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Acta Cryst. (2007). E63, m2193    [ doi:10.1107/S1600536807034538 ]

Tetrachlorido-1[kappa]Cl,2[kappa]2Cl,3[kappa]Cl-bis[[mu]-4-undecyl-1,4,7-triazacyclonon-1-yl)acetato]-1[kappa]4N,N',N'',O:2[kappa]O';2[kappa]O':3[kappa]4N,N',N'',O-tricopper(II) dihydrate

L. Nagel, C. M. Forsyth and L. L. Martin

Abstract top

In the trinuclear title compound, [Cu3Cl4(C17H38N3O2)2]·2H2O or [Cu(AcC11tacn)Cl·H2O]2·CuCl2 [tacn is 1,4,7-triazacyclononone], two Cu atoms are coordinated by a bifunctionalized 1-acetato-4-undecyl-1,4,7-triazacyclononone (AcC11tacn) macrocycle and are five-coordinate, while the third Cu atom, located on a centre of inversion, bridges these two units between two keto O atoms, with two Cl atoms completing a four-coordinate square-planar geometry. The long C11 tails on the macrocycle create well ordered multilayer packing.

Comment top

The title complex, (I), crystallizes in the monoclinic space group (P21/c), with the asymmetric unit comprising one half of the molecule [Cu(AcC11tacn)Cl.H2O]2.CuCl2, Fig. 1; the Cu2 atom is located on a crystallographic inversion centre. The three N atoms from the macrocycle coordinate facially to Cu1, which is also bound to a terminal Cl with the fifth coordination site completed by the O atom derived from the N-acetyl group. Two of these units are further connected via the keto-O atoms to a four coordinate copper dichloride entity. The Cu1—Cl1 bond distance (2.2645 (14) Å) is slightly longer than the Cu2—Cl2 distance of 2.2512 (14) Å, but this may also reflect the interaction of Cl1 with the water molecule via a O3—H31···Cl1 (2.37 (3) Å) hydrogen bond. The Cu—N distances are inequivalent with the C11 substituted N atom having the longest bond (Cu1—N2 2.289 (4) Å) whilst the secondary amine has the shortest (Cu1—N3 1.985 (4) Å).

The cell contents, when viewed along the b axis, Fig. 2, show the straight chain C11 units form interdigitated layers which separate the hydrophilic {Cu(Actacn)Cl}.CuCl2 moieties, the latter associated via intermolecular N3—H3···Cl2i hydrogen bonds (Table 1).

Related literature top

There are several reports of carboxylate functionalized 1,4,7-triazacyclononane (tacn) (Mondal et al., 2003; Neves et al., 1988; Graham et al., 1997; Studer et al., 1989; Schulz et al., 1996). In contrast, the arrangement of long hydrophobic carbon tails has been underrepresented (Fallis et al., 1998; Battle & Martin, 2006). The title complex combines both groups and results in a trinuclear copper complex. For synthesis, see: Zhang et al. (1995).

Experimental top

The title complex was synthesized using a modification of the published procedure (Zhang et al., 1995). 1-Acetato-4-undecyl-1,4,7-triazacyclononane trihydrochloride (0.1 g, 0.22 mmol) was dissolved in MeOH (5 ml) and mixed with 1 equivalent of CuCl2.6H2O (0.038 g, 0.22 mmol) dissolved in MeOH (1 ml). Addition of 1.1 equivalent NaOAc (0.0076 g, 0.2 4 mmol) dissolved in MeOH resulted in a dark-green solution. Slow evaporation of the solution resulted in the deposition of blue-green crystals suitable for X-ray diffraction analysis. The solid was collected by filtration and air-dried (0.04 g, 18%). IR (KBr): 3199, 2920, 1578 (νC—O), 1491, 1466, 1445, 1403, 1313 (νC—O) cm-1. UV/vis (MeCN): λmax(ε) 265 (934), 461 (114) nm (L.mol-1.cm).

