{6,6′-Dimeth­oxy-2,2′-[6-bromo­pyridine-2,3-diylbis(nitrilo­methyl­idyne)]­diphenol­ato}­copper(II) methanol solvate

Jia, Z.

doi:10.1107/S1600536809003316

metal-organic compounds

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Volume 65| Part 3| March 2009| Page m343

doi:10.1107/S1600536809003316

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{6,6′-Dimethoxy-2,2′-[6-bromopyridine-2,3-diylbis(nitrilomethylidyne)]diphenolato}copper(II) methanol solvate

Zhen Jia ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
^*Correspondence e-mail: dzxyjz@126.com

(Received 22 January 2009; accepted 27 January 2009; online 28 February 2009)

In the title compound, [Cu(C₂₁H₁₆BrN₃O₄)]·CH₃OH, the Cu^II ion is coordinated by two N [Cu—N = 1.814 (3) and 1.917 (3) Å] and two O [Cu—O = 1.805 (3) and 1.893 (3) Å] atoms from the tetradentate Schiff base ligand in a distorted square-planar geometry. In the crystal structure, the approximately planar Cu complex molecules are paired into centrosymmetric dimers with short intermolecular Cu⋯N distances of 3.162 (3) Å. Weak O---H...O hydrogen bonds may help to stabilize the structure.

Related literature

For a related crystal structure, see Saha et al. (2007 ). For general background, see: Ghosh et al. (2006 ); Nayak et al. (2006 ); Singh et al. (2007 ); Yu et al. (2007 ).

Experimental

Crystal data

[Cu(C₂₁H₁₆BrN₃O₄)]·CH₄O
M_r = 549.86
Triclinic, $[P \overline 1]$
a = 7.4520 (8) Å
b = 11.5402 (13) Å
c = 12.9432 (14) Å
α = 104.345 (2)°
β = 96.467 (2)°
γ = 96.531 (2)°
V = 1059.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.96 mm⁻¹
T = 293 (2) K
0.15 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.665, T_max = 0.737
5332 measured reflections
3705 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.139
S = 1.06
3705 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1	0.82	2.24	3.033 (5)	163
O5—H5⋯O3	0.82	2.63	3.165 (5)	124

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998 ); software used to prepare material for publication: XP.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003316/cv2514sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003316/cv2514Isup2.hkl

checkCIF report

Comment top

Schiff bases play an important role in the development of coordination chemistry as they readily form stable complexes with most of the transition metals, in which some could exhibit interesting properties (Yu et al., 2007; Ghosh et al., 2006; Singh et al., 2007; Nayak et al., 2006). Here, we report a new Cu^II complex based on the tetradentate Schiff-base ligand 6-bromo-2,3-diaminopyridine-N,N'-bis (3-methoxysalicylideneimine).

The geometry and labeling scheme for the crystal structure of the title complex are shown in Figure 1. The coordination sphere for the Cu^II ion in the title complex is a slightly distorted square planar, in which the four positions are occupied 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 Cu ion is only 0.0329 /A%, indicative of that these five atoms are nearly coplanar. The average bond lengths of Cu—N and Cu—O are 1.866 and 1.849 /A%, respectively, which are slightly shorter than the corresponding distances in aqua-(N,N'-ethylenebis(3-methoxysalicylaldiminato)-N,N',O,O')copper(II) (Saha, et al., 2007).

Related literature top

For a related crystal structure, see Saha et al. (2007). For general background, see: Ghosh et al. (2006); Nayak et al. (2006); Singh et al. (2007); Yu et al. (2007).

Experimental top

The Schiff base ligand was synthesized by condensation 6-bromo-2,3-diaminopyridine and 2-hydroxy-3-methoxybenzaldehyde with the ratio 1:2 in ethanol. The synthesis of the title complex was carried out by reacting Cu(ClO₄)₂.6H₂O, and the Schiff-base ligand (1:1, molar ratio) in methanol. After the stirring process was continued for about 30 min at room temperature, the mixture was filtered and the filtrate was allowed to partial evaporate in air for sevral days to produce crystals suitable for X-ray diffraction with a yield about 60%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP (Sheldrick, 1998).

Figures top

Fig. 1. View of the title compound with the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level. All H-atoms and the methanol molecule are omitted for clarity.

