research communications
Synthesis, μ5-2,5-dicarboxybenzene-1,4-dicarboxylato)strontium]
and thermal properties of poly[aqua(aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université des Frères Mentouri Constantine, 25000, Algeria, bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria, and cDepartamento de Química Física y Analítica, Universidad de Oviedo-CINN, 33006 Oviedo, Spain
*Correspondence e-mail: Bouacida_Sofiane@yahoo.fr
A coordination polymer formulated as [Sr(H2BTEC)(H2O)]n (H4BTEC = benzene-1,2,4,5-tetracarboxylic acid, C10H6O8), was synthesized hydrothermally and characterized by single-crystal and powder X-ray diffraction, and Its is made up of a zigzag inorganic chain formed by edge-sharing of [SrO8] polyhedra running along [001]. Adjacent chains are connected to each other via the carboxylate groups of the ligand, resulting in a double-layered network extending parallel to (100). O—H⋯O hydrogen bonds of medium-to-weak strength between the layers consolidate the three-dimensional structure. One of the carboxylic OH functions was found to be disordered over two sets of sites with half-occupancy.
CCDC reference: 1890785
1. Chemical context
In recent years, the self-assembly of coordination polymers (CP) and crystal engineering of metal–organic coordination frameworks have attracted great interest because of their varied molecular topologies and the potential applications of these polymers as functional materials (Pan et al., 2004; Jiang et al., 2011; Du et al., 2014). Derivatives of aromatic tetracarboxylic acids such as 1,2,4,5-benzenetetracarboxylic acid (H4BTEC, commonly known as pyromellitic acid) and their deprotonated forms (HnBTEC(4–n)–) belong to an important family of polycarboxylate O-donor ligands, which have been used extensively to prepare CPs (Liu et al., 2009). The variations in the possible binding modes of its four potentially coordinating carboxylic/carboxylate groups, along with the different coordination preferences of the metal ions, gives rise to a great variety of crystal structures.
In this communication, we report on the synthesis of [Sr(H2BTEC)(H2O)], (I), along with its characterization by single-crystal and powder X-ray diffraction, coupled with energy-dispersive and thermal analysis.
2. Structural commentary
The comprises one SrII atom, one doubly deprotonated (H2BTEC)2– anion and one coordinating water molecule O1W (Fig. 1). The SrII atom is bonded to eight oxygen atoms, seven of them coming from five carboxylate or carboxylic groups of five different (H2BTEC)2– ligands, and one oxygen atom from the water molecule. The resulting around the alkaline earth cation may be described as a distorted bicapped prism (Fig. 2a). The Sr—O bond lengths span the range 2.4915 (19)–2.8239 (19) Å for carboxylate/carboxylic acid groups, and the Sr—O(water) bond length is 2.520 (3) Å. These distances are comparable to those reported in other strontium–carboxylate complexes (He et al., 2014). The (H2BTEC)2– anion has a bridging character and connects five SrII atoms (Fig. 2b) whereby three different coordination modes are realized. The carboxylate group (O1—C1—O2) adopts both a bis-monodentate bridging mode to two SrII atoms and a bidentate chelating mode to a third SrII atom; the carboxylic group (O7/C10/O8/H8) is monodentately bound through O7 to a fourth SrII atom and shows an intramolecular O8—H8⋯O6 hydrogen bond (Table 1); the carboxylate group (O5/C9/O6) exhibits a bidentate chelating mode to a fifth SrII atom. The carboxylic group (O3/C8/O4/H4) has a disordered hydroxyl group and does not bind to a cation. The [SrO8] polyhedra share edges through (O1—O2), thus forming an infinite zigzag chain running parallel to [001] (Fig. 3a). These chains are further connected through the carboxylate groups (O1/C1/O2 and O5/C9/O6) into double layers parallel to (100) that are stacked along [100] (Fig. 3b). A topological analysis (Blatov et al., 2014) revealed that the overall structure of the coordination polymer (I) can be defined as a uninodal five-connected net with the Schläfli symbol {48.62}, and the vertex symbols of SrII and (H2BTEC)2– node is [4.4.4.4.4.4.4.4.6(3).6(3)] (Fig. 4).
