{4,4'-Dibromo-2,2'-[propane-1,3-diyl-bis(nitrilo-methyl-idyne)]diphenolato}zinc(II).

The title mononuclear zinc(II) complex, [Zn(C(17)H(14)Br(2)N(2)O(2))], possesses a crystallographically imposed C(2) axis. The Zn atom is four-coordinated by two O and two N atoms from two Schiff base ligands, forming a severely distorted square-planar geometry. The central C atom of the propyl group is disordered over two positions about the twofold axis.

Related literature

For background on the chemistry of Schiff base zinc(II) complexes and their biological activity, see: Anderson et al. (1997 ▶); Chohan & Kausar (1992 ▶, 1993 ▶); Chohan et al. (2003 ▶); Osowole et al. (2005 ▶); Yu et al., (2007 ▶). For related structures, see: Li & Zhang (2005 ▶); Wu et al. (2006 ▶); Xu et al. (2006 ▶); Ma et al. (2005 ▶); Ma, Gu et al. (2006 ▶); Ma, Lv et al. (2006 ▶); Ma, Wu et al. (2006 ▶).

Experimental

Crystal data

[Zn(C17H14Br2N2O2)]

M = 503.49

Monoclinic,

a = 21.418 (6) Å

b = 8.161 (2) Å

c = 9.524 (3) Å

β = 92.910 (3)°

V = 1662.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 6.30 mm−1

T = 298 (2) K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.143, T max = 0.152

4709 measured reflections

1809 independent reflections

1444 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.05

1809 reflections

121 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.64 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015602/rz2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015602/rz2218Isup2.hkl

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

[Zn(C17H14Br2N2O2)]	F000 = 984
Mr = 503.49	Dx = 2.011 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1595 reflections
a = 21.418 (6) Å	θ = 2.5–26.3º
b = 8.161 (2) Å	µ = 6.30 mm−1
c = 9.524 (3) Å	T = 298 (2) K
β = 92.910 (3)º	Block, colourless
V = 1662.6 (8) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1809 independent reflections
Radiation source: fine-focus sealed tube	1444 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −27→27
Tmin = 0.143, Tmax = 0.152	k = −10→9
4709 measured reflections	l = −12→11

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0396P)2 + 3.1273P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1809 reflections	Δρmax = 0.45 e Å−3
121 parameters	Δρmin = −0.64 e Å−3
3 restraints	Extinction correction: SHELXTL (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (5)

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	Occ. (<1)
Zn1	0.0000	0.01735 (7)	0.2500	0.0347 (2)
Br1	0.23023 (2)	0.25397 (6)	0.81463 (5)	0.0539 (2)
N1	0.04072 (14)	−0.1416 (3)	0.3803 (3)	0.0343 (7)
O1	0.05877 (12)	0.1867 (3)	0.2995 (3)	0.0370 (6)
C1	0.09920 (16)	0.1906 (4)	0.4060 (4)	0.0310 (8)
C2	0.10887 (15)	0.0587 (4)	0.5015 (4)	0.0298 (7)
C3	0.14983 (16)	0.0782 (5)	0.6219 (4)	0.0362 (8)
H3	0.1557	−0.0080	0.6851	0.043*
C4	0.18070 (17)	0.2229 (5)	0.6459 (4)	0.0367 (8)
C5	0.17583 (18)	0.3491 (5)	0.5466 (4)	0.0406 (9)
H5	0.1995	0.4439	0.5598	0.049*
C6	0.13625 (17)	0.3329 (5)	0.4299 (4)	0.0376 (8)
H6	0.1336	0.4176	0.3645	0.045*
C7	0.08158 (16)	−0.1003 (4)	0.4779 (4)	0.0332 (8)
H7	0.0949	−0.1827	0.5399	0.040*
C8	0.0244 (3)	−0.3170 (5)	0.3736 (5)	0.0577 (13)
H8A	0.0119	−0.3481	0.4652	0.069*
H8B	0.0623	−0.3752	0.3578	0.069*
C9	−0.0202 (3)	−0.3766 (8)	0.2766 (9)	0.0375 (17)	0.50
H9A	−0.024 (4)	−0.4935 (16)	0.280 (12)	0.080*	0.50
H9B	−0.059 (2)	−0.340 (9)	0.310 (11)	0.080*	0.50

