{4-Bromo-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato}iodido(methanol)zinc(II)

Han, C.-L.

doi:10.1107/S1600536809009234

metal-organic compounds

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Volume 65| Part 4| April 2009| Page m418

doi:10.1107/S1600536809009234

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{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]phenolato}iodido(methanol)zinc(II)

Cheng-Li Han ^a ^*

^aCollege of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, People's Republic of China
^*Correspondence e-mail: chengli_han@126.com

(Received 10 March 2009; accepted 12 March 2009; online 19 March 2009)

The title compound, [Zn(C₁₃H₁₆BrN₂O₂)I(CH₃OH)], is a new mononuclear zinc(II) complex synthesized by the reaction of equimolar quantities of 5-bromosalicylaldehyde, 2-morpholinoethylamine and ZnI₂ in methanol. The Zn atom is four-coordinate in a distorted tetrahedral geometry, binding to a phenolate O and an imine N atom of the Schiff base ligand, the O atom of a methanol molecule and one I⁻ anion. In the crystal structure, adjacent molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For the structures of related zinc(II) complexes, see: Ali et al. (2008 ); You (2005 ); Zhu & Yang (2008 ).

Experimental

Crystal data

[Zn(C₁₃H₁₆BrN₂O₂)I(CH₄O)]
M_r = 536.50
Monoclinic, P 2₁ /c
a = 7.747 (2) Å
b = 24.977 (3) Å
c = 9.598 (2) Å
β = 100.497 (4)°
V = 1826.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 5.24 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.217, T_max = 0.231
12877 measured reflections
3928 independent reflections
2994 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.096
S = 1.03
3928 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N1	2.014 (3)
Zn1—O3	2.023 (3)
Zn1—O1	2.078 (3)
Zn1—I1	2.5346 (9)

N1—Zn1—O3	114.78 (13)
N1—Zn1—O1	90.15 (12)
O3—Zn1—O1	90.42 (13)
N1—Zn1—I1	130.76 (10)
O3—Zn1—I1	113.36 (9)
O1—Zn1—I1	99.31 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.84 (5)	1.81 (5)	2.649 (4)	178 (7)
Symmetry code: (i) -x+1, -y+1, -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/S1600536809009234/sj2595sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009234/sj2595Isup2.hkl

checkCIF report

Comment top

Metal complexes of the Schiff base 4-bromo-2-[(2-morpholinoethylimino)methyl]phenol have not been reported previously. In this paper, the author reports the crystal structure of the title compound, a new mononuclear zinc(II) complex, (I), Fig. 1.

In (I), the Zn atom is four-coordinate in a tetrahedral geometry, with one O and one imine N atoms of a Schiff base ligand, one O atom of a methanol molecule, and one I atom. The tetrahedral geometry is severely distorted, as evidenced by the coordinate bond lengths and angles (Table 1). The bond lengths and angles in this complex are comparable with those in the similar zinc(II) complexes (Ali et al., 2008; You, 2005; Zhu & Yang, 2008). In the crystal structure, adjacent molecules are linked through intermolecular O–H···O hydrogen bonds (Table 2), forming centrosymmetric dimers (Fig. 2).

Related literature top

For the structures of related zinc(II) complexes, see: Ali et al. (2008); You (2005); Zhu & Yang (2008).

Experimental top

Equimolar quantities (1.0 mmol each) of 5-bromosalicyaldehyde, 2-morpholinoethylamine, and ZnI₂ were mixed in methanol. The mixture was stirred at reflux for 30 min and filtered. The filtrate was slowly evaporated for a few days, yielding yellow block-like crystals.

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 structure of the complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I) showing the formation of centrosymmetric dimers. Hydrogen bonds are shown as dashed lines.

