Bis(μ-adamantane-1,3-dicarboxyl­ato-κ4O1,O1′:O3,O3′)bis­[aqua­(3-carboxy­adam­antane-1-carboxyl­ato-κO1)(1,10-phen­an­throline-κ2N,N′)erbium(III)] dihydrate

Zhu, H.; Huang, W.; Chang, H.

doi:10.1107/S1600536811023075

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m959

doi:10.1107/S1600536811023075

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Bis(μ-adamantane-1,3-dicarboxylato-κ⁴O¹,O^1′:O³,O^3′)bis[aqua(3-carboxyadamantane-1-carboxylato-κO¹)(1,10-phenanthroline-κ²N,N′)erbium(III)] dihydrate

Hong-lin Zhu,^a ^* Wen-xiang Huang ^a and Hai-sheng Chang ^a

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: zhuhonglin1@nbu.edu.cn

(Received 8 June 2011; accepted 14 June 2011; online 22 June 2011)

The asymmetric unit of the binuclear centrosymmetric title compound, [Er₂(C₁₂H₁₄O₄)₂(C₁₂H₁₅O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]·2H₂O, contains one Er^III atom, one coordinated water molecule, one 1,10-phenanthroline (phen) ligand, two differently coordinated adamantane-1,3-dicarboxylate (H₂L) ligands and one lattice water molecule. The Er^III ion is eight-coordinated by four O atoms from bridging L²⁻, one O atom from HL⁻, one O atom from the coordinated water and two N atoms from a phen ligand. Extensive O—H⋯O hydrogen-bonding interactions result in the formation of chains which are further linked into a layer-like network by π–π stacking interactions centroid–centroid distance = 3.611 (3) Å] between adjacent phen ligands belonging to neighbouring chains. The carboxy group of the HL⁻ ligand is equally disordered over two positions.

Related literature

For 1,3-adamantanedicarboxylic acid, see: Glidewell & Ferguson (1996 ). For lanthanide 1,3-adamantanedicarboxylate complexes, see: Millange et al. (2004 ); Li et al. (2009 ).

Experimental

Crystal data

[Er₂(C₁₂H₁₄O₄)₂(C₁₂H₁₅O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]·2H₂O
M_r = 1657.94
Triclinic, $[P \overline 1]$
a = 8.6164 (17) Å
b = 13.579 (3) Å
c = 14.560 (3) Å
α = 94.53 (3)°
β = 96.36 (3)°
γ = 92.22 (3)°
V = 1685.8 (6) Å³
Z = 1
Mo Kα radiation
μ = 2.55 mm⁻¹
T = 293 K
0.34 × 0.17 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.600, T_max = 0.795
16743 measured reflections
7645 independent reflections
6761 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.067
S = 1.07
7645 reflections
448 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H91⋯O10	0.85	1.74	2.558 (4)	161.1
O9—H92⋯O1ⁱ	0.86	1.92	2.760 (4)	166.7
O10—H101⋯O6	0.85	1.87	2.653 (4)	153.6
O10—H102⋯O4ⁱ	0.85	1.87	2.692 (4)	161.8
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811023075/jh2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811023075/jh2296Isup2.hkl

checkCIF report

Comment top

As known, lanthanide ions have high affinity for hard donor atoms, and ligands with oxygen or hybrid oxygen-nitrogen atoms, especially multicarboxylate ligands are usually employed in construction for lanthanide complexes (Li et al., 2009). Herein, we report the crystal structure of title compound, [Er(phen)(H₂O)(HL)L]₂.2H₂O, which consist of 1,3-adamantanedicarboxylic acid (H₂L), 1,10-phenanthroline and ErCl₃.nH₂O. This structure indicates that hydrogen-bond and π–π interaction are responsible for supramolecular assemblies.

The asymmetric unit contains one Er^III, one coordination water, two type of 1,3-adamantanedicarboxylate ligands and one lattic water. As show in Fig.1, the Er^III ion is in a eight coordinated fashion by four oxygen atoms from L^2-, one oxygen from HL^1-, one oxygen from a coordination water and two nitrogen atoms from a 1,10-phenanthroline ligand. Three type kinds of hydrogen-bond are observed in title compound (Table 2). The presence of the extensive hydrogen-bond interaction results in formation of one-dimensional chains, which further grow into two-dimensional layer-like network by π–π stacking interaction between adjacent phen ligands belonging to neighboring chains (Fig. 2).

Related literature top

For 1,3-adamantanedicarboxylic acid, see: Glidewell et al. (1996). For lanthanide 1,3-adamantanedicarboxylate complexes, see: Millange et al. (2004); Li et al. (2009).

