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Acta Cryst. (2007). E63, m2544    [ doi:10.1107/S1600536807044546 ]

Diaquabis(1-naphthaleneacetato-[kappa]O)bis(1,10-phenanthroline-[kappa]2N,N')erbium(III) 1-naphthaleneacetate monohydrate

Y.-F. Liu, H.-T. Xia, D.-Q. Wang, S.-P. Yang and Y.-L. Meng

Abstract top

In title compound, [Er(C12H9O2)2(C12H8N2)2(H2O)2](C12H9O2)·H2O, the carboxyl groups have only a monodentate coordination mode. The ErIII atom is eight-coordinated in a distorted dodecahedral environment by four O and four N atoms from two 1-naphthaleneacetic acid (NAA) ligands, two aqua ligands and two 1,10-phenanthroline (phen) ligands. A twofold rotation axis passes through Er. The molecules are linked into sheets by O-H...O and C-H...O hydrogen bonds. There is disorder in the anion and in the solvent water molecule; the site occupancies were set equal to 0.5.

Comment top

Rare earth aromatic carboxylate complexes have received significant attention in recent years because of their special electronic structures, various coordination modes and as treasure-house of new material (An et al., 2005; Xu & Yan, 2007). It is therefore of significance to investigate the crystal structures of rare earth complexes which will provide a help for understanding the optical, magnetic properties and biological activity of complexes (Gawryszewska et al., 2005). As a part of our investigation of the crystal structures of rare earth NAA complexes with phen, this paper reports the syntheses and crystal structure of the a new complex, (I).

In the title complex, the erbium(III) center is eight-coordinated by four N atoms from two phen ligands and four O atoms from two NAA and two water ligands (Fig. 1). The Er atom situates at a distorted dodecahedron geometry. The Er—O distances are 2.947 (7) Å (carboxyl) and 2.307 (7) Å (water). The molecules of (I) are linked into sheets by O—H···O and C—H···O hydrogen bonds (Table 2). There are on direction-specific interactions between adjacent sheets in the three-dimensional network structure.

Related literature top

For related literature, see: An et al. (2005); Gawryszewska et al. (2005); Xu & Yan (2007).

Experimental top

To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) and 1,10-phenanthroline monohydrate (0.198 g, 1 mmol) in 30 ml me thanol, and a solution of Er(NO3)3·6H2O (0.461 g, 1 mmol) in water (10 ml) was added. The mixed solution was heated to 333 K and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colourless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution.

