{6,6′-Dimeth­oxy-2,2′-[4-bromo-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}nickel(II) methanol solvate

Yu, M.-M.; Xu, H.; Shi, Q.-Z.; Wei, Y.-N.; Li, Z.-X.

doi:10.1107/S1600536809002104

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m225

doi:10.1107/S1600536809002104

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{6,6′-Dimethoxy-2,2′-[4-bromo-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) methanol solvate

Ming-Ming Yu,^a Hong Xu,^a Qiu-Zhi Shi,^a Ying-Nai Wei ^b and Zhan-Xian Li ^a ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and ^bCollege of Physical Science and Engineering, Zhengzhou University, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: lizx@zzu.edu.cn

(Received 6 January 2009; accepted 16 January 2009; online 23 January 2009)

In the title compound, [Ni(C₂₂H₁₇BrN₂O₄)]·CH₃OH, the Ni^II ion is in a slightly distorted square-planar geometry involving an N₂O₂ atom set of the tetradentate Schiff base ligand. The asymmetric unit contains one nickel complex and one methanol solvent molecule. The dihedral angle between the aromatic ring planes of the central aromatic ring and other two aromatic rings are 10.8 (3) and 6.0 (2)°. The crystal structure is stabilized by intermolecular C—H⋯O and C—H⋯Br and by intramolecular O—H⋯O hydrogen bonds.

Related literature

For Schiff base complexes in coordination chemistry, inorganic biochemistry, catalysis and optical materials, see: Aurangzeb et al. (1994 ); Fun & Kia (2008 ); Hulme et al. (1997 ); Li et al. (2008 ); Fei & Fang (2008 ); Xia et al. (2007 ); Zhang & Janiak (2001 ).

Experimental

Crystal data

[Ni(C₂₂H₁₇BrN₂O₄)]·CH₄O
M_r = 544.04
Triclinic, $[P \overline 1]$
a = 7.4991 (12) Å
b = 11.8367 (18) Å
c = 12.5428 (19) Å
α = 105.042 (2)°
β = 96.971 (3)°
γ = 95.932 (3)°
V = 1056.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 295 (2) K
0.12 × 0.08 × 0.04 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.726, T_max = 0.895
5680 measured reflections
4086 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.161
S = 1.14
4086 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N2—Ni1	1.862 (3)
N3—Ni1	1.851 (3)
O1—Ni1	1.841 (3)
O2—Ni1	1.840 (3)

O2—Ni1—O1	84.82 (12)
O2—Ni1—N3	93.97 (14)
O1—Ni1—N2	94.73 (14)
N3—Ni1—N2	86.59 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5′⋯O1	0.82	2.15	2.952 (4)	165
C15—H15⋯O5ⁱ	0.93	2.37	3.203 (5)	149
C23—H23B⋯Br1ⁱⁱ	0.96	2.84	3.556 (6)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002104/hg2467sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002104/hg2467Isup2.hkl

checkCIF report

Comment top

The synthesis and structural investigation of Schiff base complexes have attracted much attention due to their interesting structures and wide potential applications. They play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis and optical materials (Aurangzeb et al., 1994; Fun & Kia, 2008; Hulme et al., 1997; Li et al., 2008; Fei & Fang, 2008; Zhang & Janiak, 2001). Here, the synthesis and crystal structure of the title complex (I) are reported.

The molecular structure of title compound is showing in Fig. 1. The dihedral angles between the aromatic ring planes of the middle aromatic ring and other two aromatic rings are 10.8 (3)° and 6.0 (2)°, respectively. The crystal structure, is stabilized by intermolecular C—H···O and C—H···Br and intramolecular O—H···O hydrogen bonds.

Related literature top

For Schiff base complexes in coordination chemistry, inorganic biochemistry, catalysis and optical

materials, see: Aurangzeb et al. (1994); Fun & Kia (2008); Hulme et al. (1997); Li et al. (2008); Fei & Fang (2008); Xia et al. (2007); Zhang & Janiak (2001).

