Poly[dimethyl­ammonium [aquadi-μ2-oxalato-samarate(III)] trihydrate]

Lv, Y.-K.; Gan, L.-H.; Liu, M.-X.; Xiong, W.

doi:10.1107/S1600536811020058

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m836

doi:10.1107/S1600536811020058

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Poly[dimethylammonium [aquadi-μ₂-oxalato-samarate(III)] trihydrate]

Yao-Kang Lv,^a Li-Hua Gan,^a ^* Ming-Xian Liu ^a and Wei Xiong ^a

^aDepartment of Chemistry, Tongji University, Shanghai 200092, People's Republic of China
^*Correspondence e-mail: ganlh@tongji.edu.cn

(Received 11 May 2011; accepted 26 May 2011; online 4 June 2011)

In the title complex, {(C₂H₈N)[Sm(C₂O₄)₂(H₂O)]·3H₂O}_n, the Sm^III atom is chelated by four oxalate ligands and one water molecule forming a distorted tricapped trigonal–prismatic geometry. Each oxalate ligand chelates to two Sm^III atoms, generating a three-dimensional anionic network with cavities in which the ammonium cations and lattice water molecules reside. Various O—H⋯O, N—H⋯O and C—H⋯O hydrogen-bonding interactions further stablize the crystal structure.

Related literature

For general background to the rational design and synthesis of metal-organic polymers, see: Kim et al. (1998 ); Lv et al. (2011 ). For related structures, see: Lv et al. (2010 ); Trombe & Mohanu (2004 ). The structure of the isotypic Eu^III compound was reported by Yang et al. (2005 ), and the Dy^III compound was reported by Ye & Lin (2010 ).

Experimental

Crystal data

(C₂H₈N)[Sm(C₂O₄)₂(H₂O)]·3H₂O
M_r = 444.55
Monoclinic, P 2₁ /c
a = 9.6711 (3) Å
b = 11.7849 (3) Å
c = 14.3863 (4) Å
β = 122.276 (2)°
V = 1386.30 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.30 mm⁻¹
T = 296 K
0.17 × 0.14 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.36, T_max = 0.43
12866 measured reflections
3225 independent reflections
2739 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.061
S = 1.03
3225 reflections
207 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2Wⁱ	0.82 (2)	1.95 (2)	2.764 (5)	174 (5)
O1W—H1WB⋯O2Wⁱⁱ	0.83 (2)	2.03 (2)	2.852 (5)	172 (4)
O2W—H2WA⋯O6ⁱⁱⁱ	0.81 (2)	2.26 (2)	3.065 (5)	175 (6)
O2W—H2WA⋯O7^iv	0.81 (2)	2.47 (5)	3.023 (5)	126 (5)
O2W—H2WB⋯O4W	0.80 (2)	2.51 (2)	3.306 (7)	179 (6)
O2W—H2WB⋯O3W^v	0.80 (2)	2.64 (5)	3.039 (8)	113 (5)
O3W—H3WA⋯O2	0.84 (2)	2.08 (3)	2.845 (5)	151 (6)
O3W—H3WB⋯O4W^iv	0.82 (2)	1.98 (2)	2.796 (6)	172 (8)
O4W—H4WA⋯O1^vi	0.83 (2)	2.15 (2)	2.967 (5)	169 (6)
O4W—H4WB⋯O3^vii	0.82 (2)	2.11 (2)	2.898 (5)	160 (6)
N1—H1A⋯O3W	0.90	1.85	2.744 (6)	171
N1—H1B⋯O8^vi	0.90	1.99	2.864 (5)	163
N1—H1B⋯O1W^vi	0.90	2.50	3.071 (5)	122
C5—H5C⋯O4ⁱⁱⁱ	0.96	2.53	3.283 (7)	135
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y, z-1; (iii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020058/om2429sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020058/om2429Isup2.hkl

