(μ-4-Bromo-2-{1-[2-(dimethyl-amino)ethyl-imino]eth-yl}phenolato)bis-[ethyl-zinc(II)].

The title complex, [Zn(2)(C(2)H(5))(2)(C(12)H(16)BrN(2)O)(2)], is dimeric, bridged through the O atoms of the phenolate anions. The molecule lies on a crystallographic twofold rotation axis. Each Zn atom is penta-coordinated by two N atoms and two bridging O atoms of the tridentate salicylideneiminate ligands and one C atom from an ethyl group, forming a distorted square-pyramidal environment.

Related literature

For related literature, see: Chamberlain et al. (2001 ▶); Chen et al. (2005 ▶, 2006 ▶); Chisholm et al. (2000 ▶); Dechy-Cabaret et al. (2004 ▶); Gref et al. (1994 ▶); Jeong et al. (1997 ▶); Williams et al. (2003 ▶); Wu et al. (2005 ▶, 2006 ▶)

Experimental

Crystal data

[Zn2(C2H5)2(C12H16BrN2O)2]

M = 757.22

Orthorhombic,

a = 21.656 (6) Å

b = 7.839 (2) Å

c = 19.114 (5) Å

V = 3244.9 (14) Å3

Z = 4

Mo Kα radiation

μ = 3.97 mm−1

T = 293 (2) K

0.17 × 0.16 × 0.15 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: none

17313 measured reflections

3207 independent reflections

1957 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.107

S = 1.00

3207 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065208/at2521sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065208/at2521Isup2.hkl

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

[Zn2(C2H5)2(C12H16BrN2O)2]	F000 = 1536
Mr = 757.22	Dx = 1.550 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3732 reflections
a = 21.656 (6) Å	θ = 2.8–24.0º
b = 7.839 (2) Å	µ = 3.97 mm−1
c = 19.114 (5) Å	T = 293 (2) K
V = 3244.9 (14) Å3	Parallelpiped, yellow
Z = 4	0.17 × 0.16 × 0.15 mm

Bruker SMART 1K CCD diffractometer	1957 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
Monochromator: graphite	θmax = 26.1º
T = 298(2) K	θmin = 1.9º
φ and ω scans	h = −26→25
Absorption correction: none	k = −9→9
17313 measured reflections	l = −13→23
3207 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
3207 reflections	Δρmax = 0.68 e Å−3
172 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Zn	0.93264 (2)	0.18811 (6)	0.70779 (3)	0.04040 (17)
Br	0.79595 (3)	0.47079 (8)	1.01986 (3)	0.0781 (2)
O1	0.97357 (12)	0.1816 (4)	0.80980 (15)	0.0476 (8)
N1	0.87340 (16)	0.0062 (4)	0.7620 (2)	0.0462 (9)
N2	0.92031 (17)	−0.0132 (5)	0.6261 (2)	0.0569 (10)
C1	0.93610 (19)	0.2386 (6)	0.8581 (2)	0.0424 (10)
C2	0.87745 (18)	0.1621 (5)	0.8681 (2)	0.0395 (10)
C3	0.8368 (2)	0.2322 (6)	0.9182 (2)	0.0461 (11)
H3A	0.7984	0.1821	0.9254	0.055*
C4	0.8534 (2)	0.3742 (6)	0.9567 (2)	0.0536 (12)
C5	0.9115 (2)	0.4456 (6)	0.9490 (3)	0.0613 (14)
H5A	0.9231	0.5387	0.9761	0.074*
C6	0.9519 (2)	0.3770 (6)	0.9005 (3)	0.0566 (13)
H6A	0.9911	0.4247	0.8961	0.068*
C7	0.85761 (18)	0.0141 (5)	0.8261 (3)	0.0428 (10)
C8	0.8185 (3)	−0.1206 (7)	0.8618 (3)	0.0779 (17)
H8A	0.8087	−0.2092	0.8289	0.117*
H8B	0.7810	−0.0697	0.8786	0.117*
H8C	0.8410	−0.1683	0.9003	0.117*
C9	0.8539 (2)	−0.1357 (6)	0.7177 (3)	0.0655 (15)
H9A	0.8114	−0.1653	0.7279	0.079*
H9B	0.8795	−0.2348	0.7269	0.079*
C10	0.8600 (2)	−0.0839 (7)	0.6419 (3)	0.0780 (18)
H10A	0.8529	−0.1827	0.6125	0.094*
H10B	0.8286	0.0002	0.6310	0.094*
C11	0.9207 (3)	0.0648 (9)	0.5561 (3)	0.104 (2)
H11A	0.9154	−0.0223	0.5213	0.156*
H11B	0.9593	0.1219	0.5486	0.156*
H11C	0.8875	0.1457	0.5526	0.156*
C12	0.9678 (3)	−0.1460 (7)	0.6266 (4)	0.092 (2)
H12A	0.9593	−0.2274	0.5903	0.138*
H12B	0.9677	−0.2026	0.6711	0.138*
H12C	1.0075	−0.0952	0.6186	0.138*
C13	0.88570 (19)	0.4061 (5)	0.6884 (2)	0.0469 (11)
H13A	0.9059	0.4986	0.7132	0.056*
H13B	0.8885	0.4307	0.6388	0.056*
C14	0.8200 (2)	0.4042 (8)	0.7084 (3)	0.0851 (19)
H14A	0.8016	0.5121	0.6970	0.128*
H14B	0.8165	0.3843	0.7578	0.128*
H14C	0.7992	0.3150	0.6834	0.128*

