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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1774-m1775
https://doi.org/10.1107/S1600536811048082

cis-Bis(2,2′-bi­pyridine-κ2N,N′)bis­­(di­methyl sulfoxide-κO)zinc bis­­(tetra­phenyl­borate) di­methyl sulfoxide monosolvate

Stefania Tomyn,a* Elżbieta Gumienna-Kontecka,b Natalia I. Usenko,a Turganbay S. Iskenderova and Elena V. Prisyazhnayac

aNational Taras Shevchenko University of Kyiv, Department of Chemistry, Volodymyrska Str. 64, 01601 Kyiv, Ukraine, bUniversity of Wrocław, Faculty of Chemistry, F. Joliot-Curie Str. 14, 50-383 Wrocław, Poland, and cKyiv National University of Construction and Architecture, Department of Chemistry, Povitroflotsky Ave. 31, 03680 Kyiv, Ukraine
*Correspondence e-mail: stefania.tomyn@gmail.com

(Received 21 October 2011; accepted 12 November 2011; online 19 November 2011)

In the mononuclear title complex, [Zn(C10H8N2)2(C2H6OS)2](C24H20B)2·C2H6OS, the ZnII ion is coordinated by four N atoms of two bidentate 2,2′-bipyridine mol­ecules and by the O atoms of two cis-disposed dimethyl sulfoxide mol­ecules in a distorted octa­hedral geometry. The S atom and the methyl groups of one of the coordinated dimethyl sulfoxide mol­ecules are disordered in a 0.509 (2):0.491 (2) ratio. The crystal packing is stabilized by C—H⋯O hydrogen bonds between the dimethyl sulfoxide solvent mol­ecules and tetra­phenyl­borate anions.

Related literature

For uses of 2,2′-bipyridine, see: Fritsky et al. (1998[Fritsky, I. O., Kozłowski, H., Sadler, P. J., Yefetova, O. P., Świątek-Kozłowska, J., Kalibabchuk, V. A. & Głowiak, T. (1998). J. Chem. Soc. Dalton Trans. pp. 3269-3274.], 2004[Fritsky, I. O., Świątek-Kozłowska, J., Dobosz, A., Sliva, T. Yu. & Dudarenko, N. M. (2004). Inorg. Chim. Acta, 346, 111-118.]); Kanderal et al. (2005[Kanderal, O. M., Kozłowski, H., Dobosz, A., Świątek-Kozłowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]); Moroz et al. (2010[Moroz, Y. S., Szyrweil, L., Demeshko, S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chem. 49, 4750-4752.]); Penkova et al. (2009[Penkova, L. V., Maciąg, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.]). For related structures, see: Fritsky et al. (2001[Fritsky, I. O., Ott, R., Pritzkow, H. & Krämer, R. (2001). Chem. Eur. J. 7, 1221-1231.]); Krämer & Fritsky (2000[Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505-3510.]); Lalioti et al. (1998[Lalioti, N., Raptopoulou, C. P., Terzis, A., Panagiotopoulos, A., Perlepes, S. P. & Manessi-Zoupa, E. (1998). J. Chem. Soc. Dalton Trans. pp. 1327-1333.]); Persson (1982[Persson, I. (1982). Acta Chem. Scand. Ser. A, 36, 7-13.]); Petrusenko et al. (1997[Petrusenko, S. R., Kokozay, V. N. & Fritsky, I. O. (1997). Polyhedron, 16, 267-274.]); Sachse et al. (2008[Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, 5, 800-806.]); Wörl et al. (2005[Wörl, S., Pritzkow, H., Fritsky, I. O. & Krämer, R. (2005). Dalton Trans. pp. 27-29.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C10H8N2)2(C2H6OS)2](C24H20B)2·C2H6OS

  • Mr = 1250.54

  • Monoclinic, P 21 /c

  • a = 13.8836 (5) Å

  • b = 18.0029 (7) Å

  • c = 26.1594 (10) Å

  • β = 90.225 (3)°

  • V = 6538.4 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.52 mm−1

  • T = 120 K

  • 0.38 × 0.25 × 0.13 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.955, Tmax = 0.987

  • 44646 measured reflections

  • 15166 independent reflections

  • 9478 reflections with I > 2σ(I)

  • Rint = 0.044
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.095

  • S = 0.94

  • 15166 reflections

  • 820 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.48 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C23—H23⋯O3i 0.93 2.41 3.336 (3) 173
C59—H59⋯O3i 0.93 2.53 3.403 (3) 156
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811048082/zl2419sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048082/zl2419Isup2.hkl

checkCIF report


Comment top

2,2'-Bipyridine and 1,10-phenantroline are chelating ligands which are widely used in coordination chemistry, in particular, for the preparation of mixed ligand complexes (Fritsky et al., 1998; Kanderal et al., 2005). They are also often used in the synthesis of discrete polynuclear complexes in order to prevent formation of coordination polymers by blocking a certain number of vacant sites in the coordination sphere of a metal ion (Fritsky et al., 2004; Moroz et al., 2010; Penkova et al., 2009). The title compound was obtained unintentionally as the product of an attempted synthesis of a pyrazolate complex of zinc (II) using 2,2'-bipyridine as an additional ligand and sodium tetraphenylborate for better crystallization of the resulting product.

The title compound, [Zn(C10H8N2)2(C2H6SO)2][(C24H20B)2].C2H6SO, consists of a cationic Zn2+ complex, two tetraphenylborate anions and a solvent dimethyl sulfoxide (DMSO) molecule. The ZnII center is coordinated by four nitrogen atoms of two bidentately coordinated molecules of 2,2'-dipyridine and by the oxygen atoms of two cis-disposed dimethyl sulfoxide molecules. In one coordinated molecule of DMSO the S atom and the methyl groups are disordered with site occupansies of 0.5086 (17) and 0.4914 (17). The central atom adopts a highly distorted octahedral geometry with bond angles of 77.02 (6)–100.08 (6)°. The Zn—O bond lengths in the coordination sphere differ noticeably: the Zn—O1 = 2.0671 (13) Å bond is shorter and the Zn—O2 = 2.1814 (15) Å bond is much longer. Similar differences have been observed before in the related zinc complexes (Lalioti et al., 1998; Persson, 1982; Petrusenko et al., 1997). The Zn—N bond distances fall in the range 2.105 (2)–2.160 (2) Å. The two dipyridine molecules are nearly planar with dihedral angles of -0.9 (3)° and 5.7 (3)° between two bonded pyridine rings. The C—C and C—N bond lengths in the bipyridine molecules exhibit normal values (Fritsky et al., 2001; Krämer & Fritsky, 2000; Sachse et al., 2008; Wörl et al., 2005). In the crystal packing the tetraphenylborate anions are linked with the solvate DMSO molecule by C—H···O hydrogen bonds and form layers coplanar the [101] plane.

Related literature top

For uses of 2,2'-bipyridine, see: Fritsky et al. (1998, 2004); Kanderal et al. (2005); Moroz et al. (2010); Penkova et al. (2009). For related structures, see: Fritsky et al. (2001); Krämer & Fritsky (2000); Lalioti et al. (1998); Persson (1982); Petrusenko et al. (1997); Sachse et al. (2008); Wörl et al. (2005).

Experimental top

The title compound was obtained accidentally as the product of an attempted synthesis of a zinc complex with 3,5-dimethylpyrazole, using slow evaporation of a dimethyl sulfoxide solution of zinc (II) chloride, sodium tetraphenylborate, 2,2'-bipyridine and 3,5-dimethylpyrazole at room temperature. A solution of ZnCl2.4H2O (0.208 g, 1 mmol) in DMSO (10 ml) was added to a mixture of 2,2'-bipyridine (0.312 g, 2 mmol) and 3,5-dimethylpyrazole (0.192 g, 2 mmol) in DMSO (10 ml). The mixture was stirred for 15 minutes at room temperature and filtered off. Then sodium tetraphenylborate (0.684 g, 2 mmol) in 5 ml of DMSO was added. The resulting mixture was stirred for 15 minutes, filtered off and set aside at room temperature. Colourless crystals of the title compound suitable for the X-ray analysis were obtained in three days (yield 0.837 g, 66.9%). Analysis calculated for C74H74B2N4O3S3Zn: C 71.07, H 5.96, N 4.48%, found C 70.92, H 5.84, N 4.39%.

