(4′-All­yloxy-2,2′:6′,2′′-terpyridine)(dibenzoyl­methanido)dinitratoerbium(III) acetonitrile solvate

Mei, Q.; Tong, B.

doi:10.1107/S1600536809055032

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m106

https://doi.org/10.1107/S1600536809055032

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(4′-Allyloxy-2,2′:6′,2′′-terpyridine)(dibenzoylmethanido)dinitratoerbium(III) acetonitrile solvate

Qunbo Mei ^a and Bihai Tong ^b ^*

^aJiangsu Key Laboratory of Organic Electronics & Information Displays and, Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, Nanjing 210046, People's Republic of China, and ^bInstitute of Molecular Engineering & Applied Chemistry, College of Metallurgy and Resources, Anhui University of Technology, Maanshan 243002, People's Republic of China
^*Correspondence e-mail: tongbihai@163.com

(Received 16 December 2009; accepted 22 December 2009; online 9 January 2010)

The title complex, [Er(C₁₅H₁₁O₂)(NO₃)₂(C₁₈H₁₅N₃O)]·CH₃CN, has been synthesized from 4′-allyloxy-2,2′:6′,2′′-terpyridine (altpy), dibenzoylmethane and erbium nitrate. The distorted monocapped square antiprismatic coordination polyhedron is formed by a bidentate dibenzoylmethanide residue, a tridentate altpy ligand and two nitrate anions that act as bidentate ligands and occupy mutually trans sites.

Related literature

For the use of lanthanide complexes as functional materials, see: Sun et al. (2005 ). For antenna effects, see: Sabbatini et al. (1993 ). For related structures, see: Niu et al. (1997 ); Neelgund et al. (2007 ); Fukuda et al. (2002 ); Hunter et al. (2007 ).

Experimental

Crystal data

[Er(C₁₅H₁₁O₂)(NO₃)₂(C₁₈H₁₅N₃O)]·C₂H₃N
M_r = 844.90
Monoclinic, P 2₁ /n
a = 13.245 (4) Å
b = 15.871 (4) Å
c = 16.135 (5) Å
β = 103.374 (6)°
V = 3299.8 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.61 mm⁻¹
T = 173 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.550, T_max = 0.598
15598 measured reflections
6429 independent reflections
4383 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.088
S = 1.04
6429 reflections
460 parameters
H-atom parameters constrained
Δρ_max = 1.65 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Table 1
Selected bond lengths (Å)

Er1—O3	2.224 (3)
Er1—O2	2.228 (4)
Er1—O4	2.410 (4)
Er1—O9	2.425 (4)
Er1—N2	2.447 (4)
Er1—N3	2.460 (4)
Er1—O5	2.465 (4)
Er1—O8	2.468 (4)
Er1—N1	2.515 (4)

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: https://doi.org/10.1107/S1600536809055032/si2232sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055032/si2232Isup2.hkl

checkCIF report

Comment top

Recently, much attention has been paid to near-infrared (NIR) luminescence of trivalent lanthanide ions such as erbium (Er³⁺) and neodymium (Nd³⁺), because they show luminescence in the telecommunication low-loss NIR-regions of silica (Sun et al., (2005)). However, it is difficult to generate this luminescence by direct excitation of these NIR-luminescence lanthanide ions due to some quenching effects as well as their poor absorption abilities. A method to avoid quenching of the excited state is to shield the lanthanide ion from the deactivating groups by a shell of organic ligands. Another benefit of using organic ligands is that energy absorbed by a ligand containing a chromophoric group, can be transferred to the lanthanide ion. This mechanism is called the antenna effect (Sabbatini et al., (1993)). In the title compound, [Er(altpy)(dbm)(NO₃)₂].CH₃CN(altpy=4'-allyloxy-2, 2':6', 2''-terpyridine, dbm=dibenzoylmethanate), each Er(III) atom is in a nine coordinate environment comprising two oxygen atoms from the bidentate dbm ligand, three nitrogen atoms from the tridentate altpy ligand and four oxygen atoms from two tertiary nitrate anions that act as bidentate ligands and occupy mutually trans sites in the coordination polyhedron. The coordination polyhedron is a distorted monocapped square antiprism. The Er—O distances lie in two groups, those to the beta-diketone oxygen atoms in the range 2.224 (3)–2.228 (4) Å and those to nitrate O atoms in the range 2.410 (4)–2.468 (4) Å. These are comparable to those [2.485 (19), 2.600 (15) Å] in the nine-coordinate complex [Er₂(O₂CMe)₄(NO₃)₂(phen)₂] (phen=1,10-phenanthroline) which also contains bidentate chelating nitrate anions (Niu et al., 1997). The O—Er—O angle (76.97 (13) °) of the beta-diketonate ligand is somewhat higher as compared to those found in the erbium tris(beta-diketonates) type of complexes (73.65 (49) °) (Neelgund et al., (2007)). The average Er—N distance (2.474 (4) Å) is slightly shorter than that in the nine-coordinate complex [Er(terpy) (acac) (NO₃)₂^-] (2.503 (4) Å)(Fukuda et al., (2002)). The geometrical parameters of the [NO₃]^- anions in the title complex are as expected with normal distances and angles, comparable to those reported by Hunter et al., (2007) for a complex also containing bidentate chelating nitrate anions.

