Poly[[diaqua­(3-carb­oxy-5-nitro­ben­zo­ato)(μ-5-nitro­benzene-1,3-dicarboxyl­ato)neodymium(III)] 2.5-hydrate]

Raime, N.-N.; Adnan, R.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536809032486

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1108-m1109

doi:10.1107/S1600536809032486

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Poly[[diaqua(3-carboxy-5-nitrobenzoato)(μ-5-nitrobenzene-1,3-dicarboxylato)neodymium(III)] 2.5-hydrate]

Nurul-Nadia Raime,^a Rohana Adnan,^a ‡ Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 27 July 2009; accepted 15 August 2009; online 22 August 2009)

In the title compound, {[Nd(C₈H₃NO₆)(C₈H₄NO₆)(H₂O)₂]·2.5H₂O}_n, the Nd^II ion is nine-coordinated by seven O atoms from five carboxylate groups and two water molecules. The [Nd(C₈H₃NO₆)(H₂O)₂]²⁺ units are bridged by 5-nitroisophthalate dianions, forming polymeric sheets parallel to the ab plane. The polymeric sheets are linked into a three-dimensional network by O—H⋯O and C—H⋯O hydrogen bonds, and π–π interactions [centroid–centroid distance = 3.5533 (11) Å]. The 5-nitroisophthalate(1−) anion is disordered over three positions with an occupancy ratio of 0.68:0.23:0.09. Two of the uncoordinated water molecules are disordered over two positions, with occupancy ratios of 0.722 (15):0.278 (15) and 0.279 (6):0.221 (6), respectively.

Related literature

For related structures, see: Ye et al. (2008 ); Eddaoudi et al. (2001 ); Bünzli & Choppin (1989 ); Huang et al. (2008 ); Cui et al. (2002 ); Yan et al. (2005 ); Ren et al. (2006 ); Li et al. (2005 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

[Nd(C₈H₃NO₆)(C₈H₄NO₆)(H₂O)₂]·2.5H₂O
M_r = 644.55
Triclinic, $[P \overline 1]$
a = 9.5748 (1) Å
b = 10.4634 (1) Å
c = 13.3285 (2) Å
α = 69.279 (1)°
β = 71.753 (1)°
γ = 66.046 (1)°
V = 1118.71 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.41 mm⁻¹
T = 100 K
0.35 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.484, T_max = 0.742
22527 measured reflections
5879 independent reflections
5725 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.057
S = 1.21
5879 reflections
398 parameters
115 restraints
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Selected bond lengths (Å)

Nd1—O7	2.3302 (13)
Nd1—O8ⁱ	2.4214 (14)
Nd1—O10ⁱⁱ	2.4481 (14)
Nd1—O1W	2.4612 (14)
Nd1—O9ⁱⁱⁱ	2.4708 (13)
Nd1—O2W	2.4775 (15)
Nd1—O2	2.5223 (13)
Nd1—O1	2.5743 (14)
Nd1—O10ⁱⁱⁱ	2.9332 (14)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) x+1, y-1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5A—H5A⋯O3W^iv	0.84	1.76	2.596 (5)	178
O1W—H1W1⋯O2^v	0.74	1.99	2.731 (3)	175
O1W—H2W1⋯O4WA	0.94	2.00	2.849 (4)	149
O2W—H1W2⋯O4WA	0.84	1.86	2.667 (3)	159
O2W—H2W2⋯O1ⁱ	0.82	2.06	2.874 (3)	172
O3W—H1W3⋯O11^vi	0.91	2.56	3.246 (3)	132
O3W—H1W3⋯O12^vi	0.91	2.05	2.902 (3)	156
O3W—H2W3⋯O9ⁱⁱⁱ	0.96	1.76	2.688 (2)	162
O4WA—H2W4⋯O3W	0.85	2.51	3.118 (6)	130
C12—H12A⋯O1ⁱⁱ	0.95	2.41	3.351 (2)	169
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) x+1, y-1, z; (iv) x-1, y, z+1; (v) -x+1, -y+1, -z+1; (vi) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032486/ci2868sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032486/ci2868Isup2.hkl

checkCIF report

Comment top

The research on the assembly of lanthanide coordination networks has increased over the years (Ye et al., 2008; Eddaoudi et al., 2001). Lanthanide provide opportunities for the discovery of unusual network topologies (Bünzli & Choppin, 1989; Huang et al., 2008; Cui et al., 2002) due to its high and variable coordination numbers and flexible coordination environments (Yan et al., 2005).

5- Nitroisophthalic acid (nia) has two carboxylic groups which may be completely or partially deprotonated and thus produces versatile coordination modes with lanthanide ions. Moreover, the existence of nitro group as an electron-withdrawing group has profound impacts on the electron density of the whole ligand, and thereby different physical phenomena can be produced (Ren et al., 2006; Li et al., 2005). In this paper, we report the crystal structure of a polymeric coordination complex formed from hydrothermal reaction between trivalent neodymium ion and nitroisophthalic acid.

The asymmetric unit of the title polymeric compound is shown in Fig. 1. In the crystal structure, each Nd^III ion adopts a nine-coordination environment being coordinated by two O atoms from two water molecules and seven O atoms from five carboxylate groups. The Nd—O distances range from 2.3302 (13) to 2.9332 (14) Å for carboxylate groups and 2.4612 (14) and 2.4775 (15) Å, respectively for O1W and O2W (Table 1). The nitro group attached to the C1-C6 benzene ring is slightly twisted, with a dihedral angle of 12.2 (3)° for the major disorder component A [ 9(1)° for B and 3(1)° for C]. The nitro group attached to the C9-C14 benzene ring is twisted by a dihedral angle of 21.2 (1)°. The dihedral angles between C1-C6 benzene rings and planes of carboxyl groups in disorder components A, B and C are 5.8 (5)°, 9(1)° and 29 (1)°, respectively. The adjacent [Nd(C₈H₃NO₆)(H₂O)₂]²⁺ units are bridged by 5-nitroisophthalate dianions to form polymeric sheets parallel to the ab plane (Fig. 2).

The polymeric sheets are linked into a three-dimensional network (Fig. 3) by O—H···O and C—H···O hydrogen bonds (Table 2). There also exist a π–π interaction between the C9–C14 benzene rings at (x, y, z) and (-x, 2-y, 1-z), with a centroid-to-centroid distance of 3.5533 (11) Å.

