Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Pages m998-m999
https://doi.org/10.1107/S1600536810028588

[2,3,7,8,13,14,17,18-Octa­kis(ethyl­sulfan­yl)-5,10,15,20-porphyrazinato]zinc(II)

Mehmet Akkurt,a* Naciye Yılmaz Coşkun,b Fatma Aytan Kılıçaslan,b Sabiha Manav Yalçın,b Orhan Büyükgüngörc and Ahmet Güld

aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Faculty of Arts and Sciences, Yıldız Technical University, 34210 Esenler, Istanbul, Turkey, cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey, and dDepartment of Chemistry, Technical University of Istanbul, 34469 Maslak, Ístanbul, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 13 July 2010; accepted 16 July 2010; online 24 July 2010)

In the title compound, [Zn(C32H40N8S8)], the ZnII ion is coordinated by four N atoms in a slightly distorted square-planar environment. In addition, there is a Zn⋯S contact involving a symmetry-related S atom which, when considered, forms a pseudo-square-pyramidal coordination with respect to the ZnII ion. Three of the ethyl groups are disordered over two sites with occupancy ratios of 0.841 (10):0.159 (10), 0.802 (10):0.198 (10) and 0.457 (13):0.543 (13). Weak intra­molecular C—H⋯N and C—H⋯S inter­actions contribute to the stability of the mol­ecular conformation. Inter­molecular C—H⋯S contacts, weak C—H⋯π inter­actions and π–π stacking inter­actions [centroid–centriod distances = 3.832 (4) and 3.850 (5) Å] contribute to the stabilization of the crystal structure.

Related literature

For the synthesis of the title complex, see: Ricciardi et al. (2000[Ricciardi, G., Belviso, S. & Lelj, F. (2000). Inorg. Chem. 39, 1618-1620.]); Belviso et al. (2000[Belviso, S., Ricciardi, G. & Lelj, F. (2000). J. Mater. Chem. 10, 297-304.]). For the synthesis and characterization of porphyrazines and their metal complexes, see: Schramm & Hoffman (1980[Schramm, C. J. & Hoffman, B. M. (1980). Inorg. Chem. 19, 383-385.]); Sakellariou et al. (2000[Sakellariou, E. G., Montalban, A. G., Meunier, H. G., Ostler, R. B., Rumbles, G., Baret, A. G. M. & Hoffman, B. M. (2000). J. Photochem. Photobiol. A, 136, 185-187.]); Ramirez et al. (2004[Ramirez, C., Antonacci, C., Ferraira, J. & Sheardy, R. D. (2004). Synth. Commun. 34, 3373-3379.]). For the Zr(IV), Mn(III), Fe(III), Cu(II), Ni(II) and some lanthanide complexes of (ethyl­sulfan­yl) porphyrazines, see: Ricciardi et al.(1996a[Ricciardi, G., Alfonso, B., Alessandro, B., Angela, R., Francesco, L. & Francesca, B. (1996a). J. Chem. Soc. Dalton Trans. 13, 2799-2807.],b[Ricciardi, G., De Benedetto, L. & Lelj, F. (1996b). Polyhedron, 15, 3183-3191.], 1998[Ricciardi, G., Belviso, S., Lelj, F. & Ristori, S. (1998). J. Porphyrins Phthalocyanins, 2, 177-188.], 1999[Ricciardi, G., Rosa, A., Ciofini, I. & Bencini, A. (1999). Inorg. Chem. 38, 1422-1431.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C32H40N8S8)]

  • Mr = 858.67

  • Orthorhombic, P b c a

  • a = 8.7973 (1) Å

  • b = 27.2813 (3) Å

  • c = 32.0903 (6) Å

  • V = 7701.73 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.11 mm−1

  • T = 295 K

  • 0.60 × 0.37 × 0.13 mm
Data collection

  • Stoe IPDS 2 diffractometer

  • Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.620, Tmax = 0.866

  • 7282 measured reflections

  • 7282 independent reflections

  • 5696 reflections with I > 2σ(I)
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.097

