Poly[dimethyl­ammonium aquadi-μ-oxalato-europate(III) trihydrate]

In the crystal structure of the polymeric title compound, (C₂H₈N)[Eu(C₂O₄)₂(H₂O)]·3H₂O, the independent oxalate that lies on a general position chelates to two Eu atoms, as do the other two oxalates that lie on different centres of inversion, the bridging mode of the oxalates giving rise to a three-dimensional anionic network. The water-coordinated Eu atom exists in a tricapped trigonal–prismatic geometry. The cations and solvent water mol­ecules occupy the cavities of the network and are involved in hydrogen bonding with each other and with the network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.026
• wR factor = 0.062
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N1
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1W2   ..  H2W1    ..       2.08 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.55
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C3_c   ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C4     -   C4_d   ...       1.55 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.840(10) ......       3.00 su-Rat
              O2W  -H2W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O3W  -H3W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.840(10) ......       4.00 su-Rat
              O3W  -H3W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O4W  -H4W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O4W  -H4W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              N1   -H1N1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.850(10) ......       4.00 su-Rat
              N1   -H1N2    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      111(5), Rep      111(2) ......       2.50 su-Rat
              H2W1 -O2W  -H2W2    1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      111(5), Rep      111(2) ......       2.50 su-Rat
              H3W1 -O3W  -H3W2    1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      110(5), Rep      109(2) ......       2.50 su-Rat
              H4W1 -O4W  -H4W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O3W  -H5#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.840(10) ......       4.00 su-Rat
              O3W  -H6#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O4W  -H7#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O4W  -H8#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              N1   -H9#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.850(10) ......       4.00 su-Rat
              N1   -H10#    1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.92(3), Rep   1.920(10) ......       3.00 su-Rat
              H1#  -O2W     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.12(4), Rep   2.120(10) ......       4.00 su-Rat
              H8#  -O3      1.555   2.545
PLAT736_ALERT_1_C H...A   Calc     1.96(3), Rep   1.960(10) ......       3.00 su-Rat
              H9#  -O3W     1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  29 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

  24 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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

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S1. Comment

Some rare earth/monovalent-cation oxalates contain water, and the compounds that are formulated as [M][(C₂O₄)₂La].nH₂O have been studied in order to understand the nature of the water molecules, as water is crucial to their applications. Such double oxalates have been structurally authenticated by both single-crystal and powder-diffraction methods; the ammonium derivative is a monohydrate, and the water molecule is involved in coordination to the Y atom in [NH₄][(C₂O₄)₂(H₂O)Y] (MacDonald & Spink, 1967). The nine-coordinate metal atom displays capped trigonal–prismatic coordination. The caesium analogue also has the rare earth atom in such a geometry (Bataille et al., 2000), as does the trihydrated sodium salt (Bataille & Louër, 1999). Another aquadioxalatoyttrate, a propyl-1,2-diammonium salt, has two solvent water molecules that interact with the cation (Vaidhyanathan et al., 2001). Double salts with other nine-coordinate water-coordinated rare earths include the erbium (Steinfink & Brunton, 1970), lanthanum (Fourcade-Cavillou & Trombe, 2002), neodymium (Fourcade-Cavillou & Trombe, 2002; Kahwa et al., 1984), samarium, europium, gadolinium and terbium (Kahwa et al., 1984) complexes.

The title dimethylammonium aquadioxalatoeuropate(III) exists as the trihydrate, (I) (Fig. 1). The Eu atom is surrounded by the eight atoms of four oxalates and the water molecule in a capped trigonal–prismatic environment (Fig. 2). The cations and solvent water molecules interact with each other along the channels of the polymeric anion (Fig. 3); extensive hydrogen bonds (Table 2) give rise to a tightly held network structure that has no solvent-accessible cavities.

S2. Experimental

A mixture of dieuropium trioxalate xhydrate (0.012 g, 0.02 mmol), 1,3,5-benzenetricarboxylic acid (0.011 g, 0.05 mmol) and water (4 ml) was heated to 333 K, and to this mixture was added di-n-propylethylamine (0.04 g, 0.05 mmol). The solution was placed in a Teflon-lined Parr bomb, which was heated to 453 K for 48 h. It was cooled at a rate of 5 K h⁻¹ to 333 K to yield colourless crystals of (I). As benzenetricarboxylic acid was not incorporated into the product, the reaction is essentially between dieuropium trixoxalate and dipropylethylamine; the dimethylammonium cation in the product probably results from the decomposition of dipropylethylamine.

