(4-Chloro-2-{[(pyridin-2-ylmeth-yl)imino]-meth-yl}phenolato)iodido(methanol)zinc(II).

The title Schiff base zinc(II) complex, [Zn(C(13)H(10)ClN(2)O)I(CH(3)OH)], was synthesized by the reaction of 5-chloro-salicyl-aldehyde, 2-amino-methyl-pyridine and zinc iodide in methanol. The Zn(II) atom is five-coordinated by one phenolate O atom, one imine and one pyridine N atom of the Schiff base ligand, one methanol O atom and one I atom, forming a distorted square-pyramidal geometry, with the I atom at the apical site. The dihedral angle between the benzene and pyridine rings is 22.9 (2)°. In the crystal, centrosymmetrically related mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming dimers.

Related literature

For the structures of Schiff bases and then class="Chemical">ir complexes, see: Ali et al. (2008 ▶); Eltayeb et al. (2007 ▶); Datta et al. (2009 ▶); Zhao et al. (2010 ▶); Temel et al. (2010 ▶); Naveenkumar et al. (2010 ▶).

Experimental

Crystal data

[Zn(C13H10ClN2O)I(CH4O)]

M = 469.99

Monoclinn class="Chemical">ic,

a = 7.0769 (9) Å

b = 12.7212 (16) Å

c = 18.225 (2) Å

β = 98.994 (1)°

V = 1620.5 (3) Å3

Z = 4

Mo Kα radiatn class="Chemical">ion

μ = 3.59 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correctn class="Chemical">ion: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.534, T max = 0.564

9273 measured reflections

3522 independent reflectn class="Chemical">ions

2947 reflections wn class="Chemical">ith I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.058

S = 1.04

3522 reflections

195 parameters

1 restraint

H atoms treated by a mn class="Chemical">ixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.91 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 datablocks global, n class="Chemical">I. DOI: 10.1107/S160053681100417X/rz2553sup1.cif

Structure factors: contains datablocks n class="Chemical">I. DOI: 10.1107/S160053681100417X/rz2553Isup2.hkl

Additn class="Chemical">ional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn(C13H10ClN2O)I(CH4O)]	F(000) = 912
Mr = 469.99	Dx = 1.926 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3746 reflections
a = 7.0769 (9) Å	θ = 2.7–27.8°
b = 12.7212 (16) Å	µ = 3.59 mm−1
c = 18.225 (2) Å	T = 298 K
β = 98.994 (1)°	Block, colorless
V = 1620.5 (3) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3522 independent reflections
Radiation source: fine-focus sealed tube	2947 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.534, Tmax = 0.564	k = −16→15
9273 measured reflections	l = −23→17

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0266P)2 + 0.3654P] where P = (Fo2 + 2Fc2)/3
3522 reflections	(Δ/σ)max = 0.003
195 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.91 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	0.56550 (5)	1.00055 (2)	0.370141 (16)	0.03411 (9)
Cl1	0.80941 (15)	0.43991 (6)	0.42899 (5)	0.0673 (3)
I1	0.20664 (3)	1.054046 (16)	0.337917 (10)	0.04454 (7)
O1	0.5675 (3)	0.87992 (14)	0.44157 (10)	0.0428 (5)
O2	0.6619 (3)	1.10027 (17)	0.45789 (11)	0.0461 (5)
N1	0.6673 (3)	0.89862 (17)	0.29675 (11)	0.0343 (5)
N2	0.6831 (3)	1.10583 (17)	0.29614 (12)	0.0353 (5)
C1	0.6966 (4)	0.7424 (2)	0.37342 (14)	0.0331 (6)
C2	0.6271 (4)	0.7827 (2)	0.43675 (14)	0.0350 (6)
C3	0.6226 (5)	0.7138 (2)	0.49658 (16)	0.0502 (8)
H3	0.5819	0.7388	0.5394	0.060*
C4	0.6768 (5)	0.6104 (2)	0.49358 (17)	0.0517 (8)
H4	0.6702	0.5664	0.5338	0.062*
C5	0.7407 (5)	0.5715 (2)	0.43160 (17)	0.0443 (7)
C6	0.7511 (4)	0.6356 (2)	0.37262 (16)	0.0394 (6)
H6	0.7951	0.6086	0.3310	0.047*
C7	0.7123 (4)	0.8024 (2)	0.30781 (15)	0.0357 (6)
H7	0.7599	0.7676	0.2697	0.043*
C8	0.6893 (5)	0.9462 (2)	0.22567 (15)	0.0450 (7)
H8A	0.5762	0.9319	0.1896	0.054*
H8B	0.7983	0.9150	0.2076	0.054*
C9	0.7177 (4)	1.0624 (2)	0.23317 (15)	0.0364 (6)
C10	0.7742 (4)	1.1230 (3)	0.17688 (15)	0.0451 (7)
H10	0.7966	1.0917	0.1329	0.054*
C11	0.7966 (4)	1.2294 (3)	0.18702 (17)	0.0492 (8)
H11	0.8336	1.2712	0.1499	0.059*
C12	0.7637 (4)	1.2735 (2)	0.25260 (17)	0.0480 (7)
H12	0.7803	1.3452	0.2610	0.058*
C13	0.7061 (4)	1.2099 (2)	0.30520 (17)	0.0437 (7)
H13	0.6817	1.2400	0.3493	0.052*
C14	0.8502 (5)	1.1310 (3)	0.48795 (17)	0.0548 (8)
H14A	0.8972	1.0869	0.5296	0.082*
H14B	0.8498	1.2029	0.5040	0.082*
H14C	0.9315	1.1240	0.4507	0.082*
H2	0.585 (4)	1.104 (2)	0.4897 (14)	0.055 (9)*

