Diaqua-(1,4,8,11-tetra-aza-cyclo-tetra-decane-κN,N,N,N)copper(II) didodeca-noate dihydrate.

The title compound, [Cu(C(10)H(24)N(4))(H(2)O)(2)][CH(3)(CH(2))(10)CO(2)](2)·2H(2)O, consists of one cationic copper(II) complex, two dodeca-noate anions and two water solvent mol-ecules. The Cu(II) atom is located on an inversion center and is chelated by the four aza N atoms of the neutral 1,4,8,11-tetra-aza-cyclo-tetra-decane (cyclam) ligand and by two water mol-ecules in axial positions, giving an octa-hedral coordination geometry, distorted as a consequence of the Jahn-Teller effect. The uncoordinated water mol-ecules link the complex cations and the dodeca-noate counter-ions through O-H⋯O hydrogen bonding, forming a layer structure parallel to (001). Inter-molecular N-H⋯O inter-actions also occur.

Related literature

For the complexation of cyclam with transition metals, see: Ahmad Tajidi et al. (2010a ▶,b ▶,c ▶,d ▶); Lindoy et al. (2003 ▶); Holanda et al. (2007 ▶); Sreedaran et al. (2008 ▶); Zgolli et al. (2010 ▶).

Experimental

Crystal data

[Cu(C10H24N4)(H2O)2](C12H23O2)2·2H2O

M = 734.54

Triclinic,

a = 6.9972 (4) Å

b = 8.8164 (5) Å

c = 17.1495 (10) Å

α = 96.218 (3)°

β = 99.137 (3)°

γ = 98.329 (3)°

V = 1024.13 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.58 mm−1

T = 150 K

0.41 × 0.41 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.796, T max = 0.955

7085 measured reflections

4623 independent reflections

4138 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.07

4623 reflections

215 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012773/dn2672sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012773/dn2672Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C10H24N4)(H2O)2](C12H23O2)2·2H2O	Z = 1
Mr = 734.54	F(000) = 403
Triclinic, P1	Dx = 1.191 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9972 (4) Å	Cell parameters from 2586 reflections
b = 8.8164 (5) Å	θ = 2.8–27.6°
c = 17.1495 (10) Å	µ = 0.58 mm−1
α = 96.218 (3)°	T = 150 K
β = 99.137 (3)°	Plate, violet
γ = 98.329 (3)°	0.41 × 0.41 × 0.08 mm
V = 1024.13 (10) Å3

Bruker SMART CCD area-detector diffractometer	4623 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 27.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −9→8
Tmin = 0.796, Tmax = 0.955	k = −11→11
7085 measured reflections	l = 0→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.109P] where P = (Fo2 + 2Fc2)/3
4623 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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 > 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.