{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]phenolato}iodido(methanol)zinc(II) top

Crystal data top

[Zn(C₁₃H₁₆BrN₂O₂)I(CH₄O)]	F(000) = 1040
M_r = 536.50	D_x = 1.951 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3128 reflections
a = 7.747 (2) Å	θ = 2.6–25.8°
b = 24.977 (3) Å	µ = 5.24 mm⁻¹
c = 9.598 (2) Å	T = 298 K
β = 100.497 (4)°	Block, yellow
V = 1826.1 (6) Å³	0.30 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3928 independent reflections
Radiation source: fine-focus sealed tube	2994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.217, T_max = 0.231	k = −30→31
12877 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0385P)² + 2.0556P] where P = (F_o² + 2F_c²)/3
3928 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.96 e Å⁻³
1 restraint	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Zn(C₁₃H₁₆BrN₂O₂)I(CH₄O)]	V = 1826.1 (6) Å³
M_r = 536.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.747 (2) Å	µ = 5.24 mm⁻¹
b = 24.977 (3) Å	T = 298 K
c = 9.598 (2) Å	0.30 × 0.30 × 0.28 mm
β = 100.497 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3928 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2994 reflections with I > 2σ(I)
T_min = 0.217, T_max = 0.231	R_int = 0.038
12877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.96 e Å⁻³
3928 reflections	Δρ_min = −0.71 e Å⁻³
203 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	0.50584 (7)	0.55343 (2)	0.28004 (5)	0.03432 (14)
I1	0.17781 (4)	0.568293 (16)	0.25354 (4)	0.05466 (14)
Br1	1.05025 (10)	0.31501 (2)	0.17245 (8)	0.0752 (2)
O1	0.5139 (4)	0.47117 (12)	0.3133 (3)	0.0403 (8)
O2	0.6023 (12)	0.73465 (19)	0.4160 (5)	0.119 (3)
O3	0.6375 (4)	0.56560 (12)	0.4796 (3)	0.0370 (7)
N1	0.6591 (4)	0.54528 (13)	0.1329 (4)	0.0276 (7)
N2	0.5630 (5)	0.65133 (14)	0.2055 (4)	0.0381 (9)
C1	0.7471 (6)	0.45205 (16)	0.1873 (4)	0.0298 (9)
C2	0.6310 (6)	0.43807 (17)	0.2793 (5)	0.0340 (10)
C3	0.6426 (7)	0.38546 (18)	0.3320 (5)	0.0464 (13)
H3	0.5649	0.3747	0.3899	0.056*
C4	0.7640 (8)	0.34916 (19)	0.3017 (5)	0.0502 (13)
H4	0.7691	0.3148	0.3396	0.060*
C5	0.8782 (7)	0.36454 (18)	0.2139 (5)	0.0409 (11)
C6	0.8706 (6)	0.41432 (18)	0.1569 (5)	0.0364 (10)
H6	0.9477	0.4237	0.0972	0.044*
C7	0.7474 (6)	0.50294 (17)	0.1163 (4)	0.0310 (9)
H7	0.8209	0.5054	0.0501	0.037*
C8	0.6873 (6)	0.59135 (17)	0.0431 (5)	0.0366 (10)
H8A	0.6722	0.5799	−0.0549	0.044*
H8B	0.8066	0.6044	0.0713	0.044*
C9	0.5603 (6)	0.63595 (17)	0.0561 (4)	0.0346 (10)
H9A	0.5897	0.6669	0.0041	0.042*
H9B	0.4426	0.6247	0.0137	0.042*
C10	0.4279 (9)	0.6926 (2)	0.2083 (6)	0.0645 (18)
H10A	0.3126	0.6775	0.1741	0.077*
H10B	0.4458	0.7219	0.1464	0.077*
C11	0.4376 (14)	0.7133 (3)	0.3593 (8)	0.099 (3)
H11A	0.3489	0.7407	0.3593	0.118*
H11B	0.4118	0.6842	0.4192	0.118*
C12	0.7298 (13)	0.6951 (3)	0.4179 (7)	0.100 (3)
H12A	0.7050	0.6656	0.4769	0.119*
H12B	0.8438	0.7097	0.4592	0.119*
C13	0.7348 (9)	0.6746 (2)	0.2692 (6)	0.0619 (16)
H13A	0.7629	0.7038	0.2106	0.074*
H13B	0.8256	0.6476	0.2735	0.074*
C14	0.8215 (7)	0.5553 (2)	0.5089 (6)	0.0561 (14)
H14A	0.8423	0.5183	0.4908	0.084*
H14B	0.8673	0.5633	0.6064	0.084*
H14C	0.8788	0.5773	0.4492	0.084*
H3A	0.592 (8)	0.554 (2)	0.547 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0288 (3)	0.0448 (3)	0.0309 (3)	0.0064 (2)	0.0093 (2)	−0.0008 (2)
I1	0.02973 (19)	0.0787 (3)	0.0568 (2)	0.00815 (16)	0.01119 (16)	0.01217 (18)
Br1	0.0901 (5)	0.0545 (4)	0.0895 (5)	0.0392 (3)	0.0386 (4)	0.0100 (3)
O1	0.046 (2)	0.0353 (17)	0.0463 (19)	0.0053 (14)	0.0257 (17)	0.0043 (14)
O2	0.253 (9)	0.041 (3)	0.068 (3)	−0.004 (4)	0.044 (4)	−0.013 (2)
O3	0.0370 (18)	0.0466 (19)	0.0286 (16)	−0.0013 (14)	0.0093 (14)	0.0038 (14)
N1	0.0282 (19)	0.0265 (18)	0.0288 (18)	0.0003 (14)	0.0067 (15)	0.0010 (14)
N2	0.053 (3)	0.0282 (19)	0.037 (2)	0.0047 (17)	0.0179 (19)	0.0044 (15)
C1	0.032 (2)	0.030 (2)	0.027 (2)	0.0010 (18)	0.0060 (19)	−0.0024 (17)
C2	0.038 (3)	0.035 (2)	0.030 (2)	−0.0023 (19)	0.008 (2)	−0.0002 (18)
C3	0.066 (4)	0.036 (3)	0.044 (3)	0.004 (2)	0.027 (3)	0.007 (2)
C4	0.075 (4)	0.029 (2)	0.048 (3)	0.005 (2)	0.014 (3)	0.005 (2)
C5	0.046 (3)	0.038 (3)	0.040 (3)	0.012 (2)	0.010 (2)	−0.005 (2)
C6	0.037 (3)	0.037 (2)	0.037 (2)	0.004 (2)	0.013 (2)	−0.0018 (19)
C7	0.029 (2)	0.038 (2)	0.027 (2)	−0.0031 (19)	0.0084 (18)	−0.0034 (18)
C8	0.042 (3)	0.034 (2)	0.036 (2)	0.000 (2)	0.015 (2)	0.0049 (19)
C9	0.038 (3)	0.033 (2)	0.033 (2)	0.0041 (19)	0.009 (2)	0.0095 (18)
C10	0.107 (5)	0.039 (3)	0.057 (3)	0.030 (3)	0.041 (4)	0.017 (2)
C11	0.174 (10)	0.065 (5)	0.073 (5)	0.055 (5)	0.064 (6)	0.022 (4)
C12	0.196 (10)	0.046 (4)	0.051 (4)	−0.041 (5)	0.007 (5)	−0.009 (3)
C13	0.087 (5)	0.046 (3)	0.053 (3)	−0.026 (3)	0.013 (3)	−0.005 (2)
C14	0.040 (3)	0.075 (4)	0.050 (3)	−0.008 (3)	0.001 (3)	0.017 (3)

