(Acetyl­acetonato-κ2O,O′)(phthalo­cyaninato-κ4N)(phen­an­throline-κ2N,N′)erbium(III)

Li, H.-F.; Yan, P.-F.

doi:10.1107/S1600536812003972

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page m251

doi:10.1107/S1600536812003972

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(Acetylacetonato-κ²O,O′)(phthalocyaninato-κ⁴N)(phenanthroline-κ²N,N′)erbium(III)

Hong-Feng Li ^a and Peng-Fei Yan ^a ^*

^aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: lhf4612@163.com

(Received 26 December 2011; accepted 30 January 2012; online 4 February 2012)

The title complex, [Er(C₃₂H₁₆N₈)(C₅H₇O₂)(C₁₂H₈N₂)], possesses a mirror plane and the asymmetric unit is half of the molecule. The Er^III cation, lying on the mirror plane, is eight-coordinated by two O atoms from acetylacetone, two N (N_phen) atoms from 1,10-phenanthroline and four isoindole N (N_iso) atoms from the phthalocyanine ligand in an antiprismatic geometry. The Er—N distances are in the range 2.376 (5)–2.529 (4) Å and the Er—O distance is 2.272 (3) Å. Notably, the Er—N_iso bonds are shorter than the Er—N_phen bonds, but longer than the Er—O bonds.

Related literature

For background to phthalocyanines, see: Kuznetsova et al. (2002 ); Kalashnikova et al. (2007 ). For a similar erbium complex, see: Zugle et al. (2011 ).

Experimental

Crystal data

[Er(C₃₂H₁₆N₈)(C₅H₇O₂)(C₁₂H₈N₂)]
M_r = 959.10
Monoclinic, P 2₁ /m
a = 9.913 (2) Å
b = 16.887 (3) Å
c = 12.622 (3) Å
β = 106.72 (3)°
V = 2023.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.13 mm⁻¹
T = 293 K
0.28 × 0.22 × 0.17 mm

Data collection

Bruker SMART1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.576, T_max = 0.696
19901 measured reflections
4769 independent reflections
3876 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.13
4769 reflections
287 parameters
H-atom parameters constrained
Δρ_max = 2.01 e Å⁻³
Δρ_min = −2.24 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003972/vm2147sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003972/vm2147Isup2.hkl

checkCIF report

Comment top

In recent years, lanthanide complexes with organic ligands have been widely used in areas such as fluorescent materials, electroluminescence and as fluorescence probes. Phthalocyanines (Pc) are of the most famous macrocyclic compounds that possess interesting physical and chemical properties (Kuznetsova et al., 2002; Kalashnikova et al., 2007; Zugle et al., 2011). Therefore, synthesis and characterization of novel phthalocyanine complexes of lanthanides remain attractive to researchers, where diverse ratio of Pc/Ln could be expected. These lanthanide phthalocyanine derivatives have high intrinsic conductivity and interesting electrochemical behavior. Herein, we present the synthesis and structure of a phthalocyaninato erbium complex Er(C₃₂H₁₆N₈)(C₁₂H₈N₂)(C₅H₇O₂). The complex is mirror-related and the central Er^III ion is located on the mirror plane. The Er^III ion is eight-coordinated to two O atoms from acetylacetone, two N (N_phen) atoms from 1,10-phenanthroline and four isoindole N (N_iso) atoms from the phthalocyanine ligand (Fig. 1). The Er—N distances are in the range of 2.376 (5)–2.529 (4) Å, and the Er—O distance is 2.272 (3) Å. The Er—N_iso bond distances are shorter than the Er—N_phen bond distances, but longer than the Er—O bond distances. The symmetry-related Pc^2- units are not parallel. The positive charge of the Er^III ion is balanced by the Pc^2- and acac^- groups. Strong π–π interactions (Fig. 2) could be found between the pyrrolyl group of Pc and the aromatic ring of 1,10-phenanthroline with a Cg1ⁱⁱ···Cg2 distance of 3.424 (3) Å and between the aromatic ring of the isoindole of Pc and the 1,10-phenanthroline with a Cg2···Cg3ⁱⁱ distance of 3.657 (3) Å (Cg1, Cg2 and Cg3 are the centroids of the rings with atoms N5, C13, C14, C13ⁱ,C14ⁱ, atoms C17, C18, C22, C17ⁱ, C18ⁱ, C22ⁱ, and atoms C14–C16, C14ⁱ-C16ⁱ, respectively; symmetry codes: (i) x, -y + 3/2, z, (ii) 1 + x, y,z).

