Heptaaqua­(3,4,5,6-tetra­chloro­phthalato-κO1)erbium(III) 2-carb­oxy-3,4,5,6-tetra­chloro­benzoate–3,4,5,6-tetra­chloro­phthalic acid–water (1/1/1)

Ouyang, Y.; Shao, J.; Hao, L.; Lu, J.

doi:10.1107/S1600536812016923

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m662-m663

doi:10.1107/S1600536812016923

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Heptaaqua(3,4,5,6-tetrachlorophthalato-κO¹)erbium(III) 2-carboxy-3,4,5,6-tetrachlorobenzoate–3,4,5,6-tetrachlorophthalic acid–water (1/1/1)

Yan Ouyang,^a ^* Jia Shao,^a Lanfang Hao ^a and Jixin Lu ^a

^aTianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China
^*Correspondence e-mail: ouyangyan@tijmu.edu.cn

(Received 22 March 2012; accepted 18 April 2012; online 25 April 2012)

In the three-dimensional tetrachlorophthalate-bridged title complex [Er(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O, the Er^III ion is coordinated in form of a distorted square antiprism by an O atom of a tetrachlorophthalate ligand and by seven water O atoms. Extensive hydrogen bonds establish a layered network structure extending parallel to (001).

Related literature

For transition metal tetrachlorophthalato complexes, see: Ma et al. (2009 ). For lanthanide tetrachlorophthalato complexes, see: Liang et al. (2004 ); Xu et al. (2008 ).

Experimental

Crystal data

[Er(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O
M_r = 1220.05
Triclinic, $[P \overline 1]$
a = 6.865 (2) Å
b = 16.229 (5) Å
c = 19.019 (7) Å
α = 67.430 (8)°
β = 86.597 (13)°
γ = 81.626 (14)°
V = 1935.9 (11) Å³
Z = 2
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 294 K
0.16 × 0.08 × 0.08 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ) T_min = 0.639, T_max = 0.791
14352 measured reflections
8732 independent reflections
7423 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.00
8732 reflections
527 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −1.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O6ⁱ	0.82 (2)	1.77 (2)	2.566 (3)	162 (3)
O10—H10⋯O4ⁱⁱ	0.82 (3)	1.77 (3)	2.566 (3)	164 (3)
O12—H12⋯O5ⁱⁱⁱ	0.82 (3)	1.77 (2)	2.583 (3)	174 (5)
O13—H13A⋯O9^iv	0.84	2.57	2.969 (3)	110
O13—H13A⋯O2^v	0.84	2.03	2.814 (3)	155
O13—H13B⋯O20^vi	0.84	1.93	2.733 (3)	159
O14—H14A⋯O2^v	0.85	1.82	2.663 (3)	169
O14—H14B⋯O3^vii	0.85	1.92	2.724 (3)	157
O15—H15A⋯O3	0.84	2.03	2.868 (3)	169
O15—H15B⋯O4^viii	0.85	1.90	2.738 (3)	168
O16—H16A⋯O8^ix	0.85	1.95	2.774 (3)	166
O16—H16B⋯O3^vii	0.85	1.98	2.764 (3)	153
O17—H17A⋯O6^ix	0.84	1.92	2.750 (3)	168
O17—H17B⋯Cl5ⁱⁱ	0.84	2.83	3.614 (3)	157
O18—H18A⋯O20^vi	0.84	1.93	2.741 (4)	161
O18—H18B⋯O5^x	0.84	2.30	2.809 (4)	119
O19—H19A⋯O11^iv	0.84	2.09	2.909 (3)	167
O19—H19B⋯O5^xi	0.84	2.51	3.119 (3)	131
O19—H19B⋯O8^ix	0.84	2.31	3.010 (3)	141
O20—H20A⋯O11^vii	0.85	2.04	2.781 (3)	146
O20—H20B⋯O10	0.85	2.17	2.834 (3)	134
O20—H20B⋯O12	0.85	2.59	3.080 (3)	118
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) x+1, y, z+1; (v) -x+2, -y+1, -z+2; (vi) x, y, z+1; (vii) x+1, y, z; (viii) -x+1, -y+1, -z+2; (ix) -x+2, -y+1, -z+1; (x) x, y-1, z+1; (xi) x+1, y-1, z+1.

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016923/bt5856sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016923/bt5856Isup2.hkl

checkCIF report

Comment top

As a versatile bridge ligand, tcph₂ anion (H₂tcph=tetrachlorophthalic acid) with versatility of coordination modes was successfully used as bridge for the design and synthesis of a wide variety of polynuclear species, often having both interesting structures and properties. To date, most of the published work concerns transition metal tetrachlorophthalato complexes (Ma et al., 2009). In order to provide more examples of lanthanide–tetrachlorophthalate complexes with novel structure in this study, we selected Erbium(III) ion to obtain the title complex.

