Tetra­kis(μ-2-phen­oxy­propionato)-κ3O,O′:O′;κ3O:O,O′,κ4O:O′-bis­[(1,10-phenanthroline-κ2N,N′)(2-phen­oxy­propionato-κ2O,O′)dysprosium(III)]

Shen, J.-B.; Liu, J.-L.; Zhao, G.-L.

doi:10.1107/S1600536811034696

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1320

doi:10.1107/S1600536811034696

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Tetrakis(μ-2-phenoxypropionato)-κ³O,O′:O′;κ³O:O,O′,κ⁴O:O′-bis[(1,10-phenanthroline-κ²N,N′)(2-phenoxypropionato-κ²O,O′)dysprosium(III)]

Jin-Bei Shen,^a Jia-Lu Liu ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 14 August 2011; accepted 24 August 2011; online 31 August 2011)

In the centrosymmetric binuclear title complex, [Dy₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂], the two Dy^III ions are linked by four 2-phenoxypropionate (L) groups through their bi- and tridentate bridging modes. Each Dy^III ion is nine-coordinated by one 1,10-phenanthroline molecule, one bidentate carboxylate group and four bridging carboxylate groups in a distorted DyN₂O₇ monocapped square-antiprismatic geometry. The title compound is isotypic with its terbium-containing analogue.

Related literature

For the terbium analogue of the title compound, see: Shen et al. (2011 ). For a related structure, see: Liu et al. (2010 ).

Experimental

Crystal data

[Dy₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]
M_r = 1676.38
Monoclinic, P 2₁ /c
a = 11.4738 (1) Å
b = 25.8057 (3) Å
c = 13.8525 (2) Å
β = 120.657 (1)°
V = 3528.32 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.18 mm⁻¹
T = 296 K
0.32 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.710, T_max = 0.840
47810 measured reflections
6224 independent reflections
5057 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.053
S = 1.05
6224 reflections
463 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Selected bond lengths (Å)

Dy1—O8ⁱ	2.3252 (18)
Dy1—O4	2.3328 (18)
Dy1—O5ⁱ	2.3731 (19)
Dy1—O1	2.412 (2)
Dy1—O7	2.4421 (19)
Dy1—O2	2.462 (2)
Dy1—N2	2.518 (2)
Dy1—N1	2.594 (2)
Dy1—O8	2.622 (2)
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034696/hb6365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034696/hb6365Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of 2-phenoxypropionic acid complexes (Shen et al., 2011) we describe a new Dy^III complex.

The structure of the title compound (1) is a dinuclear dysprosium complex with Dy—Dy separation of 3.9857 (3) Å. The structure of the complex (Fig. 1) reveals that the molecule contains six L, two phen molecules and two Dy^III ions. Each Dy(III) ion is coordinated to nine atoms, of which five oxygen atoms are from the bridging carboxylates, two oxygen atoms from the bidentate chelating carboxylate group, and two nitrogen atoms from a 1,10- phenanthroline molecule. The L ligands are coordinated to the Dy^III ions in three different modes: chelating,bridging and bridging tridentate.The analysis of structural features indicates that the central Dy(III) ion adopts a distorted monocapped square antiprism geometry(Fig. 2).The Dy—O distances are all within the range 2.3252 (18)–2.622 (2) Å, and the Dy—N distances rang from 2.518 (2)–2.594 (2) Å, all of which are within the range of those of other nine-coordinated Dy^III complexes with carboxylic donor ligands and 1,10- phenanthroline (Liu et al., 2010). The selected bond lengths and angles for complex 1 are listed in Table 1. In addition, there are no classical hydrogen bonds in the crystal structure, because good hydrogen bond donors are absent. The most significant intermolecular interactions are C—H···O hydrogen bonds (Table 2) and weak π···π aromatic interactions from phen molecules and aromatic rings of the L ligands.

Related literature top

For the terbium analogue of the title compound, see: Shen et al. (2011). For a related structure, see: Liu et al. (2010).

Experimental top

Reagents and solvents used were of commercially available quality and without purified before using. 2-phenoxypropionic acid (1.5 mmol), Dy(NO₃)₃.5H₂O (0.5 mmol) and 1,10-phenanthroline (0.5 mmol) were dissolved in 20 ml e nthanol, then 10 ml water was added to the above solution. The mixed solution was stirred for 12 h at room temperature. At last, deposit was filtered out and the colourless solution was kept in the open air. Colourless blocks of (I) were obtained after several days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The coordination environment of the Dy(III) ion.

