Poly[[octa­aqua­tetra­kis­(μ3-pyridine-2,5-dicarboxyl­ato)copper(II)diytterbium(III)] monohydrate]

Lush, S.F.; Shen, F.M.

doi:10.1107/S1600536811014048

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m615-m616

doi:10.1107/S1600536811014048

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Poly[[octaaquatetrakis(μ₃-pyridine-2,5-dicarboxylato)copper(II)diytterbium(III)] monohydrate]

Shie Fu Lush ^a and Fwu Ming Shen ^b ^*

^aDepartment of General Education Center, Yuanpei University, HsinChu 30015, Taiwan, and ^bDepartment of Biotechnology, Yuanpei University, No. 306 Yuanpei St., HsinChu 30015, Taiwan
^*Correspondence e-mail: fmshen@mail.ypu.edu.tw

(Received 29 March 2011; accepted 14 April 2011; online 22 April 2011)

The asymmetric unit of the title heterometallic polymeric coordination compound, {[CuYb₂(C₇H₃NO₄)₄(H₂O)₈]·H₂O}_n, contains one Cu^II cation located on an inversion center, a Yb^III cation, two pyridine-2,5-dicarboxylate (pda) anions, four coordination water molecules a disordered lattice water molecule, which is half-occupied and is located close to an inversion center. The Cu^II cation is N,O-chelated by two pda anions in the coordination basal plane and further coordinated by two carboxyl O atoms at the apical positions, with an elongated octahedral geometry. The Yb^III atom is eight-coordinated in a distorted square-antiprismatic geometry formed by two carboxylate O atoms from two pda anions, and is N,O-chelated by one pda anion and four coordinated water molecules. The pda anions bridge adjacent Yb and Cu cations, forming a three-dimensional polymeric structure. The crystal structure features extensive O—H⋯O hydrogen bonds. π–π stacking is observed between parallel pyridine rings, the centroid–centroid distance being 3.843 (4) Å.

Related literature

For related structures, see: Bai et al. (2008 ); Chi et al. (2009 ); Wang et al. (2009 ); Yue et al. (2007 ); Zhang et al. (2006 ). For structures in which the Cu atom displays an elongated octahedral geometry with a longer Cu—O bond, see: Chuang et al. (2008 ); Ghosh et al. (2004 ).

Experimental

Crystal data

[CuYb₂(C₇H₃NO₄)₄(H₂O)₈]·H₂O
M_r = 1232.19
Triclinic, $[P \overline 1]$
a = 7.7120 (5) Å
b = 9.2713 (6) Å
c = 13.2452 (9) Å
α = 75.529 (1)°
β = 76.216 (1)°
γ = 78.117 (1)°
V = 879.73 (10) Å³
Z = 1
Mo Kα radiation
μ = 5.98 mm⁻¹
T = 294 K
0.15 × 0.15 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.646, T_max = 0.984
7620 measured reflections
3150 independent reflections
3010 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.095
S = 1.18
3150 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 2.78 e Å⁻³
Δρ_min = −2.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Yb1—N1	2.495 (7)
Yb1—O1	2.365 (6)
Yb1—O2	2.254 (7)
Yb1—O3	2.330 (8)
Yb1—O4	2.346 (7)
Yb1—O5	2.297 (5)
Yb1—O8ⁱ	2.297 (6)
Yb1—O9	2.334 (8)
Cu1—N2	1.985 (7)
Cu1—O7ⁱⁱ	2.641 (6)
Cu1—O11	1.944 (6)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O12ⁱⁱⁱ	0.81	1.96	2.757 (9)	165
O1—H1B⋯O11^iv	0.82	2.02	2.782 (9)	153
O2—H2A⋯O10	0.88	1.88	2.670 (11)	149
O2—H2B⋯O5^v	0.82	1.87	2.667 (9)	163
O3—H3A⋯O7ⁱ	0.84	1.82	2.607 (9)	155
O3—H3B⋯O13	0.82	1.95	2.73 (2)	159
O4—H4A⋯O10^vi	0.82	1.95	2.760 (10)	167
O4—H4B⋯O6^vii	0.82	1.98	2.802 (9)	179
O13—H13A⋯O10	0.87	2.20	3.03 (2)	161
O13—H13B⋯O12ⁱ	0.85	1.96	2.81 (2)	177
Symmetry codes: (i) x, y-1, z; (iii) x+1, y-1, z; (iv) -x, -y+2, -z+2; (v) -x+1, -y+1, -z+1; (vi) x+1, y, z; (vii) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014048/xu5183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014048/xu5183Isup2.hkl