Related literature top

For related structures, see: Ye et al. (2008); Eddaoudi et al. (2001); Bünzli & Choppin (1989); Huang et al. (2008); Cui et al. (2002); Yan et al. (2005); Ren et al. (2006); Li et al. (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 5-nitroisophthalic acid (0.4243 g, 2.0 mmol), sodium hydroxide (0.140 g, 3.5 mmol) and distilled water (30 ml) was heated till boiling. The solution was left to cool to room temperature before neodymium(III) nitrate hexahydrate salt, Nd(NO₃).6H₂O (0.4380 g, 1.0 mmol) was added to it. The pH of the mixture was controlled to be between 3–4 by adding 1 M NaOH or 1 M HNO₃. Subsequently the solution was poured into a 40 ml Teflon tube, which was then sealed and heated at 403 K for 3 d. Upon cooling to room temperature, light purple crystals of the title compound were obtained which were filtered, washed with distilled water and left to dry in air.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. All disorder components are shown. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Part of the polymeric sheet, showing the coordination environment of Nd^III ion. Displacement ellipsoids are drawn at the 50% probability level. Only major disorder components are shown. Uncoordinated water molecules and H atoms have been omitted for clarity. Symmetry codes: (A) -x, 1-y, 1-z ; (B) -x, 2-y, 1-z; (c) 1+x, -1+y, z.
	Fig. 3. The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. Only major disorder components are shown.

Poly[[diaqua(3-carboxy-5-nitrobenzoato)(µ-5-nitrobenzene-1,3- dicarboxylato)neodymium(III)] 2.5-hydrate] top

Crystal data top

[Nd(C₈H₃NO₆)(C₈H₄NO₆)(H₂O)₂]·2.5H₂O	Z = 2
M_r = 644.55	F(000) = 636
Triclinic, P1	D_x = 1.913 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5748 (1) Å	Cell parameters from 9930 reflections
b = 10.4634 (1) Å	θ = 2.7–29.0°
c = 13.3285 (2) Å	µ = 2.41 mm⁻¹
α = 69.279 (1)°	T = 100 K
β = 71.753 (1)°	Plate, purple
γ = 66.046 (1)°	0.35 × 0.24 × 0.13 mm
V = 1118.71 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5879 independent reflections
Radiation source: fine-focus sealed tube	5725 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 29.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.484, T_max = 0.742	k = −14→14
22527 measured reflections	l = −18→18