Refinement top

The S atoms and methyl groups of one coordinated dimethylsulfoxide molecule were disordered. This was modelled with two different orientations and from refinement the site occupancies were 0.5086 (17):0.4914 (17). The highest positive peak on the residual map (σ = 0.05 e/Å3) is equal to 0.42 e/Å3 (0.18 Å from S3) and the deepest hole is -0.48 e/Å3 (0.74 Å from S3). All H atoms of metyl groups were positioned geometrically and refined using a riding model, with C—H = 0.96 Å and with Uiso(H) = 1.5×Ueq(C). All H atoms of dipyridine and phenyl rings were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and with Uiso(H) = 1.2×Ueq(C).

Structure description top

2,2'-Bipyridine and 1,10-phenantroline are chelating ligands which are widely used in coordination chemistry, in particular, for the preparation of mixed ligand complexes (Fritsky et al., 1998; Kanderal et al., 2005). They are also often used in the synthesis of discrete polynuclear complexes in order to prevent formation of coordination polymers by blocking a certain number of vacant sites in the coordination sphere of a metal ion (Fritsky et al., 2004; Moroz et al., 2010; Penkova et al., 2009). The title compound was obtained unintentionally as the product of an attempted synthesis of a pyrazolate complex of zinc (II) using 2,2'-bipyridine as an additional ligand and sodium tetraphenylborate for better crystallization of the resulting product.

The title compound, [Zn(C10H8N2)2(C2H6SO)2][(C24H20B)2].C2H6SO, consists of a cationic Zn2+ complex, two tetraphenylborate anions and a solvent dimethyl sulfoxide (DMSO) molecule. The ZnII center is coordinated by four nitrogen atoms of two bidentately coordinated molecules of 2,2'-dipyridine and by the oxygen atoms of two cis-disposed dimethyl sulfoxide molecules. In one coordinated molecule of DMSO the S atom and the methyl groups are disordered with site occupansies of 0.5086 (17) and 0.4914 (17). The central atom adopts a highly distorted octahedral geometry with bond angles of 77.02 (6)–100.08 (6)°. The Zn—O bond lengths in the coordination sphere differ noticeably: the Zn—O1 = 2.0671 (13) Å bond is shorter and the Zn—O2 = 2.1814 (15) Å bond is much longer. Similar differences have been observed before in the related zinc complexes (Lalioti et al., 1998; Persson, 1982; Petrusenko et al., 1997). The Zn—N bond distances fall in the range 2.105 (2)–2.160 (2) Å. The two dipyridine molecules are nearly planar with dihedral angles of -0.9 (3)° and 5.7 (3)° between two bonded pyridine rings. The C—C and C—N bond lengths in the bipyridine molecules exhibit normal values (Fritsky et al., 2001; Krämer & Fritsky, 2000; Sachse et al., 2008; Wörl et al., 2005). In the crystal packing the tetraphenylborate anions are linked with the solvate DMSO molecule by C—H···O hydrogen bonds and form layers coplanar the [101] plane.

For uses of 2,2'-bipyridine, see: Fritsky et al. (1998, 2004); Kanderal et al. (2005); Moroz et al. (2010); Penkova et al. (2009). For related structures, see: Fritsky et al. (2001); Krämer & Fritsky (2000); Lalioti et al. (1998); Persson (1982); Petrusenko et al. (1997); Sachse et al. (2008); Wörl et al. (2005).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL7 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The crystal structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H–atoms are omitted for clarity. The S atoms and methyl groups of one coordinated dimethyl sulfoxide molecule are disordered in a ratio of 0.509 (2):0.491 (2).
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along [010]. H–atoms not involved in H—bonds and disordered atoms are omitted for clarity.
cis-Bis(2,2'-bipyridine-κ2N,N')bis(dimethyl sulfoxide-κO)zinc bis(tetraphenylborate) dimethyl sulfoxide monosolvate top
Crystal data top
[Zn(C10H8N2)2(C2H6OS)2](C24H20B)2·C2H6OSF(000) = 2632
Mr = 1250.54Dx = 1.270 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4578 reflections
a = 13.8836 (5) Åθ = 3.0–27.5°
b = 18.0029 (7) ŵ = 0.52 mm−1
c = 26.1594 (10) ÅT = 120 K
β = 90.225 (3)°Block, colourless
V = 6538.4 (4) Å30.38 × 0.25 × 0.13 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer		15166 independent reflections
Radiation source: fine-focus sealed tube9478 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.044
Detector resolution: 9 pixels mm-1θmax = 28.5°, θmin = 3.0°
φ scans and ω scans with κ offseth = −18→18
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)		k = −23→20
Tmin = 0.955, Tmax = 0.987l = −27→33
44646 measured 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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0455P)2]
where P = (Fo2 + 2Fc2)/3
15166 reflections(Δ/σ)max = 0.001
820 parametersΔρmax = 0.42 e Å−3
6 restraintsΔρmin = −0.48 e Å−3
Crystal data top
[Zn(C10H8N2)2(C2H6OS)2](C24H20B)2·C2H6OSV = 6538.4 (4) Å3
Mr = 1250.54Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.8836 (5) ŵ = 0.52 mm−1
b = 18.0029 (7) ÅT = 120 K
c = 26.1594 (10) Å0.38 × 0.25 × 0.13 mm
β = 90.225 (3)°
Data collection top
Nonius KappaCCD
diffractometer		15166 independent reflections
Absorption correction: multi-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)		9478 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.987Rint = 0.044
44646 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0426 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 0.94Δρmax = 0.42 e Å−3
15166 reflectionsΔρmin = −0.48 e Å−3
820 parameters
Special details top