Single crystal X-ray diffraction analysis reveals that complex (I) consists of a [Er(tcph)(H₂O)₇]⁺ cation(Figure 1), a neutral (H₂tcph) molecule, an (Htcph)^- anion and an uncoordinated water molecule. Selected bond lengths and angles are presented in Table 1. The Er^III ion is coordinated by eight O atoms, one from a tcph ligand and others from coordinated water molecular. The Er–O band distances range from 2.291 (2) Å to 2.382 (2) Å. It is interesting that the complex contains several kinds of hydrogen bonds. The oxygen atoms from carboxylate act as acceptors and the coordinated water molecules as donors. Thus along a axis neighbouring mononuclear structural units form an unusual dimer by means of two short hydrogen bonds (O2–O13=2.814 (3) Å, O2–O14 = 2.663 (3) Å) between uncoordinated carboxylate O atom and coordinated water molecule (Figure 2), and Er–Er distance is 6.218 Å. Along b axis,two adjacent [Er(tcph)(H₂O)₇]⁺ cation are linked by short hydrogen bonds (O3–O16 = 2.732 (3) Å, O3–O14 = 2.764 (3) Å) (Figure 3), and Er–Er distance is 6.865 Å. Furthermore, there are some hydrogen bonds between [Er(tcph)(H₂O)₇]⁺ cations and (Htcph)^- anions. A two-dimensional network is constructed via a series of extensive hydrogen bonds. (Figure. 4) There are many hydrogen bonds owing to the presence of fully deprotonated carboxylate groups and a significant number of water molecules. Hydrogen bonding distances and angles are presented in Table 2. For clarity the conventional description of hydrogen bonding structural parameters has been adopted: D–A indicates the distance between a donor D atom and acceptor A atom, H–A the distance between a donor hydrogen atom bound to D and acceptor, while DHA indicates the angle.

IR spectra of the title complex exhibit the bands expected for the carbonyl stretching (1721 cm_-1), the bands for water stretching (3200–3100 cm_-1) and the bands for benzene (1500–1410 cm_-1). The absorption bands in the spectrum of the title complex were red-shifted relative to strong hydrogen bonds.

Related literature top

For transition metal tetrachlorophthalato complexes, see: Ma et al. (2009). For lanthanide tetrachlorophthalato complexes, see: Liang et al. (2004); Xu et al. (2008).

Experimental top

A solution of Er(NO₃)₃.6H₂O(0.5 mmol) in H₂O (10 ml) was added to a suspension of a suspension of H₂tcph (0.5 mmol) in H₂O (30 ml). The mixture was stirred at room temperature for 30 min. After filtration,the solution was left undisturbed and white crystal was obtain after 15 days.analysis, calculated for C₁₂H₈Cl₁₂ErO₂₀: C 23.63, H 1.57%; found: C 23.55, H 1.50%.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalStructure (Rigaku, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. [Symmetry codes:(i) -x, -y+1, -z; (ii) x+1, y, z; (iii) -x-1, -y+1, -z; (iv) -x+1, -y+1, -z; (v) x-1, y-1, z; (vi) x, y-1, z; (vii) x-1, y, z; (viii) -x+1, -y+2, -z]. H atoms have been omitted for clarity.
	Fig. 2. Fragment of the crystal structure of title complex showing the dimeric unit formed by hydrogen bonds with view along the a axis.
	Fig. 3. Fragment of the crystal structure of title complex showing the dimeric unit formed by hydrogen bonds with view along the b axis.
	Fig. 4. Packing diagram of the title compound.

Heptaaqua(3,4,5,6-tetrachlorophthalato-κO¹)erbium(III) 2-carboxy-3,4,5,6-tetrachlorobenzoate–3,4,5,6-tetrachlorophthalic acid–water (1/1/1) top

Crystal data top

[Er(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O	Z = 2
M_r = 1220.05	F(000) = 1190
Triclinic, P1	D_x = 2.093 Mg m⁻³
a = 6.865 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 16.229 (5) Å	Cell parameters from 6109 reflections
c = 19.019 (7) Å	θ = 2.2–28.0°
α = 67.430 (8)°	µ = 3.08 mm⁻¹
β = 86.597 (13)°	T = 294 K
γ = 81.626 (14)°	Block, colorless
V = 1935.9 (11) Å³	0.16 × 0.08 × 0.08 mm

Data collection top

Rigaku Saturn diffractometer	8732 independent reflections
Radiation source: fine-focus sealed tube	7423 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.6°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	k = −21→19
T_min = 0.639, T_max = 0.791	l = −24→22
14352 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0349P)²] where P = (F_o² + 2F_c²)/3
8732 reflections	(Δ/σ)_max = 0.003
527 parameters	Δρ_max = 0.75 e Å⁻³
3 restraints	Δρ_min = −1.29 e Å⁻³

Crystal data top

[Er(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O	γ = 81.626 (14)°
M_r = 1220.05	V = 1935.9 (11) Å³
Triclinic, P1	Z = 2
a = 6.865 (2) Å	Mo Kα radiation
b = 16.229 (5) Å	µ = 3.08 mm⁻¹
c = 19.019 (7) Å	T = 294 K
α = 67.430 (8)°	0.16 × 0.08 × 0.08 mm
β = 86.597 (13)°

