[5,5′-Dihydr­oxy-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato}copper(II) methanol disolvate

Niu, M.; Fan, S.; Liu, K.; Cao, Z.; Wang, D.

doi:10.1107/S1600536809053720

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m77

doi:10.1107/S1600536809053720

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[5,5′-Dihydroxy-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}copper(II) methanol disolvate

Meiju Niu,^a ^* Shumei Fan,^b Kai Liu,^a Zhiqiang Cao ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bDongchang College Liaocheng University, Shandong 252000, People's Republic of China
^*Correspondence e-mail: niumeiju@163.com

(Received 26 November 2009; accepted 14 December 2009; online 19 December 2009)

In the title compound, [Cu(C₂₀H₁₄N₂O₄)]·2CH₃OH, the Cu^II ion is coordinated by two N [Cu—N = 1.933 (2) and 1.941 (2) Å] and two O [Cu—O = 1.890 (2) and 1.9038 (19) Å] atoms from the tetradentate Schiff base ligand 5,5′-dihydroxy-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolate (L) in a distorted square-planar geometry. In the crystal, intermolecular O—H⋯O hydrogen bonds link two CuL molecules and four solvent molecules into a centrosymmetric cluster. The crystal packing exhibits short intermolecular C⋯C contacts of 3.185 (4) and 3.232 (4) Å.

Related literature

For related structures, see: Amirnasr et al. (2006 ); Arola-Arnal et al. (2008 ); Sundaravel et al. (2009 ); Lu et al. (2006 ).

Experimental

Crystal data

[Cu(C₂₀H₁₄N₂O₄)]·2CH₄O
M_r = 473.96
Triclinic, $[P \overline 1]$
a = 7.9520 (17) Å
b = 11.066 (2) Å
c = 11.870 (2) Å
α = 91.796 (2)°
β = 94.604 (3)°
γ = 94.241 (3)°
V = 1037.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 293 K
0.53 × 0.48 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.595, T_max = 0.803
5360 measured reflections
3592 independent reflections
2873 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.00
3592 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.82	1.91	2.704 (3)	163
O4—H4⋯O6ⁱⁱ	0.82	1.82	2.602 (4)	159
O5—H5⋯O4ⁱⁱⁱ	0.82	1.97	2.788 (3)	176
O6—H6⋯O1	0.82	2.18	2.777 (3)	130
O6—H6⋯O3	0.82	2.34	3.037 (4)	144
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+2, -z+1; (iii) -x+2, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536809053720/cv2670sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053720/cv2670Isup2.hkl

checkCIF report

Comment top

Copper complexes have attracted intensive interest in the past decade because they play important roles on the fields of coordination chemistry, bioinorganic chemistry, redox enzyme systems and others (Amirnasr et al., 2006). In a continuation of a study of Schiff base ligands and their copper(II) complexes, we report here the title complex, (I).

In (I) (Fig. 1),the main plane being formed by the three phenyl and the N₂O₂. The angles O1—Cu1—N2 (178.64 (9)°) and O3—Cu1—N1 (178.39 (9)°) indicate that the coordination geometry of the copper atom is four-coordinate in an approximately square planar, which acts as a tetradentate ligand through its o-phenylenediamine N atoms and its deprotonated phenol O atoms. This square planar geometry is the most usual for Cu^II complexes (Arola-Arnal et al., 2008) in the N₂0₂ donor set with Schiff base ligands. The Cu—O distances of 1.9022 (19)Å and 1.889 (2)Å are very close to the corresponding values in related structures (1.904 (2)Å and 1.884 (3) Å; Sundaravel et al., 2009). The Cu—N distances of 1.932 (2)Å and 1.942 (2)Å are very close to the corresponding values in related structures(1.946 (2) Å; Lu et al., 2006). Intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into a centrosymmetric cluster.

Related literature top

For related structures, see: Amirnasr et al. (2006); Arola-Arnal et al. (2008); Sundaravel et al. (2009); Lu et al. (2006).

Experimental top

o-Phenylenediamine(1 mmol, 108.22 mg) was dissolved in hot ethanol (20 ml) and added dropwise to a ethanol solution (10 ml) of 2,4-dihydroxybenzaldehyde (2 mmol, 276.2 mg). The mixture was then stirred at 323 K for 4 h. The triethylamine solution (3 ml) of Copper (II) acetate (1.5 mmol, 299.5 mg) was then added dropwise and the mixture stirred for another 5 h, at which point a red precipitate collected by suction filtration and washed with ethanol and ether. Crystals of the title compound suitable for X-ray analysis were from the methanol and dimethylformamide solution after about two weeks.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 of the title compound showing the atomic labels and 30% probability displacement ellipsoids.