	x	y	z	Uiso*/Ueq
Cu1	1.0000	0.0000	1.0000	0.01254 (12)
O2W	0.6641 (2)	0.00995 (16)	0.93529 (9)	0.0230 (3)
H2WA	0.5631	−0.0637	0.9110	0.034*
H2WB	0.6086	0.0954	0.9319	0.034*
N1	1.1080 (2)	0.18383 (18)	0.95170 (10)	0.0151 (3)
H1	1.2439	0.1913	0.9617	0.018*
N2	0.9722 (2)	0.15474 (18)	1.09264 (9)	0.0159 (3)
H2	0.8416	0.1686	1.0853	0.019*
C1	1.1016 (3)	0.0404 (3)	0.81813 (12)	0.0234 (5)
H1A	1.0855	0.0541	0.7610	0.028*
H1B	1.2416	0.0352	0.8367	0.028*
C2	1.0491 (3)	0.1814 (2)	0.86470 (12)	0.0210 (4)
H2A	1.1157	0.2767	0.8484	0.025*
H2B	0.9057	0.1799	0.8518	0.025*
C3	1.0621 (3)	0.3232 (2)	0.99684 (13)	0.0203 (4)
H3A	0.9248	0.3356	0.9778	0.024*
H3B	1.1501	0.4166	0.9888	0.024*
C4	1.0903 (3)	0.3035 (2)	1.08367 (13)	0.0207 (4)
H4A	1.2308	0.3037	1.1043	0.025*
H4B	1.0478	0.3902	1.1145	0.025*
C5	1.0207 (3)	0.1110 (3)	1.17381 (12)	0.0221 (4)
H5A	0.9975	0.1934	1.2135	0.027*
H5B	1.1615	0.1019	1.1851	0.027*
O1	0.3901 (2)	0.76965 (15)	0.84556 (8)	0.0201 (3)
O2	0.3977 (3)	0.54859 (17)	0.89662 (9)	0.0277 (4)
C6	1.5268 (4)	0.8928 (3)	0.31756 (16)	0.0379 (6)
H6A	1.6020	0.9753	0.3585	0.057*
H6B	1.5357	0.9224	0.2646	0.057*
H6C	1.5804	0.7970	0.3229	0.057*
C7	1.3129 (3)	0.8673 (3)	0.32783 (13)	0.0302 (5)
H7A	1.2590	0.9636	0.3204	0.036*
H7B	1.2380	0.7852	0.2856	0.036*
C8	1.2814 (3)	0.8219 (3)	0.40846 (12)	0.0216 (4)
H8A	1.3601	0.9020	0.4509	0.026*
H8B	1.3301	0.7233	0.4151	0.026*
C9	1.0669 (3)	0.8029 (3)	0.41888 (12)	0.0217 (4)
H9A	1.0194	0.9024	0.4136	0.026*
H9B	0.9879	0.7250	0.3755	0.026*
C10	1.0328 (3)	0.7534 (3)	0.49849 (12)	0.0227 (4)
H10A	1.1154	0.8293	0.5420	0.027*
H10B	1.0755	0.6520	0.5030	0.027*
C11	0.8192 (3)	0.7402 (3)	0.50970 (12)	0.0223 (4)
H11A	0.7362	0.6671	0.4652	0.027*
H11B	0.7779	0.8426	0.5069	0.027*
C12	0.7825 (3)	0.6855 (3)	0.58845 (13)	0.0241 (5)
H12A	0.8202	0.5819	0.5907	0.029*
H12B	0.8676	0.7572	0.6330	0.029*
C13	0.5699 (3)	0.6768 (3)	0.59969 (12)	0.0225 (4)
H13A	0.4846	0.6099	0.5534	0.027*
H13B	0.5348	0.7817	0.6002	0.027*
C14	0.5274 (3)	0.6143 (2)	0.67581 (12)	0.0214 (4)
H14A	0.6137	0.6802	0.7222	0.026*
H14B	0.5598	0.5086	0.6750	0.026*
C15	0.3140 (3)	0.6090 (2)	0.68655 (12)	0.0202 (4)
H15A	0.2270	0.5519	0.6379	0.024*
H15B	0.2853	0.7160	0.6928	0.024*
C16	0.2673 (3)	0.5319 (2)	0.75860 (11)	0.0192 (4)
H16A	0.3117	0.4302	0.7555	0.023*
H16B	0.1231	0.5128	0.7554	0.023*
C17	0.3612 (3)	0.6252 (2)	0.83941 (11)	0.0154 (4)
O1W	0.5329 (2)	0.29510 (16)	0.95510 (9)	0.0208 (3)
H1WA	0.5554	0.3337	1.0070	0.031*
H1WB	0.4965	0.3679	0.9255	0.031*