Experimental. One of the coordinated DMSO molecules was found to be disordered over two positions, its sulfur and carbon atoms were refined with occupancy factors 0.502/0.498.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.724530 (16)0.214565 (13)0.146456 (9)0.02207 (7)
S10.52919 (4)0.26321 (3)0.20025 (2)0.02365 (12)
S30.80680 (5)0.72158 (4)0.11760 (3)0.04729 (18)
O10.63747 (9)0.27658 (7)0.19410 (5)0.0258 (3)
O20.67453 (10)0.11039 (8)0.17966 (6)0.0354 (4)
O30.74093 (14)0.78001 (12)0.14009 (7)0.0691 (6)
N10.74779 (12)0.31086 (9)0.09891 (7)0.0237 (4)
N20.61621 (11)0.20371 (9)0.09039 (6)0.0203 (4)
N30.84193 (11)0.22497 (9)0.19728 (6)0.0203 (4)
N40.83624 (12)0.15402 (9)0.10881 (6)0.0235 (4)
C10.81369 (15)0.36383 (12)0.10584 (9)0.0299 (5)
H10.85560.35950.13350.036*
C20.82311 (16)0.42462 (12)0.07435 (10)0.0383 (6)
H20.86990.46050.08050.046*
C30.76070 (17)0.43066 (13)0.03322 (11)0.0461 (7)
H30.76510.47090.01100.055*
C40.69177 (16)0.37650 (13)0.02536 (9)0.0382 (6)
H40.64940.3799−0.00210.046*
C50.68637 (15)0.31702 (12)0.05881 (8)0.0272 (5)
C60.61165 (14)0.25696 (11)0.05425 (8)0.0218 (5)
C70.54197 (16)0.25689 (13)0.01688 (8)0.0326 (5)
H70.54140.2931−0.00850.039*
C80.47225 (16)0.20144 (13)0.01774 (8)0.0323 (5)
H80.42380.2008−0.00690.039*
C90.47470 (14)0.14803 (12)0.05463 (8)0.0251 (5)
H90.42830.11080.05570.030*
C100.54796 (14)0.15072 (11)0.09034 (8)0.0230 (5)
H100.55030.11430.11550.028*
C110.83799 (15)0.26015 (11)0.24241 (8)0.0243 (5)
H110.77940.27970.25300.029*
C120.91734 (15)0.26855 (11)0.27372 (8)0.0252 (5)
H120.91210.29180.30530.030*
C131.00477 (15)0.24159 (11)0.25703 (8)0.0247 (5)
H131.05980.24780.27700.030*
C141.01016 (14)0.20537 (11)0.21058 (8)0.0220 (5)
H141.06870.18710.19890.026*
C150.92685 (14)0.19666 (10)0.18153 (7)0.0184 (4)
C160.92294 (14)0.15331 (10)0.13289 (8)0.0202 (4)
C170.99905 (14)0.11158 (11)0.11420 (8)0.0246 (5)
H171.05840.11210.13080.029*
C180.98597 (15)0.06919 (12)0.07069 (9)0.0304 (5)
H181.03600.04020.05810.036*
C190.89800 (15)0.07036 (12)0.04606 (9)0.0312 (5)
H190.88770.04250.01660.037*
C200.82551 (15)0.11386 (12)0.06609 (9)0.0306 (5)
H200.76650.11530.04910.037*
C210.19753 (13)0.32486 (11)0.14914 (8)0.0203 (5)
C220.20579 (14)0.33028 (11)0.20236 (8)0.0223 (5)
H220.18460.37350.21820.027*
C230.24422 (14)0.27406 (12)0.23266 (8)0.0251 (5)
H230.24840.28030.26790.030*
C240.27621 (14)0.20897 (12)0.21053 (8)0.0279 (5)
H240.30070.17080.23070.033*
C250.27139 (15)0.20142 (12)0.15797 (9)0.0283 (5)
H250.29380.15830.14250.034*
C260.23315 (14)0.25828 (11)0.12828 (8)0.0231 (5)
H260.23100.25210.09300.028*
C270.26357 (15)0.42973 (11)0.09225 (9)0.0278 (5)
C280.30957 (16)0.40473 (13)0.04815 (9)0.0389 (6)
H280.27720.37160.02690.047*
C290.40246 (19)0.42752 (17)0.03459 (12)0.0568 (8)
H290.43050.40930.00490.068*
C300.45232 (19)0.47648 (18)0.06485 (15)0.0662 (10)
H300.51420.49140.05600.079*
C310.40942 (19)0.50331 (14)0.10863 (13)0.0565 (9)
H310.44210.53690.12940.068*
C320.31695 (16)0.47995 (12)0.12172 (10)0.0385 (6)
H320.28950.49870.15140.046*
C330.09388 (14)0.36593 (11)0.06429 (7)0.0196 (4)
C340.04322 (14)0.29878 (11)0.06323 (8)0.0236 (5)
H340.05220.26530.08990.028*
C35−0.02016 (15)0.27994 (12)0.02387 (8)0.0290 (5)
H35−0.05280.23480.02480.035*
C36−0.03473 (16)0.32817 (12)−0.01664 (8)0.0307 (5)
H36−0.07640.3157−0.04320.037*
C370.01389 (15)0.39551 (12)−0.01688 (8)0.0287 (5)
H370.00490.4286−0.04380.034*
C380.07559 (15)0.41336 (11)0.02278 (8)0.0246 (5)
H380.10660.45910.02190.030*
C390.09334 (14)0.45402 (11)0.14258 (8)0.0231 (5)
C400.02083 (15)0.42923 (12)0.17619 (8)0.0260 (5)
H400.01670.37880.18350.031*
C41−0.04465 (16)0.47739 (13)0.19885 (8)0.0331 (6)
H41−0.09180.45880.22060.040*
C42−0.03988 (18)0.55261 (14)0.18919 (9)0.0387 (6)
H42−0.08310.58500.20460.046*
C430.02955 (17)0.57935 (12)0.15653 (9)0.0348 (6)
H430.03280.62990.14950.042*
C440.09491 (16)0.53073 (12)0.13393 (8)0.0278 (5)
H440.14150.55010.11220.033*
C450.67243 (14)0.46433 (11)0.32789 (7)0.0204 (4)
C460.69461 (15)0.43942 (12)0.27845 (8)0.0274 (5)
H460.73770.40020.27500.033*
C470.65573 (16)0.47026 (13)0.23464 (8)0.0318 (5)
H470.67400.45250.20270.038*
C480.58957 (16)0.52754 (12)0.23819 (8)0.0311 (5)
H480.56290.54850.20890.037*
C490.56395 (16)0.55301 (12)0.28611 (8)0.0302 (5)
H490.51900.59100.28920.036*
C500.60518 (14)0.52191 (11)0.32977 (8)0.0245 (5)
H500.58710.54030.36150.029*
C510.70368 (14)0.47599 (11)0.43037 (8)0.0206 (4)
C520.64824 (14)0.46009 (11)0.47371 (8)0.0228 (5)
H520.61050.41740.47380.027*
C530.64757 (15)0.50574 (11)0.51668 (8)0.0260 (5)
H530.60870.49360.54430.031*
C540.70394 (15)0.56890 (11)0.51879 (8)0.0249 (5)
H540.70510.59830.54800.030*
C550.75887 (14)0.58759 (12)0.47635 (8)0.0241 (5)
H550.79630.63040.47660.029*
C560.75753 (14)0.54186 (11)0.43360 (8)0.0221 (5)