Experimental top

6,6'-Dimethoxy-2,2'-[-4-bromo-o-phenylenebis (nitrilomethylidyne)]diphenol was synthesized according to modified reported methods (Xia, et al., 2007). A mixture of NiCl₂.6H₂O (1 mmol, 237.7 mg), 6,6'-Dimethoxy-2,2'-[-4-bromo-o-phenylenebis (nitrilomethylidyne)]diphenol (1 mmol, 455.3 mg) in 40 ml methanol and 20 ml water was refluxed for forty minutes. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation at room temperature for three weeks.

Computing details top

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

Figures top

	Fig. 1. A view of complex (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

{6,6'-Dimethoxy-2,2'-[4-bromo-o- phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) methanol solvate top

Crystal data top

[Ni(C₂₂H₁₇BrN₂O₄)]·CH₄O	Z = 2
M_r = 544.04	F(000) = 552
Triclinic, P1	D_x = 1.710 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4991 (12) Å	Cell parameters from 4086 reflections
b = 11.8367 (18) Å	θ = 1.7–26.0°
c = 12.5428 (19) Å	µ = 2.85 mm⁻¹
α = 105.042 (2)°	T = 295 K
β = 96.971 (3)°	Block, brown
γ = 95.932 (3)°	0.12 × 0.08 × 0.04 mm
V = 1056.6 (3) Å³