Experimental top

Pink powder of ErCl₃.nH₂O was obtained by slow evaporation of a solution of Er₂O₃ (0.150 mmol, 0.0574 g) dissolved in HCl (5 ml) under water boiling condition. A mixture of 1,3-adamantanedicarboxylic acid (0.300 mmol, 0.0595 g) in water (10 ml) was stirred for 30 min, and sealed in a 23 ml Teflon-lined stainless autoclave, which was heated at 170°C for three days and thereafter cooled slowly to room temperature, and pink crystals were separated by filtering and washing.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound. The dispalcement ellipsoids are drawn at 35% probability level. (# = -x + 1, -y + 1, -z + 1)
	Fig. 2. two-dimensional layer-like structure of the title crystal viewed down the b axis. O—H···O hydrogen bonds are shown as dashed line.

Bis(µ-adamantane-1,3-dicarboxylato- κ⁴O¹,O^1':O³,O^3')bis[aqua(3- carboxyadamantane-1-carboxylato-κO¹)(1,10- phenanthroline-κ²N,N')erbium(III)] dihydrate top

Crystal data top

[Er₂(C₁₂H₁₄O₄)₂(C₁₂H₁₅O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]·2H₂O	Z = 1
M_r = 1657.94	F(000) = 836
Triclinic, P1	D_x = 1.631 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6164 (17) Å	Cell parameters from 16743 reflections
b = 13.579 (3) Å	θ = 3.0–27.5°
c = 14.560 (3) Å	µ = 2.55 mm⁻¹
α = 94.53 (3)°	T = 293 K
β = 96.36 (3)°	Platelet, pink
γ = 92.22 (3)°	0.34 × 0.17 × 0.09 mm
V = 1685.8 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	7645 independent reflections
Radiation source: fine-focus sealed tube	6761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −9→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
T_min = 0.600, T_max = 0.795	l = −18→18
16743 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0268P)² + 1.2992P] where P = (F_o² + 2F_c²)/3
7645 reflections	(Δ/σ)_max = 0.001
448 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Er₂(C₁₂H₁₄O₄)₂(C₁₂H₁₅O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]·2H₂O	γ = 92.22 (3)°
M_r = 1657.94	V = 1685.8 (6) Å³
Triclinic, P1	Z = 1
a = 8.6164 (17) Å	Mo Kα radiation
b = 13.579 (3) Å	µ = 2.55 mm⁻¹
c = 14.560 (3) Å	T = 293 K
α = 94.53 (3)°	0.34 × 0.17 × 0.09 mm
β = 96.36 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	7645 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	6761 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.795	R_int = 0.031
16743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.07	Δρ_max = 0.77 e Å⁻³
7645 reflections	Δρ_min = −0.45 e Å⁻³
448 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)
Er	0.854312 (16)	0.436085 (10)	0.306019 (10)	0.02576 (5)
O1	0.8026 (3)	0.4032 (2)	0.45688 (17)	0.0447 (7)
O2	0.6851 (3)	0.30718 (18)	0.34156 (16)	0.0395 (6)
C1	0.7032 (4)	0.3337 (2)	0.4261 (2)	0.0287 (7)
C2	0.6055 (4)	0.2855 (2)	0.4926 (2)	0.0283 (6)
C3	0.4990 (4)	0.1997 (2)	0.4425 (2)	0.0348 (8)
H3A	0.4298	0.2238	0.3929	0.042*
H3B	0.5619	0.1498	0.4156	0.042*
C4	0.4028 (5)	0.1547 (2)	0.5124 (3)	0.0425 (9)
H4A	0.3359	0.0995	0.4807	0.051*
C5	0.5110 (5)	0.1166 (3)	0.5897 (3)	0.0540 (11)
H5A	0.5749	0.0664	0.5642	0.065*
H5B	0.4499	0.0869	0.6333	0.065*
C6	0.6162 (5)	0.2030 (3)	0.6399 (3)	0.0426 (9)
H6A	0.6857	0.1784	0.6900	0.051*
C7	0.7134 (4)	0.2479 (3)	0.5719 (3)	0.0371 (8)
H7A	0.7796	0.1986	0.5471	0.044*
H7B	0.7802	0.3022	0.6034	0.044*
C8	0.5023 (4)	0.3646 (2)	0.5333 (2)	0.0261 (6)
H8A	0.5679	0.4198	0.5642	0.031*
H8B	0.4338	0.3892	0.4837	0.031*