checkCIF report

Comment top

In recent year, many studies select pyridine-2,5-dicarboxylic acid as a bridging ligand, because it offers both N– and O-donors. Thus, the carboxylate group can bond to the lanthanide, while the nitrogen atom can bond to transition metal ions, allowing the possibility of 3 d-4f heterometallic coordination polymers (Zhang et al., 2006; Yue et al., 2007; Bai et al., 2008; Chi et al., 2009; Wang et al., 2009).

Herein, we successfully prepared a heterometallic coordination polymer, [CuYb₂(C₇H₃NO₄)₄(H₂O)₈.H₂O]_n, from a hydrothermal reaction. Fig. 1 shows the structure unit of the title complex, which contains one Cu^II and two Yb^III atoms, four pda ligands, eight coordinating and one non-coordinating water molecules. The Yb^III center is eight-coordinated [YbNO₃(H₂O)₄] in a slightly distorted square-antiprismatic geometry formed by two carboxylate O atoms from two pda anions, N,O-chelated by one pda anion and four coordinated water molecules. One Cu^II atom is N,O-chelated by two pda anions in the coordination basal plane and coordinated by two carboxyl O atoms at the apical position with an elongated octahedral geometry (selected bond lengths are given in Table 1) (Ghosh et al.,2004; Chuang et al., 2008). The molecular structure contains both Cu and Yb atoms, with pda ligands bridging the six coordinate Cu^II centers and eight coordinate Yb^III centers to form a three-dimensional net structure.

The crystal structure contains the extensive O—H···O (shown as Fig. 2 and Table 2). π···π stackings are present in the crystal structure, the shortest centroid distance between parallel pyridine rings Cg5^iv···Cg5((N2/C8—C12) is 3.843 (4) Å, respectively [symmetry code:(iv)=-X, 2-Y,2-Z].

Related literature top

For related structures, see: Bai et al. (2008); Chi et al. (2009); Wang et al. (2009); Yue et al. (2007); Zhang et al. (2006). For structures in which the Cu atom displays an elongated octahedral geometry with a longer Cu—O bond, see: Chuang et al. (2008); Ghosh et al. (2004).

Experimental top

A solution of Cu(OAc)₂.H₂O (0.0205 g, 0.10 mmol), Yb₂O₃ (0.0199 g, 0.050 mmol) and 2,5-pyridinedicarboxylic acid (0.0343 g, 0.20 mmol) were mixed in 10 ml deionized water. After stirring half an hour, the mixture was placed in 23 ml Teflon-lined reactor. After heating for four days at 418 K, the mixture was cooling to room-temperature. Green block-like crystals were isolated in 42% yield (based on Yb).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.H atoms have been omitted for clarity.[symmetry code:(i)x, y - 1, z; (ii) x - 1, y, z; (iii) -x - 1, -y + 2, -z + 2; (iv) -x, -y + 2, -z + 2].
	Fig. 2. The molecular packing for the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

Poly[[octaaquatetrakis(µ₃-pyridine-2,5- dicarboxylato)copper(II)diytterbium(III)] monohydrate] top

Crystal data top

[CuYb₂(C₇H₃NO₄)₄(H₂O)₈]·H₂O	Z = 1
M_r = 1232.19	F(000) = 595
Triclinic, P1	D_x = 2.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7120 (5) Å	Cell parameters from 5946 reflections
b = 9.2713 (6) Å	θ = 2.5–25.0°
c = 13.2452 (9) Å	µ = 5.98 mm⁻¹
α = 75.529 (1)°	T = 294 K
β = 76.216 (1)°	Tabular, green
γ = 78.117 (1)°	0.15 × 0.15 × 0.03 mm
V = 879.73 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3150 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9 pixels mm^-1	θ_max = 25.2°, θ_min = 1.6°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −11→10
T_min = 0.646, T_max = 0.984	l = −15→15
7620 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0263P)² + 10.305P] where P = (F_o² + 2F_c²)/3
3150 reflections	(Δ/σ)_max = 0.005
271 parameters	Δρ_max = 2.78 e Å⁻³
0 restraints	Δρ_min = −2.60 e Å⁻³

