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The title compound, (C6H16N4O2)[Cu(C2O4)2(H2O)2]·2H2O, consists of a [Cu(ox)2(H2O)2]2− dianion (ox is oxalate), a doubly protonated N,N′-bis­(2-ammonio­ethyl)oxamide dication (H4aeoxd2+) and two uncoordinated water mol­ecules. Both the cation and the anion are centrosymmetric. The structural components are linked into a three-dimensional supra­molecular structure by a combination of strong N—H...O and O—H...O, and weak C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050434/bg2014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050434/bg2014Isup2.hkl
Contains datablock I

CCDC reference: 629426

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C5 - C5_b ... 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.55 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-Bis(2-ammonioethyl)oxamide diaquabis(oxalato-κ2O,O')copper(II) dihydrate top
Crystal data top
(C6H16N4O2)[Cu(C2O4)2(H2O)2]·2H2OZ = 1
Mr = 487.88F(000) = 253
Triclinic, P1Dx = 1.708 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7889 (14) ÅCell parameters from 1733 reflections
b = 7.5799 (15) Åθ = 3.0–28.1°
c = 10.255 (2) ŵ = 1.23 mm1
α = 72.49 (3)°T = 298 K
β = 83.48 (3)°Flake, blue
γ = 70.51 (3)°0.45 × 0.38 × 0.29 mm
V = 474.4 (2) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1703 independent reflections
Radiation source: fine-focus sealed tube1518 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 87
Tmin = 0.595, Tmax = 0.702k = 79
2535 measured reflectionsl = 1112
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.3253P]
where P = (Fo2 + 2Fc2)/3
1703 reflections(Δ/σ)max < 0.001
134 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.53 e Å3
Special details top