	U11	U22	U33	U12	U13	U23
Cu1	0.01428 (19)	0.01012 (17)	0.01465 (18)	0.00220 (12)	0.00653 (13)	0.00193 (12)
O2W	0.0123 (7)	0.0189 (7)	0.0358 (9)	0.0048 (6)	0.0002 (6)	−0.0017 (6)
N1	0.0121 (8)	0.0136 (8)	0.0210 (8)	0.0032 (6)	0.0051 (6)	0.0044 (6)
N2	0.0122 (8)	0.0170 (8)	0.0185 (8)	0.0028 (6)	0.0044 (6)	−0.0010 (6)
C1	0.0183 (11)	0.0389 (12)	0.0173 (10)	0.0080 (9)	0.0088 (8)	0.0097 (9)
C2	0.0174 (10)	0.0254 (10)	0.0231 (10)	0.0038 (8)	0.0059 (8)	0.0122 (8)
C3	0.0161 (10)	0.0101 (8)	0.0367 (12)	0.0022 (7)	0.0100 (9)	0.0036 (8)
C4	0.0175 (10)	0.0136 (9)	0.0298 (11)	−0.0002 (8)	0.0080 (8)	−0.0042 (8)
C5	0.0207 (11)	0.0306 (11)	0.0149 (9)	0.0069 (9)	0.0037 (8)	−0.0024 (8)
O1	0.0231 (8)	0.0157 (7)	0.0213 (7)	0.0048 (6)	0.0033 (6)	0.0001 (5)
O2	0.0426 (10)	0.0209 (8)	0.0188 (7)	0.0039 (7)	0.0029 (7)	0.0052 (6)
C6	0.0286 (14)	0.0546 (17)	0.0364 (14)	0.0053 (12)	0.0196 (11)	0.0141 (12)
C7	0.0229 (12)	0.0478 (14)	0.0213 (11)	0.0013 (10)	0.0098 (9)	0.0090 (10)
C8	0.0182 (11)	0.0290 (11)	0.0185 (10)	0.0018 (8)	0.0077 (8)	0.0037 (8)
C9	0.0189 (11)	0.0281 (11)	0.0170 (10)	−0.0017 (8)	0.0059 (8)	0.0020 (8)
C10	0.0204 (11)	0.0292 (11)	0.0196 (10)	0.0018 (9)	0.0086 (8)	0.0030 (8)
C11	0.0203 (11)	0.0272 (11)	0.0191 (10)	−0.0008 (8)	0.0089 (8)	0.0000 (8)
C12	0.0216 (11)	0.0313 (12)	0.0215 (11)	0.0041 (9)	0.0100 (9)	0.0044 (9)
C13	0.0225 (11)	0.0275 (11)	0.0190 (10)	0.0017 (9)	0.0104 (8)	0.0025 (8)
C14	0.0201 (11)	0.0271 (11)	0.0182 (10)	0.0040 (8)	0.0072 (8)	0.0028 (8)
C15	0.0214 (11)	0.0253 (10)	0.0137 (9)	0.0019 (8)	0.0065 (8)	−0.0002 (8)
C16	0.0220 (11)	0.0189 (10)	0.0160 (9)	−0.0008 (8)	0.0063 (8)	0.0006 (7)
C17	0.0127 (9)	0.0180 (9)	0.0178 (9)	0.0046 (7)	0.0076 (7)	0.0019 (7)
O1W	0.0201 (8)	0.0195 (7)	0.0234 (7)	0.0054 (6)	0.0033 (6)	0.0025 (6)

