Poly[μ4-glutarato-di-μ3-glutarato-bis­(1,10-phenanthroline)diyttrium(III)]

Jin, L.; Zhu, H.

doi:10.1107/S1600536811027188

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1088

doi:10.1107/S1600536811027188

Open

access

Poly[μ₄-glutarato-di-μ₃-glutarato-bis(1,10-phenanthroline)diyttrium(III)]

Ling Jin ^a and Hong-lin Zhu ^a ^*

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: Zhuhonglin1@nbu.edu.cn

(Received 16 June 2011; accepted 7 July 2011; online 13 July 2011)

In the title complex, [Y₂(C₅H₆O₄)₃(C₁₂H₈N₂)₂]_n, three glutarate groups and two 1,10-phenanthroline molecules surround the two Y^III ions. Both Y^III ions are coordinated by two N atoms from the 1,10-phenanthroline, seven O atoms from five glutarate groups in a distorted tricapped trigonal–prismatic geometry. The Y^III ions are bridged by glutarate ligands in three modes, forming a layered, polymeric structure. The resulting layers are assembled by π–π stacking interactions [centroid–centroid distances = 3.740 (3) and 3.571 (3) Å] into a three-dimensional supramolecular architecture.

Related literature

For general background to applications of coordination polymers as functional materials, see: Koo et al. (2010 ). For related structures, see: Zhang et al. (2003 ): Yin & Yu (2007 ).

Experimental

Crystal data

[Y₂(C₅H₆O₄)₃(C₁₂H₈N₂)₂]
M_r = 928.52
Triclinic, $[P \overline 1]$
a = 8.7681 (18) Å
b = 13.418 (3) Å
c = 16.410 (3) Å
α = 83.83 (3)°
β = 84.41 (3)°
γ = 75.09 (3)°
V = 1849.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 3.19 mm⁻¹
T = 293 K
0.23 × 0.17 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.790, T_max = 0.810
17986 measured reflections
8240 independent reflections
5620 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.076
S = 1.02
8240 reflections
514 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Y1—O2ⁱ	2.314 (2)
Y1—O1ⁱⁱ	2.314 (2)
Y1—O6ⁱⁱⁱ	2.315 (2)
Y1—O3	2.386 (2)
Y1—O5	2.441 (3)
Y1—O4	2.455 (3)
Y1—O6	2.537 (2)
Y1—N2	2.538 (3)
Y1—N1	2.592 (3)
Y2—O10^iv	2.269 (3)
Y2—O12^v	2.317 (2)
Y2—O11ⁱ	2.329 (2)
Y2—O7	2.375 (3)
Y2—O9	2.397 (3)
Y2—O8	2.413 (3)
Y2—N4	2.570 (3)
Y2—N3	2.649 (3)
Y2—O10	2.823 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1; (iii) -x+2, -y, -z+1; (iv) -x+2, -y+1, -z+2; (v) -x+1, -y+1, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027188/kp2336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027188/kp2336Isup2.hkl

checkCIF report

Comment top

In the past decades, growing attention has been paid to rational design and synthesis of coordination polymers due to their potential applications as functional materials (Koo et al., 2010). We report here the preparation and crystal structures of one interesting coordination polymers constructed by Yttrium(III) centers, 1,10-phenanthroline and glutarate, namely [Y₂(phen)₂(glu)₃]_n.

The asymmetric unit of the title compound contains two Y^III ions, two phen molecules and three glutarate anions. Both Y^III ions are coordinated by seven oxygen atoms from five glutarate ligands and two nitrogen atoms from a chelating phen ligand (Fig. 1). The Y-O/N bond distances fall in a range from 2.269 to 2.823 Å (Table 1). Each of Y^III ions exhibits the coordination geometry of distorted tricapped trigonal prism. The glutarate ligands exhibit three types of linking modes to bridge Y^III ions into the polymeric structure: (a) bridging bidentate and chelating bidentate; (b) chelating/bridging tridentate and bridging bidentate; (c) chelating/bridging tridentate and chelating bidentate (Zhang et al., 2003). The Y^III ions are bridged by glutarate anions to form layers parallel to (011) (Fig. 2). π–π stacking interactions of phen ligands with separation distances between centres of gravity of 3.740 (3)Å and 3.571 (3) Å [involving the rings: N1-C15-C14_C13_C12-C16 and C9-C10-C11-C12-C16-C17 with symmetry operation of the second ring (1-x,1-y,1-z), and the ring C26-C27-C28-C29-C33-C34 and its symmetry related one (3-x,-y,2-z)] generate a three-dimensional structure (Yin et al., 2007).

Related literature top

For general background to applications of coordination polymers as functional materials , see: Koo et al. (2010). For related structures, see: Zhang et al. (2003): Yin & Yu (2007).

Experimental top

YCl₃.nH₂O were prepared by dissolving 0.0339 g Y₂O₃ (0.15 mmol) in dilute hydrochloric acid and then dried. A mixture of YCl₃.nH₂O, H₂glu (0.0396 g, 0.30 mmol), phen (0.0595 g, 0.30 mmol) and H₂O (10 mL) was stirred and adjusted to pH 4.0 with a 1M NaOH solution, then transferred and sealed into an 23 mL-Teflon-lined autoclave, which was heated at 443 K for three days. After cooling to room temperature at a rate of 10 K /3 h, colourless block-like crystals were obtained, washed with ethanol and dried in air.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound. The dispalcement ellipsoids are drawn at the 30% probability level. [Symmetry codes used: (#1)-x + 1, -y, -z + 1;(#2)-x + 2, -y, -z + 1; (#3)x + 1, y, z;(#4)-x + 2, -y + 1, -z + 2;(#5)-x + 1, -y + 1, -z + 2].
	Fig. 2. The view of layered structure parallel to (011).

