Diaqua­bis(1-naphthaleneacetato-κO)bis­(1,10-phenanthroline-κ2N,N′)erbium(III) 1-naphthalene­acetate monohydrate

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

doi:10.1107/S1600536807044546

Diaquabis(1-naphthaleneacetato-κO)bis(1,10-phenanthroline-κ²N,N′)erbium(III) 1-naphthaleneacetate monohydrate

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

In title compound, [Er(C₁₂H₉O₂)₂(C₁₂H₈N₂)₂(H₂O)₂](C₁₂H₉O₂)·H₂O, the carboxyl groups have only a monodentate coordination mode. The Er^III 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044546/at2395sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044546/at2395Isup2.hkl Contains datablock I

CCDC reference: 655255

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.031 Å
Disorder in main residue
R factor = 0.078
wR factor = 0.220
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT342_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         31

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.17
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.51
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C28    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C31    ...       1.38 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      75.00 A   3 
PLAT722_ALERT_1_C Angle   Calc      111.00, Rep      109.70 Dev...       1.30 Deg.
              C25  -C26  -H26A    1.555   1.555   1.555
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.12 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.00 Deg.
              O4   -C25  -C25     2.656   1.555   2.656
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      10.10 Deg.
              C26  -C27  -H27     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

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)·H₂O	F(000) = 2308
M_r = 1137.29	D_x = 1.389 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4270 reflections
a = 24.645 (3) Å	θ = 2.4–25.1°
b = 14.1144 (19) Å	µ = 1.60 mm⁻¹
c = 18.162 (2) Å	T = 298 K
β = 120.575 (2)°	Block, colourless
V = 5439.4 (12) Å³	0.31 × 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 tube	3523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→29
T_min = 0.636, T_max = 0.856	k = −16→15
13646 measured reflections	l = −21→21

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1579P)²] where P = (F_o² + 2F_c²)/3
4691 reflections	(Δ/σ)_max = 0.001
357 parameters	Δρ_max = 2.52 e Å⁻³
0 restraints	Δρ_min = −2.37 e Å⁻³

Crystal data top

[Er(C₁₂H₉O₂)₂(C₁₂H₈N₂)₂(H₂O)₂](C₁₂H₉O₂)·H₂O	V = 5439.4 (12) Å³
M_r = 1137.29	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.645 (3) Å	µ = 1.60 mm⁻¹
b = 14.1144 (19) Å	T = 298 K
c = 18.162 (2) Å	0.31 × 0.12 × 0.10 mm
β = 120.575 (2)°

