Aqua­[bis­(2-ethyl-5-methyl-1H-imidazol-4-yl-κN3)methane]­oxalatocopper(II) dihydrate

Luo, Y.-H.; Qian, X.-M.; Gao, G.; Li, J.-F.; Mao, S.-L.

doi:10.1107/S1600536811001012

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m172

doi:10.1107/S1600536811001012

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Aqua[bis(2-ethyl-5-methyl-1H-imidazol-4-yl-κN³)methane]oxalatocopper(II) dihydrate

Yang-Hui Luo,^a ^* Xiao-Min Qian,^a Ge Gao,^a Jin-Feng Li ^a and Shu-Lin Mao ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 30 December 2010; accepted 7 January 2011; online 15 January 2011)

In the title compound, [Cu(C₂O₄)(C₁₃H₂₀N₄)(H₂O)]·2H₂O, the Cu^II atom exhibits a distorted square-pyramidal geometry with the two N atoms of the imidazole ligand and the two O atoms of the oxalate ligand forming the basal plane, while the O atom of the coordinated water molecule is in an apical position. The Cu^II atom is shifted 0.232 (2) Å out of the basal plane toward the water molecule. The asymmetric unit is completed by two solvent water molecules. These water molecules participate in the formation of an intricate three-dimensionnal network of hydrogen bonds involving the coordinated water molecule and the NH groups.

Related literature

For the chemical properties of imidazole derivatives, see: Bouwman et al. (2000 ). For synthesis, see: Delgado et al. (2008 ). For related structures, see: Beznischenko et al. (2007 ); Pajunen (1981 ).

Experimental

Crystal data

[Cu(C₂O₄)(C₁₃H₂₀N₄)(H₂O)]·2H₂O
M_r = 437.94
Monoclinic, P 2₁ /c
a = 12.1711 (13) Å
b = 23.167 (2) Å
c = 7.4400 (8) Å
β = 107.304 (1)°
V = 2002.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 298 K
0.35 × 0.18 × 0.12 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.693, T_max = 0.876
10119 measured reflections
3528 independent reflections
1958 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.092
S = 0.81
3528 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4ⁱ	0.85	2.58	3.177 (4)	128
O5—H52⋯O4ⁱⁱ	0.85	1.90	2.748 (4)	174
N2—H2⋯O2ⁱⁱⁱ	0.86	2.09	2.943 (4)	171
N4—H4⋯O7	0.86	2.03	2.847 (4)	158
O6—H6F⋯O5^iv	0.85	2.50	3.259 (4)	149
O6—H6G⋯O4^v	0.85	2.30	3.057 (5)	148
O7—H7C⋯O3^vi	0.85	2.03	2.882 (4)	178
O7—H7D⋯O6	0.85	1.97	2.818 (4)	177
Symmetry codes: (i) x, y, z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001012/dn2649sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001012/dn2649Isup2.hkl

checkCIF report

Comment top

Imidazole derivatives are versatile ligands towards transition metal ions both in man-made and natural systems. They are not only used for catalytic and biocatalysts but also for dioxygen transport and electron storage (Bouwman et al., 2000). As part of our interest in imidazole derivatives, we report here the crystal structure of a new copper complex.

The structure around Cu^II is best decribed as distorted square pyramid environnement with the two N atoms of the imidazole ligand and the two O atoms of the oxalate forming the basal plane whereas the oxygen atom of the coordinated water molecule is in apical position. As expected, the copper atom is shifted ca 0.232 (2)Å out of the basal plane toward the water molecule. The asymmetric unit is completed by two solvate water molecules. The distances and angles within the square pyramid framework agree with related structures (Beznischenko et al., 2007); Pajunen, 1981).

These water molecules participate to the formation of an intricated hydrogen bonds resulting in three dimensionnal network involving the coordinated water molecule and the NH groups (Table 1, Fig. 2).

