metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Di­aqua­(1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N1,N4,N8,N11)copper(II) bis­­(4-methyl­benzoate) monohydrate

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

(Received 30 June 2010; accepted 1 July 2010; online 7 July 2010)

The CuII atom in the title salt, [Cu(C10H24N4)(H2O)2](C8H7O2)2·H2O, 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 of tetra­gonally distorted octa­hedral geometry. The cations, anions and lattice water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds to form a layer structure parallel to (001).

Related literature

For related (1,4,8,11-tetra­aza­cyclo­tetra­deca­ne)copper carboxyl­ates, see: Lindoy et al. (2003[Lindoy, L. F., Mahinay, M. S., Skelton, B. W. & White, A. H. (2003). J. Coord. Chem. 56, 1203-1213.]); Hunter et al. (2005[Hunter, T. M., McNae, I. W., Liang, X., Bella, J., Parsons, S., Walkinshaw, M. D. & Sadler, P. J. (2005). Proc. Natl Acad. Sci. USA, 102, 2288-2292.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C10H24N4)(H2O)2](C8H7O2)2·H2O

  • Mr = 588.19

  • Monoclinic, C 2/c

  • a = 31.925 (3) Å

  • b = 7.1779 (6) Å

  • c = 28.750 (3) Å

  • β = 121.880 (1)°

  • V = 5594.4 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.83 mm−1

  • T = 100 K

  • 0.30 × 0.10 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.789, Tmax = 0.960

  • 26024 measured reflections

  • 6434 independent reflections

  • 4523 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.109

  • S = 1.01

  • 6434 reflections

  • 385 parameters

  • 10 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.53 e Å−3

Table 1
Selected bond lengths (Å)

Cu1—N1 2.025 (2)
Cu1—N2 2.012 (2)
Cu1—N3 2.028 (2)
Cu1—N4 2.010 (2)
Cu1—O1w 2.481 (2)
Cu1—O2w 2.531 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2 0.85 (1) 2.13 (1) 2.971 (3) 167 (3)
N2—H2⋯O1i 0.86 (1) 2.06 (2) 2.847 (3) 151 (3)
N3—H3⋯O3wi 0.86 (1) 2.57 (2) 3.291 (3) 143 (2)
N4—H4⋯O3ii 0.86 (1) 2.14 (2) 2.927 (3) 152 (3)
O1w—H11⋯O1 0.84 (1) 1.95 (1) 2.792 (2) 177 (4)
O1w—H12⋯O3w 0.84 (1) 1.96 (1) 2.795 (3) 173 (3)
O2w—H21⋯O3 0.84 (1) 1.99 (1) 2.825 (3) 173 (3)
O2w—H22⋯O2i 0.84 (1) 1.98 (1) 2.813 (3) 172 (3)
O3w—H31⋯O4iii 0.83 (1) 2.02 (1) 2.835 (3) 166 (4)
OwW—H32⋯O4ii 0.84 (1) 1.85 (1) 2.688 (3) 174 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. ]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. ]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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 to 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(CH3C6H4CO2)-.H2O (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 (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 p-toluate (0.68 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The amino and water H-atoms were located in a difference Fourier map, and were refined isotropically with distance restraints of N–H 0.86±0.01, O–H 0.84±0.01 Å.

Structure description 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 to 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(CH3C6H4CO2)-.H2O (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 (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.

