[(2R,3S)-Butane-1,2,3,4-tetraol-κ3O1,O2,O3](ethanol-κO)tris­(nitrato-κ2O,O′)samarium(III)

Xue, J.-H.; Hua, X.-H.; Yang, L.-M.; Xu, Y.-Z.; Wu, J.-G.

doi:10.1107/S1600536813003255

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages m182-m183

doi:10.1107/S1600536813003255

Open

access

[(2R,3S)-Butane-1,2,3,4-tetraol-κ³O¹,O²,O³](ethanol-κO)tris(nitrato-κ²O,O′)samarium(III)

Jun-Hui Xue,^a Xiao-Hui Hua,^b Li-Min Yang,^c ^* Yi-Zhuang Xu ^b and Jin-Guang Wu ^b

^aChemical Engineering College, Inner Mongolia University of Technology, People's Republic of China, ^bBeijing National Laboratory for Molecular Sciences, The State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing, People's Republic of China, and ^cState Key Laboratory of Nuclear Physics and Technology, Institute of Heavy Ion Physics, School of Physics, Peking University, Beijing, People's Republic of China
^*Correspondence e-mail: yanglm@pku.edu.cn

(Received 4 December 2012; accepted 31 January 2013; online 2 March 2013)

The title Sm^III–erythritol complex, [Sm(NO₃)₃(C₂H₆O)(C₄H₁₀O₄)], is isotypic with its Nd, Eu, Y, Gd, Tb and Ho analogues. The Sm^III cation exhibits a coordination number of ten and is chelated by a tridentate erythritol ligand and three bidentate nitrate anions. It is additionally coordinated by an O atom of an ethanol molecule, completing an irregular coordination sphere. The Sm—O bond lengths range from 2.416 (2) to 2.611 (2) Å. In the crystal, extensive O—H⋯O hydrogen bonding involving all hydroxy groups and some of the nitrate O atoms links the molecules into a three-dimensional network.

Related literature

For background to the coordination behaviour of sugars to metal cations, see: Gottschaldt & Schubert (2009 ). For the crystal structure of free erythritol, see: Bekoe & Powell (1959 ). For isotypic structures of the title compound, see: Yang et al. (2003 , 2004 , 2012 ); Hua et al. (2013 ).

Experimental

Crystal data

[Sm(NO₃)₃(C₂H₆O)(C₄H₁₀O₄)]
M_r = 504.57
Monoclinic, P 2₁ /c
a = 7.8537 (16) Å
b = 12.875 (3) Å
c = 15.252 (3) Å
β = 100.92 (3)°
V = 1514.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.96 mm⁻¹
T = 173 K
0.27 × 0.21 × 0.16 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.488, T_max = 1.000
10349 measured reflections
3446 independent reflections
3315 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.057
S = 1.22
3446 reflections
218 parameters
Δρ_max = 1.33 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.84	1.83	2.668 (3)	175
O2—H2⋯O7ⁱⁱ	0.84	1.96	2.802 (3)	174
O2—H2⋯O8ⁱⁱ	0.84	2.54	3.146 (4)	130
O3—H3⋯O12ⁱⁱⁱ	0.84	2.07	2.903 (3)	174
O4—H4⋯O8^iv	0.84	2.09	2.910 (4)	165
O4—H4⋯O6^iv	0.84	2.55	3.235 (3)	140
O5—H5⋯O11^v	0.84	2.00	2.827 (4)	167
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) -x, -y, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813003255/wm2711sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813003255/wm2711Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813003255/wm2711Isup3.cdx

checkCIF report

Comment top

Metal ions play important roles in the catalysis of numerous chemical and biological reactions. Interactions between carbohydrates (sugars) and metal ions may be involved in many biochemical processes (Gottschaldt & Schubert, 2009). Here the sugar alcohol erythritol was chosen as a model compound to study the coordination behavior of hydroxyl groups to f-block metal ions.

