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

In the title Ho(III)-erythritol complex, [Ho(NO3)3(C4H10O4)(C2H5OH)], the Ho(III) cation is chelated by a tridentate erythritol ligand and three bidentate nitrate anions. An ethanol mol-ecule further coordinates the Ho(III) cation, completing the irregular O10 coordination geometry. In the crystal, an extensive O-H⋯O hydrogen-bond network 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 ▶).

Experimental

Crystal data

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

M = 519.15

Monoclinic,

a = 7.7501 (16) Å

b = 12.783 (3) Å

c = 15.164 (3) Å

β = 100.35 (3)°

V = 1477.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.44 mm−1

T = 173 K

0.26 × 0.19 × 0.19 mm

Data collection

Rigaku Saturn724+ CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.25, T max = 0.36

10146 measured reflections

3376 independent reflections

3198 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.061

S = 1.19

3376 reflections

218 parameters

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.83 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/S160053681300305X/xu5656sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300305X/xu5656Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300305X/xu5656Isup3.hkl

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

[Ho(NO3)3(C4H10O4)(C2H6O)]	F(000) = 1008
Mr = 519.15	Dx = 2.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5233 reflections
a = 7.7501 (16) Å	θ = 2.1–27.5°
b = 12.783 (3) Å	µ = 5.44 mm−1
c = 15.164 (3) Å	T = 173 K
β = 100.35 (3)°	Block, colorless
V = 1477.8 (5) Å3	0.26 × 0.19 × 0.19 mm
Z = 4

Rigaku Saturn724+ CCD diffractometer	3376 independent reflections
Radiation source: fine-focus sealed tube	3198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
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 = −14→16
Tmin = 0.25, Tmax = 0.36	l = −19→19
10146 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) = 0.061	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0123P)2 + 3.0745P] where P = (Fo2 + 2Fc2)/3
3376 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −0.83 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
Ho1	0.87485 (2)	0.104079 (12)	0.252907 (11)	0.01270 (6)
O1	0.8663 (3)	0.1741 (2)	0.10772 (18)	0.0164 (6)
H1	0.8036	0.1410	0.0660	0.025*
O2	1.1423 (3)	0.1887 (2)	0.24123 (17)	0.0148 (6)
H2	1.1406	0.2509	0.2589	0.022*
O3	1.0696 (3)	0.00635 (19)	0.16970 (17)	0.0150 (5)
H3	1.0969	−0.0551	0.1861	0.023*
O4	1.2729 (4)	−0.0786 (2)	0.04468 (19)	0.0211 (6)
H4	1.3661	−0.0846	0.0823	0.025*
O5	0.6941 (4)	0.0507 (2)	0.3547 (2)	0.0226 (6)
H5	0.7317	0.0052	0.3933	0.027*
O6	1.0213 (4)	0.1747 (2)	0.39669 (19)	0.0231 (6)
O7	1.0682 (4)	0.0119 (2)	0.3731 (2)	0.0229 (6)
O8	1.2006 (4)	0.0879 (3)	0.4970 (2)	0.0307 (7)
O9	0.6021 (4)	0.2037 (2)	0.2129 (2)	0.0213 (6)
O10	0.8267 (4)	0.2959 (2)	0.2684 (2)	0.0209 (6)
O11	0.5809 (4)	0.3735 (2)	0.2135 (2)	0.0281 (7)
O12	0.8170 (4)	−0.0952 (2)	0.23689 (19)	0.0178 (6)
O13	0.6491 (4)	0.0108 (2)	0.14891 (19)	0.0185 (6)
O14	0.6096 (4)	−0.1565 (2)	0.1343 (2)	0.0279 (7)
N1	1.0997 (5)	0.0912 (3)	0.4249 (2)	0.0200 (7)
N2	0.6662 (4)	0.2943 (3)	0.2309 (2)	0.0178 (7)
N3	0.6893 (4)	−0.0825 (3)	0.1723 (2)	0.0175 (7)
C1	1.0234 (5)	0.2218 (3)	0.0869 (3)	0.0178 (8)
H1A	1.0180	0.2987	0.0934	0.021*
H1B	1.0350	0.2055	0.0244	0.021*
C2	1.1784 (5)	0.1781 (3)	0.1517 (3)	0.0157 (8)
H2A	1.2861	0.2190	0.1464	0.019*
C3	1.2153 (5)	0.0621 (3)	0.1435 (3)	0.0144 (7)
H3A	1.3245	0.0444	0.1869	0.017*
C4	1.2410 (5)	0.0312 (3)	0.0504 (3)	0.0183 (8)
H4A	1.1350	0.0501	0.0065	0.022*
H4B	1.3415	0.0704	0.0348	0.022*
C5	0.5492 (6)	0.0933 (3)	0.3922 (3)	0.0270 (10)
H5A	0.4776	0.0351	0.4092	0.032*
H5B	0.4735	0.1356	0.3460	0.032*
C6	0.6115 (6)	0.1606 (3)	0.4734 (3)	0.0287 (10)
H6A	0.6832	0.1184	0.5202	0.043*
H6B	0.5100	0.1884	0.4961	0.043*
H6C	0.6817	0.2187	0.4568	0.043*