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
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Cu(H2O)2(C10H24N4)]2+ 2(CH3C6H4CO2)-.H2O 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(4-methylbenzoate) monohydrate top
Crystal data top
[Cu(C10H24N4)(H2O)2](C8H7O2)2·H2OF(000) = 2504
Mr = 588.19Dx = 1.397 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3327 reflections
a = 31.925 (3) Åθ = 2.4–28.3°
b = 7.1779 (6) ŵ = 0.83 mm1
c = 28.750 (3) ÅT = 100 K
β = 121.880 (1)°Block, purple
V = 5594.4 (8) Å30.30 × 0.10 × 0.05 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
6434 independent reflections
Radiation source: fine-focus sealed tube4523 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3941
Tmin = 0.789, Tmax = 0.960k = 89
26024 measured reflectionsl = 3737
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0467P)2 + 3.0196P]
where P = (Fo2 + 2Fc2)/3
6434 reflections(Δ/σ)max = 0.002
385 parametersΔρmax = 0.37 e Å3
10 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Cu(C10H24N4)(H2O)2](C8H7O2)2·H2OV = 5594.4 (8) Å3
Mr = 588.19Z = 8
Monoclinic, C2/cMo Kα radiation
a = 31.925 (3) ŵ = 0.83 mm1
b = 7.1779 (6) ÅT = 100 K
c = 28.750 (3) Å0.30 × 0.10 × 0.05 mm
β = 121.880 (1)°
Data collection top
Bruker SMART APEX
diffractometer
6434 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4523 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 0.960Rint = 0.073
26024 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04210 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.37 e Å3
6434 reflectionsΔρmin = 0.53 e Å3
385 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
xyzUiso*/Ueq
Cu10.412658 (11)0.34713 (4)0.559593 (12)0.01501 (10)
O10.47818 (6)0.1771 (2)0.66496 (7)0.0174 (4)
O20.50203 (6)0.1284 (2)0.60553 (7)0.0182 (4)
O30.33915 (6)0.8743 (2)0.44684 (7)0.0221 (4)
O1W0.39877 (7)0.0374 (3)0.58743 (8)0.0204 (4)
O2W0.42053 (7)0.6641 (3)0.52635 (8)0.0220 (4)
O3W0.30940 (8)0.1475 (3)0.54990 (8)0.0291 (5)
O40.27168 (7)0.7719 (3)0.44369 (7)0.0249 (4)
N10.47989 (8)0.2709 (3)0.57497 (8)0.0159 (5)
H10.4817 (10)0.1556 (16)0.5829 (11)0.016 (7)*
N20.44938 (8)0.4440 (3)0.63695 (8)0.0164 (5)
H20.4495 (10)0.5631 (15)0.6338 (11)0.024 (8)*
N30.34589 (8)0.4280 (3)0.54508 (9)0.0185 (5)
H30.3441 (10)0.5449 (16)0.5386 (11)0.020 (8)*
N40.37563 (8)0.2541 (3)0.48193 (8)0.0174 (5)
H40.3719 (11)0.1360 (16)0.4836 (12)0.031 (9)*
C10.51636 (9)0.3789 (4)0.62349 (10)0.0187 (6)
H1A0.51770.50890.61280.022*
H1B0.54950.32290.63970.022*
C20.50050 (9)0.3757 (4)0.66449 (10)0.0204 (6)
H2A0.50250.24720.67800.024*
H2B0.52240.45640.69610.024*
C30.42706 (10)0.4097 (4)0.66988 (11)0.0228 (6)
H3A0.44820.46580.70660.027*
H3B0.42560.27370.67470.027*
C40.37544 (10)0.4909 (4)0.64307 (12)0.0272 (7)
H4A0.36450.48320.66950.033*
H4B0.37700.62450.63560.033*
C50.33683 (10)0.3979 (4)0.59015 (12)0.0248 (6)
H5A0.33670.26250.59650.030*
H5B0.30390.44780.57900.030*
