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Acta Cryst. (2011). E67, m599-m600    [ doi:10.1107/S1600536811013559 ]

Bis([mu]-hexadecanoato-[kappa]2O:O)bis[(2,2'-bipyridine-[kappa]2N,N')(hexadecanoato-[kappa]O)copper(II)] methanol disolvate

A. N. Che Mat, N. Abdullah, H. Khaledi and J. T. Tee

Abstract top

The asymmetric unit of the title compound, [Cu2(C16H31O2)4(C10H8N2)2]·2CH3OH, contains one half-molecule of the metal complex solvated by a methanol molecule. In the complex, two of the metal atoms are doubly bridged by two monodentate bridging hexadecanoate ligands around a center of inversion. The square-pyramidal geometry around each CuII ion is completed by a terminal hexadecanoate O atom and two N atoms from a 2,2'-bipyridine ligand. The alkyl chains of the carboxylate ligands are arranged in a parallel manner with an all-trans conformation. In the crystal, a [pi]-[pi] interaction formed by the bipyridine rings [centroid-centroid separation = 3.7723 (17) Å] and intermolecular C-H...O hydrogen bonds link the complex molecules into infinite chains along the b axis. An O-H...O interaction between the methanol solvate and one of the carboxylate O atoms is also observed.

Comment top

Metallomesogens are metal containing liquid crystals. Active research in this field started around 30 years ago (Giroud-Godquin, 1998), and these materials have found useful applications as ordered solvents, catalysts, and templates for synthesis, optical and ferroelectric systems, electronic or ionic conductors, and membranes. However, most metallomesogens have high melting points (greater than 523 K), high viscosity, and narrow isotropic range. Our research group is focused on functional low-temperature and thermally stable metallomesogens for spintronic, electronic, photonic and catalytic applications. To achieve this, we applied the concept of symmetry reduction and use of ligands with long (linear or branched) alkyl chains. Herein, we report the crystal structure of one such complex.

The title compound is a centrosymmetric dinuclear copper(II) complex in which the metal ions are five-coordinate in a square-pyramidal geometry with the τ value (Addison et al., 1984) of 0.016. The coordination geometry around each metal center is defined by two nitrogen atoms from a 2,2'-bipyridine and two O atoms from two monodentate hexadecanoato ligands at the basal positions. The square-pyramidal coordination of Cu(II) is completed by bonding to the bridging hexadecanoate O atom in the axial direction with Cu—O distance of 2.349 (2) Å. Within this double bridged dimer, the Cu···Cu distance [3.3740 (6) Å] is comparable to those observed in similar structures (Antolini et al., 1985; Zhang et al., 2006). The alkyl chains of the carboxylate ligands are arranged in a parallel manner with an all trans conformation. The methanol solvent molecule is a hydrogen bond donor to the carboxylate O2 atom. In the crystal, intermolecular C—H···O interactions (Table 1) connect the molecules into infinite chains along the b axis. The one-dimensional link is supplemented by a π-π stacking interaction between the anti-parallely arranged bipyridine rings of the adjacent molecules, the pyridyl rings centroid-centroid separation being 3.7723 (17) Å. Intramolecular C—H···O interactions are also observed.

Related literature top

For background to metallomesogens, see: Giroud-Godquin (1998). For the structures of similar copper(II) complexes, see: Antolini et al. (1985); Zhang et al. (2006). For a description of the geometry of complexes with a five-coordinate metal atom, see: Addison et al. (1984).

Experimental top

An aqueous solution of copper(II)nitrate trihydrate (5.7 g, 23.4 mmol) was added portionwise to a hot ethanolic solution (150 ml) of hexadecanoic acid (6 g, 23.4 mmol) and p-aminobenzoic acid (3.2 g, 23.6 mmol). The green solution formed was allowed to cool to room temperature, and then an excess amount of ammonia (30%) was added. The purple solution formed was stirred at room temperature overnight, and then heated gently to remove excess ammonia and get the pale blue precipitate of [Cu2(p-H2NC6H4COO)2(CH3(CH2)14COO)2]. 2,2'-Bipyridine (0.19 g, 1.2 mmol) was added to a suspension of [Cu2(p-H2NC6H4COO)2(CH3(CH2)14COO)2] (1 g, 1.1 mmol) in a 1:2 mixture of methanol-ethanol (60 ml). The mixture was heated for 30 minutes and the black precipitate was filtered off. The small blue crystals obtained from the filtrate, on standing overnight, were recrystallized from methanol-THF (1:1), to give the dark blue crystals of the title compound after two weeks.

