Yttrium ethyl­enediammonium squarate tetra­hydrate

Zenkhri, L.; Audebrand, N.; Bataille, T.

doi:10.1107/S1600536811011251

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m529-m530

doi:10.1107/S1600536811011251

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Yttrium ethylenediammonium squarate tetrahydrate

Louiza Zenkhri,^a ^* Nathalie Audebrand ^b and Thierry Bataille ^b

^aFaculté des Sciences et Technologie et Sciences de la Matière, Université Kasdi Merbah Ouargla, Route Gardaia, Ourgla, Algeria, and ^bLaboratoire Sciences Chimiques de Rennes (CNRS, UMR 6226), Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes Cedex, France
^*Correspondence e-mail: louizazenkhri@yahoo.fr

(Received 7 March 2011; accepted 25 March 2011; online 7 April 2011)

The title compound, {(C₂H₁₀N₂)_1.5[Y(C₄O₄)₃(H₂O)₄]}_n {systematic name: catena-poly[sesqui(ethylenediammonium) [[tetraaquabis(squarato-κO)yttrium(III)]-μ-squarato-κ²O:O′]]}, was synthesized by slow evaporation of an acid solution. The asymetric unit contains one yttrium cation in an antiprismatic environnement, three squarate groups, one and a half protonated ethylenediamine molecules and four water molecules. YO₈ polyhedra are connected through bis(monodentate) squarates, leading to infinite zigzag chains, in between which are located ammonium groups. A framework of hydrogen bonds between protonated amine N atoms, water molecules and squarate anions ensures the cohesion of the structure.

Related literature

For a related structure, see: Kazerouni et al. (1994). The title compound was obtained together with two polymorphs of (C₂H₁₀N₂)(HC₄O₄)₂(H₂O) (Mathew et al., 2002 ; Zenkhri et al., 2011). For related yttrium squarates with potassium, see: Mahé & Bataille (2004 ).

Experimental

Crystal data

(C₂H₁₀N₂)_1.5[Y(C₄O₄)₃(H₂O)₄]
M_r = 590.27
Monoclinic, P 2₁ /c
a = 8.9780 (2) Å
b = 13.2864 (3) Å
c = 18.3970 (4) Å
β = 90.935 (1)°
V = 2194.20 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.75 mm⁻¹
T = 293 K
0.22 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: analytical (de Meulenaer & Tompa, 1965) T_min = 0.583, T_max = 0.734
23285 measured reflections
5016 independent reflections
4140 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.103
S = 1.10
5016 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 1.77 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H12⋯O3ⁱ	0.87	2.21	3.027 (4)	157
N1—H12⋯O9ⁱⁱ	0.87	2.36	2.929 (4)	123
N1—H11⋯O4ⁱ	0.87	2.36	2.995 (4)	131
N1—H11⋯O7ⁱⁱ	0.87	2.28	2.987 (4)	138
N1—H13⋯O6ⁱⁱ	0.87	2.36	2.970 (4)	127
N1—H13⋯O12ⁱⁱ	0.87	2.26	3.032 (4)	148
N2—H23⋯O2	0.85	1.87	2.707 (4)	167
N2—H21⋯O4ⁱ	0.96	1.92	2.832 (4)	159
N2—H21⋯O7ⁱⁱ	0.96	2.46	2.952 (4)	112
N2—H22⋯O5ⁱⁱⁱ	0.95	2.01	2.929 (4)	163
N3—H31⋯O4	0.87	2.22	2.843 (4)	129
N3—H32⋯O8^iv	0.87	2.18	2.788 (4)	127
N3—H33⋯OW1^v	0.87	2.40	2.997 (4)	126
OW1—H911⋯O11^v	0.94	1.74	2.676 (3)	175
OW1—H912⋯O5	0.93	1.78	2.687 (3)	166
OW2—H922⋯O11	0.94	1.95	2.885 (4)	173
OW2—H921⋯O10^v	0.94	1.79	2.726 (3)	179
OW3—H931⋯O8^vi	0.93	1.94	2.857 (4)	172
OW3—H932⋯O1ⁱ	0.94	2.04	2.954 (5)	163
OW4—H942⋯O5^vi	0.92	1.86	2.779 (3)	172
OW4—H941⋯O10^vii	0.93	1.86	2.761 (4)	163
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x-1, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011251/ru2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011251/ru2003Isup2.hkl

checkCIF report

Comment top

In the course of a study on mixed squarate of amines and metals, the role of the amine group has been investigated in the topology of the organic-inorganic framework. The synthesis led to a new mixed squarate of yttrium and ethylenediamine.

