Diaqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N1,N4,N8,N11)copper(II) bis­(2,3,4,5,6-penta­fluoro­benzoate) dihydrate

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

doi:10.1107/S1600536810025705

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m889

https://doi.org/10.1107/S1600536810025705

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Diaqua(1,4,8,11-tetraazacyclotetradecane-κ⁴N¹,N⁴,N⁸,N¹¹)copper(II) bis(2,3,4,5,6-pentafluorobenzoate) 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](C₆F₅CO₂)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 Jahn–Teller-type tetragonally 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 (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](C₇F₅O₂)₂·2H₂O
M_r = 758.08
Triclinic, $[P \overline 1]$
a = 7.1976 (6) Å
b = 8.7632 (7) Å
c = 12.1574 (10) Å
α = 79.378 (1)°
β = 75.408 (1)°
γ = 80.606 (1)°
V = 723.85 (10) Å³
Z = 1
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.750, T_max = 0.958
6996 measured reflections
3306 independent reflections
3028 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.111
S = 1.06
3306 reflections
238 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.75 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2wⁱ	0.86 (1)	2.17 (2)	2.997 (2)	157 (3)
N2—H2⋯O1w	0.86 (1)	2.70 (3)	3.123 (2)	112 (2)
O1w—H11⋯O2ⁱ	0.83 (1)	1.98 (1)	2.785 (2)	162 (3)
O1w—H12⋯O2w	0.83 (1)	2.10 (2)	2.898 (2)	160 (3)
O2w—H21⋯O1	0.83 (1)	1.90 (1)	2.723 (2)	169 (3)
O2w—H22⋯O1ⁱⁱ	0.83 (1)	2.08 (2)	2.842 (2)	152 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1.

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/S1600536810025705/bt5287sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025705/bt5287Isup2.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(C₆F₅CO₂)^-.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 (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 pentafluorobenzoate (1.22 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 (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(C₆F₅CO₂)^-.2H₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Diaqua(1,4,8,11-tetraazacyclotetradecane- κ⁴N¹,N⁴,N⁸,N¹¹)copper(II) bis(2,3,4,5,6-pentafluorobenzoate) dihydrate top

Crystal data top

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇F₅O₂)₂·2H₂O	Z = 1
M_r = 758.08	F(000) = 387
Triclinic, P1	D_x = 1.739 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1976 (6) Å	Cell parameters from 3327 reflections
b = 8.7632 (7) Å	θ = 2.4–28.3°
c = 12.1574 (10) Å	µ = 0.87 mm⁻¹
α = 79.378 (1)°	T = 100 K
β = 75.408 (1)°	Plate, purple
γ = 80.606 (1)°	0.35 × 0.15 × 0.05 mm
V = 723.85 (10) Å³

Data collection top

Bruker SMART APEX diffractometer	3306 independent reflections
Radiation source: fine-focus sealed tube	3028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.750, T_max = 0.958	k = −11→11
6996 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0585P)² + 0.8764P] where P = (F_o² + 2F_c²)/3
3306 reflections	(Δ/σ)_max < 0.001
238 parameters	Δρ_max = 0.49 e Å⁻³
6 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇F₅O₂)₂·2H₂O	γ = 80.606 (1)°
M_r = 758.08	V = 723.85 (10) Å³
Triclinic, P1	Z = 1
a = 7.1976 (6) Å	Mo Kα radiation
b = 8.7632 (7) Å	µ = 0.87 mm⁻¹
c = 12.1574 (10) Å	T = 100 K
α = 79.378 (1)°	0.35 × 0.15 × 0.05 mm
β = 75.408 (1)°

Data collection top

Bruker SMART APEX diffractometer	3306 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3028 reflections with I > 2σ(I)
T_min = 0.750, T_max = 0.958	R_int = 0.026
6996 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	6 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.49 e Å⁻³
3306 reflections	Δρ_min = −0.75 e Å⁻³
238 parameters