Related literature top

For the chemical properties of imidazole derivatives, see: Bouwman et al. (2000). For synthesis, see: Delgado et al. (2008). For related structures, see: Beznischenko et al. (2007); Pajunen (1981)

Experimental top

Crystals of the title compound were synthesized by the reaction between copper(II) nitrate trihydrate, potassium oxalate and 4,4'-methanediylbis(2-ethyl-5-methyl-1H-imidazole) ligand. Copper salt and oxalate chemicals used (reagent grade) were commercially available, the 4,4'-methanediylbis(2-ethyl-5-methyl-1H-imidazole) ligand was synthesized as described below . 0.2 mmol(48.4 mg) solid copper(II) nitrate trihydrate was added to a 15 ml aqueous solution of 0.1 mmol(16.6 mg) potassium oxalate under continuous stirring. The suspension was heated at 40–50 °C during 1 h. Then this suspension was mixed with a 5 ml EtOH solution of 0.1 mmol(23.2mg)4,4'-methanediylbis(2-ethyl-5-methyl-1H-imidazole). Finally, the blue solution which results from the mixture was filtered off and allowed to evaporate at room temperature(Delgado, et al.,2008). Single crystals of the title compound as blue prisms were grown from the solution by slow evaporation at room temperature within a few days.

The ligand 4,4'-methanediylbis(2-ethyl-5-methyl-1H-imidazole) was synthesized as follows: 4.35 g (30 mmol) 2-ethyl-5-methylimidazole was added to a solution of 1.5 g (15 mmol)glycine (40% in H₂O). This suspension was vigorously stirred, and 3.1 g (30 mmol) formaldehyde (37% in H₂O) was added dropwise. The resulting turbid mixture was made alkaline with a concentrated sodium hydroxide solution until a pH of 12 was reached(Bouwman, et al.,2000). The reaction mixture was stirred for 8 days at room temperature in a closed vessel. During which time a white solid formed. The white solid was collected by filtration, washed with acetonitrile and diethyl ether, and air-dry at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A packing view down the a axis showing the three dimensionnal network. Hydrogen bonds are shown as dashed lines. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

Aqua[bis(2-ethyl-5-methyl-1H-imidazol-4-yl- κN³)methane]oxalatocopper(II) dihydrate top

Crystal data top

[Cu(C₂O₄)(C₁₃H₂₀N₄)(H₂O)]·2H₂O	F(000) = 916
M_r = 437.94	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1383 reflections
a = 12.1711 (13) Å	θ = 3.0–26.0°
b = 23.167 (2) Å	µ = 1.13 mm⁻¹
c = 7.4400 (8) Å	T = 298 K
β = 107.304 (1)°	Prism, blue
V = 2002.9 (4) Å³	0.35 × 0.18 × 0.12 mm
Z = 4

Data collection top

Rigaku MODEL? CCD area-detector diffractometer	3528 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 8.192 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −27→21
T_min = 0.693, T_max = 0.876	l = −8→8
10119 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0336P)²] where P = (F_o² + 2F_c²)/3
3528 reflections	(Δ/σ)_max = 0.003
248 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₂O₄)(C₁₃H₂₀N₄)(H₂O)]·2H₂O	V = 2002.9 (4) Å³
M_r = 437.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1711 (13) Å	µ = 1.13 mm⁻¹
b = 23.167 (2) Å	T = 298 K
c = 7.4400 (8) Å	0.35 × 0.18 × 0.12 mm
β = 107.304 (1)°