Related literature top

For background to phthalocyanines, see: Kuznetsova et al. 2002; Kalashnikova et al. 2007. For a similar erbium complex, see: Zugle et al. 2011.

Experimental top

A mixture of Er(acac)₃.H₂O (0.0481 g, 0.10 mmol), dicyanobenzene (0.0512 g, 0.40 mmol), and DBU (0.076 g, 0.50 mmol) in n-pentanol (3 ml) was heated at 100 ° for 1.5 h under a slow stream of nitrogen (acac: acetylacetone; DBU: 1,8-diazabicyclo(5.4.0)undec-7-ene). After the volatiles were removed in vacuo, the residue was chromatographed on a silica gel column with CHCl₃ with 2.5% of methanol (v:v) as the eluent to give a blue band containing Er(Pc)(acac)(phen) (23 mg, 20%). Single crystals suitable for X-ray analyses were obtained by slow diffusion of methanol into the chloroform solution of the complex. Calc. for C₄₉H₃₁ErN₁₀O₂: C 31.26, H 3.26, N 14.60. Found: C 31.20, H 3.24, N 14.61.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids [symmetry code A: x, -y + 3/2, z].
	Fig. 2. π–π interaction between the phthalocyanine isoindole group and the adjacent 1,10-phenanthroline ring as shown by the red dashed line [symmetry code: 1 + x, y, z].

(Acetylacetonato-κ²O,O')(phthalocyaninato- κ⁴N)(phenanthroline-κ²N,N')erbium(III) top

Crystal data top

[Er(C₃₂H₁₆N₈)(C₅H₇O₂)(C₁₂H₈N₂)]	F(000) = 958
M_r = 959.10	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 15893 reflections
a = 9.913 (2) Å	θ = 6.2–54.9°
b = 16.887 (3) Å	µ = 2.13 mm⁻¹
c = 12.622 (3) Å	T = 293 K
β = 106.72 (3)°	Block, purple
V = 2023.7 (7) Å³	0.28 × 0.22 × 0.17 mm
Z = 2

Data collection top

Bruker SMART1000 CCD diffractometer	4769 independent reflections
Radiation source: fine-focus sealed tube	3876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −21→21
T_min = 0.576, T_max = 0.696	l = −16→16
19901 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0219P)² + 5.3744P] where P = (F_o² + 2F_c²)/3
4769 reflections	(Δ/σ)_max < 0.001
287 parameters	Δρ_max = 2.01 e Å⁻³
0 restraints	Δρ_min = −2.24 e Å⁻³

Crystal data top

[Er(C₃₂H₁₆N₈)(C₅H₇O₂)(C₁₂H₈N₂)]	V = 2023.7 (7) Å³
M_r = 959.10	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 9.913 (2) Å	µ = 2.13 mm⁻¹
b = 16.887 (3) Å	T = 293 K
c = 12.622 (3) Å	0.28 × 0.22 × 0.17 mm
β = 106.72 (3)°