Crystal data top

[CuYb₂(C₇H₃NO₄)₄(H₂O)₈]·H₂O	γ = 78.117 (1)°
M_r = 1232.19	V = 879.73 (10) Å³
Triclinic, P1	Z = 1
a = 7.7120 (5) Å	Mo Kα radiation
b = 9.2713 (6) Å	µ = 5.98 mm⁻¹
c = 13.2452 (9) Å	T = 294 K
α = 75.529 (1)°	0.15 × 0.15 × 0.03 mm
β = 76.216 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3150 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3010 reflections with I > 2σ(I)
T_min = 0.646, T_max = 0.984	R_int = 0.036
7620 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0263P)² + 10.305P] where P = (F_o² + 2F_c²)/3
3150 reflections	Δρ_max = 2.78 e Å⁻³
271 parameters	Δρ_min = −2.60 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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)
Yb1	0.54822 (5)	0.55527 (4)	0.70031 (3)	0.0202 (1)
Cu1	−0.50000	1.00000	1.00000	0.0294 (5)
O1	0.6110 (8)	0.6005 (7)	0.8550 (5)	0.0303 (17)
O2	0.3316 (9)	0.5549 (8)	0.6123 (6)	0.040 (2)
O3	0.3630 (10)	0.4196 (7)	0.8421 (6)	0.045 (2)
O4	0.8540 (8)	0.4781 (7)	0.7109 (5)	0.036 (2)
O5	0.6911 (8)	0.6043 (6)	0.5249 (4)	0.0292 (19)
O6	0.8886 (10)	0.7235 (7)	0.3948 (5)	0.044 (3)
O7	0.4698 (8)	1.1486 (6)	0.8054 (5)	0.0300 (19)
O8	0.6197 (8)	1.3112 (6)	0.6768 (5)	0.033 (2)
O9	0.3050 (9)	0.7337 (9)	0.7547 (7)	0.0534 (19)
O10	0.0479 (9)	0.6787 (9)	0.7398 (7)	0.0534 (19)
O11	−0.4478 (8)	1.1832 (6)	1.0248 (5)	0.0300 (17)
O12	−0.2411 (9)	1.3353 (7)	0.9741 (5)	0.034 (2)
N1	0.6426 (9)	0.8097 (7)	0.6374 (5)	0.0213 (19)
N2	−0.2416 (9)	0.9775 (8)	0.9285 (5)	0.024 (2)
C1	0.7354 (11)	0.8421 (9)	0.5374 (7)	0.026 (3)
C2	0.7878 (14)	0.9813 (10)	0.4904 (7)	0.038 (3)
C3	0.7363 (14)	1.0958 (10)	0.5471 (8)	0.037 (3)
C4	0.6381 (11)	1.0647 (9)	0.6510 (7)	0.023 (2)
C5	0.5969 (11)	0.9204 (8)	0.6927 (6)	0.021 (2)
C6	0.7773 (12)	0.7156 (10)	0.4794 (7)	0.029 (3)
C7	0.5715 (11)	1.1839 (9)	0.7168 (7)	0.025 (3)
C8	−0.1440 (12)	0.8674 (10)	0.8796 (7)	0.030 (3)
C9	0.0322 (11)	0.8752 (9)	0.8247 (7)	0.026 (3)
C10	0.1051 (11)	1.0033 (9)	0.8160 (7)	0.026 (2)
C11	0.0035 (11)	1.1185 (9)	0.8637 (7)	0.027 (3)
C12	−0.1703 (11)	1.1007 (9)	0.9198 (6)	0.023 (2)
C13	0.1376 (12)	0.7481 (11)	0.7720 (8)	0.035 (3)
C14	−0.2915 (11)	1.2177 (9)	0.9759 (6)	0.022 (2)
O13	0.035 (3)	0.497 (2)	0.9652 (15)	0.073 (8)	0.500
H1A	0.66390	0.53210	0.89360	0.0800*
H1B	0.53470	0.64950	0.89350	0.0800*
H2A	0.21830	0.57560	0.64460	0.0800*
H2B	0.33500	0.49070	0.57830	0.0800*
H2C	0.85660	0.99810	0.42180	0.0450*
H3A	0.36350	0.33120	0.83550	0.0800*
H3B	0.28010	0.43640	0.89150	0.0800*
