Dibromido{2-morpholino-N-[1-(2-pyrid-yl)ethyl-idene]ethanamine-κN,N',N''}zinc(II).

In the title complex, [ZnBr(2)(C(13)H(19)N(3)O)], the Zn(II) atom is five-coordinated by the three N-donor atoms of the Schiff base ligand and by two Br atoms in a distorted square-pyramidal geometry. The morpholine ring adopts a chair conformation.

Related literature

For background to Schiff base complexes, see: Dhar & Chakravarty (2003 ▶); Das et al. (2006 ▶); Nayak et al. (2006 ▶). For the crystal structures of similar Schiff base–zinc(II) complexes, see: Wang (2010 ▶); Zhu et al. (2007 ▶); Li & Zhang (2004 ▶); Zhu & Yang (2008 ▶).

Experimental

Crystal data

[ZnBr2(C13H19N3O)]

M = 458.50

Monoclinic,

a = 9.831 (4) Å

b = 13.985 (6) Å

c = 12.183 (5) Å

β = 106.626 (4)°

V = 1604.9 (11) Å3

Z = 4

Mo Kα radiation

μ = 6.51 mm−1

T = 298 K

0.35 × 0.32 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.209, T max = 0.230

12426 measured reflections

3411 independent reflections

2159 reflections with I > 2σ(I)

R int = 0.108

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.177

S = 1.05

3411 reflections

182 parameters

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −1.26 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2007 ▶); 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 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002753/su2250sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002753/su2250Isup2.hkl

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

[ZnBr2(C13H19N3O)]	F(000) = 904
Mr = 458.50	Dx = 1.898 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1887 reflections
a = 9.831 (4) Å	θ = 2.3–25.1°
b = 13.985 (6) Å	µ = 6.51 mm−1
c = 12.183 (5) Å	T = 298 K
β = 106.626 (4)°	Block, colourless
V = 1604.9 (11) Å3	0.35 × 0.32 × 0.32 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3411 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 2σ(I)
graphite	Rint = 0.108
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.209, Tmax = 0.230	k = −17→17
12426 measured reflections	l = −15→15

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0584P)2 + 5.9893P] where P = (Fo2 + 2Fc2)/3
3411 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 1.35 e Å−3
0 restraints	Δρmin = −1.26 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	0.27265 (9)	0.91109 (6)	0.83908 (8)	0.0207 (3)
Br1	0.45896 (10)	0.79761 (8)	0.87089 (9)	0.0448 (3)
Br2	0.04314 (10)	0.86043 (7)	0.72941 (9)	0.0418 (3)
O1	0.3163 (7)	0.9365 (6)	0.4853 (6)	0.0490 (19)
N1	0.2385 (7)	0.8835 (5)	1.0100 (6)	0.0247 (16)
N2	0.2537 (7)	1.0444 (5)	0.9095 (6)	0.0252 (16)
N3	0.3418 (6)	1.0118 (5)	0.7105 (5)	0.0227 (15)
C1	0.1995 (7)	0.9617 (6)	1.0565 (6)	0.0210 (18)
C2	0.1623 (9)	0.9559 (7)	1.1573 (7)	0.033 (2)
H2	0.1349	1.0105	1.1889	0.040*
C3	0.1660 (11)	0.8680 (8)	1.2116 (8)	0.044 (3)
H3	0.1394	0.8630	1.2788	0.053*
C4	0.2089 (10)	0.7900 (8)	1.1649 (8)	0.042 (3)
H4	0.2155	0.7307	1.2006	0.051*
C5	0.2422 (10)	0.8003 (7)	1.0642 (8)	0.036 (2)
H5	0.2690	0.7460	1.0314	0.043*
C6	0.2071 (8)	1.0522 (6)	0.9937 (7)	0.0251 (19)
C7	0.1620 (9)	1.1447 (6)	1.0362 (8)	0.036 (2)
H7A	0.2439	1.1770	1.0840	0.054*
H7B	0.0967	1.1315	1.0797	0.054*
H7C	0.1167	1.1847	0.9721	0.054*
C8	0.2824 (10)	1.1260 (6)	0.8452 (8)	0.036 (2)
H8A	0.3204	1.1785	0.8969	0.043*
H8B	0.1954	1.1472	0.7902	0.043*
C9	0.3870 (10)	1.0959 (6)	0.7849 (8)	0.037 (2)
H9A	0.4031	1.1489	0.7388	0.045*
H9B	0.4764	1.0815	0.8414	0.045*
C10	0.4615 (9)	0.9792 (7)	0.6732 (8)	0.038 (2)
H10A	0.5339	0.9538	0.7384	0.045*
H10B	0.5020	1.0331	0.6434	0.045*
C11	0.4195 (12)	0.9037 (7)	0.5826 (9)	0.046 (3)
H11A	0.5026	0.8835	0.5610	0.055*
H11B	0.3829	0.8487	0.6135	0.055*
C12	0.1956 (11)	0.9629 (8)	0.5184 (8)	0.048 (3)
H12A	0.1594	0.9073	0.5485	0.057*
H12B	0.1223	0.9850	0.4516	0.057*
C13	0.2283 (9)	1.0409 (7)	0.6081 (8)	0.036 (2)
H13A	0.2573	1.0982	0.5759	0.043*
H13B	0.1432	1.0558	0.6298	0.043*

