Poly[(6-carboxy­picolinato-κ3O2,N,O6)(μ3-pyridine-2,6-dicarboxyl­ato-κ5O2,N,O6:O2′:O6′)dysprosium(III)]

Li, X.; Lian, Q.-Y.; Meng, Q.-H.; Luo, Y.-F.; Zeng, R.-H.

doi:10.1107/S1600536809039075

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages m1288-m1289

https://doi.org/10.1107/S1600536809039075

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Poly[(6-carboxypicolinato-κ³O²,N,O⁶)(μ₃-pyridine-2,6-dicarboxylato-κ⁵O²,N,O⁶:O^2′:O^6′)dysprosium(III)]

Xu Li,^a Qing-Yang Lian,^a Qiu-Hui Meng,^a Yi-Fan Luo ^a ^* and Rong-Hua Zeng ^a,^b

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China., and ^bSouth China Normal University, Key Laboratory of Technology of Electrochemical Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: luoyf2004@yahoo.com.cn

(Received 15 September 2009; accepted 26 September 2009; online 3 October 2009)

In the title complex, [Dy(C₇H₃NO₄)(C₇H₄NO₄)]_n, one of the ligands is fully deprotonated while the second has lost only one H atom. Each Dy^III ion is coordinated by six O atoms and two N atoms from two pyridine-2,6-dicarboxylate and two 6-carboxypicolinate ligands, displaying a bicapped trigonal-prismatic geometry. The average Dy—O bond distance is 2.40 Å, some 0.1Å longer than the corresponding Ho—O distance in the isotypic holmium complex. Adjacent Dy^III ions are linked by the pyridine-2,6-dicarboxylate ligands, forming a layer in (100). These layers are further connected by π–π stacking interactions between neighboring pyridyl rings [centroid–centroid distance = 3.827 (3) Å] and C—H⋯O hydrogen-bonding interactions, assembling a three-dimensional supramolecular network. Within each layer, there are other π–π stacking interactions between neighboring pyridyl rings [centroid–centroid distance = 3.501 (2) Å] and O—H⋯O and C—H⋯O hydrogen-bonding interactions, which further stabilize the structure.

Related literature

For the isotypic holmium analogue, see: Fernandes et al. (2001 ). For other related structures, see: Hong (2007 ); Huang et al. (2008 ); Idrees et al. (2009 ); Rafizadeh & Amani (2006 ); Thallapally et al. (2008 ).

Experimental

Crystal data

[Dy(C₇H₃NO₄)(C₇H₄NO₄)]
M_r = 493.72
Monoclinic, P 2₁ /c
a = 12.2151 (14) Å
b = 8.3703 (10) Å
c = 13.4698 (16) Å
β = 102.332 (1)°
V = 1345.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 5.61 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.359, T_max = 0.415
6670 measured reflections
2413 independent reflections
2305 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.12
2413 reflections
229 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −1.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Dy1—O8ⁱ	2.266 (2)
Dy1—O6ⁱⁱ	2.314 (3)
Dy1—O1	2.328 (2)
Dy1—O5	2.385 (3)
Dy1—O7	2.405 (2)
Dy1—N2	2.469 (3)
Dy1—N1	2.488 (3)
Dy1—O4	2.513 (2)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O4ⁱⁱⁱ	0.811 (19)	1.73 (2)	2.518 (3)	164 (5)
O2—H2A⋯O3ⁱⁱⁱ	0.811 (19)	2.65 (3)	3.303 (4)	139 (4)
C9—H9⋯O1^iv	0.93	2.42	3.332 (4)	165
C1—H1⋯O5^v	0.93	2.42	3.123 (5)	133
C2—H2⋯O3ⁱⁱⁱ	0.93	2.47	3.393 (5)	174
Symmetry code: (iii) x, y+1, z; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809039075/sj2654sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039075/sj2654Isup2.hkl