[5,5'-Dihydroxy-2,2'-[o- phenylenebis(nitrilomethylidyne)]diphenolato}copper(II) methanol disolvate top

Crystal data top

[Cu(C₂₀H₁₄N₂O₄)]·2CH₄O	Z = 2
M_r = 473.96	F(000) = 490
Triclinic, P1	D_x = 1.517 Mg m⁻³
a = 7.9520 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.066 (2) Å	Cell parameters from 2490 reflections
c = 11.870 (2) Å	θ = 2.5–26.4°
α = 91.796 (2)°	µ = 1.10 mm⁻¹
β = 94.604 (3)°	T = 293 K
γ = 94.241 (3)°	Block, red
V = 1037.6 (4) Å³	0.53 × 0.48 × 0.21 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	2873 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.595, T_max = 0.803	k = −12→13
5360 measured reflections	l = −14→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0446P)² + 0.5623P] where P = (F_o² + 2F_c²)/3
3592 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Cu(C₂₀H₁₄N₂O₄)]·2CH₄O	γ = 94.241 (3)°
M_r = 473.96	V = 1037.6 (4) Å³
Triclinic, P1	Z = 2
a = 7.9520 (17) Å	Mo Kα radiation
b = 11.066 (2) Å	µ = 1.10 mm⁻¹
c = 11.870 (2) Å	T = 293 K
α = 91.796 (2)°	0.53 × 0.48 × 0.21 mm
β = 94.604 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3592 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2873 reflections with I > 2σ(I)
T_min = 0.595, T_max = 0.803	R_int = 0.027
5360 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.46 e Å⁻³
3592 reflections	Δρ_min = −0.36 e Å⁻³
280 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	0.84950 (4)	0.91865 (3)	0.07516 (3)	0.03348 (14)
N1	0.7711 (3)	0.9467 (2)	−0.07955 (19)	0.0322 (5)
N2	0.9482 (3)	0.7807 (2)	0.00880 (19)	0.0317 (5)
O1	0.7530 (2)	1.05584 (16)	0.13697 (16)	0.0356 (5)
O2	0.4653 (3)	1.41526 (18)	0.14493 (19)	0.0522 (6)
H2	0.4991	1.4142	0.2120	0.078*
O3	0.9320 (3)	0.89012 (18)	0.22501 (16)	0.0433 (5)
O4	1.2805 (4)	0.7377 (2)	0.52128 (19)	0.0724 (8)
H4	1.2474	0.7960	0.5551	0.109*
O5	0.6076 (4)	0.4576 (2)	0.3584 (2)	0.0780 (8)
H5	0.6454	0.4010	0.3927	0.117*
O6	0.7454 (6)	1.0573 (3)	0.3705 (3)	0.1286 (17)
H6	0.8050	1.0433	0.3191	0.193*
C1	0.8192 (4)	0.8588 (3)	−0.1582 (2)	0.0374 (7)
C2	0.9139 (4)	0.7681 (3)	−0.1106 (3)	0.0373 (7)
C3	0.9676 (4)	0.6789 (3)	−0.1807 (3)	0.0455 (8)
H3	1.0314	0.6191	−0.1498	0.055*
C4	0.9275 (5)	0.6780 (3)	−0.2961 (3)	0.0581 (9)
H4A	0.9624	0.6170	−0.3425	0.070*
C5	0.8358 (6)	0.7674 (3)	−0.3423 (3)	0.0670 (11)
H5A	0.8101	0.7672	−0.4201	0.080*
C6	0.7815 (5)	0.8574 (3)	−0.2742 (3)	0.0561 (9)
H6A	0.7193	0.9174	−0.3063	0.067*
C7	0.6728 (4)	1.0312 (3)	−0.1095 (2)	0.0351 (7)
H7	0.6340	1.0315	−0.1855	0.042*
C8	0.6194 (3)	1.1225 (2)	−0.0376 (2)	0.0318 (6)
C9	0.6652 (3)	1.1344 (2)	0.0815 (2)	0.0314 (6)
C10	0.6127 (4)	1.2337 (2)	0.1415 (3)	0.0366 (7)
H10	0.6430	1.2431	0.2188	0.044*
C11	0.5170 (4)	1.3183 (3)	0.0890 (3)	0.0378 (7)
C12	0.4682 (4)	1.3056 (3)	−0.0271 (3)	0.0436 (8)
H12	0.4022	1.3618	−0.0624	0.052*
C13	0.5181 (4)	1.2108 (3)	−0.0873 (3)	0.0395 (7)
H13	0.4849	1.2029	−0.1643	0.047*
C14	1.0398 (4)	0.7072 (2)	0.0662 (2)	0.0357 (7)
H14	1.0792	0.6432	0.0259	0.043*
C15	1.0849 (4)	0.7158 (2)	0.1845 (2)	0.0361 (7)
