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

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ISSN: 2056-9890

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

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 CuII 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[Amirnasr, M., Schenk, K. J., Meghdadi, S. & Morshedi, M. (2006). Polyhedron, 25, 671-677.]); Arola-Arnal et al. (2008[Arola-Arnal, A., Benet-Buchholz, J., Neidle, S. & Viler, R. (2008). Inorg. Chem. 47, 11910-11919.]); Sundaravel et al. (2009[Sundaravel, K., Suresh, E. & Palaniandavar, M. (2009). Inorg. Chim. Acta, 362, 199-207.]); Lu et al. (2006[Lu, X. Q., Bao, F., Kang, B. S., Wu, Q., Liu, H. Q. & Zhu, F. M. (2006). J. Organomet. Chem. 691, 821-828.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C20H14N2O4)]·2CH4O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.595, Tmax = 0.803

  • 5360 measured reflections

  • 3592 independent reflections

  • 2873 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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 CuII 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.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms with C—H = 0.96 Å (methylene) or 0.93 Å (aromatic), 0.82 Å (hydroxyl) and Uiso(H) = 1.2-1.5Ueq of the parent atom.

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
[Figure 1] 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)]·2CH4OZ = 2
Mr = 473.96F(000) = 490
Triclinic, P1Dx = 1.517 Mg m3
a = 7.9520 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.066 (2) ÅCell parameters from 2490 reflections
c = 11.870 (2) Åθ = 2.5–26.4°
α = 91.796 (2)°µ = 1.10 mm1
β = 94.604 (3)°T = 293 K
γ = 94.241 (3)°Block, red
V = 1037.6 (4) Å30.53 × 0.48 × 0.21 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3592 independent reflections
Radiation source: fine-focus sealed tube2873 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.595, Tmax = 0.803k = 1213
5360 measured reflectionsl = 1410
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-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 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
[Cu(C20H14N2O4)]·2CH4Oγ = 94.241 (3)°
Mr = 473.96V = 1037.6 (4) Å3
Triclinic, P1Z = 2
a = 7.9520 (17) ÅMo Kα radiation
b = 11.066 (2) ŵ = 1.10 mm1
c = 11.870 (2) ÅT = 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)
Tmin = 0.595, Tmax = 0.803Rint = 0.027
5360 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.00Δρmax = 0.46 e Å3
3592 reflectionsΔρmin = 0.36 e Å3
280 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.84950 (4)0.91865 (3)0.07516 (3)0.03348 (14)
N10.7711 (3)0.9467 (2)0.07955 (19)0.0322 (5)
N20.9482 (3)0.7807 (2)0.00880 (19)0.0317 (5)
O10.7530 (2)1.05584 (16)0.13697 (16)0.0356 (5)
O20.4653 (3)1.41526 (18)0.14493 (19)0.0522 (6)
H20.49911.41420.21200.078*
O30.9320 (3)0.89012 (18)0.22501 (16)0.0433 (5)
O41.2805 (4)0.7377 (2)0.52128 (19)0.0724 (8)
H41.24740.79600.55510.109*
O50.6076 (4)0.4576 (2)0.3584 (2)0.0780 (8)
