Dichlorido[2-({[3-(cyclo-hexyl-aza-nium-yl)prop-yl]imino}-meth-yl)-5-meth-oxy-phenolate]zinc.

The title mononuclear zinc complex, [ZnCl(2)(C(17)H(26)N(2)O(2))], was obtained by the reaction of 2-hy-droxy-4-meth-oxy-benzaldehyde, N-cyclo-hexyl-propane-1,3-diamine and zinc chloride in methanol. The Zn(II) atom is four-coordinated by the phenolate O atom and imine N atom of the bidentate zwitterionic Schiff base ligand 2-{[3-(cyclo-hexyl-amino)-prop-yl]imino-meth-yl}-5-meth-oxy-phenol, and by two chloride ions, generating a distorted ZnONCl(2) tetra-hedral geometry. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains along the c-axis direction.

Related literature

For the Schiff base complexes we reported previously, see: Wang (2009 ▶); Wang & Ye (2011 ▶). For similar zinc complexes, see: Zhu (2008 ▶); Wang (2007 ▶); Ikmal Hisham et al. (2011 ▶); Datta et al. (2009 ▶).

Experimental

Crystal data

[ZnCl2(C17H26N2O2)]

M = 426.67

Monoclinic,

a = 25.118 (2) Å

b = 10.543 (1) Å

c = 14.992 (2) Å

β = 91.435 (1)°

V = 3968.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 1.52 mm−1

T = 298 K

0.33 × 0.30 × 0.29 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.634, T max = 0.667

10824 measured reflections

4104 independent reflections

3101 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.03

4104 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027085/hb5943sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027085/hb5943Isup2.hkl

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

[ZnCl2(C17H26N2O2)]	F(000) = 1776
Mr = 426.67	Dx = 1.428 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.118 (2) Å	Cell parameters from 3616 reflections
b = 10.543 (1) Å	θ = 2.5–26.9°
c = 14.992 (2) Å	µ = 1.52 mm−1
β = 91.435 (1)°	T = 298 K
V = 3968.9 (7) Å3	Block, colorless
Z = 8	0.33 × 0.30 × 0.29 mm

Bruker SMART CCD diffractometer	4104 independent reflections
Radiation source: fine-focus sealed tube	3101 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→30
Tmin = 0.634, Tmax = 0.667	k = −8→13
10824 measured reflections	l = −18→18