The molecular structure of the title complex, [Sm(C₄H₁₀O₄)(C₂H₅OH)(NO₃)₃], denoted as SmEN, where E stands for erythritol, N stands for nitrate, is shown in Fig. 1. In the title compound the Sm^III cation is 10-fold coordinated by three hydroxyl groups (O1, O2 and O3) from one erythritol molecule, by one hydroxyl group from ethanol (O5), and by three bidentate nitrate ions through O6, O7; O9, O10; O12, O13. The structure of SmEN is isotypic with its Nd, Eu, Y, Gd, Tb (Yang et al., 2003, 2004, 2012) and Ho (Hua et al., 2013) analogues. The Sm—O distances range from 2.416 (2) to 2.611 (2) Å, the average Sm—O distance being 2.499 Å. The C—C—C and the O—C–C bond angles of the central backbone in the free centrosymmetric erythritol molecule are 113° and 107°, respectively (Bekoe & Powell, 1959). After coordination, the C—C—C bond angles are 112.6 (3) and 116.7 (3)° and the O—C—C bond angles range from 104.0 (3) to 111.6 (3)° in SmEN, which indicates a subtle change of the conformation of erythritol.

The extensive hydrogen bond network in SmEN is formed by O—H···O hydrogen bonds from coordinating and uncoordinating hydroxyl groups of erythritol and ethanol and the nitrate O atoms. The coordinating hydroxyl groups O1 of erythritol forms a hydrogen bond with the uncoordinating O4 hydroxyl group of a neighbouring erythritol molecule. The coordinating O2 hydroxyl group forms a bifurcated hydrogen bonds with two oxygen atoms from a nitrate ion (O7, O8). The coordinating hydroxyl group O3 forms a hydrogen bond with an oxygen atom from another nitrate ion (O12). The non-coordinating hydroxyl group O4 is a donor of a bifurcated hydrogen bond to O8 and O6 from one nitrate ion. The ethanol hydroxy group (O5) forms a hydrogen bond with an oxygen atom from a nitrate ion (O11). Details of the hydrogen bonding are given in Table 1 and Fig. 2.

Related literature top

For background to the coordination behaviour of sugars to metal cations, see: Gottschaldt & Schubert (2009). For the crystal structure of free erythritol, see: Bekoe & Powell (1959). For isotypic structures of the title compound, see: Yang et al. (2003, 2004, 2012); Hua et al. (2013).

Experimental top

Sm(NO₃)₃^.6H₂O (3 mmol) and erythritol (3 mmol) were dissolved in 6 ml water and 6 ml ethanol. The solution was put on a water bath, and the temperature was raised to 353 K. Small aliquots of EtOH were periodically added to the solution during the heating process to prolong the reaction time. The resulting mixture was filtered and left for crystallization at room temperature. Suitable crystals for X-ray diffraction measuraments were obtained in the course of two weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. The packing of the title complex, showing hydrogen bond interactions as dashed lines.

[(2R,3S)-Butane-1,2,3,4-tetraol-κ³O¹,O²,O³](ethanol-κO)tris(nitrato-κ²O,O')samarium(III) top

Crystal data top

[Sm(NO₃)₃(C₂H₆O)(C₄H₁₀O₄)]	F(000) = 988
M_r = 504.57	D_x = 2.213 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5882 reflections
a = 7.8537 (16) Å	θ = 1.4–27.5°
b = 12.875 (3) Å	µ = 3.96 mm⁻¹
c = 15.252 (3) Å	T = 173 K
β = 100.92 (3)°	Block, colorless
V = 1514.4 (5) Å³	0.27 × 0.21 × 0.16 mm
Z = 4

Data collection top

Rigaku Saturn724+ CCD diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	3315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
ω scans fixed at = 45°	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −16→15
T_min = 0.488, T_max = 1.000	l = −19→19
10349 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.010P)² + 2.6923P] where P = (F_o² + 2F_c²)/3
3446 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 1.33 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Sm(NO₃)₃(C₂H₆O)(C₄H₁₀O₄)]	V = 1514.4 (5) Å³
M_r = 504.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8537 (16) Å	µ = 3.96 mm⁻¹
b = 12.875 (3) Å	T = 173 K
c = 15.252 (3) Å	0.27 × 0.21 × 0.16 mm
β = 100.92 (3)°