	U11	U22	U33	U12	U13	U23
Zn1	0.0158 (5)	0.0246 (5)	0.0212 (5)	−0.0006 (4)	0.0046 (4)	−0.0044 (4)
Br1	0.0322 (6)	0.0540 (7)	0.0475 (7)	0.0094 (5)	0.0102 (5)	0.0007 (5)
Br2	0.0264 (5)	0.0500 (6)	0.0486 (7)	−0.0049 (4)	0.0101 (4)	−0.0081 (5)
O1	0.038 (4)	0.083 (5)	0.030 (4)	0.004 (4)	0.016 (3)	−0.002 (4)
N1	0.022 (4)	0.032 (4)	0.019 (4)	0.004 (3)	0.004 (3)	−0.001 (3)
N2	0.024 (4)	0.027 (4)	0.022 (4)	0.000 (3)	0.001 (3)	−0.004 (3)
N3	0.018 (3)	0.028 (4)	0.020 (4)	−0.003 (3)	0.004 (3)	0.005 (3)
C1	0.007 (4)	0.037 (5)	0.015 (4)	0.000 (3)	−0.003 (3)	−0.005 (3)
C2	0.025 (5)	0.049 (6)	0.027 (5)	−0.005 (4)	0.007 (4)	−0.015 (4)
C3	0.046 (6)	0.070 (8)	0.014 (5)	−0.009 (5)	0.006 (4)	0.002 (5)
C4	0.052 (6)	0.049 (6)	0.025 (5)	−0.006 (5)	0.010 (5)	0.009 (5)
C5	0.035 (5)	0.034 (5)	0.036 (6)	0.006 (4)	0.007 (4)	0.000 (4)
C6	0.021 (4)	0.028 (4)	0.023 (5)	−0.003 (3)	0.002 (4)	−0.010 (4)
C7	0.028 (5)	0.034 (5)	0.047 (6)	0.010 (4)	0.014 (4)	−0.012 (4)
C8	0.051 (6)	0.026 (5)	0.031 (5)	−0.008 (4)	0.012 (5)	−0.006 (4)
C9	0.040 (6)	0.032 (5)	0.037 (6)	−0.023 (4)	0.006 (4)	−0.002 (4)
C10	0.020 (5)	0.055 (6)	0.041 (6)	−0.003 (4)	0.011 (4)	0.008 (5)
C11	0.051 (6)	0.055 (7)	0.041 (6)	0.007 (5)	0.027 (5)	−0.003 (5)
C12	0.043 (6)	0.072 (8)	0.023 (5)	−0.005 (5)	0.002 (5)	−0.003 (5)
C13	0.030 (5)	0.042 (6)	0.035 (5)	0.002 (4)	0.007 (4)	0.008 (4)