H3C	0.76680	1.19130	0.51630	0.0450*
H4A	0.91280	0.52870	0.72840	0.0800*
H4B	0.92920	0.41980	0.67930	0.0800*
H5A	0.53430	0.89870	0.76270	0.0250*
H8A	−0.19600	0.78400	0.88270	0.0350*
H10A	0.22200	1.01180	0.77820	0.0300*
H11A	0.05020	1.20550	0.85840	0.0320*
H13A	0.01660	0.56250	0.90790	0.0800*	0.500
H13B	−0.04850	0.44950	0.96530	0.0800*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Yb1	0.0224 (2)	0.0149 (2)	0.0232 (2)	−0.0037 (1)	0.0008 (1)	−0.0086 (1)
Cu1	0.0187 (7)	0.0260 (8)	0.0449 (9)	−0.0005 (6)	0.0028 (6)	−0.0211 (7)
O1	0.035 (3)	0.026 (3)	0.029 (3)	0.007 (3)	−0.006 (3)	−0.014 (3)
O2	0.029 (3)	0.049 (4)	0.052 (4)	−0.003 (3)	−0.004 (3)	−0.036 (3)
O3	0.056 (5)	0.021 (3)	0.045 (4)	−0.006 (3)	0.016 (3)	−0.009 (3)
O4	0.025 (3)	0.039 (4)	0.050 (4)	0.000 (3)	−0.003 (3)	−0.028 (3)
O5	0.043 (4)	0.024 (3)	0.024 (3)	−0.013 (3)	0.004 (3)	−0.015 (2)
O6	0.058 (5)	0.030 (4)	0.037 (4)	−0.016 (3)	0.022 (3)	−0.016 (3)
O7	0.041 (4)	0.019 (3)	0.030 (3)	−0.007 (3)	−0.001 (3)	−0.009 (2)
O8	0.037 (4)	0.017 (3)	0.046 (4)	−0.011 (3)	0.005 (3)	−0.014 (3)
O9	0.026 (3)	0.061 (3)	0.088 (4)	−0.008 (2)	0.006 (3)	−0.058 (3)
O10	0.026 (3)	0.061 (3)	0.088 (4)	−0.008 (2)	0.006 (3)	−0.058 (3)
O11	0.030 (3)	0.025 (3)	0.035 (3)	0.000 (3)	0.000 (3)	−0.016 (3)
O12	0.036 (4)	0.020 (3)	0.048 (4)	−0.002 (3)	−0.008 (3)	−0.013 (3)
N1	0.024 (4)	0.017 (3)	0.023 (3)	−0.004 (3)	0.001 (3)	−0.009 (3)
N2	0.021 (4)	0.023 (4)	0.030 (4)	0.000 (3)	−0.004 (3)	−0.014 (3)
C1	0.021 (4)	0.024 (4)	0.030 (5)	0.000 (3)	−0.002 (3)	−0.005 (4)
C2	0.050 (6)	0.031 (5)	0.030 (5)	−0.014 (4)	0.010 (4)	−0.012 (4)
C3	0.052 (6)	0.020 (5)	0.037 (5)	−0.011 (4)	0.003 (4)	−0.007 (4)
C4	0.023 (4)	0.018 (4)	0.031 (4)	−0.005 (3)	−0.005 (3)	−0.011 (3)
C5	0.023 (4)	0.016 (4)	0.026 (4)	−0.003 (3)	−0.004 (3)	−0.008 (3)
C6	0.031 (5)	0.027 (5)	0.027 (5)	−0.011 (4)	−0.006 (4)	0.001 (4)
C7	0.024 (4)	0.019 (4)	0.036 (5)	0.000 (3)	−0.009 (4)	−0.012 (4)
C8	0.025 (4)	0.028 (5)	0.040 (5)	−0.005 (4)	−0.002 (4)	−0.019 (4)
C9	0.026 (5)	0.024 (4)	0.029 (4)	−0.001 (4)	−0.004 (4)	−0.012 (4)
C10	0.021 (4)	0.025 (4)	0.029 (4)	−0.001 (3)	−0.001 (3)	−0.008 (4)
C11	0.028 (5)	0.019 (4)	0.032 (5)	−0.001 (3)	−0.006 (4)	−0.004 (3)
C12	0.026 (4)	0.018 (4)	0.021 (4)	0.001 (3)	−0.004 (3)	−0.004 (3)
C13	0.021 (5)	0.032 (5)	0.058 (6)	0.001 (4)	−0.005 (4)	−0.028 (5)
C14	0.027 (4)	0.020 (4)	0.019 (4)	0.002 (3)	−0.004 (3)	−0.007 (3)
O13	0.061 (12)	0.087 (13)	0.076 (14)	−0.033 (10)	0.026 (9)	−0.047 (12)