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0337P)² + 0.5091P] where P = (F_o² + 2F_c²)/3
5879 reflections	(Δ/σ)_max = 0.001
398 parameters	Δρ_max = 1.18 e Å⁻³
115 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Nd(C₈H₃NO₆)(C₈H₄NO₆)(H₂O)₂]·2.5H₂O	γ = 66.046 (1)°
M_r = 644.55	V = 1118.71 (2) Å³
Triclinic, P1	Z = 2
a = 9.5748 (1) Å	Mo Kα radiation
b = 10.4634 (1) Å	µ = 2.41 mm⁻¹
c = 13.3285 (2) Å	T = 100 K
α = 69.279 (1)°	0.35 × 0.24 × 0.13 mm
β = 71.753 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5879 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5725 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.742	R_int = 0.019
22527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	115 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.21	Δρ_max = 1.18 e Å⁻³
5879 reflections	Δρ_min = −0.77 e Å⁻³
398 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
Nd1	0.285572 (9)	0.468414 (9)	0.486911 (7)	0.01037 (4)
O3A	0.5272 (5)	−0.1271 (4)	0.9533 (3)	0.0330 (9)	0.68
O4A	0.3769 (4)	−0.1558 (3)	1.1135 (2)	0.0463 (8)	0.68
O5A	−0.1663 (5)	0.1114 (5)	1.1553 (3)	0.0263 (8)	0.68
H5A	−0.2601	0.1301	1.1875	0.039*	0.68
O6A	−0.2644 (3)	0.3037 (5)	1.0252 (3)	0.0605 (13)	0.68
N1A	0.4039 (6)	−0.0919 (4)	1.0164 (3)	0.0297 (7)	0.68
C1A	0.0383 (3)	0.2754 (4)	0.8934 (3)	0.0205 (8)	0.68
H1AA	−0.0439	0.3572	0.8654	0.025*	0.68
C2A	0.0078 (3)	0.1835 (5)	0.9962 (3)	0.0198 (8)	0.68
C3A	0.1281 (4)	0.0639 (4)	1.0372 (2)	0.0238 (9)	0.68
H3AA	0.1072	0.0011	1.1075	0.029*	0.68
C4A	0.2789 (4)	0.0361 (3)	0.9754 (3)	0.0245 (8)	0.68
C5A	0.3094 (3)	0.1279 (4)	0.8726 (3)	0.0189 (9)	0.68
H5AA	0.4125	0.1089	0.8304	0.023*	0.68
C6A	0.1891 (4)	0.2476 (4)	0.8316 (3)	0.0165 (13)	0.68
C15A	−0.1548 (5)	0.2079 (7)	1.0602 (3)	0.0268 (9)	0.68
O3B	0.4896 (15)	−0.1413 (17)	0.9604 (13)	0.027 (3)*	0.23
O4B	0.3076 (14)	−0.1937 (12)	1.0907 (9)	0.056 (3)*	0.23
O5B	−0.1948 (16)	0.1468 (13)	1.1445 (11)	0.025 (3)*	0.23
H5B	−0.2852	0.1742	1.1814	0.037*	0.23
O6B	−0.2641 (10)	0.3699 (8)	1.0410 (7)	0.0257 (18)*	0.23
N1B	0.3557 (15)	−0.1115 (12)	1.0079 (10)	0.040 (3)*	0.23
C1B	0.0367 (14)	0.3066 (10)	0.8974 (11)	0.016 (3)*	0.23
H1BA	−0.0349	0.4004	0.8737	0.019*	0.23
C2B	−0.0066 (12)	0.2128 (14)	0.9957 (11)	0.038 (5)*	0.23
C3B	0.0982 (14)	0.0756 (13)	1.0304 (10)	0.039 (5)*	0.23
H3BA	0.0686	0.0115	1.0976	0.046*	0.23
C4B	0.2463 (12)	0.0322 (10)	0.9668 (10)	0.021 (3)*	0.23
C5B	0.2896 (12)	0.1260 (15)	0.8684 (10)	0.028 (4)*	0.23
H5BA	0.3907	0.0963	0.8249	0.033*	0.23
C6B	0.1848 (16)	0.2632 (14)	0.8337 (10)	0.016 (4)*	0.23
C15B	−0.1695 (13)	0.2567 (12)	1.0630 (10)	0.019 (3)*	0.23
O3C	0.449 (2)	−0.130 (3)	0.9824 (19)	0.0208 (13)*	0.09
O4C	0.272 (2)	−0.1538 (18)	1.1276 (12)	0.0208 (13)*	0.09
O5C	−0.2380 (19)	0.2386 (18)	1.1423 (12)	0.0208 (13)*	0.09
H5C	−0.3302	0.2675	1.1873	0.025*	0.09
O6C	−0.2201 (18)	0.4585 (14)	1.0575 (13)	0.0208 (13)*	0.09
N1C	0.318 (2)	−0.0826 (18)	1.0374 (14)	0.0208 (13)*	0.09
C1C	0.0294 (19)	0.3429 (15)	0.9028 (13)	0.0208 (13)*	0.09
H1CA	−0.0355	0.4382	0.8740	0.025*	0.09
C2C	−0.0198 (15)	0.2637 (16)	1.0071 (12)	0.0208 (13)*	0.09
C3C	0.0750 (18)	0.1244 (16)	1.0493 (11)	0.0208 (13)*	0.09
H3CA	0.0414	0.0702	1.1206	0.025*	0.09
C4C	0.2191 (19)	0.0642 (16)	0.9873 (14)	0.0208 (13)*	0.09
C5C	0.2683 (19)	0.143 (2)	0.8830 (15)	0.0208 (13)*	0.09
H5CA	0.3668	0.1023	0.8406	0.025*	0.09
C6C	0.173 (2)	0.283 (2)	0.8408 (12)	0.0208 (13)*	0.09
C15C	−0.174 (2)	0.3312 (17)	1.0721 (15)	0.0208 (13)*	0.09
O1	0.11719 (16)	0.45727 (15)	0.68090 (11)	0.0170 (3)
O2	0.36376 (16)	0.31566 (15)	0.66785 (11)	0.0165 (3)
O7	0.05148 (16)	0.65931 (14)	0.46945 (12)	0.0176 (3)
O8	−0.19586 (17)	0.73727 (15)	0.45331 (13)	0.0209 (3)
O9	−0.49580 (16)	1.26834 (15)	0.42188 (12)	0.0188 (3)
O10	−0.37511 (16)	1.38214 (14)	0.45852 (11)	0.0157 (3)
O11	0.1860 (2)	1.24682 (18)	0.22910 (16)	0.0325 (4)
O12	0.32156 (17)	1.02380 (18)	0.29539 (14)	0.0253 (3)
N2	0.19668 (19)	1.12233 (19)	0.28241 (14)	0.0178 (3)
C7	0.2251 (2)	0.3495 (2)	0.72073 (15)	0.0155 (3)
C8	−0.0736 (2)	0.75718 (19)	0.44717 (14)	0.0122 (3)
C9	−0.0762 (2)	0.91156 (18)	0.41124 (14)	0.0107 (3)
C10	−0.2178 (2)	1.02243 (19)	0.42723 (14)	0.0115 (3)
H10A	−0.3122	1.0009	0.4554	0.014*
