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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 80| Part 3| March 2024| Pages 335-338
https://doi.org/10.1107/S205698902400166X

Crystal structure of tetra­kis­(μ-2-hy­dr­oxy-3,5-di­isoprop­yl­benzoato)bis­­[(di­methyl sulfoxide)copper(II)]

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Daniel G. Shlian,a Rachael H. Summers,b Katelyn Martinezb and Rita K. Upmacisb*

aDepartment of Chemistry, Columbia University, New York, NY 10027, USA, and bDepartment of Chemistry & Physical Sciences, Pace University, New York, NY 10038, USA
*Correspondence e-mail: rupmacis@pace.edu

Edited by S. P. Kelley, University of Missouri-Columbia, USA (Received 30 November 2023; accepted 19 February 2024; online 27 February 2024)

Metal complexes of 3,5-diiso­propyl­salicylate are reported to have anti-inflammatory and anti-convulsant activities. The title binuclear copper complex, [Cu2(C13H17O3)4(C2H6OS)2] or [Cu(II)2(3,5-DIPS)4(DMSO)2], contains two five-coordinate copper atoms that are bridged by four 3,5-diiso­propyl­salicylate ligands and capped by two axial dimethyl sulfoxide (DMSO) moieties. Each copper atom is attached to four oxygen atoms in an almost square-planar fashion, with the addition of a DMSO ligand in an apical position leading to a square-pyramidal arrangement. The hy­droxy group of the diiso­propyl­salicylate ligands participates in intra­molecular O—H⋯O hydrogen-bonding inter­actions.

CCDC reference: 2333981

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1. Chemical context

A variety of binuclear CuII complexes bound to carboxyl­ate moieties and donor ligands are known (Doedens, 1976[Doedens, R. J. (1976). Structure and Metal-Metal interactions in Copper(II) Carboxylate Complexes. In Progress in Inorganic Chemistry, Vol. 21, edited by S. J. Lippard, pp. 209-231. New York: John Wiley & Sons, Inc.]). These include, for instance, CuII complexes with di­alkyl­salicylates (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]; Benisvy et al., 2006[Benisvy, L., Mutikainen, I., Quesada, M., Turpeinen, U., Gamez, P. & Reedijk, J. (2006). Chem. Commun. pp. 3723-3725.]; Seguin et al., 2021[Seguin, A. K., Wrighton-Araneda, K., Cortés-Arriagada, D., Cruz, C., Venegas-Yazigi, D. & Paredes-García, V. (2021). J. Mol. Struct. 1224, 129172.]) and non-steroidal anti-inflammatory drugs (NSAIDs) (Dendrinou-Samara et al., 1990[Dendrinou-Samara, C., Kessissoglou, D. P., Manoussakis, G. E., Mentzafos, D. & Terzis, A. (1990). J. Chem. Soc. Dalton Trans. pp. 959-965.]; Kovala-Demertzi et al., 1997[Kovala-Demertzi, D., Theodorou, A., Demertzis, M. A., Raptopoulou, C. P. & Terzis, A. (1997). J. Inorg. Biochem. 65, 151-157.]; Guessous et al., 1998[Guessous, F., Daran, J.-C. B. V., Viossat, B., Morgant, G., Labouze, X., Leroy, A. L., Roch-Arveiller, M. & Dung, N. H. (1998). Met.-Based Drugs, 5, 337-345.]; Greenaway et al., 1999[Greenaway, F. T., Riviere, E., Girerd, J. J., Labouze, X., Morgant, G., Viossat, B., Daran, J. C., Roch Arveiller, M. & Dung, N. H. (1999). J. Inorg. Biochem. 76, 19-27.]; Viossat et al., 2003[Viossat, B., Daran, J. C., Savouret, G., Morgant, G., Greenaway, F. T., Dung, N. H., Pham-Tran, V. A. & Sorenson, J. R. J. (2003). J. Inorg. Biochem. 96, 375-385.], 2005[Viossat, B., Greenaway, F. T., Morgant, G., Daran, J. C., Dung, N. H. & Sorenson, J. R. J. (2005). J. Inorg. Biochem. 99, 355-367.]). With regard to CuII complexes with di­alkyl­salicylates, several complexes containing 3,5-diiso­propyl­salicylate (3,5-DIPS) of the type [Cu(II)2(3,5-DIPS)4(L)2], in which L is a donor mol­ecule, are known and have been characterized by electron paramagnetic resonance (EPR), infrared (IR) and ultraviolet–visible (UV–Vis) spectroscopies (Greenaway et al., 1988[Greenaway, F. T., Joseph Norris, L. & Sorenson, J. R. J. (1988). Inorg. Chim. Acta, 145, 279-284.]). However, compounds featuring dimethyl formamide (DMF) and di­ethyl­ether giving rise to [Cu(II)2(3,5-DIPS)4(DMF)2] and [Cu(II)2(3,5-DIPS)4(OEt2)2], respectively, have been characterized by X-ray diffraction (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]).

In contrast to the binuclear structures of these copper compounds, the structure of the zinc counterpart that is obtained from dimethyl sulfoxide (DMSO) is mononuclear, [Zn(II)(3,5-DIPS)2(DMSO)2], as determined by X-ray crystallography (Morgant et al., 1998[Morgant, G., Viossat, B., Daran, J. C., Roch-Arveiller, M., Giroud, J. P., Nguyen, H. D. & Sorenson, J. R. J. (1998). J. Inorg. Biochem. 70, 137-143.]). Since CuII and ZnII complexes of 3,5-DIPS are of inter­est because they inhibit polymorphonuclear leukocyte oxidative metabolism in vitro and have anti­convulsant activity (Morgant et al., 1998[Morgant, G., Viossat, B., Daran, J. C., Roch-Arveiller, M., Giroud, J. P., Nguyen, H. D. & Sorenson, J. R. J. (1998). J. Inorg. Biochem. 70, 137-143.], 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]), it is pertinent to determine the structure of the corresponding copper complex. Therefore, herein, we describe the X-ray crystallography structure of the binuclear copper complex, [Cu(II)2(3,5-DIPS)4(DMSO)2], which is obtained from a solution of copper(II) 3,5-diiso­propyl­salicylate hydrate in DMSO.