H560.79440.55560.40550.027*
C570.65599 (14)0.34436 (11)0.38358 (7)0.0227 (5)
C580.55499 (15)0.34609 (12)0.38794 (7)0.0242 (5)
H580.52470.39200.39050.029*
C590.49837 (16)0.28232 (12)0.38860 (8)0.0285 (5)
H590.43180.28620.39140.034*
C600.54128 (17)0.21295 (13)0.38513 (8)0.0342 (6)
H600.50410.17000.38610.041*
C610.64034 (18)0.20865 (13)0.38029 (9)0.0371 (6)
H610.67010.16250.37770.045*
C620.69562 (16)0.27315 (12)0.37923 (8)0.0313 (5)
H620.76200.26870.37550.038*
C630.83386 (14)0.41010 (11)0.37502 (8)0.0224 (5)
C640.88322 (15)0.36738 (12)0.41138 (8)0.0289 (5)
H640.84790.34480.43720.035*
C650.98235 (16)0.35709 (13)0.41071 (9)0.0353 (6)
H651.01170.32800.43570.042*
C661.03740 (16)0.38984 (13)0.37327 (9)0.0353 (6)
H661.10370.38230.37230.042*
C670.99264 (15)0.43398 (12)0.33710 (9)0.0313 (5)
H671.02900.45720.31200.038*
C680.89287 (15)0.44376 (11)0.33823 (8)0.0250 (5)
H680.86430.47390.31360.030*
C690.50666 (17)0.29225 (16)0.26363 (9)0.0485 (7)
H69A0.53910.25960.28700.073*
H69B0.43860.29090.27000.073*
H69C0.53000.34200.26830.073*
C700.47176 (15)0.33676 (12)0.16722 (9)0.0335 (6)
H70A0.50000.38320.17740.050*
H70B0.40440.33700.17530.050*
H70C0.47970.33000.13110.050*
C730.79903 (18)0.73640 (16)0.05111 (9)0.0499 (7)
H73A0.73300.73290.04040.075*
H73B0.83640.69950.03370.075*
H73C0.82350.78490.04310.075*
C740.7449 (2)0.6357 (2)0.11890 (16)0.1125 (16)
H74A0.73510.62080.15370.169*
H74B0.78230.59870.10150.169*
H74C0.68370.64110.10210.169*
B10.16154 (17)0.39404 (12)0.11232 (9)0.0217 (5)
B20.71656 (17)0.42268 (13)0.37894 (9)0.0219 (5)
S2A0.74891 (8)0.04806 (6)0.18867 (4)0.0311 (4)0.5086 (17)
C71A0.6866 (8)−0.0346 (6)0.1753 (4)0.052 (3)0.5086 (17)
H71D0.6813−0.04090.13900.079*0.5086 (17)
H71E0.6234−0.03220.18990.079*0.5086 (17)
H71F0.7211−0.07590.18970.079*0.5086 (17)
C72A0.7508 (7)0.0468 (4)0.2561 (2)0.084 (3)0.5086 (17)
H72D0.79270.00790.26770.127*0.5086 (17)
H72E0.68680.03820.26860.127*0.5086 (17)
H72F0.77380.09370.26860.127*0.5086 (17)
S2B0.68459 (8)0.05333 (7)0.22553 (5)0.0311 (4)0.4914 (17)
C71B0.6625 (7)−0.0331 (5)0.1969 (4)0.070 (4)0.4914 (17)
H71A0.5976−0.03450.18420.104*0.4914 (17)
H71B0.6715−0.07180.22170.104*0.4914 (17)
H71C0.7065−0.04040.16910.104*0.4914 (17)
C72B0.8110 (3)0.0438 (3)0.2349 (2)0.0315 (13)0.4914 (17)
H72A0.83560.08730.25170.047*0.4914 (17)
H72B0.84200.03820.20240.047*0.4914 (17)
H72C0.82360.00090.25560.047*0.4914 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01550 (12)0.01983 (13)0.03086 (15)0.00145 (10)−0.00370 (10)−0.00303 (11)
S10.0174 (3)0.0262 (3)0.0274 (3)0.0014 (2)−0.0017 (2)0.0019 (2)
S30.0360 (4)0.0647 (5)0.0411 (4)−0.0026 (3)−0.0098 (3)0.0117 (3)
O10.0156 (7)0.0286 (8)0.0333 (9)0.0012 (6)−0.0006 (6)−0.0052 (7)
O20.0274 (9)0.0264 (9)0.0523 (11)−0.0006 (7)−0.0144 (8)0.0136 (7)
O30.0524 (13)0.1097 (18)0.0451 (12)0.0091 (12)0.0062 (10)−0.0272 (11)
N10.0173 (9)0.0204 (9)0.0333 (11)−0.0003 (7)0.0032 (8)−0.0036 (8)
N20.0161 (9)0.0207 (9)0.0242 (10)−0.0004 (7)0.0003 (7)−0.0026 (7)
N30.0162 (9)0.0177 (9)0.0270 (10)0.0006 (7)−0.0003 (7)−0.0023 (7)
N40.0201 (9)0.0197 (9)0.0308 (11)0.0008 (7)−0.0045 (8)−0.0069 (8)
C10.0244 (12)0.0228 (12)0.0424 (14)−0.0043 (10)−0.0012 (10)−0.0032 (10)
C20.0254 (13)0.0244 (13)0.0653 (18)−0.0047 (10)0.0067 (12)−0.0011 (12)
C30.0354 (15)0.0313 (15)0.072 (2)−0.0041 (11)0.0086 (14)0.0194 (13)
C40.0293 (13)0.0395 (15)0.0459 (15)−0.0020 (11)0.0003 (11)0.0147 (12)
C50.0226 (12)0.0241 (12)0.0349 (14)0.0038 (9)0.0046 (10)0.0033 (10)
C60.0220 (11)0.0216 (11)0.0217 (11)0.0034 (9)0.0028 (9)0.0000 (9)
C70.0330 (13)0.0361 (14)0.0288 (13)−0.0026 (11)−0.0018 (10)0.0092 (11)
C80.0261 (12)0.0457 (15)0.0249 (13)−0.0043 (11)−0.0075 (10)0.0008 (11)
C90.0201 (11)0.0322 (13)0.0230 (12)−0.0054 (9)0.0002 (9)−0.0048 (10)
C100.0229 (11)0.0231 (11)0.0228 (12)0.0000 (9)0.0029 (9)−0.0002 (9)
C110.0204 (11)0.0216 (11)0.0310 (13)0.0037 (9)0.0013 (9)−0.0044 (9)
C120.0270 (12)0.0281 (12)0.0206 (11)0.0007 (9)−0.0004 (9)−0.0024 (9)
C130.0185 (11)0.0307 (12)0.0249 (12)−0.0034 (9)−0.0053 (9)0.0006 (10)
C140.0174 (11)0.0220 (11)0.0266 (12)0.0010 (9)0.0012 (9)0.0013 (9)
C150.0181 (11)0.0138 (10)0.0233 (11)−0.0011 (8)0.0001 (8)0.0036 (8)
C160.0196 (11)0.0133 (10)0.0276 (12)−0.0024 (8)−0.0018 (9)0.0010 (9)
C170.0171 (11)0.0230 (12)0.0336 (13)0.0010 (9)−0.0015 (9)−0.0025 (10)
C180.0227 (12)0.0256 (12)0.0429 (15)0.0022 (9)0.0045 (10)−0.0106 (11)
C190.0301 (13)0.0270 (13)0.0363 (14)−0.0006 (10)−0.0033 (10)−0.0145 (10)
C200.0220 (12)0.0315 (13)0.0384 (14)0.0006 (10)−0.0082 (10)−0.0115 (11)
C210.0142 (10)0.0204 (11)0.0264 (12)−0.0039 (8)−0.0023 (9)0.0016 (9)
C220.0182 (11)0.0217 (11)0.0270 (12)−0.0027 (9)−0.0014 (9)−0.0016 (9)
C230.0185 (11)0.0325 (13)0.0243 (12)−0.0065 (9)−0.0033 (9)0.0058 (10)
