Literature DB >> 24046576

Bis{1-[(E)-(2-chloro-phen-yl)diazen-yl]naphthalen-2-olato}copper(II).

Mohamed Amine Benaouida1, Ali Benosmane, Hassiba Bouguerria, Salah Eddine Bouaoud, Hocine Merazig.   

Abstract

The Cu(II) atom in the title compound, [Cu(C16H10ClN2O)2], is located on an inversion center and is tetra-coordinated by two N and two O atoms from two bidentate 1-[(E)-(2-chloro-phen-yl)diazen-yl]naphthalen-2-olate ligands, forming a square-planar complex. In the crystal, mol-ecules are linked via weak C-H⋯O and C-H⋯Cl hydrogen bonds, forming chains propagating along [010]. There are also π-π inter-actions present involving adjacent naphthalene rings [centroid-centroid distance = 3.661 (13) Å].

Entities:  

Year:  2013        PMID： 24046576      PMCID： PMC3772433          DOI： 10.1107/S1600536813016681

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


Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). For related structures, see: Tai et al. (2010 ▶); Lin et al. (2010 ▶).

Experimental

Crystal data

[Cu(C16H10ClN2O)2] M = 626.99 Monoclinic, a = 10.2218 (4) Å b = 7.8348 (3) Å c = 17.5678 (6) Å β = 111.941 (2)° V = 1305.03 (9) Å3 Z = 2 Mo Kα radiation μ = 1.08 mm−1 T = 273 K 0.01 × 0.01 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer 7327 measured reflections 2299 independent reflections 1979 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.082 S = 1.04 2299 reflections 187 parameters H-atom parameters constrained Δρmax = 0.48 e Å−3 Δρmin = −0.28 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016681/su2613sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016681/su2613Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C16H10ClN2O)2]Z = 2
Mr = 626.99F(000) = 638
Monoclinic, P21/cLeast Squares Treatment of 25 SET4 setting angles.
Hall symbol: -P 2ybcDx = 1.595 Mg m−3
a = 10.2218 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8348 (3) ŵ = 1.08 mm−1
c = 17.5678 (6) ÅT = 273 K
β = 111.941 (2)°Block, black
V = 1305.03 (9) Å30.01 × 0.01 × 0.01 mm
Bruker APEXII CCD diffractometer1979 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.1°, θmin = 2.6°
phi and ω scansh = −11→12
7327 measured reflectionsk = −9→9
2299 independent reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0406P)2 + 0.9147P] where P = (Fo2 + 2Fc2)/3
2299 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.48 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cu11.000000.000000.500000.0201 (1)
Cl10.86221 (8)0.03646 (8)0.30754 (4)0.0321 (2)
O10.87383 (17)−0.1495 (2)0.52340 (10)0.0247 (6)
N10.7529 (2)0.1928 (3)0.49516 (12)0.0215 (6)
N20.8458 (2)0.1667 (3)0.46293 (12)0.0211 (6)
C10.8501 (2)0.2972 (3)0.40751 (15)0.0214 (7)
C20.8675 (3)0.2510 (3)0.33477 (15)0.0232 (8)
C30.8873 (3)0.3725 (4)0.28366 (16)0.0282 (8)
C40.8913 (3)0.5422 (4)0.30481 (17)0.0310 (9)
C50.8705 (3)0.5902 (3)0.37502 (16)0.0291 (8)
C60.8498 (3)0.4678 (3)0.42576 (16)0.0263 (8)
