Dibromido{2-[1-(cyclo-propyl-imino)-eth-yl]pyridine}-zinc(II).

In the title compound, [ZnBr(2)(C(10)H(12)N(2))], the Zn(2+) ion is coordinated by the N,N'-bidentate Schiff base ligand and two bromode ions in a distorted tetra-hedral arrangement. The dihedral angle between the pyridine and the cyclo-propyl rings is 95.4 (8)°.

Related literature

For background to Schiff bases as chelating ligands, see: Hamaker et al. (2010 ▶); Wang et al. (2010 ▶); Mirkhani et al. (2010 ▶); Liu & Yang (2009 ▶). For similar zinc complexes, see: Zakrzewski & Lingafelter (1970 ▶); Gourbatsis et al. (1999 ▶); Merino et al. (2001 ▶); Majumder et al. (2006 ▶).

Experimental

Crystal data

[ZnBr2(C10H12N2)]

M = 385.41

Monoclinic,

a = 7.029 (3) Å

b = 14.090 (3) Å

c = 7.037 (2) Å

β = 111.820 (3)°

V = 647.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 8.04 mm−1

T = 298 K

0.23 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.259, T max = 0.283

4060 measured reflections

2408 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.165

S = 0.95

2408 reflections

137 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −1.09 e Å−3

Absolute structure: Flack (1983 ▶), 957 Friedel pairs

Flack parameter: −0.05 (3)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536810025201/hb5526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025201/hb5526Isup2.hkl

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

[ZnBr2(C10H12N2)]	F(000) = 372
Mr = 385.41	Dx = 1.978 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.029 (3) Å	Cell parameters from 1405 reflections
b = 14.090 (3) Å	θ = 2.8–25.0°
c = 7.037 (2) Å	µ = 8.04 mm−1
β = 111.820 (3)°	T = 298 K
V = 647.0 (4) Å3	Block, colourless
Z = 2	0.23 × 0.23 × 0.21 mm

Bruker APEXII CCD diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	1708 reflections with I > 2σ(I)
graphite	Rint = 0.104
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.259, Tmax = 0.283	k = −18→17
4060 measured reflections	l = −8→8

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0966P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
2408 reflections	Δρmax = 0.96 e Å−3
137 parameters	Δρmin = −1.09 e Å−3
1 restraint	Absolute structure: Flack (1983), 957 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.01583 (18)	0.10050 (8)	0.5412 (2)	0.0380 (3)
Br1	−0.0650 (2)	−0.05302 (9)	0.6175 (2)	0.0601 (4)
Br2	0.0576 (2)	0.12235 (9)	0.2262 (2)	0.0559 (4)
N1	−0.1663 (14)	0.2047 (7)	0.5832 (15)	0.040 (2)
N2	0.2313 (14)	0.1748 (7)	0.7783 (14)	0.036 (2)
C1	−0.3710 (18)	0.2147 (10)	0.491 (2)	0.050 (3)
H1	−0.4447	0.1674	0.4022	0.060*
C2	−0.477 (2)	0.2918 (10)	0.524 (2)	0.053 (3)
H2	−0.6184	0.2965	0.4582	0.064*
C3	−0.369 (2)	0.3597 (10)	0.652 (2)	0.057 (4)
H3	−0.4351	0.4134	0.6742	0.069*
C4	−0.158 (2)	0.3503 (9)	0.753 (2)	0.047 (3)
H4	−0.0833	0.3966	0.8450	0.056*
C5	−0.0622 (16)	0.2727 (8)	0.7166 (16)	0.034 (2)
C6	0.1628 (17)	0.2531 (8)	0.8195 (16)	0.036 (2)
C7	0.288 (2)	0.3276 (9)	0.968 (2)	0.058 (4)
H7A	0.2300	0.3390	1.0702	0.087*
H7B	0.2870	0.3854	0.8960	0.087*
H7C	0.4265	0.3057	1.0337	0.087*
C8	0.4414 (17)	0.1441 (9)	0.8788 (19)	0.044 (3)
H8	0.5438	0.1939	0.9385	0.053*
C9	0.471 (2)	0.0526 (10)	0.995 (2)	0.051 (3)
H9A	0.3501	0.0188	0.9917	0.061*
H9B	0.5889	0.0474	1.1220	0.061*
C10	0.511 (2)	0.0589 (11)	0.799 (2)	0.058 (4)
H10A	0.6518	0.0572	0.8084	0.070*
H10B	0.4131	0.0285	0.6781	0.070*