Yttrium is eightfold coordinated in the shape of a square antiprism. YO₈ polyhedra are connected along the b axis through bis(monodentate) squarates in the form of zigzag chains (Figures 1, 2). Amine groups are located between the chains (Figure 2) and are connected to them through hydrogen bonds involving oxygen atoms from squarate groups (Table 1). Other hydrogen bonds between water molecules and squarate groups contribute also to the formation of a three-dimensional molecular framework (Table 1). One ethylenediammonium possesses a gauche conformation as already reported for this molecule (Kazerouni et al., 1994).

Related literature top

For a related structure, see: Kazerouni et al. (1994). The title compound was obtained together with together with two polymorphs of (HC₄O₄)₂(C₂H₁₀N₂)(H₂O) (Mathew et al., 2002; Zenkhri et al., 2011). For related literature [on what subject?], see: Mahé & Bataille (2004). Scheme – is an extra bond needed extending out of the square brackets to show the connectivity?

Experimental top

The title compound, Y(C₄O₄)₃(C₂H₁₀N₂)_1.54H₂O was prepared from an aquous solution (20 ml) of dissolved yttrium nitrate (0.5 mmol), ethylenediamine (0.1 mmol) and 3,4-dihydroxy-3-cyclobutene-1,2-dione, also named squaric acid (0.1 mmol). The slow evaporation at room temperature leads after some hours to the formation of the title compound together with two polymorphs of (HC₄O₄)₂(C₂H₁₀N₂)(H₂O) (Mathew et al., 2002; Zenkhri et al.., 2011).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top

	Fig. 1. View of the molecular structure of the title compound. Ellipsoids are shown at the 50% probability level. (i) 1 - x, -1 - y, 2 - z; (ii) 2 - x, -1/2 + y, 3/2 - z.
	Fig. 2. View of the structure of the title compound along the a axis displaying chains alternating with amine groups.

catena-poly[sesqui(ethylenediammonium) [[tetraaquabis(squarato-κO)yttrium(III)]-µ-squarato- κ²O:O']] top

Crystal data top

(C₂H₁₀N₂)_1.5[Y(C₄O₄)₃(H₂O)₄]	F(000) = 1204
M_r = 590.27	D_x = 1.787 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9780 (2) Å	Cell parameters from 57148 reflections
b = 13.2864 (3) Å	θ = 2.9–27.5°
c = 18.3970 (4) Å	µ = 2.75 mm⁻¹
β = 90.935 (1)°	T = 293 K
V = 2194.20 (8) Å³	Prism, colourless
Z = 4	0.22 × 0.14 × 0.12 mm

Data collection top

Nonius KappaCCD diffractometer	5016 independent reflections
Radiation source: fine-focus sealed tube	4140 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.065
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
CCD scans	h = −11→11
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = −17→17
T_min = 0.583, T_max = 0.734	l = −23→23
23285 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0368P)² + 4.9093P] where P = (F_o² + 2F_c²)/3
5016 reflections	(Δ/σ)_max = 0.002
316 parameters	Δρ_max = 1.77 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

(C₂H₁₀N₂)_1.5[Y(C₄O₄)₃(H₂O)₄]	V = 2194.20 (8) Å³
M_r = 590.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9780 (2) Å	µ = 2.75 mm⁻¹
b = 13.2864 (3) Å	T = 293 K
c = 18.3970 (4) Å	0.22 × 0.14 × 0.12 mm
β = 90.935 (1)°

Data collection top

Nonius KappaCCD diffractometer	5016 independent reflections
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	4140 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.734	R_int = 0.065
23285 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.10	Δρ_max = 1.77 e Å⁻³
5016 reflections	Δρ_min = −0.62 e Å⁻³
316 parameters