Poly[µ₄-glutarato-di-µ₃-glutarato-bis(1,10-phenanthroline)diyttrium(III)] top

Crystal data top

[Y₂(C₅H₆O₄)₃(C₁₂H₈N₂)₂]	Z = 2
M_r = 928.52	F(000) = 940
Triclinic, P1	D_x = 1.667 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7681 (18) Å	Cell parameters from 17986 reflections
b = 13.418 (3) Å	θ = 3.1–27.5°
c = 16.410 (3) Å	µ = 3.19 mm⁻¹
α = 83.83 (3)°	T = 293 K
β = 84.41 (3)°	Block, colorless
γ = 75.09 (3)°	0.23 × 0.17 × 0.08 mm
V = 1849.9 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	8240 independent reflections
Radiation source: fine-focus sealed tube	5620 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −10→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→17
T_min = 0.790, T_max = 0.810	l = −21→21
17986 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0145P)² + 1.8882P] where P = (F_o² + 2F_c²)/3
8240 reflections	(Δ/σ)_max = 0.001
514 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Y₂(C₅H₆O₄)₃(C₁₂H₈N₂)₂]	γ = 75.09 (3)°
M_r = 928.52	V = 1849.9 (6) Å³
Triclinic, P1	Z = 2
a = 8.7681 (18) Å	Mo Kα radiation
b = 13.418 (3) Å	µ = 3.19 mm⁻¹
c = 16.410 (3) Å	T = 293 K
α = 83.83 (3)°	0.23 × 0.17 × 0.08 mm
β = 84.41 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	8240 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5620 reflections with I > 2σ(I)
T_min = 0.790, T_max = 0.810	R_int = 0.056
17986 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
8240 reflections	Δρ_min = −0.43 e Å⁻³
514 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
Y1	0.86495 (3)	0.13918 (2)	0.47569 (2)	0.02109 (9)
Y2	1.08369 (4)	0.36263 (3)	0.95322 (2)	0.02321 (9)
O1	0.2367 (3)	−0.05407 (18)	0.40997 (15)	0.0315 (6)
O2	0.0995 (2)	0.11228 (18)	0.39369 (15)	0.0289 (6)
C1	0.2239 (4)	0.0409 (3)	0.3887 (2)	0.0235 (8)
C2	0.3754 (4)	0.0700 (3)	0.3574 (2)	0.0288 (8)
H2A	0.4246	0.0274	0.3132	0.035*
H2B	0.4465	0.0527	0.4014	0.035*
C3	0.3610 (4)	0.1817 (3)	0.3264 (2)	0.0301 (9)
H3A	0.3145	0.2255	0.3703	0.036*
H3B	0.2910	0.2002	0.2819	0.036*
C4	0.5215 (4)	0.2014 (3)	0.2958 (2)	0.0352 (9)
H4A	0.5637	0.1603	0.2498	0.042*
H4B	0.5054	0.2736	0.2754	0.042*
C5	0.6438 (4)	0.1773 (3)	0.3585 (2)	0.0289 (8)
O3	0.6014 (3)	0.1760 (2)	0.43423 (16)	0.0344 (6)
O4	0.7872 (3)	0.1615 (2)	0.33384 (16)	0.0381 (7)
C6	0.9464 (5)	0.3403 (3)	0.3483 (3)	0.0496 (12)
H6A	0.9873	0.2855	0.3158	0.059*
C7	0.9710 (5)	0.4368 (4)	0.3198 (3)	0.0716 (18)
H7A	1.0257	0.4459	0.2692	0.086*
C8	0.9139 (5)	0.5172 (4)	0.3667 (4)	0.0727 (18)
H8A	0.9322	0.5816	0.3492	0.087*
C9	0.8272 (5)	0.5034 (3)	0.4419 (3)	0.0506 (12)
C10	0.7514 (6)	0.5851 (3)	0.4922 (4)	0.0662 (15)
H10A	0.7674	0.6508	0.4780	0.079*
C11	0.6573 (6)	0.5693 (3)	0.5594 (3)	0.0636 (15)
H11A	0.6075	0.6245	0.5901	0.076*
C12	0.6328 (5)	0.4693 (3)	0.5841 (3)	0.0435 (10)
C13	0.5314 (5)	0.4493 (3)	0.6519 (3)	0.0529 (12)
H13A	0.4770	0.5028	0.6833	0.063*
C14	0.5121 (5)	0.3519 (3)	0.6718 (3)	0.0510 (12)
H14A	0.4435	0.3385	0.7160	0.061*
C15	0.5979 (4)	0.2725 (3)	0.6243 (2)	0.0381 (10)
H15A	0.5863	0.2058	0.6391	0.046*
C16	0.7104 (4)	0.3848 (3)	0.5381 (2)	0.0303 (9)
C17	0.8068 (4)	0.4031 (3)	0.4656 (3)	0.0352 (9)
N1	0.6947 (3)	0.2871 (2)	0.55945 (19)	0.0301 (7)
N2	0.8689 (3)	0.3220 (2)	0.41867 (19)	0.0334 (8)
O5	1.0269 (3)	0.19778 (18)	0.56407 (17)	0.0349 (6)
