Bis{6,6′-dimeth­oxy-2,2′-[ethane-1,2-diyl­bis(imino­methyl­ene)]diphenolato(1.5−)-κ4O,N,N′,O′}erbium(III)

Xia, H.-T.; Rong, Y.-Y.; Zhang, Y.-Y.; Yang, S.-P.; Wang, D.-Q.

doi:10.1107/S1600536809001421

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m198-m199

doi:10.1107/S1600536809001421

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Bis{6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5−)-κ⁴O,N,N′,O′}erbium(III)

Hai-Tao Xia,^a ^* De-Fu Rong,^b Ying-Ying Zhang,^b Shu-Ping Yang ^a and Da-Qi Wang ^c

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bBeilun Entry–Exit Inspection and Quarantine Bureau of China, Ningbo Zhejiang, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: xht161006@hhit.edu.cn

(Received 14 November 2008; accepted 12 January 2009; online 17 January 2009)

In the title compound, [Er(C₁₈H_22.5N₂O₄)₂], the Er atom is located on a twofold rotation axis and is eight-coordinated by four O atoms and four N atoms from two symmetry-related 6,6′-dimethoxy-2,2′-(ethane-1,2-diyldiiminodimethylene)diphenolate(1.5−) ligands. Due to disorder of one phenolate H atom with half-occupation, the overall charge of one tetradentate ligand is −1.5. The ligand molecules are stabilised by intramolecular N—H⋯O and O—H⋯O hydrogen bonds and are linked into a chain parallel to the a axis by a C—H⋯O hydrogen bond. Neighbouring chains are connected by van der Waals forces, resulting in a three-dimensional network.

Related literature

For related structures, see: Liu et al. (2007 ); Xia et al. (2006 ). For isotypic structures, see: Xia et al. (2009a , 2009b ).

Experimental

Crystal data

[Er(C₁₈H_22.5N₂O₄)₂]
M_r = 829.02
Orthorhombic, I b a 2
a = 11.1542 (10) Å
b = 21.958 (2) Å
c = 14.1751 (15) Å
V = 3471.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 298 (2) K
0.20 × 0.15 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.637, T_max = 0.723
7986 measured reflections
3007 independent reflections
2199 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.162
S = 1.06
3007 reflections
224 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −1.42 e Å⁻³
Absolute structure: Flack (1983 ), 1400 Friedel pairs
Flack parameter: 0.02 (5)

Table 1
Selected bond lengths (Å)

Er1—O3ⁱ	2.202 (6)
Er1—O3	2.202 (6)
Er1—O1	2.203 (6)
Er1—O1ⁱ	2.203 (6)
Er1—N2	2.595 (8)
Er1—N2ⁱ	2.595 (8)
Er1—N1ⁱ	2.628 (8)
Er1—N1	2.628 (8)
Symmetry code: (i) -x+2, -y+2, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O4ⁱⁱ	0.96	2.70	3.49 (3)	140
N2—H2⋯O2ⁱ	0.91	2.34	3.230 (10)	166
N1—H1C⋯O4ⁱ	0.91	2.59	3.462 (12)	162
O1—H1⋯O2	0.82	2.21	2.646 (9)	113
Symmetry codes: (i) -x+2, -y+2, z; (ii) -x+3, -y+2, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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: 10.1107/S1600536809001421/at2680sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001421/at2680Isup2.hkl

checkCIF report

Comment top

Diamine derivatives are potentially multidentate ligands. We have recently reported the crystal structure (C₁₈H₂₄O₂N₄) (II) (Xia et al., 2006) which is the ligand of the title compound and a complex [Ce(C₁₈H₂₂N₂O₄)₂] (III) (Liu et al., 2007). We report here the crystal structure of new rare earth complex (I).