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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.5000	0.5000	0.01239 (13)
F1	0.30292 (19)	1.10724 (17)	0.18468 (12)	0.0207 (3)
F2	0.2995 (2)	1.34413 (17)	0.01066 (13)	0.0238 (3)
F3	−0.0014 (2)	1.41338 (16)	−0.09309 (12)	0.0232 (3)
F4	−0.3014 (2)	1.23540 (18)	−0.02310 (13)	0.0257 (3)
F5	−0.29974 (19)	0.99746 (17)	0.14925 (13)	0.0201 (3)
O1	0.0371 (2)	0.94440 (19)	0.36194 (14)	0.0171 (3)
O2	−0.0383 (3)	0.78296 (19)	0.26114 (14)	0.0185 (4)
O1W	0.1535 (2)	0.4892 (2)	0.59710 (15)	0.0184 (4)
H11	0.095 (4)	0.418 (3)	0.641 (2)	0.027 (8)*
H12	0.059 (3)	0.558 (3)	0.598 (3)	0.030 (9)*
O2W	−0.1025 (2)	0.77849 (19)	0.57103 (14)	0.0149 (3)
H21	−0.057 (4)	0.818 (4)	0.5037 (13)	0.025 (8)*
H22	−0.101 (5)	0.843 (3)	0.613 (3)	0.038 (10)*
N1	0.4818 (3)	0.3368 (2)	0.40734 (15)	0.0101 (3)
H1	0.3625 (19)	0.321 (3)	0.428 (2)	0.018 (7)*
N2	0.4084 (3)	0.6798 (2)	0.38696 (16)	0.0112 (4)
H2	0.2840 (15)	0.687 (3)	0.404 (2)	0.015 (7)*
C1	0.4771 (3)	0.6699 (3)	0.26255 (19)	0.0136 (4)
H1A	0.6192	0.6702	0.2399	0.016*
H1B	0.4176	0.7627	0.2179	0.016*
C2	0.4258 (3)	0.5219 (3)	0.23401 (19)	0.0142 (4)
H2A	0.2861	0.5155	0.2660	0.017*
H2B	0.4499	0.5295	0.1494	0.017*
C3	0.5400 (3)	0.3721 (3)	0.28057 (18)	0.0133 (4)
H3A	0.5188	0.2837	0.2467	0.016*
H3B	0.6798	0.3832	0.2572	0.016*
C4	0.5931 (3)	0.1921 (2)	0.45282 (19)	0.0129 (4)
H4A	0.7335	0.1972	0.4225	0.016*
H4B	0.5591	0.1002	0.4289	0.016*
C5	0.5434 (3)	0.1775 (3)	0.58302 (19)	0.0139 (4)
H5A	0.4041	0.1679	0.6137	0.017*
H5B	0.6190	0.0835	0.6163	0.017*
C6	0.0001 (3)	0.9099 (3)	0.27439 (18)	0.0120 (4)
C7	0.0021 (3)	1.0433 (2)	0.17373 (18)	0.0109 (4)
C8	0.1511 (3)	1.1355 (3)	0.13503 (19)	0.0134 (4)
C9	0.1521 (3)	1.2583 (3)	0.04536 (19)	0.0155 (4)
C10	−0.0004 (4)	1.2919 (3)	−0.00841 (19)	0.0160 (5)
C11	−0.1512 (3)	1.2027 (3)	0.0274 (2)	0.0160 (4)
C12	−0.1483 (3)	1.0797 (3)	0.11656 (19)	0.0133 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0154 (2)	0.0093 (2)	0.0126 (2)	−0.00158 (14)	−0.00413 (14)	−0.00071 (14)
F1	0.0142 (6)	0.0252 (8)	0.0237 (7)	−0.0079 (6)	−0.0080 (6)	0.0036 (6)
F2	0.0242 (7)	0.0200 (7)	0.0245 (8)	−0.0133 (6)	0.0020 (6)	0.0023 (6)
F3	0.0431 (9)	0.0114 (7)	0.0126 (7)	−0.0011 (6)	−0.0065 (6)	0.0031 (5)
F4	0.0268 (8)	0.0269 (8)	0.0255 (8)	0.0027 (6)	−0.0174 (6)	0.0015 (6)
F5	0.0137 (6)	0.0226 (7)	0.0254 (7)	−0.0070 (5)	−0.0070 (5)	0.0008 (6)
O1	0.0234 (8)	0.0172 (8)	0.0119 (7)	−0.0064 (7)	−0.0057 (6)	0.0003 (6)
O2	0.0269 (9)	0.0103 (8)	0.0185 (8)	−0.0056 (6)	−0.0049 (7)	−0.0001 (6)
O1W	0.0117 (8)	0.0138 (8)	0.0253 (9)	−0.0024 (6)	−0.0008 (7)	0.0039 (7)
O2W	0.0165 (8)	0.0135 (8)	0.0143 (8)	−0.0046 (6)	−0.0025 (6)	−0.0002 (6)
N1	0.0088 (8)	0.0090 (8)	0.0124 (9)	−0.0023 (7)	−0.0021 (7)	−0.0011 (7)
N2	0.0096 (8)	0.0100 (8)	0.0136 (9)	−0.0022 (7)	−0.0027 (7)	−0.0001 (7)
C1	0.0153 (10)	0.0117 (10)	0.0132 (10)	−0.0033 (8)	−0.0043 (8)	0.0024 (8)
C2	0.0164 (10)	0.0154 (11)	0.0112 (10)	−0.0042 (8)	−0.0042 (8)	0.0000 (8)
C3	0.0134 (10)	0.0147 (10)	0.0113 (10)	−0.0029 (8)	−0.0005 (8)	−0.0032 (8)
C4	0.0139 (10)	0.0074 (9)	0.0172 (11)	0.0000 (8)	−0.0041 (8)	−0.0014 (8)
C5	0.0161 (10)	0.0089 (10)	0.0174 (11)	−0.0024 (8)	−0.0068 (8)	0.0009 (8)
C6	0.0097 (9)	0.0120 (10)	0.0121 (10)	0.0006 (8)	−0.0009 (8)	−0.0002 (8)
C7	0.0121 (10)	0.0094 (9)	0.0103 (9)	−0.0005 (8)	−0.0013 (8)	−0.0017 (8)
C8	0.0129 (10)	0.0135 (10)	0.0140 (10)	−0.0016 (8)	−0.0031 (8)	−0.0024 (8)
C9	0.0181 (11)	0.0118 (10)	0.0142 (10)	−0.0054 (8)	0.0027 (8)	−0.0013 (8)
C10	0.0266 (12)	0.0089 (10)	0.0093 (10)	0.0007 (9)	−0.0017 (9)	0.0005 (8)
C11	0.0172 (11)	0.0164 (11)	0.0145 (10)	0.0041 (9)	−0.0074 (8)	−0.0031 (8)
C12	0.0133 (10)	0.0129 (10)	0.0143 (10)	−0.0015 (8)	−0.0030 (8)	−0.0037 (8)

