[N,N′-Bis(3-meth­oxy-2-oxidobenzyl­idene)ethane-1,2-diaminium-κ4O,O′,O′′,O′′′]tris­(nitrato-κ2O,O′)erbium(III)

Gao, T.; Li, G.-M.; Gao, P.; Yan, P.-F.; Hou, G.-F.

doi:10.1107/S1600536809055184

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m107

https://doi.org/10.1107/S1600536809055184

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[N,N′-Bis(3-methoxy-2-oxidobenzylidene)ethane-1,2-diaminium-κ⁴O,O′,O′′,O′′′]tris(nitrato-κ²O,O′)erbium(III)

Ting Gao,^a Guang-Ming Li,^a Po Gao,^a Peng-Fei Yan ^a ^* and Guang-Feng Hou ^a

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

(Received 1 December 2009; accepted 23 December 2009; online 9 January 2010)

In the mononuclear salen-type complex, [Er(NO₃)₃(C₁₈H₂₀N₂O₄)], the Er^III ion is ten-coordinated in a distorted hexadecahedral geometry by six O atoms of three nitrate anions and four O atoms of the salen-like ligand. Intermolecular N—H⋯O hydrogen bonds occur. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For similar lanthanide complexes of the same salen-like ligand, see: Gao et al. (2008 , 2009 ).

Experimental

Crystal data

[Er(NO₃)₃(C₁₈H₂₀N₂O₄)]
M_r = 681.65
Monoclinic, P 2₁ /n
a = 14.098 (3) Å
b = 11.865 (2) Å
c = 14.571 (3) Å
β = 103.98 (3)°
V = 2365.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 291 K
0.37 × 0.36 × 0.34 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.344, T_max = 0.368
21792 measured reflections
5358 independent reflections
4748 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.049
S = 1.04
5358 reflections
344 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.85 (1)	1.89 (3)	2.574 (3)	137 (3)
N1—H1⋯O1	0.85 (1)	1.84 (2)	2.567 (3)	143 (3)
C7—H7⋯O5ⁱ	0.93	2.33	3.073 (3)	137
C9—H9A⋯O12ⁱⁱ	0.97	2.50	3.241 (3)	133
C10—H10⋯O9ⁱⁱⁱ	0.93	2.57	3.395 (4)	148
C14—H14⋯O12^iv	0.93	2.50	3.341 (4)	150
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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 global, I. DOI: https://doi.org/10.1107/S1600536809055184/pk2218sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055184/pk2218Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of salen-type lanthanide complexes (Gao et al., 2008, 2009), we present here the crystal structure of the title compound. As shown in Fig. 1, the ten-coordinate Er^III ion adopts a hexadecahedral geometry provided by the O atoms of three bidentate nitrate anions and by one ligand that utilizes two hydroxyl and two methoxy oxygen atoms, while the protonated nitrogen atoms remain uncoordinated. This compound is isostructural with the corresponding Nd, Eu, Tb and Dy complexes (Gao et al., 2008, 2009). The Er—O bond distances range from 2.2462 (19) to 2.682 (2) Å, with the shorter bonds involving the O1 and O3 deprotonated phenol oxygen atoms. The crystal structure is stabilized by intra- and intermolecular N—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For similar lanthanide complexes of the same salen-like ligand, see: Gao et al. (2008, 2009).

Experimental top

The title complex was obtained by the treatment of erbium (III) nitrate hexahydrate (0.114 g, 0.25 mmol) with the salen-type ligand (0.083 g, 0.25 mmol) in acetonitrile/methanol (10 ml/10 ml). The mixture was stirred for 3 h. The reaction mixture was filtered; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for for C₁₈H₂₀Er₁N₅O₁₃: C 31.72, H 2.96, N 10.27%; found: C 32.08, H 3.00, N 10.38%.

Structure description top

For similar lanthanide complexes of the same salen-like ligand, see: Gao et al. (2008, 2009).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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 the the title compound, showing 30% probability displacement ellipsoids.

