Poly[[μ3-3-(3-pyrid­yl)acrylato-κ3N:O:O′][μ2-3-(3-pyrid­yl)acrylato-κ3O,O′:O][μ2-3-(3-pyrid­yl)acrylato-κ2O:O′)]gadolinium(III)]

Qiu, Z.-H.; Liang, F.-P.; Ruan, Q.-F.; Chen, Z.-L.

doi:10.1107/S1600536808012270

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m766-m767

doi:10.1107/S1600536808012270

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Poly[[μ₃-3-(3-pyridyl)acrylato-κ³N:O:O′][μ₂-3-(3-pyridyl)acrylato-κ³O,O′:O][μ₂-3-(3-pyridyl)acrylato-κ²O:O′)]gadolinium(III)]

Zhi-Hui Qiu,^a,^b Fu-Pei Liang,^a ^* Qing-Feng Ruan ^c and Zi-Lu Chen ^a

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China, ^bFaculty of Earth Sciences, China University of Geosciences, Wuhan 430074, People's Republic of China, and ^cDepartment of Resources and Environmental Engineering, Guilin University of Technology, Guilin,541004, People's Republic of China
^*Correspondence e-mail: fupeiliang@yahoo.cn

(Received 14 April 2008; accepted 28 April 2008; online 3 May 2008)

In the title compound, [Gd(C₈H₆NO₂)₃]_n, the Gd^III ion is in a bicapped trigonal prismatic coordination environment formed by seven O atoms and one N atom, derived from seven different 3-(3-pyridyl)acrylate (3-PYA) ligands. Gd^III ions are bridged by bidentate and tridentate 3-PYA ligands, resulting in a two-dimensional structure.

Related literature

For related literature, see: Ayyappan et al. (2001 ); Gunning & Cahill (2005 ); Zhang et al. (2000 ) Liu et al. (2006 ); Liu et al. (2004 ); Zhou et al. (2004 ); Li et al. (2007 ). For related structures, see: Zhou et al., (2003 ).

Experimental

Crystal data

[Gd(C₈H₆NO₂)₃]
M_r = 601.66
Monoclinic, P 2₁ /c
a = 7.7197 (17) Å
b = 25.646 (6) Å
c = 11.445 (2) Å
β = 95.684 (3)°
V = 2254.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.99 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.534, T_max = 0.615 (expected range = 0.507–0.584)
12572 measured reflections
4654 independent reflections
3517 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.090
S = 1.05
4654 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 2.06 e Å⁻³
Δρ_min = −1.17 e Å⁻³

Table 1
Selected bond lengths (Å)

Gd1—O4ⁱ	2.305 (3)
Gd1—O2ⁱ	2.305 (3)
Gd1—O1	2.332 (3)
Gd1—O3	2.353 (3)
Gd1—O6ⁱⁱ	2.383 (3)
Gd1—O5	2.440 (3)
Gd1—O6	2.546 (3)
Gd1—N1ⁱⁱⁱ	2.628 (4)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+2.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012270/lh2617sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012270/lh2617Isup2.hkl

checkCIF report

Comment top

The bifunctional compound 3-pyridylacrylic acid (3-HPYA) is a potential multidentate ligand, and several types of complexes formed with 3-HPYA have been studied (Ayyappan et al., 2001; Gunning & Cahill, 2005; Zhang et al., 2000). Until now, however, only a few crystallographic studies of 4f-block metal complexes of HPYA have been reported (Liu et al.,2006; Liu et al.,2004; Zhou et al.,2004; Zhou et al.,2003; Li et al., 2007).

Here, we report the synthesis and structure of the title complex, [Gd(TPA)₃]_n (I) (Fig.1). The Gd^III ion is eight-coordinated by seven O atoms and one N atom derived from seven different 3-PYA ligands. The topology of (I) is a two-dimensional structure mediated by bridging 3-PYA ligands. Symmetry-related Gd^III centres are bridged by two bidentate and two tridentate 3-PYA ligands, which results in the formation of a one-dimensional chain along a axis (Fig.2). Different chains are connected by tridentate 3-PYA ligands, which results in the formation of a two-dimensional framework parallel to (100) (Fig.3). Gd—O distances are in the range 2.305 (3) to 2.546 (3) Å, and the Gd—N distance is 2.628 (4) Å.