Special details top

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 > 2σ(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

	x	y	z	U_iso*/U_eq
Y1	0.81967 (3)	0.09385 (2)	0.775395 (16)	0.01739 (9)
OW1	0.6982 (2)	−0.02399 (18)	0.69447 (13)	0.0255 (5)
H911	0.6156	−0.0626	0.7085	0.038*
H912	0.7647	−0.0720	0.6785	0.038*
OW2	0.5760 (3)	0.15385 (18)	0.74497 (16)	0.0332 (6)
H921	0.4774	0.1303	0.7446	0.050*
H922	0.5568	0.2216	0.7550	0.050*
OW3	0.7609 (4)	0.1825 (2)	0.88343 (19)	0.0653 (12)
H931	0.7880	0.2376	0.9116	0.098*
H932	0.7345	0.1447	0.9243	0.098*
OW4	1.0544 (3)	0.16009 (19)	0.82212 (15)	0.0332 (6)
H941	1.1451	0.1438	0.8013	0.050*
H942	1.0623	0.2267	0.8356	0.050*
C1	0.3965 (4)	−0.0751 (3)	0.9370 (2)	0.0344 (9)
O1	0.2824 (3)	−0.0919 (3)	0.97182 (19)	0.0618 (10)
C2	0.4625 (4)	0.0166 (3)	0.90558 (19)	0.0308 (8)
O2	0.4298 (4)	0.1078 (2)	0.90299 (18)	0.0567 (9)
C3	0.5884 (4)	−0.0427 (2)	0.88126 (17)	0.0215 (6)
O3	0.7096 (2)	−0.02378 (17)	0.84855 (13)	0.0260 (5)
C4	0.5259 (4)	−0.1337 (3)	0.91110 (19)	0.0270 (7)
O4	0.5696 (3)	−0.2235 (2)	0.91517 (16)	0.0389 (6)
C5	0.9863 (4)	−0.0763 (2)	0.60978 (17)	0.0212 (6)
O5	0.8971 (3)	−0.14412 (17)	0.62986 (14)	0.0283 (5)
C6	1.0043 (4)	0.0306 (2)	0.62387 (17)	0.0212 (6)
O6	0.9443 (3)	0.09575 (17)	0.66401 (13)	0.0278 (5)
C7	1.1316 (4)	0.0349 (2)	0.57414 (18)	0.0228 (6)
O7	1.2148 (3)	0.10214 (18)	0.55251 (16)	0.0356 (6)
C8	1.1158 (4)	−0.0751 (2)	0.56315 (18)	0.0227 (7)
O8	1.1858 (3)	−0.14202 (19)	0.53033 (16)	0.0368 (6)
C9	0.8814 (3)	0.4399 (2)	0.72880 (17)	0.0190 (6)
O9	1.0131 (2)	0.46219 (16)	0.71244 (13)	0.0244 (5)
C10	0.7446 (4)	0.4939 (2)	0.74815 (18)	0.0225 (6)
O10	0.7095 (3)	0.58392 (18)	0.75490 (17)	0.0360 (6)
C11	0.6683 (3)	0.3960 (2)	0.75669 (18)	0.0216 (6)
O11	0.5417 (3)	0.3661 (2)	0.77318 (16)	0.0351 (6)
C12	0.8066 (3)	0.3451 (2)	0.73838 (17)	0.0203 (6)
O12	0.8488 (3)	0.25554 (17)	0.73267 (15)	0.0316 (6)
N1	0.1150 (3)	0.2173 (2)	1.13530 (16)	0.0276 (6)
H11	0.1863	0.2579	1.1230	0.033*
H12	0.1531	0.1615	1.1520	0.033*
H13	0.0618	0.2454	1.1688	0.033*
C13	0.0190 (4)	0.1952 (3)	1.0706 (2)	0.0315 (8)
H131	−0.0192	0.2581	1.0511	0.038*
H132	−0.0654	0.1553	1.0858	0.038*
C14	0.0985 (4)	0.1398 (3)	1.0114 (2)	0.0317 (8)
H141	0.1488	0.0817	1.0323	0.038*
H142	0.0257	0.1156	0.9760	0.038*
N2	0.2096 (3)	0.2041 (2)	0.97398 (16)	0.0300 (7)
H21	0.2778	0.2278	1.0107	0.036*
H22	0.1607	0.2561	0.9477	0.036*
H23	0.2683	0.1717	0.9464	0.036*
N3	0.4125 (4)	−0.4070 (3)	0.93482 (18)	0.0392 (8)
H31	0.4774	−0.3779	0.9072	0.047*
H32	0.3940	−0.3685	0.9718	0.047*
H33	0.3306	−0.4175	0.9100	0.047*
C15	0.4730 (4)	−0.5043 (3)	0.9610 (2)	0.0348 (9)
H151	0.5550	−0.5246	0.9306	0.042*
