Literature DB >> 21201884

Bis{μ-2,2'-[o-phenyl-enebis(nitrilo-methyl-idyne)]diphenolato}dicopper(II) N,N'-dimethyl-formamide disolvate.

Guofeng Yu1, Yu Ding, Li Wang, Zhengbing Fu, Xinliang Hu.   

Abstract

The title compound, [Cu(2)(C(20)H(14)N(2)O(2))(2)]·2C(3)H(7)NO, consists of a centrosymmetric dimer composed of two copper(II) ions and two tetra-dentate salphen ligands {H(2)salphen is 2,2'-[o-phenyl-enebis(nitrilo-methyl-idyne)]diphenol}, and two dimethyl-formamide solvent mol-ecules. The Cu(II) atom is bonded to two N imino atoms and three phenolate O atoms of salphen. One deprotonated phenol group of each ligand bridges two Cu atoms, forming the dimer. The geometry about the five-coordinate Cu atom can best be described as slightly distorted recta-ngular pyramidal. The crystal structure is stabilized by π-π inter-actions [centroid-centroid distance 3.779 (2) Å] and C-H⋯O hydrogen bonds.

Entities:  

Year:  2008        PMID： 21201884      PMCID： PMC2960754          DOI： 10.1107/S1600536808005394

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Suzuki et al. (1997 ▶).