Related literature top

For related literature, see: Ayyappan et al. (2001); Gunning & Cahill (2005); Zhang et al. (2000) Liu et al. (2006); Liu et al. (2004); Zhou et al. (2004); Li et al. (2007). For related structures, see: Zhou et al., (2003).

Experimental top

A mixture of Gd₂O₃(0.5 mmol), 3-pyridylacrylic acid (2.0 mmol), H₂O(14 ml) was sealed in a 25 ml Teflon-lined stainless reactor and heated at 468 K for six days under autogenous pressure, then followed by slow cooling to room temperature, when a few colourless crystals were obtained. Analysis:found C 47.41,H 3.08,N 7.03%; C₂₄H₂₀GdN₃O₇ requires C 47.45,H 2.97,N 6.92%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. A portion of the structure of (I) showing the coordination environment of the Gd^III ion, with displacement ellipsoids at the 30% probability level. All H atoms are omitted for clarity. [Symmetry codes:(a)-x,1 - y,-z;(b)-x,1 - y,1 - z;(c)1 - x,1 - y,1 - z.]
	Fig. 2. Part of a chain structure of (I), along the a axis. All H atoms are omitted.
	Fig. 3. The two-dimensional structure of (I) parallel to (100), All H atoms have been omitted for clearity.

Poly[[µ₃-3-(3-pyridyl)acrylato-κ³N:O:O'][µ₂- 3-(3-pyridyl)acrylato-κ³O,O':O][µ₂-3-(3- pyridyl)acrylato-κ²O:O')]gadolinium(III)] top

Crystal data top

[Gd(C₈H₆NO₂)₃]	F(000) = 1180
M_r = 601.66	D_x = 1.772 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5417 reflections
a = 7.7197 (17) Å	θ = 2.7–26.5°
b = 25.646 (6) Å	µ = 2.99 mm⁻¹
c = 11.445 (2) Å	T = 294 K
β = 95.684 (3)°	Block, colourless
V = 2254.8 (8) Å³	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4654 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 26.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.534, T_max = 0.615	k = −30→32
12572 measured reflections	l = −14→7

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0357P)² + 2.29P] where P = (F_o² + 2F_c²)/3
4654 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 2.06 e Å⁻³
0 restraints	Δρ_min = −1.17 e Å⁻³

Crystal data top

[Gd(C₈H₆NO₂)₃]	V = 2254.8 (8) Å³
M_r = 601.66	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7197 (17) Å	µ = 2.99 mm⁻¹
b = 25.646 (6) Å	T = 294 K
c = 11.445 (2) Å	0.24 × 0.20 × 0.18 mm
β = 95.684 (3)°