H50.64540.40100.39270.117*
O60.7454 (6)1.0573 (3)0.3705 (3)0.1286 (17)
H60.80501.04330.31910.193*
C10.8192 (4)0.8588 (3)0.1582 (2)0.0374 (7)
C20.9139 (4)0.7681 (3)0.1106 (3)0.0373 (7)
C30.9676 (4)0.6789 (3)0.1807 (3)0.0455 (8)
H31.03140.61910.14980.055*
C40.9275 (5)0.6780 (3)0.2961 (3)0.0581 (9)
H4A0.96240.61700.34250.070*
C50.8358 (6)0.7674 (3)0.3423 (3)0.0670 (11)
H5A0.81010.76720.42010.080*
C60.7815 (5)0.8574 (3)0.2742 (3)0.0561 (9)
H6A0.71930.91740.30630.067*
C70.6728 (4)1.0312 (3)0.1095 (2)0.0351 (7)
H70.63401.03150.18550.042*
C80.6194 (3)1.1225 (2)0.0376 (2)0.0318 (6)
C90.6652 (3)1.1344 (2)0.0815 (2)0.0314 (6)
C100.6127 (4)1.2337 (2)0.1415 (3)0.0366 (7)
H100.64301.24310.21880.044*
C110.5170 (4)1.3183 (3)0.0890 (3)0.0378 (7)
C120.4682 (4)1.3056 (3)0.0271 (3)0.0436 (8)
H120.40221.36180.06240.052*
C130.5181 (4)1.2108 (3)0.0873 (3)0.0395 (7)
H130.48491.20290.16430.047*
C141.0398 (4)0.7072 (2)0.0662 (2)0.0357 (7)
H141.07920.64320.02590.043*
C151.0849 (4)0.7158 (2)0.1845 (2)0.0361 (7)
C161.0355 (4)0.8091 (2)0.2577 (2)0.0356 (7)
C171.1031 (4)0.8149 (3)0.3713 (3)0.0444 (8)
H171.07410.87610.41980.053*
C181.2108 (4)0.7320 (3)0.4118 (3)0.0487 (8)
C191.2564 (4)0.6381 (3)0.3410 (3)0.0500 (8)
H191.32790.58130.36900.060*
C201.1945 (4)0.6318 (3)0.2312 (3)0.0438 (8)
H201.22530.56960.18440.053*
C210.7229 (7)0.5589 (4)0.3737 (5)0.1056 (17)
H21A0.70130.60450.44040.158*
H21B0.71100.60870.30920.158*
H21C0.83580.53320.38200.158*
C220.6689 (6)0.9506 (5)0.4033 (4)0.0857 (14)
H22A0.67130.95130.48430.129*
H22B0.72820.88400.37720.129*
H22C0.55370.94180.37140.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0365 (2)0.0294 (2)0.0349 (2)0.00663 (14)0.00252 (14)0.00080 (14)
N10.0339 (13)0.0275 (12)0.0353 (13)0.0012 (10)0.0054 (10)0.0027 (10)
N20.0280 (12)0.0304 (12)0.0360 (13)0.0005 (10)0.0034 (10)0.0040 (10)
O10.0411 (11)0.0303 (10)0.0356 (11)0.0106 (9)0.0022 (9)0.0002 (8)
O20.0675 (15)0.0326 (12)0.0578 (14)0.0219 (11)0.0016 (11)0.0014 (10)
O30.0554 (14)0.0415 (12)0.0356 (11)0.0245 (10)0.0028 (10)0.0013 (9)
O40.111 (2)0.0646 (17)0.0450 (14)0.0490 (16)0.0096 (14)0.0024 (12)
O50.113 (2)0.0505 (16)0.0681 (17)0.0266 (16)0.0249 (16)0.0026 (13)
O60.272 (5)0.072 (2)0.0547 (19)0.053 (3)0.061 (3)0.0016 (16)
C10.0372 (16)0.0361 (16)0.0380 (17)0.0040 (13)0.0053 (13)0.0033 (13)
C20.0354 (16)0.0331 (15)0.0423 (17)0.0042 (13)0.0070 (13)0.0082 (13)
C30.0447 (19)0.0407 (18)0.050 (2)0.0028 (14)0.0047 (15)0.0109 (15)
C40.073 (3)0.051 (2)0.051 (2)0.0060 (18)0.0110 (18)0.0194 (17)
C50.101 (3)0.065 (2)0.0360 (19)0.018 (2)0.0022 (19)0.0094 (17)
C60.080 (3)0.050 (2)0.0397 (19)0.0174 (18)0.0036 (17)0.0033 (16)
C70.0366 (16)0.0346 (16)0.0330 (16)0.0040 (13)0.0020 (13)0.0027 (13)
C80.0290 (15)0.0286 (14)0.0373 (16)0.0023 (12)0.0026 (12)0.0047 (12)
C90.0265 (14)0.0266 (14)0.0402 (16)0.0030 (11)0.0006 (12)0.0020 (12)
C100.0374 (17)0.0301 (15)0.0416 (17)0.0024 (12)0.0008 (13)0.0009 (13)
C110.0348 (16)0.0283 (15)0.0498 (18)0.0011 (12)0.0006 (14)0.0046 (13)
C120.0433 (18)0.0337 (16)0.055 (2)0.0091 (14)0.0009 (15)0.0154 (15)