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)
T_min = 0.636, T_max = 0.856	R_int = 0.089
13646 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.00	Δρ_max = 2.52 e Å⁻³
4691 reflections	Δρ_min = −2.37 e Å⁻³
357 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	Occ. (<1)
Er1	0.5000	0.53049 (3)	0.7500	0.0479 (3)
N1	0.5510 (4)	0.5715 (6)	0.9090 (5)	0.0572 (19)
N2	0.4950 (4)	0.3990 (6)	0.8417 (5)	0.0599 (19)
O1	0.3989 (3)	0.4731 (5)	0.6841 (5)	0.0689 (19)
O2	0.3239 (4)	0.5813 (9)	0.6529 (7)	0.110 (3)
O3	0.5604 (4)	0.6579 (5)	0.7551 (4)	0.0643 (17)
H3A	0.5976	0.6569	0.7983	0.077*
H3B	0.5430	0.7113	0.7507	0.077*
O4	0.5331 (13)	0.8380 (12)	0.7814 (18)	0.115 (8)	0.50
O5	0.4485 (16)	0.8284 (16)	0.7910 (18)	0.126 (8)	0.50
O6	0.3437 (15)	0.9071 (17)	0.6725 (19)	0.146 (9)	0.50
H6A	0.3616	0.8869	0.7237	0.175*	0.50
H6B	0.3699	0.9009	0.6555	0.175*	0.50
C1	0.3427 (6)	0.5022 (12)	0.6397 (8)	0.080 (3)
C2	0.2962 (6)	0.4362 (12)	0.5690 (9)	0.091 (4)
H2A	0.2538	0.4535	0.5544	0.109*
H2B	0.2995	0.4458	0.5186	0.109*
C3	0.3062 (7)	0.3329 (13)	0.5923 (10)	0.100 (5)
C4	0.3382 (7)	0.2802 (14)	0.5617 (11)	0.110 (5)
H4	0.3513	0.3088	0.5271	0.132*
C5	0.3508 (8)	0.1849 (17)	0.5827 (13)	0.125 (6)
H5	0.3722	0.1497	0.5622	0.150*
C6	0.3313 (11)	0.1423 (18)	0.6344 (15)	0.142 (8)
H6	0.3397	0.0785	0.6484	0.170*
C7	0.2993 (10)	0.195 (2)	0.6651 (14)	0.131 (7)
C8	0.2867 (7)	0.2903 (16)	0.6440 (10)	0.108 (5)
C9	0.2547 (8)	0.3430 (16)	0.6747 (11)	0.117 (6)
H9	0.2463	0.4068	0.6606	0.140*
C10	0.2352 (10)	0.300 (2)	0.7263 (14)	0.145 (8)
H10	0.2138	0.3355	0.7469	0.174*
C11	0.2478 (10)	0.205 (2)	0.7473 (14)	0.143 (8)
H11	0.2347	0.1764	0.7819	0.172*
C12	0.2798 (11)	0.152 (2)	0.7167 (15)	0.147 (8)
H12	0.2882	0.0885	0.7308	0.176*
C13	0.5766 (6)	0.6542 (8)	0.9433 (8)	0.072 (3)
H13	0.5691	0.7046	0.9063	0.086*
C14	0.6140 (6)	0.6717 (9)	1.0312 (8)	0.077 (3)
H14	0.6312	0.7313	1.0516	0.092*
C15	0.6247 (5)	0.5977 (10)	1.0867 (7)	0.077 (3)
H15	0.6506	0.6062	1.1454	0.093*
C16	0.5965 (6)	0.5108 (9)	1.0544 (7)	0.066 (3)
C17	0.5607 (5)	0.4977 (8)	0.9650 (7)	0.060 (2)
C18	0.5315 (5)	0.4073 (8)	0.9300 (6)	0.058 (2)
C19	0.5390 (5)	0.3316 (8)	0.9847 (7)	0.069 (3)
C20	0.5084 (6)	0.2451 (8)	0.9483 (9)	0.079 (3)
H20	0.5125	0.1937	0.9827	0.095*
C21	0.4726 (6)	0.2385 (8)	0.8615 (9)	0.079 (3)
H21	0.4520	0.1822	0.8359	0.095*
C22	0.4671 (5)	0.3182 (7)	0.8106 (7)	0.062 (2)
H22	0.4421	0.3124	0.7515	0.075*
C23	0.6053 (6)	0.4298 (10)	1.1102 (8)	0.077 (3)
H23	0.6304	0.4365	1.1692	0.092*
C24	0.5780 (6)	0.3474 (10)	1.0772 (8)	0.080 (3)
H24	0.5837	0.2977	1.1141	0.096*
C25	0.492 (3)	0.872 (2)	0.794 (3)	0.122 (13)	0.50
C26	0.503 (3)	0.9720 (18)	0.826 (3)	0.125 (14)	0.50
H26A	0.5347	1.0018	0.8177	0.150*	0.50
H26B	0.4639	1.0078	0.7938	0.150*	0.50
C27	0.5229 (18)	0.9724 (12)	0.9185 (19)	0.144 (9)
H27	0.5034	0.9691	0.8592	0.172*	0.50
C28	0.5870 (19)	0.9554 (14)	0.969 (2)	0.155 (10)
H28	0.6098	0.9361	0.9434	0.186*
