{4,4'-Dibromo-6,6'-dimeth-oxy-2,2'-[1,2-phenyl-enebis(nitrilo-methanylyl-idene)]-κO,N,N',O}nickel(II).

In the title complex, [Ni(C(22)H(16)Br(2)N(2)O(4))], the Ni(II) ion is coordinated by two N atoms and two O atoms of a tetra-dentate Schiff base ligand, forming a slightly distorted square-planar coordination environment. The dihedral angle between the two bromo-substituted benzene rings is 10.1 (3)°.

Related literature

For Schiff base ligands in coordination chemistry, see: Ghosh et al. (2006 ▶); Nayak et al. (2006 ▶). For related structures, see: Wang et al. (1994 ▶); Bhattacharya et al. (2011 ▶); Yu et al. (2009 ▶); Kargar et al. (2009 ▶); Felices et al. (2009 ▶).

Experimental

Crystal data

[Ni(C22H16Br2N2O4)]

M = 590.90

Monoclinic,

a = 15.288 (7) Å

b = 8.213 (3) Å

c = 16.473 (7) Å

β = 90.171 (8)°

V = 2068.3 (15) Å3

Z = 4

Mo Kα radiation

μ = 4.84 mm−1

T = 293 K

0.17 × 0.15 × 0.12 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.494, T max = 0.595

9492 measured reflections

3613 independent reflections

2628 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.170

S = 1.02

3613 reflections

282 parameters

H-atom parameters constrained

Δρmax = 1.61 e Å−3

Δρmin = −1.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812004321/lh5411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004321/lh5411Isup2.hkl

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

[Ni(C22H16Br2N2O4)]	F(000) = 1168
Mr = 590.90	Dx = 1.898 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2246 reflections
a = 15.288 (7) Å	θ = 2.5–25.7°
b = 8.213 (3) Å	µ = 4.84 mm−1
c = 16.473 (7) Å	T = 293 K
β = 90.171 (8)°	Block, red-brown
V = 2068.3 (15) Å3	0.17 × 0.15 × 0.12 mm
Z = 4

Bruker APEXII diffractometer	3613 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→18
Tmin = 0.494, Tmax = 0.595	k = −9→9
9492 measured reflections	l = −19→17