Geometric parameters (Å, º) top

Yb1—N1	2.495 (7)	O3—H3A	0.8400
Yb1—O1	2.365 (6)	O4—H4A	0.8200
Yb1—O2	2.254 (7)	O4—H4B	0.8200
Yb1—O3	2.330 (8)	O13—H13B	0.8500
Yb1—O4	2.346 (7)	O13—H13A	0.8700
Yb1—O5	2.297 (5)	N1—C1	1.340 (11)
Yb1—O8ⁱ	2.297 (6)	N1—C5	1.348 (10)
Yb1—O9	2.334 (8)	N2—C12	1.335 (11)
Cu1—N2	1.985 (7)	N2—C8	1.345 (12)
Cu1—N2ⁱⁱ	1.985 (7)	C1—C6	1.499 (12)
Cu1—O7ⁱⁱⁱ	2.641 (6)	C1—C2	1.382 (13)
Cu1—O7^iv	2.641 (6)	C2—C3	1.390 (13)
Cu1—O11	1.944 (6)	C3—C4	1.395 (13)
Cu1—O11ⁱⁱ	1.944 (6)	C4—C7	1.510 (12)
O5—C6	1.285 (11)	C4—C5	1.385 (11)
O6—C6	1.235 (11)	C8—C9	1.387 (13)
O7—C7	1.255 (11)	C9—C10	1.384 (12)
O8—C7	1.259 (10)	C9—C13	1.511 (13)
O9—C13	1.241 (12)	C10—C11	1.382 (12)
O10—C13	1.239 (13)	C11—C12	1.390 (12)
O11—C14	1.288 (11)	C12—C14	1.502 (12)
O12—C14	1.224 (11)	C2—H2C	0.9300
O1—H1A	0.8100	C3—H3C	0.9300
O1—H1B	0.8200	C5—H5A	0.9300
O2—H2A	0.8800	C8—H8A	0.9300
O2—H2B	0.8200	C10—H10A	0.9300
O3—H3B	0.8200	C11—H11A	0.9300

