{(E)-2-[3-(Dimethyl-ammonio)propyl-iminometh-yl]phenolato}diiodidozinc(II).

The title complex, [ZnI(2)(C(12)H(18)N(2)O)], is a mononuclear zinc(II) compound derived from the zwitterionic form of the Schiff base (E)-2-[(3-dimethyl-amino-propyl-imino)meth-yl]phenol. The Zn(II) atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two iodide ions in a tetra-hedral coordination geometry. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008 ▶); Biswas et al. (2008 ▶); Chen et al. (2008 ▶); Darensbourg & Frantz (2007 ▶); Habibi et al. (2007 ▶); Kawamoto et al. (2008 ▶); Lipscomb & Sträter (1996 ▶); Tomat et al. (2007 ▶); Wu et al. (2008 ▶); Yuan et al. (2007 ▶). For related structures, see: Qiu (2006a ▶,b ▶); Wei et al. (2007 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

[ZnI2(C12H18N2O)]

M = 525.45

Orthorhombic,

a = 13.892 (3) Å

b = 16.640 (2) Å

c = 7.372 (3) Å

V = 1704.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 5.06 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.431, T max = 0.463 (expected range = 0.375–0.402)

12154 measured reflections

3669 independent reflections

3271 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.04

3669 reflections

165 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.82 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1660 Friedel pairs

Flack parameter: 0.00 (4)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808023659/sj2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023659/sj2522Isup2.hkl

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

[ZnI2(C12H18N2O)]	F000 = 992
Mr = 525.45	Dx = 2.048 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4125 reflections
a = 13.892 (3) Å	θ = 2.4–25.0º
b = 16.640 (2) Å	µ = 5.06 mm−1
c = 7.372 (3) Å	T = 298 (2) K
V = 1704.1 (8) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	3669 independent reflections
Radiation source: fine-focus sealed tube	3271 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −17→17
Tmin = 0.431, Tmax = 0.463	k = −20→21
12154 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.9395P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 1.82 e Å−3
3669 reflections	Δρmin = −0.46 e Å−3
165 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1660 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (4)
Secondary atom site location: difference Fourier map

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	0.75194 (6)	0.90239 (4)	0.72869 (14)	0.03631 (19)
I1	0.58993 (3)	0.92236 (3)	0.88834 (9)	0.04992 (15)
I2	0.89258 (4)	0.98333 (3)	0.85716 (9)	0.05741 (18)
N1	0.7294 (4)	0.9228 (3)	0.4634 (8)	0.0379 (13)
N2	0.8361 (5)	1.1716 (3)	0.3321 (11)	0.0544 (19)
H2A	0.7857	1.2052	0.3106	0.065*
O1	0.7847 (4)	0.7893 (3)	0.6946 (7)	0.0429 (12)
C1	0.8309 (5)	0.7664 (4)	0.5451 (11)	0.0385 (16)
C2	0.8869 (6)	0.6960 (5)	0.5496 (14)	0.053 (2)
H2	0.8923	0.6672	0.6573	0.063*
C3	0.9338 (6)	0.6691 (5)	0.396 (2)	0.070 (3)
H3	0.9722	0.6234	0.4030	0.084*
C4	0.9256 (7)	0.7066 (5)	0.2392 (16)	0.063 (3)
H4	0.9575	0.6865	0.1380	0.075*
C5	0.8701 (7)	0.7758 (5)	0.2225 (15)	0.063 (2)
H5	0.8653	0.8019	0.1113	0.075*
C6	0.8209 (5)	0.8061 (4)	0.3760 (13)	0.0422 (15)
C7	0.7648 (5)	0.8782 (4)	0.3445 (10)	0.0389 (16)
H7	0.7542	0.8926	0.2243	0.047*
C8	0.6691 (5)	0.9919 (4)	0.4056 (12)	0.0456 (19)
H8A	0.6074	0.9889	0.4667	0.055*
H8B	0.6574	0.9880	0.2761	0.055*
C9	0.7143 (6)	1.0712 (4)	0.4458 (11)	0.0459 (19)
H9A	0.7358	1.0721	0.5710	0.055*
H9B	0.6668	1.1134	0.4305	0.055*
C10	0.7992 (6)	1.0871 (4)	0.3217 (13)	0.049 (2)
H10A	0.8510	1.0505	0.3531	0.059*
H10B	0.7802	1.0758	0.1977	0.059*
C11	0.8730 (10)	1.1894 (6)	0.5117 (19)	0.100 (5)
H11A	0.9164	1.1476	0.5488	0.150*
H11B	0.8205	1.1926	0.5960	0.150*
H11C	0.9066	1.2398	0.5092	0.150*
C12	0.9089 (8)	1.1848 (6)	0.186 (2)	0.101 (5)
H12A	0.9269	1.2405	0.1834	0.151*
H12B	0.8819	1.1699	0.0711	0.151*
H12C	0.9648	1.1525	0.2099	0.151*