Experimental

Crystal data

[Cu2(C20H14N2O2)2]·2C3H7NO M = 901.94 Monoclinic, a = 8.1864 (5) Å b = 14.792 (1) Å c = 16.9584 (11) Å β = 93.252 (1)° V = 2050.2 (2) Å3 Z = 2 Mo Kα radiation μ = 1.09 mm−1 T = 294 (2) K 0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.811, T max = 0.898 13976 measured reflections 4468 independent reflections 3126 reflections with I > 2σ(I) R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.129 S = 0.98 4468 reflections 273 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.36 e Å−3 Data collection: SMART (Bruker, 2001 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global, New_Global_Publ_Block_1. DOI: 10.1107/S1600536808005394/br2066sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005394/br2066Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu2(C20H14N2O2)2]·2C3H7NOF000 = 932
Mr = 901.94Dx = 1.461 Mg m−3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3178 reflections
a = 8.1864 (5) Åθ = 2.8–23.0º
b = 14.7920 (10) ŵ = 1.10 mm−1
c = 16.9584 (11) ÅT = 294 (2) K
β = 93.252 (1)ºBlock, black
V = 2050.2 (2) Å30.20 × 0.10 × 0.10 mm
Z = 2
Bruker SMART CCD area-detector diffractometer4468 independent reflections
Radiation source: fine-focus sealed tube3126 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.083
T = 294(2) Kθmax = 27.0º
φ and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2001)h = −10→10
Tmin = 0.811, Tmax = 0.898k = −14→18
13976 measured reflectionsl = −20→21
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.129  w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
4468 reflectionsΔρmax = 0.52 e Å−3
273 parametersΔρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
Cu10.87999 (4)0.02801 (2)0.07623 (2)0.03962 (15)
C10.7432 (3)0.2022 (2)0.05569 (18)0.0394 (7)
C20.6560 (4)0.2775 (2)0.0271 (2)0.0506 (8)
H20.59410.2742−0.02050.061*
C30.6622 (5)0.3569 (2)0.0699 (2)0.0614 (10)
H30.60530.40750.05080.074*
C40.7528 (5)0.3612 (2)0.1410 (3)0.0688 (11)
H40.75470.41460.17000.083*
C50.8397 (4)0.2880 (2)0.1695 (2)0.0546 (9)
H50.90140.29210.21710.065*
C60.8359 (3)0.2075 (2)0.12719 (18)0.0392 (7)
C70.6479 (4)0.0977 (2)−0.04292 (18)0.0399 (7)
H70.58580.1452−0.06470.048*
C80.6304 (4)0.0124 (2)−0.08095 (17)0.0412 (7)
C90.7215 (4)−0.0655 (2)−0.05630 (19)0.0419 (7)
C100.6853 (4)−0.1464 (2)−0.0970 (2)0.0509 (8)
H100.7399−0.1991−0.08120.061*
C110.5710 (4)−0.1499 (3)−0.1597 (2)0.0585 (10)
H110.5500−0.2046−0.18530.070*
C120.4865 (4)−0.0729 (3)−0.1852 (2)0.0566 (9)
H120.4112−0.0753−0.22830.068*
C130.5161 (4)0.0058 (2)−0.1460 (2)0.0495 (9)
H130.45880.0573−0.16270.059*
C140.9997 (4)0.1198 (2)0.21836 (19)0.0473 (8)
H141.00890.17180.24920.057*
C151.0785 (4)0.0411 (2)0.2491 (2)0.0478 (8)
C161.0733 (4)−0.0430 (2)0.2097 (2)0.0483 (9)
C171.1600 (5)−0.1157 (3)0.2469 (2)0.0654 (11)
H171.1591−0.17200.22260.078*
C181.2455 (5)−0.1043 (3)0.3184 (3)0.0746 (12)
H181.3026−0.15290.34110.090*
C191.2486 (5)−0.0225 (3)0.3570 (2)0.0787 (14)
H191.3061−0.01590.40550.094*
C201.1659 (5)0.0486 (3)0.3230 (2)0.0652 (11)
H201.16710.10380.34930.078*
