Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N1,N4,N8,N11)copper(II) dihepta­noate dihydrate

Ahmad Tajidi, N.S.; Abdullah, N.; Arifin, Z.; Tan, K.W.; Ng, S.W.

doi:10.1107/S1600536810025687

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m887

https://doi.org/10.1107/S1600536810025687

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Diaqua(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)copper(II) diheptanoate dihydrate

Nur Syamimi Ahmad Tajidi,^a Norbani Abdullah,^a Zainudin Arifin,^a Kong Wai Tan ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 30 June 2010; accepted 30 June 2010; online 7 July 2010)

The Cu^II atom in the title salt, [Cu(C₁₀H₂₄N₄)(H₂O)₂][CH₃(CH₂)₅CO₂]₂·2H₂O, is chelated by the four N atoms of the 1,4,8,11-tetraazacyclotetradecane (cyclam) ligand and is coordinated by two water molecules in a tetragonally Jahn–Teller-distorted octahedral geometry. The Cu^II atom lies on a center of inversion. The cations, anions and uncoordinated water molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, forming a layer structure parallel to (100). The alkyl chain of the anion is disordered over two positions in a 0.82 (1):0.18 (1) ratio.

Related literature

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

Experimental

Crystal data

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇H₁₃O₂)₂·2H₂O
M_r = 594.28
Monoclinic, P 2₁ /c
a = 11.7257 (6) Å
b = 9.9426 (5) Å
c = 13.4573 (7) Å
β = 103.1363 (7)°
V = 1527.85 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 100 K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.776, T_max = 0.894
14358 measured reflections
3506 independent reflections
3140 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.079
S = 1.06
3506 reflections
212 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	2.026 (1)
Cu1—N2	2.025 (1)
Cu1—O1w	2.499 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (1)	2.30 (1)	2.983 (2)	137 (2)
N2—H2⋯O2	0.86 (1)	2.12 (1)	2.924 (2)	156 (2)
O1w—H11⋯O2	0.83 (1)	1.93 (1)	2.730 (2)	162 (2)
O1w—H12⋯O2w	0.83 (1)	1.95 (1)	2.777 (2)	174 (2)
O2w—H21⋯O1ⁱⁱ	0.83 (1)	2.02 (1)	2.833 (2)	166 (2)
O2w—H22⋯O1ⁱ	0.84 (1)	1.91 (1)	2.743 (2)	171 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810025687/bt5285sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025687/bt5285Isup2.hkl

checkCIF report

Comment top

The copper(II) ion forms a number of complexes with 1,4,8,11-tetraazacyclotetradecane in which the metal atom is coordinated by the four amino donor-atoms of the cyclic ligand. Among the carboxylate derivatives, neither the acetate nor the benzoate ions bind directly with the copper atom. The copper atom is coordinated instead by water molecules so that the carboxylate group interacts indirectly with the metal atom through the coordinated water molecules (Hunter et al., 2005; Lindoy et al., 2003). The copper(II) atom in the salt, [Cu(H₂O)₂(C₁₀H₂₄N₄)]²⁺ 2[CH₃(CH₂)₅CO₂]^-.2H₂O (Scheme I), is chelated by the four nitrogen atoms of the cyclam ligand and is coordinated by two water molecules in a Jahn-Teller type of tetragonally distorted octahedral geometry. The copper atom lies on a center of inversion (Fig. 1). The cations, anions and lattice water molecules are linked by N–H···O and O–H···O hydrogen bonds to form a layer structure.

Related literature top

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

Experimental top

1,4,8,11-Tetraazacyclotetradecane (0.50 g, 2.50 mmol) dissolved in ethanol (25 ml) was mixed with a suspension of copper heptanoate (0.80 g, 2.5 mmol) in ethanol (50 ml) to give a purple solution. The solution was heated for an hour and then filtered. Prismatic crystals separated from the solution when it was left to cool slowly.