Data collection top

Bruker SMART CCD diffractometer	4654 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3517 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.615	R_int = 0.048
12572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.06	Δρ_max = 2.06 e Å⁻³
4654 reflections	Δρ_min = −1.17 e Å⁻³
307 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
Gd1	0.75345 (2)	0.501980 (8)	0.574129 (16)	0.01502 (9)
O1	0.9665 (4)	0.52846 (14)	0.7208 (3)	0.0273 (7)
O2	1.1908 (5)	0.52067 (14)	0.6134 (3)	0.0311 (8)
O3	0.8511 (4)	0.58040 (13)	0.4964 (3)	0.0306 (8)
O4	1.0842 (4)	0.57303 (13)	0.3946 (3)	0.0302 (8)
O5	0.6072 (4)	0.57155 (13)	0.6716 (3)	0.0262 (7)
O6	0.4848 (4)	0.55290 (13)	0.4935 (2)	0.0236 (7)
N1	1.3676 (5)	0.53963 (15)	1.2405 (3)	0.0240 (9)
C5	0.5075 (6)	0.58425 (18)	0.5821 (4)	0.0219 (10)
C6	0.9606 (6)	0.59796 (18)	0.4321 (4)	0.0236 (10)
C7	1.2073 (6)	0.5432 (2)	0.9203 (4)	0.0275 (11)
H7	1.0910	0.5364	0.9292	0.033*
C9	0.3667 (7)	0.72221 (19)	0.6627 (4)	0.0298 (11)
C10	0.8451 (7)	0.6892 (2)	0.4348 (4)	0.0330 (12)
H10	0.7659	0.6781	0.4857	0.040*
C11	0.4341 (7)	0.6688 (2)	0.6617 (4)	0.0314 (12)
H11	0.4939	0.6570	0.7312	0.038*
C12	1.2511 (6)	0.54388 (19)	0.8113 (4)	0.0245 (10)
H12	1.3640	0.5534	0.7986	0.029*
C13	1.3224 (6)	0.55200 (19)	1.0284 (4)	0.0248 (10)
C14	0.7726 (8)	0.7816 (2)	0.4738 (6)	0.0453 (15)
H14	0.7220	0.7695	0.5390	0.054*
C15	1.5195 (6)	0.5655 (2)	1.2392 (4)	0.0288 (11)
H15	1.5874	0.5703	1.3101	0.035*
N2	0.3364 (7)	0.80038 (19)	0.7784 (4)	0.0468 (13)
C17	0.9503 (7)	0.6539 (2)	0.3963 (5)	0.0347 (13)
H17	1.0246	0.6649	0.3420	0.042*
C18	0.4192 (6)	0.6355 (2)	0.5732 (4)	0.0290 (11)
H18	0.3521	0.6444	0.5041	0.035*
C20	0.2839 (7)	0.7472 (2)	0.5650 (4)	0.0370 (13)
H20	0.2652	0.7298	0.4937	0.044*
C21	0.8437 (7)	0.7449 (2)	0.4033 (5)	0.0332 (12)
C22	0.2294 (8)	0.7983 (2)	0.5747 (5)	0.0447 (15)
H22	0.1733	0.8155	0.5102	0.054*
C23	1.4821 (6)	0.5782 (2)	1.0315 (4)	0.0309 (12)
H23	1.5217	0.5907	0.9627	0.037*
N3	0.7710 (7)	0.8333 (2)	0.4554 (5)	0.0582 (15)
C25	0.3879 (8)	0.7510 (2)	0.7660 (5)	0.0425 (14)