C9	0.3001 (4)	0.2325 (2)	0.5525 (3)	0.0378 (8)
H9A	0.2371	0.2034	0.5955	0.045*
H9B	0.2302	0.2561	0.5029	0.045*
C10	0.5148 (4)	0.2816 (3)	0.6807 (3)	0.0388 (8)
H10A	0.4547	0.2534	0.7256	0.047*
H10B	0.5811	0.3361	0.7123	0.047*
C11	0.4039 (4)	0.3195 (2)	0.6031 (2)	0.0289 (7)
C12	0.3065 (4)	0.4003 (2)	0.6422 (2)	0.0314 (7)
O3	0.1614 (3)	0.39715 (18)	0.6249 (2)	0.0431 (6)
O4	0.3746 (3)	0.47357 (17)	0.69327 (19)	0.0409 (6)
O5	1.0009 (3)	0.32069 (17)	0.25012 (19)	0.0390 (6)
O6	1.2280 (3)	0.2688 (2)	0.2129 (3)	0.0664 (10)
C13	1.0941 (4)	0.2530 (2)	0.2328 (3)	0.0352 (7)
C14	1.0322 (4)	0.1460 (2)	0.2345 (3)	0.0334 (7)
C15	0.8883 (4)	0.1286 (2)	0.1626 (3)	0.0356 (8)
H15A	0.9174	0.1394	0.1016	0.043*
H15B	0.8103	0.1754	0.1769	0.043*
C16	0.8190 (5)	0.0223 (3)	0.1624 (3)	0.0438 (9)
C17	0.7737 (5)	0.0062 (3)	0.2584 (3)	0.0518 (10)
H17A	0.6951	0.0520	0.2739	0.062*
H17B	0.7297	−0.0605	0.2588	0.062*
C18	0.9169 (5)	0.0224 (3)	0.3297 (3)	0.0540 (11)
H18A	0.8866	0.0116	0.3912	0.065*
C19	0.9834 (5)	0.1288 (3)	0.3303 (3)	0.0438 (9)
H19A	0.9051	0.1748	0.3456	0.053*
H19B	1.0732	0.1401	0.3769	0.053*
C20	1.1548 (4)	0.0721 (2)	0.2106 (3)	0.0434 (9)
H20A	1.2469	0.0826	0.2556	0.052*
H20B	1.1855	0.0822	0.1498	0.052*
C21	1.0402 (6)	−0.0498 (3)	0.3064 (4)	0.0630 (13)
H21A	1.1311	−0.0395	0.3523	0.076*
H21B	0.9988	−0.1172	0.3074	0.076*
C22	1.0864 (5)	−0.0340 (3)	0.2113 (3)	0.0536 (11)
H22A	1.1653	−0.0809	0.1962	0.064*
C23	0.9438 (5)	−0.0501 (3)	0.1385 (3)	0.0527 (11)
H23A	0.9015	−0.1175	0.1370	0.063*
H23B	0.9741	−0.0395	0.0777	0.063*
C24	0.6791 (5)	0.0091 (3)	0.0904 (3)	0.0540 (11)
O7A	0.542 (3)	0.0103 (12)	0.1176 (19)	0.105 (5)	0.50
O8A	0.705 (5)	0.037 (5)	0.020 (3)	0.127 (6)	0.50
O7B	0.562 (3)	−0.0412 (12)	0.1035 (19)	0.105 (5)	0.50
O8B	0.687 (5)	0.014 (5)	0.000 (3)	0.127 (6)	0.50
H81	0.6139	0.0253	−0.0385	0.153*
N1	0.9027 (4)	0.5395 (2)	0.1781 (2)	0.0382 (7)
C25	1.0004 (5)	0.6182 (3)	0.1918 (3)	0.0511 (10)
H25A	1.0530	0.6341	0.2508	0.061*
C26	1.0279 (6)	0.6785 (3)	0.1210 (4)	0.0625 (13)
H26A	1.0967	0.7337	0.1331	0.075*
C27	0.9532 (6)	0.6557 (3)	0.0348 (4)	0.0668 (14)
H27A	0.9709	0.6948	−0.0129	0.080*
C28	0.8494 (5)	0.5730 (3)	0.0178 (3)	0.0510 (10)
C29	0.8251 (4)	0.5169 (3)	0.0924 (3)	0.0388 (8)
C30	0.7153 (4)	0.4327 (3)	0.0783 (2)	0.0378 (8)
C31	0.7663 (6)	0.5436 (4)	−0.0716 (3)	0.0634 (13)
H31A	0.7833	0.5796	−0.1217	0.076*
C32	0.6651 (6)	0.4659 (4)	−0.0844 (3)	0.0640 (13)
H32A	0.6127	0.4492	−0.1432	0.077*
C33	0.6346 (5)	0.4071 (3)	−0.0103 (3)	0.0496 (10)
C34	0.5274 (6)	0.3257 (3)	−0.0201 (3)	0.0592 (12)
H34A	0.4745	0.3050	−0.0780	0.071*
C35	0.5011 (5)	0.2774 (3)	0.0544 (3)	0.0525 (10)
H35A	0.4282	0.2243	0.0488	0.063*
C36	0.5851 (4)	0.3083 (3)	0.1406 (3)	0.0402 (8)
H36A	0.5657	0.2747	0.1917	0.048*
N2	0.6905 (3)	0.3827 (2)	0.1527 (2)	0.0338 (6)
O9	1.0952 (3)	0.4876 (2)	0.37803 (19)	0.0491 (7)
H91	1.1783	0.4627	0.3623	0.059*
H92	1.1200	0.5139	0.4333	0.059*
O10	1.3385 (3)	0.4392 (3)	0.3024 (2)	0.0754 (12)
H101	1.3302	0.3787	0.2822	0.090*
H102	1.4354	0.4554	0.3092	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er	0.02433 (7)	0.02698 (7)	0.02613 (8)	0.00104 (5)	0.00666 (5)	−0.00200 (5)
O1	0.0479 (15)	0.0530 (15)	0.0310 (14)	−0.0201 (13)	0.0093 (11)	−0.0047 (11)
O2	0.0471 (14)	0.0451 (13)	0.0251 (12)	−0.0129 (12)	0.0098 (10)	−0.0044 (10)
C1	0.0283 (15)	0.0290 (15)	0.0286 (17)	0.0006 (13)	0.0057 (13)	−0.0018 (12)