Related literature top

For the use of lanthanide complexes as functional materials, see: Sun et al. (2005). For antenna effects, see: Sabbatini et al. (1993). For related structures, see: Niu et al. (1997); Neelgund et al. (2007); Fukuda et al. (2002); Hunter et al. (2007).

Experimental top

The title compound was obtained by refluxing erbium nitrate, 4'-allyloxy-2, 2':6',2''-terpyridine and dibenzoylmethanate in ethanol to give the title compound as a yellow precipitate in 81% yield. Recrystallization from ethanol and acetonitrile (1:1) gave yellow block-like crystals suitable for an X-ray diffraction determination. Anal.Calcd. for C₃₅H₂₉ErN₆O₉: C, 52.60, H, 3.46, N, 9.95%. Found:C, 51.70, H, 3.71, N, 9.87%.

Structure description top

For the use of lanthanide complexes as functional materials, see: Sun et al. (2005). For antenna effects, see: Sabbatini et al. (1993). For related structures, see: Niu et al. (1997); Neelgund et al. (2007); Fukuda et al. (2002); Hunter et al. (2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

(4'-Allyloxy-2,2':6',2''-terpyridine)(dibenzoylmethanido)dinitratoerbium(III) acetonitrile solvate top

Crystal data top

[Er(C₁₅H₁₁O₂)(NO₃)₂(C₁₈H₁₅N₃O)]·C₂H₃N	F(000) = 1684
M_r = 844.90	D_x = 1.701 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4650 reflections
a = 13.245 (4) Å	θ = 2.6–26.6°
b = 15.871 (4) Å	µ = 2.61 mm⁻¹
c = 16.135 (5) Å	T = 173 K
β = 103.374 (6)°	Block, yellow
V = 3299.8 (16) Å³	0.26 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6429 independent reflections
Radiation source: fine-focus sealed tube	4383 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→16
T_min = 0.550, T_max = 0.598	k = −19→19
15598 measured reflections	l = −19→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0365P)²] where P = (F_o² + 2F_c²)/3
6429 reflections	(Δ/σ)_max = 0.002
460 parameters	Δρ_max = 1.65 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[Er(C₁₅H₁₁O₂)(NO₃)₂(C₁₈H₁₅N₃O)]·C₂H₃N	V = 3299.8 (16) Å³
M_r = 844.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.245 (4) Å	µ = 2.61 mm⁻¹
b = 15.871 (4) Å	T = 173 K
c = 16.135 (5) Å	0.26 × 0.24 × 0.22 mm
β = 103.374 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6429 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	4383 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.598	R_int = 0.052