O6	1.0951 (3)	0.03082 (18)	0.55413 (15)	0.0283 (6)
C18	1.1170 (4)	0.1111 (3)	0.5808 (2)	0.0253 (8)
C19	1.2573 (4)	0.0989 (3)	0.6293 (2)	0.0327 (9)
H19A	1.3475	0.1038	0.5913	0.039*
H19B	1.2809	0.0300	0.6575	0.039*
C20	1.2400 (4)	0.1761 (3)	0.6919 (2)	0.0302 (8)
H20A	1.2121	0.2453	0.6645	0.036*
H20B	1.3413	0.1667	0.7146	0.036*
C21	1.1166 (4)	0.1671 (3)	0.7617 (2)	0.0391 (10)
H21A	1.0130	0.1869	0.7400	0.047*
H21B	1.1351	0.0953	0.7836	0.047*
C22	1.1154 (4)	0.2328 (3)	0.8310 (2)	0.0303 (8)
O7	1.0446 (3)	0.2144 (2)	0.89935 (16)	0.0391 (7)
O8	1.1848 (3)	0.30470 (19)	0.81974 (16)	0.0350 (6)
N3	1.1495 (3)	0.2053 (2)	1.06709 (19)	0.0322 (7)
N4	1.3751 (3)	0.2628 (2)	0.96125 (19)	0.0309 (7)
C23	1.4860 (4)	0.2898 (3)	0.9096 (3)	0.0397 (10)
H23A	1.4543	0.3431	0.8689	0.048*
C24	1.6475 (4)	0.2434 (3)	0.9121 (3)	0.0484 (12)
H24A	1.7211	0.2678	0.8762	0.058*
C25	1.6946 (4)	0.1624 (3)	0.9681 (3)	0.0482 (12)
H25A	1.8018	0.1304	0.9706	0.058*
C26	1.5831 (4)	0.1261 (3)	1.0222 (3)	0.0399 (10)
C27	1.6204 (5)	0.0371 (3)	1.0784 (3)	0.0488 (12)
H27A	1.7254	−0.0002	1.0809	0.059*
C28	1.5091 (5)	0.0050 (3)	1.1281 (3)	0.0505 (12)
H28A	1.5382	−0.0539	1.1641	0.061*
C29	1.3447 (5)	0.0601 (3)	1.1268 (3)	0.0393 (10)
C30	1.2247 (5)	0.0300 (3)	1.1789 (3)	0.0477 (11)
H30A	1.2485	−0.0291	1.2152	0.057*
C31	1.0733 (5)	0.0883 (3)	1.1757 (3)	0.0517 (12)
H31A	0.9926	0.0709	1.2109	0.062*
C32	1.0410 (5)	0.1744 (3)	1.1188 (3)	0.0453 (11)
H32A	0.9366	0.2129	1.1169	0.054*
C33	1.3023 (4)	0.1483 (3)	1.0723 (2)	0.0310 (9)
C34	1.4212 (4)	0.1816 (3)	1.0173 (2)	0.0316 (9)
O9	0.8805 (3)	0.4364 (2)	0.86084 (17)	0.0397 (7)
O10	0.8741 (3)	0.5612 (2)	0.93698 (16)	0.0369 (6)
C35	0.8169 (4)	0.5247 (3)	0.8827 (2)	0.0267 (8)
C36	0.6670 (4)	0.5873 (3)	0.8467 (2)	0.0294 (8)
H36A	0.6680	0.5733	0.7899	0.035*
H36B	0.6593	0.6605	0.8482	0.035*
C37	0.5252 (4)	0.5590 (3)	0.8961 (2)	0.0366 (10)
H37A	0.5392	0.4847	0.8975	0.044*
H37B	0.5243	0.5758	0.9522	0.044*
C38	0.3649 (4)	0.6125 (3)	0.8636 (2)	0.0299 (9)
H38A	0.3441	0.6865	0.8675	0.036*
H38B	0.3668	0.6009	0.8062	0.036*
C39	0.2333 (4)	0.5717 (3)	0.9121 (2)	0.0254 (8)
O11	0.2193 (3)	0.48505 (19)	0.89713 (16)	0.0320 (6)
O12	0.1485 (3)	0.62867 (18)	0.96418 (15)	0.0301 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Y1	0.01882 (17)	0.01929 (18)	0.0244 (2)	−0.00400 (12)	−0.00107 (13)	−0.00074 (15)
Y2	0.01906 (17)	0.0280 (2)	0.0232 (2)	−0.00726 (13)	0.00089 (14)	−0.00379 (16)
O1	0.0322 (13)	0.0228 (14)	0.0346 (16)	−0.0032 (10)	0.0066 (11)	0.0014 (11)
O2	0.0202 (12)	0.0280 (14)	0.0339 (15)	−0.0022 (10)	0.0023 (10)	0.0042 (11)
C1	0.0223 (17)	0.025 (2)	0.022 (2)	−0.0055 (13)	−0.0008 (14)	−0.0014 (15)
C2	0.0203 (17)	0.031 (2)	0.033 (2)	−0.0043 (14)	−0.0017 (15)	−0.0011 (17)
C3	0.0236 (18)	0.030 (2)	0.039 (2)	−0.0097 (14)	−0.0111 (15)	0.0052 (17)
C4	0.032 (2)	0.043 (2)	0.034 (2)	−0.0173 (16)	−0.0100 (16)	0.0111 (19)
C5	0.029 (2)	0.022 (2)	0.034 (2)	−0.0070 (14)	−0.0031 (16)	0.0049 (16)
O3	0.0246 (13)	0.0450 (17)	0.0326 (16)	−0.0065 (11)	−0.0026 (11)	−0.0040 (13)
O4	0.0224 (13)	0.0559 (18)	0.0341 (16)	−0.0092 (11)	−0.0009 (11)	0.0019 (13)
C6	0.046 (2)	0.040 (3)	0.051 (3)	−0.0022 (19)	0.013 (2)	0.014 (2)
C7	0.063 (3)	0.047 (3)	0.080 (4)	0.004 (2)	0.030 (3)	0.028 (3)