Structure description top

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

Computing details top

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

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Cu(H₂O)₂(C₁₀H₂₄N₄)]²⁺ 2[CH₃(CH₂)₅CO₂]^-.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the alkyl chain is not shown.

Diaqua(1,4,8,11-tetraazacyclotetradecane- κ⁴N¹,N⁴,N⁸,N¹¹)copper(II) diheptanoate dihydrate top

Crystal data top

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇H₁₃O₂)₂·2H₂O	F(000) = 646
M_r = 594.28	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8003 reflections
a = 11.7257 (6) Å	θ = 2.6–28.3°
b = 9.9426 (5) Å	µ = 0.76 mm⁻¹
c = 13.4573 (7) Å	T = 100 K
β = 103.1363 (7)°	Block, purple
V = 1527.85 (14) Å³	0.35 × 0.25 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	3506 independent reflections
Radiation source: fine-focus sealed tube	3140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.776, T_max = 0.894	k = −12→12
14358 measured reflections	l = −17→17

Refinement top

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0406P)² + 0.7328P] where P = (F_o² + 2F_c²)/3
3506 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.81 e Å⁻³
12 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇H₁₃O₂)₂·2H₂O	V = 1527.85 (14) Å³
M_r = 594.28	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7257 (6) Å	µ = 0.76 mm⁻¹
b = 9.9426 (5) Å	T = 100 K
c = 13.4573 (7) Å	0.35 × 0.25 × 0.15 mm
β = 103.1363 (7)°