C2	0.0317 (16)	0.0274 (14)	0.0266 (16)	0.0026 (13)	0.0076 (13)	0.0011 (12)
C3	0.0405 (18)	0.0298 (15)	0.0344 (19)	−0.0008 (15)	0.0123 (15)	−0.0062 (13)
C4	0.051 (2)	0.0226 (15)	0.054 (2)	−0.0067 (16)	0.0202 (19)	−0.0064 (15)
C5	0.074 (3)	0.0287 (17)	0.067 (3)	0.0111 (19)	0.034 (2)	0.0138 (18)
C6	0.057 (2)	0.0387 (18)	0.037 (2)	0.0179 (17)	0.0118 (18)	0.0140 (15)
C7	0.0410 (19)	0.0342 (17)	0.037 (2)	0.0134 (15)	0.0067 (15)	0.0031 (14)
C8	0.0303 (15)	0.0230 (13)	0.0252 (16)	0.0010 (12)	0.0041 (12)	0.0023 (11)
C9	0.0362 (18)	0.0314 (16)	0.047 (2)	−0.0051 (15)	0.0145 (16)	−0.0034 (15)
C10	0.049 (2)	0.0393 (18)	0.0314 (19)	0.0094 (16)	0.0137 (16)	0.0077 (14)
C11	0.0313 (16)	0.0239 (14)	0.0324 (17)	0.0025 (13)	0.0099 (13)	−0.0009 (12)
C12	0.0309 (16)	0.0300 (15)	0.0346 (18)	0.0024 (14)	0.0125 (14)	−0.0016 (13)
O3	0.0300 (12)	0.0370 (13)	0.0603 (18)	0.0024 (11)	0.0068 (12)	−0.0120 (12)
O4	0.0302 (12)	0.0352 (12)	0.0550 (17)	0.0021 (11)	0.0078 (11)	−0.0159 (11)
O5	0.0355 (13)	0.0301 (11)	0.0510 (16)	0.0065 (10)	0.0061 (11)	−0.0030 (11)
O6	0.0457 (16)	0.0422 (15)	0.115 (3)	−0.0023 (14)	0.0343 (18)	−0.0069 (17)
C13	0.0346 (17)	0.0290 (16)	0.042 (2)	0.0049 (14)	0.0054 (15)	−0.0030 (14)
C14	0.0302 (16)	0.0309 (16)	0.0388 (19)	0.0059 (14)	0.0018 (14)	0.0021 (14)
C15	0.0341 (17)	0.0301 (16)	0.041 (2)	−0.0003 (14)	−0.0005 (15)	0.0023 (14)
C16	0.044 (2)	0.0324 (17)	0.053 (2)	0.0002 (16)	−0.0001 (18)	−0.0009 (16)
C17	0.052 (2)	0.044 (2)	0.061 (3)	−0.0044 (19)	0.014 (2)	0.0074 (19)
C18	0.063 (3)	0.055 (2)	0.047 (2)	0.000 (2)	0.010 (2)	0.0157 (19)
C19	0.048 (2)	0.044 (2)	0.039 (2)	0.0058 (18)	0.0029 (17)	0.0019 (16)
C20	0.0353 (18)	0.0336 (18)	0.060 (3)	0.0086 (16)	0.0033 (18)	−0.0024 (17)
C21	0.069 (3)	0.043 (2)	0.076 (3)	0.003 (2)	−0.009 (3)	0.022 (2)
C22	0.051 (2)	0.0339 (19)	0.076 (3)	0.0162 (18)	0.004 (2)	0.0011 (19)
C23	0.061 (3)	0.0276 (17)	0.068 (3)	0.0018 (18)	0.007 (2)	−0.0054 (17)
C24	0.047 (2)	0.053 (2)	0.058 (3)	−0.013 (2)	0.000 (2)	−0.004 (2)
O7A	0.057 (6)	0.161 (16)	0.092 (8)	−0.030 (11)	−0.012 (5)	0.021 (12)
O8A	0.064 (9)	0.26 (3)	0.039 (13)	−0.042 (10)	−0.024 (8)	−0.014 (11)
O7B	0.057 (6)	0.161 (16)	0.092 (8)	−0.030 (11)	−0.012 (5)	0.021 (12)
O8B	0.064 (9)	0.26 (3)	0.039 (13)	−0.042 (10)	−0.024 (8)	−0.014 (11)
N1	0.0420 (17)	0.0344 (15)	0.0405 (18)	0.0049 (13)	0.0130 (14)	0.0048 (12)
C25	0.051 (2)	0.042 (2)	0.064 (3)	0.0014 (19)	0.020 (2)	0.0091 (19)
C26	0.066 (3)	0.039 (2)	0.089 (4)	0.005 (2)	0.029 (3)	0.018 (2)
C27	0.080 (3)	0.054 (3)	0.080 (4)	0.023 (2)	0.042 (3)	0.031 (2)
C28	0.060 (3)	0.053 (2)	0.048 (2)	0.025 (2)	0.024 (2)	0.0204 (19)
C29	0.0420 (19)	0.0410 (18)	0.038 (2)	0.0188 (16)	0.0156 (16)	0.0078 (15)
C30	0.044 (2)	0.0426 (18)	0.0296 (18)	0.0190 (16)	0.0097 (15)	0.0025 (14)
C31	0.086 (4)	0.072 (3)	0.041 (3)	0.037 (3)	0.023 (2)	0.023 (2)
C32	0.084 (3)	0.079 (3)	0.032 (2)	0.035 (3)	0.007 (2)	0.004 (2)
C33	0.056 (2)	0.066 (3)	0.028 (2)	0.028 (2)	0.0028 (17)	−0.0042 (17)
C34	0.065 (3)	0.068 (3)	0.039 (2)	0.017 (2)	−0.009 (2)	−0.012 (2)
C35	0.046 (2)	0.055 (2)	0.050 (3)	0.004 (2)	−0.0093 (19)	−0.011 (2)
C36	0.0388 (19)	0.0399 (19)	0.039 (2)	0.0026 (16)	−0.0014 (16)	−0.0037 (15)
N2	0.0345 (15)	0.0379 (15)	0.0295 (15)	0.0089 (13)	0.0051 (12)	−0.0006 (12)
O9	0.0301 (13)	0.0638 (17)	0.0483 (17)	0.0018 (13)	0.0023 (12)	−0.0239 (13)
O10	0.0380 (16)	0.094 (2)	0.088 (3)	−0.0218 (17)	0.0258 (16)	−0.048 (2)