Geometric parameters (Å, º) top

Zn1—N1	2.014 (3)	C4—H4	0.9300
Zn1—O3	2.023 (3)	C5—C6	1.355 (6)
Zn1—O1	2.078 (3)	C6—H6	0.9300
Zn1—I1	2.5346 (9)	C7—H7	0.9300
Br1—C5	1.913 (4)	C8—C9	1.507 (6)
O1—C2	1.311 (5)	C8—H8A	0.9700
O2—C12	1.394 (10)	C8—H8B	0.9700
O2—C11	1.398 (11)	C9—H9A	0.9700
O3—C14	1.425 (6)	C9—H9B	0.9700
O3—H3A	0.84 (5)	C10—C11	1.528 (9)
N1—C7	1.285 (5)	C10—H10A	0.9700
N1—C8	1.478 (5)	C10—H10B	0.9700
N2—C10	1.472 (6)	C11—H11A	0.9700
N2—C13	1.478 (7)	C11—H11B	0.9700
N2—C9	1.481 (5)	C12—C13	1.525 (8)
C1—C6	1.411 (6)	C12—H12A	0.9700
C1—C2	1.414 (6)	C12—H12B	0.9700
C1—C7	1.442 (6)	C13—H13A	0.9700
C2—C3	1.405 (6)	C13—H13B	0.9700
C3—C4	1.375 (7)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.383 (7)	C14—H14C	0.9600