C60.30837 (9)0.3366 (4)0.49338 (11)0.0231 (6)
H6A0.27650.40310.47730.028*
H6B0.30340.20620.50060.028*
C70.32624 (9)0.3411 (4)0.45436 (10)0.0222 (6)
H7A0.30320.27170.42050.027*
H7B0.32810.47130.44430.027*
C80.39989 (10)0.2750 (4)0.45028 (10)0.0218 (6)
H8A0.40300.40930.44470.026*
H8B0.37890.21730.41380.026*
C90.45044 (11)0.1862 (4)0.47853 (11)0.0248 (6)
H9A0.46180.18040.45250.030*
H9B0.44800.05690.48880.030*
C100.48843 (10)0.2908 (4)0.52945 (11)0.0232 (6)
H10A0.52170.24320.54130.028*
H10B0.48740.42450.52050.028*
C110.50985 (9)0.1325 (3)0.65344 (10)0.0150 (5)
C120.56003 (9)0.0723 (4)0.70001 (10)0.0146 (5)
C130.57185 (9)0.0785 (4)0.75417 (10)0.0166 (5)
H130.54860.12590.76230.020*
C140.61733 (9)0.0159 (4)0.79610 (10)0.0164 (5)
H140.62530.02470.83290.020*
C150.65166 (9)0.0597 (4)0.78562 (10)0.0170 (5)
C160.63953 (9)0.0675 (4)0.73143 (10)0.0173 (5)
H160.66230.11980.72330.021*
C170.59464 (9)0.0000 (4)0.68914 (10)0.0166 (5)
H170.58740.00300.65260.020*
C180.70144 (9)0.1270 (4)0.83133 (10)0.0207 (6)
H18A0.72720.07880.82580.031*
H18B0.70730.08230.86650.031*
H18C0.70210.26350.83140.031*
C190.29372 (10)0.8409 (4)0.42210 (10)0.0194 (6)
C200.26273 (9)0.8875 (3)0.36134 (11)0.0177 (6)
C210.28361 (9)0.9741 (4)0.33499 (10)0.0182 (6)
H21A0.31771.00480.35510.022*
C220.25492 (10)1.0159 (4)0.27958 (11)0.0210 (6)
H22A0.26951.07820.26240.025*
C230.20511 (10)0.9682 (4)0.24858 (10)0.0193 (6)
C240.18443 (10)0.8818 (4)0.27541 (11)0.0197 (6)
H240.15050.84890.25540.024*
C250.21318 (9)0.8438 (4)0.33112 (10)0.0183 (5)
H250.19840.78650.34880.022*
C260.17495 (11)1.0007 (4)0.18760 (11)0.0268 (7)
H26A0.13991.00420.17520.040*
H26B0.18090.89950.16890.040*
H26C0.18451.11970.17910.040*
H110.4219 (9)0.029 (4)0.6111 (11)0.052 (11)*
H120.3716 (7)0.018 (5)0.5734 (13)0.057 (12)*
H210.3952 (7)0.724 (4)0.5043 (10)0.036 (10)*
H220.4431 (9)0.736 (4)0.5482 (11)0.036 (10)*
H310.2885 (11)0.178 (5)0.5575 (15)0.062 (13)*
H320.2992 (11)0.168 (5)0.5169 (5)0.038 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01367 (16)0.01757 (17)0.01320 (15)0.00050 (13)0.00669 (12)0.00049 (13)
O10.0142 (9)0.0203 (10)0.0183 (9)0.0012 (7)0.0089 (8)0.0002 (7)
O20.0184 (9)0.0215 (10)0.0138 (8)0.0010 (8)0.0078 (7)0.0007 (7)
O30.0153 (9)0.0199 (10)0.0230 (10)0.0016 (8)0.0047 (8)0.0001 (8)
O1W0.0165 (10)0.0175 (10)0.0236 (10)0.0018 (8)0.0081 (9)0.0044 (8)
O2W0.0203 (10)0.0178 (10)0.0195 (10)0.0016 (9)0.0048 (9)0.0017 (8)
O3W0.0240 (11)0.0426 (13)0.0185 (10)0.0106 (10)0.0098 (9)0.0009 (10)
O40.0256 (10)0.0320 (12)0.0197 (9)0.0064 (9)0.0139 (9)0.0013 (8)
N10.0176 (11)0.0144 (12)0.0166 (11)0.0013 (9)0.0097 (9)0.0025 (9)
N20.0186 (11)0.0147 (12)0.0171 (11)0.0002 (9)0.0102 (9)0.0011 (9)
N30.0183 (11)0.0150 (12)0.0233 (12)0.0010 (9)0.0117 (10)0.0010 (9)
N40.0198 (11)0.0130 (12)0.0158 (11)0.0008 (9)0.0069 (9)0.0015 (9)
C10.0145 (12)0.0175 (14)0.0219 (13)0.0004 (10)0.0080 (11)0.0005 (10)
C20.0177 (13)0.0223 (15)0.0148 (12)0.0025 (11)0.0043 (11)0.0005 (10)