Data collection top

Bruker SMART1000 CCD diffractometer	4769 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3876 reflections with I > 2σ(I)
T_min = 0.576, T_max = 0.696	R_int = 0.050
19901 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.13	Δρ_max = 2.01 e Å⁻³
4769 reflections	Δρ_min = −2.24 e Å⁻³
287 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	0.56660 (3)	0.7500	0.21203 (3)	0.03343 (10)
O1	0.5186 (3)	0.83217 (18)	0.0633 (3)	0.0439 (8)
N1	0.6747 (6)	0.7500	0.4083 (5)	0.0414 (13)
N2	0.7009 (4)	0.8908 (2)	0.4457 (3)	0.0474 (10)
N3	0.4958 (4)	0.8662 (2)	0.2898 (3)	0.0380 (8)
N4	0.2664 (4)	0.8910 (2)	0.1574 (3)	0.0406 (9)
N5	0.3167 (5)	0.7500	0.1645 (5)	0.0375 (12)
N6	0.7888 (4)	0.8299 (2)	0.2344 (3)	0.0425 (9)
C1	1.0327 (7)	0.7909 (4)	0.7333 (6)	0.097 (3)
H1A	1.0939	0.8181	0.7918	0.117*
C2	0.9429 (6)	0.8332 (4)	0.6473 (6)	0.082 (2)
H2A	0.9435	0.8883	0.6472	0.098*
C3	0.8524 (5)	0.7913 (3)	0.5617 (4)	0.0537 (14)
C4	0.7385 (5)	0.8153 (3)	0.4657 (4)	0.0432 (11)
C5	0.5860 (5)	0.9128 (3)	0.3669 (4)	0.0421 (11)
C6	0.5352 (5)	0.9944 (3)	0.3562 (4)	0.0479 (12)
C7	0.5881 (7)	1.0633 (3)	0.4118 (5)	0.0688 (18)
H7A	0.6729	1.0636	0.4678	0.083*
C8	0.5102 (8)	1.1316 (3)	0.3812 (6)	0.086 (2)
H8A	0.5440	1.1788	0.4169	0.103*
C9	0.3831 (8)	1.1317 (3)	0.2985 (6)	0.0763 (19)
H9A	0.3333	1.1788	0.2800	0.092*
C10	0.3293 (6)	1.0629 (3)	0.2435 (5)	0.0584 (14)
H10A	0.2431	1.0626	0.1890	0.070*
C11	0.4085 (5)	0.9943 (3)	0.2722 (4)	0.0430 (11)
C12	0.3848 (5)	0.9130 (2)	0.2331 (4)	0.0405 (11)
C13	0.2344 (4)	0.8157 (3)	0.1314 (4)	0.0384 (10)
C14	0.0918 (4)	0.7912 (3)	0.0671 (4)	0.0445 (11)
C15	−0.0314 (5)	0.8337 (3)	0.0220 (4)	0.0534 (13)
H15A	−0.0315	0.8888	0.0213	0.064*
C16	−0.1538 (5)	0.7911 (3)	−0.0217 (5)	0.0614 (15)
H16A	−0.2380	0.8181	−0.0517	0.074*
C17	0.9133 (4)	0.7927 (3)	0.2813 (4)	0.0402 (10)
C18	1.0409 (5)	0.8338 (3)	0.3219 (4)	0.0461 (12)
C19	1.0361 (6)	0.9163 (3)	0.3109 (5)	0.0586 (15)
H19A	1.1178	0.9460	0.3380	0.070*
C20	0.9121 (5)	0.9531 (3)	0.2606 (5)	0.0600 (15)
H20A	0.9089	1.0077	0.2508	0.072*
C21	0.7899 (5)	0.9078 (3)	0.2238 (5)	0.0500 (13)
H21A	0.7054	0.9336	0.1904	0.060*
C22	1.1681 (5)	0.7899 (3)	0.3668 (4)	0.0546 (14)
H22A	1.2522	0.8169	0.3966	0.066*
C23	0.3996 (6)	0.8988 (3)	−0.1003 (5)	0.0666 (16)
H23A	0.3257	0.9225	−0.0758	0.100*
H23B	0.3651	0.8871	−0.1778	0.100*
H23C	0.4774	0.9349	−0.0877	0.100*
