Literature DB >> 22590174

Chlorido[N,N'-dibenzyl-N,N'-bis-(pyridin-2-ylmeth-yl)ethane-1,2-diamine]-copper(II) perchlorate methanol monosolvate.

Hui-Ting Song, Jia-Wei Mao, Ming Liu, Zhi-Quan Pan.   

Abstract

In the title solvated mol-ecular salt, [CuCl(C(28)H(30)N(4))]ClO(4)·CH(3)OH, the Cu(2+) ion is coordinated by the N,N',N'',N'''-tetra-dentate ligand and a chloride ion, generating a very distorted square-based pyramidal CuN(4)Cl coordination geometry with the Cl(-) ion in the basal position. In the crystal, the solvent mol-ecules and anions are linked by weak O-H⋯O hydrogen bonding.

Entities:  

Year:  2012        PMID: 22590174      PMCID: PMC3344412          DOI: 10.1107/S1600536812017941

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


Related literature

For related copper complexes, see: Cejudo et al. (2006 ▶); Vaidyanathan & Nair (2003 ▶); Wang et al. (2007 ▶); Xiao et al. (2011 ▶). For further synthetic details, see: Hamid & Hamid (2010 ▶); Fenton et al. (1995 ▶); Sun et al. (2002 ▶). For geometric descriptors of five-coordinate metal ions, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CuCl(C28H30N4)]ClO4·CH4O M = 653.04 Monoclinic, a = 17.800 (2) Å b = 10.5804 (13) Å c = 18.107 (2) Å β = 118.374 (1)° V = 3000.3 (6) Å3 Z = 4 Mo Kα radiation μ = 0.95 mm−1 T = 291 K 0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.777, T max = 0.818 16310 measured reflections 5885 independent reflections 4329 reflections with I > 2σ(I) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.110 S = 1.04 5885 reflections 372 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.36 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017941/hb6747sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017941/hb6747Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[CuCl(C28H30N4)]ClO4·CH4OF(000) = 1356
Mr = 653.04Dx = 1.446 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4897 reflections
a = 17.800 (2) Åθ = 2.2–24.4°
b = 10.5804 (13) ŵ = 0.95 mm1
c = 18.107 (2) ÅT = 291 K
β = 118.374 (1)°Block, blue
V = 3000.3 (6) Å30.28 × 0.24 × 0.22 mm
Z = 4
Bruker SMART APEX CCD diffractometer5885 independent reflections
Radiation source: sealed tube4329 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
phi and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −21→21
Tmin = 0.777, Tmax = 0.818k = −13→12
16310 measured reflectionsl = −22→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.05P)2 + 1.22P] where P = (Fo2 + 2Fc2)/3
5885 reflections(Δ/σ)max = 0.001
372 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.36 e Å3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C10.8517 (2)−0.0164 (3)0.6532 (2)0.0510 (8)
