research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages 791-794

Crystal structure of a mixed-ligand dinuclear Ba—Zn complex with 2-meth­­oxy­ethanol having tri­phenyl­acetate and chloride bridges

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aFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland, and bFaculty of Chemistry, Wrocław University of Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wrocław, Poland
*Correspondence e-mail: maria.sobocinska@chem.uni.wroc.pl

Edited by G. Smith, Queensland University of Technology, Australia (Received 29 April 2015; accepted 9 June 2015; online 17 June 2015)

The dinuclear barium–zinc complex, μ-chlorido-1:2κ2Cl:Cl-chlorido-2κCl-bis­(2-meth­oxy­ethanol-1κO)bis­(2-meth­oxy­ethanol-1κ2O,O′)bis­(μ-tri­phenyl­acetato-1:2κ2O:O′)bariumzinc, [BaZn(C20H15O2)2Cl2(C3H8O2)4], has been synthesized by the reaction of barium tri­phenyl­acetate, anhydrous zinc chloride and 2-meth­oxy­ethanol in the presence of toluene. The barium and zinc metal cations in the dinuclear complex are linked via one chloride anion and carboxyl­ate O atoms of the tri­phenyl­acetate ligands, giving a Ba⋯Zn separation of 3.9335 (11) Å. The irregular nine-coordinate BaO8Cl coordination centres comprise eight O-atom donors, six of them from 2-meth­oxy­ethanol ligands (four from two bidentate O,O′-chelate inter­actions and two from monodentate inter­actions), two from bridging tri­phenyl­acetate ligands and one from a bridging Cl donor. The distorted tetra­hedral coordination sphere of zinc comprises two O-atom donors from the tri­phenyl­acetate ligands and two Cl donors (one bridging and one terminal). In the crystal, O—H⋯Cl, O—H⋯O and C—H⋯Cl inter­molecular inter­actions form a layered structure, lying parallel to (001).

1. Chemical context

Only a few polynuclear heterometallic compounds containing barium and zinc connected by carboxyl­ate bridges are known (Akine et al., 2006[Akine, S., Taniguchi, T. & Nabeshima, T. (2006). J. Am. Chem. Soc. 128, 15765-15774.], 2009[Akine, S., Morita, Y., Utsuno, F. & Nabeshima, T. (2009). Inorg. Chem. 48, 10670-10678.], 2010[Akine, S., Kagiyama, S. & Nabeshima, T. (2010). Inorg. Chem. 49, 2141-2152.]; Zhang et al., 2012[Zhang, X., Huang, Y.-Y., Cheng, J.-K., Yao, Y.-G., Zhang, J. & Wang, F. (2012). CrystEngComm, 14, 4843-4849.]; Bo et al., 2013[Bo, Q.-B., Wang, H.-Y. & Wang, D.-Q. (2013). New J. Chem. 37, 380-390.]). We have been studying the reactions of the tri­phenyl­acetate anion with metal salts and we have obtained several anhydrous polynuclear MnII tri­phenyl­acetate-containing clusters (Utko et al., 2014[Utko, J., Canaj, A. B., Milios, C. J., Dobrzyńska, D., Pawlus, K., Mikołajczyk, A. & Lis, T. (2014). Inorg. Chim. Acta, 409, 458-464.]). The complexes with some metals (for example: Fe, Ni, Cu, Ru, Rh, Ag) are reported in the literature (Yamanaka et al., 1993[Yamanaka, M., Ohba, S., Tokii, T., Jury, C. F., Steward, O. W. & Kato, M. (1993). Acta Cryst. C49, 1469-1473.]; Cotton et al., 1994[Cotton, F. A., Daniels, L. M., Kibala, P. A., Matusz, M., Roth, W. J., Schwotzer, W., Wenning, W. & Bianxiao, Z. (1994). Inorg. Chim. Acta, 215, 9-15.]; Akhbari & Morsali, 2010[Akhbari, K. & Morsali, A. (2010). CrystEngComm, 12, 3394-3396.]; Barberis et al., 2001[Barberis, M., Lahuerta, P., Perez-Prieto, J. & Sanau, M. (2001). Chem. Commun. pp. 439-440.]; Cadiou et al., 2002[Cadiou, C., Coxal, R. A., Graham, A., Harisson, A., Helliwell, M., Parsons, S. & Winpenny, R. R. P. (2002). Chem. Commun. pp. 1106-1107.]; Do & Lippard, 2011[Do, L. H. & Lippard, S. J. (2011). J. Am. Chem. Soc. 133, 10568-10581.]). However, among polynuclear complexes with tri­phenyl­acetate ligands, dinuclear Ba–Zn representatives have not previously been reported. In the present work, we aimed to create a mixed-ligand compound containing zinc and barium cations, using barium tri­phenyl­acetate as a means of displacing chlorine atoms from zinc chloride. This procedure for removal of chlorine using tri­phenyl­acetate was successfully carried out in a reaction leading to the formation of a mixed-metal complex with a [Ba4Ti2] core (Kosińska-Klähn et al., 2014[Kosińska-Klähn, M., Łukasz, J., Drąg-Jarząbek, A., Utko, J., Petrus, R., Jerzykiewicz, L. B. & Sobota, P. (2014). Inorg. Chem. 53, 1630-1636.]). In the present paper we report the synthesis and structural characterization of a dinuclear Ba–Zn complex, namely μ-chlorido-1:2κ2Cl:Cl-chlorido-2κCl-bis­(2-meth­oxyethanol-1κO)bis­(2-meth­oxy­ethanol-1κ2O,O′)bis­(μ-tri­phenylacetato-1:2κ2O:O′)bariumzinc, (I)[link], and the structure is discussed herein.

[Scheme 1]

2. Structural commentary

In the structure of (I)[link], the asymmetric unit contains one dinuclear complex of [BaZn(Ph3CCOO)2(CH3OCH2CH2OH)4Cl2] (Fig. 1[link]), in which the dinuclear [BaZn]4+ cationic core is bridged by two carboxyl­ate arms of the tri­phenyl­acetate ligands in a κ1:κ1:μ2 coordination mode and by one bridging chlorine atom (μ2-Cl). The Ba⋯Zn distance in the dinuclear complex is 3.9335 (11) Å. Oxygen atoms have the largest contribution to the filling of the coordination sphere of barium [Ba—O bond-length range, 2.6925 (19)– 2.985 (2) Å; Table 1[link]]. Barium is bonded to one bridging chloride atom (μ2-Cl), two O-atoms of two carboxyl­ate groups and also to six O atoms from the 2-meth­oxy­ethanol ligands (four from two bidentate O,O1-chelate inter­actions and two from monodentate inter­actions). 2-Meth­oxy­ethanol is coordinated only to the Ba2+ cation. The coordination mode is achieved in two different ways. Two terminal mol­ecules representing an κ1:κ1 mode form two five-membered rings completed by the barium atom. Two other mol­ecules of 2-meth­oxy­ethanol coordinate to Ba only through the hydroxyl O atoms.

Table 1
Selected bond lengths (Å)

Ba—O3 2.6925 (19) Ba—O2G 2.985 (2)
Ba—O1 2.7073 (19) Ba—Cl1 3.1118 (11)
Ba—O1J 2.7572 (19) Zn—O2 1.9682 (17)
Ba—O1H 2.783 (2) Zn—O4 1.9683 (18)
Ba—O2J 2.7908 (19) Zn—Cl1 2.2595 (10)
Ba—O1G 2.799 (2) Zn—Cl2 2.2653 (9)
Ba—O1I 2.810 (2)    
[Figure 1]
Figure 1
The mol­ecular structure of the title complex, with displacement ellipsoids drawn at the 50% probability level. Dashed lines represent intra-complex hydrogen bonds. C-bonded H atoms have been omitted for clarity.

