N,N′-Bis(2-ammonio­ethyl)oxamide diaqua­bis(oxalato-κ²O,O′)cuprate(II) dihydrate

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.

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

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Computing details

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

Crystal data

(C6H16N4O2)[Cu(C2O4)2(H2O)2]·2H2O	Z = 1
Mr = 487.88	F(000) = 253
Triclinic, P1	Dx = 1.708 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7889 (14) Å	Cell parameters from 1733 reflections
b = 7.5799 (15) Å	θ = 3.0–28.1°
c = 10.255 (2) Å	µ = 1.23 mm^−1
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) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	1703 independent reflections
Radiation source: fine-focus sealed tube	1518 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→7
Tmin = 0.595, Tmax = 0.702	k = −7→9
2535 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.3253P] where P = (Fo^2 + 2Fc^2)/3
1703 reflections	(Δ/σ)max < 0.001
134 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. IR (KBr pellet, cm^-1): ν(O—H) 3443, ν(N—H) and δ(N—H) 3065 and 1518, ν(O—C═O) and ν(N—C═O) 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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.0000	0.0000	0.03005 (19)
O1	−0.0585 (3)	−0.2237 (3)	0.13070 (18)	0.0277 (4)
O2	−0.0727 (3)	0.1175 (3)	0.15083 (19)	0.0338 (5)
O3	−0.1643 (3)	−0.3123 (3)	0.3466 (2)	0.0324 (5)
O4	−0.1626 (3)	0.0398 (3)	0.37096 (19)	0.0314 (5)
C1	−0.1155 (4)	−0.1955 (4)	0.2474 (3)	0.0238 (6)
C2	−0.1190 (4)	0.0041 (4)	0.2598 (3)	0.0243 (6)
C3	0.2606 (5)	0.2368 (4)	0.2956 (3)	0.0314 (6)
H3A	0.2111	0.2351	0.2111	0.038*
H3B	0.3530	0.1072	0.3378	0.038*
C4	0.3806 (4)	0.3797 (4)	0.2639 (3)	0.0305 (6)
H4A	0.4871	0.3499	0.1953	0.037*
H4B	0.2862	0.5099	0.2257	0.037*
C5	0.4327 (4)	0.5225 (4)	0.4380 (3)	0.0271 (6)
N1	0.0792 (4)	0.2869 (3)	0.3888 (2)	0.0291 (5)
H1A	0.1249	0.2727	0.4704	0.044*
H1B	0.0035	0.2080	0.3974	0.044*
H1C	0.0005	0.4099	0.3542	0.044*
N2	0.4799 (4)	0.3770 (3)	0.3835 (2)	0.0285 (5)
H2	0.5769	0.2721	0.4213	0.034*
O5	0.2948 (4)	0.6801 (3)	0.4000 (2)	0.0464 (6)
O6W	0.3813 (5)	−0.1327 (5)	0.0716 (4)	0.0892 (11)
H6A	0.3532	−0.1400	0.1556	0.080*
H6B	0.5056	−0.2067	0.0660	0.080*
O7W	−0.2542 (4)	−0.4513 (4)	0.0523 (3)	0.0546 (7)
H7A	−0.2126	−0.5752	0.0744	0.080*
H7B	−0.1767	−0.4161	0.0921	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0492 (4)	0.0242 (3)	0.0207 (3)	−0.0178 (2)	0.0068 (2)	−0.00780 (19)
O1	0.0409 (11)	0.0226 (9)	0.0220 (9)	−0.0138 (8)	0.0032 (8)	−0.0068 (7)
O2	0.0561 (14)	0.0259 (10)	0.0243 (10)	−0.0199 (10)	0.0072 (9)	−0.0090 (8)
O3	0.0444 (12)	0.0290 (10)	0.0262 (10)	−0.0189 (9)	0.0073 (9)	−0.0058 (8)
O4	0.0416 (12)	0.0266 (10)	0.0242 (10)	−0.0064 (9)	0.0023 (8)	−0.0107 (8)
C1	0.0232 (14)	0.0219 (13)	0.0241 (13)	−0.0045 (10)	−0.0018 (10)	−0.0056 (11)
C2	0.0229 (14)	0.0221 (13)	0.0252 (14)	−0.0029 (11)	−0.0031 (11)	−0.0064 (11)
C3	0.0330 (16)	0.0327 (15)	0.0326 (15)	−0.0099 (13)	0.0013 (12)	−0.0160 (12)
C4	0.0302 (15)	0.0380 (16)	0.0246 (14)	−0.0108 (13)	0.0014 (12)	−0.0115 (12)
C5	0.0206 (14)	0.0303 (15)	0.0310 (15)	−0.0068 (11)	−0.0011 (11)	−0.0103 (11)
N1	0.0318 (13)	0.0276 (12)	0.0276 (12)	−0.0118 (10)	−0.0013 (10)	−0.0043 (10)
N2	0.0231 (12)	0.0303 (12)	0.0311 (13)	−0.0030 (10)	−0.0048 (10)	−0.0118 (10)
O5	0.0423 (13)	0.0397 (13)	0.0532 (14)	0.0067 (10)	−0.0220 (11)	−0.0217 (11)
O6W	0.0440 (17)	0.068 (2)	0.148 (3)	−0.0165 (15)	−0.0041 (19)	−0.019 (2)
O7W	0.0507 (15)	0.0460 (14)	0.0746 (18)	−0.0175 (12)	−0.0073 (13)	−0.0229 (13)