C24	0.4475 (5)	0.8234 (3)	−0.0367 (4)	0.0461 (12)
C25	0.4112 (8)	0.7500	−0.0880 (6)	0.0535 (19)
H25A	0.3588	0.7500	−0.1621	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.02919 (14)	0.02436 (13)	0.04208 (18)	0.000	0.00285 (11)	0.000
O1	0.0430 (17)	0.0388 (17)	0.045 (2)	−0.0011 (14)	0.0052 (15)	0.0044 (15)
N1	0.042 (3)	0.026 (2)	0.047 (3)	0.000	−0.002 (2)	0.000
N2	0.054 (2)	0.0318 (19)	0.047 (2)	0.0002 (18)	−0.0009 (19)	−0.0036 (17)
N3	0.0399 (19)	0.0301 (18)	0.041 (2)	−0.0003 (16)	0.0077 (16)	−0.0020 (16)
N4	0.0355 (19)	0.0347 (19)	0.050 (2)	0.0057 (16)	0.0099 (17)	0.0045 (17)
N5	0.027 (2)	0.034 (3)	0.050 (3)	0.000	0.009 (2)	0.000
N6	0.0366 (19)	0.0291 (18)	0.057 (3)	0.0018 (16)	0.0049 (17)	0.0027 (17)
C1	0.078 (4)	0.075 (4)	0.097 (5)	−0.003 (3)	−0.042 (4)	−0.008 (4)
C2	0.074 (4)	0.052 (3)	0.089 (5)	−0.002 (3)	−0.028 (4)	−0.013 (3)
C3	0.050 (3)	0.041 (3)	0.056 (3)	0.001 (2)	−0.009 (2)	−0.004 (2)
C4	0.042 (2)	0.034 (2)	0.047 (3)	0.002 (2)	0.003 (2)	−0.003 (2)
C5	0.049 (3)	0.030 (2)	0.043 (3)	0.000 (2)	0.006 (2)	−0.002 (2)
C6	0.063 (3)	0.029 (2)	0.047 (3)	0.005 (2)	0.007 (2)	0.000 (2)
C7	0.099 (5)	0.034 (3)	0.056 (4)	0.003 (3)	−0.005 (3)	−0.009 (2)
C8	0.131 (6)	0.031 (3)	0.075 (5)	0.009 (3)	−0.002 (4)	−0.011 (3)
C9	0.103 (5)	0.032 (3)	0.084 (5)	0.023 (3)	0.012 (4)	0.000 (3)
C10	0.072 (4)	0.035 (3)	0.064 (4)	0.013 (3)	0.013 (3)	0.006 (2)
C11	0.051 (3)	0.031 (2)	0.048 (3)	0.006 (2)	0.016 (2)	0.003 (2)
C12	0.040 (2)	0.027 (2)	0.054 (3)	0.0056 (19)	0.013 (2)	0.003 (2)
C13	0.032 (2)	0.037 (2)	0.045 (3)	0.0018 (18)	0.0104 (19)	0.003 (2)
C14	0.034 (2)	0.049 (3)	0.046 (3)	0.002 (2)	0.004 (2)	0.002 (2)
C15	0.040 (3)	0.060 (3)	0.054 (3)	0.010 (2)	0.004 (2)	0.006 (3)
C16	0.034 (2)	0.082 (4)	0.059 (3)	0.007 (2)	−0.001 (2)	0.001 (3)
C17	0.035 (2)	0.039 (2)	0.043 (3)	−0.0030 (19)	0.0060 (19)	−0.001 (2)
C18	0.035 (2)	0.052 (3)	0.049 (3)	−0.008 (2)	0.008 (2)	−0.003 (2)
C19	0.047 (3)	0.049 (3)	0.073 (4)	−0.019 (2)	0.007 (3)	−0.007 (3)
C20	0.053 (3)	0.034 (2)	0.088 (5)	−0.012 (2)	0.012 (3)	0.000 (3)
C21	0.041 (2)	0.035 (2)	0.071 (4)	0.000 (2)	0.010 (2)	0.003 (2)
C22	0.037 (2)	0.063 (3)	0.055 (3)	−0.010 (2)	−0.001 (2)	−0.003 (3)
C23	0.077 (4)	0.061 (4)	0.055 (4)	0.003 (3)	0.008 (3)	0.021 (3)
C24	0.037 (2)	0.048 (3)	0.050 (3)	0.001 (2)	0.008 (2)	0.007 (2)
C25	0.052 (4)	0.058 (5)	0.042 (4)	0.000	0.000 (3)	0.000