Zinc is four-coordinated with a distorted tetra­hedral ZnO2Cl2 stereochemistry (Table 1[link]), with Zn—Cl1 (bridging) = 2.2595 (10) Å and Zn—Cl2 (monodentate) = 2.2653 (9) Å and Zn—O (both from the bridging tri­phenyl­acetate groups = 1.96817 (2) and 1.9683 (18) Å). A comparison with other structurally characterized mixed-metallic zinc–barium complexes reveals that the Zn–Cl–Ba linkage has been observed for the first time in the present compound. There are only a few compounds containing both of these metals and only one is a dimeric structure, with a distance between the atoms of 3.629 (2) Å, significantly shorter than in the title complex [3.9335 (11) Å], but zinc and barium are connected only via bridging oxygen atoms (μ2-O) from organic ligands (Van Veggel et al., 1989[Van Veggel, F. C. J. M., Harkema, S., Bos, M., Verboom, W., Van Staveren, C. J., Gerritsma, G. J. & Reinhoudt, D. N. (1989). Inorg. Chem. 28, 1133-1148.]). Also, in other structures without carboxyl­ate bridges, the Zn⋯Ba distances are often much shorter than in the title complex with values in the range 3.4325 (5) to 4.850 (3) Å (Westerhausen et al., 2001[Westerhausen, M., Gückel, C., Habereder, T., Vogt, M., Warchhold, M. & Nöth, H. (2001). Organometallics, 20, 893-899.], 2006[Westerhausen, M., Sapelza, G. & Mayer, P. (2006). Inorg. Chem. Commun. 9, 949-951.]; Baggio et al., 2004[Baggio, R., Stoilova, D., Polla, G., Leyva, G. & Garland, M. T. (2004). J. Mol. Struct. 697, 173-180.]; John et al., 2008[John, Ł., Utko, J., Szafert, S., Jerzykiewicz, L. B., Kepiński, L. & Sobota, P. (2008). Chem. Mater. 20, 4231-4239.]). In those cases where the oxygen atom (μ2-O) and also carboxyl­ates connect zinc and barium, the Zn⋯Ba distance is not longer than 3.638 (1) Å (Akine et al., 2006[Akine, S., Taniguchi, T. & Nabeshima, T. (2006). J. Am. Chem. Soc. 128, 15765-15774.], 2009[Akine, S., Morita, Y., Utsuno, F. & Nabeshima, T. (2009). Inorg. Chem. 48, 10670-10678.], 2010[Akine, S., Kagiyama, S. & Nabeshima, T. (2010). Inorg. Chem. 49, 2141-2152.]). In a polymeric structure where zinc and barium cations are bridged via two carboxyl­ate arms and also via one mol­ecule of water, the distance between them is 4.0208 (5) Å (Zhang et al., 2012[Zhang, X., Huang, Y.-Y., Cheng, J.-K., Yao, Y.-G., Zhang, J. & Wang, F. (2012). CrystEngComm, 14, 4843-4849.]).

3. Supra­molecular features

In the crystal, there are intra­molecular O—H⋯O hydrogen bonds (Table 2[link]). One is formed between a hydroxyl group O1I and an O-atom acceptor from the ether atom (O2H) of a 2-meth­oxy­ethanol ligand, the second is formed between a hydroxyl group O1H and an O-atom acceptor from a carboxyl group (O3) of a Ph3CCOO ligand (Fig. 1[link]). The presence of electronegative atoms (oxygen and chlorine) also leads to the occurrence of inter­molecular hydrogen bonds in the crystal structure. The neighbouring dinuclear mol­ecules inter­act through O—H⋯O, O—H⋯Cl and C—H⋯Cl hydrogen bonds. The first one occurs between the hydroxyl group O1G and an ether O-atom acceptor O2Ii, the second occurs between the hydroxyl group O1J and the terminal chlorine atom Cl2iii. In the third inter­action, the H-donor atom is from a 2-meth­oxy­ethanol carbon (C2I), with the bridging chlorine atom (Cl1I)ii acting as the H-atom acceptor (for symmetry codes, see Table 2[link]). A two-dimensional network structure is generated (Fig. 2[link]), lying parallel to (001).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1G—H1G⋯O2Ii 0.84 1.91 2.728 (3) 163
O1I—H1I⋯O2H 0.84 1.99 2.817 (3) 170
C2I—H2I2⋯Cl1ii 0.99 2.81 3.660 (3) 144
O1J—H1J⋯Cl2iii 0.84 2.17 3.012 (2) 174
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) x, y+1, z.
[Figure 2]
Figure 2
Part of the crystal structure of the complex. Dashed lines represent intra- and inter­molecular hydrogen bonds. C-bonded H atoms not involved in hydrogen bonding have been omitted for clarity. For symmetry codes, see Table 2[link].

4. Synthesis and crystallization

For the preparation of Ba(Ph3CCOO)2, a mixture of metallic barium (0.521 g, 3.8 mmol), tri­phenyl­acetic acid (2.209 g, 7.66 mmol), C6H5CH3 (50 ml) and THF (10 ml) was stirred at 363–373 K for 24 h until all the metal had reacted. The solution, which included a white precipitate, was concentrated to about 20 ml and then hexane (50 ml) was added while stirring, which led to further precipitation. The product was filtered on a Schlenk flask (yield: 2.520 g, 93.26%). Elemental analysis (%) calculated for Ba(Ph3CCOO)2: C 67.48, H 5.38, Ba 19.29; found: C 67.56, H 5.51, Ba 19.44. Solid ZnCl2 (0.273 g, 2.0 mmol) and Ba(Ph3CCOO)2 (1.426 g, 2.0 mmol) were then added to a solution of CH3OCH2CH2OH (30 ml) and C6H5CH3 (15 ml) and the resulting mixture was stirred under a nitro­gen atmosphere for 24 h. The solution was filtered and then concentrated to about 20 ml. Afterwards 20 ml of hexane was funneled into the reaction solution, leading to the creation of two layers and the mixture was left to crystallize at room temperature. After one week, colorless crystals suitable for the X-ray experiment were obtained (1.289 g, yield: 55.83%). Knowledge of the mol­ecular structure of the final product enables representation of the chemical equation for the reaction as: ZnCl2 + Ba((C6H5)3CCOO)2 + 4 (CH3OCH2CH2OH) → [BaZnCl2[(C6H5)3CCOO]2(CH3OCH2CH2OH)4]. Elemental analysis: (%) calculated for the complex: C 54.14, H 5.38, Cl 6.3, Zn 5.67, Ba 11.91; found: C 52.94, H 5.67, Zn 5.48, Ba 11.24.

5. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. All C-bonded H atoms were positioned geometrically and treated as riding atoms: methyl H atoms were constrained to an ideal geometry, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C); the remaining H atoms were afixed to C atoms, with Csp2—H = 0.95 Å and Csp3—H = 0.99 Å, and with Uiso(H) = 1.2Ueq(C). The locations of H atoms of the hydroxyl groups were determined from a difference-Fourier map and finally constrained to ride on their parent atoms, with O—H = 0.84 Å and Uiso(H) = 1.5Ueq(O).

Table 3
Experimental details

Crystal data
Chemical formula [BaZn(C20H15O2)2Cl2(C3H8O2)4]
Mr 1152.62
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 9.706 (3), 10.643 (3), 25.073 (6)
α, β, γ (°) 89.62 (3), 89.26 (3), 82.73 (3)
V3) 2569.0 (12)
Z 2
Radiation type Mo Kα
μ (mm−1) 1.39
Crystal size (mm) 0.31 × 0.23 × 0.21
 
Data collection
Diffractometer Oxford Diffraction KM-4-CCD
Absorption correction Analytical [CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])]
Tmin, Tmax 0.687, 0.780
No. of measured, independent and observed [I > 2σ(I)] reflections 24098, 12296, 10742
Rint 0.025
(sin θ/λ)max−1) 0.705
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.100, 1.14
No. of reflections 12296
No. of parameters 617
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.89, −0.57
Computer programs: CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Yarnton, England.]), SHELXS97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Supporting information


Chemical context top

\ Only a few polynuclear heterometallic compounds containing barium and zinc connected by carboxyl­ate bridges are known (Akine et al., 2006, 2009, 2010; Zhang et al., 2012; Bo et al., 2013). We have been studying the reactions of the tri­phenyl­acetate anion with metal salts and we have obtained several anhydrous polynuclear MnII tri­phenyl­acetate-containing clusters (Utko et al., 2014). The complexes with some metals (for example: Fe, Ni, Cu, Ru, Rh, Ag) are reported in the literature (Yamanaka et al., 1993; Cotton et al., 1994; Akhbari & Morsali, 2010; Barberis et al., 2001; Cadiou et al., 2002; Do & Lippard, 2011). However, among polynuclear complexes with tri­phenyl­acetate ligands, Ba–Zn clusters have not previously been reported. In the present work, we aimed to create a mixed-ligand compound containing zinc and barium metals, using barium tri­phenyl­acetate as a means of displacing chlorine atoms from zinc chloride. This procedure for removal of chlorine using tri­phenyl­acetate was successfully carried out in a reaction leading to the formation of a mixed-metal complex with a [Ba4Ti2] core (Kosińska-Klähn et al., 2014). In the present paper we report the synthesis and structural characterization of a dinuclear Ba–Zn complex, namely µ-chlorido-1:2κ2Cl:Cl-chlorido-2κCl-bis­(2-\ meth­oxy­ethanol-1κO)bis­(2-meth­oxy­ethanol-1κ2O,O')\ bis­(µ-tri­phenyl­acetato-1:2κ2O:O')bariumzinc, (I), and the structure is discussed herein.

