Diiodido{2-(morpholin-4-yl)-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}zinc.

In the title compound, [ZnI(2)(C(13)H(19)N(3)O)], the Zn(II) ion is five-coordinated in a distorted square-pyramidal geometry, in which the basal plane is defined by three N atoms from the Schiff base ligand and one iodide ion. A second iodide ligand, situated in the apical position, completes the coordination geometry. In the crystal structure, C-H⋯O hydrogen bonds link a pair of mol-ecules around an inversion centre into a dimer.

Related literature

For the structure of an analogous ZnCl2 complex, see: Ikmal Hisham et al. (2011 ▶). For square-pyramidal ZnI2 complexes with N,N′,N′′-tridentate ligands, see: Drew & Hollis (1978 ▶); Yousefi (2010 ▶). For a description of the geometry of complexes with five-coordinated metal ions, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[ZnI2(C13H19N3O)]

M = 552.48

Triclinic,

a = 8.8874 (3) Å

b = 10.3117 (4) Å

c = 10.3643 (4) Å

α = 68.8810 (18)°

β = 81.959 (2)°

γ = 66.3990 (17)°

V = 811.91 (6) Å3

Z = 2

Mo Kα radiation

μ = 5.31 mm−1

T = 100 K

0.17 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.465, T max = 0.646

7292 measured reflections

3517 independent reflections

3260 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.045

S = 1.05

3517 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −1.23 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/S1600536811014656/hy2422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014656/hy2422Isup2.hkl

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

[ZnI2(C13H19N3O)]	Z = 2
Mr = 552.48	F(000) = 524
Triclinic, P1	Dx = 2.260 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8874 (3) Å	Cell parameters from 6030 reflections
b = 10.3117 (4) Å	θ = 2.3–30.4°
c = 10.3643 (4) Å	µ = 5.31 mm−1
α = 68.8810 (18)°	T = 100 K
β = 81.959 (2)°	Block, brown
γ = 66.3990 (17)°	0.17 × 0.13 × 0.09 mm
V = 811.91 (6) Å3

Bruker APEXII CCD diffractometer	3517 independent reflections
Radiation source: fine-focus sealed tube	3260 reflections with I > 2σ(I)
graphite	Rint = 0.013
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.465, Tmax = 0.646	k = −13→13
7292 measured reflections	l = −13→13

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0197P)2 + 1.3278P] where P = (Fo2 + 2Fc2)/3
3517 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −1.23 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.77476 (4)	0.81170 (3)	0.66161 (3)	0.01267 (7)
I1	0.64389 (2)	1.103488 (18)	0.584395 (17)	0.01508 (5)
I2	1.05998 (2)	0.694938 (19)	0.791314 (17)	0.01566 (5)
O1	0.3717 (2)	0.8562 (2)	1.0506 (2)	0.0212 (4)
N1	0.8699 (3)	0.8016 (2)	0.4558 (2)	0.0135 (4)
N2	0.7235 (3)	0.6403 (2)	0.6380 (2)	0.0137 (4)
N3	0.6122 (3)	0.7619 (2)	0.8469 (2)	0.0137 (4)
C1	0.9527 (3)	0.8810 (3)	0.3702 (3)	0.0161 (5)
H1	0.9697	0.9537	0.3959	0.019*
C2	1.0153 (3)	0.8615 (3)	0.2446 (3)	0.0181 (5)
H2	1.0767	0.9176	0.1868	0.022*
C3	0.9859 (3)	0.7587 (3)	0.2062 (3)	0.0190 (6)
H3	1.0239	0.7455	0.1197	0.023*
C4	0.9002 (3)	0.6744 (3)	0.2951 (3)	0.0165 (5)
H4	0.8797	0.6024	0.2709	0.020*
C5	0.8456 (3)	0.6981 (3)	0.4199 (3)	0.0145 (5)
C6	0.7574 (3)	0.6108 (3)	0.5253 (3)	0.0139 (5)
C7	0.7137 (3)	0.5006 (3)	0.4920 (3)	0.0181 (5)
H7A	0.6732	0.4412	0.5754	0.027*
H7B	0.8112	0.4336	0.4582	0.027*
H7C	0.6280	0.5547	0.4204	0.027*
C8	0.6366 (3)	0.5663 (3)	0.7513 (3)	0.0161 (5)
H8A	0.6837	0.4566	0.7693	0.019*
H8B	0.5189	0.6052	0.7275	0.019*
C9	0.6557 (3)	0.5993 (3)	0.8785 (3)	0.0150 (5)
H9A	0.5839	0.5643	0.9531	0.018*
H9B	0.7707	0.5435	0.9119	0.018*
C10	0.4339 (3)	0.8512 (3)	0.8159 (3)	0.0157 (5)
H10A	0.4008	0.8254	0.7440	0.019*
H10B	0.4152	0.9594	0.7782	0.019*
C11	0.3273 (3)	0.8231 (3)	0.9429 (3)	0.0177 (5)
H11A	0.2107	0.8864	0.9174	0.021*
H11B	0.3391	0.7166	0.9766	0.021*
C12	0.5400 (3)	0.7684 (3)	1.0885 (3)	0.0188 (6)
H12A	0.5561	0.6608	1.1276	0.023*
H12B	0.5690	0.7960	1.1610	0.023*
C13	0.6531 (3)	0.7918 (3)	0.9652 (3)	0.0168 (5)
H13A	0.6466	0.8967	0.9338	0.020*
H13B	0.7676	0.7247	0.9950	0.020*

