C11—H11B	108.1
C2—C3—C4	119.35 (17)	O1—C12—C13	111.41 (15)
C2—C3—H3	120.3	O1—C12—H12A	109.3
C4—C3—H3	120.3	C13—C12—H12A	109.3
C5—C4—C3	118.75 (17)	O1—C12—H12B	109.3
C5—C4—H4	120.6	C13—C12—H12B	109.3
C3—C4—H4	120.6	H12A—C12—H12B	108.0
N1—C5—C4	121.95 (16)	N3—C13—C12	112.83 (15)
N1—C5—C6	114.30 (15)	N3—C13—H13A	109.0
C4—C5—C6	123.69 (16)	C12—C13—H13A	109.0
N2—C6—C7	126.57 (17)	N3—C13—H13B	109.0
N2—C6—C5	113.71 (16)	C12—C13—H13B	109.0
C7—C6—C5	119.70 (16)	H13A—C13—H13B	107.8
C6—C7—H7A	109.5	H2A—O2—H2B	101 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···Cl2i	0.84 (2)	2.35 (2)	3.1829 (16)	173 (2)
O2—H2B···Cl1	0.83 (2)	2.48 (2)	3.2841 (18)	164 (2)
C2—H2···O2ii	0.95	2.41	3.307 (2)	156
C3—H3···Cl2iii	0.95	2.82	3.619 (2)	142
C4—H4···O2iv	0.95	2.50	3.445 (2)	172
C7—H7A···Cl1v	0.98	2.68	3.6179 (19)	161
C8—H8A···O1vi	0.99	2.47	3.336 (2)	146
C10—H10B···Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A···Cl2	0.99	2.71	3.3566 (19)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯Cl2i	0.84 (2)	2.35 (2)	3.1829 (16)	173 (2)
O2—H2B⋯Cl1	0.83 (2)	2.48 (2)	3.2841 (18)	164 (2)
C2—H2⋯O2ii	0.95	2.41	3.307 (2)	156
C3—H3⋯Cl2iii	0.95	2.82	3.619 (2)	142
C4—H4⋯O2iv	0.95	2.50	3.445 (2)	172
C7—H7A⋯Cl1v	0.98	2.68	3.6179 (19)	161
C8—H8A⋯O1vi	0.99	2.47	3.336 (2)	146
C10—H10B⋯Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A⋯Cl2	0.99	2.71	3.3566 (19)	123

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