checkCIF report

Comment top

Carbohydrates and their derivatives are the most widely distributed naturally occurring compounds and are indispensable to living organisms as an energy source and building blocks. Many carbohydrate-derived ligands were prepared and occasionally lead to novel and versatile metal-organic polymers with interesting structures (Kim et al., 1998; Lv et al., 2011). Oxalate, which usually represent one of the products of the degradation of carbohydrates, is one of the simplest multidentate organic ligands potentially able to bridge metal ions in a bidentate chelating manner (Lv et al., 2010; Trombe & Mohanu, 2004). We report herein the synthesis and structure of a new samarium(III) complex, (C₂H₈N)[Sm(C₂O₄)₂(H₂O)].3H₂O. The oxalate ligands in this complex arise from the decomposition of potassium hydrogen saccharate.

Single-crystal X-ray diffraction analysis revealed that the title complex crystallizes in the monoclinic system with space group P2₁/c, and is isostructural with its Eu^III analogue (Yang et al., 2005) and Dy^III analogues (Ye & Lin, 2010). As shown in Fig. 1, the Sm^III atom is chelated by four oxalate ligands and one water molecule forming a distorted tricapped trigonal-prismatic geometry. Each oxalate ligand bridges two Sm^III atoms, generating a three-dimensional anionic network with cavities where the ammonium cations and lattice water molecules reside (Fig. 2). Furthermore, there are various hydrogen-bonding interactions (N—H···O, O—H···O and C—H···O) stablizing the crystal framework.

Related literature top

For general background to the rational design and synthesis of metal-organic polymers, see: Kim et al. (1998); Lv et al. (2011). For related structures, see: Lv et al. (2010); Trombe & Mohanu (2004). The structure of the isotypic Eu^III compound was reported by Yang et al. (2005), and the Dy^III compound was reported by Ye & Lin (2010).

Experimental top

A mixture of potassium hydrogen saccharate (0.248 g, 1.0 mmol), Sm(NO₃)₃.6H₂O (0.222 g, 0.5 mmol) and N, N-Dimethylformamide (20 ml) was stirred and heated at 373 K for 60 minute, the resulted colorless solution was kept at 20°C. Colorless block crystals suitable for X-ray crystallographic study were crystralized via slow evaporation in 2 weeks.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Structure of the title compound showing the atom labeling, thermal displacement parameters are shown at the 30% probability level. All the hydrogen atoms are omitted for clarity. [Symmetry code: (i) -x + 1, y + 1/2, -z + 1/2 (ii) -x + 1, -y + 2, -z + 1; (iii) -x + 2, -y + 2, -z + 1.]
	Fig. 2. View of the three-dimensional framework. All the hydrogen atoms are omitted for clarity.

Poly[dimethylammonium [aquadi-µ₂-oxalato-samarate(III)] trihydrate] top

Crystal data top

(C₂H₈N)[Sm(C₂O₄)₂(H₂O)]·3H₂O	F(000) = 868
M_r = 444.55	D_x = 2.130 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3706 reflections
a = 9.6711 (3) Å	θ = 2.5–27.7°
b = 11.7849 (3) Å	µ = 4.30 mm⁻¹
c = 14.3863 (4) Å	T = 296 K
β = 122.276 (2)°	Block, colourless
V = 1386.30 (7) Å³	0.17 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3225 independent reflections
Radiation source: fine-focus sealed tube	2739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.36, T_max = 0.43	k = −15→14
12866 measured reflections	l = −16→18

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0215P)² + 2.7236P] where P = (F_o² + 2F_c²)/3
3225 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 0.69 e Å⁻³
12 restraints	Δρ_min = −0.98 e Å⁻³