Refinement top

All H atoms were located in a difference Fourier map and then treated as riding atoms, with C—H = distances of 0.93 (aryl), 0.97 Å (methylene), and O—H distances of 0.85, and with Uiso(H) = 1.2Ueq(C) (aryl and methylene) or 1.5Ueq(O) (water). The carboxylate radical methylene and H atoms bonded to C27, C27(B) and uncoordinated water were found to be disordered. The coordinates of the carboxylate radical methylene, H atom and the water were refined with the occupancies to half unity.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] 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) 1 − x, y, 3/2 − z, (B) 1 − x, 2 − y, 2 − z].
Diaquabis(1-naphthaleneacetato-κO)bis(1,10-phenanthroline- κ2N,N')erbium(III) 1-naphthaleneacetate monohydrate top
Crystal data top
[Er(C12H9O2)2(C12H8N2)2(H2O)2](C12H9O2)·H2OF000 = 2308
Mr = 1137.29Dx = 1.389 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4270 reflections
a = 24.645 (3) Åθ = 2.4–25.1º
b = 14.1144 (19) ŵ = 1.60 mm−1
c = 18.162 (2) ÅT = 298 (2) K
β = 120.575 (2)ºBlock, colourless
V = 5439.4 (12) Å30.31 × 0.12 × 0.10 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		4691 independent reflections
Radiation source: fine-focus sealed tube3523 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.089
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −28→29
Tmin = 0.636, Tmax = 0.856k = −16→15
13646 measured reflectionsl = −21→21
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.220  w = 1/[σ2(Fo2) + (0.1579P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4691 reflectionsΔρmax = 2.52 e Å−3
357 parametersΔρmin = −2.37 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Er(C12H9O2)2(C12H8N2)2(H2O)2](C12H9O2)·H2OV = 5439.4 (12) Å3
Mr = 1137.29Z = 4
Monoclinic, C2/cMo Kα
a = 24.645 (3) ŵ = 1.60 mm−1
b = 14.1144 (19) ÅT = 298 (2) K
c = 18.162 (2) Å0.31 × 0.12 × 0.10 mm
β = 120.575 (2)º
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer		4691 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3523 reflections with I > 2σ(I)
Tmin = 0.636, Tmax = 0.856Rint = 0.089
13646 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.078357 parameters
wR(F2) = 0.220H-atom parameters constrained
S = 1.00Δρmax = 2.52 e Å−3
4691 reflectionsΔρmin = −2.37 e Å−3
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
xyzUiso*/UeqOcc. (<1)
Er10.50000.53049 (3)0.75000.0479 (3)
N10.5510 (4)0.5715 (6)0.9090 (5)0.0572 (19)
N20.4950 (4)0.3990 (6)0.8417 (5)0.0599 (19)
O10.3989 (3)0.4731 (5)0.6841 (5)0.0689 (19)