	U11	U22	U33	U12	U13	U23
Zn1	0.01377 (14)	0.01207 (14)	0.01168 (14)	−0.00432 (11)	0.00086 (11)	−0.00440 (11)
I1	0.01607 (9)	0.01218 (8)	0.01448 (9)	−0.00349 (6)	0.00078 (6)	−0.00401 (6)
I2	0.01406 (9)	0.01676 (9)	0.01511 (9)	−0.00421 (7)	−0.00121 (6)	−0.00553 (7)
O1	0.0184 (10)	0.0264 (11)	0.0200 (10)	−0.0062 (8)	0.0039 (8)	−0.0130 (9)
N1	0.0131 (10)	0.0134 (10)	0.0120 (10)	−0.0034 (8)	0.0003 (8)	−0.0039 (8)
N2	0.0130 (10)	0.0110 (10)	0.0147 (11)	−0.0028 (8)	−0.0011 (8)	−0.0033 (8)
N3	0.0150 (11)	0.0130 (10)	0.0116 (10)	−0.0047 (9)	0.0001 (8)	−0.0032 (8)
C1	0.0148 (12)	0.0163 (12)	0.0164 (13)	−0.0051 (10)	−0.0007 (10)	−0.0051 (10)
C2	0.0142 (12)	0.0194 (13)	0.0178 (13)	−0.0053 (11)	0.0010 (10)	−0.0047 (11)
C3	0.0171 (13)	0.0214 (14)	0.0138 (13)	−0.0024 (11)	0.0017 (10)	−0.0067 (11)
C4	0.0153 (13)	0.0178 (13)	0.0160 (13)	−0.0034 (10)	−0.0007 (10)	−0.0084 (11)
C5	0.0108 (12)	0.0140 (12)	0.0160 (13)	−0.0014 (10)	−0.0011 (9)	−0.0053 (10)
C6	0.0116 (12)	0.0123 (12)	0.0159 (13)	−0.0012 (10)	−0.0012 (9)	−0.0057 (10)
C7	0.0187 (13)	0.0189 (13)	0.0185 (14)	−0.0070 (11)	0.0010 (10)	−0.0085 (11)
C8	0.0176 (13)	0.0155 (12)	0.0165 (13)	−0.0077 (10)	0.0038 (10)	−0.0064 (10)
C9	0.0167 (13)	0.0123 (12)	0.0135 (13)	−0.0048 (10)	0.0009 (10)	−0.0028 (10)
C10	0.0145 (12)	0.0169 (12)	0.0148 (13)	−0.0042 (10)	0.0003 (10)	−0.0061 (10)
C11	0.0151 (13)	0.0192 (13)	0.0186 (14)	−0.0055 (11)	0.0020 (10)	−0.0079 (11)
C12	0.0183 (13)	0.0256 (14)	0.0123 (13)	−0.0071 (11)	0.0008 (10)	−0.0076 (11)
C13	0.0181 (13)	0.0197 (13)	0.0124 (13)	−0.0064 (11)	0.0018 (10)	−0.0067 (10)