[N,N'-Bis(3-methoxy-2-oxidobenzylidene)ethane-1,2-diaminium- κ⁴O,O',O'',O''']tris(nitrato- κ²O,O')erbium(III) top

Crystal data top

[Er(NO₃)₃(C₁₈H₂₀N₂O₄)]	F(000) = 1340
M_r = 681.65	D_x = 1.914 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 19557 reflections
a = 14.098 (3) Å	θ = 6.7–55.0°
b = 11.865 (2) Å	µ = 3.63 mm⁻¹
c = 14.571 (3) Å	T = 291 K
β = 103.98 (3)°	Block, brown
V = 2365.1 (8) Å³	0.37 × 0.36 × 0.34 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5358 independent reflections
Radiation source: fine-focus sealed tube	4748 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −18→18
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→13
T_min = 0.344, T_max = 0.368	l = −18→18
21792 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0212P)² + 1.495P] where P = (F_o² + 2F_c²)/3
5358 reflections	(Δ/σ)_max = 0.002
344 parameters	Δρ_max = 0.97 e Å⁻³
2 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Er(NO₃)₃(C₁₈H₂₀N₂O₄)]	V = 2365.1 (8) Å³
M_r = 681.65	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.098 (3) Å	µ = 3.63 mm⁻¹
b = 11.865 (2) Å	T = 291 K
c = 14.571 (3) Å	0.37 × 0.36 × 0.34 mm
β = 103.98 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5358 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4748 reflections with I > 2σ(I)
T_min = 0.344, T_max = 0.368	R_int = 0.024
21792 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	2 restraints
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.97 e Å⁻³
5358 reflections	Δρ_min = −0.32 e Å⁻³
344 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
C1	1.11705 (18)	0.8605 (2)	0.45224 (18)	0.0382 (5)
C2	1.20341 (19)	0.8854 (2)	0.42275 (19)	0.0407 (5)
C3	1.28633 (19)	0.9208 (2)	0.4865 (2)	0.0473 (6)
H3	1.3434	0.9334	0.4667	0.057*
C4	1.2851 (2)	0.9379 (2)	0.5812 (2)	0.0514 (7)
H4	1.3416	0.9618	0.6241	0.062*
C5	1.2025 (2)	0.9199 (2)	0.6108 (2)	0.0482 (6)
H5	1.2021	0.9338	0.6736	0.058*
C6	1.11664 (18)	0.8802 (2)	0.54721 (17)	0.0398 (5)
C7	1.03136 (19)	0.8571 (2)	0.57937 (18)	0.0419 (6)
H7	1.0340	0.8661	0.6433	0.050*
C8	0.8585 (2)	0.8013 (2)	0.5501 (2)	0.0476 (6)
H8A	0.8190	0.8692	0.5424	0.057*
H8B	0.8721	0.7791	0.6161	0.057*
C9	0.8026 (2)	0.7084 (2)	0.4892 (2)	0.0463 (6)
H9A	0.8384	0.6381	0.5029	0.056*
H9B	0.7395	0.6985	0.5038	0.056*
C10	0.71313 (18)	0.7852 (2)	0.33653 (19)	0.0405 (6)