checkCIF report

Comment top

Research on the design and synthesis of metal-organic frameworks (MOFs) in recent years has become an active area in the fields of crystal engineering and supramolecular chemistry, not only because of their tremendous potential applications in gas storage, chemical separations, ion exchange, microelectronics, nonlinear optics, and heterogeneous catalysis, but also because of their intriguing variety of architectures and topologies (Hong, 2007; Thallapally et al., 2008). The synthesis of such species is often based on the self-assembly of suitable building blocks to give supramolecular networks constructed by coordination or/and hydrogen bonds or other weaker supromolecular interactions, such as π-π stacking interactions. As a building block, the pyridine-2,6-dicarboxylic acid is a good ligand with multifunctional coordination sites providing intriguing architectures and topologies (Fernandes et al., 2001; Rafizadeh & Amani, 2006; Huang et al., 2008; Idrees et al., 2009). Recently, we obtained the title coordination polymer, which was synthesized under hydrothermal conditions.

In the structure of the title compound (Fig. 1), one of the ligands is fully deprotonated while the second carries an OH group. Each Dy^III centre is eight -coordinated by six oxygen atoms two N atoms from two pyridine-2,6-dicarboxylato and two 6-carboxypicolinato ligands, and can described as having a bicapped trigonal prismatic geometry with Dy—O distances and O—Dy—O angles ranging from 2.266 (2) Å to 2.513 (2) Å (Table 1) and 76.75.30 (8) %A to 153.60 (9) %A, respectively. It is of interest that the Dy···O and Dy···N distances are slightly longer than the corresponding values in the isostructural Ho complex (Fernandes et al., 2001). Indeed the average Dy—O bond distance is 2.396 Å, some 0.1 Å longer than the corresponding distance (Ho—O = 2.385Å) in the isomorphous holmium complex as anticipated due to the lanthanide contraction. The pyridine-2,6-dicarboxylato ligands act as bridges linking adjacent Dy^III metal centres into a layer parallel to the (1 0 0) plane. Within the layer, the 6-carboxypicolinato ligands are both hydrogen bond donors and hydrogen bond acceptors with O—H···O and C—H···O hydrogen bonding interactions stabilizing the crystal structure (Table 2). π-π stacking interactions (the centroid-centroid distance between neighboring pyridyl rings is 3.827 (3) Å) and C—H···O hydrogen bonding interactions connect those layers to produce a three-dimensional supramolecular motif (Fig. 2). Other π-π stacking interactions between neighboring pyridyl rings are also present in each layer, the centroid-centroid distance is 3.501 (2) Å.

Related literature top

For the isomorphous holmium analogue, see: Fernandes et al. (2001). For other related structures, see: Hong (2007); Huang et al. (2008); Idrees et al. (2009); Rafizadeh & Amani (2006); Thallapally et al. (2008).

Experimental top

A mixture of Dy₂O₃ (0.375 g; 1 mmol), pyridine-2,6-dicarboxylic acid (0.167 g; 1 mmol), water (10 ml) and HNO₃ (0.024 g; 0.385 mmol) was stirred vigorously for 20 min and then sealed in a Teflon-lined stainless-steel autoclave (20 ml, capacity). The autoclave was heated and maintained at 433 K for 3 days, and then cooled to room temperature at 5 K h^-1 to yield colorless block-like crystals.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing the atomic-numbering scheme, with displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (#1) x, 0.5-y, -0.5+z; (#2) -x, 0.5+y, 1.5-z.
	Fig. 2. A view of the three-dimensional supramolecular network. Hydrogen bonds are shown as dashed lines.