C240.0217 (11)0.0273 (12)0.0346 (13)−0.0018 (10)−0.0062 (10)0.0102 (10)
C250.0224 (12)0.0236 (12)0.0389 (14)0.0032 (9)−0.0042 (10)0.0009 (10)
C260.0216 (11)0.0221 (11)0.0256 (12)−0.0001 (9)−0.0019 (9)0.0011 (9)
C270.0217 (12)0.0197 (12)0.0419 (14)0.0028 (9)−0.0025 (10)0.0113 (10)
C280.0286 (13)0.0395 (15)0.0486 (16)0.0042 (11)0.0019 (12)0.0147 (12)
C290.0318 (15)0.065 (2)0.073 (2)0.0095 (14)0.0176 (15)0.0388 (17)
C300.0209 (15)0.059 (2)0.119 (3)−0.0032 (14)0.0008 (17)0.059 (2)
C310.0296 (15)0.0306 (15)0.109 (3)−0.0083 (12)−0.0241 (16)0.0281 (16)
C320.0290 (13)0.0260 (13)0.0603 (17)−0.0049 (11)−0.0121 (12)0.0113 (12)
C330.0190 (11)0.0200 (11)0.0198 (11)0.0037 (8)0.0031 (8)0.0002 (9)
C340.0261 (12)0.0227 (12)0.0222 (11)0.0007 (9)0.0005 (9)0.0014 (9)
C350.0297 (12)0.0258 (12)0.0315 (13)−0.0035 (10)−0.0035 (10)−0.0058 (10)
C360.0307 (13)0.0364 (14)0.0249 (13)0.0073 (11)−0.0081 (10)−0.0085 (10)
C370.0342 (13)0.0297 (13)0.0221 (12)0.0101 (10)−0.0015 (10)0.0058 (10)
C380.0259 (12)0.0202 (11)0.0278 (12)0.0015 (9)0.0021 (10)0.0026 (9)
C390.0233 (11)0.0228 (12)0.0232 (12)−0.0010 (9)−0.0122 (9)−0.0034 (9)
C400.0250 (12)0.0263 (12)0.0268 (12)0.0015 (9)−0.0057 (10)−0.0024 (10)
C410.0318 (13)0.0422 (15)0.0254 (13)0.0037 (11)−0.0017 (10)−0.0067 (11)
C420.0475 (16)0.0400 (15)0.0287 (14)0.0195 (12)−0.0079 (12)−0.0144 (11)
C430.0493 (16)0.0221 (12)0.0327 (14)0.0115 (11)−0.0127 (12)−0.0054 (10)
C440.0349 (13)0.0246 (12)0.0239 (12)0.0023 (10)−0.0079 (10)−0.0017 (9)
C450.0185 (11)0.0197 (11)0.0231 (11)−0.0049 (9)0.0015 (9)−0.0011 (9)
C460.0266 (12)0.0259 (12)0.0298 (13)0.0048 (9)−0.0006 (10)−0.0035 (10)
C470.0337 (13)0.0385 (14)0.0234 (12)−0.0037 (11)−0.0006 (10)−0.0048 (10)
C480.0383 (14)0.0292 (13)0.0256 (13)−0.0046 (11)−0.0083 (10)0.0055 (10)
C490.0353 (13)0.0234 (12)0.0318 (13)0.0060 (10)−0.0048 (10)0.0011 (10)
C500.0270 (12)0.0252 (12)0.0213 (12)0.0015 (9)0.0005 (9)−0.0011 (9)
C510.0168 (10)0.0218 (11)0.0232 (11)0.0048 (9)−0.0034 (9)0.0044 (9)
C520.0234 (11)0.0199 (11)0.0253 (12)−0.0017 (9)−0.0007 (9)0.0034 (9)
C530.0300 (12)0.0278 (12)0.0201 (12)0.0019 (10)0.0019 (9)0.0057 (9)
C540.0293 (12)0.0252 (12)0.0203 (12)0.0066 (9)−0.0064 (10)−0.0011 (9)
C550.0201 (11)0.0232 (12)0.0289 (13)−0.0002 (9)−0.0060 (9)0.0011 (9)
C560.0157 (11)0.0270 (12)0.0236 (12)0.0022 (9)0.0003 (9)0.0033 (9)
C570.0253 (12)0.0239 (12)0.0188 (11)−0.0003 (9)0.0019 (9)−0.0003 (9)
C580.0291 (12)0.0245 (12)0.0189 (11)0.0000 (9)0.0027 (9)−0.0001 (9)
C590.0284 (12)0.0354 (13)0.0218 (12)−0.0070 (11)0.0031 (9)0.0011 (10)
C600.0443 (15)0.0271 (13)0.0312 (13)−0.0125 (11)0.0045 (11)0.0014 (10)
C610.0455 (15)0.0236 (13)0.0423 (15)0.0025 (11)0.0029 (12)−0.0007 (11)
C620.0277 (12)0.0274 (13)0.0388 (14)0.0001 (10)0.0037 (10)0.0016 (10)
C630.0222 (11)0.0207 (11)0.0244 (12)0.0023 (9)0.0008 (9)−0.0024 (9)
C640.0244 (12)0.0321 (13)0.0302 (13)0.0014 (10)0.0017 (10)0.0072 (10)
C650.0270 (13)0.0371 (14)0.0419 (15)0.0072 (11)−0.0057 (11)0.0083 (11)
C660.0161 (11)0.0403 (15)0.0495 (16)0.0026 (10)0.0001 (11)0.0019 (12)
C670.0250 (12)0.0343 (13)0.0345 (14)−0.0009 (10)0.0070 (10)0.0006 (11)
C680.0247 (12)0.0245 (12)0.0258 (12)0.0027 (9)0.0003 (9)−0.0007 (9)
C690.0241 (13)0.091 (2)0.0309 (14)−0.0020 (14)0.0028 (11)−0.0040 (14)
C700.0219 (12)0.0317 (13)0.0469 (15)0.0042 (10)−0.0039 (11)0.0097 (11)
C730.0400 (16)0.075 (2)0.0352 (15)0.0169 (14)0.0018 (12)−0.0133 (14)
C740.061 (2)0.088 (3)0.188 (4)−0.029 (2)−0.032 (3)0.067 (3)
B10.0229 (13)0.0165 (12)0.0256 (14)−0.0012 (10)−0.0040 (10)0.0019 (10)
B20.0201 (12)0.0201 (13)0.0256 (14)0.0016 (10)0.0000 (10)−0.0010 (10)
S2A0.0255 (7)0.0288 (7)0.0391 (8)0.0034 (5)−0.0019 (5)0.0142 (5)
C71A0.068 (6)0.032 (4)0.057 (5)0.002 (3)0.003 (4)−0.015 (4)
C72A0.166 (9)0.042 (4)0.044 (4)0.014 (5)−0.050 (5)0.008 (3)
S2B0.0233 (7)0.0374 (7)0.0326 (8)0.0003 (5)0.0000 (5)0.0149 (5)
C71B0.066 (6)0.024 (4)0.118 (10)−0.004 (4)−0.057 (7)0.015 (5)
C72B0.022 (3)0.039 (3)0.034 (3)0.002 (2)−0.004 (2)0.015 (3)
Geometric parameters (Å, º) top
Zn1—O12.0671 (13)C37—H370.9300
Zn1—N22.1055 (16)C38—H380.9300
Zn1—N32.1076 (16)C39—C441.399 (3)
Zn1—N42.1390 (16)C39—C401.412 (3)
Zn1—N12.1586 (17)C39—B11.642 (3)
Zn1—O22.1814 (14)C40—C411.391 (3)
S1—O11.5316 (14)C40—H400.9300
S1—C691.767 (2)C41—C421.379 (3)
S1—C701.769 (2)C41—H410.9300
S3—O31.514 (2)C42—C431.377 (3)
S3—C731.763 (2)C42—H420.9300
S3—C741.769 (3)C43—C441.394 (3)
O2—S2A1.5425 (17)C43—H430.9300
O2—S2B1.5854 (18)C44—H440.9300
N1—C11.334 (2)C45—C501.396 (3)
N1—C51.354 (3)C45—C461.404 (3)
N2—C101.345 (2)C45—B21.647 (3)
N2—C61.348 (2)C46—C471.381 (3)
N3—C111.341 (2)C46—H460.9300
N3—C151.350 (2)C47—C481.384 (3)
N4—C201.339 (3)C47—H470.9300
N4—C161.356 (2)C48—C491.383 (3)
C1—C21.376 (3)C48—H480.9300
C1—H10.9300C49—C501.393 (3)