	U11	U22	U33	U12	U13	U23
Zn1	0.03959 (19)	0.03446 (17)	0.03043 (16)	0.00566 (13)	0.01222 (13)	0.00098 (12)
Cl1	0.0921 (7)	0.0349 (4)	0.0725 (6)	0.0165 (4)	0.0054 (5)	−0.0032 (4)
I1	0.03836 (12)	0.05586 (13)	0.04069 (12)	0.01147 (9)	0.01019 (8)	0.00744 (8)
O1	0.0617 (13)	0.0352 (10)	0.0351 (10)	0.0147 (9)	0.0191 (9)	0.0028 (8)
O2	0.0553 (14)	0.0511 (12)	0.0363 (11)	−0.0032 (10)	0.0210 (10)	−0.0105 (9)
N1	0.0387 (13)	0.0371 (12)	0.0285 (11)	0.0009 (10)	0.0102 (9)	−0.0023 (9)
N2	0.0354 (13)	0.0385 (12)	0.0333 (12)	0.0014 (10)	0.0096 (10)	0.0029 (10)
C1	0.0311 (14)	0.0365 (14)	0.0320 (13)	0.0031 (11)	0.0055 (11)	−0.0022 (11)
C2	0.0359 (15)	0.0360 (14)	0.0327 (14)	0.0056 (11)	0.0045 (11)	−0.0002 (11)
C3	0.072 (2)	0.0460 (17)	0.0355 (15)	0.0140 (16)	0.0157 (15)	0.0035 (13)
C4	0.072 (2)	0.0411 (16)	0.0431 (17)	0.0130 (16)	0.0112 (15)	0.0108 (14)
C5	0.0494 (18)	0.0337 (14)	0.0481 (17)	0.0080 (13)	0.0023 (14)	−0.0022 (12)
C6	0.0381 (16)	0.0379 (15)	0.0421 (16)	0.0038 (12)	0.0063 (12)	−0.0065 (12)
C7	0.0356 (15)	0.0401 (15)	0.0330 (14)	0.0003 (12)	0.0104 (11)	−0.0102 (12)
C8	0.061 (2)	0.0469 (17)	0.0299 (14)	0.0002 (14)	0.0149 (14)	−0.0022 (12)
C9	0.0304 (15)	0.0473 (16)	0.0323 (14)	0.0017 (12)	0.0079 (11)	0.0051 (12)
C10	0.0418 (17)	0.061 (2)	0.0338 (15)	0.0001 (14)	0.0104 (13)	0.0063 (13)
C11	0.0449 (18)	0.0580 (19)	0.0461 (17)	−0.0019 (14)	0.0111 (14)	0.0198 (15)
C12	0.0471 (18)	0.0418 (16)	0.0557 (19)	0.0003 (14)	0.0101 (15)	0.0103 (14)
C13	0.0485 (18)	0.0404 (16)	0.0433 (16)	0.0046 (13)	0.0108 (13)	0.0030 (13)
C14	0.057 (2)	0.066 (2)	0.0415 (17)	−0.0016 (17)	0.0095 (15)	0.0005 (15)