Structural commentary top

In the structure of (I), the asymmetric unit contains one dinuclear complex of [BaZn(Ph3CCOO)2(CH3OCH2CH2OH)4Cl2] (Fig. 1), in which the dinuclear [BaZn]4+ cationic core is bridged by two carboxyl­ate arms of the tri­phenyl­acetate ligands in a η1:η12 coordination mode and by one bridging chlorine atom (µ2-Cl). To the best of our knowledge, the (µ2-Cl) bridge between zinc and barium has been found for the first time in the structure of the title compound. The Ba···Zn distance in this dimer is 3.9335 (11) Å. Oxygen atoms have the largest contribution to the filling of the coordination sphere of barium [Ba—O bond-length range, 2.6925 (19)– 2.985 (2) Å; Table 1]. Barium is bonded to one bridging chloride atom (µ2-Cl), two O-atoms of two carboxyl­ate groups and also to six O atoms from the 2-meth­oxy­ethanol ligands (four from two bidentate O,O1 chelate inter­actions and two from monodentate inter­actions). 2-Meth­oxy­ethanol is coordinated only to the Ba atom. The coordination mode is achieved in two different ways. Two terminal molecules representing an η1:η1 mode form two five-membered rings completed by the barium atom. Two other molecules of 2-meth­oxy­ethanol coordinate to Ba only through the hydroxyl O atoms.

Zinc is four-coordinated with a distorted tetra­hedral ZnO2Cl2 stereochemistry (Table 1), with Zn—Cl1 (bridging) = 2.2595 (10) Å and Zn—Cl2 (monodentate) = 2.2653 (9) Å and Zn—O (both from the bridging tri­phenyl­acetate groups = 1.96817 (2) and 1.9683 (18) Å). A comparison with other structurally characterized mixed-metallic zinc–barium complexes reveals that the Zn–Cl–Ba linkage has been observed for the first time in the present compound. There are only a few compounds containing both of these metals and only one is a dinuclear structure, with a distance between the atoms of 3.629 (2) Å, significantly shorter than in the title complex [3.9335 (11) Å], but zinc and barium are connected only via bridging oxygen atoms (µ2-O) from organic ligands (Van Veggel et al., 1989). Also, in other structures without carboxyl­ate bridges, the Zn···Ba distances are often much shorter than in the title complex with values in the range 3.4325 (5) to 4.850 (3) Å (Westerhausen et al., 2001, 2006; Baggio et al., 2004; Łukasz et al., 2008). In those cases where the oxygen atom (µ2-O) and also carboxyl­ates connect zinc and barium, the Zn···Ba distance is not longer than 3.638 (1) Å (Akine et al., 2006, 2009, 2010). In a polymeric structure where zinc and barium atoms are bridged via two carboxyl­ate arms and also via one molecule of water, the distance between them is 4.0208 (5) Å (Zhang et al., 2012).

Supra­molecular features top

In the crystal, there are intra­molecular O—H···O hydrogen bonds (Table 2). One is formed between a hydroxyl group O1I and an O-atom acceptor from the ether group (O2H) of a 2-meth­oxy­ethanol ligand, the second is formed between a hydroxyl group O1H and an O-atom acceptor from a carboxyl group (O3) of a Ph3CCOO- ligand (Fig. 2). The presence of electronegative atoms (oxygen and chlorine) also leads to the occurrence of inter­molecular hydrogen bonds in the crystal structure. The neighbouring dinuclear molecules inter­act through O—H···O, O—H···Cl and C—H···Cl hydrogen bonds. The first one occurs between the hydroxyl group O1G and an ether O-atom acceptor O2Ii, the second occurs between the hydroxyl group O1J and the terminal chlorine atom Cl2iii. In the third inter­action, the H-donor atom is from a 2-meth­oxy­ethanol carbon (C2I), with the bridging chlorine atom (Cl1I)ii acting as the H-atom acceptor (for symmetry codes, see Table 2). A two-dimensional network structure is generated (Fig. 3), lying parallel to (001).

Synthesis and crystallization top

For the preparation of Ba(Ph3CCOO)2, a mixture of metallic barium (0.521 g, 3.8 mmol), tri­phenyl­acetic acid (2.209 g, 7.66 mmol), C6H5CH3 (50 ml) and THF (10 ml) was stirred at 363– 373 K for 24 hours until all the metal had reacted. The solution, which included a white precipitate, was concentrated to about 20 ml and then hexane (50 ml) was added while stirring, which led to further precipitation. The product was filtered on a Schlenk flask (yield: 2.520 g, 93.26%). Elemental analysis (%) calculated for Ba(Ph3CCOO)2: C 67.48, H 5.38, Ba 19.29; found: C 67.56, H 5.51, Ba 19.44. Solid ZnCl2 (0.273 g, 2.0 mmol) and Ba(Ph3CCOO)2 (1.426 g, 2.0 mmol) were then added to a solution of CH3OCH2CH2OH (30 ml) and C6H5CH3 (15 ml) and the resulting mixture was stirred under a nitro­gen atmosphere for 24 hours. The solution was filtered and then concentrated to about 20 ml. Afterwards 20 ml of hexane was funneled into the reaction solution, leading to the creation of two layers and the mixture was left to crystallize at room temperature. After one week, colorless crystals suitable for the X-ray experiment were obtained (1.289 g, yield: 55.83%). Knowledge of the molecular structure of the final product enables representation of the chemical equation for the reaction as: ZnCl2 + Ba((C6H5)3CCOO)2 + 4 (CH3OCH2CH2OH) [BaZnCl2((C6H5)3CCOO)2(CH3OCH2CH2OH)4]. Elemental analysis: (%) calculated for the complex: C 54.14, H 5.38, Cl 6.3, Zn 5.67, Ba 11.91; found: C 52.94, H 5.67, Zn 5.48, Ba 11.24.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 3. All C-bonded H atoms were positioned geometrically and treated as riding atoms: methyl H atoms were constrained to an ideal geometry, with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C); the remaining H atoms were afixed to C atoms, with Csp2—H = 0.95 Å and Csp3—H = 0.99 Å, and with Uiso(H) = 1.2Ueq(C). The locations of H atoms of the hydroxyl groups were determined from a difference-Fourier map and finally constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(O).

Related literature top

For related literature, see: Akhbari & Morsali (2010); Akine et al. (2006, 2009, 2010); Baggio et al. (2004); Barberis et al. (2001); Bo et al. (2013); Cadiou et al. (2002); Cotton et al. (1994); Do & Lippard (2011); Łukasz et al. (2008); Kosińska-Klähn, Łukasz, Drąg-Jarząbek, Utko, Petrus, Jerzykiewicz & Sobota (2014); Utko et al. (2014); Veggel et al. (1989); Westerhausen et al. (2001, 2006); Yamanaka et al. (1993); Zhang et al. (2012).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 50% probability level. Dashed lines represent intra-complex hydrogen bonds. C-bonded H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Part of the crystal structure of the complex. Dashed lines represent intra- and intermolecular hydrogen bonds. C-bonded H atoms not involved in hydrogen bonding have been omitted for clarity. For symmetry codes, see Table 2.
µ-Chlorido-1:2κ2Cl:Cl-chlorido-2κCl-bis(2-methoxyethanol-1κO)bis(2-methoxyethanol-1κ2O,O')bis(µ-triphenylacetato-1:2κ2O:O')bariumzinc top
Crystal data top
[BaZn(C20H15O2)2Cl2(C3H8O2)4]Z = 2
Mr = 1152.62F(000) = 1180
Triclinic, P1Dx = 1.490 Mg m3
a = 9.706 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.643 (3) ÅCell parameters from 17769 reflections
c = 25.073 (6) Åθ = 2–31°
α = 89.62 (3)°µ = 1.39 mm1
β = 89.26 (3)°T = 100 K
γ = 82.73 (3)°Block, colorless
V = 2569.0 (12) Å30.31 × 0.23 × 0.21 mm
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer
10742 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
ω scansθmax = 30.1°, θmin = 2.8°
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
h = 1212
Tmin = 0.687, Tmax = 0.780k = 1313
24098 measured reflectionsl = 3335
12296 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.064P)2]
where P = (Fo2 + 2Fc2)/3
12296 reflections(Δ/σ)max = 0.001
617 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.57 e Å3
Crystal data top
[BaZn(C20H15O2)2Cl2(C3H8O2)4]γ = 82.73 (3)°
Mr = 1152.62V = 2569.0 (12) Å3
Triclinic, P1Z = 2
a = 9.706 (3) ÅMo Kα radiation
b = 10.643 (3) ŵ = 1.39 mm1
c = 25.073 (6) ÅT = 100 K
α = 89.62 (3)°0.31 × 0.23 × 0.21 mm
β = 89.26 (3)°
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer
12296 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
10742 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.780Rint = 0.025
24098 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.14Δρmax = 0.89 e Å3
12296 reflectionsΔρmin = 0.57 e Å3
617 parameters
Special details top

Experimental. The O-bonded H atoms were found from a difference-Fourier map. These H atoms were included in the refinement with constraint:;finally with instruction Afix 3.