Tetrakis(µ-2-phenoxypropionato)-κ³O,O':O'; κ³O:O,O',κ⁴O:O'- bis[(1,10-phenanthroline-κ²N,N')(2- phenoxypropionato-κ²O,O')dysprosium(III)] top

Crystal data top

[Dy₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]	F(000) = 1684
M_r = 1676.38	D_x = 1.578 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9890 reflections
a = 11.4738 (1) Å	θ = 1.6–25.0°
b = 25.8057 (3) Å	µ = 2.18 mm⁻¹
c = 13.8525 (2) Å	T = 296 K
β = 120.657 (1)°	Block, colourless
V = 3528.32 (7) Å³	0.32 × 0.14 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	6224 independent reflections
Radiation source: fine-focus sealed tube	5057 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.710, T_max = 0.840	k = −30→30
47810 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.053	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0204P)² + 2.0937P] where P = (F_o² + 2F_c²)/3
6224 reflections	(Δ/σ)_max = 0.002
463 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

[Dy₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]	V = 3528.32 (7) Å³
M_r = 1676.38	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4738 (1) Å	µ = 2.18 mm⁻¹
b = 25.8057 (3) Å	T = 296 K
c = 13.8525 (2) Å	0.32 × 0.14 × 0.08 mm
β = 120.657 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6224 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5057 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.840	R_int = 0.043
47810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.053	H-atom parameters constrained
S = 1.05	Δρ_max = 0.76 e Å⁻³
6224 reflections	Δρ_min = −0.49 e Å⁻³
463 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
Dy1	0.453434 (12)	0.502684 (5)	0.840438 (10)	0.02670 (5)
O1	0.6186 (2)	0.51253 (8)	0.78321 (18)	0.0434 (5)
O2	0.5317 (2)	0.58487 (8)	0.80244 (17)	0.0396 (5)
O3	0.5945 (2)	0.63358 (8)	0.65590 (18)	0.0525 (6)
O4	0.5818 (2)	0.43014 (7)	0.93621 (16)	0.0378 (5)
O6	0.8286 (2)	0.34859 (9)	1.15437 (19)	0.0545 (6)
O7	0.24603 (19)	0.45817 (7)	0.80147 (15)	0.0351 (5)
O8	0.38341 (19)	0.46859 (7)	0.98205 (15)	0.0347 (5)
O9	0.0919 (2)	0.38935 (8)	0.84166 (18)	0.0428 (5)
N1	0.3810 (2)	0.43228 (9)	0.68656 (19)	0.0324 (6)
N2	0.2821 (2)	0.53041 (9)	0.64369 (19)	0.0327 (6)
C1	0.6015 (3)	0.56069 (13)	0.7717 (2)	0.0366 (7)
C2	0.6729 (3)	0.59088 (13)	0.7208 (3)	0.0461 (8)