O1—Yb1—O2	145.9 (2)	H3A—O3—H3B	107.00
O1—Yb1—O3	74.7 (2)	Yb1—O3—H3B	138.00
O1—Yb1—O4	68.0 (2)	H4A—O4—H4B	105.00
O1—Yb1—O5	132.0 (2)	Yb1—O4—H4B	128.00
O1—Yb1—O9	75.8 (3)	Yb1—O4—H4A	123.00
O1—Yb1—N1	77.2 (2)	H13A—O13—H13B	93.00
O1—Yb1—O8ⁱ	116.9 (2)	Yb1—N1—C5	125.5 (5)
O2—Yb1—O3	82.9 (3)	C1—N1—C5	117.5 (7)
O2—Yb1—O4	145.5 (2)	Yb1—N1—C1	116.9 (5)
O2—Yb1—O5	76.6 (2)	Cu1—N2—C12	111.4 (6)
O2—Yb1—O9	73.8 (3)	C8—N2—C12	119.2 (7)
O2—Yb1—N1	106.8 (2)	Cu1—N2—C8	128.8 (6)
O2—Yb1—O8ⁱ	80.5 (2)	C2—C1—C6	122.2 (8)
O3—Yb1—O4	111.2 (2)	N1—C1—C6	114.8 (7)
O3—Yb1—O5	151.4 (2)	N1—C1—C2	123.0 (8)
O3—Yb1—O9	74.9 (3)	C1—C2—C3	119.1 (9)
O3—Yb1—N1	140.3 (2)	C2—C3—C4	118.7 (9)
O3—Yb1—O8ⁱ	75.0 (2)	C5—C4—C7	119.7 (8)
O4—Yb1—O5	77.5 (2)	C3—C4—C7	122.1 (8)
O4—Yb1—O9	139.4 (3)	C3—C4—C5	118.1 (8)
O4—Yb1—N1	82.8 (2)	N1—C5—C4	123.5 (7)
O4—Yb1—O8ⁱ	73.7 (2)	O6—C6—C1	119.9 (8)
O5—Yb1—O9	117.1 (3)	O5—C6—C1	115.0 (8)
O5—Yb1—N1	66.0 (2)	O5—C6—O6	125.2 (8)
O5—Yb1—O8ⁱ	82.0 (2)	O7—C7—C4	117.2 (7)
O9—Yb1—N1	71.5 (3)	O8—C7—C4	117.0 (8)
O8ⁱ—Yb1—O9	142.3 (3)	O7—C7—O8	125.7 (8)
O8ⁱ—Yb1—N1	143.8 (2)	N2—C8—C9	121.7 (8)
O11—Cu1—N2	83.1 (3)	C8—C9—C13	119.9 (8)
O7^iv—Cu1—O11	87.9 (2)	C10—C9—C13	121.4 (8)
O11—Cu1—O11ⁱⁱ	180.00	C8—C9—C10	118.7 (8)
O11—Cu1—N2ⁱⁱ	96.9 (3)	C9—C10—C11	119.8 (8)
O7ⁱⁱⁱ—Cu1—O11	92.1 (2)	C10—C11—C12	118.2 (8)
O7^iv—Cu1—N2	80.1 (2)	N2—C12—C14	115.0 (7)
O11ⁱⁱ—Cu1—N2	96.9 (3)	N2—C12—C11	122.4 (8)
N2—Cu1—N2ⁱⁱ	180.00	C11—C12—C14	122.7 (8)
O7ⁱⁱⁱ—Cu1—N2	99.9 (2)	O10—C13—C9	116.1 (9)
O7^iv—Cu1—O11ⁱⁱ	92.1 (2)	O9—C13—O10	126.0 (10)
O7^iv—Cu1—N2ⁱⁱ	99.9 (2)	O9—C13—C9	117.4 (9)
O7^iv—Cu1—O7ⁱⁱⁱ	180.00	O12—C14—C12	121.1 (8)
O11ⁱⁱ—Cu1—N2ⁱⁱ	83.1 (3)	O11—C14—C12	114.8 (7)
O7ⁱⁱⁱ—Cu1—O11ⁱⁱ	87.9 (2)	O11—C14—O12	124.1 (8)
O7ⁱⁱⁱ—Cu1—N2ⁱⁱ	80.1 (2)	C1—C2—H2C	120.00
Yb1—O5—C6	125.3 (5)	C3—C2—H2C	120.00
Cu1^v—O7—C7	138.2 (6)	C4—C3—H3C	121.00
Yb1^vi—O8—C7	140.4 (6)	C2—C3—H3C	121.00
Yb1—O9—C13	136.8 (7)	N1—C5—H5A	118.00
Cu1—O11—C14	114.7 (5)	C4—C5—H5A	118.00
H1A—O1—H1B	107.00	C9—C8—H8A	119.00
Yb1—O1—H1A	119.00	N2—C8—H8A	119.00
Yb1—O1—H1B	121.00	C9—C10—H10A	120.00
Yb1—O2—H2A	117.00	C11—C10—H10A	120.00
Yb1—O2—H2B	124.00	C10—C11—H11A	121.00
H2A—O2—H2B	107.00	C12—C11—H11A	121.00
Yb1—O3—H3A	113.00