S3. Refinement

The C-bound H atoms were placed in calculated positions, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C), and were included in the refinement in the riding-model approximation. Water and ammonium H atoms were located in difference Fourier maps, and were refined with distance restraints of O—H = N—H = 0.85 (1) Å and H···H = 1.39 (1) Å and with U_iso(H) = 1.2U_eq(O,N). The short H1W2···H2W1 distance of 2.08 Å is probably a consequence of some disorder in atom O2W, but the disorder could not be resolved. The largest peak in the final difference Fourier map of 1.08 e⁻ Å⁻³ was about 1 Å from Eu1.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. A view of a portion of the three-dimensional motif, showing the geometry of the Eu atom in polymeric (I). Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 3/2 − x, y − 1/2, 1/2 − z; (ii) 1 − x, 1 − y, 1 − z; (iii) 2 − x, 1 − y, 1 − z.]
	Fig. 2. The trigonal–prismatic geometry of the Eu atom in (I).
	Fig. 3. A view of the polymeric [(C2O4)2(H2O)Eu] network in (I).

Poly[dimethylammonium aquadi-µ-oxalato-europate(III) trihydrate]

Crystal data

(C2H8N)[Eu(C2O4)2(H2O)]·3H2O	F(000) = 872
Mr = 446.16	Dx = 2.143 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 885 reflections
a = 9.674 (1) Å	θ = 2.4–27.2°
b = 11.761 (1) Å	µ = 4.60 mm^−1
c = 12.315 (2) Å	T = 295 K
β = 99.285 (2)°	Block, colourless
V = 1382.8 (3) Å^3	0.06 × 0.05 × 0.05 mm
Z = 4

Data collection

Bruker SMART 1000 area-detector diffractometer	3113 independent reflections
Radiation source: fine-focus sealed tube	2578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ϕ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→7
Tmin = 0.702, Tmax = 0.803	k = −15→14
8455 measured reflections	l = −15→15