15598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.04	Δρ_max = 1.65 e Å⁻³
6429 reflections	Δρ_min = −1.14 e Å⁻³
460 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
Er1	0.756234 (17)	0.801711 (15)	0.037240 (16)	0.01847 (8)
O2	0.6625 (3)	0.6940 (2)	0.0666 (2)	0.0255 (9)
O9	0.7831 (3)	0.8367 (3)	0.1870 (3)	0.0384 (11)
N5	0.6926 (4)	0.8638 (3)	0.1844 (3)	0.0277 (12)
O3	0.8761 (3)	0.7066 (2)	0.0928 (2)	0.0278 (9)
O8	0.6304 (3)	0.8630 (3)	0.1117 (2)	0.0306 (10)
N2	0.7337 (3)	0.9511 (3)	0.0000 (3)	0.0227 (10)
C13	0.4028 (4)	0.8715 (4)	−0.1717 (4)	0.0326 (15)
H13A	0.3365	0.8842	−0.2069	0.039*
N1	0.9170 (3)	0.8903 (3)	0.0826 (3)	0.0257 (11)
N3	0.5943 (3)	0.8339 (3)	−0.0678 (3)	0.0244 (11)
C26	0.7835 (4)	0.5834 (4)	0.1087 (3)	0.0235 (13)
H26	0.7901	0.5246	0.1200	0.028*
C24	0.5947 (4)	0.5659 (3)	0.1060 (4)	0.0240 (13)
C6	0.8061 (4)	1.0085 (4)	0.0366 (4)	0.0244 (13)
C20	0.4118 (4)	0.5409 (4)	0.0781 (4)	0.0333 (15)
H20A	0.3431	0.5574	0.0511	0.040*
C23	0.6107 (4)	0.4949 (4)	0.1589 (4)	0.0280 (14)
H23A	0.6792	0.4786	0.1864	0.034*
O7	0.6658 (3)	0.8903 (3)	0.2473 (3)	0.0425 (12)
C1	1.0107 (4)	0.8569 (4)	0.1162 (4)	0.0296 (14)
H1A	1.0168	0.7973	0.1201	0.035*
C18	0.9133 (5)	1.2961 (4)	0.0249 (4)	0.0433 (16)
H18A	0.9352	1.2855	0.0843	0.052*
H18B	0.9627	1.3111	−0.0068	0.052*
C33	1.0601 (4)	0.6243 (4)	0.1839 (4)	0.0282 (14)
H33A	1.0537	0.6808	0.2013	0.034*
C27	0.8725 (4)	0.6284 (4)	0.1095 (4)	0.0254 (13)
C25	0.6834 (4)	0.6185 (4)	0.0921 (3)	0.0233 (13)
C4	0.9941 (4)	1.0266 (4)	0.1053 (4)	0.0290 (14)
H4A	0.9867	1.0861	0.1012	0.035*
C3	1.0896 (4)	0.9908 (4)	0.1391 (3)	0.0284 (14)
H3A	1.1490	1.0255	0.1579	0.034*
C19	0.4941 (4)	0.5886 (4)	0.0659 (3)	0.0272 (14)
H19A	0.4821	0.6368	0.0301	0.033*
C5	0.9095 (4)	0.9748 (3)	0.0775 (4)	0.0246 (13)
C28	0.9739 (4)	0.5836 (4)	0.1333 (4)	0.0252 (13)
C11	0.5651 (4)	0.9147 (4)	−0.0845 (3)	0.0228 (13)
C22	0.5273 (4)	0.4488 (4)	0.1709 (4)	0.0326 (15)
H22A	0.5386	0.4020	0.2087	0.039*
C14	0.4322 (4)	0.7896 (4)	−0.1555 (3)	0.0283 (14)
H14A	0.3874	0.7448	−0.1798	0.034*
C15	0.5281 (4)	0.7731 (4)	−0.1033 (3)	0.0247 (13)
H15A	0.5482	0.7161	−0.0920	0.030*
C29	0.9859 (4)	0.5007 (4)	0.1094 (4)	0.0371 (16)
H29A	0.9283	0.4713	0.0758	0.044*
C10	0.6405 (4)	0.9802 (3)	−0.0439 (3)	0.0244 (13)
C12	0.4691 (4)	0.9361 (4)	−0.1370 (4)	0.0294 (14)
H12A	0.4500	0.9933	−0.1486	0.035*
