catena-Poly[[di­aqua­[μ2-4-(4-carb­oxy­phen­oxy)benzoato](μ2-4,4′-oxydibenzo­ato)praseodymium(III)] monohydrate]

Li, P.; Su, D.-M.; Zheng, C.-G.

doi:10.1107/S1600536813026421

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages m586-m587

doi:10.1107/S1600536813026421

Open

access

catena-Poly[[diaqua[μ₂-4-(4-carboxyphenoxy)benzoato](μ₂-4,4′-oxydibenzoato)praseodymium(III)] monohydrate]

Ping Li,^a Duo-Meng Su ^a and Chang-Ge Zheng ^a ^*

^aSchool of Chemical and Material Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province 214122, People's Republic of China
^*Correspondence e-mail: cgzheng@jiangnan.edu.cn

(Received 4 September 2013; accepted 24 September 2013; online 5 October 2013)

In the title compound, {[Pr(C₁₄H₈O₅)(C₁₄H₉O₅)(H₂O)₂]·H₂O}_n, the Pr^III cation is eight-coordinated by six carboxyl O atoms from both a monoanionic 4-(4-carboxyphenoxy)benzoate and a dianionic 4,4′-oxydibenzoate ligand (four bridging with two from a bidentate chelate interaction), and two O-atom donors from water molecules. A single water molecule of solvation is also present. The complex units are linked through carboxyl O:O′ bridges giving a two-dimensional sheet polymer lying parallel to (001). An overall three-dimensional network structure is generated through intermolecular carboxylic acid and water O—H⋯O hydrogen bonds and weak C—H⋯O interactions.

CCDC reference: 962964

Related literature

For the potential properties of metal-organic complexes involving polycarboxylate ligands, see: Li et al. (2011 ); Wang et al. (2004 , 2005 ); Lin et al. (2010 ); Sun et al. (2009 ); Xu et al. (2011 ); Łyszczek & Mazur (2012 ). For similar structures, see: Thirumurugan & Natarajan (2004 ); Zhang et al. (2005 ).

Experimental

Crystal data

[Pr(C₁₄H₈O₅)(C₁₄H₉O₅)(H₂O)₂]·H₂O
M_r = 708.37
Monoclinic, C 2/c
a = 27.3970 (17) Å
b = 9.5764 (6) Å
c = 21.6754 (14) Å
β = 97.433 (1)°
V = 5639.1 (6) Å³
Z = 8
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 296 K
0.21 × 0.16 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.704, T_max = 0.774
20449 measured reflections
4972 independent reflections
4498 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.059
S = 1.08
4972 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Pr1—O9ⁱ	2.3983 (18)
Pr1—O5	2.4105 (19)
Pr1—O12ⁱⁱ	2.412 (2)
Pr1—O8ⁱⁱⁱ	2.4692 (19)
Pr1—O11	2.4719 (18)
Pr1—O10	2.5152 (19)
Pr1—O1	2.5163 (19)
Pr1—O7ⁱⁱⁱ	2.6534 (19)
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z; (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1^iv	0.82	2.02	2.822 (3)	166
O10—H10B⋯O2^v	0.85	2.09	2.880 (3)	154
O11—H11A⋯O4^vi	0.84	1.84	2.683 (3)	176
O11—H11B⋯O8^vii	0.84	1.89	2.707 (3)	163
C9—H9⋯O3^vi	0.93	2.48	3.337 (4)	153
C25—H25⋯O13ⁱⁱⁱ	0.93	2.59	3.454 (7)	155
Symmetry codes: (iii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+1, z-{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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

CCDC reference: 962964

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026421/zs2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026421/zs2278Isup2.hkl

checkCIF report

Comment top

Metal–organic frameworks (MOFs) with lanthanides have attracted much attention because of their abundant structural chemistry and valuable optical and magnetic properties (Lin et al., 2010). In contrast to coordination polymers with other transition metals, the architecture of lanthanide coordination polymers is hard to control owing to large coordination numbers and flexible coordination geometries of the lanthanide atom. The ligand 4-(4-carboxyphenoxy)benzoic acid (H₂oba) can be deprotonated, giving Hoba^- or oba^2- species and as V-shaped ligands, they can offer more many coordination modes compared to a linear ligand. Owing to the nonlinear flexibility around the etheric oxygen, this ligand can readily generate helical coordination polymers (Łyszczek & Mazur, 2012).