Geometric parameters (Å, º) top

Er—O5	2.212 (2)	C16—C17	1.521 (6)
Er—O9	2.277 (3)	C16—C23	1.534 (6)
Er—O2	2.360 (2)	C17—C18	1.519 (6)
Er—O1	2.362 (3)	C17—H17A	0.9700
Er—O4ⁱ	2.363 (2)	C17—H17B	0.9700
Er—O3ⁱ	2.419 (2)	C18—C21	1.521 (7)
Er—N1	2.480 (3)	C18—C19	1.532 (5)
Er—N2	2.543 (3)	C18—H18A	0.9800
Er—C1	2.727 (3)	C19—H19A	0.9700
Er—C12ⁱ	2.763 (3)	C19—H19B	0.9700
O1—C1	1.270 (4)	C20—C22	1.537 (5)
O2—C1	1.246 (4)	C20—H20A	0.9700
C1—C2	1.520 (4)	C20—H20B	0.9700
C2—C7	1.533 (5)	C21—C22	1.512 (7)
C2—C3	1.539 (4)	C21—H21A	0.9700
C2—C8	1.544 (4)	C21—H21B	0.9700
C3—C4	1.530 (5)	C22—C23	1.529 (6)
C3—H3A	0.9700	C22—H22A	0.9800
C3—H3B	0.9700	C23—H23A	0.9700
C4—C5	1.517 (6)	C23—H23B	0.9700
C4—C9	1.526 (5)	C24—O8A	1.16 (6)
C4—H4A	0.9800	C24—O7B	1.23 (3)
C5—C6	1.538 (6)	C24—O7A	1.29 (3)
C5—H5A	0.9700	C24—O8B	1.33 (5)
C5—H5B	0.9700	O8A—H81	1.0865
C6—C7	1.515 (5)	O8B—H81	0.8244
C6—C10	1.531 (5)	N1—C25	1.323 (5)
C6—H6A	0.9800	N1—C29	1.356 (5)
C7—H7A	0.9700	C25—C26	1.401 (6)
C7—H7B	0.9700	C25—H25A	0.9300
C8—C11	1.541 (4)	C26—C27	1.353 (8)
C8—H8A	0.9700	C26—H26A	0.9300
C8—H8B	0.9700	C27—C28	1.396 (7)
C9—C11	1.541 (4)	C27—H27A	0.9300
C9—H9A	0.9700	C28—C29	1.405 (5)
C9—H9B	0.9700	C28—C31	1.434 (7)
C10—C11	1.532 (5)	C29—C30	1.442 (5)
C10—H10A	0.9700	C30—N2	1.356 (5)
C10—H10B	0.9700	C30—C33	1.407 (5)
C11—C12	1.520 (4)	C31—C32	1.330 (7)
C12—O3	1.246 (4)	C31—H31A	0.9300
C12—O4	1.276 (4)	C32—C33	1.433 (6)
C12—Erⁱ	2.763 (3)	C32—H32A	0.9300
O3—Erⁱ	2.419 (2)	C33—C34	1.401 (7)
O4—Erⁱ	2.363 (2)	C34—C35	1.347 (7)
O5—C13	1.272 (4)	C34—H34A	0.9300
O6—C13	1.236 (4)	C35—C36	1.402 (5)
C13—C14	1.530 (4)	C35—H35A	0.9300
C14—C15	1.529 (5)	C36—N2	1.320 (5)
C14—C19	1.533 (5)	C36—H36A	0.9300
C14—C20	1.534 (5)	O9—H91	0.8498
C15—C16	1.541 (5)	O9—H92	0.8558
C15—H15A	0.9700	O10—H101	0.8480
C15—H15B	0.9700	O10—H102	0.8481
C16—C24	1.503 (6)