H25	0.4425	0.7345	0.8321	0.051*
C26	0.8422 (8)	0.8500 (2)	0.3614 (6)	0.0539 (17)
H26	0.8422	0.8856	0.3465	0.065*
C27	1.5802 (6)	0.5853 (2)	1.1382 (4)	0.0326 (12)
H27	1.6855	0.6031	1.1421	0.039*
C28	0.9162 (8)	0.7645 (2)	0.3054 (5)	0.0429 (14)
H28	0.9645	0.7418	0.2542	0.052*
C29	0.9163 (9)	0.8174 (2)	0.2846 (6)	0.0515 (16)
H29	0.9653	0.8308	0.2200	0.062*
C30	0.2599 (8)	0.8233 (2)	0.6821 (5)	0.0441 (15)
H30	0.2253	0.8578	0.6873	0.053*
C33	1.1260 (6)	0.52998 (18)	0.7078 (4)	0.0203 (9)
C34	1.2735 (6)	0.53395 (19)	1.1353 (4)	0.0272 (11)
H34	1.1676	0.5166	1.1340	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.01666 (12)	0.01601 (13)	0.01255 (12)	−0.00038 (9)	0.00230 (8)	−0.00069 (9)
O1	0.0229 (17)	0.036 (2)	0.0223 (17)	−0.0025 (15)	−0.0008 (14)	−0.0003 (14)
O2	0.038 (2)	0.036 (2)	0.0197 (17)	−0.0029 (16)	0.0062 (15)	−0.0066 (15)
O3	0.0317 (19)	0.0241 (19)	0.038 (2)	−0.0019 (15)	0.0136 (16)	0.0060 (15)
O4	0.0315 (19)	0.0218 (18)	0.038 (2)	0.0080 (15)	0.0080 (16)	0.0036 (15)
O5	0.0279 (18)	0.0274 (19)	0.0230 (17)	0.0059 (14)	0.0011 (14)	−0.0011 (14)
O6	0.0245 (17)	0.0224 (17)	0.0241 (17)	−0.0025 (13)	0.0027 (14)	−0.0061 (13)
N1	0.026 (2)	0.024 (2)	0.021 (2)	−0.0016 (17)	−0.0005 (16)	0.0013 (16)
C5	0.022 (2)	0.021 (2)	0.022 (2)	−0.0032 (19)	0.0024 (19)	0.0027 (19)
C6	0.028 (3)	0.019 (2)	0.023 (2)	−0.0021 (19)	0.000 (2)	0.0005 (18)
C7	0.026 (2)	0.036 (3)	0.020 (2)	−0.011 (2)	−0.0020 (19)	−0.001 (2)
C9	0.035 (3)	0.027 (3)	0.028 (3)	0.003 (2)	0.005 (2)	−0.007 (2)
C10	0.036 (3)	0.027 (3)	0.037 (3)	0.003 (2)	0.009 (2)	0.004 (2)
C11	0.037 (3)	0.031 (3)	0.025 (3)	0.007 (2)	0.001 (2)	0.000 (2)
C12	0.023 (2)	0.032 (3)	0.019 (2)	−0.007 (2)	0.0044 (19)	−0.0048 (19)
C13	0.029 (3)	0.026 (3)	0.020 (2)	−0.005 (2)	0.003 (2)	−0.0030 (19)
C14	0.047 (4)	0.036 (3)	0.054 (4)	0.012 (3)	0.008 (3)	0.004 (3)
C15	0.030 (3)	0.032 (3)	0.023 (3)	0.000 (2)	−0.004 (2)	0.003 (2)
N2	0.064 (3)	0.033 (3)	0.043 (3)	0.007 (2)	0.003 (3)	−0.012 (2)
C17	0.033 (3)	0.029 (3)	0.046 (3)	0.007 (2)	0.017 (2)	0.013 (2)