C30.0306 (15)0.0239 (15)0.0188 (13)0.0005 (12)0.0165 (12)0.0014 (11)
C40.0317 (16)0.0285 (17)0.0326 (16)0.0015 (13)0.0246 (14)0.0052 (13)
C50.0255 (15)0.0229 (15)0.0347 (16)0.0007 (12)0.0219 (13)0.0012 (12)
C60.0148 (13)0.0184 (14)0.0266 (14)0.0008 (11)0.0044 (11)0.0027 (12)
C70.0188 (13)0.0207 (14)0.0189 (13)0.0020 (12)0.0043 (11)0.0030 (11)
C80.0288 (15)0.0230 (15)0.0140 (12)0.0003 (12)0.0115 (12)0.0010 (11)
C90.0373 (17)0.0242 (16)0.0240 (14)0.0029 (13)0.0238 (13)0.0030 (12)
C100.0249 (14)0.0270 (16)0.0256 (14)0.0005 (12)0.0188 (12)0.0017 (12)
C110.0164 (12)0.0108 (12)0.0171 (12)0.0036 (10)0.0085 (10)0.0013 (10)
C120.0154 (12)0.0117 (12)0.0171 (12)0.0015 (10)0.0087 (10)0.0002 (10)
C130.0156 (12)0.0159 (13)0.0193 (13)0.0011 (10)0.0100 (11)0.0015 (10)
C140.0189 (13)0.0161 (13)0.0138 (12)0.0008 (10)0.0084 (10)0.0021 (10)
C150.0161 (12)0.0120 (13)0.0216 (13)0.0013 (10)0.0091 (11)0.0026 (10)
C160.0135 (12)0.0173 (13)0.0212 (13)0.0003 (10)0.0093 (11)0.0029 (11)
C170.0169 (13)0.0169 (13)0.0164 (12)0.0021 (10)0.0090 (10)0.0035 (10)
C180.0165 (13)0.0221 (15)0.0202 (13)0.0012 (11)0.0073 (11)0.0010 (11)
C190.0217 (13)0.0153 (13)0.0214 (13)0.0021 (11)0.0115 (11)0.0037 (11)
C200.0201 (13)0.0141 (13)0.0208 (13)0.0013 (10)0.0120 (11)0.0017 (10)
C210.0180 (13)0.0154 (14)0.0239 (13)0.0015 (10)0.0129 (11)0.0030 (11)
C220.0251 (14)0.0182 (14)0.0250 (14)0.0009 (11)0.0168 (12)0.0003 (11)
C230.0234 (14)0.0155 (13)0.0185 (13)0.0027 (11)0.0107 (11)0.0029 (10)
C240.0170 (13)0.0189 (14)0.0226 (14)0.0014 (11)0.0101 (11)0.0042 (11)
C250.0206 (13)0.0140 (13)0.0230 (13)0.0018 (11)0.0134 (11)0.0028 (11)
C260.0311 (16)0.0298 (17)0.0204 (14)0.0000 (13)0.0142 (13)0.0000 (12)
Geometric parameters (Å, º) top
Cu1—N12.025 (2)C6—H6A0.9900
Cu1—N22.012 (2)C6—H6B0.9900
Cu1—N32.028 (2)C7—H7A0.9900
Cu1—N42.010 (2)C7—H7B0.9900
Cu1—O1w2.481 (2)C8—C91.512 (4)
Cu1—O2w2.531 (2)C8—H8A0.9900
O1—C111.260 (3)C8—H8B0.9900
O2—C111.264 (3)C9—C101.517 (4)
O3—C191.256 (3)C9—H9A0.9900
O1W—H110.841 (10)C9—H9B0.9900
O1W—H120.839 (10)C10—H10A0.9900
O2W—H210.838 (10)C10—H10B0.9900
O2W—H220.837 (10)C11—C121.510 (3)
O3W—H310.833 (10)C12—C131.396 (3)
O3W—H320.838 (10)C12—C171.397 (3)
O4—C191.260 (3)C13—C141.384 (3)
N1—C101.478 (3)C13—H130.9500
N1—C11.479 (3)C14—C151.391 (4)
N1—H10.852 (10)C14—H140.9500
N2—C21.472 (3)C15—C161.394 (3)
N2—C31.476 (3)C15—C181.510 (3)
N2—H20.860 (10)C16—C171.388 (3)
N3—C61.481 (3)C16—H160.9500
N3—C51.485 (3)C17—H170.9500
N3—H30.855 (10)C18—H18A0.9800
N4—C71.478 (3)C18—H18B0.9800
N4—C81.482 (3)C18—H18C0.9800
N4—H40.861 (10)C19—C201.522 (4)
C1—C21.509 (4)C20—C251.380 (3)
C1—H1A0.9900C20—C211.392 (4)
C1—H1B0.9900C21—C221.388 (4)
C2—H2A0.9900C21—H21A0.9500
C2—H2B0.9900C22—C231.394 (4)
C3—C41.519 (4)C22—H22A0.9500
C3—H3A0.9900C23—C241.398 (4)
C3—H3B0.9900C23—C261.507 (3)
C4—C51.516 (4)C24—C251.389 (4)
C4—H4A0.9900C24—H240.9500
C4—H4B0.9900C25—H250.9500
C5—H5A0.9900C26—H26A0.9800