C8	0.062 (3)	0.037 (3)	0.106 (5)	−0.010 (2)	0.019 (3)	0.026 (3)
C9	0.046 (2)	0.024 (2)	0.077 (4)	−0.0073 (18)	−0.001 (2)	0.008 (2)
C10	0.077 (3)	0.022 (3)	0.099 (5)	−0.015 (2)	−0.001 (3)	−0.002 (3)
C11	0.076 (3)	0.028 (3)	0.087 (4)	−0.008 (2)	0.001 (3)	−0.019 (3)
C12	0.044 (2)	0.032 (2)	0.055 (3)	−0.0070 (17)	−0.001 (2)	−0.013 (2)
C13	0.057 (3)	0.047 (3)	0.053 (3)	−0.001 (2)	0.003 (2)	−0.026 (2)
C14	0.061 (3)	0.053 (3)	0.039 (3)	−0.015 (2)	0.014 (2)	−0.018 (2)
C15	0.038 (2)	0.035 (2)	0.039 (3)	−0.0058 (17)	0.0079 (18)	−0.0083 (19)
C16	0.0248 (18)	0.023 (2)	0.041 (2)	−0.0009 (14)	−0.0078 (16)	−0.0046 (17)
C17	0.0265 (19)	0.026 (2)	0.050 (3)	−0.0027 (15)	−0.0052 (17)	0.0024 (19)
N1	0.0261 (16)	0.0282 (17)	0.0347 (19)	−0.0050 (12)	−0.0029 (13)	−0.0002 (14)
N2	0.0312 (17)	0.0286 (18)	0.036 (2)	−0.0036 (13)	0.0020 (14)	0.0059 (15)
O5	0.0334 (14)	0.0221 (14)	0.0481 (18)	0.0020 (10)	−0.0158 (12)	−0.0086 (12)
O6	0.0308 (13)	0.0267 (14)	0.0294 (15)	−0.0083 (10)	−0.0074 (10)	−0.0034 (12)
C18	0.0214 (17)	0.030 (2)	0.025 (2)	−0.0053 (14)	0.0003 (14)	−0.0077 (16)
C19	0.0267 (19)	0.032 (2)	0.038 (2)	0.0019 (14)	−0.0105 (16)	−0.0133 (18)
C20	0.0301 (19)	0.028 (2)	0.035 (2)	−0.0071 (14)	−0.0072 (16)	−0.0081 (17)
C21	0.043 (2)	0.044 (3)	0.036 (2)	−0.0173 (18)	−0.0023 (18)	−0.010 (2)
C22	0.0267 (19)	0.031 (2)	0.033 (2)	−0.0054 (15)	−0.0039 (16)	−0.0077 (17)
O7	0.0433 (15)	0.0429 (17)	0.0338 (17)	−0.0169 (12)	0.0061 (12)	−0.0077 (13)
O8	0.0347 (14)	0.0405 (16)	0.0349 (16)	−0.0179 (11)	0.0054 (11)	−0.0118 (13)
N3	0.0293 (16)	0.0290 (18)	0.037 (2)	−0.0052 (12)	−0.0002 (14)	−0.0040 (15)
N4	0.0271 (16)	0.0334 (18)	0.0319 (19)	−0.0078 (12)	0.0002 (13)	−0.0030 (15)
C23	0.033 (2)	0.040 (2)	0.046 (3)	−0.0083 (17)	0.0017 (18)	−0.007 (2)
C24	0.032 (2)	0.049 (3)	0.064 (3)	−0.0100 (18)	0.009 (2)	−0.015 (2)
C25	0.026 (2)	0.054 (3)	0.063 (3)	−0.0017 (18)	0.000 (2)	−0.018 (2)
C26	0.032 (2)	0.043 (3)	0.043 (3)	0.0027 (17)	−0.0106 (18)	−0.018 (2)
C27	0.037 (2)	0.051 (3)	0.048 (3)	0.0100 (19)	−0.016 (2)	−0.003 (2)
C28	0.059 (3)	0.039 (3)	0.044 (3)	0.010 (2)	−0.019 (2)	0.002 (2)
C29	0.048 (2)	0.036 (2)	0.033 (2)	−0.0033 (18)	−0.0126 (19)	−0.0070 (19)
C30	0.069 (3)	0.033 (2)	0.037 (3)	−0.008 (2)	−0.011 (2)	0.004 (2)
C31	0.057 (3)	0.046 (3)	0.050 (3)	−0.017 (2)	0.004 (2)	0.007 (2)
C32	0.038 (2)	0.040 (3)	0.052 (3)	−0.0071 (18)	0.006 (2)	0.006 (2)
C33	0.035 (2)	0.029 (2)	0.029 (2)	−0.0054 (15)	−0.0077 (16)	−0.0068 (17)
C34	0.0282 (19)	0.035 (2)	0.030 (2)	−0.0003 (15)	−0.0102 (16)	−0.0093 (18)
O9	0.0385 (15)	0.0385 (17)	0.0366 (17)	0.0027 (12)	−0.0061 (12)	−0.0058 (13)
O10	0.0367 (14)	0.0544 (18)	0.0282 (15)	−0.0261 (12)	−0.0073 (11)	−0.0009 (13)
C35	0.0163 (17)	0.043 (2)	0.0202 (19)	−0.0097 (15)	0.0013 (14)	0.0051 (17)
C36	0.0257 (18)	0.036 (2)	0.028 (2)	−0.0121 (15)	−0.0047 (15)	0.0035 (17)
C37	0.0272 (19)	0.046 (2)	0.037 (2)	−0.0164 (16)	−0.0046 (16)	0.0134 (19)
C38	0.0220 (18)	0.034 (2)	0.031 (2)	−0.0068 (14)	0.0035 (15)	0.0038 (17)
C39	0.0189 (17)	0.029 (2)	0.027 (2)	−0.0054 (14)	−0.0026 (14)	0.0005 (16)
O11	0.0277 (13)	0.0332 (15)	0.0356 (16)	−0.0109 (10)	0.0061 (11)	−0.0043 (12)
O12	0.0242 (13)	0.0307 (14)	0.0343 (16)	−0.0075 (10)	0.0037 (11)	−0.0016 (12)

