(Butane-1,2,3,4-tetraol-κ(3) O (1),O (2),O (3))(ethanol-κO)tris-(nitrato-κ(2) O,O')erbium(III).

In the title Er(III)-erythritol complex, [Er(NO3)3(C2H5OH)(C4H10O4)], the Er(III) cation is chelated by one erythritol mol-ecule, three nitrate anions and an ethanol mol-ecule, completing an irregular ErO10 coordination geometry. The Er-O bond lengths are in the range 2.348 (3)-2.583 (3) Å. In the crystal, extensive O-H⋯O hydrogen bonding links the mol-ecules into a three-dimensional supra-molecular structure.

Related literature

For crystal structures of related lanthanide nitrate–erythritol complexes, see: Gyurcsik & Nagy (2000 ▶); Yang et al. (2003 ▶, 2004 ▶, 2012 ▶). For the isotypic HoIII complex, see: Hua et al. (2013 ▶). For the structure of erythritol, see: Bekoe & Powell (1959 ▶).

Experimental

Crystal data

[Er(NO3)3(C2H6O)(C4H10O4)]

M = 521.48

Monoclinic,

a = 7.7521 (16) Å

b = 12.772 (3) Å

c = 15.121 (3) Å

β = 100.26 (3)°

V = 1473.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.78 mm−1

T = 173 K

0.23 × 0.20 × 0.06 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.12, T max = 0.35

10846 measured reflections

3359 independent reflections

3174 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.063

S = 1.20

3359 reflections

218 parameters

H-atom parameters constrained

Δρmax = 1.46 e Å−3

Δρmin = −0.62 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: 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/S1600536813008003/xu5657sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008003/xu5657Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008003/xu5657Isup3.cdx

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

[Er(NO3)3(C2H6O)(C4H10O4)]	F(000) = 1012
Mr = 521.48	Dx = 2.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5453 reflections
a = 7.7521 (16) Å	θ = 2.1–27.5°
b = 12.772 (3) Å	µ = 5.78 mm−1
c = 15.121 (3) Å	T = 173 K
β = 100.26 (3)°	Plate, pink
V = 1473.3 (5) Å3	0.23 × 0.20 × 0.06 mm
Z = 4

Rigaku Saturn724+ CCD diffractometer	3359 independent reflections
Radiation source: fine-focus sealed tube	3174 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 at fixed χ = 45°	h = −10→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −16→16
Tmin = 0.12, Tmax = 0.35	l = −19→19
10846 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.021P)2 + 2.6512P] where P = (Fo2 + 2Fc2)/3
3359 reflections	(Δ/σ)max = 0.002
218 parameters	Δρmax = 1.46 e Å−3
0 restraints	Δρmin = −0.62 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
Er1	0.62537 (2)	0.895819 (13)	0.247063 (10)	0.01275 (7)
O9	0.6818 (4)	1.0948 (2)	0.26286 (19)	0.0189 (6)
O13	0.6726 (4)	0.7044 (2)	0.23165 (19)	0.0204 (6)
O6	0.4323 (4)	0.9877 (2)	0.12708 (19)	0.0228 (6)
O14	0.9187 (4)	0.6272 (2)	0.2866 (2)	0.0271 (7)
O10	0.8493 (4)	0.9889 (2)	0.35026 (19)	0.0182 (6)
O11	0.8904 (4)	1.1563 (2)	0.3659 (2)	0.0265 (7)
N1	0.4019 (5)	0.9082 (3)	0.0754 (2)	0.0200 (8)
O7	0.4806 (4)	0.8252 (2)	0.10336 (18)	0.0220 (6)
O8	0.3011 (4)	0.9117 (3)	0.0031 (2)	0.0280 (7)
N3	0.8336 (5)	0.7066 (3)	0.2691 (2)	0.0189 (7)
N2	0.8098 (5)	1.0823 (3)	0.3274 (2)	0.0179 (7)
O5	0.8049 (4)	0.9494 (2)	0.14542 (19)	0.0206 (6)
H5	0.7677	1.0027	0.1153	0.025*
C5	0.9524 (6)	0.9070 (4)	0.1084 (3)	0.0240 (10)
H5A	1.0284	0.8651	0.1549	0.029*
H5B	1.0233	0.9653	0.0906	0.029*
O12	0.8972 (4)	0.7972 (2)	0.2864 (2)	0.0220 (6)
C6	0.8876 (6)	0.8393 (4)	0.0278 (3)	0.0271 (10)
H6A	0.8125	0.7837	0.0447	0.041*
H6B	0.9878	0.8079	0.0063	0.041*
H6C	0.8201	0.8821	−0.0200	0.041*
O2	0.3580 (3)	0.8114 (2)	0.25801 (16)	0.0144 (6)
H2	0.3579	0.7470	0.2467	0.017*
O1	0.6345 (4)	0.8266 (2)	0.39163 (17)	0.0157 (6)
H1	0.6813	0.8600	0.4375	0.019*
O3	0.4312 (4)	0.9935 (2)	0.32999 (17)	0.0156 (6)
H3	0.3967	1.0527	0.3100	0.019*
C3	0.2846 (5)	0.9375 (3)	0.3562 (3)	0.0141 (8)
H3A	0.1758	0.9552	0.3126	0.017*
C2	0.3211 (5)	0.8219 (3)	0.3484 (2)	0.0155 (8)
H2A	0.2139	0.7806	0.3540	0.019*
O4	0.2278 (4)	1.0783 (2)	0.45507 (19)	0.0204 (6)
H4	0.1250	1.0921	0.4295	0.025*
C1	0.4774 (5)	0.7790 (3)	0.4124 (3)	0.0188 (8)
H1A	0.4663	0.7952	0.4752	0.023*
H1B	0.4832	0.7020	0.4060	0.023*
C4	0.2584 (6)	0.9690 (3)	0.4493 (3)	0.0191 (8)
H4A	0.1573	0.9301	0.4648	0.023*
H4B	0.3637	0.9496	0.4935	0.023*

