Dichlorido{2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}zinc(II).

In the title compound, [ZnCl(2)(C(13)H(19)N(3)O)], the Schiff base ligand acts as an N,N',N''-tridentate chelating agent, making two five-membered rings with the Zn(II) ion. The metal atom is five-coordinated by the Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry. An intra-molecular C-H⋯Cl inter-action occurs. In the crystal, adjacent mol-ecules are linked together via C-H⋯Cl hydrogen-bonding and long range C-H⋯O and C-H⋯Cl inter-actions into a three-dimensional network.

Related literature

For the crystal structure of an analogous CdII complex, see: Ikmal Hisham et al. (2010 ▶). For crystal structures of similar ZnII complexes, see: Chattopadhyay et al. (2009 ▶); Sun (2005 ▶).

Experimental

Crystal data

[ZnCl2(C13H19N3O)]

M = 369.58

Monoclinic,

a = 9.5737 (12) Å

b = 13.7064 (17) Å

c = 12.0766 (15) Å

β = 106.643 (2)°

V = 1518.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.97 mm−1

T = 100 K

0.35 × 0.21 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.546, T max = 0.908

13693 measured reflections

2979 independent reflections

2552 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.08

2979 reflections

182 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.39 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050671/pv2366sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050671/pv2366Isup2.hkl

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

[ZnCl2(C13H19N3O)]	F(000) = 760
Mr = 369.58	Dx = 1.617 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3471 reflections
a = 9.5737 (12) Å	θ = 2.3–27.5°
b = 13.7064 (17) Å	µ = 1.97 mm−1
c = 12.0766 (15) Å	T = 100 K
β = 106.643 (2)°	Plate, yellow
V = 1518.3 (3) Å3	0.35 × 0.21 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	2979 independent reflections
Radiation source: fine-focus sealed tube	2552 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.546, Tmax = 0.908	k = −16→16
13693 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.4492P] where P = (Fo2 + 2Fc2)/3
2979 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 1.03 e Å−3
0 restraints	Δρmin = −0.39 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
Zn1	0.72733 (3)	0.08854 (2)	0.16005 (3)	0.01368 (12)
Cl1	0.95230 (7)	0.13655 (5)	0.26836 (6)	0.01677 (16)
Cl2	0.54542 (7)	0.19943 (5)	0.13205 (6)	0.01828 (17)
O1	0.6851 (2)	0.06197 (15)	0.51473 (16)	0.0224 (4)
N1	0.7630 (2)	0.11923 (16)	−0.01195 (19)	0.0156 (5)
N2	0.7468 (2)	−0.04614 (15)	0.08710 (18)	0.0145 (5)
N3	0.6560 (2)	−0.01499 (15)	0.28543 (18)	0.0146 (5)
C1	0.7536 (3)	0.20493 (19)	−0.0655 (2)	0.0183 (6)
H1	0.7219	0.2601	−0.0317	0.022*
C2	0.7881 (3)	0.2169 (2)	−0.1689 (2)	0.0208 (6)
H2	0.7788	0.2788	−0.2057	0.025*
C3	0.8363 (3)	0.1366 (2)	−0.2170 (2)	0.0191 (6)
H3	0.8633	0.1430	−0.2865	0.023*
C4	0.8449 (3)	0.0468 (2)	−0.1625 (2)	0.0172 (6)
H4	0.8764	−0.0095	−0.1946	0.021*
C5	0.8064 (3)	0.04073 (18)	−0.0604 (2)	0.0147 (6)
C6	0.7974 (3)	−0.05297 (19)	0.0006 (2)	0.0148 (6)
C7	0.8414 (3)	−0.14742 (19)	−0.0420 (2)	0.0178 (6)
H7A	0.8954	−0.1870	0.0240	0.027*
H7B	0.9034	−0.1342	−0.0922	0.027*
H7C	0.7541	−0.1829	−0.0856	0.027*
C8	0.7172 (3)	−0.13162 (19)	0.1493 (2)	0.0186 (6)
H8A	0.8078	−0.1542	0.2064	0.022*
H8B	0.6782	−0.1856	0.0947	0.022*
C9	0.6064 (3)	−0.10075 (19)	0.2097 (2)	0.0184 (6)
H9A	0.5134	−0.0847	0.1511	0.022*
H9B	0.5879	−0.1558	0.2567	0.022*
C10	0.5308 (3)	0.0196 (2)	0.3241 (2)	0.0181 (6)
H10A	0.4885	−0.0360	0.3557	0.022*
H10B	0.4546	0.0459	0.2570	0.022*
C11	0.5765 (3)	0.0979 (2)	0.4155 (2)	0.0217 (6)
H11A	0.6157	0.1546	0.3833	0.026*
H11B	0.4905	0.1200	0.4386	0.026*
C12	0.8104 (3)	0.0335 (2)	0.4810 (2)	0.0208 (6)
H12A	0.8865	0.0092	0.5495	0.025*
H12B	0.8501	0.0910	0.4507	0.025*
C13	0.7736 (3)	−0.0452 (2)	0.3896 (2)	0.0197 (6)
H13A	0.8621	−0.0616	0.3666	0.024*
H13B	0.7425	−0.1046	0.4226	0.024*