Data collection top

Rigaku MODEL? CCD area-detector diffractometer	3528 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1958 reflections with I > 2σ(I)
T_min = 0.693, T_max = 0.876	R_int = 0.071
10119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 0.81	Δρ_max = 0.34 e Å⁻³
3528 reflections	Δρ_min = −0.31 e Å⁻³
248 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Cu1	0.76270 (4)	0.413233 (19)	0.51168 (7)	0.03980 (17)
O1	0.7228 (2)	0.49415 (10)	0.4554 (4)	0.0521 (8)
O2	0.7628 (2)	0.56946 (12)	0.2999 (4)	0.0607 (9)
O3	0.8807 (2)	0.43059 (12)	0.3849 (4)	0.0489 (8)
O4	0.9308 (3)	0.50045 (13)	0.2201 (5)	0.0744 (11)
O5	0.8745 (2)	0.44573 (12)	0.8111 (4)	0.0598 (8)
H51	0.8928	0.4356	0.9259	0.090*
H52	0.9316	0.4637	0.7948	0.090*
N1	0.6093 (2)	0.39498 (13)	0.5450 (4)	0.0350 (8)
N2	0.4439 (3)	0.39461 (14)	0.6014 (5)	0.0454 (9)
H2	0.3882	0.4056	0.6423	0.055*
N3	0.8036 (3)	0.33050 (12)	0.5306 (5)	0.0392 (8)
N4	0.8869 (3)	0.24674 (13)	0.5968 (5)	0.0435 (9)
H4	0.9396	0.2212	0.6395	0.052*
C1	0.5428 (3)	0.42338 (16)	0.6240 (5)	0.0355 (10)
C2	0.4464 (3)	0.34484 (17)	0.5008 (6)	0.0455 (11)
C3	0.5486 (3)	0.34484 (16)	0.4666 (6)	0.0365 (10)
C4	0.5695 (3)	0.47801 (16)	0.7361 (6)	0.0441 (11)
H4A	0.6252	0.5000	0.6946	0.053*
H4B	0.4998	0.5009	0.7111	0.053*
C5	0.6159 (4)	0.46803 (18)	0.9430 (7)	0.0665 (14)
H5A	0.6874	0.4474	0.9698	0.100*
H5B	0.5617	0.4458	0.9850	0.100*
H5C	0.6284	0.5045	1.0073	0.100*
C6	0.3461 (3)	0.30308 (19)	0.4455 (7)	0.0729 (16)
H6A	0.3218	0.2942	0.5538	0.109*
H6B	0.3696	0.2683	0.3973	0.109*
H6C	0.2835	0.3203	0.3503	0.109*
C7	0.9028 (3)	0.30417 (17)	0.6091 (6)	0.0403 (10)
C8	0.7732 (4)	0.23503 (16)	0.5055 (6)	0.0417 (11)
C9	0.7212 (3)	0.28746 (16)	0.4628 (6)	0.0385 (10)
C10	1.0158 (3)	0.33196 (18)	0.7043 (7)	0.0669 (15)
H10A	1.0293	0.3614	0.6207	0.080*
H10B	1.0092	0.3514	0.8161	0.080*
C11	1.1157 (4)	0.2954 (2)	0.7594 (10)	0.116 (3)
H11A	1.1282	0.2785	0.6494	0.173*
H11B	1.1038	0.2654	0.8408	0.173*
H11C	1.1816	0.3180	0.8248	0.173*
C12	0.7272 (3)	0.17517 (16)	0.4687 (6)	0.0559 (13)
H12A	0.6454	0.1766	0.4111	0.084*
H12B	0.7438	0.1544	0.5854	0.084*
H12C	0.7626	0.1560	0.3860	0.084*
C13	0.5996 (3)	0.30202 (16)	0.3626 (6)	0.0450 (11)
H13A	0.5540	0.2669	0.3434	0.054*
H13B	0.5952	0.3176	0.2398	0.054*
C14	0.7802 (3)	0.51976 (19)	0.3595 (6)	0.0420 (11)
C15	0.8731 (4)	0.48180 (19)	0.3153 (6)	0.0465 (11)
O6	1.1845 (3)	0.07904 (14)	0.6127 (5)	0.0904 (11)
H6F	1.1814	0.0493	0.6779	0.136*
H6G	1.1552	0.0701	0.4975	0.136*
O7	1.0089 (3)	0.14122 (14)	0.7024 (6)	0.1067 (15)
H7C	0.9722	0.1194	0.7563	0.160*
H7D	1.0608	0.1214	0.6762	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0386 (3)	0.0339 (3)	0.0511 (3)	0.0007 (2)	0.0197 (3)	0.0014 (3)