H10.8516−0.08320.61990.061*
C20.8816 (2)−0.0377 (3)0.7372 (2)0.0506 (8)
H20.9009−0.11730.76010.061*
C30.8824 (2)0.0609 (4)0.7866 (2)0.0529 (9)
H30.90280.04920.84390.064*
C40.8530 (2)0.1772 (3)0.7508 (2)0.0476 (8)
H40.85300.24510.78340.057*
C50.82358 (18)0.1917 (3)0.66583 (18)0.0356 (6)
C60.7922 (2)0.3167 (3)0.62251 (18)0.0400 (7)
H6A0.76110.36000.64690.048*
H6B0.84080.36880.63180.048*
C70.72963 (18)0.4225 (3)0.48671 (18)0.0364 (6)
H7A0.69930.40580.42690.044*
H7B0.78690.44910.50040.044*
C80.68568 (18)0.5318 (3)0.50492 (18)0.0360 (6)
C90.7309 (2)0.6120 (3)0.5716 (2)0.0436 (7)
H90.78820.59600.60830.052*
C100.6910 (2)0.7169 (3)0.5842 (2)0.0499 (8)
H100.72170.76990.62980.060*
C110.6071 (2)0.7426 (3)0.5301 (2)0.0515 (8)
H110.58110.81340.53840.062*
C120.5617 (2)0.6636 (3)0.4638 (2)0.0542 (9)
H120.50450.68030.42740.065*
C130.6003 (2)0.5599 (3)0.4508 (2)0.0441 (7)
H130.56890.50740.40510.053*
C140.8694 (2)−0.0635 (3)0.4603 (2)0.0523 (8)
H140.9185−0.01470.47940.063*
C150.8721 (2)−0.1880 (4)0.4398 (2)0.0550 (9)
H150.9223−0.22350.44510.066*
C160.7996 (2)−0.2578 (4)0.4116 (2)0.0547 (9)
H160.8000−0.34240.39790.066*
C170.7244 (2)−0.2037 (3)0.4031 (2)0.0512 (8)
H170.6743−0.25060.38240.061*
C180.7261 (2)−0.0808 (3)0.4257 (2)0.0440 (7)
C190.65156 (19)−0.0122 (3)0.4241 (2)0.0420 (7)
H19A0.5985−0.04940.38230.050*
H19B0.6534−0.01850.47840.050*
C200.6269 (2)0.1318 (3)0.31094 (19)0.0419 (7)
H20A0.65770.06990.29610.050*
H20B0.56670.11060.28050.050*
C210.63972 (19)0.2601 (3)0.28309 (18)0.0420 (7)
C220.5718 (2)0.3417 (4)0.2408 (2)0.0567 (9)
H220.51670.31520.22630.068*
C230.5853 (2)0.4638 (4)0.2196 (2)0.0579 (9)
H230.53950.51880.19210.070*
C240.6649 (3)0.5012 (4)0.2394 (2)0.0601 (10)
H240.67400.58220.22540.072*
C250.7326 (2)0.4209 (4)0.2799 (2)0.0561 (9)
H250.78730.44730.29270.067*
C260.7200 (2)0.3020 (4)0.3015 (2)0.0498 (8)
H260.76650.24840.32930.060*
C270.65133 (19)0.2506 (3)0.51552 (19)0.0402 (7)
H27A0.61910.31620.52540.048*
H27B0.65980.18150.55390.048*
C280.60207 (18)0.2044 (3)0.4264 (2)0.0414 (7)
H28A0.55260.15690.41990.050*
H28B0.58190.27630.38870.050*
C290.5166 (3)0.8830 (4)0.1346 (3)0.0703 (11)
H29A0.47100.94270.10700.105*
H29B0.51990.82930.09350.105*
H29C0.56950.92760.16520.105*
Cl10.39157 (5)0.94576 (7)0.32224 (5)0.04209 (18)
Cl20.90470 (5)0.25490 (9)0.50649 (6)0.0526 (2)
Cu10.78296 (2)0.15945 (3)0.49085 (2)0.03736 (12)
N10.82264 (17)0.0959 (2)0.61692 (16)0.0436 (6)
N20.73604 (15)0.3018 (2)0.53140 (15)0.0349 (5)
N30.79833 (15)−0.0104 (2)0.45376 (16)0.0407 (6)
N40.65620 (15)0.1222 (2)0.40350 (15)0.0362 (5)
O10.50092 (17)0.8086 (3)0.19076 (18)0.0680 (7)