Crystal data top

(C₂H₈N)[Sm(C₂O₄)₂(H₂O)]·3H₂O	V = 1386.30 (7) Å³
M_r = 444.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6711 (3) Å	µ = 4.30 mm⁻¹
b = 11.7849 (3) Å	T = 296 K
c = 14.3863 (4) Å	0.17 × 0.14 × 0.08 mm
β = 122.276 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	3225 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2739 reflections with I > 2σ(I)
T_min = 0.36, T_max = 0.43	R_int = 0.039
12866 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	12 restraints
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.69 e Å⁻³
3225 reflections	Δρ_min = −0.98 e Å⁻³
207 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 > 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

	x	y	z	U_iso*/U_eq
Sm1	0.61680 (2)	0.983582 (14)	0.330364 (15)	0.01793 (7)
O1	0.7036 (3)	0.7832 (2)	0.3435 (2)	0.0284 (6)
O2	0.6156 (3)	0.6045 (2)	0.3014 (2)	0.0293 (7)
O3	0.3063 (3)	0.6799 (2)	0.1732 (2)	0.0242 (6)
O4	0.3978 (3)	0.8576 (2)	0.2047 (2)	0.0241 (6)
O6	0.5172 (3)	0.8817 (2)	0.4343 (2)	0.0286 (6)
O7	0.5330 (4)	1.1081 (2)	0.4324 (3)	0.0334 (7)
O8	0.8912 (3)	0.9847 (2)	0.3572 (2)	0.0253 (6)
O9	0.8415 (3)	0.9876 (2)	0.5228 (2)	0.0289 (6)
O1W	0.6084 (4)	0.9755 (3)	0.1530 (2)	0.0330 (7)
H1WA	0.608 (6)	1.033 (2)	0.121 (3)	0.040*
H1WB	0.544 (5)	0.932 (3)	0.103 (3)	0.040*
O2W	1.3864 (6)	0.8423 (3)	0.9661 (4)	0.0614 (11)
H2WA	1.426 (7)	0.783 (3)	0.962 (5)	0.074*
H2WB	1.306 (5)	0.827 (5)	0.966 (6)	0.074*
O3W	0.8362 (7)	0.5053 (4)	0.5101 (4)	0.0799 (15)
H3WA	0.793 (9)	0.521 (5)	0.443 (2)	0.096*
H3WB	0.876 (8)	0.442 (3)	0.517 (5)	0.096*
O4W	1.0543 (5)	0.7816 (4)	0.9682 (4)	0.0767 (14)
H4WA	0.958 (3)	0.763 (6)	0.942 (5)	0.092*
H4WB	1.106 (6)	0.742 (5)	1.024 (4)	0.092*
N1	0.9284 (5)	0.6293 (4)	0.6960 (3)	0.0430 (10)
H1A	0.8867	0.5890	0.6334	0.052*
H1B	0.8947	0.5962	0.7369	0.052*
C1	0.5958 (4)	0.7095 (3)	0.2949 (3)	0.0212 (8)
C2	0.4172 (4)	0.7536 (3)	0.2173 (3)	0.0200 (7)
C3	0.4950 (4)	0.9348 (3)	0.5004 (3)	0.0238 (8)
C4	1.0168 (4)	0.9999 (3)	0.4541 (3)	0.0202 (8)
C5	1.1056 (7)	0.6231 (7)	0.7555 (5)	0.076 (2)
H5A	1.1392	0.5450	0.7687	0.091*
H5B	1.1514	0.6621	0.8243	0.091*
H5C	1.1433	0.6579	0.7126	0.091*
C6	0.8628 (9)	0.7443 (6)	0.6685 (6)	0.083 (2)
H6A	0.7455	0.7414	0.6256	0.100*
H6B	0.9012	0.7813	0.6269	0.100*
H6C	0.8987	0.7861	0.7349	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.01682 (10)	0.01446 (10)	0.01891 (10)	−0.00015 (7)	0.00713 (8)	−0.00032 (7)
O1	0.0186 (14)	0.0194 (14)	0.0365 (17)	−0.0004 (10)	0.0076 (12)	−0.0044 (11)
O2	0.0225 (14)	0.0156 (13)	0.0327 (16)	0.0014 (10)	0.0032 (12)	−0.0002 (11)
O3	0.0199 (13)	0.0176 (13)	0.0313 (15)	0.0008 (10)	0.0111 (12)	−0.0021 (11)
O4	0.0222 (14)	0.0171 (13)	0.0234 (14)	0.0010 (10)	0.0057 (12)	0.0003 (10)
O6	0.0358 (16)	0.0225 (14)	0.0311 (16)	−0.0052 (11)	0.0203 (13)	−0.0054 (11)
O7	0.0479 (18)	0.0213 (14)	0.0428 (18)	0.0052 (12)	0.0322 (16)	0.0063 (12)
O8	0.0199 (13)	0.0337 (15)	0.0169 (13)	−0.0009 (11)	0.0061 (11)	−0.0030 (11)
O9	0.0195 (14)	0.0437 (17)	0.0235 (14)	−0.0032 (12)	0.0114 (12)	−0.0030 (12)
O1W	0.0363 (17)	0.0349 (17)	0.0209 (15)	−0.0056 (13)	0.0108 (13)	−0.0013 (12)
O2W	0.073 (3)	0.035 (2)	0.063 (3)	0.0036 (18)	0.028 (2)	0.0070 (19)
O3W	0.084 (3)	0.078 (3)	0.047 (3)	0.027 (3)	0.014 (3)	−0.003 (2)
O4W	0.056 (3)	0.053 (3)	0.069 (3)	−0.008 (2)	−0.002 (2)	0.014 (2)
N1	0.035 (2)	0.057 (3)	0.036 (2)	−0.0080 (18)	0.0180 (18)	0.0077 (18)
C1	0.0196 (19)	0.0201 (19)	0.0190 (18)	0.0007 (13)	0.0069 (16)	−0.0017 (14)
C2	0.0209 (19)	0.0206 (19)	0.0171 (17)	0.0011 (14)	0.0092 (15)	0.0001 (14)
C3	0.0196 (18)	0.025 (2)	0.0225 (19)	0.0000 (14)	0.0081 (15)	0.0006 (15)
C4	0.0217 (19)	0.0137 (17)	0.0190 (18)	−0.0016 (13)	0.0068 (15)	0.0015 (13)
C5	0.041 (3)	0.126 (6)	0.051 (4)	−0.010 (4)	0.018 (3)	0.020 (4)
C6	0.104 (6)	0.067 (4)	0.086 (5)	0.012 (4)	0.056 (5)	0.017 (4)