C9	0.6173 (4)	1.0647 (4)	−0.0499 (3)	0.0260 (14)
H9A	0.5514	1.0830	−0.0818	0.031*
C7	0.7868 (4)	1.0951 (3)	0.0333 (4)	0.0262 (13)
H7A	0.8392	1.1336	0.0600	0.031*
C17	0.8142 (5)	1.2901 (4)	−0.0134 (4)	0.0371 (16)
H17A	0.7946	1.3011	−0.0729	0.045*
C8	0.6904 (4)	1.1238 (4)	−0.0091 (4)	0.0277 (14)
O1	0.6601 (3)	1.2051 (2)	−0.0152 (3)	0.0344 (10)
C32	1.1545 (4)	0.5835 (4)	0.2091 (4)	0.0345 (15)
H32A	1.2123	0.6120	0.2435	0.041*
C21	0.4271 (4)	0.4697 (4)	0.1288 (4)	0.0329 (15)
H21A	0.3700	0.4359	0.1346	0.040*
C31	1.1647 (5)	0.5019 (4)	0.1844 (4)	0.0431 (17)
H31A	1.2294	0.4737	0.2017	0.052*
C34	0.9374 (6)	0.2095 (5)	0.2523 (4)	0.0456 (18)
C35	1.0307 (5)	0.2525 (5)	0.2958 (5)	0.064 (2)
H35A	1.0281	0.3112	0.2767	0.096*
H35B	1.0912	0.2246	0.2828	0.096*
H35C	1.0361	0.2508	0.3574	0.096*
N6	0.8619 (6)	0.1790 (4)	0.2183 (4)	0.069 (2)
O5	0.7447 (3)	0.6999 (3)	−0.0800 (3)	0.0328 (9)
O4	0.8224 (3)	0.8173 (3)	−0.0890 (3)	0.0379 (11)
N4	0.7853 (4)	0.7484 (3)	−0.1245 (3)	0.0319 (12)
C2	1.0982 (4)	0.9046 (4)	0.1452 (4)	0.0293 (14)
H2A	1.1631	0.8787	0.1690	0.035*
C16	0.7312 (4)	1.2670 (4)	0.0308 (4)	0.0345 (16)
H16A	0.7636	1.2446	0.0880	0.041*
H16B	0.6919	1.3184	0.0386	0.041*
C30	1.0801 (5)	0.4608 (4)	0.1338 (5)	0.051 (2)
H30A	1.0874	0.4046	0.1159	0.061*
O6	0.7867 (4)	0.7318 (3)	−0.1977 (3)	0.0538 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.01372 (12)	0.01403 (13)	0.02633 (15)	0.00049 (12)	0.00190 (9)	0.00175 (13)
O2	0.0199 (19)	0.022 (2)	0.034 (2)	0.0043 (18)	0.0059 (16)	0.0071 (19)
O9	0.024 (2)	0.043 (3)	0.046 (3)	0.005 (2)	0.0030 (19)	−0.002 (2)
N5	0.026 (3)	0.029 (3)	0.026 (3)	−0.003 (2)	0.001 (2)	−0.001 (2)
O3	0.020 (2)	0.018 (2)	0.045 (3)	0.0015 (17)	0.0047 (17)	0.0048 (19)
O8	0.029 (2)	0.037 (3)	0.024 (2)	0.0065 (19)	0.0013 (18)	0.0023 (19)
N2	0.018 (2)	0.020 (3)	0.029 (3)	0.000 (2)	0.0032 (19)	0.000 (2)
C13	0.023 (3)	0.044 (4)	0.029 (4)	0.005 (3)	0.003 (3)	0.002 (3)
N1	0.020 (3)	0.025 (3)	0.031 (3)	0.003 (2)	0.004 (2)	−0.001 (2)
N3	0.026 (3)	0.019 (3)	0.029 (3)	−0.001 (2)	0.007 (2)	0.001 (2)
C26	0.019 (3)	0.020 (3)	0.031 (4)	0.005 (2)	0.004 (2)	0.005 (3)
C24	0.021 (3)	0.022 (3)	0.030 (3)	−0.002 (2)	0.008 (2)	0.002 (3)
C6	0.013 (3)	0.026 (3)	0.034 (4)	0.004 (2)	0.006 (2)	0.006 (3)
C20	0.023 (3)	0.026 (4)	0.050 (4)	−0.001 (3)	0.006 (3)	0.004 (3)
C23	0.023 (3)	0.029 (4)	0.029 (4)	−0.002 (3)	0.000 (3)	0.003 (3)