Poly[(6-carboxypicolinato-κ³O²,N,O⁶)(µ₃-pyridine-2,6-dicarboxylato-κ⁵O²,N,O⁶:O^2':O^6')dysprosium(III)] top

Crystal data top

[Dy(C₇H₃NO₄)(C₇H₄NO₄)]	F(000) = 940
M_r = 493.72	D_x = 2.437 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5626 reflections
a = 12.2151 (14) Å	θ = 2.4–27.8°
b = 8.3703 (10) Å	µ = 5.61 mm⁻¹
c = 13.4698 (16) Å	T = 296 K
β = 102.332 (1)°	Block, colourless
V = 1345.4 (3) Å³	0.23 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	2413 independent reflections
Radiation source: fine-focus sealed tube	2305 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→12
T_min = 0.359, T_max = 0.415	k = −8→10
6670 measured reflections	l = −16→16

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0241P)² + 1.92P] where P = (F_o² + 2F_c²)/3
2413 reflections	(Δ/σ)_max = 0.002
229 parameters	Δρ_max = 0.58 e Å⁻³
1 restraint	Δρ_min = −1.43 e Å⁻³

Crystal data top

[Dy(C₇H₃NO₄)(C₇H₄NO₄)]	V = 1345.4 (3) Å³
M_r = 493.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2151 (14) Å	µ = 5.61 mm⁻¹
b = 8.3703 (10) Å	T = 296 K
c = 13.4698 (16) Å	0.23 × 0.21 × 0.19 mm
β = 102.332 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2413 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2305 reflections with I > 2σ(I)
T_min = 0.359, T_max = 0.415	R_int = 0.024
6670 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	1 restraint
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.58 e Å⁻³
2413 reflections	Δρ_min = −1.43 e Å⁻³
229 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Dy1	0.197015 (13)	0.232131 (18)	0.818183 (11)	0.00903 (7)
C2	0.5158 (3)	0.5574 (5)	0.8746 (3)	0.0243 (9)
H2	0.5247	0.6677	0.8750	0.029*
C3	0.4095 (3)	0.4901 (4)	0.8567 (3)	0.0184 (8)
C4	0.4836 (3)	0.2361 (4)	0.8735 (3)	0.0187 (8)
C1	0.6084 (3)	0.4572 (5)	0.8919 (3)	0.0282 (9)
H1	0.6805	0.4990	0.9030	0.034*
C5	0.5912 (3)	0.2933 (5)	0.8922 (3)	0.0274 (9)
H5	0.6518	0.2233	0.9049	0.033*
N1	0.3933 (2)	0.3321 (3)	0.8555 (2)	0.0136 (6)
C6	0.3019 (3)	0.5872 (4)	0.8367 (3)	0.0201 (8)
O1	0.2131 (2)	0.5091 (3)	0.82690 (18)	0.0180 (6)
O2	0.3085 (3)	0.7328 (3)	0.8293 (3)	0.0452 (10)
C7	0.4611 (3)	0.0608 (4)	0.8716 (3)	0.0203 (8)
O4	0.3508 (2)	0.0270 (3)	0.8468 (2)	0.0202 (6)
O3	0.5333 (2)	−0.0385 (3)	0.8889 (3)	0.0368 (8)
C13	0.2072 (3)	0.1845 (4)	1.0625 (2)	0.0128 (7)
C8	0.1581 (3)	0.0254 (4)	1.0222 (2)	0.0122 (7)
O5	0.2310 (2)	0.2782 (3)	0.9969 (2)	0.0200 (6)
N2	0.1355 (2)	0.0186 (3)	0.9205 (2)	0.0107 (6)