of compound (I)3. Supramolecular features
In the , neighbouring layers are linked to each other along the stacking direction by intermolecular O—H⋯O hydrogen bonds of medium-to-weak strength involving the coordinating water molecule with the carbonyl O atom (O3) of the non-coordinating carboxylic acid group as acceptor, as well as the disordered O4—H4 function of this carboxylic acid group and carboxylate O atom O4 as an acceptor group (Table 1). The hydrogen-bonding scheme is completed by two weak intermolecular C—H⋯O interactions involving aromatic H atoms (Table 1). Based on the connectivity of these hydrogen bonds, four different motifs (Etter et al., 1990) can be distinguished, viz. R22(8), R22(10), R22(13) and R22(15) (Fig. 5), leading to a three-dimensional supramolecular structure (Figs. 6, 7).
of (I)4. Crystal morophology and characterization
SEM images show the appearance of the microcrystalline powder, while EDX measurements provided qualitative confirmation about the presence of all non-hydrogen atoms (Fig. 8). The FT–IR spectrum of complex (I) (Fig. S1 in the supporting information) shows broad absorption bands near 3440 cm−1, which are assigned to O—H stretching vibrations of the –COOH groups and water molecules, respectively. The bands located at 3164 cm−1 can be attributed to aromatic C—H stretching vibration. In addition, the symmetric [νs(OCO) = 1414 and 1346 cm−1] and asymmetric [νas(OCO) = 1626 and 1533 cm−1] stretching vibrations in (I) can be attributed to the split of the absorption bands of the carboxylate groups. The Δ(νas–νs) values of 187–212 cm−1 indicate that some of the carboxylate groups are monodentate and bridging to the SrII atoms. A strong absorption at 1731 cm−1 confirms the presence of the carboxylic acid function. All these results are in agreement with the crystallographic data.
Plots of the experimental and simulated powder X-ray diffraction (PXRD) patterns of the title compound are shown in Fig. 9, revealing a good match and thus phase purity and repeatable synthesis. TG/DTG, SDTA curves and the analysis are depicted in Fig. 10a. TG/DTG curves of (I) reveal a total mass loss of ca 60.5% (calc. 58.1%) from room temperature up to 1273 K, with SrO as the final product. The mass loss of (I), under a dry N2 atmosphere, proceeds in four steps. The first one, between 298 and 550 K with a mass loss of ca 5.2% (cal. 5.0%), is associated with an (491 K in the SDTA curve) and corresponds to the loss of the coordinating water molecule. The second step, between 557 and 719 K with a mass loss of ca 22.1% (calc. 25.7%) and an (peak at 609 K), is attributed to the beginning of the decomposition of the (H2BTEC)2– ligand. The third step, between 706 and 908 K with a mass loss of about 15.3% is exothermic (peak at 882 K), and may be attributed to the complete decomposition of the organic anion. The fourth step, between 908 and 1147 K with a mass loss of 17.9% is also exothermic (peak at 1121 K), and may be due to another evaporation of trapped organic moieties. The associated m/z 18 (H2O), 44 (CO2), and 76 (C6H4) curves (Fig. 10b) are in agreement with the TG/DTG data. The m/z 18 curve has four maxima, the first and second maxima at 565 and 639 K correspond to the loss of the coordinating water molecules. The third maximum at 682 K coincides with the m/z 44 and 76 curves, which is attributed to the first decomposition step of the organic anion, and the last maximum at 806 K coincides with the second maximum of m/z 44 and 76.
5. Database survey
A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016) resulted in 196 hits for the (H4BTEC)2– dianion. To the best of our knowledge, there are only two alkaline earth coordination polymers made up from the (H2BTEC)2– dianion, viz. Ba(H2BTEC)(H2O)5]n (Dale et al., 2003) and [Sr2(H2BTEC)2(H2O)2]n (Balegroune et al., 2011). In the Ba compound, the alkaline earth cation displays a monocapped square-antiprismatic coordination environment, and the coordination mode of the (H2BTEC)2– ligand is monodentate to four cations at a time. The Sr compound is based on [SrO8] and [SrO9] polyhedra sharing edges, with the two independent (H2BTEC)2– ligands coordinating to five- and six-metal cations, respectively. Compound (I) with its layered structure has a different set-up and is not comparable with these two previously reported structures.