Geometric parameters (Å, º) top

Sm1—O4	2.422 (3)	O2W—H2WA	0.811 (19)
Sm1—O3ⁱ	2.440 (2)	O2W—H2WB	0.798 (19)
Sm1—O9	2.442 (3)	O3W—H3WA	0.839 (19)
Sm1—O8	2.469 (3)	O3W—H3WB	0.819 (19)
Sm1—O2ⁱ	2.474 (3)	O4W—H4WA	0.83 (2)
Sm1—O6	2.479 (3)	O4W—H4WB	0.823 (19)
Sm1—O1	2.479 (3)	N1—C5	1.452 (7)
Sm1—O7	2.497 (3)	N1—C6	1.459 (8)
Sm1—O1W	2.512 (3)	N1—H1A	0.9001
O1—C1	1.246 (4)	N1—H1B	0.9001
O2—C1	1.248 (4)	C1—C2	1.562 (5)
O2—Sm1ⁱⁱ	2.474 (3)	C3—O7ⁱⁱⁱ	1.242 (5)
O3—C2	1.257 (4)	C3—C3ⁱⁱⁱ	1.541 (8)
O3—Sm1ⁱⁱ	2.440 (2)	C4—O9^iv	1.234 (5)
O4—C2	1.238 (4)	C4—C4^iv	1.519 (8)
O6—C3	1.248 (5)	C5—H5A	0.9600
O7—C3ⁱⁱⁱ	1.242 (5)	C5—H5B	0.9600
O8—C4	1.282 (4)	C5—H5C	0.9600
O9—C4^iv	1.234 (5)	C6—H6A	0.9600
O1W—H1WA	0.817 (18)	C6—H6B	0.9600
O1W—H1WB	0.828 (18)	C6—H6C	0.9600

