Literature DB >> 21754691

{N,N'-[2,2'-(Ethane-1,2-diyldisulfanediyl)di-o-phenyl-ene]bis-(quinoline-2-carboxamidato)}copper(II).

Soraia Meghdadi, Valiollah Mirkhani, Peter C Ford.   

Abstract

In the title compound, [Cu(C(34)H(24)N(4)O(2)S(2))] or [Cu(bqdapte)], where H(2)bqdapte is 1,2-{bis-[2-(quinoline-2-carboxamido)-phen-yl]sulfan-yl}ethane, the Cu(II) ion is coordinated to the dianionic hexa-dentate bqdapte(2-) ligand by two amide and two quinoline N atoms and two thio-ether S atoms. In the observed conformation of the hexa-dentate ligand, the quinoline rings attain positions related by a twofold axis. The Cu atom displays a Jahn-Teller-distorted octa-hedral CuN(4)S(2) geometry axially compressed along the two trans-configured Cu-N(amidate) bonds.

Entities:  

Year:  2011        PMID： 21754691      PMCID： PMC3120416          DOI： 10.1107/S1600536811019581

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


Related literature

For general background to the applications of transition metal complexes of hybrid N,S-donor ligands, see: Kouroulis et al. (2009 ▶); Lee et al. (2007 ▶); Ronson et al. (2006 ▶); Sarkar et al. (2009 ▶); Tavacoli et al. (2003 ▶); Xie et al. (2005 ▶). For related structures, see: Kouroulis et al. (2009 ▶); Sarkar et al. (2009 ▶); Singh & Mukherjee (2005 ▶); Sunatsuki et al. (1998 ▶); Zhang et al. (2004 ▶). For the synthesis of the ligand see: Meghdadi et al. (2011 ▶).

Experimental

Crystal data

[Cu(C34H24N4O2S2)] M = 648.23 Orthorhombic, a = 11.4124 (15) Å b = 13.5097 (18) Å c = 18.606 (2) Å V = 2868.6 (7) Å3 Z = 4 Mo Kα radiation μ = 0.95 mm−1 T = 150 K 0.30 × 0.25 × 0.08 mm