C11	−0.2213 (2)	1.16466 (19)	0.40205 (14)	0.0113 (3)
C12	−0.0849 (2)	1.19940 (19)	0.35355 (14)	0.0124 (3)
H12A	−0.0861	1.2963	0.3343	0.015*
C13	0.0528 (2)	1.0867 (2)	0.33446 (14)	0.0129 (3)
C14	0.0619 (2)	0.94284 (19)	0.36509 (14)	0.0124 (3)
H14A	0.1593	0.8681	0.3549	0.015*
C16	−0.3728 (2)	1.27944 (19)	0.42875 (14)	0.0127 (3)
O1W	0.39421 (17)	0.62127 (17)	0.31765 (11)	0.0214 (3)
H1W1	0.4595	0.6422	0.3181	0.032*
H2W1	0.4207	0.6070	0.2475	0.032*
O2W	0.20344 (18)	0.4620 (2)	0.33051 (13)	0.0285 (4)
H1W2	0.2599	0.4648	0.2674	0.043*
H2W2	0.1146	0.4785	0.3245	0.043*
O3W	0.5412 (2)	0.1731 (2)	0.24946 (15)	0.0377 (4)
H1W3	0.4742	0.1364	0.2425	0.057*
H2W3	0.5221	0.1903	0.3193	0.057*
O4WA	0.4139 (3)	0.5063 (6)	0.1473 (2)	0.0342 (12)	0.722 (15)
H1W4	0.3780	0.5660	0.0913	0.051*	0.722 (15)
H2W4	0.4716	0.4275	0.1301	0.051*	0.722 (15)
O4WB	0.4055 (9)	0.4415 (15)	0.1312 (8)	0.037 (3)	0.278 (15)
H3W4	0.3704	0.4757	0.0809	0.056*	0.278 (15)
H4W4	0.4353	0.3561	0.1412	0.056*	0.278 (15)
O5WA	0.6107 (14)	0.5930 (14)	0.0951 (10)	0.082 (4)	0.279 (6)
H1W5	0.7059	0.5714	0.0630	0.123*	0.279 (6)
H2W5	0.5861	0.5169	0.1155	0.123*	0.279 (6)
O5WB	0.9195 (14)	0.4364 (12)	0.0923 (8)	0.051 (3)	0.221 (6)
H3W5	0.8615	0.4864	0.1375	0.077*	0.221 (6)
H4W5	1.0037	0.3835	0.1152	0.077*	0.221 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Nd1	0.00707 (6)	0.00691 (6)	0.01558 (6)	−0.00155 (4)	−0.00089 (3)	−0.00326 (4)
O3A	0.038 (2)	0.0212 (16)	0.0264 (15)	−0.0010 (16)	−0.0073 (15)	−0.0004 (11)
O4A	0.064 (2)	0.0291 (15)	0.0201 (12)	−0.0069 (14)	−0.0055 (13)	0.0107 (10)
O5A	0.0263 (18)	0.037 (2)	0.0144 (13)	−0.0199 (18)	0.0051 (12)	−0.0027 (14)
O6A	0.0223 (14)	0.103 (3)	0.0277 (14)	−0.0250 (18)	−0.0064 (11)	0.0225 (18)
N1A	0.043 (2)	0.0183 (15)	0.0194 (14)	−0.0077 (16)	−0.0092 (15)	0.0041 (11)
C1A	0.0177 (17)	0.027 (2)	0.0192 (16)	−0.0148 (15)	−0.0041 (11)	−0.0003 (16)
C2A	0.0189 (16)	0.034 (2)	0.0095 (14)	−0.0193 (14)	−0.0011 (10)	0.0016 (13)
C3A	0.036 (2)	0.0240 (19)	0.0128 (14)	−0.0182 (16)	−0.0061 (15)	0.0037 (11)
C4A	0.035 (2)	0.0231 (19)	0.0186 (16)	−0.0142 (16)	−0.0103 (16)	0.0006 (12)
C5A	0.0233 (17)	0.0150 (17)	0.0155 (15)	−0.0079 (14)	−0.0039 (13)	0.0010 (11)
C6A	0.018 (2)	0.019 (2)	0.0147 (17)	−0.0128 (14)	−0.0026 (10)	0.0009 (12)
C15A	0.0245 (18)	0.044 (3)	0.0150 (16)	−0.0223 (19)	−0.0037 (12)	0.0009 (17)
O1	0.0127 (6)	0.0151 (6)	0.0183 (6)	−0.0033 (5)	−0.0015 (5)	−0.0018 (5)
O2	0.0112 (6)	0.0155 (6)	0.0192 (6)	−0.0062 (5)	−0.0027 (5)	0.0014 (5)
O7	0.0123 (6)	0.0091 (6)	0.0256 (7)	0.0005 (5)	−0.0037 (5)	−0.0026 (5)
O8	0.0148 (7)	0.0110 (6)	0.0374 (8)	−0.0051 (5)	−0.0068 (6)	−0.0047 (6)
O9	0.0096 (6)	0.0161 (7)	0.0311 (7)	−0.0019 (5)	−0.0015 (5)	−0.0117 (6)
O10	0.0170 (6)	0.0099 (6)	0.0203 (6)	−0.0039 (5)	−0.0009 (5)	−0.0072 (5)
O11	0.0217 (8)	0.0195 (8)	0.0512 (10)	−0.0135 (6)	0.0080 (7)	−0.0089 (7)
O12	0.0092 (6)	0.0269 (8)	0.0378 (8)	−0.0053 (6)	0.0001 (6)	−0.0111 (7)
N2	0.0120 (7)	0.0190 (8)	0.0244 (8)	−0.0080 (6)	0.0022 (6)	−0.0099 (6)
C7	0.0139 (8)	0.0152 (9)	0.0172 (8)	−0.0072 (7)	−0.0030 (6)	−0.0014 (6)
C8	0.0118 (8)	0.0086 (7)	0.0145 (7)	−0.0024 (6)	−0.0007 (6)	−0.0040 (6)
C9	0.0091 (7)	0.0079 (7)	0.0143 (7)	−0.0014 (6)	−0.0028 (6)	−0.0030 (6)
C10	0.0081 (7)	0.0107 (8)	0.0150 (7)	−0.0027 (6)	−0.0014 (6)	−0.0039 (6)
C11	0.0085 (7)	0.0097 (8)	0.0148 (7)	−0.0014 (6)	−0.0018 (6)	−0.0048 (6)
C12	0.0111 (8)	0.0109 (8)	0.0155 (7)	−0.0041 (6)	−0.0008 (6)	−0.0048 (6)
C13	0.0094 (8)	0.0139 (8)	0.0168 (7)	−0.0057 (6)	0.0003 (6)	−0.0059 (6)
C14	0.0086 (7)	0.0121 (8)	0.0155 (7)	−0.0023 (6)	−0.0013 (6)	−0.0048 (6)
C16	0.0113 (8)	0.0089 (8)	0.0155 (7)	−0.0024 (6)	−0.0001 (6)	−0.0038 (6)
O1W	0.0170 (7)	0.0319 (8)	0.0164 (6)	−0.0145 (6)	−0.0027 (5)	−0.0008 (6)
O2W	0.0138 (7)	0.0522 (11)	0.0270 (7)	−0.0106 (7)	−0.0007 (6)	−0.0222 (7)
O3W	0.0305 (9)	0.0669 (13)	0.0304 (8)	−0.0311 (9)	0.0039 (7)	−0.0205 (9)
O4WA	0.0301 (14)	0.046 (3)	0.0198 (11)	−0.0101 (13)	−0.0026 (9)	−0.0065 (11)
O4WB	0.027 (3)	0.045 (5)	0.030 (3)	−0.013 (3)	0.005 (3)	−0.005 (4)
O5WA	0.072 (6)	0.091 (7)	0.103 (7)	−0.024 (5)	−0.012 (5)	−0.058 (6)
O5WB	0.063 (6)	0.052 (6)	0.045 (5)	−0.022 (5)	−0.011 (4)	−0.017 (4)