[Scheme 1]

2. Structural commentary

The structure of [Cu(II)2(3,5-DIPS)4(DMSO)2], shown in Fig. 1[link], reveals that the compound is a centrosymmetric binuclear complex containing two copper atoms, with a Cu⋯Cu distance of 2.6170 (7) Å, that are bridged by four 3,5-diiso­propyl­salicylate (DIPS) ligands. The inter­nal symmetry element (inversion center) allows for half of the complex to be represented in the asymmetric unit. As found with other [Cu(II)(3,5-DIPS)] compounds, the OH moiety attached to the aromatic ring is not involved in bonding to the copper centers (Ranford et al., 1993[Ranford, J. D., Sadler, P. J. & Tocher, D. A. (1993). J. Chem. Soc. Dalton Trans. pp. 3393-3399.]; Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]). Each Cu atom forms an almost square-planar geometry with four oxygen atoms from the carboxyl­ate groups of the 3,5-DIPS moieties, with Cu—O distances ranging between 1.958 (2) and 1.972 (2) Å. The O—Cu—O angles range from 88.12 (9) to 90.21 (9)° for cis and 168.77 (7) to 168.80 (8)° for trans positions, indicating that the arrangement is close to an idealized square-planar geometry.

[Figure 1]
Figure 1
Crystal structure of [Cu(II)2(3,5-DIPS)4(DMSO)2]. For clarity, hydrogen atoms on carbon have been omitted. The OH group is disordered over two sites on each aromatic ring, namely C13/C17 and C33/C37, with site occupancy ratios of 0.723 (6):0.277 (6) and 0.859 (5):0.141 (5), respectively; for clarity, only the major component with its hydrogen-bonding inter­actions is illustrated. Displacement ellipsoids are shown at the 30% probability level.

Each Cu atom is also capped by a DMSO ligand in the apical position with a Cu—OSMe2 distance of 2.1226 (19) Å leading to a square-pyramidal arrangement. The O11—Cu—OSMe2, O12—Cu—OSMe2, O31—Cu—OSMe2 and O32—Cu—OSMe2 angles range from 95.41 (8) to 95.79 (7)°, indicating a slight deviation from the 90° angle expected for an idealized square-pyramidal arrangement. In accord with this description, the τ5 geometry index (Addison et al., 1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]) for the [CuO5] moiety is close to zero (0.00005); for reference, a τ5 geometry index of 0.00 corresponds to a square-pyramidal geometry while a value of 1.00 corresponds to an idealized trigonal–bipyramidal geometry (Addison et al., 1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]; Palmer & Parkin, 2014[Palmer, J. H. & Parkin, G. (2014). Dalton Trans. 43, 13874-13882.]).

The OH group is disordered over two sites on each aromatic ring, namely C13/C17 and C33/C37, with site occupancy ratios of 0.723 (6):0.277 (6) and 0.859 (5):0.141 (5), respectively. This type of disorder has previously been observed for other [Cu(II)(3,5-DIPS)] compounds, such as [Cu(II)2(3,5-DIPS)4(DMF)2] and mononuclear [Cu(II)(3,5-DIPS)2(1,10-phenanthroline)] (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]; Ranford et al., 1993[Ranford, J. D., Sadler, P. J. & Tocher, D. A. (1993). J. Chem. Soc. Dalton Trans. pp. 3393-3399.]). For comparison, the OH group disorder for [Cu(II)2(3,5-DIPS)4(DMF)2] occurs in a 64:36 ratio for each 3,5-DIPS ligand (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]), while for the mononuclear Cu structure containing 1,10-phenanthroline, the disorder occurs in a 60:40 ratio (Ranford et al., 1993[Ranford, J. D., Sadler, P. J. & Tocher, D. A. (1993). J. Chem. Soc. Dalton Trans. pp. 3393-3399.]).

3. Supra­molecular features

Fig. 2[link] shows the packing in the unit cell. There are no significant inter­molecular inter­actions. However, the structure displays hydrogen-bonding inter­actions within the mol­ecule, which are those between the aromatic OH groups and an oxygen atom of the carboxyl­ate group within the 3,5-DIPS ligand. The hydrogen bond O—H⋯O distances and angles for O13—H⋯O11, O13A—H⋯O12, O33—H⋯O31 and O33A—H⋯O32 are reported in Table 1[link]. As a result of the OH disorder observed, there are two O—H⋯O distances recorded for each aromatic ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O13—H13B⋯O11 0.75 (3) 1.91 (3) 2.568 (4) 147 (4)
O13A—H13C⋯O12 0.75 (3) 1.90 (4) 2.458 (8) 131 (4)
O33—H33B⋯O31 0.74 (3) 1.90 (3) 2.567 (3) 149 (4)
O33A—H33C⋯O32 0.75 (4) 1.90 (4) 2.511 (14) 138 (5)
[Figure 2]
Figure 2
Unit-cell packing diagram of [Cu(II)2(3,5-DIPS)4(DMSO)2].