C210.7335 (6)0.1052 (3)0.4145 (3)0.0950 (15)
H21A0.82990.09980.38520.142*
H21B0.65120.06430.39320.142*
H21C0.75970.09050.46890.142*
C220.5134 (5)0.2143 (3)0.4363 (3)0.0993 (17)
H22A0.49180.27800.43260.149*
H22B0.50930.19530.49020.149*
H22C0.43250.18200.40420.149*
C230.7679 (5)0.2604 (3)0.3829 (2)0.0601 (10)
H230.72430.31840.38000.072*
N10.7417 (3)0.11587 (16)0.01899 (14)0.0367 (6)
N20.9162 (3)0.12659 (17)0.15158 (14)0.0384 (6)
N30.6731 (4)0.1958 (2)0.40887 (18)0.0592 (8)
O10.8363 (3)−0.06591 (14)0.00094 (13)0.0492 (6)
O20.9963 (3)−0.05820 (15)0.14172 (14)0.0524 (6)
O30.9070 (3)0.25103 (17)0.36246 (15)0.0639 (7)
U11U22U33U12U13U23
Cu10.0424 (2)0.0340 (2)0.0420 (2)0.00078 (17)−0.00157 (16)0.00026 (17)
C10.0368 (16)0.0327 (17)0.0494 (18)−0.0021 (13)0.0080 (13)0.0017 (14)
C20.052 (2)0.0390 (19)0.060 (2)−0.0029 (16)−0.0039 (16)0.0066 (17)
C30.069 (2)0.035 (2)0.080 (3)0.0043 (17)−0.001 (2)0.0036 (19)
C40.094 (3)0.033 (2)0.080 (3)−0.002 (2)0.004 (2)−0.011 (2)
C50.067 (2)0.044 (2)0.052 (2)−0.0055 (17)−0.0006 (17)−0.0067 (17)
C60.0384 (16)0.0331 (18)0.0468 (18)−0.0044 (13)0.0090 (13)−0.0004 (14)
C70.0396 (16)0.0368 (18)0.0431 (17)0.0010 (14)0.0015 (13)0.0054 (14)
C80.0402 (17)0.0428 (19)0.0410 (18)−0.0072 (14)0.0065 (13)−0.0002 (15)
C90.0402 (17)0.0417 (19)0.0445 (18)−0.0069 (15)0.0090 (14)−0.0039 (15)
C100.054 (2)0.043 (2)0.057 (2)−0.0049 (16)0.0113 (17)−0.0072 (17)
C110.059 (2)0.060 (3)0.058 (2)−0.0212 (19)0.0127 (18)−0.0195 (19)
C120.048 (2)0.072 (3)0.049 (2)−0.0140 (19)0.0005 (16)−0.012 (2)
C130.0421 (19)0.057 (2)0.049 (2)−0.0032 (16)0.0006 (15)0.0002 (17)
C140.0434 (18)0.054 (2)0.0449 (19)−0.0027 (16)0.0038 (15)−0.0066 (16)
C150.0367 (17)0.060 (2)0.0468 (19)−0.0023 (15)0.0010 (14)0.0082 (17)
C160.0377 (17)0.056 (2)0.051 (2)−0.0013 (15)0.0059 (15)0.0180 (17)
C170.067 (2)0.060 (3)0.068 (3)0.004 (2)0.001 (2)0.024 (2)
C180.068 (3)0.080 (3)0.075 (3)0.003 (2)−0.006 (2)0.039 (3)
C190.071 (3)0.108 (4)0.055 (2)−0.005 (3)−0.016 (2)0.026 (3)
C200.062 (2)0.083 (3)0.049 (2)−0.005 (2)−0.0043 (18)0.007 (2)
C210.113 (4)0.057 (3)0.119 (4)0.005 (3)0.038 (3)0.011 (3)
C220.066 (3)0.095 (4)0.140 (5)−0.001 (3)0.032 (3)−0.015 (3)
C230.073 (3)0.047 (2)0.060 (2)0.001 (2)0.002 (2)−0.0103 (19)
N10.0376 (13)0.0332 (14)0.0393 (14)−0.0014 (11)0.0030 (11)0.0017 (11)
N20.0356 (13)0.0390 (15)0.0405 (14)−0.0020 (11)0.0026 (11)−0.0006 (12)
N30.0649 (19)0.0447 (19)0.070 (2)0.0021 (15)0.0183 (16)−0.0075 (16)
O10.0563 (14)0.0337 (12)0.0564 (14)0.0036 (11)−0.0077 (11)−0.0049 (11)
O20.0599 (15)0.0405 (13)0.0557 (14)0.0052 (11)−0.0063 (11)0.0072 (11)
O30.0575 (16)0.0729 (18)0.0617 (16)−0.0080 (14)0.0076 (13)−0.0121 (14)
Cu1—O11.907 (2)C12—C131.355 (5)
Cu1—O21.909 (2)C12—H120.9300
Cu1—N11.946 (2)C13—H130.9300
Cu1—N21.950 (2)C14—N21.293 (4)
Cu1—O1i2.783 (11).C14—C151.416 (4)
C1—C21.395 (4)C14—H140.9300
C1—C61.396 (4)C15—C201.411 (5)
C1—N11.420 (4)C15—C161.412 (5)
C2—C31.380 (5)C16—O21.302 (4)
C2—H20.9300C16—C171.416 (4)
C3—C41.381 (6)C17—C181.375 (6)
C3—H30.9300C17—H170.9300
C4—C51.369 (5)C18—C191.375 (6)