H10	0.6585	0.7963	0.3607	0.049*
C11	0.70956 (17)	0.8234 (2)	0.24387 (18)	0.0378 (5)
C12	0.62437 (19)	0.8736 (2)	0.1881 (2)	0.0487 (6)
H12	0.5690	0.8799	0.2118	0.058*
C13	0.6223 (2)	0.9123 (3)	0.1009 (2)	0.0562 (8)
H13	0.5652	0.9442	0.0647	0.067*
C14	0.7057 (2)	0.9052 (2)	0.0634 (2)	0.0509 (7)
H14	0.7033	0.9319	0.0029	0.061*
C15	0.78977 (18)	0.8588 (2)	0.11660 (18)	0.0393 (5)
C16	0.79432 (17)	0.8157 (2)	0.20754 (18)	0.0353 (5)
C17	0.8799 (3)	0.8857 (3)	−0.0015 (2)	0.0660 (9)
H15	0.8287	0.8495	−0.0475	0.099*
H16	0.9420	0.8669	−0.0135	0.099*
H17	0.8708	0.9659	−0.0056	0.099*
C18	1.2751 (3)	0.8925 (4)	0.2892 (3)	0.0813 (12)
H18	1.2967	0.9685	0.3043	0.122*
H19	1.2567	0.8835	0.2217	0.122*
H20	1.3270	0.8411	0.3158	0.122*
Er1	1.027172 (8)	0.791612 (9)	0.235283 (7)	0.03487 (4)
H1	0.954 (2)	0.824 (3)	0.4667 (10)	0.055 (9)*
H2	0.8358 (18)	0.723 (3)	0.364 (2)	0.065 (10)*
N1	0.95017 (17)	0.8241 (2)	0.52382 (16)	0.0431 (5)
N2	0.78847 (16)	0.7357 (2)	0.38932 (16)	0.0410 (5)
N3	1.0155 (2)	1.0328 (2)	0.1988 (2)	0.0662 (7)
N4	1.07427 (19)	0.6872 (2)	0.07369 (18)	0.0498 (6)
N5	1.08572 (16)	0.57223 (19)	0.31635 (15)	0.0422 (5)
O1	1.04131 (13)	0.82028 (18)	0.39117 (13)	0.0500 (5)
O2	1.19230 (13)	0.86931 (18)	0.32755 (13)	0.0500 (5)
O3	0.87510 (12)	0.77016 (15)	0.25531 (12)	0.0393 (4)
O4	0.87710 (14)	0.84819 (17)	0.09111 (13)	0.0485 (4)
O5	0.97238 (19)	0.9849 (2)	0.25442 (16)	0.0729 (7)
O6	1.0101 (3)	1.1337 (2)	0.1861 (3)	0.1093 (11)
O7	1.06391 (17)	0.96856 (19)	0.15897 (16)	0.0613 (6)
O8	1.12293 (19)	0.7666 (2)	0.11639 (19)	0.0714 (7)
O9	1.0911 (2)	0.6461 (2)	0.00302 (18)	0.0794 (7)
O10	1.00528 (15)	0.6536 (2)	0.10706 (16)	0.0615 (6)
O11	1.14616 (13)	0.64176 (18)	0.29752 (16)	0.0543 (5)
O12	1.11095 (15)	0.48027 (17)	0.35168 (15)	0.0566 (5)
O13	0.99850 (14)	0.60343 (17)	0.29684 (16)	0.0547 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0425 (13)	0.0366 (14)	0.0352 (13)	−0.0009 (10)	0.0089 (10)	0.0014 (10)
C2	0.0466 (14)	0.0346 (13)	0.0415 (14)	−0.0049 (10)	0.0119 (10)	−0.0005 (11)
C3	0.0432 (14)	0.0371 (14)	0.0607 (18)	−0.0041 (11)	0.0111 (12)	−0.0004 (13)
C4	0.0519 (16)	0.0423 (16)	0.0522 (17)	−0.0049 (12)	−0.0025 (12)	−0.0064 (13)
C5	0.0614 (17)	0.0391 (15)	0.0390 (15)	0.0005 (12)	0.0023 (12)	−0.0049 (11)
C6	0.0511 (14)	0.0329 (13)	0.0347 (13)	0.0027 (10)	0.0092 (10)	−0.0002 (10)