6. Synthesis and crystallization
6.1. Synthesis
Chemicals were purchased from commercial sources and used without any further purification. Compound (I) was synthesized under hydrothermal conditions. 0.26 g (1 mmol) of SrCl2,6H2O, 0.25 g (1 mmol) of pyromellitic acid (H4BTEC) and 0.04 g (1 mmol) of NaOH were dissolved in water (13 ml). The reaction mixture was stirred at room temperature to and then placed in a Teflon-lined stainless vessel (40 ml) and heated to 433 K for 3 d under autogenous pressure, and afterwards cooled to room temperature. The resulting product of plate-like single crystals and microcrystalline powder was filtered off, washed thoroughly with distilled water, and finally air-dried at room temperature.
6.2. Experimental details
Powder X-ray diffraction patterns were recorded on a Philips X'pert diffractometer with Cu Kα radiation. The samples were gently ground in an agate mortar in order to minimize the All data were collected at room temperature over the 2θ angular range of 4–60° with a step of 0.01° and a counting time of 1.5 s per step. IR spectra were recorded with a JASCO FTIR-6300 spectrometer in the region 4000–600 cm−1. SEM micrographs and X-ray microanalysis (SEM/EDX) were recorded by using a JEOL-6610LV scanning electron microscope operating at 30 kV coupled with an Oxford X-Max microanalysis system (EDX). A Mettler–Toledo TGA/SDTA851e was used for the in a nitrogen dynamic atmosphere (50 ml min−1) at a heating rate of 10 K min−1. In this case, ca 10 mg of a powder sample were thermally treated, and blank runs were performed with the empty crucible.
7. Refinement
Crystal data, data collection and structure . C-bound hydrogen atoms were placed in idealized positions and refined with C—H = 0.93 Å and Uiso = 1.2Ueq(C). The hydrogen atoms of the water molecule and of the carboxylic groups were located in a difference-Fourier map and were refined with O—H = 0.93 and 0.92 Å, respectively, and with Uiso(H) = 1.5Ueq(O). One of the carboxylic OH functions (O4—H4) was found to be disordered over two sets of sites of equal occupancy.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1890785
https://doi.org/10.1107/S2056989020002005/wm5542sup1.cif
contains datablocks SM112, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020002005/wm5542Isup2.hkl
Figure S1. DOI: https://doi.org/10.1107/S2056989020002005/wm5542sup3.tif
Data collection: CrysAlis CCD (Oxford Diffraction, 2015); cell