C5—H5B0.9900C26—H26B0.9800
C6—C71.504 (4)C26—H26C0.9800
N4—Cu1—N2179.18 (10)C7—C6—H6B110.0
N4—Cu1—N194.96 (9)H6A—C6—H6B108.4
N2—Cu1—N185.44 (9)N4—C7—C6108.0 (2)
N4—Cu1—N385.92 (9)N4—C7—H7A110.1
N2—Cu1—N393.67 (9)C6—C7—H7A110.1
N1—Cu1—N3178.90 (10)N4—C7—H7B110.1
N4—Cu1—O1W87.71 (8)C6—C7—H7B110.1
N2—Cu1—O1W93.00 (8)H7A—C7—H7B108.4
N1—Cu1—O1W92.10 (8)N4—C8—C9112.5 (2)
N3—Cu1—O1W88.59 (8)N4—C8—H8A109.1
N4—Cu1—O2W89.81 (8)C9—C8—H8A109.1
N2—Cu1—O2W89.46 (8)N4—C8—H8B109.1
N1—Cu1—O2W91.16 (8)C9—C8—H8B109.1
N3—Cu1—O2W88.18 (8)H8A—C8—H8B107.8
O1W—Cu1—O2W176.06 (6)C8—C9—C10113.1 (2)
Cu1—O1W—H11123 (3)C8—C9—H9A109.0
Cu1—O1W—H12126 (3)C10—C9—H9A109.0
H11—O1W—H12111 (4)C8—C9—H9B109.0
Cu1—O2W—H21120 (2)C10—C9—H9B109.0
Cu1—O2W—H22119 (2)H9A—C9—H9B107.8
H21—O2W—H22111 (3)N1—C10—C9112.3 (2)
H31—O3W—H32112 (3)N1—C10—H10A109.1
C10—N1—C1111.3 (2)C9—C10—H10A109.1
C10—N1—Cu1116.79 (16)N1—C10—H10B109.1
C1—N1—Cu1106.24 (15)C9—C10—H10B109.1
C10—N1—H1108.2 (19)H10A—C10—H10B107.9
C1—N1—H1110.4 (18)O1—C11—O2124.6 (2)
Cu1—N1—H1103.6 (19)O1—C11—C12117.6 (2)
C2—N2—C3111.9 (2)O2—C11—C12117.8 (2)
C2—N2—Cu1108.23 (16)C13—C12—C17118.8 (2)
C3—N2—Cu1117.02 (16)C13—C12—C11121.0 (2)
C2—N2—H2108.9 (19)C17—C12—C11120.1 (2)
C3—N2—H2105.3 (19)C14—C13—C12120.2 (2)
Cu1—N2—H2105.0 (19)C14—C13—H13119.9
C6—N3—C5112.6 (2)C12—C13—H13119.9
C6—N3—Cu1106.55 (16)C13—C14—C15121.5 (2)
C5—N3—Cu1116.53 (17)C13—C14—H14119.3
C6—N3—H3106.9 (19)C15—C14—H14119.3
C5—N3—H3108.2 (19)C14—C15—C16118.2 (2)
Cu1—N3—H3105.4 (19)C14—C15—C18121.6 (2)
C7—N4—C8112.5 (2)C16—C15—C18120.2 (2)
C7—N4—Cu1106.88 (16)C17—C16—C15120.9 (2)
C8—N4—Cu1117.20 (16)C17—C16—H16119.5
C7—N4—H4108 (2)C15—C16—H16119.5
C8—N4—H4105 (2)C16—C17—C12120.4 (2)
Cu1—N4—H4107 (2)C16—C17—H17119.8
N1—C1—C2107.9 (2)C12—C17—H17119.8
N1—C1—H1A110.1C15—C18—H18A109.5
C2—C1—H1A110.1C15—C18—H18B109.5
N1—C1—H1B110.1H18A—C18—H18B109.5
C2—C1—H1B110.1C15—C18—H18C109.5
H1A—C1—H1B108.4H18A—C18—H18C109.5
N2—C2—C1108.0 (2)H18B—C18—H18C109.5
N2—C2—H2A110.1O3—C19—O4125.1 (2)
C1—C2—H2A110.1O3—C19—C20117.7 (2)
N2—C2—H2B110.1O4—C19—C20117.3 (2)
C1—C2—H2B110.1C25—C20—C21118.5 (2)
H2A—C2—H2B108.4C25—C20—C19120.5 (2)
N2—C3—C4111.9 (2)C21—C20—C19121.0 (2)
N2—C3—H3A109.2C22—C21—C20120.4 (2)
C4—C3—H3A109.2C22—C21—H21A119.8
N2—C3—H3B109.2C20—C21—H21A119.8
C4—C3—H3B109.2C21—C22—C23121.3 (3)
H3A—C3—H3B107.9C21—C22—H22A119.4
C5—C4—C3115.4 (2)C23—C22—H22A119.4
C5—C4—H4A108.4C22—C23—C24117.9 (2)
C3—C4—H4A108.4C22—C23—C26121.2 (2)
C5—C4—H4B108.4C24—C23—C26120.9 (2)
C3—C4—H4B108.4C25—C24—C23120.4 (2)
H4A—C4—H4B107.5C25—C24—H24119.8
N3—C5—C4112.5 (2)C23—C24—H24119.8
N3—C5—H5A109.1C20—C25—C24121.4 (2)
C4—C5—H5A109.1C20—C25—H25119.3
N3—C5—H5B109.1C24—C25—H25119.3
C4—C5—H5B109.1C23—C26—H26A109.5
H5A—C5—H5B107.8C23—C26—H26B109.5
N3—C6—C7108.3 (2)H26A—C26—H26B109.5
N3—C6—H6A110.0C23—C26—H26C109.5
C7—C6—H6A110.0H26A—C26—H26C109.5
N3—C6—H6B110.0H26B—C26—H26C109.5
N4—Cu1—N1—C1036.50 (19)Cu1—N3—C5—C456.2 (3)