Refinement top

The amine-H3 atom and the water-H31 and H32 atoms and were located and refined with the latter having O—H distances restrained to approximately 0.90 Å. Otherwise, all H atoms were included in the riding model approximation with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C). The maximum and minimum electron density peaks were located 1.23 and 1.81 Å from the H3A and H6A atoms, respectively.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of (I) showing atomic labelling and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Cell contents as viewed down the b axis. H atoms have been omitted for clarity.
Tetrachlorido-1κCl,2κ2Cl,3κCl- bis[µ-4-undecyl-1,4,7-triazacyclonon-1-yl)acetato]-1κ4N,N',N'',O:2κO'; 2κO':3κ4N,N',N'',O-tricopper(II) dihydrate top
Crystal data top
[Cu3Cl4(C17H38N3O2)2]·2H2OF(000) = 1106
Mr = 1049.50Dx = 1.422 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25491 reflections
a = 22.1182 (11) Åθ = 2.8–27.5°
b = 7.8330 (4) ŵ = 1.56 mm−1
c = 14.6177 (7) ÅT = 123 K
β = 104.570 (2)°Plate, blue-green
V = 2451.1 (2) Å30.20 × 0.10 × 0.05 mm
Z = 2
Data collection top
Bruker X8 APEX CCD
diffractometer		5625 independent reflections
Radiation source: fine-focus sealed tube4994 reflections with I > 2σ(I)
graphiteRint = 0.071
φ scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −28→28
Tmin = 0.746, Tmax = 0.926k = −10→10
25491 measured reflectionsl = −18→18
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)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.32 w = 1/[σ2(Fo2) + 12.2399P]
where P = (Fo2 + 2Fc2)/3
5625 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 0.62 e Å−3
3 restraintsΔρmin = −1.02 e Å−3
Crystal data top
[Cu3Cl4(C17H38N3O2)2]·2H2OV = 2451.1 (2) Å3
Mr = 1049.50Z = 2
Monoclinic, P21/cMo Kα radiation
a = 22.1182 (11) ŵ = 1.56 mm−1
b = 7.8330 (4) ÅT = 123 K
c = 14.6177 (7) Å0.20 × 0.10 × 0.05 mm
β = 104.570 (2)°
Data collection top
Bruker X8 APEX CCD
diffractometer		5625 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4994 reflections with I > 2σ(I)
Tmin = 0.746, Tmax = 0.926Rint = 0.071
25491 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.084 w = 1/[σ2(Fo2) + 12.2399P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142Δρmax = 0.62 e Å−3
S = 1.32Δρmin = −1.02 e Å−3
5625 reflectionsAbsolute structure: ?
271 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
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
Cu10.61289 (3)0.74292 (8)−0.20823 (4)0.01211 (15)
Cu20.50000.50000.00000.0165 (2)
Cl10.61753 (6)1.00100 (16)−0.13697 (9)0.0193 (3)
Cl20.41046 (7)0.64527 (17)−0.05565 (10)0.0252 (3)
O10.56465 (17)0.6326 (5)−0.1290 (2)0.0154 (8)
O20.49883 (18)0.4205 (5)−0.1271 (3)0.0189 (8)
O30.7218 (3)1.1587 (10)0.0423 (4)0.0563 (16)