H2A	0.6912	0.5677	0.6741	0.055*
C3	0.8052 (4)	0.61361 (16)	0.8136 (3)	0.0701 (12)
H3A	0.8499	0.6317	0.7810	0.105*
H3B	0.8626	0.5862	0.8607	0.105*
H3C	0.7867	0.6373	0.8576	0.105*
C4	0.4858 (3)	0.62449 (13)	0.5497 (3)	0.0445 (8)
C5	0.4495 (4)	0.57701 (14)	0.4988 (3)	0.0523 (9)
H5A	0.4959	0.5473	0.5373	0.063*
C6	0.3424 (4)	0.57372 (17)	0.3886 (3)	0.0648 (11)
H6A	0.3185	0.5417	0.3527	0.078*
C7	0.2717 (4)	0.6172 (2)	0.3327 (3)	0.0696 (12)
H7A	0.1996	0.6148	0.2593	0.084*
C8	0.3082 (4)	0.66421 (18)	0.3855 (4)	0.0695 (12)
H8A	0.2607	0.6938	0.3474	0.083*
C9	0.4138 (4)	0.66828 (14)	0.4940 (3)	0.0570 (10)
H9A	0.4369	0.7003	0.5297	0.068*
C10	0.6565 (3)	0.41422 (10)	1.0358 (2)	0.0310 (7)
C11	0.7397 (3)	0.36640 (12)	1.0443 (3)	0.0409 (8)
H11A	0.6765	0.3383	1.0024	0.049*
C12	0.8235 (4)	0.37670 (15)	0.9910 (3)	0.0615 (10)
H12A	0.8721	0.3458	0.9941	0.092*
H12B	0.8868	0.4041	1.0309	0.092*
H12C	0.7653	0.3867	0.9142	0.092*
C13	0.7780 (4)	0.31777 (12)	1.2062 (3)	0.0483 (9)
C14	0.6469 (4)	0.31529 (13)	1.1806 (3)	0.0580 (10)
H14A	0.5802	0.3334	1.1192	0.070*
C15	0.6133 (5)	0.28599 (16)	1.2454 (5)	0.0848 (14)
H15A	0.5238	0.2845	1.2282	0.102*
C16	0.7106 (8)	0.25915 (19)	1.3345 (5)	0.1028 (19)
H16A	0.6872	0.2396	1.3785	0.123*
C17	0.8423 (7)	0.26066 (17)	1.3603 (4)	0.0971 (18)
H17A	0.9079	0.2415	1.4204	0.117*
C18	0.8778 (4)	0.29032 (14)	1.2974 (3)	0.0677 (12)
H18A	0.9677	0.2921	1.3155	0.081*
C19	0.2736 (3)	0.45226 (10)	0.9000 (2)	0.0284 (6)
C20	0.1737 (3)	0.42670 (11)	0.9256 (2)	0.0351 (7)
H20A	0.2227	0.4098	0.9992	0.042*
C21	0.0777 (3)	0.46674 (14)	0.9259 (3)	0.0513 (9)
H21A	0.0140	0.4502	0.9412	0.077*
H21B	0.0300	0.4833	0.8538	0.077*
H21C	0.1283	0.4922	0.9827	0.077*
C22	0.1558 (3)	0.34625 (12)	0.8335 (3)	0.0464 (9)
C23	0.0787 (4)	0.31532 (14)	0.7417 (3)	0.0624 (11)
H23A	−0.0101	0.3246	0.6897	0.075*
C24	0.1336 (5)	0.27023 (16)	0.7269 (4)	0.0831 (14)
H24A	0.0814	0.2494	0.6645	0.100*
C25	0.2633 (5)	0.25611 (16)	0.8029 (4)	0.0919 (16)
H25A	0.3003	0.2260	0.7925	0.110*
C26	0.3375 (5)	0.28667 (17)	0.8938 (5)	0.1056 (19)
H26A	0.4250	0.2766	0.9472	0.127*
C27	0.2861 (4)	0.33248 (15)	0.9089 (4)	0.0812 (15)
H27A	0.3400	0.3537	0.9700	0.097*
C28	0.4289 (3)	0.38448 (12)	0.7054 (3)	0.0426 (8)
H28A	0.5034	0.3769	0.7756	0.051*
