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

The Cu(II) atom in the title salt, [Cu(C(10)H(24)N(4))(H(2)O)(2)][CH(3)(CH(2))(8)CO(2)](2)·2H(2)O, is chelated by the four N atoms of the 1,4,8,11-tetra-aza-cyclo-tetra-decane (cyclam) ligand and is coordinated by two water mol-ecules in a Jahn-Teller-type tetra-gonally distorted octa-hedral geometry. The Cu(II) atom lies on a center of inversion. The cations, anions and uncoordinated water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a layer structure parallel to (001).

Related literature

For related (1,4,8,11-tetra­aza­cyclo­tetra­deca­ne)copper carb­oxy­l­ates, see: Lindoy et al. (2003 ▶); Hunter et al. (2005 ▶).

Experimental

Crystal data

[Cu(C10H24N4)(H2O)2](C10H19O2)2·2H2O

M = 678.44

Triclinic,

a = 6.9820 (6) Å

b = 8.8006 (8) Å

c = 15.3291 (13) Å

α = 95.045 (1)°

β = 93.158 (1)°

γ = 98.423 (1)°

V = 925.93 (14) Å3

Z = 1

Mo Kα radiation

μ = 0.64 mm−1

T = 100 K

0.30 × 0.20 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.832, T max = 0.987

8967 measured reflections

4230 independent reflections

3736 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.06

4230 reflections

220 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025699/bt5286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025699/bt5286Isup2.hkl

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

[Cu(C10H24N4)(H2O)2](C10H19O2)2·2H2O	Z = 1
Mr = 678.44	F(000) = 371
Triclinic, P1	Dx = 1.217 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9820 (6) Å	Cell parameters from 3079 reflections
b = 8.8006 (8) Å	θ = 2.4–28.1°
c = 15.3291 (13) Å	µ = 0.64 mm−1
α = 95.045 (1)°	T = 100 K
β = 93.158 (1)°	Plate, purple
γ = 98.423 (1)°	0.30 × 0.20 × 0.02 mm
V = 925.93 (14) Å3