Data collection top

Bruker SMART APEX diffractometer	3506 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3140 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.894	R_int = 0.022
14358 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	12 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.81 e Å⁻³
3506 reflections	Δρ_min = −0.31 e Å⁻³
212 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.5000	0.5000	0.5000	0.01672 (8)
O1	0.37230 (9)	0.57029 (10)	0.88828 (7)	0.0254 (2)
O2	0.35970 (10)	0.48007 (10)	0.73553 (8)	0.0260 (2)
O1W	0.35364 (10)	0.35174 (11)	0.55509 (8)	0.0262 (2)
H11	0.3445 (19)	0.378 (2)	0.6109 (10)	0.047 (6)*
H12	0.3586 (17)	0.2684 (10)	0.5589 (15)	0.035 (5)*
O2W	0.38768 (10)	0.07550 (11)	0.57173 (8)	0.0272 (2)
H21	0.372 (2)	0.031 (2)	0.5184 (11)	0.045 (6)*
H22	0.4606 (9)	0.070 (2)	0.5895 (16)	0.046 (6)*
N1	0.62254 (10)	0.35391 (11)	0.53855 (9)	0.0196 (2)
H1	0.5925 (14)	0.2927 (14)	0.5699 (12)	0.025 (4)*
N2	0.54008 (11)	0.58808 (11)	0.63930 (8)	0.0196 (2)
H2	0.5052 (14)	0.5435 (16)	0.6783 (11)	0.022 (4)*
C1	0.73634 (13)	0.39280 (15)	0.60465 (11)	0.0246 (3)
H1A	0.7760	0.4571	0.5676	0.030*
H1B	0.7866	0.3120	0.6205	0.030*
C2	0.72217 (14)	0.45693 (16)	0.70380 (11)	0.0267 (3)
H2A	0.8003	0.4645	0.7507	0.032*
H2B	0.6740	0.3967	0.7363	0.032*
C3	0.66565 (13)	0.59536 (15)	0.69082 (10)	0.0242 (3)
H3A	0.6738	0.6376	0.7587	0.029*
H3B	0.7070	0.6528	0.6502	0.029*
C4	0.48410 (14)	0.72262 (14)	0.62714 (11)	0.0244 (3)
H4A	0.5314	0.7860	0.5964	0.029*
H4B	0.4781	0.7584	0.6944	0.029*
C5	0.36356 (13)	0.70700 (14)	0.55851 (10)	0.0231 (3)
H5A	0.3146	0.6484	0.5914	0.028*
H5B	0.3249	0.7958	0.5453	0.028*
C6	0.31775 (13)	0.50923 (13)	0.80991 (11)	0.0203 (3)
C7	0.18993 (17)	0.4746 (2)	0.81018 (17)	0.0289 (5)	0.822 (3)
H7A	0.1856	0.3788	0.8288	0.035*	0.822 (3)
H7B	0.1655	0.5291	0.8634	0.035*	0.822 (3)
C8	0.10391 (17)	0.49936 (19)	0.70811 (18)	0.0318 (5)	0.822 (3)
H8A	0.1308	0.4489	0.6542	0.038*	0.822 (3)
H8B	0.0263	0.4633	0.7119	0.038*	0.822 (3)
C9	0.09044 (18)	0.6455 (2)	0.67784 (15)	0.0299 (5)	0.822 (3)
H9A	0.1691	0.6840	0.6812	0.036*	0.822 (3)
H9B	0.0556	0.6942	0.7279	0.036*	0.822 (3)
C10	0.01464 (18)	0.6690 (2)	0.57143 (18)	0.0357 (5)	0.822 (3)
H10A	0.0433	0.6106	0.5227	0.043*	0.822 (3)
H10B	−0.0665	0.6411	0.5709	0.043*	0.822 (3)
C11	0.01253 (18)	0.8120 (3)	0.53458 (18)	0.0402 (6)	0.822 (3)
H11A	0.0928	0.8384	0.5306	0.048*	0.822 (3)
H11B	−0.0118	0.8714	0.5851	0.048*	0.822 (3)
C12	−0.0696 (3)	0.8339 (5)	0.4308 (2)	0.0541 (9)	0.822 (3)
H12A	−0.0671	0.9286	0.4112	0.081*	0.822 (3)
H12B	−0.1497	0.8101	0.4344	0.081*	0.822 (3)
H12C	−0.0450	0.7771	0.3799	0.081*	0.822 (3)
C7'	0.2043 (7)	0.4295 (9)	0.7967 (10)	0.0289 (5)	0.18