{6,6'-Dimethoxy-2,2'-[6-bromopyridine-2,3- diylbis(nitrilomethylidyne)]diphenolato}copper(II) methanol solvate top

Crystal data top

[Cu(C₂₁H₁₆BrN₃O₄)]·CH₄O	Z = 2
M_r = 549.86	F(000) = 554
Triclinic, P1	D_x = 1.723 Mg m⁻³ D_m = 1.723 Mg m⁻³ D_m measured by not measured
a = 7.4520 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5402 (13) Å	Cell parameters from 1770 reflections
c = 12.9432 (14) Å	θ = 3.0–24.5°
α = 104.345 (2)°	µ = 2.96 mm⁻¹
β = 96.467 (2)°	T = 293 K
γ = 96.531 (2)°	Block, blue
V = 1059.9 (2) Å³	0.15 × 0.13 × 0.11 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3705 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
T_min = 0.665, T_max = 0.737	k = −13→9
5332 measured reflections	l = −15→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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0831P)² + 0.2066P] where P = (F_o² + 2F_c²)/3
3705 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Cu(C₂₁H₁₆BrN₃O₄)]·CH₄O	γ = 96.531 (2)°
M_r = 549.86	V = 1059.9 (2) Å³
Triclinic, P1	Z = 2
a = 7.4520 (8) Å	Mo Kα radiation
b = 11.5402 (13) Å	µ = 2.96 mm⁻¹
c = 12.9432 (14) Å	T = 293 K
α = 104.345 (2)°	0.15 × 0.13 × 0.11 mm
β = 96.467 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2885 reflections with I > 2σ(I)
T_min = 0.665, T_max = 0.737	R_int = 0.019
5332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	Δρ_max = 0.73 e Å⁻³
3705 reflections	Δρ_min = −0.45 e Å⁻³
293 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
Cu1	0.36241 (7)	−0.01108 (4)	0.60230 (4)	0.03577 (19)
Br1	0.23295 (10)	−0.51353 (5)	0.16747 (4)	0.0761 (3)
O1	0.2903 (4)	0.1323 (3)	0.5995 (2)	0.0383 (7)
O2	0.2316 (5)	0.3501 (3)	0.6365 (3)	0.0485 (8)
O3	0.4745 (4)	0.0684 (3)	0.7448 (2)	0.0405 (7)
O4	0.6350 (5)	0.2207 (3)	0.9307 (3)	0.0634 (10)
O5	0.1419 (5)	0.2035 (3)	0.8114 (3)	0.0625 (10)
H5	0.2014	0.1945	0.7612	0.075*
N1	0.4117 (5)	−0.3542 (3)	0.4995 (3)	0.0425 (9)
N2	0.4290 (4)	−0.1555 (3)	0.6099 (3)	0.0332 (8)
N3	0.2583 (4)	−0.0873 (3)	0.4554 (3)	0.0314 (7)
C1	0.3764 (5)	−0.2447 (4)	0.5091 (3)	0.0360 (9)
C2	0.2886 (5)	−0.2069 (3)	0.4228 (3)	0.0334 (9)
C3	0.2440 (6)	−0.2854 (4)	0.3183 (4)	0.0451 (11)
H3	0.1896	−0.2613	0.2603	0.054*
C4	0.2859 (6)	−0.3987 (4)	0.3081 (4)	0.0450 (11)
C5	0.3641 (6)	−0.4313 (4)	0.3988 (4)	0.0465 (11)
H5A	0.3850	−0.5109	0.3896	0.056*
C6	0.1301 (5)	0.0772 (4)	0.4117 (3)	0.0359 (9)
C7	0.1961 (5)	0.1589 (4)	0.5164 (3)	0.0342 (9)
C8	0.1615 (6)	0.2776 (4)	0.5331 (4)	0.0397 (10)
C9	0.0664 (6)	0.3116 (4)	0.4483 (4)	0.0478 (12)
H9	0.0452	0.3913	0.4597	0.057*
C10	0.0008 (6)	0.2296 (5)	0.3456 (4)	0.0501 (12)
H10	−0.0619	0.2564	0.2919	0.060*
C11	0.0288 (6)	0.1147 (4)	0.3262 (4)	0.0443 (11)
H11	−0.0153	0.0602	0.2598	0.053*
C12	0.1635 (5)	−0.0414 (4)	0.3872 (3)	0.0366 (10)
H12	0.1166	−0.0913	0.3191	0.044*
C13	0.2030 (8)	0.4705 (4)	0.6604 (4)	0.0583 (14)
H13A	0.2575	0.5096	0.6117	0.087*
H13B	0.2576	0.5108	0.7331	0.087*
H13C	0.0743	0.4741	0.6527	0.087*
C14	0.5858 (6)	−0.0953 (4)	0.7995 (3)	0.0379 (10)
C15	0.5660 (6)	0.0254 (4)	0.8168 (3)	0.0372 (10)
C16	0.6525 (6)	0.1045 (4)	0.9197 (4)	0.0446 (11)
C17	0.7470 (7)	0.0636 (5)	1.0005 (4)	0.0547 (13)
H17	0.7998	0.1177	1.0657	0.066*
C18	0.7609 (7)	−0.0570 (5)	0.9823 (4)	0.0546 (13)
H18	0.8209	−0.0859	1.0356	0.066*
C19	0.6857 (7)	−0.1340 (5)	0.8852 (4)	0.0501 (12)
H19	0.6988	−0.2152	0.8731	0.060*
C20	0.5175 (6)	−0.1781 (4)	0.6964 (3)	0.0380 (10)
H20	0.5376	−0.2576	0.6890	0.046*
C21	0.7138 (11)	0.3026 (5)	1.0320 (5)	0.088 (2)