C29	0.6169 (18)	0.9667 (13)	1.056 (2)	0.160 (11)
H29	0.6601	0.9566	1.0895	0.192*
C30	0.5817 (18)	0.9935 (16)	1.0932 (19)	0.155 (10)
H30	0.6029	1.0043	1.1518	0.186*
C31	0.4880 (17)	0.9944 (14)	0.9563 (16)	0.140 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.0420 (4)	0.0472 (4)	0.0390 (4)	0.000	0.0093 (3)	0.000
N1	0.051 (5)	0.063 (5)	0.048 (5)	−0.001 (4)	0.019 (4)	0.000 (4)
N2	0.056 (5)	0.059 (4)	0.055 (5)	0.003 (4)	0.022 (4)	0.005 (4)
O1	0.037 (4)	0.082 (5)	0.063 (5)	−0.008 (3)	0.008 (3)	0.002 (4)
O2	0.053 (5)	0.132 (8)	0.103 (7)	0.019 (6)	0.009 (5)	−0.032 (7)
O3	0.065 (4)	0.063 (4)	0.054 (4)	−0.010 (3)	0.023 (3)	−0.002 (3)
O4	0.17 (2)	0.059 (10)	0.12 (2)	0.009 (11)	0.070 (17)	−0.001 (11)
O5	0.19 (3)	0.082 (13)	0.13 (2)	0.014 (15)	0.10 (2)	−0.006 (13)
O6	0.19 (3)	0.108 (16)	0.15 (2)	0.019 (18)	0.09 (2)	0.007 (16)
C1	0.051 (7)	0.118 (9)	0.060 (7)	−0.017 (7)	0.020 (6)	−0.017 (7)
C2	0.052 (7)	0.134 (11)	0.066 (8)	−0.024 (7)	0.015 (6)	−0.021 (8)
C3	0.059 (8)	0.139 (13)	0.077 (9)	−0.036 (8)	0.017 (7)	−0.027 (9)
C4	0.069 (9)	0.138 (14)	0.087 (10)	−0.033 (9)	0.014 (8)	−0.018 (10)
C5	0.075 (11)	0.149 (17)	0.099 (13)	−0.032 (11)	0.007 (9)	−0.027 (12)
C6	0.090 (14)	0.151 (17)	0.104 (15)	−0.046 (13)	−0.010 (11)	−0.016 (14)
C7	0.086 (13)	0.16 (2)	0.093 (13)	−0.049 (14)	0.008 (10)	−0.012 (14)
C8	0.066 (9)	0.149 (15)	0.080 (10)	−0.046 (10)	0.016 (8)	−0.017 (10)
C9	0.077 (10)	0.160 (15)	0.090 (11)	−0.048 (11)	0.025 (9)	−0.015 (11)
C10	0.100 (14)	0.19 (2)	0.102 (14)	−0.049 (15)	0.020 (11)	−0.022 (14)
C11	0.095 (15)	0.18 (2)	0.103 (15)	−0.049 (16)	0.015 (12)	−0.007 (16)
C12	0.099 (15)	0.17 (2)	0.106 (15)	−0.047 (15)	0.004 (12)	−0.008 (15)
C13	0.067 (7)	0.077 (7)	0.063 (7)	−0.011 (6)	0.028 (6)	−0.007 (5)
C14	0.060 (7)	0.096 (8)	0.059 (7)	−0.015 (6)	0.019 (6)	−0.015 (6)
C15	0.055 (7)	0.108 (9)	0.050 (6)	−0.001 (6)	0.013 (5)	−0.012 (7)
C16	0.053 (6)	0.095 (7)	0.048 (6)	0.006 (5)	0.023 (5)	0.005 (5)
C17	0.051 (6)	0.077 (6)	0.054 (6)	0.004 (5)	0.029 (5)	0.003 (5)
C18	0.046 (5)	0.071 (6)	0.058 (6)	0.006 (5)	0.029 (5)	0.007 (5)
C19	0.061 (7)	0.077 (7)	0.062 (7)	0.013 (5)	0.025 (5)	0.013 (5)
C20	0.074 (8)	0.078 (7)	0.079 (9)	0.006 (6)	0.034 (7)	0.022 (6)
C21	0.067 (8)	0.065 (6)	0.087 (9)	−0.005 (5)	0.027 (7)	0.010 (6)
C22	0.051 (6)	0.059 (5)	0.066 (7)	−0.004 (4)	0.022 (5)	0.007 (5)
C23	0.068 (8)	0.102 (9)	0.051 (6)	0.011 (7)	0.023 (6)	0.010 (6)
C24	0.068 (8)	0.098 (9)	0.065 (7)	0.013 (7)	0.027 (6)	0.023 (7)
C25	0.19 (4)	0.08 (2)	0.12 (3)	0.01 (3)	0.09 (3)	0.007 (19)
C26	0.20 (5)	0.077 (19)	0.12 (3)	0.01 (2)	0.09 (3)	0.012 (16)
C27	0.22 (3)	0.090 (12)	0.13 (2)	0.009 (14)	0.09 (2)	0.012 (11)
C28	0.21 (3)	0.096 (12)	0.15 (2)	0.013 (15)	0.09 (2)	0.011 (13)
C29	0.23 (3)	0.105 (15)	0.15 (2)	0.017 (14)	0.10 (3)	0.013 (13)
C30	0.23 (4)	0.095 (12)	0.15 (2)	0.004 (17)	0.10 (3)	0.014 (14)
C31	0.22 (3)	0.084 (10)	0.129 (19)	0.019 (15)	0.10 (2)	0.010 (12)