	U11	U22	U33	U12	U13	U23
Ho1	0.01219 (10)	0.01246 (10)	0.01306 (10)	0.00054 (6)	0.00127 (7)	0.00034 (6)
O1	0.0137 (14)	0.0171 (14)	0.0166 (14)	−0.0037 (11)	−0.0024 (11)	0.0009 (10)
O2	0.0186 (14)	0.0102 (13)	0.0160 (14)	−0.0010 (11)	0.0043 (11)	−0.0037 (10)
O3	0.0164 (14)	0.0118 (13)	0.0178 (14)	−0.0010 (11)	0.0055 (11)	0.0020 (10)
O4	0.0194 (15)	0.0230 (15)	0.0199 (15)	0.0016 (12)	0.0005 (12)	−0.0056 (11)
O5	0.0223 (15)	0.0237 (16)	0.0232 (16)	0.0044 (12)	0.0080 (13)	0.0064 (12)
O6	0.0278 (17)	0.0220 (16)	0.0179 (15)	0.0052 (13)	−0.0001 (13)	−0.0004 (11)
O7	0.0230 (15)	0.0203 (15)	0.0243 (16)	0.0022 (12)	0.0017 (13)	0.0010 (12)
O8	0.0273 (18)	0.0436 (19)	0.0188 (16)	0.0073 (15)	−0.0024 (14)	0.0043 (13)
O9	0.0172 (14)	0.0150 (14)	0.0311 (17)	−0.0017 (12)	0.0026 (12)	0.0001 (12)
O10	0.0141 (14)	0.0198 (15)	0.0270 (16)	0.0023 (12)	−0.0013 (12)	−0.0045 (11)
O11	0.0257 (17)	0.0181 (15)	0.040 (2)	0.0102 (13)	0.0039 (15)	0.0035 (13)
O12	0.0122 (13)	0.0180 (14)	0.0219 (15)	0.0005 (11)	−0.0002 (12)	0.0033 (11)
O13	0.0169 (14)	0.0125 (13)	0.0243 (15)	0.0012 (11)	−0.0008 (12)	0.0017 (11)
O14	0.0308 (18)	0.0150 (15)	0.0356 (19)	−0.0063 (13)	−0.0003 (14)	−0.0042 (12)
N1	0.0182 (18)	0.0266 (19)	0.0147 (17)	0.0032 (15)	0.0019 (14)	0.0017 (14)
N2	0.0175 (17)	0.0168 (18)	0.0198 (17)	0.0038 (14)	0.0053 (14)	0.0012 (13)
N3	0.0160 (17)	0.0163 (17)	0.0201 (18)	0.0003 (14)	0.0033 (14)	−0.0019 (13)
C1	0.0162 (19)	0.018 (2)	0.020 (2)	−0.0032 (16)	0.0041 (16)	0.0033 (15)
C2	0.0152 (19)	0.0173 (19)	0.0153 (19)	−0.0023 (15)	0.0044 (15)	−0.0015 (14)
C3	0.0121 (18)	0.0134 (18)	0.0172 (19)	−0.0006 (15)	0.0010 (15)	−0.0001 (14)
C4	0.019 (2)	0.019 (2)	0.018 (2)	0.0010 (16)	0.0051 (16)	0.0007 (15)
C5	0.025 (2)	0.029 (2)	0.029 (2)	−0.0022 (19)	0.007 (2)	−0.0033 (18)
C6	0.033 (3)	0.024 (2)	0.028 (2)	0.0014 (19)	0.002 (2)	−0.0043 (18)