Zn1—O1	2.0111 (18)	C4—C5	1.373 (4)
Zn1—N1	2.071 (2)	C4—H4	0.9300
Zn1—O2	2.071 (2)	C5—C6	1.361 (4)
Zn1—N2	2.158 (2)	C6—H6	0.9300
Zn1—I1	2.6060 (5)	C7—H7	0.9300
Cl1—C5	1.746 (3)	C8—C9	1.496 (4)
O1—C2	1.314 (3)	C8—H8A	0.9700
O2—C14	1.415 (4)	C8—H8B	0.9700
O2—H2	0.86 (3)	C9—C10	1.391 (4)
N1—C7	1.272 (3)	C10—C11	1.372 (4)
N1—C8	1.460 (3)	C10—H10	0.9300
N2—C9	1.330 (3)	C11—C12	1.372 (4)
N2—C13	1.340 (3)	C11—H11	0.9300
C1—C6	1.412 (4)	C12—C13	1.365 (4)
C1—C2	1.419 (3)	C12—H12	0.9300
C1—C7	1.438 (4)	C13—H13	0.9300
C2—C3	1.403 (4)	C14—H14A	0.9600
C3—C4	1.373 (4)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
O1—Zn1—N1	88.42 (8)	C4—C5—Cl1	119.8 (2)
O1—Zn1—O2	89.96 (8)	C5—C6—C1	121.3 (3)
N1—Zn1—O2	140.91 (9)	C5—C6—H6	119.4
O1—Zn1—N2	156.05 (8)	C1—C6—H6	119.4
N1—Zn1—N2	77.17 (8)	N1—C7—C1	126.4 (2)
O2—Zn1—N2	89.42 (8)	N1—C7—H7	116.8
O1—Zn1—I1	104.65 (6)	C1—C7—H7	116.8
N1—Zn1—I1	116.29 (6)	N1—C8—C9	111.1 (2)
O2—Zn1—I1	101.87 (6)	N1—C8—H8A	109.4
N2—Zn1—I1	98.90 (6)	C9—C8—H8A	109.4
C2—O1—Zn1	130.13 (16)	N1—C8—H8B	109.4
C14—O2—Zn1	130.14 (18)	C9—C8—H8B	109.4
C14—O2—H2	112 (2)	H8A—C8—H8B	108.0
Zn1—O2—H2	113 (2)	N2—C9—C10	121.3 (3)
C7—N1—C8	118.7 (2)	N2—C9—C8	116.7 (2)
C7—N1—Zn1	127.11 (18)	C10—C9—C8	122.0 (2)
C8—N1—Zn1	114.18 (16)	C11—C10—C9	119.2 (3)
C9—N2—C13	118.8 (2)	C11—C10—H10	120.4
C9—N2—Zn1	115.00 (17)	C9—C10—H10	120.4
C13—N2—Zn1	125.93 (18)	C12—C11—C10	119.2 (3)
C6—C1—C2	119.1 (2)	C12—C11—H11	120.4
C6—C1—C7	116.5 (2)	C10—C11—H11	120.4
C2—C1—C7	124.4 (2)	C13—C12—C11	118.7 (3)
O1—C2—C3	119.3 (2)	C13—C12—H12	120.7
O1—C2—C1	123.4 (2)	C11—C12—H12	120.7
C3—C2—C1	117.3 (2)	N2—C13—C12	122.9 (3)
C4—C3—C2	121.8 (3)	N2—C13—H13	118.6
C4—C3—H3	119.1	C12—C13—H13	118.6
C2—C3—H3	119.1	O2—C14—H14A	109.5
C5—C4—C3	120.5 (3)	O2—C14—H14B	109.5
C5—C4—H4	119.7	H14A—C14—H14B	109.5
C3—C4—H4	119.7	O2—C14—H14C	109.5
C6—C5—C4	120.0 (3)	H14A—C14—H14C	109.5
C6—C5—Cl1	120.2 (2)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.86 (3)	1.79 (3)	2.643 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.86 (3)	1.79 (3)	2.643 (3)	176 (3)

Symmetry code: (i) .