Geometric parameters (Å, º) top

Er1—O1	2.294 (7)	C10—C11	1.39 (3)
Er1—O1ⁱ	2.294 (7)	C10—H10	0.9300
Er1—O3	2.307 (7)	C11—C12	1.39 (3)
Er1—O3ⁱ	2.307 (7)	C11—H11	0.9300
Er1—N2ⁱ	2.537 (8)	C12—H12	0.9300
Er1—N2	2.537 (8)	C13—C14	1.401 (16)
Er1—N1	2.561 (8)	C13—H13	0.9300
Er1—N1ⁱ	2.561 (8)	C14—C15	1.381 (17)
N1—C13	1.322 (14)	C14—H14	0.9300
N1—C17	1.390 (14)	C15—C16	1.385 (18)
N2—C22	1.303 (13)	C15—H15	0.9300
N2—C18	1.388 (13)	C16—C17	1.411 (16)
O1—C1	1.265 (16)	C16—C23	1.468 (18)
O2—C1	1.277 (18)	C17—C18	1.444 (16)
O3—H3A	0.8500	C18—C19	1.406 (14)
O3—H3B	0.8500	C19—C20	1.411 (17)
O4—C25	1.23 (5)	C19—C24	1.467 (18)
O4—C25ⁱ	1.27 (4)	C20—C21	1.362 (18)
O4—O4ⁱ	1.44 (5)	C20—H20	0.9300
O4—O5ⁱ	1.60 (4)	C21—C22	1.419 (15)
O5—C25	1.22 (5)	C21—H21	0.9300
O5—O4ⁱ	1.60 (4)	C22—H22	0.9300
O6—H6A	0.8499	C23—C24	1.326 (19)
O6—H6B	0.8500	C23—H23	0.9300
C1—C2	1.527 (18)	C24—H24	0.9300
C2—C3	1.50 (2)	C25—O4ⁱ	1.27 (4)
C2—H2A	0.9700	C25—C26	1.50 (4)
C2—H2B	0.9700	C26—C27	1.49 (5)
C3—C4	1.39 (2)	C26—H26A	0.9700
C3—C8	1.39 (2)	C26—H26B	0.9700
C4—C5	1.39 (3)	C27—C31	1.38 (4)
C4—H4	0.9300	C27—C28	1.38 (4)
C5—C6	1.39 (3)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.37 (4)
C6—C7	1.39 (3)	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.40 (4)
C7—C12	1.39 (3)	C29—H29	0.9300
C7—C8	1.39 (3)	C30—C31ⁱⁱ	1.49 (4)
C8—C9	1.39 (3)	C30—H30	0.9300
C9—C10	1.39 (3)	C31—C31ⁱⁱ	1.39 (5)
C9—H9	0.9300	C31—C30ⁱⁱ	1.49 (4)