O1	0.0566 (19)	0.0352 (17)	0.078 (2)	0.0074 (13)	0.0411 (18)	0.0105 (15)
O2	0.066 (2)	0.041 (2)	0.084 (3)	0.0000 (15)	0.0355 (19)	0.0150 (17)
O3	0.0421 (17)	0.046 (2)	0.066 (2)	0.0043 (13)	0.0285 (16)	0.0026 (15)
O4	0.079 (2)	0.064 (2)	0.105 (3)	−0.0064 (17)	0.067 (2)	0.012 (2)
O5	0.0454 (18)	0.084 (2)	0.051 (2)	−0.0148 (15)	0.0156 (16)	−0.0019 (16)
N1	0.0313 (18)	0.037 (2)	0.039 (2)	0.0026 (14)	0.0142 (17)	0.0010 (15)
N2	0.033 (2)	0.047 (2)	0.060 (3)	0.0009 (16)	0.0204 (18)	0.0009 (18)
N3	0.036 (2)	0.033 (2)	0.050 (2)	0.0015 (16)	0.0155 (18)	0.0029 (16)
N4	0.044 (2)	0.035 (2)	0.055 (3)	0.0080 (16)	0.0182 (19)	0.0012 (17)
C1	0.035 (2)	0.033 (3)	0.038 (3)	0.0006 (19)	0.009 (2)	0.0045 (19)
C2	0.039 (3)	0.041 (3)	0.055 (3)	−0.002 (2)	0.012 (2)	−0.006 (2)
C3	0.029 (2)	0.040 (3)	0.037 (3)	−0.0010 (18)	0.006 (2)	−0.0020 (19)
C4	0.045 (3)	0.035 (3)	0.057 (3)	0.0029 (19)	0.022 (2)	0.000 (2)
C5	0.070 (3)	0.065 (3)	0.061 (4)	0.013 (3)	0.014 (3)	−0.006 (3)
C6	0.046 (3)	0.068 (4)	0.109 (5)	−0.016 (2)	0.032 (3)	−0.021 (3)
C7	0.040 (3)	0.031 (3)	0.052 (3)	0.003 (2)	0.017 (2)	0.000 (2)
C8	0.057 (3)	0.034 (2)	0.043 (3)	−0.002 (2)	0.028 (2)	−0.007 (2)
C9	0.040 (3)	0.040 (3)	0.038 (3)	−0.002 (2)	0.015 (2)	−0.008 (2)
C10	0.042 (3)	0.052 (3)	0.100 (5)	0.003 (2)	0.011 (3)	−0.001 (3)
C11	0.051 (4)	0.068 (4)	0.205 (8)	0.010 (3)	0.004 (4)	0.008 (4)
C12	0.065 (3)	0.038 (3)	0.073 (4)	−0.005 (2)	0.034 (3)	−0.011 (2)
C13	0.044 (3)	0.042 (3)	0.050 (3)	−0.003 (2)	0.016 (2)	−0.010 (2)
C14	0.040 (3)	0.042 (3)	0.042 (3)	−0.007 (2)	0.011 (2)	0.003 (2)
C15	0.043 (3)	0.046 (3)	0.053 (3)	−0.009 (2)	0.017 (2)	−0.001 (2)
O6	0.086 (3)	0.076 (3)	0.114 (3)	0.0166 (19)	0.038 (2)	−0.001 (2)
O7	0.119 (3)	0.070 (2)	0.167 (4)	0.045 (2)	0.098 (3)	0.062 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.951 (2)	C4—H4B	0.9700
Cu1—N3	1.975 (3)	C5—H5A	0.9600
Cu1—O3	1.980 (3)	C5—H5B	0.9600
Cu1—N1	2.000 (3)	C5—H5C	0.9600
Cu1—O5	2.362 (3)	C6—H6A	0.9600
O1—C14	1.283 (4)	C6—H6B	0.9600
O2—C14	1.230 (4)	C6—H6C	0.9600
O3—C15	1.287 (4)	C7—C10	1.493 (5)
O4—C15	1.216 (4)	C8—C9	1.363 (5)
O5—H51	0.8489	C8—C12	1.490 (5)
O5—H52	0.8497	C9—C13	1.485 (5)
N1—C1	1.311 (4)	C10—C11	1.437 (5)
N1—C3	1.407 (4)	C10—H10A	0.9700
N2—C1	1.342 (4)	C10—H10B	0.9700
N2—C2	1.380 (5)	C11—H11A	0.9600
N2—H2	0.8599	C11—H11B	0.9600
N3—C7	1.323 (4)	C11—H11C	0.9600
N3—C9	1.398 (4)	C12—H12A	0.9600
N4—C7	1.344 (4)	C12—H12B	0.9600
N4—C8	1.375 (5)	C12—H12C	0.9600
N4—H4	0.8603	C13—H13A	0.9700
C1—C4	1.497 (5)	C13—H13B	0.9700
C2—C3	1.341 (5)	C14—C15	1.543 (5)
C2—C6	1.515 (5)	O6—H6F	0.8505
C3—C13	1.501 (5)	O6—H6G	0.8503
C4—C5	1.491 (6)	O7—H7C	0.8504
C4—H4A	0.9700	O7—H7D	0.8495