Refinement top

The C-bound hydrogen atoms were placed at calculated positions (C–H 0.93–0.97 Å), and were treated as riding on their parent carbon atoms. The oxygen-bound H atom was located in a difference Fourier map and refined with distance restraint of O–H 0.82±0.02 Å. For hydrogen atoms Uiso(H) were set to 1.2–1.5 times Ueq(carrier atom).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of the title compound at the 30% probability level. Atom labels for consecutively numbered rings and alkyl chains, as well as C-bound hydrogen atoms have been omitted for clarity. Symmetry code: ' = -x+2, –y+1, -z+1.
[Figure 2] Fig. 2. Packing view looking down the crystallographic a axis.
Bis(µ-hexadecanoato-κ2O:O)bis[(2,2'-bipyridine- κ2N,N')(hexadecanoato-κO)copper(II)] methanol disolvate top
Crystal data top
[Cu2(C16H31O2)4(C10H8N2)2]·2CH4OZ = 1
Mr = 1525.16F(000) = 830
Triclinic, P1Dx = 1.146 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6064 (3) ÅCell parameters from 2321 reflections
b = 9.7506 (3) Åθ = 2.5–21.5°
c = 24.0234 (8) ŵ = 0.54 mm−1
α = 92.559 (2)°T = 296 K
β = 98.681 (2)°Block, blue
γ = 95.516 (2)°0.40 × 0.27 × 0.09 mm
V = 2210.14 (12) Å3
Data collection top
Bruker APEXII CCD
diffractometer		8088 independent reflections
Radiation source: fine-focus sealed tube5498 reflections with I > 2σ(I)
graphiteRint = 0.034
φ and ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.814, Tmax = 0.953k = −11→11
13457 measured reflectionsl = −29→29
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.061P)2]
where P = (Fo2 + 2Fc2)/3
8088 reflections(Δ/σ)max = 0.011
466 parametersΔρmax = 0.31 e Å−3
1 restraintΔρmin = −0.24 e Å−3
Crystal data top
[Cu2(C16H31O2)4(C10H8N2)2]·2CH4Oγ = 95.516 (2)°
Mr = 1525.16V = 2210.14 (12) Å3
Triclinic, P1Z = 1
a = 9.6064 (3) ÅMo Kα radiation
b = 9.7506 (3) ŵ = 0.54 mm−1
c = 24.0234 (8) ÅT = 296 K
α = 92.559 (2)°0.40 × 0.27 × 0.09 mm
β = 98.681 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		8088 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5498 reflections with I > 2σ(I)
Tmin = 0.814, Tmax = 0.953Rint = 0.034
13457 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127Δρmax = 0.31 e Å−3
S = 0.99Δρmin = −0.24 e Å−3
8088 reflectionsAbsolute structure: ?
466 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.91189 (3)0.34121 (3)0.498126 (15)0.03823 (13)
O10.7446 (2)0.42240 (19)0.51491 (9)0.0475 (5)
O20.6702 (2)0.2457 (2)0.56137 (10)0.0619 (6)
O30.96731 (19)0.53048 (18)0.44537 (8)0.0426 (5)