H21A	0.6589	0.2793	1.0888	0.132*
H21B	0.6927	0.3831	1.0316	0.132*
H21C	0.8428	0.3006	1.0435	0.132*
C22	0.2129 (10)	0.3101 (5)	0.8876 (5)	0.0784 (18)
H22A	0.2649	0.2925	0.9523	0.118*
H22B	0.1175	0.3582	0.9032	0.118*
H22C	0.3060	0.3538	0.8604	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0395 (3)	0.0311 (3)	0.0352 (3)	0.0046 (2)	0.0021 (2)	0.0076 (2)
Br1	0.1168 (6)	0.0451 (3)	0.0517 (4)	0.0169 (3)	−0.0020 (3)	−0.0105 (3)
O1	0.0485 (17)	0.0308 (15)	0.0337 (15)	0.0054 (13)	−0.0022 (13)	0.0085 (12)
O2	0.066 (2)	0.0302 (16)	0.0483 (19)	0.0142 (15)	0.0021 (16)	0.0084 (14)
O3	0.0484 (17)	0.0341 (16)	0.0364 (16)	0.0062 (13)	−0.0035 (14)	0.0086 (13)
O4	0.092 (3)	0.039 (2)	0.047 (2)	0.0006 (18)	−0.0166 (19)	0.0059 (16)
O5	0.071 (2)	0.062 (2)	0.048 (2)	0.0059 (19)	0.0110 (18)	0.0016 (18)
N1	0.045 (2)	0.032 (2)	0.050 (2)	0.0079 (16)	0.0042 (18)	0.0097 (18)
N2	0.0338 (18)	0.0295 (18)	0.0352 (19)	0.0026 (14)	0.0053 (15)	0.0074 (15)
N3	0.0306 (17)	0.0291 (18)	0.0335 (18)	0.0022 (14)	0.0043 (14)	0.0078 (15)
C1	0.032 (2)	0.035 (2)	0.039 (2)	0.0020 (18)	0.0081 (18)	0.0070 (19)
C2	0.033 (2)	0.028 (2)	0.036 (2)	−0.0014 (17)	0.0079 (18)	0.0032 (18)
C3	0.050 (3)	0.038 (3)	0.045 (3)	0.007 (2)	0.002 (2)	0.007 (2)
C4	0.054 (3)	0.034 (2)	0.039 (2)	0.006 (2)	0.007 (2)	−0.003 (2)
C5	0.051 (3)	0.034 (2)	0.054 (3)	0.011 (2)	0.014 (2)	0.006 (2)
C6	0.030 (2)	0.043 (3)	0.037 (2)	0.0034 (18)	0.0054 (18)	0.017 (2)
C7	0.032 (2)	0.034 (2)	0.039 (2)	0.0039 (17)	0.0082 (18)	0.0132 (19)
C8	0.038 (2)	0.039 (2)	0.043 (3)	0.0040 (19)	0.005 (2)	0.014 (2)
C9	0.045 (3)	0.048 (3)	0.059 (3)	0.015 (2)	0.009 (2)	0.024 (2)
C10	0.047 (3)	0.059 (3)	0.050 (3)	0.015 (2)	−0.002 (2)	0.026 (3)
C11	0.040 (2)	0.051 (3)	0.041 (3)	0.005 (2)	0.001 (2)	0.015 (2)
C12	0.035 (2)	0.040 (2)	0.033 (2)	−0.0013 (18)	0.0057 (18)	0.0082 (19)
C13	0.077 (4)	0.034 (3)	0.066 (3)	0.015 (2)	0.011 (3)	0.014 (2)
C14	0.037 (2)	0.043 (3)	0.036 (2)	0.0122 (19)	0.0084 (19)	0.011 (2)
C15	0.037 (2)	0.041 (2)	0.035 (2)	0.0035 (18)	0.0057 (18)	0.0137 (19)
C16	0.046 (3)	0.045 (3)	0.040 (3)	0.002 (2)	0.000 (2)	0.010 (2)
C17	0.053 (3)	0.065 (3)	0.040 (3)	0.001 (2)	−0.005 (2)	0.011 (2)
C18	0.063 (3)	0.059 (3)	0.042 (3)	0.020 (3)	−0.007 (2)	0.017 (2)
C19	0.057 (3)	0.052 (3)	0.049 (3)	0.020 (2)	0.006 (2)	0.022 (2)
C20	0.040 (2)	0.035 (2)	0.043 (2)	0.0151 (19)	0.009 (2)	0.014 (2)
C21	0.139 (6)	0.042 (3)	0.060 (4)	−0.012 (3)	−0.032 (4)	0.002 (3)
C22	0.104 (5)	0.064 (4)	0.053 (3)	0.016 (3)	−0.008 (3)	−0.004 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.805 (3)	C7—C8	1.392 (6)
Cu1—N2	1.814 (3)	C8—C9	1.400 (6)
Cu1—O3	1.893 (3)	C9—C10	1.423 (7)
Cu1—N3	1.917 (3)	C9—H9	0.9300
Br1—C4	1.936 (4)	C10—C11	1.332 (6)
O1—C7	1.337 (5)	C10—H10	0.9300
O2—C13	1.393 (5)	C11—H11	0.9300
O2—C8	1.398 (5)	C12—H12	0.9300
O3—C15	1.320 (5)	C13—H13A	0.9600
O4—C16	1.335 (6)	C13—H13B	0.9600
O4—C21	1.430 (6)	C13—H13C	0.9600
O5—C22	1.378 (6)	C14—C15	1.382 (6)
O5—H5	0.8200	C14—C20	1.434 (6)
N1—C1	1.298 (5)	C14—C19	1.456 (6)
N1—C5	1.366 (6)	C15—C16	1.447 (6)
N2—C20	1.331 (5)	C16—C17	1.402 (6)
N2—C1	1.430 (5)	C17—C18	1.371 (7)
N3—C12	1.317 (5)	C17—H17	0.9300
N3—C2	1.392 (5)	C18—C19	1.364 (7)
C1—C2	1.417 (6)	C18—H18	0.9300
C2—C3	1.408 (6)	C19—H19	0.9300
C3—C4	1.356 (6)	C20—H20	0.9300
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.405 (7)	C21—H21B	0.9600
C5—H5A	0.9300	C21—H21C	0.9600
C6—C12	1.385 (6)	C22—H22A	0.9600
C6—C7	1.441 (6)	C22—H22B	0.9600
C6—C11	1.451 (6)	C22—H22C	0.9600