	U11	U22	U33	U12	U13	U23
Zn1	0.01259 (19)	0.01472 (18)	0.01459 (18)	−0.00019 (11)	0.00529 (13)	−0.00150 (11)
Cl1	0.0128 (3)	0.0199 (3)	0.0179 (3)	−0.0021 (2)	0.0048 (3)	−0.0023 (2)
Cl2	0.0152 (3)	0.0206 (3)	0.0194 (3)	0.0037 (3)	0.0056 (3)	0.0007 (2)
O1	0.0203 (11)	0.0347 (11)	0.0144 (10)	0.0023 (9)	0.0085 (9)	0.0005 (8)
N1	0.0126 (12)	0.0185 (11)	0.0154 (11)	−0.0004 (9)	0.0037 (9)	0.0002 (9)
N2	0.0138 (12)	0.0159 (11)	0.0133 (11)	−0.0016 (9)	0.0030 (9)	−0.0005 (9)
N3	0.0142 (12)	0.0156 (11)	0.0145 (11)	−0.0015 (9)	0.0051 (9)	−0.0004 (9)
C1	0.0172 (14)	0.0179 (13)	0.0186 (14)	−0.0009 (11)	0.0033 (12)	−0.0023 (10)
C2	0.0228 (16)	0.0228 (14)	0.0146 (13)	−0.0042 (12)	0.0019 (12)	0.0021 (10)
C3	0.0148 (14)	0.0292 (15)	0.0135 (13)	−0.0032 (12)	0.0044 (11)	−0.0010 (11)
C4	0.0108 (14)	0.0222 (14)	0.0186 (14)	−0.0002 (11)	0.0044 (11)	−0.0034 (11)
C5	0.0119 (13)	0.0168 (13)	0.0137 (13)	−0.0013 (10)	0.0010 (11)	−0.0018 (10)
C6	0.0099 (13)	0.0187 (13)	0.0139 (13)	−0.0015 (10)	0.0005 (11)	−0.0010 (10)
C7	0.0171 (14)	0.0179 (13)	0.0201 (14)	−0.0003 (11)	0.0081 (12)	−0.0026 (10)
C8	0.0248 (16)	0.0147 (13)	0.0174 (14)	−0.0013 (11)	0.0077 (12)	0.0003 (10)
C9	0.0171 (15)	0.0190 (13)	0.0203 (14)	−0.0056 (11)	0.0070 (12)	−0.0013 (11)
C10	0.0110 (14)	0.0257 (15)	0.0190 (14)	−0.0028 (11)	0.0065 (11)	0.0018 (11)
C11	0.0212 (16)	0.0268 (15)	0.0196 (15)	0.0055 (12)	0.0099 (13)	0.0007 (11)
C12	0.0113 (14)	0.0355 (16)	0.0149 (13)	−0.0003 (12)	0.0028 (11)	0.0017 (12)
C13	0.0166 (15)	0.0231 (14)	0.0194 (14)	0.0026 (11)	0.0052 (12)	0.0039 (11)