O7	0.042 (3)	0.052 (3)	0.036 (3)	−0.006 (2)	0.014 (2)	−0.014 (2)
C1	0.019 (3)	0.020 (3)	0.048 (4)	0.000 (3)	0.004 (3)	0.000 (3)
C18	0.048 (4)	0.040 (4)	0.044 (4)	−0.009 (4)	0.015 (3)	−0.003 (3)
C33	0.024 (3)	0.028 (3)	0.035 (4)	0.000 (3)	0.011 (3)	0.004 (3)
C27	0.024 (3)	0.023 (3)	0.029 (3)	0.003 (3)	0.006 (3)	0.002 (3)
C25	0.019 (3)	0.029 (3)	0.018 (3)	−0.003 (2)	−0.003 (2)	0.001 (3)
C4	0.031 (3)	0.022 (3)	0.033 (4)	−0.006 (3)	0.004 (3)	0.001 (3)
C3	0.024 (3)	0.031 (4)	0.027 (4)	−0.008 (3)	0.000 (3)	−0.003 (3)
C19	0.025 (3)	0.028 (3)	0.028 (3)	0.003 (3)	0.005 (3)	0.010 (3)
C5	0.021 (3)	0.020 (3)	0.033 (4)	0.002 (2)	0.005 (3)	0.004 (3)
C28	0.018 (3)	0.027 (3)	0.030 (4)	0.004 (3)	0.005 (2)	0.009 (3)
C11	0.020 (3)	0.027 (3)	0.022 (3)	0.001 (3)	0.005 (2)	−0.003 (3)
C22	0.037 (4)	0.028 (4)	0.034 (4)	−0.002 (3)	0.010 (3)	0.008 (3)
C14	0.022 (3)	0.037 (4)	0.023 (3)	−0.006 (3)	0.000 (2)	−0.006 (3)
C15	0.027 (3)	0.022 (3)	0.024 (3)	−0.003 (2)	0.002 (3)	−0.002 (2)
C29	0.025 (3)	0.030 (4)	0.052 (4)	0.002 (3)	0.001 (3)	−0.004 (3)
C10	0.023 (3)	0.023 (3)	0.027 (3)	−0.002 (2)	0.006 (2)	0.003 (3)
C12	0.023 (3)	0.033 (4)	0.031 (4)	0.006 (3)	0.002 (3)	−0.004 (3)
C9	0.022 (3)	0.027 (3)	0.028 (3)	0.006 (3)	0.002 (2)	0.002 (3)
C7	0.025 (3)	0.015 (3)	0.038 (4)	−0.005 (2)	0.006 (3)	−0.001 (3)
C17	0.050 (4)	0.027 (4)	0.033 (4)	−0.001 (3)	0.006 (3)	0.003 (3)
C8	0.030 (3)	0.020 (3)	0.034 (4)	−0.001 (3)	0.010 (3)	0.002 (3)
O1	0.031 (2)	0.020 (2)	0.047 (3)	0.0040 (19)	−0.0023 (19)	0.001 (2)
C32	0.017 (3)	0.045 (4)	0.036 (4)	−0.001 (3)	−0.005 (3)	0.002 (3)
C21	0.026 (3)	0.030 (4)	0.047 (4)	−0.009 (3)	0.017 (3)	−0.003 (3)
C31	0.027 (4)	0.043 (4)	0.055 (5)	0.016 (3)	0.003 (3)	−0.001 (4)
C34	0.058 (5)	0.048 (5)	0.027 (4)	0.005 (4)	0.003 (3)	0.001 (3)
C35	0.047 (5)	0.084 (6)	0.062 (6)	−0.002 (5)	0.015 (4)	−0.008 (5)
N6	0.083 (5)	0.072 (5)	0.038 (4)	−0.017 (4)	−0.012 (4)	0.001 (3)
O5	0.034 (2)	0.027 (2)	0.039 (2)	−0.004 (2)	0.0119 (18)	0.001 (2)
O4	0.039 (3)	0.029 (3)	0.051 (3)	−0.005 (2)	0.021 (2)	−0.001 (2)
N4	0.037 (3)	0.020 (3)	0.039 (4)	0.006 (2)	0.011 (3)	0.001 (3)
C2	0.016 (3)	0.030 (4)	0.037 (4)	0.000 (3)	−0.003 (3)	0.005 (3)
C16	0.040 (4)	0.014 (3)	0.047 (4)	0.006 (3)	0.005 (3)	0.002 (3)
C30	0.041 (4)	0.039 (4)	0.068 (5)	0.017 (3)	0.004 (4)	−0.012 (4)
O6	0.083 (4)	0.049 (3)	0.036 (3)	0.004 (3)	0.026 (3)	−0.008 (2)