In the title praseodymium(III) complex with 4-(4-carboxyphenoxy)benzoic acid, {[Pr(C₁₄H₁₁O₆)(C₁₄H₁₀O₆)(H₂O)₂] . H₂O}_n, the Pr^III cations have irregular eight-coordinate stereochemistry, the asymmetric unit comprising one Pr^III cation, an an Hoba^- ligand, an oba^2- ligand, two monodentate water molecules (O10 and O11) and one water molecule of solvation (O13) (Fig. 1). There are two types of coordination modes with the oba^2- and Hoba^- ligands: (a) two carboxylate groups of the oba^2- ligand adopt a bridging bidentate mode (O5, O12ⁱⁱ) and a bidentate chelate mode (O7ⁱⁱⁱ, O8ⁱⁱⁱ), respectively, connecting three Pr^III atoms; (b) one carboxylate group of the Hoba^- ligand adopts a bridging bidentate (O1, O9ⁱ) mode, connecting two Pr^III atoms. For symmetry codes, see Table 1. The carboxylic acid group (O4, O3) is un-coordinated. The Pr—O bond lengths [range 2.3983 (18)–2.6534 (19) Å] (Table 1) are comparable with those in similar Pr^III complexes (Thirumurugan & Natarajan, 2004; Zhang et al., 2005). A two-dimensional coordination polymer is generated, lying parallel to (0 0 1). Adjacent layers are joined into a three-dimensional framework structure (Fig. 2) through intermolecular carboxylic acid and water O—H···O hydrogen bonds and weak C—H···O hydrogen-bonding interactions (Table 2).

Related literature top

For the potential properties of metal-organic complexes involving polycarboxylate ligands, see: Li et al. (2011); Wang et al. (2004, 2005); Lin et al. (2010); Sun et al. (2009); Xu et al. (2011); Łyszczek & Mazur (2012). For similar structures, see: Thirumurugan & Natarajan (2004); Zhang et al. (2005).

Experimental top

A mixture of 4-(4-carboxyphenoxy)benzoic acid (0.026 g, 0.1 mmol), Pr(NO₃)₃ 6H₂O (0.15 mmol, 62.2 mg), and deionized water (8 ml) was sealed in a teflon-lined stainless steel vessel (25 ml) and heated at 433 K for 72 h. The vessel was then cooled slowly to room temperature. Green block-like crystals were obtained by filtration and washed with water. Yield: 50.4 mg (47.5%, based on Pr). Elemental analysis: calcd. for C₂₈H₂₃O₁₃Pr, C 47.59%, H 3.25%. Found: C 47.48%, H 3.19%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The asymmetric unit of the title complex showing 30% probability displacement ellipsoids and the atom-numbering scheme. For symmetry codes: (i) -x, -y +1, -z; (ii) -x, -y, -z; (iii) x -1/2, y +1/2, z.
	Fig. 2. A packing diagram for the three-dimensional structure formed through O—H···O and C—H···O hydrogen-bonding interactions. Hydrogen bonds are indicated by dashed lines.

catena-Poly[[diaqua[µ₂-4-(4-carboxyphenoxy)benzoato](µ₂-4,4'-oxydibenzoato)praseodymium(III)] monohydrate] top

Crystal data top

[Pr(C₁₄H₈O₅)(C₁₄H₉O₅)(H₂O)₂]·H₂O	F(000) = 2832
M_r = 708.37	D_x = 1.669 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9984 reflections
a = 27.3970 (17) Å	θ = 2.4–27.6°
b = 9.5764 (6) Å	µ = 1.80 mm⁻¹
c = 21.6754 (14) Å	T = 296 K
β = 97.433 (1)°	Block, green
V = 5639.1 (6) Å³	0.21 × 0.16 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4972 independent reflections
Radiation source: fine-focus sealed tube	4498 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −32→27
T_min = 0.704, T_max = 0.774	k = −11→11
20449 measured reflections	l = −25→25

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0163P)² + 15.8309P] where P = (F_o² + 2F_c²)/3
4972 reflections	(Δ/σ)_max = 0.001
381 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Pr(C₁₄H₈O₅)(C₁₄H₉O₅)(H₂O)₂]·H₂O	V = 5639.1 (6) Å³
M_r = 708.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.3970 (17) Å	µ = 1.80 mm⁻¹
b = 9.5764 (6) Å	T = 296 K
c = 21.6754 (14) Å	0.21 × 0.16 × 0.15 mm
β = 97.433 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4972 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	4498 reflections with I > 2σ(I)
T_min = 0.704, T_max = 0.774	R_int = 0.026
20449 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0163P)² + 15.8309P] where P = (F_o² + 2F_c²)/3
4972 reflections	Δρ_max = 0.59 e Å⁻³
381 parameters	Δρ_min = −0.51 e Å⁻³

