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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2025 Nov 6;81(Pt 12):1106–1110. doi: 10.1107/S2056989025009508

A lanthanum coordination polymer with 3,6-di­chloro­phthalate and 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate as ligands

Christine Hénaff a,*, Thierry Roisnel b, Chloé Blais a, Olivier Guillou a,c, Carole Daiguebonne a
Editor: F F Ferreirad
PMCID: PMC12810302  PMID: 41551386

A one-dimensional lanthanum coordination polymer based on 3,6-di­chloro­phthalate has been prepared by microwaves-assisted synthesis and structurally described.

Keywords: crystal structure; lanthanum; 3,6-di­chloro­phthalate; coordination polymer; luminescent marker

Abstract

A one-dimensional lanthanum-based coordination polymer based on 3,6-di­chloro­phthalate has been prepared and structurally described, namely, poly[[tetra­aqua­[2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoato](μ3-3,6-di­chloro­phthal­ato)lanthanum(III)] monohydrate], {[La(C8H2Cl2O4)(C10H7Cl2O4)(H2O)4]·H2O}∞. Its crystal structure can be described based on mol­ecular double chains in which lanthanum ions are linked to each other by ligands. There are several structural features that seem promising as far as luminescence properties are concerned, such as the presence of strong hydrogen bonds and of short halogen contacts, as well as quite long inter­metallic distances. It is a pity that, to date, only a lanthanum-based compound has been obtained.

1. Chemical context

Materials traceability is an ongoing challenge. Indeed, the consumption of plastics is continuously growing worldwide, and their recycling is an environmental emergency. However, whatever the recycling process, homogeneous waste batches are required and marking plastics would enable rigorous waste sorting (Vollmer et al., 2020 ▸). However, plastics must not only be marked according to the polymer matrix but also according to their complete formulation. Therefore, because of the wide variety of plastic formulations, marking them requires a large number of markers.

Our group was the first to design luminescent hetero-lanthanide coordination polymers (Kerbellec et al., 2009 ▸) and to demonstrate that these compounds behave like true mol­ecular alloys (Blais et al., 2023 ▸; Ferlay & Hosseini, 2004 ▸; Haquin et al., 2013 ▸). Luminescent markers based on lanthanide coordination polymers have proved their efficiency in the fight against counterfeiting (Guillou et al., 2016 ▸). They could also be relevant for marking plastics to improve their recyclability (Daiguebonne et al., 2025 ▸).

Recent studies strongly suggest that hetero-lanthanide coordination polymers with halogeno-derivatives of phthalic acid (Fig. 1 ▸) exhibit very promising luminescent properties and could be suitable for materials traceability (Blais et al., 2025 ▸; Ngom et al., 2024 ▸; Pointel, Suffren et al., 2020 ▸; Pointel, Houard et al., 2020 ▸; Hénaff et al., 2026 ▸). There are several reasons that can explain such promising luminescent properties (Bünzli, 2010 ▸, 2015 ▸): (i) the adjacent positions of the two carboxyl­ate functions enable the ligand to bridge several metal ions (Fig. 2 ▸), which can induce a fairly high rigidity of the mol­ecular motif and therefore helps to limit non-radiative vibrational de-excitation; (ii) halogeno substituents can be involved in halogen-bond networks (Cavallo et al., 2016 ▸; Fourmigué, 2009 ▸) that can keep mol­ecular motifs away from each other and prevent π-stacking inter­actions, which is beneficial for reducing inter­metallic energy transfers (Förster, 1960 ▸; Dexter, 1953 ▸; Blais et al., 2022 ▸; Imbert et al., 2003 ▸). The nature and the position of the halogeno substituents influence the energy of the first singlet and triplet excited states (Latva et al., 1997 ▸; Steemers et al., 1995 ▸), the photo-induced electron transfer (PET) mechanism (Freslon et al., 2014 ▸) and the strength of the halogen inter­actions (Metrangolo et al., 2008 ▸; Metrangolo & Resnati, 2001 ▸). However, contrary to halogenoterephthalate-based lanthanide coordination polymers (Smith et al., 2024 ▸), halogenophthalate-based lanthanide coordination polymers have been little studied. So, for example, the only lanthanide coordination polymers based on di­chloro­phthalates described today are those involving 4,5-di­chloro­phthalate (Badiane et al., 2018 ▸; Qiao et al., 2018 ▸; He et al., 2017 ▸) and, to the best of our knowledge, there is no example of lanthanide coordination polymers based on 3,6-di­chloro­phthalate (3,6-dcpa2−) in the literature.

Figure 1.

Figure 1

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Schematic representations of benzene-1,2-di­carb­oxy­lic or phthalic acid (a), 3,6-di­chloro­phthalic acid (b), 4,7-di­chloro­benzo­furan-1,3-dione (c) and 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate (d).

Figure 2.

Figure 2

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Coordination modes observed in lanthanide coordination polymers based on a phthalate ligand.

