trans-Diaqua-bis(ethyl-enediamine-κN,N')copper(II) bis[3-(3-pyrid-yl)propionate] dihydrate.

The asymmetric unit of the title complex, [Cu(C(2)H(8)N(2))(2)(H(2)O)(2)](C(8)H(8)NO(2))(2)·2H(2)O, contains one anion, one half-cation and one water mol-ecule. The Cu(II) atom in the [Cu(en)(2)(H(2)O)(2)](2+) cation (en is ethyl-enediamine) lies on an inversion centre. The four N atoms of the en ligands in the equatorial plane around the Cu(II) atom form a slightly distorted square-planar arrangement, while the slightly distorted Jahn-Teller octa-hedral coordination is completed by two water O atoms in axial positions. In the crystal structure, intra- and inter-molecular N-H⋯O and O-H⋯O hydrogen bonds form a three-dimensional network.

Related literature

For general background, see: Hathaway & Hodgson (1973 ▶); Bernstein et al. (1995 ▶); Janiak (2000 ▶); Jeffrey (1997 ▶). For similar structures, see: Jašková et al. (2007 ▶); Mimino­shvili et al. (2005 ▶); Carballo et al. (2005 ▶); Segla et al. (2000 ▶); Liu et al. (2004 ▶); Sharma et al. (2005 ▶); Anacona et al. (2002 ▶); Emsley et al. (1988 ▶, 1990 ▶); Li et al. (2005 ▶); Gonzalez-Alvarez et al. (2003 ▶); Lee et al. (2005 ▶); Mahadevan et al. (1986 ▶); Kovbasyuk et al. (1997 ▶); Harrison et al. (2007 ▶).

Experimental

Crystal data

[Cu(C2H8N2)2(H2O)2](C8H8NO2)2·2H2O

M = 556.13

Triclinic,

a = 6.2620 (1) Å

b = 8.5660 (2) Å

c = 13.3550 (4) Å

α = 75.271 (1)°

β = 83.809 (1)°

γ = 70.863 (1)°

V = 654.30 (3) Å3

Z = 1

Ag Kα radiation

μ = 0.47 mm−1

T = 153 (2) K

0.45 × 0.25 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997 ▶) T min = 0.808, T max = 0.915

15039 measured reflections

2989 independent reflections

2644 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.086

S = 1.07

2989 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.31 e Å−3

Data collection: KappaCCD Software (Nonius, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005400/hk2427sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005400/hk2427Isup2.hkl

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

[Cu(C2H8N2)2(H2O1)2](C8H8NO2)2·2H2O	Z = 1
Mr = 556.13	F000 = 295
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Ag Kα radiation λ = 0.56085 Å
a = 6.2620 (1) Å	Cell parameters from 2489 reflections
b = 8.5660 (2) Å	θ = 3.3–21.4º
c = 13.3550 (4) Å	µ = 0.47 mm−1
α = 75.271 (1)º	T = 153 (2) K
β = 83.809 (1)º	Prism, violet
γ = 70.863 (1)º	0.45 × 0.25 × 0.20 mm
V = 654.30 (3) Å3

Bruker–Nonius KappaCCD diffractometer	2989 independent reflections
Radiation source: fine-focus sealed tube	2644 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.079
T = 153(2) K	θmax = 21.4º
ω and φ scans	θmin = 3.3º
Absorption correction: numerical(HABITUS; Herrendorf & Bärnighausen, 1997)	h = −8→8
Tmin = 0.808, Tmax = 0.915	k = −11→11
15039 measured reflections	l = −17→17

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0215P)2 + 0.3896P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2989 reflections	Δρmax = 0.38 e Å−3
160 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)2.3086 (0.0059) x + 8.2273 (0.0023) y - 0.2376 (0.0130) z = 6.3254 (0.0154)* 0.0032 (0.0016) N3* -0.0044 (0.0016) C6* 0.0010 (0.0017) C7* -0.0039 (0.0017) C8* 0.0003 (0.0018) C9* 0.0038 (0.0017) C103.3255 (0.0028) N3_$63.3331 (0.0028) C6_$63.3277 (0.0030) C7_$63.3326 (0.0031) C8_$63.3285 (0.0029) C9_$63.3249 (0.0030) C10_$6Rms deviation of fitted atoms = 0.0032