The intra­molecular hydrogen-bond distances and angles reported in Table 1[link] are within the typical range of other reported [Cu(II)2(3,5-DIPS)4(L)2] compounds. For instance, the hydrogen-bond O—H⋯O distances and angles reported for [Cu(II)2(3,5-DIPS)4(DMF)2] range from 2.493 (4) to 2.559 (4) Å and 137.0 to 147.6°, respectively (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]).

Similar intra­molecular hydrogen-bond O—H⋯O distances and angles are also reported for related binuclear copper(II) compounds containing 3,5-diiso­butyl­salicylate (3,5-DIBS) that also bear a ring mol­ecule with ortho carb­oxy­lic and alcohol functional groups. For example, [Cu(II)2(3,5-DIBS)4(CH3OH)2] displays intra­molecular hydrogen-bond O—H⋯O distances ranging from 2.575 (6) to 2.565 (6) Å, and O—H⋯O angles between 131 and 146° (Benisvy et al., 2006[Benisvy, L., Mutikainen, I., Quesada, M., Turpeinen, U., Gamez, P. & Reedijk, J. (2006). Chem. Commun. pp. 3723-3725.]).

4. Database survey

Crystal structures of 3,5-diiso­propyl­salicylate copper(II) complexes bound to additional axial donors (L) of the form [Cu(II)2(3,5-DIPS)4(L)2] are known, and include the DMF and di­ethyl­ether ligated compounds (Morgant et al., 2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.]). The title compound, as well as others containing different solvent mol­ecules, such as the di­aqua variant, have been previously characterized as [Cu(II)2(3,5-DIPS)4(L)2] compounds, but crystal structures were not published (Greenaway et al., 1988[Greenaway, F. T., Joseph Norris, L. & Sorenson, J. R. J. (1988). Inorg. Chim. Acta, 145, 279-284.]; Ranford et al., 1993[Ranford, J. D., Sadler, P. J. & Tocher, D. A. (1993). J. Chem. Soc. Dalton Trans. pp. 3393-3399.]).

Other ternary CuII complexes containing solvents bound in the axial positions where 3,5-DIPS is replaced by non-steroidal anti-inflammatory drugs (NSAIDs) of the form [Cu(II)2(NSAID)4(L)2] are also known. These include: [Cu(II)2(naproxen)4(DMSO)2] (Dendrinou-Samara et al., 1990[Dendrinou-Samara, C., Kessissoglou, D. P., Manoussakis, G. E., Mentzafos, D. & Terzis, A. (1990). J. Chem. Soc. Dalton Trans. pp. 959-965.]); [Cu(II)2(diclofenac)4(DMF)2] (Kovala-Demertzi et al., 1997[Kovala-Demertzi, D., Theodorou, A., Demertzis, M. A., Raptopoulou, C. P. & Terzis, A. (1997). J. Inorg. Biochem. 65, 151-157.]); [Cu(II)2(indomethacinate)4(DMF)2] (Guessous et al., 1998[Guessous, F., Daran, J.-C. B. V., Viossat, B., Morgant, G., Labouze, X., Leroy, A. L., Roch-Arveiller, M. & Dung, N. H. (1998). Met.-Based Drugs, 5, 337-345.]); [Cu(II)2(niflumate)4(DMSO)2] (Greenaway et al., 1999[Greenaway, F. T., Riviere, E., Girerd, J. J., Labouze, X., Morgant, G., Viossat, B., Daran, J. C., Roch Arveiller, M. & Dung, N. H. (1999). J. Inorg. Biochem. 76, 19-27.]); [Cu(II)2(aspirinate)4(DMSO)2] (Viossat et al., 2003[Viossat, B., Daran, J. C., Savouret, G., Morgant, G., Greenaway, F. T., Dung, N. H., Pham-Tran, V. A. & Sorenson, J. R. J. (2003). J. Inorg. Biochem. 96, 375-385.]) and [Cu(II)2(niflumate)4(H2O)2·4DMA] (DMA = di­methyl­acetamide; Viossat et al., 2005[Viossat, B., Greenaway, F. T., Morgant, G., Daran, J. C., Dung, N. H. & Sorenson, J. R. J. (2005). J. Inorg. Biochem. 99, 355-367.]). Notably, the title compound has similar structural features to previously characterized NSAID analogs (Table 2[link]).

Table 2
Comparison of selected structural characteristics (Å, °) of ternary CuII complexes with various axial ligands (L = DMSO, DMF, OEt2, H2O)