We have thus undertaken a study of such compounds based on 3,6-di­chloro­phthalate. For reasons of commercial availability, and because anhydrides easily hydrolyse leading to the corresponding carb­oxy­lic acids, we have chosen to use 4,7-di­chloro­benzo­furan-1,3-dione as starting reactant. In the frame of this study, we have obtained a lanthanum coordination polymer with chemical formula [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞. In this compound, as expected, 3,6-di­chloro-phthalate comes from 4,7-di­chloro­benzo­furan-1,3-dione. Unexpectedly, a second ligand is also produced: 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate. This kind of re-organization of the ligand is commonly observed (Feng et al., 2016 ▸; Abdallah et al., 2020 ▸). To the best of our knowledge, this compound constitutes the first example of a lanthanide coordination polymer based on the 3,6-dcpa2− ligand. Despite great synthetic effort, to date we have not not succeeded in synthesizing isomorphous compounds that involve luminescent lanthanide ions.1.

2. Structural commentary

Microwave-assisted reaction in water between lanthanum chloride and 4,7-di­chloro­benzo­furan-1,3-dione leads to a coordination polymer with chemical formula [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞ where 3,6-dcpa2− symbolizes 3,6-di­chloro­phtalate (CCDC-2430840) (Fig. 3 ▸).

Figure 3.

Figure 3

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Projection view of an extended asymmetric unit with the numbering scheme of [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) −1 + x, y, z; (ii) 1 − x, 1 − y, 2 − z]. The crystallization water mol­ecule is omitted.

There is one independent lanthanum ion in this crystal structure. It is ninefold coordinated by nine oxygen atoms. Four out of the nine are from four coordination water mol­ecules (O1, O2, O3 and O6), four more (O4, O7i, O8ii and O9ii) are from carboxyl­ate functions that belong to three different 3,6-dcpa2− ligands and the remaining one (O5) is from a carboxyl­ate function that belongs to the 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate ligand. They form a spherical capped square anti­prism (Table S1) (Casanova et al., 2005 ▸; Alvarez et al., 2005 ▸). There is also one independent 3,6-dcpa2− ligand and one independent 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate ligand in the crystal structure. The former is μ3(η1η1η2) and the latter is μ1(η1) (Fig. 4 ▸) Finally, there is one crystallization water mol­ecule (H13A–O13–H13B) in the crystal structure.

Figure 4.

Figure 4

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Schematic representation of the neighbourhood of the La3+ ion (left) and coordination modes of the 3,6-dcpa2− ligand (top right) and of the 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoate ligand (bottom right) of [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞.

The crystal structure is mono-dimensional and can be described based on mol­ecular double chains that spread parallel to the a axis (Fig. 5 ▸). Inside these mol­ecular double chains, lanthanum ions are linked to each other by 3,6-dcpa2− ligands while the ethyl groups of the 2,4-di­chloro-6-(eth­oxy­carbon­yl)benzoates point toward the inter­molecular space. The shortest distances between lanthanide ions that belong to the same mol­ecular motif are about 6 Å (Fig. 5 ▸).

Figure 5.

Figure 5

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Left: Projection view along the b axis of a mol­ecular double chain of [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞. Shortest inter­metallic distances are d(La—Lai) = 6.8045 (8) Å, d(La—Laii) = 6.0680 (4) Å and d(Lai—Laii) = 6.3651 (3) Å [Symmetry codes: (i) −1 + x, y, z; (ii) −x, 1 − y, 2 − z]. Right: Projection view along the a axis of two adjacent mol­ecular motifs. Dotted blue lines indicate hydrogen bonds.

It is noticeable that there is a dense network of strong intra- and inter-mol­ecular hydrogen bonds (Fig. 5 ▸ and Table 1 ▸) in this crystal structure. Additionally, there are some weak π–π inter­actions (shortest centroid–centroid distances are 3.7 Å).

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O13 0.84 (4) 2.00 (4) 2.787 (4) 155 (4)
O1—H1B⋯O10iii 0.80 (4) 1.89 (5) 2.663 (4) 164 (4)
O2—H2A⋯O10iii 0.77 (5) 2.28 (5) 2.972 (4) 150 (4)
O2—H2B⋯O1iii 0.80 (5) 2.11 (5) 2.868 (4) 159 (4)
O3—H3A⋯O10iii 0.82 (5) 2.10 (5) 2.850 (4) 152 (4)
O3—H3B⋯O13i 0.76 (5) 2.13 (5) 2.883 (4) 174 (5)
O6—H6A⋯O9iv 0.78 (4) 2.10 (4) 2.864 (3) 166 (4)
O6—H6B⋯O8 0.85 (4) 1.92 (4) 2.772 (3) 175 (4)
O13—H13A⋯O11iii 0.81 (5) 2.16 (5) 2.948 (4) 164 (5)
O13—H13B⋯O9v 0.87 (5) 2.30 (5) 3.008 (4) 139 (4)
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Symmetry codes: (i) Inline graphic; (iii) Inline graphic; (iv) Inline graphic; (v) Inline graphic.

3. Supra­molecular features

The crystal structure can be described as a juxtaposition of mol­ecular chains that spread along the a-axis direction. Beyond the network of strong hydrogen bonds, the cohesion of the crystal packing is reinforced by Cl⋯Cl inter­actions (Table 2 ▸). There are seven La3+ ions closer than 10 Å from a given La3+ ion (Table 3 ▸). All seven belong to two adjacent mol­ecular motifs spreading parallel to the ac plane (Fig. 6 ▸).

Table 2. Selected interatomic distances (Å).

Cl2i⋯Cl3 3.4185 (16) Cl3ii⋯Cl4 3.4645 (15)
Cl2⋯Cl3 3.4287 (15)    
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Table 3. La⋯La distances (Å) shorter than 10 Å in [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4·H2O]∞.