H152	0.3963	−0.5555	0.9574	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Y1	0.01584 (14)	0.01229 (13)	0.02423 (15)	0.00006 (11)	0.00636 (10)	0.00037 (12)
OW1	0.0212 (11)	0.0241 (12)	0.0313 (12)	−0.0036 (9)	0.0061 (9)	−0.0030 (10)
OW2	0.0161 (11)	0.0211 (12)	0.0625 (18)	0.0014 (9)	0.0049 (11)	0.0036 (12)
OW3	0.099 (3)	0.0388 (17)	0.060 (2)	−0.0325 (18)	0.055 (2)	−0.0255 (15)
OW4	0.0302 (13)	0.0235 (12)	0.0456 (16)	−0.0003 (10)	−0.0048 (11)	−0.0100 (11)
C1	0.0197 (16)	0.058 (3)	0.0259 (18)	−0.0034 (16)	0.0021 (13)	0.0039 (16)
O1	0.0269 (15)	0.104 (3)	0.055 (2)	−0.0107 (17)	0.0177 (14)	0.011 (2)
C2	0.0284 (18)	0.042 (2)	0.0228 (17)	0.0099 (16)	0.0066 (14)	0.0032 (15)
O2	0.068 (2)	0.0505 (19)	0.0524 (19)	0.0358 (17)	0.0266 (17)	0.0089 (15)
C3	0.0219 (15)	0.0236 (16)	0.0190 (15)	0.0011 (13)	0.0032 (12)	0.0002 (12)
O3	0.0234 (11)	0.0234 (12)	0.0317 (13)	0.0022 (9)	0.0116 (10)	0.0058 (10)
C4	0.0217 (16)	0.0335 (18)	0.0257 (17)	−0.0081 (14)	−0.0004 (13)	0.0042 (14)
O4	0.0408 (15)	0.0259 (13)	0.0498 (17)	−0.0086 (12)	0.0008 (13)	0.0090 (12)
C5	0.0258 (16)	0.0155 (14)	0.0224 (15)	0.0002 (12)	0.0017 (12)	0.0011 (11)
O5	0.0297 (12)	0.0183 (11)	0.0373 (14)	−0.0060 (10)	0.0110 (10)	−0.0002 (10)
C6	0.0249 (15)	0.0158 (14)	0.0232 (16)	−0.0003 (12)	0.0055 (12)	0.0006 (12)
O6	0.0352 (13)	0.0170 (11)	0.0317 (13)	−0.0019 (10)	0.0166 (10)	−0.0012 (10)
C7	0.0238 (16)	0.0182 (15)	0.0265 (16)	0.0022 (12)	0.0068 (13)	0.0024 (12)
O7	0.0364 (14)	0.0196 (12)	0.0517 (16)	−0.0027 (11)	0.0238 (12)	0.0033 (11)
C8	0.0243 (16)	0.0182 (15)	0.0258 (16)	0.0005 (12)	0.0025 (13)	−0.0006 (12)
O8	0.0382 (14)	0.0227 (13)	0.0500 (17)	0.0037 (11)	0.0193 (12)	−0.0081 (11)
C9	0.0183 (14)	0.0160 (14)	0.0229 (15)	0.0008 (11)	0.0034 (12)	−0.0004 (12)
O9	0.0177 (11)	0.0168 (11)	0.0390 (14)	−0.0030 (9)	0.0086 (9)	−0.0019 (10)
C10	0.0195 (15)	0.0193 (15)	0.0289 (17)	0.0032 (12)	0.0023 (12)	−0.0001 (13)
O10	0.0253 (12)	0.0161 (12)	0.0668 (19)	0.0064 (10)	0.0064 (12)	−0.0027 (12)
C11	0.0174 (14)	0.0193 (15)	0.0282 (16)	0.0020 (12)	0.0045 (12)	0.0017 (13)
O11	0.0181 (11)	0.0275 (13)	0.0602 (18)	0.0025 (10)	0.0131 (11)	0.0071 (12)
C12	0.0185 (14)	0.0177 (14)	0.0247 (16)	0.0015 (12)	0.0040 (12)	0.0036 (12)
O12	0.0275 (12)	0.0132 (11)	0.0546 (16)	0.0009 (9)	0.0149 (11)	0.0046 (11)
N1	0.0320 (15)	0.0198 (13)	0.0314 (16)	0.0027 (12)	0.0110 (12)	0.0010 (12)
C13	0.0216 (16)	0.0338 (19)	0.039 (2)	0.0014 (14)	0.0029 (14)	0.0051 (16)
C14	0.040 (2)	0.0239 (17)	0.0309 (19)	0.0005 (15)	−0.0044 (15)	0.0000 (14)
N2	0.0353 (16)	0.0283 (15)	0.0267 (15)	0.0109 (13)	0.0061 (12)	−0.0009 (12)
N3	0.0367 (18)	0.046 (2)	0.0351 (17)	−0.0108 (16)	0.0085 (14)	−0.0034 (15)
C15	0.0296 (18)	0.044 (2)	0.031 (2)	−0.0111 (16)	0.0079 (15)	−0.0092 (16)