H1B0.51930.85400.24240.082*
O110.44953 (15)0.9508 (2)0.40876 (14)0.0556 (6)
O120.43016 (16)0.9986 (3)0.27602 (17)0.0634 (7)
O130.36408 (16)0.8190 (2)0.30031 (17)0.0628 (7)
O140.31790 (16)1.0195 (3)0.30381 (17)0.0639 (7)
U11U22U33U12U13U23
C10.0486 (18)0.0393 (18)0.0505 (19)0.0061 (15)0.0116 (16)0.0060 (15)
C20.0488 (18)0.0376 (18)0.0486 (19)0.0091 (14)0.0095 (15)0.0165 (15)
C30.0494 (19)0.061 (2)0.0385 (17)0.0044 (17)0.0126 (15)0.0105 (16)
C40.0482 (18)0.0468 (19)0.0387 (17)0.0063 (15)0.0134 (15)0.0055 (14)
C50.0362 (15)0.0360 (16)0.0380 (15)0.0020 (12)0.0203 (13)0.0036 (12)
C60.0468 (17)0.0354 (17)0.0341 (15)0.0025 (13)0.0163 (13)0.0003 (12)
C70.0338 (14)0.0349 (16)0.0345 (15)−0.0009 (12)0.0114 (12)0.0020 (12)
C80.0361 (14)0.0320 (15)0.0336 (15)0.0005 (12)0.0114 (12)0.0059 (12)
C90.0452 (17)0.0414 (17)0.0375 (16)−0.0043 (14)0.0144 (14)0.0005 (13)
C100.055 (2)0.0382 (18)0.0450 (18)−0.0043 (15)0.0140 (16)−0.0050 (15)
C110.057 (2)0.0370 (18)0.0508 (19)0.0074 (15)0.0175 (17)0.0027 (15)
C120.0476 (19)0.0454 (19)0.053 (2)0.0141 (16)0.0103 (16)0.0078 (16)
C130.0472 (17)0.0385 (17)0.0379 (16)−0.0009 (14)0.0132 (14)−0.0007 (13)
C140.0478 (18)0.0432 (19)0.054 (2)0.0122 (15)0.0150 (16)−0.0007 (15)
C150.0447 (18)0.056 (2)0.055 (2)0.0162 (16)0.0160 (16)0.0022 (17)
C160.054 (2)0.0446 (19)0.053 (2)0.0180 (16)0.0161 (17)0.0082 (16)
C170.0456 (18)0.0356 (17)0.060 (2)0.0038 (14)0.0153 (16)0.0067 (15)
C180.0410 (16)0.0374 (17)0.0469 (18)0.0051 (13)0.0154 (14)0.0054 (14)
C190.0388 (16)0.0300 (15)0.0464 (18)−0.0062 (12)0.0115 (14)−0.0010 (13)
C200.0447 (17)0.0391 (17)0.0400 (16)−0.0047 (13)0.0186 (14)−0.0091 (13)
C210.0381 (15)0.0504 (19)0.0300 (15)0.0026 (14)0.0100 (13)−0.0046 (13)
C220.0435 (18)0.061 (2)0.052 (2)0.0088 (16)0.0112 (16)0.0169 (18)
C230.059 (2)0.055 (2)0.051 (2)0.0086 (18)0.0198 (18)0.0135 (17)
C240.066 (2)0.052 (2)0.052 (2)−0.0044 (18)0.0199 (18)0.0146 (17)
C250.052 (2)0.053 (2)0.053 (2)−0.0111 (16)0.0163 (17)0.0013 (17)
C260.0442 (18)0.056 (2)0.0389 (17)0.0007 (15)0.0112 (14)−0.0035 (15)
C270.0394 (16)0.0392 (16)0.0386 (16)0.0036 (13)0.0156 (13)0.0075 (13)
C280.0287 (14)0.0338 (16)0.0509 (19)−0.0001 (12)0.0101 (13)−0.0057 (13)
C290.073 (3)0.061 (3)0.063 (3)−0.013 (2)0.021 (2)−0.010 (2)
Cl10.0397 (4)0.0399 (4)0.0418 (4)0.0014 (3)0.0154 (3)0.0004 (3)
Cl20.0352 (4)0.0541 (5)0.0591 (5)−0.0073 (3)0.0146 (4)0.0039 (4)
Cu10.03061 (19)0.0358 (2)0.0403 (2)−0.00030 (15)0.01249 (15)−0.00317 (16)
N10.0446 (14)0.0358 (14)0.0408 (14)0.0050 (11)0.0126 (12)0.0044 (11)
N20.0360 (12)0.0325 (13)0.0308 (12)−0.0019 (10)0.0114 (10)−0.0002 (10)
N30.0369 (13)0.0390 (14)0.0406 (14)0.0019 (11)0.0139 (11)−0.0011 (11)