O4—Sm1—O3ⁱ	136.09 (9)	C3—O6—Sm1	119.8 (2)
O4—Sm1—O9	138.78 (9)	C3ⁱⁱⁱ—O7—Sm1	119.5 (2)
O3ⁱ—Sm1—O9	84.76 (9)	C4—O8—Sm1	119.1 (2)
O4—Sm1—O8	123.92 (9)	C4^iv—O9—Sm1	119.7 (2)
O3ⁱ—Sm1—O8	71.56 (9)	Sm1—O1W—H1WA	122 (3)
O9—Sm1—O8	65.88 (9)	Sm1—O1W—H1WB	120 (3)
O4—Sm1—O2ⁱ	72.94 (8)	H1WA—O1W—H1WB	104 (3)
O3ⁱ—Sm1—O2ⁱ	66.43 (8)	H2WA—O2W—H2WB	108 (3)
O9—Sm1—O2ⁱ	138.73 (9)	H3WA—O3W—H3WB	105 (3)
O8—Sm1—O2ⁱ	125.24 (9)	H4WA—O4W—H4WB	105 (3)
O4—Sm1—O6	71.76 (9)	C5—N1—C6	114.3 (5)
O3ⁱ—Sm1—O6	133.88 (9)	C5—N1—H1A	108.6
O9—Sm1—O6	73.91 (9)	C6—N1—H1A	108.8
O8—Sm1—O6	129.79 (9)	C5—N1—H1B	108.5
O2ⁱ—Sm1—O6	104.74 (10)	C6—N1—H1B	108.8
O4—Sm1—O1	66.34 (8)	H1A—N1—H1B	107.6
O3ⁱ—Sm1—O1	144.12 (9)	O1—C1—O2	126.9 (3)
O9—Sm1—O1	82.65 (9)	O1—C1—C2	116.3 (3)
O8—Sm1—O1	72.62 (9)	O2—C1—C2	116.8 (3)
O2ⁱ—Sm1—O1	137.62 (9)	O4—C2—O3	126.0 (3)
O6—Sm1—O1	73.62 (9)	O4—C2—C1	117.2 (3)
O4—Sm1—O7	111.72 (10)	O3—C2—C1	116.8 (3)
O3ⁱ—Sm1—O7	69.72 (9)	O7ⁱⁱⁱ—C3—O6	125.9 (4)
O9—Sm1—O7	72.18 (10)	O7ⁱⁱⁱ—C3—C3ⁱⁱⁱ	116.9 (4)
O8—Sm1—O7	124.34 (9)	O6—C3—C3ⁱⁱⁱ	117.2 (4)
O2ⁱ—Sm1—O7	70.42 (10)	O9^iv—C4—O8	125.5 (4)
O6—Sm1—O7	64.99 (9)	O9^iv—C4—C4^iv	119.2 (4)
O1—Sm1—O7	135.89 (10)	O8—C4—C4^iv	115.3 (4)
O4—Sm1—O1W	71.17 (10)	N1—C5—H5A	109.5
O3ⁱ—Sm1—O1W	81.92 (10)	N1—C5—H5B	109.5
O9—Sm1—O1W	132.76 (10)	H5A—C5—H5B	109.5
O8—Sm1—O1W	66.90 (9)	N1—C5—H5C	109.5
O2ⁱ—Sm1—O1W	73.75 (10)	H5A—C5—H5C	109.5
O6—Sm1—O1W	141.50 (9)	H5B—C5—H5C	109.5
O1—Sm1—O1W	82.35 (10)	N1—C6—H6A	109.5
O7—Sm1—O1W	140.82 (10)	N1—C6—H6B	109.5
C1—O1—Sm1	118.3 (2)	H6A—C6—H6B	109.5
C1—O2—Sm1ⁱⁱ	118.2 (2)	N1—C6—H6C	109.5
C2—O3—Sm1ⁱⁱ	118.6 (2)	H6A—C6—H6C	109.5
C2—O4—Sm1	119.6 (2)	H6B—C6—H6C	109.5

