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Acta Cryst. (2007). E63, m1977-m1978    [ doi:10.1107/S1600536807029583 ]

A cofacial binuclear copper(II) complex with a bridging 1,4-dithiane ligand

S. Burton, F. R. Fronczek and A. W. Maverick

Abstract top

The molecule of ([mu]-1,4-dithiane-[kappa]2S:S')bis{[mu]-3,3'-[naphthalene-2,7-diylbis(methylene)]bis(pentane-2,4-dionato)-[kappa]4O,O':O'',O'''}dicopper(II), [Cu2(C22H22O4)(C4H8S2)], lies on an inversion center, with a Cu...Cu distance of 8.130 (1) Å. The CuII centers have square-pyramidal coordination geometry, with Cu-O distances in the range 1.905 (2)-1.925 (2) Å and a Cu-S distance of 2.8088 (10) Å. The host binuclear complex is distorted from a rectangular shape. The inversion symmetry of the molecule requires that the two coordination planes be parallel. However, they are `slipped': the normals to the two coordination planes at the Cu atoms are 1.865 (1) Å apart. Another measure of this `slipping' is provided by the four CH2 groups, whose C atoms form a parallelogram with interior angles of 87.2 (3) and 92.8 (3)°. The two chelate rings tilt differently from the coordination plane, with one Cu atom lying only 0.0131 (5) Å out of one C3O2 mean plane, but 0.4416 (5) Å out of the other. Those two chelate planes form a dihedral angle of 11.2 (4)°. This relatively large deviation is believed to be due to the large size of the 1,4-dithiane guest.

Comment top

Our group has previously prepared binuclear metal complexes derived from polydentate liands, which have been shown to intramolecularly bind bridging substrate molecules, similar to those produced by several other flexible binucleating macrocycles. This work was undertaken in an attempt to associate and quantify the binding between di-sulfur bases and their previously studied nitrogen analogues, see Related Literature section.

The molecule is centrosymmetric, and inclusion of the 1,4-dithiane molecule organizes the host such that the Cu···Cu distance, 8.130 (1) Å, is longer than in complexes with other guests, see Related Literature section. Several distortions take place in this organization. The Cu2(NBA)2 unit is not rectangular, but slipped such that the four CH2 groups (C6, C17 and their inversion equivalents) form a parallelogram with sides 7.578 (5) and 9.570 (5) Å, and interior angles differing from orthogonality by 2.8 (3)°. This involves a slippage of the coordination planes horizontally by 1.865 (1) Å.

The coordination sphere is square pyramidal, with distances given in the Abstract and geometric details table. The two chelate rings tilt differently from the coordination plane, with Cu1 lying only 0.0131 (5) Å out of the best plane O1/O2/C2/C3/C4, but 0.4416 (5) Å out of the best plane O3/O4/C19/C20/C21. Those two planes form a dihedral angle of 11.2 (4)°. The Cu—S bond is tilted away from O1 and O2 (O—Cu—S angles 98.91 (8) and 96.32 (7)°) and toward O3 and O4 (angles 86.77 (7) and 87.66 (7)°), and forms an angle of 20.15 (5)° with the Cu···Cu vector.

Related literature top

Cu2(NBA)2 forms a crystalline solvate with two CHCl3 molecules, in which the Cu···Cu distance is 7.349 (1) Å at room temperature (Maverick et al., 1986) and 7.298 (1) Å at 100 K (Burton et al., 2002). With µ-Dabco (define Dabco?), the Cu···Cu distance is 7.403 (4) Å (Maverick et al., 1986), with µ-2,5-dimethylpyrazine it is 7.559 (2) and 7.596 (2) Å (Maverick et al., 1990), and with µ-2-methylpyrazine it is 7.4801 (8) Å (Maverick et al., 2001). For related literature, see: Martin et al. (1959).