H7'1	0.1981	0.3868	0.8617	0.035*	0.178 (3)
H7'2	0.1995	0.3589	0.7441	0.035*	0.178 (3)
C8'	0.1079 (7)	0.5358 (9)	0.7631 (8)	0.0318 (5)	0.18
H8'1	0.0302	0.4928	0.7548	0.038*	0.178 (3)
H8'2	0.1152	0.6057	0.8165	0.038*	0.178 (3)
C9'	0.1167 (9)	0.6010 (11)	0.6632 (7)	0.0299 (5)	0.18
H9'1	0.1238	0.5297	0.6137	0.036*	0.178 (3)
H9'2	0.1889	0.6561	0.6750	0.036*	0.178 (3)
C10'	0.0116 (8)	0.6905 (12)	0.6166 (8)	0.0357 (5)	0.18
H10C	−0.0619	0.6384	0.6088	0.043*	0.178 (3)
H10D	0.0080	0.7676	0.6624	0.043*	0.178 (3)
C11'	0.0239 (9)	0.7419 (15)	0.5123 (8)	0.0402 (6)	0.18
H11C	0.0363	0.6646	0.4696	0.048*	0.178 (3)
H11D	0.0934	0.8010	0.5215	0.048*	0.178 (3)
C12'	−0.0852 (14)	0.820 (3)	0.4572 (14)	0.0541 (9)	0.18
H12D	−0.0733	0.8539	0.3918	0.081*	0.178 (3)
H12E	−0.0983	0.8964	0.4996	0.081*	0.178 (3)
H12F	−0.1536	0.7608	0.4450	0.081*	0.178 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02403 (13)	0.01387 (12)	0.01321 (12)	−0.00126 (8)	0.00619 (9)	−0.00200 (7)
O1	0.0350 (6)	0.0224 (5)	0.0193 (5)	0.0001 (4)	0.0071 (4)	−0.0030 (4)
O2	0.0375 (6)	0.0262 (5)	0.0170 (5)	−0.0036 (4)	0.0114 (4)	−0.0006 (4)
O1W	0.0414 (6)	0.0197 (5)	0.0214 (5)	−0.0041 (4)	0.0155 (5)	−0.0017 (4)
O2W	0.0334 (6)	0.0254 (5)	0.0243 (5)	0.0020 (4)	0.0098 (5)	−0.0037 (4)
N1	0.0278 (6)	0.0160 (5)	0.0168 (5)	−0.0017 (4)	0.0087 (5)	0.0008 (4)
N2	0.0286 (6)	0.0164 (5)	0.0154 (5)	−0.0036 (4)	0.0086 (5)	−0.0012 (4)
C1	0.0262 (7)	0.0244 (7)	0.0236 (7)	0.0000 (6)	0.0062 (6)	0.0026 (5)
C2	0.0281 (7)	0.0309 (7)	0.0195 (7)	−0.0030 (6)	0.0023 (6)	0.0020 (6)
C3	0.0296 (7)	0.0261 (7)	0.0167 (6)	−0.0071 (6)	0.0048 (5)	−0.0043 (5)
C4	0.0397 (8)	0.0157 (6)	0.0200 (7)	−0.0013 (6)	0.0114 (6)	−0.0040 (5)
C5	0.0348 (8)	0.0175 (6)	0.0201 (7)	0.0028 (5)	0.0129 (6)	0.0003 (5)
C6	0.0256 (7)	0.0181 (6)	0.0180 (6)	−0.0008 (5)	0.0067 (5)	0.0044 (5)
C7	0.0285 (9)	0.0325 (12)	0.0286 (11)	−0.0059 (9)	0.0126 (7)	0.0039 (9)
C8	0.0227 (9)	0.0334 (11)	0.0399 (13)	−0.0077 (7)	0.0084 (9)	−0.0050 (8)
C9	0.0235 (10)	0.0395 (13)	0.0263 (10)	−0.0052 (8)	0.0048 (7)	−0.0021 (8)
C10	0.0227 (8)	0.0492 (12)	0.0325 (12)	−0.0052 (8)	0.0008 (9)	−0.0009 (10)
C11	0.0225 (9)	0.0668 (17)	0.0313 (11)	0.0054 (11)	0.0064 (8)	0.0068 (11)
C12	0.0371 (14)	0.0795 (19)	0.039 (2)	0.0062 (13)	−0.0047 (11)	0.0093 (15)
C7'	0.0285 (9)	0.0325 (12)	0.0286 (11)	−0.0059 (9)	0.0126 (7)	0.0039 (9)
C8'	0.0227 (9)	0.0334 (11)	0.0399 (13)	−0.0077 (7)	0.0084 (9)	−0.0050 (8)
C9'	0.0235 (10)	0.0395 (13)	0.0263 (10)	−0.0052 (8)	0.0048 (7)	−0.0021 (8)
C10'	0.0227 (8)	0.0492 (12)	0.0325 (12)	−0.0052 (8)	0.0008 (9)	−0.0009 (10)
C11'	0.0225 (9)	0.0668 (17)	0.0313 (11)	0.0054 (11)	0.0064 (8)	0.0068 (11)
C12'	0.0371 (14)	0.0795 (19)	0.039 (2)	0.0062 (13)	−0.0047 (11)	0.0093 (15)