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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F^2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0359P)^2] where P = (Fo^2 + 2Fc^2)/3
3113 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 1.07 e Å^−3
15 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. A dimensionless value of 2r*µ = 0.30 was used in the SADABS step.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Eu1	0.71368 (2)	0.51552 (1)	0.33081 (1)	0.02102 (7)
O1	0.8070 (3)	0.6409 (2)	0.2055 (2)	0.0272 (6)
O2	0.8660 (3)	0.8194 (2)	0.1726 (2)	0.0253 (6)
O3	0.6396 (3)	0.7159 (2)	0.3435 (2)	0.0288 (6)
O4	0.6851 (3)	0.8950 (2)	0.3006 (2)	0.0318 (6)
O5	0.6813 (3)	0.5115 (2)	0.5224 (2)	0.0305 (6)
O6	0.5335 (3)	0.4854 (2)	0.6428 (2)	0.0263 (6)
O7	0.9160 (3)	0.6182 (2)	0.4341 (2)	0.0306 (6)
O8	1.1006 (3)	0.6088 (2)	0.5673 (2)	0.0347 (7)
O1W	0.5452 (3)	0.5236 (3)	0.1537 (2)	0.0374 (7)
O2W	0.4196 (5)	0.3424 (3)	0.0340 (3)	0.066 (1)
O3W	0.1705 (6)	0.5038 (4)	0.0076 (3)	0.079 (1)
O4W	0.0859 (5)	0.2816 (4)	0.0322 (4)	0.077 (1)
N1	0.2682 (5)	0.6312 (4)	0.1956 (4)	0.051 (1)
C1	0.8002 (4)	0.7455 (3)	0.2175 (3)	0.0220 (7)
C2	0.6990 (4)	0.7897 (3)	0.2946 (3)	0.0225 (8)
C3	0.5625 (4)	0.4992 (3)	0.5474 (3)	0.0219 (7)
C4	1.0046 (4)	0.5657 (3)	0.4997 (3)	0.0256 (8)
C5	0.1511 (7)	0.6242 (7)	0.2548 (5)	0.084 (2)
C6	0.3064 (8)	0.7458 (6)	0.1680 (5)	0.087 (2)
H1W1	0.514 (5)	0.462 (2)	0.122 (3)	0.045*
H1W2	0.572 (4)	0.568 (2)	0.107 (2)	0.045*
H2W1	0.334 (2)	0.355 (4)	0.014 (5)	0.079*
H2W2	0.435 (5)	0.273 (1)	0.046 (5)	0.079*
H3W1	0.160 (6)	0.543 (4)	−0.051 (3)	0.095*
H3W2	0.121 (6)	0.445 (3)	−0.001 (5)	0.095*
H4W1	0.077 (6)	0.253 (5)	−0.032 (2)	0.093*
H4W2	0.017 (4)	0.262 (5)	0.063 (4)	0.093*
H1N1	0.252 (5)	0.589 (3)	0.139 (2)	0.061*
H1N2	0.338 (4)	0.605 (4)	0.240 (3)	0.061*
H5A	0.1756	0.6599	0.3254	0.127*
H5B	0.1283	0.5459	0.2646	0.127*
H5C	0.0717	0.6623	0.2137	0.127*
H6A	0.2260	0.7835	0.1280	0.130*
H6B	0.3792	0.7424	0.1236	0.130*
H6C	0.3394	0.7871	0.2344	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Eu1	0.0240 (1)	0.0177 (1)	0.0222 (1)	0.0001 (1)	0.0063 (1)	0.0002 (1)
O1	0.039 (2)	0.016 (1)	0.030 (1)	0.001 (1)	0.015 (1)	−0.001 (1)
O2	0.024 (2)	0.021 (1)	0.033 (2)	0.001 (1)	0.010 (1)	0.004 (1)
O3	0.035 (2)	0.021 (1)	0.035 (2)	0.001 (1)	0.019 (1)	0.003 (1)
O4	0.048 (2)	0.018 (1)	0.034 (2)	0.001 (1)	0.020 (1)	0.001 (1)
O5	0.023 (1)	0.043 (2)	0.026 (1)	−0.003 (1)	0.005 (1)	−0.001 (1)
O6	0.025 (1)	0.034 (1)	0.020 (1)	0.002 (1)	0.004 (1)	0.002 (1)
O7	0.032 (2)	0.023 (1)	0.036 (2)	−0.003 (1)	0.001 (1)	0.007 (1)
O8	0.032 (2)	0.023 (1)	0.045 (2)	0.002 (1)	−0.006 (1)	−0.007 (1)
O1W	0.043 (2)	0.042 (2)	0.028 (2)	−0.006 (1)	0.005 (1)	0.001 (1)
O2W	0.093 (3)	0.038 (2)	0.068 (3)	0.000 (2)	0.010 (2)	−0.007 (2)
O3W	0.124 (4)	0.073 (3)	0.045 (2)	−0.021 (3)	0.023 (3)	0.002 (2)
O4W	0.113 (4)	0.059 (3)	0.072 (3)	−0.018 (2)	0.051 (3)	−0.013 (2)
N1	0.043 (3)	0.065 (3)	0.046 (3)	0.019 (2)	0.011 (2)	0.011 (2)
C1	0.024 (2)	0.024 (2)	0.018 (2)	0.000 (1)	0.002 (2)	0.002 (1)
C2	0.025 (2)	0.021 (2)	0.021 (2)	0.002 (1)	0.004 (2)	0.000 (1)
C3	0.026 (2)	0.017 (2)	0.023 (2)	−0.001 (1)	0.005 (2)	0.000 (1)
C4	0.024 (2)	0.027 (2)	0.027 (2)	0.001 (2)	0.009 (2)	−0.002 (2)
C5	0.061 (4)	0.136 (7)	0.060 (4)	0.029 (4)	0.019 (3)	0.019 (4)
C6	0.098 (6)	0.063 (4)	0.097 (5)	−0.002 (4)	0.007 (4)	0.019 (4)

Geometric parameters (Å, º)