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4086 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.726, T_max = 0.895	k = −14→12
5680 measured reflections	l = −13→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0951P)² + 0.0167P] where P = (F_o² + 2F_c²)/3
4086 reflections	(Δ/σ)_max = 0.003
291 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Ni(C₂₂H₁₇BrN₂O₄)]·CH₄O	γ = 95.932 (3)°
M_r = 544.04	V = 1056.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.4991 (12) Å	Mo Kα radiation
b = 11.8367 (18) Å	µ = 2.85 mm⁻¹
c = 12.5428 (19) Å	T = 295 K
α = 105.042 (2)°	0.12 × 0.08 × 0.04 mm
β = 96.971 (3)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4086 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3123 reflections with I > 2σ(I)
T_min = 0.726, T_max = 0.895	R_int = 0.018
5680 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.14	Δρ_max = 0.67 e Å⁻³
4086 reflections	Δρ_min = −0.61 e Å⁻³
291 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
C3	0.8652 (7)	0.0691 (4)	0.3998 (4)	0.0510 (12)
H3	0.8869	−0.0085	0.3912	0.061*
C4	0.7842 (7)	0.1013 (4)	0.3070 (4)	0.0471 (11)
C5	0.7428 (6)	0.2142 (4)	0.3178 (4)	0.0443 (10)
H5	0.6876	0.2363	0.2573	0.053*
C6	0.7873 (5)	0.2926 (4)	0.4224 (3)	0.0357 (9)
C1	0.8774 (6)	0.2549 (4)	0.5093 (3)	0.0370 (9)
C7	1.0169 (6)	0.3214 (4)	0.6961 (4)	0.0393 (10)
H7	1.0357	0.2435	0.6888	0.047*
C8	1.0843 (6)	0.4041 (4)	0.7991 (4)	0.0413 (10)
C9	1.1868 (7)	0.3673 (5)	0.8839 (4)	0.0521 (12)
H9	1.2006	0.2879	0.8717	0.063*
C10	1.2639 (7)	0.4443 (5)	0.9811 (4)	0.0569 (13)
H10	1.3277	0.4176	1.0358	0.068*
C11	1.2491 (7)	0.5644 (5)	1.0008 (4)	0.0552 (13)
H11	1.3035	0.6174	1.0683	0.066*
C12	1.1539 (7)	0.6045 (4)	0.9200 (4)	0.0477 (11)
C13	1.0650 (6)	0.5251 (4)	0.8169 (3)	0.0397 (10)
C14	1.2135 (11)	0.8037 (5)	1.0330 (5)	0.093 (2)
H14B	1.3419	0.8015	1.0451	0.139*
H14A	1.1605	0.7842	1.0930	0.139*
H14C	1.1918	0.8815	1.0304	0.139*
C15	0.6634 (5)	0.4582 (4)	0.3866 (3)	0.0368 (9)
H15	0.6145	0.4089	0.3162	0.044*
C16	0.6301 (5)	0.5774 (4)	0.4112 (3)	0.0371 (9)
C17	0.5302 (6)	0.6144 (5)	0.3271 (4)	0.0489 (11)
H17	0.4833	0.5601	0.2588	0.059*
C18	0.5021 (7)	0.7289 (5)	0.3451 (4)	0.0517 (12)
H18	0.4382	0.7527	0.2883	0.062*
C19	0.5680 (6)	0.8118 (4)	0.4482 (4)	0.0503 (12)
H19	0.5483	0.8900	0.4591	0.060*
C20	0.6611 (6)	0.7783 (4)	0.5328 (4)	0.0395 (10)
C21	0.6960 (5)	0.6590 (4)	0.5160 (3)	0.0343 (9)
C22	0.7016 (8)	0.9703 (4)	0.6604 (4)	0.0581 (13)
H22A	0.7580	1.0111	0.7354	0.087*
H22B	0.5737	0.9744	0.6532	0.087*
H22C	0.7536	1.0067	0.6091	0.087*
C23	0.7099 (11)	0.8110 (6)	0.8879 (5)	0.087 (2)
H23A	0.8401	0.8205	0.8984	0.131*
H23B	0.6687	0.8131	0.9578	0.131*
H23C	0.6685	0.8739	0.8607	0.131*
C2	0.9109 (5)	0.1459 (3)	0.4982 (3)	0.0303 (8)