Experimental top

The NBAH2, (2,7-naphthalenediylbis(methylene)bis(acetylacetone)) ligand was prepared previously by the general nucleophilic substitution method outlined by Martin et al. (1959). The Cu2(NBA)2 was also prepared by previously published procedures, see Related Literature section. Bis(3,3'-(naphthalene-2,7-diylbis(methylene)bis(2,4-pentanedionato)))\ dicopper(µ-1,4-dithiane) was prepared by combining a 5.05 mMolar chloroform solution of Cu2(NBA)2 with a 1.02 Molar chloroform solution of 1,4-dithiane. The resulting mixture was layered with acetonitrile and afforded light blue (turquoise) crystals of Cu2(NBA)2(µ-1,4-dithiane) after standing for 5 days.

Refinement top

H atoms were placed in idealized positions with C—H distances 0.95 − 0.99 Å and thereafter treated as riding. Uiso for H was assigned as 1.2 times Ueq of the attached C atoms (1.5 for methyl). A torsional parameter was refined for each methyl group.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Numbering scheme and ellipsoids at the 50% level. H atoms are represented with arbitrary radius.
(µ-1,4-Dithiane-κ2S:S')bis[µ-3,3'-(naphthalene-2,7- diyldimethylene)bis(pentane-2,4-dionato)-κ4O,O':O'',O''']dicopper, top
Crystal data top
[Cu2(C22H22O4)(C4H8S2)]F000 = 988
Mr = 948.10Dx = 1.466 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6304 reflections
a = 7.758 (2) Åθ = 2.5–25.0º
b = 28.981 (7) ŵ = 1.14 mm−1
c = 9.640 (3) ÅT = 120 K
β = 97.840 (15)ºPrism, light blue
V = 2147.1 (10) Å30.15 × 0.08 × 0.07 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer with an Oxford Cryosystems Cryostream cooler		3491 independent reflections
Radiation source: fine-focus sealed tube2598 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
T = 120 Kθmax = 25.0º
ω scans with κ offsetsθmin = 2.5º
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		h = −9→9
Tmin = 0.878, Tmax = 0.924k = −33→34
10982 measured reflectionsl = −11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0425P)2 + 2.9798P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3491 reflectionsΔρmax = 0.30 e Å−3
275 parametersΔρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu2(C22H22O4)(C4H8S2)]V = 2147.1 (10) Å3
Mr = 948.10Z = 2
Monoclinic, P21/cMo Kα
a = 7.758 (2) ŵ = 1.14 mm−1
b = 28.981 (7) ÅT = 120 K
c = 9.640 (3) Å0.15 × 0.08 × 0.07 mm
β = 97.840 (15)º
Data collection top
Nonius KappaCCD