O1—Cu1—N3	171.72 (13)	C2—C6—H6A	109.5
O1—Cu1—O3	82.66 (11)	C2—C6—H6B	109.5
N3—Cu1—O3	91.60 (12)	H6A—C6—H6B	109.5
O1—Cu1—N1	92.73 (11)	C2—C6—H6C	109.5
N3—Cu1—N1	90.62 (12)	H6A—C6—H6C	109.5
O3—Cu1—N1	159.73 (12)	H6B—C6—H6C	109.5
O1—Cu1—O5	86.16 (11)	N3—C7—N4	109.4 (3)
N3—Cu1—O5	100.35 (12)	N3—C7—C10	127.0 (4)
O3—Cu1—O5	95.07 (11)	N4—C7—C10	123.6 (4)
N1—Cu1—O5	104.34 (11)	C9—C8—N4	105.6 (3)
C14—O1—Cu1	114.9 (3)	C9—C8—C12	131.6 (4)
C15—O3—Cu1	113.8 (2)	N4—C8—C12	122.9 (4)
Cu1—O5—H51	140.0	C8—C9—N3	108.5 (3)
Cu1—O5—H52	106.7	C8—C9—C13	130.1 (4)
H51—O5—H52	107.4	N3—C9—C13	121.4 (3)
C1—N1—C3	106.3 (3)	C11—C10—C7	117.6 (4)
C1—N1—Cu1	132.3 (3)	C11—C10—H10A	107.9
C3—N1—Cu1	121.2 (2)	C7—C10—H10A	107.9
C1—N2—C2	108.6 (3)	C11—C10—H10B	107.9
C1—N2—H2	125.5	C7—C10—H10B	107.9
C2—N2—H2	125.8	H10A—C10—H10B	107.2
C7—N3—C9	107.0 (3)	C10—C11—H11A	109.5
C7—N3—Cu1	131.0 (3)	C10—C11—H11B	109.5
C9—N3—Cu1	121.9 (3)	H11A—C11—H11B	109.5
C7—N4—C8	109.4 (3)	C10—C11—H11C	109.5
C7—N4—H4	125.3	H11A—C11—H11C	109.5
C8—N4—H4	125.2	H11B—C11—H11C	109.5
N1—C1—N2	110.2 (3)	C8—C12—H12A	109.5
N1—C1—C4	127.8 (3)	C8—C12—H12B	109.5
N2—C1—C4	121.9 (3)	H12A—C12—H12B	109.5
C3—C2—N2	105.9 (3)	C8—C12—H12C	109.5
C3—C2—C6	131.7 (4)	H12A—C12—H12C	109.5
N2—C2—C6	122.3 (3)	H12B—C12—H12C	109.5
C2—C3—N1	108.9 (3)	C9—C13—C3	113.3 (3)
C2—C3—C13	130.3 (4)	C9—C13—H13A	108.9
N1—C3—C13	120.8 (3)	C3—C13—H13A	108.9
C5—C4—C1	113.4 (3)	C9—C13—H13B	108.9
C5—C4—H4A	108.9	C3—C13—H13B	108.9
C1—C4—H4A	108.9	H13A—C13—H13B	107.7
C5—C4—H4B	108.9	O2—C14—O1	124.7 (4)
C1—C4—H4B	108.9	O2—C14—C15	121.0 (4)
H4A—C4—H4B	107.7	O1—C14—C15	114.2 (4)
C4—C5—H5A	109.5	O4—C15—O3	125.3 (4)
C4—C5—H5B	109.5	O4—C15—C14	120.6 (4)
H5A—C5—H5B	109.5	O3—C15—C14	114.2 (4)
C4—C5—H5C	109.5	H6F—O6—H6G	107.5
H5A—C5—H5C	109.5	H7C—O7—H7D	108.5
H5B—C5—H5C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱ	0.85	2.58	3.177 (4)	128
O5—H52···O4ⁱⁱ	0.85	1.90	2.748 (4)	174
N2—H2···O2ⁱⁱⁱ	0.86	2.09	2.943 (4)	171
N4—H4···O7	0.86	2.03	2.847 (4)	158
O6—H6F···O5^iv	0.85	2.50	3.259 (4)	149
O6—H6G···O4^v	0.85	2.30	3.057 (5)	148
O7—H7C···O3^vi	0.85	2.03	2.882 (4)	178
O7—H7D···O6	0.85	1.97	2.818 (4)	177