C16	1.0355 (4)	0.8091 (2)	0.2577 (2)	0.0356 (7)
C17	1.1031 (4)	0.8149 (3)	0.3713 (3)	0.0444 (8)
H17	1.0741	0.8761	0.4198	0.053*
C18	1.2108 (4)	0.7320 (3)	0.4118 (3)	0.0487 (8)
C19	1.2564 (4)	0.6381 (3)	0.3410 (3)	0.0500 (8)
H19	1.3279	0.5813	0.3690	0.060*
C20	1.1945 (4)	0.6318 (3)	0.2312 (3)	0.0438 (8)
H20	1.2253	0.5696	0.1844	0.053*
C21	0.7229 (7)	0.5589 (4)	0.3737 (5)	0.1056 (17)
H21A	0.7013	0.6045	0.4404	0.158*
H21B	0.7110	0.6087	0.3092	0.158*
H21C	0.8358	0.5332	0.3820	0.158*
C22	0.6689 (6)	0.9506 (5)	0.4033 (4)	0.0857 (14)
H22A	0.6713	0.9513	0.4843	0.129*
H22B	0.7282	0.8840	0.3772	0.129*
H22C	0.5537	0.9418	0.3714	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0365 (2)	0.0294 (2)	0.0349 (2)	0.00663 (14)	0.00252 (14)	−0.00080 (14)
N1	0.0339 (13)	0.0275 (12)	0.0353 (13)	0.0012 (10)	0.0054 (10)	−0.0027 (10)
N2	0.0280 (12)	0.0304 (12)	0.0360 (13)	−0.0005 (10)	0.0034 (10)	−0.0040 (10)
O1	0.0411 (11)	0.0303 (10)	0.0356 (11)	0.0106 (9)	−0.0022 (9)	0.0002 (8)
O2	0.0675 (15)	0.0326 (12)	0.0578 (14)	0.0219 (11)	−0.0016 (11)	−0.0014 (10)
O3	0.0554 (14)	0.0415 (12)	0.0356 (11)	0.0245 (10)	0.0028 (10)	−0.0013 (9)
O4	0.111 (2)	0.0646 (17)	0.0450 (14)	0.0490 (16)	−0.0096 (14)	0.0024 (12)
O5	0.113 (2)	0.0505 (16)	0.0681 (17)	0.0266 (16)	−0.0249 (16)	−0.0026 (13)
O6	0.272 (5)	0.072 (2)	0.0547 (19)	0.053 (3)	0.061 (3)	−0.0016 (16)
C1	0.0372 (16)	0.0361 (16)	0.0380 (17)	−0.0040 (13)	0.0053 (13)	−0.0033 (13)
C2	0.0354 (16)	0.0331 (15)	0.0423 (17)	−0.0042 (13)	0.0070 (13)	−0.0082 (13)
C3	0.0447 (19)	0.0407 (18)	0.050 (2)	0.0028 (14)	0.0047 (15)	−0.0109 (15)
C4	0.073 (3)	0.051 (2)	0.051 (2)	0.0060 (18)	0.0110 (18)	−0.0194 (17)
C5	0.101 (3)	0.065 (2)	0.0360 (19)	0.018 (2)	0.0022 (19)	−0.0094 (17)
C6	0.080 (3)	0.050 (2)	0.0397 (19)	0.0174 (18)	0.0036 (17)	−0.0033 (16)
C7	0.0366 (16)	0.0346 (16)	0.0330 (16)	−0.0040 (13)	0.0020 (13)	0.0027 (13)
C8	0.0290 (15)	0.0286 (14)	0.0373 (16)	−0.0023 (12)	0.0026 (12)	0.0047 (12)
C9	0.0265 (14)	0.0266 (14)	0.0402 (16)	−0.0030 (11)	0.0006 (12)	0.0020 (12)
C10	0.0374 (17)	0.0301 (15)	0.0416 (17)	0.0024 (12)	−0.0008 (13)	0.0009 (13)
C11	0.0348 (16)	0.0283 (15)	0.0498 (18)	0.0011 (12)	0.0006 (14)	0.0046 (13)
C12	0.0433 (18)	0.0337 (16)	0.055 (2)	0.0091 (14)	0.0009 (15)	0.0154 (15)
C13	0.0403 (17)	0.0387 (17)	0.0388 (16)	−0.0007 (14)	−0.0011 (13)	0.0100 (14)
C14	0.0351 (16)	0.0257 (14)	0.0468 (18)	0.0017 (12)	0.0097 (13)	−0.0053 (13)
C15	0.0395 (17)	0.0271 (15)	0.0429 (17)	0.0043 (12)	0.0090 (13)	0.0015 (13)
C16	0.0384 (17)	0.0306 (15)	0.0394 (16)	0.0071 (13)	0.0079 (13)	0.0042 (13)
C17	0.058 (2)	0.0395 (17)	0.0384 (17)	0.0193 (15)	0.0086 (15)	0.0000 (14)
C18	0.060 (2)	0.0445 (18)	0.0445 (19)	0.0187 (16)	0.0029 (16)	0.0093 (15)
C19	0.062 (2)	0.0371 (17)	0.055 (2)	0.0244 (16)	0.0060 (17)	0.0118 (15)
C20	0.052 (2)	0.0307 (16)	0.0510 (19)	0.0140 (14)	0.0117 (16)	0.0022 (14)
C21	0.113 (4)	0.073 (3)	0.125 (4)	0.007 (3)	−0.021 (3)	−0.008 (3)
C22	0.093 (3)	0.116 (4)	0.055 (3)	0.039 (3)	0.016 (2)	0.007 (3)