Data collection top

Rigaku Saturn diffractometer	8732 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	7423 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.791	R_int = 0.023
14352 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	3 restraints
wR(F²) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.75 e Å⁻³
8732 reflections	Δρ_min = −1.29 e Å⁻³
527 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
Er1	1.052036 (16)	0.306469 (7)	0.999997 (6)	0.01887 (4)
Cl1	0.23002 (10)	0.64640 (5)	0.70586 (4)	0.03329 (16)
Cl2	0.40662 (13)	0.62105 (6)	0.55990 (4)	0.0467 (2)
Cl3	0.83345 (14)	0.52578 (6)	0.56071 (4)	0.0494 (2)
Cl4	1.07603 (11)	0.44511 (5)	0.71106 (4)	0.03644 (17)
Cl5	0.29591 (13)	0.70136 (5)	0.22781 (5)	0.0445 (2)
Cl6	0.53509 (14)	0.63458 (5)	0.37689 (4)	0.0446 (2)
Cl7	0.89471 (14)	0.72812 (6)	0.38416 (5)	0.0478 (2)
Cl8	0.98710 (11)	0.90094 (5)	0.24659 (5)	0.03817 (18)
Cl9	0.35448 (12)	−0.13570 (5)	0.39175 (5)	0.03755 (17)
Cl10	0.25335 (11)	−0.14158 (5)	0.55549 (4)	0.03720 (18)
Cl11	0.18423 (11)	0.03707 (6)	0.58473 (4)	0.03692 (17)
Cl12	0.21450 (12)	0.21921 (5)	0.45154 (5)	0.03884 (18)
O1	0.9205 (3)	0.39196 (12)	0.88147 (11)	0.0284 (4)
O2	0.9131 (3)	0.53332 (13)	0.87227 (11)	0.0319 (5)
O3	0.4634 (3)	0.49189 (12)	0.90040 (11)	0.0273 (4)
O4	0.4521 (3)	0.64077 (12)	0.84992 (11)	0.0259 (4)
O5	0.6653 (3)	1.03878 (12)	0.12137 (11)	0.0283 (4)
O6	0.7917 (3)	0.95674 (12)	0.05412 (10)	0.0275 (4)
O7	0.3216 (3)	0.95054 (14)	0.08330 (12)	0.0338 (5)
O8	0.4082 (3)	0.82485 (14)	0.06107 (12)	0.0346 (5)
O9	0.1761 (3)	0.27388 (14)	0.27974 (13)	0.0385 (5)
O10	0.4774 (3)	0.21429 (13)	0.26018 (12)	0.0334 (5)
O11	0.2508 (3)	0.07482 (16)	0.22111 (12)	0.0402 (5)
O12	0.5607 (3)	0.02273 (14)	0.25825 (12)	0.0294 (4)
O13	1.0399 (3)	0.29762 (13)	1.12704 (11)	0.0337 (5)
H13A	1.0773	0.3381	1.1385	0.051*
H13B	0.9765	0.2627	1.1627	0.051*
O14	1.1809 (3)	0.42624 (13)	1.00583 (11)	0.0277 (4)
H14A	1.1573	0.4452	1.0417	0.042*
H14B	1.2490	0.4605	0.9712	0.042*
O15	0.7405 (3)	0.37720 (15)	1.01578 (11)	0.0361 (5)
H15A	0.6606	0.4053	0.9796	0.054*
H15B	0.6831	0.3636	1.0587	0.054*
O16	1.3350 (3)	0.33085 (13)	0.91965 (13)	0.0357 (5)
H16A	1.4251	0.2865	0.9297	0.054*
H16B	1.3832	0.3802	0.8994	0.054*
O17	1.0434 (3)	0.21430 (13)	0.93003 (12)	0.0358 (5)
H17A	1.0812	0.1592	0.9399	0.054*
H17B	0.9955	0.2413	0.8862	0.054*
O18	0.8761 (4)	0.18711 (16)	1.07183 (15)	0.0521 (7)
H18A	0.8605	0.1666	1.1193	0.078*
H18B	0.8347	0.1562	1.0506	0.078*
O19	1.3023 (3)	0.18593 (16)	1.06132 (12)	0.0436 (6)
H19A	1.2811	0.1620	1.1082	0.065*
H19B	1.4033	0.1611	1.0469	0.065*
O20	0.8655 (3)	0.15500 (16)	0.22431 (14)	0.0484 (7)
H20A	0.9651	0.1161	0.2414	0.073*
H20B	0.7703	0.1443	0.2557	0.073*
C1	0.7625 (4)	0.51060 (16)	0.77524 (14)	0.0185 (5)
C2	0.5750 (4)	0.55643 (16)	0.77357 (14)	0.0191 (5)
C3	0.4646 (4)	0.59134 (17)	0.70701 (15)	0.0220 (5)
C4	0.5435 (4)	0.58012 (18)	0.64150 (15)	0.0268 (6)
C5	0.7336 (4)	0.53640 (18)	0.64217 (15)	0.0272 (6)
C6	0.8423 (4)	0.50157 (17)	0.70945 (15)	0.0221 (5)
C7	0.8776 (4)	0.47622 (17)	0.84880 (14)	0.0206 (5)
C8	0.4899 (3)	0.56417 (17)	0.84657 (14)	0.0197 (5)
C9	0.6767 (4)	0.88031 (17)	0.17843 (15)	0.0214 (5)
C10	0.5244 (4)	0.83474 (17)	0.17318 (15)	0.0222 (5)
C11	0.4843 (4)	0.75752 (18)	0.23404 (16)	0.0254 (6)
C12	0.5953 (4)	0.72585 (18)	0.30030 (15)	0.0273 (6)
C13	0.7518 (4)	0.76896 (18)	0.30458 (15)	0.0275 (6)
C14	0.7928 (4)	0.84635 (18)	0.24325 (16)	0.0247 (6)
C15	0.7153 (4)	0.96574 (17)	0.11282 (15)	0.0213 (5)
C16	0.4111 (4)	0.86923 (17)	0.09957 (15)	0.0230 (5)
C17	0.2958 (3)	0.12420 (17)	0.36129 (15)	0.0206 (5)
C18	0.3315 (4)	0.04388 (17)	0.34871 (15)	0.0208 (5)
C19	0.3178 (4)	−0.03821 (17)	0.40924 (16)	0.0226 (5)
C20	0.2706 (4)	−0.04027 (18)	0.48194 (15)	0.0251 (6)
C21	0.2376 (3)	0.03923 (19)	0.49491 (15)	0.0233 (6)
C22	0.2496 (4)	0.12182 (18)	0.43436 (15)	0.0231 (5)
C23	0.3072 (4)	0.21319 (17)	0.29615 (15)	0.0214 (5)
C24	0.3774 (4)	0.04817 (17)	0.26904 (15)	0.0220 (5)
H7	0.281 (5)	0.970 (2)	0.0392 (10)	0.056 (12)*
H10	0.477 (5)	0.2633 (14)	0.2246 (16)	0.054 (12)*
H12	0.602 (6)	0.028 (3)	0.2158 (11)	0.064 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Er1	0.02195 (6)	0.01616 (6)	0.01900 (7)	−0.00219 (4)	0.00221 (4)	−0.00767 (5)