Data collection top

Rigaku Saturn724+ CCD diffractometer	3446 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3315 reflections with I > 2σ(I)
T_min = 0.488, T_max = 1.000	R_int = 0.035
10349 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.22	Δρ_max = 1.33 e Å⁻³
3446 reflections	Δρ_min = −0.72 e Å⁻³
218 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.12473 (2)	0.103866 (13)	0.245568 (11)	0.01311 (6)
O2	−0.1453 (3)	0.19005 (18)	0.26026 (15)	0.0152 (5)
H2	−0.1627	0.2536	0.2497	0.018*
O7	0.1854 (3)	−0.09504 (18)	0.26433 (17)	0.0191 (5)
O12	0.1760 (3)	0.2978 (2)	0.23049 (18)	0.0226 (6)
O9	−0.0707 (3)	0.0131 (2)	0.11892 (18)	0.0237 (6)
O3	−0.0744 (3)	0.00648 (18)	0.32999 (16)	0.0172 (5)
H3	−0.1087	−0.0539	0.3152	0.021*
O1	0.1328 (3)	0.17252 (18)	0.39375 (16)	0.0171 (5)
H1	0.1753	0.1387	0.4398	0.021*
O10	−0.0309 (3)	0.1772 (2)	0.10178 (17)	0.0219 (5)
O14	0.4196 (3)	0.3751 (2)	0.2861 (2)	0.0298 (6)
O11	−0.2048 (3)	0.0930 (2)	−0.00145 (18)	0.0284 (6)
O6	0.3562 (3)	0.00887 (19)	0.35122 (17)	0.0202 (5)
O4	−0.2725 (3)	−0.0768 (2)	0.45451 (17)	0.0217 (5)
H4	−0.3741	−0.0886	0.4274	0.026*
N1	0.3140 (4)	−0.0835 (2)	0.3280 (2)	0.0187 (6)
N2	−0.1050 (4)	0.0942 (2)	0.0709 (2)	0.0209 (7)
O13	0.3997 (3)	0.20661 (19)	0.28786 (18)	0.0233 (6)
O8	0.3934 (4)	−0.1577 (2)	0.36532 (19)	0.0288 (6)
O5	0.3062 (3)	0.0520 (2)	0.14084 (17)	0.0225 (6)
H5	0.2654	0.0050	0.1047	0.027*
N3	0.3355 (4)	0.2958 (2)	0.2693 (2)	0.0180 (6)
C5	0.4524 (4)	0.0950 (3)	0.1065 (3)	0.0218 (8)
H5A	0.5248	0.0378	0.0904	0.026*
H5B	0.5250	0.1374	0.1535	0.026*
C3	−0.2160 (4)	0.0631 (3)	0.3569 (2)	0.0155 (7)
H3A	−0.3252	0.0467	0.3137	0.019*
C4	−0.2402 (4)	0.0320 (3)	0.4494 (2)	0.0195 (7)
H4A	−0.1348	0.0504	0.4933	0.023*
H4B	−0.3388	0.0712	0.4650	0.023*
C2	−0.1785 (4)	0.1780 (3)	0.3500 (2)	0.0166 (7)
H2A	−0.2836	0.2190	0.3562	0.020*
C1	−0.0225 (4)	0.2200 (3)	0.4137 (2)	0.0191 (7)
H1A	−0.0164	0.2964	0.4072	0.023*
H1B	−0.0328	0.2042	0.4760	0.023*
C6	0.3896 (5)	0.1610 (3)	0.0262 (3)	0.0275 (9)
H6A	0.3223	0.1182	−0.0212	0.041*
H6B	0.4892	0.1912	0.0052	0.041*
H6C	0.3162	0.2168	0.0421	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.01387 (8)	0.01135 (10)	0.01389 (10)	−0.00053 (6)	0.00207 (6)	−0.00031 (7)
O2	0.0215 (12)	0.0087 (12)	0.0153 (12)	0.0035 (9)	0.0037 (9)	0.0039 (10)
O7	0.0174 (11)	0.0155 (13)	0.0231 (14)	−0.0022 (9)	0.0010 (10)	−0.0016 (11)
O12	0.0181 (12)	0.0197 (14)	0.0275 (14)	−0.0009 (10)	−0.0017 (10)	0.0055 (11)
O9	0.0284 (13)	0.0166 (13)	0.0248 (14)	−0.0026 (10)	0.0019 (11)	0.0012 (12)
O3	0.0183 (11)	0.0105 (12)	0.0238 (13)	−0.0014 (9)	0.0068 (9)	−0.0022 (10)
O1	0.0166 (11)	0.0180 (13)	0.0160 (12)	0.0031 (9)	0.0012 (9)	−0.0009 (10)
O10	0.0270 (13)	0.0205 (14)	0.0164 (13)	−0.0053 (10)	−0.0001 (10)	0.0012 (11)
O14	0.0291 (15)	0.0187 (14)	0.0410 (18)	−0.0112 (11)	0.0052 (12)	−0.0063 (13)
O11	0.0265 (14)	0.0382 (17)	0.0175 (14)	−0.0043 (12)	−0.0032 (10)	−0.0024 (13)
O6	0.0203 (12)	0.0134 (13)	0.0251 (14)	−0.0014 (9)	−0.0003 (10)	−0.0033 (11)
O4	0.0221 (12)	0.0227 (14)	0.0191 (13)	−0.0042 (10)	0.0007 (10)	0.0073 (11)
N1	0.0196 (14)	0.0170 (16)	0.0195 (16)	0.0000 (11)	0.0033 (11)	−0.0010 (13)
N2	0.0178 (14)	0.0254 (18)	0.0192 (16)	−0.0023 (12)	0.0026 (11)	−0.0017 (14)
O13	0.0179 (12)	0.0166 (13)	0.0341 (15)	−0.0003 (10)	0.0016 (10)	0.0005 (12)
O8	0.0349 (15)	0.0151 (14)	0.0336 (16)	0.0075 (11)	−0.0005 (12)	0.0065 (12)
O5	0.0235 (13)	0.0224 (14)	0.0238 (14)	−0.0037 (10)	0.0102 (10)	−0.0061 (12)
N3	0.0186 (14)	0.0140 (15)	0.0216 (16)	−0.0031 (11)	0.0045 (11)	0.0005 (13)
C5	0.0175 (16)	0.024 (2)	0.026 (2)	0.0004 (14)	0.0094 (14)	0.0040 (17)
C3	0.0139 (15)	0.0161 (18)	0.0167 (17)	0.0029 (12)	0.0033 (12)	0.0012 (14)
C4	0.0222 (17)	0.0183 (19)	0.0178 (18)	−0.0003 (14)	0.0036 (13)	0.0040 (15)
C2	0.0175 (15)	0.0160 (18)	0.0176 (18)	0.0031 (13)	0.0066 (13)	0.0007 (15)
C1	0.0207 (17)	0.0159 (18)	0.0215 (19)	0.0023 (13)	0.0062 (14)	−0.0031 (15)
C6	0.035 (2)	0.023 (2)	0.023 (2)	−0.0038 (16)	0.0037 (16)	0.0020 (17)