Geometric parameters (Å, º) top

Y1—O3	2.297 (2)	C8—O8	1.250 (4)
Y1—O12	2.304 (2)	C9—O9	1.261 (4)
Y1—O9ⁱ	2.314 (2)	C9—C12	1.439 (4)
Y1—O6	2.351 (2)	C9—C10	1.471 (4)
Y1—OW3	2.377 (3)	O9—Y1ⁱⁱ	2.314 (2)
Y1—OW2	2.386 (2)	C10—O10	1.244 (4)
Y1—OW1	2.409 (2)	C10—C11	1.479 (4)
Y1—OW4	2.428 (2)	C11—O11	1.247 (4)
OW1—H911	0.9405	C11—C12	1.458 (4)
OW1—H912	0.9255	C12—O12	1.254 (4)
OW2—H921	0.9388	N1—C13	1.487 (5)
OW2—H922	0.9354	N1—H11	0.8700
OW3—H931	0.9277	N1—H12	0.8700
OW3—H932	0.9382	N1—H13	0.8700
OW4—H941	0.9307	C13—C14	1.504 (5)
OW4—H942	0.9214	C13—H131	0.9700
C1—O1	1.237 (4)	C13—H132	0.9700
C1—C2	1.476 (5)	C14—N2	1.491 (5)
C1—C4	1.484 (5)	C14—H141	0.9700
C2—O2	1.249 (5)	C14—H142	0.9700
C2—C3	1.454 (5)	N2—H21	0.9571
C3—O3	1.277 (4)	N2—H22	0.9479
C3—C4	1.445 (5)	N2—H23	0.8528
C4—O4	1.257 (5)	N3—C15	1.479 (5)
C5—O5	1.265 (4)	N3—H31	0.8700
C5—C6	1.453 (4)	N3—H32	0.8700
C5—C8	1.456 (4)	N3—H33	0.8700
C6—O6	1.264 (4)	C15—C15ⁱⁱⁱ	1.512 (8)
C6—C7	1.476 (4)	C15—H151	0.9700
C7—O7	1.234 (4)	C15—H152	0.9700
C7—C8	1.482 (4)