Cl1	0.0258 (3)	0.0352 (4)	0.0349 (4)	0.0050 (3)	−0.0031 (3)	−0.0117 (3)
Cl2	0.0585 (5)	0.0546 (5)	0.0215 (4)	0.0068 (4)	−0.0125 (3)	−0.0117 (4)
Cl3	0.0618 (5)	0.0639 (6)	0.0207 (4)	0.0050 (5)	0.0104 (3)	−0.0202 (4)
Cl4	0.0315 (4)	0.0410 (4)	0.0374 (4)	0.0057 (3)	0.0091 (3)	−0.0206 (3)
Cl5	0.0492 (5)	0.0335 (4)	0.0461 (5)	−0.0213 (4)	0.0003 (4)	−0.0043 (4)
Cl6	0.0657 (5)	0.0316 (4)	0.0233 (4)	−0.0068 (4)	0.0111 (4)	0.0027 (3)
Cl7	0.0676 (6)	0.0442 (5)	0.0249 (4)	0.0038 (4)	−0.0170 (4)	−0.0073 (3)
Cl8	0.0342 (4)	0.0396 (4)	0.0431 (5)	−0.0058 (3)	−0.0090 (3)	−0.0168 (4)
Cl9	0.0471 (4)	0.0217 (3)	0.0424 (5)	−0.0033 (3)	0.0030 (3)	−0.0115 (3)
Cl10	0.0322 (4)	0.0335 (4)	0.0297 (4)	−0.0056 (3)	0.0017 (3)	0.0060 (3)
Cl11	0.0315 (4)	0.0611 (5)	0.0181 (3)	−0.0096 (3)	0.0049 (3)	−0.0144 (3)
Cl12	0.0490 (4)	0.0393 (4)	0.0386 (4)	−0.0105 (3)	0.0108 (3)	−0.0261 (4)
O1	0.0385 (11)	0.0187 (9)	0.0240 (10)	0.0065 (8)	−0.0019 (8)	−0.0073 (8)
O2	0.0493 (13)	0.0248 (10)	0.0242 (11)	−0.0067 (9)	−0.0018 (9)	−0.0115 (8)
O3	0.0356 (11)	0.0177 (9)	0.0225 (10)	−0.0026 (8)	0.0109 (8)	−0.0031 (8)
O4	0.0355 (11)	0.0163 (9)	0.0230 (10)	0.0007 (8)	0.0115 (8)	−0.0073 (8)
O5	0.0431 (12)	0.0178 (9)	0.0250 (11)	−0.0041 (8)	0.0067 (8)	−0.0102 (8)
O6	0.0392 (11)	0.0220 (9)	0.0179 (10)	0.0026 (8)	0.0044 (8)	−0.0069 (8)
O7	0.0482 (13)	0.0250 (10)	0.0255 (12)	0.0076 (9)	−0.0093 (9)	−0.0097 (9)
O8	0.0465 (13)	0.0285 (11)	0.0317 (12)	0.0005 (9)	−0.0085 (9)	−0.0155 (9)
O9	0.0318 (11)	0.0285 (11)	0.0431 (14)	0.0070 (9)	0.0055 (9)	−0.0051 (10)
O10	0.0322 (11)	0.0217 (10)	0.0344 (12)	−0.0001 (9)	0.0149 (9)	−0.0010 (9)
O11	0.0315 (11)	0.0609 (15)	0.0253 (11)	0.0046 (10)	−0.0040 (9)	−0.0163 (11)
O12	0.0269 (10)	0.0374 (11)	0.0233 (11)	0.0021 (9)	0.0057 (8)	−0.0139 (9)
O13	0.0485 (13)	0.0310 (11)	0.0239 (11)	−0.0151 (9)	0.0054 (9)	−0.0104 (9)
O14	0.0362 (11)	0.0267 (10)	0.0255 (11)	−0.0137 (8)	0.0140 (8)	−0.0143 (8)
O15	0.0289 (11)	0.0483 (13)	0.0215 (11)	0.0092 (10)	0.0071 (8)	−0.0090 (10)
O16	0.0350 (11)	0.0275 (11)	0.0451 (14)	−0.0061 (9)	0.0171 (9)	−0.0162 (10)
O17	0.0520 (13)	0.0212 (10)	0.0372 (13)	0.0088 (9)	−0.0138 (10)	−0.0172 (9)
O18	0.0636 (16)	0.0413 (14)	0.0581 (17)	−0.0322 (12)	0.0180 (13)	−0.0201 (12)
O19	0.0376 (12)	0.0476 (13)	0.0284 (12)	0.0136 (11)	0.0048 (9)	−0.0030 (10)
O20	0.0298 (12)	0.0402 (13)	0.0556 (16)	−0.0034 (10)	0.0149 (10)	0.0010 (11)
C1	0.0238 (12)	0.0144 (11)	0.0166 (12)	−0.0031 (10)	0.0041 (9)	−0.0055 (10)
C2	0.0244 (13)	0.0159 (11)	0.0164 (12)	−0.0044 (10)	0.0062 (9)	−0.0059 (10)
C3	0.0228 (13)	0.0191 (12)	0.0214 (13)	0.0006 (10)	0.0000 (10)	−0.0059 (10)
C4	0.0394 (16)	0.0225 (13)	0.0148 (13)	−0.0008 (12)	−0.0022 (11)	−0.0040 (11)
C5	0.0407 (16)	0.0233 (13)	0.0155 (13)	−0.0035 (12)	0.0096 (11)	−0.0068 (11)
C6	0.0261 (13)	0.0195 (12)	0.0204 (13)	−0.0006 (10)	0.0068 (10)	−0.0091 (10)
C7	0.0210 (12)	0.0238 (13)	0.0147 (12)	−0.0001 (10)	0.0054 (9)	−0.0064 (10)
C8	0.0154 (11)	0.0227 (13)	0.0174 (13)	−0.0007 (10)	0.0042 (9)	−0.0051 (10)
C9	0.0274 (13)	0.0163 (12)	0.0196 (13)	0.0005 (10)	0.0024 (10)	−0.0073 (10)
C10	0.0278 (13)	0.0163 (12)	0.0211 (13)	−0.0012 (10)	0.0021 (10)	−0.0065 (10)
C11	0.0307 (14)	0.0198 (13)	0.0264 (15)	−0.0027 (11)	0.0051 (11)	−0.0105 (11)
C12	0.0436 (16)	0.0186 (13)	0.0148 (13)	0.0030 (12)	0.0074 (11)	−0.0046 (10)
C13	0.0384 (16)	0.0243 (14)	0.0159 (13)	0.0065 (12)	−0.0027 (11)	−0.0066 (11)
C14	0.0300 (14)	0.0215 (13)	0.0234 (14)	0.0006 (11)	−0.0004 (11)	−0.0109 (11)
C15	0.0214 (12)	0.0204 (13)	0.0224 (14)	−0.0009 (10)	−0.0018 (10)	−0.0088 (11)
C16	0.0244 (13)	0.0216 (13)	0.0224 (14)	−0.0025 (10)	0.0013 (10)	−0.0080 (11)
C17	0.0151 (11)	0.0247 (13)	0.0205 (13)	−0.0008 (10)	0.0016 (9)	−0.0077 (11)
C18	0.0151 (11)	0.0239 (13)	0.0210 (13)	−0.0011 (10)	0.0014 (9)	−0.0068 (11)
C19	0.0175 (12)	0.0213 (13)	0.0263 (14)	−0.0017 (10)	−0.0002 (10)	−0.0065 (11)
C20	0.0164 (12)	0.0289 (14)	0.0204 (13)	−0.0053 (11)	−0.0011 (9)	0.0022 (11)
C21	0.0139 (12)	0.0357 (15)	0.0168 (13)	−0.0028 (11)	0.0019 (9)	−0.0065 (11)
C22	0.0177 (12)	0.0299 (14)	0.0250 (14)	−0.0066 (11)	0.0051 (10)	−0.0134 (12)
C23	0.0225 (13)	0.0208 (13)	0.0216 (13)	−0.0035 (10)	0.0019 (10)	−0.0089 (11)
C24	0.0252 (13)	0.0184 (12)	0.0214 (14)	0.0001 (10)	0.0025 (10)	−0.0078 (10)