In the title complex (I), the coordination environment of the Er atom and coordination modes of (I) ligands to Er^III ion is in agreement with the complexes reported above (Fig. 1). The average bond lengths of between the Erbium center oxygen atoms are 2.203 (6)Å and nitrogen atom are 2.612 (8) Å, longer than the 2.199 (4)Å and shorter than the 2.624 (4)Å of complexes (III), respectively. The dihedral angles between phenyl ring (C2-C7 ring) and anotother phenyl ring are 42.20 (28)°(C10—C15 ring), 42.29 (26)°(C2A—C7A ring) and 15.47 (43)°(C10A—C15A ring) [symmetry codes: (A) 2 - x, 2 - y, z].

In (I), the Er atom is eight-coordinated by four O atoms and four N atoms from two 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol. The molecules are linked into a chain parallel to the a axis by one C—H···O hydrogen bond. Neighbouring chains are connected by van der Waals forces, resulting in a three-dimensional network.

Related literature top

For related structures, see: Liu et al. (2007); Xia et al. (2006). For isotypic structures, see: Xia et al. (2009a,b).

Experimental top

A solution of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene) diphenol (0.328 g, 2 mmol) in ethanol (20 ml), and then a solution of Er(NO₃)₃.6H₂O (0.461 g, 1 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred for 3 h in the air and then filtered. X-ray quality crystals of (I) were obtained by evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. For clarity, H atoms have been omitted. [symmetry codes: (A) 2 - x, 2 - y, z].
	Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds [symmetry codes: (A) 2 - x, 2 - y, z; (B) 3 - x, 2 - y, 2, z; (C) -1 + x, y, z].

Bis{6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(iminomethylene)]diphenolato(1.5-)- κ⁴O,N,N',O'}erbium(III) top

Crystal data top

[Er(C₁₈H_22.5N₂O₄)₂]	F(000) = 1684
M_r = 829.02	D_x = 1.586 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 4129 reflections
a = 11.1542 (10) Å	θ = 2.9–25.7°
b = 21.958 (2) Å	µ = 2.48 mm⁻¹
c = 14.1751 (15) Å	T = 298 K
V = 3471.8 (6) Å³	Block, brown
Z = 4	0.20 × 0.15 × 0.14 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3007 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.637, T_max = 0.723	k = −20→26
7986 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.1143P)² + 1.9553P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3007 reflections	Δρ_max = 0.75 e Å⁻³
224 parameters	Δρ_min = −1.42 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1400 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

[Er(C₁₈H_22.5N₂O₄)₂]	V = 3471.8 (6) Å³
M_r = 829.02	Z = 4
Orthorhombic, Iba2	Mo Kα radiation
a = 11.1542 (10) Å	µ = 2.48 mm⁻¹
b = 21.958 (2) Å	T = 298 K
c = 14.1751 (15) Å	0.20 × 0.15 × 0.14 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3007 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2199 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.723	R_int = 0.031
7986 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.162	Δρ_max = 0.75 e Å⁻³
S = 1.06	Δρ_min = −1.42 e Å⁻³
3007 reflections	Absolute structure: Flack (1983), 1400 Freidel pairs
224 parameters	Absolute structure parameter: 0.02 (5)
1 restraint

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	Occ. (<1)
Er1	1.0000	1.0000	0.0158 (2)	0.0342 (2)
O1	0.9418 (5)	1.0681 (3)	0.1202 (4)	0.0297 (13)
H1	0.9919	1.0955	0.1209	0.045*	0.50
O2	0.9141 (6)	1.1865 (3)	0.0933 (5)	0.0479 (18)
O3	1.1356 (6)	0.9653 (3)	−0.0834 (5)	0.0389 (16)
O4	1.3687 (7)	0.9386 (4)	−0.0660 (7)	0.065 (3)
N1	0.7906 (7)	0.9657 (4)	0.0823 (6)	0.040 (2)
H1C	0.7358	0.9838	0.0439	0.048*
N2	0.9283 (8)	0.8957 (4)	−0.0492 (6)	0.043 (2)
H2	0.9673	0.8670	−0.0146	0.052*
C1	0.7624 (12)	0.9901 (6)	0.1789 (10)	0.049 (3)
H1A	0.6906	0.9706	0.2029	0.058*
H1B	0.8279	0.9809	0.2216	0.058*
C2	0.7440 (9)	1.0568 (5)	0.1748 (7)	0.042 (3)
C3	0.8366 (9)	1.0926 (5)	0.1404 (7)	0.039 (3)
C4	0.8159 (9)	1.1552 (5)	0.1290 (7)	0.041 (2)
C5	0.7089 (10)	1.1808 (6)	0.1508 (8)	0.051 (3)
H5	0.6957	1.2223	0.1429	0.061*
C6	0.6169 (10)	1.1415 (7)	0.1866 (9)	0.056 (3)
H6	0.5428	1.1582	0.2021	0.067*
C7	0.6330 (9)	1.0854 (7)	0.1977 (9)	0.057 (3)
H7	0.5708	1.0618	0.2216	0.068*
C8	0.8935 (13)	1.2474 (5)	0.0637 (10)	0.064 (3)
H8A	0.8112	1.2519	0.0451	0.095*
H8B	0.9447	1.2567	0.0112	0.095*
H8C	0.9107	1.2747	0.1149	0.095*
C9	0.9606 (16)	0.8829 (7)	−0.1469 (9)	0.061 (4)
H9A	0.9455	0.9184	−0.1860	0.073*
H9B	0.9135	0.8492	−0.1709	0.073*
C10	1.0949 (14)	0.8668 (6)	−0.1482 (8)	0.054 (3)
C11	1.1731 (11)	0.9109 (5)	−0.1134 (7)	0.043 (3)
C12	1.2992 (13)	0.8958 (6)	−0.1052 (8)	0.056 (3)
C13	1.3345 (14)	0.8375 (6)	−0.1369 (9)	0.063 (4)
H13	1.4149	0.8264	−0.1333	0.076*
C14	1.2544 (16)	0.7976 (7)	−0.1721 (10)	0.070 (4)
H14	1.2804	0.7590	−0.1897	0.084*
C15	1.1369 (14)	0.8120 (6)	−0.1826 (9)	0.066 (4)
H15	1.0850	0.7852	−0.2128	0.079*
C16	1.4901 (11)	0.9202 (11)	−0.0443 (19)	0.092 (7)
H16A	1.5326	0.9538	−0.0167	0.139*
H16B	1.5298	0.9078	−0.1013	0.139*
H16C	1.4885	0.8868	−0.0007	0.139*
C17	0.7704 (9)	0.9017 (5)	0.0703 (9)	0.051 (3)
H17A	0.6876	0.8920	0.0849	0.061*
H17B	0.8216	0.8789	0.1127	0.061*
C18	0.7979 (11)	0.8845 (5)	−0.0316 (10)	0.052 (3)
H18A	0.7792	0.8419	−0.0422	0.063*
H18B	0.7498	0.9089	−0.0743	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.0382 (3)	0.0267 (3)	0.0377 (3)	0.0000 (2)	0.000	0.000
O1	0.018 (3)	0.033 (4)	0.038 (3)	0.003 (3)	0.005 (3)	−0.004 (3)
O2	0.053 (4)	0.035 (4)	0.055 (4)	0.009 (3)	0.001 (3)	−0.007 (3)
O3	0.056 (4)	0.026 (4)	0.034 (4)	0.014 (3)	0.011 (3)	−0.001 (3)
O4	0.055 (5)	0.055 (6)	0.085 (7)	0.019 (4)	0.031 (4)	0.023 (5)
N1	0.031 (4)	0.038 (5)	0.052 (5)	−0.009 (4)	−0.007 (4)	0.012 (4)
N2	0.051 (6)	0.026 (4)	0.052 (5)	−0.003 (4)	−0.024 (4)	0.003 (4)
C1	0.041 (6)	0.055 (8)	0.050 (7)	−0.002 (5)	0.001 (5)	0.017 (5)
C2	0.032 (5)	0.048 (7)	0.046 (6)	0.008 (5)	0.005 (4)	0.005 (5)
C3	0.036 (6)	0.045 (7)	0.036 (6)	0.005 (5)	−0.009 (4)	−0.003 (5)
C4	0.043 (6)	0.041 (6)	0.040 (5)	0.010 (5)	−0.008 (5)	−0.004 (5)
C5	0.046 (6)	0.051 (7)	0.055 (7)	0.018 (6)	−0.003 (5)	−0.006 (5)
C6	0.042 (7)	0.066 (9)	0.060 (8)	0.019 (6)	0.007 (5)	0.007 (6)
C7	0.036 (6)	0.071 (10)	0.063 (8)	0.006 (6)	0.015 (5)	0.010 (7)
C8	0.079 (9)	0.025 (6)	0.087 (9)	−0.003 (6)	0.010 (7)	0.008 (6)
C9	0.086 (9)	0.045 (8)	0.052 (8)	−0.001 (7)	−0.019 (7)	−0.007 (6)
C10	0.084 (9)	0.036 (6)	0.043 (6)	0.015 (6)	−0.005 (6)	−0.003 (5)
C11	0.063 (8)	0.041 (7)	0.024 (6)	0.021 (6)	0.007 (5)	0.010 (5)
C12	0.076 (9)	0.047 (7)	0.045 (6)	0.029 (7)	0.021 (6)	0.011 (6)
C13	0.084 (10)	0.051 (9)	0.056 (8)	0.034 (8)	0.022 (7)	0.011 (6)
C14	0.104 (12)	0.049 (8)	0.057 (8)	0.024 (8)	0.011 (7)	−0.003 (7)
C15	0.105 (12)	0.045 (8)	0.047 (7)	0.019 (7)	−0.005 (7)	−0.011 (6)
C16	0.060 (10)	0.089 (15)	0.128 (17)	0.026 (7)	0.030 (8)	0.031 (13)
C17	0.037 (6)	0.040 (7)	0.075 (10)	−0.011 (5)	−0.017 (6)	0.013 (6)
C18	0.057 (7)	0.023 (6)	0.076 (8)	−0.016 (5)	−0.029 (6)	0.011 (5)

Geometric parameters (Å, º) top

Er1—O3ⁱ	2.202 (6)	C5—C6	1.433 (19)
Er1—O3	2.202 (6)	C5—H5	0.9300
Er1—O1	2.203 (6)	C6—C7	1.254 (19)
Er1—O1ⁱ	2.203 (6)	C6—H6	0.9300
Er1—N2	2.595 (8)	C7—H7	0.9300
Er1—N2ⁱ	2.595 (8)	C8—H8A	0.9600
Er1—N1ⁱ	2.628 (8)	C8—H8B	0.9600
Er1—N1	2.628 (8)	C8—H8C	0.9600
O1—C3	1.321 (12)	C9—C10	1.54 (2)
O1—H1	0.8200	C9—H9A	0.9700
O2—C4	1.389 (13)	C9—H9B	0.9700
O2—C8	1.419 (14)	C10—C15	1.379 (17)
O3—C11	1.334 (13)	C10—C11	1.394 (19)
O4—C12	1.340 (16)	C11—C12	1.450 (17)
O4—C16	1.446 (16)	C12—C13	1.412 (17)
N1—C17	1.433 (14)	C13—C14	1.35 (2)
N1—C1	1.504 (16)	C13—H13	0.9300
N1—H1C	0.9094	C14—C15	1.36 (2)
N2—C9	1.458 (16)	C14—H14	0.9300
N2—C18	1.495 (15)	C15—H15	0.9300
N2—H2	0.9105	C16—H16A	0.9600
C1—C2	1.479 (15)	C16—H16B	0.9600
C1—H1A	0.9700	C16—H16C	0.9600
C1—H1B	0.9700	C17—C18	1.523 (17)
C2—C3	1.387 (15)	C17—H17A	0.9700
C2—C7	1.426 (15)	C17—H17B	0.9700
C3—C4	1.404 (15)	C18—H18A	0.9700
C4—C5	1.355 (15)	C18—H18B	0.9700

O3ⁱ—Er1—O3	100.6 (4)	C5—C4—C3	121.7 (11)
O3ⁱ—Er1—O1	89.5 (2)	O2—C4—C3	113.4 (8)
O3—Er1—O1	150.1 (2)	C4—C5—C6	117.5 (12)
O3ⁱ—Er1—O1ⁱ	150.1 (2)	C4—C5—H5	121.3
O3—Er1—O1ⁱ	89.5 (2)	C6—C5—H5	121.3
O1—Er1—O1ⁱ	95.6 (3)	C7—C6—C5	122.2 (11)
O3ⁱ—Er1—N2	82.4 (3)	C7—C6—H6	118.9
O3—Er1—N2	71.3 (3)	C5—C6—H6	118.9
O1—Er1—N2	138.4 (3)	C6—C7—C2	121.9 (12)
O1ⁱ—Er1—N2	74.3 (2)	C6—C7—H7	119.1
O3ⁱ—Er1—N2ⁱ	71.3 (3)	C2—C7—H7	119.1
O3—Er1—N2ⁱ	82.4 (3)	O2—C8—H8A	109.5
O1—Er1—N2ⁱ	74.3 (2)	O2—C8—H8B	109.5
O1ⁱ—Er1—N2ⁱ	138.4 (3)	H8A—C8—H8B	109.5
N2—Er1—N2ⁱ	138.4 (4)	O2—C8—H8C	109.5
O3ⁱ—Er1—N1ⁱ	137.8 (3)	H8A—C8—H8C	109.5
O3—Er1—N1ⁱ	73.6 (2)	H8B—C8—H8C	109.5
O1—Er1—N1ⁱ	80.0 (2)	N2—C9—C10	107.3 (10)
O1ⁱ—Er1—N1ⁱ	72.0 (2)	N2—C9—H9A	110.3
N2—Er1—N1ⁱ	130.8 (3)	C10—C9—H9A	110.3
N2ⁱ—Er1—N1ⁱ	66.5 (3)	N2—C9—H9B	110.3
O3ⁱ—Er1—N1	73.6 (2)	C10—C9—H9B	110.3
O3—Er1—N1	137.8 (3)	H9A—C9—H9B	108.5
O1—Er1—N1	72.0 (2)	C15—C10—C11	121.3 (13)
O1ⁱ—Er1—N1	80.0 (2)	C15—C10—C9	122.4 (12)
N2—Er1—N1	66.5 (3)	C11—C10—C9	116.4 (10)
N2ⁱ—Er1—N1	130.8 (3)	O3—C11—C10	122.6 (10)
N1ⁱ—Er1—N1	138.0 (4)	O3—C11—C12	118.9 (11)
C3—O1—Er1	133.1 (6)	C10—C11—C12	118.4 (11)
C3—O1—H1	107.7	O4—C12—C13	127.4 (13)
Er1—O1—H1	107.7	O4—C12—C11	115.7 (10)
C4—O2—C8	116.5 (9)	C13—C12—C11	116.9 (14)
C11—O3—Er1	136.7 (7)	C14—C13—C12	121.5 (14)
C12—O4—C16	115.7 (13)	C14—C13—H13	119.3
C17—N1—C1	115.1 (9)	C12—C13—H13	119.3
C17—N1—Er1	112.2 (6)	C13—C14—C15	121.9 (13)
C1—N1—Er1	114.2 (7)	C13—C14—H14	119.0
C17—N1—H1C	104.5	C15—C14—H14	119.0
C1—N1—H1C	104.4	C14—C15—C10	119.6 (14)
Er1—N1—H1C	105.0	C14—C15—H15	120.2
C9—N2—C18	111.6 (10)	C10—C15—H15	120.2
C9—N2—Er1	115.5 (8)	O4—C16—H16A	109.5
C18—N2—Er1	112.7 (6)	O4—C16—H16B	109.5
C9—N2—H2	105.1	H16A—C16—H16B	109.5
C18—N2—H2	105.1	O4—C16—H16C	109.5
Er1—N2—H2	105.8	H16A—C16—H16C	109.5
C2—C1—N1	110.2 (9)	H16B—C16—H16C	109.5
C2—C1—H1A	109.6	N1—C17—C18	108.9 (9)
N1—C1—H1A	109.6	N1—C17—H17A	109.9
C2—C1—H1B	109.6	C18—C17—H17A	109.9
N1—C1—H1B	109.6	N1—C17—H17B	109.9
H1A—C1—H1B	108.1	C18—C17—H17B	109.9
C3—C2—C7	118.5 (11)	H17A—C17—H17B	108.3
C3—C2—C1	118.1 (10)	N2—C18—C17	108.3 (8)
C7—C2—C1	123.2 (10)	N2—C18—H18A	110.0
O1—C3—C2	120.5 (10)	C17—C18—H18A	110.0
O1—C3—C4	121.3 (9)	N2—C18—H18B	110.0
C2—C3—C4	118.2 (9)	C17—C18—H18B	110.0
C5—C4—O2	124.9 (10)	H18A—C18—H18B	108.4

O3ⁱ—Er1—O1—C3	33.8 (8)	Er1—O1—C3—C2	64.0 (13)
O3—Er1—O1—C3	144.6 (8)	Er1—O1—C3—C4	−116.8 (9)
O1ⁱ—Er1—O1—C3	−116.7 (9)	C7—C2—C3—O1	178.5 (10)
N2—Er1—O1—C3	−44.0 (10)	C1—C2—C3—O1	−6.0 (15)
N2ⁱ—Er1—O1—C3	104.5 (9)	C7—C2—C3—C4	−0.7 (15)
N1ⁱ—Er1—O1—C3	172.7 (9)	C1—C2—C3—C4	174.8 (10)
N1—Er1—O1—C3	−39.1 (8)	C8—O2—C4—C5	−10.6 (15)
O3ⁱ—Er1—O3—C11	−106.2 (10)	C8—O2—C4—C3	168.9 (10)
O1—Er1—O3—C11	145.9 (9)	O1—C3—C4—C5	−179.0 (10)
O1ⁱ—Er1—O3—C11	45.5 (10)	C2—C3—C4—C5	0.2 (16)
N2—Er1—O3—C11	−28.1 (9)	O1—C3—C4—O2	1.5 (14)
N2ⁱ—Er1—O3—C11	−175.4 (10)	C2—C3—C4—O2	−179.3 (9)
N1ⁱ—Er1—O3—C11	116.9 (10)	O2—C4—C5—C6	179.7 (10)
N1—Er1—O3—C11	−29.0 (11)	C3—C4—C5—C6	0.2 (17)
O3ⁱ—Er1—N1—C17	107.2 (7)	C4—C5—C6—C7	0 (2)
O3—Er1—N1—C17	19.4 (8)	C5—C6—C7—C2	0 (2)
O1—Er1—N1—C17	−157.9 (7)	C3—C2—C7—C6	0.9 (18)
O1ⁱ—Er1—N1—C17	−58.7 (7)	C1—C2—C7—C6	−174.4 (13)
N2—Er1—N1—C17	18.5 (6)	C18—N2—C9—C10	−154.4 (9)
N2ⁱ—Er1—N1—C17	153.1 (7)	Er1—N2—C9—C10	75.2 (10)
N1ⁱ—Er1—N1—C17	−107.1 (7)	N2—C9—C10—C15	122.1 (13)
O3ⁱ—Er1—N1—C1	−119.5 (7)	N2—C9—C10—C11	−58.5 (14)
O3—Er1—N1—C1	152.8 (6)	Er1—O3—C11—C10	52.0 (14)
O1—Er1—N1—C1	−24.5 (7)	Er1—O3—C11—C12	−124.9 (10)
O1ⁱ—Er1—N1—C1	74.7 (7)	C15—C10—C11—O3	177.0 (10)
N2—Er1—N1—C1	151.9 (7)	C9—C10—C11—O3	−2.4 (16)
N2ⁱ—Er1—N1—C1	−73.6 (8)	C15—C10—C11—C12	−6.0 (17)
N1ⁱ—Er1—N1—C1	26.3 (6)	C9—C10—C11—C12	174.5 (9)
O3ⁱ—Er1—N2—C9	69.5 (9)	C16—O4—C12—C13	−7.5 (19)
O3—Er1—N2—C9	−34.5 (9)	C16—O4—C12—C11	170.7 (12)
O1—Er1—N2—C9	150.1 (8)	O3—C11—C12—O4	0.9 (14)
O1ⁱ—Er1—N2—C9	−129.4 (9)	C10—C11—C12—O4	−176.1 (11)
N2ⁱ—Er1—N2—C9	19.2 (8)	O3—C11—C12—C13	179.3 (10)
N1ⁱ—Er1—N2—C9	−81.1 (9)	C10—C11—C12—C13	2.3 (15)
N1—Er1—N2—C9	144.9 (9)	O4—C12—C13—C14	177.5 (12)
O3ⁱ—Er1—N2—C18	−60.3 (7)	C11—C12—C13—C14	−0.7 (17)
O3—Er1—N2—C18	−164.3 (7)	C12—C13—C14—C15	3 (2)
O1—Er1—N2—C18	20.2 (8)	C13—C14—C15—C10	−6 (2)
O1ⁱ—Er1—N2—C18	100.8 (7)	C11—C10—C15—C14	8 (2)
N2ⁱ—Er1—N2—C18	−110.7 (7)	C9—C10—C15—C14	−172.5 (12)
N1ⁱ—Er1—N2—C18	149.1 (6)	C1—N1—C17—C18	177.7 (9)
N1—Er1—N2—C18	15.1 (6)	Er1—N1—C17—C18	−49.4 (9)
C17—N1—C1—C2	−159.7 (9)	C9—N2—C18—C17	−177.3 (10)
Er1—N1—C1—C2	68.3 (10)	Er1—N2—C18—C17	−45.5 (9)
N1—C1—C2—C3	−58.1 (13)	N1—C17—C18—N2	63.8 (10)
N1—C1—C2—C7	117.1 (12)

Symmetry code: (i) −x+2, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O4ⁱⁱ	0.96	2.70	3.49 (3)	140
N2—H2···O2ⁱ	0.91	2.34	3.230 (10)	166
N1—H1C···O4ⁱ	0.91	2.59	3.462 (12)	162
O1—H1···O2	0.82	2.21	2.646 (9)	113

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

Experimental details

Crystal data
Chemical formula	[Er(C₁₈H_22.5N₂O₄)₂]
M_r	829.02
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	298
a, b, c (Å)	11.1542 (10), 21.958 (2), 14.1751 (15)
V (Å³)	3471.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.20 × 0.15 × 0.14

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.637, 0.723
No. of measured, independent and observed [I > 2σ(I)] reflections	7986, 3007, 2199
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.162, 1.06
No. of reflections	3007
No. of parameters	224
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −1.42
Absolute structure	Flack (1983), 1400 Freidel pairs
Absolute structure parameter	0.02 (5)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Er1—O3ⁱ	2.202 (6)	Er1—N2	2.595 (8)
Er1—O3	2.202 (6)	Er1—N2ⁱ	2.595 (8)
Er1—O1	2.203 (6)	Er1—N1ⁱ	2.628 (8)
Er1—O1ⁱ	2.203 (6)	Er1—N1	2.628 (8)

Symmetry code: (i) −x+2, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O4ⁱⁱ	0.96	2.70	3.49 (3)	140.2
N2—H2···O2ⁱ	0.91	2.34	3.230 (10)	166.2
N1—H1C···O4ⁱ	0.91	2.59	3.462 (12)	161.9
O1—H1···O2	0.82	2.21	2.646 (9)	113.1

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

Acknowledgements

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, Y.-F., Xia, H.-T., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m484–m486. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2006). Acta Cryst. E62, o5864–o5865. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2009a). Acta Cryst. E65, m200. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2009b). Acta Cryst. E65, m201. Web of Science CSD CrossRef IUCr Journals Google Scholar

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