O3—Y1—O12	152.48 (8)	C5—C6—C7	90.7 (3)
O3—Y1—O9ⁱ	73.35 (8)	C6—O6—Y1	135.7 (2)
O12—Y1—O9ⁱ	131.37 (8)	O7—C7—C6	134.9 (3)
O3—Y1—O6	137.19 (8)	O7—C7—C8	136.6 (3)
O12—Y1—O6	68.55 (8)	C6—C7—C8	88.4 (2)
O9ⁱ—Y1—O6	77.00 (8)	O8—C8—C5	133.6 (3)
O3—Y1—OW3	75.14 (9)	O8—C8—C7	136.0 (3)
O12—Y1—OW3	81.46 (10)	C5—C8—C7	90.3 (2)
O9ⁱ—Y1—OW3	116.50 (12)	O9—C9—C12	132.6 (3)
O6—Y1—OW3	147.03 (9)	O9—C9—C10	137.1 (3)
O3—Y1—OW2	87.89 (8)	C12—C9—C10	90.2 (2)
O12—Y1—OW2	73.57 (8)	C9—O9—Y1ⁱⁱ	139.9 (2)
O9ⁱ—Y1—OW2	150.02 (8)	O10—C10—C9	135.0 (3)
O6—Y1—OW2	103.86 (9)	O10—C10—C11	135.7 (3)
OW3—Y1—OW2	79.37 (13)	C9—C10—C11	89.2 (2)
O3—Y1—OW1	74.04 (8)	O11—C11—C12	133.8 (3)
O12—Y1—OW1	116.61 (9)	O11—C11—C10	137.0 (3)
O9ⁱ—Y1—OW1	81.66 (8)	C12—C11—C10	89.2 (2)
O6—Y1—OW1	71.68 (8)	O12—C12—C9	132.7 (3)
OW3—Y1—OW1	137.23 (10)	O12—C12—C11	135.9 (3)
OW2—Y1—OW1	70.61 (9)	C9—C12—C11	91.4 (2)
O3—Y1—OW4	114.74 (9)	C12—O12—Y1	145.1 (2)
O12—Y1—OW4	71.35 (9)	C13—N1—H11	109.5
O9ⁱ—Y1—OW4	71.44 (8)	C13—N1—H12	109.5
O6—Y1—OW4	83.21 (9)	H11—N1—H12	109.5
OW3—Y1—OW4	74.20 (11)	C13—N1—H13	109.5
OW2—Y1—OW4	138.51 (9)	H11—N1—H13	109.5
OW1—Y1—OW4	146.71 (8)	H12—N1—H13	109.5
Y1—OW1—H911	122.4	N1—C13—C14	113.6 (3)
Y1—OW1—H912	110.8	N1—C13—H131	108.8
H911—OW1—H912	103.1	C14—C13—H131	108.8
Y1—OW2—H921	138.7	N1—C13—H132	108.8
Y1—OW2—H922	116.5	C14—C13—H132	108.8
H921—OW2—H922	98.3	H131—C13—H132	107.7
Y1—OW3—H931	142.9	N2—C14—C13	112.5 (3)
Y1—OW3—H932	117.9	N2—C14—H141	109.1
H931—OW3—H932	92.4	C13—C14—H141	109.1
Y1—OW4—H941	122.0	N2—C14—H142	109.1
Y1—OW4—H942	120.4	C13—C14—H142	109.1
H941—OW4—H942	105.7	H141—C14—H142	107.8
O1—C1—C2	133.9 (4)	C14—N2—H21	106.7
O1—C1—C4	136.9 (4)	C14—N2—H22	110.2
C2—C1—C4	89.2 (3)	H21—N2—H22	113.9
O2—C2—C3	134.3 (4)	C14—N2—H23	114.2
O2—C2—C1	136.1 (3)	H21—N2—H23	101.0
C3—C2—C1	89.6 (3)	H22—N2—H23	110.5
O3—C3—C4	133.1 (3)	C15—N3—H31	109.5
O3—C3—C2	135.3 (3)	C15—N3—H32	109.5
C4—C3—C2	91.6 (3)	H31—N3—H32	109.5
C3—O3—Y1	142.0 (2)	C15—N3—H33	109.5
O4—C4—C3	133.9 (3)	H31—N3—H33	109.5
O4—C4—C1	136.4 (3)	H32—N3—H33	109.5
C3—C4—C1	89.6 (3)	N3—C15—C15ⁱⁱⁱ	110.7 (4)
O5—C5—C6	135.6 (3)	N3—C15—H151	109.5
O5—C5—C8	134.0 (3)	C15ⁱⁱⁱ—C15—H151	109.5
C6—C5—C8	90.4 (2)	N3—C15—H152	109.5
O6—C6—C5	136.6 (3)	C15ⁱⁱⁱ—C15—H152	109.5
O6—C6—C7	132.6 (3)	H151—C15—H152	108.1