Cu1—N1i	2.0048 (16)	C7—C8	1.521 (3)
Cu1—N1	2.0048 (16)	C7—H7A	0.9900
Cu1—N2i	2.0319 (15)	C7—H7B	0.9900
Cu1—N2	2.0319 (15)	C8—C9	1.527 (3)
O2W—H2WA	0.8998	C8—H8A	0.9900
O2W—H2WB	0.8994	C8—H8B	0.9900
N1—C2	1.481 (2)	C9—C10	1.521 (3)
N1—C3	1.483 (2)	C9—H9A	0.9900
N1—H1	0.9300	C9—H9B	0.9900
N2—C4	1.482 (3)	C10—C11	1.527 (3)
N2—C5	1.485 (2)	C10—H10A	0.9900
N2—H2	0.9300	C10—H10B	0.9900
C1—C5i	1.510 (3)	C11—C12	1.529 (3)
C1—C2	1.526 (3)	C11—H11A	0.9900
C1—H1A	0.9900	C11—H11B	0.9900
C1—H1B	0.9900	C12—C13	1.523 (3)
C2—H2A	0.9900	C12—H12A	0.9900
C2—H2B	0.9900	C12—H12B	0.9900
C3—C4	1.503 (3)	C13—C14	1.526 (3)
C3—H3A	0.9900	C13—H13A	0.9900
C3—H3B	0.9900	C13—H13B	0.9900
C4—H4A	0.9900	C14—C15	1.528 (3)
C4—H4B	0.9900	C14—H14A	0.9900
C5—C1i	1.510 (3)	C14—H14B	0.9900
C5—H5A	0.9900	C15—C16	1.530 (3)
C5—H5B	0.9900	C15—H15A	0.9900
O1—C17	1.250 (2)	C15—H15B	0.9900
O2—C17	1.264 (2)	C16—C17	1.529 (3)
C6—C7	1.522 (3)	C16—H16A	0.9900
C6—H6A	0.9800	C16—H16B	0.9900
C6—H6B	0.9800	O1W—H1WA	0.8986
C6—H6C	0.9800	O1W—H1WB	0.9006
N1i—Cu1—N1	180.0	H7A—C7—H7B	107.6
N1i—Cu1—N2i	86.18 (7)	C7—C8—C9	113.37 (18)
N1—Cu1—N2i	93.82 (7)	C7—C8—H8A	108.9
N1i—Cu1—N2	93.82 (7)	C9—C8—H8A	108.9
N1—Cu1—N2	86.18 (7)	C7—C8—H8B	108.9
N2i—Cu1—N2	180.000 (1)	C9—C8—H8B	108.9
H2WA—O2W—H2WB	100.8	H8A—C8—H8B	107.7
C2—N1—C3	111.39 (15)	C10—C9—C8	113.87 (17)
C2—N1—Cu1	117.57 (13)	C10—C9—H9A	108.8
C3—N1—Cu1	107.35 (12)	C8—C9—H9A	108.8
C2—N1—H1	106.6	C10—C9—H9B	108.8
C3—N1—H1	106.6	C8—C9—H9B	108.8
Cu1—N1—H1	106.6	H9A—C9—H9B	107.7
C4—N2—C5	112.33 (16)	C9—C10—C11	113.57 (17)
C4—N2—Cu1	106.22 (12)	C9—C10—H10A	108.9
C5—N2—Cu1	116.78 (12)	C11—C10—H10A	108.9
C4—N2—H2	107.0	C9—C10—H10B	108.9
C5—N2—H2	107.0	C11—C10—H10B	108.9
Cu1—N2—H2	107.0	H10A—C10—H10B	107.7
C5i—C1—C2	114.02 (17)	C10—C11—C12	113.90 (18)
C5i—C1—H1A	108.7	C10—C11—H11A	108.8
C2—C1—H1A	108.7	C12—C11—H11A	108.8
C5i—C1—H1B	108.7	C10—C11—H11B	108.8
C2—C1—H1B	108.7	C12—C11—H11B	108.8
H1A—C1—H1B	107.6	H11A—C11—H11B	107.7
N1—C2—C1	111.41 (15)	C13—C12—C11	113.29 (18)
N1—C2—H2A	109.3	C13—C12—H12A	108.9
C1—C2—H2A	109.3	C11—C12—H12A	108.9
N1—C2—H2B	109.3	C13—C12—H12B	108.9
C1—C2—H2B	109.3	C11—C12—H12B	108.9
H2A—C2—H2B	108.0	H12A—C12—H12B	107.7