O20.3239 (4)0.5813 (9)0.6529 (7)0.110 (3)
O30.5604 (4)0.6579 (5)0.7551 (4)0.0643 (17)
H3A0.59760.65690.79830.077*
H3B0.54300.71130.75070.077*
O40.5331 (13)0.8380 (12)0.7814 (18)0.115 (8)0.50
O50.4485 (16)0.8284 (16)0.7910 (18)0.126 (8)0.50
O60.3437 (15)0.9071 (17)0.6725 (19)0.146 (9)0.50
H6A0.36160.88690.72370.175*0.50
H6B0.36990.90090.65550.175*0.50
C10.3427 (6)0.5022 (12)0.6397 (8)0.080 (3)
C20.2962 (6)0.4362 (12)0.5690 (9)0.091 (4)
H2A0.25380.45350.55440.109*
H2B0.29950.44580.51860.109*
C30.3062 (7)0.3329 (13)0.5923 (10)0.100 (5)
C40.3382 (7)0.2802 (14)0.5617 (11)0.110 (5)
H40.35130.30880.52710.132*
C50.3508 (8)0.1849 (17)0.5827 (13)0.125 (6)
H50.37220.14970.56220.150*
C60.3313 (11)0.1423 (18)0.6344 (15)0.142 (8)
H60.33970.07850.64840.170*
C70.2993 (10)0.195 (2)0.6651 (14)0.131 (7)
C80.2867 (7)0.2903 (16)0.6440 (10)0.108 (5)
C90.2547 (8)0.3430 (16)0.6747 (11)0.117 (6)
H90.24630.40680.66060.140*
C100.2352 (10)0.300 (2)0.7263 (14)0.145 (8)
H100.21380.33550.74690.174*
C110.2478 (10)0.205 (2)0.7473 (14)0.143 (8)
H110.23470.17640.78190.172*
C120.2798 (11)0.152 (2)0.7167 (15)0.147 (8)
H120.28820.08850.73080.176*
C130.5766 (6)0.6542 (8)0.9433 (8)0.072 (3)
H130.56910.70460.90630.086*
C140.6140 (6)0.6717 (9)1.0312 (8)0.077 (3)
H140.63120.73131.05160.092*
C150.6247 (5)0.5977 (10)1.0867 (7)0.077 (3)
H150.65060.60621.14540.093*
C160.5965 (6)0.5108 (9)1.0544 (7)0.066 (3)
C170.5607 (5)0.4977 (8)0.9650 (7)0.060 (2)
C180.5315 (5)0.4073 (8)0.9300 (6)0.058 (2)
C190.5390 (5)0.3316 (8)0.9847 (7)0.069 (3)
C200.5084 (6)0.2451 (8)0.9483 (9)0.079 (3)
H200.51250.19370.98270.095*
C210.4726 (6)0.2385 (8)0.8615 (9)0.079 (3)
H210.45200.18220.83590.095*
C220.4671 (5)0.3182 (7)0.8106 (7)0.062 (2)
H220.44210.31240.75150.075*
C230.6053 (6)0.4298 (10)1.1102 (8)0.077 (3)
H230.63040.43651.16920.092*
C240.5780 (6)0.3474 (10)1.0772 (8)0.080 (3)
H240.58370.29771.11410.096*
C250.492 (3)0.872 (2)0.794 (3)0.122 (13)0.50
C260.503 (3)0.9720 (18)0.826 (3)0.125 (14)0.50
H26A0.53471.00180.81770.150*0.50
H26B0.46391.00780.79380.150*0.50
C270.5229 (18)0.9724 (12)0.9185 (19)0.144 (9)
H270.50340.96910.85920.172*0.50
C280.5870 (19)0.9554 (14)0.969 (2)0.155 (10)
H280.60980.93610.94340.186*
C290.6169 (18)0.9667 (13)1.056 (2)0.160 (11)
H290.66010.95661.08950.192*
C300.5817 (18)0.9935 (16)1.0932 (19)0.155 (10)
H300.60291.00431.15180.186*
C310.4880 (17)0.9944 (14)0.9563 (16)0.140 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Er10.0420 (4)0.0472 (4)0.0390 (4)0.0000.0093 (3)0.000
N10.051 (5)0.063 (5)0.048 (5)−0.001 (4)0.019 (4)0.000 (4)