O40.9778 (2)0.7002 (2)0.38786 (10)0.0602 (6)
N11.0740 (2)0.2359 (2)0.48224 (10)0.0378 (6)
N20.8058 (2)0.1916 (2)0.44362 (10)0.0394 (6)
C10.6751 (3)0.3687 (3)0.55073 (14)0.0452 (8)
C20.5984 (3)0.4670 (3)0.58304 (14)0.0542 (9)
H2A0.55580.53140.55770.065*
H2B0.52360.41540.59870.065*
C30.7025 (3)0.5457 (3)0.63028 (14)0.0556 (9)
H3A0.74960.47960.65340.067*
H3B0.77410.59980.61380.067*
C40.6373 (3)0.6407 (3)0.66775 (14)0.0606 (9)
H4A0.59320.70910.64500.073*
H4B0.56350.58740.68340.073*
C50.7410 (4)0.7138 (4)0.71538 (15)0.0671 (10)
H5A0.81280.76890.69930.081*
H5B0.78780.64480.73690.081*
C60.6812 (4)0.8064 (4)0.75564 (15)0.0641 (10)
H6A0.63780.87810.73470.077*
H6B0.60720.75250.77090.077*
C70.7877 (4)0.8737 (4)0.80388 (15)0.0657 (10)
H7A0.86210.92640.78840.079*
H7B0.83040.80170.82490.079*
C80.7305 (4)0.9680 (4)0.84449 (15)0.0666 (10)
H8A0.68611.03920.82350.080*
H8B0.65760.91500.86070.080*
C90.8383 (4)1.0361 (4)0.89138 (15)0.0695 (11)
H9A0.91041.08960.87490.083*
H9B0.88370.96450.91170.083*
C100.7853 (4)1.1292 (4)0.93316 (15)0.0681 (10)
H10A0.73871.20000.91270.082*
H10B0.71401.07530.95000.082*
C110.8932 (4)1.1989 (4)0.97973 (16)0.0720 (11)
H11A0.93891.12831.00060.086*
H11B0.96501.25220.96300.086*
C120.8389 (4)1.2925 (4)1.02059 (15)0.0724 (11)
H12A0.76821.23861.03770.087*
H12B0.79141.36170.99950.087*
C130.9456 (4)1.3652 (4)1.06694 (16)0.0772 (11)
H13A0.99271.29601.08820.093*
H13B1.01671.41881.04990.093*
C140.8910 (4)1.4587 (4)1.10716 (16)0.0781 (12)
H14A0.81961.40501.12400.094*
H14B0.84391.52771.08570.094*
C150.9958 (5)1.5325 (5)1.15394 (19)0.0965 (14)
H15A1.04221.46411.17600.116*
H15B1.06781.58611.13740.116*
C160.9367 (5)1.6263 (5)1.19290 (19)0.1150 (18)
H16A0.89611.69851.17220.172*
H16B1.01101.66591.22210.172*
H16C0.86491.57481.20950.172*
C170.9304 (3)0.5849 (3)0.39814 (13)0.0421 (7)
C180.8202 (3)0.4979 (3)0.35562 (13)0.0512 (8)
H18A0.74880.45380.37540.061*
H18B0.77390.55820.32930.061*
C190.8802 (3)0.3880 (3)0.32266 (13)0.0482 (8)
H19A0.95340.43150.30360.058*
H19B0.92380.32570.34870.058*
C200.7695 (3)0.3054 (3)0.27940 (14)0.0565 (9)
H20A0.69930.25840.29900.068*
H20B0.72190.36910.25510.068*
C210.8245 (3)0.1999 (3)0.24292 (14)0.0590 (9)
H21A0.86560.13180.26680.071*
H21B0.89940.24550.22530.071*
C220.7130 (4)0.1261 (4)0.19725 (15)0.0657 (10)
H22A0.64240.07430.21510.079*
H22B0.66600.19480.17560.079*
C230.7670 (4)0.0293 (4)0.15724 (15)0.0678 (10)
H23A0.8096−0.04220.17860.081*
H23B0.84100.08000.14080.081*
C240.6571 (4)−0.0390 (4)0.10995 (15)0.0671 (10)
H24A0.5851−0.09300.12640.081*
H24B0.61170.03240.08950.081*