O4—Sm1—O1—C1	−10.9 (3)	O4—Sm1—O8—C4	−141.7 (2)
O3ⁱ—Sm1—O1—C1	−148.3 (3)	O3ⁱ—Sm1—O8—C4	84.6 (2)
O9—Sm1—O1—C1	141.3 (3)	O9—Sm1—O8—C4	−7.9 (2)
O8—Sm1—O1—C1	−151.8 (3)	O2ⁱ—Sm1—O8—C4	125.8 (2)
O2ⁱ—Sm1—O1—C1	−28.1 (4)	O6—Sm1—O8—C4	−47.7 (3)
O6—Sm1—O1—C1	66.0 (3)	O1—Sm1—O8—C4	−97.6 (3)
O7—Sm1—O1—C1	86.5 (3)	O7—Sm1—O8—C4	36.7 (3)
O1W—Sm1—O1—C1	−83.6 (3)	O1W—Sm1—O8—C4	173.5 (3)
O3ⁱ—Sm1—O4—C2	158.7 (3)	O4—Sm1—O9—C4^iv	122.0 (3)
O9—Sm1—O4—C2	−31.0 (3)	O3ⁱ—Sm1—O9—C4^iv	−64.8 (3)
O8—Sm1—O4—C2	60.2 (3)	O8—Sm1—O9—C4^iv	7.4 (3)
O2ⁱ—Sm1—O4—C2	−178.4 (3)	O2ⁱ—Sm1—O9—C4^iv	−109.3 (3)
O6—Sm1—O4—C2	−66.0 (3)	O6—Sm1—O9—C4^iv	156.6 (3)
O1—Sm1—O4—C2	13.6 (3)	O1—Sm1—O9—C4^iv	81.6 (3)
O7—Sm1—O4—C2	−118.4 (3)	O7—Sm1—O9—C4^iv	−135.1 (3)
O1W—Sm1—O4—C2	103.4 (3)	O1W—Sm1—O9—C4^iv	9.2 (3)
O4—Sm1—O6—C3	−136.1 (3)	Sm1—O1—C1—O2	−172.2 (3)
O3ⁱ—Sm1—O6—C3	1.2 (3)	Sm1—O1—C1—C2	8.1 (4)
O9—Sm1—O6—C3	67.1 (3)	Sm1ⁱⁱ—O2—C1—O1	−169.5 (3)
O8—Sm1—O6—C3	104.5 (3)	Sm1ⁱⁱ—O2—C1—C2	10.2 (5)
O2ⁱ—Sm1—O6—C3	−70.1 (3)	Sm1—O4—C2—O3	165.1 (3)
O1—Sm1—O6—C3	154.0 (3)	Sm1—O4—C2—C1	−15.0 (4)
O7—Sm1—O6—C3	−10.4 (3)	Sm1ⁱⁱ—O3—C2—O4	162.8 (3)
O1W—Sm1—O6—C3	−152.4 (3)	Sm1ⁱⁱ—O3—C2—C1	−17.2 (4)
O4—Sm1—O7—C3ⁱⁱⁱ	66.9 (3)	O1—C1—C2—O4	4.4 (5)
O3ⁱ—Sm1—O7—C3ⁱⁱⁱ	−160.3 (3)	O2—C1—C2—O4	−175.4 (4)
O9—Sm1—O7—C3ⁱⁱⁱ	−69.4 (3)	O1—C1—C2—O3	−175.7 (3)
O8—Sm1—O7—C3ⁱⁱⁱ	−111.7 (3)	O2—C1—C2—O3	4.5 (5)
O2ⁱ—Sm1—O7—C3ⁱⁱⁱ	128.4 (3)	Sm1—O6—C3—O7ⁱⁱⁱ	−169.7 (3)
O6—Sm1—O7—C3ⁱⁱⁱ	10.8 (3)	Sm1—O6—C3—C3ⁱⁱⁱ	9.6 (5)
O1—Sm1—O7—C3ⁱⁱⁱ	−11.0 (4)	Sm1—O8—C4—O9^iv	−173.2 (3)
O1W—Sm1—O7—C3ⁱⁱⁱ	153.4 (3)	Sm1—O8—C4—C4^iv	7.9 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2W^iv	0.82 (2)	1.95 (2)	2.764 (5)	174 (5)
O1W—H1WB···O2W^v	0.83 (2)	2.03 (2)	2.852 (5)	172 (4)
O2W—H2WA···O6^vi	0.81 (2)	2.26 (2)	3.065 (5)	175 (6)
O2W—H2WA···O7^vii	0.81 (2)	2.47 (5)	3.023 (5)	126 (5)
O2W—H2WB···O4W	0.80 (2)	2.51 (2)	3.306 (7)	179 (6)
O2W—H2WB···O3W^viii	0.80 (2)	2.64 (5)	3.039 (8)	113 (5)
O3W—H3WA···O2	0.84 (2)	2.08 (3)	2.845 (5)	151 (6)
O3W—H3WB···O4W^vii	0.82 (2)	1.98 (2)	2.796 (6)	172 (8)
O4W—H4WA···O1^ix	0.83 (2)	2.15 (2)	2.967 (5)	169 (6)
O4W—H4WB···O3^x	0.82 (2)	2.11 (2)	2.898 (5)	160 (6)
N1—H1A···O3W	0.90	1.85	2.744 (6)	171
N1—H1B···O8^ix	0.90	1.99	2.864 (5)	163
N1—H1B···O1W^ix	0.90	2.50	3.071 (5)	122
C5—H5C···O4^vi	0.96	2.53	3.283 (7)	135