Geometric parameters (Å, º) top

Cu1—N1	2.0149 (18)	C1—C2	1.525 (3)
Cu1—N1ⁱ	2.0149 (18)	C1—H1A	0.9900
Cu1—N2	2.0313 (18)	C1—H1B	0.9900
Cu1—N2ⁱ	2.0313 (18)	C2—C3	1.526 (3)
Cu1—O1W	2.4849 (17)	C2—H2A	0.9900
F1—C8	1.345 (3)	C2—H2B	0.9900
F2—C9	1.337 (3)	C3—H3A	0.9900
F3—C10	1.338 (3)	C3—H3B	0.9900
F4—C11	1.340 (3)	C4—C5	1.518 (3)
F5—C12	1.341 (3)	C4—H4A	0.9900
O1—C6	1.258 (3)	C4—H4B	0.9900
O2—C6	1.236 (3)	C5—N2ⁱ	1.479 (3)
O1W—H11	0.834 (10)	C5—H5A	0.9900
O1W—H12	0.832 (10)	C5—H5B	0.9900
O2W—H21	0.833 (10)	C6—C7	1.528 (3)
O2W—H22	0.830 (10)	C7—C8	1.383 (3)
N1—C3	1.479 (3)	C7—C12	1.393 (3)
N1—C4	1.480 (3)	C8—C9	1.383 (3)
N1—H1	0.859 (10)	C9—C10	1.380 (3)
N2—C5ⁱ	1.479 (3)	C10—C11	1.376 (3)
N2—C1	1.482 (3)	C11—C12	1.382 (3)
N2—H2	0.861 (10)