C130.0403 (17)0.0387 (17)0.0388 (16)0.0007 (14)0.0011 (13)0.0100 (14)
C140.0351 (16)0.0257 (14)0.0468 (18)0.0017 (12)0.0097 (13)0.0053 (13)
C150.0395 (17)0.0271 (15)0.0429 (17)0.0043 (12)0.0090 (13)0.0015 (13)
C160.0384 (17)0.0306 (15)0.0394 (16)0.0071 (13)0.0079 (13)0.0042 (13)
C170.058 (2)0.0395 (17)0.0384 (17)0.0193 (15)0.0086 (15)0.0000 (14)
C180.060 (2)0.0445 (18)0.0445 (19)0.0187 (16)0.0029 (16)0.0093 (15)
C190.062 (2)0.0371 (17)0.055 (2)0.0244 (16)0.0060 (17)0.0118 (15)
C200.052 (2)0.0307 (16)0.0510 (19)0.0140 (14)0.0117 (16)0.0022 (14)
C210.113 (4)0.073 (3)0.125 (4)0.007 (3)0.021 (3)0.008 (3)
C220.093 (3)0.116 (4)0.055 (3)0.039 (3)0.016 (2)0.007 (3)
Geometric parameters (Å, º) top
Cu1—O31.890 (2)C7—C81.412 (4)
Cu1—O11.9038 (19)C7—H70.9300
Cu1—N11.933 (2)C8—C131.425 (4)
Cu1—N21.941 (2)C8—C91.430 (4)
N1—C71.303 (4)C9—C101.398 (4)
N1—C11.421 (4)C10—C111.382 (4)
N2—C141.303 (3)C10—H100.9300
N2—C21.422 (4)C11—C121.401 (4)
O1—C91.315 (3)C12—C131.352 (4)
O2—C111.351 (4)C12—H120.9300
O2—H20.8200C13—H130.9300
O3—C161.308 (3)C14—C151.420 (4)
O4—C181.368 (4)C14—H140.9300
O4—H40.8200C15—C201.416 (4)
O5—C211.392 (5)C15—C161.426 (4)
O5—H50.8200C16—C171.408 (4)
O6—C221.369 (6)C17—C181.373 (4)
O6—H60.8200C17—H170.9300
C1—C61.385 (4)C18—C191.402 (4)
C1—C21.405 (4)C19—C201.354 (5)
C2—C31.385 (4)C19—H190.9300
C3—C41.381 (5)C20—H200.9300
C3—H30.9300C21—H21A0.9600
C4—C51.374 (5)C21—H21B0.9600
C4—H4A0.9300C21—H21C0.9600
C5—C61.378 (5)C22—H22A0.9600
C5—H5A0.9300C22—H22B0.9600
C6—H6A0.9300C22—H22C0.9600
C7···C9i3.185 (4)C8···C14ii3.232 (4)
O3—Cu1—O186.42 (8)C11—C10—C9121.7 (3)
O3—Cu1—N1178.39 (9)C11—C10—H10119.2
O1—Cu1—N194.78 (9)C9—C10—H10119.2
O3—Cu1—N294.77 (9)O2—C11—C10122.8 (3)
O1—Cu1—N2178.65 (9)O2—C11—C12116.9 (3)
N1—Cu1—N284.02 (9)C10—C11—C12120.3 (3)
C7—N1—C1122.4 (2)C13—C12—C11119.2 (3)
C7—N1—Cu1124.2 (2)C13—C12—H12120.4
C1—N1—Cu1113.23 (18)C11—C12—H12120.4
C14—N2—C2122.5 (2)C12—C13—C8122.7 (3)
C14—N2—Cu1124.2 (2)C12—C13—H13118.7
C2—N2—Cu1113.32 (18)C8—C13—H13118.7
C9—O1—Cu1127.17 (18)N2—C14—C15126.1 (3)
C11—O2—H2109.5N2—C14—H14117.0
C16—O3—Cu1127.11 (18)C15—C14—H14117.0
C18—O4—H4109.5C20—C15—C14118.0 (3)
C21—O5—H5109.5C20—C15—C16118.1 (3)
C22—O6—H6109.5C14—C15—C16123.7 (3)
C6—C1—C2119.5 (3)O3—C16—C17118.3 (3)
C6—C1—N1125.5 (3)O3—C16—C15123.7 (3)
C2—C1—N1115.1 (2)C17—C16—C15118.1 (3)
C3—C2—C1119.2 (3)C18—C17—C16121.4 (3)
C3—C2—N2126.4 (3)C18—C17—H17119.3
C1—C2—N2114.4 (2)C16—C17—H17119.3
C4—C3—C2120.7 (3)O4—C18—C17122.2 (3)
C4—C3—H3119.7O4—C18—C19117.1 (3)
C2—C3—H3119.7C17—C18—C19120.7 (3)
C5—C4—C3119.8 (3)C20—C19—C18118.8 (3)
C5—C4—H4A120.1C20—C19—H19120.6
C3—C4—H4A120.1C18—C19—H19120.6
C4—C5—C6120.5 (3)C19—C20—C15122.8 (3)
C4—C5—H5A119.7C19—C20—H20118.6
C6—C5—H5A119.7C15—C20—H20118.6
C5—C6—C1120.3 (3)O5—C21—H21A109.5
C5—C6—H6A119.9O5—C21—H21B109.5
C1—C6—H6A119.9H21A—C21—H21B109.5
N1—C7—C8126.3 (3)O5—C21—H21C109.5
N1—C7—H7116.9H21A—C21—H21C109.5
C8—C7—H7116.9H21B—C21—H21C109.5
C7—C8—C13118.0 (3)O6—C22—H22A109.5
C7—C8—C9124.3 (3)O6—C22—H22B109.5