N2—Cu1—N1—C10142.78 (19)C3—C4—C5—N367.2 (3)
O1W—Cu1—N1—C10124.38 (18)C5—N3—C6—C7168.5 (2)
O2W—Cu1—N1—C1053.41 (19)Cu1—N3—C6—C739.5 (2)
N4—Cu1—N1—C1161.28 (16)C8—N4—C7—C6171.8 (2)
N2—Cu1—N1—C117.99 (16)Cu1—N4—C7—C641.8 (2)
O1W—Cu1—N1—C1110.83 (16)N3—C6—C7—N455.1 (3)
O2W—Cu1—N1—C171.37 (16)C7—N4—C8—C9179.9 (2)
N1—Cu1—N2—C211.11 (17)Cu1—N4—C8—C955.4 (3)
N3—Cu1—N2—C2169.54 (17)N4—C8—C9—C1070.6 (3)
O1W—Cu1—N2—C280.77 (17)C1—N1—C10—C9178.1 (2)
O2W—Cu1—N2—C2102.31 (17)Cu1—N1—C10—C955.9 (3)
N1—Cu1—N2—C3138.62 (19)C8—C9—C10—N171.1 (3)
N3—Cu1—N2—C342.03 (19)O1—C11—C12—C134.4 (4)
O1W—Cu1—N2—C346.75 (19)O2—C11—C12—C13178.0 (2)
O2W—Cu1—N2—C3130.17 (18)O1—C11—C12—C17172.3 (2)
N4—Cu1—N3—C613.16 (17)O2—C11—C12—C175.3 (4)
N2—Cu1—N3—C6167.56 (17)C17—C12—C13—C140.7 (4)
O1W—Cu1—N3—C674.65 (17)C11—C12—C13—C14177.5 (2)
O2W—Cu1—N3—C6103.09 (17)C12—C13—C14—C152.0 (4)
N4—Cu1—N3—C5139.77 (19)C13—C14—C15—C161.3 (4)
N2—Cu1—N3—C540.95 (19)C13—C14—C15—C18179.6 (2)
O1W—Cu1—N3—C551.96 (18)C14—C15—C16—C170.7 (4)
O2W—Cu1—N3—C5130.29 (18)C18—C15—C16—C17177.6 (2)
N1—Cu1—N4—C7163.46 (17)C15—C16—C17—C121.9 (4)
N3—Cu1—N4—C715.88 (17)C13—C12—C17—C161.2 (4)
O1W—Cu1—N4—C7104.62 (16)C11—C12—C17—C16175.5 (2)
O2W—Cu1—N4—C772.32 (16)O3—C19—C20—C25176.1 (2)
N1—Cu1—N4—C836.14 (19)O4—C19—C20—C254.0 (4)
N3—Cu1—N4—C8143.20 (19)O3—C19—C20—C213.7 (4)
O1W—Cu1—N4—C8128.05 (18)O4—C19—C20—C21176.2 (2)
O2W—Cu1—N4—C855.01 (18)C25—C20—C21—C220.3 (4)
C10—N1—C1—C2171.4 (2)C19—C20—C21—C22180.0 (2)
Cu1—N1—C1—C243.2 (2)C20—C21—C22—C231.8 (4)
C3—N2—C2—C1168.1 (2)C21—C22—C23—C242.0 (4)
Cu1—N2—C2—C137.7 (2)C21—C22—C23—C26175.4 (2)
N1—C1—C2—N254.6 (3)C22—C23—C24—C250.7 (4)
C2—N2—C3—C4176.4 (2)C26—C23—C24—C25176.7 (2)
Cu1—N2—C3—C457.9 (3)C21—C20—C25—C241.0 (4)
N2—C3—C4—C567.7 (3)C19—C20—C25—C24178.7 (2)
C6—N3—C5—C4179.8 (2)C23—C24—C25—C200.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.85 (1)2.13 (1)2.971 (3)167 (3)
N2—H2···O1i0.86 (1)2.06 (2)2.847 (3)151 (3)
N3—H3···O3wi0.86 (1)2.57 (2)3.291 (3)143 (2)
N4—H4···O3ii0.86 (1)2.14 (2)2.927 (3)152 (3)
O1w—H11···O10.84 (1)1.95 (1)2.792 (2)177 (4)
O1w—H12···O3w0.84 (1)1.96 (1)2.795 (3)173 (3)
O2w—H21···O30.84 (1)1.99 (1)2.825 (3)173 (3)
O2w—H22···O2i0.84 (1)1.98 (1)2.813 (3)172 (3)
O3w—H31···O4iii0.83 (1)2.02 (1)2.835 (3)166 (4)
OwW—H32···O4ii0.84 (1)1.85 (1)2.688 (3)174 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C10H24N4)(H2O)2](C8H7O2)2·H2O
Mr588.19
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)31.925 (3), 7.1779 (6), 28.750 (3)
β (°) 121.880 (1)
V3)5594.4 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.83
Crystal size (mm)0.30 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.789, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
26024, 6434, 4523
Rint0.073
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.109, 1.01
No. of reflections6434
No. of parameters385
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.53