C250.7126 (4)−0.1317 (4)0.06851 (15)0.0679 (10)
H25A0.7834−0.07720.05170.081*
H25B0.7598−0.20190.08910.081*
C260.6041 (4)−0.2025 (4)0.02180 (15)0.0679 (10)
H26A0.5341−0.25840.03850.081*
H26B0.5558−0.13250.00150.081*
C270.6611 (4)−0.2929 (4)−0.01978 (15)0.0679 (10)
H27A0.7115−0.36110.00080.082*
H27B0.7295−0.2363−0.03700.082*
C280.5540 (4)−0.3672 (4)−0.06597 (15)0.0697 (10)
H28A0.4855−0.4239−0.04880.084*
H28B0.5037−0.2991−0.08670.084*
C290.6122 (4)−0.4565 (4)−0.10674 (15)0.0720 (11)
H29A0.6636−0.5234−0.08570.086*
H29B0.6802−0.3992−0.12390.086*
C300.5078 (4)−0.5336 (4)−0.15314 (16)0.0751 (11)
H30A0.4400−0.5910−0.13590.090*
H30B0.4561−0.4667−0.17410.090*
C310.5658 (5)−0.6224 (4)−0.19391 (17)0.0912 (14)
H31A0.6188−0.6884−0.17300.109*
H31B0.6322−0.5647−0.21170.109*
C320.4606 (5)−0.7003 (5)−0.23923 (18)0.1087 (17)
H32A0.4007−0.7659−0.22260.163*
H32B0.5096−0.7480−0.26490.163*
H32C0.4039−0.6370−0.25930.163*
C331.2115 (3)0.2658 (3)0.50422 (13)0.0452 (8)
H331.23890.34730.52640.054*
C341.3123 (3)0.1815 (3)0.49531 (14)0.0481 (8)
H341.40650.20640.51080.058*
C351.2743 (3)0.0604 (3)0.46349 (14)0.0495 (8)
H351.34150.00070.45790.059*
C361.1338 (3)0.0283 (3)0.43977 (13)0.0462 (8)
H361.1054−0.05290.41750.055*
C371.0366 (3)0.1174 (3)0.44938 (12)0.0374 (7)
C380.8836 (3)0.0946 (3)0.42662 (12)0.0367 (7)
C390.8228 (3)−0.0172 (3)0.39013 (13)0.0497 (8)
H390.8778−0.08360.37870.060*
C400.6794 (4)−0.0272 (3)0.37133 (14)0.0572 (9)
H400.6364−0.10090.34680.069*
C410.5997 (3)0.0712 (3)0.38858 (14)0.0539 (9)
H410.50270.06490.37610.065*
C420.6662 (3)0.1794 (3)0.42469 (13)0.0456 (8)
H420.61240.24640.43640.055*
O50.6666 (4)0.1341 (4)0.66351 (13)0.1153 (12)
H50.656 (7)0.175 (5)0.6327 (15)0.173*
C430.7910 (5)0.1699 (5)0.6985 (2)0.1218 (19)
H43A0.84720.09340.70000.183*
H43B0.77240.19400.73560.183*
H43C0.84150.24750.68450.183*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0363 (2)0.0308 (2)0.0444 (2)0.00502 (14)−0.00033 (16)−0.01253 (15)
O10.0442 (11)0.0392 (11)0.0593 (15)0.0086 (9)0.0092 (11)−0.0083 (11)
O20.0750 (15)0.0396 (13)0.0710 (17)0.0061 (11)0.0141 (13)−0.0066 (11)
O30.0505 (12)0.0330 (10)0.0406 (12)0.0066 (9)−0.0032 (10)−0.0084 (9)
O40.0753 (15)0.0399 (12)0.0614 (15)0.0001 (12)0.0018 (12)0.0020 (11)
N10.0379 (12)0.0287 (12)0.0446 (15)0.0048 (10)0.0013 (11)−0.0066 (11)
N20.0396 (13)0.0326 (12)0.0444 (15)0.0048 (10)0.0029 (12)−0.0072 (11)
C10.0363 (16)0.0461 (19)0.049 (2)0.0046 (14)−0.0028 (15)−0.0146 (16)
C20.0430 (17)0.0542 (19)0.063 (2)0.0080 (15)0.0056 (16)−0.0197 (17)