CrysAlis RED (Oxford Diffraction, 2015); data reduction: CrysAlis RED (Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).[Sr(C10H4O8)(H2O)] | F(000) = 1408 |
Mr = 357.77 | Dx = 2.151 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5087 reflections |
a = 25.8191 (7) Å | θ = 2.9–30.9° |
b = 11.9726 (3) Å | µ = 4.93 mm−1 |
c = 7.1467 (2) Å | T = 295 K |
β = 90.662 (2)° | Prism, colorless |
V = 2209.05 (10) Å3 | 0.23 × 0.14 × 0.10 mm |
Z = 8 |
Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer | 3417 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2700 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.2673 pixels mm-1 | θmax = 31.5°, θmin = 2.9° |
CCD rotation images, thick slices scans | h = −36→37 |
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2015) | k = −17→16 |
Tmin = 0.833, Tmax = 1.000 | l = −9→10 |
16106 measured reflections |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0329P)2 + 3.281P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.007 |
3417 reflections | Δρmax = 0.70 e Å−3 |
199 parameters | Δρmin = −0.41 e Å−3 |
2 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.86646 (10) | 0.8405 (2) | 0.6041 (4) | 0.0220 (5) | |
C2 | 0.86705 (10) | 0.7142 (2) | 0.6075 (3) | 0.0212 (5) | |
C3 | 0.82120 (11) | 0.6600 (2) | 0.6499 (4) | 0.0245 (6) | |
H3 | 0.7921 | 0.703 | 0.6754 | 0.029* | |
C4 | 0.81681 (10) | 0.5436 (2) | 0.6561 (4) | 0.0222 (5) | |
C5 | 0.86102 (10) | 0.4787 (2) | 0.6146 (3) | 0.0206 (5) | |
C6 | 0.90708 (11) | 0.5344 (2) | 0.5760 (4) | 0.0252 (6) | |
H6 | 0.9366 | 0.4923 | 0.5527 | 0.03* | |
C7 | 0.91076 (11) | 0.6508 (2) | 0.5708 (4) | 0.0240 (6) | |
C8 | 0.96109 (11) | 0.7054 (2) | 0.5286 (4) | 0.0310 (6) | |
C9 | 0.86422 (11) | 0.3525 (2) | 0.6049 (4) | 0.0253 (6) | |
C10 | 0.76333 (11) | 0.5051 (2) | 0.7169 (4) | 0.0290 (6) | |
O1 | 0.86950 (8) | 0.89053 (15) | 0.7574 (3) | 0.0306 (5) | |
O2 | 0.86043 (9) | 0.88916 (15) | 0.4518 (3) | 0.0346 (5) | |
O1W | 0.95292 (11) | 0.9470 (2) | 1.1096 (5) | 0.0641 (8) | |
H2W | 0.9779 (14) | 0.908 (4) | 1.077 (7) | 0.096* | |
H1W | 0.959 (2) | 1.012 (2) | 1.076 (7) | 0.096* | |
O3 | 0.96836 (9) | 0.80320 (18) | 0.5342 (5) | 0.0607 (8) | |
O4A | 1.0004 (6) | 0.6356 (8) | 0.533 (7) | 0.049 (6) | 0.50 (7) |
H4A | 1.0275 | 0.6705 | 0.5217 | 0.073* | 0.50 (7) |
O4B | 0.9931 (6) | 0.6371 (9) | 0.438 (6) | 0.044 (4) | 0.50 (7) |
H4B | 1.022 | 0.6653 | 0.4338 | 0.066* | 0.50 (7) |
O5 | 0.90652 (8) | 0.30446 (16) | 0.5932 (3) | 0.0361 (5) | |
