[N-(2-Hydroxy-ethyl)ethyl-enediamine]oxalatocopper(II).

In the title mononuclear copper(II) compound, [Cu(C(2)O(4))(C(4)H(12)N(2)O)], the Cu(II) ion has a slightly distorted square-pyramidal geometry, with a tridentate N-(2-hydroxy-ethyl)ethyl-enediamine (HydEt-en) and a bidentate oxalate (ox) ligand. The N atoms of the HydEt-en ligand and the O atoms of ox ligand form the basal plane, while the O atom of the ethanol group of the HydEt-en ligand is located in the axial position. The complex mol-ecules participate in a supra-molecular assembly through N-H⋯O and O-H⋯O hydrogen bonds between HydEt-en and ox ligands.

Related literature

For general background to the HydEt-en ligand, see: Karadağ et al. (2004 ▶, 2005 ▶); Paşaoğlu et al. (2005 ▶). For transition metal complexes of oxalate, see: Scott et al. (1973 ▶); Xia et al. (2004 ▶); Yılmaz et al. (2003 ▶); Youngme et al. (2003 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Cu(C2O4)(C4H12N2O)]

M = 255.72

Orthorhombic,

a = 7.9766 (5) Å

b = 8.7263 (4) Å

c = 13.0191 (7) Å

V = 906.21 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.41 mm−1

T = 296 K

0.52 × 0.42 × 0.23 mm

Data collection

Stoe IPDS-II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.570, T max = 0.781

10045 measured reflections

1868 independent reflections

1780 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.065

S = 1.08

1868 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −1.30 e Å−3

Absolute structure: Flack (1983 ▶), 797 Friedel pairs

Flack parameter: 0.017 (17)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040264/ci2929sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040264/ci2929Isup2.hkl

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

[Cu(C2O4)(C4H12N2O)]	F(000) = 524
Mr = 255.72	Dx = 1.874 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10045 reflections
a = 7.9766 (5) Å	θ = 1.6–28.0°
b = 8.7263 (4) Å	µ = 2.41 mm−1
c = 13.0191 (7) Å	T = 296 K
V = 906.21 (9) Å3	Prism, violet
Z = 4	0.52 × 0.42 × 0.23 mm

Stoe IPDS-II diffractometer	1868 independent reflections
Radiation source: fine-focus sealed tube	1780 reflections with I > 2σ(I)
plane graphite	Rint = 0.063
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.8°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.570, Tmax = 0.781	l = −15→16
10045 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0427P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1868 reflections	Δρmax = 0.22 e Å−3
143 parameters	Δρmin = −1.30 e Å−3
0 restraints	Absolute structure: Flack (1983), 797 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.017 (17)

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.

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.