Geometric parameters (Å, º) top

Y1—O2ⁱ	2.314 (2)	C16—N1	1.358 (4)
Y1—O1ⁱⁱ	2.314 (2)	C16—C17	1.428 (5)
Y1—O6ⁱⁱⁱ	2.315 (2)	C17—N2	1.366 (5)
Y1—O3	2.386 (2)	O5—C18	1.246 (4)
Y1—O5	2.441 (3)	O6—C18	1.270 (4)
Y1—O4	2.455 (3)	O6—Y1ⁱⁱⁱ	2.315 (2)
Y1—O6	2.537 (2)	C18—C19	1.495 (5)
Y1—N2	2.538 (3)	C19—C20	1.505 (5)
Y1—N1	2.592 (3)	C19—H19A	0.9700
Y1—C5	2.779 (4)	C19—H19B	0.9700
Y1—C18	2.859 (4)	C20—C21	1.514 (5)
Y1—Y1ⁱⁱⁱ	3.9205 (15)	C20—H20A	0.9700
Y2—O10^iv	2.269 (3)	C20—H20B	0.9700
Y2—O12^v	2.317 (2)	C21—C22	1.509 (5)
Y2—O11ⁱ	2.329 (2)	C21—H21A	0.9700
Y2—O7	2.375 (3)	C21—H21B	0.9700
Y2—O9	2.397 (3)	C22—O8	1.256 (4)
Y2—O8	2.413 (3)	C22—O7	1.260 (4)
Y2—N4	2.570 (3)	N3—C32	1.330 (4)
Y2—N3	2.649 (3)	N3—C33	1.367 (4)
Y2—C22	2.744 (4)	N4—C23	1.324 (4)
Y2—O10	2.823 (3)	N4—C34	1.352 (4)
Y2—C35	2.985 (4)	C23—C24	1.395 (5)
O1—C1	1.264 (4)	C23—H23A	0.9300
O1—Y1ⁱⁱ	2.314 (2)	C24—C25	1.351 (6)
O2—C1	1.255 (4)	C24—H24A	0.9300
O2—Y1^vi	2.314 (2)	C25—C26	1.402 (6)
C1—C2	1.507 (4)	C25—H25A	0.9300
C2—C3	1.508 (5)	C26—C27	1.416 (6)
C2—H2A	0.9700	C26—C34	1.429 (5)
C2—H2B	0.9700	C27—C28	1.337 (6)
C3—C4	1.525 (4)	C27—H27A	0.9300
C3—H3A	0.9700	C28—C29	1.442 (5)
C3—H3B	0.9700	C28—H28A	0.9300
C4—C5	1.510 (5)	C29—C33	1.396 (5)
C4—H4A	0.9700	C29—C30	1.404 (6)
C4—H4B	0.9700	C30—C31	1.359 (6)
C5—O4	1.254 (4)	C30—H30A	0.9300
C5—O3	1.261 (4)	C31—C32	1.392 (5)
C6—N2	1.314 (5)	C31—H31A	0.9300
C6—C7	1.392 (6)	C32—H32A	0.9300
C6—H6A	0.9300	C33—C34	1.438 (5)
C7—C8	1.354 (7)	O9—C35	1.248 (4)
C7—H7A	0.9300	O10—C35	1.262 (4)
C8—C9	1.406 (6)	O10—Y2^iv	2.269 (3)
C8—H8A	0.9300	C35—C36	1.502 (4)
C9—C17	1.411 (5)	C36—C37	1.526 (4)
C9—C10	1.427 (6)	C36—H36A	0.9700
C10—C11	1.343 (6)	C36—H36B	0.9700
C10—H10A	0.9300	C37—C38	1.523 (5)
C11—C12	1.424 (6)	C37—H37A	0.9700
C11—H11A	0.9300	C37—H37B	0.9700
C12—C13	1.402 (6)	C38—C39	1.522 (4)
C12—C16	1.416 (5)	C38—H38A	0.9700
C13—C14	1.362 (6)	C38—H38B	0.9700
C13—H13A	0.9300	C39—O11	1.253 (4)
C14—C15	1.400 (5)	C39—O12	1.261 (4)
C14—H14A	0.9300	O11—Y2^vi	2.329 (2)
C15—N1	1.325 (4)	O12—Y2^v	2.317 (2)
C15—H15A	0.9300