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
Pr1	0.014443 (5)	0.250000 (14)	0.008512 (7)	0.02218 (6)
C1	0.08267 (9)	−0.0154 (3)	0.06113 (13)	0.0281 (6)
C2	0.12798 (9)	−0.0851 (3)	0.09282 (12)	0.0257 (6)
C3	0.05948 (9)	0.5746 (3)	0.17173 (12)	0.0258 (6)
C4	0.04362 (9)	0.5108 (3)	0.10933 (12)	0.0254 (6)
C5	0.21188 (10)	−0.2111 (3)	0.15102 (14)	0.0341 (7)
C6	0.26088 (11)	0.8308 (3)	0.39077 (15)	0.0377 (7)
C7	0.33610 (11)	−0.3437 (3)	0.18593 (14)	0.0397 (7)
H7	0.3323	−0.3976	0.2207	0.048*
C8	0.09428 (10)	0.6972 (3)	0.28360 (13)	0.0327 (6)
C9	0.15967 (11)	−0.0134 (3)	0.13644 (16)	0.0418 (8)
H9	0.1527	0.0785	0.1459	0.050*
C10	0.08283 (12)	0.4950 (3)	0.22016 (14)	0.0401 (7)
H10	0.0867	0.3995	0.2148	0.048*
C11	0.10043 (13)	0.5567 (4)	0.27647 (14)	0.0447 (8)
H11	0.1162	0.5033	0.3089	0.054*
C12	0.34745 (11)	−0.1805 (3)	0.08407 (14)	0.0378 (7)
H12	0.3513	−0.1246	0.0500	0.045*
C13	0.29695 (11)	−0.2675 (3)	0.15686 (14)	0.0324 (7)
C14	0.05244 (12)	0.7155 (3)	0.18124 (14)	0.0365 (7)
H14	0.0355	0.7690	0.1496	0.044*
C15	0.31376 (12)	0.8545 (3)	0.41214 (17)	0.0430 (8)
C16	0.17743 (11)	0.8314 (4)	0.41406 (14)	0.0432 (8)
H16	0.1548	0.8484	0.4417	0.052*
C17	0.16187 (11)	0.7811 (3)	0.35461 (14)	0.0333 (7)
C18	0.13862 (12)	−0.2214 (3)	0.07976 (17)	0.0437 (8)
H18	0.1172	−0.2720	0.0513	0.052*
C19	0.20161 (12)	−0.0762 (4)	0.16618 (16)	0.0459 (8)
H19	0.2225	−0.0279	0.1960	0.055*
C20	0.18108 (13)	−0.2837 (4)	0.10883 (18)	0.0492 (9)
H20	0.1884	−0.3754	0.0994	0.059*
C21	0.30232 (11)	−0.1854 (4)	0.10597 (15)	0.0413 (8)
H21	0.2759	−0.1340	0.0866	0.050*
C22	0.38089 (11)	−0.3398 (3)	0.16320 (14)	0.0357 (7)
H22	0.4071	−0.3926	0.1823	0.043*
C23	0.24464 (12)	0.7818 (4)	0.33152 (15)	0.0414 (8)
H23	0.2672	0.7660	0.3037	0.050*
C24	0.22675 (12)	0.8557 (4)	0.43135 (15)	0.0452 (8)
H24	0.2374	0.8894	0.4710	0.054*
C25	0.07024 (12)	0.7778 (3)	0.23706 (14)	0.0396 (7)
H25	0.0660	0.8730	0.2430	0.048*
C26	0.38714 (10)	−0.2577 (3)	0.11215 (14)	0.0284 (6)
C27	0.19530 (12)	0.7562 (3)	0.31339 (15)	0.0404 (8)
H27	0.1847	0.7224	0.2737	0.048*
C28	0.43485 (10)	−0.2515 (3)	0.08701 (13)	0.0273 (6)
O1	0.05551 (7)	0.3854 (2)	0.10037 (9)	0.0348 (5)
O2	0.11178 (8)	0.7623 (2)	0.34028 (10)	0.0405 (6)
O3	0.34277 (8)	0.8348 (3)	0.36883 (12)	0.0494 (6)
H3	0.3715	0.8454	0.3840	0.074*
O4	0.32852 (9)	0.8911 (3)	0.46497 (12)	0.0614 (7)
O5	0.08076 (8)	0.1151 (2)	0.06299 (11)	0.0446 (6)
O6	0.25350 (8)	−0.2782 (3)	0.18227 (11)	0.0452 (6)
O7	0.46781 (7)	−0.3427 (2)	0.10035 (9)	0.0312 (4)
O8	0.44170 (7)	−0.1528 (2)	0.04974 (10)	0.0350 (5)
O9	0.01975 (7)	0.5838 (2)	0.06788 (9)	0.0328 (4)
O10	0.04446 (8)	0.1241 (2)	−0.08121 (10)	0.0385 (5)
H10A	0.0200	0.0888	−0.1040	0.058*
H10B	0.0591	0.1815	−0.1024	0.058*
O11	0.08179 (7)	0.38020 (19)	−0.03119 (9)	0.0326 (4)
H11B	0.0752	0.4617	−0.0446	0.039*
H11A	0.1106	0.3833	−0.0120	0.039*
O12	0.04866 (7)	−0.0880 (2)	0.03345 (10)	0.0393 (5)
O13	0.5392 (3)	0.6238 (7)	0.2092 (3)	0.251 (4)
H13B	0.5098	0.5933	0.2009	0.377*
H13A	0.5419	0.6668	0.1755	0.377*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.01793 (9)	0.02186 (9)	0.02589 (10)	0.00108 (5)	−0.00048 (6)	0.00062 (5)