N1—Cu1—N1ⁱ	180.00 (9)	N1—C3—H3A	109.3
N1—Cu1—N2	93.24 (7)	C2—C3—H3A	109.3
N1ⁱ—Cu1—N2	86.76 (7)	N1—C3—H3B	109.3
N1—Cu1—N2ⁱ	86.76 (7)	C2—C3—H3B	109.3
N1ⁱ—Cu1—N2ⁱ	93.24 (7)	H3A—C3—H3B	107.9
N2—Cu1—N2ⁱ	180.0	N1—C4—C5	108.02 (17)
N1—Cu1—O1W	88.91 (7)	N1—C4—H4A	110.1
N1ⁱ—Cu1—O1W	91.09 (7)	C5—C4—H4A	110.1
N2—Cu1—O1W	86.87 (6)	N1—C4—H4B	110.1
N2ⁱ—Cu1—O1W	93.13 (6)	C5—C4—H4B	110.1
Cu1—O1W—H11	132 (2)	H4A—C4—H4B	108.4
Cu1—O1W—H12	131 (2)	N2ⁱ—C5—C4	107.48 (17)
H11—O1W—H12	97 (3)	N2ⁱ—C5—H5A	110.2
H21—O2W—H22	107 (3)	C4—C5—H5A	110.2
C3—N1—C4	111.85 (17)	N2ⁱ—C5—H5B	110.2
C3—N1—Cu1	118.22 (13)	C4—C5—H5B	110.2
C4—N1—Cu1	105.50 (13)	H5A—C5—H5B	108.5
C3—N1—H1	110 (2)	O2—C6—O1	127.9 (2)
C4—N1—H1	106 (2)	O2—C6—C7	117.14 (19)
Cu1—N1—H1	104 (2)	O1—C6—C7	114.94 (19)
C5ⁱ—N2—C1	112.36 (17)	C8—C7—C12	116.3 (2)
C5ⁱ—N2—Cu1	105.50 (13)	C8—C7—C6	122.22 (19)
C1—N2—Cu1	118.01 (14)	C12—C7—C6	121.49 (19)
C5ⁱ—N2—H2	106 (2)	F1—C8—C9	117.3 (2)
C1—N2—H2	108.4 (19)	F1—C8—C7	120.12 (19)
Cu1—N2—H2	105.8 (19)	C9—C8—C7	122.6 (2)
N2—C1—C2	111.28 (17)	F2—C9—C10	120.0 (2)
N2—C1—H1A	109.4	F2—C9—C8	120.5 (2)
C2—C1—H1A	109.4	C10—C9—C8	119.5 (2)
N2—C1—H1B	109.4	F3—C10—C9	119.3 (2)
C2—C1—H1B	109.4	F3—C10—C11	120.9 (2)
H1A—C1—H1B	108.0	C9—C10—C11	119.7 (2)
C3—C2—C1	113.62 (18)	F4—C11—C10	120.3 (2)
C3—C2—H2A	108.8	F4—C11—C12	120.0 (2)
C1—C2—H2A	108.8	C10—C11—C12	119.7 (2)
C3—C2—H2B	108.8	F5—C12—C11	117.48 (19)
C1—C2—H2B	108.8	F5—C12—C7	120.30 (19)
H2A—C2—H2B	107.7	C11—C12—C7	122.2 (2)
N1—C3—C2	111.72 (18)