	U11	U22	U33	U12	U13	U23
Zn1	0.0393 (6)	0.0335 (7)	0.0441 (7)	−0.0027 (6)	0.0189 (5)	−0.0084 (6)
Br1	0.0749 (9)	0.0420 (7)	0.0784 (10)	−0.0192 (7)	0.0460 (8)	−0.0117 (7)
Br2	0.0672 (8)	0.0607 (9)	0.0464 (7)	−0.0071 (6)	0.0287 (7)	−0.0038 (6)
N1	0.039 (5)	0.039 (6)	0.039 (5)	0.000 (4)	0.010 (4)	−0.005 (4)
N2	0.040 (5)	0.037 (5)	0.029 (5)	0.004 (4)	0.011 (4)	0.009 (4)
C1	0.043 (7)	0.061 (8)	0.045 (7)	0.001 (6)	0.016 (6)	0.001 (6)
C2	0.056 (8)	0.056 (8)	0.056 (8)	0.029 (7)	0.030 (7)	0.009 (7)
C3	0.069 (9)	0.045 (8)	0.066 (9)	0.028 (7)	0.035 (8)	0.013 (7)
C4	0.066 (8)	0.034 (6)	0.045 (7)	0.006 (6)	0.026 (7)	0.001 (5)
C5	0.035 (6)	0.038 (6)	0.028 (5)	0.003 (5)	0.009 (5)	0.009 (5)
C6	0.051 (7)	0.031 (6)	0.030 (6)	−0.002 (5)	0.020 (5)	0.001 (4)
C7	0.065 (9)	0.041 (8)	0.061 (9)	−0.007 (6)	0.016 (8)	−0.014 (6)
C8	0.032 (6)	0.043 (7)	0.052 (7)	0.002 (5)	0.009 (5)	0.001 (6)
C9	0.052 (8)	0.047 (7)	0.054 (7)	0.012 (6)	0.019 (7)	0.015 (6)
C10	0.046 (7)	0.079 (10)	0.047 (7)	0.018 (7)	0.015 (6)	0.007 (7)

Zn1—N1	2.041 (9)	C4—H4	0.9300
Zn1—N2	2.073 (10)	C5—C6	1.500 (15)
Zn1—Br1	2.3488 (18)	C6—C7	1.514 (16)
Zn1—Br2	2.3616 (19)	C7—H7A	0.9600
N1—C1	1.348 (15)	C7—H7B	0.9600
N1—C5	1.350 (15)	C7—H7C	0.9600
N2—C6	1.279 (15)	C8—C10	1.48 (2)
N2—C8	1.446 (14)	C8—C9	1.498 (18)
C1—C2	1.383 (18)	C8—H8	0.9800
C1—H1	0.9300	C9—C10	1.506 (19)
C2—C3	1.34 (2)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.392 (19)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.358 (17)
N1—Zn1—N2	80.2 (4)	N2—C6—C5	117.9 (10)
N1—Zn1—Br1	114.3 (3)	N2—C6—C7	125.7 (11)
N2—Zn1—Br1	116.6 (3)	C5—C6—C7	116.4 (10)
N1—Zn1—Br2	110.2 (3)	C6—C7—H7A	109.5
N2—Zn1—Br2	112.4 (3)	C6—C7—H7B	109.5
Br1—Zn1—Br2	117.36 (7)	H7A—C7—H7B	109.5
C1—N1—C5	117.7 (10)	C6—C7—H7C	109.5
C1—N1—Zn1	128.4 (8)	H7A—C7—H7C	109.5
C5—N1—Zn1	113.8 (7)	H7B—C7—H7C	109.5
C6—N2—C8	123.3 (11)	N2—C8—C10	118.4 (11)
C6—N2—Zn1	113.2 (7)	N2—C8—C9	115.8 (10)
C8—N2—Zn1	123.4 (8)	C10—C8—C9	60.7 (9)
N1—C1—C2	123.2 (13)	N2—C8—H8	116.7
N1—C1—H1	118.4	C10—C8—H8	116.7
C2—C1—H1	118.4	C9—C8—H8	116.7
C3—C2—C1	117.8 (12)	C8—C9—C10	59.1 (9)
C3—C2—H2	121.1	C8—C9—H9A	117.9
C1—C2—H2	121.1	C10—C9—H9A	117.9
C2—C3—C4	120.3 (12)	C8—C9—H9B	117.9
C2—C3—H3	119.8	C10—C9—H9B	117.9
C4—C3—H3	119.8	H9A—C9—H9B	115.0
C5—C4—C3	119.3 (12)	C8—C10—C9	60.2 (8)
C5—C4—H4	120.4	C8—C10—H10A	117.8
C3—C4—H4	120.4	C9—C10—H10A	117.8
N1—C5—C4	121.6 (10)	C8—C10—H10B	117.8
N1—C5—C6	114.0 (10)	C9—C10—H10B	117.8
C4—C5—C6	124.3 (11)	H10A—C10—H10B	114.9

Table 1

Selected bond lengths (Å)

Zn1—N1	2.041 (9)
Zn1—N2	2.073 (10)
Zn1—Br1	2.3488 (18)
Zn1—Br2	2.3616 (19)