	U11	U22	U33	U12	U13	U23
Er1	0.01351 (10)	0.01084 (10)	0.01385 (10)	0.00053 (7)	0.00234 (7)	0.00034 (6)
O9	0.0162 (14)	0.0161 (15)	0.0238 (14)	0.0023 (12)	0.0024 (12)	0.0028 (11)
O13	0.0159 (14)	0.0188 (16)	0.0254 (15)	0.0029 (13)	0.0006 (12)	−0.0029 (12)
O6	0.0266 (17)	0.0178 (15)	0.0232 (15)	0.0030 (13)	0.0026 (13)	−0.0017 (12)
O14	0.0247 (17)	0.0164 (15)	0.0392 (18)	0.0115 (14)	0.0030 (14)	0.0050 (13)
O10	0.0182 (15)	0.0093 (14)	0.0254 (14)	0.0008 (12)	−0.0006 (12)	0.0031 (11)
O11	0.0318 (18)	0.0123 (15)	0.0330 (17)	−0.0075 (14)	−0.0008 (14)	−0.0056 (13)
N1	0.0213 (19)	0.023 (2)	0.0160 (16)	−0.0027 (16)	0.0049 (14)	0.0022 (14)
O7	0.0269 (16)	0.0203 (16)	0.0181 (14)	0.0069 (14)	0.0023 (12)	0.0006 (12)
O8	0.0251 (17)	0.0375 (19)	0.0188 (15)	0.0062 (15)	−0.0032 (13)	0.0043 (13)
N3	0.0188 (18)	0.0185 (19)	0.0198 (16)	0.0051 (15)	0.0047 (14)	0.0024 (14)
N2	0.0170 (18)	0.0167 (18)	0.0215 (17)	−0.0005 (15)	0.0077 (14)	0.0012 (14)
O5	0.0219 (15)	0.0179 (15)	0.0237 (15)	0.0044 (13)	0.0090 (12)	0.0044 (12)
C5	0.021 (2)	0.028 (2)	0.025 (2)	−0.0008 (19)	0.0086 (18)	−0.0017 (18)
O12	0.0195 (15)	0.0134 (15)	0.0325 (16)	−0.0018 (13)	0.0028 (13)	−0.0011 (12)
C6	0.033 (3)	0.020 (2)	0.028 (2)	0.005 (2)	0.007 (2)	−0.0003 (18)
O2	0.0174 (14)	0.0099 (13)	0.0161 (13)	−0.0012 (11)	0.0032 (11)	−0.0025 (10)
O1	0.0159 (14)	0.0152 (14)	0.0149 (13)	−0.0022 (12)	−0.0001 (11)	−0.0007 (11)
O3	0.0186 (15)	0.0097 (13)	0.0194 (13)	0.0007 (11)	0.0060 (11)	0.0017 (10)
C3	0.0117 (18)	0.0124 (19)	0.0182 (18)	−0.0020 (16)	0.0032 (15)	−0.0011 (15)
C2	0.017 (2)	0.0118 (19)	0.0185 (18)	−0.0049 (16)	0.0055 (15)	−0.0013 (15)
O4	0.0221 (16)	0.0169 (15)	0.0216 (14)	0.0046 (13)	0.0024 (12)	−0.0051 (11)
C1	0.016 (2)	0.018 (2)	0.023 (2)	−0.0033 (17)	0.0034 (16)	0.0031 (16)
C4	0.023 (2)	0.019 (2)	0.0160 (18)	−0.0012 (18)	0.0037 (16)	−0.0030 (16)