Geometric parameters (Å, º) top

Cu1—O3	1.890 (2)	C7—C8	1.412 (4)
Cu1—O1	1.9038 (19)	C7—H7	0.9300
Cu1—N1	1.933 (2)	C8—C13	1.425 (4)
Cu1—N2	1.941 (2)	C8—C9	1.430 (4)
N1—C7	1.303 (4)	C9—C10	1.398 (4)
N1—C1	1.421 (4)	C10—C11	1.382 (4)
N2—C14	1.303 (3)	C10—H10	0.9300
N2—C2	1.422 (4)	C11—C12	1.401 (4)
O1—C9	1.315 (3)	C12—C13	1.352 (4)
O2—C11	1.351 (4)	C12—H12	0.9300
O2—H2	0.8200	C13—H13	0.9300
O3—C16	1.308 (3)	C14—C15	1.420 (4)
O4—C18	1.368 (4)	C14—H14	0.9300
O4—H4	0.8200	C15—C20	1.416 (4)
O5—C21	1.392 (5)	C15—C16	1.426 (4)
O5—H5	0.8200	C16—C17	1.408 (4)
O6—C22	1.369 (6)	C17—C18	1.373 (4)
O6—H6	0.8200	C17—H17	0.9300
C1—C6	1.385 (4)	C18—C19	1.402 (4)
C1—C2	1.405 (4)	C19—C20	1.354 (5)
C2—C3	1.385 (4)	C19—H19	0.9300
C3—C4	1.381 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.374 (5)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.378 (5)	C22—H22A	0.9600
C5—H5A	0.9300	C22—H22B	0.9600
C6—H6A	0.9300	C22—H22C	0.9600

C7···C9ⁱ	3.185 (4)	C8···C14ⁱⁱ	3.232 (4)