N10.5975 (2)0.5189 (5)−0.2818 (3)0.0145 (9)
N20.7136 (2)0.6474 (6)−0.1574 (3)0.0147 (9)
N30.6437 (2)0.8278 (6)−0.3163 (3)0.0167 (9)
C10.6565 (2)0.4132 (6)−0.2570 (4)0.0150 (10)
H1A0.67880.4268−0.30730.018*
H1B0.64510.2913−0.25490.018*
C20.6998 (3)0.4626 (6)−0.1629 (4)0.0176 (11)
H2A0.68040.4307−0.11130.021*
H2B0.73940.3982−0.15370.021*
C30.7453 (3)0.7104 (7)−0.2280 (4)0.0191 (11)
H3A0.74630.6189−0.27440.023*
H3B0.78890.7416−0.19640.023*
C40.7115 (3)0.8647 (7)−0.2790 (4)0.0212 (12)
H4A0.71690.9627−0.23490.025*
H4B0.72980.8961−0.33190.025*
C50.6297 (3)0.7046 (7)−0.3966 (4)0.0182 (11)
H5A0.66850.6444−0.40000.022*
H5B0.61370.7668−0.45680.022*
C60.5813 (3)0.5755 (7)−0.3828 (3)0.0166 (11)
H6A0.53920.6282−0.39920.020*
H6B0.58070.4759−0.42470.020*
C70.5455 (2)0.4318 (7)−0.2560 (4)0.0167 (11)
H7A0.55410.3077−0.25050.020*
H7B0.50680.4494−0.30660.020*
C80.5361 (2)0.4972 (7)−0.1645 (4)0.0164 (11)
C90.7438 (2)0.7052 (7)−0.0614 (4)0.0195 (12)
H9A0.71540.6792−0.02050.023*
H9B0.74810.8309−0.06280.023*
C100.8079 (3)0.6299 (8)−0.0148 (4)0.0269 (14)
H10A0.80350.5073−0.00140.032*
H10B0.83540.6397−0.05850.032*
C110.8375 (2)0.7237 (8)0.0771 (4)0.0214 (12)
H11A0.84430.84420.06180.026*
H11B0.80750.72300.11720.026*
C120.8988 (3)0.6509 (8)0.1337 (4)0.0258 (13)
H12A0.93110.67060.09870.031*
H12B0.89420.52600.13980.031*
C130.9208 (3)0.7283 (8)0.2317 (4)0.0274 (14)
H13A0.92580.85290.22510.033*
H13B0.88790.71070.26580.033*
C140.9817 (3)0.6562 (8)0.2914 (4)0.0265 (13)
H14A1.01550.68140.26000.032*
H14B0.97790.53060.29470.032*
C150.9999 (3)0.7275 (9)0.3913 (4)0.0276 (14)
H15A1.00330.85320.38770.033*
H15B0.96610.70180.42250.033*
C161.0606 (3)0.6581 (9)0.4518 (4)0.0278 (14)
H16A1.09460.68510.42110.033*
H16B1.05750.53230.45490.033*
C171.0781 (3)0.7283 (8)0.5517 (4)0.0289 (14)
H17A1.04420.70100.58250.035*
H17B1.08100.85420.54860.035*
C181.1396 (3)0.6591 (9)0.6132 (4)0.0301 (15)
H18A1.13690.53330.61720.036*
H18B1.17380.68660.58310.036*
C191.1551 (3)0.7339 (11)0.7131 (5)0.0417 (18)
H19A1.19470.68610.74990.063*
H19B1.12170.70510.74360.063*
H19C1.15880.85820.70960.063*
H30.622 (3)0.919 (6)−0.343 (5)0.05 (2)*
H310.695 (5)1.105 (16)−0.006 (6)0.16 (6)*
H320.714 (8)1.266 (8)0.059 (11)0.22 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0141 (3)0.0100 (3)0.0124 (3)−0.0002 (2)0.0038 (2)−0.0010 (2)
Cu20.0238 (5)0.0127 (4)0.0126 (4)−0.0055 (4)0.0041 (4)0.0013 (3)
Cl10.0247 (7)0.0129 (6)0.0199 (6)−0.0012 (5)0.0051 (5)−0.0045 (5)
Cl20.0362 (8)0.0131 (6)0.0223 (7)0.0035 (6)0.0000 (6)−0.0011 (5)
O10.021 (2)0.0137 (18)0.0123 (18)−0.0014 (15)0.0064 (15)−0.0017 (14)
O20.021 (2)0.023 (2)0.0146 (19)−0.0062 (16)0.0069 (16)−0.0001 (15)
O30.051 (4)0.075 (5)0.042 (3)−0.008 (3)0.008 (3)−0.007 (3)
N10.016 (2)0.012 (2)0.014 (2)0.0021 (17)0.0015 (17)−0.0001 (17)