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) = 0.170	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1048P)2] where P = (Fo2 + 2Fc2)/3
3613 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 1.61 e Å−3
0 restraints	Δρmin = −1.16 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
Ni1	0.03371 (5)	0.81849 (9)	0.06315 (4)	0.0308 (3)
Br1	0.20569 (5)	0.28032 (9)	−0.25514 (4)	0.0469 (3)
Br2	0.01289 (5)	1.43548 (10)	0.38330 (5)	0.0626 (3)
O1	0.1366 (3)	0.7166 (5)	0.0303 (3)	0.0393 (11)
O2	0.2972 (3)	0.6233 (6)	0.0006 (3)	0.0521 (13)
O3	0.1011 (3)	0.9012 (5)	0.1472 (2)	0.0376 (10)
O4	0.2250 (3)	1.0180 (5)	0.2414 (3)	0.0446 (12)
N1	−0.0338 (3)	0.7335 (6)	−0.0210 (3)	0.0325 (12)
N2	−0.0688 (3)	0.9208 (6)	0.0960 (3)	0.0326 (12)
C1	−0.1227 (4)	0.7828 (7)	−0.0186 (4)	0.0368 (15)
C2	−0.1425 (4)	0.8846 (7)	0.0455 (4)	0.0337 (14)
C3	−0.2253 (4)	0.9459 (8)	0.0556 (4)	0.0434 (17)
H3	−0.2377	1.0151	0.0988	0.052*
C4	−0.2910 (5)	0.9029 (10)	0.0002 (4)	0.0535 (19)
H4	−0.3474	0.9436	0.0061	0.064*
C5	−0.2714 (5)	0.7999 (9)	−0.0633 (4)	0.0500 (18)
H5	−0.3151	0.7710	−0.0999	0.060*
C6	−0.1887 (4)	0.7393 (8)	−0.0735 (4)	0.0404 (15)
H6	−0.1765	0.6698	−0.1165	0.048*
C7	0.0816 (4)	0.5844 (7)	−0.0892 (3)	0.0327 (14)
C8	0.1486 (4)	0.6307 (7)	−0.0341 (4)	0.0334 (14)
C9	0.2345 (4)	0.5739 (8)	−0.0532 (4)	0.0394 (16)
C10	0.2505 (4)	0.4733 (8)	−0.1171 (4)	0.0373 (15)
H10	0.3069	0.4355	−0.1268	0.045*
C11	0.1814 (5)	0.4272 (7)	−0.1684 (4)	0.0388 (16)
C12	0.0991 (4)	0.4797 (7)	−0.1560 (4)	0.0368 (15)
H12	0.0541	0.4480	−0.1907	0.044*
C13	−0.0056 (4)	0.6388 (7)	−0.0782 (4)	0.0358 (15)
H13	−0.0468	0.6029	−0.1158	0.043*
C14	0.3853 (5)	0.5783 (12)	−0.0163 (6)	0.079 (3)
H14A	0.3907	0.4619	−0.0148	0.118*
H14B	0.4235	0.6256	0.0236	0.118*
H14C	0.4012	0.6171	−0.0692	0.118*
C15	−0.0078 (4)	1.0701 (7)	0.2093 (4)	0.0317 (14)
C16	0.0768 (4)	1.0105 (7)	0.1998 (4)	0.0332 (14)
C17	0.1444 (4)	1.0825 (7)	0.2515 (4)	0.0363 (15)
C18	0.1245 (5)	1.2049 (8)	0.3053 (4)	0.0429 (17)
H18	0.1681	1.2509	0.3374	0.051*
C19	0.0388 (5)	1.2591 (8)	0.3112 (4)	0.0413 (16)
C20	−0.0283 (4)	1.1942 (7)	0.2665 (4)	0.0371 (15)
H20	−0.0855	1.2302	0.2732	0.045*
C21	−0.0772 (4)	1.0202 (7)	0.1578 (4)	0.0329 (14)
H21	−0.1328	1.0609	0.1686	0.039*
C22	0.2969 (4)	1.1049 (9)	0.2789 (4)	0.0475 (18)
H22A	0.2974	1.2154	0.2598	0.071*
H22B	0.3511	1.0530	0.2649	0.071*
H22C	0.2899	1.1040	0.3367	0.071*