C1	0.0228 (14)	0.0318 (16)	0.0294 (15)	0.0028 (12)	0.0028 (11)	0.0000 (12)
C2	0.0199 (13)	0.0250 (14)	0.0317 (15)	0.0013 (11)	0.0016 (11)	0.0019 (11)
C3	0.0234 (14)	0.0281 (14)	0.0245 (14)	−0.0003 (11)	−0.0014 (11)	−0.0007 (11)
C4	0.0202 (13)	0.0269 (14)	0.0289 (14)	−0.0007 (11)	0.0020 (11)	−0.0017 (11)
C5	0.0213 (15)	0.0440 (17)	0.0377 (17)	0.0088 (13)	0.0071 (12)	0.0143 (14)
C6	0.0304 (16)	0.0357 (17)	0.0446 (18)	−0.0017 (13)	−0.0044 (13)	0.0023 (14)
C7	0.0328 (16)	0.0498 (19)	0.0375 (17)	0.0124 (14)	0.0086 (13)	0.0182 (15)
C8	0.0258 (15)	0.0468 (18)	0.0249 (15)	−0.0038 (13)	0.0009 (11)	−0.0083 (13)
C9	0.0391 (18)	0.0255 (15)	0.056 (2)	0.0058 (13)	−0.0112 (15)	−0.0054 (14)
C10	0.054 (2)	0.0275 (16)	0.0357 (17)	0.0031 (14)	−0.0073 (14)	0.0014 (13)
C11	0.056 (2)	0.0457 (19)	0.0278 (16)	0.0031 (16)	−0.0100 (14)	0.0035 (14)
C12	0.0316 (16)	0.0418 (18)	0.0407 (17)	0.0061 (13)	0.0074 (13)	0.0163 (14)
C13	0.0248 (15)	0.0407 (17)	0.0322 (16)	0.0070 (12)	0.0053 (12)	0.0079 (13)
C14	0.0419 (18)	0.0323 (16)	0.0322 (16)	0.0088 (13)	−0.0073 (13)	−0.0025 (13)
C15	0.0335 (17)	0.0340 (17)	0.058 (2)	0.0008 (14)	−0.0056 (16)	0.0016 (15)
C16	0.0330 (17)	0.064 (2)	0.0319 (16)	−0.0041 (15)	0.0032 (13)	−0.0085 (15)
C17	0.0280 (16)	0.0407 (17)	0.0298 (16)	−0.0009 (13)	−0.0012 (12)	−0.0018 (13)
C18	0.0370 (18)	0.0334 (17)	0.057 (2)	0.0043 (14)	−0.0082 (15)	−0.0103 (15)
C19	0.0370 (18)	0.0427 (19)	0.053 (2)	0.0028 (15)	−0.0151 (15)	−0.0004 (16)
C20	0.046 (2)	0.0336 (17)	0.065 (2)	0.0169 (15)	−0.0038 (17)	−0.0079 (16)
C21	0.0266 (16)	0.052 (2)	0.0455 (19)	0.0139 (14)	0.0052 (13)	0.0185 (16)
C22	0.0276 (15)	0.0398 (17)	0.0395 (17)	0.0119 (13)	0.0040 (13)	0.0103 (14)
C23	0.0320 (18)	0.052 (2)	0.0402 (18)	−0.0020 (14)	0.0054 (14)	−0.0041 (15)
C24	0.0392 (18)	0.058 (2)	0.0354 (17)	−0.0057 (16)	−0.0077 (14)	−0.0089 (15)
C25	0.048 (2)	0.0332 (16)	0.0358 (17)	0.0049 (14)	−0.0032 (14)	−0.0105 (13)
C26	0.0241 (15)	0.0284 (15)	0.0328 (16)	0.0021 (11)	0.0042 (12)	−0.0008 (11)
C27	0.0337 (18)	0.057 (2)	0.0291 (16)	−0.0031 (14)	−0.0003 (13)	−0.0080 (14)
C28	0.0264 (15)	0.0236 (14)	0.0320 (15)	−0.0001 (11)	0.0036 (12)	−0.0045 (11)
O1	0.0362 (11)	0.0281 (11)	0.0372 (11)	0.0063 (9)	−0.0059 (9)	−0.0082 (9)
O2	0.0262 (11)	0.0669 (16)	0.0277 (11)	−0.0045 (10)	0.0008 (9)	−0.0187 (10)
O3	0.0271 (12)	0.0528 (15)	0.0660 (16)	−0.0030 (11)	−0.0029 (11)	−0.0014 (12)
O4	0.0358 (13)	0.0807 (19)	0.0625 (17)	−0.0016 (13)	−0.0140 (12)	−0.0126 (14)
O5	0.0427 (13)	0.0291 (12)	0.0562 (14)	0.0126 (9)	−0.0158 (11)	−0.0028 (10)
O6	0.0261 (12)	0.0661 (15)	0.0452 (13)	0.0183 (10)	0.0115 (10)	0.0271 (11)
O7	0.0251 (10)	0.0284 (10)	0.0404 (11)	0.0060 (8)	0.0058 (8)	0.0038 (9)
O8	0.0313 (11)	0.0269 (10)	0.0490 (13)	0.0038 (8)	0.0139 (9)	0.0085 (9)
O9	0.0336 (11)	0.0345 (11)	0.0276 (10)	0.0028 (9)	−0.0064 (8)	0.0035 (9)
O10	0.0444 (13)	0.0315 (11)	0.0424 (12)	−0.0071 (9)	0.0161 (10)	−0.0033 (9)
O11	0.0248 (10)	0.0259 (10)	0.0462 (12)	0.0007 (8)	0.0009 (9)	0.0057 (9)
O12	0.0240 (11)	0.0488 (13)	0.0428 (12)	−0.0061 (9)	−0.0045 (9)	−0.0011 (10)
O13	0.354 (10)	0.169 (6)	0.185 (6)	0.015 (6)	−0.141 (6)	0.009 (5)