C30.0507 (18)0.0547 (19)0.057 (2)0.0079 (16)0.0008 (17)−0.0182 (17)
C40.059 (2)0.064 (2)0.055 (2)0.0191 (17)−0.0021 (17)−0.0208 (18)
C50.066 (2)0.070 (2)0.063 (2)0.0134 (19)0.0036 (19)−0.0224 (19)
C60.063 (2)0.069 (2)0.058 (2)0.0150 (18)0.0021 (18)−0.0217 (18)
C70.068 (2)0.068 (2)0.060 (2)0.0147 (19)0.0034 (19)−0.0177 (19)
C80.069 (2)0.073 (2)0.055 (2)0.0106 (19)0.0043 (19)−0.0191 (19)
C90.068 (2)0.075 (2)0.062 (2)0.009 (2)0.004 (2)−0.021 (2)
C100.070 (2)0.075 (2)0.056 (2)0.008 (2)0.0067 (19)−0.0178 (19)
C110.067 (2)0.078 (3)0.065 (3)0.003 (2)0.001 (2)−0.021 (2)
C120.076 (2)0.075 (2)0.061 (2)0.010 (2)0.000 (2)−0.024 (2)
C130.077 (3)0.079 (3)0.069 (3)0.003 (2)0.001 (2)−0.020 (2)
C140.081 (3)0.082 (3)0.063 (3)0.008 (2)−0.007 (2)−0.019 (2)
C150.092 (3)0.106 (3)0.079 (3)−0.002 (3)−0.006 (3)−0.028 (3)
C160.140 (4)0.109 (4)0.084 (3)0.004 (3)−0.004 (3)−0.039 (3)
C170.0434 (16)0.0392 (17)0.0420 (19)0.0115 (14)−0.0002 (15)−0.0090 (15)
C180.0495 (18)0.0500 (18)0.049 (2)0.0106 (15)−0.0102 (15)−0.0089 (15)
C190.0520 (18)0.0460 (17)0.0429 (19)0.0037 (15)0.0000 (15)−0.0081 (15)
C200.059 (2)0.0553 (19)0.049 (2)−0.0006 (16)−0.0012 (17)−0.0160 (16)
C210.0565 (19)0.061 (2)0.053 (2)0.0002 (17)−0.0026 (17)−0.0195 (17)
C220.064 (2)0.065 (2)0.062 (2)−0.0002 (18)0.0034 (19)−0.0245 (19)
C230.064 (2)0.072 (2)0.060 (2)0.0040 (19)−0.0010 (19)−0.0249 (19)
C240.066 (2)0.068 (2)0.061 (2)−0.0003 (19)0.0018 (19)−0.0249 (19)
C250.068 (2)0.071 (2)0.059 (2)0.0068 (19)−0.0021 (19)−0.0239 (19)
C260.070 (2)0.070 (2)0.057 (2)0.0007 (19)0.0009 (19)−0.0244 (19)
C270.071 (2)0.071 (2)0.056 (2)0.0050 (19)0.0004 (19)−0.0215 (19)
C280.074 (2)0.071 (2)0.057 (2)0.002 (2)0.0013 (19)−0.0211 (19)
C290.075 (2)0.075 (2)0.059 (2)0.010 (2)−0.005 (2)−0.023 (2)
C300.082 (3)0.078 (3)0.058 (2)0.005 (2)−0.004 (2)−0.020 (2)
C310.102 (3)0.094 (3)0.069 (3)0.016 (3)−0.006 (2)−0.036 (2)
C320.115 (4)0.118 (4)0.080 (3)0.013 (3)−0.015 (3)−0.047 (3)
C330.0416 (16)0.0331 (15)0.058 (2)0.0040 (13)0.0018 (15)−0.0085 (14)
C340.0368 (16)0.0427 (17)0.064 (2)0.0066 (14)0.0046 (16)−0.0007 (16)
C350.0483 (18)0.0391 (17)0.065 (2)0.0141 (14)0.0161 (16)−0.0040 (16)
C360.0509 (18)0.0346 (16)0.053 (2)0.0048 (14)0.0114 (16)−0.0117 (14)
C370.0434 (16)0.0287 (14)0.0398 (17)0.0027 (12)0.0075 (14)−0.0034 (13)
C380.0441 (16)0.0300 (14)0.0345 (16)0.0012 (12)0.0036 (13)−0.0024 (12)
C390.0553 (19)0.0392 (17)0.050 (2)0.0023 (15)0.0021 (16)−0.0167 (15)
C400.065 (2)0.0416 (18)0.055 (2)−0.0066 (16)−0.0075 (17)−0.0188 (16)