	U11	U22	U33	U12	U13	U23
Ni1	0.0287 (5)	0.0273 (5)	0.0365 (5)	−0.0011 (3)	−0.0063 (3)	−0.0006 (3)
Br1	0.0521 (5)	0.0431 (5)	0.0457 (4)	−0.0035 (3)	0.0063 (3)	−0.0091 (3)
Br2	0.0549 (5)	0.0639 (6)	0.0688 (6)	0.0049 (4)	−0.0057 (4)	−0.0335 (4)
O1	0.034 (3)	0.038 (3)	0.045 (3)	−0.0006 (19)	−0.0068 (19)	−0.008 (2)
O2	0.034 (3)	0.063 (3)	0.059 (3)	0.001 (2)	−0.008 (2)	−0.021 (3)
O3	0.031 (2)	0.035 (2)	0.046 (3)	0.0019 (19)	−0.0116 (18)	−0.005 (2)
O4	0.036 (3)	0.038 (3)	0.060 (3)	0.001 (2)	−0.016 (2)	−0.012 (2)
N1	0.030 (3)	0.032 (3)	0.035 (3)	−0.006 (2)	−0.004 (2)	0.003 (2)
N2	0.030 (3)	0.029 (3)	0.039 (3)	−0.003 (2)	−0.006 (2)	0.005 (2)
C1	0.044 (4)	0.027 (3)	0.039 (4)	−0.003 (3)	−0.006 (3)	0.005 (3)
C2	0.030 (3)	0.028 (3)	0.043 (4)	−0.001 (3)	−0.009 (3)	0.005 (3)
C3	0.035 (4)	0.048 (4)	0.047 (4)	0.007 (3)	−0.007 (3)	−0.003 (3)
C4	0.030 (4)	0.074 (5)	0.056 (5)	0.005 (4)	−0.007 (3)	−0.004 (4)
C5	0.045 (4)	0.055 (5)	0.050 (4)	−0.004 (3)	−0.017 (3)	0.003 (3)
C6	0.036 (4)	0.046 (4)	0.039 (4)	−0.003 (3)	−0.011 (3)	−0.001 (3)
C7	0.036 (4)	0.028 (3)	0.035 (3)	−0.002 (3)	−0.006 (3)	0.005 (3)
C8	0.032 (3)	0.031 (3)	0.037 (3)	0.000 (3)	−0.005 (3)	0.002 (3)
C9	0.033 (4)	0.035 (4)	0.049 (4)	−0.007 (3)	−0.001 (3)	0.002 (3)
C10	0.032 (4)	0.036 (4)	0.044 (4)	0.003 (3)	0.006 (3)	0.001 (3)
C11	0.055 (5)	0.027 (3)	0.034 (4)	−0.001 (3)	0.002 (3)	0.000 (3)
C12	0.044 (4)	0.030 (3)	0.037 (4)	−0.007 (3)	−0.010 (3)	0.002 (3)
C13	0.044 (4)	0.025 (3)	0.038 (4)	−0.008 (3)	−0.012 (3)	0.002 (3)
C14	0.032 (4)	0.117 (8)	0.087 (6)	0.003 (5)	−0.011 (4)	−0.041 (6)
C15	0.036 (4)	0.025 (3)	0.034 (3)	−0.004 (3)	−0.003 (3)	0.001 (2)
C16	0.039 (4)	0.024 (3)	0.036 (3)	−0.003 (3)	−0.010 (3)	0.001 (3)
C17	0.030 (4)	0.029 (3)	0.050 (4)	0.002 (3)	−0.005 (3)	0.001 (3)
C18	0.043 (4)	0.040 (4)	0.045 (4)	−0.003 (3)	−0.012 (3)	−0.009 (3)
C19	0.047 (4)	0.039 (4)	0.038 (4)	0.002 (3)	−0.004 (3)	−0.009 (3)
C20	0.041 (4)	0.031 (4)	0.040 (4)	0.003 (3)	−0.001 (3)	−0.002 (3)
C21	0.029 (3)	0.030 (3)	0.040 (4)	−0.001 (3)	0.001 (3)	0.003 (3)
C22	0.036 (4)	0.045 (4)	0.061 (4)	−0.005 (3)	−0.018 (3)	−0.007 (3)