diffractometer with an Oxford Cryosystems Cryostream cooler		3491 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		2598 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.924Rint = 0.046
10982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050275 parameters
wR(F2) = 0.110H-atom parameters constrained
S = 1.06Δρmax = 0.30 e Å−3
3491 reflectionsΔρmin = −0.44 e Å−3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.88337 (6)0.458966 (15)0.80517 (5)0.02939 (16)
S10.66505 (12)0.46085 (3)0.54758 (10)0.0331 (3)
O11.0347 (3)0.50850 (8)0.7737 (2)0.0290 (6)
O20.7427 (3)0.49798 (8)0.9033 (2)0.0291 (6)
O30.2550 (3)0.59178 (8)0.1455 (2)0.0300 (6)
O4−0.0323 (3)0.58236 (8)0.2801 (2)0.0291 (6)
C11.1720 (4)0.58089 (13)0.7810 (4)0.0356 (10)
H1A1.24650.58950.86760.053*
H1B1.12320.60880.73360.053*
H1C1.24110.56420.71940.053*
C21.0269 (5)0.55050 (12)0.8153 (4)0.0289 (9)
C30.8971 (4)0.56851 (12)0.8897 (4)0.0280 (9)
C40.7629 (4)0.54102 (13)0.9297 (4)0.0285 (9)
C50.6320 (4)0.56102 (12)1.0147 (4)0.0340 (10)
H5A0.53410.53961.01410.051*
H5B0.58970.59060.97400.051*
H5C0.68710.56591.11120.051*
C60.9059 (4)0.61985 (11)0.9282 (4)0.0293 (9)
H6A0.84580.62431.01140.035*
H6B1.02960.62820.95560.035*
C70.3945 (5)0.66348 (12)0.1506 (4)0.0393 (10)
H7A0.50200.66250.21710.059*
H7B0.34990.69510.14350.059*
H7C0.41870.65310.05850.059*
C80.2612 (4)0.63233 (13)0.2010 (4)0.0296 (9)
C90.1539 (4)0.64831 (12)0.2977 (4)0.0257 (9)
C100.0089 (4)0.62301 (13)0.3266 (4)0.0294 (9)
C11−0.1178 (5)0.64297 (13)0.4144 (4)0.0398 (10)
H11A−0.20970.62040.42340.060*
H11B−0.16950.67100.36990.060*
H11C−0.05700.65050.50760.060*
C120.1908 (4)0.69621 (12)0.3596 (4)0.0317 (9)
H12A0.18200.71870.28170.038*
H12B0.09850.70390.41730.038*
C130.8278 (4)0.65323 (12)0.8151 (4)0.0282 (9)
C140.9166 (5)0.69515 (11)0.7956 (4)0.0317 (9)
H141.02520.70110.85110.038*
C150.8490 (5)0.72711 (12)0.6989 (4)0.0324 (9)
H150.91190.75470.68810.039*
C160.6881 (4)0.71991 (12)0.6148 (4)0.0285 (9)
C170.6175 (4)0.75160 (12)0.5128 (4)0.0305 (9)
H170.67880.77930.49980.037*
C180.4621 (5)0.74330 (12)0.4318 (4)0.0323 (9)
H180.41760.76520.36260.039*
C190.3664 (4)0.70273 (12)0.4493 (4)0.0288 (9)
C200.4350 (4)0.67094 (12)0.5462 (4)0.0285 (9)
H200.37290.64320.55650.034*
C210.5968 (4)0.67833 (12)0.6320 (4)0.0271 (9)
C220.6716 (4)0.64566 (12)0.7320 (4)0.0303 (9)
H220.61170.61750.74200.036*
C230.4616 (5)0.46546 (13)0.6187 (4)0.0360 (10)
H23A0.43430.43510.65770.043*