Geometric parameters (Å, º) top

Sm1—O1	2.416 (2)	O6—N1	1.267 (4)
Sm1—O5	2.427 (3)	O4—C4	1.429 (4)
Sm1—O2	2.441 (2)	O4—H4	0.8400
Sm1—O10	2.486 (3)	N1—O8	1.221 (4)
Sm1—O6	2.507 (2)	O13—N3	1.265 (4)
Sm1—O13	2.511 (2)	O5—C5	1.459 (4)
Sm1—O9	2.516 (3)	O5—H5	0.8400
Sm1—O3	2.537 (2)	C5—C6	1.496 (5)
Sm1—O12	2.547 (3)	C5—H5A	0.9900
Sm1—O7	2.611 (2)	C5—H5B	0.9900
O2—C2	1.448 (4)	C3—C4	1.512 (5)
O2—H2	0.8400	C3—C2	1.516 (5)
O7—N1	1.270 (4)	C3—H3A	1.0000
O12—N3	1.280 (4)	C4—H4A	0.9900
O9—N2	1.275 (4)	C4—H4B	0.9900
O3—C3	1.453 (4)	C2—C1	1.512 (5)
O3—H3	0.8400	C2—H2A	1.0000
O1—C1	1.448 (4)	C1—H1A	0.9900
O1—H1	0.8400	C1—H1B	0.9900
O10—N2	1.265 (4)	C6—H6A	0.9800
O14—N3	1.216 (4)	C6—H6B	0.9800
O11—N2	1.227 (4)	C6—H6C	0.9800

