Dichlorido{2-[2-(piperidin-1-yl)ethyl-imino-meth-yl]phenolato}zinc(II) monohydrate.

In the title mononuclear zinc(II) complex, [ZnCl(2)(C(14)H(20)N(2)O)]·H(2)O, the Zn(II) atom is four-coordinated by the phenolate O and imine N atoms of the Schiff base ligand and by two Cl atoms in a tetra-hedral geometry. In the crystal structure, O-H⋯Cl, O-H⋯O and N-H⋯O hydrogen bonds involving the water mol-ecules bridge adjacent complexes into a ladder-like structure running along the c axis.

Related literature

For general background on Schiff base complexes, see: Kawamoto et al. (2008 ▶); Tomat et al. (2007 ▶). For biological properties of Schiff base compounds, see: Abd-Elzaher (2004 ▶); Iqbal et al. (2005 ▶); Osowole et al. (2005 ▶); Raman & Thangaraja (2005 ▶). For related structures, see: Ali et al. (2008 ▶); Li (2007 ▶); Tatar et al. (2002 ▶); Wang (2007 ▶).

Experimental

Crystal data

[ZnCl2(C14H20N2O)]·H2O

M = 386.61

Monoclinic,

a = 9.1860 (18) Å

b = 19.875 (4) Å

c = 9.966 (2) Å

β = 110.20 (3)°

V = 1707.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.76 mm−1

T = 298 (2) K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.720, T max = 0.754

14151 measured reflections

3882 independent reflections

2685 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.104

S = 0.97

3882 reflections

199 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014311/ci2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014311/ci2598Isup2.hkl