C70.7306 (2)0.0731 (3)0.54482 (15)0.0207 (7)
C80.7818 (3)−0.0968 (3)0.55231 (15)0.0219 (7)
C90.7262 (3)−0.2196 (3)0.59274 (16)0.0274 (8)
C100.6318 (3)−0.1733 (4)0.62659 (16)0.0304 (9)
C110.5848 (3)−0.0025 (4)0.62456 (16)0.0267 (8)
C120.4917 (3)0.0451 (4)0.66382 (16)0.0317 (9)
C130.4493 (3)0.2096 (4)0.66213 (17)0.0360 (10)
C140.4949 (3)0.3334 (4)0.62085 (17)0.0345 (9)
C150.5854 (3)0.2909 (4)0.58222 (16)0.0286 (8)
C160.6323 (2)0.1228 (3)0.58341 (15)0.0227 (8)
H30.897900.340500.235300.0340*
H40.908200.624900.271600.0370*
H50.870500.705200.388100.0350*
H60.835500.501000.472900.0310*
H90.75520−0.332800.595800.0330*
H100.59690−0.256200.651900.0360*
H120.45960−0.037000.690900.0380*
H130.389300.239900.688700.0430*
H140.464100.445500.619400.0410*
H150.615600.374800.555100.0340*
U11U22U33U12U13U23
Cu10.0171 (2)0.0261 (2)0.0214 (2)0.0055 (2)0.0123 (2)0.0032 (2)
Cl10.0429 (4)0.0302 (4)0.0314 (4)0.0010 (3)0.0235 (3)−0.0026 (3)
O10.0221 (9)0.0280 (10)0.0301 (10)0.0037 (8)0.0169 (8)0.0024 (8)
N10.0169 (10)0.0304 (12)0.0199 (10)0.0027 (9)0.0101 (9)0.0008 (9)
N20.0183 (10)0.0276 (11)0.0220 (11)0.0058 (9)0.0129 (9)0.0027 (9)
C10.0155 (12)0.0287 (13)0.0224 (13)0.0061 (10)0.0099 (11)0.0058 (11)
C20.0205 (13)0.0276 (14)0.0233 (13)0.0049 (11)0.0104 (11)0.0016 (11)
C30.0289 (15)0.0391 (16)0.0200 (13)0.0039 (12)0.0131 (12)0.0059 (12)
C40.0313 (15)0.0342 (16)0.0279 (15)0.0045 (12)0.0116 (13)0.0109 (12)
C50.0294 (15)0.0260 (14)0.0306 (15)0.0067 (12)0.0096 (13)0.0055 (12)
C60.0242 (13)0.0326 (15)0.0246 (14)0.0090 (11)0.0121 (12)0.0033 (11)
C70.0139 (12)0.0304 (13)0.0190 (12)−0.0001 (11)0.0074 (10)−0.0008 (11)
C80.0153 (12)0.0322 (14)0.0181 (12)0.0000 (11)0.0062 (10)−0.0008 (11)
C90.0265 (14)0.0269 (14)0.0297 (14)−0.0013 (11)0.0117 (12)0.0000 (12)
C100.0288 (15)0.0426 (16)0.0252 (14)−0.0069 (13)0.0164 (12)0.0021 (13)
C110.0185 (12)0.0432 (16)0.0201 (12)−0.0012 (12)0.0091 (11)−0.0018 (13)
C120.0232 (14)0.0547 (19)0.0226 (14)−0.0019 (13)0.0147 (12)−0.0012 (13)
C130.0254 (15)0.060 (2)0.0304 (15)0.0014 (14)0.0193 (13)−0.0092 (15)
C140.0283 (15)0.0435 (17)0.0368 (16)0.0055 (13)0.0179 (13)−0.0092 (14)
C150.0231 (14)0.0393 (16)0.0274 (14)0.0040 (12)0.0139 (12)−0.0019 (13)
C160.0150 (12)0.0364 (15)0.0176 (12)−0.0006 (11)0.0070 (11)−0.0040 (11)
Cu1—Cl13.1525 (7)C8—C91.434 (4)
Cu1—O11.8975 (17)C9—C101.358 (4)
Cu1—N21.961 (2)C10—C111.418 (4)
Cu1—Cl1i3.1525 (7)C11—C121.418 (4)
Cu1—O1i1.8975 (17)C11—C161.409 (4)
Cu1—N2i1.961 (2)C12—C131.357 (4)
Cl1—C21.743 (2)C13—C141.392 (4)
O1—C81.292 (4)C14—C151.377 (4)
N1—N21.291 (3)C15—C161.399 (4)
N1—C71.357 (3)C3—H30.9300
N2—C11.424 (3)C4—H40.9300
C1—C21.402 (4)C5—H50.9300
C1—C61.375 (3)C6—H60.9300
C2—C31.375 (4)C9—H90.9300
C3—C41.377 (4)C10—H100.9300
C4—C51.380 (4)C12—H120.9300
C5—C61.378 (4)C13—H130.9300
C7—C81.418 (3)C14—H140.9300
C7—C161.459 (3)C15—H150.9300
Cl1—Cu1—O1102.76 (5)O1—C8—C9117.5 (2)
Cl1—Cu1—N266.55 (6)C7—C8—C9118.4 (3)