Geometric parameters (Å, º) top

Nd1—O7	2.3302 (13)	C1C—C2C	1.39
Nd1—O8ⁱ	2.4214 (14)	C1C—C6C	1.39
Nd1—O10ⁱⁱ	2.4481 (14)	C1C—H1CA	0.95
Nd1—O1W	2.4612 (14)	C2C—C3C	1.39
Nd1—O9ⁱⁱⁱ	2.4708 (13)	C2C—C15C	1.486 (13)
Nd1—O2W	2.4775 (15)	C3C—C4C	1.39
Nd1—O2	2.5223 (13)	C3C—H3CA	0.95
Nd1—O1	2.5743 (14)	C4C—C5C	1.39
Nd1—C7	2.8822 (18)	C5C—C6C	1.39
Nd1—O10ⁱⁱⁱ	2.9332 (14)	C5C—H5CA	0.95
Nd1—C16ⁱⁱⁱ	3.0749 (18)	C6C—C7	1.512 (12)
O3A—N1A	1.218 (6)	O1—C7	1.263 (2)
O4A—N1A	1.228 (4)	O2—C7	1.263 (2)
O5A—C15A	1.317 (5)	O7—C8	1.258 (2)
O5A—H5A	0.84	O8—C8	1.243 (2)
O6A—C15A	1.202 (6)	O8—Nd1ⁱ	2.4214 (14)
N1A—C4A	1.454 (4)	O9—C16	1.263 (2)
C1A—C2A	1.39	O9—Nd1^iv	2.4708 (13)
C1A—C6A	1.39	O10—C16	1.261 (2)
C1A—H1AA	0.95	O10—Nd1ⁱⁱ	2.4482 (14)
C2A—C3A	1.39	O10—Nd1^iv	2.9332 (14)
C2A—C15A	1.489 (4)	O11—N2	1.222 (2)
C3A—C4A	1.39	O12—N2	1.235 (2)
C3A—H3AA	0.95	N2—C13	1.468 (2)
C4A—C5A	1.39	C8—C9	1.505 (2)
C5A—C6A	1.39	C9—C14	1.391 (2)
C5A—H5AA	0.95	C9—C10	1.395 (2)
C6A—C7	1.518 (3)	C10—C11	1.393 (2)
O3B—N1B	1.203 (14)	C10—H10A	0.95
O4B—N1B	1.225 (12)	C11—C12	1.395 (2)
O5B—C15B	1.319 (13)	C11—C16	1.496 (2)
O5B—H5B	0.84	C12—C13	1.390 (2)
O6B—C15B	1.166 (12)	C12—H12A	0.95
N1B—C4B	1.469 (11)	C13—C14	1.386 (3)
C1B—C2B	1.39	C14—H14A	0.95
C1B—C6B	1.39	C16—Nd1^iv	3.0749 (18)
C1B—H1BA	0.95	O1W—H1W1	0.74
C2B—C3B	1.39	O1W—H2W1	0.94
C2B—C15B	1.511 (11)	O2W—H1W2	0.84
C3B—C4B	1.39	O2W—H2W2	0.82
C3B—H3BA	0.95	O3W—H1W3	0.91
C4B—C5B	1.39	O3W—H2W3	0.96
C5B—C6B	1.39	O4WA—H1W4	0.85
C5B—H5BA	0.95	O4WA—H2W4	0.85
C6B—C7	1.480 (9)	O4WB—H3W4	0.75
O3C—N1C	1.239 (16)	O4WB—H4W4	0.79
O4C—N1C	1.223 (15)	O5WA—H1W5	0.85
O5C—C15C	1.294 (15)	O5WA—H2W5	0.85
O5C—H5C	0.90	O5WB—H3W5	0.85
O6C—C15C	1.184 (16)	O5WB—H4W5	0.85
N1C—C4C	1.481 (13)