O1—Sm1—O5	143.28 (8)	C1—O1—H1	105.1
O1—Sm1—O2	67.50 (8)	Sm1—O1—H1	121.9
O5—Sm1—O2	144.50 (8)	N2—O10—Sm1	97.0 (2)
O1—Sm1—O10	127.41 (8)	N1—O6—Sm1	99.15 (18)
O5—Sm1—O10	77.06 (9)	C4—O4—H4	108.2
O2—Sm1—O10	67.52 (8)	O8—N1—O6	121.3 (3)
O1—Sm1—O6	71.93 (8)	O8—N1—O7	121.8 (3)
O5—Sm1—O6	81.04 (9)	O6—N1—O7	116.8 (3)
O2—Sm1—O6	134.38 (8)	O11—N2—O10	121.1 (3)
O10—Sm1—O6	158.09 (9)	O11—N2—O9	122.4 (3)
O1—Sm1—O13	72.42 (9)	O10—N2—O9	116.5 (3)
O5—Sm1—O13	74.36 (9)	N3—O13—Sm1	97.69 (18)
O2—Sm1—O13	117.19 (8)	C5—O5—Sm1	137.0 (2)
O10—Sm1—O13	106.37 (9)	C5—O5—H5	105.5
O6—Sm1—O13	66.94 (8)	Sm1—O5—H5	115.6
O1—Sm1—O9	142.39 (8)	O14—N3—O13	122.5 (3)
O5—Sm1—O9	73.49 (9)	O14—N3—O12	121.7 (3)
O2—Sm1—O9	82.37 (8)	O13—N3—O12	115.8 (3)
O10—Sm1—O9	51.15 (8)	O5—C5—C6	110.4 (3)
O6—Sm1—O9	121.97 (8)	O5—C5—H5A	109.6
O13—Sm1—O9	144.30 (9)	C6—C5—H5A	109.6
O1—Sm1—O3	67.40 (8)	O5—C5—H5B	109.6
O5—Sm1—O3	133.87 (8)	C6—C5—H5B	109.6
O2—Sm1—O3	63.15 (8)	H5A—C5—H5B	108.1
O10—Sm1—O3	112.83 (8)	O3—C3—C4	111.6 (3)
O6—Sm1—O3	82.77 (8)	O3—C3—C2	107.5 (3)
O13—Sm1—O3	135.47 (8)	C4—C3—C2	112.6 (3)
O9—Sm1—O3	79.34 (8)	O3—C3—H3A	108.3
O1—Sm1—O12	75.47 (8)	C4—C3—H3A	108.3
O5—Sm1—O12	95.05 (9)	C2—C3—H3A	108.3
O2—Sm1—O12	73.59 (8)	O4—C4—C3	111.5 (3)
O10—Sm1—O12	66.89 (8)	O4—C4—H4A	109.3
O6—Sm1—O12	115.38 (8)	C3—C4—H4A	109.3
O13—Sm1—O12	50.47 (8)	O4—C4—H4B	109.3
O9—Sm1—O12	118.03 (8)	C3—C4—H4B	109.3
O3—Sm1—O12	130.81 (8)	H4A—C4—H4B	108.0
O1—Sm1—O7	106.52 (8)	O2—C2—C1	107.5 (3)
O5—Sm1—O7	71.60 (8)	O2—C2—C3	104.0 (3)
O2—Sm1—O7	125.41 (8)	C1—C2—C3	116.7 (3)
O10—Sm1—O7	121.23 (8)	O2—C2—H2A	109.5
O6—Sm1—O7	49.91 (8)	C1—C2—H2A	109.5
O13—Sm1—O7	111.01 (8)	C3—C2—H2A	109.5
O9—Sm1—O7	72.58 (8)	O1—C1—C2	109.1 (3)
O3—Sm1—O7	64.96 (8)	O1—C1—H1A	109.9
O12—Sm1—O7	160.58 (8)	C2—C1—H1A	109.9
C2—O2—Sm1	110.65 (18)	O1—C1—H1B	109.9
C2—O2—H2	103.5	C2—C1—H1B	109.9
Sm1—O2—H2	122.5	H1A—C1—H1B	108.3
N1—O7—Sm1	94.10 (18)	C5—C6—H6A	109.5
N3—O12—Sm1	95.50 (19)	C5—C6—H6B	109.5
N2—O9—Sm1	95.30 (19)	H6A—C6—H6B	109.5
C3—O3—Sm1	118.28 (18)	C5—C6—H6C	109.5
C3—O3—H3	108.5	H6A—C6—H6C	109.5
Sm1—O3—H3	121.2	H6B—C6—H6C	109.5
C1—O1—Sm1	118.48 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.83	2.668 (3)	175
O2—H2···O7ⁱⁱ	0.84	1.96	2.802 (3)	174
O2—H2···O8ⁱⁱ	0.84	2.54	3.146 (4)	130
O3—H3···O12ⁱⁱⁱ	0.84	2.07	2.903 (3)	174
O4—H4···O8^iv	0.84	2.09	2.910 (4)	165
O4—H4···O6^iv	0.84	2.55	3.235 (3)	140
O5—H5···O11^v	0.84	2.00	2.827 (4)	167