N20.056 (5)0.059 (4)0.055 (5)0.003 (4)0.022 (4)0.005 (4)
O10.037 (4)0.082 (5)0.063 (5)−0.008 (3)0.008 (3)0.002 (4)
O20.053 (5)0.132 (8)0.103 (7)0.019 (6)0.009 (5)−0.032 (7)
O30.065 (4)0.063 (4)0.054 (4)−0.010 (3)0.023 (3)−0.002 (3)
O40.17 (2)0.059 (10)0.12 (2)0.009 (11)0.070 (17)−0.001 (11)
O50.19 (3)0.082 (13)0.13 (2)0.014 (15)0.10 (2)−0.006 (13)
O60.19 (3)0.108 (16)0.15 (2)0.019 (18)0.09 (2)0.007 (16)
C10.051 (7)0.118 (9)0.060 (7)−0.017 (7)0.020 (6)−0.017 (7)
C20.052 (7)0.134 (11)0.066 (8)−0.024 (7)0.015 (6)−0.021 (8)
C30.059 (8)0.139 (13)0.077 (9)−0.036 (8)0.017 (7)−0.027 (9)
C40.069 (9)0.138 (14)0.087 (10)−0.033 (9)0.014 (8)−0.018 (10)
C50.075 (11)0.149 (17)0.099 (13)−0.032 (11)0.007 (9)−0.027 (12)
C60.090 (14)0.151 (17)0.104 (15)−0.046 (13)−0.010 (11)−0.016 (14)
C70.086 (13)0.16 (2)0.093 (13)−0.049 (14)0.008 (10)−0.012 (14)
C80.066 (9)0.149 (15)0.080 (10)−0.046 (10)0.016 (8)−0.017 (10)
C90.077 (10)0.160 (15)0.090 (11)−0.048 (11)0.025 (9)−0.015 (11)
C100.100 (14)0.19 (2)0.102 (14)−0.049 (15)0.020 (11)−0.022 (14)
C110.095 (15)0.18 (2)0.103 (15)−0.049 (16)0.015 (12)−0.007 (16)
C120.099 (15)0.17 (2)0.106 (15)−0.047 (15)0.004 (12)−0.008 (15)
C130.067 (7)0.077 (7)0.063 (7)−0.011 (6)0.028 (6)−0.007 (5)
C140.060 (7)0.096 (8)0.059 (7)−0.015 (6)0.019 (6)−0.015 (6)
C150.055 (7)0.108 (9)0.050 (6)−0.001 (6)0.013 (5)−0.012 (7)
C160.053 (6)0.095 (7)0.048 (6)0.006 (5)0.023 (5)0.005 (5)
C170.051 (6)0.077 (6)0.054 (6)0.004 (5)0.029 (5)0.003 (5)
C180.046 (5)0.071 (6)0.058 (6)0.006 (5)0.029 (5)0.007 (5)
C190.061 (7)0.077 (7)0.062 (7)0.013 (5)0.025 (5)0.013 (5)
C200.074 (8)0.078 (7)0.079 (9)0.006 (6)0.034 (7)0.022 (6)
C210.067 (8)0.065 (6)0.087 (9)−0.005 (5)0.027 (7)0.010 (6)
C220.051 (6)0.059 (5)0.066 (7)−0.004 (4)0.022 (5)0.007 (5)
C230.068 (8)0.102 (9)0.051 (6)0.011 (7)0.023 (6)0.010 (6)
C240.068 (8)0.098 (9)0.065 (7)0.013 (7)0.027 (6)0.023 (7)
C250.19 (4)0.08 (2)0.12 (3)0.01 (3)0.09 (3)0.007 (19)
C260.20 (5)0.077 (19)0.12 (3)0.01 (2)0.09 (3)0.012 (16)
C270.22 (3)0.090 (12)0.13 (2)0.009 (14)0.09 (2)0.012 (11)
C280.21 (3)0.096 (12)0.15 (2)0.013 (15)0.09 (2)0.011 (13)
C290.23 (3)0.105 (15)0.15 (2)0.017 (14)0.10 (3)0.013 (13)
C300.23 (4)0.095 (12)0.15 (2)0.004 (17)0.10 (3)0.014 (14)
C310.22 (3)0.084 (10)0.129 (19)0.019 (15)0.10 (2)0.010 (12)
Geometric parameters (Å, °) top
Er1—O12.294 (7)C10—C111.39 (3)
Er1—O1i2.294 (7)C10—H100.9300
Er1—O32.307 (7)C11—C121.39 (3)
Er1—O3i2.307 (7)C11—H110.9300
Er1—N2i2.537 (8)C12—H120.9300
Er1—N22.537 (8)C13—C141.401 (16)
Er1—N12.561 (8)C13—H130.9300