Geometric parameters (Å, º) top

Er1—O1ⁱ	2.272 (3)	C8—C9	1.386 (9)
Er1—O1	2.272 (3)	C8—H8A	0.9300
Er1—N5	2.376 (5)	C9—C10	1.379 (8)
Er1—N3ⁱ	2.388 (4)	C9—H9A	0.9300
Er1—N3	2.388 (4)	C10—C11	1.388 (6)
Er1—N1	2.400 (6)	C10—H10A	0.9300
Er1—N6	2.529 (4)	C11—C12	1.454 (6)
Er1—N6ⁱ	2.529 (4)	C13—C14	1.472 (6)
O1—C24	1.264 (6)	C14—C15	1.389 (6)
N1—C4	1.371 (5)	C14—C14ⁱ	1.393 (10)
N1—C4ⁱ	1.371 (5)	C15—C16	1.382 (7)
N2—C5	1.331 (6)	C15—H15A	0.9300
N2—C4	1.332 (6)	C16—C16ⁱ	1.388 (12)
N3—C5	1.366 (6)	C16—H16A	0.9300
N3—C12	1.377 (5)	C17—C18	1.404 (6)
N4—C13	1.330 (6)	C17—C17ⁱ	1.443 (9)
N4—C12	1.335 (6)	C18—C19	1.400 (7)
N5—C13ⁱ	1.369 (5)	C18—C22	1.432 (7)
N5—C13	1.369 (5)	C19—C20	1.361 (7)
N6—C21	1.323 (6)	C19—H19A	0.9300
N6—C17	1.359 (5)	C20—C21	1.394 (7)
C1—C1ⁱ	1.383 (13)	C20—H20A	0.9300
C1—C2	1.387 (8)	C21—H21A	0.9300
C1—H1A	0.9300	C22—C22ⁱ	1.346 (11)
C2—C3	1.384 (7)	C22—H22A	0.9300
C2—H2A	0.9300	C23—C24	1.508 (7)
C3—C3ⁱ	1.394 (10)	C23—H23A	0.9600
C3—C4	1.456 (6)	C23—H23B	0.9600
C5—C6	1.461 (6)	C23—H23C	0.9600
C6—C7	1.381 (7)	C24—C25	1.397 (6)
C6—C11	1.391 (7)	C25—C24ⁱ	1.397 (6)
C7—C8	1.380 (8)	C25—H25A	0.9300
C7—H7A	0.9300