C29	0.3745 (4)	0.34462 (13)	0.6264 (3)	0.0553 (10)
H29A	0.4127	0.3117	0.6436	0.066*
C30	0.2646 (3)	0.35470 (13)	0.5238 (3)	0.0503 (9)
H30A	0.2263	0.3285	0.4704	0.060*
C31	0.0942 (3)	0.41847 (14)	0.3935 (3)	0.0485 (9)
H31A	0.0510	0.3931	0.3388	0.058*
C32	0.0467 (3)	0.46716 (14)	0.3716 (3)	0.0454 (8)
H32A	−0.0284	0.4749	0.3020	0.055*
C33	0.0656 (3)	0.55867 (13)	0.4337 (3)	0.0433 (8)
H33A	−0.0074	0.5684	0.3645	0.052*
C34	0.1306 (3)	0.59444 (13)	0.5165 (3)	0.0447 (8)
H34A	0.1040	0.6290	0.5040	0.054*
C35	0.2374 (3)	0.57857 (12)	0.6203 (2)	0.0383 (7)
H35A	0.2798	0.6034	0.6765	0.046*
C36	0.2097 (3)	0.40457 (12)	0.4990 (3)	0.0398 (8)
C37	0.2721 (3)	0.44260 (11)	0.5833 (2)	0.0313 (7)
C38	0.1095 (3)	0.50737 (12)	0.4535 (2)	0.0368 (7)
C39	0.2203 (3)	0.49463 (11)	0.5605 (2)	0.0316 (7)
O5	0.66605 (19)	0.43284 (7)	1.12245 (15)	0.0339 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.02533 (8)	0.02954 (8)	0.02117 (7)	0.00035 (6)	0.00892 (6)	0.00075 (6)
O1	0.0494 (14)	0.0361 (13)	0.0527 (14)	0.0023 (10)	0.0320 (12)	0.0056 (10)
O2	0.0366 (13)	0.0382 (12)	0.0437 (13)	−0.0001 (10)	0.0202 (11)	0.0038 (10)
O3	0.0620 (16)	0.0452 (14)	0.0407 (13)	−0.0113 (11)	0.0193 (12)	0.0073 (10)
O4	0.0455 (13)	0.0359 (11)	0.0262 (11)	0.0119 (10)	0.0140 (10)	0.0033 (9)
O6	0.0462 (15)	0.0519 (14)	0.0520 (15)	0.0093 (11)	0.0153 (12)	0.0090 (11)
O7	0.0322 (12)	0.0440 (12)	0.0247 (11)	−0.0062 (9)	0.0114 (9)	−0.0027 (9)
O8	0.0288 (11)	0.0389 (12)	0.0263 (11)	−0.0038 (9)	0.0067 (9)	−0.0005 (9)
O9	0.0275 (12)	0.0396 (13)	0.0488 (13)	−0.0041 (10)	0.0105 (10)	0.0008 (10)
N1	0.0328 (14)	0.0361 (14)	0.0268 (13)	0.0017 (11)	0.0140 (11)	0.0000 (10)
N2	0.0316 (14)	0.0359 (14)	0.0276 (13)	−0.0011 (11)	0.0128 (11)	0.0004 (11)
C1	0.0288 (17)	0.049 (2)	0.0237 (16)	−0.0053 (15)	0.0078 (14)	0.0047 (14)
C2	0.046 (2)	0.051 (2)	0.0406 (19)	−0.0046 (16)	0.0222 (17)	0.0091 (16)
C3	0.046 (2)	0.101 (3)	0.052 (2)	−0.023 (2)	0.0169 (19)	0.016 (2)
C4	0.048 (2)	0.052 (2)	0.0347 (18)	−0.0060 (16)	0.0219 (17)	0.0071 (15)
C5	0.054 (2)	0.055 (2)	0.045 (2)	0.0009 (18)	0.0238 (18)	0.0013 (17)
C6	0.060 (3)	0.083 (3)	0.050 (2)	−0.010 (2)	0.027 (2)	−0.019 (2)
C7	0.049 (2)	0.117 (4)	0.039 (2)	−0.002 (3)	0.0195 (19)	0.009 (2)
C8	0.056 (3)	0.081 (3)	0.066 (3)	0.008 (2)	0.027 (2)	0.030 (2)