Experimental. IR (KBr pellet, cm-1): ν(O—H) 3443, ν(N—H) and δ(N—H) 3065 and 1518, ν(O—CO) and ν(N—CO) 1647, 1425, 1299 and 804.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.00000.00000.00000.03005 (19)
O10.0585 (3)0.2237 (3)0.13070 (18)0.0277 (4)
O20.0727 (3)0.1175 (3)0.15083 (19)0.0338 (5)
O30.1643 (3)0.3123 (3)0.3466 (2)0.0324 (5)
O40.1626 (3)0.0398 (3)0.37096 (19)0.0314 (5)
C10.1155 (4)0.1955 (4)0.2474 (3)0.0238 (6)
C20.1190 (4)0.0041 (4)0.2598 (3)0.0243 (6)
C30.2606 (5)0.2368 (4)0.2956 (3)0.0314 (6)
H3A0.21110.23510.21110.038*
H3B0.35300.10720.33780.038*
C40.3806 (4)0.3797 (4)0.2639 (3)0.0305 (6)
H4A0.48710.34990.19530.037*
H4B0.28620.50990.22570.037*
C50.4327 (4)0.5225 (4)0.4380 (3)0.0271 (6)
N10.0792 (4)0.2869 (3)0.3888 (2)0.0291 (5)
H1A0.12490.27270.47040.044*
H1B0.00350.20800.39740.044*
H1C0.00050.40990.35420.044*
N20.4799 (4)0.3770 (3)0.3835 (2)0.0285 (5)
H20.57690.27210.42130.034*
O50.2948 (4)0.6801 (3)0.4000 (2)0.0464 (6)
O6W0.3813 (5)0.1327 (5)0.0716 (4)0.0892 (11)
H6A0.35320.14000.15560.080*
H6B0.50560.20670.06600.080*
O7W0.2542 (4)0.4513 (4)0.0523 (3)0.0546 (7)
H7A0.21260.57520.07440.080*
H7B0.17670.41610.09210.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0492 (4)0.0242 (3)0.0207 (3)0.0178 (2)0.0068 (2)0.00780 (19)
O10.0409 (11)0.0226 (9)0.0220 (9)0.0138 (8)0.0032 (8)0.0068 (7)
O20.0561 (14)0.0259 (10)0.0243 (10)0.0199 (10)0.0072 (9)0.0090 (8)
O30.0444 (12)0.0290 (10)0.0262 (10)0.0189 (9)0.0073 (9)0.0058 (8)
O40.0416 (12)0.0266 (10)0.0242 (10)0.0064 (9)0.0023 (8)0.0107 (8)
C10.0232 (14)0.0219 (13)0.0241 (13)0.0045 (10)0.0018 (10)0.0056 (11)
C20.0229 (14)0.0221 (13)0.0252 (14)0.0029 (11)0.0031 (11)0.0064 (11)
C30.0330 (16)0.0327 (15)0.0326 (15)0.0099 (13)0.0013 (12)0.0160 (12)
C40.0302 (15)0.0380 (16)0.0246 (14)0.0108 (13)0.0014 (12)0.0115 (12)
C50.0206 (14)0.0303 (15)0.0310 (15)0.0068 (11)0.0011 (11)0.0103 (11)
N10.0318 (13)0.0276 (12)0.0276 (12)0.0118 (10)0.0013 (10)0.0043 (10)
N20.0231 (12)0.0303 (12)0.0311 (13)0.0030 (10)0.0048 (10)0.0118 (10)
O50.0423 (13)0.0397 (13)0.0532 (14)0.0067 (10)0.0220 (11)0.0217 (11)
O6W0.0440 (17)0.068 (2)0.148 (3)0.0165 (15)0.0041 (19)0.019 (2)
O7W0.0507 (15)0.0460 (14)0.0746 (18)0.0175 (12)0.0073 (13)0.0229 (13)
Geometric parameters (Å, º) top
Cu1—O11.9464 (19)C4—N21.457 (3)
Cu1—O1i1.9464 (19)C4—H4A0.9700
Cu1—O2i1.9471 (19)C4—H4B0.9700
Cu1—O21.9471 (19)C5—O51.230 (3)
Cu1—O6W2.550 (3)C5—N21.313 (4)
O1—C11.273 (3)C5—C5ii1.538 (5)
O2—C21.268 (3)N1—H1A0.8900
O3—C11.227 (3)N1—H1B0.8900
O4—C21.232 (3)N1—H1C0.8900
C1—C21.548 (4)N2—H20.8600
C3—N11.487 (4)O6W—H6A0.8500
C3—C41.503 (4)O6W—H6B0.8500
C3—H3A0.9700O7W—H7A0.8500
C3—H3B0.9700O7W—H7B0.8500
O1—Cu1—O1i180.00 (17)H3A—C3—H3B107.9
O1—Cu1—O2i95.24 (8)N2—C4—C3113.0 (2)
O1i—Cu1—O2i84.76 (8)N2—C4—H4A109.0
O1—Cu1—O284.76 (8)C3—C4—H4A109.0
O1—Cu1—O6W91.02 (10)N2—C4—H4B109.0
O1i—Cu1—O295.24 (8)C3—C4—H4B109.0
O1i—Cu1—O6W88.98 (10)H4A—C4—H4B107.8
O2i—Cu1—O2180.00 (14)O5—C5—N2126.2 (3)
O2—Cu1—O6W89.54 (12)O5—C5—C5ii120.7 (3)
O2i—Cu1—O6W90.46 (12)N2—C5—C5ii113.1 (3)
C1—O1—Cu1112.53 (16)C3—N1—H1A109.5
C2—O2—Cu1112.56 (17)C3—N1—H1B109.5
O3—C1—O1125.4 (2)H1A—N1—H1B109.5
O3—C1—C2119.7 (2)C3—N1—H1C109.5
O1—C1—C2114.9 (2)H1A—N1—H1C109.5
O4—C2—O2125.6 (2)H1B—N1—H1C109.5
O4—C2—C1119.3 (2)C5—N2—C4125.0 (2)
O2—C2—C1115.2 (2)C5—N2—H2117.5
N1—C3—C4112.0 (2)C4—N2—H2117.5
N1—C3—H3A109.2Cu1—O6W—H6A94.6
C4—C3—H3A109.2Cu1—O6W—H6B150.5
N1—C3—H3B109.2H6A—O6W—H6B107.7
C4—C3—H3B109.2H7A—O7W—H7B107.7
O2i—Cu1—O1—C1179.49 (19)Cu1—O2—C2—C12.1 (3)
O2—Cu1—O1—C10.51 (19)O3—C1—C2—O42.9 (4)
O6W—Cu1—O1—C190.0 (2)O1—C1—C2—O4176.6 (2)
O1—Cu1—O2—C21.03 (19)O3—C1—C2—O2177.8 (2)
O1i—Cu1—O2—C2178.97 (19)O1—C1—C2—O22.7 (3)
O6W—Cu1—O2—C290.0 (2)N1—C3—C4—N265.1 (3)
Cu1—O1—C1—O3178.8 (2)O5—C5—N2—C42.3 (5)
Cu1—O1—C1—C21.7 (3)C5ii—C5—N2—C4178.9 (3)
Cu1—O2—C2—O4177.0 (2)C3—C4—N2—C5115.1 (3)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3iii0.892.052.912 (3)164
N1—H1B···O40.892.052.926 (3)167
N1—H1C···O3iv0.892.012.858 (3)159
N2—H2···O4v0.862.182.903 (3)141
O6W—H6A···O5vi0.852.533.307 (5)153
O6W—H6B···O7Wv0.852.052.860 (4)159
O7W—H7B···O10.852.032.828 (3)156
O7W—H7A···O2vi0.852.132.972 (3)171
C3—H3A···O20.972.583.329 (4)135
C4—H4B···O1iv0.972.593.502 (4)158
Symmetry codes: (iii) x, y, z+1; (iv) x, y+1, z; (v) x+1, y, z; (vi) x, y1, z.
 

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