Geometric parameters (Å, º) top

Cu1—N1	2.026 (1)	C7—H7B	0.9900
Cu1—N2	2.025 (1)	C8—C9	1.507 (3)
Cu1—N2ⁱ	2.025 (1)	C8—H8A	0.9900
Cu1—N1ⁱ	2.026 (1)	C8—H8B	0.9900
Cu1—O1w	2.499 (1)	C9—C10	1.522 (3)
O1—C6	1.2584 (18)	C9—H9A	0.9900
O2—C6	1.2456 (18)	C9—H9B	0.9900
O1W—H11	0.826 (10)	C10—C11	1.504 (3)
O1W—H12	0.831 (9)	C10—H10A	0.9900
O2W—H21	0.829 (10)	C10—H10B	0.9900
O2W—H22	0.836 (10)	C11—C12	1.521 (3)
N1—C1	1.4771 (19)	C11—H11A	0.9900
N1—C5ⁱ	1.4818 (17)	C11—H11B	0.9900
N1—H1	0.860 (9)	C12—H12A	0.9800
N2—C3	1.4798 (18)	C12—H12B	0.9800
N2—C4	1.4827 (18)	C12—H12C	0.9800
N2—H2	0.858 (9)	C7'—C8'	1.539 (9)
C1—C2	1.521 (2)	C7'—H7'1	0.9900
C1—H1A	0.9900	C7'—H7'2	0.9900
C1—H1B	0.9900	C8'—C9'	1.516 (8)
C2—C3	1.520 (2)	C8'—H8'1	0.9900
C2—H2A	0.9900	C8'—H8'2	0.9900
C2—H2B	0.9900	C9'—C10'	1.535 (9)
C3—H3A	0.9900	C9'—H9'1	0.9900
C3—H3B	0.9900	C9'—H9'2	0.9900
C4—C5	1.511 (2)	C10'—C11'	1.531 (9)
C4—H4A	0.9900	C10'—H10C	0.9900
C4—H4B	0.9900	C10'—H10D	0.9900
C5—N1ⁱ	1.4818 (17)	C11'—C12'	1.538 (9)
C5—H5A	0.9900	C11'—H11C	0.9900
C5—H5B	0.9900	C11'—H11D	0.9900
C6—C7'	1.524 (8)	C12'—H12D	0.9800
C6—C7	1.539 (2)	C12'—H12E	0.9800
C7—C8	1.528 (3)	C12'—H12F	0.9800
C7—H7A	0.9900