O1—Yb1—O5—C6	−31.3 (8)	Cu1^v—O7—C7—C4	80.0 (10)
O2—Yb1—O5—C6	127.4 (7)	Yb1^vi—O8—C7—O7	−13.3 (16)
O3—Yb1—O5—C6	172.9 (7)	Yb1^vi—O8—C7—C4	165.0 (6)
O4—Yb1—O5—C6	−75.6 (7)	Yb1—O9—C13—O10	−18.5 (18)
O9—Yb1—O5—C6	63.8 (7)	Yb1—O9—C13—C9	170.0 (7)
N1—Yb1—O5—C6	12.0 (7)	Cu1—O11—C14—O12	173.2 (7)
O8ⁱ—Yb1—O5—C6	−150.5 (7)	Cu1—O11—C14—C12	−7.1 (9)
O1—Yb1—O9—C13	−129.3 (11)	Yb1—N1—C1—C2	176.5 (7)
O2—Yb1—O9—C13	35.3 (10)	Yb1—N1—C1—C6	−3.0 (10)
O3—Yb1—O9—C13	−51.6 (11)	C5—N1—C1—C2	1.2 (13)
O4—Yb1—O9—C13	−156.7 (9)	C5—N1—C1—C6	−178.3 (8)
O5—Yb1—O9—C13	100.5 (11)	Yb1—N1—C5—C4	−173.7 (6)
N1—Yb1—O9—C13	149.8 (11)	C1—N1—C5—C4	1.1 (13)
O8ⁱ—Yb1—O9—C13	−13.5 (13)	Cu1—N2—C8—C9	174.0 (6)
O1—Yb1—N1—C1	145.0 (6)	C12—N2—C8—C9	3.2 (13)
O1—Yb1—N1—C5	−40.1 (7)	Cu1—N2—C12—C11	−173.7 (7)
O2—Yb1—N1—C1	−70.1 (6)	Cu1—N2—C12—C14	6.8 (8)
O2—Yb1—N1—C5	104.8 (7)	C8—N2—C12—C11	−1.4 (12)
O3—Yb1—N1—C1	−169.3 (6)	C8—N2—C12—C14	179.1 (7)
O3—Yb1—N1—C5	5.6 (9)	N1—C1—C2—C3	−2.8 (15)
O4—Yb1—N1—C1	76.0 (6)	C6—C1—C2—C3	176.7 (9)
O4—Yb1—N1—C5	−109.2 (7)	N1—C1—C6—O5	12.5 (12)
O5—Yb1—N1—C1	−3.5 (6)	N1—C1—C6—O6	−167.0 (8)
O5—Yb1—N1—C5	171.4 (7)	C2—C1—C6—O5	−167.0 (9)
O9—Yb1—N1—C1	−135.9 (7)	C2—C1—C6—O6	13.5 (14)
O9—Yb1—N1—C5	39.0 (7)	C1—C2—C3—C4	2.0 (15)
O8ⁱ—Yb1—N1—C1	26.7 (8)	C2—C3—C4—C5	0.1 (14)
O8ⁱ—Yb1—N1—C5	−158.4 (6)	C2—C3—C4—C7	−177.9 (9)
O1—Yb1—O8ⁱ—C7ⁱ	68.2 (9)	C3—C4—C5—N1	−1.8 (14)
O2—Yb1—O8ⁱ—C7ⁱ	−80.8 (9)	C7—C4—C5—N1	176.3 (8)
O3—Yb1—O8ⁱ—C7ⁱ	4.4 (9)	C3—C4—C7—O7	173.3 (9)
O4—Yb1—O8ⁱ—C7ⁱ	122.3 (9)	C3—C4—C7—O8	−5.1 (13)
O5—Yb1—O8ⁱ—C7ⁱ	−158.4 (9)	C5—C4—C7—O7	−4.7 (13)
O9—Yb1—O8ⁱ—C7ⁱ	−33.7 (11)	C5—C4—C7—O8	176.9 (8)
N1—Yb1—O8ⁱ—C7ⁱ	173.9 (8)	N2—C8—C9—C10	−3.3 (13)
N2—Cu1—O11—C14	8.6 (6)	N2—C8—C9—C13	179.3 (8)
O7^iv—Cu1—O11—C14	−71.7 (6)	C8—C9—C10—C11	1.4 (13)
N2ⁱⁱ—Cu1—O11—C14	−171.4 (6)	C13—C9—C10—C11	178.8 (8)
O7ⁱⁱⁱ—Cu1—O11—C14	108.3 (6)	C8—C9—C13—O9	−157.1 (9)
O11—Cu1—N2—C8	−179.6 (8)	C8—C9—C13—O10	30.5 (13)
O11—Cu1—N2—C12	−8.3 (5)	C10—C9—C13—O9	25.5 (14)
O7^iv—Cu1—N2—C8	−90.5 (7)	C10—C9—C13—O10	−146.9 (10)
O7^iv—Cu1—N2—C12	80.8 (5)	C9—C10—C11—C12	0.3 (13)
O11ⁱⁱ—Cu1—N2—C8	0.4 (8)	C10—C11—C12—N2	−0.3 (13)
O11ⁱⁱ—Cu1—N2—C12	171.7 (5)	C10—C11—C12—C14	179.2 (8)
O7ⁱⁱⁱ—Cu1—N2—C8	89.5 (7)	N2—C12—C14—O11	0.0 (10)
O7ⁱⁱⁱ—Cu1—N2—C12	−99.2 (5)	N2—C12—C14—O12	179.7 (8)
Yb1—O5—C6—O6	161.7 (7)	C11—C12—C14—O11	−179.5 (8)
Yb1—O5—C6—C1	−17.8 (11)	C11—C12—C14—O12	0.2 (12)
Cu1^v—O7—C7—O8	−101.7 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O12^vii	0.81	1.96	2.757 (9)	165
O1—H1B···O11ⁱⁱⁱ	0.82	2.02	2.782 (9)	153
O2—H2A···O10	0.88	1.88	2.670 (11)	149
O2—H2B···O5^viii	0.82	1.87	2.667 (9)	163
O3—H3A···O7ⁱ	0.84	1.82	2.607 (9)	155
O3—H3B···O13	0.82	1.95	2.73 (2)	159
O4—H4A···O10^v	0.82	1.95	2.760 (10)	167
O4—H4B···O6^ix	0.82	1.98	2.802 (9)	179
O13—H13A···O10	0.87	2.20	3.03 (2)	161
O13—H13B···O12ⁱ	0.85	1.96	2.81 (2)	177