N20.013 (2)0.017 (2)0.015 (2)−0.0003 (17)0.0032 (17)0.0002 (18)
N30.020 (2)0.017 (2)0.013 (2)0.0017 (19)0.0038 (18)−0.0005 (18)
C10.021 (3)0.006 (2)0.017 (3)0.001 (2)0.003 (2)0.0011 (19)
C20.020 (3)0.011 (2)0.020 (3)0.005 (2)0.003 (2)0.005 (2)
C30.017 (3)0.022 (3)0.021 (3)−0.001 (2)0.009 (2)0.001 (2)
C40.021 (3)0.018 (3)0.027 (3)−0.005 (2)0.010 (2)0.001 (2)
C50.027 (3)0.014 (3)0.016 (3)0.001 (2)0.010 (2)0.001 (2)
C60.023 (3)0.016 (3)0.009 (2)0.002 (2)0.000 (2)−0.001 (2)
C70.018 (3)0.015 (3)0.019 (3)−0.002 (2)0.007 (2)−0.008 (2)
C80.018 (3)0.018 (3)0.014 (3)0.001 (2)0.005 (2)−0.001 (2)
C90.015 (3)0.025 (3)0.016 (3)0.000 (2)0.000 (2)0.001 (2)
C100.021 (3)0.034 (3)0.023 (3)0.007 (3)−0.001 (2)−0.008 (3)
C110.018 (3)0.028 (3)0.017 (3)0.000 (2)0.001 (2)−0.002 (2)
C120.019 (3)0.030 (3)0.026 (3)0.000 (3)0.001 (2)0.002 (3)
C130.022 (3)0.034 (3)0.022 (3)−0.004 (3)−0.002 (2)0.006 (3)
C140.021 (3)0.030 (3)0.025 (3)−0.002 (3)0.001 (2)0.004 (3)
C150.018 (3)0.035 (4)0.026 (3)−0.002 (3)−0.001 (2)0.001 (3)
C160.019 (3)0.035 (4)0.026 (3)−0.001 (3)0.000 (2)0.002 (3)
C170.025 (3)0.034 (4)0.024 (3)−0.005 (3)0.000 (2)0.009 (3)
C180.021 (3)0.034 (4)0.030 (3)−0.001 (3)−0.002 (3)0.007 (3)
C190.026 (3)0.063 (5)0.032 (4)−0.004 (4)0.000 (3)−0.002 (4)
Geometric parameters (Å, °) top
Cu1—O11.962 (4)C7—C81.495 (7)
Cu1—N31.986 (5)C7—H7A0.9900
Cu1—N12.041 (4)C7—H7B0.9900
Cu1—Cl12.2645 (14)C9—C101.529 (7)
Cu1—N22.289 (4)C9—H9A0.9900
Cu2—O21.954 (4)C9—H9B0.9900
Cu2—O2i1.954 (4)C10—C111.526 (7)
Cu2—Cl22.2512 (14)C10—H10A0.9900
Cu2—Cl2i2.2512 (15)C10—H10B0.9900
O1—C81.276 (6)C11—C121.512 (7)
O2—C81.251 (6)C11—H11A0.9900
O3—H310.90 (2)C11—H11B0.9900
O3—H320.90 (2)C12—C131.519 (8)
N1—C71.466 (7)C12—H12A0.9900
N1—C61.496 (6)C12—H12B0.9900
N1—C11.510 (6)C13—C141.518 (8)
N2—C91.466 (6)C13—H13A0.9900
N2—C31.470 (7)C13—H13B0.9900
N2—C21.477 (6)C14—C151.520 (8)
N3—C41.490 (7)C14—H14A0.9900
N3—C51.491 (7)C14—H14B0.9900
N3—H30.89 (2)C15—C161.511 (8)
C1—C21.516 (7)C15—H15A0.9900
C1—H1A0.9900C15—H15B0.9900
C1—H1B0.9900C16—C171.516 (8)
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C3—C41.515 (8)C17—C181.529 (8)
C3—H3A0.9900C17—H17A0.9900
C3—H3B0.9900C17—H17B0.9900
C4—H4A0.9900C18—C191.529 (9)
C4—H4B0.9900C18—H18A0.9900
C5—C61.523 (7)C18—H18B0.9900
C5—H5A0.9900C19—H19A0.9800
C5—H5B0.9900C19—H19B0.9800
C6—H6A0.9900C19—H19C0.9800
C6—H6B0.9900
O1—Cu1—N3164.51 (17)N1—C7—H7A109.3
O1—Cu1—N183.65 (16)C8—C7—H7A109.3
N3—Cu1—N185.07 (18)N1—C7—H7B109.3
O1—Cu1—Cl195.16 (11)C8—C7—H7B109.3
N3—Cu1—Cl194.70 (14)H7A—C7—H7B108.0
N1—Cu1—Cl1172.72 (13)O2—C8—O1122.3 (5)
O1—Cu1—N2107.10 (15)O2—C8—C7118.8 (5)
N3—Cu1—N282.35 (17)O1—C8—C7118.9 (5)
N1—Cu1—N284.80 (16)N2—C9—C10117.1 (5)
Cl1—Cu1—N2102.39 (12)N2—C9—H9A108.0