H2	0.9658	0.1238	0.5588	0.036*
N2	0.7574 (4)	0.4124 (3)	0.4553 (3)	0.0349 (8)
N3	0.9301 (4)	0.3451 (3)	0.6101 (3)	0.0343 (7)
O1	0.7893 (4)	0.6322 (2)	0.5995 (2)	0.0385 (7)
O2	0.9756 (4)	0.5679 (3)	0.7446 (2)	0.0416 (7)
O3	1.1343 (6)	0.7207 (3)	0.9303 (3)	0.0678 (11)
O4	0.7307 (5)	0.8499 (3)	0.6360 (3)	0.0501 (8)
O5	0.6410 (5)	0.7031 (3)	0.8107 (3)	0.0665 (10)
H5'	0.6896	0.6966	0.7546	0.100*
Ni1	0.86214 (7)	0.48899 (4)	0.60223 (4)	0.03314 (19)
Br1	0.73229 (10)	−0.01370 (5)	0.16760 (5)	0.0796 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.053 (3)	0.038 (2)	0.064 (3)	0.013 (2)	0.013 (2)	0.013 (2)
C4	0.060 (3)	0.037 (2)	0.036 (2)	0.004 (2)	0.003 (2)	−0.0015 (19)
C5	0.051 (3)	0.042 (2)	0.036 (2)	0.006 (2)	0.004 (2)	0.0065 (19)
C6	0.034 (2)	0.033 (2)	0.037 (2)	0.0021 (16)	0.0070 (18)	0.0065 (18)
C1	0.033 (2)	0.038 (2)	0.039 (2)	0.0048 (17)	0.0081 (18)	0.0082 (19)
C7	0.038 (2)	0.040 (2)	0.044 (2)	0.0129 (18)	0.0070 (19)	0.0136 (19)
C8	0.039 (2)	0.049 (3)	0.036 (2)	0.0110 (19)	0.0031 (19)	0.013 (2)
C9	0.064 (3)	0.059 (3)	0.042 (3)	0.022 (2)	0.007 (2)	0.023 (2)
C10	0.059 (3)	0.069 (4)	0.045 (3)	0.023 (3)	−0.006 (2)	0.021 (3)
C11	0.052 (3)	0.066 (3)	0.040 (3)	0.004 (2)	−0.008 (2)	0.009 (2)
C12	0.052 (3)	0.049 (3)	0.039 (2)	0.006 (2)	−0.002 (2)	0.012 (2)
C13	0.039 (2)	0.046 (2)	0.037 (2)	0.0074 (18)	0.0071 (18)	0.0149 (19)
C14	0.146 (7)	0.053 (4)	0.055 (4)	−0.014 (4)	−0.031 (4)	0.006 (3)
C15	0.033 (2)	0.042 (2)	0.034 (2)	−0.0010 (17)	0.0043 (17)	0.0092 (18)
C16	0.029 (2)	0.046 (2)	0.038 (2)	0.0049 (17)	0.0049 (17)	0.0158 (19)
C17	0.044 (3)	0.062 (3)	0.043 (3)	0.009 (2)	−0.001 (2)	0.020 (2)
C18	0.049 (3)	0.066 (3)	0.046 (3)	0.018 (2)	−0.005 (2)	0.028 (2)
C19	0.049 (3)	0.048 (3)	0.063 (3)	0.015 (2)	0.008 (2)	0.029 (2)
C20	0.037 (2)	0.045 (2)	0.041 (2)	0.0072 (18)	0.0078 (19)	0.019 (2)
C21	0.028 (2)	0.040 (2)	0.037 (2)	0.0026 (16)	0.0065 (17)	0.0145 (18)
C22	0.074 (3)	0.036 (3)	0.066 (3)	0.018 (2)	0.012 (3)	0.014 (2)
C23	0.119 (6)	0.074 (4)	0.051 (3)	0.021 (4)	−0.015 (4)	−0.005 (3)
C2	0.034 (2)	0.0273 (19)	0.0283 (19)	0.0080 (15)	0.0012 (16)	0.0056 (16)
N2	0.0321 (17)	0.0362 (18)	0.0341 (18)	0.0026 (14)	0.0040 (15)	0.0070 (15)
N3	0.0323 (17)	0.0354 (18)	0.0341 (18)	0.0054 (14)	0.0072 (14)	0.0067 (15)
O1	0.0466 (17)	0.0355 (15)	0.0317 (15)	0.0087 (13)	−0.0023 (13)	0.0092 (12)
O2	0.0493 (17)	0.0393 (16)	0.0346 (15)	0.0074 (13)	−0.0034 (13)	0.0116 (13)
O3	0.100 (3)	0.044 (2)	0.045 (2)	−0.0022 (19)	−0.017 (2)	0.0069 (16)
O4	0.066 (2)	0.0355 (16)	0.0469 (19)	0.0123 (15)	0.0009 (16)	0.0103 (14)
O5	0.069 (3)	0.073 (3)	0.048 (2)	0.007 (2)	0.0067 (18)	0.0035 (18)
Ni1	0.0361 (3)	0.0314 (3)	0.0302 (3)	0.0051 (2)	0.0022 (2)	0.0068 (2)
Br1	0.1203 (6)	0.0507 (4)	0.0512 (4)	0.0185 (3)	−0.0019 (3)	−0.0107 (3)