O6 | 0.82258 (8) | 0.29547 (16) | 0.6041 (3) | 0.0393 (5) | |
O7 | 0.73445 (9) | 0.57112 (19) | 0.7873 (4) | 0.0531 (7) | |
O8 | 0.74913 (10) | 0.40310 (19) | 0.7001 (5) | 0.0699 (10) | |
H8 | 0.7727 | 0.3666 | 0.6541 | 0.105* | |
Sr | 0.85719 (2) | 0.90596 (2) | 1.10167 (3) | 0.02469 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0257 (14) | 0.0109 (11) | 0.0295 (13) | 0.0010 (9) | 0.0059 (11) | 0.0014 (10) |
C2 | 0.0295 (14) | 0.0118 (11) | 0.0222 (12) | 0.0040 (10) | −0.0010 (11) | 0.0013 (10) |
C3 | 0.0274 (14) | 0.0143 (12) | 0.0318 (14) | 0.0049 (10) | 0.0014 (11) | 0.0000 (11) |
C4 | 0.0276 (14) | 0.0143 (12) | 0.0247 (13) | 0.0012 (10) | 0.0004 (11) | 0.0000 (10) |
C5 | 0.0283 (13) | 0.0089 (10) | 0.0247 (12) | 0.0030 (10) | 0.0017 (10) | −0.0009 (10) |
C6 | 0.0272 (14) | 0.0132 (12) | 0.0352 (15) | 0.0028 (10) | 0.0025 (11) | 0.0009 (11) |
C7 | 0.0288 (14) | 0.0114 (12) | 0.0321 (14) | 0.0007 (10) | 0.0050 (11) | 0.0014 (10) |
C8 | 0.0293 (15) | 0.0159 (13) | 0.0479 (18) | 0.0019 (11) | 0.0065 (13) | 0.0005 (12) |
C9 | 0.0360 (16) | 0.0126 (12) | 0.0276 (13) | 0.0001 (11) | 0.0051 (12) | 0.0004 (11) |
C10 | 0.0270 (14) | 0.0197 (13) | 0.0405 (16) | 0.0008 (11) | 0.0028 (12) | −0.0007 (12) |
O1 | 0.0493 (13) | 0.0143 (9) | 0.0283 (10) | −0.0005 (8) | 0.0061 (9) | −0.0026 (8) |
O2 | 0.0604 (15) | 0.0153 (9) | 0.0281 (10) | 0.0013 (9) | −0.0010 (10) | 0.0045 (8) |
O1W | 0.0398 (15) | 0.0346 (14) | 0.118 (3) | 0.0015 (12) | 0.0062 (16) | −0.0016 (17) |
O3 | 0.0397 (13) | 0.0185 (11) | 0.124 (3) | −0.0074 (10) | 0.0248 (14) | −0.0081 (13) |
O4A | 0.028 (3) | 0.016 (2) | 0.103 (18) | 0.005 (2) | 0.017 (6) | 0.011 (5) |
O4B | 0.030 (4) | 0.024 (3) | 0.079 (12) | 0.004 (2) | 0.017 (5) | 0.004 (4) |
O5 | 0.0336 (11) | 0.0132 (9) | 0.0617 (14) | 0.0025 (8) | 0.0069 (10) | −0.0006 (9) |
O6 | 0.0342 (11) | 0.0135 (9) | 0.0704 (15) | −0.0028 (8) | 0.0131 (10) | −0.0022 (10) |
O7 | 0.0299 (12) | 0.0283 (12) | 0.102 (2) | 0.0011 (10) | 0.0166 (13) | −0.0157 (13) |
O8 | 0.0455 (15) | 0.0218 (12) | 0.143 (3) | −0.0086 (10) | 0.0482 (17) | −0.0161 (14) |
Sr | 0.03497 (15) | 0.01095 (12) | 0.02837 (14) | −0.00125 (10) | 0.01032 (10) | −0.00039 (10) |
C1—O2 | 1.243 (3) | C10—O7 | 1.201 (3) |
C1—O1 | 1.251 (3) | C10—O8 | 1.280 (3) |
C1—C2 | 1.512 (3) | O1—Sr | 2.4915 (19) |
C1—Sri | 3.045 (3) | O1—Sri | 2.6959 (19) |
C2—C3 | 1.386 (4) | O2—Sriii | 2.510 (2) |
C2—C7 | 1.388 (4) | O2—Sri | 2.6785 (19) |
C3—C4 | 1.400 (4) | O1W—Sr | 2.520 (3) |