Geometric parameters (Å, º) top

Er1—O14	2.291 (2)	O14—H14B	0.8480
Er1—O1	2.302 (2)	O15—H15A	0.8442
Er1—O15	2.336 (2)	O15—H15B	0.8488
Er1—O18	2.352 (2)	O16—H16A	0.8465
Er1—O17	2.361 (2)	O16—H16B	0.8511
Er1—O13	2.362 (2)	O17—H17A	0.8441
Er1—O19	2.376 (2)	O17—H17B	0.8395
Er1—O16	2.382 (2)	O18—H18A	0.8404
Cl1—C3	1.721 (3)	O18—H18B	0.8400
Cl2—C4	1.713 (3)	O19—H19A	0.8382
Cl3—C5	1.716 (3)	O19—H19B	0.8353
Cl4—C6	1.724 (3)	O20—H20A	0.8455
Cl5—C11	1.721 (3)	O20—H20B	0.8489
Cl6—C12	1.714 (3)	C1—C2	1.385 (3)
Cl7—C13	1.706 (3)	C1—C6	1.387 (3)
Cl8—C14	1.722 (3)	C1—C7	1.515 (3)
Cl9—C19	1.719 (3)	C2—C3	1.391 (4)
Cl10—C20	1.716 (3)	C2—C8	1.517 (3)
Cl11—C21	1.714 (3)	C3—C4	1.394 (4)
Cl12—C22	1.714 (3)	C4—C5	1.390 (4)
O1—C7	1.263 (3)	C5—C6	1.396 (4)
O2—C7	1.230 (3)	C9—C14	1.388 (4)
O3—C8	1.255 (3)	C9—C10	1.395 (4)
O4—C8	1.258 (3)	C9—C15	1.513 (4)
O5—C15	1.254 (3)	C10—C11	1.391 (4)
O6—C15	1.255 (3)	C10—C16	1.510 (4)
O7—C16	1.299 (3)	C11—C12	1.391 (4)
O7—H7	0.826 (10)	C12—C13	1.387 (4)
O8—C16	1.211 (3)	C13—C14	1.399 (4)
O9—C23	1.190 (3)	C17—C22	1.394 (4)
O10—C23	1.318 (3)	C17—C18	1.398 (4)
O10—H10	0.822 (10)	C17—C23	1.508 (4)
O11—C24	1.206 (3)	C18—C19	1.398 (4)
O12—C24	1.296 (3)	C18—C24	1.506 (4)
O12—H12	0.818 (10)	C19—C20	1.390 (4)
O13—H13A	0.8434	C20—C21	1.389 (4)
O13—H13B	0.8441	C21—C22	1.402 (4)
O14—H14A	0.8482

O14—Er1—O1	91.91 (7)	C5—C4—C3	120.1 (2)
O14—Er1—O15	87.97 (8)	C5—C4—Cl2	120.0 (2)
O1—Er1—O15	71.56 (7)	C3—C4—Cl2	119.9 (2)
O14—Er1—O18	142.46 (8)	C4—C5—C6	119.5 (2)
O1—Er1—O18	113.68 (9)	C4—C5—Cl3	120.1 (2)
O15—Er1—O18	75.73 (9)	C6—C5—Cl3	120.5 (2)
O14—Er1—O17	145.21 (8)	C1—C6—C5	120.6 (2)
O1—Er1—O17	70.35 (7)	C1—C6—Cl4	119.8 (2)
O15—Er1—O17	112.66 (8)	C5—C6—Cl4	119.6 (2)
O18—Er1—O17	71.88 (9)	O2—C7—O1	126.4 (2)
O14—Er1—O13	70.63 (7)	O2—C7—C1	116.4 (2)
O1—Er1—O13	141.86 (7)	O1—C7—C1	117.0 (2)
O15—Er1—O13	74.12 (7)	O3—C8—O4	124.4 (2)
O18—Er1—O13	72.43 (9)	O3—C8—C2	116.5 (2)
O17—Er1—O13	140.32 (7)	O4—C8—C2	119.1 (2)
O14—Er1—O19	101.22 (9)	C14—C9—C10	119.8 (2)
O1—Er1—O19	141.31 (7)	C14—C9—C15	120.7 (2)
O15—Er1—O19	144.22 (7)	C10—C9—C15	119.6 (2)
O18—Er1—O19	76.24 (9)	C11—C10—C9	119.9 (2)
O17—Er1—O19	78.65 (8)	C11—C10—C16	121.5 (2)
O13—Er1—O19	76.55 (8)	C9—C10—C16	118.5 (2)
O14—Er1—O16	71.54 (7)	C10—C11—C12	120.2 (3)
O1—Er1—O16	76.86 (8)	C10—C11—Cl5	120.0 (2)
O15—Er1—O16	141.55 (7)	C12—C11—Cl5	119.8 (2)
O18—Er1—O16	138.68 (8)	C13—C12—C11	120.0 (2)
O17—Er1—O16	75.30 (8)	C13—C12—Cl6	120.3 (2)
O13—Er1—O16	124.91 (8)	C11—C12—Cl6	119.6 (2)
O19—Er1—O16	73.26 (8)	C12—C13—C14	119.8 (3)
C7—O1—Er1	130.39 (18)	C12—C13—Cl7	120.4 (2)
C16—O7—H7	108 (3)	C14—C13—Cl7	119.8 (2)
C23—O10—H10	109 (3)	C9—C14—C13	120.2 (3)
C24—O12—H12	121 (3)	C9—C14—Cl8	118.9 (2)
Er1—O13—H13A	121.2	C13—C14—Cl8	120.9 (2)
Er1—O13—H13B	125.0	O5—C15—O6	126.0 (2)
H13A—O13—H13B	112.4	O5—C15—C9	117.4 (2)
Er1—O14—H14A	123.8	O6—C15—C9	116.6 (2)
Er1—O14—H14B	125.4	O8—C16—O7	125.3 (3)
H14A—O14—H14B	110.6	O8—C16—C10	122.5 (2)
Er1—O15—H15A	123.3	O7—C16—C10	112.2 (2)
Er1—O15—H15B	122.4	C22—C17—C18	119.8 (2)
H15A—O15—H15B	111.6	C22—C17—C23	120.0 (2)
Er1—O16—H16A	115.7	C18—C17—C23	120.2 (2)
Er1—O16—H16B	126.0	C19—C18—C17	119.8 (2)
H16A—O16—H16B	110.6	C19—C18—C24	121.3 (2)
Er1—O17—H17A	132.7	C17—C18—C24	118.9 (2)
Er1—O17—H17B	114.6	C20—C19—C18	120.2 (3)
H17A—O17—H17B	112.6	C20—C19—Cl9	120.8 (2)
Er1—O18—H18A	126.5	C18—C19—Cl9	119.0 (2)
Er1—O18—H18B	119.5	C21—C20—C19	120.2 (2)
H18A—O18—H18B	113.5	C21—C20—Cl10	120.2 (2)
Er1—O19—H19A	111.5	C19—C20—Cl10	119.6 (2)
Er1—O19—H19B	135.1	C20—C21—C22	119.9 (2)
H19A—O19—H19B	113.3	C20—C21—Cl11	120.4 (2)
H20A—O20—H20B	110.8	C22—C21—Cl11	119.7 (2)
C2—C1—C6	119.6 (2)	C17—C22—C21	120.1 (3)
C2—C1—C7	118.1 (2)	C17—C22—Cl12	120.4 (2)
C6—C1—C7	122.2 (2)	C21—C22—Cl12	119.4 (2)
C1—C2—C3	120.5 (2)	O9—C23—O10	125.1 (3)
C1—C2—C8	118.6 (2)	O9—C23—C17	123.2 (2)
C3—C2—C8	120.9 (2)	O10—C23—C17	111.7 (2)
C2—C3—C4	119.7 (2)	O11—C24—O12	125.2 (3)
C2—C3—Cl1	120.2 (2)	O11—C24—C18	120.9 (2)
C4—C3—Cl1	120.1 (2)	O12—C24—C18	113.9 (2)