Geometric parameters (Å, º) top

C3—C2	1.310 (6)	C15—N2	1.307 (5)
C3—C4	1.406 (7)	C15—C16	1.419 (6)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.380 (7)	C16—C17	1.408 (6)
C4—Br1	1.885 (4)	C16—C21	1.411 (6)
C5—C6	1.376 (6)	C17—C18	1.358 (7)
C5—H5	0.9300	C17—H17	0.9300
C6—C1	1.406 (6)	C18—C19	1.401 (7)
C6—N2	1.419 (5)	C18—H18	0.9300
C1—C2	1.316 (6)	C19—C20	1.366 (6)
C1—N3	1.409 (5)	C19—H19	0.9300
C7—N3	1.301 (5)	C20—O4	1.357 (5)
C7—C8	1.402 (6)	C20—C21	1.429 (6)
C7—H7	0.9300	C21—O1	1.315 (5)
C8—C13	1.417 (6)	C22—O4	1.423 (5)
C8—C9	1.423 (6)	C22—H22A	0.9600
C9—C10	1.339 (7)	C22—H22B	0.9600
C9—H9	0.9300	C22—H22C	0.9600
C10—C11	1.397 (7)	C23—O5	1.392 (7)
C10—H10	0.9300	C23—H23A	0.9600
C11—C12	1.381 (6)	C23—H23B	0.9600
C11—H11	0.9300	C23—H23C	0.9600
C12—O3	1.373 (6)	C2—H2	0.9300
C12—C13	1.425 (6)	N2—Ni1	1.862 (3)
C13—O2	1.299 (5)	N3—Ni1	1.851 (3)
C14—O3	1.419 (6)	O1—Ni1	1.841 (3)
C14—H14B	0.9600	O2—Ni1	1.840 (3)
C14—H14A	0.9600	O5—H5'	0.8200
C14—H14C	0.9600

C2—C3—C4	121.5 (4)	C18—C17—C16	120.4 (4)
C2—C3—H3	119.3	C18—C17—H17	119.8
C4—C3—H3	119.3	C16—C17—H17	119.8
C5—C4—C3	120.8 (4)	C17—C18—C19	120.9 (4)
C5—C4—Br1	120.8 (4)	C17—C18—H18	119.6
C3—C4—Br1	118.4 (4)	C19—C18—H18	119.6
C6—C5—C4	116.7 (4)	C20—C19—C18	120.4 (4)
C6—C5—H5	121.6	C20—C19—H19	119.8
C4—C5—H5	121.6	C18—C19—H19	119.8
C5—C6—C1	118.7 (4)	O4—C20—C19	125.8 (4)
C5—C6—N2	127.6 (4)	O4—C20—C21	114.0 (4)
C1—C6—N2	113.7 (3)	C19—C20—C21	120.2 (4)
C2—C1—C6	123.6 (4)	O1—C21—C16	123.9 (4)
C2—C1—N3	122.6 (4)	O1—C21—C20	117.6 (4)
C6—C1—N3	113.9 (4)	C16—C21—C20	118.5 (4)
N3—C7—C8	125.1 (4)	O4—C22—H22A	109.5
N3—C7—H7	117.4	O4—C22—H22B	109.5
C8—C7—H7	117.4	H22A—C22—H22B	109.5
C7—C8—C13	121.2 (4)	O4—C22—H22C	109.5
C7—C8—C9	119.1 (4)	H22A—C22—H22C	109.5
C13—C8—C9	119.5 (4)	H22B—C22—H22C	109.5
C10—C9—C8	121.5 (5)	O5—C23—H23A	109.5
C10—C9—H9	119.3	O5—C23—H23B	109.5
C8—C9—H9	119.3	H23A—C23—H23B	109.5
C9—C10—C11	120.5 (4)	O5—C23—H23C	109.5
C9—C10—H10	119.7	H23A—C23—H23C	109.5
C11—C10—H10	119.7	H23B—C23—H23C	109.5
C12—C11—C10	120.0 (5)	C3—C2—C1	118.5 (4)
C12—C11—H11	120.0	C3—C2—H2	120.7
C10—C11—H11	120.0	C1—C2—H2	120.7
O3—C12—C11	124.5 (4)	C15—N2—C6	121.1 (3)
O3—C12—C13	114.2 (4)	C15—N2—Ni1	126.4 (3)
C11—C12—C13	121.3 (5)	C6—N2—Ni1	112.5 (3)
O2—C13—C8	124.3 (4)	C7—N3—C1	119.6 (4)
O2—C13—C12	118.5 (4)	C7—N3—Ni1	127.2 (3)
C8—C13—C12	117.2 (4)	C1—N3—Ni1	113.2 (3)
O3—C14—H14B	109.5	C21—O1—Ni1	127.9 (3)
O3—C14—H14A	109.5	C13—O2—Ni1	128.0 (3)
H14B—C14—H14A	109.5	C12—O3—C14	116.9 (4)
O3—C14—H14C	109.5	C20—O4—C22	117.9 (4)
H14B—C14—H14C	109.5	C23—O5—H5'	109.5
H14A—C14—H14C	109.5	O2—Ni1—O1	84.82 (12)
N2—C15—C16	125.1 (4)	O2—Ni1—N3	93.97 (14)
N2—C15—H15	117.5	O1—Ni1—N3	177.54 (13)
C16—C15—H15	117.5	O2—Ni1—N2	177.07 (14)
C17—C16—C21	119.7 (4)	O1—Ni1—N2	94.73 (14)
C17—C16—C15	118.3 (4)	N3—Ni1—N2	86.59 (15)
C21—C16—C15	122.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5′···O1	0.82	2.15	2.952 (4)	165
C15—H15···O5ⁱ	0.93	2.37	3.203 (5)	149
C23—H23B···Br1ⁱⁱ	0.96	2.84	3.556 (6)	133