Bruker SMART APEX diffractometer	4230 independent reflections
Radiation source: fine-focus sealed tube	3736 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.832, Tmax = 0.987	k = −11→11
8967 measured reflections	l = −19→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0348P)2 + 0.1911P] where P = (Fo2 + 2Fc2)/3
4230 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.33 e Å−3
6 restraints	Δρmin = −0.43 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.5000	0.5000	0.01105 (9)
O1	0.9257 (2)	0.05590 (14)	0.38643 (8)	0.0242 (3)
O2	0.93155 (17)	0.28063 (13)	0.33012 (8)	0.0179 (3)
O1W	0.81745 (18)	0.48550 (14)	0.57137 (9)	0.0204 (3)
H11	0.900 (3)	0.555 (2)	0.5970 (13)	0.035 (6)*
H12	0.870 (3)	0.4065 (17)	0.5704 (15)	0.037 (7)*
O2W	0.95494 (18)	0.20230 (14)	0.54959 (9)	0.0185 (3)
H21	0.945 (3)	0.160 (2)	0.4983 (8)	0.040 (7)*
H22	0.982 (3)	0.1320 (19)	0.5783 (13)	0.029 (6)*
N1	0.55275 (19)	0.35212 (15)	0.39806 (9)	0.0135 (3)
H1	0.6723 (15)	0.342 (2)	0.4045 (12)	0.022 (5)*
N2	0.6209 (2)	0.68731 (15)	0.44674 (9)	0.0130 (3)
H2	0.7437 (14)	0.692 (2)	0.4559 (12)	0.017 (5)*
C1	0.5260 (3)	0.4008 (2)	0.30884 (11)	0.0184 (4)
H1A	0.3879	0.4104	0.2963	0.022*
H1B	0.5602	0.3211	0.2653	0.022*
C2	0.6516 (3)	0.5543 (2)	0.29990 (11)	0.0200 (4)
H2A	0.6509	0.5722	0.2370	0.024*
H2B	0.7869	0.5480	0.3205	0.024*
C3	0.5859 (3)	0.6912 (2)	0.35105 (11)	0.0186 (4)
H3A	0.6570	0.7881	0.3332	0.022*
H3B	0.4457	0.6902	0.3367	0.022*
C4	0.5625 (2)	0.82300 (18)	0.49625 (12)	0.0179 (4)
H4A	0.4297	0.8361	0.4754	0.021*
H4B	0.6522	0.9174	0.4871	0.021*
C5	0.5685 (2)	0.79793 (18)	0.59202 (12)	0.0181 (4)
H5A	0.7039	0.7967	0.6145	0.022*
H5B	0.5178	0.8826	0.6259	0.022*
C6	0.9049 (2)	0.13621 (18)	0.32350 (11)	0.0137 (3)
C7	0.8332 (3)	0.04950 (19)	0.23452 (11)	0.0172 (4)
H7A	0.6895	0.0311	0.2309	0.021*
H7B	0.8776	−0.0525	0.2313	0.021*
C8	0.8998 (2)	0.1307 (2)	0.15509 (11)	0.0177 (4)
H8A	0.8265	0.0760	0.1015	0.021*
H8B	0.8690	0.2372	0.1613	0.021*
C9	1.1168 (2)	0.1371 (2)	0.14399 (12)	0.0194 (4)
H9A	1.1902	0.2006	0.1949	0.023*
H9B	1.1499	0.0314	0.1437	0.023*
C10	1.1795 (2)	0.2040 (2)	0.06012 (11)	0.0189 (4)
H10A	1.1426	0.3084	0.0598	0.023*
H10B	1.1078	0.1389	0.0093	0.023*
C11	1.3965 (3)	0.2155 (2)	0.04841 (12)	0.0204 (4)