C11	0.0664 (3)	−0.2478 (4)	0.9275 (3)	0.0171 (8)
H11	0.0339	−0.3386	0.8937	0.021*
C12	0.0876 (3)	−0.1133 (4)	0.8745 (2)	0.0115 (7)
O7	0.1092 (2)	0.0071 (3)	0.72203 (17)	0.0148 (5)
O6	0.2198 (2)	0.2145 (3)	1.15526 (19)	0.0184 (6)
C14	0.0590 (3)	−0.0988 (4)	0.7607 (2)	0.0115 (7)
C9	0.1386 (3)	−0.1020 (4)	1.0812 (3)	0.0152 (7)
H9	0.1539	−0.0945	1.1517	0.018*
C10	0.0953 (3)	−0.2420 (4)	1.0324 (3)	0.0183 (8)
H10	0.0858	−0.3317	1.0703	0.022*
O8	−0.0153 (2)	−0.1898 (3)	0.71176 (18)	0.0171 (5)
H2A	0.334 (3)	0.822 (3)	0.838 (3)	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.00974 (11)	0.00762 (10)	0.01008 (11)	−0.00032 (5)	0.00291 (7)	0.00052 (5)
C2	0.026 (2)	0.0179 (19)	0.030 (2)	−0.0111 (16)	0.0069 (17)	−0.0045 (16)
C3	0.022 (2)	0.0131 (17)	0.0203 (19)	−0.0011 (15)	0.0048 (15)	0.0002 (14)
C4	0.015 (2)	0.0168 (18)	0.024 (2)	−0.0005 (14)	0.0039 (16)	−0.0011 (14)
C1	0.019 (2)	0.025 (2)	0.040 (3)	−0.0099 (16)	0.0056 (18)	−0.0064 (17)
C5	0.015 (2)	0.023 (2)	0.042 (3)	−0.0006 (16)	0.0021 (18)	−0.0035 (18)
N1	0.0122 (15)	0.0120 (14)	0.0171 (15)	−0.0013 (12)	0.0043 (12)	0.0005 (11)
C6	0.025 (2)	0.0145 (18)	0.0207 (19)	0.0017 (15)	0.0048 (16)	0.0005 (14)
O1	0.0183 (14)	0.0111 (13)	0.0251 (14)	−0.0001 (10)	0.0057 (11)	0.0010 (9)
O2	0.039 (2)	0.0065 (14)	0.088 (3)	−0.0048 (12)	0.009 (2)	0.0015 (15)
C7	0.016 (2)	0.0165 (18)	0.029 (2)	0.0006 (15)	0.0053 (16)	−0.0004 (15)
O4	0.0121 (13)	0.0105 (12)	0.0378 (16)	−0.0023 (10)	0.0048 (11)	0.0001 (10)
O3	0.0185 (15)	0.0197 (15)	0.070 (2)	0.0055 (12)	0.0043 (15)	0.0011 (14)
C13	0.0114 (17)	0.0152 (17)	0.0122 (18)	0.0025 (13)	0.0031 (14)	0.0011 (13)
C8	0.0097 (17)	0.0157 (17)	0.0124 (17)	0.0037 (13)	0.0049 (13)	−0.0021 (13)
O5	0.0295 (16)	0.0178 (13)	0.0137 (14)	−0.0094 (11)	0.0066 (12)	−0.0016 (10)
N2	0.0102 (14)	0.0123 (14)	0.0102 (14)	−0.0009 (11)	0.0036 (11)	−0.0004 (11)
C11	0.024 (2)	0.0125 (17)	0.017 (2)	−0.0039 (13)	0.0096 (17)	−0.0024 (13)
C12	0.0103 (17)	0.0112 (16)	0.0143 (17)	−0.0011 (13)	0.0053 (13)	0.0000 (13)
O7	0.0177 (13)	0.0146 (12)	0.0131 (12)	−0.0036 (10)	0.0054 (10)	−0.0004 (9)
O6	0.0262 (15)	0.0182 (13)	0.0119 (13)	−0.0017 (11)	0.0064 (11)	−0.0037 (10)
C14	0.0093 (17)	0.0120 (16)	0.0139 (17)	0.0019 (13)	0.0043 (13)	−0.0033 (13)
C9	0.0166 (18)	0.0191 (18)	0.0107 (17)	0.0001 (14)	0.0044 (14)	0.0015 (13)
C10	0.019 (2)	0.0191 (18)	0.018 (2)	−0.0012 (14)	0.0068 (16)	0.0061 (13)
O8	0.0159 (13)	0.0198 (13)	0.0163 (13)	−0.0061 (11)	0.0052 (10)	−0.0045 (10)