C410.0457 (17)0.0539 (19)0.053 (2)−0.0041 (16)−0.0114 (16)−0.0064 (16)
C420.0405 (16)0.0432 (17)0.051 (2)0.0041 (14)0.0019 (15)−0.0063 (15)
O50.116 (2)0.135 (3)0.078 (2)−0.052 (2)0.003 (2)0.003 (2)
C430.120 (4)0.148 (5)0.085 (4)−0.033 (4)0.003 (3)0.012 (3)
Geometric parameters (Å, °) top
Cu1—O11.945 (2)C19—C201.512 (4)
Cu1—O3i1.9617 (17)C19—H19A0.9700
Cu1—N22.005 (2)C19—H19B0.9700
Cu1—N12.019 (2)C20—C211.507 (4)
Cu1—O32.349 (2)C20—H20A0.9700
O1—C11.268 (4)C20—H20B0.9700
O2—C11.235 (4)C21—C221.515 (4)
O3—C171.289 (3)C21—H21A0.9700
O3—Cu1i1.9617 (17)C21—H21B0.9700
O4—C171.222 (3)C22—C231.499 (4)
N1—C331.346 (3)C22—H22A0.9700
N1—C371.357 (3)C22—H22B0.9700
N2—C421.342 (3)C23—C241.511 (4)
N2—C381.347 (3)C23—H23A0.9700
C1—C21.519 (4)C23—H23B0.9700
C2—C31.519 (4)C24—C251.505 (4)
C2—H2A0.9700C24—H24A0.9700
C2—H2B0.9700C24—H24B0.9700
C3—C41.506 (4)C25—C261.504 (4)
C3—H3A0.9700C25—H25A0.9700
C3—H3B0.9700C25—H25B0.9700
C4—C51.502 (4)C26—C271.502 (4)
C4—H4A0.9700C26—H26A0.9700
C4—H4B0.9700C26—H26B0.9700
C5—C61.507 (4)C27—C281.502 (4)
C5—H5A0.9700C27—H27A0.9700
C5—H5B0.9700C27—H27B0.9700
C6—C71.505 (4)C28—C291.487 (5)
C6—H6A0.9700C28—H28A0.9700
C6—H6B0.9700C28—H28B0.9700
C7—C81.510 (4)C29—C301.502 (4)
C7—H7A0.9700C29—H29A0.9700
C7—H7B0.9700C29—H29B0.9700
C8—C91.493 (4)C30—C311.484 (5)
C8—H8A0.9700C30—H30A0.9700
C8—H8B0.9700C30—H30B0.9700
C9—C101.501 (4)C31—C321.493 (5)
C9—H9A0.9700C31—H31A0.9700
C9—H9B0.9700C31—H31B0.9700
C10—C111.495 (4)C32—H32A0.9600
C10—H10A0.9700C32—H32B0.9600
C10—H10B0.9700C32—H32C0.9600
C11—C121.494 (4)C33—C341.363 (4)
C11—H11A0.9700C33—H330.9300
C11—H11B0.9700C34—C351.365 (4)
C12—C131.496 (4)C34—H340.9300
C12—H12A0.9700C35—C361.384 (4)
C12—H12B0.9700C35—H350.9300
C13—C141.486 (5)C36—C371.372 (4)
C13—H13A0.9700C36—H360.9300
C13—H13B0.9700C37—C381.481 (4)
C14—C151.497 (5)C38—C391.391 (3)
C14—H14A0.9700C39—C401.377 (4)
C14—H14B0.9700C39—H390.9300
C15—C161.490 (5)C40—C411.371 (4)
C15—H15A0.9700C40—H400.9300
C15—H15B0.9700C41—C421.377 (4)
C16—H16A0.9600C41—H410.9300
C16—H16B0.9600C42—H420.9300
C16—H16C0.9600O5—C431.359 (5)
C17—C181.519 (4)O5—H50.86 (2)
C18—C191.513 (4)C43—H43A0.9600
C18—H18A0.9700C43—H43B0.9600
C18—H18B0.9700C43—H43C0.9600
O1—Cu1—O3i90.51 (8)C20—C19—C18113.0 (2)
O1—Cu1—N295.52 (9)C20—C19—H19A109.0
O3i—Cu1—N2172.47 (8)C18—C19—H19A109.0
O1—Cu1—N1173.45 (9)C20—C19—H19B109.0
O3i—Cu1—N193.43 (8)C18—C19—H19B109.0
N2—Cu1—N180.17 (9)H19A—C19—H19B107.8
O1—Cu1—O389.86 (8)C21—C20—C19115.3 (3)
O3i—Cu1—O377.36 (8)C21—C20—H20A108.4
N2—Cu1—O3107.08 (8)C19—C20—H20A108.4