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₂₂H₁₇BrN₂O₄)]·CH₄O
M_r	544.04
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.4991 (12), 11.8367 (18), 12.5428 (19)
α, β, γ (°)	105.042 (2), 96.971 (3), 95.932 (3)
V (Å³)	1056.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.85
Crystal size (mm)	0.12 × 0.08 × 0.04

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.726, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	5680, 4086, 3123
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.161, 1.14
No. of reflections	4086
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.61

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

N2—Ni1	1.862 (3)	O1—Ni1	1.841 (3)
N3—Ni1	1.851 (3)	O2—Ni1	1.840 (3)

O2—Ni1—O1	84.82 (12)	O1—Ni1—N2	94.73 (14)
O2—Ni1—N3	93.97 (14)	N3—Ni1—N2	86.59 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5'···O1	0.8200	2.1510	2.952 (4)	164.84
C15—H15···O5ⁱ	0.9300	2.3673	3.203 (5)	149.35
C23—H23B···Br1ⁱⁱ	0.9600	2.8369	3.556 (6)	132.47

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z+1.

Acknowledgements

This work was supported by the Natural Science Foundation of China (grant No. 50873093).

References

Aurangzeb, N., Hulme, C. E., McAuliffe, C. A., Pritchard, R. G., Watkinson, M., Bermejo, M. R. & Sousa, A. (1994). J. Chem. Soc. Chem. Commun. pp. 2193–2195. CrossRef Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, m1116–m1117. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hulme, C. E., Watkinson, M., Haynes, M., Pritchard, R. G., McAuliffe, C. A., Jaiboon, N., Beagley, B., Sousa, A., Bermejo, M. R. & Fondo, M. (1997). J. Chem. Soc. Dalton Trans. pp. 1805–1814. CSD CrossRef Web of Science Google Scholar
Li, C.-H., Huang, K.-L., Dou, J.-M., Chi, Y.-N., Xu, Y.-Q., Shen, L., Wang, D.-Q. & Hu, C.-W. (2008). CrystEngComm, 8, 3141–3143. CAS Google Scholar
Fei, L. & Fang, Z. (2008). Acta Cryst. E64, m406. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2007). Acta Cryst. E63, o40–o41. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 2| February 2009| Page m225

doi:10.1107/S1600536809002104

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{6,6′-Dimeth­­oxy-2,2′-[4-bromo-o-phenyl­enebis(nitrilo­methyl­­idyne)]diphenolato}nickel(II) methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{6,6′-Dimethoxy-2,2′-[4-bromo-o-phenylenebis(nitrilomethylidyne)]diphenolato}nickel(II) methanol solvate