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
Cu	0.5000	0.5000	0.5000	0.02500 (12)
N1	0.5413 (3)	0.7274 (2)	0.48893 (14)	0.0328 (4)
H1A	0.6147	0.7242	0.5459	0.039*
H1B	0.6270	0.7540	0.4306	0.039*
N2	0.1813 (3)	0.6372 (2)	0.45504 (14)	0.0307 (4)
H2A	0.1410	0.5969	0.4047	0.037*
H2B	0.0813	0.6297	0.5104	0.037*
N3	−0.0294 (4)	0.8099 (3)	1.12361 (17)	0.0520 (6)
O1	−0.0720 (3)	0.6040 (3)	0.66095 (13)	0.0493 (5)
O2	−0.4121 (3)	0.7310 (2)	0.71927 (15)	0.0518 (5)
O1W	0.3984 (3)	0.4843 (2)	0.68797 (15)	0.0515 (5)
H1W	0.4422	0.5531	0.7088	0.063*
H2W	0.2570	0.5084	0.6916	0.063*
O2W	0.6770 (4)	0.9227 (3)	0.29173 (16)	0.0682 (6)
H3W	0.7363	0.8948	0.2368	0.063*
H4W	0.6086	1.0274	0.2809	0.063*
C1	0.1767 (4)	0.8158 (3)	0.41381 (19)	0.0399 (5)
H1C	0.0192	0.8928	0.4130	0.048*
H1D	0.2402	0.8312	0.3421	0.048*
C2	0.3163 (4)	0.8558 (3)	0.4831 (2)	0.0399 (5)
H2C	0.3294	0.9709	0.4542	0.048*
H2D	0.2442	0.8520	0.5530	0.048*
C3	−0.2033 (4)	0.6638 (3)	0.72904 (17)	0.0339 (5)
C4	−0.1063 (4)	0.6478 (3)	0.83208 (19)	0.0418 (5)
H4A	−0.2050	0.6083	0.8890	0.050*
H4B	0.0448	0.5608	0.8387	0.050*
C5	−0.0846 (6)	0.8114 (3)	0.8436 (2)	0.0575 (8)
H5A	−0.2360	0.8978	0.8392	0.069*
H5B	0.0113	0.8527	0.7860	0.069*
C6	0.0179 (4)	0.7906 (3)	0.94565 (19)	0.0389 (5)
C7	−0.1118 (4)	0.8301 (3)	1.0313 (2)	0.0458 (6)
H7	−0.2711	0.8749	1.0242	0.055*
C8	0.1937 (5)	0.7467 (3)	1.1312 (2)	0.0507 (7)
H8	0.2567	0.7298	1.1962	0.061*
C9	0.3376 (4)	0.7045 (3)	1.0513 (2)	0.0460 (6)
H9	0.4963	0.6603	1.0606	0.055*
C10	0.2489 (4)	0.7271 (3)	0.95738 (19)	0.0417 (5)
H10	0.3462	0.6992	0.9005	0.050*

	U11	U22	U33	U12	U13	U23
Cu	0.02142 (18)	0.02502 (19)	0.0296 (2)	−0.00597 (13)	−0.00336 (13)	−0.00873 (14)
N1	0.0370 (10)	0.0319 (10)	0.0332 (10)	−0.0132 (8)	−0.0058 (8)	−0.0086 (8)
N2	0.0266 (8)	0.0378 (10)	0.0292 (9)	−0.0082 (7)	−0.0023 (7)	−0.0121 (8)
N3	0.0777 (16)	0.0397 (12)	0.0397 (13)	−0.0190 (11)	0.0090 (11)	−0.0145 (10)
O1	0.0421 (9)	0.0819 (14)	0.0342 (9)	−0.0235 (9)	0.0035 (7)	−0.0280 (9)
O2	0.0401 (9)	0.0620 (12)	0.0555 (12)	−0.0036 (8)	−0.0106 (8)	−0.0300 (9)
O1W	0.0399 (9)	0.0668 (12)	0.0526 (11)	−0.0158 (8)	0.0015 (8)	−0.0243 (9)
O2W	0.0781 (14)	0.0525 (12)	0.0540 (13)	−0.0063 (10)	0.0207 (11)	−0.0053 (10)
C1	0.0364 (12)	0.0340 (12)	0.0404 (13)	0.0026 (9)	−0.0085 (10)	−0.0078 (10)
C2	0.0478 (13)	0.0284 (11)	0.0425 (14)	−0.0068 (10)	−0.0010 (10)	−0.0129 (10)
C3	0.0380 (12)	0.0386 (12)	0.0311 (12)	−0.0163 (9)	−0.0034 (9)	−0.0119 (9)
C4	0.0532 (14)	0.0418 (13)	0.0336 (13)	−0.0141 (11)	−0.0079 (10)	−0.0126 (10)
C5	0.089 (2)	0.0386 (14)	0.0508 (17)	−0.0225 (14)	−0.0349 (15)	−0.0035 (12)
C6	0.0540 (14)	0.0294 (11)	0.0378 (13)	−0.0159 (10)	−0.0144 (11)	−0.0068 (10)
C7	0.0436 (13)	0.0338 (12)	0.0636 (18)	−0.0142 (10)	−0.0036 (12)	−0.0137 (12)
C8	0.083 (2)	0.0384 (14)	0.0338 (14)	−0.0169 (13)	−0.0209 (13)	−0.0078 (11)
C9	0.0479 (14)	0.0426 (14)	0.0516 (16)	−0.0146 (11)	−0.0149 (12)	−0.0121 (12)
C10	0.0519 (14)	0.0419 (13)	0.0353 (13)	−0.0169 (11)	−0.0005 (10)	−0.0132 (10)