O2ⁱ—Y1—O1ⁱⁱ	136.47 (8)	O4—C5—Y1	62.0 (2)
O2ⁱ—Y1—O6ⁱⁱⁱ	77.41 (9)	O3—C5—Y1	58.93 (19)
O1ⁱⁱ—Y1—O6ⁱⁱⁱ	73.73 (9)	C4—C5—Y1	178.2 (3)
O2ⁱ—Y1—O3	128.25 (9)	C5—O3—Y1	94.2 (2)
O1ⁱⁱ—Y1—O3	83.72 (9)	C5—O4—Y1	91.1 (2)
O6ⁱⁱⁱ—Y1—O3	89.75 (9)	N2—C6—C7	123.8 (4)
O2ⁱ—Y1—O5	80.79 (9)	N2—C6—H6A	118.1
O1ⁱⁱ—Y1—O5	89.26 (9)	C7—C6—H6A	118.1
O6ⁱⁱⁱ—Y1—O5	124.28 (8)	C8—C7—C6	119.0 (4)
O3—Y1—O5	141.65 (9)	C8—C7—H7A	120.5
O2ⁱ—Y1—O4	74.53 (8)	C6—C7—H7A	120.5
O1ⁱⁱ—Y1—O4	128.63 (9)	C7—C8—C9	120.1 (4)
O6ⁱⁱⁱ—Y1—O4	78.31 (9)	C7—C8—H8A	120.0
O3—Y1—O4	53.73 (8)	C9—C8—H8A	120.0
O5—Y1—O4	141.72 (9)	C8—C9—C17	117.0 (4)
O2ⁱ—Y1—O6	68.63 (8)	C8—C9—C10	124.1 (4)
O1ⁱⁱ—Y1—O6	71.91 (8)	C17—C9—C10	118.8 (4)
O6ⁱⁱⁱ—Y1—O6	72.29 (10)	C11—C10—C9	121.6 (4)
O3—Y1—O6	152.82 (8)	C11—C10—H10A	119.2
O5—Y1—O6	52.02 (8)	C9—C10—H10A	119.2
O4—Y1—O6	136.72 (8)	C10—C11—C12	120.9 (4)
O2ⁱ—Y1—N2	77.91 (9)	C10—C11—H11A	119.6
O1ⁱⁱ—Y1—N2	139.47 (9)	C12—C11—H11A	119.6
O6ⁱⁱⁱ—Y1—N2	145.78 (10)	C13—C12—C16	117.0 (4)
O3—Y1—N2	87.22 (10)	C13—C12—C11	123.2 (4)
O5—Y1—N2	74.03 (10)	C16—C12—C11	119.7 (4)
O4—Y1—N2	72.51 (10)	C14—C13—C12	120.3 (4)
O6—Y1—N2	119.13 (9)	C14—C13—H13A	119.9
O2ⁱ—Y1—N1	136.02 (9)	C12—C13—H13A	119.9
O1ⁱⁱ—Y1—N1	75.86 (9)	C13—C14—C15	118.6 (4)
O6ⁱⁱⁱ—Y1—N1	146.27 (8)	C13—C14—H14A	120.7
O3—Y1—N1	72.67 (9)	C15—C14—H14A	120.7
O5—Y1—N1	69.05 (9)	N1—C15—C14	123.6 (4)
O4—Y1—N1	110.76 (9)	N1—C15—H15A	118.2
O6—Y1—N1	111.37 (9)	C14—C15—H15A	118.2
N2—Y1—N1	63.74 (10)	N1—C16—C12	122.6 (4)
O2ⁱ—Y1—C5	101.34 (10)	N1—C16—C17	118.5 (3)
O1ⁱⁱ—Y1—C5	106.81 (10)	C12—C16—C17	118.9 (3)
O6ⁱⁱⁱ—Y1—C5	83.31 (10)	N2—C17—C9	122.3 (4)
O3—Y1—C5	26.92 (9)	N2—C17—C16	117.5 (3)
O5—Y1—C5	151.60 (9)	C9—C17—C16	120.1 (4)
O4—Y1—C5	26.82 (9)	C15—N1—C16	117.8 (3)
O6—Y1—C5	155.01 (9)	C15—N1—Y1	123.8 (2)
N2—Y1—C5	78.72 (11)	C16—N1—Y1	118.3 (2)
N1—Y1—C5	91.86 (10)	C6—N2—C17	117.9 (3)
O2ⁱ—Y1—C18	72.41 (9)	C6—N2—Y1	121.5 (3)
O1ⁱⁱ—Y1—C18	80.43 (9)	C17—N2—Y1	120.1 (2)
O6ⁱⁱⁱ—Y1—C18	98.61 (10)	C18—O5—Y1	96.2 (2)
O3—Y1—C18	159.19 (9)	C18—O6—Y1ⁱⁱⁱ	160.8 (2)
O5—Y1—C18	25.67 (8)	C18—O6—Y1	91.13 (19)
O4—Y1—C18	146.64 (8)	Y1ⁱⁱⁱ—O6—Y1	107.71 (10)
O6—Y1—C18	26.36 (8)	O5—C18—O6	120.5 (3)
N2—Y1—C18	96.11 (11)	O5—C18—C19	121.3 (3)
N1—Y1—C18	90.35 (10)	O6—C18—C19	118.1 (3)
C5—Y1—C18	172.75 (10)	O5—C18—Y1	58.08 (18)
O2ⁱ—Y1—Y1ⁱⁱⁱ	68.62 (6)	O6—C18—Y1	62.51 (17)
O1ⁱⁱ—Y1—Y1ⁱⁱⁱ	68.51 (6)	C19—C18—Y1	175.0 (2)
O6ⁱⁱⁱ—Y1—Y1ⁱⁱⁱ	38.06 (6)	C18—C19—C20	115.8 (3)
O3—Y1—Y1ⁱⁱⁱ	124.96 (7)	C18—C19—H19A	108.3
O5—Y1—Y1ⁱⁱⁱ	86.24 (6)	C20—C19—H19A	108.3
O4—Y1—Y1ⁱⁱⁱ	110.58 (7)	C18—C19—H19B	108.3
O6—Y1—Y1ⁱⁱⁱ	34.23 (6)	C20—C19—H19B	108.3
N2—Y1—Y1ⁱⁱⁱ	143.45 (6)	H19A—C19—H19B	107.4
N1—Y1—Y1ⁱⁱⁱ	136.64 (7)	C19—C20—C21	113.9 (3)
C5—Y1—Y1ⁱⁱⁱ	121.18 (8)	C19—C20—H20A	108.8
C18—Y1—Y1ⁱⁱⁱ	60.56 (8)	C21—C20—H20A	108.8
O10^iv—Y2—O12^v	77.40 (9)	C19—C20—H20B	108.8
O10^iv—Y2—O11ⁱ	75.51 (9)	C21—C20—H20B	108.8
O12^v—Y2—O11ⁱ	133.77 (9)	H20A—C20—H20B	107.7
O10^iv—Y2—O7	148.71 (9)	C22—C21—C20	114.2 (3)
O12^v—Y2—O7	88.66 (9)	C22—C21—H21A	108.7
O11ⁱ—Y2—O7	131.21 (9)	C20—C21—H21A	108.7
O10^iv—Y2—O9	124.70 (9)	C22—C21—H21B	108.7
O12^v—Y2—O9	76.41 (9)	C20—C21—H21B	108.7
O11ⁱ—Y2—O9	89.28 (9)	H21A—C21—H21B	107.6
O7—Y2—O9	77.41 (10)	O8—C22—O7	121.1 (4)
O10^iv—Y2—O8	146.55 (8)	O8—C22—C21	119.6 (3)
O12^v—Y2—O8	135.99 (9)	O7—C22—C21	119.3 (3)
O11ⁱ—Y2—O8	76.75 (9)	O8—C22—Y2	61.55 (19)