H23B0.47630.48790.69680.043*
C240.6918 (5)0.51949 (12)0.4876 (4)0.0369 (10)
H24A0.70300.54070.56880.044*
H24B0.80020.52150.44440.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0288 (3)0.0309 (3)0.0285 (3)−0.0002 (2)0.00385 (19)−0.0009 (2)
S10.0315 (6)0.0372 (6)0.0301 (6)0.0030 (5)0.0023 (4)0.0026 (5)
O10.0273 (14)0.0293 (15)0.0310 (16)−0.0012 (11)0.0069 (11)−0.0013 (12)
O20.0309 (15)0.0271 (15)0.0299 (16)−0.0005 (11)0.0066 (12)−0.0040 (13)
O30.0332 (15)0.0310 (15)0.0260 (16)−0.0016 (12)0.0053 (12)−0.0006 (12)
O40.0316 (14)0.0269 (14)0.0281 (15)0.0012 (12)0.0008 (12)−0.0017 (13)
C10.036 (2)0.038 (2)0.034 (2)−0.0012 (19)0.0103 (19)−0.004 (2)
C20.026 (2)0.036 (2)0.022 (2)0.0000 (18)−0.0056 (17)0.0004 (19)
C30.025 (2)0.033 (2)0.025 (2)0.0034 (18)0.0019 (17)−0.0008 (19)
C40.030 (2)0.034 (2)0.019 (2)0.003 (2)−0.0028 (16)−0.001 (2)
C50.030 (2)0.036 (2)0.036 (2)0.0006 (18)0.0068 (19)−0.001 (2)
C60.030 (2)0.031 (2)0.026 (2)−0.0019 (17)0.0003 (17)−0.0024 (19)
C70.044 (3)0.034 (2)0.041 (3)−0.0044 (19)0.011 (2)0.001 (2)
C80.031 (2)0.033 (2)0.023 (2)−0.0018 (18)−0.0048 (18)0.0065 (19)
C90.022 (2)0.026 (2)0.027 (2)0.0017 (17)−0.0013 (17)0.0027 (18)
C100.030 (2)0.038 (2)0.018 (2)0.0090 (19)−0.0032 (17)0.0033 (19)
C110.037 (2)0.041 (2)0.043 (3)−0.004 (2)0.010 (2)−0.002 (2)
C120.032 (2)0.029 (2)0.034 (2)0.0052 (17)0.0032 (18)0.0004 (19)
C130.030 (2)0.030 (2)0.025 (2)−0.0011 (18)0.0009 (18)−0.0041 (19)
C140.036 (2)0.026 (2)0.031 (2)−0.0062 (19)−0.0021 (19)−0.005 (2)
C150.038 (2)0.027 (2)0.032 (2)−0.0063 (18)0.0036 (19)−0.005 (2)
C160.027 (2)0.032 (2)0.025 (2)0.0016 (19)0.0014 (18)0.0009 (19)
C170.031 (2)0.027 (2)0.034 (2)−0.0059 (18)0.0080 (19)0.001 (2)
C180.036 (2)0.031 (2)0.029 (2)0.0044 (19)0.0024 (19)0.0053 (19)
C190.030 (2)0.030 (2)0.026 (2)0.0016 (18)0.0029 (18)−0.0034 (19)
C200.031 (2)0.024 (2)0.030 (2)−0.0033 (17)0.0058 (19)−0.0018 (19)
C210.031 (2)0.024 (2)0.025 (2)0.0025 (17)0.0016 (18)−0.0039 (18)
C220.038 (2)0.024 (2)0.029 (2)−0.0057 (18)0.0058 (19)−0.0019 (19)
C230.033 (2)0.043 (2)0.032 (2)−0.005 (2)0.0045 (18)0.008 (2)
C240.035 (2)0.043 (2)0.033 (2)−0.0076 (19)0.0058 (19)0.001 (2)
Geometric parameters (Å, °) top
Cu1—O11.905 (2)C9—C101.402 (5)
Cu1—O21.910 (2)C9—C121.523 (5)
Cu1—O3i1.918 (2)C10—C111.499 (5)
Cu1—O4i1.925 (2)C11—H11A0.9800
Cu1—S12.8088 (10)C11—H11B0.9800
S1—C231.809 (4)C11—H11C0.9800
S1—C241.816 (4)C12—C191.522 (5)