O3—Cu1—O1	86.42 (8)	C11—C10—C9	121.7 (3)
O3—Cu1—N1	178.39 (9)	C11—C10—H10	119.2
O1—Cu1—N1	94.78 (9)	C9—C10—H10	119.2
O3—Cu1—N2	94.77 (9)	O2—C11—C10	122.8 (3)
O1—Cu1—N2	178.65 (9)	O2—C11—C12	116.9 (3)
N1—Cu1—N2	84.02 (9)	C10—C11—C12	120.3 (3)
C7—N1—C1	122.4 (2)	C13—C12—C11	119.2 (3)
C7—N1—Cu1	124.2 (2)	C13—C12—H12	120.4
C1—N1—Cu1	113.23 (18)	C11—C12—H12	120.4
C14—N2—C2	122.5 (2)	C12—C13—C8	122.7 (3)
C14—N2—Cu1	124.2 (2)	C12—C13—H13	118.7
C2—N2—Cu1	113.32 (18)	C8—C13—H13	118.7
C9—O1—Cu1	127.17 (18)	N2—C14—C15	126.1 (3)
C11—O2—H2	109.5	N2—C14—H14	117.0
C16—O3—Cu1	127.11 (18)	C15—C14—H14	117.0
C18—O4—H4	109.5	C20—C15—C14	118.0 (3)
C21—O5—H5	109.5	C20—C15—C16	118.1 (3)
C22—O6—H6	109.5	C14—C15—C16	123.7 (3)
C6—C1—C2	119.5 (3)	O3—C16—C17	118.3 (3)
C6—C1—N1	125.5 (3)	O3—C16—C15	123.7 (3)
C2—C1—N1	115.1 (2)	C17—C16—C15	118.1 (3)
C3—C2—C1	119.2 (3)	C18—C17—C16	121.4 (3)
C3—C2—N2	126.4 (3)	C18—C17—H17	119.3
C1—C2—N2	114.4 (2)	C16—C17—H17	119.3
C4—C3—C2	120.7 (3)	O4—C18—C17	122.2 (3)
C4—C3—H3	119.7	O4—C18—C19	117.1 (3)
C2—C3—H3	119.7	C17—C18—C19	120.7 (3)
C5—C4—C3	119.8 (3)	C20—C19—C18	118.8 (3)
C5—C4—H4A	120.1	C20—C19—H19	120.6
C3—C4—H4A	120.1	C18—C19—H19	120.6
C4—C5—C6	120.5 (3)	C19—C20—C15	122.8 (3)
C4—C5—H5A	119.7	C19—C20—H20	118.6
C6—C5—H5A	119.7	C15—C20—H20	118.6
C5—C6—C1	120.3 (3)	O5—C21—H21A	109.5
C5—C6—H6A	119.9	O5—C21—H21B	109.5
C1—C6—H6A	119.9	H21A—C21—H21B	109.5
N1—C7—C8	126.3 (3)	O5—C21—H21C	109.5
N1—C7—H7	116.9	H21A—C21—H21C	109.5
C8—C7—H7	116.9	H21B—C21—H21C	109.5
C7—C8—C13	118.0 (3)	O6—C22—H22A	109.5
C7—C8—C9	124.3 (3)	O6—C22—H22B	109.5
C13—C8—C9	117.7 (3)	H22A—C22—H22B	109.5
O1—C9—C10	118.7 (3)	O6—C22—H22C	109.5
O1—C9—C8	123.0 (3)	H22A—C22—H22C	109.5
C10—C9—C8	118.4 (2)	H22B—C22—H22C	109.5