H11A	1.4684	0.2866	0.0968	0.024*
H11B	1.4356	0.1125	0.0525	0.024*
C12	1.4536 (2)	0.2727 (2)	−0.03877 (11)	0.0188 (4)
H12A	1.4084	0.3732	−0.0439	0.023*
H12B	1.3857	0.1989	−0.0870	0.023*
C13	1.6711 (3)	0.2921 (2)	−0.05047 (11)	0.0196 (4)
H13A	1.7394	0.3678	−0.0032	0.024*
H13B	1.7174	0.1922	−0.0444	0.024*
C14	1.7228 (3)	0.3460 (2)	−0.13872 (12)	0.0253 (4)
H14A	1.6723	0.4440	−0.1454	0.030*
H14B	1.6570	0.2685	−0.1857	0.030*
C15	1.9396 (3)	0.3709 (3)	−0.15119 (14)	0.0329 (5)
H15A	1.9617	0.4047	−0.2095	0.049*
H15B	1.9908	0.2740	−0.1458	0.049*
H15C	2.0058	0.4501	−0.1062	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.01256 (15)	0.00841 (14)	0.01241 (16)	0.00162 (10)	0.00342 (11)	0.00065 (10)
O1	0.0374 (8)	0.0185 (6)	0.0167 (7)	0.0035 (5)	−0.0007 (6)	0.0043 (5)
O2	0.0220 (6)	0.0131 (5)	0.0184 (6)	0.0051 (5)	−0.0005 (5)	−0.0012 (5)
O1W	0.0139 (6)	0.0158 (6)	0.0306 (8)	0.0045 (5)	−0.0032 (5)	−0.0027 (5)
O2W	0.0200 (6)	0.0159 (6)	0.0200 (7)	0.0046 (5)	0.0001 (5)	0.0010 (5)
N1	0.0089 (7)	0.0154 (7)	0.0157 (7)	0.0023 (5)	0.0020 (6)	−0.0020 (5)
N2	0.0096 (7)	0.0127 (6)	0.0176 (7)	0.0030 (5)	0.0031 (6)	0.0028 (5)
C1	0.0170 (9)	0.0250 (9)	0.0133 (9)	0.0061 (7)	0.0014 (7)	−0.0026 (7)
C2	0.0177 (9)	0.0310 (10)	0.0133 (9)	0.0062 (7)	0.0045 (7)	0.0074 (7)
C3	0.0170 (9)	0.0211 (8)	0.0193 (9)	0.0037 (7)	0.0017 (7)	0.0098 (7)
C4	0.0144 (8)	0.0085 (7)	0.0312 (10)	0.0019 (6)	0.0050 (7)	0.0014 (7)
C5	0.0148 (8)	0.0109 (7)	0.0270 (10)	0.0001 (6)	0.0039 (7)	−0.0052 (7)
C6	0.0098 (8)	0.0163 (8)	0.0155 (9)	0.0034 (6)	0.0040 (6)	−0.0002 (6)
C7	0.0184 (9)	0.0157 (8)	0.0163 (9)	−0.0006 (6)	0.0040 (7)	−0.0016 (7)
C8	0.0179 (9)	0.0211 (8)	0.0133 (8)	0.0003 (7)	0.0030 (7)	−0.0002 (7)
C9	0.0176 (9)	0.0240 (9)	0.0168 (9)	0.0027 (7)	0.0032 (7)	0.0017 (7)
C10	0.0174 (9)	0.0234 (9)	0.0156 (9)	0.0009 (7)	0.0036 (7)	0.0024 (7)
C11	0.0192 (9)	0.0259 (9)	0.0162 (9)	0.0025 (7)	0.0054 (7)	0.0021 (7)
C12	0.0165 (9)	0.0242 (9)	0.0150 (9)	0.0003 (7)	0.0031 (7)	0.0018 (7)
C13	0.0186 (9)	0.0250 (9)	0.0154 (9)	0.0024 (7)	0.0033 (7)	0.0027 (7)
C14	0.0210 (10)	0.0367 (11)	0.0182 (10)	0.0012 (8)	0.0044 (7)	0.0071 (8)
C15	0.0250 (10)	0.0443 (12)	0.0316 (12)	0.0039 (9)	0.0138 (9)	0.0104 (9)