Compound Cu⋯Cu C—O (basal) C—O (axial) Cu—O—C O—C—O Reference
[Cu(II)2(naproxen)4(DMSO)2] 2.629 (1) 1.995 (4) 1.958 (4) 2.155 (5) 2.123 (5) 123.1 (4) 121.7 (4) 125.7 (5) 126.2 (5) Dendrinou-Samara et al. (1990[Dendrinou-Samara, C., Kessissoglou, D. P., Manoussakis, G. E., Mentzafos, D. & Terzis, A. (1990). J. Chem. Soc. Dalton Trans. pp. 959-965.])
[Cu(II)2(diclofenac)4(DMF)2] 2.6265 (8) 1.981 (2) 1.953 (2) 2.122 (2) 124.7 (2) 121.2 (2) 125.5 (3) Kovala-Demertzi et al. (1997[Kovala-Demertzi, D., Theodorou, A., Demertzis, M. A., Raptopoulou, C. P. & Terzis, A. (1997). J. Inorg. Biochem. 65, 151-157.])
[Cu(II)2(indomethacinate)4(DMF)2] 2.629 (2) 1.956 (7) 1.967 (7) 2.154 (6) 122.3 (6) 123.6 (6) 125.1 (9) 125.9 (8) Guessous et al. (1998[Guessous, F., Daran, J.-C. B. V., Viossat, B., Morgant, G., Labouze, X., Leroy, A. L., Roch-Arveiller, M. & Dung, N. H. (1998). Met.-Based Drugs, 5, 337-345.])
[Cu(II)2(niflumate)4(DMSO)2] 2.6272 (5) 1.952 (2) 1.968 (2) 2.152 (2) 117.2 (2) 130.5 (2) 123.8 (2) 124.1 (2) Greenaway et al. (1999[Greenaway, F. T., Riviere, E., Girerd, J. J., Labouze, X., Morgant, G., Viossat, B., Daran, J. C., Roch Arveiller, M. & Dung, N. H. (1999). J. Inorg. Biochem. 76, 19-27.])
[Cu(II)2(3,5-DIPS)4(DMF)2] 2.6139 (9) 1.950 (2) 1.967 (2) 2.129 (2) 121.9 (2) 125.29 (2) 123.8 (3) 123.9 (3) Morgant et al. (2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.])
[Cu(II)2(3,5-DIPS)4(OEt)2] 2.613 (1) 1.948 (3) 1.957 (3) 2.230 (3) 119.7 (3) 127.0 (3) 124.0 (4) 124.1 (4) Morgant et al. (2000[Morgant, G., Dung, N. H., Daran, J. C., Viossat, B., Labouze, X., Roch-Arveiller, M., Greenaway, F. T., Cordes, W. & Sorenson, J. R. (2000). J. Inorg. Biochem. 81, 11-22.])
[Cu(II)2(aspirinate)4(DMF)2] 2.6154 (4) 1.953 (1) 1.971 (1) 2.154 (1) 119.(1) 125.2 (1) 125.7 (2) 125.8 (2) Viossat et al. (2003[Viossat, B., Daran, J. C., Savouret, G., Morgant, G., Greenaway, F. T., Dung, N. H., Pham-Tran, V. A. & Sorenson, J. R. J. (2003). J. Inorg. Biochem. 96, 375-385.])
[Cu(II)2(niflumate)4(H2O)2]·4DMA 2.6439 (7) 1.952 (2) 1.970 (2) 2.128 (2) 120.9 (2) 127.2 (2) 123.8 (3) 124.6 (3) Viossat et al. (2005[Viossat, B., Greenaway, F. T., Morgant, G., Daran, J. C., Dung, N. H. & Sorenson, J. R. J. (2005). J. Inorg. Biochem. 99, 355-367.])
[Cu(II)2(3,5-DIPS)4(DMSO)2] 2.6170 (7) 1.958 (2) 1.972 (2) 2.1226 (19) 122.04 (19) 125.71 (19) 123.3 (3) 123.3 (3) This work

Related ternary binuclear copper(II) containing 3,5-diiso­butyl­salicylate (3,5-DIBS) compounds that contain solvent ligands are also known. For instance, compounds such as [Cu(II)2(3,5-DIBS)4(CH3OH)2] and [Cu(II)2(3,5-DIBS)4(EtOH)2] have also been characterized (Benisvy et al., 2006[Benisvy, L., Mutikainen, I., Quesada, M., Turpeinen, U., Gamez, P. & Reedijk, J. (2006). Chem. Commun. pp. 3723-3725.]; Seguin et al., 2021[Seguin, A. K., Wrighton-Araneda, K., Cortés-Arriagada, D., Cruz, C., Venegas-Yazigi, D. & Paredes-García, V. (2021). J. Mol. Struct. 1224, 129172.]).

In contrast to these binuclear copper structures, other motifs are observed for different metals. For example, the zinc compound contains a mononuclear zinc center surrounded by two 3,5-DIPS ligands and two DMSO solvent mol­ecules of the form [Zn(II)(3,5-DIPS)2(DMSO)2] (Morgant et al., 1998[Morgant, G., Viossat, B., Daran, J. C., Roch-Arveiller, M., Giroud, J. P., Nguyen, H. D. & Sorenson, J. R. J. (1998). J. Inorg. Biochem. 70, 137-143.]). The ZnII complex of 3,5-DIPS has anti­convulsant activity and inhibits polymorphonuclear leukocyte oxidative bursts in vitro (Morgant et al., 1998[Morgant, G., Viossat, B., Daran, J. C., Roch-Arveiller, M., Giroud, J. P., Nguyen, H. D. & Sorenson, J. R. J. (1998). J. Inorg. Biochem. 70, 137-143.]). The (3,5-DIPS) compounds of Fe and Mn also exhibit anti-oxidant activity (Tavadyan et al., 2004[Tavadyan, L. A., Sedrakyan, G. Z., Minasyan, S. H., Greenaway, F. T. & Sorenson, J. R. J. (2004). Transition Met. Chem. 29, 684-696.]).

5. Synthesis and crystallization

A green block of [Cu(II)2(3,5-DIPS)4(DMSO)2] suitable for X-ray diffraction was obtained by directing a flow of air above a solution of copper(II) 3,5-diiso­propyl­salicylate hydrate (0.07 g, 0.14 mmol) in DMSO (15 mL) over several days at room temperature. In the absence of a flow of air, crystals were also obtained over a period of 11 months.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Disordered groups were treated using fully constrained refinement (site occupancies, coord­inates, thermal parameters) with SHELXTL (Version 2014/7; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]). Hydrogen atoms on carbon were placed in calculated positions (C—H = 0.95–1.00 Å) and included as riding contributions with isotropic displacement parameters Uiso(H) = 1.2Ueq(Csp2) or 1.5Ueq(Csp3). The disorder of the hydroxyl groups was modeled such that the sum of their site occupancies is 1.0.