N2—Cu1—N1—C3	38.53 (15)	C12—C7—C8—F1	−179.30 (19)
N2ⁱ—Cu1—N1—C3	−141.47 (15)	C6—C7—C8—F1	1.4 (3)
O1W—Cu1—N1—C3	125.34 (15)	C12—C7—C8—C9	0.5 (3)
N2—Cu1—N1—C4	164.50 (13)	C6—C7—C8—C9	−178.8 (2)
N2ⁱ—Cu1—N1—C4	−15.50 (13)	F1—C8—C9—F2	0.0 (3)
O1W—Cu1—N1—C4	−108.70 (13)	C7—C8—C9—F2	−179.9 (2)
N1—Cu1—N2—C5ⁱ	−165.17 (14)	F1—C8—C9—C10	180.0 (2)
N1ⁱ—Cu1—N2—C5ⁱ	14.83 (14)	C7—C8—C9—C10	0.1 (4)
O1W—Cu1—N2—C5ⁱ	106.10 (14)	F2—C9—C10—F3	−1.8 (3)
N1—Cu1—N2—C1	−38.68 (15)	C8—C9—C10—F3	178.2 (2)
N1ⁱ—Cu1—N2—C1	141.32 (15)	F2—C9—C10—C11	179.7 (2)
O1W—Cu1—N2—C1	−127.41 (15)	C8—C9—C10—C11	−0.3 (3)
C5ⁱ—N2—C1—C2	179.95 (17)	F3—C10—C11—F4	0.7 (3)
Cu1—N2—C1—C2	56.8 (2)	C9—C10—C11—F4	179.1 (2)
N2—C1—C2—C3	−69.8 (2)	F3—C10—C11—C12	−178.7 (2)
C4—N1—C3—C2	−179.63 (17)	C9—C10—C11—C12	−0.3 (3)
Cu1—N1—C3—C2	−56.8 (2)	F4—C11—C12—F5	−0.2 (3)
C1—C2—C3—N1	69.8 (2)	C10—C11—C12—F5	179.2 (2)
C3—N1—C4—C5	172.46 (17)	F4—C11—C12—C7	−178.4 (2)
Cu1—N1—C4—C5	42.67 (18)	C10—C11—C12—C7	1.0 (4)
N1—C4—C5—N2ⁱ	−58.0 (2)	C8—C7—C12—F5	−179.24 (19)
O2—C6—C7—C8	−132.7 (2)	C6—C7—C12—F5	0.1 (3)
O1—C6—C7—C8	47.8 (3)	C8—C7—C12—C11	−1.1 (3)
O2—C6—C7—C12	48.0 (3)	C6—C7—C12—C11	178.2 (2)
O1—C6—C7—C12	−131.5 (2)

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···O2wⁱⁱ	0.86 (1)	2.17 (2)	2.997 (2)	157 (3)
N2—H2···O1w	0.86 (1)	2.70 (3)	3.123 (2)	112 (2)
O1w—H11···O2ⁱⁱ	0.83 (1)	1.98 (1)	2.785 (2)	162 (3)
O1w—H12···O2w	0.83 (1)	2.10 (2)	2.898 (2)	160 (3)
O2w—H21···O1	0.83 (1)	1.90 (1)	2.723 (2)	169 (3)
O2w—H22···O1ⁱⁱⁱ	0.83 (1)	2.08 (2)	2.842 (2)	152 (4)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₀H₂₄N₄)(H₂O)₂](C₇F₅O₂)₂·2H₂O
M_r	758.08
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.1976 (6), 8.7632 (7), 12.1574 (10)
α, β, γ (°)	79.378 (1), 75.408 (1), 80.606 (1)
V (Å³)	723.85 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.35 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.750, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	6996, 3306, 3028
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.111, 1.06
No. of reflections	3306
No. of parameters	238
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.75

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2wⁱ	0.86 (1)	2.17 (2)	2.997 (2)	157 (3)
N2—H2···O1w	0.86 (1)	2.70 (3)	3.123 (2)	112 (2)
O1w—H11···O2ⁱ	0.83 (1)	1.98 (1)	2.785 (2)	162 (3)
O1w—H12···O2w	0.83 (1)	2.10 (2)	2.898 (2)	160 (3)
O2w—H21···O1	0.83 (1)	1.90 (1)	2.723 (2)	169 (3)
O2w—H22···O1ⁱⁱ	0.83 (1)	2.08 (2)	2.842 (2)	152 (4)

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

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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