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0333P)2 + 1.6888P] where P = (Fo2 + 2Fc2)/3
4104 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 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
Zn1	0.159066 (10)	0.50173 (2)	0.107303 (15)	0.04105 (9)
Cl1	0.08297 (2)	0.50677 (5)	0.18660 (4)	0.04897 (14)
Cl2	0.19579 (3)	0.68984 (6)	0.08640 (4)	0.06432 (18)
N1	0.20745 (6)	0.36504 (17)	0.15451 (10)	0.0402 (4)
N2	0.11696 (6)	0.38198 (15)	0.37490 (10)	0.0352 (4)
H2A	0.0999	0.4227	0.3298	0.042*
H2B	0.1262	0.4405	0.4162	0.042*
O1	0.14586 (6)	0.42308 (13)	−0.00928 (8)	0.0435 (3)
O2	0.12094 (6)	0.07054 (15)	−0.20497 (11)	0.0587 (4)
C1	0.15368 (7)	0.30174 (18)	−0.02645 (12)	0.0344 (4)
C2	0.13357 (7)	0.25212 (19)	−0.10742 (13)	0.0381 (5)
H2	0.1160	0.3056	−0.1477	0.046*
C3	0.13941 (8)	0.1257 (2)	−0.12835 (14)	0.0429 (5)
C4	0.16610 (10)	0.0448 (2)	−0.06927 (17)	0.0562 (6)
H4	0.1695	−0.0409	−0.0826	0.067*
C5	0.18707 (9)	0.0919 (2)	0.00792 (16)	0.0553 (6)
H5	0.2055	0.0371	0.0462	0.066*
C6	0.18229 (8)	0.2201 (2)	0.03293 (13)	0.0399 (5)
C7	0.09238 (12)	0.1469 (3)	−0.26836 (17)	0.0747 (8)
H7A	0.0606	0.1786	−0.2421	0.112*
H7B	0.0831	0.0968	−0.3199	0.112*
H7C	0.1143	0.2169	−0.2858	0.112*
C8	0.20912 (8)	0.2578 (2)	0.11472 (14)	0.0443 (5)
H8	0.2304	0.1963	0.1422	0.053*
C9	0.23994 (8)	0.3838 (2)	0.23653 (13)	0.0476 (5)
H9A	0.2670	0.4472	0.2260	0.057*
H9B	0.2577	0.3050	0.2525	0.057*
C10	0.20563 (8)	0.4261 (2)	0.31269 (13)	0.0431 (5)
H10A	0.1861	0.5017	0.2948	0.052*
H10B	0.2284	0.4479	0.3636	0.052*
C11	0.16647 (8)	0.3247 (2)	0.34013 (14)	0.0416 (5)
H11A	0.1576	0.2716	0.2891	0.050*
H11B	0.1829	0.2715	0.3858	0.050*
C12	0.07854 (7)	0.29055 (19)	0.41592 (13)	0.0377 (4)
H12	0.0977	0.2403	0.4615	0.045*
C13	0.05542 (8)	0.2016 (2)	0.34577 (15)	0.0494 (5)
H13A	0.0838	0.1523	0.3201	0.059*
H13B	0.0383	0.2506	0.2983	0.059*
C14	0.01487 (10)	0.1127 (2)	0.38684 (19)	0.0663 (7)
H14A	−0.0010	0.0598	0.3404	0.080*
H14B	0.0329	0.0575	0.4297	0.080*
C15	−0.02850 (9)	0.1850 (2)	0.43294 (18)	0.0616 (7)
H15A	−0.0520	0.1258	0.4619	0.074*
H15B	−0.0494	0.2324	0.3890	0.074*
C16	−0.00489 (9)	0.2753 (3)	0.50150 (17)	0.0676 (8)
H16A	0.0127	0.2271	0.5488	0.081*
H16B	−0.0332	0.3243	0.5276	0.081*
C17	0.03513 (8)	0.3651 (2)	0.46006 (15)	0.0511 (6)
H17A	0.0171	0.4186	0.4162	0.061*
H17B	0.0507	0.4194	0.5060	0.061*