C7	0.0570 (16)	0.0376 (14)	0.0321 (13)	0.0075 (11)	0.0127 (11)	−0.0027 (10)
C8	0.0512 (15)	0.0602 (18)	0.0377 (14)	0.0090 (12)	0.0229 (11)	0.0051 (12)
C9	0.0495 (15)	0.0522 (16)	0.0425 (15)	0.0046 (11)	0.0217 (11)	0.0143 (12)
C10	0.0382 (13)	0.0407 (14)	0.0461 (15)	−0.0002 (10)	0.0170 (10)	−0.0042 (11)
C11	0.0364 (12)	0.0369 (13)	0.0406 (14)	0.0045 (9)	0.0102 (10)	−0.0024 (10)
C12	0.0402 (14)	0.0496 (16)	0.0546 (17)	0.0106 (11)	0.0084 (11)	−0.0028 (13)
C13	0.0496 (16)	0.0533 (18)	0.0577 (19)	0.0179 (13)	−0.0027 (13)	0.0056 (14)
C14	0.0638 (18)	0.0448 (16)	0.0390 (15)	0.0085 (12)	0.0022 (12)	0.0072 (12)
C15	0.0460 (14)	0.0371 (14)	0.0347 (13)	0.0039 (10)	0.0094 (10)	0.0018 (10)
C16	0.0378 (12)	0.0328 (13)	0.0353 (13)	0.0031 (9)	0.0091 (9)	0.0009 (9)
C17	0.081 (2)	0.084 (2)	0.0378 (16)	0.0008 (18)	0.0249 (15)	0.0118 (16)
C18	0.068 (2)	0.121 (3)	0.066 (2)	−0.041 (2)	0.0381 (18)	−0.012 (2)
Er1	0.03856 (7)	0.04067 (7)	0.02990 (6)	−0.00224 (4)	0.01707 (4)	0.00026 (4)
N1	0.0496 (13)	0.0531 (14)	0.0309 (12)	0.0030 (10)	0.0181 (9)	0.0011 (10)
N2	0.0410 (12)	0.0482 (13)	0.0382 (12)	0.0027 (9)	0.0183 (9)	0.0038 (9)
N3	0.107 (2)	0.0498 (17)	0.0492 (15)	−0.0087 (14)	0.0328 (15)	−0.0004 (13)
N4	0.0628 (15)	0.0502 (15)	0.0439 (13)	0.0119 (11)	0.0270 (11)	0.0006 (11)
N5	0.0452 (12)	0.0476 (13)	0.0352 (11)	0.0032 (9)	0.0124 (9)	0.0028 (9)
O1	0.0430 (10)	0.0761 (14)	0.0332 (10)	−0.0144 (9)	0.0136 (8)	−0.0086 (9)
O2	0.0476 (10)	0.0648 (13)	0.0430 (11)	−0.0166 (9)	0.0215 (8)	−0.0047 (9)
O3	0.0348 (9)	0.0484 (11)	0.0360 (9)	0.0081 (7)	0.0109 (7)	0.0099 (7)
O4	0.0574 (11)	0.0581 (12)	0.0335 (10)	0.0032 (9)	0.0179 (8)	0.0075 (8)
O5	0.127 (2)	0.0497 (14)	0.0611 (15)	−0.0098 (12)	0.0588 (15)	−0.0098 (10)
O6	0.192 (3)	0.0431 (16)	0.116 (3)	0.0054 (17)	0.082 (2)	0.0152 (16)
O7	0.0805 (15)	0.0568 (13)	0.0560 (13)	−0.0025 (11)	0.0344 (11)	0.0099 (11)
O8	0.0880 (17)	0.0701 (16)	0.0739 (17)	−0.0253 (13)	0.0539 (14)	−0.0199 (13)
O9	0.118 (2)	0.0705 (17)	0.0685 (16)	0.0085 (14)	0.0590 (15)	−0.0145 (13)
O10	0.0520 (12)	0.0793 (16)	0.0589 (14)	−0.0083 (10)	0.0245 (10)	−0.0197 (11)
O11	0.0397 (10)	0.0558 (13)	0.0686 (14)	−0.0013 (8)	0.0151 (9)	0.0030 (10)
O12	0.0679 (13)	0.0489 (12)	0.0524 (12)	0.0159 (9)	0.0132 (9)	0.0122 (10)
O13	0.0414 (10)	0.0518 (12)	0.0753 (14)	0.0058 (8)	0.0225 (9)	0.0181 (10)