Table 3
Experimental details

Crystal data
Chemical formula [Cu2(C13H17O3)4(C2H6OS)2]
Mr 1168.40
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 180
a, b, c (Å) 10.2990 (17), 11.734 (2), 12.846 (2)
α, β, γ (°) 87.275 (3), 88.918 (3), 72.096 (2)
V (Å3) 1475.6 (4)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.85
Crystal size (mm) 0.13 × 0.08 × 0.05
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Empirical (using intensity measurements) (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.692, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 19892, 6767, 4879
Rint 0.046
(sin θ/λ)max (Å−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.130, 1.09
No. of reflections 6767
No. of parameters 367
No. of restraints 12
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.61, −0.52
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXTL (Sheldrick 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), and SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Supporting information

CCDC reference: 2333981

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902400166X/ev2003sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902400166X/ev2003Isup2.hkl

checkCIF report


Computing details top

Tetrakis(µ-2-hydroxy-3,5-diisopropylbenzoato)bis[(dimethyl sulfoxide)copper(II)] top
Crystal data top
[Cu2(C13H17O3)4(C2H6OS)2]Z = 1
Mr = 1168.40F(000) = 618
Triclinic, P1Dx = 1.315 Mg m−3
a = 10.2990 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.734 (2) ÅCell parameters from 6990 reflections
c = 12.846 (2) Åθ = 2.3–28.4°
α = 87.275 (3)°µ = 0.85 mm−1
β = 88.918 (3)°T = 180 K
γ = 72.096 (2)°Block, green
V = 1475.6 (4) Å30.13 × 0.08 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer		4879 reflections with I > 2σ(I)
φ and ω scansRint = 0.046
Absorption correction: empirical (using intensity measurements)
(SADABS; Krause et al., 2015)		θmax = 27.5°, θmin = 1.6°
Tmin = 0.692, Tmax = 0.746h = −13→13
19892 measured reflectionsk = −15→15
6767 independent reflectionsl = −16→16
Refinement top
Refinement on F212 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.2858P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
6767 reflectionsΔρmax = 0.61 e Å−3
367 parametersΔρmin = −0.52 e Å−3
Special details top

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. X-ray diffraction data were collected on a Bruker APEXII diffractometer using Mo-Kα radiation. The structures were solved by using direct methods and standard difference map techniques and were refined by full-matrix least-squares procedures on F2 with SHELXTL (Version 2014/7).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cu0.37845 (3)0.49460 (3)0.47832 (2)0.02804 (12)
S0.17501 (7)0.37569 (7)0.38084 (6)0.0393 (2)
O10.18432 (19)0.48200 (18)0.43872 (16)0.0389 (5)
C10.0029 (3)0.4164 (3)0.3402 (3)0.0507 (9)
H1A−0.01160.35120.30160.076*
H1B−0.05730.43100.40140.076*
H1C−0.01780.48940.29510.076*
C20.1689 (4)0.2664 (4)0.4795 (4)0.0768 (14)
H2A0.16270.19420.44720.115*
H2B0.25180.24610.52180.115*
H2C0.08880.29840.52400.115*
O110.6237 (2)0.56862 (18)0.37685 (15)0.0372 (5)
O120.4147 (2)0.56118 (19)0.34213 (15)0.0399 (5)
O130.7689 (3)0.6204 (3)0.2281 (3)0.0555 (12)0.723 (6)
H13B0.750 (4)0.609 (4)0.284 (3)0.050 (10)*0.723 (6)
O13A0.3219 (9)0.6118 (9)0.1651 (6)0.053 (3)0.277 (6)
H13C0.317 (9)0.579 (10)0.215 (4)0.050 (10)*0.277 (6)
C110.5242 (3)0.5824 (2)0.3152 (2)0.0347 (6)
C120.5380 (3)0.6236 (3)0.2058 (2)0.0373 (7)
C130.6608 (3)0.6379 (3)0.1690 (2)0.0427 (7)
H130.73500.62480.21570.051*0.277 (6)
C140.6762 (4)0.6711 (3)0.0650 (3)0.0577 (10)
C150.5636 (5)0.6937 (3)0.0008 (3)0.0617 (10)
H15A0.57170.7184−0.06980.074*
C160.4389 (5)0.6821 (3)0.0352 (3)0.0624 (11)
C170.4288 (4)0.6456 (3)0.1381 (3)0.0516 (9)
H170.34550.63550.16300.062*0.723 (6)
C210.8506 (7)0.6300 (7)−0.0806 (5)0.161 (3)
H21A0.85110.5462−0.07730.242*
H21B0.78390.6758−0.13250.242*
H21C0.94150.6338−0.10050.242*
C220.8122 (5)0.6828 (4)0.0253 (3)0.0814 (14)
H22A0.88430.63700.07580.098*
C230.8107 (5)0.8131 (5)0.0221 (4)0.0937 (16)
H23A0.78580.84590.09100.141*
H23B0.90150.81760.00260.141*
H23C0.74390.8596−0.02940.141*
C240.3386 (9)0.6856 (6)−0.1406 (5)0.208 (5)
H24A0.40080.6039−0.14610.313*
H24B0.25210.6921−0.17460.313*
H24C0.37980.7427−0.17460.313*
C250.3147 (7)0.7109 (6)−0.0361 (4)0.109 (2)
H25A0.26300.6559−0.00950.131*
C260.2219 (6)0.8322 (9)−0.0186 (5)0.188 (4)
H26A0.20980.84360.05640.282*
H26B0.26100.8920−0.05030.282*
H26C0.13330.8415−0.05040.282*
O310.31003 (18)0.65648 (16)0.53077 (16)0.0351 (5)
O320.51797 (18)0.66681 (17)0.56497 (15)0.0338 (4)
O330.0967 (2)0.8246 (2)0.5838 (2)0.0379 (7)0.859 (5)
H33B0.138 (3)0.772 (3)0.555 (3)0.050 (10)*0.859 (5)
O33A0.5527 (15)0.8378 (14)0.6593 (16)0.054 (6)0.141 (5)
H33C0.578 (12)0.789 (14)0.622 (14)0.050 (10)*0.141 (5)
C310.3898 (3)0.7105 (2)0.5652 (2)0.0295 (6)
C320.3274 (3)0.8303 (2)0.6083 (2)0.0286 (6)
C330.1852 (3)0.8809 (2)0.6158 (2)0.0304 (6)
H330.12740.83880.59120.036*0.141 (5)
C340.1278 (3)0.9922 (3)0.6591 (2)0.0313 (6)
C350.2159 (3)1.0517 (2)0.6925 (2)0.0320 (6)
H35A0.17791.12840.72070.038*
C360.3580 (3)1.0038 (2)0.6866 (2)0.0317 (6)
C370.4114 (3)0.8930 (2)0.6445 (2)0.0320 (6)
H370.50760.85850.64010.038*0.859 (5)
C41−0.0798 (3)1.1751 (3)0.6886 (3)0.0557 (9)
H41A−0.17921.19960.69680.084*
H41B−0.03871.19360.75130.084*
H41C−0.05581.21850.62790.084*
C42−0.0267 (3)1.0413 (3)0.6728 (2)0.0398 (7)
H42A−0.06921.02590.60780.048*
C43−0.0731 (3)0.9727 (4)0.7631 (3)0.0625 (11)
H43A−0.03830.88640.75220.094*
H43B−0.03770.98990.82880.094*
H43C−0.17300.99780.76590.094*
C440.5460 (4)1.0940 (3)0.6422 (3)0.0520 (9)
H44A0.49371.13310.58030.078*
H44B0.59541.14590.66850.078*
H44C0.61121.01740.62360.078*
C450.4495 (3)1.0721 (3)0.7256 (3)0.0394 (7)
H45A0.38881.15240.74560.047*
C460.5272 (4)1.0117 (3)0.8226 (3)0.0575 (10)
H46C0.46280.99840.87540.086*
H46D0.59230.93450.80500.086*
H46A0.57651.06300.84990.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.02434 (18)0.02916 (19)0.0328 (2)−0.01076 (14)0.00134 (13)−0.00635 (14)
S0.0299 (4)0.0473 (5)0.0447 (5)−0.0169 (3)−0.0029 (3)−0.0084 (4)
O10.0289 (10)0.0425 (12)0.0486 (13)−0.0146 (9)0.0000 (9)−0.0120 (10)
C10.0322 (16)0.071 (2)0.054 (2)−0.0201 (16)−0.0063 (14)−0.0122 (18)
C20.077 (3)0.070 (3)0.097 (3)−0.047 (2)−0.037 (2)0.035 (2)
O110.0368 (11)0.0413 (12)0.0333 (11)−0.0120 (9)0.0022 (9)−0.0004 (9)
O120.0422 (12)0.0466 (13)0.0357 (11)−0.0206 (10)−0.0020 (9)−0.0023 (9)
O130.0343 (18)0.073 (3)0.047 (2)−0.0008 (16)0.0075 (15)0.0165 (18)
O13A0.055 (6)0.085 (7)0.030 (5)−0.038 (5)−0.010 (4)0.010 (4)
C110.0403 (17)0.0274 (15)0.0356 (16)−0.0086 (13)0.0035 (13)−0.0070 (12)
C120.0453 (17)0.0332 (16)0.0315 (16)−0.0090 (13)0.0031 (13)−0.0056 (12)
C130.0461 (19)0.0387 (17)0.0379 (17)−0.0054 (14)0.0068 (14)−0.0040 (14)
C140.066 (2)0.050 (2)0.048 (2)−0.0044 (18)0.0175 (18)0.0020 (17)
C150.094 (3)0.055 (2)0.0348 (19)−0.020 (2)0.009 (2)−0.0002 (16)
C160.095 (3)0.063 (3)0.0359 (19)−0.034 (2)−0.0154 (19)0.0015 (17)
C170.067 (2)0.058 (2)0.0380 (19)−0.0307 (19)−0.0072 (16)−0.0014 (16)
C210.177 (7)0.184 (7)0.138 (6)−0.074 (6)0.114 (5)−0.078 (5)
C220.069 (3)0.098 (4)0.057 (3)0.000 (2)0.034 (2)0.018 (2)
C230.070 (3)0.135 (5)0.087 (4)−0.048 (3)0.016 (3)−0.005 (3)
C240.321 (12)0.114 (5)0.131 (6)0.036 (6)−0.134 (7)−0.053 (5)
C250.146 (5)0.158 (6)0.048 (3)−0.086 (5)−0.049 (3)0.028 (3)
C260.079 (4)0.298 (11)0.127 (6)0.046 (5)−0.056 (4)−0.092 (6)
O310.0268 (10)0.0308 (11)0.0498 (12)−0.0105 (8)−0.0015 (9)−0.0120 (9)
O320.0240 (10)0.0324 (11)0.0458 (12)−0.0087 (8)0.0040 (8)−0.0119 (9)
O330.0240 (12)0.0396 (15)0.0538 (17)−0.0135 (11)−0.0009 (11)−0.0140 (12)
O33A0.029 (8)0.032 (9)0.107 (16)−0.014 (7)0.004 (8)−0.030 (9)
C310.0265 (14)0.0309 (15)0.0328 (15)−0.0108 (12)0.0008 (11)−0.0041 (12)
C320.0241 (13)0.0292 (14)0.0342 (15)−0.0104 (11)0.0022 (11)−0.0038 (11)
C330.0257 (13)0.0326 (15)0.0335 (15)−0.0098 (12)−0.0004 (11)−0.0012 (12)
C340.0243 (13)0.0356 (16)0.0332 (15)−0.0083 (12)−0.0014 (11)0.0012 (12)
C350.0320 (15)0.0265 (14)0.0338 (15)−0.0030 (12)0.0001 (12)−0.0058 (12)
C360.0257 (14)0.0290 (15)0.0396 (16)−0.0069 (11)−0.0016 (12)−0.0026 (12)
C370.0219 (13)0.0318 (15)0.0411 (17)−0.0062 (11)0.0003 (11)−0.0049 (12)
C410.0314 (17)0.053 (2)0.073 (3)0.0015 (15)0.0025 (16)−0.0090 (18)
C420.0234 (14)0.0443 (18)0.0475 (18)−0.0039 (13)0.0008 (13)−0.0045 (14)
C430.0325 (18)0.071 (3)0.077 (3)−0.0082 (17)0.0171 (17)0.008 (2)
C440.052 (2)0.054 (2)0.062 (2)−0.0333 (17)−0.0034 (17)0.0014 (17)
C450.0319 (15)0.0307 (16)0.058 (2)−0.0109 (13)−0.0031 (14)−0.0125 (14)
C460.057 (2)0.074 (3)0.052 (2)−0.035 (2)−0.0099 (17)−0.0036 (19)
Geometric parameters (Å, º) top
Cu—O121.958 (2)C21—C221.518 (7)
Cu—O311.9595 (19)C22—C231.522 (7)
Cu—O32i1.9672 (19)C24—C251.389 (8)
Cu—O11i1.972 (2)C25—C261.474 (8)
Cu—O12.1226 (19)O31—C311.278 (3)
Cu—Cui2.6170 (7)O32—C311.261 (3)
S—O11.511 (2)O32—Cui1.9672 (19)
S—C11.770 (3)C31—C321.483 (4)
S—C21.774 (4)C32—C371.394 (4)
O11—C111.273 (3)C32—C331.404 (4)
O11—Cui1.972 (2)C33—C341.394 (4)
O12—C111.267 (3)C34—C351.388 (4)
C11—C121.483 (4)C34—C421.527 (4)
C12—C171.387 (4)C35—C361.400 (4)
C12—C131.397 (4)C36—C371.379 (4)
C13—C141.394 (4)C36—C451.517 (4)
C14—C151.386 (6)C41—C421.517 (4)
C14—C221.525 (6)C42—C431.532 (4)
C15—C161.393 (6)C44—C451.514 (4)
C16—C171.382 (5)C45—C461.516 (4)
C16—C251.529 (6)
O12—Cu—O3190.21 (9)C17—C16—C25120.0 (4)
O12—Cu—O32i89.59 (9)C15—C16—C25122.2 (4)
O31—Cu—O32i168.77 (7)C16—C17—C12121.3 (4)
O12—Cu—O11i168.80 (8)C21—C22—C23110.4 (4)
O31—Cu—O11i88.12 (9)C21—C22—C14112.3 (5)
O32i—Cu—O11i89.91 (8)C23—C22—C14111.0 (3)
O12—Cu—O195.71 (8)C24—C25—C26114.0 (5)
O31—Cu—O195.79 (7)C24—C25—C16117.3 (6)
O32i—Cu—O195.41 (8)C26—C25—C16110.6 (4)
O11i—Cu—O195.48 (8)C31—O31—Cu122.11 (17)
O12—Cu—Cui83.21 (6)C31—O32—Cui125.63 (18)
O31—Cu—Cui85.92 (6)O32—C31—O31123.3 (3)
O32i—Cu—Cui82.91 (6)O32—C31—C32118.8 (2)
O11i—Cu—Cui85.63 (6)O31—C31—C32117.9 (2)
O1—Cu—Cui177.99 (6)C37—C32—C33119.1 (3)
O1—S—C1104.47 (14)C37—C32—C31119.4 (2)
O1—S—C2105.02 (18)C33—C32—C31121.4 (2)
C1—S—C298.30 (18)C34—C33—C32120.9 (2)
S—O1—Cu119.72 (11)C35—C34—C33117.8 (2)
C11—O11—Cui122.04 (19)C35—C34—C42122.4 (3)
C11—O12—Cu125.71 (19)C33—C34—C42119.8 (2)
O12—C11—O11123.3 (3)C34—C35—C36122.9 (3)
O12—C11—C12118.3 (3)C37—C36—C35117.8 (2)
O11—C11—C12118.4 (3)C37—C36—C45121.5 (2)
C17—C12—C13119.4 (3)C35—C36—C45120.7 (2)
C17—C12—C11119.8 (3)C36—C37—C32121.5 (2)
C13—C12—C11120.8 (3)C41—C42—C34114.4 (3)
C14—C13—C12121.0 (3)C41—C42—C43110.1 (3)
C15—C14—C13117.4 (3)C34—C42—C43110.0 (2)
C15—C14—C22122.2 (3)C44—C45—C46110.9 (3)
C13—C14—C22120.4 (4)C44—C45—C36112.5 (3)
C14—C15—C16123.1 (3)C46—C45—C36112.0 (3)
C17—C16—C15117.8 (4)
C1—S—O1—Cu−167.93 (15)C15—C16—C25—C26−98.5 (7)
C2—S—O1—Cu89.15 (19)Cui—O32—C31—O31−4.4 (4)
Cu—O12—C11—O11−4.0 (4)Cui—O32—C31—C32175.15 (17)
Cu—O12—C11—C12175.03 (18)Cu—O31—C31—O322.6 (4)
Cui—O11—C11—O122.6 (4)Cu—O31—C31—C32−176.86 (17)
Cui—O11—C11—C12−176.39 (18)O32—C31—C32—C371.9 (4)
O12—C11—C12—C174.4 (4)O31—C31—C32—C37−178.6 (3)
O11—C11—C12—C17−176.6 (3)O32—C31—C32—C33−176.6 (3)
O12—C11—C12—C13−174.1 (3)O31—C31—C32—C333.0 (4)
O11—C11—C12—C135.0 (4)C37—C32—C33—C34−0.2 (4)
C17—C12—C13—C14−1.6 (5)C31—C32—C33—C34178.3 (2)
C11—C12—C13—C14176.9 (3)C32—C33—C34—C351.1 (4)
C12—C13—C14—C152.5 (5)C32—C33—C34—C42−176.0 (3)
C12—C13—C14—C22−178.3 (3)C33—C34—C35—C36−1.4 (4)
C13—C14—C15—C16−1.6 (6)C42—C34—C35—C36175.7 (3)
C22—C14—C15—C16179.2 (4)C34—C35—C36—C370.6 (4)
C14—C15—C16—C17−0.3 (6)C34—C35—C36—C45−179.2 (3)
C14—C15—C16—C25178.2 (4)C35—C36—C37—C320.4 (4)
C15—C16—C17—C121.3 (6)C45—C36—C37—C32−179.8 (3)
C25—C16—C17—C12−177.3 (4)C33—C32—C37—C36−0.6 (4)
C13—C12—C17—C16−0.4 (5)C31—C32—C37—C36−179.1 (3)
C11—C12—C17—C16−178.8 (3)C35—C34—C42—C4120.9 (4)
C15—C14—C22—C21−42.9 (6)C33—C34—C42—C41−162.2 (3)
C13—C14—C22—C21137.9 (5)C35—C34—C42—C43−103.7 (3)
C15—C14—C22—C2381.2 (5)C33—C34—C42—C4373.3 (4)
C13—C14—C22—C23−98.0 (4)C37—C36—C45—C4457.2 (4)
C17—C16—C25—C24−146.9 (6)C35—C36—C45—C44−123.1 (3)
C15—C16—C25—C2434.6 (8)C37—C36—C45—C46−68.6 (4)
C17—C16—C25—C2680.0 (6)C35—C36—C45—C46111.2 (3)
Symmetry code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13B···O110.75 (3)1.91 (3)2.568 (4)147 (4)
O13A—H13C···O120.75 (3)1.90 (4)2.458 (8)131 (4)
O33—H33B···O310.74 (3)1.90 (3)2.567 (3)149 (4)
O33A—H33C···O320.75 (4)1.90 (4)2.511 (14)138 (5)
Comparison of selected structural characteristics (Å, °) of ternary CuII complexes with various axial ligands (L = DMSO, DMF, OEt2, H2O) top
CompoundCu···CuC—O (basal)C—O (axial)Cu—O—CO—C—OReference
[Cu(II)2(naproxen)4(DMSO)2]2.629 (1)1.995 (4) 1.958 (4)2.155 (5) 2.123 (5)123.1 (4) 121.7 (4)125.7 (5) 126.2 (5)Dendrinou-Samara et al. (1990)
[Cu(II)2(diclofenac)4(DMF)2]2.6265 (8)1.981 (2) 1.953 (2)2.122 (2)124.7 (2) 121.2 (2)125.5 (3)(Kovala-Demertzi et al. (1997)
[Cu(II)2(indomethacinate)4(DMF)2]2.629 (2)1.956 (7) 1.967 (7)2.154 (6)122.3 (6) 123.6 (6)125.1 (9) 125.9 (8)Guessous et al. (1998)
[Cu(II)2(niflumate)4(DMSO)2]2.6272 (5)1.952 (2) 1.968 (2)2.152 (2)117.2 (2) 130.5 (2)123.8 (2) 124.1 (2)Greenaway et al. (1999)
[Cu(II)2(3,5-DIPS)4(DMF)2]2.6139 (9)1.950 (2) 1.967 (2)2.129 (2)121.9 (2) 125.29 (2)123.8 (3) 123.9 (3)Morgant et al. (2000)
[Cu(II)2(3,5-DIPS)4(OEt)2]2.613 (1)1.948 (3) 1.957 (3)2.230 (3)119.7 (3) 127.0 (3)124.0 (4) 124.1 (4)Morgant et al. (2000)
[Cu(II)2(aspirinate)4(DMF)2]2.6154 (4)1.953 (1) 1.971 (1)2.154 (1)119.(1) 125.2 (1)125.7 (2) 125.8 (2)Viossat et al. (2003)
[Cu(II)2(niflumate)4(H2O)2]·4DMA2.6439 (7)1.952 (2) 1.970 (2)2.128 (2)120.9 (2) 127.2 (2)123.8 (3) 124.6 (3)Viossat et al. (2005)
[Cu(II)2(3,5-DIPS)4(DMSO)2]2.6170 (7)1.958 (2) 1.972 (2)2.1226 (19)122.04 (19) 125.71 (19)123.3 (3) 123.3 (3)This work
 

Acknowledgements

Gerard Parkin (Columbia University) is thanked for helpful discussions. RKU would like to thank Pace University for Scholarly Research support awards. KM would like to thank the Collegiate Science and Technology Program of Pace University for financial support.

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Volume 80| Part 3| March 2024| Pages 335-338
https://doi.org/10.1107/S205698902400166X
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