Absorption correction: CrysAlis RED (Oxford Diffraction, 2010), employing an analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid (Clark & Reid, 1995).

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
xyzUiso*/Ueq
Ba0.13461 (2)0.39066 (2)0.25149 (2)0.01587 (5)
Zn0.09859 (3)0.02666 (2)0.25185 (2)0.01406 (7)
Cl10.07279 (6)0.19070 (6)0.25860 (3)0.02295 (13)
Cl20.00737 (6)0.14768 (6)0.23751 (2)0.02093 (12)
O10.24715 (19)0.19812 (16)0.31457 (7)0.0202 (4)
O20.20140 (18)0.00059 (16)0.31895 (6)0.0178 (3)
C10.2527 (2)0.0946 (2)0.33730 (9)0.0147 (4)
C20.3316 (2)0.0704 (2)0.39131 (9)0.0131 (4)
C1A0.3078 (2)0.1863 (2)0.42871 (9)0.0141 (4)
C2A0.3301 (3)0.3070 (2)0.41065 (9)0.0196 (5)
H2A0.35400.31900.37430.024*
C3A0.3179 (3)0.4090 (2)0.44516 (10)0.0238 (5)
H3A0.33400.49000.43210.029*
C4A0.2824 (3)0.3948 (2)0.49867 (10)0.0247 (5)
H4A0.27290.46540.52200.030*
C5A0.2613 (3)0.2763 (2)0.51715 (10)0.0222 (5)
H5A0.23720.26480.55350.027*
C6A0.2752 (3)0.1736 (2)0.48271 (9)0.0180 (5)
H6A0.26210.09230.49630.022*
C1B0.2833 (2)0.0447 (2)0.41952 (9)0.0148 (4)
C2B0.3746 (3)0.1460 (2)0.43841 (9)0.0175 (5)
H2B0.47120.14880.43110.021*
C3B0.3268 (3)0.2436 (2)0.46791 (10)0.0217 (5)
H3B0.39070.31200.48050.026*
C4B0.1867 (3)0.2410 (2)0.47891 (10)0.0233 (5)
H4B0.15430.30710.49930.028*
C5B0.0933 (3)0.1414 (2)0.46006 (10)0.0208 (5)
H5B0.00330.13930.46730.025*
C6B0.1418 (3)0.0450 (2)0.43054 (9)0.0177 (5)
H6B0.07730.02240.41750.021*
C1C0.4882 (2)0.0448 (2)0.37655 (9)0.0144 (4)
C2C0.5884 (3)0.0737 (2)0.41205 (9)0.0187 (5)
H2C0.55990.11500.44460.022*
C3C0.7289 (3)0.0433 (2)0.40100 (10)0.0216 (5)
H3C0.79550.06340.42590.026*
C4C0.7723 (3)0.0164 (3)0.35348 (10)0.0233 (5)
H4C0.86840.03800.34580.028*
C5C0.6735 (3)0.0441 (3)0.31737 (10)0.0256 (6)
H5C0.70230.08440.28470.031*
C6C0.5329 (3)0.0136 (2)0.32859 (10)0.0203 (5)
H6C0.46640.03270.30340.024*
O30.2094 (2)0.22740 (16)0.17158 (7)0.0244 (4)
O40.22946 (18)0.02259 (16)0.19108 (6)0.0195 (4)
C30.2431 (3)0.1152 (2)0.16032 (9)0.0167 (5)
C40.3131 (2)0.0801 (2)0.10490 (9)0.0164 (4)
C1D0.3201 (3)0.2003 (2)0.07098 (9)0.0189 (5)
C2D0.4423 (3)0.2304 (3)0.04765 (10)0.0245 (5)
H2D0.52750.17940.05510.029*
C3D0.4417 (4)0.3342 (3)0.01355 (11)0.0335 (7)
H3D0.52640.35240.00240.040*
C4D0.3199 (4)0.4111 (3)0.00251 (12)0.0355 (7)
H4D0.31980.48170.02080.043*
C5D0.1979 (4)0.3830 (3)0.02615 (12)0.0356 (7)
H5D0.11330.43560.01940.043*
C6D0.1978 (3)0.2785 (3)0.05973 (11)0.0253 (5)
H6D0.11280.26010.07530.030*
C1E0.4604 (2)0.0178 (2)0.11792 (9)0.0175 (5)
C2E0.5232 (3)0.0894 (2)0.09188 (9)0.0201 (5)
H2E0.47250.12970.06630.024*
C3E0.6595 (3)0.1387 (3)0.10280 (10)0.0248 (5)
H3E0.70100.21200.08450.030*
C4E0.7351 (3)0.0822 (3)0.13997 (11)0.0281 (6)
H4E0.82850.11590.14700.034*
C5E0.6736 (3)0.0245 (3)0.16711 (11)0.0283 (6)
H5E0.72440.06340.19310.034*
C6E0.5379 (3)0.0737 (3)0.15608 (10)0.0248 (5)
H6E0.49640.14660.17470.030*
C1F0.2325 (2)0.0103 (2)0.07292 (9)0.0167 (5)
C2F0.2503 (3)0.0153 (3)0.01745 (10)0.0249 (5)
H2F0.30670.04020.00050.030*
C3F0.1875 (3)0.0990 (3)0.01334 (10)0.0277 (6)
H3F0.20150.10000.05090.033*
C4F0.1055 (3)0.1806 (3)0.00986 (11)0.0296 (6)
H4F0.06460.23980.01100.036*
C5F0.0841 (3)0.1744 (3)0.06440 (12)0.0351 (7)
H5F0.02530.22850.08090.042*
C6F0.1463 (3)0.0909 (3)0.09569 (11)0.0279 (6)
H6F0.12980.08900.13310.034*
O1G0.12372 (19)0.54119 (18)0.25180 (8)0.0257 (4)
H1G0.17900.53480.27740.039*
C1G0.1947 (3)0.5900 (3)0.20479 (11)0.0276 (6)
H1G10.22280.68230.20810.033*
H1G20.27920.54840.19960.033*
C2G0.0963 (3)0.5630 (3)0.15848 (12)0.0299 (6)
H2G10.14540.58960.12510.036*
H2G20.01860.61420.16210.036*
O2G0.0411 (2)0.43219 (19)0.15458 (8)0.0293 (4)
C3G0.1399 (4)0.3533 (3)0.13765 (13)0.0390 (7)
H3G10.21840.36030.16290.058*
H3G20.09620.26520.13630.058*
H3G30.17320.38020.10210.058*
O1H0.2695 (2)0.4717 (2)0.16137 (8)0.0352 (5)
H1H0.27430.40480.14350.053*
C1H0.3414 (4)0.5586 (3)0.13328 (13)0.0425 (8)
H1H10.29290.58390.09960.051*
H1H20.43650.51880.12430.051*
C2H0.3480 (4)0.6720 (3)0.16707 (13)0.0366 (7)
H2H10.37830.74150.14520.044*
H2H20.25490.70130.18230.044*
O2H0.4452 (2)0.63873 (17)0.20935 (8)0.0255 (4)
C3H0.4607 (3)0.7504 (3)0.23808 (13)0.0328 (6)
H3H10.48420.81610.21320.049*
H3H20.53520.73200.26410.049*
H3H30.37350.78010.25680.049*
O1I0.40709 (19)0.43145 (18)0.27599 (8)0.0280 (4)
H1I0.42670.49430.25830.042*