Data collection

Bruker SMART 100 diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.770, T max = 0.927 21464 measured reflections 2926 independent reflections 2467 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.119 S = 1.22 2926 reflections 195 parameters H-atom parameters constrained Δρmax = 0.83 e Å−3 Δρmin = −0.40 e Å−3 Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019581/qk2010sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019581/qk2010Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C34H24N4O2S2)]Dx = 1.501 Mg m−3
Mr = 648.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 118 reflections
a = 11.4124 (15) Åθ = 17.8–27.3°
b = 13.5097 (18) ŵ = 0.95 mm−1
c = 18.606 (2) ÅT = 150 K
V = 2868.6 (7) Å3Plate, green
Z = 40.3 × 0.25 × 0.08 mm
F(000) = 1332
Bruker SMART 100 diffractometer2926 independent reflections
Radiation source: fine-focus sealed tube2467 reflections with I > 2σ(I)
graphiteRint = 0.040
ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −14→14
Tmin = 0.770, Tmax = 0.927k = −16→15
21464 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.22w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
2926 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.83 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
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
C10.95359 (19)0.63312 (18)0.40463 (12)0.0287 (5)
C20.97185 (18)0.72050 (18)0.45446 (11)0.0254 (5)
C31.07936 (19)0.72879 (19)0.49149 (13)0.0324 (6)
H31.13950.68370.48320.039*
C41.09359 (19)0.80390 (19)0.53956 (12)0.0326 (6)
H41.16420.81120.56390.039*
C51.00127 (18)0.87021 (17)0.55221 (11)0.0267 (5)
C61.0075 (2)0.9476 (2)0.60300 (13)0.0329 (6)
H61.07660.95760.62850.040*
C70.9143 (2)1.0077 (2)0.61517 (12)0.0336 (6)
H70.92001.05790.64920.040*
C80.8095 (2)0.99472 (18)0.57677 (13)0.0320 (5)
H80.74601.03600.58580.038*
C90.80010 (19)0.92180 (18)0.52621 (12)0.0284 (5)
H90.73080.91460.50040.034*
C100.89525 (18)0.85719 (17)0.51284 (11)0.0236 (5)
C110.81073 (18)0.54899 (17)0.33282 (11)0.0260 (5)
C120.85951 (19)0.45376 (19)0.33824 (13)0.0321 (5)
H120.92000.44260.37070.039*
C130.8195 (2)0.37658 (19)0.29635 (13)0.0358 (6)
H130.85350.31430.30100.043*
C140.7295 (2)0.39057 (19)0.24748 (13)0.0340 (6)
H140.70450.33850.21860.041*
C150.6777 (2)0.48159 (18)0.24211 (12)0.0309 (5)
H150.61620.49090.21000.037*
C160.71616 (19)0.56053 (18)0.28432 (12)0.0267 (5)
C170.6849 (2)0.7377 (2)0.20459 (13)0.0427 (7)
H17A0.66770.69820.16230.051*
H17B0.64100.79890.20050.051*
Cu0.75000.75000.38326 (2)0.02369 (16)
N10.84546 (16)0.63022 (15)0.37545 (9)0.0242 (4)
N20.88397 (15)0.78305 (15)0.46349 (9)0.0245 (4)
O1.03533 (14)0.57507 (15)0.39668 (10)0.0433 (5)