Atom1 Atom2 Symmetry Distance
La1 La1 −x, 1 − y, 2 − z 6.0682 (6)
  La1 −x, 1 − y, 1 − z 6.2554 (7)
  La1 1 − x, 1 − y, 2 − z 6.3650 (6)
  La1 1 + x, y, z 6.8044 (8)
  La1 −1 + x, y, z 6.8046 (8)
  La1 1 − x, 1 − y, 1 − z 8.5065 (8)
  La1 −1 − x, 1 − y, 1 − z 9.9248 (9)
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Figure 6.

Figure 6

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Projection view along the b axis of two adjacent mol­ecular motifs. The dotted circle centred on the given La3+ ion (in yellow) has a 10 Å radius.

In conclusion, this crystal structure presents inter­esting features as far as luminescent properties are concerned. Indeed, the lanthanide ions are quite far from each other and the dense network of hydrogen and halogen bonds is expected to limit non-radiative vibrational de-excitation. The reproducibility of the synthesis was checked by reproducing it several times. Unfortunately, to date, we have not succeeded in synthesizing any iso-structural coordination polymer based on a luminescent lanthanide ion.

4. Database survey

A search of the Cambridge Structural Database was performed using ConQuest (version 2024.2.0, CSD version 5.45, updated September 2024; Groom et al., 2016 ▸). For lanthanide coordination polymers based on phthalate ligands, see: Li et al. (2009 ▸; CSD refcode KUGPUY); Meng et al. (2006 ▸; LEJPIA); Wan et al. (2002 ▸; WUJSID, WUJSOJ, WUJSUP, WUJTAW); Song et al. (2004 ▸, 2010 ▸; FIBWOD, YURGIC); Thirumurugan & Natarajan (2003 ▸; BEVPIC); Wang et al. (2008 ▸; FARJAL, KIWPOW) Pizon et al. (2010 ▸; IJEJOX); Luo et al. (2010 ▸; DUWRIX; Lush & Shen (2011 ▸; AZITOT); for 3,6-di­chloro­phthalate, see: Mattes & Dorau (1986 ▸; SAZQOZ); for lanthanide coordination polymers based on 4,5-di­chloro-hthalates, see: Badiane et al. (2018 ▸; BETYOR); Qiao et al. (2018 ▸; GIQCIV, GIQCOB, GIQCUH, GIQDAO, MICCEJ); He et al. (2017 ▸; DEJGAD). For a structural comparison between these crystal structures, see: Hénaff et al. (2026 ▸).

5. Synthesis and crystallization

Lanthanum oxide (4N) was purchased from Ampère. Hydrated lanthanum chloride [LaCl3(H2O)6] was prepared according to established procedures (Desreux, 1989 ▸). 4,7-Di­chloro­benzo­furan-1,3-dione (C8H2Cl2O3, 98%) was purchased from BDLpharm and used without further purification. 0.5 mmol (185.6 mg) of LaCl3(H2O)6, 0.75 mmol (162.7 mg) of C8H2Cl2O3, 1.5 mL of a solution of sodium hydroxide (1 mol L−1) and 3.5 mL of deionized water were put in a 10 mL sealed Pyrex test tube in a CEM Discover microwave oven and maintained for 10 min under stirring (T = 403 K; P = 2.5 bar). Single crystals suitable for X-ray diffraction were obtained after slow evaporation of the supernatant solution extracted after the synthesis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4 ▸. Except for O-bound H atoms that were introduced in the structural model through Fourier difference map analysis, H atoms were finally included in their calculated positions (C—H = 0.95–0.98 Å) and treated as riding on their parent atom with Uiso(H) = 1.2–1.5Ueq(C).

Table 4. Experimental details.

Crystal data
Chemical formula [La(C8H2Cl2O4)(C10H7Cl2O4)(H2O)4]·H2O
M r 724.04
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 6.8045 (7), 32.376 (3), 11.5188 (12)
β (°) 100.862 (4)
V (Å3) 2492.2 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 2.21
Crystal size (mm) 0.44 × 0.07 × 0.03
 
Data collection
Diffractometer D8 VENTURE Bruker AXS
Absorption correction Multi-scan (SADABS; Krause et al., 2015 ▸)
Tmin, Tmax 0.777, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections 19761, 5674, 5503
R int 0.028
(sin θ/λ)max (Å−1) 0.650
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.068, 1.27
No. of reflections 5674
No. of parameters 355
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.72, −1.05
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Computer programs: APEX3 (Bruker, 2015 ▸), SAINT (Bruker, 2014 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2019/2 (Sheldrick, 2015b ▸), SXGRAPH (Farrugia, 1999 ▸), Mercury (Macrae et al., 2020 ▸) and CRYSCALC (T. Roisnel, local program, 2024).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025009508/ee2020sup1.cif

e-81-01106-sup1.cif (678.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025009508/ee2020Isup3.hkl

e-81-01106-Isup3.hkl (451.4KB, hkl)

CCDC reference: 2430840

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The CDifX (Centre de Diffractométrie X) of ISCR is acknowledged for X-ray diffraction data collection.