C1I0.5361 (3)0.3481 (3)0.27592 (12)0.0294 (6)
H1I10.58770.36000.24230.035*
H1I20.51620.25910.27730.035*
C2I0.6245 (3)0.3723 (3)0.32224 (12)0.0327 (6)
H2I10.57210.36260.35580.039*
H2I20.70830.30880.32240.039*
O2I0.6661 (2)0.4974 (2)0.31999 (8)0.0334 (5)
C3I0.5953 (4)0.5833 (4)0.35674 (13)0.0435 (8)
H3I10.49620.59680.34820.065*
H3I20.63340.66420.35460.065*
H3I30.60700.54850.39290.065*
O1J0.1679 (2)0.62932 (17)0.28717 (7)0.0235 (4)
H1J0.11350.68890.27400.035*
C1J0.1615 (3)0.6484 (3)0.34373 (11)0.0279 (6)
H1J10.15300.74030.35130.033*
H1J20.24870.60790.35990.033*
C2J0.0403 (3)0.5938 (3)0.36864 (11)0.0273 (6)
H2J10.04140.60340.40790.033*
H2J20.04790.63910.35520.033*
O2J0.0511 (2)0.46206 (17)0.35502 (7)0.0238 (4)
C3J0.0263 (3)0.3905 (3)0.38985 (11)0.0300 (6)
H3J10.01410.38770.42550.045*
H3J20.02340.30410.37620.045*
H3J30.12290.43040.39180.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ba0.01883 (8)0.01347 (8)0.01522 (8)0.00166 (5)0.00076 (5)0.00073 (5)
Zn0.01664 (14)0.01436 (14)0.01128 (12)0.00221 (10)0.00157 (10)0.00034 (9)
Cl10.0179 (3)0.0180 (3)0.0328 (3)0.0018 (2)0.0001 (2)0.0005 (2)
Cl20.0215 (3)0.0179 (3)0.0242 (3)0.0053 (2)0.0049 (2)0.0010 (2)
O10.0276 (9)0.0181 (8)0.0157 (8)0.0051 (7)0.0059 (7)0.0044 (6)
O20.0229 (9)0.0175 (8)0.0136 (7)0.0042 (7)0.0039 (7)0.0004 (6)
C10.0158 (11)0.0151 (11)0.0127 (10)0.0005 (8)0.0001 (8)0.0002 (8)
C20.0152 (11)0.0121 (10)0.0123 (10)0.0030 (8)0.0005 (8)0.0006 (8)
C1A0.0126 (10)0.0153 (11)0.0144 (10)0.0010 (8)0.0017 (8)0.0021 (8)
C2A0.0262 (13)0.0184 (12)0.0150 (10)0.0057 (10)0.0037 (9)0.0002 (9)
C3A0.0340 (15)0.0139 (12)0.0234 (12)0.0017 (10)0.0070 (11)0.0015 (9)
C4A0.0302 (14)0.0203 (13)0.0227 (12)0.0013 (10)0.0057 (11)0.0065 (10)
C5A0.0237 (13)0.0279 (13)0.0149 (11)0.0028 (10)0.0008 (9)0.0042 (9)
C6A0.0220 (12)0.0181 (11)0.0143 (10)0.0039 (9)0.0004 (9)0.0018 (9)
C1B0.0211 (12)0.0128 (10)0.0110 (9)0.0042 (9)0.0008 (8)0.0018 (8)
C2B0.0221 (12)0.0152 (11)0.0152 (10)0.0018 (9)0.0033 (9)0.0012 (8)
C3B0.0323 (14)0.0147 (11)0.0184 (11)0.0040 (10)0.0043 (10)0.0012 (9)
C4B0.0373 (15)0.0184 (12)0.0168 (11)0.0131 (11)0.0029 (10)0.0005 (9)
C5B0.0230 (12)0.0228 (12)0.0183 (11)0.0097 (10)0.0045 (9)0.0038 (9)
C6B0.0196 (12)0.0166 (11)0.0162 (10)0.0000 (9)0.0012 (9)0.0021 (9)
C1C0.0163 (11)0.0136 (10)0.0132 (10)0.0013 (8)0.0016 (8)0.0017 (8)
C2C0.0203 (12)0.0227 (12)0.0132 (10)0.0032 (10)0.0005 (9)0.0014 (9)
C3C0.0178 (12)0.0271 (13)0.0203 (11)0.0046 (10)0.0033 (9)0.0023 (10)
C4C0.0151 (12)0.0284 (14)0.0255 (13)0.0003 (10)0.0047 (10)0.0026 (10)
C5C0.0244 (13)0.0321 (15)0.0200 (12)0.0027 (11)0.0071 (10)0.0068 (10)
C6C0.0188 (12)0.0251 (13)0.0176 (11)0.0045 (10)0.0009 (9)0.0061 (9)
O30.0364 (11)0.0157 (9)0.0210 (9)0.0033 (8)0.0081 (8)0.0044 (7)
O40.0247 (9)0.0196 (9)0.0141 (8)0.0032 (7)0.0025 (7)0.0011 (6)
C30.0184 (11)0.0199 (12)0.0123 (10)0.0040 (9)0.0000 (9)0.0000 (8)
C40.0180 (11)0.0159 (11)0.0154 (10)0.0028 (9)0.0002 (9)0.0007 (8)
C1D0.0248 (13)0.0197 (12)0.0131 (10)0.0059 (10)0.0019 (9)0.0012 (9)
C2D0.0304 (14)0.0247 (13)0.0199 (12)0.0092 (11)0.0040 (10)0.0016 (10)
C3D0.0497 (19)0.0309 (15)0.0241 (13)0.0219 (13)0.0011 (13)0.0016 (11)
C4D0.061 (2)0.0227 (14)0.0263 (14)0.0173 (14)0.0104 (14)0.0082 (11)
C5D0.0477 (19)0.0240 (14)0.0355 (16)0.0046 (13)0.0183 (14)0.0061 (12)
C6D0.0279 (14)0.0238 (13)0.0243 (12)0.0033 (11)0.0052 (11)0.0025 (10)
C1E0.0178 (11)0.0209 (12)0.0139 (10)0.0038 (9)0.0010 (9)0.0019 (9)
C2E0.0226 (13)0.0230 (12)0.0147 (10)0.0039 (10)0.0004 (9)0.0022 (9)
C3E0.0239 (13)0.0275 (14)0.0221 (12)0.0002 (11)0.0008 (10)0.0024 (10)
C4E0.0201 (13)0.0392 (16)0.0241 (13)0.0008 (11)0.0027 (10)0.0097 (11)
C5E0.0267 (14)0.0383 (16)0.0215 (12)0.0105 (12)0.0067 (11)0.0003 (11)
C6E0.0246 (13)0.0297 (14)0.0213 (12)0.0077 (11)0.0010 (10)0.0029 (10)
C1F0.0172 (11)0.0178 (11)0.0149 (10)0.0014 (9)0.0021 (9)0.0023 (8)
C2F0.0316 (14)0.0273 (14)0.0173 (11)0.0092 (11)0.0010 (10)0.0006 (10)
C3F0.0324 (15)0.0331 (15)0.0179 (12)0.0053 (12)0.0009 (11)0.0021 (10)
C4F0.0280 (14)0.0361 (16)0.0270 (13)0.0120 (12)0.0045 (11)0.0082 (11)
C5F0.0407 (17)0.0426 (18)0.0274 (14)0.0269 (14)0.0036 (13)0.0037 (12)
C6F0.0339 (15)0.0336 (15)0.0189 (12)0.0143 (12)0.0023 (11)0.0029 (10)
O1G0.0219 (9)0.0263 (10)0.0283 (10)0.0015 (7)0.0003 (8)0.0034 (8)
C1G0.0227 (13)0.0237 (13)0.0357 (15)0.0000 (11)0.0055 (11)0.0048 (11)