	U11	U22	U33	U12	U13	U23
Zn	0.0380 (3)	0.0341 (3)	0.0490 (3)	0.0014 (2)	−0.0007 (2)	−0.0017 (2)
Br	0.0802 (4)	0.0978 (5)	0.0562 (4)	0.0351 (3)	−0.0039 (3)	−0.0238 (3)
O1	0.0353 (15)	0.0560 (19)	0.052 (2)	0.0020 (14)	0.0015 (13)	−0.0005 (15)
N1	0.047 (2)	0.032 (2)	0.061 (3)	−0.0057 (16)	0.0050 (18)	−0.0076 (18)
N2	0.060 (3)	0.055 (2)	0.055 (3)	−0.012 (2)	0.0055 (19)	−0.019 (2)
C1	0.046 (2)	0.044 (2)	0.037 (3)	0.006 (2)	−0.005 (2)	0.002 (2)
C2	0.043 (2)	0.037 (2)	0.039 (2)	0.0009 (19)	0.0002 (19)	0.0008 (19)
C3	0.045 (2)	0.051 (3)	0.042 (3)	0.003 (2)	0.001 (2)	0.002 (2)
C4	0.056 (3)	0.062 (3)	0.043 (3)	0.020 (2)	−0.003 (2)	−0.005 (2)
C5	0.069 (3)	0.051 (3)	0.064 (4)	0.001 (3)	−0.016 (3)	−0.012 (3)
C6	0.050 (3)	0.056 (3)	0.064 (4)	−0.006 (2)	−0.006 (2)	−0.007 (3)
C7	0.041 (2)	0.035 (2)	0.052 (3)	−0.0002 (19)	0.007 (2)	0.001 (2)
C8	0.083 (4)	0.068 (4)	0.083 (4)	−0.030 (3)	0.024 (3)	0.003 (3)
C9	0.072 (3)	0.046 (3)	0.078 (4)	−0.022 (3)	0.015 (3)	−0.025 (3)
C10	0.065 (4)	0.079 (4)	0.089 (5)	−0.029 (3)	0.006 (3)	−0.041 (3)
C11	0.143 (6)	0.114 (5)	0.054 (4)	−0.046 (5)	0.003 (4)	−0.021 (4)
C12	0.083 (4)	0.065 (4)	0.128 (6)	0.003 (3)	0.020 (4)	−0.032 (4)
C13	0.046 (2)	0.029 (2)	0.066 (3)	0.0080 (19)	−0.010 (2)	0.003 (2)
C14	0.073 (4)	0.063 (4)	0.119 (5)	0.021 (3)	0.015 (4)	0.027 (4)