N1—Cu1—O396.10 (8)C21—C20—H20B108.4
C1—O1—Cu1119.20 (19)C19—C20—H20B108.4
C17—O3—Cu1i113.34 (17)H20A—C20—H20B107.5
C17—O3—Cu1142.73 (18)C20—C21—C22114.1 (3)
Cu1i—O3—Cu1102.64 (8)C20—C21—H21A108.7
C33—N1—C37117.7 (2)C22—C21—H21A108.7
C33—N1—Cu1126.72 (18)C20—C21—H21B108.7
C37—N1—Cu1115.38 (17)C22—C21—H21B108.7
C42—N2—C38118.8 (2)H21A—C21—H21B107.6
C42—N2—Cu1125.58 (19)C23—C22—C21115.3 (3)
C38—N2—Cu1115.63 (17)C23—C22—H22A108.4
O2—C1—O1124.4 (3)C21—C22—H22A108.4
O2—C1—C2119.8 (3)C23—C22—H22B108.4
O1—C1—C2115.8 (3)C21—C22—H22B108.4
C3—C2—C1109.7 (2)H22A—C22—H22B107.5
C3—C2—H2A109.7C22—C23—C24115.4 (3)
C1—C2—H2A109.7C22—C23—H23A108.4
C3—C2—H2B109.7C24—C23—H23A108.4
C1—C2—H2B109.7C22—C23—H23B108.4
H2A—C2—H2B108.2C24—C23—H23B108.4
C4—C3—C2114.7 (3)H23A—C23—H23B107.5
C4—C3—H3A108.6C25—C24—C23115.2 (3)
C2—C3—H3A108.6C25—C24—H24A108.5
C4—C3—H3B108.6C23—C24—H24A108.5
C2—C3—H3B108.6C25—C24—H24B108.5
H3A—C3—H3B107.6C23—C24—H24B108.5
C5—C4—C3113.9 (3)H24A—C24—H24B107.5
C5—C4—H4A108.8C26—C25—C24115.9 (3)
C3—C4—H4A108.8C26—C25—H25A108.3
C5—C4—H4B108.8C24—C25—H25A108.3
C3—C4—H4B108.8C26—C25—H25B108.3
H4A—C4—H4B107.7C24—C25—H25B108.3
C4—C5—C6116.4 (3)H25A—C25—H25B107.4
C4—C5—H5A108.2C27—C26—C25115.3 (3)
C6—C5—H5A108.2C27—C26—H26A108.4
C4—C5—H5B108.2C25—C26—H26A108.4
C6—C5—H5B108.2C27—C26—H26B108.4
H5A—C5—H5B107.3C25—C26—H26B108.4
C7—C6—C5114.7 (3)H26A—C26—H26B107.5
C7—C6—H6A108.6C26—C27—C28116.2 (3)
C5—C6—H6A108.6C26—C27—H27A108.2
C7—C6—H6B108.6C28—C27—H27A108.2
C5—C6—H6B108.6C26—C27—H27B108.2
H6A—C6—H6B107.6C28—C27—H27B108.2
C6—C7—C8115.7 (3)H27A—C27—H27B107.4
C6—C7—H7A108.4C29—C28—C27115.5 (3)
C8—C7—H7A108.4C29—C28—H28A108.4
C6—C7—H7B108.4C27—C28—H28A108.4
C8—C7—H7B108.4C29—C28—H28B108.4
H7A—C7—H7B107.4C27—C28—H28B108.4
C9—C8—C7114.9 (3)H28A—C28—H28B107.5
C9—C8—H8A108.5C28—C29—C30116.9 (3)
C7—C8—H8A108.5C28—C29—H29A108.1
C9—C8—H8B108.5C30—C29—H29A108.1
C7—C8—H8B108.5C28—C29—H29B108.1
H8A—C8—H8B107.5C30—C29—H29B108.1
C8—C9—C10116.6 (3)H29A—C29—H29B107.3
C8—C9—H9A108.2C31—C30—C29116.9 (3)
C10—C9—H9A108.2C31—C30—H30A108.1
C8—C9—H9B108.2C29—C30—H30A108.1
C10—C9—H9B108.2C31—C30—H30B108.1
H9A—C9—H9B107.3C29—C30—H30B108.1
C11—C10—C9116.7 (3)H30A—C30—H30B107.3
C11—C10—H10A108.1C30—C31—C32116.4 (4)
C9—C10—H10A108.1C30—C31—H31A108.2
C11—C10—H10B108.1C32—C31—H31A108.2
C9—C10—H10B108.1C30—C31—H31B108.2
H10A—C10—H10B107.3C32—C31—H31B108.2
C12—C11—C10116.0 (3)H31A—C31—H31B107.3
C12—C11—H11A108.3C31—C32—H32A109.5
C10—C11—H11A108.3C31—C32—H32B109.5
C12—C11—H11B108.3H32A—C32—H32B109.5
C10—C11—H11B108.3C31—C32—H32C109.5