O1ⁱ—Er1—O1	75.28 (16)	C8—C7—C6	117.5 (5)
O1ⁱ—Er1—N5	80.57 (14)	C8—C7—H7A	121.3
O1—Er1—N5	80.57 (14)	C6—C7—H7A	121.3
O1ⁱ—Er1—N3ⁱ	79.71 (13)	C7—C8—C9	121.7 (5)
O1—Er1—N3ⁱ	145.58 (12)	C7—C8—H8A	119.1
N5—Er1—N3ⁱ	72.25 (11)	C9—C8—H8A	119.1
O1ⁱ—Er1—N3	145.58 (12)	C10—C9—C8	121.0 (5)
O1—Er1—N3	79.71 (12)	C10—C9—H9A	119.5
N5—Er1—N3	72.25 (11)	C8—C9—H9A	119.5
N3ⁱ—Er1—N3	110.52 (18)	C9—C10—C11	117.6 (5)
O1ⁱ—Er1—N1	141.10 (9)	C9—C10—H10A	121.2
O1—Er1—N1	141.10 (9)	C11—C10—H10A	121.2
N5—Er1—N1	112.6 (2)	C10—C11—C6	121.1 (5)
N3ⁱ—Er1—N1	70.88 (11)	C10—C11—C12	132.5 (5)
N3—Er1—N1	70.88 (11)	C6—C11—C12	106.4 (4)
O1ⁱ—Er1—N6	112.75 (13)	N4—C12—N3	128.2 (4)
O1—Er1—N6	74.62 (12)	N4—C12—C11	121.9 (4)
N5—Er1—N6	147.12 (8)	N3—C12—C11	109.8 (4)
N3ⁱ—Er1—N6	137.93 (12)	N4—C13—N5	128.4 (4)
N3—Er1—N6	82.25 (12)	N4—C13—C14	121.8 (4)
N1—Er1—N6	76.65 (15)	N5—C13—C14	109.6 (4)
O1ⁱ—Er1—N6ⁱ	74.62 (12)	C15—C14—C14ⁱ	121.1 (3)
O1—Er1—N6ⁱ	112.75 (13)	C15—C14—C13	132.3 (5)
N5—Er1—N6ⁱ	147.12 (8)	C14ⁱ—C14—C13	106.3 (3)
N3ⁱ—Er1—N6ⁱ	82.25 (12)	C16—C15—C14	117.6 (5)
N3—Er1—N6ⁱ	137.93 (12)	C16—C15—H15A	121.2
N1—Er1—N6ⁱ	76.65 (15)	C14—C15—H15A	121.2
N6—Er1—N6ⁱ	64.52 (16)	C15—C16—C16ⁱ	121.4 (3)
C24—O1—Er1	132.6 (3)	C15—C16—H16A	119.3
C4—N1—C4ⁱ	107.2 (5)	C16ⁱ—C16—H16A	119.3
C4—N1—Er1	123.2 (3)	N6—C17—C18	122.7 (4)
C4ⁱ—N1—Er1	123.2 (3)	N6—C17—C17ⁱ	117.5 (2)
C5—N2—C4	122.7 (4)	C18—C17—C17ⁱ	119.6 (3)
C5—N3—C12	107.5 (4)	C19—C18—C17	117.0 (4)
C5—N3—Er1	123.8 (3)	C19—C18—C22	123.8 (4)
C12—N3—Er1	123.0 (3)	C17—C18—C22	119.1 (5)
C13—N4—C12	122.8 (4)	C20—C19—C18	120.1 (5)
C13ⁱ—N5—C13	108.2 (5)	C20—C19—H19A	119.9
C13ⁱ—N5—Er1	124.3 (2)	C18—C19—H19A	119.9
C13—N5—Er1	124.3 (2)	C19—C20—C21	119.1 (5)
C21—N6—C17	118.1 (4)	C19—C20—H20A	120.4
C21—N6—Er1	123.5 (3)	C21—C20—H20A	120.4
C17—N6—Er1	117.0 (3)	N6—C21—C20	122.9 (5)
C1ⁱ—C1—C2	121.0 (4)	N6—C21—H21A	118.6
C1ⁱ—C1—H1A	119.5	C20—C21—H21A	118.6
C2—C1—H1A	119.5	C22ⁱ—C22—C18	121.2 (3)
C3—C2—C1	118.3 (6)	C22ⁱ—C22—H22A	119.4
C3—C2—H2A	120.9	C18—C22—H22A	119.4
C1—C2—H2A	120.9	C24—C23—H23A	109.5
C2—C3—C3ⁱ	120.8 (3)	C24—C23—H23B	109.5
C2—C3—C4	132.9 (5)	H23A—C23—H23B	109.5
C3ⁱ—C3—C4	106.2 (3)	C24—C23—H23C	109.5
N2—C4—N1	127.5 (4)	H23A—C23—H23C	109.5
N2—C4—C3	122.2 (4)	H23B—C23—H23C	109.5
N1—C4—C3	110.2 (4)	O1—C24—C25	124.2 (5)
N2—C5—N3	128.0 (4)	O1—C24—C23	115.6 (5)
N2—C5—C6	122.0 (4)	C25—C24—C23	120.2 (5)
N3—C5—C6	109.9 (4)	C24—C25—C24ⁱ	125.1 (7)
C7—C6—C11	121.1 (5)	C24—C25—H25A	117.5
C7—C6—C5	132.6 (5)	C24ⁱ—C25—H25A	117.5
C11—C6—C5	106.3 (4)