Geometric parameters (Å, º) top

Pr1—O9ⁱ	2.3983 (18)	C12—C26	1.389 (4)
Pr1—O5	2.4105 (19)	C12—H12	0.9300
Pr1—O12ⁱⁱ	2.412 (2)	C13—C21	1.378 (4)
Pr1—O8ⁱⁱⁱ	2.4692 (19)	C13—O6	1.379 (3)
Pr1—O11	2.4719 (18)	C14—C25	1.380 (4)
Pr1—O10	2.5152 (19)	C14—H14	0.9300
Pr1—O1	2.5163 (19)	C15—O4	1.216 (4)
Pr1—O7ⁱⁱⁱ	2.6534 (19)	C15—O3	1.320 (4)
C1—O5	1.252 (3)	C16—C24	1.375 (4)
C1—O12	1.252 (3)	C16—C17	1.390 (4)
C1—C2	1.496 (4)	C16—H16	0.9300
C2—C18	1.375 (4)	C17—O2	1.379 (4)
C2—C9	1.381 (4)	C17—C27	1.380 (4)
C3—C14	1.382 (4)	C18—C20	1.384 (5)
C3—C10	1.385 (4)	C18—H18	0.9300
C3—C4	1.497 (4)	C19—H19	0.9300
C4—O9	1.254 (3)	C20—H20	0.9300
C4—O1	1.266 (3)	C21—H21	0.9300
C5—C20	1.353 (5)	C22—C26	1.386 (4)
C5—C19	1.371 (5)	C22—H22	0.9300
C5—O6	1.404 (3)	C23—C27	1.380 (5)
C6—C24	1.385 (5)	C23—H23	0.9300
C6—C23	1.386 (4)	C24—H24	0.9300
C6—C15	1.480 (4)	C25—H25	0.9300
C7—C22	1.381 (4)	C26—C28	1.481 (4)
C7—C13	1.381 (4)	C27—H27	0.9300
C7—H7	0.9300	C28—O7	1.262 (3)
C8—C11	1.367 (5)	C28—O8	1.273 (3)
C8—C25	1.369 (4)	O3—H3	0.8200
C8—O2	1.406 (3)	O10—H10A	0.8499
C9—C19	1.381 (4)	O10—H10B	0.8500
C9—H9	0.9300	O11—H11B	0.8444
C10—C11	1.385 (4)	O11—H11A	0.8444
C10—H10	0.9300	O13—H13B	0.8542
C11—H11	0.9300	O13—H13A	0.8500
C12—C21	1.381 (4)