C2G0.0265 (14)0.0283 (14)0.0341 (15)0.0010 (11)0.0035 (12)0.0108 (11)
O2G0.0281 (10)0.0294 (10)0.0291 (10)0.0013 (8)0.0033 (8)0.0011 (8)
C3G0.0416 (18)0.0429 (18)0.0327 (16)0.0052 (14)0.0105 (14)0.0042 (13)
O1H0.0540 (14)0.0334 (11)0.0229 (10)0.0244 (10)0.0042 (9)0.0042 (8)
C1H0.056 (2)0.049 (2)0.0284 (15)0.0296 (17)0.0075 (14)0.0014 (13)
C2H0.0457 (19)0.0329 (16)0.0339 (16)0.0152 (14)0.0050 (14)0.0050 (12)
O2H0.0266 (10)0.0213 (9)0.0286 (10)0.0032 (7)0.0051 (8)0.0014 (7)
C3H0.0376 (17)0.0208 (14)0.0404 (16)0.0056 (12)0.0005 (13)0.0063 (12)
O1I0.0222 (10)0.0286 (10)0.0338 (10)0.0052 (8)0.0057 (8)0.0094 (8)
C1I0.0243 (14)0.0274 (14)0.0356 (15)0.0003 (11)0.0037 (11)0.0007 (11)
C2I0.0244 (14)0.0381 (17)0.0343 (15)0.0004 (12)0.0005 (12)0.0103 (13)
O2I0.0245 (10)0.0441 (13)0.0321 (11)0.0066 (9)0.0032 (8)0.0031 (9)
C3I0.046 (2)0.055 (2)0.0287 (15)0.0026 (16)0.0039 (14)0.0069 (14)
O1J0.0294 (10)0.0184 (9)0.0221 (9)0.0001 (7)0.0021 (8)0.0024 (7)
C1J0.0347 (15)0.0243 (14)0.0251 (13)0.0052 (11)0.0037 (11)0.0033 (10)
C2J0.0327 (15)0.0253 (14)0.0231 (12)0.0003 (11)0.0020 (11)0.0073 (10)
O2J0.0286 (10)0.0231 (9)0.0194 (8)0.0025 (8)0.0035 (7)0.0005 (7)
C3J0.0266 (14)0.0391 (16)0.0253 (13)0.0084 (12)0.0014 (11)0.0032 (11)
Geometric parameters (Å, º) top
Ba—O32.6925 (19)C1E—C2E1.387 (3)
Ba—O12.7073 (19)C1E—C6E1.405 (3)
Ba—O1J2.7572 (19)C2E—C3E1.389 (4)
Ba—O1H2.783 (2)C2E—H2E0.9500
Ba—O2J2.7908 (19)C3E—C4E1.381 (4)
Ba—O1G2.799 (2)C3E—H3E0.9500
Ba—O1I2.810 (2)C4E—C5E1.392 (4)
Ba—O2G2.985 (2)C4E—H4E0.9500
Ba—Cl13.1118 (11)C5E—C6E1.385 (4)
Ba—Zn3.9335 (11)C5E—H5E0.9500
Zn—O21.9682 (17)C6E—H6E0.9500
Zn—O41.9683 (18)C1F—C6F1.388 (4)
Zn—Cl12.2595 (10)C1F—C2F1.400 (3)
Zn—Cl22.2653 (9)C2F—C3F1.386 (4)
O1—C11.233 (3)C2F—H2F0.9500
O2—C11.275 (3)C3F—C4F1.372 (4)
C1—C21.568 (3)C3F—H3F0.9500
C2—C1B1.531 (3)C4F—C5F1.381 (4)
C2—C1A1.547 (3)C4F—H4F0.9500
C2—C1C1.550 (3)C5F—C6F1.388 (4)
C1A—C6A1.396 (3)C5F—H5F0.9500
C1A—C2A1.401 (3)C6F—H6F0.9500
C2A—C3A1.385 (3)O1G—C1G1.434 (3)
C2A—H2A0.9500O1G—H1G0.8397
C3A—C4A1.393 (4)C1G—C2G1.500 (4)
C3A—H3A0.9500C1G—H1G10.9900
C4A—C5A1.380 (4)C1G—H1G20.9900
C4A—H4A0.9500C2G—O2G1.431 (3)
C5A—C6A1.390 (3)C2G—H2G10.9900
C5A—H5A0.9500C2G—H2G20.9900
C6A—H6A0.9500O2G—C3G1.422 (4)
C1B—C2B1.391 (3)C3G—H3G10.9800
C1B—C6B1.397 (3)C3G—H3G20.9800
C2B—C3B1.394 (3)C3G—H3G30.9800
C2B—H2B0.9500O1H—C1H1.407 (4)
C3B—C4B1.381 (4)O1H—H1H0.8402
C3B—H3B0.9500C1H—C2H1.487 (4)
C4B—C5B1.389 (4)C1H—H1H10.9900
C4B—H4B0.9500C1H—H1H20.9900
C5B—C6B1.388 (3)C2H—O2H1.440 (4)
C5B—H5B0.9500C2H—H2H10.9900
C6B—H6B0.9500C2H—H2H20.9900
C1C—C2C1.390 (3)O2H—C3H1.419 (3)
C1C—C6C1.396 (3)C3H—H3H10.9800
C2C—C3C1.386 (3)C3H—H3H20.9800
C2C—H2C0.9500C3H—H3H30.9800
C3C—C4C1.390 (4)O1I—C1I1.440 (3)
C3C—H3C0.9500O1I—H1I0.8399
C4C—C5C1.387 (4)C1I—C2I1.496 (4)
C4C—H4C0.9500C1I—H1I10.9900
C5C—C6C1.388 (4)C1I—H1I20.9900
C5C—H5C0.9500C2I—O2I1.439 (4)
C6C—H6C0.9500C2I—H2I10.9900
O3—C31.232 (3)C2I—H2I20.9900
O4—C31.266 (3)O2I—C3I1.412 (4)
C3—C41.565 (3)C3I—H3I10.9800
C4—C1E1.536 (3)C3I—H3I20.9800
C4—C1D1.540 (3)C3I—H3I30.9800
C4—C1F1.549 (3)O1J—C1J1.433 (3)
C1D—C2D1.388 (4)O1J—H1J0.8403
C1D—C6D1.391 (4)C1J—C2J1.503 (4)
C2D—C3D1.392 (4)C1J—H1J10.9900
C2D—H2D0.9500C1J—H1J20.9900
C3D—C4D1.380 (5)C2J—O2J1.436 (3)
C3D—H3D0.9500C2J—H2J10.9900
C4D—C5D1.383 (5)C2J—H2J20.9900
C4D—H4D0.9500O2J—C3J1.424 (3)
C5D—C6D1.390 (4)C3J—H3J10.9800
C5D—H5D0.9500C3J—H3J20.9800
C6D—H6D0.9500C3J—H3J30.9800
O3—Ba—O184.08 (6)C4D—C3D—H3D119.5
O3—Ba—O1J142.04 (6)C2D—C3D—H3D119.5
O1—Ba—O1J114.85 (6)C3D—C4D—C5D118.6 (3)
O3—Ba—O1H60.16 (6)C3D—C4D—H4D120.7
O1—Ba—O1H122.95 (7)C5D—C4D—H4D120.7
O1J—Ba—O1H82.35 (6)C4D—C5D—C6D120.7 (3)
O3—Ba—O2J155.84 (6)C4D—C5D—H5D119.7
O1—Ba—O2J74.87 (6)C6D—C5D—H5D119.7
O1J—Ba—O2J60.31 (6)C5D—C6D—C1D121.2 (3)
O1H—Ba—O2J142.49 (6)C5D—C6D—H6D119.4
O3—Ba—O1G120.96 (6)C1D—C6D—H6D119.4
O1—Ba—O1G133.04 (6)C2E—C1E—C6E118.1 (2)
O1J—Ba—O1G71.05 (6)C2E—C1E—C4122.6 (2)
O1H—Ba—O1G103.93 (7)C6E—C1E—C4119.3 (2)
O2J—Ba—O1G68.94 (6)C1E—C2E—C3E120.8 (2)
O3—Ba—O1I95.18 (7)C1E—C2E—H2E119.6
O1—Ba—O1I71.58 (6)C3E—C2E—H2E119.6
O1J—Ba—O1I63.80 (6)C4E—C3E—C2E120.7 (3)
O1H—Ba—O1I69.50 (7)C4E—C3E—H3E119.7
O2J—Ba—O1I89.38 (6)C2E—C3E—H3E119.7
O1G—Ba—O1I134.83 (6)C3E—C4E—C5E119.6 (3)
O3—Ba—O2G65.59 (6)C3E—C4E—H4E120.2
O1—Ba—O2G139.45 (6)C5E—C4E—H4E120.2
O1J—Ba—O2G105.51 (6)C6E—C5E—C4E119.7 (3)