	U11	U22	U33	U12	U13	U23
Zn1	0.04827 (15)	0.04339 (15)	0.03132 (13)	0.00342 (11)	−0.00238 (10)	−0.00043 (10)
Cl1	0.0447 (3)	0.0621 (4)	0.0400 (3)	0.0052 (3)	−0.0005 (2)	0.0051 (3)
Cl2	0.0750 (4)	0.0583 (4)	0.0596 (4)	−0.0202 (3)	0.0004 (3)	−0.0009 (3)
N1	0.0339 (9)	0.0555 (11)	0.0311 (9)	0.0034 (8)	0.0014 (7)	0.0037 (8)
N2	0.0375 (9)	0.0386 (9)	0.0292 (8)	−0.0036 (7)	−0.0023 (7)	−0.0006 (7)
O1	0.0626 (9)	0.0365 (8)	0.0311 (7)	0.0094 (7)	−0.0061 (6)	−0.0007 (6)
O2	0.0749 (11)	0.0453 (9)	0.0555 (10)	−0.0138 (8)	−0.0046 (8)	−0.0102 (8)
C1	0.0317 (10)	0.0370 (11)	0.0348 (10)	0.0020 (8)	0.0068 (8)	0.0028 (8)
C2	0.0362 (10)	0.0412 (11)	0.0371 (11)	−0.0016 (9)	0.0029 (8)	0.0010 (9)
C3	0.0406 (11)	0.0427 (12)	0.0456 (12)	−0.0061 (10)	0.0064 (9)	−0.0047 (10)
C4	0.0659 (15)	0.0373 (12)	0.0655 (16)	0.0064 (11)	−0.0001 (13)	−0.0046 (12)
C5	0.0576 (14)	0.0468 (14)	0.0611 (15)	0.0142 (11)	−0.0058 (12)	0.0048 (12)
C6	0.0345 (10)	0.0442 (12)	0.0411 (11)	0.0065 (9)	0.0006 (9)	0.0017 (9)
C7	0.098 (2)	0.0668 (17)	0.0577 (16)	−0.0215 (16)	−0.0208 (15)	−0.0052 (14)
C8	0.0368 (11)	0.0531 (14)	0.0432 (12)	0.0113 (10)	0.0016 (9)	0.0088 (11)
C9	0.0319 (11)	0.0718 (16)	0.0389 (11)	−0.0018 (10)	−0.0018 (9)	0.0049 (11)
C10	0.0385 (11)	0.0552 (13)	0.0353 (11)	−0.0071 (10)	−0.0018 (9)	−0.0021 (10)
C11	0.0406 (11)	0.0445 (12)	0.0401 (11)	0.0029 (9)	0.0071 (9)	−0.0012 (9)
C12	0.0353 (10)	0.0423 (11)	0.0354 (10)	−0.0025 (9)	−0.0010 (8)	0.0064 (9)
C13	0.0473 (12)	0.0404 (12)	0.0607 (14)	−0.0069 (10)	0.0071 (11)	−0.0095 (11)
C14	0.0581 (15)	0.0444 (14)	0.097 (2)	−0.0137 (12)	0.0108 (14)	0.0005 (14)
C15	0.0444 (13)	0.0591 (15)	0.0817 (18)	−0.0114 (12)	0.0087 (12)	0.0103 (14)
C16	0.0505 (14)	0.089 (2)	0.0642 (16)	−0.0095 (13)	0.0186 (12)	−0.0027 (14)
C17	0.0425 (12)	0.0611 (15)	0.0501 (13)	−0.0067 (11)	0.0076 (10)	−0.0128 (11)