N40.0318 (12)0.0310 (12)0.0402 (13)−0.0034 (10)0.0126 (11)−0.0011 (10)
O10.0582 (15)0.0594 (16)0.0646 (16)0.0164 (13)0.0113 (13)0.0211 (14)
O110.0487 (13)0.0586 (15)0.0453 (13)−0.0095 (11)0.0109 (11)−0.0012 (11)
O120.0546 (14)0.0589 (16)0.0616 (16)0.0028 (12)0.0153 (13)0.0166 (13)
O130.0516 (14)0.0526 (15)0.0672 (16)−0.0052 (11)0.0145 (13)−0.0131 (13)
O140.0539 (14)0.0623 (17)0.0607 (16)0.0141 (13)0.0151 (13)0.0054 (13)
C1—N11.337 (4)C19—N41.483 (4)
C1—C21.369 (5)C19—H19A0.9700
C1—H10.9300C19—H19B0.9700
C2—C31.370 (5)C20—C211.502 (5)
C2—H20.9300C20—N41.504 (4)
C3—C41.373 (5)C20—H20A0.9700
C3—H30.9300C20—H20B0.9700
C4—C51.378 (4)C21—C261.377 (5)
C4—H40.9300C21—C221.383 (5)
C5—N11.340 (4)C22—C231.400 (5)
C5—C61.504 (4)C22—H220.9300
C6—N21.476 (4)C23—C241.347 (5)
C6—H6A0.9700C23—H230.9300
C6—H6B0.9700C24—C251.367 (5)
C7—N21.486 (4)C24—H240.9300
C7—C81.518 (4)C25—C261.368 (5)
C7—H7A0.9700C25—H250.9300
C7—H7B0.9700C26—H260.9300
C8—C91.379 (4)C27—N21.496 (4)
C8—C131.394 (4)C27—C281.505 (4)
C9—C101.393 (5)C27—H27A0.9700
C9—H90.9300C27—H27B0.9700
C10—C111.368 (5)C28—N41.496 (4)
C10—H100.9300C28—H28A0.9700
C11—C121.367 (5)C28—H28B0.9700
C11—H110.9300C29—O11.414 (5)
C12—C131.373 (5)C29—H29A0.9600
C12—H120.9300C29—H29B0.9600
C13—H130.9300C29—H29C0.9600
C14—N31.336 (4)Cl1—O111.409 (2)
C14—C151.376 (5)Cl1—O131.419 (3)
C14—H140.9300Cl1—O141.423 (3)
C15—C161.359 (5)Cl1—O121.425 (3)
C15—H150.9300Cu1—N31.983 (3)
C16—C171.394 (5)Cu1—N22.022 (2)
C16—H160.9300Cu1—N42.087 (2)
C17—C181.359 (5)Cu1—N12.152 (3)
C17—H170.9300Cu1—Cl22.2830 (9)
C18—N31.359 (4)O1—H1B0.9600
C18—C191.500 (4)
N1—C1—C2123.2 (3)C26—C21—C22117.8 (3)
N1—C1—H1118.4C26—C21—C20121.0 (3)
C2—C1—H1118.4C22—C21—C20121.2 (3)
C1—C2—C3118.5 (3)C21—C22—C23120.6 (3)
C1—C2—H2120.7C21—C22—H22119.7
C3—C2—H2120.7C23—C22—H22119.7
C2—C3—C4119.4 (3)C24—C23—C22119.6 (3)
C2—C3—H3120.3C24—C23—H23120.2
C4—C3—H3120.3C22—C23—H23120.2
C3—C4—C5118.9 (3)C23—C24—C25120.6 (4)
C3—C4—H4120.5C23—C24—H24119.7
C5—C4—H4120.5C25—C24—H24119.7
N1—C5—C4122.2 (3)C24—C25—C26120.1 (3)
N1—C5—C6115.8 (3)C24—C25—H25119.9
C4—C5—C6122.0 (3)C26—C25—H25119.9
N2—C6—C5112.0 (2)C25—C26—C21121.3 (3)
N2—C6—H6A109.2C25—C26—H26119.3
C5—C6—H6A109.2C21—C26—H26119.3
N2—C6—H6B109.2N2—C27—C28110.1 (2)
C5—C6—H6B109.2N2—C27—H27A109.6
H6A—C6—H6B107.9C28—C27—H27A109.6
N2—C7—C8116.8 (2)N2—C27—H27B109.6
N2—C7—H7A108.1C28—C27—H27B109.6
C8—C7—H7A108.1H27A—C27—H27B108.1
N2—C7—H7B108.1N4—C28—C27111.2 (2)
C8—C7—H7B108.1N4—C28—H28A109.4
H7A—C7—H7B107.3C27—C28—H28A109.4
C9—C8—C13118.2 (3)N4—C28—H28B109.4
C9—C8—C7120.8 (3)C27—C28—H28B109.4
C13—C8—C7120.8 (3)H28A—C28—H28B108.0
C8—C9—C10120.2 (3)O1—C29—H29A109.5