O1ⁱ—Er1—O1—C24	24.4 (5)	C4ⁱ—N1—C4—C3	2.5 (8)
N5—Er1—O1—C24	−58.2 (4)	Er1—N1—C4—C3	−149.8 (4)
N3ⁱ—Er1—O1—C24	−20.3 (5)	C2—C3—C4—N2	−0.7 (11)
N3—Er1—O1—C24	−131.7 (4)	C3ⁱ—C3—C4—N2	174.2 (4)
N1—Er1—O1—C24	−172.7 (4)	C2—C3—C4—N1	−176.5 (7)
N6—Er1—O1—C24	143.6 (4)	C3ⁱ—C3—C4—N1	−1.6 (5)
N6ⁱ—Er1—O1—C24	90.4 (4)	C4—N2—C5—N3	−5.7 (9)
O1ⁱ—Er1—N1—C4	150.6 (3)	C4—N2—C5—C6	171.1 (5)
O1—Er1—N1—C4	−2.5 (6)	C12—N3—C5—N2	174.0 (5)
N5—Er1—N1—C4	−106.0 (4)	Er1—N3—C5—N2	−32.0 (7)
N3ⁱ—Er1—N1—C4	−166.4 (5)	C12—N3—C5—C6	−3.1 (6)
N3—Er1—N1—C4	−45.6 (4)	Er1—N3—C5—C6	150.8 (3)
N6—Er1—N1—C4	40.8 (4)	N2—C5—C6—C7	4.0 (10)
N6ⁱ—Er1—N1—C4	107.3 (5)	N3—C5—C6—C7	−178.7 (6)
O1ⁱ—Er1—N1—C4ⁱ	2.5 (6)	N2—C5—C6—C11	−175.2 (5)
O1—Er1—N1—C4ⁱ	−150.6 (3)	N3—C5—C6—C11	2.1 (6)
N5—Er1—N1—C4ⁱ	106.0 (4)	C11—C6—C7—C8	0.2 (10)
N3ⁱ—Er1—N1—C4ⁱ	45.6 (4)	C5—C6—C7—C8	−178.8 (7)
N3—Er1—N1—C4ⁱ	166.4 (5)	C6—C7—C8—C9	0.6 (11)
N6—Er1—N1—C4ⁱ	−107.3 (5)	C7—C8—C9—C10	0.0 (12)
N6ⁱ—Er1—N1—C4ⁱ	−40.8 (4)	C8—C9—C10—C11	−1.3 (10)
O1ⁱ—Er1—N3—C5	−153.5 (3)	C9—C10—C11—C6	2.1 (9)
O1—Er1—N3—C5	−109.7 (4)	C9—C10—C11—C12	179.5 (6)
N5—Er1—N3—C5	167.0 (4)	C7—C6—C11—C10	−1.6 (9)
N3ⁱ—Er1—N3—C5	104.5 (4)	C5—C6—C11—C10	177.7 (5)
N1—Er1—N3—C5	44.5 (4)	C7—C6—C11—C12	−179.6 (6)
N6—Er1—N3—C5	−34.0 (4)	C5—C6—C11—C12	−0.3 (6)
N6ⁱ—Er1—N3—C5	3.0 (5)	C13—N4—C12—N3	5.4 (8)
O1ⁱ—Er1—N3—C12	−3.4 (5)	C13—N4—C12—C11	−170.7 (5)
O1—Er1—N3—C12	40.4 (3)	C5—N3—C12—N4	−173.5 (5)
N5—Er1—N3—C12	−42.9 (3)	Er1—N3—C12—N4	32.2 (7)
N3ⁱ—Er1—N3—C12	−105.4 (3)	C5—N3—C12—C11	2.9 (5)
N1—Er1—N3—C12	−165.4 (4)	Er1—N3—C12—C11	−151.3 (3)
N6—Er1—N3—C12	116.1 (4)	C10—C11—C12—N4	−2.5 (9)
N6ⁱ—Er1—N3—C12	153.0 (3)	C6—C11—C12—N4	175.1 (5)
O1ⁱ—Er1—N5—C13ⁱ	40.5 (4)	C10—C11—C12—N3	−179.3 (5)
O1—Er1—N5—C13ⁱ	117.0 (5)	C6—C11—C12—N3	−1.6 (6)
N3ⁱ—Er1—N5—C13ⁱ	−41.6 (4)	C12—N4—C13—N5	−7.9 (8)
N3—Er1—N5—C13ⁱ	−160.9 (5)	C12—N4—C13—C14	166.2 (5)
N1—Er1—N5—C13ⁱ	−101.2 (4)	C13ⁱ—N5—C13—N4	171.1 (3)
N6—Er1—N5—C13ⁱ	158.2 (3)	Er1—N5—C13—N4	−28.3 (8)
N6ⁱ—Er1—N5—C13ⁱ	−0.7 (7)	C13ⁱ—N5—C13—C14	−3.5 (7)
O1ⁱ—Er1—N5—C13	−117.0 (5)	Er1—N5—C13—C14	157.1 (4)
O1—Er1—N5—C13	−40.5 (4)	N4—C13—C14—C15	−0.1 (9)
N3ⁱ—Er1—N5—C13	160.9 (5)	N5—C13—C14—C15	175.0 (6)
