[(2R,3S)-Butane-1,2,3,4-tetraol-κ(3) O (1),O (2),O (3)](ethanol-κO)tris-(nitrato-κ(2) O,O')samarium(III).

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 mol-ecule, 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 hy-droxy groups and some of the nitrate O atoms links the mol-ecules 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 = 504.57

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.057

S = 1.22

3446 reflections

218 parameters

Δρmax = 1.33 e Å−3

Δρmin = −0.72 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813003255/wm2711sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003255/wm2711Isup3.cdx

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sm(NO3)3(C2H6O)(C4H10O4)]	F(000) = 988
Mr = 504.57	Dx = 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

Rigaku Saturn724+ CCD diffractometer	3446 independent reflections
Radiation source: fine-focus sealed tube	3315 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.1°
ω scans fixed at = 45°	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −16→15
Tmin = 0.488, Tmax = 1.000	l = −19→19
10349 measured reflections

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(Fo2) + (0.010P)2 + 2.6923P] where P = (Fo2 + 2Fc2)/3
3446 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 1.33 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O8iv	0.84	2.09	2.910 (4)	165
O4—H4···O6iv	0.84	2.55	3.235 (3)	140
O5—H5···O11v	0.84	2.00	2.827 (4)	167

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⋯O8iv	0.84	2.09	2.910 (4)	165
O4—H4⋯O6iv	0.84	2.55	3.235 (3)	140
O5—H5⋯O11v	0.84	2.00	2.827 (4)	167

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .