[N,N′-Bis(3-meth­oxy-2-oxidobenzyl­idene)ethyl­enediammonium-κ4O,O′,O′′,O′′′]tris­(nitrato-κ2O,O′)dysprosium(III)

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

doi:10.1107/S1600536809047436

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1585

doi:10.1107/S1600536809047436

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[N,N′-Bis(3-methoxy-2-oxidobenzylidene)ethylenediammonium-κ⁴O,O′,O′′,O′′′]tris(nitrato-κ²O,O′)dysprosium(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 27 October 2009; accepted 10 November 2009; online 14 November 2009)

In the title mononuclear Schiff base complex, [Dy(NO₃)₃(C₁₈H₂₀N₂O₄)], the Dy^III ion is ten-coordinated in a distorted hexadecahedral geometry by six O atoms of three nitrate anions and four O atoms of the Schiff base ligand. An intramolecular N—H⋯O hydrogen bond occurs. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis and crystal structure of the isostructural Nd, Eu and Tb complexes, see: Gao et al. (2008 ).

Experimental

Crystal data

[Dy(NO₃)₃(C₁₈H₂₀N₂O₄)]
M_r = 676.89
Monoclinic, P 2₁ /n
a = 14.126 (5) Å
b = 11.860 (4) Å
c = 14.628 (4) Å
β = 104.302 (12)°
V = 2374.7 (13) Å³
Z = 4
Mo Kα radiation
μ = 3.22 mm⁻¹
T = 291 K
0.29 × 0.28 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.454, T_max = 0.513
22587 measured reflections
5430 independent reflections
4850 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.045
S = 1.10
5430 reflections
344 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected bond lengths (Å)

Dy1—O1	2.2718 (18)
Dy1—O3	2.2847 (18)
Dy1—O10	2.472 (2)
Dy1—O8	2.477 (2)
Dy1—O5	2.480 (2)
Dy1—O13	2.490 (2)
Dy1—O11	2.492 (2)
Dy1—O7	2.510 (2)
Dy1—O4	2.5740 (19)
Dy1—O2	2.6794 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.850 (15)	1.87 (3)	2.570 (3)	139.3 (14)
C8—H8B⋯O12ⁱ	0.97	2.51	3.245 (3)	133
C10—H10⋯O5ⁱⁱ	0.93	2.32	3.076 (3)	138
C3—H3⋯O12ⁱⁱⁱ	0.93	2.51	3.351 (3)	151
C7—H7⋯O9^iv	0.93	2.56	3.376 (3)	147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (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: 10.1107/S1600536809047436/rz2383sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047436/rz2383Isup2.hkl

checkCIF report

Comment top

Schiff base lanthanide complexes are currently of great interest because of their unique physicochemical properties and various applications as new materials. Moreover, the luminescence and magnetic properties of lanthanide complexes have recently aroused much attention.

As shown in Fig. 1, the ten-coordinate dysprosium(III) ion adopts a hexadecahedron 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. The title compound is isostructural with the corresponding Nd, Eu and Tb complexes (Gao et al., 2008). The Dy—O bond distances (Table 1) range from 2.2718 (18) to 2.6794 (19) Å, 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 2).

Related literature top

For the synthesis and crystal structure of the isostructural Nd, Eu and Tb complexes, see: Gao et al. (2008).

Experimental top

The title complex was obtained by the treatment of dysprosium (III) nitrate hexahydrate (0.114 g, 0.25 mmol) with N,N'-ethylene-bis(3-methoxysalicylideneimine) (0.083 g, 0.25 mmol) in acetonitrile/methanol (10 ml/10 ml). The mixture was stirred for 3 h. The reaction mixture was then filtered and diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis calculated for for C₁₈H₂₀Dy₁N₅O₁₃: C 31.94, H 2.96, N 10.37%; found: C 32.08, H 3.00, N 10.48%.

Computing details top

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

[N,N'-Bis(3-methoxy-2-oxidobenzylidene)ethylenediammonium- κ⁴O,O',O'',O''']tris(nitrato- κ²O,O')dysprosium(III) top

Crystal data top

[Dy(NO₃)₃(C₁₈H₂₀N₂O₄)]	F(000) = 1332
M_r = 676.89	D_x = 1.893 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20034 reflections
a = 14.126 (5) Å	θ = 6.7–55.0°
b = 11.860 (4) Å	µ = 3.22 mm⁻¹
c = 14.628 (4) Å	T = 291 K
β = 104.302 (12)°	Block, brown
V = 2374.7 (13) Å³	0.29 × 0.28 × 0.24 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5430 independent reflections
Radiation source: fine-focus sealed tube	4850 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −18→18
T_min = 0.454, T_max = 0.513	k = −15→15
22587 measured reflections	l = −18→18

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0164P)² + 1.5062P] where P = (F_o² + 2F_c²)/3
5430 reflections	(Δ/σ)_max = 0.002
344 parameters	Δρ_max = 0.41 e Å⁻³
14 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Dy(NO₃)₃(C₁₈H₂₀N₂O₄)]	V = 2374.7 (13) Å³
M_r = 676.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.126 (5) Å	µ = 3.22 mm⁻¹
b = 11.860 (4) Å	T = 291 K
c = 14.628 (4) Å	0.29 × 0.28 × 0.24 mm
β = 104.302 (12)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5430 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4850 reflections with I > 2σ(I)
T_min = 0.454, T_max = 0.513	R_int = 0.021
22587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	14 restraints
wR(F²) = 0.045	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.41 e Å⁻³
5430 reflections	Δρ_min = −0.54 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	0.29349 (17)	0.18407 (19)	0.20773 (16)	0.0338 (5)
C2	0.28896 (19)	0.1407 (2)	0.11666 (17)	0.0384 (5)
C3	0.2045 (2)	0.0947 (2)	0.06330 (19)	0.0488 (7)
H3	0.2018	0.0683	0.0028	0.059*
C4	0.1218 (2)	0.0874 (3)	0.1004 (2)	0.0542 (7)
H4	0.0646	0.0553	0.0643	0.065*
C5	0.12392 (19)	0.1264 (2)	0.1879 (2)	0.0469 (6)
H5	0.0687	0.1201	0.2114	0.056*
C6	0.20936 (17)	0.1765 (2)	0.24346 (17)	0.0362 (5)
C7	0.21298 (18)	0.2144 (2)	0.33610 (18)	0.0385 (5)
H7	0.1585	0.2031	0.3600	0.046*
C8	0.3034 (2)	0.2907 (2)	0.48885 (18)	0.0452 (6)
H8A	0.2405	0.3002	0.5034	0.054*
H8B	0.3391	0.3610	0.5028	0.054*
C9	0.3598 (2)	0.1974 (2)	0.54950 (18)	0.0463 (6)
H9A	0.3735	0.2192	0.6154	0.056*
H9B	0.3205	0.1294	0.5415	0.056*
C10	0.5321 (2)	0.1420 (2)	0.57900 (17)	0.0407 (6)
H10	0.5346	0.1328	0.6427	0.049*
C11	0.61751 (19)	0.1191 (2)	0.54777 (16)	0.0377 (5)
C12	0.7035 (2)	0.0798 (2)	0.61169 (19)	0.0469 (6)
H12	0.7033	0.0664	0.6743	0.056*
C13	0.7860 (2)	0.0617 (2)	0.5824 (2)	0.0495 (7)
H13	0.8424	0.0375	0.6253	0.059*
C14	0.78698 (19)	0.0792 (2)	0.4876 (2)	0.0452 (6)
H14	0.8440	0.0666	0.4682	0.054*
C15	0.70435 (19)	0.1145 (2)	0.42392 (17)	0.0393 (5)
C16	0.61780 (18)	0.1388 (2)	0.45268 (16)	0.0364 (5)
C17	0.7761 (3)	0.1084 (4)	0.2912 (3)	0.0785 (11)
H17A	0.8281	0.1592	0.3194	0.118*
H17B	0.7584	0.1192	0.2241	0.118*
H17C	0.7975	0.0321	0.3052	0.118*
C18	0.3786 (3)	0.1133 (3)	−0.00104 (19)	0.0633 (9)
H18A	0.3646	0.0340	−0.0063	0.095*
H18B	0.4423	0.1268	−0.0109	0.095*
H18C	0.3307	0.1534	−0.0477	0.095*
Dy1	0.527482 (8)	0.207652 (10)	0.234090 (7)	0.03310 (4)
H1	0.3368 (15)	0.274 (2)	0.3653 (19)	0.049 (8)*
H2	0.452 (2)	0.180 (2)	0.4658 (9)	0.050 (8)*
N1	0.28886 (15)	0.26398 (19)	0.38914 (15)	0.0389 (5)
N2	0.45122 (17)	0.1750 (2)	0.52358 (14)	0.0418 (5)
N3	0.5162 (2)	−0.0351 (2)	0.19797 (19)	0.0643 (7)
N4	0.57521 (19)	0.3122 (2)	0.07175 (16)	0.0477 (6)
N5	0.58626 (16)	0.42878 (19)	0.31539 (14)	0.0412 (5)
O1	0.37477 (11)	0.22948 (15)	0.25585 (11)	0.0371 (4)
O2	0.37584 (14)	0.15168 (17)	0.09135 (12)	0.0464 (4)
O3	0.54183 (13)	0.17845 (18)	0.39131 (12)	0.0480 (5)
O4	0.69309 (13)	0.13026 (18)	0.32846 (12)	0.0483 (5)
O5	0.47264 (19)	0.01237 (19)	0.25317 (15)	0.0697 (7)
O6	0.5109 (3)	−0.1369 (2)	0.1860 (2)	0.1026 (10)
O7	0.56475 (17)	0.02863 (18)	0.15829 (15)	0.0586 (5)
O8	0.62384 (19)	0.2322 (2)	0.11513 (17)	0.0684 (7)
O9	0.5925 (2)	0.3528 (2)	0.00129 (17)	0.0767 (7)
O10	0.50641 (15)	0.3465 (2)	0.10457 (15)	0.0591 (5)
O11	0.49884 (14)	0.39756 (17)	0.29500 (16)	0.0531 (5)
O12	0.61122 (16)	0.52094 (17)	0.35117 (14)	0.0565 (5)
O13	0.64723 (13)	0.35980 (17)	0.29731 (15)	0.0532 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0348 (11)	0.0314 (11)	0.0346 (11)	−0.0017 (9)	0.0074 (9)	0.0008 (9)
C2	0.0440 (13)	0.0367 (13)	0.0341 (11)	−0.0039 (11)	0.0091 (10)	−0.0033 (10)
C3	0.0588 (17)	0.0428 (14)	0.0395 (13)	−0.0086 (13)	0.0020 (12)	−0.0061 (11)
C4	0.0464 (15)	0.0521 (16)	0.0559 (16)	−0.0168 (13)	−0.0027 (13)	−0.0037 (14)
C5	0.0362 (13)	0.0471 (15)	0.0557 (16)	−0.0084 (12)	0.0084 (12)	0.0055 (13)
C6	0.0327 (11)	0.0353 (12)	0.0406 (12)	−0.0043 (9)	0.0091 (10)	0.0028 (10)
C7	0.0349 (12)	0.0386 (12)	0.0460 (13)	−0.0003 (10)	0.0176 (10)	0.0031 (11)
C8	0.0478 (14)	0.0504 (15)	0.0433 (13)	−0.0048 (12)	0.0225 (11)	−0.0145 (12)
C9	0.0492 (14)	0.0586 (17)	0.0376 (12)	−0.0106 (13)	0.0231 (11)	−0.0047 (12)
C10	0.0553 (15)	0.0370 (13)	0.0310 (11)	−0.0091 (11)	0.0128 (11)	0.0011 (10)
C11	0.0473 (13)	0.0319 (12)	0.0323 (11)	−0.0022 (10)	0.0069 (10)	0.0017 (10)
C12	0.0585 (17)	0.0394 (14)	0.0372 (13)	−0.0020 (12)	0.0014 (12)	0.0035 (11)
C13	0.0491 (15)	0.0404 (14)	0.0510 (15)	0.0051 (12)	−0.0028 (12)	0.0060 (12)
C14	0.0400 (13)	0.0362 (13)	0.0584 (16)	0.0049 (11)	0.0103 (12)	0.0013 (12)
C15	0.0442 (13)	0.0342 (12)	0.0397 (12)	0.0047 (11)	0.0109 (11)	0.0004 (10)
C16	0.0394 (12)	0.0353 (12)	0.0339 (11)	0.0025 (10)	0.0077 (10)	0.0001 (10)
C17	0.060 (2)	0.118 (3)	0.069 (2)	0.037 (2)	0.0370 (17)	0.013 (2)
C18	0.077 (2)	0.082 (2)	0.0358 (14)	0.0003 (18)	0.0229 (14)	−0.0122 (15)
Dy1	0.03516 (6)	0.03925 (7)	0.02910 (6)	0.00211 (5)	0.01592 (4)	−0.00037 (5)
N1	0.0366 (11)	0.0468 (12)	0.0382 (11)	−0.0022 (9)	0.0185 (9)	−0.0047 (9)
N2	0.0471 (12)	0.0519 (13)	0.0294 (10)	−0.0044 (10)	0.0153 (9)	−0.0019 (9)
N3	0.102 (2)	0.0461 (14)	0.0522 (14)	0.0068 (15)	0.0325 (15)	−0.0015 (12)
N4	0.0601 (14)	0.0470 (13)	0.0439 (12)	−0.0118 (11)	0.0278 (11)	−0.0022 (10)
N5	0.0432 (12)	0.0462 (12)	0.0361 (10)	−0.0041 (10)	0.0136 (9)	−0.0033 (9)
O1	0.0298 (8)	0.0492 (10)	0.0333 (8)	−0.0072 (7)	0.0097 (7)	−0.0093 (7)
O2	0.0515 (11)	0.0581 (12)	0.0320 (8)	−0.0042 (9)	0.0151 (8)	−0.0092 (8)
O3	0.0409 (9)	0.0740 (13)	0.0309 (8)	0.0142 (9)	0.0126 (7)	0.0078 (9)
O4	0.0438 (10)	0.0643 (12)	0.0418 (9)	0.0167 (9)	0.0199 (8)	0.0047 (9)
O5	0.117 (2)	0.0492 (12)	0.0607 (13)	0.0073 (12)	0.0550 (14)	0.0087 (10)
O6	0.162 (3)	0.0501 (14)	0.113 (2)	−0.0049 (16)	0.066 (2)	−0.0142 (15)
O7	0.0759 (14)	0.0541 (12)	0.0556 (12)	0.0009 (11)	0.0345 (11)	−0.0100 (10)
O8	0.0819 (16)	0.0684 (14)	0.0724 (15)	0.0239 (13)	0.0523 (13)	0.0187 (12)
O9	0.1095 (19)	0.0714 (15)	0.0662 (14)	−0.0062 (14)	0.0538 (14)	0.0168 (12)
O10	0.0497 (11)	0.0750 (14)	0.0583 (12)	0.0095 (11)	0.0243 (10)	0.0189 (11)
O11	0.0401 (10)	0.0494 (11)	0.0741 (13)	−0.0049 (9)	0.0221 (9)	−0.0172 (10)
O12	0.0668 (13)	0.0481 (11)	0.0540 (11)	−0.0170 (10)	0.0137 (10)	−0.0135 (9)
O13	0.0377 (9)	0.0549 (12)	0.0677 (13)	0.0011 (9)	0.0142 (9)	−0.0042 (10)

Geometric parameters (Å, º) top

C1—O1	1.306 (3)	C15—O4	1.379 (3)
C1—C6	1.414 (3)	C15—C16	1.417 (3)
C1—C2	1.415 (3)	C16—O3	1.305 (3)
C2—C3	1.367 (4)	C17—O4	1.434 (3)
C2—O2	1.373 (3)	C17—H17A	0.9600
C3—C4	1.409 (4)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.353 (4)	C18—O2	1.436 (3)
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.410 (3)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—C7	1.416 (4)	Dy1—O1	2.2718 (18)
C7—N1	1.299 (3)	Dy1—O3	2.2847 (18)
C7—H7	0.9300	Dy1—O10	2.472 (2)
C8—N1	1.457 (3)	Dy1—O8	2.477 (2)
C8—C9	1.515 (4)	Dy1—O5	2.480 (2)
C8—H8A	0.9700	Dy1—O13	2.490 (2)
C8—H8B	0.9700	Dy1—O11	2.492 (2)
C9—N2	1.458 (3)	Dy1—O7	2.510 (2)
C9—H9A	0.9700	Dy1—O4	2.5740 (19)
C9—H9B	0.9700	Dy1—O2	2.6794 (19)
C10—N2	1.288 (3)	N1—H1	0.843 (10)
C10—C11	1.418 (4)	N2—H2	0.848 (10)
C10—H10	0.9300	N3—O6	1.219 (4)
C11—C16	1.411 (3)	N3—O7	1.255 (3)
C11—C12	1.416 (4)	N3—O5	1.263 (3)
C12—C13	1.355 (4)	N4—O9	1.216 (3)
C12—H12	0.9300	N4—O8	1.248 (3)
C13—C14	1.404 (4)	N4—O10	1.254 (3)
C13—H13	0.9300	N5—O12	1.225 (3)
C14—C15	1.367 (4)	N5—O11	1.253 (3)
C14—H14	0.9300	N5—O13	1.262 (3)