O14—Er1—O1—C7	−21.9 (2)	C11—C12—C13—C14	2.5 (4)
O15—Er1—O1—C7	65.3 (2)	Cl6—C12—C13—C14	−176.5 (2)
O18—Er1—O1—C7	129.8 (2)	C11—C12—C13—Cl7	−177.5 (2)
O17—Er1—O1—C7	−171.3 (2)	Cl6—C12—C13—Cl7	3.6 (3)
O13—Er1—O1—C7	38.4 (3)	C10—C9—C14—C13	−2.9 (4)
O19—Er1—O1—C7	−132.6 (2)	C15—C9—C14—C13	177.9 (2)
O16—Er1—O1—C7	−92.5 (2)	C10—C9—C14—Cl8	177.0 (2)
C6—C1—C2—C3	1.6 (4)	C15—C9—C14—Cl8	−2.1 (3)
C7—C1—C2—C3	178.4 (2)	C12—C13—C14—C9	0.4 (4)
C6—C1—C2—C8	179.1 (2)	Cl7—C13—C14—C9	−179.7 (2)
C7—C1—C2—C8	−4.1 (3)	C12—C13—C14—Cl8	−179.6 (2)
C1—C2—C3—C4	0.0 (4)	Cl7—C13—C14—Cl8	0.4 (3)
C8—C2—C3—C4	−177.4 (3)	C14—C9—C15—O5	−74.5 (3)
C1—C2—C3—Cl1	178.8 (2)	C10—C9—C15—O5	106.4 (3)
C8—C2—C3—Cl1	1.4 (3)	C14—C9—C15—O6	106.8 (3)
C2—C3—C4—C5	−1.8 (4)	C10—C9—C15—O6	−72.4 (3)
Cl1—C3—C4—C5	179.4 (2)	C11—C10—C16—O8	−59.8 (4)
C2—C3—C4—Cl2	178.7 (2)	C9—C10—C16—O8	117.9 (3)
Cl1—C3—C4—Cl2	−0.1 (3)	C11—C10—C16—O7	120.8 (3)
C3—C4—C5—C6	1.9 (4)	C9—C10—C16—O7	−61.5 (3)
Cl2—C4—C5—C6	−178.6 (2)	C22—C17—C18—C19	0.9 (4)
C3—C4—C5—Cl3	−177.9 (2)	C23—C17—C18—C19	−179.1 (2)
Cl2—C4—C5—Cl3	1.6 (4)	C22—C17—C18—C24	178.8 (2)
C2—C1—C6—C5	−1.5 (4)	C23—C17—C18—C24	−1.1 (4)
C7—C1—C6—C5	−178.2 (2)	C17—C18—C19—C20	−0.6 (4)
C2—C1—C6—Cl4	179.67 (19)	C24—C18—C19—C20	−178.4 (2)
C7—C1—C6—Cl4	3.0 (4)	C17—C18—C19—Cl9	177.91 (19)
C4—C5—C6—C1	−0.3 (4)	C24—C18—C19—Cl9	0.0 (3)
Cl3—C5—C6—C1	179.6 (2)	C18—C19—C20—C21	−0.3 (4)
C4—C5—C6—Cl4	178.6 (2)	Cl9—C19—C20—C21	−178.73 (19)
Cl3—C5—C6—Cl4	−1.6 (3)	C18—C19—C20—Cl10	179.69 (19)
Er1—O1—C7—O2	6.4 (4)	Cl9—C19—C20—Cl10	1.3 (3)
Er1—O1—C7—C1	−170.47 (16)	C19—C20—C21—C22	0.8 (4)
C2—C1—C7—O2	−61.0 (3)	Cl10—C20—C21—C22	−179.20 (19)
C6—C1—C7—O2	115.7 (3)	C19—C20—C21—Cl11	−178.69 (19)
C2—C1—C7—O1	116.2 (3)	Cl10—C20—C21—Cl11	1.3 (3)
C6—C1—C7—O1	−67.1 (3)	C18—C17—C22—C21	−0.4 (4)
C1—C2—C8—O3	−63.3 (3)	C23—C17—C22—C21	179.6 (2)
C3—C2—C8—O3	114.1 (3)	C18—C17—C22—Cl12	177.55 (19)
C1—C2—C8—O4	116.1 (3)	C23—C17—C22—Cl12	−2.5 (3)
C3—C2—C8—O4	−66.4 (3)	C20—C21—C22—C17	−0.4 (4)
C14—C9—C10—C11	2.6 (4)	Cl11—C21—C22—C17	179.05 (19)
C15—C9—C10—C11	−178.2 (2)	C20—C21—C22—Cl12	−178.41 (19)
C14—C9—C10—C16	−175.2 (2)	Cl11—C21—C22—Cl12	1.1 (3)
C15—C9—C10—C16	4.0 (4)	C22—C17—C23—O9	−55.0 (4)
C9—C10—C11—C12	0.3 (4)	C18—C17—C23—O9	125.0 (3)
C16—C10—C11—C12	178.0 (2)	C22—C17—C23—O10	125.6 (3)
C9—C10—C11—Cl5	179.8 (2)	C18—C17—C23—O10	−54.4 (3)
C16—C10—C11—Cl5	−2.5 (4)	C19—C18—C24—O11	105.4 (3)
C10—C11—C12—C13	−2.8 (4)	C17—C18—C24—O11	−72.5 (4)
Cl5—C11—C12—C13	177.7 (2)	C19—C18—C24—O12	−75.8 (3)
C10—C11—C12—Cl6	176.1 (2)	C17—C18—C24—O12	106.3 (3)
Cl5—C11—C12—Cl6	−3.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O6ⁱ	0.82 (2)	1.77 (2)	2.566 (3)	162 (3)
O10—H10···O4ⁱⁱ	0.82 (3)	1.77 (3)	2.566 (3)	164 (3)
O12—H12···O5ⁱⁱⁱ	0.82 (3)	1.77 (2)	2.583 (3)	174 (5)
O13—H13A···O9^iv	0.84	2.57	2.969 (3)	110
O13—H13A···O2^v	0.84	2.03	2.814 (3)	155
O13—H13B···O20^vi	0.84	1.93	2.733 (3)	159
O14—H14A···O2^v	0.85	1.82	2.663 (3)	169
O14—H14B···O3^vii	0.85	1.92	2.724 (3)	157
O15—H15A···O3	0.84	2.03	2.868 (3)	169
O15—H15B···O4^viii	0.85	1.90	2.738 (3)	168
O16—H16A···O8^ix	0.85	1.95	2.774 (3)	166
O16—H16B···O3^vii	0.85	1.98	2.764 (3)	153
O17—H17A···O6^ix	0.84	1.92	2.750 (3)	168
O17—H17B···Cl5ⁱⁱ	0.84	2.83	3.614 (3)	157
O18—H18A···O20^vi	0.84	1.93	2.741 (4)	161
O18—H18B···O5^x	0.84	2.30	2.809 (4)	119
O19—H19A···O11^iv	0.84	2.09	2.909 (3)	167
O19—H19B···O5^xi	0.84	2.51	3.119 (3)	131
O19—H19B···O8^ix	0.84	2.31	3.010 (3)	141
O20—H20A···O11^vii	0.85	2.04	2.781 (3)	146
O20—H20B···O10	0.85	2.17	2.834 (3)	134
O20—H20B···O12	0.85	2.59	3.080 (3)	118