O5—Er—O9	78.78 (9)	O6—C13—O5	124.0 (3)
O5—Er—O2	87.54 (9)	O6—C13—C14	119.1 (3)
O9—Er—O2	128.70 (11)	O5—C13—C14	116.9 (3)
O5—Er—O1	109.70 (10)	C15—C14—C13	108.1 (3)
O9—Er—O1	83.85 (10)	C15—C14—C19	108.6 (3)
O2—Er—O1	54.79 (8)	C13—C14—C19	110.3 (3)
O5—Er—O4ⁱ	154.07 (9)	C15—C14—C20	108.9 (3)
O9—Er—O4ⁱ	125.76 (9)	C13—C14—C20	111.6 (3)
O2—Er—O4ⁱ	82.43 (9)	C19—C14—C20	109.2 (3)
O1—Er—O4ⁱ	83.74 (10)	C14—C15—C16	110.4 (3)
O5—Er—O3ⁱ	148.03 (8)	C14—C15—H15A	109.6
O9—Er—O3ⁱ	71.80 (9)	C16—C15—H15A	109.6
O2—Er—O3ⁱ	120.65 (9)	C14—C15—H15B	109.6
O1—Er—O3ⁱ	79.70 (10)	C16—C15—H15B	109.6
O4ⁱ—Er—O3ⁱ	54.06 (8)	H15A—C15—H15B	108.1
O5—Er—N1	90.47 (10)	C24—C16—C17	111.2 (3)
O9—Er—N1	88.61 (11)	C24—C16—C23	110.3 (3)
O2—Er—N1	141.19 (10)	C17—C16—C23	109.4 (4)
O1—Er—N1	156.51 (10)	C24—C16—C15	108.2 (3)
O4ⁱ—Er—N1	82.73 (10)	C17—C16—C15	109.1 (3)
O3ⁱ—Er—N1	76.82 (10)	C23—C16—C15	108.6 (3)
O5—Er—N2	79.96 (10)	C18—C17—C16	109.8 (3)
O9—Er—N2	146.34 (10)	C18—C17—H17A	109.7
O2—Er—N2	75.75 (9)	C16—C17—H17A	109.7
O1—Er—N2	128.10 (9)	C18—C17—H17B	109.7
O4ⁱ—Er—N2	74.42 (9)	C16—C17—H17B	109.7
O3ⁱ—Er—N2	119.14 (10)	H17A—C17—H17B	108.2
N1—Er—N2	65.76 (10)	C17—C18—C21	110.0 (4)
O5—Er—C1	100.85 (10)	C17—C18—C19	109.4 (4)
O9—Er—C1	108.07 (11)	C21—C18—C19	109.8 (4)
O2—Er—C1	27.15 (9)	C17—C18—H18A	109.2
O1—Er—C1	27.72 (9)	C21—C18—H18A	109.2
O4ⁱ—Er—C1	80.62 (10)	C19—C18—H18A	109.2
O3ⁱ—Er—C1	99.93 (9)	C14—C19—C18	109.5 (3)
N1—Er—C1	161.29 (10)	C14—C19—H19A	109.8
N2—Er—C1	101.33 (10)	C18—C19—H19A	109.8
O5—Er—C12ⁱ	170.85 (9)	C14—C19—H19B	109.8
O9—Er—C12ⁱ	98.32 (10)	C18—C19—H19B	109.8
O2—Er—C12ⁱ	100.90 (9)	H19A—C19—H19B	108.2
O1—Er—C12ⁱ	78.40 (10)	C14—C20—C22	109.7 (3)
O4ⁱ—Er—C12ⁱ	27.44 (9)	C14—C20—H20A	109.7
O3ⁱ—Er—C12ⁱ	26.80 (9)	C22—C20—H20A	109.7
N1—Er—C12ⁱ	80.75 (10)	C14—C20—H20B	109.7
N2—Er—C12ⁱ	98.56 (10)	C22—C20—H20B	109.7
C1—Er—C12ⁱ	88.30 (10)	H20A—C20—H20B	108.2
C1—O1—Er	92.4 (2)	C22—C21—C18	109.4 (4)
C1—O2—Er	93.07 (19)	C22—C21—H21A	109.8
O2—C1—O1	119.4 (3)	C18—C21—H21A	109.8
O2—C1—C2	121.0 (3)	C22—C21—H21B	109.8
O1—C1—C2	119.6 (3)	C18—C21—H21B	109.8
O2—C1—Er	59.78 (17)	H21A—C21—H21B	108.2
O1—C1—Er	59.92 (17)	C21—C22—C23	110.2 (4)
C2—C1—Er	173.5 (2)	C21—C22—C20	109.6 (4)
C1—C2—C7	109.6 (3)	C23—C22—C20	109.0 (3)
C1—C2—C3	111.3 (3)	C21—C22—H22A	109.4
C7—C2—C3	110.0 (3)	C23—C22—H22A	109.4
C1—C2—C8	108.1 (2)	C20—C22—H22A	109.4
C7—C2—C8	109.0 (3)	C22—C23—C16	109.6 (3)
C3—C2—C8	108.8 (3)	C22—C23—H23A	109.8
C4—C3—C2	109.0 (3)	C16—C23—H23A	109.8
C4—C3—H3A	109.9	C22—C23—H23B	109.8
C2—C3—H3A	109.9	C16—C23—H23B	109.8