C3—H3 | 0.93 | O1W—H2W | 0.830 (19) |
C4—C5 | 1.415 (3) | O1W—H1W | 0.826 (19) |
C4—C10 | 1.524 (4) | O4A—H4A | 0.82 |
C5—C6 | 1.394 (4) | O4B—H4B | 0.82 |
C5—C9 | 1.516 (4) | O5—Srii | 2.8238 (19) |
C6—C7 | 1.397 (3) | O6—Srii | 2.572 (2) |
C6—H6 | 0.93 | O7—Sriv | 2.519 (2) |
C7—C8 | 1.488 (4) | O8—H8 | 0.82 |
C8—O3 | 1.187 (3) | Sr—O2v | 2.510 (2) |
C8—O4A | 1.314 (12) | Sr—O7iv | 2.519 (2) |
C8—O4B | 1.337 (12) | Sr—O6vi | 2.572 (2) |
C9—O5 | 1.238 (3) | Sr—O2vii | 2.6785 (19) |
C9—O6 | 1.273 (3) | Sr—O1vii | 2.6959 (19) |
C9—Srii | 3.099 (3) | Sr—O5vi | 2.8239 (19) |
O2—C1—O1 | 123.3 (2) | C1—O2—Sriii | 155.89 (18) |
O2—C1—C2 | 119.0 (2) | C1—O2—Sri | 94.78 (16) |
O1—C1—C2 | 117.7 (2) | Sriii—O2—Sri | 108.93 (7) |
O2—C1—Sri | 61.23 (14) | Sr—O1W—H2W | 131 (4) |
O1—C1—Sri | 62.05 (13) | Sr—O1W—H1W | 112 (4) |
C2—C1—Sri | 176.01 (17) | H2W—O1W—H1W | 107 (5) |
C3—C2—C7 | 118.9 (2) | C8—O4A—H4A | 109.5 |
C3—C2—C1 | 117.6 (2) | C8—O4B—H4B | 109.5 |
C7—C2—C1 | 123.5 (2) | C9—O5—Srii | 90.82 (16) |
C2—C3—C4 | 122.9 (2) | C9—O6—Srii | 102.06 (16) |
C2—C3—H3 | 118.6 | C10—O7—Sriv | 142.5 (2) |
C4—C3—H3 | 118.6 | C10—O8—H8 | 109.5 |
C3—C4—C5 | 118.3 (2) | O1—Sr—O2v | 167.19 (7) |
C3—C4—C10 | 112.6 (2) | O1—Sr—O7iv | 116.75 (9) |
C5—C4—C10 | 129.0 (2) | O2v—Sr—O7iv | 73.47 (9) |
C6—C5—C4 | 118.1 (2) | O1—Sr—O1W | 84.28 (10) |
C6—C5—C9 | 114.9 (2) | O2v—Sr—O1W | 88.39 (10) |
C4—C5—C9 | 127.0 (2) | O7iv—Sr—O1W | 153.66 (10) |
C5—C6—C7 | 122.7 (2) | O1—Sr—O6vi | 89.16 (7) |
C5—C6—H6 | 118.6 | O2v—Sr—O6vi | 85.74 (7) |
C7—C6—H6 | 118.6 | O7iv—Sr—O6vi | 76.84 (7) |
C2—C7—C6 | 119.0 (2) | O1W—Sr—O6vi | 121.57 (8) |
C2—C7—C8 | 120.8 (2) | O1—Sr—O2vii | 70.61 (6) |
C6—C7—C8 | 120.2 (2) | O2v—Sr—O2vii | 118.11 (5) |
O3—C8—O4A | 120.3 (7) | O7iv—Sr—O2vii | 93.44 (8) |
O3—C8—O4B | 121.4 (6) | O1W—Sr—O2vii | 78.18 (9) |
O3—C8—C7 | 124.4 (3) | O6vi—Sr—O2vii | 150.91 (7) |
O4A—C8—C7 | 113.1 (5) | O1—Sr—O1vii | 117.32 (5) |
O4B—C8—C7 | 112.1 (5) | O2v—Sr—O1vii | 70.04 (6) |
O5—C9—O6 | 119.8 (2) | O7iv—Sr—O1vii | 83.01 (7) |
O5—C9—C5 | 121.0 (2) | O1W—Sr—O1vii | 72.76 (8) |
O6—C9—C5 | 119.2 (2) | O6vi—Sr—O1vii | 152.13 (7) |
O5—C9—Srii | 65.65 (14) | O2vii—Sr—O1vii | 48.19 (6) |
O6—C9—Srii | 54.25 (13) | O1—Sr—O5vi | 81.37 (6) |
C5—C9—Srii | 173.12 (18) | O2v—Sr—O5vi | 86.56 (7) |
O7—C10—O8 | 119.3 (3) | O7iv—Sr—O5vi | 121.96 (7) |
O7—C10—C4 | 119.3 (3) | O1W—Sr—O5vi | 74.46 (8) |
O8—C10—C4 | 121.4 (2) | O6vi—Sr—O5vi | 47.19 (6) |