Cu1—N1	2.029 (1)	C5—H5B	0.9900
Cu1—N1i	2.029 (1)	C6—C7	1.524 (2)
Cu1—N2	2.000 (1)	C7—C8	1.526 (2)
Cu1—N2i	2.000 (1)	C7—H7A	0.9900
Cu1—O1w	2.443 (1)	C7—H7B	0.9900
O1—C6	1.259 (2)	C8—C9	1.527 (2)
O2—C6	1.2515 (19)	C8—H8A	0.9900
O1W—H11	0.832 (10)	C8—H8B	0.9900
O1W—H12	0.831 (9)	C9—C10	1.520 (2)
O2W—H21	0.834 (9)	C9—H9A	0.9900
O2W—H22	0.828 (9)	C9—H9B	0.9900
N1—C1	1.479 (2)	C10—C11	1.525 (2)
N1—C5i	1.485 (2)	C10—H10A	0.9900
N1—H1	0.855 (9)	C10—H10B	0.9900
N2—C3	1.478 (2)	C11—C12	1.522 (2)
N2—C4	1.478 (2)	C11—H11A	0.9900
N2—H2	0.854 (9)	C11—H11B	0.9900
C1—C2	1.520 (2)	C12—C13	1.525 (2)
C1—H1A	0.9900	C12—H12A	0.9900
C1—H1B	0.9900	C12—H12B	0.9900
C2—C3	1.521 (2)	C13—C14	1.517 (2)
C2—H2A	0.9900	C13—H13A	0.9900
C2—H2B	0.9900	C13—H13B	0.9900
C3—H3A	0.9900	C14—C15	1.522 (3)
C3—H3B	0.9900	C14—H14A	0.9900
C4—C5	1.503 (3)	C14—H14B	0.9900
C4—H4A	0.9900	C15—H15A	0.9800
C4—H4B	0.9900	C15—H15B	0.9800
C5—N1i	1.485 (2)	C15—H15C	0.9800
C5—H5A	0.9900
N2—Cu1—N2i	180.000 (1)	O2—C6—C7	118.55 (15)
N2—Cu1—N1	93.73 (6)	O1—C6—C7	116.87 (14)
N2i—Cu1—N1	86.27 (6)	C6—C7—C8	115.27 (13)
N2—Cu1—N1i	86.27 (6)	C6—C7—H7A	108.5
N2i—Cu1—N1i	93.73 (6)	C8—C7—H7A	108.5
N1—Cu1—N1i	180.00 (5)	C6—C7—H7B	108.5
N2—Cu1—O1W	88.48 (5)	C8—C7—H7B	108.5
N2i—Cu1—O1W	91.52 (5)	H7A—C7—H7B	107.5
N1—Cu1—O1W	90.25 (5)	C9—C8—C7	113.07 (15)
N1i—Cu1—O1W	89.75 (5)	C9—C8—H8A	109.0
Cu1—O1W—H11	130.2 (16)	C7—C8—H8A	109.0
Cu1—O1W—H12	124.9 (16)	C9—C8—H8B	109.0
H11—O1W—H12	105 (2)	C7—C8—H8B	109.0
H21—O2W—H22	102 (2)	H8A—C8—H8B	107.8
C1—N1—C5i	112.07 (13)	C10—C9—C8	113.02 (15)
C1—N1—Cu1	117.07 (10)	C10—C9—H9A	109.0
C5i—N1—Cu1	106.17 (10)	C8—C9—H9A	109.0
C1—N1—H1	105.4 (13)	C10—C9—H9B	109.0
C5i—N1—H1	108.8 (13)	C8—C9—H9B	109.0
Cu1—N1—H1	107.0 (13)	H9A—C9—H9B	107.8
C3—N2—C4	111.44 (13)	C9—C10—C11	114.15 (15)
C3—N2—Cu1	117.71 (10)	C9—C10—H10A	108.7
C4—N2—Cu1	107.26 (10)	C11—C10—H10A	108.7
C3—N2—H2	105.7 (13)	C9—C10—H10B	108.7
C4—N2—H2	107.8 (13)	C11—C10—H10B	108.7
Cu1—N2—H2	106.5 (13)	H10A—C10—H10B	107.6
N1—C1—C2	111.30 (14)	C12—C11—C10	113.15 (15)
N1—C1—H1A	109.4	C12—C11—H11A	108.9
C2—C1—H1A	109.4	C10—C11—H11A	108.9
N1—C1—H1B	109.4	C12—C11—H11B	108.9
C2—C1—H1B	109.4	C10—C11—H11B	108.9
H1A—C1—H1B	108.0	H11A—C11—H11B	107.8
C1—C2—C3	113.84 (14)	C11—C12—C13	114.24 (15)
C1—C2—H2A	108.8	C11—C12—H12A	108.7
C3—C2—H2A	108.8	C13—C12—H12A	108.7