C4—C3—H3B	109.9	H23A—C23—H23B	108.2
C2—C3—H3B	109.9	O8A—C24—O7B	126 (2)
H3A—C3—H3B	108.3	O8A—C24—O7A	122 (3)
C5—C4—C9	110.0 (3)	O7B—C24—O7A	34.3 (12)
C5—C4—C3	109.9 (3)	O8A—C24—O8B	18 (5)
C9—C4—C3	109.8 (3)	O7B—C24—O8B	111 (2)
C5—C4—H4A	109.1	O7A—C24—O8B	117 (2)
C9—C4—H4A	109.1	O8A—C24—C16	112.4 (18)
C3—C4—H4A	109.1	O7B—C24—C16	120.9 (13)
C4—C5—C6	109.4 (3)	O7A—C24—C16	118.4 (12)
C4—C5—H5A	109.8	O8B—C24—C16	123.7 (19)
C6—C5—H5A	109.8	C24—O8A—H81	118.2
C4—C5—H5B	109.8	C24—O8B—H81	126.2
C6—C5—H5B	109.8	C25—N1—C29	118.7 (3)
H5A—C5—H5B	108.3	C25—N1—Er	121.6 (3)
C7—C6—C10	109.6 (3)	C29—N1—Er	119.8 (2)
C7—C6—C5	109.6 (3)	N1—C25—C26	122.6 (5)
C10—C6—C5	109.6 (3)	N1—C25—H25A	118.7
C7—C6—H6A	109.3	C26—C25—H25A	118.7
C10—C6—H6A	109.3	C27—C26—C25	119.2 (4)
C5—C6—H6A	109.3	C27—C26—H26A	120.4
C6—C7—C2	109.7 (3)	C25—C26—H26A	120.4
C6—C7—H7A	109.7	C26—C27—C28	119.8 (4)
C2—C7—H7A	109.7	C26—C27—H27A	120.1
C6—C7—H7B	109.7	C28—C27—H27A	120.1
C2—C7—H7B	109.7	C27—C28—C29	118.0 (4)
H7A—C7—H7B	108.2	C27—C28—C31	123.1 (4)
C11—C8—C2	109.9 (2)	C29—C28—C31	118.9 (4)
C11—C8—H8A	109.7	N1—C29—C28	121.8 (4)
C2—C8—H8A	109.7	N1—C29—C30	118.6 (3)
C11—C8—H8B	109.7	C28—C29—C30	119.7 (4)
C2—C8—H8B	109.7	N2—C30—C33	122.3 (4)
H8A—C8—H8B	108.2	N2—C30—C29	118.0 (3)
C4—C9—C11	109.6 (3)	C33—C30—C29	119.7 (4)
C4—C9—H9A	109.8	C32—C31—C28	121.3 (4)
C11—C9—H9A	109.8	C32—C31—H31A	119.4
C4—C9—H9B	109.8	C28—C31—H31A	119.4
C11—C9—H9B	109.8	C31—C32—C33	122.0 (4)
H9A—C9—H9B	108.2	C31—C32—H32A	119.0
C11—C10—C6	109.8 (3)	C33—C32—H32A	119.0
C11—C10—H10A	109.7	C34—C33—C30	117.5 (4)
C6—C10—H10A	109.7	C34—C33—C32	124.0 (4)
C11—C10—H10B	109.7	C30—C33—C32	118.5 (4)
C6—C10—H10B	109.7	C35—C34—C33	119.9 (4)
H10A—C10—H10B	108.2	C35—C34—H34A	120.0
C12—C11—C10	110.4 (3)	C33—C34—H34A	120.0
C12—C11—C9	111.6 (3)	C34—C35—C36	119.1 (4)
C10—C11—C9	109.5 (3)	C34—C35—H35A	120.5
C12—C11—C8	107.9 (2)	C36—C35—H35A	120.5
C10—C11—C8	108.6 (3)	N2—C36—C35	123.2 (4)
C9—C11—C8	108.8 (3)	N2—C36—H36A	118.4
O3—C12—O4	119.0 (3)	C35—C36—H36A	118.4
O3—C12—C11	121.5 (3)	C36—N2—C30	118.0 (3)
O4—C12—C11	119.4 (3)	C36—N2—Er	124.2 (2)
O3—C12—Erⁱ	61.06 (17)	C30—N2—Er	117.8 (2)
O4—C12—Erⁱ	58.57 (16)	Er—O9—H91	122.1
C11—C12—Erⁱ	171.5 (2)	Er—O9—H92	128.7
C12—O3—Erⁱ	92.14 (19)	H91—O9—H92	105.2
C12—O4—Erⁱ	94.0 (2)	H101—O10—H102	106.4
C13—O5—Er	169.9 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H91···O10	0.85	1.74	2.558 (4)	161.1
O9—H92···O1ⁱⁱ	0.86	1.92	2.760 (4)	166.7
O10—H101···O6	0.85	1.87	2.653 (4)	153.6
O10—H102···O4ⁱⁱ	0.85	1.87	2.692 (4)	161.8