C4—H40.9300C18—H180.9300
C5—C61.389 (4)C19—C201.360 (6)
C5—H50.9300C19—H190.9300
C6—N21.416 (4)C20—H200.9300
C7—N11.294 (4)C21—N31.431 (5)
C7—C81.421 (4)C21—H21A0.9600
C7—H70.9300C21—H21B0.9600
C8—C131.409 (4)C21—H21C0.9600
C8—C91.423 (5)C22—N31.438 (5)
C9—O11.312 (4)C22—H22A0.9600
C9—C101.405 (4)C22—H22B0.9600
C10—C111.376 (5)C22—H22C0.9600
C10—H100.9300C23—O31.216 (4)
C11—C121.389 (5)C23—N31.321 (5)
C11—H110.9300C23—H230.9300
O1—Cu1—O288.35 (10)N2—C14—H14116.8
O1—Cu1—N194.06 (10)C15—C14—H14116.8
O2—Cu1—N1173.09 (10)C20—C15—C16119.3 (3)
O1—Cu1—N2177.59 (9)C20—C15—C14117.4 (4)
O2—Cu1—N293.78 (10)C16—C15—C14123.3 (3)
N1—Cu1—N283.69 (10)O2—C16—C15124.8 (3)
C2—C1—C6119.9 (3)O2—C16—C17118.0 (3)
C2—C1—N1125.1 (3)C15—C16—C17117.2 (3)
C6—C1—N1115.0 (3)C18—C17—C16121.1 (4)
C3—C2—C1119.6 (3)C18—C17—H17119.4
C3—C2—H2120.2C16—C17—H17119.4
C1—C2—H2120.2C17—C18—C19121.5 (4)
C2—C3—C4120.0 (3)C17—C18—H18119.3
C2—C3—H3120.0C19—C18—H18119.3
C4—C3—H3120.0C20—C19—C18118.8 (4)
C5—C4—C3120.9 (4)C20—C19—H19120.6
C5—C4—H4119.5C18—C19—H19120.6
C3—C4—H4119.5C19—C20—C15122.1 (4)
C4—C5—C6120.0 (3)C19—C20—H20119.0
C4—C5—H5120.0C15—C20—H20119.0
C6—C5—H5120.0N3—C21—H21A109.5
C5—C6—C1119.5 (3)N3—C21—H21B109.5
C5—C6—N2125.2 (3)H21A—C21—H21B109.5
C1—C6—N2115.2 (3)N3—C21—H21C109.5
N1—C7—C8126.3 (3)H21A—C21—H21C109.5
N1—C7—H7116.8H21B—C21—H21C109.5
C8—C7—H7116.8N3—C22—H22A109.5
C13—C8—C7117.5 (3)N3—C22—H22B109.5
C13—C8—C9119.2 (3)H22A—C22—H22B109.5
C7—C8—C9123.3 (3)N3—C22—H22C109.5
O1—C9—C10118.9 (3)H22A—C22—H22C109.5
O1—C9—C8124.2 (3)H22B—C22—H22C109.5
C10—C9—C8116.9 (3)O3—C23—N3126.1 (4)
C11—C10—C9121.8 (3)O3—C23—H23116.9
C11—C10—H10119.1N3—C23—H23116.9
C9—C10—H10119.1C7—N1—C1122.1 (3)
C10—C11—C12121.0 (3)C7—N1—Cu1124.6 (2)
C10—C11—H11119.5C1—N1—Cu1113.06 (19)
C12—C11—H11119.5C14—N2—C6122.3 (3)
C13—C12—C11118.6 (3)C14—N2—Cu1124.7 (2)
C13—C12—H12120.7C6—N2—Cu1112.94 (19)
C11—C12—H12120.7C23—N3—C21119.5 (3)
C12—C13—C8122.4 (4)C23—N3—C22122.2 (3)
C12—C13—H13118.8C21—N3—C22118.3 (3)
C8—C13—H13118.8C9—O1—Cu1126.3 (2)
N2—C14—C15126.4 (3)C16—O2—Cu1126.9 (2)
D—H···AD—HH···AD···AD—H···A
C14—H14···O30.932.443.244 (4)145
C5—H5···O30.932.543.333 (4)144
C23—H23···O2ii0.932.583.457 (5)158
C7—H7···O3iii0.932.413.333 (4)170
C2—H2···O3iii0.932.473.389 (4)172
C21—H21A···O30.962.362.756 (5)104
Table 1

Selected bond lengths (Å)

Cu1—O11.907 (2)
Cu1—O21.909 (2)
Cu1—N11.946 (2)
Cu1—N21.950 (2)
Cu1—O1i2.783 (11).

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14⋯O30.932.443.244 (4)145
C5—H5⋯O30.932.543.333 (4)144
C23—H23⋯O2ii0.932.583.457 (5)158
C7—H7⋯O3iii0.932.413.333 (4)170
C2—H2⋯O3iii0.932.473.389 (4)172
C21—H21A⋯O30.962.362.756 (5)104

Symmetry codes: (ii) ; (iii) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  Bis[μ-4-hydr-oxy-N'-(4-meth-oxy-2-oxido-benzyl-idene)benzohydrazidato]bis-[pyridine-copper(II)].

Authors:  Nooraziah Mohd Lair; Hamid Khaledi; Hapipah Mohd Ali; Rustam Puteh
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-31
  1 in total

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