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

[ZnCl2(C14H20N2O)]·H2O	F000 = 800
Mr = 386.61	Dx = 1.504 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2461 reflections
a = 9.1860 (18) Å	θ = 2.4–25.0º
b = 19.875 (4) Å	µ = 1.76 mm−1
c = 9.966 (2) Å	T = 298 (2) K
β = 110.20 (3)º	Block, yellow
V = 1707.6 (7) Å3	0.20 × 0.18 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3882 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.056
T = 298(2) K	θmax = 27.5º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.720, Tmax = 0.755	k = −25→25
14151 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
3882 reflections	Δρmax = 0.49 e Å−3
199 parameters	Δρmin = −0.58 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Zn1	0.30417 (4)	0.444609 (17)	0.67776 (4)	0.03531 (13)
Cl1	0.53819 (11)	0.40618 (5)	0.68728 (10)	0.0547 (3)
Cl2	0.13426 (12)	0.36691 (5)	0.68208 (10)	0.0566 (3)
O1	0.3309 (3)	0.51454 (10)	0.8185 (2)	0.0466 (6)
O2	0.2673 (3)	0.48851 (13)	0.0627 (3)	0.0540 (7)
N1	0.2172 (3)	0.50529 (13)	0.5054 (2)	0.0330 (6)
N2	0.1661 (3)	0.38887 (13)	0.1946 (3)	0.0322 (6)
C6	0.2940 (3)	0.60705 (15)	0.6525 (3)	0.0349 (7)
C1	0.3412 (4)	0.57904 (16)	0.7920 (3)	0.0360 (7)
C2	0.3972 (4)	0.62356 (17)	0.9080 (3)	0.0423 (8)
H2	0.4311	0.6063	1.0004	0.051*
C3	0.4035 (4)	0.69155 (18)	0.8893 (4)	0.0494 (9)
H3	0.4404	0.7197	0.9684	0.059*
C4	0.3549 (4)	0.71867 (18)	0.7520 (4)	0.0553 (10)
H4	0.3586	0.7649	0.7392	0.066*
C5	0.3019 (4)	0.67719 (17)	0.6368 (4)	0.0481 (9)
H5	0.2702	0.6956	0.5454	0.058*
C7	0.2314 (4)	0.56952 (15)	0.5204 (3)	0.0351 (7)
H7	0.1976	0.5948	0.4367	0.042*
C8	0.1417 (4)	0.48009 (16)	0.3607 (3)	0.0420 (8)
H8A	0.1519	0.5126	0.2919	0.050*
H8B	0.0321	0.4730	0.3428	0.050*
C9	0.2177 (4)	0.41441 (16)	0.3450 (3)	0.0379 (8)
H9A	0.3293	0.4206	0.3789	0.045*
H9B	0.1945	0.3807	0.4051	0.045*
C10	0.2450 (4)	0.32330 (17)	0.1916 (3)	0.0414 (8)
H10A	0.2136	0.2904	0.2482	0.050*
H10B	0.3564	0.3292	0.2339	0.050*
C11	0.2048 (4)	0.29752 (17)	0.0403 (3)	0.0454 (9)
H11A	0.2538	0.2542	0.0419	0.054*
H11B	0.2446	0.3284	−0.0141	0.054*
C12	0.0304 (4)	0.29045 (18)	−0.0318 (4)	0.0507 (9)
H12A	0.0064	0.2773	−0.1308	0.061*
H12B	−0.0082	0.2558	0.0158	0.061*
C13	−0.0471 (4)	0.35675 (18)	−0.0247 (3)	0.0476 (9)
H13A	−0.1587	0.3514	−0.0667	0.057*
H13B	−0.0156	0.3900	−0.0805	0.057*
C14	−0.0063 (4)	0.38173 (17)	0.1267 (3)	0.0422 (8)
H14A	−0.0555	0.4249	0.1267	0.051*
H14B	−0.0442	0.3503	0.1814	0.051*
H2C	0.198 (5)	0.4214 (14)	0.148 (4)	0.080*
H2B	0.295 (4)	0.492 (2)	−0.009 (2)	0.080*
H2A	0.330 (4)	0.5124 (18)	0.128 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Zn1	0.0448 (3)	0.0329 (2)	0.0281 (2)	0.00015 (17)	0.01246 (17)	0.00067 (15)
Cl1	0.0473 (6)	0.0665 (6)	0.0490 (5)	0.0112 (5)	0.0150 (4)	0.0005 (5)
Cl2	0.0635 (6)	0.0507 (5)	0.0599 (6)	−0.0155 (5)	0.0266 (5)	0.0007 (4)
O1	0.0800 (18)	0.0341 (13)	0.0296 (12)	−0.0072 (12)	0.0238 (12)	−0.0028 (10)
O2	0.0692 (19)	0.0562 (16)	0.0411 (14)	−0.0195 (13)	0.0248 (14)	−0.0026 (12)
N1	0.0398 (16)	0.0353 (14)	0.0255 (13)	0.0008 (12)	0.0132 (12)	−0.0010 (11)
N2	0.0331 (15)	0.0381 (14)	0.0252 (13)	0.0002 (12)	0.0099 (11)	0.0004 (11)
C6	0.0319 (18)	0.0368 (17)	0.0374 (18)	0.0024 (14)	0.0138 (15)	0.0022 (14)
C1	0.0355 (19)	0.0385 (17)	0.0386 (19)	0.0004 (14)	0.0187 (15)	−0.0065 (14)
C2	0.046 (2)	0.047 (2)	0.0370 (19)	−0.0021 (16)	0.0183 (16)	−0.0113 (15)
C3	0.037 (2)	0.045 (2)	0.068 (3)	−0.0056 (16)	0.0200 (19)	−0.0248 (19)
C4	0.050 (2)	0.0339 (19)	0.080 (3)	0.0040 (17)	0.020 (2)	−0.0045 (19)
C5	0.049 (2)	0.0342 (18)	0.060 (2)	0.0049 (16)	0.0171 (19)	0.0042 (17)
C7	0.0336 (18)	0.0404 (19)	0.0336 (18)	0.0073 (14)	0.0145 (15)	0.0088 (14)
C8	0.047 (2)	0.048 (2)	0.0294 (17)	0.0098 (17)	0.0113 (16)	0.0019 (15)
C9	0.043 (2)	0.0495 (19)	0.0190 (16)	0.0072 (16)	0.0082 (14)	−0.0001 (13)
C10	0.039 (2)	0.0447 (19)	0.0378 (19)	0.0078 (16)	0.0102 (16)	0.0010 (15)
C11	0.045 (2)	0.045 (2)	0.045 (2)	0.0031 (16)	0.0135 (17)	−0.0076 (16)
C12	0.049 (2)	0.053 (2)	0.047 (2)	−0.0069 (18)	0.0124 (18)	−0.0116 (17)
C13	0.036 (2)	0.063 (2)	0.0363 (19)	−0.0028 (17)	0.0029 (16)	−0.0081 (17)
C14	0.0313 (19)	0.050 (2)	0.041 (2)	0.0048 (16)	0.0077 (15)	−0.0008 (16)