Geometric parameters (Å, º) top

Er1—O3	2.224 (3)	C33—H33A	0.9500
Er1—O2	2.228 (4)	C27—C28	1.490 (7)
Er1—O4	2.410 (4)	C4—C5	1.378 (7)
Er1—O9	2.425 (4)	C4—C3	1.379 (7)
Er1—N2	2.447 (4)	C4—H4A	0.9500
Er1—N3	2.460 (4)	C3—C2	1.375 (8)
Er1—O5	2.465 (4)	C3—H3A	0.9500
Er1—O8	2.468 (4)	C19—H19A	0.9500
Er1—N1	2.515 (4)	C28—C29	1.390 (8)
Er1—N4	2.853 (6)	C11—C12	1.397 (7)
Er1—N5	2.872 (5)	C11—C10	1.486 (7)
O2—C25	1.275 (6)	C22—C21	1.385 (7)
O9—N5	1.265 (6)	C22—H22A	0.9500
N5—O7	1.224 (6)	C14—C15	1.377 (7)
N5—O8	1.268 (5)	C14—H14A	0.9500
O3—C27	1.274 (6)	C15—H15A	0.9500
N2—C10	1.355 (6)	C29—C30	1.372 (8)
N2—C6	1.355 (7)	C29—H29A	0.9500
C13—C14	1.365 (8)	C10—C9	1.373 (8)
C13—C12	1.381 (8)	C12—H12A	0.9500
C13—H13A	0.9500	C9—C8	1.399 (7)
N1—C1	1.343 (6)	C9—H9A	0.9500
N1—C5	1.347 (7)	C7—C8	1.379 (7)
N3—C15	1.340 (7)	C7—H7A	0.9500
N3—C11	1.348 (7)	C17—C16	1.488 (8)
C26—C27	1.376 (7)	C17—H17A	0.9500
C26—C25	1.406 (7)	C8—O1	1.349 (6)
C26—H26	0.9500	O1—C16	1.442 (7)
C24—C19	1.387 (7)	C32—C31	1.370 (9)
C24—C23	1.398 (7)	C32—H32A	0.9500
C24—C25	1.501 (7)	C21—H21A	0.9500
C6—C7	1.396 (7)	C31—C30	1.387 (9)
C6—C5	1.476 (7)	C31—H31A	0.9500
C20—C19	1.378 (7)	C34—N6	1.132 (8)
C20—C21	1.382 (8)	C34—C35	1.443 (10)
C20—H20A	0.9500	C35—H35A	0.9800
C23—C22	1.376 (7)	C35—H35B	0.9800
C23—H23A	0.9500	C35—H35C	0.9800
C1—C2	1.373 (7)	O5—N4	1.256 (6)
C1—H1A	0.9500	O4—N4	1.279 (6)
C18—C17	1.318 (8)	N4—O6	1.214 (6)
C18—H18A	0.9500	C2—H2A	0.9500
C18—H18B	0.9500	C16—H16A	0.9900
C33—C32	1.383 (7)	C16—H16B	0.9900
C33—C28	1.399 (7)	C30—H30A	0.9500