O7—Nd1—O8ⁱ	100.76 (5)	C5B—C6B—C1B	120.0
O7—Nd1—O10ⁱⁱ	88.82 (5)	C5B—C6B—C7	118.1 (8)
O8ⁱ—Nd1—O10ⁱⁱ	145.95 (5)	C1B—C6B—C7	121.1 (8)
O7—Nd1—O1W	84.42 (5)	O6B—C15B—O5B	124.3 (11)
O8ⁱ—Nd1—O1W	139.99 (5)	O6B—C15B—C2B	124.3 (10)
O10ⁱⁱ—Nd1—O1W	72.98 (5)	O5B—C15B—C2B	111.2 (10)
O7—Nd1—O9ⁱⁱⁱ	151.36 (5)	C15C—O5C—H5C	121.2
O8ⁱ—Nd1—O9ⁱⁱⁱ	73.06 (5)	O4C—N1C—O3C	121.9 (17)
O10ⁱⁱ—Nd1—O9ⁱⁱⁱ	112.18 (5)	O4C—N1C—C4C	121.7 (16)
O1W—Nd1—O9ⁱⁱⁱ	83.59 (5)	O3C—N1C—C4C	116.4 (15)
O7—Nd1—O2W	74.02 (5)	C2C—C1C—C6C	120.0
O8ⁱ—Nd1—O2W	72.51 (6)	C2C—C1C—H1CA	120.0
O10ⁱⁱ—Nd1—O2W	141.22 (5)	C6C—C1C—H1CA	120.0
O1W—Nd1—O2W	70.97 (5)	C3C—C2C—C1C	120.0
O9ⁱⁱⁱ—Nd1—O2W	77.50 (5)	C3C—C2C—C15C	121.1 (10)
O7—Nd1—O2	123.94 (5)	C1C—C2C—C15C	118.9 (10)
O8ⁱ—Nd1—O2	72.14 (5)	C4C—C3C—C2C	120.0
O10ⁱⁱ—Nd1—O2	75.40 (5)	C4C—C3C—H3CA	120.0
O1W—Nd1—O2	136.59 (5)	C2C—C3C—H3CA	120.0
O9ⁱⁱⁱ—Nd1—O2	81.61 (5)	C3C—C4C—C5C	120.0
O2W—Nd1—O2	142.83 (6)	C3C—C4C—N1C	117.9 (11)
O7—Nd1—O1	73.37 (5)	C5C—C4C—N1C	122.1 (11)
O8ⁱ—Nd1—O1	70.84 (5)	C6C—C5C—C4C	120.0
O10ⁱⁱ—Nd1—O1	81.06 (5)	C6C—C5C—H5CA	120.0
O1W—Nd1—O1	146.05 (5)	C4C—C5C—H5CA	120.0
O9ⁱⁱⁱ—Nd1—O1	127.22 (5)	C5C—C6C—C1C	120.0
O2W—Nd1—O1	124.29 (5)	C5C—C6C—C7	115.6 (10)
O2—Nd1—O1	51.38 (4)	C1C—C6C—C7	123.6 (10)
O7—Nd1—C7	99.34 (5)	O6C—C15C—O5C	128.0 (16)
O8ⁱ—Nd1—C7	65.51 (5)	O6C—C15C—C2C	118.1 (14)
O10ⁱⁱ—Nd1—C7	80.77 (5)	O5C—C15C—C2C	113.8 (14)
O1W—Nd1—C7	153.43 (5)	C7—O1—Nd1	90.75 (11)
O9ⁱⁱⁱ—Nd1—C7	102.98 (5)	C7—O2—Nd1	93.16 (11)
O2W—Nd1—C7	135.46 (6)	C8—O7—Nd1	171.21 (13)
O2—Nd1—C7	25.94 (5)	C8—O8—Nd1ⁱ	136.37 (12)
O1—Nd1—C7	25.99 (5)	C16—O9—Nd1^iv	106.33 (11)
O7—Nd1—O10ⁱⁱⁱ	146.58 (4)	C16—O10—Nd1ⁱⁱ	160.39 (12)
O8ⁱ—Nd1—O10ⁱⁱⁱ	112.58 (4)	C16—O10—Nd1^iv	84.27 (11)
O10ⁱⁱ—Nd1—O10ⁱⁱⁱ	64.92 (5)	Nd1ⁱⁱ—O10—Nd1^iv	115.08 (5)
O1W—Nd1—O10ⁱⁱⁱ	68.84 (4)	O11—N2—O12	124.08 (17)
O9ⁱⁱⁱ—Nd1—O10ⁱⁱⁱ	47.27 (4)	O11—N2—C13	118.38 (17)
O2W—Nd1—O10ⁱⁱⁱ	113.16 (4)	O12—N2—C13	117.54 (16)
O2—Nd1—O10ⁱⁱⁱ	71.17 (4)	O2—C7—O1	122.11 (17)
O1—Nd1—O10ⁱⁱⁱ	119.02 (4)	O2—C7—C6B	120.1 (5)
C7—Nd1—O10ⁱⁱⁱ	96.50 (5)	O1—C7—C6B	117.7 (5)
O7—Nd1—C16ⁱⁱⁱ	159.88 (5)	O2—C7—C6C	125.0 (7)
O8ⁱ—Nd1—C16ⁱⁱⁱ	92.18 (5)	O1—C7—C6C	112.3 (7)
O10ⁱⁱ—Nd1—C16ⁱⁱⁱ	88.96 (5)	O2—C7—C6A	117.2 (2)
O1W—Nd1—C16ⁱⁱⁱ	75.82 (5)	O1—C7—C6A	120.5 (2)
O9ⁱⁱⁱ—Nd1—C16ⁱⁱⁱ	23.21 (5)	O2—C7—Nd1	60.91 (9)
O2W—Nd1—C16ⁱⁱⁱ	95.64 (5)	O1—C7—Nd1	63.26 (10)
O2—Nd1—C16ⁱⁱⁱ	74.63 (5)	C6B—C7—Nd1	166.1 (8)
O1—Nd1—C16ⁱⁱⁱ	125.93 (4)	C6C—C7—Nd1	171.4 (11)
C7—Nd1—C16ⁱⁱⁱ	100.03 (5)	C6A—C7—Nd1	160.6 (3)
O10ⁱⁱⁱ—Nd1—C16ⁱⁱⁱ	24.08 (4)	O8—C8—O7	125.51 (17)
C15A—O5A—H5A	109.5	O8—C8—C9	117.18 (16)
O3A—N1A—O4A	124.8 (4)	O7—C8—C9	117.30 (16)
O3A—N1A—C4A	118.3 (3)	C14—C9—C10	120.32 (16)
O4A—N1A—C4A	116.9 (4)	C14—C9—C8	120.22 (15)
C2A—C1A—C6A	120.0	C10—C9—C8	119.44 (16)
C2A—C1A—H1AA	120.0	C11—C10—C9	120.31 (16)
C6A—C1A—H1AA	120.0	C11—C10—H10A	119.8
C3A—C2A—C1A	120.0	C9—C10—H10A	119.8
C3A—C2A—C15A	119.6 (3)	C10—C11—C12	120.42 (16)
C1A—C2A—C15A	120.3 (3)	C10—C11—C16	119.21 (16)
C4A—C3A—C2A	120.0	C12—C11—C16	120.37 (16)
C4A—C3A—H3AA	120.0	C13—C12—C11	117.41 (16)
C2A—C3A—H3AA	120.0	C13—C12—H12A	121.3
C3A—C4A—C5A	120.0	C11—C12—H12A	121.3
C3A—C4A—N1A	120.1 (3)	C14—C13—C12	123.58 (16)
C5A—C4A—N1A	119.9 (3)	C14—C13—N2	118.54 (16)
C4A—C5A—C6A	120.0	C12—C13—N2	117.84 (16)
C4A—C5A—H5AA	120.0	C13—C14—C9	117.75 (16)
C6A—C5A—H5AA	120.0	C13—C14—H14A	121.1
C5A—C6A—C1A	120.0	C9—C14—H14A	121.1
C5A—C6A—C7	119.4 (2)	O10—C16—O9	122.04 (17)
C1A—C6A—C7	120.6 (2)	O10—C16—C11	119.94 (16)
O6A—C15A—O5A	124.1 (4)	O9—C16—C11	118.02 (16)
O6A—C15A—C2A	122.3 (3)	O10—C16—Nd1^iv	71.65 (10)
O5A—C15A—C2A	113.5 (4)	O9—C16—Nd1^iv	50.45 (9)
C15B—O5B—H5B	109.5	C11—C16—Nd1^iv	167.91 (13)
O3B—N1B—O4B	123.1 (13)	Nd1—O1W—H1W1	118.6
O3B—N1B—C4B	118.3 (12)	Nd1—O1W—H2W1	125.6
O4B—N1B—C4B	118.5 (12)	H1W1—O1W—H2W1	102.4
C2B—C1B—C6B	120.0	Nd1—O2W—H1W2	123.6
C2B—C1B—H1BA	120.0	Nd1—O2W—H2W2	127.6
C6B—C1B—H1BA	120.0	H1W2—O2W—H2W2	106.9
C3B—C2B—C1B	120.0	H1W3—O3W—H2W3	115.1
C3B—C2B—C15B	119.6 (8)	H1W4—O4WA—H2W4	107.4
C1B—C2B—C15B	120.3 (8)	H1W4—O4WA—H3W4	54.4
C2B—C3B—C4B	120.0	H2W4—O4WA—H3W4	64.4
C2B—C3B—H3BA	120.0	H1W4—O4WB—H2W4	97.0
C4B—C3B—H3BA	120.0	H1W4—O4WB—H3W4	60.6
C3B—C4B—C5B	120.0	H2W4—O4WB—H3W4	123.4
C3B—C4B—N1B	118.5 (9)	H1W4—O4WB—H4W4	164.0
C5B—C4B—N1B	121.5 (9)	H2W4—O4WB—H4W4	79.4
C6B—C5B—C4B	120.0	H3W4—O4WB—H4W4	108.3
C6B—C5B—H5BA	120.0	H1W5—O5WA—H2W5	107.4
C4B—C5B—H5BA	120.0	H3W5—O5WB—H4W5	107.7

