{4-Bromo-2-[(2-morpholinoeth-yl)imino-meth-yl]phenolato}iodido(methanol)zinc(II).

The title compound, [Zn(C(13)H(16)BrN(2)O(2))I(CH(3)OH)], is a new mononuclear zinc(II) complex synthesized by the reaction of equimolar quanti-ties of 5-bromo-salicylaldehyde, 2-morpholinoethyl-amine and ZnI(2) in methanol. The Zn atom is four-coordinate in a distorted tetra-hedral geometry, binding to a phenolate O and an imine N atom of the Schiff base ligand, the O atom of a methanol mol-ecule and one I(-) anion. In the crystal structure, adjacent mol-ecules are linked through inter-molecular 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 = 536.50

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.096

S = 1.03

3928 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.71 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, I. DOI: 10.1107/S1600536809009234/sj2595sup1.cif

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

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

[Zn(C13H16BrN2O2)I(CH4O)]	F(000) = 1040
Mr = 536.50	Dx = 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

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

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(Fo2) + (0.0385P)2 + 2.0556P] where P = (Fo2 + 2Fc2)/3
3928 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.96 e Å−3
1 restraint	Δρmin = −0.71 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	0.50584 (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*

	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)

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

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)

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) .