O1—Cu1—N2	177.45 (14)	C9—C10—H10	119.9
O1—Cu1—O3	85.51 (12)	C10—C11—C6	118.1 (4)
N2—Cu1—O3	93.31 (13)	C10—C11—H11	121.0
O1—Cu1—N3	93.72 (13)	C6—C11—H11	121.0
N2—Cu1—N3	87.57 (14)	N3—C12—C6	123.4 (4)
O3—Cu1—N3	177.17 (13)	N3—C12—H12	118.3
C7—O1—Cu1	127.0 (3)	C6—C12—H12	118.3
C13—O2—C8	117.2 (4)	O2—C13—H13A	109.5
C15—O3—Cu1	129.7 (3)	O2—C13—H13B	109.5
C16—O4—C21	116.2 (4)	H13A—C13—H13B	109.5
C22—O5—H5	109.5	O2—C13—H13C	109.5
C1—N1—C5	115.7 (4)	H13A—C13—H13C	109.5
C20—N2—C1	123.0 (3)	H13B—C13—H13C	109.5
C20—N2—Cu1	125.7 (3)	C15—C14—C20	119.8 (4)
C1—N2—Cu1	111.3 (3)	C15—C14—C19	118.7 (4)
C12—N3—C2	119.4 (3)	C20—C14—C19	121.3 (4)
C12—N3—Cu1	128.3 (3)	O3—C15—C14	123.0 (4)
C2—N3—Cu1	112.3 (3)	O3—C15—C16	120.7 (4)
N1—C1—C2	123.0 (4)	C14—C15—C16	116.2 (4)
N1—C1—N2	120.0 (4)	O4—C16—C17	122.9 (4)
C2—C1—N2	116.9 (4)	O4—C16—C15	113.8 (4)
N3—C2—C3	127.0 (4)	C17—C16—C15	123.3 (4)
N3—C2—C1	111.8 (3)	C18—C17—C16	119.3 (5)
C3—C2—C1	121.3 (4)	C18—C17—H17	120.3
C4—C3—C2	115.3 (4)	C16—C17—H17	120.3
C4—C3—H3	122.4	C19—C18—C17	119.1 (4)
C2—C3—H3	122.4	C19—C18—H18	120.4
C3—C4—C5	120.1 (4)	C17—C18—H18	120.4
C3—C4—Br1	118.7 (4)	C18—C19—C14	123.2 (4)
C5—C4—Br1	121.2 (3)	C18—C19—H19	118.4
N1—C5—C4	124.5 (4)	C14—C19—H19	118.4
N1—C5—H5A	117.7	N2—C20—C14	128.2 (4)
C4—C5—H5A	117.7	N2—C20—H20	115.9
C12—C6—C7	121.2 (4)	C14—C20—H20	115.9
C12—C6—C11	116.5 (4)	O4—C21—H21A	109.5
C7—C6—C11	122.3 (4)	O4—C21—H21B	109.5
O1—C7—C8	116.2 (4)	H21A—C21—H21B	109.5
O1—C7—C6	126.3 (4)	O4—C21—H21C	109.5
C8—C7—C6	117.5 (4)	H21A—C21—H21C	109.5
C7—C8—O2	113.3 (4)	H21B—C21—H21C	109.5
C7—C8—C9	118.9 (4)	O5—C22—H22A	109.5
O2—C8—C9	127.8 (4)	O5—C22—H22B	109.5
C8—C9—C10	123.0 (4)	H22A—C22—H22B	109.5
C8—C9—H9	118.5	O5—C22—H22C	109.5
C10—C9—H9	118.5	H22A—C22—H22C	109.5
C11—C10—C9	120.3 (4)	H22B—C22—H22C	109.5
C11—C10—H10	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.82	2.24	3.033 (5)	163
O5—H5···O3	0.82	2.63	3.165 (5)	124