C6A—C1A—C2A—C3A	0.0	C5B—C6B—C7—Nd1	73 (2)
C6A—C1A—C2A—C15A	−176.5 (5)	C1B—C6B—C7—Nd1	−96 (2)
C1A—C2A—C3A—C4A	0.0	C5C—C6C—C7—O2	−25.6 (17)
C15A—C2A—C3A—C4A	176.6 (5)	C1C—C6C—C7—O2	164.7 (10)
C2A—C3A—C4A—C5A	0.0	C5C—C6C—C7—O1	163.1 (9)
C2A—C3A—C4A—N1A	−177.8 (4)	C1C—C6C—C7—O1	−6.7 (19)
O3A—N1A—C4A—C3A	167.1 (4)	C5C—C6C—C7—C6B	33 (8)
O4A—N1A—C4A—C3A	−13.6 (6)	C1C—C6C—C7—C6B	−137 (10)
O3A—N1A—C4A—C5A	−10.7 (6)	C5C—C6C—C7—C6A	36 (3)
O4A—N1A—C4A—C5A	168.6 (4)	C1C—C6C—C7—C6A	−134 (5)
C3A—C4A—C5A—C6A	0.0	C5A—C6A—C7—O2	3.6 (4)
N1A—C4A—C5A—C6A	177.8 (4)	C1A—C6A—C7—O2	−178.3 (3)
C4A—C5A—C6A—C1A	0.0	C5A—C6A—C7—O1	178.6 (2)
C4A—C5A—C6A—C7	178.2 (5)	C1A—C6A—C7—O1	−3.2 (5)
C2A—C1A—C6A—C5A	0.0	C5A—C6A—C7—C6B	−117 (7)
C2A—C1A—C6A—C7	−178.2 (5)	C1A—C6A—C7—C6B	61 (7)
C3A—C2A—C15A—O6A	−174.7 (5)	C5A—C6A—C7—C6C	−122 (4)
C1A—C2A—C15A—O6A	1.8 (8)	C1A—C6A—C7—C6C	56 (4)
C3A—C2A—C15A—O5A	2.6 (6)	C5A—C6A—C7—Nd1	82.8 (6)
C1A—C2A—C15A—O5A	179.2 (4)	C1A—C6A—C7—Nd1	−99.0 (5)
C6B—C1B—C2B—C3B	0.0	O7—Nd1—C7—O2	−162.80 (11)
C6B—C1B—C2B—C15B	−177.4 (17)	O8ⁱ—Nd1—C7—O2	99.56 (12)
C1B—C2B—C3B—C4B	0.0	O10ⁱⁱ—Nd1—C7—O2	−75.54 (11)
C15B—C2B—C3B—C4B	177.4 (17)	O1W—Nd1—C7—O2	−66.56 (17)
C2B—C3B—C4B—C5B	0.0	O9ⁱⁱⁱ—Nd1—C7—O2	35.26 (12)
C2B—C3B—C4B—N1B	177.8 (12)	O2W—Nd1—C7—O2	120.53 (12)
O3B—N1B—C4B—C3B	−170.2 (14)	O1—Nd1—C7—O2	−164.04 (19)
O4B—N1B—C4B—C3B	7.7 (19)	O10ⁱⁱⁱ—Nd1—C7—O2	−12.32 (12)
O3B—N1B—C4B—C5B	8 (2)	C16ⁱⁱⁱ—Nd1—C7—O2	11.75 (12)
O4B—N1B—C4B—C5B	−174.5 (13)	O7—Nd1—C7—O1	1.25 (12)
C3B—C4B—C5B—C6B	0.0	O8ⁱ—Nd1—C7—O1	−96.39 (12)
N1B—C4B—C5B—C6B	−177.8 (12)	O10ⁱⁱ—Nd1—C7—O1	88.51 (11)
C4B—C5B—C6B—C1B	0.0	O1W—Nd1—C7—O1	97.48 (15)
C4B—C5B—C6B—C7	−169.7 (17)	O9ⁱⁱⁱ—Nd1—C7—O1	−160.70 (11)
C2B—C1B—C6B—C5B	0.0	O2W—Nd1—C7—O1	−75.42 (13)
C2B—C1B—C6B—C7	169.3 (17)	O2—Nd1—C7—O1	164.04 (19)
C3B—C2B—C15B—O6B	178.9 (11)	O10ⁱⁱⁱ—Nd1—C7—O1	151.72 (11)
C1B—C2B—C15B—O6B	−4 (2)	C16ⁱⁱⁱ—Nd1—C7—O1	175.79 (11)
C3B—C2B—C15B—O5B	−6.3 (17)	O7—Nd1—C7—C6B	99 (2)
C1B—C2B—C15B—O5B	171.1 (13)	O8ⁱ—Nd1—C7—C6B	1 (2)
C6C—C1C—C2C—C3C	0.0	O10ⁱⁱ—Nd1—C7—C6B	−174 (2)
C6C—C1C—C2C—C15C	179.4 (19)	O1W—Nd1—C7—C6B	−165 (2)
C1C—C2C—C3C—C4C	0.0	O9ⁱⁱⁱ—Nd1—C7—C6B	−63 (2)
C15C—C2C—C3C—C4C	−179 (2)	O2W—Nd1—C7—C6B	22 (2)
C2C—C3C—C4C—C5C	0.0	O2—Nd1—C7—C6B	−98 (2)
C2C—C3C—C4C—N1C	178 (2)	O1—Nd1—C7—C6B	98 (2)
O4C—N1C—C4C—C3C	5 (3)	O10ⁱⁱⁱ—Nd1—C7—C6B	−111 (2)
O3C—N1C—C4C—C3C	−176 (2)	C16ⁱⁱⁱ—Nd1—C7—C6B	−86 (2)
O4C—N1C—C4C—C5C	−177 (2)	O7—Nd1—C7—C6A	107.5 (5)
O3C—N1C—C4C—C5C	2 (3)	O8ⁱ—Nd1—C7—C6A	9.9 (5)
C3C—C4C—C5C—C6C	0.0	O10ⁱⁱ—Nd1—C7—C6A	−165.2 (5)
N1C—C4C—C5C—C6C	−178 (2)	O1W—Nd1—C7—C6A	−156.2 (5)
C4C—C5C—C6C—C1C	0.0	O9ⁱⁱⁱ—Nd1—C7—C6A	−54.4 (5)
C4C—C5C—C6C—C7	−170 (2)	O2W—Nd1—C7—C6A	30.9 (5)
C2C—C1C—C6C—C5C	0.0	O2—Nd1—C7—C6A	−89.7 (5)
C2C—C1C—C6C—C7	169 (2)	O1—Nd1—C7—C6A	106.3 (5)
C3C—C2C—C15C—O6C	149.3 (18)	O10ⁱⁱⁱ—Nd1—C7—C6A	−102.0 (5)
C1C—C2C—C15C—O6C	−30 (3)	C16ⁱⁱⁱ—Nd1—C7—C6A	−77.9 (5)
C3C—C2C—C15C—O5C	−28 (3)	Nd1ⁱ—O8—C8—O7	4.0 (3)
C1C—C2C—C15C—O5C	152.6 (16)	Nd1ⁱ—O8—C8—C9	−175.30 (12)
O7—Nd1—O1—C7	−178.71 (12)	O8—C8—C9—C14	−156.86 (17)
O8ⁱ—Nd1—O1—C7	73.22 (11)	O7—C8—C9—C14	23.8 (2)
O10ⁱⁱ—Nd1—O1—C7	−87.26 (11)	O8—C8—C9—C10	24.8 (2)
O1W—Nd1—O1—C7	−127.43 (12)	O7—C8—C9—C10	−154.54 (17)
O9ⁱⁱⁱ—Nd1—O1—C7	23.86 (13)	C14—C9—C10—C11	−3.1 (3)
O2W—Nd1—O1—C7	124.75 (12)	C8—C9—C10—C11	175.22 (15)
O2—Nd1—O1—C7	−8.85 (11)	C9—C10—C11—C12	4.5 (3)
O10ⁱⁱⁱ—Nd1—O1—C7	−32.57 (12)	C9—C10—C11—C16	−174.87 (16)
C16ⁱⁱⁱ—Nd1—O1—C7	−5.12 (13)	C10—C11—C12—C13	−1.6 (3)
O7—Nd1—O2—C7	20.60 (13)	C16—C11—C12—C13	177.77 (16)
O8ⁱ—Nd1—O2—C7	−70.53 (12)	C11—C12—C13—C14	−2.8 (3)
O10ⁱⁱ—Nd1—O2—C7	99.01 (12)	C11—C12—C13—N2	179.38 (16)
O1W—Nd1—O2—C7	143.33 (11)	O11—N2—C13—C14	160.22 (19)
O9ⁱⁱⁱ—Nd1—O2—C7	−145.35 (12)	O12—N2—C13—C14	−19.7 (3)
O2W—Nd1—O2—C7	−89.17 (13)	O11—N2—C13—C12	−21.9 (3)
O1—Nd1—O2—C7	8.87 (11)	O12—N2—C13—C12	158.19 (17)
O10ⁱⁱⁱ—Nd1—O2—C7	167.05 (12)	C12—C13—C14—C9	4.1 (3)
C16ⁱⁱⁱ—Nd1—O2—C7	−168.00 (12)	N2—C13—C14—C9	−178.07 (16)
Nd1—O2—C7—O1	−16.8 (2)	C10—C9—C14—C13	−1.1 (3)
Nd1—O2—C7—C6B	164.1 (9)	C8—C9—C14—C13	−179.40 (16)
Nd1—O2—C7—C6C	172.6 (13)	Nd1ⁱⁱ—O10—C16—O9	173.8 (3)
Nd1—O2—C7—C6A	158.1 (3)	Nd1^iv—O10—C16—O9	2.76 (17)
Nd1—O1—C7—O2	16.47 (19)	Nd1ⁱⁱ—O10—C16—C11	−5.2 (5)
Nd1—O1—C7—C6B	−164.4 (9)	Nd1^iv—O10—C16—C11	−176.24 (15)
Nd1—O1—C7—C6C	−171.9 (12)	Nd1ⁱⁱ—O10—C16—Nd1^iv	171.0 (4)
Nd1—O1—C7—C6A	−158.3 (3)	Nd1^iv—O9—C16—O10	−3.4 (2)
C5B—C6B—C7—O2	−17.0 (11)	Nd1^iv—O9—C16—C11	175.62 (12)
C1B—C6B—C7—O2	173.5 (8)	C10—C11—C16—O10	145.14 (17)
C5B—C6B—C7—O1	163.9 (5)	C12—C11—C16—O10	−34.2 (2)
C1B—C6B—C7—O1	−5.6 (16)	C10—C11—C16—O9	−33.9 (2)
C5B—C6B—C7—C6C	−143 (9)	C12—C11—C16—O9	146.75 (17)
C1B—C6B—C7—C6C	47 (8)	C10—C11—C16—Nd1^iv	−17.6 (7)
C5B—C6B—C7—C6A	45 (7)	C12—C11—C16—Nd1^iv	163.1 (5)
C1B—C6B—C7—C6A	−124 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5A···O3W^v	0.84	1.76	2.596 (5)	178
O1W—H1W1···O2^vi	0.74	1.99	2.731 (3)	175
O1W—H2W1···O4WA	0.94	2.00	2.849 (4)	149
O2W—H1W2···O4WA	0.84	1.86	2.667 (3)	159
O2W—H2W2···O1ⁱ	0.82	2.06	2.874 (3)	172
O3W—H1W3···O11^vii	0.91	2.56	3.246 (3)	132
O3W—H1W3···O12^vii	0.91	2.05	2.902 (3)	156
O3W—H2W3···O9ⁱⁱⁱ	0.96	1.76	2.688 (2)	162
O4WA—H2W4···O3W	0.85	2.51	3.118 (6)	130
C12—H12A···O1ⁱⁱ	0.95	2.41	3.351 (2)	169