H11A—C11—H11B107.4H32A—C32—H32C109.5
C11—C12—C13116.9 (3)H32B—C32—H32C109.5
C11—C12—H12A108.1N1—C33—C34122.7 (3)
C13—C12—H12A108.1N1—C33—H33118.6
C11—C12—H12B108.1C34—C33—H33118.6
C13—C12—H12B108.1C33—C34—C35119.7 (3)
H12A—C12—H12B107.3C33—C34—H34120.2
C14—C13—C12116.5 (3)C35—C34—H34120.2
C14—C13—H13A108.2C34—C35—C36118.6 (3)
C12—C13—H13A108.2C34—C35—H35120.7
C14—C13—H13B108.2C36—C35—H35120.7
C12—C13—H13B108.2C37—C36—C35119.4 (3)
H13A—C13—H13B107.3C37—C36—H36120.3
C13—C14—C15117.5 (3)C35—C36—H36120.3
C13—C14—H14A107.9N1—C37—C36121.8 (2)
C15—C14—H14A107.9N1—C37—C38113.6 (2)
C13—C14—H14B107.9C36—C37—C38124.6 (2)
C15—C14—H14B107.9N2—C38—C39121.7 (3)
H14A—C14—H14B107.2N2—C38—C37114.8 (2)
C16—C15—C14115.7 (4)C39—C38—C37123.4 (3)
C16—C15—H15A108.4C40—C39—C38118.3 (3)
C14—C15—H15A108.4C40—C39—H39120.8
C16—C15—H15B108.4C38—C39—H39120.8
C14—C15—H15B108.4C41—C40—C39120.2 (3)
H15A—C15—H15B107.4C41—C40—H40119.9
C15—C16—H16A109.5C39—C40—H40119.9
C15—C16—H16B109.5C40—C41—C42118.6 (3)
H16A—C16—H16B109.5C40—C41—H41120.7
C15—C16—H16C109.5C42—C41—H41120.7
H16A—C16—H16C109.5N2—C42—C41122.4 (3)
H16B—C16—H16C109.5N2—C42—H42118.8
O4—C17—O3123.0 (3)C41—C42—H42118.8
O4—C17—C18121.1 (3)C43—O5—H5116 (4)
O3—C17—C18115.9 (3)O5—C43—H43A109.5
C19—C18—C17113.9 (2)O5—C43—H43B109.5
C19—C18—H18A108.8H43A—C43—H43B109.5
C17—C18—H18A108.8O5—C43—H43C109.5
C19—C18—H18B108.8H43A—C43—H43C109.5
C17—C18—H18B108.8H43B—C43—H43C109.5
H18A—C18—H18B107.7
Symmetry codes: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O1i0.932.503.093 (3)122
C33—H33···O3i0.932.573.071 (3)114
C35—H35···O2ii0.932.423.129 (3)134
C39—H39···O4iii0.932.413.258 (4)152
C41—H41···O5iv0.932.463.153 (4)131
C42—H42···O10.932.593.096 (3)115
O5—H5···O20.86 (2)1.89 (3)2.732 (4)166 (6)
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) x, y−1, z; (iv) −x+1, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C33—H33···O1i0.932.503.093 (3)122
C33—H33···O3i0.932.573.071 (3)114
C35—H35···O2ii0.932.423.129 (3)134
C39—H39···O4iii0.932.413.258 (4)152
C41—H41···O5iv0.932.463.153 (4)131
C42—H42···O10.932.593.096 (3)115
O5—H5···O20.86 (2)1.89 (3)2.732 (4)166 (6)
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) x, y−1, z; (iv) −x+1, −y, −z+1.
Acknowledgements top

The authors thank the Malaysian government for the Fundamental Research Grant Scheme (FRGS FP046/2008, FP017/2009), and the University of Malaya Grants (RG039/09SUS, PS339/2009 C).

references
References top

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