O1—C1—C6	122.3 (2)	O3—Dy1—O8	142.89 (8)
O1—C1—C2	119.1 (2)	O10—Dy1—O8	50.68 (7)
C6—C1—C2	118.6 (2)	O1—Dy1—O5	75.92 (7)
C3—C2—O2	126.5 (2)	O3—Dy1—O5	72.40 (7)
C3—C2—C1	120.9 (2)	O10—Dy1—O5	136.61 (8)
O2—C2—C1	112.6 (2)	O8—Dy1—O5	115.47 (7)
C2—C3—C4	119.6 (3)	O1—Dy1—O13	116.54 (6)
C2—C3—H3	120.2	O3—Dy1—O13	81.53 (7)
C4—C3—H3	120.2	O10—Dy1—O13	75.16 (8)
C5—C4—C3	121.1 (2)	O8—Dy1—O13	74.63 (8)
C5—C4—H4	119.4	O5—Dy1—O13	146.88 (8)
C3—C4—H4	119.4	O1—Dy1—O11	66.62 (6)
C4—C5—C6	120.4 (3)	O3—Dy1—O11	76.05 (7)
C4—C5—H5	119.8	O10—Dy1—O11	70.88 (8)
C6—C5—H5	119.8	O8—Dy1—O11	108.11 (8)
C5—C6—C1	119.4 (2)	O5—Dy1—O11	136.15 (7)
C5—C6—C7	120.6 (2)	O13—Dy1—O11	50.77 (6)
C1—C6—C7	119.9 (2)	O1—Dy1—O7	117.92 (7)
N1—C7—C6	123.0 (2)	O3—Dy1—O7	109.89 (7)
N1—C7—H7	118.5	O10—Dy1—O7	102.92 (8)
C6—C7—H7	118.5	O8—Dy1—O7	65.02 (8)
N1—C8—C9	110.6 (2)	O5—Dy1—O7	50.60 (7)
N1—C8—H8A	109.5	O13—Dy1—O7	125.42 (7)
C9—C8—H8A	109.5	O11—Dy1—O7	173.06 (7)
N1—C8—H8B	109.5	O1—Dy1—O4	137.24 (6)
C9—C8—H8B	109.5	O3—Dy1—O4	64.10 (6)
H8A—C8—H8B	108.1	O10—Dy1—O4	124.75 (6)
N2—C9—C8	110.6 (2)	O8—Dy1—O4	80.47 (7)
N2—C9—H9A	109.5	O5—Dy1—O4	82.78 (8)
C8—C9—H9A	109.5	O13—Dy1—O4	67.37 (7)
N2—C9—H9B	109.5	O11—Dy1—O4	109.69 (7)
C8—C9—H9B	109.5	O7—Dy1—O4	70.93 (7)
H9A—C9—H9B	108.1	O1—Dy1—O2	62.19 (6)
N2—C10—C11	123.3 (2)	O3—Dy1—O2	127.01 (6)
N2—C10—H10	118.4	O10—Dy1—O2	69.28 (7)
C11—C10—H10	118.4	O8—Dy1—O2	87.36 (8)
C16—C11—C12	119.6 (2)	O5—Dy1—O2	69.17 (7)
C16—C11—C10	119.7 (2)	O13—Dy1—O2	143.90 (7)
C12—C11—C10	120.6 (2)	O11—Dy1—O2	109.48 (6)
C13—C12—C11	120.5 (3)	O7—Dy1—O2	70.17 (7)
C13—C12—H12	119.7	O4—Dy1—O2	140.83 (6)
C11—C12—H12	119.7	C7—N1—C8	126.0 (2)
C12—C13—C14	120.5 (2)	C7—N1—H1	117 (2)
C12—C13—H13	119.7	C8—N1—H1	117 (2)
C14—C13—H13	119.7	C10—N2—C9	126.7 (2)
C15—C14—C13	120.2 (3)	C10—N2—H2	115 (2)
C15—C14—H14	119.9	C9—N2—H2	118 (2)
C13—C14—H14	119.9	O6—N3—O7	123.5 (3)
C14—C15—O4	126.7 (2)	O6—N3—O5	120.7 (3)
C14—C15—C16	120.9 (2)	O7—N3—O5	115.8 (2)
O4—C15—C16	112.4 (2)	O9—N4—O8	122.1 (3)
O3—C16—C11	122.4 (2)	O9—N4—O10	122.2 (3)
O3—C16—C15	119.5 (2)	O8—N4—O10	115.7 (2)
C11—C16—C15	118.1 (2)	O12—N5—O11	121.9 (2)
O4—C17—H17A	109.5	O12—N5—O13	121.9 (2)
O4—C17—H17B	109.5	O11—N5—O13	116.2 (2)
H17A—C17—H17B	109.5	C1—O1—Dy1	128.06 (15)
O4—C17—H17C	109.5	C2—O2—C18	117.2 (2)
H17A—C17—H17C	109.5	C2—O2—Dy1	114.15 (13)
H17B—C17—H17C	109.5	C18—O2—Dy1	127.57 (18)
O2—C18—H18A	109.5	C16—O3—Dy1	126.91 (15)
O2—C18—H18B	109.5	C15—O4—C17	117.4 (2)
H18A—C18—H18B	109.5	C15—O4—Dy1	116.98 (14)
O2—C18—H18C	109.5	C17—O4—Dy1	125.54 (18)
H18A—C18—H18C	109.5	N3—O5—Dy1	97.43 (18)
H18B—C18—H18C	109.5	N3—O7—Dy1	96.15 (16)
O1—Dy1—O3	74.18 (6)	N4—O8—Dy1	96.75 (16)
O1—Dy1—O10	95.32 (7)	N4—O10—Dy1	96.83 (16)
O3—Dy1—O10	146.76 (8)	N5—O11—Dy1	96.59 (15)
O1—Dy1—O8	142.24 (7)	N5—O13—Dy1	96.40 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.85 (2)	1.87 (3)	2.570 (3)	139 (1)
C8—H8B···O12ⁱ	0.97	2.51	3.245 (3)	133
C10—H10···O5ⁱⁱ	0.93	2.32	3.076 (3)	138
C3—H3···O12ⁱⁱⁱ	0.93	2.51	3.351 (3)	151
C7—H7···O9^iv	0.93	2.56	3.376 (3)	147