O3—Cu1—N1—C7	−144 (3)	Cu1—N1—C7—C8	6.1 (4)
O1—Cu1—N1—C7	−5.2 (2)	N1—C7—C8—C13	177.0 (3)
N2—Cu1—N1—C7	175.4 (2)	N1—C7—C8—C9	−0.8 (4)
O3—Cu1—N1—C1	42 (3)	Cu1—O1—C9—C10	−176.41 (18)
O1—Cu1—N1—C1	−179.98 (18)	Cu1—O1—C9—C8	4.1 (4)
N2—Cu1—N1—C1	0.65 (18)	C7—C8—C9—O1	−4.7 (4)
O3—Cu1—N2—C14	−1.3 (2)	C13—C8—C9—O1	177.5 (2)
O1—Cu1—N2—C14	150 (4)	C7—C8—C9—C10	175.8 (3)
N1—Cu1—N2—C14	177.7 (2)	C13—C8—C9—C10	−2.0 (4)
O3—Cu1—N2—C2	179.91 (18)	O1—C9—C10—C11	−178.6 (2)
O1—Cu1—N2—C2	−28 (4)	C8—C9—C10—C11	0.9 (4)
N1—Cu1—N2—C2	−1.15 (18)	C9—C10—C11—O2	−179.7 (3)
O3—Cu1—O1—C9	179.2 (2)	C9—C10—C11—C12	0.7 (4)
N1—Cu1—O1—C9	0.3 (2)	O2—C11—C12—C13	179.3 (3)
N2—Cu1—O1—C9	27 (4)	C10—C11—C12—C13	−1.0 (4)
O1—Cu1—O3—C16	−172.9 (2)	C11—C12—C13—C8	−0.2 (5)
N1—Cu1—O3—C16	−34 (3)	C7—C8—C13—C12	−176.3 (3)
N2—Cu1—O3—C16	6.5 (2)	C9—C8—C13—C12	1.7 (4)
C7—N1—C1—C6	5.7 (5)	C2—N2—C14—C15	177.7 (3)
Cu1—N1—C1—C6	−179.4 (3)	Cu1—N2—C14—C15	−1.1 (4)
C7—N1—C1—C2	−174.9 (2)	N2—C14—C15—C20	−176.1 (3)
Cu1—N1—C1—C2	0.0 (3)	N2—C14—C15—C16	−0.5 (5)
C6—C1—C2—C3	−0.1 (4)	Cu1—O3—C16—C17	170.0 (2)
N1—C1—C2—C3	−179.5 (2)	Cu1—O3—C16—C15	−9.4 (4)
C6—C1—C2—N2	178.5 (3)	C20—C15—C16—O3	−178.4 (3)
N1—C1—C2—N2	−0.9 (4)	C14—C15—C16—O3	6.0 (5)
C14—N2—C2—C3	1.0 (4)	C20—C15—C16—C17	2.1 (4)
Cu1—N2—C2—C3	179.9 (2)	C14—C15—C16—C17	−173.5 (3)
C14—N2—C2—C1	−177.4 (2)	O3—C16—C17—C18	179.2 (3)
Cu1—N2—C2—C1	1.4 (3)	C15—C16—C17—C18	−1.3 (5)
C1—C2—C3—C4	−0.7 (5)	C16—C17—C18—O4	178.6 (3)
N2—C2—C3—C4	−179.0 (3)	C16—C17—C18—C19	−0.3 (5)
C2—C3—C4—C5	1.1 (5)	O4—C18—C19—C20	−177.8 (3)
C3—C4—C5—C6	−0.9 (6)	C17—C18—C19—C20	1.1 (5)
C4—C5—C6—C1	0.1 (6)	C18—C19—C20—C15	−0.2 (5)
C2—C1—C6—C5	0.3 (5)	C14—C15—C20—C19	174.4 (3)
N1—C1—C6—C5	179.7 (3)	C16—C15—C20—C19	−1.4 (5)
C1—N1—C7—C8	−179.6 (2)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱⁱⁱ	0.82	1.91	2.704 (3)	163
O4—H4···O6^iv	0.82	1.82	2.602 (4)	159
O5—H5···O4^v	0.82	1.97	2.788 (3)	176
O6—H6···O1	0.82	2.18	2.777 (3)	130
O6—H6···O3	0.82	2.34	3.037 (4)	144

Symmetry codes: (iii) x, y+1, z; (iv) −x+2, −y+2, −z+1; (v) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₀H₁₄N₂O₄)]·2CH₄O
M_r	473.96
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9520 (17), 11.066 (2), 11.870 (2)
α, β, γ (°)	91.796 (2), 94.604 (3), 94.241 (3)
V (Å³)	1037.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.10
Crystal size (mm)	0.53 × 0.48 × 0.21

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.595, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	5360, 3592, 2873
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.00
No. of reflections	3592
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.36

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.82	1.91	2.704 (3)	163.0
O4—H4···O6ⁱⁱ	0.82	1.82	2.602 (4)	159.2
O5—H5···O4ⁱⁱⁱ	0.82	1.97	2.788 (3)	175.8
O6—H6···O1	0.82	2.18	2.777 (3)	129.9
O6—H6···O3	0.82	2.34	3.037 (4)	143.9

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+2, −z+1; (iii) −x+2, −y+1, −z+1.

Acknowledgements

We acknowledge the financial support of the National Natural Science Foundation of China (grant No. 20671048).

References

Amirnasr, M., Schenk, K. J., Meghdadi, S. & Morshedi, M. (2006). Polyhedron, 25, 671–677. Web of Science CSD CrossRef CAS Google Scholar
Arola-Arnal, A., Benet-Buchholz, J., Neidle, S. & Viler, R. (2008). Inorg. Chem. 47, 11910–11919. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lu, X. Q., Bao, F., Kang, B. S., Wu, Q., Liu, H. Q. & Zhu, F. M. (2006). J. Organomet. Chem. 691, 821–828. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sundaravel, K., Suresh, E. & Palaniandavar, M. (2009). Inorg. Chim. Acta, 362, 199–207. Web of Science CSD CrossRef CAS Google Scholar

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Volume 66| Part 1| January 2010| Page m77

doi:10.1107/S1600536809053720

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

[5,5′-Dihydr­­oxy-2,2′-[o-phenyl­enebis(nitrilo­methyl­­idyne)]diphenolato}copper(II) methanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[5,5′-Dihydroxy-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}copper(II) methanol disolvate