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

Experimental details

Crystal data
Chemical formula	(C₂H₈N)[Sm(C₂O₄)₂(H₂O)]·3H₂O
M_r	444.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6711 (3), 11.7849 (3), 14.3863 (4)
β (°)	122.276 (2)
V (Å³)	1386.30 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.30
Crystal size (mm)	0.17 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.36, 0.43
No. of measured, independent and observed [I > 2σ(I)] reflections	12866, 3225, 2739
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.061, 1.03
No. of reflections	3225
No. of parameters	207
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.98

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2Wⁱ	0.817 (18)	1.95 (2)	2.764 (5)	174 (5)
O1W—H1WB···O2Wⁱⁱ	0.828 (18)	2.03 (2)	2.852 (5)	172 (4)
O2W—H2WA···O6ⁱⁱⁱ	0.811 (19)	2.26 (2)	3.065 (5)	175 (6)
O2W—H2WA···O7^iv	0.811 (19)	2.47 (5)	3.023 (5)	126 (5)
O2W—H2WB···O4W	0.798 (19)	2.51 (2)	3.306 (7)	179 (6)
O2W—H2WB···O3W^v	0.798 (19)	2.64 (5)	3.039 (8)	113 (5)
O3W—H3WA···O2	0.839 (19)	2.08 (3)	2.845 (5)	151 (6)
O3W—H3WB···O4W^iv	0.819 (19)	1.98 (2)	2.796 (6)	172 (8)
O4W—H4WA···O1^vi	0.83 (2)	2.15 (2)	2.967 (5)	169 (6)
O4W—H4WB···O3^vii	0.823 (19)	2.11 (2)	2.898 (5)	160 (6)
N1—H1A···O3W	0.90	1.85	2.744 (6)	171
N1—H1B···O8^vi	0.90	1.99	2.864 (5)	163
N1—H1B···O1W^vi	0.90	2.50	3.071 (5)	122
C5—H5C···O4ⁱⁱⁱ	0.96	2.53	3.283 (7)	135

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

Acknowledgements

The present work was supported financially by the National Natural Science Foundation of China (No. 20973127) and Shanghai Nanotechnology Promotion Center (No. 0952nm00800).

References

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