O7—Y2—O8	54.46 (8)	O7—C22—Y2	59.85 (19)
O9—Y2—O8	72.94 (9)	C21—C22—Y2	174.3 (3)
O10^iv—Y2—N4	84.42 (10)	C22—O7—Y2	92.8 (2)
O12^v—Y2—N4	135.98 (9)	C22—O8—Y2	91.2 (2)
O11ⁱ—Y2—N4	77.18 (9)	C32—N3—C33	116.5 (3)
O7—Y2—N4	86.64 (10)	C32—N3—Y2	123.9 (2)
O9—Y2—N4	143.92 (10)	C33—N3—Y2	119.5 (2)
O8—Y2—N4	71.46 (10)	C23—N4—C34	117.6 (3)
O10^iv—Y2—N3	77.12 (10)	C23—N4—Y2	120.4 (2)
O12^v—Y2—N3	74.34 (9)	C34—N4—Y2	122.0 (2)
O11ⁱ—Y2—N3	132.89 (9)	N4—C23—C24	124.2 (4)
O7—Y2—N3	72.15 (10)	N4—C23—H23A	117.9
O9—Y2—N3	137.77 (10)	C24—C23—H23A	117.9
O8—Y2—N3	109.74 (9)	C25—C24—C23	118.5 (4)
N4—Y2—N3	62.57 (9)	C25—C24—H24A	120.7
O10^iv—Y2—C22	163.37 (10)	C23—C24—H24A	120.7
O12^v—Y2—C22	112.29 (10)	C24—C25—C26	120.5 (4)
O11ⁱ—Y2—C22	103.94 (10)	C24—C25—H25A	119.8
O7—Y2—C22	27.30 (9)	C26—C25—H25A	119.8
O9—Y2—C22	71.66 (10)	C25—C26—C27	124.3 (4)
O8—Y2—C22	27.24 (9)	C25—C26—C34	116.9 (4)
N4—Y2—C22	79.32 (10)	C27—C26—C34	118.8 (4)
N3—Y2—C22	92.18 (11)	C28—C27—C26	121.9 (4)
O10^iv—Y2—O10	76.57 (10)	C28—C27—H27A	119.0
O12^v—Y2—O10	68.15 (8)	C26—C27—H27A	119.0
O11ⁱ—Y2—O10	69.54 (8)	C27—C28—C29	121.2 (4)
O7—Y2—O10	124.08 (8)	C27—C28—H28A	119.4
O9—Y2—O10	48.56 (9)	C29—C28—H28A	119.4
O8—Y2—O10	110.43 (9)	C33—C29—C30	118.2 (4)
N4—Y2—O10	144.79 (8)	C33—C29—C28	118.9 (4)
N3—Y2—O10	137.84 (8)	C30—C29—C28	122.9 (4)
C22—Y2—O10	119.18 (9)	C31—C30—C29	119.2 (4)
O10^iv—Y2—C35	101.03 (11)	C31—C30—H30A	120.4
O12^v—Y2—C35	69.16 (9)	C29—C30—H30A	120.4
O11ⁱ—Y2—C35	80.16 (9)	C30—C31—C32	118.9 (4)
O7—Y2—C35	99.85 (10)	C30—C31—H31A	120.6
O9—Y2—C35	23.74 (10)	C32—C31—H31A	120.6
O8—Y2—C35	92.24 (10)	N3—C32—C31	124.4 (4)
N4—Y2—C35	154.55 (9)	N3—C32—H32A	117.8
N3—Y2—C35	142.85 (9)	C31—C32—H32A	117.8
C22—Y2—C35	95.17 (11)	N3—C33—C29	122.8 (3)
O10—Y2—C35	24.90 (9)	N3—C33—C34	117.1 (3)
O10^iv—Y2—Y2^iv	43.19 (7)	C29—C33—C34	120.1 (3)
O12^v—Y2—Y2^iv	67.34 (7)	N4—C34—C26	122.2 (3)
O11ⁱ—Y2—Y2^iv	67.20 (6)	N4—C34—C33	118.7 (3)
O7—Y2—Y2^iv	151.36 (6)	C26—C34—C33	119.1 (4)
O9—Y2—Y2^iv	81.74 (7)	C35—O9—Y2	105.6 (2)
O8—Y2—Y2^iv	135.85 (7)	C35—O10—Y2^iv	166.4 (2)
N4—Y2—Y2^iv	121.33 (8)	C35—O10—Y2	84.7 (2)
N3—Y2—Y2^iv	113.30 (7)	Y2^iv—O10—Y2	103.43 (10)
C22—Y2—Y2^iv	152.26 (8)	O9—C35—O10	120.7 (3)
O10—Y2—Y2^iv	33.38 (6)	O9—C35—C36	120.1 (3)
C35—Y2—Y2^iv	57.99 (8)	O10—C35—C36	119.2 (3)
C1—O1—Y1ⁱⁱ	132.1 (2)	O9—C35—Y2	50.68 (18)
C1—O2—Y1^vi	135.6 (2)	O10—C35—Y2	70.3 (2)
O2—C1—O1	126.3 (3)	C36—C35—Y2	167.8 (3)
O2—C1—C2	117.9 (3)	C35—C36—C37	109.4 (3)
O1—C1—C2	115.8 (3)	C35—C36—H36A	109.8
C1—C2—C3	116.5 (3)	C37—C36—H36A	109.8
C1—C2—H2A	108.2	C35—C36—H36B	109.8
C3—C2—H2A	108.2	C37—C36—H36B	109.8
C1—C2—H2B	108.2	H36A—C36—H36B	108.2
C3—C2—H2B	108.2	C38—C37—C36	115.1 (3)
H2A—C2—H2B	107.3	C38—C37—H37A	108.5
C2—C3—C4	111.6 (3)	C36—C37—H37A	108.5
C2—C3—H3A	109.3	C38—C37—H37B	108.5
C4—C3—H3A	109.3	C36—C37—H37B	108.5
C2—C3—H3B	109.3	H37A—C37—H37B	107.5
C4—C3—H3B	109.3	C39—C38—C37	111.0 (3)
H3A—C3—H3B	108.0	C39—C38—H38A	109.4
C5—C4—C3	115.7 (3)	C37—C38—H38A	109.4
C5—C4—H4A	108.4	C39—C38—H38B	109.4
C3—C4—H4A	108.4	C37—C38—H38B	109.4
C5—C4—H4B	108.4	H38A—C38—H38B	108.0
C3—C4—H4B	108.4	O11—C39—O12	126.0 (3)
H4A—C4—H4B	107.4	O11—C39—C38	117.4 (3)
O4—C5—O3	121.0 (3)	O12—C39—C38	116.6 (3)
O4—C5—C4	118.8 (3)	C39—O11—Y2^vi	138.4 (2)
O3—C5—C4	120.2 (3)	C39—O12—Y2^v	138.6 (2)