supplementary crystallographic information

Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Crystal data

[La(C8H2Cl2O4)(C10H7Cl2O4)(H2O)4]·H2O F(000) = 1424
Mr = 724.04 Dx = 1.930 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 6.8045 (7) Å Cell parameters from 9930 reflections
b = 32.376 (3) Å θ = 2.6–27.5°
c = 11.5188 (12) Å µ = 2.21 mm−1
β = 100.862 (4)° T = 150 K
V = 2492.2 (4) Å3 Stick, colourless
Z = 4 0.44 × 0.07 × 0.03 mm
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Data collection

D8 VENTURE Bruker AXS diffractometer 5674 independent reflections
Radiation source: Incoatec microfocus sealed tube 5503 reflections with I > 2σ(I)
Multilayer monochromator Rint = 0.028
Detector resolution: 7.39 pixels mm-1 θmax = 27.5°, θmin = 1.9°
rotation images scans h = −8→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015) k = −41→41
Tmin = 0.777, Tmax = 0.936 l = −14→14
19761 measured reflections
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + 7.126P] where P = (Fo2 + 2Fc2)/3
S = 1.27 (Δ/σ)max = 0.002
5674 reflections Δρmax = 0.72 e Å−3
355 parameters Δρmin = −1.05 e Å−3
0 restraints
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Special details