C1—C2—H2B	108.8	C11—C12—H12B	108.7
C3—C2—H2B	108.8	C13—C12—H12B	108.7
H2A—C2—H2B	107.7	H12A—C12—H12B	107.6
N2—C3—C2	111.53 (13)	C14—C13—C12	112.92 (15)
N2—C3—H3A	109.3	C14—C13—H13A	109.0
C2—C3—H3A	109.3	C12—C13—H13A	109.0
N2—C3—H3B	109.3	C14—C13—H13B	109.0
C2—C3—H3B	109.3	C12—C13—H13B	109.0
H3A—C3—H3B	108.0	H13A—C13—H13B	107.8
N2—C4—C5	108.50 (13)	C13—C14—C15	114.09 (16)
N2—C4—H4A	110.0	C13—C14—H14A	108.7
C5—C4—H4A	110.0	C15—C14—H14A	108.7
N2—C4—H4B	110.0	C13—C14—H14B	108.7
C5—C4—H4B	110.0	C15—C14—H14B	108.7
H4A—C4—H4B	108.4	H14A—C14—H14B	107.6
N1i—C5—C4	108.31 (13)	C14—C15—H15A	109.5
N1i—C5—H5A	110.0	C14—C15—H15B	109.5
C4—C5—H5A	110.0	H15A—C15—H15B	109.5
N1i—C5—H5B	110.0	C14—C15—H15C	109.5
C4—C5—H5B	110.0	H15A—C15—H15C	109.5
H5A—C5—H5B	108.4	H15B—C15—H15C	109.5
O2—C6—O1	124.52 (15)
N2—Cu1—N1—C1	−39.47 (12)	C4—N2—C3—C2	178.27 (13)
N2i—Cu1—N1—C1	140.53 (12)	Cu1—N2—C3—C2	−57.23 (16)
O1W—Cu1—N1—C1	−127.96 (11)	C1—C2—C3—N2	70.00 (18)
N2—Cu1—N1—C5i	−165.46 (11)	C3—N2—C4—C5	170.11 (13)
N2i—Cu1—N1—C5i	14.54 (11)	Cu1—N2—C4—C5	39.93 (15)
O1W—Cu1—N1—C5i	106.05 (11)	N2—C4—C5—N1i	−54.24 (17)
N1—Cu1—N2—C3	39.47 (12)	O2—C6—C7—C8	31.5 (2)
N1i—Cu1—N2—C3	−140.53 (12)	O1—C6—C7—C8	−151.30 (16)
O1W—Cu1—N2—C3	129.61 (11)	C6—C7—C8—C9	69.42 (19)
N1—Cu1—N2—C4	166.02 (11)	C7—C8—C9—C10	174.47 (14)
N1i—Cu1—N2—C4	−13.98 (11)	C8—C9—C10—C11	178.58 (14)
O1W—Cu1—N2—C4	−103.84 (10)	C9—C10—C11—C12	176.14 (14)
C5i—N1—C1—C2	−179.84 (13)	C10—C11—C12—C13	177.40 (14)
Cu1—N1—C1—C2	57.16 (16)	C11—C12—C13—C14	178.81 (15)
N1—C1—C2—C3	−70.19 (19)	C12—C13—C14—C15	178.29 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86 (1)	2.30 (1)	3.025 (2)	144 (2)
N2—H2···O2wii	0.85 (1)	2.18 (1)	2.974 (2)	154 (2)
O1w—H11···O2ii	0.83 (1)	1.95 (1)	2.774 (2)	172 (2)
O1w—H12···O2w	0.83 (1)	1.98 (1)	2.799 (2)	169 (2)
O2w—H21···O1	0.83 (1)	1.86 (1)	2.694 (2)	177 (2)
O2w—H22···O1iii	0.83 (1)	1.97 (1)	2.771 (2)	163 (2)

Table 1

Selected bond lengths (Å)

Cu1—N1	2.029 (1)
Cu1—N2	2.000 (1)
Cu1—O1w	2.443 (1)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86 (1)	2.30 (1)	3.025 (2)	144 (2)
N2—H2⋯O2wi	0.85 (1)	2.18 (1)	2.974 (2)	154 (2)
O1w—H11⋯O2i	0.83 (1)	1.95 (1)	2.774 (2)	172 (2)
O1w—H12⋯O2w	0.83 (1)	1.98 (1)	2.799 (2)	169 (2)
O2w—H21⋯O1	0.83 (1)	1.86 (1)	2.694 (2)	177 (2)
O2w—H22⋯O1ii	0.83 (1)	1.97 (1)	2.771 (2)	163 (2)

Symmetry codes: (i) ; (ii) .