[5,5'-Dihydr-oxy-2,2'-[o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}copper(II) methanol disolvate.

In the title compound, [Cu(C(20)H(14)N(2)O(4))]·2CH(3)OH, 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 tetra-dentate Schiff base ligand 5,5'-dihydr-oxy-2,2'-[o-phenyl-enebis(nitrilo-methyl-idyne)]diphen-olate (L) in a distorted square-planar geometry. In the crystal, inter-molecular O-H⋯O hydrogen bonds link two CuL mol-ecules and four solvent mol-ecules into a centrosymmetric cluster. The crystal packing exhibits short inter-molecular 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 = 473.96

Triclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.00

3592 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.36 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053720/cv2670sup1.cif

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

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

[Cu(C20H14N2O4)]·2CH4O	Z = 2
Mr = 473.96	F(000) = 490
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0446P)2 + 0.5623P] where P = (Fo2 + 2Fc2)/3
3592 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O6iv	0.82	1.82	2.602 (4)	159
O5—H5···O4v	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

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) ; (ii) ; (iii) .