O3—Er1—O2	76.97 (13)	C17—C18—H18B	120.0
O3—Er1—O4	92.59 (14)	H18A—C18—H18B	120.0
O2—Er1—O4	126.04 (14)	C32—C33—C28	121.1 (6)
O3—Er1—O9	80.05 (14)	C32—C33—H33A	119.5
O2—Er1—O9	85.66 (14)	C28—C33—H33A	119.5
O4—Er1—O9	145.20 (14)	O3—C27—C26	125.4 (5)
O3—Er1—N2	142.34 (13)	O3—C27—C28	116.3 (5)
O2—Er1—N2	138.91 (13)	C26—C27—C28	118.3 (5)
O4—Er1—N2	74.94 (14)	O2—C25—C26	124.0 (5)
O9—Er1—N2	90.25 (15)	O2—C25—C24	116.9 (5)
O3—Er1—N3	147.82 (14)	C26—C25—C24	119.1 (5)
O2—Er1—N3	82.30 (14)	C5—C4—C3	119.1 (5)
O4—Er1—N3	79.97 (15)	C5—C4—H4A	120.5
O9—Er1—N3	122.85 (14)	C3—C4—H4A	120.5
N2—Er1—N3	65.93 (14)	C2—C3—C4	119.4 (5)
O3—Er1—O5	77.08 (14)	C2—C3—H3A	120.3
O2—Er1—O5	73.83 (13)	C4—C3—H3A	120.3
O4—Er1—O5	52.32 (13)	C20—C19—C24	119.8 (5)
O9—Er1—O5	152.10 (14)	C20—C19—H19A	120.1
N2—Er1—O5	117.65 (14)	C24—C19—H19A	120.1
N3—Er1—O5	73.64 (14)	N1—C5—C4	122.0 (5)
O3—Er1—O8	124.80 (13)	N1—C5—C6	115.9 (5)
O2—Er1—O8	74.14 (13)	C4—C5—C6	122.0 (5)
O4—Er1—O8	142.14 (13)	C29—C28—C33	117.9 (5)
O9—Er1—O8	52.00 (13)	C29—C28—C27	122.4 (5)
N2—Er1—O8	71.35 (14)	C33—C28—C27	119.7 (5)
N3—Er1—O8	70.99 (14)	N3—C11—C12	122.1 (5)
O5—Er1—O8	134.65 (13)	N3—C11—C10	116.4 (5)
O3—Er1—N1	77.54 (14)	C12—C11—C10	121.5 (5)
O2—Er1—N1	147.48 (14)	C23—C22—C21	120.9 (6)
O4—Er1—N1	74.91 (14)	C23—C22—H22A	119.6
O9—Er1—N1	70.29 (14)	C21—C22—H22A	119.6
N2—Er1—N1	64.97 (14)	C13—C14—C15	118.7 (5)
N3—Er1—N1	128.97 (15)	C13—C14—H14A	120.7
O5—Er1—N1	119.19 (14)	C15—C14—H14A	120.7
O8—Er1—N1	105.04 (14)	N3—C15—C14	123.0 (5)
O3—Er1—N4	86.12 (14)	N3—C15—H15A	118.5
O2—Er1—N4	99.60 (14)	C14—C15—H15A	118.5
O4—Er1—N4	26.44 (13)	C30—C29—C28	120.8 (6)
O9—Er1—N4	163.74 (14)	C30—C29—H29A	119.6
N2—Er1—N4	95.58 (15)	C28—C29—H29A	119.6
N3—Er1—N4	73.29 (14)	N2—C10—C9	122.1 (5)
O5—Er1—N4	26.02 (13)	N2—C10—C11	115.5 (5)
O8—Er1—N4	144.24 (13)	C9—C10—C11	122.4 (5)
N1—Er1—N4	98.48 (15)	C13—C12—C11	118.0 (6)
O3—Er1—N5	102.61 (14)	C13—C12—H12A	121.0
O2—Er1—N5	78.62 (13)	C11—C12—H12A	121.0
O4—Er1—N5	153.86 (14)	C10—C9—C8	120.1 (5)
O9—Er1—N5	25.92 (12)	C10—C9—H9A	119.9
N2—Er1—N5	80.12 (14)	C8—C9—H9A	119.9
N3—Er1—N5	97.02 (14)	C8—C7—C6	119.0 (5)
O5—Er1—N5	151.79 (13)	C8—C7—H7A	120.5
O8—Er1—N5	26.08 (12)	C6—C7—H7A	120.5
N1—Er1—N5	87.62 (14)	C18—C17—C16	123.9 (6)
N4—Er1—N5	170.31 (13)	C18—C17—H17A	118.0
C25—O2—Er1	134.4 (3)	C16—C17—H17A	118.0
N5—O9—Er1	97.2 (3)	O1—C8—C7	125.3 (5)
O7—N5—O9	122.9 (5)	O1—C8—C9	116.4 (5)
O7—N5—O8	121.3 (5)	C7—C8—C9	118.2 (5)
O9—N5—O8	115.7 (5)	C8—O1—C16	117.8 (4)
O7—N5—Er1	179.8 (4)	C31—C32—C33	120.0 (6)
O9—N5—Er1	56.9 (3)	C31—C32—H32A	120.0