Zn1—N2	2.077 (2)	C4—H4	0.9500
Zn1—N1	2.239 (2)	C5—C6	1.495 (4)
Zn1—Cl2	2.2628 (7)	C6—C7	1.497 (4)
Zn1—Cl1	2.2736 (7)	C7—H7A	0.9800
Zn1—N3	2.316 (2)	C7—H7B	0.9800
O1—C12	1.427 (3)	C7—H7C	0.9800
O1—C11	1.430 (3)	C8—C9	1.510 (4)
N1—C1	1.331 (3)	C8—H8A	0.9900
N1—C5	1.346 (3)	C8—H8B	0.9900
N2—C6	1.274 (3)	C9—H9A	0.9900
N2—C8	1.463 (3)	C9—H9B	0.9900
N3—C9	1.482 (3)	C10—C11	1.511 (4)
N3—C10	1.484 (3)	C10—H10A	0.9900
N3—C13	1.487 (3)	C10—H10B	0.9900
C1—C2	1.390 (4)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.384 (4)	C12—C13	1.511 (4)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.387 (4)	C12—H12B	0.9900
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.387 (4)	C13—H13B	0.9900
N2—Zn1—N1	73.58 (8)	C6—C7—H7B	109.5
N2—Zn1—Cl2	133.83 (6)	H7A—C7—H7B	109.5
N1—Zn1—Cl2	92.90 (6)	C6—C7—H7C	109.5
N2—Zn1—Cl1	108.41 (6)	H7A—C7—H7C	109.5
N1—Zn1—Cl1	96.22 (6)	H7B—C7—H7C	109.5
Cl2—Zn1—Cl1	116.95 (3)	N2—C8—C9	106.9 (2)
N2—Zn1—N3	79.16 (8)	N2—C8—H8A	110.4
N1—Zn1—N3	150.85 (8)	C9—C8—H8A	110.4
Cl2—Zn1—N3	98.68 (6)	N2—C8—H8B	110.4
Cl1—Zn1—N3	102.08 (6)	C9—C8—H8B	110.4
C12—O1—C11	108.9 (2)	H8A—C8—H8B	108.6
C1—N1—C5	118.7 (2)	N3—C9—C8	112.0 (2)
C1—N1—Zn1	127.53 (19)	N3—C9—H9A	109.2
C5—N1—Zn1	113.63 (17)	C8—C9—H9A	109.2
C6—N2—C8	122.5 (2)	N3—C9—H9B	109.2
C6—N2—Zn1	120.96 (18)	C8—C9—H9B	109.2
C8—N2—Zn1	116.09 (17)	H9A—C9—H9B	107.9
C9—N3—C10	107.6 (2)	N3—C10—C11	111.5 (2)
C9—N3—C13	109.5 (2)	N3—C10—H10A	109.3
C10—N3—C13	107.9 (2)	C11—C10—H10A	109.3
C9—N3—Zn1	100.66 (15)	N3—C10—H10B	109.3
C10—N3—Zn1	115.21 (16)	C11—C10—H10B	109.3
C13—N3—Zn1	115.49 (16)	H10A—C10—H10B	108.0
N1—C1—C2	122.7 (3)	O1—C11—C10	110.9 (2)
N1—C1—H1	118.7	O1—C11—H11A	109.5
C2—C1—H1	118.7	C10—C11—H11A	109.5
C3—C2—C1	118.5 (3)	O1—C11—H11B	109.5
C3—C2—H2	120.8	C10—C11—H11B	109.5
C1—C2—H2	120.8	H11A—C11—H11B	108.1
C2—C3—C4	119.2 (3)	O1—C12—C13	111.4 (2)
C2—C3—H3	120.4	O1—C12—H12A	109.4
C4—C3—H3	120.4	C13—C12—H12A	109.4
C3—C4—C5	118.7 (3)	O1—C12—H12B	109.4
C3—C4—H4	120.6	C13—C12—H12B	109.4
C5—C4—H4	120.6	H12A—C12—H12B	108.0
N1—C5—C4	122.1 (2)	N3—C13—C12	112.4 (2)
N1—C5—C6	113.8 (2)	N3—C13—H13A	109.1
C4—C5—C6	123.9 (2)	C12—C13—H13A	109.1
N2—C6—C5	115.5 (2)	N3—C13—H13B	109.1
N2—C6—C7	123.8 (2)	C12—C13—H13B	109.1
C5—C6—C7	120.8 (2)	H13A—C13—H13B	107.9
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cl1i	0.95	2.71	3.625 (3)	161
C7—H7C···Cl2ii	0.98	2.77	3.619 (3)	146
C12—H12B···Cl1	0.99	2.73	3.526 (3)	138
C10—H10A···O1iii	0.99	2.61	3.408 (3)	137
C9—H9B···Cl1iv	0.99	2.88	3.665 (3)	137
C7—H7B···Cl1i	0.98	2.85	3.807 (3)	166
C8—H8A···Cl2iv	0.99	2.87	3.750 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cl1i	0.95	2.71	3.625 (3)	161
C7—H7C⋯Cl2ii	0.98	2.77	3.619 (3)	146
C12—H12B⋯Cl1	0.99	2.73	3.526 (3)	138
C10—H10A⋯O1iii	0.99	2.61	3.408 (3)	137
C9—H9B⋯Cl1iv	0.99	2.88	3.665 (3)	137
C7—H7B⋯Cl1i	0.98	2.85	3.807 (3)	166
C8—H8A⋯Cl2iv	0.99	2.87	3.750 (3)	149

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