Experimental. A suitable crystal for X-ray diffraction single crystal experiment (colourless stick, dimensions = 0.030 x 0.070 x 0.440 mm) was selected and mounted with a cryoloop on the goniometer head of a D8 Venture (Bruker-AXS) diffractometer equipped with a CMOS-PHOTON70 detector, using Mo-Kα radiation (λ = 0.71073 Å, multilayer monochromator) at T = 150 (2) K. Crystal structure has been described in monoclinic symmetry and P 21/c (I.T.#14) centric space group (Rint=0.0280; Rsigma=0.0262 ). Cell parameters have been refined as follows: a = 6.8045 (7) Å, b = 32.376 (3) Å, c=11.5188 (12) Å, β = 100.862 (4) °, V = 2492.2 (4) Å3. Number of formula unit Z is equal to 4 and calculated density d and absorption coefficient µ values are 1.930 g.cm-3 and 2.207mm-1 respectively. Crystal structure was solved by dual-space algorithm using SHELXT program and then refined with full-matrix least-squares methods based on F2 (SHELXL program). All non-Hydrogen atoms were refined with anisotropic atomic displacement parameters. Except Hydrogen atoms linked to Oxygen atoms that were introduced in the structural model through Fourier difference maps analysis, H atoms were finally included in their calculated positions and treated as riding on their parent atom with constrained thermal parameters. A final refinement on F2 with 5674 unique intensities and 355 parameters converged at ωR(F2)=0.0678 (RF = 0.0325) for 5503 observed reflections with I > 2σ.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
La1 0.15728 (3) 0.49053 (2) 0.77186 (2) 0.01071 (6)
Cl1 0.52632 (12) 0.57653 (3) 0.57191 (7) 0.02214 (17)
Cl2 0.86113 (15) 0.66386 (3) 1.04825 (9) 0.0310 (2)
Cl3 0.35058 (15) 0.65895 (3) 1.01756 (8) 0.0320 (2)
Cl4 0.1852 (2) 0.74928 (3) 0.62045 (10) 0.0402 (3)
O1 −0.1375 (4) 0.45586 (8) 0.6315 (2) 0.0190 (5)
H1A −0.216 (7) 0.4425 (13) 0.666 (4) 0.023*
H1B −0.111 (6) 0.4389 (13) 0.586 (4) 0.023*
O2 0.2230 (4) 0.48617 (8) 0.5597 (2) 0.0201 (5)
H2A 0.195 (7) 0.4665 (14) 0.522 (4) 0.024*
H2B 0.227 (6) 0.5050 (14) 0.515 (4) 0.024*
O3 0.2806 (4) 0.41711 (8) 0.7131 (2) 0.0214 (5)
H3A 0.234 (7) 0.4074 (13) 0.648 (4) 0.026*
H3B 0.390 (7) 0.4112 (14) 0.728 (4) 0.026*
O4 0.5011 (3) 0.51206 (7) 0.7824 (2) 0.0185 (5)
O5 0.0711 (4) 0.55684 (7) 0.6732 (2) 0.0187 (5)
O6 0.2443 (4) 0.53789 (8) 0.9496 (2) 0.0162 (5)
H6A 0.172 (6) 0.5421 (13) 0.994 (4) 0.019*
H6B 0.365 (7) 0.5414 (13) 0.985 (4) 0.019*
O7 0.8332 (3) 0.51060 (7) 0.8259 (2) 0.0175 (5)
O8 0.6424 (3) 0.55065 (7) 1.05147 (19) 0.0160 (5)
O9 0.9632 (3) 0.56660 (7) 1.08782 (19) 0.0163 (5)
O10 −0.0218 (4) 0.59396 (8) 0.5099 (2) 0.0203 (5)
O11 0.1928 (5) 0.66501 (9) 0.4265 (2) 0.0350 (7)
O12 −0.1099 (4) 0.68329 (9) 0.4598 (2) 0.0321 (6)
O13 −0.3045 (4) 0.39310 (9) 0.7472 (3) 0.0286 (6)
H13A −0.272 (7) 0.3738 (15) 0.711 (4) 0.034*
H13B −0.220 (7) 0.3931 (15) 0.814 (4) 0.034*
C1 0.6686 (5) 0.52900 (10) 0.8040 (3) 0.0139 (6)
C2 0.6774 (4) 0.57584 (10) 0.8076 (3) 0.0135 (6)
C3 0.6275 (5) 0.59966 (11) 0.7059 (3) 0.0158 (6)
C4 0.6544 (5) 0.64206 (11) 0.7079 (3) 0.0208 (7)
H4 0.622165 0.657699 0.637085 0.025*
C5 0.7287 (5) 0.66131 (11) 0.8138 (3) 0.0215 (7)
H5 0.747350 0.690401 0.816744 0.026*
C6 0.7758 (5) 0.63795 (11) 0.9160 (3) 0.0192 (7)
C7 0.7527 (5) 0.59551 (10) 0.9149 (3) 0.0138 (6)
C8 0.7894 (5) 0.56959 (9) 1.0260 (3) 0.0128 (6)
C9 0.0562 (5) 0.59016 (10) 0.6172 (3) 0.0140 (6)
C10 0.1326 (5) 0.62886 (10) 0.6833 (3) 0.0153 (6)
C11 0.1994 (5) 0.62682 (10) 0.8049 (3) 0.0163 (6)
H11 0.203366 0.601080 0.844882 0.020*