Er1—N1i2.561 (8)C14—C151.381 (17)
N1—C131.322 (14)C14—H140.9300
N1—C171.390 (14)C15—C161.385 (18)
N2—C221.303 (13)C15—H150.9300
N2—C181.388 (13)C16—C171.411 (16)
O1—C11.265 (16)C16—C231.468 (18)
O2—C11.277 (18)C17—C181.444 (16)
O3—H3A0.8500C18—C191.406 (14)
O3—H3B0.8500C19—C201.411 (17)
O4—C251.23 (5)C19—C241.467 (18)
O4—C25i1.27 (4)C20—C211.362 (18)
O4—O4i1.44 (5)C20—H200.9300
O4—O5i1.60 (4)C21—C221.419 (15)
O5—C251.22 (5)C21—H210.9300
O5—O4i1.60 (4)C22—H220.9300
O6—H6A0.8499C23—C241.326 (19)
O6—H6B0.8500C23—H230.9300
C1—C21.527 (18)C24—H240.9300
C2—C31.50 (2)C25—O4i1.27 (4)
C2—H2A0.9700C25—C261.50 (4)
C2—H2B0.9700C26—C271.49 (5)
C3—C41.39 (2)C26—H26A0.9700
C3—C81.39 (2)C26—H26B0.9700
C4—C51.39 (3)C27—C311.38 (4)
C4—H40.9300C27—C281.38 (4)
C5—C61.39 (3)C27—H270.9300
C5—H50.9300C28—C291.37 (4)
C6—C71.39 (3)C28—H280.9300
C6—H60.9300C29—C301.40 (4)
C7—C121.39 (3)C29—H290.9300
C7—C81.39 (3)C30—C31ii1.49 (4)
C8—C91.39 (3)C30—H300.9300
C9—C101.39 (3)C31—C31ii1.39 (5)
C9—H90.9300C31—C30ii1.49 (4)
O1—Er1—O1i138.7 (4)C11—C10—H10120.0
O1—Er1—O3143.5 (3)C12—C11—C10120 (3)
O1i—Er1—O375.3 (3)C12—C11—H11120.0
O1—Er1—O3i75.3 (3)C10—C11—H11120.0
O1i—Er1—O3i143.5 (3)C11—C12—C7120 (3)
O3—Er1—O3i77.6 (4)C11—C12—H12120.0
O1—Er1—N2i78.6 (3)C7—C12—H12120.0
O1i—Er1—N2i71.5 (3)N1—C13—C14124.9 (11)
O3—Er1—N2i110.5 (2)N1—C13—H13117.6
O3i—Er1—N2i142.2 (3)C14—C13—H13117.6
O1—Er1—N271.5 (3)C15—C14—C13118.0 (11)
O1i—Er1—N278.6 (3)C15—C14—H14121.0
O3—Er1—N2142.2 (3)C13—C14—H14121.0
O3i—Er1—N2110.5 (2)C14—C15—C16119.4 (10)
N2i—Er1—N286.0 (4)C14—C15—H15120.3
O1—Er1—N1116.6 (3)C16—C15—H15120.3
O1i—Er1—N173.2 (3)C15—C16—C17119.3 (11)
O3—Er1—N180.9 (2)C15—C16—C23122.0 (11)
O3i—Er1—N178.8 (3)C17—C16—C23118.6 (12)
N2i—Er1—N1138.2 (3)N1—C17—C16121.2 (10)
N2—Er1—N165.5 (3)N1—C17—C18118.6 (9)
O1—Er1—N1i73.2 (3)C16—C17—C18120.1 (10)
O1i—Er1—N1i116.6 (3)N2—C18—C19121.9 (10)
O3—Er1—N1i78.8 (3)N2—C18—C17117.9 (9)
O3i—Er1—N1i80.9 (2)C19—C18—C17120.2 (10)
N2i—Er1—N1i65.5 (3)C18—C19—C20118.6 (11)
N2—Er1—N1i138.2 (3)C18—C19—C24117.9 (11)
N1—Er1—N1i153.9 (4)C20—C19—C24123.4 (11)
C13—N1—C17117.0 (9)C21—C20—C19118.6 (10)
C13—N1—Er1125.0 (7)C21—C20—H20120.7
C17—N1—Er1117.3 (7)C19—C20—H20120.7
C22—N2—C18117.6 (9)C20—C21—C22119.4 (11)
C22—N2—Er1123.1 (7)C20—C21—H21120.3
C18—N2—Er1118.5 (6)C22—C21—H21120.3
C1—O1—Er1139.9 (8)N2—C22—C21123.8 (11)
Er1—O3—H3A113.2N2—C22—H22118.1
Er1—O3—H3B113.7C21—C22—H22118.1
H3A—O3—H3B110.9C24—C23—C16120.6 (11)
C25—O4—C25i93 (4)C24—C23—H23119.7
C25—O4—O4i56 (3)C16—C23—H23119.7
C25i—O4—O4i54 (3)C23—C24—C19122.4 (11)