N2—Cu1—N2ⁱ	180.0	H7A—C7—H7B	107.7
N2—Cu1—N1ⁱ	85.92 (5)	C9—C8—C7	113.91 (17)
N2ⁱ—Cu1—N1ⁱ	94.08 (5)	C9—C8—H8A	108.8
N2—Cu1—N1	94.08 (5)	C7—C8—H8A	108.8
N2ⁱ—Cu1—N1	85.92 (5)	C9—C8—H8B	108.8
N1ⁱ—Cu1—N1	180.0	C7—C8—H8B	108.8
N2—Cu1—O1W	90.63 (4)	H8A—C8—H8B	107.7
N2ⁱ—Cu1—O1W	89.37 (4)	C8—C9—C10	113.94 (18)
N1ⁱ—Cu1—O1W	90.23 (4)	C8—C9—H9A	108.8
N1—Cu1—O1W	89.77 (4)	C10—C9—H9A	108.8
Cu1—O1W—H11	108.7 (16)	C8—C9—H9B	108.8
Cu1—O1W—H12	124.3 (14)	C10—C9—H9B	108.8
H11—O1W—H12	106 (2)	H9A—C9—H9B	107.7
H21—O2W—H22	103 (2)	C11—C10—C9	114.72 (19)
C1—N1—C5ⁱ	111.88 (11)	C11—C10—H10A	108.6
C1—N1—Cu1	117.23 (9)	C9—C10—H10A	108.6
C5ⁱ—N1—Cu1	106.32 (8)	C11—C10—H10B	108.6
C1—N1—H1	107.7 (12)	C9—C10—H10B	108.6
C5ⁱ—N1—H1	106.4 (12)	H10A—C10—H10B	107.6
Cu1—N1—H1	106.7 (12)	C10—C11—C12	113.4 (3)
C3—N2—C4	112.08 (11)	C10—C11—H11A	108.9
C3—N2—Cu1	116.85 (9)	C12—C11—H11A	108.9
C4—N2—Cu1	106.51 (8)	C10—C11—H11B	108.9
C3—N2—H2	107.5 (12)	C12—C11—H11B	108.9
C4—N2—H2	105.9 (12)	H11A—C11—H11B	107.7
Cu1—N2—H2	107.4 (12)	C11—C12—H12A	109.5
N1—C1—C2	111.97 (12)	C11—C12—H12B	109.5
N1—C1—H1A	109.2	H12A—C12—H12B	109.5
C2—C1—H1A	109.2	C11—C12—H12C	109.5
N1—C1—H1B	109.2	H12A—C12—H12C	109.5
C2—C1—H1B	109.2	H12B—C12—H12C	109.5
H1A—C1—H1B	107.9	C6—C7'—C8'	103.9 (6)
C1—C2—C3	114.22 (12)	C6—C7'—H7'1	111.0
C1—C2—H2A	108.7	C8'—C7'—H7'1	111.0
C3—C2—H2A	108.7	C6—C7'—H7'2	111.0
C1—C2—H2B	108.7	C8'—C7'—H7'2	111.0
C3—C2—H2B	108.7	H7'1—C7'—H7'2	109.0
H2A—C2—H2B	107.6	C9'—C8'—C7'	111.2 (8)
N2—C3—C2	111.77 (11)	C9'—C8'—H8'1	109.4
N2—C3—H3A	109.3	C7'—C8'—H8'1	109.4
C2—C3—H3A	109.3	C9'—C8'—H8'2	109.4
N2—C3—H3B	109.3	C7'—C8'—H8'2	109.4
C2—C3—H3B	109.3	H8'1—C8'—H8'2	108.0
H3A—C3—H3B	107.9	C8'—C9'—C10'	113.6 (8)
N2—C4—C5	107.69 (11)	C8'—C9'—H9'1	108.9
N2—C4—H4A	110.2	C10'—C9'—H9'1	108.9
C5—C4—H4A	110.2	C8'—C9'—H9'2	108.9
N2—C4—H4B	110.2	C10'—C9'—H9'2	108.9
C5—C4—H4B	110.2	H9'1—C9'—H9'2	107.7
H4A—C4—H4B	108.5	C11'—C10'—C9'	109.5 (8)
N1ⁱ—C5—C4	107.82 (11)	C11'—C10'—H10C	109.8
N1ⁱ—C5—H5A	110.1	C9'—C10'—H10C	109.8
C4—C5—H5A	110.1	C11'—C10'—H10D	109.8
N1ⁱ—C5—H5B	110.1	C9'—C10'—H10D	109.8
C4—C5—H5B	110.1	H10C—C10'—H10D	108.2
H5A—C5—H5B	108.5	C10'—C11'—C12'	111.7 (10)
O2—C6—O1	124.58 (14)	C10'—C11'—H11C	109.3
O2—C6—C7'	106.2 (5)	C12'—C11'—H11C	109.3
O1—C6—C7'	127.8 (5)	C10'—C11'—H11D	109.3
O2—C6—C7	120.84 (14)	C12'—C11'—H11D	109.3
O1—C6—C7	114.56 (14)	H11C—C11'—H11D	107.9
C7'—C6—C7	19.8 (4)	C11'—C12'—H12D	109.5
C8—C7—C6	113.97 (16)	C11'—C12'—H12E	109.5
C8—C7—H7A	108.8	H12D—C12'—H12E	109.5
C6—C7—H7A	108.8	C11'—C12'—H12F	109.5
C8—C7—H7B	108.8	H12D—C12'—H12F	109.5
C6—C7—H7B	108.8	H12E—C12'—H12F	109.5