O9ⁱ—Pr1—O5	153.69 (8)	O6—C13—C7	116.0 (3)
O9ⁱ—Pr1—O12ⁱⁱ	88.26 (7)	C25—C14—C3	120.8 (3)
O5—Pr1—O12ⁱⁱ	107.34 (7)	C25—C14—H14	119.6
O9ⁱ—Pr1—O8ⁱⁱⁱ	74.83 (7)	C3—C14—H14	119.6
O5—Pr1—O8ⁱⁱⁱ	128.11 (7)	O4—C15—O3	123.6 (3)
O12ⁱⁱ—Pr1—O8ⁱⁱⁱ	78.82 (7)	O4—C15—C6	122.1 (3)
O9ⁱ—Pr1—O11	70.57 (6)	O3—C15—C6	114.2 (3)
O5—Pr1—O11	83.78 (7)	C24—C16—C17	118.9 (3)
O12ⁱⁱ—Pr1—O11	136.39 (7)	C24—C16—H16	120.5
O8ⁱⁱⁱ—Pr1—O11	127.57 (6)	C17—C16—H16	120.5
O9ⁱ—Pr1—O10	85.53 (7)	O2—C17—C27	123.8 (3)
O5—Pr1—O10	79.66 (7)	O2—C17—C16	115.5 (3)
O12ⁱⁱ—Pr1—O10	71.94 (7)	C27—C17—C16	120.7 (3)
O8ⁱⁱⁱ—Pr1—O10	145.13 (7)	C2—C18—C20	120.2 (3)
O11—Pr1—O10	68.85 (6)	C2—C18—H18	119.9
O9ⁱ—Pr1—O1	107.40 (6)	C20—C18—H18	119.9
O5—Pr1—O1	69.94 (7)	C5—C19—C9	118.9 (3)
O12ⁱⁱ—Pr1—O1	148.79 (7)	C5—C19—H19	120.6
O8ⁱⁱⁱ—Pr1—O1	79.55 (7)	C9—C19—H19	120.6
O11—Pr1—O1	74.82 (7)	C5—C20—C18	120.0 (3)
O10—Pr1—O1	134.54 (7)	C5—C20—H20	120.0
O9ⁱ—Pr1—O7ⁱⁱⁱ	123.84 (6)	C18—C20—H20	120.0
O5—Pr1—O7ⁱⁱⁱ	81.88 (7)	C13—C21—C12	119.2 (3)
O12ⁱⁱ—Pr1—O7ⁱⁱⁱ	71.13 (7)	C13—C21—H21	120.4
O8ⁱⁱⁱ—Pr1—O7ⁱⁱⁱ	50.58 (6)	C12—C21—H21	120.4
O11—Pr1—O7ⁱⁱⁱ	152.06 (6)	C7—C22—C26	120.5 (3)
O10—Pr1—O7ⁱⁱⁱ	131.07 (6)	C7—C22—H22	119.7
O1—Pr1—O7ⁱⁱⁱ	77.77 (6)	C26—C22—H22	119.7
O5—C1—O12	122.6 (3)	C27—C23—C6	120.6 (3)
O5—C1—C2	117.8 (2)	C27—C23—H23	119.7
O12—C1—C2	119.7 (2)	C6—C23—H23	119.7
C18—C2—C9	118.8 (3)	C16—C24—C6	121.2 (3)
C18—C2—C1	121.0 (3)	C16—C24—H24	119.4
C9—C2—C1	120.2 (2)	C6—C24—H24	119.4
C14—C3—C10	118.9 (3)	C8—C25—C14	118.9 (3)
C14—C3—C4	120.3 (2)	C8—C25—H25	120.5
C10—C3—C4	120.8 (2)	C14—C25—H25	120.5
O9—C4—O1	122.7 (2)	C22—C26—C12	118.8 (3)
O9—C4—C3	118.9 (2)	C22—C26—C28	121.5 (3)
O1—C4—C3	118.4 (2)	C12—C26—C28	119.7 (3)
C20—C5—C19	121.1 (3)	C23—C27—C17	119.5 (3)
C20—C5—O6	119.2 (3)	C23—C27—H27	120.3
C19—C5—O6	119.6 (3)	C17—C27—H27	120.3
C24—C6—C23	119.0 (3)	O7—C28—O8	119.9 (3)
C24—C6—C15	119.3 (3)	O7—C28—C26	121.8 (2)
C23—C6—C15	121.7 (3)	O8—C28—C26	118.2 (2)
C22—C7—C13	119.8 (3)	O7—C28—Pr1^iv	64.72 (15)
C22—C7—H7	120.1	O8—C28—Pr1^iv	56.40 (14)
C13—C7—H7	120.1	C26—C28—Pr1^iv	166.2 (2)
C11—C8—C25	121.7 (3)	C4—O1—Pr1	120.84 (17)
C11—C8—O2	120.2 (3)	C17—O2—C8	118.1 (2)
C25—C8—O2	118.1 (3)	C15—O3—H3	109.5
C19—C9—C2	121.0 (3)	C1—O5—Pr1	123.47 (18)
C19—C9—H9	119.5	C13—O6—C5	117.6 (2)
C2—C9—H9	119.5	C28—O7—Pr1^iv	89.80 (16)
C3—C10—C11	120.5 (3)	C28—O8—Pr1^iv	98.18 (16)
C3—C10—H10	119.8	C4—O9—Pr1ⁱ	170.37 (18)
C11—C10—H10	119.8	Pr1—O10—H10A	109.2
C8—C11—C10	119.0 (3)	Pr1—O10—H10B	109.4
C8—C11—H11	120.5	H10A—O10—H10B	109.5
C10—C11—H11	120.5	Pr1—O11—H11B	116.8
C21—C12—C26	121.1 (3)	Pr1—O11—H11A	122.6
C21—C12—H12	119.5	H11B—O11—H11A	106.3
C26—C12—H12	119.5	C1—O12—Pr1ⁱⁱ	172.3 (2)
C21—C13—O6	123.3 (3)	H13B—O13—H13A	99.7
C21—C13—C7	120.7 (3)