C12 0.2599 (5) 0.66250 (11) 0.8673 (3) 0.0192 (7)
C13 0.2529 (6) 0.70049 (11) 0.8124 (3) 0.0235 (7)
H13 0.290133 0.724962 0.856623 0.028*
C14 0.1899 (6) 0.70185 (11) 0.6906 (3) 0.0227 (7)
C15 0.1311 (5) 0.66659 (11) 0.6241 (3) 0.0184 (7)
C16 0.0752 (6) 0.67031 (11) 0.4919 (3) 0.0235 (7)
C17 −0.1740 (9) 0.69157 (16) 0.3343 (4) 0.0497 (13)
H17A −0.180144 0.665521 0.288787 0.060*
H17B −0.078142 0.710400 0.306355 0.060*
C18 −0.3711 (10) 0.7106 (2) 0.3177 (6) 0.076 (2)
H18A −0.418000 0.716488 0.233614 0.114*
H18B −0.464813 0.691644 0.345401 0.114*
H18C −0.363204 0.736350 0.362901 0.114*
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
La1 0.00833 (9) 0.01307 (9) 0.01034 (8) −0.00037 (7) 0.00073 (6) −0.00107 (7)
Cl1 0.0187 (4) 0.0346 (5) 0.0126 (3) 0.0022 (3) 0.0016 (3) 0.0008 (3)
Cl2 0.0370 (5) 0.0243 (4) 0.0304 (5) −0.0050 (4) 0.0029 (4) −0.0104 (4)
Cl3 0.0349 (5) 0.0384 (5) 0.0217 (4) −0.0004 (4) 0.0030 (4) −0.0065 (4)
Cl4 0.0657 (8) 0.0160 (4) 0.0377 (5) −0.0049 (5) 0.0063 (5) 0.0054 (4)
O1 0.0181 (12) 0.0223 (13) 0.0159 (11) −0.0045 (10) 0.0018 (9) −0.0044 (10)
O2 0.0268 (13) 0.0183 (13) 0.0158 (12) −0.0007 (11) 0.0057 (10) −0.0012 (10)
O3 0.0206 (13) 0.0244 (13) 0.0177 (12) 0.0044 (11) −0.0003 (10) −0.0039 (10)
O4 0.0123 (11) 0.0225 (12) 0.0204 (11) −0.0030 (10) 0.0023 (9) −0.0013 (10)
O5 0.0223 (12) 0.0144 (11) 0.0197 (11) 0.0004 (10) 0.0046 (10) 0.0012 (9)
O6 0.0098 (11) 0.0244 (13) 0.0144 (11) 0.0002 (10) 0.0024 (9) −0.0049 (9)
O7 0.0120 (11) 0.0191 (12) 0.0216 (11) 0.0032 (9) 0.0039 (9) 0.0006 (10)
O8 0.0115 (11) 0.0222 (12) 0.0133 (10) −0.0031 (9) −0.0001 (8) 0.0017 (9)
O9 0.0108 (10) 0.0227 (12) 0.0148 (11) 0.0010 (9) 0.0009 (9) 0.0008 (9)
O10 0.0220 (12) 0.0208 (12) 0.0163 (11) 0.0026 (10) −0.0007 (9) −0.0006 (9)
O11 0.0485 (18) 0.0363 (16) 0.0247 (14) −0.0026 (14) 0.0189 (13) 0.0013 (12)
O12 0.0415 (17) 0.0302 (15) 0.0211 (13) 0.0112 (13) −0.0028 (12) 0.0021 (11)
O13 0.0266 (15) 0.0311 (15) 0.0281 (15) −0.0008 (12) 0.0054 (12) −0.0013 (12)
C1 0.0136 (15) 0.0200 (16) 0.0089 (13) −0.0008 (12) 0.0040 (11) −0.0007 (12)
C2 0.0081 (13) 0.0184 (15) 0.0148 (14) 0.0017 (12) 0.0039 (11) 0.0001 (12)
C3 0.0109 (14) 0.0231 (17) 0.0138 (14) 0.0035 (13) 0.0034 (12) 0.0009 (12)
C4 0.0173 (16) 0.0215 (17) 0.0248 (17) 0.0072 (14) 0.0073 (14) 0.0098 (14)
C5 0.0194 (17) 0.0165 (16) 0.0293 (18) 0.0016 (14) 0.0065 (14) 0.0035 (14)
C6 0.0167 (16) 0.0195 (17) 0.0213 (16) −0.0018 (13) 0.0034 (13) −0.0037 (13)
C7 0.0105 (14) 0.0173 (15) 0.0142 (14) 0.0004 (12) 0.0041 (11) 0.0019 (12)
C8 0.0153 (15) 0.0129 (14) 0.0100 (13) 0.0010 (12) 0.0022 (11) −0.0010 (11)
C9 0.0112 (14) 0.0148 (15) 0.0172 (15) −0.0007 (12) 0.0058 (12) −0.0017 (12)
C10 0.0152 (15) 0.0146 (15) 0.0177 (15) 0.0006 (12) 0.0069 (12) −0.0011 (12)
C11 0.0159 (15) 0.0167 (15) 0.0172 (15) −0.0009 (13) 0.0058 (12) 0.0012 (12)
C12 0.0174 (16) 0.0247 (18) 0.0151 (15) 0.0001 (14) 0.0024 (12) −0.0034 (13)
C13 0.0258 (18) 0.0191 (17) 0.0254 (18) −0.0032 (15) 0.0039 (15) −0.0057 (14)
C14 0.0292 (19) 0.0148 (16) 0.0252 (18) 0.0003 (14) 0.0078 (15) 0.0024 (14)
C15 0.0190 (16) 0.0192 (16) 0.0175 (16) 0.0013 (13) 0.0050 (13) 0.0019 (13)
C16 0.035 (2) 0.0151 (16) 0.0211 (17) 0.0008 (15) 0.0069 (15) 0.0030 (13)
C17 0.071 (4) 0.046 (3) 0.023 (2) 0.011 (3) −0.013 (2) 0.0057 (19)
C18 0.065 (4) 0.086 (5) 0.063 (4) 0.016 (4) −0.022 (3) 0.019 (4)
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Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Geometric parameters (Å, º)

La1—O4 2.422 (2) O12—C17 1.454 (5)
La1—O5 2.448 (2) O13—H13A 0.81 (5)
La1—O7i 2.488 (2) O13—H13B 0.87 (5)
La1—O6 2.537 (2) C1—C2 1.518 (5)
La1—O2 2.570 (2) C2—C3 1.390 (4)
La1—O1 2.584 (2) C2—C7 1.398 (4)
La1—O8ii 2.595 (2) C3—C4 1.385 (5)
La1—O3 2.651 (3) C4—C5 1.379 (5)
La1—O9ii 2.684 (2) C4—H4 0.9500
La1—C8ii 3.004 (3) C5—C6 1.385 (5)
Cl1—C3 1.737 (3) C5—H5 0.9500
Cl2—C6 1.740 (4) C6—C7 1.383 (5)
Cl3—C12 1.729 (3) C7—C8 1.511 (4)
Cl4—C14 1.733 (4) C9—C10 1.507 (4)
O1—H1A 0.84 (4) C10—C11 1.390 (5)
O1—H1B 0.80 (4) C10—C15 1.398 (5)
O2—H2A 0.77 (5) C11—C12 1.381 (5)
O2—H2B 0.80 (5) C11—H11 0.9500
O3—H3A 0.82 (5) C12—C13 1.379 (5)
O3—H3B 0.76 (5) C13—C14 1.388 (5)
O4—C1 1.247 (4) C13—H13 0.9500
O5—C9 1.251 (4) C14—C15 1.391 (5)
O6—H6A 0.78 (4) C15—C16 1.504 (5)
O6—H6B 0.85 (4) C17—C18 1.455 (8)
O7—C1 1.252 (4) C17—H17A 0.9900
O8—C8 1.255 (4) C17—H17B 0.9900
O9—C8 1.263 (4) C18—H18A 0.9800
O10—C9 1.257 (4) C18—H18B 0.9800
O11—C16 1.210 (5) C18—H18C 0.9800
O12—C16 1.313 (5)
Cl2iii···Cl3 3.4185 (16) Cl3iv···Cl4 3.4645 (15)
Cl2···Cl3 3.4287 (15)
O4—La1—O5 85.14 (8) O4—C1—O7 125.5 (3)
O4—La1—O7i 143.67 (8) O4—C1—C2 118.4 (3)
O5—La1—O7i 75.00 (8) O7—C1—C2 116.1 (3)
O4—La1—O6 73.11 (8) C3—C2—C7 118.9 (3)
O5—La1—O6 81.00 (8) C3—C2—C1 121.9 (3)
O7i—La1—O6 73.93 (8) C7—C2—C1 119.0 (3)
O4—La1—O2 73.96 (8) C4—C3—C2 121.7 (3)
O5—La1—O2 71.11 (8) C4—C3—Cl1 118.1 (3)
O7i—La1—O2 125.01 (8) C2—C3—Cl1 120.2 (3)
O6—La1—O2 138.13 (8) C5—C4—C3 119.2 (3)
O4—La1—O1 141.71 (8) C5—C4—H4 120.4
O5—La1—O1 90.05 (8) C3—C4—H4 120.4
O7i—La1—O1 69.51 (8) C4—C5—C6 119.5 (3)
O6—La1—O1 143.43 (8) C4—C5—H5 120.2
O2—La1—O1 68.58 (8) C6—C5—H5 120.2
O4—La1—O8ii 75.46 (7) C7—C6—C5 121.8 (3)
O5—La1—O8ii 149.22 (8) C7—C6—Cl2 120.4 (3)
O7i—La1—O8ii 107.29 (7) C5—C6—Cl2 117.8 (3)
O6—La1—O8ii 70.69 (8) C6—C7—C2 118.9 (3)
O2—La1—O8ii 123.90 (8) C6—C7—C8 122.9 (3)
O1—La1—O8ii 119.92 (8) C2—C7—C8 118.0 (3)
O4—La1—O3 85.50 (8) O8—C8—O9 122.2 (3)
O5—La1—O3 136.70 (8) O8—C8—C7 117.2 (3)
O7i—La1—O3 129.51 (8) O9—C8—C7 120.5 (3)
O6—La1—O3 135.31 (8) O8—C8—La1ii 59.15 (16)
O2—La1—O3 65.67 (8) O9—C8—La1ii 63.26 (16)
O1—La1—O3 72.34 (8) C7—C8—La1ii 173.1 (2)
O8ii—La1—O3 66.07 (8) O5—C9—O10 124.8 (3)
O4—La1—O9ii 124.74 (7) O5—C9—C10 118.0 (3)
O5—La1—O9ii 144.12 (7) O10—C9—C10 117.2 (3)
O7i—La1—O9ii 69.12 (7) C11—C10—C15 120.2 (3)
O6—La1—O9ii 88.95 (7) C11—C10—C9 119.1 (3)
O2—La1—O9ii 131.49 (8) C15—C10—C9 120.7 (3)
O1—La1—O9ii 77.78 (7) C12—C11—C10 119.5 (3)
O8ii—La1—O9ii 49.35 (7) C12—C11—H11 120.2
O3—La1—O9ii 71.52 (7) C10—C11—H11 120.2
O4—La1—C8ii 99.99 (8) C13—C12—C11 121.8 (3)
O5—La1—C8ii 155.69 (8) C13—C12—Cl3 119.5 (3)
O7i—La1—C8ii 87.61 (8) C11—C12—Cl3 118.7 (3)
O6—La1—C8ii 77.89 (8) C12—C13—C14 117.9 (3)
O2—La1—C8ii 133.19 (8) C12—C13—H13 121.0
O1—La1—C8ii 99.77 (8) C14—C13—H13 121.0
O8ii—La1—C8ii 24.53 (8) C13—C14—C15 122.2 (3)
O3—La1—C8ii 67.60 (8) C13—C14—Cl4 118.3 (3)
O9ii—La1—C8ii 24.86 (8) C15—C14—Cl4 119.5 (3)
La1—O1—H1A 114 (3) C14—C15—C10 118.3 (3)
La1—O1—H1B 118 (3) C14—C15—C16 118.9 (3)
H1A—O1—H1B 101 (4) C10—C15—C16 122.7 (3)
La1—O2—H2A 120 (3) O11—C16—O12 125.6 (4)
La1—O2—H2B 127 (3) O11—C16—C15 123.2 (4)
H2A—O2—H2B 108 (4) O12—C16—C15 110.9 (3)
La1—O3—H3A 120 (3) O12—C17—C18 107.8 (5)
La1—O3—H3B 121 (3) O12—C17—H17A 110.2
H3A—O3—H3B 107 (4) C18—C17—H17A 110.2
C1—O4—La1 167.0 (2) O12—C17—H17B 110.2
C9—O5—La1 169.9 (2) C18—C17—H17B 110.2
La1—O6—H6A 123 (3) H17A—C17—H17B 108.5
La1—O6—H6B 122 (3) C17—C18—H18A 109.5
H6A—O6—H6B 109 (4) C17—C18—H18B 109.5
C1—O7—La1iii 151.1 (2) H18A—C18—H18B 109.5
C8—O8—La1ii 96.32 (18) C17—C18—H18C 109.5
C8—O9—La1ii 91.88 (18) H18A—C18—H18C 109.5
C16—O12—C17 115.5 (3) H18B—C18—H18C 109.5
H13A—O13—H13B 105 (5)
La1—O4—C1—O7 133.7 (9) C6—C7—C8—O9 −65.7 (4)
La1—O4—C1—C2 −44.7 (11) C2—C7—C8—O9 119.3 (3)
La1iii—O7—C1—O4 111.9 (4) La1—O5—C9—O10 90.4 (13)
La1iii—O7—C1—C2 −69.7 (5) La1—O5—C9—C10 −91.1 (13)
O4—C1—C2—C3 −70.8 (4) O5—C9—C10—C11 −5.8 (4)
O7—C1—C2—C3 110.6 (3) O10—C9—C10—C11 172.9 (3)
O4—C1—C2—C7 114.2 (3) O5—C9—C10—C15 176.1 (3)
O7—C1—C2—C7 −64.3 (4) O10—C9—C10—C15 −5.2 (4)
C7—C2—C3—C4 1.4 (5) C15—C10—C11—C12 1.5 (5)
C1—C2—C3—C4 −173.6 (3) C9—C10—C11—C12 −176.6 (3)
C7—C2—C3—Cl1 −178.0 (2) C10—C11—C12—C13 1.1 (5)
C1—C2—C3—Cl1 7.0 (4) C10—C11—C12—Cl3 −177.7 (2)
C2—C3—C4—C5 −1.4 (5) C11—C12—C13—C14 −2.4 (5)
Cl1—C3—C4—C5 178.0 (3) Cl3—C12—C13—C14 176.4 (3)
C3—C4—C5—C6 0.3 (5) C12—C13—C14—C15 1.2 (6)
C4—C5—C6—C7 0.8 (5) C12—C13—C14—Cl4 −178.8 (3)
C4—C5—C6—Cl2 −177.9 (3) C13—C14—C15—C10 1.2 (5)
C5—C6—C7—C2 −0.8 (5) Cl4—C14—C15—C10 −178.7 (3)
Cl2—C6—C7—C2 177.9 (2) C13—C14—C15—C16 −176.8 (3)
C5—C6—C7—C8 −175.7 (3) Cl4—C14—C15—C16 3.2 (5)
Cl2—C6—C7—C8 3.0 (4) C11—C10—C15—C14 −2.6 (5)
C3—C2—C7—C6 −0.3 (4) C9—C10—C15—C14 175.5 (3)
C1—C2—C7—C6 174.8 (3) C11—C10—C15—C16 175.4 (3)
C3—C2—C7—C8 174.9 (3) C9—C10—C15—C16 −6.5 (5)
C1—C2—C7—C8 −10.0 (4) C17—O12—C16—O11 0.2 (6)
La1ii—O8—C8—O9 −4.8 (3) C17—O12—C16—C15 174.7 (3)
La1ii—O8—C8—C7 173.3 (2) C14—C15—C16—O11 93.0 (5)
La1ii—O9—C8—O8 4.7 (3) C10—C15—C16—O11 −85.0 (5)
La1ii—O9—C8—C7 −173.4 (2) C14—C15—C16—O12 −81.6 (4)
C6—C7—C8—O8 116.1 (3) C10—C15—C16—O12 100.4 (4)
C2—C7—C8—O8 −58.8 (4) C16—O12—C17—C18 −172.7 (4)
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Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z; (iv) x, −y+3/2, z+1/2.