O1H—Ba—O2G64.98 (6)C6E—C5E—H5E120.2
O2J—Ba—O2G125.48 (6)C4E—C5E—H5E120.2
O1G—Ba—O2G57.15 (6)C5E—C6E—C1E121.2 (3)
O1I—Ba—O2G134.31 (6)C5E—C6E—H6E119.4
O3—Ba—Cl174.73 (5)C1E—C6E—H6E119.4
O1—Ba—Cl171.96 (5)C6F—C1F—C2F117.0 (2)
O1J—Ba—Cl1140.95 (4)C6F—C1F—C4124.4 (2)
O1H—Ba—Cl1128.16 (5)C2F—C1F—C4118.6 (2)
O2J—Ba—Cl187.39 (5)C3F—C2F—C1F121.7 (2)
O1G—Ba—Cl177.39 (5)C3F—C2F—H2F119.2
O1I—Ba—Cl1142.95 (4)C1F—C2F—H2F119.2
O2G—Ba—Cl174.38 (5)C4F—C3F—C2F120.7 (2)
O3—Ba—Zn53.90 (4)C4F—C3F—H3F119.6
O1—Ba—Zn48.34 (4)C2F—C3F—H3F119.6
O1J—Ba—Zn160.81 (4)C3F—C4F—C5F118.2 (3)
O1H—Ba—Zn113.88 (5)C3F—C4F—H4F120.9
O2J—Ba—Zn102.37 (5)C5F—C4F—H4F120.9
O1G—Ba—Zn112.26 (5)C4F—C5F—C6F121.6 (3)
O1I—Ba—Zn110.85 (5)C4F—C5F—H5F119.2
O2G—Ba—Zn91.21 (5)C6F—C5F—H5F119.2
Cl1—Ba—Zn35.01 (2)C1F—C6F—C5F120.7 (2)
O2—Zn—O4110.00 (8)C1F—C6F—H6F119.6
O2—Zn—Cl1111.30 (6)C5F—C6F—H6F119.6
O4—Zn—Cl1118.74 (6)C1G—O1G—Ba124.47 (16)
O2—Zn—Cl2107.44 (6)C1G—O1G—H1G111.8
O4—Zn—Cl2102.14 (6)Ba—O1G—H1G119.0
Cl1—Zn—Cl2106.19 (3)O1G—C1G—C2G107.4 (2)
O2—Zn—Ba91.95 (6)O1G—C1G—H1G1110.2
O4—Zn—Ba83.59 (6)C2G—C1G—H1G1110.2
Cl1—Zn—Ba52.20 (3)O1G—C1G—H1G2110.2
Cl2—Zn—Ba156.02 (2)C2G—C1G—H1G2110.2
Zn—Cl1—Ba92.79 (3)H1G1—C1G—H1G2108.5
C1—O1—Ba155.72 (16)O2G—C2G—C1G113.0 (2)
C1—O2—Zn116.35 (15)O2G—C2G—H2G1109.0
O1—C1—O2124.3 (2)C1G—C2G—H2G1109.0
O1—C1—C2120.6 (2)O2G—C2G—H2G2109.0
O2—C1—C2115.06 (19)C1G—C2G—H2G2109.0
C1B—C2—C1A109.37 (18)H2G1—C2G—H2G2107.8
C1B—C2—C1C110.82 (18)C3G—O2G—C2G113.5 (2)
C1A—C2—C1C108.82 (18)C3G—O2G—Ba125.66 (17)
C1B—C2—C1109.40 (18)C2G—O2G—Ba102.89 (15)
C1A—C2—C1112.19 (18)O2G—C3G—H3G1109.5
C1C—C2—C1106.20 (17)O2G—C3G—H3G2109.5
C6A—C1A—C2A117.2 (2)H3G1—C3G—H3G2109.5
C6A—C1A—C2121.6 (2)O2G—C3G—H3G3109.5
C2A—C1A—C2121.0 (2)H3G1—C3G—H3G3109.5
C3A—C2A—C1A120.8 (2)H3G2—C3G—H3G3109.5
C3A—C2A—H2A119.6C1H—O1H—Ba152.75 (18)
C1A—C2A—H2A119.6C1H—O1H—H1H108.3
C2A—C3A—C4A121.1 (2)Ba—O1H—H1H98.5
C2A—C3A—H3A119.5O1H—C1H—C2H109.1 (3)
C4A—C3A—H3A119.5O1H—C1H—H1H1109.9
C5A—C4A—C3A118.8 (2)C2H—C1H—H1H1109.9
C5A—C4A—H4A120.6O1H—C1H—H1H2109.9
C3A—C4A—H4A120.6C2H—C1H—H1H2109.9
C4A—C5A—C6A120.2 (2)H1H1—C1H—H1H2108.3
C4A—C5A—H5A119.9O2H—C2H—C1H108.8 (3)
C6A—C5A—H5A119.9O2H—C2H—H2H1109.9
C5A—C6A—C1A121.9 (2)C1H—C2H—H2H1109.9
C5A—C6A—H6A119.0O2H—C2H—H2H2109.9
C1A—C6A—H6A119.0C1H—C2H—H2H2109.9
C2B—C1B—C6B117.7 (2)H2H1—C2H—H2H2108.3
C2B—C1B—C2123.1 (2)C3H—O2H—C2H108.2 (2)
C6B—C1B—C2119.1 (2)O2H—C3H—H3H1109.5
C1B—C2B—C3B121.2 (2)O2H—C3H—H3H2109.5
C1B—C2B—H2B119.4H3H1—C3H—H3H2109.5
C3B—C2B—H2B119.4O2H—C3H—H3H3109.5
C4B—C3B—C2B120.1 (2)H3H1—C3H—H3H3109.5
C4B—C3B—H3B119.9H3H2—C3H—H3H3109.5
C2B—C3B—H3B119.9C1I—O1I—Ba131.91 (16)
C3B—C4B—C5B119.8 (2)C1I—O1I—H1I103.1
C3B—C4B—H4B120.1Ba—O1I—H1I108.4
C5B—C4B—H4B120.1O1I—C1I—C2I111.8 (2)
C6B—C5B—C4B119.6 (2)O1I—C1I—H1I1109.3
C6B—C5B—H5B120.2C2I—C1I—H1I1109.3
C4B—C5B—H5B120.2O1I—C1I—H1I2109.3
C5B—C6B—C1B121.6 (2)C2I—C1I—H1I2109.3
C5B—C6B—H6B119.2H1I1—C1I—H1I2107.9
C1B—C6B—H6B119.2O2I—C2I—C1I111.8 (2)
C2C—C1C—C6C118.1 (2)O2I—C2I—H2I1109.3
C2C—C1C—C2120.7 (2)C1I—C2I—H2I1109.3
C6C—C1C—C2121.0 (2)O2I—C2I—H2I2109.3
C3C—C2C—C1C121.4 (2)C1I—C2I—H2I2109.3
C3C—C2C—H2C119.3H2I1—C2I—H2I2107.9
C1C—C2C—H2C119.3C3I—O2I—C2I114.1 (3)
C2C—C3C—C4C120.0 (2)O2I—C3I—H3I1109.5
C2C—C3C—H3C120.0O2I—C3I—H3I2109.5
C4C—C3C—H3C120.0H3I1—C3I—H3I2109.5
C5C—C4C—C3C119.2 (2)O2I—C3I—H3I3109.5
C5C—C4C—H4C120.4H3I1—C3I—H3I3109.5
C3C—C4C—H4C120.4H3I2—C3I—H3I3109.5
C4C—C5C—C6C120.6 (2)C1J—O1J—Ba116.81 (15)
C4C—C5C—H5C119.7C1J—O1J—H1J105.9
C6C—C5C—H5C119.7Ba—O1J—H1J115.3
C5C—C6C—C1C120.7 (2)O1J—C1J—C2J111.5 (2)
C5C—C6C—H6C119.7O1J—C1J—H1J1109.3
C1C—C6C—H6C119.7C2J—C1J—H1J1109.3
C3—O3—Ba144.65 (16)O1J—C1J—H1J2109.3
C3—O4—Zn125.09 (16)C2J—C1J—H1J2109.3
O3—C3—O4125.0 (2)H1J1—C1J—H1J2108.0
O3—C3—C4119.3 (2)O2J—C2J—C1J108.4 (2)
O4—C3—C4115.6 (2)O2J—C2J—H2J1110.0
C1E—C4—C1D110.1 (2)C1J—C2J—H2J1110.0
C1E—C4—C1F111.38 (19)O2J—C2J—H2J2110.0
C1D—C4—C1F107.84 (18)C1J—C2J—H2J2110.0
C1E—C4—C3105.03 (18)H2J1—C2J—H2J2108.4
C1D—C4—C3110.38 (19)C3J—O2J—C2J113.4 (2)
C1F—C4—C3112.12 (19)C3J—O2J—Ba124.66 (16)
C2D—C1D—C6D117.8 (2)C2J—O2J—Ba118.34 (15)
C2D—C1D—C4122.9 (2)O2J—C3J—H3J1109.5
C6D—C1D—C4119.2 (2)O2J—C3J—H3J2109.5
C1D—C2D—C3D120.9 (3)H3J1—C3J—H3J2109.5
C1D—C2D—H2D119.5O2J—C3J—H3J3109.5
C3D—C2D—H2D119.5H3J1—C3J—H3J3109.5
C4D—C3D—C2D120.9 (3)H3J2—C3J—H3J3109.5
Ba—O1—C1—O231.5 (5)O4—C3—C4—C1D178.6 (2)