O1—Er1—O1ⁱ	138.7 (4)	C11—C10—H10	120.0
O1—Er1—O3	143.5 (3)	C12—C11—C10	120 (3)
O1ⁱ—Er1—O3	75.3 (3)	C12—C11—H11	120.0
O1—Er1—O3ⁱ	75.3 (3)	C10—C11—H11	120.0
O1ⁱ—Er1—O3ⁱ	143.5 (3)	C11—C12—C7	120 (3)
O3—Er1—O3ⁱ	77.6 (4)	C11—C12—H12	120.0
O1—Er1—N2ⁱ	78.6 (3)	C7—C12—H12	120.0
O1ⁱ—Er1—N2ⁱ	71.5 (3)	N1—C13—C14	124.9 (11)
O3—Er1—N2ⁱ	110.5 (2)	N1—C13—H13	117.6
O3ⁱ—Er1—N2ⁱ	142.2 (3)	C14—C13—H13	117.6
O1—Er1—N2	71.5 (3)	C15—C14—C13	118.0 (11)
O1ⁱ—Er1—N2	78.6 (3)	C15—C14—H14	121.0
O3—Er1—N2	142.2 (3)	C13—C14—H14	121.0
O3ⁱ—Er1—N2	110.5 (2)	C14—C15—C16	119.4 (10)
N2ⁱ—Er1—N2	86.0 (4)	C14—C15—H15	120.3
O1—Er1—N1	116.6 (3)	C16—C15—H15	120.3
O1ⁱ—Er1—N1	73.2 (3)	C15—C16—C17	119.3 (11)
O3—Er1—N1	80.9 (2)	C15—C16—C23	122.0 (11)
O3ⁱ—Er1—N1	78.8 (3)	C17—C16—C23	118.6 (12)
N2ⁱ—Er1—N1	138.2 (3)	N1—C17—C16	121.2 (10)
N2—Er1—N1	65.5 (3)	N1—C17—C18	118.6 (9)
O1—Er1—N1ⁱ	73.2 (3)	C16—C17—C18	120.1 (10)
O1ⁱ—Er1—N1ⁱ	116.6 (3)	N2—C18—C19	121.9 (10)
O3—Er1—N1ⁱ	78.8 (3)	N2—C18—C17	117.9 (9)
O3ⁱ—Er1—N1ⁱ	80.9 (2)	C19—C18—C17	120.2 (10)
N2ⁱ—Er1—N1ⁱ	65.5 (3)	C18—C19—C20	118.6 (11)
N2—Er1—N1ⁱ	138.2 (3)	C18—C19—C24	117.9 (11)
N1—Er1—N1ⁱ	153.9 (4)	C20—C19—C24	123.4 (11)
C13—N1—C17	117.0 (9)	C21—C20—C19	118.6 (10)
C13—N1—Er1	125.0 (7)	C21—C20—H20	120.7
C17—N1—Er1	117.3 (7)	C19—C20—H20	120.7
C22—N2—C18	117.6 (9)	C20—C21—C22	119.4 (11)
C22—N2—Er1	123.1 (7)	C20—C21—H21	120.3
C18—N2—Er1	118.5 (6)	C22—C21—H21	120.3
C1—O1—Er1	139.9 (8)	N2—C22—C21	123.8 (11)
Er1—O3—H3A	113.2	N2—C22—H22	118.1
Er1—O3—H3B	113.7	C21—C22—H22	118.1
H3A—O3—H3B	110.9	C24—C23—C16	120.6 (11)
C25—O4—C25ⁱ	93 (4)	C24—C23—H23	119.7
C25—O4—O4ⁱ	56 (3)	C16—C23—H23	119.7
C25ⁱ—O4—O4ⁱ	54 (3)	C23—C24—C19	122.4 (11)
C25—O4—O5ⁱ	141 (4)	C23—C24—H24	118.8
C25ⁱ—O4—O5ⁱ	49 (3)	C19—C24—H24	118.8
O4ⁱ—O4—O5ⁱ	92 (3)	O5—C25—O4	126 (3)
C25—O5—O4ⁱ	51 (2)	O5—C25—O4ⁱ	80 (4)
H6A—O6—H6B	107.2	O4—C25—O4ⁱ	70 (3)
O1—C1—O2	123.3 (12)	O5—C25—C26	117 (4)
O1—C1—C2	116.6 (13)	O4—C25—C26	116 (5)
O2—C1—C2	120.1 (13)	O4ⁱ—C25—C26	132 (3)
C3—C2—C1	114.2 (13)	O5—C25—C25ⁱ	123 (5)
C3—C2—H2A	108.7	O4—C25—C25ⁱ	45 (3)
C1—C2—H2A	108.7	O4ⁱ—C25—C25ⁱ	43 (2)
C3—C2—H2B	108.7	C26—C25—C25ⁱ	106 (2)
C1—C2—H2B	108.7	C27—C26—C25	110 (3)
H2A—C2—H2B	107.6	C27—C26—H26A	109.7
C4—C3—C8	120.0 (18)	C25—C26—H26A	109.7
C4—C3—C2	116.9 (15)	C27—C26—H26B	109.7
C8—C3—C2	123.1 (17)	C25—C26—H26B	109.7
C5—C4—C3	120.0 (18)	H26A—C26—H26B	108.2
C5—C4—H4	120.0	C31—C27—C28	120 (3)
C3—C4—H4	120.0	C31—C27—C26	129 (4)
C6—C5—C4	120 (2)	C28—C27—C26	111 (3)
C6—C5—H5	120.0	C31—C27—H27	120.0
C4—C5—H5	120.0	C28—C27—H27	120.0
C5—C6—C7	120 (2)	C26—C27—H27	10.1
C5—C6—H6	120.0	C29—C28—C27	120 (3)
C7—C6—H6	120.0	C29—C28—H28	119.8
C12—C7—C8	120 (3)	C27—C28—H28	119.8
C12—C7—C6	120 (3)	C28—C29—C30	119 (3)
C8—C7—C6	120 (2)	C28—C29—H29	120.4
C3—C8—C7	120 (2)	C30—C29—H29	120.4
C3—C8—C9	120 (2)	C29—C30—C31ⁱⁱ	123 (3)
C7—C8—C9	120 (2)	C29—C30—H30	118.4
C10—C9—C8	120 (2)	C31ⁱⁱ—C30—H30	118.4
C10—C9—H9	120.0	C27—C31—C31ⁱⁱ	126 (4)
C8—C9—H9	120.0	C27—C31—C30ⁱⁱ	123 (3)
C9—C10—C11	120 (3)	C31ⁱⁱ—C31—C30ⁱⁱ	111 (3)
C9—C10—H10	120.0