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

Experimental details

Crystal data
Chemical formula	[Cu(C₂O₄)(C₁₃H₂₀N₄)(H₂O)]·2H₂O
M_r	437.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.1711 (13), 23.167 (2), 7.4400 (8)
β (°)	107.304 (1)
V (Å³)	2002.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.35 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku MODEL? CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.693, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	10119, 3528, 1958
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.092, 0.81
No. of reflections	3528
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.31

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱ	0.85	2.58	3.177 (4)	128
O5—H52···O4ⁱⁱ	0.85	1.90	2.748 (4)	174
N2—H2···O2ⁱⁱⁱ	0.86	2.09	2.943 (4)	171
N4—H4···O7	0.86	2.03	2.847 (4)	158
O6—H6F···O5^iv	0.85	2.50	3.259 (4)	149
O6—H6G···O4^v	0.85	2.30	3.057 (5)	148
O7—H7C···O3^vi	0.85	2.03	2.882 (4)	178
O7—H7D···O6	0.85	1.97	2.818 (4)	177

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

References

Beznischenko, A. O., Makhankova, V. G., Kokozay, V. N., Zubatyuk, R. I. & Shishkin, O. V. (2007). Inorg. Chim. Acta, 10, 1325–1329 CAS Google Scholar
Bouwman, E., Douziech, B., Gutierrez-Soto, L., Beretta, M., Driessen, W. L., Reedijk, J. & Mendoza-Daz, G. (2000). Inorg. Chim. Acta, 304, 250–259. Web of Science CSD CrossRef CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Delgado, F. S., Lahoz, F., Lloret, F., Julve, M. & Ruiz-Pérez, C. (2008). J. Cryst. Growth Des. 8, 3219–3232. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Pajunen, A. (1981). Cryst. Struct. Commun. 10, 957–958. CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page m172

doi:10.1107/S1600536811001012

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