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

Experimental details

Crystal data
Chemical formula	[Dy(NO₃)₃(C₁₈H₂₀N₂O₄)]
M_r	676.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	14.126 (5), 11.860 (4), 14.628 (4)
β (°)	104.302 (12)
V (Å³)	2374.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.22
Crystal size (mm)	0.29 × 0.28 × 0.24

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.454, 0.513
No. of measured, independent and observed [I > 2σ(I)] reflections	22587, 5430, 4850
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.045, 1.10
No. of reflections	5430
No. of parameters	344
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.54

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

Selected bond lengths (Å) top

Dy1—O1	2.2718 (18)	Dy1—O13	2.490 (2)
Dy1—O3	2.2847 (18)	Dy1—O11	2.492 (2)
Dy1—O10	2.472 (2)	Dy1—O7	2.510 (2)
Dy1—O8	2.477 (2)	Dy1—O4	2.5740 (19)
Dy1—O5	2.480 (2)	Dy1—O2	2.6794 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.850 (15)	1.87 (3)	2.570 (3)	139.3 (14)
C8—H8B···O12ⁱ	0.97	2.51	3.245 (3)	133
C10—H10···O5ⁱⁱ	0.93	2.32	3.076 (3)	138
C3—H3···O12ⁱⁱⁱ	0.93	2.51	3.351 (3)	151
C7—H7···O9^iv	0.93	2.56	3.376 (3)	147

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

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