Geometric parameters (Å, º)

Cu1—O1	1.9464 (19)	C4—N2	1.457 (3)
Cu1—O1^i	1.9464 (19)	C4—H4A	0.9700
Cu1—O2^i	1.9471 (19)	C4—H4B	0.9700
Cu1—O2	1.9471 (19)	C5—O5	1.230 (3)
Cu1—O6W	2.550 (3)	C5—N2	1.313 (4)
O1—C1	1.273 (3)	C5—C5^ii	1.538 (5)
O2—C2	1.268 (3)	N1—H1A	0.8900
O3—C1	1.227 (3)	N1—H1B	0.8900
O4—C2	1.232 (3)	N1—H1C	0.8900
C1—C2	1.548 (4)	N2—H2	0.8600
C3—N1	1.487 (4)	O6W—H6A	0.8500
C3—C4	1.503 (4)	O6W—H6B	0.8500
C3—H3A	0.9700	O7W—H7A	0.8500
C3—H3B	0.9700	O7W—H7B	0.8500
O1—Cu1—O1^i	180.00 (17)	H3A—C3—H3B	107.9
O1—Cu1—O2^i	95.24 (8)	N2—C4—C3	113.0 (2)
O1^i—Cu1—O2^i	84.76 (8)	N2—C4—H4A	109.0
O1—Cu1—O2	84.76 (8)	C3—C4—H4A	109.0
O1—Cu1—O6W	91.02 (10)	N2—C4—H4B	109.0
O1^i—Cu1—O2	95.24 (8)	C3—C4—H4B	109.0
O1^i—Cu1—O6W	88.98 (10)	H4A—C4—H4B	107.8
O2^i—Cu1—O2	180.00 (14)	O5—C5—N2	126.2 (3)
O2—Cu1—O6W	89.54 (12)	O5—C5—C5^ii	120.7 (3)
O2^i—Cu1—O6W	90.46 (12)	N2—C5—C5^ii	113.1 (3)
C1—O1—Cu1	112.53 (16)	C3—N1—H1A	109.5
C2—O2—Cu1	112.56 (17)	C3—N1—H1B	109.5
O3—C1—O1	125.4 (2)	H1A—N1—H1B	109.5
O3—C1—C2	119.7 (2)	C3—N1—H1C	109.5
O1—C1—C2	114.9 (2)	H1A—N1—H1C	109.5
O4—C2—O2	125.6 (2)	H1B—N1—H1C	109.5
O4—C2—C1	119.3 (2)	C5—N2—C4	125.0 (2)
O2—C2—C1	115.2 (2)	C5—N2—H2	117.5
N1—C3—C4	112.0 (2)	C4—N2—H2	117.5
N1—C3—H3A	109.2	Cu1—O6W—H6A	94.6
C4—C3—H3A	109.2	Cu1—O6W—H6B	150.5
N1—C3—H3B	109.2	H6A—O6W—H6B	107.7
C4—C3—H3B	109.2	H7A—O7W—H7B	107.7
O2^i—Cu1—O1—C1	−179.49 (19)	Cu1—O2—C2—C1	−2.1 (3)
O2—Cu1—O1—C1	0.51 (19)	O3—C1—C2—O4	2.9 (4)
O6W—Cu1—O1—C1	90.0 (2)	O1—C1—C2—O4	−176.6 (2)
O1—Cu1—O2—C2	1.03 (19)	O3—C1—C2—O2	−177.8 (2)
O1^i—Cu1—O2—C2	−178.97 (19)	O1—C1—C2—O2	2.7 (3)
O6W—Cu1—O2—C2	−90.0 (2)	N1—C3—C4—N2	65.1 (3)
Cu1—O1—C1—O3	178.8 (2)	O5—C5—N2—C4	2.3 (5)
Cu1—O1—C1—C2	−1.7 (3)	C5^ii—C5—N2—C4	−178.9 (3)
Cu1—O2—C2—O4	177.0 (2)	C3—C4—N2—C5	−115.1 (3)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^iii	0.89	2.05	2.912 (3)	164
N1—H1B···O4	0.89	2.05	2.926 (3)	167
N1—H1C···O3^iv	0.89	2.01	2.858 (3)	159
N2—H2···O4^v	0.86	2.18	2.903 (3)	141
O6W—H6A···O5^vi	0.85	2.53	3.307 (5)	153
O6W—H6B···O7W^v	0.85	2.05	2.860 (4)	159
O7W—H7B···O1	0.85	2.03	2.828 (3)	156
O7W—H7A···O2^vi	0.85	2.13	2.972 (3)	171
C3—H3A···O2	0.97	2.58	3.329 (4)	135
C4—H4B···O1^iv	0.97	2.59	3.502 (4)	158

Symmetry codes: (iii) −x, −y, −z+1; (iv) x, y+1, z; (v) x+1, y, z; (vi) x, y−1, z.