C2—C31.383 (3)C49—H490.9300
C2—H20.9300C50—H500.9300
C3—C41.381 (3)C51—C521.402 (3)
C3—H30.9300C51—C561.404 (3)
C4—C51.385 (3)C51—B21.663 (3)
C4—H40.9300C52—C531.393 (3)
C5—C61.503 (3)C52—H520.9300
C6—C71.372 (3)C53—C541.381 (3)
C7—C81.391 (3)C53—H530.9300
C7—H70.9300C54—C551.391 (3)
C8—C91.363 (3)C54—H540.9300
C8—H80.9300C55—C561.389 (3)
C9—C101.379 (3)C55—H550.9300
C9—H90.9300C56—H560.9300
C10—H100.9300C57—C621.400 (3)
C11—C121.378 (3)C57—C581.408 (3)
C11—H110.9300C57—B21.646 (3)
C12—C131.380 (3)C58—C591.392 (3)
C12—H120.9300C58—H580.9300
C13—C141.381 (3)C59—C601.387 (3)
C13—H130.9300C59—H590.9300
C14—C151.390 (3)C60—C611.384 (3)
C14—H140.9300C60—H600.9300
C15—C161.494 (3)C61—C621.392 (3)
C16—C171.387 (3)C61—H610.9300
C17—C181.382 (3)C62—H620.9300
C17—H170.9300C63—C641.400 (3)
C18—C191.379 (3)C63—C681.404 (3)
C18—H180.9300C63—B21.648 (3)
C19—C201.380 (3)C64—C651.389 (3)
C19—H190.9300C64—H640.9300
C20—H200.9300C65—C661.377 (3)
C21—C221.400 (3)C65—H650.9300
C21—C261.408 (3)C66—C671.381 (3)
C21—B11.651 (3)C66—H660.9300
C22—C231.391 (3)C67—C681.397 (3)
C22—H220.9300C67—H670.9300
C23—C241.381 (3)C68—H680.9300
C23—H230.9300C69—H69A0.9600
C24—C251.383 (3)C69—H69B0.9600
C24—H240.9300C69—H69C0.9600
C25—C261.389 (3)C70—H70A0.9600
C25—H250.9300C70—H70B0.9600
C26—H260.9300C70—H70C0.9600
C27—C281.395 (3)C73—H73A0.9600
C27—C321.399 (3)C73—H73B0.9600
C27—B11.643 (3)C73—H73C0.9600
C28—C291.400 (3)C74—H74A0.9600
C28—H280.9300C74—H74B0.9600
C29—C301.370 (4)C74—H74C0.9600
C29—H290.9300S2A—C71A1.756 (9)
C30—C311.380 (4)S2A—C72A1.763 (6)
C30—H300.9300C71A—H71D0.9600
C31—C321.395 (3)C71A—H71E0.9600
C31—H310.9300C71A—H71F0.9600
C32—H320.9300C72A—H72D0.9600
C33—C341.399 (3)C72A—H72E0.9600
C33—C381.404 (3)C72A—H72F0.9600
C33—B11.645 (3)S2B—C71B1.754 (8)
C34—C351.394 (3)S2B—C72B1.779 (5)
C34—H340.9300C71B—H71A0.9600
C35—C361.384 (3)C71B—H71B0.9600
C35—H350.9300C71B—H71C0.9600
C36—C371.388 (3)C72B—H72A0.9600
C36—H360.9300C72B—H72B0.9600
C37—C381.381 (3)C72B—H72C0.9600
O1—Zn1—N293.00 (6)C37—C38—C33123.3 (2)
O1—Zn1—N391.39 (6)C37—C38—H38118.3
N2—Zn1—N3174.92 (6)C33—C38—H38118.3
O1—Zn1—N4168.40 (6)C44—C39—C40115.10 (19)
N2—Zn1—N498.58 (6)C44—C39—B1124.17 (19)
N3—Zn1—N477.02 (6)C40—C39—B1120.43 (18)
O1—Zn1—N190.16 (6)C41—C40—C39122.5 (2)
N2—Zn1—N177.36 (6)C41—C40—H40118.7
N3—Zn1—N1100.08 (6)C39—C40—H40118.7
N4—Zn1—N191.92 (6)C42—C41—C40120.1 (2)
O1—Zn1—O292.09 (6)C42—C41—H41119.9
N2—Zn1—O288.28 (6)C40—C41—H41119.9
N3—Zn1—O294.12 (6)C43—C42—C41119.4 (2)
N4—Zn1—O288.72 (6)C43—C42—H42120.3
N1—Zn1—O2165.57 (6)C41—C42—H42120.3
O1—S1—C69103.26 (10)C42—C43—C44120.1 (2)
O1—S1—C70105.77 (9)C42—C43—H43119.9
C69—S1—C7098.96 (12)C44—C43—H43119.9
O3—S3—C73104.10 (12)C43—C44—C39122.7 (2)
O3—S3—C74107.78 (16)C43—C44—H44118.6
C73—S3—C7497.08 (17)C39—C44—H44118.6
S1—O1—Zn1123.71 (8)C50—C45—C46114.75 (18)
S2A—O2—S2B49.91 (7)C50—C45—B2123.78 (18)
S2A—O2—Zn1118.20 (9)C46—C45—B2121.27 (18)
S2B—O2—Zn1146.23 (10)C47—C46—C45123.3 (2)
C1—N1—C5118.45 (18)C47—C46—H46118.3
C1—N1—Zn1126.88 (15)C45—C46—H46118.3
C5—N1—Zn1114.65 (13)C46—C47—C48120.1 (2)
C10—N2—C6118.21 (17)C46—C47—H47120.0
C10—N2—Zn1124.60 (14)C48—C47—H47120.0
C6—N2—Zn1117.01 (13)C49—C48—C47118.8 (2)
C11—N3—C15119.04 (17)C49—C48—H48120.6
C11—N3—Zn1124.28 (13)C47—C48—H48120.6
C15—N3—Zn1116.62 (13)C48—C49—C50120.2 (2)
C20—N4—C16118.57 (17)C48—C49—H49119.9
C20—N4—Zn1125.51 (14)C50—C49—H49119.9
C16—N4—Zn1115.77 (13)C49—C50—C45122.8 (2)
N1—C1—C2123.6 (2)C49—C50—H50118.6
N1—C1—H1118.2C45—C50—H50118.6
C2—C1—H1118.2C52—C51—C56114.67 (18)
C1—C2—C3117.9 (2)C52—C51—B2126.69 (18)
C1—C2—H2121.1C56—C51—B2118.50 (17)
C3—C2—H2121.1C53—C52—C51122.52 (19)
C4—C3—C2119.5 (2)C53—C52—H52118.7
C4—C3—H3120.3C51—C52—H52118.7
C2—C3—H3120.3C54—C53—C52120.8 (2)
C3—C4—C5119.4 (2)C54—C53—H53119.6
C3—C4—H4120.3C52—C53—H53119.6
C5—C4—H4120.3C53—C54—C55118.65 (19)
N1—C5—C4121.2 (2)C53—C54—H54120.7
N1—C5—C6115.79 (18)C55—C54—H54120.7
C4—C5—C6123.0 (2)C56—C55—C54119.6 (2)
N2—C6—C7122.01 (19)C56—C55—H55120.2
N2—C6—C5115.17 (18)C54—C55—H55120.2
C7—C6—C5122.79 (19)C55—C56—C51123.68 (19)
C6—C7—C8118.5 (2)C55—C56—H56118.2
C6—C7—H7120.7C51—C56—H56118.2
C8—C7—H7120.7C62—C57—C58114.76 (19)
C9—C8—C7120.2 (2)C62—C57—B2125.26 (18)
C9—C8—H8119.9C58—C57—B2119.75 (18)
C7—C8—H8119.9C59—C58—C57123.1 (2)
C8—C9—C10118.1 (2)C59—C58—H58118.5
C8—C9—H9120.9C57—C58—H58118.5
C10—C9—H9120.9C60—C59—C58120.0 (2)
N2—C10—C9122.92 (19)C60—C59—H59120.0
N2—C10—H10118.5C58—C59—H59120.0
C9—C10—H10118.5C61—C60—C59118.9 (2)
N3—C11—C12122.67 (19)C61—C60—H60120.5
N3—C11—H11118.7C59—C60—H60120.5
C12—C11—H11118.7C60—C61—C62120.2 (2)
C11—C12—C13118.38 (19)C60—C61—H61119.9
C11—C12—H12120.8C62—C61—H61119.9
C13—C12—H12120.8C61—C62—C57123.1 (2)
C12—C13—C14119.68 (19)C61—C62—H62118.5