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y, z+1; (v) −x+2, −y+1, −z+2; (vi) x, y, z+1; (vii) x+1, y, z; (viii) −x+1, −y+1, −z+2; (ix) −x+2, −y+1, −z+1; (x) x, y−1, z+1; (xi) x+1, y−1, z+1.

Experimental details

Crystal data
Chemical formula	[Er(C₈Cl₄O₄)(H₂O)₇](C₈HCl₄O₄)·C₈H₂Cl₄O₄·H₂O
M_r	1220.05
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.865 (2), 16.229 (5), 19.019 (7)
α, β, γ (°)	67.430 (8), 86.597 (13), 81.626 (14)
V (Å³)	1935.9 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.16 × 0.08 × 0.08

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 1999)
T_min, T_max	0.639, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	14352, 8732, 7423
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.00
No. of reflections	8732
No. of parameters	527
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.75, −1.29

Computer programs: CrystalClear (Rigaku, 1999), CrystalStructure (Rigaku, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O6ⁱ	0.82 (2)	1.77 (2)	2.566 (3)	162 (3)
O10—H10···O4ⁱⁱ	0.82 (3)	1.77 (3)	2.566 (3)	164 (3)
O12—H12···O5ⁱⁱⁱ	0.82 (3)	1.77 (2)	2.583 (3)	174 (5)
O13—H13A···O9^iv	0.84	2.57	2.969 (3)	110
O13—H13A···O2^v	0.84	2.03	2.814 (3)	155
O13—H13B···O20^vi	0.84	1.93	2.733 (3)	159
O14—H14A···O2^v	0.85	1.82	2.663 (3)	169
O14—H14B···O3^vii	0.85	1.92	2.724 (3)	157
O15—H15A···O3	0.84	2.03	2.868 (3)	169
O15—H15B···O4^viii	0.85	1.90	2.738 (3)	168
O16—H16A···O8^ix	0.85	1.95	2.774 (3)	166
O16—H16B···O3^vii	0.85	1.98	2.764 (3)	153
O17—H17A···O6^ix	0.84	1.92	2.750 (3)	168
O17—H17B···Cl5ⁱⁱ	0.84	2.83	3.614 (3)	157
O18—H18A···O20^vi	0.84	1.93	2.741 (4)	161
O18—H18B···O5^x	0.84	2.30	2.809 (4)	119
O19—H19A···O11^iv	0.84	2.09	2.909 (3)	167
O19—H19B···O5^xi	0.84	2.51	3.119 (3)	131
O19—H19B···O8^ix	0.84	2.31	3.010 (3)	141
O20—H20A···O11^vii	0.85	2.04	2.781 (3)	146
O20—H20B···O10	0.85	2.17	2.834 (3)	134
O20—H20B···O12	0.85	2.59	3.080 (3)	118

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 20971099, 10904111).

References

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