S0.63335 (5)0.67137 (5)0.28325 (3)0.03301 (19)
U11U22U33U12U13U23
C10.0220 (11)0.0413 (14)0.0229 (11)0.0030 (10)0.0022 (9)−0.0047 (10)
C20.0188 (10)0.0374 (12)0.0199 (10)0.0012 (9)−0.0004 (8)−0.0011 (9)
C30.0200 (11)0.0451 (14)0.0321 (13)0.0074 (10)−0.0029 (9)−0.0080 (11)
C40.0188 (11)0.0490 (16)0.0300 (12)0.0028 (10)−0.0053 (9)−0.0047 (11)
C50.0225 (11)0.0362 (13)0.0212 (11)0.0010 (9)0.0002 (9)0.0008 (9)
C60.0254 (12)0.0450 (15)0.0283 (12)−0.0028 (10)−0.0032 (9)−0.0056 (11)
C70.0346 (13)0.0385 (14)0.0276 (12)−0.0005 (11)0.0019 (9)−0.0086 (10)
C80.0284 (12)0.0345 (13)0.0331 (13)0.0059 (10)0.0062 (10)−0.0002 (10)
C90.0228 (11)0.0370 (14)0.0255 (11)0.0042 (10)0.0026 (9)0.0017 (10)
C100.0206 (10)0.0320 (12)0.0180 (10)0.0008 (9)0.0042 (8)0.0027 (9)
C110.0222 (10)0.0341 (13)0.0216 (11)−0.0017 (9)0.0040 (9)−0.0018 (9)
C120.0274 (11)0.0410 (14)0.0280 (12)−0.0023 (10)0.0020 (10)0.0032 (11)
C130.0402 (13)0.0314 (14)0.0359 (13)−0.0009 (11)0.0079 (11)0.0008 (10)
C140.0420 (14)0.0330 (14)0.0269 (12)−0.0085 (11)0.0052 (10)−0.0045 (10)
C150.0327 (12)0.0388 (14)0.0212 (11)−0.0093 (10)0.0022 (9)−0.0009 (10)
C160.0244 (10)0.0352 (13)0.0206 (11)−0.0021 (9)0.0028 (9)−0.0006 (9)
C170.0633 (18)0.0398 (16)0.0249 (13)0.0066 (13)−0.0162 (12)−0.0024 (10)
Cu0.0172 (2)0.0340 (3)0.0199 (2)−0.00048 (15)0.0000.000
N10.0192 (9)0.0337 (11)0.0199 (9)0.0004 (8)0.0008 (7)−0.0029 (8)
N20.0174 (8)0.0361 (10)0.0201 (9)0.0009 (8)0.0012 (7)0.0021 (8)
O0.0219 (9)0.0598 (13)0.0481 (11)0.0127 (8)−0.0052 (8)−0.0262 (9)
S0.0244 (3)0.0392 (4)0.0354 (4)0.0007 (2)−0.0049 (2)−0.0076 (3)
C1—O1.228 (3)C11—N11.411 (3)
C1—N11.349 (3)C11—C161.415 (3)
C1—C21.515 (3)C12—C131.379 (4)
C2—N21.322 (3)C12—H120.9300
C2—C31.412 (3)C13—C141.385 (4)
C3—C41.362 (3)C13—H130.9300
C3—H30.9300C14—C151.368 (4)
C4—C51.403 (3)C14—H140.9300
C4—H40.9300C15—C161.395 (3)
C5—C61.411 (3)C15—H150.9300
C5—C101.425 (3)C16—S1.771 (2)
C6—C71.357 (3)C17—C17i1.523 (6)
C6—H60.9300C17—S1.814 (3)
C7—C81.405 (3)C17—H17A0.9700
C7—H70.9300C17—H17B0.9700
C8—C91.366 (3)Cu—N1i1.9561 (19)
C8—H80.9300Cu—N11.956 (2)
C9—C101.415 (3)Cu—N22.1830 (18)
C9—H90.9300Cu—N2i2.1830 (18)
C10—N21.365 (3)Cu—S2.5225 (7)
C11—C121.405 (3)Cu—Si2.5225 (7)
O—C1—N1128.9 (2)C15—C14—C13119.4 (2)
O—C1—C2117.83 (19)C15—C14—H14120.3
N1—C1—C2113.24 (19)C13—C14—H14120.3
N2—C2—C3123.1 (2)C14—C15—C16120.6 (2)
N2—C2—C1118.12 (19)C14—C15—H15119.7
C3—C2—C1118.7 (2)C16—C15—H15119.7
C4—C3—C2118.9 (2)C15—C16—C11121.0 (2)
C4—C3—H3120.6C15—C16—S118.16 (17)
C2—C3—H3120.6C11—C16—S120.48 (17)
C3—C4—C5119.7 (2)C17i—C17—S115.10 (14)
C3—C4—H4120.1C17i—C17—H17A108.5
C5—C4—H4120.1S—C17—H17A108.5
C4—C5—C6123.2 (2)C17i—C17—H17B108.5
C4—C5—C10118.2 (2)S—C17—H17B108.5
C6—C5—C10118.6 (2)H17A—C17—H17B107.5