C12—C13—H13120.2C57—C62—H62118.5
C14—C13—H13120.2C64—C63—C68114.67 (18)
C13—C14—C15119.09 (18)C64—C63—B2120.96 (18)
C13—C14—H14120.5C68—C63—B2124.25 (18)
C15—C14—H14120.5C65—C64—C63123.2 (2)
N3—C15—C14121.08 (18)C65—C64—H64118.4
N3—C15—C16115.36 (17)C63—C64—H64118.4
C14—C15—C16123.50 (17)C66—C65—C64120.3 (2)
N4—C16—C17121.15 (18)C66—C65—H65119.8
N4—C16—C15114.83 (17)C64—C65—H65119.8
C17—C16—C15123.92 (18)C65—C66—C67118.9 (2)
C18—C17—C16119.45 (19)C65—C66—H66120.5
C18—C17—H17120.3C67—C66—H66120.5
C16—C17—H17120.3C66—C67—C68120.1 (2)
C19—C18—C17119.3 (2)C66—C67—H67119.9
C19—C18—H18120.3C68—C67—H67119.9
C17—C18—H18120.3C67—C68—C63122.8 (2)
C18—C19—C20118.5 (2)C67—C68—H68118.6
C18—C19—H19120.7C63—C68—H68118.6
C20—C19—H19120.7S1—C69—H69A109.5
N4—C20—C19122.98 (19)S1—C69—H69B109.5
N4—C20—H20118.5H69A—C69—H69B109.5
C19—C20—H20118.5S1—C69—H69C109.5
C22—C21—C26114.67 (18)H69A—C69—H69C109.5
C22—C21—B1123.45 (18)H69B—C69—H69C109.5
C26—C21—B1121.49 (18)S1—C70—H70A109.5
C23—C22—C21123.08 (19)S1—C70—H70B109.5
C23—C22—H22118.5H70A—C70—H70B109.5
C21—C22—H22118.5S1—C70—H70C109.5
C24—C23—C22120.1 (2)H70A—C70—H70C109.5
C24—C23—H23119.9H70B—C70—H70C109.5
C22—C23—H23119.9S3—C73—H73A109.5
C23—C24—C25119.06 (19)S3—C73—H73B109.5
C23—C24—H24120.5H73A—C73—H73B109.5
C25—C24—H24120.5S3—C73—H73C109.5
C24—C25—C26120.0 (2)H73A—C73—H73C109.5
C24—C25—H25120.0H73B—C73—H73C109.5
C26—C25—H25120.0S3—C74—H74A109.5
C25—C26—C21123.0 (2)S3—C74—H74B109.5
C25—C26—H26118.5H74A—C74—H74B109.5
C21—C26—H26118.5S3—C74—H74C109.5
C28—C27—C32114.9 (2)H74A—C74—H74C109.5
C28—C27—B1122.4 (2)H74B—C74—H74C109.5
C32—C27—B1122.1 (2)C39—B1—C27113.36 (17)
C27—C28—C29122.7 (3)C39—B1—C33104.00 (16)
C27—C28—H28118.7C27—B1—C33111.51 (17)
C29—C28—H28118.7C39—B1—C21112.87 (17)
C30—C29—C28120.4 (3)C27—B1—C21102.83 (16)
C30—C29—H29119.8C33—B1—C21112.58 (16)
C28—C29—H29119.8C57—B2—C63113.08 (17)
C29—C30—C31119.1 (3)C57—B2—C45105.14 (16)
C29—C30—H30120.5C63—B2—C45112.13 (17)
C31—C30—H30120.5C57—B2—C51112.21 (17)
C30—C31—C32119.9 (3)C63—B2—C51103.83 (16)
C30—C31—H31120.0C45—B2—C51110.63 (16)
C32—C31—H31120.0O2—S2A—C71A104.9 (4)
C31—C32—C27123.1 (3)O2—S2A—C72A99.7 (3)
C31—C32—H32118.5C71A—S2A—C72A101.2 (4)
C27—C32—H32118.5O2—S2B—C71B103.7 (4)
C34—C33—C38114.89 (18)O2—S2B—C72B104.50 (19)
C34—C33—B1124.51 (17)C71B—S2B—C72B98.3 (4)
C38—C33—B1120.30 (17)S2B—C71B—H71A109.5
C35—C34—C33122.75 (19)S2B—C71B—H71B109.5
C35—C34—H34118.6H71A—C71B—H71B109.5
C33—C34—H34118.6S2B—C71B—H71C109.5
C36—C35—C34120.2 (2)H71A—C71B—H71C109.5
C36—C35—H35119.9H71B—C71B—H71C109.5
C34—C35—H35119.9S2B—C72B—H72A109.5
C35—C36—C37118.8 (2)S2B—C72B—H72B109.5
C35—C36—H36120.6H72A—C72B—H72B109.5
C37—C36—H36120.6S2B—C72B—H72C109.5
C38—C37—C36120.0 (2)H72A—C72B—H72C109.5
C38—C37—H37120.0H72B—C72B—H72C109.5
C36—C37—H37120.0
C69—S1—O1—Zn1150.41 (12)C32—C27—C28—C290.6 (3)
C70—S1—O1—Zn1−106.12 (12)B1—C27—C28—C29−171.0 (2)
N2—Zn1—O1—S136.34 (10)C27—C28—C29—C30−0.2 (4)
N3—Zn1—O1—S1−146.23 (10)C28—C29—C30—C31−0.4 (4)
N4—Zn1—O1—S1−145.9 (3)C29—C30—C31—C320.6 (4)
N1—Zn1—O1—S1113.69 (10)C30—C31—C32—C27−0.2 (4)
O2—Zn1—O1—S1−52.05 (10)C28—C27—C32—C31−0.4 (3)
O1—Zn1—O2—S2A−140.15 (11)B1—C27—C32—C31171.2 (2)
N2—Zn1—O2—S2A126.91 (11)C38—C33—C34—C350.4 (3)
N3—Zn1—O2—S2A−48.61 (11)B1—C33—C34—C35174.04 (19)
N4—Zn1—O2—S2A28.28 (11)C33—C34—C35—C360.5 (3)
N1—Zn1—O2—S2A121.0 (2)C34—C35—C36—C37−0.8 (3)
O1—Zn1—O2—S2B−81.01 (19)C35—C36—C37—C380.1 (3)
N2—Zn1—O2—S2B−173.95 (19)C36—C37—C38—C330.9 (3)
N3—Zn1—O2—S2B10.54 (19)C34—C33—C38—C37−1.1 (3)
N4—Zn1—O2—S2B87.42 (19)B1—C33—C38—C37−175.04 (19)
N1—Zn1—O2—S2B−179.84 (19)C44—C39—C40—C410.4 (3)
O1—Zn1—N1—C185.16 (17)B1—C39—C40—C41−173.66 (18)
N2—Zn1—N1—C1178.20 (18)C39—C40—C41—C42−0.6 (3)
N3—Zn1—N1—C1−6.28 (18)C40—C41—C42—C430.7 (3)
N4—Zn1—N1—C1−83.43 (17)C41—C42—C43—C44−0.7 (3)
O2—Zn1—N1—C1−175.8 (2)C42—C43—C44—C390.5 (3)
O1—Zn1—N1—C5−93.39 (14)C40—C39—C44—C43−0.3 (3)
N2—Zn1—N1—C5−0.34 (14)B1—C39—C44—C43173.45 (19)
N3—Zn1—N1—C5175.18 (14)C50—C45—C46—C471.8 (3)
N4—Zn1—N1—C598.02 (14)B2—C45—C46—C47176.8 (2)
O2—Zn1—N1—C55.7 (3)C45—C46—C47—C48−1.6 (3)
O1—Zn1—N2—C10−85.83 (15)C46—C47—C48—C490.2 (3)
N4—Zn1—N2—C1094.62 (16)C47—C48—C49—C500.8 (3)
N1—Zn1—N2—C10−175.33 (16)C48—C49—C50—C45−0.5 (3)
O2—Zn1—N2—C106.17 (15)C46—C45—C50—C49−0.7 (3)
O1—Zn1—N2—C689.30 (14)B2—C45—C50—C49−175.57 (19)
N4—Zn1—N2—C6−90.25 (14)C56—C51—C52—C53−0.6 (3)
N1—Zn1—N2—C6−0.20 (14)B2—C51—C52—C53175.05 (19)
O2—Zn1—N2—C6−178.69 (14)C51—C52—C53—C54−1.3 (3)
O1—Zn1—N3—C112.14 (16)C52—C53—C54—C552.3 (3)
N4—Zn1—N3—C11−177.79 (17)C53—C54—C55—C56−1.4 (3)
N1—Zn1—N3—C1192.56 (16)C54—C55—C56—C51−0.5 (3)
O2—Zn1—N3—C11−90.06 (16)C52—C51—C56—C551.5 (3)
O1—Zn1—N3—C15−174.96 (14)B2—C51—C56—C55−174.51 (18)
N4—Zn1—N3—C155.11 (13)C62—C57—C58—C590.8 (3)