Zn1—N2	2.083 (7)	C4—H4	0.9300
Zn1—N1	2.235 (7)	C5—H5	0.9300
Zn1—N3	2.347 (6)	C6—C7	1.507 (11)
Zn1—Br1	2.3701 (15)	C7—H7A	0.9600
Zn1—Br2	2.3775 (15)	C7—H7B	0.9600
O1—C11	1.398 (12)	C7—H7C	0.9600
O1—C12	1.407 (12)	C8—C9	1.485 (13)
N1—C5	1.334 (11)	C8—H8A	0.9700
N1—C1	1.337 (10)	C8—H8B	0.9700
N2—C6	1.241 (11)	C9—H9A	0.9700
N2—C8	1.457 (11)	C9—H9B	0.9700
N3—C10	1.451 (11)	C10—C11	1.496 (13)
N3—C13	1.474 (10)	C10—H10A	0.9700
N3—C9	1.474 (10)	C10—H10B	0.9700
C1—C2	1.380 (12)	C11—H11A	0.9700
C1—C6	1.492 (11)	C11—H11B	0.9700
C2—C3	1.391 (14)	C12—C13	1.512 (13)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.352 (14)	C12—H12B	0.9700
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.365 (13)	C13—H13B	0.9700
N2—Zn1—N1	73.5 (3)	C6—C7—H7B	109.5
N2—Zn1—N3	79.4 (3)	H7A—C7—H7B	109.5
N1—Zn1—N3	151.0 (2)	C6—C7—H7C	109.5
N2—Zn1—Br1	133.48 (18)	H7A—C7—H7C	109.5
N1—Zn1—Br1	92.70 (17)	H7B—C7—H7C	109.5
N3—Zn1—Br1	98.80 (16)	N2—C8—C9	108.2 (7)
N2—Zn1—Br2	108.40 (19)	N2—C8—H8A	110.1
N1—Zn1—Br2	95.80 (18)	C9—C8—H8A	110.1
N3—Zn1—Br2	102.32 (16)	N2—C8—H8B	110.1
Br1—Zn1—Br2	117.20 (6)	C9—C8—H8B	110.1
C11—O1—C12	108.1 (7)	H8A—C8—H8B	108.4
C5—N1—C1	118.3 (8)	N3—C9—C8	113.6 (7)
C5—N1—Zn1	128.4 (6)	N3—C9—H9A	108.8
C1—N1—Zn1	113.1 (5)	C8—C9—H9A	108.8
C6—N2—C8	123.3 (7)	N3—C9—H9B	108.8
C6—N2—Zn1	121.2 (6)	C8—C9—H9B	108.8
C8—N2—Zn1	115.2 (5)	H9A—C9—H9B	107.7
C10—N3—C13	107.9 (7)	N3—C10—C11	112.0 (7)
C10—N3—C9	108.4 (7)	N3—C10—H10A	109.2
C13—N3—C9	108.8 (7)	C11—C10—H10A	109.2
C10—N3—Zn1	115.9 (5)	N3—C10—H10B	109.2
C13—N3—Zn1	115.9 (5)	C11—C10—H10B	109.2
C9—N3—Zn1	99.3 (5)	H10A—C10—H10B	107.9
N1—C1—C2	120.6 (8)	O1—C11—C10	112.0 (8)
N1—C1—C6	114.4 (7)	O1—C11—H11A	109.2
C2—C1—C6	124.9 (8)	C10—C11—H11A	109.2
C1—C2—C3	119.9 (9)	O1—C11—H11B	109.2
C1—C2—H2	120.1	C10—C11—H11B	109.2
C3—C2—H2	120.1	H11A—C11—H11B	107.9
C4—C3—C2	118.7 (9)	O1—C12—C13	112.0 (8)
C4—C3—H3	120.6	O1—C12—H12A	109.2
C2—C3—H3	120.6	C13—C12—H12A	109.2
C3—C4—C5	118.5 (9)	O1—C12—H12B	109.2
C3—C4—H4	120.7	C13—C12—H12B	109.2
C5—C4—H4	120.7	H12A—C12—H12B	107.9
N1—C5—C4	123.9 (9)	N3—C13—C12	111.5 (8)
N1—C5—H5	118.1	N3—C13—H13A	109.3
C4—C5—H5	118.1	C12—C13—H13A	109.3
N2—C6—C1	115.7 (7)	N3—C13—H13B	109.3
N2—C6—C7	125.1 (8)	C12—C13—H13B	109.3
C1—C6—C7	119.3 (8)	H13A—C13—H13B	108.0
C6—C7—H7A	109.5