Geometric parameters (Å, º) top

Dy1—O8ⁱ	2.266 (2)	O2—H2A	0.811 (19)
Dy1—O6ⁱⁱ	2.314 (3)	C7—O3	1.198 (5)
Dy1—O1	2.328 (2)	C7—O4	1.347 (4)
Dy1—O5	2.385 (3)	C13—O6	1.251 (4)
Dy1—O7	2.405 (2)	C13—O5	1.261 (4)
Dy1—N2	2.469 (3)	C13—C8	1.513 (5)
Dy1—N1	2.488 (3)	C8—N2	1.341 (4)
Dy1—O4	2.513 (2)	C8—C9	1.381 (5)
C2—C1	1.388 (6)	N2—C12	1.338 (4)
C2—C3	1.389 (6)	C11—C10	1.382 (6)
C2—H2	0.9300	C11—C12	1.387 (5)
C3—N1	1.336 (4)	C11—H11	0.9300
C3—C6	1.519 (5)	C12—C14	1.502 (5)
C4—N1	1.344 (5)	O7—C14	1.253 (4)
C4—C5	1.371 (6)	O6—Dy1ⁱⁱⁱ	2.314 (3)
C4—C7	1.492 (5)	C14—O8	1.257 (4)
C1—C5	1.388 (6)	C9—C10	1.392 (5)
C1—H1	0.9300	C9—H9	0.9300
C5—H5	0.9300	C10—H10	0.9300
C6—O2	1.226 (4)	O8—Dy1^iv	2.266 (2)
C6—O1	1.250 (5)

O8ⁱ—Dy1—O6ⁱⁱ	95.01 (9)	C1—C5—H5	120.5
O8ⁱ—Dy1—O1	77.91 (9)	C3—N1—C4	118.4 (3)
O6ⁱⁱ—Dy1—O1	80.18 (9)	C3—N1—Dy1	117.9 (2)
O8ⁱ—Dy1—O5	94.91 (9)	C4—N1—Dy1	123.6 (2)
O6ⁱⁱ—Dy1—O5	153.60 (9)	O2—C6—O1	125.5 (4)
O1—Dy1—O5	78.08 (8)	O2—C6—C3	118.5 (4)
O8ⁱ—Dy1—O7	79.79 (9)	O1—C6—C3	115.9 (3)
O6ⁱⁱ—Dy1—O7	76.74 (8)	C6—O1—Dy1	126.0 (2)
O1—Dy1—O7	146.15 (8)	C6—O2—H2A	159 (3)
O5—Dy1—O7	129.18 (8)	O3—C7—O4	124.0 (3)
O8ⁱ—Dy1—N2	84.53 (9)	O3—C7—C4	123.6 (4)
O6ⁱⁱ—Dy1—N2	141.40 (9)	O4—C7—C4	112.4 (3)
O1—Dy1—N2	136.47 (9)	C7—O4—Dy1	124.8 (2)
O5—Dy1—N2	64.02 (8)	O6—C13—O5	125.3 (3)
O7—Dy1—N2	65.15 (8)	O6—C13—C8	119.3 (3)
O8ⁱ—Dy1—N1	143.55 (10)	O5—C13—C8	115.4 (3)
O6ⁱⁱ—Dy1—N1	79.66 (9)	N2—C8—C9	122.2 (3)
O1—Dy1—N1	65.64 (9)	N2—C8—C13	112.5 (3)
O5—Dy1—N1	77.84 (10)	C9—C8—C13	125.3 (3)
O7—Dy1—N1	132.22 (9)	C13—O5—Dy1	126.2 (2)
N2—Dy1—N1	121.72 (9)	C12—N2—C8	118.8 (3)
O8ⁱ—Dy1—O4	153.64 (9)	C12—N2—Dy1	119.6 (2)
O6ⁱⁱ—Dy1—O4	92.28 (9)	C8—N2—Dy1	121.3 (2)
O1—Dy1—O4	128.35 (8)	C10—C11—C12	117.6 (3)
O5—Dy1—O4	89.58 (9)	C10—C11—H11	121.2
O7—Dy1—O4	77.30 (8)	C12—C11—H11	121.2
N2—Dy1—O4	74.15 (9)	N2—C12—C11	122.9 (3)
N1—Dy1—O4	62.74 (8)	N2—C12—C14	112.9 (3)
C1—C2—C3	118.9 (3)	C11—C12—C14	124.2 (3)
C1—C2—H2	120.6	C14—O7—Dy1	122.1 (2)
C3—C2—H2	120.6	C13—O6—Dy1ⁱⁱⁱ	166.3 (2)
N1—C3—C2	122.2 (3)	O7—C14—O8	125.0 (3)
N1—C3—C6	114.1 (3)	O7—C14—C12	116.9 (3)
C2—C3—C6	123.7 (3)	O8—C14—C12	118.1 (3)
N1—C4—C5	122.8 (3)	C8—C9—C10	118.2 (3)
N1—C4—C7	116.3 (3)	C8—C9—H9	120.9
C5—C4—C7	120.8 (3)	C10—C9—H9	120.9
C2—C1—C5	118.7 (4)	C11—C10—C9	120.1 (3)
C2—C1—H1	120.7	C11—C10—H10	120.0
C5—C1—H1	120.7	C9—C10—H10	120.0
C4—C5—C1	119.0 (4)	C14—O8—Dy1^iv	146.8 (2)
C4—C5—H5	120.5