Experimental details

Crystal data
Chemical formula	[Cu(C₂₁H₁₆BrN₃O₄)]·CH₄O
M_r	549.86
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4520 (8), 11.5402 (13), 12.9432 (14)
α, β, γ (°)	104.345 (2), 96.467 (2), 96.531 (2)
V (Å³)	1059.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.96
Crystal size (mm)	0.15 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.665, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	5332, 3705, 2885
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.139, 1.06
No. of reflections	3705
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.45

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.82	2.24	3.033 (5)	163.2
O5—H5···O3	0.82	2.63	3.165 (5)	124.1

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ghosh, R., Rahaman, S. H., Lin, C. N., Lu, T. H. & Ghosh, B. K. (2006). Polyhedron, 25, 3104–3112. Web of Science CSD CrossRef CAS Google Scholar
Nayak, M., Koner, R., Lin, H. H., Flörke, U., Wei, H. H. & Mohanta, S. (2006). Inorg. Chem. 45, 10764–10773. Web of Science CSD CrossRef PubMed CAS Google Scholar
Saha, P. K., Dutta, B., Jana, S., Bera, R., Saha, S., Okamoto, K. & Koner, S. (2007). Polyhedron, 26, 563–571. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, K., Barwa, M. S. & Tyagi, P. (2007). Eur. J. Med. Chem. 42, 394–402. Web of Science CrossRef PubMed CAS Google Scholar
Yu, T. Z., Zhang, K., Zhao, Y. L., Yang, C. H., Zhang, H., Fan, D. W. & Dong, W. K. (2007). Inorg. Chem. Commun. 10, 401–403. Web of Science CSD CrossRef CAS Google Scholar

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Volume 65| Part 3| March 2009| Page m343

doi:10.1107/S1600536809003316

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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′-[6-bromo­pyridine-2,3-diylbis(nitrilo­methyl­­idyne)]­diphenol­ato}­copper(II) methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

{6,6′-Dimethoxy-2,2′-[6-bromopyridine-2,3-diylbis(nitrilomethylidyne)]diphenolato}copper(II) methanol solvate