	x	y	z	Uiso*/Ueq
C1	0.6054 (2)	0.4652 (2)	0.44437 (15)	0.0242 (4)
C2	0.7217 (3)	0.3322 (2)	0.41059 (16)	0.0274 (4)
C3	0.1649 (3)	0.2157 (3)	0.28011 (18)	0.0389 (5)
H3A	0.0821	0.1836	0.3302	0.047*
H3B	0.1451	0.1589	0.2172	0.047*
C4	0.1448 (3)	0.3853 (2)	0.25922 (18)	0.0374 (5)
H4A	0.0389	0.4029	0.2244	0.045*
H4B	0.1422	0.4404	0.3239	0.045*
C5	0.2752 (3)	0.3933 (3)	0.08732 (16)	0.0334 (4)
H5A	0.1974	0.4569	0.0492	0.040*
H5B	0.2357	0.2883	0.0845	0.040*
C6	0.4476 (3)	0.4039 (3)	0.04004 (16)	0.0339 (4)
H6A	0.4487	0.3530	−0.0262	0.041*
H6B	0.4780	0.5105	0.0299	0.041*
Cu1	0.50643 (3)	0.38250 (2)	0.252350 (16)	0.02606 (11)
N1	0.2830 (2)	0.44501 (19)	0.19527 (13)	0.0271 (4)
N2	0.5680 (2)	0.3297 (2)	0.11000 (14)	0.0282 (4)
O1	0.48949 (18)	0.49776 (14)	0.38029 (11)	0.0288 (3)
O2	0.6303 (2)	0.53159 (18)	0.52577 (12)	0.0364 (4)
O3	0.8216 (2)	0.27578 (18)	0.47136 (13)	0.0408 (4)
O4	0.70385 (19)	0.28980 (16)	0.31740 (11)	0.0328 (3)
O5	0.3275 (2)	0.18117 (19)	0.31756 (14)	0.0351 (3)
H1	0.280 (3)	0.542 (3)	0.1959 (18)	0.028 (6)*
H2A	0.559 (3)	0.223 (3)	0.102 (2)	0.038 (7)*
H2B	0.668 (4)	0.371 (4)	0.093 (2)	0.052 (8)*
H5	0.319 (3)	0.186 (3)	0.373 (2)	0.030 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0248 (9)	0.0247 (8)	0.0231 (9)	−0.0019 (7)	−0.0017 (8)	−0.0006 (7)
C2	0.0259 (9)	0.0240 (8)	0.0323 (10)	0.0001 (8)	−0.0045 (8)	0.0010 (8)
C3	0.0350 (12)	0.0418 (11)	0.0400 (11)	−0.0101 (10)	−0.0008 (10)	0.0076 (9)
C4	0.0307 (10)	0.0416 (11)	0.0399 (13)	0.0025 (8)	0.0031 (9)	0.0028 (11)
C5	0.0340 (10)	0.0397 (10)	0.0266 (10)	−0.0020 (10)	−0.0076 (8)	0.0005 (9)
C6	0.0419 (11)	0.0360 (9)	0.0238 (10)	−0.0051 (9)	−0.0019 (9)	0.0035 (8)
Cu1	0.02695 (16)	0.02892 (15)	0.02230 (18)	0.00454 (9)	−0.00390 (9)	−0.00309 (8)
N1	0.0286 (8)	0.0228 (8)	0.0299 (9)	0.0020 (6)	−0.0050 (7)	−0.0012 (6)
N2	0.0280 (9)	0.0289 (8)	0.0276 (9)	−0.0039 (7)	0.0030 (7)	−0.0019 (7)
O1	0.0315 (7)	0.0291 (6)	0.0258 (6)	0.0055 (6)	−0.0055 (6)	−0.0039 (5)
O2	0.0366 (9)	0.0409 (7)	0.0316 (8)	0.0008 (7)	−0.0068 (7)	−0.0103 (7)
O3	0.0415 (9)	0.0449 (8)	0.0359 (8)	0.0151 (7)	−0.0119 (7)	−0.0018 (7)
O4	0.0321 (7)	0.0363 (8)	0.0299 (7)	0.0109 (6)	−0.0046 (7)	−0.0068 (6)
O5	0.0370 (8)	0.0366 (8)	0.0318 (8)	−0.0002 (7)	0.0049 (7)	0.0061 (7)