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—N12.025 (2)Cu1—N42.010 (2)
Cu1—N22.012 (2)Cu1—O1w2.481 (2)
Cu1—N32.028 (2)Cu1—O2w2.531 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.85 (1)2.13 (1)2.971 (3)167 (3)
N2—H2···O1i0.86 (1)2.06 (2)2.847 (3)151 (3)
N3—H3···O3wi0.86 (1)2.57 (2)3.291 (3)143 (2)
N4—H4···O3ii0.86 (1)2.14 (2)2.927 (3)152 (3)
O1w—H11···O10.84 (1)1.95 (1)2.792 (2)177 (4)
O1w—H12···O3w0.84 (1)1.96 (1)2.795 (3)173 (3)
O2w—H21···O30.84 (1)1.99 (1)2.825 (3)173 (3)
O2w—H22···O2i0.84 (1)1.98 (1)2.813 (3)172 (3)
O3w—H31···O4iii0.83 (1)2.02 (1)2.835 (3)166 (4)
OwW—H32···O4ii0.84 (1)1.85 (1)2.688 (3)174 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1/2, y+1/2, z+1.
 

Acknowledgements

The authors thank the University of Malaya (grant No. RG039/09SUS) and the Ministry of Higher Education (grant No. FP017/2009) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHunter, T. M., McNae, I. W., Liang, X., Bella, J., Parsons, S., Walkinshaw, M. D. & Sadler, P. J. (2005). Proc. Natl Acad. Sci. USA, 102, 2288–2292.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationLindoy, L. F., Mahinay, M. S., Skelton, B. W. & White, A. H. (2003). J. Coord. Chem. 56, 1203–1213.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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