C9	0.061 (3)	0.050 (2)	0.061 (2)	−0.0015 (18)	0.031 (2)	0.0117 (18)
C10	0.0313 (17)	0.0276 (15)	0.0307 (17)	−0.0014 (12)	0.0133 (14)	0.0010 (12)
C11	0.0383 (19)	0.0416 (18)	0.0350 (17)	0.0110 (14)	0.0130 (15)	0.0021 (14)
C12	0.050 (2)	0.071 (3)	0.069 (3)	0.0174 (19)	0.035 (2)	0.007 (2)
C13	0.064 (3)	0.0311 (18)	0.051 (2)	0.0070 (17)	0.031 (2)	0.0046 (15)
C14	0.065 (3)	0.038 (2)	0.069 (3)	0.0000 (18)	0.033 (2)	0.0031 (18)
C15	0.108 (4)	0.052 (3)	0.124 (4)	−0.005 (3)	0.081 (4)	−0.003 (3)
C16	0.183 (7)	0.060 (3)	0.101 (4)	0.001 (4)	0.098 (5)	0.013 (3)
C17	0.144 (5)	0.059 (3)	0.053 (3)	0.004 (3)	0.025 (3)	0.018 (2)
C18	0.073 (3)	0.041 (2)	0.064 (3)	0.0025 (19)	0.016 (2)	0.0033 (19)
C19	0.0257 (16)	0.0265 (15)	0.0291 (16)	0.0027 (12)	0.0113 (14)	−0.0003 (12)
C20	0.0312 (17)	0.0406 (17)	0.0306 (16)	−0.0025 (14)	0.0137 (14)	0.0023 (13)
C21	0.047 (2)	0.063 (2)	0.058 (2)	0.0026 (18)	0.0369 (19)	0.0013 (18)
C22	0.038 (2)	0.0361 (18)	0.054 (2)	−0.0052 (15)	0.0153 (17)	0.0058 (15)
C23	0.057 (2)	0.055 (2)	0.058 (2)	−0.0035 (19)	0.017 (2)	−0.0062 (19)
C24	0.094 (4)	0.054 (3)	0.075 (3)	−0.009 (2)	0.024 (3)	−0.019 (2)
C25	0.092 (4)	0.049 (3)	0.111 (4)	0.009 (2)	0.034 (3)	−0.019 (3)
C26	0.075 (3)	0.058 (3)	0.130 (4)	0.022 (2)	0.013 (3)	−0.020 (3)
C27	0.055 (3)	0.048 (2)	0.091 (3)	0.0095 (19)	0.001 (2)	−0.016 (2)
C28	0.044 (2)	0.0434 (19)	0.0331 (17)	0.0058 (15)	0.0142 (15)	−0.0015 (14)
C29	0.067 (3)	0.0393 (19)	0.056 (2)	0.0042 (17)	0.029 (2)	−0.0084 (16)
C30	0.055 (2)	0.048 (2)	0.043 (2)	−0.0107 (17)	0.0217 (18)	−0.0172 (16)
C31	0.047 (2)	0.063 (2)	0.0309 (18)	−0.0149 (18)	0.0162 (16)	−0.0160 (16)
C32	0.039 (2)	0.067 (2)	0.0246 (17)	−0.0079 (17)	0.0119 (15)	−0.0001 (16)
C33	0.0367 (19)	0.057 (2)	0.0293 (17)	0.0050 (16)	0.0117 (15)	0.0118 (15)
C34	0.045 (2)	0.047 (2)	0.0380 (18)	0.0113 (16)	0.0185 (16)	0.0110 (15)
C35	0.0413 (19)	0.0390 (18)	0.0293 (16)	0.0033 (14)	0.0142 (15)	0.0022 (13)
C36	0.0402 (19)	0.0454 (19)	0.0343 (17)	−0.0115 (15)	0.0194 (15)	−0.0095 (14)
C37	0.0316 (17)	0.0387 (17)	0.0282 (16)	−0.0058 (13)	0.0185 (14)	−0.0044 (13)
C38	0.0293 (16)	0.055 (2)	0.0247 (15)	−0.0046 (14)	0.0127 (13)	0.0020 (14)
C39	0.0297 (16)	0.0407 (17)	0.0253 (14)	−0.0014 (13)	0.0148 (13)	0.0027 (13)
O5	0.0376 (12)	0.0351 (11)	0.0260 (11)	0.0050 (9)	0.0141 (9)	0.0009 (9)