C1—O2	1.224 (2)	C5—H5A	0.97
C1—O1	1.277 (2)	C5—H5B	0.97
C1—C2	1.549 (3)	C6—N2	1.473 (3)
C2—O3	1.226 (3)	C6—H6A	0.97
C2—O4	1.276 (3)	C6—H6B	0.97
C3—O5	1.418 (3)	Cu1—O1	1.9505 (13)
C3—C4	1.514 (3)	Cu1—O4	1.9625 (14)
C3—H3A	0.97	Cu1—N2	1.9717 (18)
C3—H3B	0.97	Cu1—N1	2.0066 (18)
C4—N1	1.477 (3)	Cu1—O5	2.4174 (16)
C4—H4A	0.97	N1—H1	0.85 (3)
C4—H4B	0.97	N2—H2A	0.94 (3)
C5—N1	1.477 (3)	N2—H2B	0.91 (3)
C5—C6	1.509 (3)	O5—H5	0.72 (3)
O2—C1—O1	125.27 (18)	H6A—C6—H6B	108.4
O2—C1—C2	120.22 (17)	O1—Cu1—O4	84.24 (6)
O1—C1—C2	114.50 (16)	O1—Cu1—N2	160.11 (7)
O3—C2—O4	124.72 (19)	O4—Cu1—N2	96.29 (7)
O3—C2—C1	120.44 (18)	O1—Cu1—N1	96.58 (6)
O4—C2—C1	114.83 (16)	O4—Cu1—N1	169.93 (7)
O5—C3—C4	111.52 (19)	N2—Cu1—N1	86.36 (7)
O5—C3—H3A	109.3	O1—Cu1—O5	91.94 (6)
C4—C3—H3A	109.3	O4—Cu1—O5	91.30 (6)
O5—C3—H3B	109.3	N2—Cu1—O5	107.90 (7)
C4—C3—H3B	109.3	N1—Cu1—O5	78.65 (7)
H3A—C3—H3B	108.0	C4—N1—C5	113.41 (17)
N1—C4—C3	111.52 (19)	C4—N1—Cu1	111.01 (13)
N1—C4—H4A	109.3	C5—N1—Cu1	107.84 (13)
C3—C4—H4A	109.3	C4—N1—H1	109.0 (17)
N1—C4—H4B	109.3	C5—N1—H1	108.3 (16)
C3—C4—H4B	109.3	Cu1—N1—H1	107.1 (16)
H4A—C4—H4B	108.0	C6—N2—Cu1	108.44 (13)
N1—C5—C6	109.33 (17)	C6—N2—H2A	108.3 (16)
N1—C5—H5A	109.8	Cu1—N2—H2A	108.5 (16)
C6—C5—H5A	109.8	C6—N2—H2B	104 (2)
N1—C5—H5B	109.8	Cu1—N2—H2B	111 (2)
C6—C5—H5B	109.8	H2A—N2—H2B	116 (3)
H5A—C5—H5B	108.3	C1—O1—Cu1	113.13 (11)
N2—C6—C5	108.33 (17)	C2—O4—Cu1	112.35 (12)
N2—C6—H6A	110.0	C3—O5—Cu1	105.36 (12)
C5—C6—H6A	110.0	C3—O5—H5	104 (2)
N2—C6—H6B	110.0	Cu1—O5—H5	112 (2)
C5—C6—H6B	110.0
O2—C1—C2—O3	11.9 (3)	O4—Cu1—N2—C6	−173.13 (13)
O1—C1—C2—O3	−169.41 (19)	N1—Cu1—N2—C6	16.62 (13)
O2—C1—C2—O4	−167.92 (19)	O5—Cu1—N2—C6	93.46 (14)
O1—C1—C2—O4	10.8 (2)	O2—C1—O1—Cu1	173.14 (16)
O5—C3—C4—N1	50.6 (3)	C2—C1—O1—Cu1	−5.5 (2)
N1—C5—C6—N2	49.2 (2)	O4—Cu1—O1—C1	0.32 (13)
C3—C4—N1—C5	71.6 (2)	N2—Cu1—O1—C1	−92.3 (2)
C3—C4—N1—Cu1	−50.0 (2)	N1—Cu1—O1—C1	170.23 (14)
C6—C5—N1—C4	−157.56 (17)	O5—Cu1—O1—C1	91.43 (13)
C6—C5—N1—Cu1	−34.2 (2)	O3—C2—O4—Cu1	170.12 (18)
O1—Cu1—N1—C4	−64.96 (14)	C1—C2—O4—Cu1	−10.1 (2)
O4—Cu1—N1—C4	29.1 (4)	O1—Cu1—O4—C2	5.92 (14)
N2—Cu1—N1—C4	134.79 (14)	N2—Cu1—O4—C2	165.93 (14)
O5—Cu1—N1—C4	25.71 (13)	N1—Cu1—O4—C2	−89.3 (4)
O1—Cu1—N1—C5	170.23 (13)	O5—Cu1—O4—C2	−85.90 (14)
O4—Cu1—N1—C5	−95.7 (4)	C4—C3—O5—Cu1	−25.7 (2)
N2—Cu1—N1—C5	9.98 (14)	O1—Cu1—O5—C3	96.66 (14)
O5—Cu1—N1—C5	−99.10 (14)	O4—Cu1—O5—C3	−179.06 (14)
C5—C6—N2—Cu1	−39.46 (19)	N2—Cu1—O5—C3	−82.02 (15)
O1—Cu1—N2—C6	−82.7 (2)	N1—Cu1—O5—C3	0.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.85 (3)	2.17 (3)	3.015 (2)	173 (2)
N2—H2A···O1ii	0.94 (3)	2.02 (3)	2.936 (2)	165 (2)
N2—H2B···O2iii	0.91 (3)	2.02 (3)	2.909 (2)	168 (3)
O5—H5···O3iv	0.72 (3)	2.06 (3)	2.774 (3)	171 (3)

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9505 (13)
Cu1—O4	1.9625 (14)
Cu1—N2	1.9717 (18)
Cu1—N1	2.0066 (18)
Cu1—O5	2.4174 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.85 (3)	2.17 (3)	3.015 (2)	173 (2)
N2—H2A⋯O1ii	0.94 (3)	2.02 (3)	2.936 (2)	165 (2)
N2—H2B⋯O2iii	0.91 (3)	2.02 (3)	2.909 (2)	168 (3)
O5—H5⋯O3iv	0.72 (3)	2.06 (3)	2.774 (3)	171 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .