Poly[(μ4-benzene-1,3,5-tricarboxyl­ato)bis­(dimethyl sulfoxide-κO)­neodymium(III)]

Li, Z.; Liu, K.

doi:10.1107/S1600536811049622

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1833

https://doi.org/10.1107/S1600536811049622

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Poly[(μ₄-benzene-1,3,5-tricarboxylato)bis(dimethyl sulfoxide-κO)neodymium(III)]

Zhongyue Li ^a ^* and Kun Liu ^a

^aThe Department of Physics–Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: lizhongyue@hpu.edu.cn

(Received 18 October 2011; accepted 21 November 2011; online 25 November 2011)

The asymmetric unit of the title compound, [Nd(C₉H₃O₆)(C₂H₆OS)₂]_n, contains one Nd³⁺ ion, one benzene-1,3,5-tricarboxylic ligand and two coordinating dimethyl sulfoxide molecules. The Nd³⁺ ion is coordinated by six O atoms from four carboxylate groups of the benzene-1,3,5-tricarboxylate ligands and two O atoms from two dimethyl sulfoxide molecules. The metal-organic cluster formed upon symmetry expansion of the asymmetric unit consists of two metal atoms and four benzene-1,3,5-tricarboxylate groups, creating a paddle-wheel-type building block arrangement. The remaining coordination sites are occupied by additional benzene-1,3,5-tricarboxylate groups and dimethyl sulfoxide molecules, forming a three-dimensional polymeric rare earth metal-organic framework structure.

Related literature

For metal-organic framework structures with adsorption, catalytic and fluorescence properties, see: Sun et al. (2006 ); Ravon et al. (2008 ); Allendorf et al. (2009 ). For isostructural rare earth complexes, see: Thirumurugan & Natarajan (2004 ); For rare earth coordination polymers, see: Guo et al. (2006 ).

Experimental

Crystal data

[Nd(C₉H₃O₆)(C₂H₆OS)₂]
M_r = 507.61
Monoclinic, P 2₁ /n
a = 10.380 (2) Å
b = 10.752 (3) Å
c = 16.025 (4) Å
β = 106.419 (4)°
V = 1715.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 3.31 mm⁻¹
T = 273 K
0.50 × 0.40 × 0.40 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.289, T_max = 0.351
8925 measured reflections
3008 independent reflections
2453 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.082
S = 0.98
3008 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 1.92 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049622/jj2108sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049622/jj2108Isup2.hkl

checkCIF report

Comment top

Metal-organic framework design and construction is currently a flourishing field of research owing to the intriguing molecular topologies and the potentially exploitable adsorption (Sun et al., 2006), catalytic (Ravon et al., 2008) and fluorescence (Allendorf et al., 2009) properties of these types of compounds. As functional metal centers, rare earth metals are attracting more attention from synthetic chemists for their unusual coordination properties and special chemical characteristics arising from interactions with the 4f electrons and the propensity to form isostructural complexes (Thirumurugan & Natarajan, 2004). Many coordination polymers utilizing the rare earth elements have been synthesized (Guo et al., 2006).

The title compound poly[(benzene-1,3,5-tricarboxylato)bis(dimethyl sulfoxide)neodymium(III)]n represents a rare-earth three-dimensional metal-organic framework structure (Fig. 1). In this compound, the asymmetric unit, Nd(C₉H₃O₆)(C₂H₆OS)₂, contains one eight-coordinated Nd³⁺ ion, one benzene-1,3,5-tricarboxylate ligand and two coordinated dimethyl sulfoxide molecules, without any guest molecule. Each of two metal center Nd³⁺ ions in a formed cluster is coordinated with six oxygen atoms from four carboxylate groups of the 1,3,5- benzenetricarboxylic ligands and two oxygen atoms from two terminal dimethyl sulfoxide molecules. Upon symmetry expansion of the asymmetric unit, the metal organic cluster formed therefore consists of two metal centers and four benzene-1,3,5-tricarboxylate groups creating a paddle-wheel type building block arrangement. The remaining coordination sites are occupied by additional benzene-1,3,5-tricarboxylate groups and dimethyl sulfoxide molecules forming a polymeric rare earth three-dimensional metal-organic framework structure.

Related literature top

For metal-organic framework structures with adsorption, catalytic and fluorescence properties, see: Sun et al. (2006); Ravon et al. (2008); Allendorf et al. (2009). For isostructural rare earth complexes, see: Thirumurugan & Natarajan (2004); For rare earth coordination polymers, see: Guo et al. (2006).

Experimental top

All reagents were of analytical grade. A mixture of neodymium nitrate (40 mg, 0.10 mmol) and benzene-1,3,5-tricarboxylate acid (10 mg, 0.05 mmol) was dissolved in N,N'-dimethylformamide (15 ml) and dimethyl sulfoxide (10 ml) at room temperature. Two drops of NaOH (aq, 2 M) was added, followed by some nitric acid (aq, 2 M) until the solution is clear. This mixture was placed at 55°C for 20 days giving rise to purple rod crystals suitable for x-ray crystallographic analysis.

Structure description top

For metal-organic framework structures with adsorption, catalytic and fluorescence properties, see: Sun et al. (2006); Ravon et al. (2008); Allendorf et al. (2009). For isostructural rare earth complexes, see: Thirumurugan & Natarajan (2004); For rare earth coordination polymers, see: Guo et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of (I) showing the atom-numbering scheme of the asymmetric unit and symmetry expanded metal-organic framework structure. Displacement ellipsoids are drawn at the 30% probability level.

Poly[(µ₄-benzene-1,3,5-tricarboxylato)bis(dimethyl sulfoxide-κO) neodymium(III)] top

Crystal data top

[Nd(C₉H₃O₆)(C₂H₆OS)₂]	F(000) = 996
M_r = 507.61	D_x = 1.965 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2282 reflections
a = 10.380 (2) Å	θ = 2.3–24.8°
b = 10.752 (3) Å	µ = 3.31 mm⁻¹
c = 16.025 (4) Å	T = 273 K
β = 106.419 (4)°	Rod, purple
V = 1715.6 (7) Å³	0.50 × 0.40 × 0.40 mm
Z = 4

Data collection top

Bruker APEX CCD diffractometer	3008 independent reflections
Radiation source: fine-focus sealed tube	2453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
phi and ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −10→12
T_min = 0.289, T_max = 0.351	l = −18→19
8925 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0335P)²] where P = (F_o² + 2F_c²)/3
3008 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 1.92 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Nd(C₉H₃O₆)(C₂H₆OS)₂]	V = 1715.6 (7) Å³
M_r = 507.61	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.380 (2) Å	µ = 3.31 mm⁻¹
b = 10.752 (3) Å	T = 273 K
c = 16.025 (4) Å	0.50 × 0.40 × 0.40 mm
β = 106.419 (4)°

Data collection top

Bruker APEX CCD diffractometer	3008 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2453 reflections with I > 2σ(I)
T_min = 0.289, T_max = 0.351	R_int = 0.049
8925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 0.98	Δρ_max = 1.92 e Å⁻³
3008 reflections	Δρ_min = −0.83 e Å⁻³
221 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
Nd1	0.36554 (3)	0.12931 (3)	0.02773 (2)	0.01539 (12)
S1	0.0680 (2)	0.2768 (2)	−0.08861 (14)	0.0492 (6)
S2	0.3373 (3)	0.4585 (2)	0.08367 (18)	0.0664 (8)
O1	0.1446 (4)	0.0876 (4)	0.0571 (3)	0.0280 (11)
O2	0.2784 (4)	0.2139 (4)	0.1508 (3)	0.0301 (11)
O3	−0.3430 (4)	0.0586 (4)	0.0532 (3)	0.0297 (11)
O4	−0.4178 (4)	0.1981 (4)	0.1279 (3)	0.0360 (12)
O5	0.0801 (4)	0.4650 (4)	0.3619 (3)	0.0268 (11)
O6	−0.0472 (4)	0.3271 (4)	0.4070 (3)	0.0309 (11)
O7	0.1768 (5)	0.1920 (5)	−0.1004 (3)	0.0462 (14)
O8	0.3616 (5)	0.3615 (4)	0.0214 (3)	0.0476 (14)
C1	0.1662 (6)	0.1639 (5)	0.1191 (4)	0.0204 (15)
C2	0.0514 (6)	0.1983 (6)	0.1562 (4)	0.0179 (14)
C3	−0.0760 (6)	0.1517 (5)	0.1195 (4)	0.0196 (14)
H3	−0.0916	0.0987	0.0719	0.024*
C4	−0.1821 (6)	0.1837 (6)	0.1535 (4)	0.0190 (14)
C5	−0.1545 (6)	0.2560 (5)	0.2286 (4)	0.0202 (15)
H5	−0.2228	0.2735	0.2540	0.024*
C6	−0.0262 (6)	0.3024 (5)	0.2661 (4)	0.0165 (13)
C7	0.0737 (6)	0.2764 (5)	0.2272 (4)	0.0196 (14)
H7	0.1579	0.3123	0.2494	0.024*
C8	−0.3236 (6)	0.1436 (6)	0.1090 (4)	0.0223 (15)
C9	0.0043 (6)	0.3722 (6)	0.3517 (4)	0.0204 (14)
C10	0.3202 (10)	0.6008 (7)	0.0260 (7)	0.080 (3)
H10A	0.3911	0.6083	−0.0013	0.121*
H10B	0.3251	0.6687	0.0657	0.121*
H10C	0.2350	0.6025	−0.0176	0.121*
C11	0.4971 (10)	0.4797 (10)	0.1533 (7)	0.106 (4)
H11A	0.5345	0.4005	0.1752	0.159*
H11B	0.4922	0.5318	0.2010	0.159*
H11C	0.5531	0.5186	0.1224	0.159*
C12	0.0497 (10)	0.3915 (8)	−0.1710 (6)	0.075 (3)
H12A	0.1285	0.4430	−0.1580	0.113*
H12B	−0.0275	0.4420	−0.1733	0.113*
H12C	0.0383	0.3515	−0.2262	0.113*
C13	−0.0810 (8)	0.1947 (9)	−0.1314 (7)	0.079 (3)
H13A	−0.0857	0.1672	−0.1892	0.119*
H13B	−0.1561	0.2478	−0.1333	0.119*
H13C	−0.0832	0.1239	−0.0953	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.01401 (19)	0.01665 (19)	0.01629 (19)	0.00024 (16)	0.00554 (13)	−0.00076 (15)
S1	0.0391 (12)	0.0561 (14)	0.0477 (14)	0.0094 (11)	0.0047 (10)	0.0119 (10)
S2	0.102 (2)	0.0324 (12)	0.082 (2)	−0.0009 (13)	0.0536 (17)	−0.0043 (12)
O1	0.024 (3)	0.037 (3)	0.027 (3)	−0.002 (2)	0.012 (2)	−0.012 (2)
O2	0.019 (3)	0.037 (3)	0.037 (3)	−0.004 (2)	0.014 (2)	−0.011 (2)
O3	0.032 (3)	0.024 (3)	0.028 (3)	−0.003 (2)	0.001 (2)	−0.009 (2)
O4	0.014 (3)	0.049 (3)	0.045 (3)	−0.001 (2)	0.008 (2)	−0.017 (3)
O5	0.031 (3)	0.028 (3)	0.023 (3)	−0.011 (2)	0.009 (2)	−0.006 (2)
O6	0.033 (3)	0.039 (3)	0.025 (3)	−0.011 (2)	0.015 (2)	−0.013 (2)
O7	0.032 (3)	0.065 (4)	0.045 (4)	0.019 (3)	0.017 (3)	0.012 (3)
O8	0.071 (4)	0.023 (3)	0.053 (4)	−0.001 (3)	0.025 (3)	−0.009 (2)
C1	0.019 (4)	0.023 (4)	0.021 (4)	0.001 (3)	0.010 (3)	0.004 (3)
C2	0.016 (3)	0.024 (4)	0.015 (3)	−0.002 (3)	0.008 (3)	0.000 (3)
C3	0.020 (3)	0.023 (4)	0.015 (3)	0.002 (3)	0.003 (3)	−0.003 (3)
C4	0.017 (3)	0.023 (3)	0.019 (4)	0.000 (3)	0.007 (3)	0.000 (3)
C5	0.014 (3)	0.023 (4)	0.025 (4)	−0.002 (3)	0.009 (3)	−0.005 (3)
C6	0.015 (3)	0.015 (3)	0.018 (4)	0.002 (3)	0.002 (3)	0.001 (3)
C7	0.015 (3)	0.021 (3)	0.021 (4)	−0.001 (3)	0.002 (3)	0.000 (3)
C8	0.025 (4)	0.021 (4)	0.020 (4)	−0.004 (3)	0.004 (3)	0.004 (3)
C9	0.015 (3)	0.028 (4)	0.019 (4)	0.001 (3)	0.007 (3)	−0.006 (3)
C10	0.091 (8)	0.038 (6)	0.118 (10)	0.004 (5)	0.038 (7)	−0.004 (5)
C11	0.112 (10)	0.112 (10)	0.072 (9)	0.054 (8)	−0.009 (7)	−0.003 (7)
C12	0.098 (8)	0.054 (6)	0.065 (7)	0.008 (5)	0.009 (6)	0.035 (5)
C13	0.029 (5)	0.106 (8)	0.092 (9)	−0.007 (5)	−0.001 (5)	−0.004 (7)

Geometric parameters (Å, º) top

Nd1—O3ⁱ	2.376 (4)	C1—C2	1.519 (8)
Nd1—O6ⁱⁱ	2.403 (4)	C2—C3	1.381 (8)
Nd1—O5ⁱⁱⁱ	2.451 (4)	C2—C7	1.380 (8)
Nd1—O4^iv	2.478 (4)	C3—C4	1.401 (8)
Nd1—O7	2.497 (5)	C3—H3	0.9300
Nd1—O8	2.498 (4)	C4—C5	1.394 (8)
Nd1—O1	2.509 (4)	C4—C8	1.503 (8)
Nd1—O2	2.559 (4)	C5—C6	1.390 (8)
Nd1—C1	2.878 (6)	C5—H5	0.9300
S1—O7	1.505 (5)	C6—C7	1.381 (8)
S1—C13	1.744 (8)	C6—C9	1.515 (8)
S1—C12	1.777 (8)	C7—H7	0.9300
S2—O8	1.513 (5)	C10—H10A	0.9600
S2—C11	1.733 (10)	C10—H10B	0.9600
S2—C10	1.770 (9)	C10—H10C	0.9600
O1—C1	1.258 (7)	C11—H11A	0.9600
O2—C1	1.253 (7)	C11—H11B	0.9600
O3—C8	1.255 (7)	C11—H11C	0.9600
O3—Nd1ⁱ	2.376 (4)	C12—H12A	0.9600
O4—C8	1.249 (7)	C12—H12B	0.9600
O4—Nd1^v	2.478 (4)	C12—H12C	0.9600
O5—C9	1.253 (7)	C13—H13A	0.9600
O5—Nd1^vi	2.451 (4)	C13—H13B	0.9600
O6—C9	1.255 (7)	C13—H13C	0.9600
O6—Nd1^vii	2.403 (4)

O3ⁱ—Nd1—O6ⁱⁱ	74.21 (15)	O1—C1—C2	118.9 (5)
O3ⁱ—Nd1—O5ⁱⁱⁱ	75.39 (15)	O2—C1—Nd1	62.7 (3)
O6ⁱⁱ—Nd1—O5ⁱⁱⁱ	131.26 (14)	O1—C1—Nd1	60.5 (3)
O3ⁱ—Nd1—O4^iv	122.58 (15)	C2—C1—Nd1	170.6 (4)
O6ⁱⁱ—Nd1—O4^iv	89.06 (16)	C3—C2—C7	119.2 (5)
O5ⁱⁱⁱ—Nd1—O4^iv	76.48 (15)	C3—C2—C1	120.5 (5)
O3ⁱ—Nd1—O7	81.22 (16)	C7—C2—C1	120.3 (5)
O6ⁱⁱ—Nd1—O7	70.85 (15)	C2—C3—C4	120.6 (6)
O5ⁱⁱⁱ—Nd1—O7	139.05 (16)	C2—C3—H3	119.7
O4^iv—Nd1—O7	144.05 (17)	C4—C3—H3	119.7
O3ⁱ—Nd1—O8	146.04 (16)	C5—C4—C3	118.7 (6)
O6ⁱⁱ—Nd1—O8	77.17 (15)	C5—C4—C8	120.3 (5)
O5ⁱⁱⁱ—Nd1—O8	138.39 (15)	C3—C4—C8	121.0 (5)
O4^iv—Nd1—O8	74.30 (16)	C6—C5—C4	120.8 (5)
O7—Nd1—O8	72.36 (17)	C6—C5—H5	119.6
O3ⁱ—Nd1—O1	89.81 (14)	C4—C5—H5	119.6
O6ⁱⁱ—Nd1—O1	139.36 (15)	C7—C6—C5	118.8 (5)
O5ⁱⁱⁱ—Nd1—O1	76.81 (14)	C7—C6—C9	121.2 (5)
O4^iv—Nd1—O1	129.95 (14)	C5—C6—C9	119.9 (5)
O7—Nd1—O1	69.90 (15)	C2—C7—C6	121.6 (6)
O8—Nd1—O1	100.41 (15)	C2—C7—H7	119.2
O3ⁱ—Nd1—O2	136.16 (14)	C6—C7—H7	119.2
O6ⁱⁱ—Nd1—O2	147.93 (15)	O4—C8—O3	122.4 (6)
O5ⁱⁱⁱ—Nd1—O2	76.07 (14)	O4—C8—C4	118.6 (5)
O4^iv—Nd1—O2	81.29 (14)	O3—C8—C4	119.1 (6)
O7—Nd1—O2	99.90 (15)	O5—C9—O6	126.3 (6)
O8—Nd1—O2	70.79 (15)	O5—C9—C6	118.4 (5)
O1—Nd1—O2	51.48 (13)	O6—C9—C6	115.3 (5)
O3ⁱ—Nd1—C1	114.43 (16)	S2—C10—H10A	109.5
O6ⁱⁱ—Nd1—C1	150.90 (16)	S2—C10—H10B	109.5
O5ⁱⁱⁱ—Nd1—C1	77.15 (15)	H10A—C10—H10B	109.5
O4^iv—Nd1—C1	106.46 (17)	S2—C10—H10C	109.5
O7—Nd1—C1	82.76 (16)	H10A—C10—H10C	109.5
O8—Nd1—C1	83.44 (16)	H10B—C10—H10C	109.5
O1—Nd1—C1	25.87 (15)	S2—C11—H11A	109.5
O2—Nd1—C1	25.79 (15)	S2—C11—H11B	109.5
O7—S1—C13	104.9 (4)	H11A—C11—H11B	109.5
O7—S1—C12	104.7 (4)	S2—C11—H11C	109.5
C13—S1—C12	99.3 (5)	H11A—C11—H11C	109.5
O8—S2—C11	102.0 (4)	H11B—C11—H11C	109.5
O8—S2—C10	105.2 (4)	S1—C12—H12A	109.5
C11—S2—C10	99.2 (5)	S1—C12—H12B	109.5
C1—O1—Nd1	93.7 (4)	H12A—C12—H12B	109.5
C1—O2—Nd1	91.5 (4)	S1—C12—H12C	109.5
C8—O3—Nd1ⁱ	168.4 (4)	H12A—C12—H12C	109.5
C8—O4—Nd1^v	109.4 (4)	H12B—C12—H12C	109.5
C9—O5—Nd1^vi	132.6 (4)	S1—C13—H13A	109.5
C9—O6—Nd1^vii	145.7 (4)	S1—C13—H13B	109.5
S1—O7—Nd1	120.2 (3)	H13A—C13—H13B	109.5
S2—O8—Nd1	131.7 (3)	S1—C13—H13C	109.5
O2—C1—O1	122.5 (5)	H13A—C13—H13C	109.5
O2—C1—C2	118.6 (5)	H13B—C13—H13C	109.5

O3ⁱ—Nd1—O1—C1	162.7 (4)	O7—Nd1—C1—O2	−131.4 (4)
O6ⁱⁱ—Nd1—O1—C1	−132.2 (4)	O8—Nd1—C1—O2	−58.4 (4)
O5ⁱⁱⁱ—Nd1—O1—C1	87.7 (4)	O1—Nd1—C1—O2	170.7 (6)
O4^iv—Nd1—O1—C1	28.3 (4)	O3ⁱ—Nd1—C1—O1	−19.0 (4)
O7—Nd1—O1—C1	−116.5 (4)	O6ⁱⁱ—Nd1—C1—O1	82.6 (5)
O8—Nd1—O1—C1	−49.8 (4)	O5ⁱⁱⁱ—Nd1—C1—O1	−86.2 (4)
O2—Nd1—O1—C1	5.1 (3)	O4^iv—Nd1—C1—O1	−157.7 (4)
O3ⁱ—Nd1—O2—C1	−38.5 (4)	O7—Nd1—C1—O1	57.9 (4)
O6ⁱⁱ—Nd1—O2—C1	118.6 (4)	O8—Nd1—C1—O1	130.8 (4)
O5ⁱⁱⁱ—Nd1—O2—C1	−89.2 (4)	O2—Nd1—C1—O1	−170.7 (6)
O4^iv—Nd1—O2—C1	−167.4 (4)	O2—C1—C2—C3	175.7 (6)
O7—Nd1—O2—C1	49.1 (4)	O1—C1—C2—C3	−3.3 (9)
O8—Nd1—O2—C1	116.3 (4)	O2—C1—C2—C7	−4.5 (9)
O1—Nd1—O2—C1	−5.2 (3)	O1—C1—C2—C7	176.5 (6)
C13—S1—O7—Nd1	−123.4 (4)	C7—C2—C3—C4	0.4 (9)
C12—S1—O7—Nd1	132.5 (4)	C1—C2—C3—C4	−179.8 (5)
O3ⁱ—Nd1—O7—S1	144.9 (3)	C2—C3—C4—C5	−4.5 (9)
O6ⁱⁱ—Nd1—O7—S1	−138.8 (4)	C2—C3—C4—C8	174.1 (5)
O5ⁱⁱⁱ—Nd1—O7—S1	89.5 (4)	C3—C4—C5—C6	4.1 (9)
O4^iv—Nd1—O7—S1	−79.4 (4)	C8—C4—C5—C6	−174.5 (5)
O8—Nd1—O7—S1	−56.7 (3)	C4—C5—C6—C7	0.5 (9)
O1—Nd1—O7—S1	51.9 (3)	C4—C5—C6—C9	−175.2 (6)
O2—Nd1—O7—S1	9.4 (3)	C3—C2—C7—C6	4.4 (9)
C1—Nd1—O7—S1	28.7 (3)	C1—C2—C7—C6	−175.4 (5)
C11—S2—O8—Nd1	87.3 (5)	C5—C6—C7—C2	−4.9 (9)
C10—S2—O8—Nd1	−169.6 (4)	C9—C6—C7—C2	170.7 (6)
O3ⁱ—Nd1—O8—S2	157.4 (3)	Nd1^v—O4—C8—O3	−6.6 (7)
O6ⁱⁱ—Nd1—O8—S2	−169.6 (4)	Nd1^v—O4—C8—C4	171.9 (4)
O5ⁱⁱⁱ—Nd1—O8—S2	−29.9 (5)	Nd1ⁱ—O3—C8—O4	−105 (2)
O4^iv—Nd1—O8—S2	−76.9 (4)	Nd1ⁱ—O3—C8—C4	76 (2)
O7—Nd1—O8—S2	116.7 (4)	C5—C4—C8—O4	16.2 (9)
O1—Nd1—O8—S2	51.9 (4)	C3—C4—C8—O4	−162.4 (6)
O2—Nd1—O8—S2	9.2 (4)	C5—C4—C8—O3	−165.3 (6)
C1—Nd1—O8—S2	32.3 (4)	C3—C4—C8—O3	16.1 (9)
Nd1—O2—C1—O1	9.6 (6)	Nd1^vi—O5—C9—O6	−14.0 (10)
Nd1—O2—C1—C2	−169.4 (5)	Nd1^vi—O5—C9—C6	168.5 (4)
Nd1—O1—C1—O2	−9.8 (7)	Nd1^vii—O6—C9—O5	32.1 (11)
Nd1—O1—C1—C2	169.2 (5)	Nd1^vii—O6—C9—C6	−150.3 (5)
O3ⁱ—Nd1—C1—O2	151.7 (3)	C7—C6—C9—O5	43.1 (8)
O6ⁱⁱ—Nd1—C1—O2	−106.7 (5)	C5—C6—C9—O5	−141.3 (6)
O5ⁱⁱⁱ—Nd1—C1—O2	84.5 (4)	C7—C6—C9—O6	−134.6 (6)
O4^iv—Nd1—C1—O2	13.0 (4)	C5—C6—C9—O6	40.9 (8)

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

Experimental details

Crystal data
Chemical formula	[Nd(C₉H₃O₆)(C₂H₆OS)₂]
M_r	507.61
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	10.380 (2), 10.752 (3), 16.025 (4)
β (°)	106.419 (4)
V (Å³)	1715.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.31
Crystal size (mm)	0.50 × 0.40 × 0.40

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.289, 0.351
No. of measured, independent and observed [I > 2σ(I)] reflections	8925, 3008, 2453
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.082, 0.98
No. of reflections	3008
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.92, −0.83

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We would like to thank the Open Research Fund of the State Key Laboratory of Inorganic Synthesis and Preparative Chemistry (grant No. 2011–08).

References

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