Geometric parameters (Å, º) top

C1—O1	1.304 (3)	C15—C16	1.407 (3)
C1—C6	1.405 (3)	C16—O3	1.300 (3)
C1—C2	1.417 (3)	C17—O4	1.430 (3)
C2—C3	1.371 (4)	C17—H15	0.9600
C2—O2	1.371 (3)	C17—H16	0.9600
C3—C4	1.399 (4)	C17—H17	0.9600
C3—H3	0.9300	C18—O2	1.437 (3)
C4—C5	1.354 (4)	C18—H18	0.9600
C4—H4	0.9300	C18—H19	0.9600
C5—C6	1.416 (4)	C18—H20	0.9600
C5—H5	0.9300	Er1—O3	2.2469 (17)
C6—C7	1.419 (4)	Er1—O1	2.2576 (19)
C7—N1	1.293 (3)	Er1—O10	2.447 (2)
C7—H7	0.9300	Er1—O5	2.458 (2)
C8—N1	1.460 (3)	Er1—O8	2.458 (2)
C8—C9	1.512 (4)	Er1—O11	2.462 (2)
C8—H8A	0.9700	Er1—O13	2.476 (2)
C8—H8B	0.9700	Er1—O7	2.488 (2)
C9—N2	1.457 (3)	Er1—O2	2.562 (2)
C9—H9A	0.9700	Er1—O4	2.682 (2)
C9—H9B	0.9700	Er1—N4	2.877 (2)
C10—N2	1.292 (3)	Er1—N5	2.895 (2)
C10—C11	1.413 (4)	N1—H1	0.846 (10)
C10—H10	0.9300	N2—H2	0.847 (10)
C11—C12	1.409 (4)	N3—O6	1.211 (4)
C11—C16	1.422 (3)	N3—O7	1.255 (3)
C12—C13	1.344 (4)	N3—O5	1.260 (3)
C12—H12	0.9300	N4—O9	1.213 (3)
C13—C14	1.413 (4)	N4—O8	1.241 (3)
C13—H13	0.9300	N4—O10	1.253 (3)
C14—C15	1.365 (4)	N5—O12	1.222 (3)
C14—H14	0.9300	N5—O13	1.249 (3)
C15—O4	1.375 (3)	N5—O11	1.263 (3)