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

Experimental details

Crystal data
Chemical formula	[CuYb₂(C₇H₃NO₄)₄(H₂O)₈]·H₂O
M_r	1232.19
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.7120 (5), 9.2713 (6), 13.2452 (9)
α, β, γ (°)	75.529 (1), 76.216 (1), 78.117 (1)
V (Å³)	879.73 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	5.98
Crystal size (mm)	0.15 × 0.15 × 0.03

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.646, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7620, 3150, 3010
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.095, 1.18
No. of reflections	3150
No. of parameters	271
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0263P)² + 10.305P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.78, −2.60

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Yb1—N1	2.495 (7)	Yb1—O8ⁱ	2.297 (6)
Yb1—O1	2.365 (6)	Yb1—O9	2.334 (8)
Yb1—O2	2.254 (7)	Cu1—N2	1.985 (7)
Yb1—O3	2.330 (8)	Cu1—O7ⁱⁱ	2.641 (6)
Yb1—O4	2.346 (7)	Cu1—O11	1.944 (6)
Yb1—O5	2.297 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O12ⁱⁱⁱ	0.81	1.96	2.757 (9)	165
O1—H1B···O11^iv	0.82	2.02	2.782 (9)	153
O2—H2A···O10	0.88	1.88	2.670 (11)	149
O2—H2B···O5^v	0.82	1.87	2.667 (9)	163
O3—H3A···O7ⁱ	0.84	1.82	2.607 (9)	155
O3—H3B···O13	0.82	1.95	2.73 (2)	159
O4—H4A···O10^vi	0.82	1.95	2.760 (10)	167
O4—H4B···O6^vii	0.82	1.98	2.802 (9)	179
O13—H13A···O10	0.87	2.20	3.03 (2)	161
O13—H13B···O12ⁱ	0.85	1.96	2.81 (2)	177

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

Acknowledgements

This work was supported financially by Yuanpei University, Taiwan.

References

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