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4^v	0.81 (2)	1.73 (2)	2.518 (3)	164 (5)
O2—H2A···O3^v	0.81 (2)	2.65 (3)	3.303 (4)	139 (4)
C9—H9···O1ⁱⁱⁱ	0.93	2.42	3.332 (4)	165
C1—H1···O5^vi	0.93	2.42	3.123 (5)	133
C2—H2···O3^v	0.93	2.47	3.393 (5)	174

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

Experimental details

Crystal data
Chemical formula	[Dy(C₇H₃NO₄)(C₇H₄NO₄)]
M_r	493.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.2151 (14), 8.3703 (10), 13.4698 (16)
β (°)	102.332 (1)
V (Å³)	1345.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.61
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.359, 0.415
No. of measured, independent and observed [I > 2σ(I)] reflections	6670, 2413, 2305
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.12
No. of reflections	2413
No. of parameters	229
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −1.43

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Dy1—O8ⁱ	2.266 (2)	Dy1—O7	2.405 (2)
Dy1—O6ⁱⁱ	2.314 (3)	Dy1—N2	2.469 (3)
Dy1—O1	2.328 (2)	Dy1—N1	2.488 (3)
Dy1—O5	2.385 (3)	Dy1—O4	2.513 (2)

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4ⁱⁱⁱ	0.811 (19)	1.73 (2)	2.518 (3)	164 (5)
O2—H2A···O3ⁱⁱⁱ	0.811 (19)	2.65 (3)	3.303 (4)	139 (4)
C9—H9···O1^iv	0.93	2.42	3.332 (4)	165.3
C1—H1···O5^v	0.93	2.42	3.123 (5)	132.6
C2—H2···O3ⁱⁱⁱ	0.93	2.47	3.393 (5)	173.5

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

Acknowledgements

The authors acknowledge the Chan Xue Yan Cooperative Special Project of Guangdong Province and the Ministry of Science and Technology of the People's Republic of China (Project No, 2007A090302046), the Project of Science and Technology of Guangdong Province (Project No. 2007A020200002-4) and the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for supporting this work.

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