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

Experimental details

Crystal data
Chemical formula	[Sm(NO₃)₃(C₂H₆O)(C₄H₁₀O₄)]
M_r	504.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.8537 (16), 12.875 (3), 15.252 (3)
β (°)	100.92 (3)
V (Å³)	1514.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.96
Crystal size (mm)	0.27 × 0.21 × 0.16

Data collection
Diffractometer	Rigaku Saturn724+ CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.488, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10349, 3446, 3315
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.057, 1.22
No. of reflections	3446
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.33, −0.72

Computer programs: CrystalClear (Rigaku, 2007), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.83	2.668 (3)	174.6
O2—H2···O7ⁱⁱ	0.84	1.96	2.802 (3)	174.3
O2—H2···O8ⁱⁱ	0.84	2.54	3.146 (4)	129.7
O3—H3···O12ⁱⁱⁱ	0.84	2.07	2.903 (3)	174.1
O4—H4···O8^iv	0.84	2.09	2.910 (4)	165.2
O4—H4···O6^iv	0.84	2.55	3.235 (3)	140.0
O5—H5···O11^v	0.84	2.00	2.827 (4)	166.8

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grants Nos. 50973003 and 21001009) and the National High-Tech R&D Program of China (863 Program) of MOST (No. 2010 A A03A406). Special thanks to Drs Hao, Wang and Liang for their assistance with the data collection.

References

Bekoe, A. & Powell, H. M. (1959). Proc. R. Soc. London Ser. A, 250, 301–315. CrossRef CAS Google Scholar
Gottschaldt, M. & Schubert, U. S. (2009). Chem. Eur. J. 15, 1548–1557. Web of Science CrossRef PubMed CAS Google Scholar
Hua, X.-H., Xue, J.-H., Yang, L.-M., Xu, Y.-Z. & Wu, J.-G. (2013). Acta Cryst. E69, m162–m163. CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Inc., Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, L. M., Hua, X. H., Xue, J. H., Pan, Q. H., Yu, L., Li, W. H., Xu, Y. Z., Zhao, G. Z., Liu, L. M., Liu, K. X., Chen, J. E. & Wu, J. G. (2012). Inorg. Chem. 51, 499–510. Web of Science CSD CrossRef CAS PubMed Google Scholar
Yang, L. M., Su, Y. L., Xu, Y. Z., Wang, Z. M., Guo, Z. H., Weng, S. F., Yan, C. H., Zhang, S. W. & Wu, J. G. (2003). Inorg. Chem. 42, 5844–5856. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yang, L. M., Su, Y. L., Xu, Y. Z., Zhang, S. W., Wu, J. G. & Zhao, K. (2004). J. Inorg. Biochem. 98, 1251–1260. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.