Cu—O1Wi	2.503 (2)	C1—C2	1.506 (3)
Cu—O1W	2.503 (2)	C1—H1C	0.9900
Cu—N1i	2.015 (2)	C1—H1D	0.9900
Cu—N1	2.015 (2)	C2—H2C	0.9900
Cu—N2i	2.022 (2)	C2—H2D	0.9900
Cu—N2	2.022 (2)	C3—C4	1.521 (3)
O1—C3	1.251 (3)	C4—C5	1.498 (3)
O2—C3	1.250 (3)	C4—H4A	0.9900
O1W—H1W	0.84	C4—H4B	0.9900
O1W—H2W	0.84	C5—C6	1.513 (3)
O2W—H3W	0.84	C5—H5A	0.9900
O2W—H4W	0.84	C5—H5B	0.9900
N1—C2	1.472 (3)	C6—C7	1.378 (4)
N1—H1A	0.9200	C6—C10	1.379 (3)
N1—H1B	0.9200	C7—H7	0.9500
N2—C1	1.480 (3)	C8—C9	1.363 (4)
N2—H2A	0.9200	C8—H8	0.9500
N2—H2B	0.9200	C9—C10	1.370 (3)
N3—C8	1.327 (4)	C9—H9	0.9500
N3—C7	1.337 (4)	C10—H10	0.9500
O1Wi—Cu—O1W	180.0	H1C—C1—H1D	108.5
N1i—Cu—O1Wi	88.72 (7)	N1—C2—C1	107.48 (18)
N1—Cu—O1Wi	91.28 (7)	N1—C2—H2C	110.2
N2i—Cu—O1Wi	93.19 (6)	C1—C2—H2C	110.2
N2—Cu—O1Wi	86.81 (6)	N1—C2—H2D	110.2
N1i—Cu—O1W	91.28 (7)	C1—C2—H2D	110.2
N1—Cu—O1W	88.72 (7)	H2C—C2—H2D	108.5
N2i—Cu—O1W	86.81 (6)	O2—C3—O1	124.1 (2)
N2—Cu—O1W	93.19 (6)	O2—C3—C4	117.4 (2)
N1i—Cu—N1	180.00 (11)	O1—C3—C4	118.4 (2)
N1i—Cu—N2i	84.91 (7)	C5—C4—C3	113.0 (2)
N1—Cu—N2i	95.09 (7)	C5—C4—H4A	109.0
N1i—Cu—N2	95.09 (7)	C3—C4—H4A	109.0
N1—Cu—N2	84.91 (7)	C5—C4—H4B	109.0
N2i—Cu—N2	180.0	C3—C4—H4B	109.0
C2—N1—Cu	108.14 (13)	H4A—C4—H4B	107.8
C2—N1—H1A	110.1	C4—C5—C6	111.8 (2)
Cu—N1—H1A	110.1	C4—C5—H5A	109.2
C2—N1—H1B	110.1	C6—C5—H5A	109.2
Cu—N1—H1B	110.1	C4—C5—H5B	109.2
H1A—N1—H1B	108.4	C6—C5—H5B	109.2
C1—N2—Cu	107.44 (13)	H5A—C5—H5B	107.9
C1—N2—H2A	110.2	C7—C6—C10	116.7 (2)
Cu—N2—H2A	110.2	C7—C6—C5	122.5 (2)
C1—N2—H2B	110.2	C10—C6—C5	120.8 (2)
Cu—N2—H2B	110.2	N3—C7—C6	124.6 (2)
H2A—N2—H2B	108.5	N3—C7—H7	117.7
C8—N3—C7	116.3 (2)	C6—C7—H7	117.7
Cu—O1W—H1W	110.3	N3—C8—C9	123.8 (2)
Cu—O1W—H2W	104.9	N3—C8—H8	118.1
H1W—O1W—H2W	111.9	C9—C8—H8	118.1
H3W—O2W—H4W	111.2	C8—C9—C10	118.7 (2)
N2—C1—C2	107.81 (18)	C8—C9—H9	120.7
N2—C1—H1C	110.1	C10—C9—H9	120.7
C2—C1—H1C	110.1	C9—C10—C6	119.8 (2)
N2—C1—H1D	110.1	C9—C10—H10	120.1
C2—C1—H1D	110.1	C6—C10—H10	120.1
N2i—Cu—N1—C2	−165.34 (14)	O1—C3—C4—C5	104.8 (3)
N2—Cu—N1—C2	14.66 (14)	C3—C4—C5—C6	−178.5 (2)
O1Wi—Cu—N1—C2	101.34 (14)	C4—C5—C6—C7	−96.9 (3)
O1W—Cu—N1—C2	−78.66 (14)	C4—C5—C6—C10	81.8 (3)
N1i—Cu—N2—C1	−165.31 (14)	C8—N3—C7—C6	−0.2 (4)
N1—Cu—N2—C1	14.70 (14)	C10—C6—C7—N3	−0.5 (4)
O1Wi—Cu—N2—C1	−76.88 (14)	C5—C6—C7—N3	178.2 (2)
O1W—Cu—N2—C1	103.12 (14)	C7—N3—C8—C9	0.7 (4)
Cu—N2—C1—C2	−40.8 (2)	N3—C8—C9—C10	−0.4 (4)
Cu—N1—C2—C1	−40.7 (2)	C8—C9—C10—C6	−0.4 (4)
N2—C1—C2—N1	54.5 (2)	C7—C6—C10—C9	0.8 (3)
O2—C3—C4—C5	−77.7 (3)	C5—C6—C10—C9	−178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ii	0.92	2.32	3.130 (3)	147
N1—H1A···O1ii	0.92	2.41	3.247 (2)	152
N1—H1B···O2W	0.92	2.11	2.944 (3)	151
N2—H2A···O1iii	0.92	2.29	3.150 (3)	155
N2—H2B···O1	0.92	2.12	3.019 (2)	164
O1W—H1W···O2ii	0.84	2.06	2.873 (3)	164
O1W—H2W···O1	0.84	2.00	2.814 (2)	164
O2W—H3W···N3iv	0.84	2.08	2.899 (3)	163
O2W—H4W···O2v	0.84	2.03	2.859 (3)	169