O5—C1—C2—C18	−163.0 (3)	C7—C22—C26—C12	−0.5 (5)
O12—C1—C2—C18	16.2 (4)	C7—C22—C26—C28	179.8 (3)
O5—C1—C2—C9	17.7 (4)	C21—C12—C26—C22	−0.4 (5)
O12—C1—C2—C9	−163.1 (3)	C21—C12—C26—C28	179.2 (3)
C14—C3—C4—O9	−6.8 (4)	C6—C23—C27—C17	0.7 (5)
C10—C3—C4—O9	175.4 (3)	O2—C17—C27—C23	178.2 (3)
C14—C3—C4—O1	172.3 (3)	C16—C17—C27—C23	−0.1 (5)
C10—C3—C4—O1	−5.6 (4)	C22—C26—C28—O7	17.2 (4)
C18—C2—C9—C19	0.6 (5)	C12—C26—C28—O7	−162.4 (3)
C1—C2—C9—C19	179.9 (3)	C22—C26—C28—O8	−164.6 (3)
C14—C3—C10—C11	−2.3 (5)	C12—C26—C28—O8	15.7 (4)
C4—C3—C10—C11	175.5 (3)	C22—C26—C28—Pr1^iv	131.9 (7)
C25—C8—C11—C10	1.5 (5)	C12—C26—C28—Pr1^iv	−47.8 (9)
O2—C8—C11—C10	180.0 (3)	O9—C4—O1—Pr1	−16.0 (4)
C3—C10—C11—C8	0.2 (5)	C3—C4—O1—Pr1	165.01 (17)
C22—C7—C13—C21	−1.1 (5)	O9ⁱ—Pr1—O1—C4	21.5 (2)
C22—C7—C13—O6	179.5 (3)	O5—Pr1—O1—C4	173.8 (2)
C10—C3—C14—C25	2.9 (5)	O12ⁱⁱ—Pr1—O1—C4	−95.6 (2)
C4—C3—C14—C25	−175.0 (3)	O8ⁱⁱⁱ—Pr1—O1—C4	−48.8 (2)
C24—C6—C15—O4	2.3 (5)	O11—Pr1—O1—C4	85.0 (2)
C23—C6—C15—O4	−176.4 (3)	O10—Pr1—O1—C4	122.68 (19)
C24—C6—C15—O3	−176.6 (3)	O7ⁱⁱⁱ—Pr1—O1—C4	−100.5 (2)
C23—C6—C15—O3	4.7 (5)	C28ⁱⁱⁱ—Pr1—O1—C4	−74.6 (2)
C24—C16—C17—O2	−178.6 (3)	C27—C17—O2—C8	8.6 (4)
C24—C16—C17—C27	−0.2 (5)	C16—C17—O2—C8	−173.0 (3)
C9—C2—C18—C20	−1.7 (5)	C11—C8—O2—C17	73.5 (4)
C1—C2—C18—C20	179.0 (3)	C25—C8—O2—C17	−108.0 (3)
C20—C5—C19—C9	−1.6 (5)	O12—C1—O5—Pr1	−4.2 (4)
O6—C5—C19—C9	−177.9 (3)	C2—C1—O5—Pr1	174.99 (17)
C2—C9—C19—C5	1.0 (5)	O9ⁱ—Pr1—O5—C1	−115.7 (2)
C19—C5—C20—C18	0.6 (5)	O12ⁱⁱ—Pr1—O5—C1	8.3 (3)
O6—C5—C20—C18	176.9 (3)	O8ⁱⁱⁱ—Pr1—O5—C1	97.6 (2)
C2—C18—C20—C5	1.1 (6)	O11—Pr1—O5—C1	−128.5 (2)
O6—C13—C21—C12	179.5 (3)	O10—Pr1—O5—C1	−58.9 (2)
C7—C13—C21—C12	0.2 (5)	O1—Pr1—O5—C1	155.5 (3)
C26—C12—C21—C13	0.6 (5)	O7ⁱⁱⁱ—Pr1—O5—C1	75.6 (2)
C13—C7—C22—C26	1.3 (5)	C28ⁱⁱⁱ—Pr1—O5—C1	82.5 (2)
C24—C6—C23—C27	−0.9 (5)	C21—C13—O6—C5	5.7 (5)
C15—C6—C23—C27	177.9 (3)	C7—C13—O6—C5	−175.0 (3)
C17—C16—C24—C6	−0.1 (5)	C20—C5—O6—C13	92.8 (4)
C23—C6—C24—C16	0.6 (5)	C19—C5—O6—C13	−90.9 (4)
C15—C6—C24—C16	−178.2 (3)	O8—C28—O7—Pr1^iv	−12.0 (3)
C11—C8—C25—C14	−1.0 (5)	C26—C28—O7—Pr1^iv	166.1 (2)
O2—C8—C25—C14	−179.5 (3)	O7—C28—O8—Pr1^iv	13.1 (3)
C3—C14—C25—C8	−1.2 (5)	C26—C28—O8—Pr1^iv	−165.1 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^v	0.82	2.02	2.822 (3)	166
O10—H10B···O2^vi	0.85	2.09	2.880 (3)	154
O11—H11A···O4^vii	0.84	1.84	2.683 (3)	176
O11—H11B···O8^viii	0.84	1.89	2.707 (3)	163
C9—H9···O3^vii	0.93	2.48	3.337 (4)	153
C25—H25···O13ⁱⁱⁱ	0.93	2.59	3.454 (7)	155