Ba—O1—C1—C2151.1 (3)O3—C3—C4—C1F123.7 (2)
Zn—O2—C1—O13.5 (3)O4—C3—C4—C1F58.3 (3)
Zn—O2—C1—C2178.94 (14)C1E—C4—C1D—C2D11.6 (3)
O1—C1—C2—C1B161.4 (2)C1F—C4—C1D—C2D110.1 (3)
O2—C1—C2—C1B21.0 (3)C3—C4—C1D—C2D127.2 (2)
O1—C1—C2—C1A39.8 (3)C1E—C4—C1D—C6D173.1 (2)
O2—C1—C2—C1A142.6 (2)C1F—C4—C1D—C6D65.2 (3)
O1—C1—C2—C1C79.0 (3)C3—C4—C1D—C6D57.6 (3)
O2—C1—C2—C1C98.7 (2)C6D—C1D—C2D—C3D0.9 (4)
C1B—C2—C1A—C6A12.2 (3)C4—C1D—C2D—C3D174.4 (2)
C1C—C2—C1A—C6A109.0 (2)C1D—C2D—C3D—C4D0.8 (4)
C1—C2—C1A—C6A133.8 (2)C2D—C3D—C4D—C5D0.1 (4)
C1B—C2—C1A—C2A173.5 (2)C3D—C4D—C5D—C6D0.9 (4)
C1C—C2—C1A—C2A65.3 (3)C4D—C5D—C6D—C1D0.8 (4)
C1—C2—C1A—C2A51.9 (3)C2D—C1D—C6D—C5D0.1 (4)
C6A—C1A—C2A—C3A1.0 (4)C4—C1D—C6D—C5D175.4 (2)
C2—C1A—C2A—C3A175.6 (2)C1D—C4—C1E—C2E103.2 (3)
C1A—C2A—C3A—C4A0.3 (4)C1F—C4—C1E—C2E16.4 (3)
C2A—C3A—C4A—C5A0.9 (4)C3—C4—C1E—C2E138.0 (2)
C3A—C4A—C5A—C6A0.1 (4)C1D—C4—C1E—C6E74.1 (3)
C4A—C5A—C6A—C1A1.3 (4)C1F—C4—C1E—C6E166.3 (2)
C2A—C1A—C6A—C5A1.8 (4)C3—C4—C1E—C6E44.7 (3)
C2—C1A—C6A—C5A176.3 (2)C6E—C1E—C2E—C3E0.9 (4)
C1A—C2—C1B—C2B108.0 (2)C4—C1E—C2E—C3E176.4 (2)
C1C—C2—C1B—C2B12.0 (3)C1E—C2E—C3E—C4E0.3 (4)
C1—C2—C1B—C2B128.7 (2)C2E—C3E—C4E—C5E0.6 (4)
C1A—C2—C1B—C6B67.2 (3)C3E—C4E—C5E—C6E0.8 (4)
C1C—C2—C1B—C6B172.85 (19)C4E—C5E—C6E—C1E0.1 (4)
C1—C2—C1B—C6B56.1 (3)C2E—C1E—C6E—C5E0.7 (4)
C6B—C1B—C2B—C3B0.9 (3)C4—C1E—C6E—C5E176.7 (2)
C2—C1B—C2B—C3B174.4 (2)C1E—C4—C1F—C6F92.9 (3)
C1B—C2B—C3B—C4B0.0 (4)C1D—C4—C1F—C6F146.2 (3)
C2B—C3B—C4B—C5B0.6 (4)C3—C4—C1F—C6F24.4 (3)
C3B—C4B—C5B—C6B0.3 (4)C1E—C4—C1F—C2F84.8 (3)
C4B—C5B—C6B—C1B0.6 (4)C1D—C4—C1F—C2F36.1 (3)
C2B—C1B—C6B—C5B1.1 (3)C3—C4—C1F—C2F157.8 (2)
C2—C1B—C6B—C5B174.3 (2)C6F—C1F—C2F—C3F1.6 (4)
C1B—C2—C1C—C2C89.5 (3)C4—C1F—C2F—C3F176.3 (2)
C1A—C2—C1C—C2C30.8 (3)C1F—C2F—C3F—C4F0.1 (4)
C1—C2—C1C—C2C151.7 (2)C2F—C3F—C4F—C5F1.8 (5)
C1B—C2—C1C—C6C87.1 (3)C3F—C4F—C5F—C6F1.9 (5)
C1A—C2—C1C—C6C152.6 (2)C2F—C1F—C6F—C5F1.5 (4)
C1—C2—C1C—C6C31.7 (3)C4—C1F—C6F—C5F176.2 (3)
C6C—C1C—C2C—C3C1.3 (4)C4F—C5F—C6F—C1F0.2 (5)
C2—C1C—C2C—C3C175.4 (2)Ba—O1G—C1G—C2G8.8 (3)
C1C—C2C—C3C—C4C0.4 (4)O1G—C1G—C2G—O2G54.1 (3)
C2C—C3C—C4C—C5C0.5 (4)C1G—C2G—O2G—C3G71.7 (3)
C3C—C4C—C5C—C6C0.5 (4)C1G—C2G—O2G—Ba67.0 (2)
C4C—C5C—C6C—C1C0.4 (4)Ba—O1H—C1H—C2H4.1 (7)
C2C—C1C—C6C—C5C1.2 (4)O1H—C1H—C2H—O2H72.7 (4)
C2—C1C—C6C—C5C175.4 (2)C1H—C2H—O2H—C3H174.4 (2)
Ba—O3—C3—O413.4 (5)Ba—O1I—C1I—C2I140.4 (2)
Ba—O3—C3—C4164.39 (19)O1I—C1I—C2I—O2I63.6 (3)
Zn—O4—C3—O322.2 (3)C1I—C2I—O2I—C3I105.6 (3)
Zn—O4—C3—C4159.98 (15)Ba—O1J—C1J—C2J46.1 (3)
O3—C3—C4—C1E115.2 (2)O1J—C1J—C2J—O2J56.2 (3)
O4—C3—C4—C1E62.8 (3)C1J—C2J—O2J—C3J159.6 (2)
O3—C3—C4—C1D3.4 (3)C1J—C2J—O2J—Ba40.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1G—H1G···O2Ii0.841.912.728 (3)163
O1H—H1H···O30.842.172.746 (3)125
O1I—H1I···O2H0.841.992.817 (3)170
C2I—H2I2···Cl1ii0.992.813.660 (3)144
O1J—H1J···Cl2iii0.842.173.012 (2)174
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y+1, z.
Selected bond lengths (Å) top
Ba—O32.6925 (19)Ba—O2G2.985 (2)
Ba—O12.7073 (19)Ba—Cl13.1118 (11)
Ba—O1J2.7572 (19)Zn—O21.9682 (17)
Ba—O1H2.783 (2)Zn—O41.9683 (18)
Ba—O2J2.7908 (19)Zn—Cl12.2595 (10)
Ba—O1G2.799 (2)Zn—Cl22.2653 (9)
Ba—O1I2.810 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1G—H1G···O2Ii0.841.912.728 (3)163
O1I—H1I···O2H0.841.992.817 (3)170
C2I—H2I2···Cl1ii0.992.813.660 (3)144
O1J—H1J···Cl2iii0.842.173.012 (2)174
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[BaZn(C20H15O2)2Cl2(C3H8O2)4]
Mr1152.62
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.706 (3), 10.643 (3), 25.073 (6)
α, β, γ (°)89.62 (3), 89.26 (3), 82.73 (3)
V3)2569.0 (12)
Z2
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.31 × 0.23 × 0.21
Data collection
DiffractometerOxford Diffraction KM-4-CCD
diffractometer
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.687, 0.780
No. of measured, independent and
observed [I > 2σ(I)] reflections
24098, 12296, 10742
Rint0.025
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.100, 1.14
No. of reflections12296
No. of parameters617
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.89, 0.57

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), SHELXTL (Sheldrick, 2008).

 

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Volume 71| Part 7| July 2015| Pages 791-794
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