Cl1—Cu1—Cl1i180.00C8—C9—C10121.0 (2)
Cl1—Cu1—O1i77.24 (5)C9—C10—C11122.0 (3)
Cl1—Cu1—N2i113.45 (6)C10—C11—C12121.2 (3)
O1—Cu1—N287.48 (8)C10—C11—C16119.5 (3)
Cl1i—Cu1—O177.24 (5)C12—C11—C16119.3 (3)
O1—Cu1—O1i180.00C11—C12—C13120.4 (3)
O1—Cu1—N2i92.52 (8)C12—C13—C14120.5 (3)
Cl1i—Cu1—N2113.45 (6)C13—C14—C15120.4 (3)
O1i—Cu1—N292.52 (8)C14—C15—C16120.7 (3)
N2—Cu1—N2i180.00C7—C16—C11118.8 (2)
Cl1i—Cu1—O1i102.76 (5)C7—C16—C15122.4 (2)
Cl1i—Cu1—N2i66.55 (6)C11—C16—C15118.8 (2)
O1i—Cu1—N2i87.48 (8)C2—C3—H3120.00
Cu1—Cl1—C280.64 (8)C4—C3—H3120.00
Cu1—O1—C8122.78 (15)C3—C4—H4120.00
N2—N1—C7120.0 (2)C5—C4—H4120.00
Cu1—N2—N1126.26 (17)C4—C5—H5120.00
Cu1—N2—C1118.61 (16)C6—C5—H5120.00
N1—N2—C1113.7 (2)C1—C6—H6120.00
N2—C1—C2119.0 (2)C5—C6—H6120.00
N2—C1—C6122.4 (2)C8—C9—H9119.00
C2—C1—C6118.4 (2)C10—C9—H9120.00
Cl1—C2—C1119.85 (19)C9—C10—H10119.00
Cl1—C2—C3119.1 (2)C11—C10—H10119.00
C1—C2—C3121.1 (2)C11—C12—H12120.00
C2—C3—C4119.3 (3)C13—C12—H12120.00
C3—C4—C5120.4 (3)C12—C13—H13120.00
C4—C5—C6120.0 (2)C14—C13—H13120.00
C1—C6—C5120.8 (2)C13—C14—H14120.00
N1—C7—C8124.3 (2)C15—C14—H14120.00
N1—C7—C16115.1 (2)C14—C15—H15120.00
C8—C7—C16120.1 (2)C16—C15—H15120.00
O1—C8—C7124.1 (2)
O1—Cu1—Cl1—C2123.11 (12)N2—C1—C6—C5172.4 (3)
N2—Cu1—Cl1—C241.58 (13)C2—C1—C6—C5−2.0 (4)
O1i—Cu1—Cl1—C2−56.89 (12)Cl1—C2—C3—C4179.9 (2)
N2i—Cu1—Cl1—C2−138.42 (13)C1—C2—C3—C40.6 (5)
Cl1—Cu1—O1—C8−102.24 (18)C2—C3—C4—C5−2.4 (5)
N2—Cu1—O1—C8−36.98 (19)C3—C4—C5—C62.0 (5)
Cl1i—Cu1—O1—C877.76 (18)C4—C5—C6—C10.3 (5)
N2i—Cu1—O1—C8143.03 (19)N1—C7—C8—O111.7 (4)
Cl1—Cu1—N2—N1142.2 (2)N1—C7—C8—C9−166.8 (2)
Cl1—Cu1—N2—C1−52.32 (16)C16—C7—C8—O1−176.7 (2)
O1—Cu1—N2—N137.1 (2)C16—C7—C8—C94.8 (4)
O1—Cu1—N2—C1−157.39 (18)N1—C7—C16—C11169.5 (2)
Cl1i—Cu1—N2—N1−37.8 (2)N1—C7—C16—C15−11.7 (3)
Cl1i—Cu1—N2—C1127.68 (16)C8—C7—C16—C11−2.9 (4)
O1i—Cu1—N2—N1−142.9 (2)C8—C7—C16—C15176.0 (2)
O1i—Cu1—N2—C122.61 (18)O1—C8—C9—C10178.3 (2)
Cu1—Cl1—C2—C1−33.3 (2)C7—C8—C9—C10−3.1 (4)
Cu1—Cl1—C2—C3147.4 (3)C8—C9—C10—C11−0.7 (4)
Cu1—O1—C8—C721.9 (3)C9—C10—C11—C12−176.8 (3)
Cu1—O1—C8—C9−159.62 (18)C9—C10—C11—C162.7 (4)
C7—N1—N2—Cu1−18.4 (3)C10—C11—C12—C13179.1 (3)
C7—N1—N2—C1175.5 (2)C16—C11—C12—C13−0.3 (4)
N2—N1—C7—C8−13.2 (4)C10—C11—C16—C7−0.8 (4)
N2—N1—C7—C16174.8 (2)C10—C11—C16—C15−179.8 (3)
Cu1—N2—C1—C253.1 (3)C12—C11—C16—C7178.6 (2)
Cu1—N2—C1—C6−121.3 (2)C12—C11—C16—C15−0.3 (4)
N1—N2—C1—C2−139.7 (2)C11—C12—C13—C141.0 (4)
N1—N2—C1—C646.0 (3)C12—C13—C14—C15−1.0 (4)
N2—C1—C2—Cl17.7 (3)C13—C14—C15—C160.4 (4)
N2—C1—C2—C3−173.0 (3)C14—C15—C16—C7−178.6 (3)
C6—C1—C2—Cl1−177.7 (2)C14—C15—C16—C110.3 (4)
C6—C1—C2—C31.6 (4)
D—H···AD—HH···AD···AD—H···A
C5—H5···O1ii0.932.623.300 (3)130
C5—H5···Cl1ii0.932.943.682 (3)138
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C5—H5⋯O1i 0.932.623.300 (3)130
C5—H5⋯Cl1i 0.932.943.682 (3)138

Symmetry code: (i) .

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