N3—Er1—N5—C13	41.6 (4)	N4—C13—C14—C14ⁱ	−172.9 (4)
N1—Er1—N5—C13	101.2 (4)	N5—C13—C14—C14ⁱ	2.2 (4)
N6—Er1—N5—C13	0.7 (7)	C14ⁱ—C14—C15—C16	0.6 (6)
N6ⁱ—Er1—N5—C13	−158.2 (3)	C13—C14—C15—C16	−171.4 (5)
O1ⁱ—Er1—N6—C21	114.3 (4)	C14—C15—C16—C16ⁱ	−0.6 (6)
O1—Er1—N6—C21	48.0 (4)	C21—N6—C17—C18	2.2 (8)
N5—Er1—N6—C21	5.6 (6)	Er1—N6—C17—C18	−164.8 (4)
N3ⁱ—Er1—N6—C21	−145.6 (4)	C21—N6—C17—C17ⁱ	−173.3 (4)
N3—Er1—N6—C21	−33.4 (4)	Er1—N6—C17—C17ⁱ	19.7 (4)
N1—Er1—N6—C21	−105.5 (4)	N6—C17—C18—C19	−0.9 (8)
N6ⁱ—Er1—N6—C21	173.1 (4)	C17ⁱ—C17—C18—C19	174.5 (4)
O1ⁱ—Er1—N6—C17	−79.5 (4)	N6—C17—C18—C22	−178.0 (5)
O1—Er1—N6—C17	−145.8 (4)	C17ⁱ—C17—C18—C22	−2.6 (6)
N5—Er1—N6—C17	171.8 (4)	C17—C18—C19—C20	−1.4 (9)
N3ⁱ—Er1—N6—C17	20.6 (4)	C22—C18—C19—C20	175.6 (6)
N3—Er1—N6—C17	132.8 (4)	C18—C19—C20—C21	2.2 (9)
N1—Er1—N6—C17	60.7 (3)	C17—N6—C21—C20	−1.3 (8)
N6ⁱ—Er1—N6—C17	−20.7 (4)	Er1—N6—C21—C20	164.8 (4)
C1ⁱ—C1—C2—C3	0.4 (9)	C19—C20—C21—N6	−0.9 (9)
C1—C2—C3—C3ⁱ	−0.4 (9)	C19—C18—C22—C22ⁱ	−174.3 (4)
C1—C2—C3—C4	173.9 (7)	C17—C18—C22—C22ⁱ	2.6 (6)
C5—N2—C4—N1	4.0 (9)	Er1—O1—C24—C25	−19.4 (8)
C5—N2—C4—C3	−171.0 (5)	Er1—O1—C24—C23	159.7 (4)
C4ⁱ—N1—C4—N2	−172.9 (3)	O1—C24—C25—C24ⁱ	0.2 (12)
Er1—N1—C4—N2	34.7 (8)	C23—C24—C25—C24ⁱ	−178.8 (5)

Symmetry code: (i) x, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	[Er(C₃₂H₁₆N₈)(C₅H₇O₂)(C₁₂H₈N₂)]
M_r	959.10
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	9.913 (2), 16.887 (3), 12.622 (3)
β (°)	106.72 (3)
V (Å³)	2023.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.28 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.576, 0.696
No. of measured, independent and observed [I > 2σ(I)] reflections	19901, 4769, 3876
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.13
No. of reflections	4769
No. of parameters	287
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.01, −2.24

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (grant Nos. 20872030 and 20972043), Heilongjiang Province (grant Nos. 2009RFXXG201, GC09A402 and 2010td03) and Heilongjiang University.

References

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