Ho1—O1	2.367 (3)	O8—N1	1.225 (4)
Ho1—O2	2.373 (3)	O9—N2	1.271 (4)
Ho1—O3	2.473 (3)	O10—N2	1.272 (4)
Ho1—O5	2.364 (3)	O11—N2	1.212 (4)
Ho1—O6	2.443 (3)	O12—N3	1.272 (4)
Ho1—O7	2.444 (3)	O13—N3	1.267 (4)
Ho1—O9	2.449 (3)	O14—N3	1.217 (4)
Ho1—O10	2.497 (3)	C1—C2	1.515 (5)
Ho1—O12	2.590 (3)	C1—H1A	0.9900
Ho1—O13	2.445 (3)	C1—H1B	0.9900
O1—C1	1.446 (4)	C2—C3	1.520 (5)
O1—H1	0.8399	C2—H2A	1.0000
O2—C2	1.441 (4)	C3—C4	1.514 (5)
O2—H2	0.8400	C3—H3A	1.0000
O3—C3	1.450 (4)	C4—H4A	0.9900
O3—H3	0.8400	C4—H4B	0.9900
O4—C4	1.430 (5)	C5—C6	1.509 (6)
O4—H4	0.8401	C5—H5A	0.9900
O5—C5	1.453 (5)	C5—H5B	0.9900
O5—H5	0.8400	C6—H6A	0.9800
O6—N1	1.265 (4)	C6—H6B	0.9800
O7—N1	1.279 (4)	C6—H6C	0.9800
O5—Ho1—O1	142.74 (10)	C5—O5—Ho1	137.5 (2)
O5—Ho1—O2	143.95 (10)	C5—O5—H5	100.5
O1—Ho1—O2	68.71 (9)	Ho1—O5—H5	118.9
O5—Ho1—O6	76.03 (10)	N1—O6—Ho1	96.2 (2)
O1—Ho1—O6	128.42 (9)	N1—O7—Ho1	95.8 (2)
O2—Ho1—O6	68.05 (10)	N2—O9—Ho1	97.7 (2)
O5—Ho1—O7	74.33 (10)	N2—O10—Ho1	95.3 (2)
O1—Ho1—O7	141.90 (10)	N3—O12—Ho1	92.5 (2)
O2—Ho1—O7	81.29 (9)	N3—O13—Ho1	99.6 (2)
O6—Ho1—O7	52.28 (10)	O8—N1—O6	121.5 (3)
O5—Ho1—O13	80.85 (10)	O8—N1—O7	122.8 (3)
O1—Ho1—O13	71.78 (9)	O6—N1—O7	115.7 (3)
O2—Ho1—O13	135.05 (9)	O11—N2—O9	122.5 (3)
O6—Ho1—O13	156.88 (10)	O11—N2—O10	122.4 (3)
O7—Ho1—O13	121.18 (9)	O9—N2—O10	115.1 (3)
O5—Ho1—O9	74.06 (10)	O14—N3—O13	121.4 (3)
O1—Ho1—O9	72.19 (10)	O14—N3—O12	121.6 (3)
O2—Ho1—O9	118.12 (9)	O13—N3—O12	117.0 (3)
O6—Ho1—O9	105.73 (10)	O1—C1—C2	107.7 (3)
O7—Ho1—O9	145.26 (10)	O1—C1—H1A	110.2
O13—Ho1—O9	66.90 (9)	C2—C1—H1A	110.2
O5—Ho1—O3	132.46 (9)	O1—C1—H1B	110.2
O1—Ho1—O3	68.54 (9)	C2—C1—H1B	110.2
O2—Ho1—O3	64.58 (9)	H1A—C1—H1B	108.5
O6—Ho1—O3	114.44 (9)	O2—C2—C1	108.1 (3)
O7—Ho1—O3	77.77 (9)	O2—C2—C3	103.8 (3)