Geometric parameters (Å, º) top

Dy1—O8ⁱ	2.3252 (18)	C13—C14	1.359 (5)
Dy1—O4	2.3328 (18)	C13—C18	1.391 (5)
Dy1—O5ⁱ	2.3731 (19)	C14—C15	1.370 (5)
Dy1—O1	2.412 (2)	C14—H14A	0.9300
Dy1—O7	2.4421 (19)	C15—C16	1.358 (7)
Dy1—O2	2.462 (2)	C15—H15A	0.9300
Dy1—N2	2.518 (2)	C16—C17	1.365 (7)
Dy1—N1	2.594 (2)	C16—H16A	0.9300
Dy1—O8	2.622 (2)	C17—C18	1.368 (6)
Dy1—Dy1ⁱ	3.9857 (3)	C17—H17A	0.9300
O1—C1	1.256 (4)	C18—H18A	0.9300
O2—C1	1.249 (4)	C19—C20	1.514 (4)
O3—C4	1.379 (4)	C20—C21	1.511 (4)
O3—C2	1.417 (4)	C20—H20A	0.9800
O4—C10	1.265 (3)	C21—H21A	0.9600
O6—C13	1.382 (4)	C21—H21B	0.9600
O6—C11	1.411 (4)	C21—H21C	0.9600
O7—C19	1.243 (3)	C22—C27	1.364 (5)
O8—C19	1.263 (3)	C22—C23	1.375 (5)
O8—Dy1ⁱ	2.3252 (18)	C23—C24	1.388 (5)
O9—C22	1.368 (4)	C23—H23A	0.9300
O9—C20	1.431 (3)	C24—C25	1.364 (6)
N1—C28	1.321 (4)	C24—H24A	0.9300
N1—C37	1.362 (3)	C25—C26	1.356 (6)
N2—C35	1.320 (4)	C25—H25A	0.9300
N2—C39	1.360 (4)	C26—C27	1.384 (5)
C1—C2	1.537 (4)	C26—H26A	0.9300
C2—C3	1.520 (5)	C27—H27A	0.9300
C2—H2A	0.9800	C28—C29	1.396 (4)
C3—H3A	0.9600	C28—H28A	0.9300
C3—H3B	0.9600	C29—C30	1.360 (5)
C3—H3C	0.9600	C29—H29A	0.9300
C4—C5	1.369 (5)	C30—C36	1.397 (4)
C4—C9	1.380 (5)	C30—H30A	0.9300
C5—C6	1.391 (5)	C31—C32	1.341 (5)
C5—H5A	0.9300	C31—C36	1.430 (4)
C6—C7	1.370 (5)	C31—H31A	0.9300
C6—H6A	0.9300	C32—C38	1.432 (4)
C7—C8	1.368 (6)	C32—H32A	0.9300
C7—H7A	0.9300	C33—C34	1.361 (4)
C8—C9	1.371 (5)	C33—C38	1.393 (4)
C8—H8A	0.9300	C33—H33A	0.9300
C9—H9A	0.9300	C34—C35	1.393 (4)
C10—O5	1.245 (3)	C34—H34A	0.9300
C10—C11	1.528 (4)	C35—H35A	0.9300
C11—C12	1.504 (5)	C36—C37	1.410 (4)
C11—H11A	0.9800	C37—C39	1.437 (4)
C12—H12A	0.9600	C38—C39	1.414 (4)
C12—H12B	0.9600	O5—Dy1ⁱ	2.3731 (19)
C12—H12C	0.9600