C25—O4—O5i141 (4)C23—C24—H24118.8
C25i—O4—O5i49 (3)C19—C24—H24118.8
O4i—O4—O5i92 (3)O5—C25—O4126 (3)
C25—O5—O4i51 (2)O5—C25—O4i80 (4)
H6A—O6—H6B107.2O4—C25—O4i70 (3)
O1—C1—O2123.3 (12)O5—C25—C26117 (4)
O1—C1—C2116.6 (13)O4—C25—C26116 (5)
O2—C1—C2120.1 (13)O4i—C25—C26132 (3)
C3—C2—C1114.2 (13)O5—C25—C25i123 (5)
C3—C2—H2A108.7O4—C25—C25i45 (3)
C1—C2—H2A108.7O4i—C25—C25i43 (2)
C3—C2—H2B108.7C26—C25—C25i106 (2)
C1—C2—H2B108.7C27—C26—C25110 (3)
H2A—C2—H2B107.6C27—C26—H26A109.7
C4—C3—C8120.0 (18)C25—C26—H26A109.7
C4—C3—C2116.9 (15)C27—C26—H26B109.7
C8—C3—C2123.1 (17)C25—C26—H26B109.7
C5—C4—C3120.0 (18)H26A—C26—H26B108.2
C5—C4—H4120.0C31—C27—C28120 (3)
C3—C4—H4120.0C31—C27—C26129 (4)
C6—C5—C4120 (2)C28—C27—C26111 (3)
C6—C5—H5120.0C31—C27—H27120.0
C4—C5—H5120.0C28—C27—H27120.0
C5—C6—C7120 (2)C26—C27—H2710.1
C5—C6—H6120.0C29—C28—C27120 (3)
C7—C6—H6120.0C29—C28—H28119.8
C12—C7—C8120 (3)C27—C28—H28119.8
C12—C7—C6120 (3)C28—C29—C30119 (3)
C8—C7—C6120 (2)C28—C29—H29120.4
C3—C8—C7120 (2)C30—C29—H29120.4
C3—C8—C9120 (2)C29—C30—C31ii123 (3)
C7—C8—C9120 (2)C29—C30—H30118.4
C10—C9—C8120 (2)C31ii—C30—H30118.4
C10—C9—H9120.0C27—C31—C31ii126 (4)
C8—C9—H9120.0C27—C31—C30ii123 (3)
C9—C10—C11120 (3)C31ii—C31—C30ii111 (3)
C9—C10—H10120.0
O1—Er1—N1—C13−126.0 (9)Er1—N1—C13—C14−168.1 (9)
O1i—Er1—N1—C1397.4 (9)N1—C13—C14—C15−0.9 (18)
O3—Er1—N1—C1320.1 (9)C13—C14—C15—C16−2.4 (17)
O3i—Er1—N1—C13−58.9 (9)C14—C15—C16—C174.2 (17)
N2i—Er1—N1—C13130.8 (8)C14—C15—C16—C23−179.2 (11)
N2—Er1—N1—C13−177.8 (10)C13—N1—C17—C16−0.2 (14)
N1i—Er1—N1—C13−19.2 (8)Er1—N1—C17—C16170.8 (8)
O1—Er1—N1—C1763.7 (7)C13—N1—C17—C18177.6 (9)
O1i—Er1—N1—C17−72.8 (7)Er1—N1—C17—C18−11.3 (11)
O3—Er1—N1—C17−150.1 (7)C15—C16—C17—N1−2.9 (16)
O3i—Er1—N1—C17130.9 (7)C23—C16—C17—N1−179.6 (9)
N2i—Er1—N1—C17−39.4 (8)C15—C16—C17—C18179.3 (10)
N2—Er1—N1—C1712.0 (6)C23—C16—C17—C182.5 (15)
N1i—Er1—N1—C17170.5 (7)C22—N2—C18—C190.5 (14)
O1—Er1—N2—C2245.6 (8)Er1—N2—C18—C19−170.0 (7)
O1i—Er1—N2—C22−105.5 (8)C22—N2—C18—C17−177.8 (9)
O3—Er1—N2—C22−152.5 (7)Er1—N2—C18—C1711.8 (11)
O3i—Er1—N2—C22111.4 (8)N1—C17—C18—N2−0.1 (13)
N2i—Er1—N2—C22−33.6 (7)C16—C17—C18—N2177.7 (9)
N1—Er1—N2—C22177.9 (9)N1—C17—C18—C19−178.4 (9)
N1i—Er1—N2—C2211.9 (10)C16—C17—C18—C19−0.5 (14)
O1—Er1—N2—C18−144.5 (7)N2—C18—C19—C200.0 (15)
O1i—Er1—N2—C1864.4 (7)C17—C18—C19—C20178.2 (10)
O3—Er1—N2—C1817.4 (9)N2—C18—C19—C24−179.3 (9)
O3i—Er1—N2—C18−78.7 (7)C17—C18—C19—C24−1.1 (14)
N2i—Er1—N2—C18136.3 (8)C18—C19—C20—C21−0.2 (17)
N1—Er1—N2—C18−12.2 (6)C24—C19—C20—C21179.1 (11)