O8—N5—Er1	58.9 (3)	C33—C32—H32A	120.0
C27—O3—Er1	133.5 (3)	C20—C21—C22	118.6 (5)
N5—O8—Er1	95.0 (3)	C20—C21—H21A	120.7
C10—N2—C6	117.8 (5)	C22—C21—H21A	120.7
C10—N2—Er1	120.2 (3)	C32—C31—C30	119.7 (6)
C6—N2—Er1	120.7 (3)	C32—C31—H31A	120.2
C14—C13—C12	120.2 (5)	C30—C31—H31A	120.2
C14—C13—H13A	119.9	N6—C34—C35	176.9 (9)
C12—C13—H13A	119.9	C34—C35—H35A	109.5
C1—N1—C5	117.8 (5)	C34—C35—H35B	109.5
C1—N1—Er1	122.6 (4)	H35A—C35—H35B	109.5
C5—N1—Er1	119.5 (3)	C34—C35—H35C	109.5
C15—N3—C11	118.0 (5)	H35A—C35—H35C	109.5
C15—N3—Er1	121.7 (4)	H35B—C35—H35C	109.5
C11—N3—Er1	120.0 (3)	N4—O5—Er1	94.5 (3)
C27—C26—C25	124.3 (5)	N4—O4—Er1	96.5 (3)
C27—C26—H26	117.9	O6—N4—O5	121.9 (5)
C25—C26—H26	117.9	O6—N4—O4	122.0 (5)
C19—C24—C23	119.2 (5)	O5—N4—O4	116.0 (5)
C19—C24—C25	119.0 (5)	O6—N4—Er1	171.8 (4)
C23—C24—C25	121.7 (5)	O5—N4—Er1	59.5 (3)
N2—C6—C7	122.7 (5)	O4—N4—Er1	57.0 (3)
N2—C6—C5	116.2 (5)	C1—C2—C3	118.4 (5)
C7—C6—C5	121.0 (5)	C1—C2—H2A	120.8
C19—C20—C21	121.4 (5)	C3—C2—H2A	120.8
C19—C20—H20A	119.3	O1—C16—C17	112.8 (5)
C21—C20—H20A	119.3	O1—C16—H16A	109.0
C22—C23—C24	120.0 (5)	C17—C16—H16A	109.0
C22—C23—H23A	120.0	O1—C16—H16B	109.0
C24—C23—H23A	120.0	C17—C16—H16B	109.0
N1—C1—C2	123.2 (5)	H16A—C16—H16B	107.8
N1—C1—H1A	118.4	C29—C30—C31	120.6 (6)
C2—C1—H1A	118.4	C29—C30—H30A	119.7
C17—C18—H18A	120.0	C31—C30—H30A	119.7

Experimental details

Crystal data
Chemical formula	[Er(C₁₅H₁₁O₂)(NO₃)₂(C₁₈H₁₅N₃O)]·C₂H₃N
M_r	844.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	13.245 (4), 15.871 (4), 16.135 (5)
β (°)	103.374 (6)
V (Å³)	3299.8 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.61
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.550, 0.598
No. of measured, independent and observed [I > 2σ(I)] reflections	15598, 6429, 4383
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.088, 1.04
No. of reflections	6429
No. of parameters	460
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.65, −1.14

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Er1—O3	2.224 (3)	Er1—N3	2.460 (4)
Er1—O2	2.228 (4)	Er1—O5	2.465 (4)
Er1—O4	2.410 (4)	Er1—O8	2.468 (4)
Er1—O9	2.425 (4)	Er1—N1	2.515 (4)
Er1—N2	2.447 (4)

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 50903001, 50803027), the Jiangsu Natural Science Foundation (No. 08KJD430020), the Natural Science Foundation of Anhui Province (grant No. 070414197) and the Nanjing University of Posts & Telecommunications Grant (NUPT) (No. NY207039) for financial support.

References

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