C13—C8—C9117.7 (3)H22A—C22—H22B109.5
O1—C9—C10118.7 (3)O6—C22—H22C109.5
O1—C9—C8123.0 (3)H22A—C22—H22C109.5
C10—C9—C8118.4 (2)H22B—C22—H22C109.5
O3—Cu1—N1—C7144 (3)Cu1—N1—C7—C86.1 (4)
O1—Cu1—N1—C75.2 (2)N1—C7—C8—C13177.0 (3)
N2—Cu1—N1—C7175.4 (2)N1—C7—C8—C90.8 (4)
O3—Cu1—N1—C142 (3)Cu1—O1—C9—C10176.41 (18)
O1—Cu1—N1—C1179.98 (18)Cu1—O1—C9—C84.1 (4)
N2—Cu1—N1—C10.65 (18)C7—C8—C9—O14.7 (4)
O3—Cu1—N2—C141.3 (2)C13—C8—C9—O1177.5 (2)
O1—Cu1—N2—C14150 (4)C7—C8—C9—C10175.8 (3)
N1—Cu1—N2—C14177.7 (2)C13—C8—C9—C102.0 (4)
O3—Cu1—N2—C2179.91 (18)O1—C9—C10—C11178.6 (2)
O1—Cu1—N2—C228 (4)C8—C9—C10—C110.9 (4)
N1—Cu1—N2—C21.15 (18)C9—C10—C11—O2179.7 (3)
O3—Cu1—O1—C9179.2 (2)C9—C10—C11—C120.7 (4)
N1—Cu1—O1—C90.3 (2)O2—C11—C12—C13179.3 (3)
N2—Cu1—O1—C927 (4)C10—C11—C12—C131.0 (4)
O1—Cu1—O3—C16172.9 (2)C11—C12—C13—C80.2 (5)
N1—Cu1—O3—C1634 (3)C7—C8—C13—C12176.3 (3)
N2—Cu1—O3—C166.5 (2)C9—C8—C13—C121.7 (4)
C7—N1—C1—C65.7 (5)C2—N2—C14—C15177.7 (3)
Cu1—N1—C1—C6179.4 (3)Cu1—N2—C14—C151.1 (4)
C7—N1—C1—C2174.9 (2)N2—C14—C15—C20176.1 (3)
Cu1—N1—C1—C20.0 (3)N2—C14—C15—C160.5 (5)
C6—C1—C2—C30.1 (4)Cu1—O3—C16—C17170.0 (2)
N1—C1—C2—C3179.5 (2)Cu1—O3—C16—C159.4 (4)
C6—C1—C2—N2178.5 (3)C20—C15—C16—O3178.4 (3)
N1—C1—C2—N20.9 (4)C14—C15—C16—O36.0 (5)
C14—N2—C2—C31.0 (4)C20—C15—C16—C172.1 (4)
Cu1—N2—C2—C3179.9 (2)C14—C15—C16—C17173.5 (3)
C14—N2—C2—C1177.4 (2)O3—C16—C17—C18179.2 (3)
Cu1—N2—C2—C11.4 (3)C15—C16—C17—C181.3 (5)
C1—C2—C3—C40.7 (5)C16—C17—C18—O4178.6 (3)
N2—C2—C3—C4179.0 (3)C16—C17—C18—C190.3 (5)
C2—C3—C4—C51.1 (5)O4—C18—C19—C20177.8 (3)
C3—C4—C5—C60.9 (6)C17—C18—C19—C201.1 (5)
C4—C5—C6—C10.1 (6)C18—C19—C20—C150.2 (5)
C2—C1—C6—C50.3 (5)C14—C15—C20—C19174.4 (3)
N1—C1—C6—C5179.7 (3)C16—C15—C20—C191.4 (5)
C1—N1—C7—C8179.6 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+2, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5iii0.821.912.704 (3)163
O4—H4···O6iv0.821.822.602 (4)159
O5—H5···O4v0.821.972.788 (3)176
O6—H6···O10.822.182.777 (3)130
O6—H6···O30.822.343.037 (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
Mr473.96
Crystal system, space groupTriclinic, 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)
V3)1037.6 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.10
Crystal size (mm)0.53 × 0.48 × 0.21
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.595, 0.803
No. of measured, independent and
observed [I > 2σ(I)] reflections
5360, 3592, 2873
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.099, 1.00
No. of reflections3592
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O2—H2···O5i0.821.912.704 (3)163.0
O4—H4···O6ii0.821.822.602 (4)159.2
O5—H5···O4iii0.821.972.788 (3)175.8
O6—H6···O10.822.182.777 (3)129.9
O6—H6···O30.822.343.037 (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

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First citationSundaravel, K., Suresh, E. & Palaniandavar, M. (2009). Inorg. Chim. Acta, 362, 199–207.  Web of Science CSD CrossRef CAS Google Scholar

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