Poly[[tetraaqua[2,4-dichloro-6-(ethoxycarbonyl)benzoato](µ3-3,6-dichlorophthalato)lanthanum(III)] monohydrate] . Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O1—H1A···O13 0.84 (4) 2.00 (4) 2.787 (4) 155 (4)
O1—H1B···O10v 0.80 (4) 1.89 (5) 2.663 (4) 164 (4)
O2—H2A···O10v 0.77 (5) 2.28 (5) 2.972 (4) 150 (4)
O2—H2B···O1v 0.80 (5) 2.11 (5) 2.868 (4) 159 (4)
O3—H3A···O10v 0.82 (5) 2.10 (5) 2.850 (4) 152 (4)
O3—H3B···O13iii 0.76 (5) 2.13 (5) 2.883 (4) 174 (5)
O6—H6A···O9i 0.78 (4) 2.10 (4) 2.864 (3) 166 (4)
O6—H6B···O8 0.85 (4) 1.92 (4) 2.772 (3) 175 (4)
O13—H13A···O11v 0.81 (5) 2.16 (5) 2.948 (4) 164 (5)
O13—H13B···O9ii 0.87 (5) 2.30 (5) 3.008 (4) 139 (4)
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Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z; (v) −x, −y+1, −z+1.

Continuous Shape Measurements (CShM) for [La(3,6-dcpa)(C10H7Cl2O4)(H2O)4.H2O]∞. The lower is the CShM value, the better is the agreement with the given coordination polyhedron.

[ML9] EP-9 OPY-9 HBPY-9 JTC-9 JCCU-9 CCU-9 JCSAPR-9 CSAPR-9 JTCTPR-9 TCTPR-9 JTDIC-9 HH-9 MFF-9
La 35.863 21.416 20.115 15.640 11.075 9.311 2.176 1.059 2.715 1.073 13.106 10.786 1.588
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EP-9 ≡D9h-Enneagon; OPY-9 ≡C8v-Octagonal pyramid; HBPY-9 ≡D7h-Heptagonal bipyramid; JTC-9≡C3v-Johnson triangular cupola J3; JCCU-9 ≡C4v-Capped cube J8; CCU-9 ≡C4v-Spherical-relaxed capped cube; JCSAPR-9 C4v-Capped square antiprism J10; CSAPR-9 ≡C4v-Spherical capped square antiprism; JTCTPR-9 ≡D3h-Tricapped trigonal prism J51; TCTPR-9 ≡D3h Spherical tricapped trigonal prism; JTDIC-9 ≡C3v-Tridiminished icosahedron J63; HH-9 ≡C2v-Hula-hoop; MFF-9 ≡Cs-Muffin.

Funding Statement

Funding for this research was provided by: Région Bretagne (grant No. ARED-COH24014).

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989025009508/ee2020sup1.cif

e-81-01106-sup1.cif (678.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989025009508/ee2020Isup3.hkl

e-81-01106-Isup3.hkl (451.4KB, hkl)

CCDC reference: 2430840

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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