Zn1—N1	2.205 (2)	C4—H4	0.9500
Zn1—N2	2.093 (2)	C5—C6	1.495 (4)
Zn1—N3	2.269 (2)	C6—C7	1.495 (4)
Zn1—I1	2.6018 (4)	C7—H7A	0.9800
Zn1—I2	2.6506 (4)	C7—H7B	0.9800
O1—C11	1.423 (3)	C7—H7C	0.9800
O1—C12	1.426 (3)	C8—C9	1.521 (4)
N1—C1	1.332 (3)	C8—H8A	0.9900
N1—C5	1.349 (3)	C8—H8B	0.9900
N2—C6	1.277 (3)	C9—H9A	0.9900
N2—C8	1.459 (3)	C9—H9B	0.9900
N3—C9	1.479 (3)	C10—C11	1.521 (4)
N3—C13	1.490 (3)	C10—H10A	0.9900
N3—C10	1.491 (3)	C10—H10B	0.9900
C1—C2	1.394 (4)	C11—H11A	0.9900
C1—H1	0.9500	C11—H11B	0.9900
C2—C3	1.380 (4)	C12—C13	1.521 (4)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.394 (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	74.71 (8)	C6—C7—H7B	109.5
N2—Zn1—N3	78.31 (8)	H7A—C7—H7B	109.5
N1—Zn1—N3	151.54 (8)	C6—C7—H7C	109.5
N2—Zn1—I1	137.01 (6)	H7A—C7—H7C	109.5
N1—Zn1—I1	95.53 (6)	H7B—C7—H7C	109.5
N3—Zn1—I1	98.03 (6)	N2—C8—C9	107.5 (2)
N2—Zn1—I2	109.52 (6)	N2—C8—H8A	110.2
N1—Zn1—I2	98.21 (6)	C9—C8—H8A	110.2
N3—Zn1—I2	99.18 (6)	N2—C8—H8B	110.2
I1—Zn1—I2	113.325 (12)	C9—C8—H8B	110.2
C11—O1—C12	110.8 (2)	H8A—C8—H8B	108.5
C1—N1—C5	118.9 (2)	N3—C9—C8	111.1 (2)
C1—N1—Zn1	126.70 (18)	N3—C9—H9A	109.4
C5—N1—Zn1	114.34 (17)	C8—C9—H9A	109.4
C6—N2—C8	122.6 (2)	N3—C9—H9B	109.4
C6—N2—Zn1	120.65 (18)	C8—C9—H9B	109.4
C8—N2—Zn1	116.61 (16)	H9A—C9—H9B	108.0
C9—N3—C13	111.1 (2)	N3—C10—C11	112.5 (2)
C9—N3—C10	112.5 (2)	N3—C10—H10A	109.1
C13—N3—C10	107.4 (2)	C11—C10—H10A	109.1
C9—N3—Zn1	100.98 (15)	N3—C10—H10B	109.1
C13—N3—Zn1	111.80 (16)	C11—C10—H10B	109.1
C10—N3—Zn1	113.10 (15)	H10A—C10—H10B	107.8
N1—C1—C2	122.6 (3)	O1—C11—C10	111.4 (2)
N1—C1—H1	118.7	O1—C11—H11A	109.3
C2—C1—H1	118.7	C10—C11—H11A	109.3
C3—C2—C1	118.3 (3)	O1—C11—H11B	109.3
C3—C2—H2	120.8	C10—C11—H11B	109.3
C1—C2—H2	120.8	H11A—C11—H11B	108.0
C2—C3—C4	119.6 (3)	O1—C12—C13	111.7 (2)
C2—C3—H3	120.2	O1—C12—H12A	109.3
C4—C3—H3	120.2	C13—C12—H12A	109.3
C5—C4—C3	118.4 (3)	O1—C12—H12B	109.3
C5—C4—H4	120.8	C13—C12—H12B	109.3
C3—C4—H4	120.8	H12A—C12—H12B	107.9
N1—C5—C4	122.1 (2)	N3—C13—C12	113.3 (2)
N1—C5—C6	114.8 (2)	N3—C13—H13A	108.9
C4—C5—C6	123.1 (2)	C12—C13—H13A	108.9
N2—C6—C5	115.4 (2)	N3—C13—H13B	108.9
N2—C6—C7	125.4 (2)	C12—C13—H13B	108.9
C5—C6—C7	119.2 (2)	H13A—C13—H13B	107.7
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.99	2.55	3.491 (3)	159

Table 1

Selected bond lengths (Å)

Zn1—N1	2.205 (2)
Zn1—N2	2.093 (2)
Zn1—N3	2.269 (2)
Zn1—I1	2.6018 (4)
Zn1—I2	2.6506 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.99	2.55	3.491 (3)	159

Symmetry code: (i) .