C18	0.030 (3)	0.027 (3)	0.029 (3)	0.003 (2)	0.000 (2)	−0.004 (2)
C20	0.048 (3)	0.029 (3)	0.033 (3)	0.004 (2)	−0.001 (3)	−0.003 (2)
C21	0.037 (3)	0.026 (3)	0.036 (3)	0.006 (2)	0.003 (2)	0.004 (2)
C22	0.059 (4)	0.026 (3)	0.048 (4)	0.007 (3)	0.002 (3)	0.004 (3)
C23	0.032 (3)	0.038 (3)	0.024 (2)	−0.011 (2)	0.004 (2)	0.003 (2)
N3	0.068 (4)	0.026 (3)	0.081 (4)	0.013 (3)	0.009 (3)	−0.004 (3)
C25	0.053 (4)	0.036 (3)	0.036 (3)	0.013 (3)	−0.004 (3)	−0.005 (2)
C26	0.059 (4)	0.024 (3)	0.075 (5)	0.007 (3)	−0.014 (4)	0.008 (3)
C27	0.028 (3)	0.040 (3)	0.030 (3)	−0.011 (2)	0.000 (2)	0.003 (2)
C28	0.057 (4)	0.032 (3)	0.041 (3)	0.008 (3)	0.013 (3)	0.006 (2)
C29	0.065 (4)	0.033 (3)	0.057 (4)	0.005 (3)	0.008 (3)	0.016 (3)
C30	0.052 (4)	0.023 (3)	0.059 (4)	0.004 (3)	0.013 (3)	0.000 (3)
C33	0.024 (2)	0.021 (2)	0.016 (2)	−0.0032 (19)	0.0031 (18)	−0.0010 (17)
C34	0.028 (3)	0.030 (3)	0.023 (2)	−0.011 (2)	0.000 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Gd1—O4ⁱ	2.305 (3)	C11—C18	1.321 (6)
Gd1—O2ⁱ	2.305 (3)	C11—H11	0.9300
Gd1—O1	2.332 (3)	C12—C33	1.495 (6)
Gd1—O3	2.353 (3)	C12—H12	0.9300
Gd1—O6ⁱⁱ	2.383 (3)	C13—C34	1.394 (6)
Gd1—O5	2.440 (3)	C13—C23	1.401 (6)
Gd1—O6	2.546 (3)	C14—N3	1.343 (8)
Gd1—N1ⁱⁱⁱ	2.628 (4)	C14—C21	1.389 (8)
Gd1—C5	2.846 (5)	C14—H14	0.9300
O1—C33	1.255 (5)	C15—C27	1.385 (7)
O2—C33	1.257 (5)	C15—H15	0.9300
O2—Gd1ⁱ	2.305 (3)	N2—C30	1.333 (7)
O3—C6	1.258 (5)	N2—C25	1.340 (7)
O4—C6	1.259 (6)	C17—H17	0.9300
O4—Gd1ⁱ	2.305 (3)	C18—H18	0.9300
O5—C5	1.262 (5)	C20—C22	1.383 (8)
O6—C5	1.293 (5)	C20—H20	0.9300
O6—Gd1ⁱⁱ	2.383 (3)	C21—C28	1.395 (7)
N1—C15	1.348 (6)	C22—C30	1.386 (8)
N1—C34	1.351 (6)	C22—H22	0.9300
N1—Gd1ⁱⁱⁱ	2.628 (4)	C23—C27	1.383 (7)
C5—C18	1.479 (7)	C23—H23	0.9300
C6—C17	1.492 (7)	N3—C26	1.326 (8)
C7—C12	1.325 (6)	C25—H25	0.9300
C7—C13	1.468 (6)	C26—C29	1.378 (9)
C7—H7	0.9300	C26—H26	0.9300
C9—C20	1.388 (7)	C27—H27	0.9300
C9—C25	1.389 (7)	C28—C29	1.377 (8)
C9—C11	1.466 (7)	C28—H28	0.9300
C10—C17	1.321 (7)	C29—H29	0.9300
C10—C21	1.472 (7)	C30—H30	0.9300
C10—H10	0.9300	C34—H34	0.9300