O1—C1—C6	122.4 (2)	O8—Er1—O13	108.19 (8)
O1—C1—C2	119.4 (2)	O11—Er1—O13	51.07 (6)
C6—C1—C2	118.2 (2)	O3—Er1—O7	117.50 (7)
C3—C2—O2	126.7 (2)	O1—Er1—O7	110.20 (8)
C3—C2—C1	120.9 (2)	O10—Er1—O7	103.00 (8)
O2—C2—C1	112.4 (2)	O5—Er1—O7	50.82 (7)
C2—C3—C4	120.1 (3)	O8—Er1—O7	65.02 (8)
C2—C3—H3	120.0	O11—Er1—O7	125.25 (7)
C4—C3—H3	120.0	O13—Er1—O7	173.13 (7)
C5—C4—C3	120.6 (3)	O3—Er1—O2	138.34 (6)
C5—C4—H4	119.7	O1—Er1—O2	64.51 (6)
C3—C4—H4	119.7	O10—Er1—O2	124.92 (7)
C4—C5—C6	120.6 (3)	O5—Er1—O2	82.83 (8)
C4—C5—H5	119.7	O8—Er1—O2	80.16 (8)
C6—C5—H5	119.7	O11—Er1—O2	67.34 (7)
C1—C6—C5	119.6 (2)	O13—Er1—O2	109.97 (7)
C1—C6—C7	119.9 (2)	O7—Er1—O2	70.74 (7)
C5—C6—C7	120.4 (2)	O3—Er1—O4	62.17 (6)
N1—C7—C6	123.0 (2)	O1—Er1—O4	127.71 (7)
N1—C7—H7	118.5	O10—Er1—O4	68.86 (7)
C6—C7—H7	118.5	O5—Er1—O4	69.22 (8)
N1—C8—C9	110.5 (2)	O8—Er1—O4	86.66 (8)
N1—C8—H8A	109.6	O11—Er1—O4	143.86 (7)
C9—C8—H8A	109.6	O13—Er1—O4	110.04 (7)
N1—C8—H8B	109.6	O7—Er1—O4	69.43 (7)
C9—C8—H8B	109.6	O2—Er1—O4	139.98 (7)
H8A—C8—H8B	108.1	O3—Er1—N4	118.27 (8)
N2—C9—C8	110.5 (2)	O1—Er1—N4	155.06 (7)
N2—C9—H9A	109.5	O10—Er1—N4	25.63 (7)
C8—C9—H9A	109.5	O5—Er1—N4	129.48 (7)
N2—C9—H9B	109.5	O8—Er1—N4	25.37 (7)
C8—C9—H9B	109.5	O11—Er1—N4	73.69 (7)
H9A—C9—H9B	108.1	O13—Er1—N4	89.91 (7)
N2—C10—C11	123.3 (2)	O7—Er1—N4	83.31 (7)
N2—C10—H10	118.4	O2—Er1—N4	102.96 (7)
C11—C10—H10	118.4	O4—Er1—N4	76.17 (7)
C12—C11—C10	121.0 (2)	O3—Er1—N5	91.84 (6)
C12—C11—C16	119.2 (2)	O1—Er1—N5	77.16 (7)
C10—C11—C16	119.7 (2)	O10—Er1—N5	71.38 (8)
C13—C12—C11	120.7 (3)	O5—Er1—N5	149.24 (7)
C13—C12—H12	119.7	O8—Er1—N5	91.62 (8)
C11—C12—H12	119.7	O11—Er1—N5	25.67 (6)
C12—C13—C14	121.0 (2)	O13—Er1—N5	25.39 (6)
C12—C13—H13	119.5	O7—Er1—N5	150.63 (7)
C14—C13—H13	119.5	O2—Er1—N5	88.63 (7)
C15—C14—C13	119.6 (3)	O4—Er1—N5	129.63 (6)
C15—C14—H14	120.2	N4—Er1—N5	81.22 (7)
C13—C14—H14	120.2	C7—N1—C8	126.7 (2)
C14—C15—O4	126.5 (2)	C7—N1—H1	111 (2)
C14—C15—C16	121.1 (2)	C8—N1—H1	122 (2)
O4—C15—C16	112.4 (2)	C10—N2—C9	126.2 (2)
O3—C16—C15	119.3 (2)	C10—N2—H2	116 (2)
O3—C16—C11	122.2 (2)	C9—N2—H2	117 (2)
C15—C16—C11	118.4 (2)	O6—N3—O7	123.4 (3)
O4—C17—H15	109.5	O6—N3—O5	121.5 (3)
O4—C17—H16	109.5	O7—N3—O5	115.1 (3)
H15—C17—H16	109.5	O6—N3—Er1	178.1 (2)
O4—C17—H17	109.5	O7—N3—Er1	58.24 (15)
H15—C17—H17	109.5	O5—N3—Er1	56.87 (16)
H16—C17—H17	109.5	O9—N4—O8	122.3 (3)
O2—C18—H18	109.5	O9—N4—O10	122.0 (3)
O2—C18—H19	109.5	O8—N4—O10	115.7 (2)
H18—C18—H19	109.5	O9—N4—Er1	177.1 (2)
O2—C18—H20	109.5	O8—N4—Er1	58.09 (13)
H18—C18—H20	109.5	O10—N4—Er1	57.67 (14)
H19—C18—H20	109.5	O12—N5—O13	122.0 (2)
O3—Er1—O1	75.02 (7)	O12—N5—O11	122.1 (2)
O3—Er1—O10	94.30 (7)	O13—N5—O11	115.8 (2)
O1—Er1—O10	146.42 (8)	O12—N5—Er1	179.17 (19)
O3—Er1—O5	75.82 (7)	O13—N5—Er1	58.18 (13)
O1—Er1—O5	72.48 (8)	O11—N5—Er1	57.65 (13)
O10—Er1—O5	136.56 (9)	C1—O1—Er1	126.89 (16)
O3—Er1—O8	141.41 (8)	C2—O2—C18	117.5 (2)
O1—Er1—O8	142.88 (8)	C2—O2—Er1	116.64 (14)
O10—Er1—O8	51.00 (7)	C18—O2—Er1	125.79 (19)
O5—Er1—O8	115.70 (8)	C16—O3—Er1	128.54 (15)
O3—Er1—O11	117.19 (6)	C15—O4—C17	117.2 (2)
O1—Er1—O11	81.46 (8)	C15—O4—Er1	113.57 (14)
O10—Er1—O11	75.35 (8)	C17—O4—Er1	128.36 (18)
O5—Er1—O11	146.82 (8)	N3—O5—Er1	97.71 (18)
O8—Er1—O11	74.41 (9)	N3—O7—Er1	96.36 (16)
O3—Er1—O13	66.82 (6)	N4—O8—Er1	96.54 (16)
O1—Er1—O13	75.74 (8)	N4—O10—Er1	96.69 (17)
O10—Er1—O13	70.83 (8)	N5—O11—Er1	96.68 (14)
O5—Er1—O13	135.84 (7)	N5—O13—Er1	96.42 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.85 (1)	1.89 (3)	2.574 (3)	137 (3)
N1—H1···O1	0.85 (1)	1.84 (2)	2.567 (3)	143 (3)
C7—H7···O5ⁱ	0.93	2.33	3.073 (3)	137
C9—H9A···O12ⁱⁱ	0.97	2.50	3.241 (3)	133
C10—H10···O9ⁱⁱⁱ	0.93	2.57	3.395 (4)	148
C14—H14···O12^iv	0.93	2.50	3.341 (4)	150