X2	Cu–N1	Cu–N2	Cu–OW	Ta	N1–Cu–N2
(3-pypr)2.2H2O	2.015 (2)	2.022 (2)	2.503 (2)	0.81	84.91 (7)
(2,6-(MeO)2nic)2b	2.018 (2)	2.020 (2)	2.467 (2)	0.82	83.96 (8)
(4-O2Nbz)2c	2.015 (2)	2.027 (2)	2.537 (2)	0.80	84.92 (7)
(2-NH2bz)2d	2.012 (4)	2.020 (5)	2.503 (4)	0.81	84.52 (9)
(benz)2e	2.009 (4)	2.017 (4)	2.653 (5)	0.76	84.8 (2)
(isonic)2f	2.021 (2)	2.018 (2)	2.598 (2)	0.78	84.98 (6)
(4-Fbz)2g	2.018 (4)	2.021 (4)	2.579 (4)	0.78	85.0 (2)
(naphs)2h	2.020 (2)	2.018 (2)	2.513 (1)	0.80	84.63 (7)
(stz)2.2H2Oi	2.042 (3)	2.033 (3)	2.484 (3)	0.82	84.1 (1)
F2.4H2Oj	2.019 (5)	2.023 (5)	2.571 (6)	0.78	84.6 (2)
(NH2naphs)2.2H2Ok	2.023 (2)	2.012 (2)	2.437 (2)	0.83	84.30 (9)
(Clbtts)2l	2.019 (4)	2.049 (3)	2.416 (3)	0.84	84.2 (2)
(Cl-Fbz)2m	2.009 (2)	2.016 (2)	2.618 (1)	0.77	84.30 (6)
(BPh4)2.2DMSOn	2.022 (10)	2.055 (8)	2.693 (9)	0.76	84.9 (4)
(edcarb).2H2Oo	1.996 (2)	2.022 (2)	2.556 (2)	0.79	84.78 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.92	2.32	3.130 (3)	147
N1—H1A⋯O1i	0.92	2.41	3.247 (2)	152
N1—H1B⋯O2W	0.92	2.11	2.944 (3)	151
N2—H2A⋯O1ii	0.92	2.29	3.150 (3)	155
N2—H2B⋯O1	0.92	2.12	3.019 (2)	164
O1W—H1W⋯O2i	0.84	2.06	2.873 (3)	164
O1W—H2W⋯O1	0.84	2.00	2.814 (2)	164
O2W—H3W⋯N3iii	0.84	2.08	2.899 (3)	163
O2W—H4W⋯O2iv	0.84	2.03	2.859 (3)	169

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