O1—Er1—N1—C13	−126.0 (9)	Er1—N1—C13—C14	−168.1 (9)
O1ⁱ—Er1—N1—C13	97.4 (9)	N1—C13—C14—C15	−0.9 (18)
O3—Er1—N1—C13	20.1 (9)	C13—C14—C15—C16	−2.4 (17)
O3ⁱ—Er1—N1—C13	−58.9 (9)	C14—C15—C16—C17	4.2 (17)
N2ⁱ—Er1—N1—C13	130.8 (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—C16	170.8 (8)
O1—Er1—N1—C17	63.7 (7)	C13—N1—C17—C18	177.6 (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—C17	130.9 (7)	C23—C16—C17—N1	−179.6 (9)
N2ⁱ—Er1—N1—C17	−39.4 (8)	C15—C16—C17—C18	179.3 (10)
N2—Er1—N1—C17	12.0 (6)	C23—C16—C17—C18	2.5 (15)
N1ⁱ—Er1—N1—C17	170.5 (7)	C22—N2—C18—C19	0.5 (14)
O1—Er1—N2—C22	45.6 (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—C17	11.8 (11)
O3ⁱ—Er1—N2—C22	111.4 (8)	N1—C17—C18—N2	−0.1 (13)
N2ⁱ—Er1—N2—C22	−33.6 (7)	C16—C17—C18—N2	177.7 (9)
N1—Er1—N2—C22	177.9 (9)	N1—C17—C18—C19	−178.4 (9)
N1ⁱ—Er1—N2—C22	11.9 (10)	C16—C17—C18—C19	−0.5 (14)
O1—Er1—N2—C18	−144.5 (7)	N2—C18—C19—C20	0.0 (15)
O1ⁱ—Er1—N2—C18	64.4 (7)	C17—C18—C19—C20	178.2 (10)
O3—Er1—N2—C18	17.4 (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—C18	136.3 (8)	C18—C19—C20—C21	−0.2 (17)
N1—Er1—N2—C18	−12.2 (6)	C24—C19—C20—C21	179.1 (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—C21	169.1 (8)
O3ⁱ—Er1—O1—C1	26.1 (12)	C20—C21—C22—N2	0.7 (18)
N2ⁱ—Er1—O1—C1	−126.3 (13)	C15—C16—C23—C24	−179.6 (12)
N2—Er1—O1—C1	144.1 (13)	C17—C16—C23—C24	−3.0 (17)
N1—Er1—O1—C1	95.2 (13)	C16—C23—C24—C19	1.3 (19)
N1ⁱ—Er1—O1—C1	−58.6 (12)	C18—C19—C24—C23	0.7 (17)
Er1—O1—C1—O2	−38 (2)	C20—C19—C24—C23	−178.6 (12)
Er1—O1—C1—C2	143.5 (11)	O4ⁱ—O5—C25—O4	−56 (4)
O1—C1—C2—C3	37.5 (17)	O4ⁱ—O5—C25—C26	132 (5)
O2—C1—C2—C3	−141.0 (15)	O4ⁱ—O5—C25—C25ⁱ	−2 (3)
C1—C2—C3—C4	−100.0 (15)	C25ⁱ—O4—C25—O5	102 (7)
C1—C2—C3—C8	78.1 (17)	O4ⁱ—O4—C25—O5	61 (5)
C8—C3—C4—C5	0 (2)	O5ⁱ—O4—C25—O5	99 (5)
C2—C3—C4—C5	178.2 (13)	C25ⁱ—O4—C25—O4ⁱ	42 (3)
C3—C4—C5—C6	0 (2)	O5ⁱ—O4—C25—O4ⁱ	39 (5)
C4—C5—C6—C7	0 (2)	C25ⁱ—O4—C25—C26	−86 (3)
C5—C6—C7—C12	180.0 (16)	O4ⁱ—O4—C25—C26	−128 (4)