C8—C9—H9119.9O1—C29—H29B109.5
C10—C9—H9119.9H29A—C29—H29B109.5
C11—C10—C9120.6 (3)O1—C29—H29C109.5
C11—C10—H10119.7H29A—C29—H29C109.5
C9—C10—H10119.7H29B—C29—H29C109.5
C12—C11—C10119.7 (3)O11—Cl1—O13108.66 (16)
C12—C11—H11120.2O11—Cl1—O14110.26 (16)
C10—C11—H11120.2O13—Cl1—O14107.23 (17)
C11—C12—C13120.3 (3)O11—Cl1—O12109.60 (15)
C11—C12—H12119.9O13—Cl1—O12113.89 (17)
C13—C12—H12119.9O14—Cl1—O12107.14 (16)
C12—C13—C8121.1 (3)N3—Cu1—N2161.01 (10)
C12—C13—H13119.4N3—Cu1—N481.13 (10)
C8—C13—H13119.4N2—Cu1—N486.06 (10)
N3—C14—C15122.1 (3)N3—Cu1—N192.73 (10)
N3—C14—H14118.9N2—Cu1—N180.29 (10)
C15—C14—H14118.9N4—Cu1—N1115.89 (10)
C16—C15—C14118.1 (3)N3—Cu1—Cl299.64 (8)
C16—C15—H15120.9N2—Cu1—Cl299.03 (7)
C14—C15—H15120.9N4—Cu1—Cl2142.95 (7)
C15—C16—C17120.6 (3)N1—Cu1—Cl2101.12 (8)
C15—C16—H16119.7C1—N1—C5117.8 (3)
C17—C16—H16119.7C1—N1—Cu1130.9 (2)
C18—C17—C16118.5 (3)C5—N1—Cu1111.08 (19)
C18—C17—H17120.7C6—N2—C7110.6 (2)
C16—C17—H17120.7C6—N2—C27109.8 (2)
N3—C18—C17121.2 (3)C7—N2—C27113.4 (2)
N3—C18—C19114.4 (3)C6—N2—Cu1107.97 (18)
C17—C18—C19124.4 (3)C7—N2—Cu1112.35 (17)
N4—C19—C18108.3 (3)C27—N2—Cu1102.29 (18)
N4—C19—H19A110.0C14—N3—C18119.4 (3)
C18—C19—H19A110.0C14—N3—Cu1128.9 (2)
N4—C19—H19B110.0C18—N3—Cu1111.4 (2)
C18—C19—H19B110.0C19—N4—C28111.5 (2)
H19A—C19—H19B108.4C19—N4—C20108.3 (2)
C21—C20—N4114.1 (2)C28—N4—C20110.0 (2)
C21—C20—H20A108.7C19—N4—Cu199.18 (17)
N4—C20—H20A108.7C28—N4—Cu1106.68 (17)
C21—C20—H20B108.7C20—N4—Cu1120.60 (18)
N4—C20—H20B108.7C29—O1—H1B109.3
H20A—C20—H20B107.6
D—H···AD—HH···AD···AD—H···A
O1—H1B···O120.962.483.140 (4)126
Table 1

Selected bond lengths (Å)

Cu1—N31.983 (3)
Cu1—N22.022 (2)
Cu1—N42.087 (2)
Cu1—N12.152 (3)
Cu1—Cl22.2830 (9)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O1—H1B⋯O120.962.483.140 (4)126
  4 in total

1.  A short history of SHELX.

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

2.  DNA cleavage reaction induced by dimeric copper(II) complexes of N-substituted thiazole sulfonamides.

Authors:  R Cejudo; G Alzuet; M González-Alvarez; J L García-Gimenez; J Borrás; M Liu-González
Journal:  J Inorg Biochem       Date:  2005-11-28       Impact factor: 4.155

3.  Oxidative cleavage of DNA by tridentate copper (II) complex.

Authors:  Vaidyanathan Ganesan Vaidyanathan; Balachandran Unni Nair
Journal:  J Inorg Biochem       Date:  2003-01-15       Impact factor: 4.155

4.  Bis[N-(2-furylmeth-yl)ethane-1,2-di-amine]-bis-(perchlorato)copper(II).

Authors:  Wei Xiao; Shi-Rong Li; Hong Zhou; Zhi-Quan Pan; Qimao Huang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-07
  4 in total

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