O8ⁱ—Dy1—O4	73.74 (7)	C7—C8—C9	120.9 (4)
O8ⁱ—Dy1—O5ⁱ	77.87 (7)	C7—C8—H8A	119.6
O4—Dy1—O5ⁱ	134.95 (7)	C9—C8—H8A	119.6
O8ⁱ—Dy1—O1	88.29 (7)	C8—C9—C4	119.5 (4)
O4—Dy1—O1	84.10 (7)	C8—C9—H9A	120.2
O5ⁱ—Dy1—O1	129.42 (7)	C4—C9—H9A	120.2
O8ⁱ—Dy1—O7	123.51 (7)	O5—C10—O4	127.1 (3)
O4—Dy1—O7	90.56 (7)	O5—C10—C11	119.5 (2)
O5ⁱ—Dy1—O7	76.83 (7)	O4—C10—C11	113.3 (3)
O1—Dy1—O7	144.82 (7)	O6—C11—C12	107.3 (3)
O8ⁱ—Dy1—O2	76.51 (7)	O6—C11—C10	115.2 (3)
O4—Dy1—O2	128.28 (7)	C12—C11—C10	110.5 (3)
O5ⁱ—Dy1—O2	75.89 (7)	O6—C11—H11A	107.9
O1—Dy1—O2	53.54 (7)	C12—C11—H11A	107.9
O7—Dy1—O2	141.10 (7)	C10—C11—H11A	107.9
O8ⁱ—Dy1—N2	144.82 (7)	C11—C12—H12A	109.5
O4—Dy1—N2	139.62 (7)	C11—C12—H12B	109.5
O5ⁱ—Dy1—N2	79.44 (7)	H12A—C12—H12B	109.5
O1—Dy1—N2	85.71 (8)	C11—C12—H12C	109.5
O7—Dy1—N2	76.07 (7)	H12A—C12—H12C	109.5
O2—Dy1—N2	72.09 (7)	H12B—C12—H12C	109.5
O8ⁱ—Dy1—N1	147.16 (7)	C14—C13—O6	126.4 (3)
O4—Dy1—N1	75.53 (7)	C14—C13—C18	120.1 (4)
O5ⁱ—Dy1—N1	133.69 (7)	O6—C13—C18	113.3 (4)
O1—Dy1—N1	77.28 (7)	C13—C14—C15	119.9 (4)
O7—Dy1—N1	67.74 (7)	C13—C14—H14A	120.1
O2—Dy1—N1	115.25 (7)	C15—C14—H14A	120.1
N2—Dy1—N1	64.11 (7)	C16—C15—C14	120.1 (5)
O8ⁱ—Dy1—O8	72.80 (7)	C16—C15—H15A	119.9
O4—Dy1—O8	69.56 (7)	C14—C15—H15A	119.9
O5ⁱ—Dy1—O8	69.02 (6)	C15—C16—C17	120.6 (5)
O1—Dy1—O8	150.83 (7)	C15—C16—H16A	119.7
O7—Dy1—O8	51.08 (6)	C17—C16—H16A	119.7
O2—Dy1—O8	137.15 (7)	C16—C17—C18	119.9 (5)
N2—Dy1—O8	122.48 (7)	C16—C17—H17A	120.0
N1—Dy1—O8	106.73 (7)	C18—C17—H17A	120.0
O8ⁱ—Dy1—C1	83.52 (8)	C17—C18—C13	119.3 (5)
O4—Dy1—C1	107.99 (9)	C17—C18—H18A	120.4
O5ⁱ—Dy1—C1	102.64 (9)	C13—C18—H18A	120.4
O1—Dy1—C1	26.90 (8)	O7—C19—O8	121.7 (3)
O7—Dy1—C1	151.28 (7)	O7—C19—C20	120.8 (2)
O2—Dy1—C1	26.79 (8)	O8—C19—C20	117.5 (2)
N2—Dy1—C1	75.64 (8)	O7—C19—Dy1	56.71 (14)
N1—Dy1—C1	95.25 (9)	O8—C19—Dy1	65.02 (15)
O8—Dy1—C1	155.99 (7)	C20—C19—Dy1	177.16 (19)
O8ⁱ—Dy1—C19	98.53 (7)	O9—C20—C21	106.6 (2)
O4—Dy1—C19	79.17 (7)	O9—C20—C19	111.3 (2)
O5ⁱ—Dy1—C19	71.26 (7)	C21—C20—C19	110.0 (2)
O1—Dy1—C19	159.31 (7)	O9—C20—H20A	109.6
O7—Dy1—C19	25.19 (7)	C21—C20—H20A	109.6
O2—Dy1—C19	147.06 (7)	C19—C20—H20A	109.6
N2—Dy1—C19	99.19 (8)	C20—C21—H21A	109.5
N1—Dy1—C19	86.74 (8)	C20—C21—H21B	109.5
O8—Dy1—C19	25.89 (6)	H21A—C21—H21B	109.5
C1—Dy1—C19	172.83 (9)	C20—C21—H21C	109.5
O8ⁱ—Dy1—Dy1ⁱ	38.94 (5)	H21A—C21—H21C	109.5
O4—Dy1—Dy1ⁱ	66.85 (5)	H21B—C21—H21C	109.5
O5ⁱ—Dy1—Dy1ⁱ	69.01 (4)	C27—C22—O9	125.0 (3)
O1—Dy1—Dy1ⁱ	123.85 (5)	C27—C22—C23	119.6 (3)
O7—Dy1—Dy1ⁱ	84.77 (4)	O9—C22—C23	115.4 (3)
O2—Dy1—Dy1ⁱ	110.26 (5)	C22—C23—C24	119.8 (4)
N2—Dy1—Dy1ⁱ	146.11 (6)	C22—C23—H23A	120.1
N1—Dy1—Dy1ⁱ	132.80 (5)	C24—C23—H23A	120.1
O8—Dy1—Dy1ⁱ	33.87 (4)	C25—C24—C23	120.6 (4)
C1—Dy1—Dy1ⁱ	122.35 (6)	C25—C24—H24A	119.7
C19—Dy1—Dy1ⁱ	59.65 (5)	C23—C24—H24A	119.7
C1—O1—Dy1	92.75 (19)	C26—C25—C24	118.9 (4)
C1—O2—Dy1	90.56 (18)	C26—C25—H25A	120.6
C4—O3—C2	118.7 (3)	C24—C25—H25A	120.6
C10—O4—Dy1	139.55 (18)	C25—C26—C27	121.5 (4)
C13—O6—C11	119.1 (3)	C25—C26—H26A	119.2