Eu1—O1	2.412 (2)	C1—C2	1.560 (5)
Eu1—O2^i	2.430 (2)	C3—C3^ii	1.540 (7)
Eu1—O3	2.476 (2)	C4—C4^iii	1.547 (8)
Eu1—O4^i	2.469 (2)	O1W—H1W1	0.85 (1)
Eu1—O5	2.430 (3)	O1W—H1W2	0.85 (1)
Eu1—O6^ii	2.465 (3)	O2W—H2W1	0.84 (1)
Eu1—O7	2.471 (3)	O2W—H2W2	0.85 (1)
Eu1—O8^iii	2.492 (3)	O3W—H3W1	0.85 (1)
Eu1—O1W	2.505 (3)	O3W—H3W2	0.84 (1)
O1—C1	1.242 (4)	O4W—H4W1	0.85 (1)
O2—C1	1.257 (4)	O4W—H4W2	0.85 (1)
O3—C2	1.247 (4)	N1—H1N1	0.85 (1)
O4—C2	1.249 (4)	N1—H1N2	0.85 (1)
O5—C3	1.245 (4)	C5—H5A	0.96
O6—C3	1.261 (4)	C5—H5B	0.96
O7—C4	1.244 (4)	C5—H5C	0.96
O8—C4	1.250 (4)	C6—H6A	0.96
N1—C5	1.445 (7)	C6—H6B	0.96
N1—C6	1.452 (8)	C6—H6C	0.96
O1—Eu1—O2^i	136.0 (1)	C3—O5—Eu1	120.8 (2)
O1—Eu1—O3	66.4 (1)	C3—O6—Eu1^ii	119.3 (2)
O1—Eu1—O4^i	72.7 (1)	C4—O7—Eu1	119.8 (2)
O1—Eu1—O5	138.9 (1)	C4—O8—Eu1^iii	119.7 (2)
O1—Eu1—O6^ii	123.9 (1)	C5—N1—C6	114.9 (5)
O1—Eu1—O7	71.5 (1)	O1—C1—O2	126.4 (3)
O1—Eu1—O8^iii	111.5 (1)	O1—C1—C2	116.9 (3)
O1—Eu1—O1W	71.2 (1)	O2—C1—C2	116.7 (3)
O2^i—Eu1—O3	144.2 (1)	O3—C2—O4	126.8 (3)
O2^i—Eu1—O4^i	66.5 (1)	O3—C2—C1	116.4 (3)
O2^i—Eu1—O5	84.7 (1)	O4—C2—C1	116.7 (3)
O2^i—Eu1—O6^ii	71.7 (1)	O5—C3—O6	126.8 (3)
O2^i—Eu1—O7	134.1 (1)	O5—C3—C3^ii	117.0 (4)
O2^i—Eu1—O8^iii	69.7 (1)	O6—C3—C3^ii	116.3 (4)
O2^i—Eu1—O1W	82.0 (1)	O7—C4—O8	126.2 (4)
O3—Eu1—O4^i	137.5 (1)	O7—C4—C4^iii	117.7 (4)
O3—Eu1—O5	82.7 (1)	O8—C4—C4^iii	116.1 (4)
O3—Eu1—O6^ii	72.5 (1)	Eu1—O1W—H1W1	120 (3)
O3—Eu1—O7	73.5 (1)	Eu1—O1W—H1W2	113 (3)
O3—Eu1—O8^iii	136.0 (1)	H1W1—O1W—H1W2	110 (2)
O3—Eu1—O1W	82.2 (1)	H2W1—O2W—H2W2	111 (2)
O4^i—Eu1—O5	138.7 (1)	H3W1—O3W—H3W2	111 (2)
O4^i—Eu1—O6^ii	125.4 (1)	H4W1—O4W—H4W2	109 (2)
O4^i—Eu1—O7	104.7 (1)	C5—N1—H1N1	109 (4)
O4^i—Eu1—O8^iii	70.3 (1)	C6—N1—H1N1	112 (4)
O4^i—Eu1—O1W	73.9 (1)	C5—N1—H1N2	105 (4)
O5—Eu1—O6^ii	65.9 (1)	C6—N1—H1N2	106 (4)
O5—Eu1—O7	74.1 (1)	H1N1—N1—H1N2	110 (2)
O5—Eu1—O8^iii	72.3 (1)	N1—C5—H5A	109.5
O5—Eu1—O1W	132.7 (1)	N1—C5—H5B	109.5
O6^ii—Eu1—O7	129.7 (1)	H5A—C5—H5B	109.5
O6^ii—Eu1—O8^iii	124.5 (1)	N1—C5—H5C	109.5
O6^ii—Eu1—O1W	66.8 (1)	H5A—C5—H5C	109.5
O7—Eu1—O8^iii	65.2 (1)	H5B—C5—H5C	109.5
O7—Eu1—O1W	141.2 (1)	N1—C6—H6A	109.5