O13—Ho1—O3	81.74 (9)	C1—C2—C3	116.5 (3)
O9—Ho1—O3	135.65 (10)	O2—C2—H2A	109.4
O5—Ho1—O10	96.08 (10)	C1—C2—H2A	109.4
O1—Ho1—O10	74.71 (9)	C3—C2—H2A	109.4
O2—Ho1—O10	72.95 (9)	O3—C3—C4	111.5 (3)
O6—Ho1—O10	66.84 (9)	O3—C3—C2	106.9 (3)
O7—Ho1—O10	119.02 (9)	C4—C3—C2	112.9 (3)
O13—Ho1—O10	115.95 (9)	O3—C3—H3A	108.5
O9—Ho1—O10	51.40 (9)	C4—C3—H3A	108.5
O3—Ho1—O10	131.23 (9)	C2—C3—H3A	108.5
O5—Ho1—O12	70.39 (9)	O4—C4—C3	111.4 (3)
O1—Ho1—O12	108.02 (9)	O4—C4—H4A	109.3
O2—Ho1—O12	125.46 (9)	C3—C4—H4A	109.3
O6—Ho1—O12	119.47 (9)	O4—C4—H4B	109.3
O7—Ho1—O12	70.65 (9)	C3—C4—H4B	109.3
O13—Ho1—O12	50.82 (9)	H4A—C4—H4B	108.0
O9—Ho1—O12	111.14 (9)	O5—C5—C6	112.1 (4)
O3—Ho1—O12	64.32 (9)	O5—C5—H5A	109.2
O10—Ho1—O12	161.43 (9)	C6—C5—H5A	109.2
C1—O1—Ho1	118.6 (2)	O5—C5—H5B	109.2
C1—O1—H1	116.3	C6—C5—H5B	109.2
Ho1—O1—H1	115.3	H5A—C5—H5B	107.9
C2—O2—Ho1	110.3 (2)	C5—C6—H6A	109.5
C2—O2—H2	114.0	C5—C6—H6B	109.5
Ho1—O2—H2	110.1	H6A—C6—H6B	109.5
C3—O3—Ho1	117.9 (2)	C5—C6—H6C	109.5
C3—O3—H3	112.0	H6A—C6—H6C	109.5
Ho1—O3—H3	117.8	H6B—C6—H6C	109.5
C4—O4—H4	100.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.84	1.86	2.665 (4)	161
O2—H2···O12ii	0.84	1.99	2.794 (4)	159
O3—H3···O10iii	0.84	2.08	2.914 (4)	177
O4—H4···O14iv	0.84	2.12	2.894 (4)	153
O5—H5···O8v	0.84	2.03	2.863 (4)	169

Table 1

Selected bond lengths (Å)

Ho1—O1	2.367 (3)
Ho1—O2	2.373 (3)
Ho1—O3	2.473 (3)
Ho1—O5	2.364 (3)
Ho1—O6	2.443 (3)
Ho1—O7	2.444 (3)
Ho1—O9	2.449 (3)
Ho1—O10	2.497 (3)
Ho1—O12	2.590 (3)
Ho1—O13	2.445 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.84	1.86	2.665 (4)	161
O2—H2⋯O12ii	0.84	1.99	2.794 (4)	159
O3—H3⋯O10iii	0.84	2.08	2.914 (4)	177
O4—H4⋯O14iv	0.84	2.12	2.894 (4)	153
O5—H5⋯O8v	0.84	2.03	2.863 (4)	169

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