{4,4′-Dibromo-6,6′-dimeth­oxy-2,2′-[1,2-phenyl­enebis(nitrilo­methanylyl­idene)]-κ4O1,N,N′,O1′}nickel(II)

Sun, Y.

doi:10.1107/S1600536812004321

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m282

doi:10.1107/S1600536812004321

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{4,4′-Dibromo-6,6′-dimethoxy-2,2′-[1,2-phenylenebis(nitrilomethanylylidene)]-κ⁴O¹,N,N′,O^1′}nickel(II)

Yongling Sun ^a ^*

^aDepartment of Biology, Dezhou University, Dezhou 253023, People's Republic of China
^*Correspondence e-mail: sylswx@163.com

(Received 26 January 2012; accepted 2 February 2012; online 10 February 2012)

In the title complex, [Ni(C₂₂H₁₆Br₂N₂O₄)], the Ni^II ion is coordinated by two N atoms and two O atoms of a tetradentate 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_r = 590.90
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.170
S = 1.02
3613 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 1.61 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004321/lh5411sup1.cif

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

checkCIF report

Comment top

Schiff-bases ligands, especially for those which are chelating, play an important role in the development of coordination chemistry as they readily form stable complexes with most transition metals (Ghosh et al., 2006; Nayak et al., 2006). Here, we present the structure of a new Ni(II) complex based on the tetradentate chelating Schiff-base ligand 1,2-diaminobenzene-N,N'-bis (5-bromo-3-methoxysalicylideneimine).

The molecular structure of the title complex is shown in Figure 1. The coordination of the Ni^II ion is slightly distorted square-planar, formed by two N atoms and two O atoms of the Schiff-base ligand. The mean deviation from the plane formed by the two N atoms, two O atoms and the Ni^II ion is 0.0426 Å. The Ni—N and Ni—O bond lengths are consistent with the corresponding distances in other nickel(II) complexes containing similar chelating tetradentate schiff-base ligands (Wang et al., 1994; Bhattacharya et al., 2011; Yu et al., 2009; Kargar et al., 2009; Felices et al., 2009).

Related literature top

For Schiff bases 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 top

The Schiff-base ligand can be readily synthesized by condensation 1,2-diaminobenzene and 5-bromo-2-hydroxy-3-methoxybenzaldehyde with the ratio 1:2 in ethanol. The preparation of the title complex was carried out by the reaction of Ni(ClO₄)₂.6H₂O and the schiff-base ligand (1:1, molar ratio) in methanol. After the stirring process was continued for about half an hour at room temperature, the mixture was filtered and the filtrate was allowed to slowly evaporate in air for several days to produce crystals suitable for X-ray diffraction with a yield about 56%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001; 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure. Displacement ellipsoids are drawn at the 30% probability level.

{4,4'-Dibromo-6,6'-dimethoxy-2,2'-[1,2- phenylenebis(nitrilomethanylylidene)]- κ⁴O¹,N,N',O^1'}nickel(II) top

Crystal data top

[Ni(C₂₂H₁₆Br₂N₂O₄)]	F(000) = 1168
M_r = 590.90	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1048P)²] where P = (F_o² + 2F_c²)/3
3613 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 1.61 e Å⁻³
0 restraints	Δρ_min = −1.16 e Å⁻³

Crystal data top

[Ni(C₂₂H₁₆Br₂N₂O₄)]	V = 2068.3 (15) Å³
M_r = 590.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.288 (7) Å	µ = 4.84 mm⁻¹
b = 8.213 (3) Å	T = 293 K
c = 16.473 (7) Å	0.17 × 0.15 × 0.12 mm
β = 90.171 (8)°

Data collection top

Bruker APEXII diffractometer	3613 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2628 reflections with I > 2σ(I)
T_min = 0.494, T_max = 0.595	R_int = 0.088
9492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.02	Δρ_max = 1.61 e Å⁻³
3613 reflections	Δρ_min = −1.16 e Å⁻³
282 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₂H₁₆Br₂N₂O₄)]
M_r	590.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	15.288 (7), 8.213 (3), 16.473 (7)
β (°)	90.171 (8)
V (Å³)	2068.3 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.84
Crystal size (mm)	0.17 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.494, 0.595
No. of measured, independent and observed [I > 2σ(I)] reflections	9492, 3613, 2628
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.170, 1.02
No. of reflections	3613
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.61, −1.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2001), SAINT (Bruker, 2001, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

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