N1—Zn1—O3	114.78 (13)	C9—C8—H8A	109.4
N1—Zn1—O1	90.15 (12)	N1—C8—H8B	109.4
O3—Zn1—O1	90.42 (13)	C9—C8—H8B	109.4
N1—Zn1—I1	130.76 (10)	H8A—C8—H8B	108.0
O3—Zn1—I1	113.36 (9)	N2—C9—C8	112.2 (4)
O1—Zn1—I1	99.31 (9)	N2—C9—H9A	109.2
C2—O1—Zn1	126.0 (3)	C8—C9—H9A	109.2
C12—O2—C11	109.3 (5)	N2—C9—H9B	109.2
C14—O3—Zn1	118.2 (3)	C8—C9—H9B	109.2
C14—O3—H3A	109 (4)	H9A—C9—H9B	107.9
Zn1—O3—H3A	118 (4)	N2—C10—C11	110.1 (5)
C7—N1—C8	115.5 (3)	N2—C10—H10A	109.6
C7—N1—Zn1	124.4 (3)	C11—C10—H10A	109.6
C8—N1—Zn1	119.9 (3)	N2—C10—H10B	109.6
C10—N2—C13	107.9 (4)	C11—C10—H10B	109.6
C10—N2—C9	108.4 (4)	H10A—C10—H10B	108.2
C13—N2—C9	110.8 (4)	O2—C11—C10	112.5 (6)
C6—C1—C2	119.8 (4)	O2—C11—H11A	109.1
C6—C1—C7	115.6 (4)	C10—C11—H11A	109.1
C2—C1—C7	124.6 (4)	O2—C11—H11B	109.1
O1—C2—C3	120.1 (4)	C10—C11—H11B	109.1
O1—C2—C1	123.2 (4)	H11A—C11—H11B	107.8
C3—C2—C1	116.7 (4)	O2—C12—C13	111.4 (6)
C4—C3—C2	122.8 (4)	O2—C12—H12A	109.4
C4—C3—H3	118.6	C13—C12—H12A	109.4
C2—C3—H3	118.6	O2—C12—H12B	109.4
C3—C4—C5	118.9 (4)	C13—C12—H12B	109.4
C3—C4—H4	120.5	H12A—C12—H12B	108.0
C5—C4—H4	120.5	N2—C13—C12	110.2 (6)
C6—C5—C4	121.0 (4)	N2—C13—H13A	109.6
C6—C5—Br1	119.3 (4)	C12—C13—H13A	109.6
C4—C5—Br1	119.6 (4)	N2—C13—H13B	109.6
C5—C6—C1	120.7 (4)	C12—C13—H13B	109.6
C5—C6—H6	119.7	H13A—C13—H13B	108.1
C1—C6—H6	119.7	O3—C14—H14A	109.5
N1—C7—C1	128.3 (4)	O3—C14—H14B	109.5
N1—C7—H7	115.8	H14A—C14—H14B	109.5
C1—C7—H7	115.8	O3—C14—H14C	109.5
N1—C8—C9	111.1 (3)	H14A—C14—H14C	109.5
N1—C8—H8A	109.4	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.84 (5)	1.81 (5)	2.649 (4)	178 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₁₆BrN₂O₂)I(CH₄O)]
M_r	536.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.747 (2), 24.977 (3), 9.598 (2)
β (°)	100.497 (4)
V (Å³)	1826.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.24
Crystal size (mm)	0.30 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.217, 0.231
No. of measured, independent and observed [I > 2σ(I)] reflections	12877, 3928, 2994
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.096, 1.03
No. of reflections	3928
No. of parameters	203
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)	0.96, −0.71

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

Selected geometric parameters (Å, º) top

Zn1—N1	2.014 (3)	Zn1—O1	2.078 (3)
Zn1—O3	2.023 (3)	Zn1—I1	2.5346 (9)

N1—Zn1—O3	114.78 (13)	N1—Zn1—I1	130.76 (10)
N1—Zn1—O1	90.15 (12)	O3—Zn1—I1	113.36 (9)
O3—Zn1—O1	90.42 (13)	O1—Zn1—I1	99.31 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.84 (5)	1.81 (5)	2.649 (4)	178 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The author acknowledges a research grant from Qiqihar 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
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m418

doi:10.1107/S1600536809009234

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

{4-Bromo-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato}iodido(methanol)zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]phenolato}iodido(methanol)zinc(II)