O8^iii—Eu1—O1W	140.9 (1)	N1—C6—H6B	109.5
C1—O1—Eu1	119.8 (2)	H6A—C6—H6B	109.5
C1—O2—Eu1^iv	118.9 (2)	N1—C6—H6C	109.5
C2—O3—Eu1	118.1 (2)	H6A—C6—H6C	109.5
C2—O4—Eu1^iv	118.3 (2)	H6B—C6—H6C	109.5
O5—Eu1—O1—C1	−31.3 (3)	O6^ii—Eu1—O7—C4	105.3 (3)
O2^i—Eu1—O1—C1	158.8 (2)	O4^i—Eu1—O7—C4	−69.8 (3)
O6^ii—Eu1—O1—C1	60.0 (3)	O3—Eu1—O7—C4	154.4 (3)
O4^i—Eu1—O1—C1	−178.5 (3)	O8^iii—Eu1—O7—C4	−10.0 (3)
O7—Eu1—O1—C1	−65.9 (3)	O1W—Eu1—O7—C4	−152.2 (2)
O3—Eu1—O1—C1	13.6 (3)	Eu1—O1—C1—O2	165.9 (3)
O8^iii—Eu1—O1—C1	−118.6 (3)	Eu1—O1—C1—C2	−14.9 (4)
O1W—Eu1—O1—C1	103.1 (3)	Eu1^iv—O2—C1—O1	163.0 (3)
O1—Eu1—O3—C2	−10.8 (3)	Eu1^iv—O2—C1—C2	−16.2 (4)
O5—Eu1—O3—C2	141.3 (3)	Eu1—O3—C2—O4	−172.5 (3)
O2^i—Eu1—O3—C2	−148.2 (2)	Eu1—O3—C2—C1	7.9 (4)
O6^ii—Eu1—O3—C2	−151.7 (3)	Eu1^iv—O4—C2—O3	−169.7 (3)
O4^i—Eu1—O3—C2	−27.9 (3)	Eu1^iv—O4—C2—C1	9.9 (4)
O7—Eu1—O3—C2	65.9 (3)	O1—C1—C2—O3	4.4 (5)
O8^iii—Eu1—O3—C2	86.4 (3)	O2—C1—C2—O3	−176.3 (3)
O1W—Eu1—O3—C2	−83.6 (3)	Eu1^iv—C1—C2—O3	172.8 (3)
O1—Eu1—O5—C3	122.0 (2)	O1—C1—C2—O4	−175.2 (3)
O2^i—Eu1—O5—C3	−65.0 (3)	O2—C1—C2—O4	4.1 (5)
O6^ii—Eu1—O5—C3	7.3 (2)	Eu1^iv—C1—C2—O4	−6.8 (3)
O4^i—Eu1—O5—C3	−109.7 (3)	Eu1—O5—C3—O6	173.0 (3)
O7—Eu1—O5—C3	156.1 (3)	Eu1—O5—C3—C3^ii	−6.8 (5)
O3—Eu1—O5—C3	81.3 (3)	Eu1^ii—O6—C3—O5	173.3 (3)
O8^iii—Eu1—O5—C3	−135.4 (3)	Eu1^ii—O6—C3—C3^ii	−6.8 (5)
O1W—Eu1—O5—C3	9.0 (3)	Eu1—O7—C4—O8	−169.8 (3)
O1—Eu1—O7—C4	−135.5 (3)	Eu1—O7—C4—C4^iii	9.1 (5)
O5—Eu1—O7—C4	67.4 (3)	Eu1^iii—O8—C4—O7	−170.6 (3)
O2^i—Eu1—O7—C4	1.6 (3)	Eu1^iii—O8—C4—C4^iii	10.4 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2W	0.85 (1)	1.92 (1)	2.759 (5)	169 (4)
O1W—H1W2···O2W^v	0.85 (1)	2.05 (2)	2.862 (5)	162 (4)
O2W—H2W2···O7^i	0.85 (1)	2.30 (2)	3.071 (5)	151 (4)
O2W—H2W2···O8^i	0.85 (1)	2.37 (4)	3.011 (4)	133 (5)
O3W—H3W1···O4^vi	0.85 (1)	2.02 (2)	2.838 (5)	162 (7)
O3W—H3W2···O4W	0.84 (1)	2.00 (3)	2.770 (6)	151 (5)
O4W—H4W1···O2^v	0.85 (1)	2.08 (2)	2.893 (4)	159 (5)
O4W—H4W2···O3^vii	0.85 (1)	2.12 (1)	2.962 (5)	173 (5)
N1—H1N1···O3W	0.85 (1)	1.96 (1)	2.792 (6)	167 (4)
N1—H1N2···O6^ii	0.85 (1)	2.05 (2)	2.879 (5)	165 (5)

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