	U11	U22	U33	U12	U13	U23
Zn1	0.0426 (5)	0.0328 (3)	0.0335 (4)	0.0041 (3)	0.0026 (4)	0.0028 (3)
I1	0.0415 (3)	0.0491 (2)	0.0591 (3)	0.00396 (18)	0.0126 (3)	−0.0002 (3)
I2	0.0486 (3)	0.0603 (3)	0.0633 (4)	−0.0039 (2)	−0.0084 (3)	−0.0062 (3)
N1	0.037 (3)	0.042 (3)	0.035 (3)	−0.012 (2)	−0.001 (3)	−0.004 (3)
N2	0.048 (4)	0.029 (3)	0.086 (6)	0.005 (3)	−0.002 (4)	0.007 (3)
O1	0.052 (3)	0.032 (2)	0.045 (3)	0.008 (2)	0.007 (3)	0.006 (2)
C1	0.034 (4)	0.033 (3)	0.048 (5)	−0.008 (3)	0.005 (3)	−0.002 (3)
C2	0.055 (5)	0.040 (4)	0.063 (6)	0.008 (4)	0.016 (4)	0.005 (4)
C3	0.059 (5)	0.040 (4)	0.111 (9)	0.008 (4)	0.019 (7)	−0.003 (6)
C4	0.063 (6)	0.052 (5)	0.073 (7)	0.010 (4)	0.028 (5)	−0.016 (5)
C5	0.070 (6)	0.063 (5)	0.055 (6)	0.001 (4)	0.014 (5)	−0.012 (5)
C6	0.040 (4)	0.040 (3)	0.046 (4)	0.003 (3)	0.008 (4)	−0.004 (4)
C7	0.049 (4)	0.044 (3)	0.024 (4)	0.001 (3)	0.003 (3)	0.001 (3)
C8	0.041 (4)	0.045 (3)	0.051 (5)	0.001 (3)	−0.004 (4)	0.017 (4)
C9	0.051 (5)	0.039 (4)	0.047 (5)	0.016 (3)	−0.006 (4)	0.005 (3)
C10	0.051 (5)	0.027 (3)	0.070 (6)	0.005 (3)	0.005 (4)	0.006 (3)
C11	0.111 (10)	0.054 (6)	0.135 (11)	−0.023 (6)	−0.078 (9)	0.026 (6)
C12	0.074 (7)	0.052 (5)	0.177 (15)	0.007 (5)	0.051 (8)	0.028 (8)

Zn1—O1	1.952 (4)	C5—C6	1.415 (12)
Zn1—N1	2.010 (6)	C5—H5	0.9300
Zn1—I2	2.5550 (11)	C6—C7	1.449 (9)
Zn1—I1	2.5615 (11)	C7—H7	0.9300
N1—C7	1.250 (9)	C8—C9	1.491 (10)
N1—C8	1.485 (9)	C8—H8A	0.9700
N2—C11	1.451 (14)	C8—H8B	0.9700
N2—C12	1.493 (15)	C9—C10	1.516 (12)
N2—C10	1.498 (8)	C9—H9A	0.9700
N2—H2A	0.9100	C9—H9B	0.9700
O1—C1	1.331 (9)	C10—H10A	0.9700
C1—C2	1.406 (10)	C10—H10B	0.9700
C1—C6	1.417 (12)	C11—H11A	0.9600
C2—C3	1.384 (15)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.317 (17)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.392 (12)	C12—H12C	0.9600
C4—H4	0.9300
O1—Zn1—N1	94.3 (2)	N1—C7—C6	126.2 (7)
O1—Zn1—I2	112.17 (16)	N1—C7—H7	116.9
N1—Zn1—I2	113.02 (16)	C6—C7—H7	116.9
O1—Zn1—I1	112.90 (16)	N1—C8—C9	113.0 (6)
N1—Zn1—I1	106.74 (18)	N1—C8—H8A	109.0
I2—Zn1—I1	115.67 (4)	C9—C8—H8A	109.0
C7—N1—C8	118.8 (7)	N1—C8—H8B	109.0
C7—N1—Zn1	121.4 (5)	C9—C8—H8B	109.0
C8—N1—Zn1	119.9 (5)	H8A—C8—H8B	107.8
C11—N2—C12	112.8 (9)	C8—C9—C10	111.2 (6)
C11—N2—C10	111.1 (7)	C8—C9—H9A	109.4
C12—N2—C10	109.5 (8)	C10—C9—H9A	109.4
C11—N2—H2A	107.8	C8—C9—H9B	109.4
C12—N2—H2A	107.8	C10—C9—H9B	109.4
C10—N2—H2A	107.8	H9A—C9—H9B	108.0
C1—O1—Zn1	119.6 (4)	N2—C10—C9	113.5 (6)
O1—C1—C2	119.0 (7)	N2—C10—H10A	108.9
O1—C1—C6	123.2 (6)	C9—C10—H10A	108.9
C2—C1—C6	117.6 (7)	N2—C10—H10B	108.9
C3—C2—C1	120.7 (9)	C9—C10—H10B	108.9
C3—C2—H2	119.6	H10A—C10—H10B	107.7
C1—C2—H2	119.6	N2—C11—H11A	109.5
C4—C3—C2	121.6 (8)	N2—C11—H11B	109.5
C4—C3—H3	119.2	H11A—C11—H11B	109.5
C2—C3—H3	119.2	N2—C11—H11C	109.5
C3—C4—C5	121.2 (9)	H11A—C11—H11C	109.5
C3—C4—H4	119.4	H11B—C11—H11C	109.5
C5—C4—H4	119.4	N2—C12—H12A	109.5
C4—C5—C6	119.5 (10)	N2—C12—H12B	109.5
C4—C5—H5	120.3	H12A—C12—H12B	109.5
C6—C5—H5	120.3	N2—C12—H12C	109.5
C5—C6—C1	119.3 (7)	H12A—C12—H12C	109.5
C5—C6—C7	115.2 (8)	H12B—C12—H12C	109.5
C1—C6—C7	125.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.91	1.91	2.772 (8)	157

Zn1—O1	1.952 (4)
Zn1—N1	2.010 (6)
Zn1—I2	2.5550 (11)
Zn1—I1	2.5615 (11)

O1—Zn1—N1	94.3 (2)
O1—Zn1—I2	112.17 (16)
N1—Zn1—I2	113.02 (16)
O1—Zn1—I1	112.90 (16)
N1—Zn1—I1	106.74 (18)
I2—Zn1—I1	115.67 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.91	1.91	2.772 (8)	157

Symmetry code: (i) .