	U11	U22	U33	U12	U13	U23
Zn1	0.0395 (4)	0.0264 (3)	0.0374 (4)	0.000	−0.0056 (2)	0.000
Br1	0.0500 (3)	0.0645 (4)	0.0453 (3)	−0.0064 (2)	−0.01642 (19)	−0.0038 (2)
N1	0.0442 (17)	0.0228 (15)	0.0354 (17)	0.0001 (13)	−0.0019 (14)	0.0015 (13)
O1	0.0465 (15)	0.0277 (13)	0.0354 (15)	−0.0030 (11)	−0.0111 (11)	0.0031 (11)
C1	0.0307 (18)	0.0281 (18)	0.034 (2)	0.0026 (14)	0.0015 (14)	−0.0022 (14)
C2	0.0269 (16)	0.0318 (19)	0.0304 (18)	0.0034 (14)	−0.0006 (13)	−0.0008 (14)
C3	0.0334 (18)	0.041 (2)	0.034 (2)	0.0074 (16)	0.0008 (15)	0.0032 (16)
C4	0.0270 (18)	0.045 (2)	0.037 (2)	0.0001 (15)	−0.0064 (15)	−0.0041 (17)
C5	0.039 (2)	0.036 (2)	0.046 (2)	−0.0077 (16)	−0.0026 (17)	−0.0016 (18)
C6	0.040 (2)	0.0304 (19)	0.042 (2)	−0.0015 (16)	−0.0026 (16)	0.0028 (16)
C7	0.0371 (19)	0.0305 (19)	0.0317 (19)	0.0077 (15)	−0.0009 (15)	0.0041 (15)
C8	0.097 (4)	0.025 (2)	0.051 (3)	−0.009 (2)	0.000 (3)	0.0003 (19)
C9	0.045 (5)	0.020 (3)	0.047 (5)	−0.001 (3)	−0.003 (4)	0.005 (3)

Zn1—O1	1.912 (3)	C4—C5	1.398 (6)
Zn1—O1i	1.912 (3)	C5—C6	1.370 (5)
Zn1—N1i	1.968 (3)	C5—H5	0.9300
Zn1—N1	1.968 (3)	C6—H6	0.9300
Br1—C4	1.897 (4)	C7—H7	0.9300
N1—C7	1.289 (5)	C8—C9	1.383 (9)
N1—C8	1.474 (5)	C8—C9i	1.509 (9)
O1—C1	1.301 (4)	C8—H8A	0.9600
C1—C2	1.417 (5)	C8—H8B	0.9599
C1—C6	1.419 (5)	C9—C9i	1.025 (15)
C2—C3	1.417 (5)	C9—C8i	1.509 (9)
C2—C7	1.436 (5)	C9—H9A	0.958 (10)
C3—C4	1.367 (5)	C9—H9B	0.960 (10)
C3—H3	0.9300
O1—Zn1—O1i	87.42 (16)	C5—C6—C1	121.8 (4)
O1—Zn1—N1i	153.75 (12)	C5—C6—H6	119.1
O1i—Zn1—N1i	93.21 (12)	C1—C6—H6	119.1
O1—Zn1—N1	93.21 (12)	N1—C7—C2	127.3 (3)
O1i—Zn1—N1	153.75 (12)	N1—C7—H7	116.4
N1i—Zn1—N1	97.53 (18)	C2—C7—H7	116.4
C7—N1—C8	115.9 (3)	C9—C8—N1	121.7 (5)
C7—N1—Zn1	123.0 (2)	N1—C8—C9i	110.9 (4)
C8—N1—Zn1	121.1 (3)	C9—C8—H8A	107.4
C1—O1—Zn1	127.9 (2)	N1—C8—H8A	107.1
O1—C1—C2	123.5 (3)	C9i—C8—H8A	140.4
O1—C1—C6	119.3 (3)	C9—C8—H8B	106.4
C2—C1—C6	117.2 (3)	N1—C8—H8B	106.6
C1—C2—C3	119.9 (3)	C9i—C8—H8B	72.7
C1—C2—C7	122.7 (3)	H8A—C8—H8B	106.8
C3—C2—C7	117.3 (3)	C9i—C9—C8	76.0 (9)
C4—C3—C2	120.4 (3)	C9i—C9—C8i	62.8 (8)
C4—C3—H3	119.8	C8—C9—C8i	121.7 (6)
C2—C3—H3	119.8	C9i—C9—H9A	95 (4)
C3—C4—C5	120.3 (4)	C8—C9—H9A	112 (7)
C3—C4—Br1	120.1 (3)	C8i—C9—H9A	111 (7)
C5—C4—Br1	119.6 (3)	C9i—C9—H9B	160 (5)
C6—C5—C4	120.0 (3)	C8—C9—H9B	105 (6)
C6—C5—H5	120.0	C8i—C9—H9B	102 (6)
C4—C5—H5	120.0	H9A—C9—H9B	103 (2)

Zn1—O1	1.912 (3)
Zn1—N1	1.968 (3)

O1—Zn1—O1i	87.42 (16)
O1—Zn1—N1i	153.75 (12)
O1—Zn1—N1	93.21 (12)

Symmetry code: (i) .