Zn1—O1	1.9554 (13)	C8—H8	0.9300
Zn1—N1	2.0029 (17)	C9—C10	1.515 (3)
Zn1—Cl2	2.2129 (8)	C9—H9A	0.9700
Zn1—Cl1	2.2767 (7)	C9—H9B	0.9700
N1—C8	1.279 (3)	C10—C11	1.516 (3)
N1—C9	1.472 (2)	C10—H10A	0.9700
N2—C11	1.488 (2)	C10—H10B	0.9700
N2—C12	1.506 (2)	C11—H11A	0.9700
N2—H2A	0.9000	C11—H11B	0.9700
N2—H2B	0.9000	C12—C17	1.510 (3)
O1—C1	1.320 (2)	C12—C13	1.514 (3)
O2—C3	1.359 (2)	C12—H12	0.9800
O2—C7	1.426 (3)	C13—C14	1.526 (3)
C1—C2	1.404 (3)	C13—H13A	0.9700
C1—C6	1.421 (3)	C13—H13B	0.9700
C2—C3	1.378 (3)	C14—C15	1.511 (3)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.390 (3)	C14—H14B	0.9700
C4—C5	1.354 (3)	C15—C16	1.511 (3)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.408 (3)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.525 (3)
C6—C8	1.440 (3)	C16—H16A	0.9700
C7—H7A	0.9600	C16—H16B	0.9700
C7—H7B	0.9600	C17—H17A	0.9700
C7—H7C	0.9600	C17—H17B	0.9700
O1—Zn1—N1	95.66 (6)	H9A—C9—H9B	108.1
O1—Zn1—Cl2	108.39 (5)	C9—C10—C11	112.44 (18)
N1—Zn1—Cl2	116.33 (5)	C9—C10—H10A	109.1
O1—Zn1—Cl1	110.54 (5)	C11—C10—H10A	109.1
N1—Zn1—Cl1	110.01 (5)	C9—C10—H10B	109.1
Cl2—Zn1—Cl1	114.29 (3)	C11—C10—H10B	109.1
C8—N1—C9	118.95 (18)	H10A—C10—H10B	107.8
C8—N1—Zn1	119.85 (14)	N2—C11—C10	111.25 (17)
C9—N1—Zn1	121.17 (14)	N2—C11—H11A	109.4
C11—N2—C12	115.66 (16)	C10—C11—H11A	109.4
C11—N2—H2A	108.4	N2—C11—H11B	109.4
C12—N2—H2A	108.4	C10—C11—H11B	109.4
C11—N2—H2B	108.4	H11A—C11—H11B	108.0
C12—N2—H2B	108.4	N2—C12—C17	108.84 (17)
H2A—N2—H2B	107.4	N2—C12—C13	110.56 (16)
C1—O1—Zn1	124.22 (12)	C17—C12—C13	110.99 (16)
C3—O2—C7	118.51 (18)	N2—C12—H12	108.8
O1—C1—C2	118.52 (17)	C17—C12—H12	108.8
O1—C1—C6	122.71 (17)	C13—C12—H12	108.8
C2—C1—C6	118.77 (18)	C12—C13—C14	110.40 (19)
C3—C2—C1	121.28 (19)	C12—C13—H13A	109.6
C3—C2—H2	119.4	C14—C13—H13A	109.6
C1—C2—H2	119.4	C12—C13—H13B	109.6
O2—C3—C2	124.8 (2)	C14—C13—H13B	109.6
O2—C3—C4	115.2 (2)	H13A—C13—H13B	108.1
C2—C3—C4	120.1 (2)	C15—C14—C13	111.7 (2)
C5—C4—C3	119.4 (2)	C15—C14—H14A	109.3
C5—C4—H4	120.3	C13—C14—H14A	109.3
C3—C4—H4	120.3	C15—C14—H14B	109.3
C4—C5—C6	123.1 (2)	C13—C14—H14B	109.3
C4—C5—H5	118.5	H14A—C14—H14B	107.9
C6—C5—H5	118.5	C14—C15—C16	110.7 (2)
C5—C6—C1	117.37 (19)	C14—C15—H15A	109.5
C5—C6—C8	116.79 (19)	C16—C15—H15A	109.5
C1—C6—C8	125.77 (19)	C14—C15—H15B	109.5
O2—C7—H7A	109.5	C16—C15—H15B	109.5
O2—C7—H7B	109.5	H15A—C15—H15B	108.1
H7A—C7—H7B	109.5	C15—C16—C17	111.4 (2)
O2—C7—H7C	109.5	C15—C16—H16A	109.3
H7A—C7—H7C	109.5	C17—C16—H16A	109.3
H7B—C7—H7C	109.5	C15—C16—H16B	109.3
N1—C8—C6	128.39 (19)	C17—C16—H16B	109.3
N1—C8—H8	115.8	H16A—C16—H16B	108.0
C6—C8—H8	115.8	C12—C17—C16	110.3 (2)
N1—C9—C10	110.81 (16)	C12—C17—H17A	109.6
N1—C9—H9A	109.5	C16—C17—H17A	109.6
C10—C9—H9A	109.5	C12—C17—H17B	109.6
N1—C9—H9B	109.5	C16—C17—H17B	109.6
C10—C9—H9B	109.5	H17A—C17—H17B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1	0.90	2.35	3.2106 (17)	160
N2—H2B···O1i	0.90	1.88	2.776 (2)	173

Table 1

Selected bond lengths (Å)

Zn1—O1	1.9554 (13)
Zn1—N1	2.0029 (17)
Zn1—Cl2	2.2129 (8)
Zn1—Cl1	2.2767 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1	0.90	2.35	3.2106 (17)	160
N2—H2B⋯O1i	0.90	1.88	2.776 (2)	173

Symmetry code: (i) .