(4-Chloro-2-{[(pyridin-2-ylmeth­yl)imino]­meth­yl}phenolato)iodido(methanol)zinc(II)

Huang, H.-W.

doi:10.1107/S160053681100417X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m313

doi:10.1107/S160053681100417X

Open

access

(4-Chloro-2-{[(pyridin-2-ylmethyl)imino]methyl}phenolato)iodido(methanol)zinc(II)

Hong-Wei Huang ^a ^*

^aCollege of Chemistry and Biology Engineering, Yichun University, Yichun 336000, People's Republic of China
^*Correspondence e-mail: huanghongwei_ycu@126.com

(Received 24 January 2011; accepted 3 February 2011; online 9 February 2011)

The title Schiff base zinc(II) complex, [Zn(C₁₃H₁₀ClN₂O)I(CH₃OH)], was synthesized by the reaction of 5-chlorosalicylaldehyde, 2-aminomethylpyridine 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 molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming dimers.

Related literature

For the structures of Schiff bases and their 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_r = 469.99
Monoclinic, P 2₁ /c
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 radiation
μ = 3.59 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.534, T_max = 0.564
9273 measured reflections
3522 independent reflections
2947 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.058
S = 1.04
3522 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.91 e Å⁻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) -x+1, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100417X/rz2553sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100417X/rz2553Isup2.hkl

checkCIF report

Comment top

Schiff bases and their complexes have attracted much attention for their interesting structures (Ali et al., 2008; Eltayeb et al., 2007; Datta et al., 2009; Zhao et al., 2010; Temel et al., 2010; Naveenkumar et al., 2010). In this paper, the title new Schiff base zinc(II) complex, Fig. 1, is reported.

The Zn atom in the complex is five-coordinated by one phenolate O atom, one imine and one pyridine N atoms of the Schiff base ligand, one methanol O atom, and one iodide atom to form a distorted square pyramidal geometry. The dihedral angle between the benzene and the pyridine rings is 22.9 (2)°. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked through intermolecular O—H···N hydrogen bonds (Table 1) to form dimers.

Related literature top

For the structures of Schiff bases and their 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 top

Equimolar quantities (0.1 mmol each) of 5-chlorosalicylaldehyde, 2-aminomethylpyridine, and zinc iodide were mixed and stirred in methanol for 30 min at reflux. After keeping the filtrate in air for a few days, colourless block crystals suitable for X-ray analysis were formed.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% displacements ellipsoids.
	Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen atoms not involved in hydrogen bonds (dashed lines) are omitted for clarity.

(4-Chloro-2-{[(pyridin-2- ylmethyl)imino]methyl}phenolato)iodido(methanol)zinc(II) top

Crystal data top

[Zn(C₁₃H₁₀ClN₂O)I(CH₄O)]	F(000) = 912
M_r = 469.99	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0266P)² + 0.3654P] where P = (F_o² + 2F_c²)/3
3522 reflections	(Δ/σ)_max = 0.003
195 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Zn(C₁₃H₁₀ClN₂O)I(CH₄O)]	V = 1620.5 (3) Å³
M_r = 469.99	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0769 (9) Å	µ = 3.59 mm⁻¹
b = 12.7212 (16) Å	T = 298 K
c = 18.225 (2) Å	0.20 × 0.20 × 0.18 mm
β = 98.994 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3522 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2947 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.564	R_int = 0.021
9273 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	1 restraint
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.37 e Å⁻³
3522 reflections	Δρ_min = −0.91 e Å⁻³
195 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₁₀ClN₂O)I(CH₄O)]
M_r	469.99
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.0769 (9), 12.7212 (16), 18.225 (2)
β (°)	98.994 (1)
V (Å³)	1620.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.59
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.534, 0.564
No. of measured, independent and observed [I > 2σ(I)] reflections	9273, 3522, 2947
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.058, 1.04
No. of reflections	3522
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.91

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by Yichun University.

References

Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Datta, A., Chuang, N.-T., Huang, J.-H. & Lee, H. M. (2009). Acta Cryst. E65, m964. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, m1672–m1673. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naveenkumar, H. S., Sadikun, A., Ibrahim, P., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o1918–o1919. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Temel, E., Ağar, E. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1131. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, L., Cao, D. & Cui, J. (2010). Acta Cryst. E66, o2204. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m313

doi:10.1107/S160053681100417X

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(4-Chloro-2-{[(pyridin-2-ylmeth­yl)imino]­meth­yl}phenolato)iodido(methanol)zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(4-Chloro-2-{[(pyridin-2-ylmethyl)imino]methyl}phenolato)iodido(methanol)zinc(II)