C1—O1—Sr | 153.31 (17) | O2vii—Sr—O5vi | 142.39 (6) |
C1—O1—Sri | 93.76 (15) | O1vii—Sr—O5vi | 139.83 (6) |
Sr—O1—Sri | 108.96 (7) | ||
O2—C1—C2—C3 | −96.5 (3) | C6—C7—C8—O4B | 22 (2) |
O1—C1—C2—C3 | 79.9 (3) | C6—C5—C9—O5 | 10.9 (4) |
O2—C1—C2—C7 | 83.5 (3) | C4—C5—C9—O5 | −169.8 (3) |
O1—C1—C2—C7 | −100.0 (3) | C6—C5—C9—O6 | −167.3 (2) |
C7—C2—C3—C4 | −0.5 (4) | C4—C5—C9—O6 | 12.0 (4) |
C1—C2—C3—C4 | 179.5 (2) | C3—C4—C10—O7 | −14.4 (4) |
C2—C3—C4—C5 | −0.9 (4) | C5—C4—C10—O7 | 162.8 (3) |
C2—C3—C4—C10 | 176.7 (2) | C3—C4—C10—O8 | 167.8 (3) |
C3—C4—C5—C6 | 2.1 (4) | C5—C4—C10—O8 | −15.0 (5) |
C10—C4—C5—C6 | −175.0 (3) | O2—C1—O1—Sr | 149.6 (3) |
C3—C4—C5—C9 | −177.2 (2) | C2—C1—O1—Sr | −26.7 (5) |
C10—C4—C5—C9 | 5.8 (5) | Sri—C1—O1—Sr | 148.8 (4) |
C4—C5—C6—C7 | −2.1 (4) | O2—C1—O1—Sri | 0.8 (3) |
C9—C5—C6—C7 | 177.3 (3) | C2—C1—O1—Sri | −175.5 (2) |
C3—C2—C7—C6 | 0.6 (4) | O1—C1—O2—Sriii | 168.9 (3) |
C1—C2—C7—C6 | −179.5 (3) | C2—C1—O2—Sriii | −14.9 (6) |
C3—C2—C7—C8 | −178.7 (3) | Sri—C1—O2—Sriii | 169.7 (5) |
C1—C2—C7—C8 | 1.3 (4) | O1—C1—O2—Sri | −0.8 (3) |
C5—C6—C7—C2 | 0.7 (4) | C2—C1—O2—Sri | 175.5 (2) |
C5—C6—C7—C8 | −180.0 (3) | O6—C9—O5—Srii | −3.8 (3) |
C2—C7—C8—O3 | 4.7 (5) | C5—C9—O5—Srii | 178.0 (2) |
C6—C7—C8—O3 | −174.6 (3) | O5—C9—O6—Srii | 4.3 (3) |
C2—C7—C8—O4A | 168 (2) | C5—C9—O6—Srii | −177.48 (19) |
C6—C7—C8—O4A | −12 (2) | O8—C10—O7—Sriv | −9.8 (6) |
C2—C7—C8—O4B | −159.0 (19) | C4—C10—O7—Sriv | 172.4 (3) |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) x, −y+1, z−1/2; (iii) x, y, z−1; (iv) −x+3/2, −y+3/2, −z+2; (v) x, y, z+1; (vi) x, −y+1, z+1/2; (vii) x, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O3vii | 0.83 | 2.25 | 3.0666 (3) | 170 |
O1W—H2W···O3viii | 0.83 | 2.04 | 2.864 (4) | 171 |
O4A—H4A···O5ix | 0.82 | 1.92 | 2.68 (2) | 152 |
O4B—H4B···O5ix | 0.82 | 1.89 | 2.696 (16) | 166 |
O8—H8···O6 | 0.82 | 1.59 | 2.400 (3) | 169 |
C6—H6···O4Aix | 0.93 | 2.32 | 3.240 (18) | 169 |
C6—H6···O4Bix | 0.93 | 2.39 | 3.298 (14) | 166 |
Symmetry codes: (vii) x, −y+2, z+1/2; (viii) −x+2, y, −z+3/2; (ix) −x+2, −y+1, −z+1. |
Funding information
We acknowledge the financial support from the DG-RSDT – MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique – Algérie), the Spanish Ministerio de Economía y Competitividad (MAT2016–78155-C2–1-R and FPI grant BES-2011–046948 to MSMA), Gobierno del Principado de Asturias (GRUPIN14–060) and FEDER.
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