O4ⁱ—Gd1—O2ⁱ	77.61 (12)	C17—C10—C21	124.9 (5)
O4ⁱ—Gd1—O1	78.31 (12)	C17—C10—H10	117.5
O2ⁱ—Gd1—O1	124.09 (12)	C21—C10—H10	117.5
O4ⁱ—Gd1—O3	125.63 (12)	C18—C11—C9	127.3 (5)
O2ⁱ—Gd1—O3	76.54 (12)	C18—C11—H11	116.3
O1—Gd1—O3	78.10 (12)	C9—C11—H11	116.3
O4ⁱ—Gd1—O6ⁱⁱ	87.00 (12)	C7—C12—C33	122.5 (4)
O2ⁱ—Gd1—O6ⁱⁱ	76.00 (11)	C7—C12—H12	118.7
O1—Gd1—O6ⁱⁱ	150.72 (11)	C33—C12—H12	118.7
O3—Gd1—O6ⁱⁱ	130.38 (11)	C34—C13—C23	116.8 (4)
O4ⁱ—Gd1—O5	143.96 (11)	C34—C13—C7	119.6 (4)
O2ⁱ—Gd1—O5	138.40 (12)	C23—C13—C7	123.6 (4)
O1—Gd1—O5	77.47 (11)	N3—C14—C21	125.3 (6)
O3—Gd1—O5	74.21 (11)	N3—C14—H14	117.4
O6ⁱⁱ—Gd1—O5	101.73 (11)	C21—C14—H14	117.4
O4ⁱ—Gd1—O6	153.58 (11)	N1—C15—C27	123.7 (4)
O2ⁱ—Gd1—O6	90.69 (11)	N1—C15—H15	118.1
O1—Gd1—O6	127.08 (11)	C27—C15—H15	118.1
O3—Gd1—O6	72.81 (11)	C30—N2—C25	116.1 (5)
O6ⁱⁱ—Gd1—O6	67.07 (13)	C10—C17—C6	125.8 (5)
O5—Gd1—O6	52.66 (10)	C10—C17—H17	117.1
O4ⁱ—Gd1—N1ⁱⁱⁱ	76.53 (12)	C6—C17—H17	117.1
O2ⁱ—Gd1—N1ⁱⁱⁱ	139.77 (13)	C11—C18—C5	121.1 (5)
O1—Gd1—N1ⁱⁱⁱ	79.57 (11)	C11—C18—H18	119.4
O3—Gd1—N1ⁱⁱⁱ	143.62 (12)	C5—C18—H18	119.4
O6ⁱⁱ—Gd1—N1ⁱⁱⁱ	72.39 (11)	C22—C20—C9	119.5 (5)
O5—Gd1—N1ⁱⁱⁱ	73.15 (11)	C22—C20—H20	120.2
O6—Gd1—N1ⁱⁱⁱ	99.15 (11)	C9—C20—H20	120.2
O4ⁱ—Gd1—C5	165.50 (12)	C14—C21—C28	115.8 (5)
O2ⁱ—Gd1—C5	113.80 (13)	C14—C21—C10	120.6 (5)
O1—Gd1—C5	100.73 (12)	C28—C21—C10	123.6 (5)
O3—Gd1—C5	67.56 (12)	C20—C22—C30	118.8 (5)
O6ⁱⁱ—Gd1—C5	87.27 (12)	C20—C22—H22	120.6
O5—Gd1—C5	26.20 (11)	C30—C22—H22	120.6
O6—Gd1—C5	27.02 (11)	C27—C23—C13	119.2 (4)
N1ⁱⁱⁱ—Gd1—C5	89.04 (12)	C27—C23—H23	120.4
C33—O1—Gd1	123.6 (3)	C13—C23—H23	120.4
C33—O2—Gd1ⁱ	167.0 (3)	C26—N3—C14	116.5 (5)
C6—O3—Gd1	141.8 (3)	N2—C25—C9	125.5 (5)
C6—O4—Gd1ⁱ	142.2 (3)	N2—C25—H25	117.2
C5—O5—Gd1	95.2 (3)	C9—C25—H25	117.2
C5—O6—Gd1ⁱⁱ	131.5 (3)	N3—C26—C29	123.7 (6)
C5—O6—Gd1	89.5 (3)	N3—C26—H26	118.2
Gd1ⁱⁱ—O6—Gd1	112.93 (13)	C29—C26—H26	118.2
C15—N1—C34	115.8 (4)	C23—C27—C15	119.2 (5)
C15—N1—Gd1ⁱⁱⁱ	126.0 (3)	C23—C27—H27	120.4
C34—N1—Gd1ⁱⁱⁱ	118.2 (3)	C15—C27—H27	120.4
O5—C5—O6	120.1 (4)	C29—C28—C21	120.1 (6)
O5—C5—C18	121.7 (4)	C29—C28—H28	119.9
O6—C5—C18	118.2 (4)	C21—C28—H28	119.9
O5—C5—Gd1	58.6 (2)	C26—C29—C28	118.7 (6)
O6—C5—Gd1	63.4 (2)	C26—C29—H29	120.7
C18—C5—Gd1	163.9 (3)	C28—C29—H29	120.7
O3—C6—O4	126.4 (4)	N2—C30—C22	123.5 (5)
O3—C6—C17	119.0 (4)	N2—C30—H30	118.3
O4—C6—C17	114.6 (4)	C22—C30—H30	118.3
C12—C7—C13	127.0 (5)	O1—C33—O2	125.1 (4)
C12—C7—H7	116.5	O1—C33—C12	118.5 (4)
C13—C7—H7	116.5	O2—C33—C12	116.4 (4)
C20—C9—C25	116.5 (5)	N1—C34—C13	125.3 (4)
C20—C9—C11	124.1 (4)	N1—C34—H34	117.4
C25—C9—C11	119.4 (5)	C13—C34—H34	117.4