Er1—O1	2.348 (3)	C5—H5A	0.9900
Er1—O2	2.368 (3)	C5—H5B	0.9900
Er1—O3	2.463 (3)	C6—H6A	0.9800
Er1—O5	2.352 (3)	C6—H6B	0.9800
Er1—O6	2.438 (3)	C6—H6C	0.9800
Er1—O7	2.434 (3)	O2—C2	1.451 (4)
Er1—O9	2.583 (3)	O2—H2	0.8400
Er1—O10	2.428 (3)	O1—C1	1.445 (5)
Er1—O12	2.436 (3)	O1—H1	0.8400
Er1—O13	2.489 (3)	O3—C3	1.456 (4)
O9—N2	1.271 (5)	O3—H3	0.8400
O13—N3	1.275 (4)	C3—C2	1.512 (5)
O6—N1	1.278 (4)	C3—C4	1.512 (5)
O14—N3	1.212 (4)	C3—H3A	1.0000
O10—N2	1.265 (4)	C2—C1	1.512 (6)
O11—N2	1.223 (5)	C2—H2A	1.0000
N1—O8	1.226 (5)	O4—C4	1.422 (5)
N1—O7	1.259 (5)	O4—H4	0.8400
N3—O12	1.267 (4)	C1—H1A	0.9900
O5—C5	1.464 (5)	C1—H1B	0.9900
O5—H5	0.8401	C4—H4A	0.9900
C5—C6	1.505 (6)	C4—H4B	0.9900
O1—Er1—O5	142.67 (10)	O12—N3—O13	115.2 (3)
O1—Er1—O2	69.20 (9)	O11—N2—O10	121.4 (4)
O5—Er1—O2	143.66 (10)	O11—N2—O9	122.1 (4)
O1—Er1—O10	71.74 (9)	O10—N2—O9	116.5 (3)
O5—Er1—O10	80.73 (10)	C5—O5—Er1	137.4 (2)
O2—Er1—O10	135.43 (9)	C5—O5—H5	107.9
O1—Er1—O7	128.62 (10)	Er1—O5—H5	113.8
O5—Er1—O7	75.93 (10)	O5—C5—C6	110.6 (4)
O2—Er1—O7	67.89 (9)	O5—C5—H5A	109.5
O10—Er1—O7	156.65 (10)	C6—C5—H5A	109.5
O1—Er1—O12	72.33 (10)	O5—C5—H5B	109.5
O5—Er1—O12	73.94 (10)	C6—C5—H5B	109.5
O2—Er1—O12	118.51 (9)	H5A—C5—H5B	108.1
O10—Er1—O12	66.91 (10)	N3—O12—Er1	97.7 (2)
O7—Er1—O12	105.52 (10)	C5—C6—H6A	109.5
O1—Er1—O6	141.92 (10)	C5—C6—H6B	109.5
O5—Er1—O6	74.32 (10)	H6A—C6—H6B	109.5
O2—Er1—O6	80.93 (10)	C5—C6—H6C	109.5
O10—Er1—O6	121.09 (10)	H6A—C6—H6C	109.5
O7—Er1—O6	52.40 (10)	H6B—C6—H6C	109.5
O12—Er1—O6	145.13 (10)	C2—O2—Er1	110.2 (2)
O1—Er1—O3	68.68 (9)	C2—O2—H2	106.7
O5—Er1—O3	132.20 (9)	Er1—O2—H2	113.6
O2—Er1—O3	64.73 (9)	C1—O1—Er1	118.3 (2)
O10—Er1—O3	81.76 (9)	C1—O1—H1	106.9
O7—Er1—O3	114.57 (10)	Er1—O1—H1	120.9
O12—Er1—O3	135.89 (10)	C3—O3—Er1	117.9 (2)