N1i—Er1—N2—C18−178.3 (6)C19—C20—C21—C22−0.1 (18)
O1i—Er1—O1—C1−170.1 (13)C18—N2—C22—C21−0.8 (15)
O3—Er1—O1—C1−17.1 (15)Er1—N2—C22—C21169.1 (8)
O3i—Er1—O1—C126.1 (12)C20—C21—C22—N20.7 (18)
N2i—Er1—O1—C1−126.3 (13)C15—C16—C23—C24−179.6 (12)
N2—Er1—O1—C1144.1 (13)C17—C16—C23—C24−3.0 (17)
N1—Er1—O1—C195.2 (13)C16—C23—C24—C191.3 (19)
N1i—Er1—O1—C1−58.6 (12)C18—C19—C24—C230.7 (17)
Er1—O1—C1—O2−38 (2)C20—C19—C24—C23−178.6 (12)
Er1—O1—C1—C2143.5 (11)O4i—O5—C25—O4−56 (4)
O1—C1—C2—C337.5 (17)O4i—O5—C25—C26132 (5)
O2—C1—C2—C3−141.0 (15)O4i—O5—C25—C25i−2(3)
C1—C2—C3—C4−100.0 (15)C25i—O4—C25—O5102 (7)
C1—C2—C3—C878.1 (17)O4i—O4—C25—O561 (5)
C8—C3—C4—C50(2)O5i—O4—C25—O599 (5)
C2—C3—C4—C5178.2 (13)C25i—O4—C25—O4i42 (3)
C3—C4—C5—C60(2)O5i—O4—C25—O4i39 (5)
C4—C5—C6—C70(2)C25i—O4—C25—C26−86 (3)
C5—C6—C7—C12180.0 (16)O4i—O4—C25—C26−128 (4)
C5—C6—C7—C80(3)O5i—O4—C25—C26−89 (6)
C4—C3—C8—C70(2)O4i—O4—C25—C25i−42 (3)
C2—C3—C8—C7−178.1 (14)O5i—O4—C25—C25i−3(4)
C4—C3—C8—C9180.0 (14)O5—C25—C26—C2767 (6)
C2—C3—C8—C92(2)O4—C25—C26—C27−105 (5)
C12—C7—C8—C3−180.0 (14)O4i—C25—C26—C27168 (6)
C6—C7—C8—C30(2)C25i—C25—C26—C27−152 (5)
C12—C7—C8—C90(2)C25—C26—C27—C31−103 (4)
C6—C7—C8—C9180.0 (15)C25—C26—C27—C2882 (4)
C3—C8—C9—C10180.0 (14)C31—C27—C28—C29−5(3)
C7—C8—C9—C100(2)C26—C27—C28—C29170 (2)
C8—C9—C10—C110(3)C27—C28—C29—C301(3)
C9—C10—C11—C120(3)C28—C29—C30—C31ii3(3)
C10—C11—C12—C70(3)C28—C27—C31—C31ii3(4)
C8—C7—C12—C110(3)C26—C27—C31—C31ii−171 (3)
C6—C7—C12—C11−180.0 (18)C28—C27—C31—C30ii−175 (2)
C17—N1—C13—C142.2 (16)C26—C27—C31—C30ii11 (4)
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O10.932.542.993 (12)110
C6—H6···O6iii0.932.453.37 (4)171
O6—H6B···O4i0.852.242.88 (4)132
O6—H6A···O50.852.022.62 (4)127
O3—H3B···O5i0.851.872.52 (2)132
O3—H3B···O4i0.852.443.27 (2)164
O3—H3B···O40.851.932.73 (2)158
O3—H3A···O2i0.851.982.691 (13)140
Symmetry codes: (iii) x, y−1, z; (i) −x+1, y, −z+3/2.
Table 1
Selected geometric parameters (Å) top
Er1—O12.294 (7)Er1—N22.537 (8)
Er1—O32.307 (7)Er1—N12.561 (8)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O10.932.542.993 (12)110
C6—H6···O6i0.932.453.37 (4)171
O6—H6B···O4ii0.852.242.88 (4)132
O6—H6A···O50.852.022.62 (4)127
O3—H3B···O5ii0.851.872.52 (2)132
O3—H3B···O4ii0.852.443.27 (2)164
O3—H3B···O40.851.932.73 (2)158
O3—H3A···O2ii0.851.982.691 (13)140
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y, −z+3/2.
Acknowledgements top

The authors acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

references
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