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O3^iv	0.87	2.21	3.027 (4)	157
N1—H12···O9^v	0.87	2.36	2.929 (4)	123
N1—H11···O4^iv	0.87	2.36	2.995 (4)	131
N1—H11···O7^v	0.87	2.28	2.987 (4)	138
N1—H13···O6^v	0.87	2.36	2.970 (4)	127
N1—H13···O12^v	0.87	2.26	3.032 (4)	148
N2—H23···O2	0.85	1.87	2.707 (4)	167
N2—H21···O4^iv	0.96	1.92	2.832 (4)	159
N2—H21···O7^v	0.96	2.46	2.952 (4)	112
N2—H22···O5^vi	0.95	2.01	2.929 (4)	163
N3—H31···O4	0.87	2.22	2.843 (4)	129
N3—H32···O8^vii	0.87	2.18	2.788 (4)	127
N3—H33···OW1^viii	0.87	2.40	2.997 (4)	126
OW1—H911···O11^viii	0.94	1.74	2.676 (3)	175
OW1—H912···O5	0.93	1.78	2.687 (3)	166
OW2—H922···O11	0.94	1.95	2.885 (4)	173
OW2—H921···O10^viii	0.94	1.79	2.726 (3)	179
OW3—H931···O8ⁱⁱ	0.93	1.94	2.857 (4)	172
OW3—H932···O1^iv	0.94	2.04	2.954 (5)	163
OW4—H942···O5ⁱⁱ	0.92	1.86	2.779 (3)	172
OW4—H941···O10ⁱ	0.93	1.86	2.761 (4)	163

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

Experimental details

Crystal data
Chemical formula	(C₂H₁₀N₂)_1.5[Y(C₄O₄)₃(H₂O)₄]
M_r	590.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9780 (2), 13.2864 (3), 18.3970 (4)
β (°)	90.935 (1)
V (Å³)	2194.20 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.75
Crystal size (mm)	0.22 × 0.14 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Analytical (de Meulenaer & Tompa, 1965)
T_min, T_max	0.583, 0.734
No. of measured, independent and observed [I > 2σ(I)] reflections	23285, 5016, 4140
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.103, 1.10
No. of reflections	5016
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.77, −0.62

Computer programs: COLLECT (Nonius, 2000), DIRAX/LSQ (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 2001), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O3ⁱ	0.87	2.21	3.027 (4)	157
N1—H12···O9ⁱⁱ	0.87	2.36	2.929 (4)	123
N1—H11···O4ⁱ	0.87	2.36	2.995 (4)	131
N1—H11···O7ⁱⁱ	0.87	2.28	2.987 (4)	138
N1—H13···O6ⁱⁱ	0.87	2.36	2.970 (4)	127
N1—H13···O12ⁱⁱ	0.87	2.26	3.032 (4)	148
N2—H23···O2	0.85	1.87	2.707 (4)	167
N2—H21···O4ⁱ	0.96	1.92	2.832 (4)	159
N2—H21···O7ⁱⁱ	0.96	2.46	2.952 (4)	112
N2—H22···O5ⁱⁱⁱ	0.95	2.01	2.929 (4)	163
N3—H31···O4	0.87	2.22	2.843 (4)	129
N3—H32···O8^iv	0.87	2.18	2.788 (4)	127
N3—H33···OW1^v	0.87	2.40	2.997 (4)	126
OW1—H911···O11^v	0.94	1.74	2.676 (3)	175
OW1—H912···O5	0.93	1.78	2.687 (3)	166
OW2—H922···O11	0.94	1.95	2.885 (4)	173
OW2—H921···O10^v	0.94	1.79	2.726 (3)	179
OW3—H931···O8^vi	0.93	1.94	2.857 (4)	172
OW3—H932···O1ⁱ	0.94	2.04	2.954 (5)	163
OW4—H942···O5^vi	0.92	1.86	2.779 (3)	172
OW4—H941···O10^vii	0.93	1.86	2.761 (4)	163

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

Acknowledgements

Grateful thanks are expressed to Dr T. Roisnel (Centre de Diffractométrie X, UMR CNRS 6226) for his assistance with the data collection.

References

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