N1—C3—C4	108.34 (15)	C12—C13—C14	114.26 (18)
N1—C3—H3A	110.0	C12—C13—H13A	108.7
C4—C3—H3A	110.0	C14—C13—H13A	108.7
N1—C3—H3B	110.0	C12—C13—H13B	108.7
C4—C3—H3B	110.0	C14—C13—H13B	108.7
H3A—C3—H3B	108.4	H13A—C13—H13B	107.6
N2—C4—C3	108.71 (16)	C13—C14—C15	113.37 (17)
N2—C4—H4A	109.9	C13—C14—H14A	108.9
C3—C4—H4A	109.9	C15—C14—H14A	108.9
N2—C4—H4B	109.9	C13—C14—H14B	108.9
C3—C4—H4B	109.9	C15—C14—H14B	108.9
H4A—C4—H4B	108.3	H14A—C14—H14B	107.7
N2—C5—C1i	111.54 (17)	C14—C15—C16	113.17 (17)
N2—C5—H5A	109.3	C14—C15—H15A	108.9
C1i—C5—H5A	109.3	C16—C15—H15A	108.9
N2—C5—H5B	109.3	C14—C15—H15B	108.9
C1i—C5—H5B	109.3	C16—C15—H15B	108.9
H5A—C5—H5B	108.0	H15A—C15—H15B	107.8
C7—C6—H6A	109.5	C15—C16—C17	114.68 (17)
C7—C6—H6B	109.5	C15—C16—H16A	108.6
H6A—C6—H6B	109.5	C17—C16—H16A	108.6
C7—C6—H6C	109.5	C15—C16—H16B	108.6
H6A—C6—H6C	109.5	C17—C16—H16B	108.6
H6B—C6—H6C	109.5	H16A—C16—H16B	107.6
C8—C7—C6	114.1 (2)	O1—C17—O2	124.53 (19)
C8—C7—H7A	108.7	O1—C17—C16	118.96 (17)
C6—C7—H7A	108.7	O2—C17—C16	116.46 (17)
C8—C7—H7B	108.7	H1WA—O1W—H1WB	109.5
C6—C7—H7B	108.7
C3—N1—C2—C1	178.39 (16)	C7—C8—C9—C10	178.49 (19)
Cu1—N1—C2—C1	−57.1 (2)	C8—C9—C10—C11	177.93 (18)
C5i—C1—C2—N1	70.0 (2)	C9—C10—C11—C12	178.14 (18)
C2—N1—C3—C4	169.59 (16)	C10—C11—C12—C13	178.57 (17)
Cu1—N1—C3—C4	39.57 (18)	C11—C12—C13—C14	176.93 (18)
C5—N2—C4—C3	168.83 (15)	C12—C13—C14—C15	179.07 (18)
Cu1—N2—C4—C3	40.02 (17)	C13—C14—C15—C16	174.42 (17)
N1—C3—C4—N2	−53.9 (2)	C14—C15—C16—C17	70.0 (2)
C4—N2—C5—C1i	179.78 (15)	C15—C16—C17—O1	30.9 (3)
Cu1—N2—C5—C1i	−57.2 (2)	C15—C16—C17—O2	−151.66 (19)
C6—C7—C8—C9	177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2	0.90	1.91	2.774 (2)	160.
O1W—H1WA···O2ii	0.90	1.81	2.694 (2)	168.
O2W—H2WB···O1W	0.90	1.93	2.8037 (19)	164.
O2W—H2WA···O1iii	0.90	1.89	2.777 (2)	168.
N2—H2···O1ii	0.93	2.25	3.030 (2)	141.
N1—H1···O1Wiv	0.93	2.12	2.982 (2)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2	0.90	1.91	2.774 (2)	160
O1W—H1WA⋯O2i	0.90	1.81	2.694 (2)	168
O2W—H2WB⋯O1W	0.90	1.93	2.8037 (19)	164
O2W—H2WA⋯O1ii	0.90	1.89	2.777 (2)	168
N2—H2⋯O1i	0.93	2.25	3.030 (2)	141
N1—H1⋯O1Wiii	0.93	2.12	2.982 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) .