C7—C6—C5121.0 (2)N1i—Cu—N1171.48 (10)
C7—C6—H6119.5N1i—Cu—N2105.76 (8)
C5—C6—H6119.5N1—Cu—N280.21 (7)
C6—C7—C8120.5 (2)N1i—Cu—N2i80.21 (7)
C6—C7—H7119.7N1—Cu—N2i105.76 (8)
C8—C7—H7119.7N2—Cu—N2i93.71 (9)
C9—C8—C7120.5 (2)N1i—Cu—S89.98 (6)
C9—C8—H8119.8N1—Cu—S83.73 (5)
C7—C8—H8119.8N2—Cu—S163.78 (5)
C8—C9—C10120.4 (2)N2i—Cu—S92.79 (5)
C8—C9—H9119.8N1i—Cu—Si83.73 (5)
C10—C9—H9119.8N1—Cu—Si89.98 (6)
N2—C10—C9119.90 (19)N2—Cu—Si92.79 (5)
N2—C10—C5121.08 (19)N2i—Cu—Si163.78 (5)
C9—C10—C5119.0 (2)S—Cu—Si84.93 (3)
C12—C11—N1124.1 (2)C1—N1—C11120.39 (19)
C12—C11—C16116.7 (2)C1—N1—Cu117.11 (16)
N1—C11—C16119.1 (2)C11—N1—Cu121.92 (14)
C13—C12—C11121.4 (2)C2—N2—C10118.88 (18)
C13—C12—H12119.3C2—N2—Cu108.28 (15)
C11—C12—H12119.3C10—N2—Cu132.55 (14)
C12—C13—C14120.9 (2)C16—S—C17104.70 (12)
C12—C13—H13119.6C16—S—Cu93.79 (7)
C14—C13—H13119.6C17—S—Cu102.48 (9)
O—C1—C2—N2−179.7 (2)S—Cu—N1—C1162.05 (16)
N1—C1—C2—N2−0.6 (3)Si—Cu—N1—C177.15 (15)
O—C1—C2—C3−2.6 (3)N2—Cu—N1—C11173.02 (17)
N1—C1—C2—C3176.5 (2)N2i—Cu—N1—C1181.90 (16)
N2—C2—C3—C40.8 (4)S—Cu—N1—C11−9.24 (15)
C1—C2—C3—C4−176.1 (2)Si—Cu—N1—C11−94.14 (16)
C2—C3—C4—C51.0 (4)C3—C2—N2—C10−2.6 (3)
C3—C4—C5—C6177.6 (2)C1—C2—N2—C10174.38 (19)
C3—C4—C5—C10−1.0 (3)C3—C2—N2—Cu171.95 (19)
C4—C5—C6—C7−177.6 (2)C1—C2—N2—Cu−11.1 (2)
C10—C5—C6—C71.0 (4)C9—C10—N2—C2−176.6 (2)
C5—C6—C7—C8−0.6 (4)C5—C10—N2—C22.5 (3)
C6—C7—C8—C9−0.5 (4)C9—C10—N2—Cu10.4 (3)
C7—C8—C9—C101.2 (4)C5—C10—N2—Cu−170.41 (15)
C8—C9—C10—N2178.4 (2)N1i—Cu—N2—C2−159.59 (15)
C8—C9—C10—C5−0.8 (3)N1—Cu—N2—C214.17 (15)
C4—C5—C10—N2−0.8 (3)N2i—Cu—N2—C2119.54 (17)
C6—C5—C10—N2−179.5 (2)S—Cu—N2—C26.1 (3)
C4—C5—C10—C9178.4 (2)Si—Cu—N2—C2−75.33 (15)
C6—C5—C10—C9−0.3 (3)N1i—Cu—N2—C1013.9 (2)
N1—C11—C12—C13178.2 (2)N1—Cu—N2—C10−172.3 (2)
C16—C11—C12—C132.2 (3)N2i—Cu—N2—C10−66.97 (17)
C11—C12—C13—C14−0.1 (4)S—Cu—N2—C10179.59 (13)
C12—C13—C14—C15−1.7 (4)Si—Cu—N2—C1098.16 (19)
C13—C14—C15—C161.2 (3)C15—C16—S—C17−83.65 (19)
C14—C15—C16—C111.0 (3)C11—C16—S—C17103.38 (19)
C14—C15—C16—S−171.92 (18)C15—C16—S—Cu172.39 (17)
C12—C11—C16—C15−2.7 (3)C11—C16—S—Cu−0.59 (18)
N1—C11—C16—C15−178.84 (18)C17i—C17—S—C16−59.6 (3)
C12—C11—C16—S170.09 (16)C17i—C17—S—Cu37.8 (3)
N1—C11—C16—S−6.1 (3)N1i—Cu—S—C16178.82 (9)
O—C1—N1—C114.6 (4)N1—Cu—S—C164.58 (9)
C2—C1—N1—C11−174.42 (18)N2—Cu—S—C1612.6 (2)
O—C1—N1—Cu−166.8 (2)N2i—Cu—S—C16−100.98 (9)
C2—C1—N1—Cu14.1 (2)Si—Cu—S—C1695.11 (7)
C12—C11—N1—C124.9 (3)N1i—Cu—S—C1772.85 (11)
C16—C11—N1—C1−159.3 (2)N1—Cu—S—C17−101.39 (11)
C12—C11—N1—Cu−164.14 (16)N2—Cu—S—C17−93.4 (2)
C16—C11—N1—Cu11.7 (3)N2i—Cu—S—C17153.05 (11)
N2—Cu—N1—C1−15.69 (15)Si—Cu—S—C17−10.85 (9)
N2i—Cu—N1—C1−106.81 (16)
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