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

Experimental details

Crystal data
Chemical formula	[Nd(C₈H₃NO₆)(C₈H₄NO₆)(H₂O)₂]·2.5H₂O
M_r	644.55
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5748 (1), 10.4634 (1), 13.3285 (2)
α, β, γ (°)	69.279 (1), 71.753 (1), 66.046 (1)
V (Å³)	1118.71 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.35 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.484, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	22527, 5879, 5725
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.057, 1.21
No. of reflections	5879
No. of parameters	398
No. of restraints	115
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.77

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Nd1—O7	2.3302 (13)	Nd1—O2W	2.4775 (15)
Nd1—O8ⁱ	2.4214 (14)	Nd1—O2	2.5223 (13)
Nd1—O10ⁱⁱ	2.4481 (14)	Nd1—O1	2.5743 (14)
Nd1—O1W	2.4612 (14)	Nd1—O10ⁱⁱⁱ	2.9332 (14)
Nd1—O9ⁱⁱⁱ	2.4708 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5A—H5A···O3W^iv	0.84	1.76	2.596 (5)	178
O1W—H1W1···O2^v	0.74	1.99	2.731 (3)	175
O1W—H2W1···O4WA	0.94	2.00	2.849 (4)	149
O2W—H1W2···O4WA	0.84	1.86	2.667 (3)	159
O2W—H2W2···O1ⁱ	0.82	2.06	2.874 (3)	172
O3W—H1W3···O11^vi	0.91	2.56	3.246 (3)	132
O3W—H1W3···O12^vi	0.91	2.05	2.902 (3)	156
O3W—H2W3···O9ⁱⁱⁱ	0.96	1.76	2.688 (2)	162
O4WA—H2W4···O3W	0.85	2.51	3.118 (6)	130
C12—H12A···O1ⁱⁱ	0.95	2.41	3.351 (2)	169

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

Footnotes

‡Additional corresponding author, e_mail: r_adnan@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia (USM) for a Research University grant (No. 1001/PKIMIA/811120). HKF thanks USM for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). MMR thanks the Malaysian Government and USM for the award of the post of Research Officer under the Science Fund (grant No. 305/PFIZIK/613312).

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bünzli, J. C. & Choppin, G. R. (1989). Lanthanide Probes in Life, Chemical and Earth Sciences: Theory and Practice. Amsterdam: Elsevier. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cui, Y., Ngo, H. L., White, P. S. & Lin, W. (2002). Chem. Commun. pp. 1666–1667. Web of Science CSD CrossRef Google Scholar
Eddaoudi, M., Moler, D. B., Li, H., Chen, B., Reineke, T. M., O'Keeffe, M. & Yaghi, O. M. (2001). Acc. Chem. Res. 34, 319–330. Web of Science CrossRef PubMed CAS Google Scholar
Huang, Y., Yan, B. & Shao, M. (2008). Solid State Sci. 10, 90–98. Web of Science CSD CrossRef CAS Google Scholar
Li, X. J., Cao, R., Bi, W. H., Wang, Y., Wang, Y. L., Li, X. & Guo, Z. G. (2005). Cryst. Growth Des. 5, 1651–1656. Web of Science CSD CrossRef CAS Google Scholar
Ren, H., Song, T., Xu, J., He, X., Wang, L. & Zhang, P. (2006). Transition Met. Chem. 31, 992–998. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yan, B., Bai, Y. Y. & Cgen, Z. X. (2005). J. Mol. Struct. 741, 141–147. Web of Science CrossRef CAS Google Scholar
Ye, J. W., Zhang, J. Y., Ning, G. L., Tian, G., Chen, Y. & Wang, Y. (2008). Cryst. Growth Des. 8, 3098–3106. Web of Science CSD CrossRef CAS Google Scholar

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