O1—C21.286 (4)C12—H12A0.9900
O2—C41.278 (4)C12—H12B0.9900
O3—C81.289 (4)C13—C221.376 (5)
O3—Cu1i1.918 (2)C13—C141.422 (5)
O4—C101.285 (4)C14—C151.367 (5)
O4—Cu1i1.925 (2)C14—H140.9500
C1—C21.502 (5)C15—C161.408 (5)
C1—H1A0.9800C15—H150.9500
C1—H1B0.9800C16—C171.401 (5)
C1—H1C0.9800C16—C211.419 (5)
C2—C31.413 (5)C17—C181.365 (5)
C3—C41.406 (5)C17—H170.9500
C3—C61.533 (5)C18—C191.413 (5)
C4—C51.505 (4)C18—H180.9500
C5—H5A0.9800C19—C201.367 (5)
C5—H5B0.9800C20—C211.422 (5)
C5—H5C0.9800C20—H200.9500
C6—C131.520 (5)C21—C221.418 (5)
C6—H6A0.9900C22—H220.9500
C6—H6B0.9900C23—C24i1.525 (5)
C7—C81.502 (5)C23—H23A0.9900
C7—H7A0.9800C23—H23B0.9900
C7—H7B0.9800C24—C23i1.525 (5)
C7—H7C0.9800C24—H24A0.9900
C8—C91.410 (5)C24—H24B0.9900
O1—Cu1—O292.23 (10)O4—C10—C11113.5 (3)
O1—Cu1—O3i174.31 (10)C9—C10—C11121.1 (3)
O2—Cu1—O3i87.38 (10)C10—C11—H11A109.5
O1—Cu1—O4i88.97 (10)C10—C11—H11B109.5
O2—Cu1—O4i175.62 (10)H11A—C11—H11B109.5
O3i—Cu1—O4i91.01 (10)C10—C11—H11C109.5
O1—Cu1—S198.91 (8)H11A—C11—H11C109.5
O2—Cu1—S196.32 (7)H11B—C11—H11C109.5
O3i—Cu1—S186.77 (7)C19—C12—C9116.2 (3)
O4i—Cu1—S187.66 (7)C19—C12—H12A108.2
C23—S1—C24101.26 (17)C9—C12—H12A108.2
C23—S1—Cu196.79 (13)C19—C12—H12B108.2
C24—S1—Cu1102.62 (13)C9—C12—H12B108.2
C2—O1—Cu1127.4 (2)H12A—C12—H12B107.4
C4—O2—Cu1127.8 (2)C22—C13—C14117.6 (3)
C8—O3—Cu1i126.0 (2)C22—C13—C6123.3 (3)
C10—O4—Cu1i125.7 (2)C14—C13—C6119.1 (3)
C2—C1—H1A109.5C15—C14—C13121.4 (3)
C2—C1—H1B109.5C15—C14—H14119.3
H1A—C1—H1B109.5C13—C14—H14119.3
C2—C1—H1C109.5C14—C15—C16121.3 (3)
H1A—C1—H1C109.5C14—C15—H15119.4
H1B—C1—H1C109.5C16—C15—H15119.4
O1—C2—C3125.1 (3)C17—C16—C15122.5 (3)
O1—C2—C1114.7 (3)C17—C16—C21119.0 (3)
C3—C2—C1120.2 (3)C15—C16—C21118.4 (3)
C4—C3—C2122.4 (3)C18—C17—C16121.0 (3)
C4—C3—C6119.6 (3)C18—C17—H17119.5
C2—C3—C6118.0 (3)C16—C17—H17119.5
O2—C4—C3125.0 (3)C17—C18—C19121.1 (3)
O2—C4—C5114.2 (3)C17—C18—H18119.5
C3—C4—C5120.7 (3)C19—C18—H18119.5
C4—C5—H5A109.5C20—C19—C18118.7 (3)
C4—C5—H5B109.5C20—C19—C12122.6 (3)
H5A—C5—H5B109.5C18—C19—C12118.7 (3)
C4—C5—H5C109.5C19—C20—C21121.8 (3)
H5A—C5—H5C109.5C19—C20—H20119.1
H5B—C5—H5C109.5C21—C20—H20119.1
C13—C6—C3116.3 (3)C22—C21—C16118.8 (3)
C13—C6—H6A108.2C22—C21—C20122.8 (3)
C3—C6—H6A108.2C16—C21—C20118.4 (3)
C13—C6—H6B108.2C13—C22—C21122.4 (3)
C3—C6—H6B108.2C13—C22—H22118.8
H6A—C6—H6B107.4C21—C22—H22118.8
C8—C7—H7A109.5C24i—C23—S1114.1 (3)
C8—C7—H7B109.5C24i—C23—H23A108.7