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

Experimental details

Crystal data
Chemical formula	[Y₂(C₅H₆O₄)₃(C₁₂H₈N₂)₂]
M_r	928.52
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.7681 (18), 13.418 (3), 16.410 (3)
α, β, γ (°)	83.83 (3), 84.41 (3), 75.09 (3)
V (Å³)	1849.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.19
Crystal size (mm)	0.23 × 0.17 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.790, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	17986, 8240, 5620
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.076, 1.02
No. of reflections	8240
No. of parameters	514
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.43

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected bond lengths (Å) top

Y1—O2ⁱ	2.314 (2)	Y2—O10^iv	2.269 (3)
Y1—O1ⁱⁱ	2.314 (2)	Y2—O12^v	2.317 (2)
Y1—O6ⁱⁱⁱ	2.315 (2)	Y2—O11ⁱ	2.329 (2)
Y1—O3	2.386 (2)	Y2—O7	2.375 (3)
Y1—O5	2.441 (3)	Y2—O9	2.397 (3)
Y1—O4	2.455 (3)	Y2—O8	2.413 (3)
Y1—O6	2.537 (2)	Y2—N4	2.570 (3)
Y1—N2	2.538 (3)	Y2—N3	2.649 (3)
Y1—N1	2.592 (3)	Y2—O10	2.823 (3)

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

Acknowledgements

This project was supported by the K. C. Wong Magna Fund in Ningbo University.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Koo, B. K., Kim, J. & Lee, U. (2010). Inorg. Chim. Acta, 363, 1760–1766. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, Y.-B. & Yu, H.-X. (2007). Acta Cryst. E63, m2804. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, L. P., Wan, Y. H. & Jin, L. P. (2003). J. Mol. Struct. 646, 169–178. Web of Science CSD CrossRef CAS Google Scholar