O6—Er1—O3	77.59 (9)	C3—O3—H3	109.0
O1—Er1—O13	74.73 (9)	Er1—O3—H3	117.2
O5—Er1—O13	96.36 (10)	O3—C3—C2	107.0 (3)
O2—Er1—O13	72.82 (9)	O3—C3—C4	111.3 (3)
O10—Er1—O13	116.15 (9)	C2—C3—C4	113.0 (3)
O7—Er1—O13	66.70 (10)	O3—C3—H3A	108.5
O12—Er1—O13	51.66 (9)	C2—C3—H3A	108.5
O6—Er1—O13	118.97 (10)	C4—C3—H3A	108.5
O3—Er1—O13	131.19 (9)	O2—C2—C3	103.6 (3)
O1—Er1—O9	107.95 (9)	O2—C2—C1	107.5 (3)
O5—Er1—O9	70.35 (9)	C3—C2—C1	116.3 (3)
O2—Er1—O9	125.27 (9)	O2—C2—H2A	109.7
O10—Er1—O9	50.86 (9)	C3—C2—H2A	109.7
O7—Er1—O9	119.40 (10)	C1—C2—H2A	109.7
O12—Er1—O9	111.18 (10)	C4—O4—H4	109.4
O6—Er1—O9	70.51 (10)	O1—C1—C2	108.6 (3)
O3—Er1—O9	64.11 (9)	O1—C1—H1A	110.0
O13—Er1—O9	161.77 (10)	C2—C1—H1A	110.0
N2—O9—Er1	92.5 (2)	O1—C1—H1B	110.0
N3—O13—Er1	94.9 (2)	C2—C1—H1B	110.0
N1—O6—Er1	95.4 (2)	H1A—C1—H1B	108.4
N2—O10—Er1	100.1 (2)	O4—C4—C3	111.7 (3)
O8—N1—O7	121.6 (4)	O4—C4—H4A	109.3
O8—N1—O6	122.4 (4)	C3—C4—H4A	109.3
O7—N1—O6	116.0 (3)	O4—C4—H4B	109.3
N1—O7—Er1	96.1 (2)	C3—C4—H4B	109.3
O14—N3—O12	122.8 (4)	H4A—C4—H4B	107.9
O14—N3—O13	122.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.84	1.83	2.666 (4)	173
O2—H2···O9ii	0.84	1.97	2.795 (4)	167
O3—H3···O13iii	0.84	2.08	2.917 (4)	175
O4—H4···O11iv	0.84	2.07	2.897 (5)	169
O5—H5···O8v	0.84	2.09	2.865 (4)	154

Table 1

Selected bond lengths (Å)

Er1—O1	2.348 (3)
Er1—O2	2.368 (3)
Er1—O3	2.463 (3)
Er1—O5	2.352 (3)
Er1—O6	2.438 (3)
Er1—O7	2.434 (3)
Er1—O9	2.583 (3)
Er1—O10	2.428 (3)
Er1—O12	2.436 (3)
Er1—O13	2.489 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.84	1.83	2.666 (4)	173
O2—H2⋯O9ii	0.84	1.97	2.795 (4)	167
O3—H3⋯O13iii	0.84	2.08	2.917 (4)	175
O4—H4⋯O11iv	0.84	2.07	2.897 (5)	169
O5—H5⋯O8v	0.84	2.09	2.865 (4)	154

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