C5—C6—C7—C8	0 (3)	O5ⁱ—O4—C25—C26	−89 (6)
C4—C3—C8—C7	0 (2)	O4ⁱ—O4—C25—C25ⁱ	−42 (3)
C2—C3—C8—C7	−178.1 (14)	O5ⁱ—O4—C25—C25ⁱ	−3 (4)
C4—C3—C8—C9	180.0 (14)	O5—C25—C26—C27	67 (6)
C2—C3—C8—C9	2 (2)	O4—C25—C26—C27	−105 (5)
C12—C7—C8—C3	−180.0 (14)	O4ⁱ—C25—C26—C27	168 (6)
C6—C7—C8—C3	0 (2)	C25ⁱ—C25—C26—C27	−152 (5)
C12—C7—C8—C9	0 (2)	C25—C26—C27—C31	−103 (4)
C6—C7—C8—C9	180.0 (15)	C25—C26—C27—C28	82 (4)
C3—C8—C9—C10	180.0 (14)	C31—C27—C28—C29	−5 (3)
C7—C8—C9—C10	0 (2)	C26—C27—C28—C29	170 (2)
C8—C9—C10—C11	0 (3)	C27—C28—C29—C30	1 (3)
C9—C10—C11—C12	0 (3)	C28—C29—C30—C31ⁱⁱ	3 (3)
C10—C11—C12—C7	0 (3)	C28—C27—C31—C31ⁱⁱ	3 (4)
C8—C7—C12—C11	0 (3)	C26—C27—C31—C31ⁱⁱ	−171 (3)
C6—C7—C12—C11	−180.0 (18)	C28—C27—C31—C30ⁱⁱ	−175 (2)
C17—N1—C13—C14	2.2 (16)	C26—C27—C31—C30ⁱⁱ	11 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1	0.93	2.54	2.993 (12)	110
C6—H6···O6ⁱⁱⁱ	0.93	2.45	3.37 (4)	171
O6—H6B···O4ⁱ	0.85	2.24	2.88 (4)	132
O6—H6A···O5	0.85	2.02	2.62 (4)	127
O3—H3B···O5ⁱ	0.85	1.87	2.52 (2)	132
O3—H3B···O4ⁱ	0.85	2.44	3.27 (2)	164
O3—H3B···O4	0.85	1.93	2.73 (2)	158
O3—H3A···O2ⁱ	0.85	1.98	2.691 (13)	140

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

Experimental details

Crystal data
Chemical formula	[Er(C₁₂H₉O₂)₂(C₁₂H₈N₂)₂(H₂O)₂](C₁₂H₉O₂)·H₂O
M_r	1137.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	24.645 (3), 14.1144 (19), 18.162 (2)
β (°)	120.575 (2)
V (Å³)	5439.4 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.31 × 0.12 × 0.10

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.636, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	13646, 4691, 3523
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.220, 1.00
No. of reflections	4691
No. of parameters	357
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.52, −2.37

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected bond lengths (Å) top

Er1—O1	2.294 (7)	Er1—N2	2.537 (8)
Er1—O3	2.307 (7)	Er1—N1	2.561 (8)