Zn1—O1	1.929 (2)	C4—H4	0.93
Zn1—N1	2.024 (2)	C5—H5	0.93
Zn1—Cl2	2.2066 (10)	C7—H7	0.93
Zn1—Cl1	2.2523 (10)	C8—C9	1.514 (4)
O1—C1	1.319 (4)	C8—H8A	0.97
O2—H2B	0.84 (3)	C8—H8B	0.97
O2—H2A	0.85 (3)	C9—H9A	0.97
N1—C7	1.287 (4)	C9—H9B	0.97
N1—C8	1.457 (4)	C10—C11	1.512 (4)
N2—C9	1.496 (4)	C10—H10A	0.97
N2—C10	1.496 (4)	C10—H10B	0.97
N2—C14	1.499 (4)	C11—C12	1.520 (5)
N2—H2C	0.90 (4)	C11—H11A	0.97
C6—C5	1.407 (4)	C11—H11B	0.97
C6—C1	1.420 (4)	C12—C13	1.511 (5)
C6—C7	1.448 (4)	C12—H12A	0.97
C1—C2	1.404 (4)	C12—H12B	0.97
C2—C3	1.368 (5)	C13—C14	1.507 (4)
C2—H2	0.93	C13—H13A	0.97
C3—C4	1.393 (5)	C13—H13B	0.97
C3—H3	0.93	C14—H14A	0.97
C4—C5	1.360 (5)	C14—H14B	0.97
O1—Zn1—N1	95.83 (10)	C9—C8—H8A	110.0
O1—Zn1—Cl2	113.80 (8)	N1—C8—H8B	110.0
N1—Zn1—Cl2	111.04 (8)	C9—C8—H8B	110.0
O1—Zn1—Cl1	109.48 (8)	H8A—C8—H8B	108.3
N1—Zn1—Cl1	109.22 (8)	N2—C9—C8	113.5 (2)
Cl2—Zn1—Cl1	115.66 (4)	N2—C9—H9A	108.9
C1—O1—Zn1	123.71 (18)	C8—C9—H9A	108.9
H2B—O2—H2A	106 (2)	N2—C9—H9B	108.9
C7—N1—C8	116.8 (3)	C8—C9—H9B	108.9
C7—N1—Zn1	119.9 (2)	H9A—C9—H9B	107.7
C8—N1—Zn1	123.31 (19)	N2—C10—C11	111.2 (2)
C9—N2—C10	109.1 (2)	N2—C10—H10A	109.4
C9—N2—C14	113.8 (2)	C11—C10—H10A	109.4
C10—N2—C14	110.6 (2)	N2—C10—H10B	109.4
C9—N2—H2C	103 (3)	C11—C10—H10B	109.4
C10—N2—H2C	112 (3)	H10A—C10—H10B	108.0
C14—N2—H2C	108 (3)	C10—C11—C12	110.9 (3)
C5—C6—C1	119.1 (3)	C10—C11—H11A	109.4
C5—C6—C7	115.4 (3)	C12—C11—H11A	109.4
C1—C6—C7	125.4 (3)	C10—C11—H11B	109.4
O1—C1—C2	118.6 (3)	C12—C11—H11B	109.4
O1—C1—C6	123.9 (3)	H11A—C11—H11B	108.0
C2—C1—C6	117.4 (3)	C13—C12—C11	109.5 (3)
C3—C2—C1	122.1 (3)	C13—C12—H12A	109.8
C3—C2—H2	119.0	C11—C12—H12A	109.8
C1—C2—H2	119.0	C13—C12—H12B	109.8
C2—C3—C4	120.1 (3)	C11—C12—H12B	109.8
C2—C3—H3	120.0	H12A—C12—H12B	108.2
C4—C3—H3	120.0	C12—C13—C14	112.1 (3)
C5—C4—C3	119.7 (3)	C12—C13—H13A	109.2
C5—C4—H4	120.2	C14—C13—H13A	109.2
C3—C4—H4	120.2	C12—C13—H13B	109.2
C4—C5—C6	121.6 (3)	C14—C13—H13B	109.2
C4—C5—H5	119.2	H13A—C13—H13B	107.9
C6—C5—H5	119.2	N2—C14—C13	110.0 (3)
N1—C7—C6	127.5 (3)	N2—C14—H14A	109.7
N1—C7—H7	116.2	C13—C14—H14A	109.7
C6—C7—H7	116.2	N2—C14—H14B	109.7
N1—C8—C9	108.6 (2)	C13—C14—H14B	109.7
N1—C8—H8A	110.0	H14A—C14—H14B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O2	0.90 (4)	1.81 (4)	2.712 (3)	177 (4)
O2—H2B···O1i	0.84 (3)	1.91 (3)	2.741 (3)	168 (4)
O2—H2A···Cl1ii	0.85 (3)	2.44 (3)	3.272 (3)	168 (4)

Zn1—O1	1.929 (2)
Zn1—N1	2.024 (2)
Zn1—Cl2	2.2066 (10)
Zn1—Cl1	2.2523 (10)

O1—Zn1—N1	95.83 (10)
O1—Zn1—Cl2	113.80 (8)
N1—Zn1—Cl2	111.04 (8)
O1—Zn1—Cl1	109.48 (8)
N1—Zn1—Cl1	109.22 (8)
Cl2—Zn1—Cl1	115.66 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O2	0.90 (4)	1.81 (4)	2.712 (3)	177 (4)
O2—H2B⋯O1i	0.84 (3)	1.91 (3)	2.741 (3)	168 (4)
O2—H2A⋯Cl1ii	0.85 (3)	2.44 (3)	3.272 (3)	168 (4)

Symmetry codes: (i) ; (ii) .