Zn—C13	2.022 (4)	C6—H6A	0.9300
Zn—O1i	2.060 (3)	C7—C8	1.516 (6)
Zn—O1	2.142 (3)	C8—H8A	0.9600
Zn—N1	2.180 (4)	C8—H8B	0.9600
Zn—N2	2.236 (4)	C8—H8C	0.9600
Br—C4	1.892 (4)	C9—C10	1.509 (7)
O1—C1	1.307 (5)	C9—H9A	0.9700
O1—Zni	2.060 (3)	C9—H9B	0.9700
N1—C7	1.273 (5)	C10—H10A	0.9700
N1—C9	1.460 (6)	C10—H10B	0.9700
N2—C10	1.451 (6)	C11—H11A	0.9600
N2—C12	1.464 (6)	C11—H11B	0.9600
N2—C11	1.471 (7)	C11—H11C	0.9600
C1—C6	1.398 (6)	C12—H12A	0.9600
C1—C2	1.417 (6)	C12—H12B	0.9600
C2—C3	1.413 (6)	C12—H12C	0.9600
C2—C7	1.475 (6)	C13—C14	1.472 (7)
C3—C4	1.382 (6)	C13—H13A	0.9700
C3—H3A	0.9300	C13—H13B	0.9700
C4—C5	1.384 (6)	C14—H14A	0.9600
C5—C6	1.383 (7)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C13—Zn—O1i	119.14 (15)	C7—C8—H8A	109.5
C13—Zn—O1	113.25 (15)	C7—C8—H8B	109.5
O1i—Zn—O1	74.93 (13)	H8A—C8—H8B	109.5
C13—Zn—N1	110.12 (16)	C7—C8—H8C	109.5
O1i—Zn—N1	129.91 (12)	H8A—C8—H8C	109.5
O1—Zn—N1	78.18 (13)	H8B—C8—H8C	109.5
C13—Zn—N2	114.09 (17)	N1—C9—C10	109.1 (4)
O1i—Zn—N2	89.20 (13)	N1—C9—H9A	109.9
O1—Zn—N2	131.93 (14)	C10—C9—H9A	109.9
N1—Zn—N2	78.48 (14)	N1—C9—H9B	109.9
C1—O1—Zni	136.0 (3)	C10—C9—H9B	109.9
C1—O1—Zn	112.2 (2)	H9A—C9—H9B	108.3
Zni—O1—Zn	105.00 (13)	N2—C10—C9	112.4 (4)
C7—N1—C9	121.2 (4)	N2—C10—H10A	109.1
C7—N1—Zn	125.7 (3)	C9—C10—H10A	109.1
C9—N1—Zn	113.1 (3)	N2—C10—H10B	109.1
C10—N2—C12	111.1 (4)	C9—C10—H10B	109.1
C10—N2—C11	110.7 (5)	H10A—C10—H10B	107.8
C12—N2—C11	107.3 (5)	N2—C11—H11A	109.5
C10—N2—Zn	103.4 (3)	N2—C11—H11B	109.5
C12—N2—Zn	114.4 (3)	H11A—C11—H11B	109.5
C11—N2—Zn	110.0 (3)	N2—C11—H11C	109.5
O1—C1—C6	121.5 (4)	H11A—C11—H11C	109.5
O1—C1—C2	120.4 (4)	H11B—C11—H11C	109.5
C6—C1—C2	118.0 (4)	N2—C12—H12A	109.5
C3—C2—C1	119.1 (4)	N2—C12—H12B	109.5
C3—C2—C7	119.6 (4)	H12A—C12—H12B	109.5
C1—C2—C7	121.4 (4)	N2—C12—H12C	109.5
C4—C3—C2	120.8 (4)	H12A—C12—H12C	109.5
C4—C3—H3A	119.6	H12B—C12—H12C	109.5
C2—C3—H3A	119.6	C14—C13—Zn	115.4 (3)
C3—C4—C5	120.4 (4)	C14—C13—H13A	108.4
C3—C4—Br	119.4 (4)	Zn—C13—H13A	108.4
C5—C4—Br	120.2 (4)	C14—C13—H13B	108.4
C4—C5—C6	119.3 (5)	Zn—C13—H13B	108.4
C4—C5—H5A	120.3	H13A—C13—H13B	107.5
C6—C5—H5A	120.3	C13—C14—H14A	109.5
C1—C6—C5	122.3 (4)	C13—C14—H14B	109.5
C1—C6—H6A	118.8	H14A—C14—H14B	109.5
C5—C6—H6A	118.8	C13—C14—H14C	109.5
N1—C7—C2	118.9 (4)	H14A—C14—H14C	109.5
N1—C7—C8	123.3 (4)	H14B—C14—H14C	109.5
C2—C7—C8	117.8 (4)

Zn—C13	2.022 (4)
Zn—O1i	2.060 (3)
Zn—O1	2.142 (3)
Zn—N1	2.180 (4)
Zn—N2	2.236 (4)

C13—Zn—O1i	119.14 (15)
C13—Zn—O1	113.25 (15)
O1i—Zn—O1	74.93 (13)
C13—Zn—N1	110.12 (16)
O1i—Zn—N1	129.91 (12)
O1—Zn—N1	78.18 (13)
C13—Zn—N2	114.09 (17)
O1i—Zn—N2	89.20 (13)
O1—Zn—N2	131.93 (14)
N1—Zn—N2	78.48 (14)

Symmetry code: (i) .