Ni1—O3	1.852 (4)	C7—C8	1.418 (8)
Ni1—N2	1.859 (5)	C7—C13	1.418 (9)
Ni1—N1	1.861 (5)	C7—C12	1.423 (8)
Ni1—O1	1.863 (4)	C8—C9	1.429 (9)
Br1—C11	1.908 (6)	C9—C10	1.362 (9)
Br2—C19	1.915 (6)	C10—C11	1.402 (9)
O1—C8	1.288 (7)	C10—H10	0.9300
O2—C9	1.365 (7)	C11—C12	1.347 (9)
O2—C14	1.426 (9)	C12—H12	0.9300
O3—C16	1.302 (7)	C13—H13	0.9300
O4—C17	1.351 (7)	C14—H14A	0.9600
O4—C22	1.448 (7)	C14—H14B	0.9600
N1—C13	1.297 (8)	C14—H14C	0.9600
N1—C1	1.419 (8)	C15—C16	1.392 (9)
N2—C21	1.312 (7)	C15—C21	1.417 (8)
N2—C2	1.430 (7)	C15—C20	1.423 (8)
C1—C2	1.381 (9)	C16—C17	1.462 (8)
C1—C6	1.398 (8)	C17—C18	1.375 (9)
C2—C3	1.374 (9)	C18—C19	1.387 (10)
C3—C4	1.400 (9)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.370 (9)
C4—C5	1.379 (10)	C20—H20	0.9300
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.369 (10)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
O3—Ni1—N2	94.8 (2)	C9—C10—H10	120.2
O3—Ni1—N1	179.5 (2)	C11—C10—H10	120.2
N2—Ni1—N1	85.4 (2)	C12—C11—C10	121.7 (6)
O3—Ni1—O1	85.07 (18)	C12—C11—Br1	120.0 (5)
N2—Ni1—O1	179.8 (2)	C10—C11—Br1	118.3 (5)
N1—Ni1—O1	94.7 (2)	C11—C12—C7	119.2 (5)
C8—O1—Ni1	127.5 (4)	C11—C12—H12	120.4
C9—O2—C14	117.2 (5)	C7—C12—H12	120.4
C16—O3—Ni1	126.3 (4)	N1—C13—C7	126.6 (5)
C17—O4—C22	116.5 (5)	N1—C13—H13	116.7
C13—N1—C1	120.7 (5)	C7—C13—H13	116.7
C13—N1—Ni1	125.6 (4)	O2—C14—H14A	109.5
C1—N1—Ni1	113.7 (4)	O2—C14—H14B	109.5
C21—N2—C2	120.1 (5)	H14A—C14—H14B	109.5
C21—N2—Ni1	126.3 (4)	O2—C14—H14C	109.5
C2—N2—Ni1	113.6 (4)	H14A—C14—H14C	109.5
C2—C1—C6	119.3 (6)	H14B—C14—H14C	109.5
C2—C1—N1	113.9 (5)	C16—C15—C21	121.7 (5)
C6—C1—N1	126.8 (6)	C16—C15—C20	122.2 (5)
C3—C2—C1	121.2 (5)	C21—C15—C20	115.9 (6)
C3—C2—N2	125.4 (6)	O3—C16—C15	125.7 (5)
C1—C2—N2	113.4 (5)	O3—C16—C17	117.7 (5)
C2—C3—C4	119.2 (6)	C15—C16—C17	116.6 (5)
C2—C3—H3	120.4	O4—C17—C18	124.8 (5)
C4—C3—H3	120.4	O4—C17—C16	114.3 (5)
C5—C4—C3	119.5 (7)	C18—C17—C16	120.9 (6)
C5—C4—H4	120.3	C17—C18—C19	119.4 (6)
C3—C4—H4	120.3	C17—C18—H18	120.3
C6—C5—C4	121.3 (6)	C19—C18—H18	120.3
C6—C5—H5	119.4	C20—C19—C18	122.9 (6)
C4—C5—H5	119.4	C20—C19—Br2	118.2 (5)
C5—C6—C1	119.5 (6)	C18—C19—Br2	119.0 (5)
C5—C6—H6	120.2	C19—C20—C15	118.0 (6)
C1—C6—H6	120.2	C19—C20—H20	121.0
C8—C7—C13	120.8 (5)	C15—C20—H20	121.0
C8—C7—C12	121.3 (6)	N2—C21—C15	124.7 (6)
C13—C7—C12	117.9 (5)	N2—C21—H21	117.7
O1—C8—C7	124.7 (5)	C15—C21—H21	117.7
O1—C8—C9	119.6 (5)	O4—C22—H22A	109.5
C7—C8—C9	115.7 (6)	O4—C22—H22B	109.5
C10—C9—O2	123.7 (6)	H22A—C22—H22B	109.5
C10—C9—C8	122.4 (6)	O4—C22—H22C	109.5
O2—C9—C8	113.8 (6)	H22A—C22—H22C	109.5
C9—C10—C11	119.5 (6)	H22B—C22—H22C	109.5