N1—Zn1—N3—C15−84.54 (14)B2—C57—C58—C59175.60 (19)
O2—Zn1—N3—C1592.84 (14)C57—C58—C59—C600.3 (3)
O1—Zn1—N4—C20173.3 (3)C58—C59—C60—C61−0.9 (3)
N2—Zn1—N4—C20−8.94 (18)C59—C60—C61—C620.4 (3)
N3—Zn1—N4—C20173.65 (18)C60—C61—C62—C570.9 (4)
N1—Zn1—N4—C20−86.45 (18)C58—C57—C62—C61−1.4 (3)
O2—Zn1—N4—C2079.13 (18)B2—C57—C62—C61−175.9 (2)
O1—Zn1—N4—C16−2.2 (4)C68—C63—C64—C65−1.6 (3)
N2—Zn1—N4—C16175.56 (14)B2—C63—C64—C65−177.9 (2)
N3—Zn1—N4—C16−1.85 (13)C63—C64—C65—C660.3 (4)
N1—Zn1—N4—C1698.05 (14)C64—C65—C66—C671.2 (4)
O2—Zn1—N4—C16−96.37 (14)C65—C66—C67—C68−1.2 (3)
C5—N1—C1—C2−0.2 (3)C66—C67—C68—C63−0.2 (3)
Zn1—N1—C1—C2−178.68 (16)C64—C63—C68—C671.6 (3)
N1—C1—C2—C3−0.2 (3)B2—C63—C68—C67177.65 (19)
C1—C2—C3—C40.3 (4)C44—C39—B1—C2727.5 (3)
C2—C3—C4—C50.0 (4)C40—C39—B1—C27−159.10 (18)
C1—N1—C5—C40.5 (3)C44—C39—B1—C33−93.8 (2)
Zn1—N1—C5—C4179.13 (17)C40—C39—B1—C3379.6 (2)
C1—N1—C5—C6−177.89 (18)C44—C39—B1—C21143.85 (19)
Zn1—N1—C5—C60.8 (2)C40—C39—B1—C21−42.7 (2)
C3—C4—C5—N1−0.4 (3)C28—C27—B1—C39−149.10 (19)
C3—C4—C5—C6177.9 (2)C32—C27—B1—C3939.9 (3)
C10—N2—C6—C7−2.3 (3)C28—C27—B1—C33−32.1 (3)
Zn1—N2—C6—C7−177.75 (16)C32—C27—B1—C33156.83 (19)
C10—N2—C6—C5176.11 (17)C28—C27—B1—C2188.7 (2)
Zn1—N2—C6—C50.7 (2)C32—C27—B1—C21−82.3 (2)
N1—C5—C6—N2−1.0 (3)C34—C33—B1—C39−100.8 (2)
C4—C5—C6—N2−179.3 (2)C38—C33—B1—C3972.5 (2)
N1—C5—C6—C7177.43 (19)C34—C33—B1—C27136.68 (19)
C4—C5—C6—C7−0.9 (3)C38—C33—B1—C27−50.0 (2)
N2—C6—C7—C82.3 (3)C34—C33—B1—C2121.7 (3)
C5—C6—C7—C8−176.0 (2)C38—C33—B1—C21−164.99 (18)
C6—C7—C8—C9−1.0 (3)C22—C21—B1—C39−25.4 (3)
C7—C8—C9—C10−0.3 (3)C26—C21—B1—C39162.23 (17)
C6—N2—C10—C90.9 (3)C22—C21—B1—C2797.1 (2)
Zn1—N2—C10—C9176.00 (14)C26—C21—B1—C27−75.3 (2)
C8—C9—C10—N20.4 (3)C22—C21—B1—C33−142.76 (18)
C15—N3—C11—C12−0.2 (3)C26—C21—B1—C3344.9 (2)
Zn1—N3—C11—C12−177.21 (15)C62—C57—B2—C63−6.7 (3)
N3—C11—C12—C132.1 (3)C58—C57—B2—C63179.14 (18)
C11—C12—C13—C14−1.8 (3)C62—C57—B2—C45116.0 (2)
C12—C13—C14—C15−0.2 (3)C58—C57—B2—C45−58.2 (2)
C11—N3—C15—C14−1.9 (3)C62—C57—B2—C51−123.7 (2)
Zn1—N3—C15—C14175.33 (14)C58—C57—B2—C5162.1 (2)
C11—N3—C15—C16175.37 (17)C64—C63—B2—C57−53.1 (3)
Zn1—N3—C15—C16−7.4 (2)C68—C63—B2—C57131.0 (2)
C13—C14—C15—N32.1 (3)C64—C63—B2—C45−171.78 (18)
C13—C14—C15—C16−174.98 (18)C68—C63—B2—C4512.4 (3)
C20—N4—C16—C17−0.5 (3)C64—C63—B2—C5168.8 (2)
Zn1—N4—C16—C17175.30 (15)C68—C63—B2—C51−107.1 (2)
C20—N4—C16—C15−177.14 (18)C50—C45—B2—C57100.5 (2)
Zn1—N4—C16—C15−1.3 (2)C46—C45—B2—C57−74.0 (2)
N3—C15—C16—N45.7 (2)C50—C45—B2—C63−136.23 (19)
C14—C15—C16—N4−177.10 (18)C46—C45—B2—C6349.2 (2)
N3—C15—C16—C17−170.81 (18)C50—C45—B2—C51−20.8 (3)
C14—C15—C16—C176.4 (3)C46—C45—B2—C51164.63 (18)
N4—C16—C17—C18−0.9 (3)C52—C51—B2—C57−0.6 (3)
C15—C16—C17—C18175.40 (19)C56—C51—B2—C57174.88 (17)
C16—C17—C18—C191.3 (3)C52—C51—B2—C63−123.1 (2)
C17—C18—C19—C20−0.3 (3)C56—C51—B2—C6352.4 (2)
C16—N4—C20—C191.6 (3)C52—C51—B2—C45116.4 (2)
Zn1—N4—C20—C19−173.82 (16)C56—C51—B2—C45−68.0 (2)
C18—C19—C20—N4−1.1 (3)S2B—O2—S2A—C71A75.0 (3)
C26—C21—C22—C23−1.2 (3)Zn1—O2—S2A—C71A−143.6 (3)
B1—C21—C22—C23−174.09 (18)S2B—O2—S2A—C72A−29.4 (3)
C21—C22—C23—C24−0.2 (3)Zn1—O2—S2A—C72A112.0 (3)
C22—C23—C24—C251.4 (3)S2A—O2—S2B—C71B−65.2 (4)
C23—C24—C25—C26−1.2 (3)Zn1—O2—S2B—C71B−146.7 (4)
C24—C25—C26—C21−0.4 (3)S2A—O2—S2B—C72B37.3 (2)
C22—C21—C26—C251.5 (3)Zn1—O2—S2B—C72B−44.2 (3)
B1—C21—C26—C25174.53 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O3i0.932.413.336 (3)173
C59—H59···O3i0.932.533.403 (3)156
Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C10H8N2)2(C2H6OS)2](C24H20B)2·C2H6OS
Mr1250.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)13.8836 (5), 18.0029 (7), 26.1594 (10)
β (°) 90.225 (3)
V (Å3)6538.4 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.52
Crystal size (mm)0.38 × 0.25 × 0.13
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(DENZO/SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.955, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		44646, 15166, 9478
Rint0.044
(sin θ/λ)max (Å−1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.095, 0.94
No. of reflections15166
No. of parameters820
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.42, −0.48

Computer programs: COLLECT (Nonius, 2000), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL7 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···O3i0.932.413.336 (3)172.9
C59—H59···O3i0.932.533.403 (3)155.6
Symmetry code: (i) −x+1, y−1/2, −z+1/2.
 

Acknowledgements

Financial support from the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program) is gratefully acknowledged.

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1774-m1775
https://doi.org/10.1107/S1600536811048082
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