H7A—C7—H7B109.5S1—C23—H23A108.7
C8—C7—H7C109.5C24i—C23—H23B108.7
H7A—C7—H7C109.5S1—C23—H23B108.7
H7B—C7—H7C109.5H23A—C23—H23B107.6
O3—C8—C9125.5 (3)C23i—C24—S1111.7 (3)
O3—C8—C7113.7 (3)C23i—C24—H24A109.3
C9—C8—C7120.7 (3)S1—C24—H24A109.3
C10—C9—C8121.4 (3)C23i—C24—H24B109.3
C10—C9—C12120.8 (3)S1—C24—H24B109.3
C8—C9—C12117.5 (3)H24A—C24—H24B107.9
O4—C10—C9125.4 (3)
O1—Cu1—S1—C23−125.86 (14)C12—C9—C10—O4−179.5 (3)
O2—Cu1—S1—C23−32.59 (14)C8—C9—C10—C11−171.8 (3)
O3i—Cu1—S1—C2354.41 (14)C12—C9—C10—C112.4 (5)
O4i—Cu1—S1—C23145.55 (14)C10—C9—C12—C19121.8 (4)
O1—Cu1—S1—C24−22.68 (15)C8—C9—C12—C19−63.8 (4)
O2—Cu1—S1—C2470.59 (14)C3—C6—C13—C2243.2 (5)
O3i—Cu1—S1—C24157.59 (15)C3—C6—C13—C14−138.7 (3)
O4i—Cu1—S1—C24−111.27 (15)C22—C13—C14—C150.5 (5)
O2—Cu1—O1—C21.7 (3)C6—C13—C14—C15−177.6 (3)
O4i—Cu1—O1—C2−174.1 (3)C13—C14—C15—C160.3 (5)
S1—Cu1—O1—C298.4 (3)C14—C15—C16—C17−178.6 (3)
O1—Cu1—O2—C4−0.5 (3)C14—C15—C16—C21−0.3 (5)
O3i—Cu1—O2—C4173.8 (3)C15—C16—C17—C18179.2 (3)
S1—Cu1—O2—C4−99.7 (3)C21—C16—C17—C180.9 (5)
Cu1—O1—C2—C3−2.6 (5)C16—C17—C18—C190.7 (5)
Cu1—O1—C2—C1176.5 (2)C17—C18—C19—C20−2.1 (5)
O1—C2—C3—C41.9 (5)C17—C18—C19—C12177.8 (3)
C1—C2—C3—C4−177.1 (3)C9—C12—C19—C20−43.3 (5)
O1—C2—C3—C6−178.6 (3)C9—C12—C19—C18136.8 (3)
C1—C2—C3—C62.4 (5)C18—C19—C20—C211.9 (5)
Cu1—O2—C4—C30.1 (5)C12—C19—C20—C21−178.0 (3)
Cu1—O2—C4—C5−177.7 (2)C17—C16—C21—C22177.9 (3)
C2—C3—C4—O2−0.6 (6)C15—C16—C21—C22−0.5 (5)
C6—C3—C4—O2179.9 (3)C17—C16—C21—C20−1.1 (5)
C2—C3—C4—C5177.1 (3)C15—C16—C21—C20−179.5 (3)
C6—C3—C4—C5−2.4 (5)C19—C20—C21—C22−179.2 (3)
C4—C3—C6—C13−97.4 (4)C19—C20—C21—C16−0.3 (5)
C2—C3—C6—C1383.1 (4)C14—C13—C22—C21−1.4 (5)
Cu1i—O3—C8—C9−7.1 (5)C6—C13—C22—C21176.7 (3)
Cu1i—O3—C8—C7174.3 (2)C16—C21—C22—C131.4 (5)
O3—C8—C9—C10−10.2 (6)C20—C21—C22—C13−179.7 (3)
C7—C8—C9—C10168.3 (3)C24—S1—C23—C24i59.9 (3)
O3—C8—C9—C12175.4 (3)Cu1—S1—C23—C24i164.3 (2)
C7—C8—C9—C12−6.1 (5)C23—S1—C24—C23i−58.2 (3)
Cu1i—O4—C10—C914.3 (5)Cu1—S1—C24—C23i−157.9 (2)
Cu1i—O4—C10—C11−167.5 (2)S1—C24—C23i—S1i66.0 (3)
C8—C9—C10—O46.3 (5)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

This research was supported by the Petroleum Research Fund (American Chemical Society) and by the US Department of Energy. The purchase of the diffractometer was made possible by Grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

references
References top

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