C19—O7—Dy1	98.10 (16)	C27—C26—H26A	119.2
C19—O8—Dy1ⁱ	162.47 (19)	C22—C27—C26	119.5 (4)
C19—O8—Dy1	89.09 (16)	C22—C27—H27A	120.3
Dy1ⁱ—O8—Dy1	107.20 (7)	C26—C27—H27A	120.3
C22—O9—C20	117.3 (2)	N1—C28—C29	123.9 (3)
C28—N1—C37	117.2 (3)	N1—C28—H28A	118.0
C28—N1—Dy1	124.38 (19)	C29—C28—H28A	118.0
C37—N1—Dy1	117.64 (18)	C30—C29—C28	119.0 (3)
C35—N2—C39	117.5 (2)	C30—C29—H29A	120.5
C35—N2—Dy1	121.60 (19)	C28—C29—H29A	120.5
C39—N2—Dy1	120.41 (18)	C29—C30—C36	119.7 (3)
O2—C1—O1	122.5 (3)	C29—C30—H30A	120.2
O2—C1—C2	119.2 (3)	C36—C30—H30A	120.2
O1—C1—C2	118.3 (3)	C32—C31—C36	121.6 (3)
O2—C1—Dy1	62.65 (16)	C32—C31—H31A	119.2
O1—C1—Dy1	60.35 (16)	C36—C31—H31A	119.2
C2—C1—Dy1	173.9 (2)	C31—C32—C38	121.1 (3)
O3—C2—C3	105.9 (3)	C31—C32—H32A	119.4
O3—C2—C1	111.8 (3)	C38—C32—H32A	119.4
C3—C2—C1	110.1 (3)	C34—C33—C38	119.4 (3)
O3—C2—H2A	109.7	C34—C33—H33A	120.3
C3—C2—H2A	109.7	C38—C33—H33A	120.3
C1—C2—H2A	109.7	C33—C34—C35	119.1 (3)
C2—C3—H3A	109.5	C33—C34—H34A	120.5
C2—C3—H3B	109.5	C35—C34—H34A	120.5
H3A—C3—H3B	109.5	N2—C35—C34	123.9 (3)
C2—C3—H3C	109.5	N2—C35—H35A	118.1
H3A—C3—H3C	109.5	C34—C35—H35A	118.1
H3B—C3—H3C	109.5	C30—C36—C37	117.6 (3)
C5—C4—O3	125.0 (3)	C30—C36—C31	123.3 (3)
C5—C4—C9	120.4 (3)	C37—C36—C31	119.1 (3)
O3—C4—C9	114.5 (3)	N1—C37—C36	122.7 (3)
C4—C5—C6	119.1 (3)	N1—C37—C39	117.9 (2)
C4—C5—H5A	120.4	C36—C37—C39	119.4 (3)
C6—C5—H5A	120.4	C33—C38—C39	118.0 (3)
C7—C6—C5	120.5 (4)	C33—C38—C32	123.2 (3)
C7—C6—H6A	119.7	C39—C38—C32	118.9 (3)
C5—C6—H6A	119.7	N2—C39—C38	122.1 (3)
C8—C7—C6	119.5 (4)	N2—C39—C37	118.0 (2)
C8—C7—H7A	120.3	C38—C39—C37	119.8 (3)
C6—C7—H7A	120.3	C10—O5—Dy1ⁱ	134.66 (18)

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Dy₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]
M_r	1676.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4738 (1), 25.8057 (3), 13.8525 (2)
β (°)	120.657 (1)
V (Å³)	3528.32 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.18
Crystal size (mm)	0.32 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.710, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	47810, 6224, 5057
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.053, 1.05
No. of reflections	6224
No. of parameters	463
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.49

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Dy1—O8ⁱ	2.3252 (18)	Dy1—O2	2.462 (2)
Dy1—O4	2.3328 (18)	Dy1—N2	2.518 (2)
Dy1—O5ⁱ	2.3731 (19)	Dy1—N1	2.594 (2)
Dy1—O1	2.412 (2)	Dy1—O8	2.622 (2)
Dy1—O7	2.4421 (19)

Symmetry code: (i) −x+1, −y+1, −z+2.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, J.-F., Xu, X.-D., Li, H.-Q. & Zhao, G.-L. (2010). Acta Cryst. E66, m291. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011). Acta Cryst. E67, m1234. Google Scholar

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Volume 67| Part 9| September 2011| Page m1320

doi:10.1107/S1600536811034696

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