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

Selected bond lengths (Å) top

Pr1—O9ⁱ	2.3983 (18)	Pr1—O11	2.4719 (18)
Pr1—O5	2.4105 (19)	Pr1—O10	2.5152 (19)
Pr1—O12ⁱⁱ	2.412 (2)	Pr1—O1	2.5163 (19)
Pr1—O8ⁱⁱⁱ	2.4692 (19)	Pr1—O7ⁱⁱⁱ	2.6534 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^iv	0.82	2.02	2.822 (3)	166
O10—H10B···O2^v	0.85	2.09	2.880 (3)	154
O11—H11A···O4^vi	0.84	1.84	2.683 (3)	176
O11—H11B···O8^vii	0.84	1.89	2.707 (3)	163
C9—H9···O3^vi	0.93	2.48	3.337 (4)	153
C25—H25···O13ⁱⁱⁱ	0.93	2.59	3.454 (7)	155

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

Acknowledgements

This work was supported by the Research Institute of Element-Organic Chemistry of the East China Institute of Technology

References

Bruker (1997). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, X. X., Wei, Z. Q., Yue, S. T., Wang, N., Mo, H. H. & Liu, Y. L. (2011). J. Chem. Crystallogr. 41, 757–761. Web of Science CSD CrossRef CAS Google Scholar
Lin, Y. W., Jian, B. R., Huang, S. C., Huang, C. H. & Hsu, K. F. (2010). Inorg. Chem., 49, 2316–2324. Web of Science CSD CrossRef CAS PubMed Google Scholar
Łyszczek, R. & Mazur, L. (2012). Inorg. Chem. Commun. 15, 121–125. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, C. Y., Zheng, X. B., Li, L. C. & Jin, L. P. (2009). Inorg. Chim. Acta, 362, 325–330. Web of Science CSD CrossRef CAS Google Scholar
Thirumurugan, A. & Natarajan, S. (2004). Eur. J. Inorg. Chem. pp. 762–770. CSD CrossRef Google Scholar
Wang, Y. B., Sun, C. Y., Zheng, X. J., Gao, S., Lu, S. Z. & Jin, L. P. (2005). Polyhedron, 24, 823–830. Web of Science CSD CrossRef Google Scholar
Wang, Y. B., Wang, Z. M., Yan, C. H. & Jin, L. P. (2004). J. Mol. Struct. 692, 177–186. Web of Science CSD CrossRef CAS Google Scholar
Xu, J., Su, W. P. & Hong, M. C. (2011). Inorg. Chem. Commun. 14, 1794–1797. Web of Science CSD CrossRef CAS Google Scholar
Zhang, J. J., Hu, S. M., Xiang, S. C., Wang, L. S., Li, Y. M., Zhang, H. S. & Wu, X. T. (2005). J. Mol. Struct. 748, 129–136. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.