N2—Cu1—N1—C1	−38.82 (10)	C3—N2—C4—C5	170.38 (11)
N2ⁱ—Cu1—N1—C1	141.18 (10)	Cu1—N2—C4—C5	41.42 (12)
O1W—Cu1—N1—C1	−129.43 (9)	N2—C4—C5—N1ⁱ	−56.62 (14)
N2—Cu1—N1—C5ⁱ	−164.78 (9)	O2—C6—C7—C8	−40.9 (2)
N2ⁱ—Cu1—N1—C5ⁱ	15.22 (9)	O1—C6—C7—C8	137.52 (16)
O1W—Cu1—N1—C5ⁱ	104.60 (9)	C7'—C6—C7—C8	−86.5 (15)
N1ⁱ—Cu1—N2—C3	−140.76 (10)	C6—C7—C8—C9	−66.1 (2)
N1—Cu1—N2—C3	39.24 (10)	C7—C8—C9—C10	174.03 (18)
O1W—Cu1—N2—C3	129.05 (9)	C8—C9—C10—C11	−172.59 (19)
N1ⁱ—Cu1—N2—C4	−14.63 (9)	C9—C10—C11—C12	−176.5 (2)
N1—Cu1—N2—C4	165.37 (9)	O2—C6—C7'—C8'	−105.8 (7)
O1W—Cu1—N2—C4	−104.81 (9)	O1—C6—C7'—C8'	87.6 (8)
C5ⁱ—N1—C1—C2	179.31 (11)	C7—C6—C7'—C8'	34.5 (10)
Cu1—N1—C1—C2	56.13 (14)	C6—C7'—C8'—C9'	60.9 (11)
N1—C1—C2—C3	−69.50 (16)	C7'—C8'—C9'—C10'	170.4 (9)
C4—N2—C3—C2	179.52 (11)	C8'—C9'—C10'—C11'	−175.3 (10)
Cu1—N2—C3—C2	−57.16 (13)	C9'—C10'—C11'—C12'	174.2 (15)
C1—C2—C3—N2	70.11 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.86 (1)	2.30 (1)	2.983 (2)	137 (2)
N2—H2···O2	0.86 (1)	2.12 (1)	2.924 (2)	156 (2)
O1w—H11···O2	0.83 (1)	1.93 (1)	2.730 (2)	162 (2)
O1w—H12···O2w	0.83 (1)	1.95 (1)	2.777 (2)	174 (2)
O2w—H21···O1ⁱⁱⁱ	0.83 (1)	2.02 (1)	2.833 (2)	166 (2)
O2w—H22···O1ⁱⁱ	0.84 (1)	1.91 (1)	2.743 (2)	171 (2)

Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇H₁₃O₂)₂·2H₂O
M_r	594.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.7257 (6), 9.9426 (5), 13.4573 (7)
β (°)	103.1363 (7)
V (Å³)	1527.85 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.776, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	14358, 3506, 3140
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.079, 1.06
No. of reflections	3506
No. of parameters	212
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cu1—N1	2.026 (1)	Cu1—O1w	2.499 (1)
Cu1—N2	2.025 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.30 (1)	2.983 (2)	137 (2)
N2—H2···O2	0.86 (1)	2.12 (1)	2.924 (2)	156 (2)
O1w—H11···O2	0.83 (1)	1.93 (1)	2.730 (2)	162 (2)
O1w—H12···O2w	0.83 (1)	1.95 (1)	2.777 (2)	174 (2)
O2w—H21···O1ⁱⁱ	0.83 (1)	2.02 (1)	2.833 (2)	166 (2)
O2w—H22···O1ⁱ	0.84 (1)	1.91 (1)	2.743 (2)	171 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

We thank the University of Malaya (RG039/09SUS) and the Ministry of Higher Education (FP017/2009) for supporting this study.

References

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