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1/2, −y+3/2, z+1/2; (iv) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Er(NO₃)₃(C₁₈H₂₀N₂O₄)]
M_r	681.65
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	14.098 (3), 11.865 (2), 14.571 (3)
β (°)	103.98 (3)
V (Å³)	2365.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.63
Crystal size (mm)	0.37 × 0.36 × 0.34

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.344, 0.368
No. of measured, independent and observed [I > 2σ(I)] reflections	21792, 5358, 4748
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.049, 1.04
No. of reflections	5358
No. of parameters	344
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.32

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.847 (10)	1.89 (3)	2.574 (3)	137 (3)
N1—H1···O1	0.846 (10)	1.84 (2)	2.567 (3)	143 (3)
C7—H7···O5ⁱ	0.93	2.33	3.073 (3)	136.9
C9—H9A···O12ⁱⁱ	0.97	2.50	3.241 (3)	133.2
C10—H10···O9ⁱⁱⁱ	0.93	2.57	3.395 (4)	147.5
C14—H14···O12^iv	0.93	2.50	3.341 (4)	150.4

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1/2, −y+3/2, z+1/2; (iv) x−1/2, −y+3/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (Nos. 20672032 and 20872030), the Key Laboratory of Heilongjiang Province and the Education Department of Heilongjiang Province (Nos. ZJG0504, JC200605, 1152GZD02, GZ08A401, 11531284, 2006FRFLXG031 and 2007RFQXG096) and Heilongjiang University.

References

Gao, T., Li, G.-M., Gao, P., Yan, P.-F. & Hou, G.-F. (2009). Acta Cryst. E65, m1585. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gao, T., Yan, P. F., Li, G. M., Hou, G. F. & Gao, J. S. (2008). Inorg. Chim. Acta, 361, 2051–2058. Web of Science CSD CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. 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

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