O4ⁱ—Gd1—O1—C33	63.2 (4)	O4ⁱ—Gd1—C5—C18	153.1 (10)
O2ⁱ—Gd1—O1—C33	−3.0 (4)	O2ⁱ—Gd1—C5—C18	−66.6 (12)
O3—Gd1—O1—C33	−67.5 (4)	O1—Gd1—C5—C18	68.3 (12)
O6ⁱⁱ—Gd1—O1—C33	124.6 (3)	O3—Gd1—C5—C18	−3.9 (11)
O5—Gd1—O1—C33	−143.7 (4)	O6ⁱⁱ—Gd1—C5—C18	−140.0 (12)
O6—Gd1—O1—C33	−124.9 (3)	O5—Gd1—C5—C18	96.1 (12)
N1ⁱⁱⁱ—Gd1—O1—C33	141.4 (4)	O6—Gd1—C5—C18	−100.0 (12)
C5—Gd1—O1—C33	−131.6 (4)	N1ⁱⁱⁱ—Gd1—C5—C18	147.5 (12)
O4ⁱ—Gd1—O3—C6	25.1 (5)	Gd1—O3—C6—O4	−9.9 (9)
O2ⁱ—Gd1—O3—C6	−38.6 (5)	Gd1—O3—C6—C17	171.4 (4)
O1—Gd1—O3—C6	91.1 (5)	Gd1ⁱ—O4—C6—O3	−16.9 (9)
O6ⁱⁱ—Gd1—O3—C6	−96.6 (5)	Gd1ⁱ—O4—C6—C17	161.9 (4)
O5—Gd1—O3—C6	171.3 (5)	C20—C9—C11—C18	−4.1 (9)
O6—Gd1—O3—C6	−133.6 (5)	C25—C9—C11—C18	177.1 (6)
N1ⁱⁱⁱ—Gd1—O3—C6	144.4 (5)	C13—C7—C12—C33	174.8 (5)
C5—Gd1—O3—C6	−161.8 (5)	C12—C7—C13—C34	−159.3 (5)
O4ⁱ—Gd1—O5—C5	−159.1 (3)	C12—C7—C13—C23	20.9 (8)
O2ⁱ—Gd1—O5—C5	24.2 (3)	C34—N1—C15—C27	−0.4 (7)
O1—Gd1—O5—C5	152.1 (3)	Gd1ⁱⁱⁱ—N1—C15—C27	177.8 (4)
O3—Gd1—O5—C5	71.1 (3)	C21—C10—C17—C6	176.4 (5)
O6ⁱⁱ—Gd1—O5—C5	−57.9 (3)	O3—C6—C17—C10	6.8 (8)
O6—Gd1—O5—C5	−9.1 (2)	O4—C6—C17—C10	−172.1 (5)
N1ⁱⁱⁱ—Gd1—O5—C5	−125.2 (3)	C9—C11—C18—C5	174.6 (5)
O4ⁱ—Gd1—O6—C5	147.4 (3)	O5—C5—C18—C11	−3.9 (7)
O2ⁱ—Gd1—O6—C5	−149.8 (3)	O6—C5—C18—C11	178.5 (4)
O1—Gd1—O6—C5	−14.5 (3)	Gd1—C5—C18—C11	−89.9 (12)
O3—Gd1—O6—C5	−74.2 (2)	C25—C9—C20—C22	0.6 (8)
O6ⁱⁱ—Gd1—O6—C5	135.7 (3)	C11—C9—C20—C22	−178.2 (5)
O5—Gd1—O6—C5	8.8 (2)	N3—C14—C21—C28	−0.9 (9)
N1ⁱⁱⁱ—Gd1—O6—C5	69.3 (3)	N3—C14—C21—C10	177.3 (6)
O4ⁱ—Gd1—O6—Gd1ⁱⁱ	11.7 (3)	C17—C10—C21—C14	−159.1 (6)
O2ⁱ—Gd1—O6—Gd1ⁱⁱ	74.46 (14)	C17—C10—C21—C28	18.9 (9)
O1—Gd1—O6—Gd1ⁱⁱ	−150.16 (12)	C9—C20—C22—C30	0.3 (9)
O3—Gd1—O6—Gd1ⁱⁱ	150.14 (15)	C34—C13—C23—C27	−0.8 (8)
O6ⁱⁱ—Gd1—O6—Gd1ⁱⁱ	0.0	C7—C13—C23—C27	179.0 (5)
O5—Gd1—O6—Gd1ⁱⁱ	−126.89 (17)	C21—C14—N3—C26	0.6 (10)
N1ⁱⁱⁱ—Gd1—O6—Gd1ⁱⁱ	−66.37 (14)	C30—N2—C25—C9	−0.6 (9)
C5—Gd1—O6—Gd1ⁱⁱ	−135.7 (3)	C20—C9—C25—N2	−0.5 (9)
Gd1—O5—C5—O6	16.6 (4)	C11—C9—C25—N2	178.4 (6)
Gd1—O5—C5—C18	−161.1 (4)	C14—N3—C26—C29	−0.3 (10)