Symmetry code: (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Er₂(C₁₂H₁₄O₄)₂(C₁₂H₁₅O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]·2H₂O
M_r	1657.94
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.6164 (17), 13.579 (3), 14.560 (3)
α, β, γ (°)	94.53 (3), 96.36 (3), 92.22 (3)
V (Å³)	1685.8 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.55
Crystal size (mm)	0.34 × 0.17 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.600, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	16743, 7645, 6761
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.067, 1.07
No. of reflections	7645
No. of parameters	448
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.45

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H91···O10	0.85	1.74	2.558 (4)	161.1
O9—H92···O1ⁱ	0.86	1.92	2.760 (4)	166.7
O10—H101···O6	0.85	1.87	2.653 (4)	153.6
O10—H102···O4ⁱ	0.85	1.87	2.692 (4)	161.8

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

This project was supported by the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. Y201017782). Sincere thanks are also extended to the K. C. Wong Magna Fund in Ningbo University.

References

Glidewell, C. & Ferguson, G. (1996). Acta Cryst. C52, 1466–1470. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Li, X., Wei, D. Y., Huang, S. J. & Zheng, Y. Q. (2009). J. Solid State Chem. 182, 95–101. CrossRef CAS Google Scholar
Millange, F., Serre, C., Marrot, J., Gardant, N., Pellé, F. & Férey, G. (2004). J. Mater. Chem. 14, 642–645. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). 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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