O2—Cu2—O2i180C10—C9—H9A108.0
O2—Cu2—Cl291.00 (12)N2—C9—H9B108.0
O2i—Cu2—Cl289.00 (12)C10—C9—H9B108.0
O2—Cu2—Cl2i89.00 (12)H9A—C9—H9B107.3
O2i—Cu2—Cl2i91.00 (12)C11—C10—C9110.5 (5)
Cl2—Cu2—Cl2i180C11—C10—H10A109.5
C8—O1—Cu1114.3 (3)C9—C10—H10A109.5
C8—O2—Cu2114.2 (3)C11—C10—H10B109.5
H31—O3—H32120 (10)C9—C10—H10B109.5
C7—N1—C6112.5 (4)H10A—C10—H10B108.1
C7—N1—C1111.7 (4)C12—C11—C10115.3 (5)
C6—N1—C1112.2 (4)C12—C11—H11A108.5
C7—N1—Cu1107.6 (3)C10—C11—H11A108.5
C6—N1—Cu1103.4 (3)C12—C11—H11B108.5
C1—N1—Cu1109.0 (3)C10—C11—H11B108.5
C9—N2—C3112.7 (4)H11A—C11—H11B107.5
C9—N2—C2113.1 (4)C11—C12—C13113.4 (5)
C3—N2—C2114.7 (4)C11—C12—H12A108.9
C9—N2—Cu1112.4 (3)C13—C12—H12A108.9
C3—N2—Cu1105.0 (3)C11—C12—H12B108.9
C2—N2—Cu197.6 (3)C13—C12—H12B108.9
C4—N3—C5113.8 (4)H12A—C12—H12B107.7
C4—N3—Cu1106.8 (3)C14—C13—C12114.9 (5)
C5—N3—Cu1111.4 (3)C14—C13—H13A108.5
C4—N3—H3113 (5)C12—C13—H13A108.5
C5—N3—H3101 (5)C14—C13—H13B108.5
Cu1—N3—H3111 (5)C12—C13—H13B108.5
N1—C1—C2112.9 (4)H13A—C13—H13B107.5
N1—C1—H1A109.0C13—C14—C15113.4 (5)
C2—C1—H1A109.0C13—C14—H14A108.9
N1—C1—H1B109.0C15—C14—H14A108.9
C2—C1—H1B109.0C13—C14—H14B108.9
H1A—C1—H1B107.8C15—C14—H14B108.9
N2—C2—C1112.0 (4)H14A—C14—H14B107.7
N2—C2—H2A109.2C16—C15—C14114.3 (5)
C1—C2—H2A109.2C16—C15—H15A108.7
N2—C2—H2B109.2C14—C15—H15A108.7
C1—C2—H2B109.2C16—C15—H15B108.7
H2A—C2—H2B107.9C14—C15—H15B108.7
N2—C3—C4110.5 (4)H15A—C15—H15B107.6
N2—C3—H3A109.6C15—C16—C17114.0 (5)
C4—C3—H3A109.6C15—C16—H16A108.8
N2—C3—H3B109.6C17—C16—H16A108.8
C4—C3—H3B109.6C15—C16—H16B108.8
H3A—C3—H3B108.1C17—C16—H16B108.8
N3—C4—C3110.6 (4)H16A—C16—H16B107.6
N3—C4—H4A109.5C16—C17—C18114.2 (6)
C3—C4—H4A109.5C16—C17—H17A108.7
N3—C4—H4B109.5C18—C17—H17A108.7
C3—C4—H4B109.5C16—C17—H17B108.7
H4A—C4—H4B108.1C18—C17—H17B108.7
N3—C5—C6109.8 (4)H17A—C17—H17B107.6
N3—C5—H5A109.7C19—C18—C17112.2 (6)
C6—C5—H5A109.7C19—C18—H18A109.2
N3—C5—H5B109.7C17—C18—H18A109.2
C6—C5—H5B109.7C19—C18—H18B109.2
H5A—C5—H5B108.2C17—C18—H18B109.2
N1—C6—C5109.0 (4)H18A—C18—H18B107.9
N1—C6—H6A109.9C18—C19—H19A109.5
C5—C6—H6A109.9C18—C19—H19B109.5
N1—C6—H6B109.9H19A—C19—H19B109.5
C5—C6—H6B109.9C18—C19—H19C109.5
H6A—C6—H6B108.3H19A—C19—H19C109.5
N1—C7—C8111.4 (4)H19B—C19—H19C109.5
Symmetry codes: (i) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H31···Cl10.90 (2)2.37 (3)3.267 (7)172 (12)
N3—H3···Cl2ii0.89 (2)2.31 (3)3.161 (5)160 (7)
Symmetry codes: (ii) −x+1, y+1/2, −z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H31···Cl10.90 (2)2.37 (3)3.267 (7)172 (12)
N3—H3···Cl2i0.89 (2)2.31 (3)3.161 (5)160 (7)
Symmetry codes: (i) −x+1, y+1/2, −z−1/2.
Acknowledgements top

We acknowledge support from Monash University and the Australian Research Council.

references
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