Gd1ⁱⁱ—O6—C5—O5	105.1 (5)	C13—C23—C27—C15	1.1 (8)
Gd1—O6—C5—O5	−15.8 (4)	N1—C15—C27—C23	−0.5 (8)
Gd1ⁱⁱ—O6—C5—C18	−77.2 (5)	C14—C21—C28—C29	0.9 (9)
Gd1—O6—C5—C18	161.9 (4)	C10—C21—C28—C29	−177.2 (6)
Gd1ⁱⁱ—O6—C5—Gd1	120.9 (3)	N3—C26—C29—C28	0.4 (10)
O4ⁱ—Gd1—C5—O5	57.1 (6)	C21—C28—C29—C26	−0.6 (10)
O2ⁱ—Gd1—C5—O5	−162.7 (2)	C25—N2—C30—C22	1.6 (9)
O1—Gd1—C5—O5	−27.7 (3)	C20—C22—C30—N2	−1.5 (9)
O3—Gd1—C5—O5	−99.9 (3)	Gd1—O1—C33—O2	4.5 (7)
O6ⁱⁱ—Gd1—C5—O5	123.9 (3)	Gd1—O1—C33—C12	−175.5 (3)
O6—Gd1—C5—O5	164.0 (4)	Gd1ⁱ—O2—C33—O1	−7.7 (18)
N1ⁱⁱⁱ—Gd1—C5—O5	51.5 (3)	Gd1ⁱ—O2—C33—C12	172.4 (12)
O4ⁱ—Gd1—C5—O6	−106.9 (5)	C7—C12—C33—O1	15.5 (7)
O2ⁱ—Gd1—C5—O6	33.3 (3)	C7—C12—C33—O2	−164.5 (5)
O1—Gd1—C5—O6	168.3 (2)	C15—N1—C34—C13	0.7 (7)
O3—Gd1—C5—O6	96.1 (2)	Gd1ⁱⁱⁱ—N1—C34—C13	−177.6 (4)
O6ⁱⁱ—Gd1—C5—O6	−40.1 (3)	C23—C13—C34—N1	−0.1 (8)
O5—Gd1—C5—O6	−164.0 (4)	C7—C13—C34—N1	−179.9 (5)
N1ⁱⁱⁱ—Gd1—C5—O6	−112.5 (2)

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

Experimental details

Crystal data
Chemical formula	[Gd(C₈H₆NO₂)₃]
M_r	601.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.7197 (17), 25.646 (6), 11.445 (2)
β (°)	95.684 (3)
V (Å³)	2254.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.99
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.534, 0.615
No. of measured, independent and observed [I > 2σ(I)] reflections	12572, 4654, 3517
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.090, 1.06
No. of reflections	4654
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.06, −1.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Gd1—O4ⁱ	2.305 (3)	Gd1—O6ⁱⁱ	2.383 (3)
Gd1—O2ⁱ	2.305 (3)	Gd1—O5	2.440 (3)
Gd1—O1	2.332 (3)	Gd1—O6	2.546 (3)
Gd1—O3	2.353 (3)	Gd1—N1ⁱⁱⁱ	2.628 (4)

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

Acknowledgements

This work was supported by the Natural Science Foundation of Guangxi (GKJ0639031), People's Republic of China.

References

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