  • S = 1.05

  • 7282 reflections

  • 466 parameters

  • 16 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—N1 2.004 (2)
Zn1—N3 1.994 (2)
Zn1—N5 2.004 (2)
Zn1—N7 1.994 (2)
Zn1—S5i 2.6364 (9)
Symmetry code: (i) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N3/C9–C12, Zn1/N1/N7/N8/C1/C26 and Zn1/N3/N4/N5/C10/C17 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5A—H5A1⋯S1ii 0.97 2.86 3.764 (5) 155
C7—H7A⋯N2 0.97 2.50 3.014 (5) 113
C21—H21A⋯S4i 0.97 2.77 3.660 (4) 154
C23—H23B⋯S5 0.97 2.69 3.221 (4) 115
C31B—H31D⋯N8 0.97 2.53 3.089 (9) 116
C21—H21B⋯Cg3iii 0.97 2.86 3.536 (3) 128
C22—H22A⋯Cg1iii 0.96 2.90 3.699 (4) 142
C23—H23B⋯Cg2iii 0.97 2.81 3.641 (4) 144
Symmetry codes: (i) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028588/lh5086sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028588/lh5086Isup2.hkl

checkCIF report


Comment top

The synthesis and characterization of porphyrazines (tetrapyrrole macrocycles) and their metal complexes are a topic of growing interest (Schramm & Hoffman, 1980). They have high symmetry, planarity, thermal stability and electronic delocalization. So, these types of compounds have potential applications for interesting optical, electrical, medical and catalytic properties. One synthetic route to octakis-functionalized porphyrazine is the cyclization of the functionalized dicyano precursor in the presence of magnesium alkoxide (Sakellariou et al., 2000; Ramirez et al., 2004). Their properties can be easily modified by attachment of diverse peripheral substituents, heteroatoms or alternation of the cetral metal ion.

The Zr(IV), Mn(III), Fe(III), Cu(II), Ni(II) and some lantanides complexes of (ethylsulfanyl) porphyrazines have been investigated (Ricciardi et al., 1996a,b; 1998; 1999). In this present work, we report the crystal structure of the title compound (I).

In the molecule of (I) shown in Fig. 1, the Zn—N bond distances range from from 1.994 (2) to 2.004 (2) Å. The intermolecular Zn—S distance [2.6364 (9) Å] which leads to a pseudo-square-pyramidal coordination around the ZnII ion, is shorter than the Co—S distances [alternatively 2.789 (5) and 2.842 (5) Å] in ((ethylsulfanyl)porphyrazinato)cobalt(II) (Ricciardi et al., 1999).

The molecular conformation of (I) is stabilized by weak intramolecular C—H···N and C—H···S interactions. In the crystal structure, intermolecular C—H···S contacts (Fig. 2), weak C—H···π interactions and π-π stacking interactions [Cg3···Cg4ii = 3.832 (4) Å and Cg3···Cg5ii = 3.850 (5) Å; symmetry code: (ii) 1/2 + x, y, 1/2 - z; Cg3, Cg4 and Cg5 are the centroids of the N5/C17–C20, N7/C25/C26/C27B/C28 and N7/C25/C26/C27A/C28 rings, respectively] contribute to the stabilization of the crystal structure.

Related literature top

For the synthesis of the title complex, see: Ricciardi et al. (2000); Belviso et al. (2000). For the synthesis and characterization of porphyrazines and their metal complexes, see: Schramm & Hoffman (1980); Sakellariou et al. (2000); Ramirez et al. (2004). For the Zr(IV), Mn(III), Fe(III), Cu(II), Ni(II) and some lantanides complexes of (ethylsulfanyl) porphyrazines, see: Ricciardi et al.(1996a,b, 1998, 1999).

Experimental top

All starting materials and reagents used were of standard analytical grade from Merck, Fluka and Aldrich. The title complex were synthesized according to literature (Ricciardi et al., 2000; Belviso et al., 2000).

2,3,7,8,13,17,18-Octakis(ethylsulfanyl)-5,10,15,20-porphyrazine (0.1 g, 0.12 mmol) was dissolved in CHCl3 and added to the solution of Zn(CH3COO)2.4H2O (0.306 g, 1.2 mmol) in EtOH. The mixture was refluxed under argon for 1 h. After cooling to room temperature, insoluble excess Zn(CH3COO)2 was separeted by filtering. The filtrate was evaporated and the resulting deep blue solid was purified by chromatography on silica gel using CHCl3. For single-crystal, compound (I) has been crystalized at CHCl3/ MeOH (1/9).

Refinement top

H atoms were positioned geometrically with C—H = 0.96 and 0.97 Å and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). The three ethyl groups of the title molecule are disordered over two sites in the 0.841 (10):0.159 (10) for C5A/C6A:C5B/C6B, 0.802 (10):0.198 (10) for C13A/C14A:C13B/C14B and 0.457 (13):0.543 (13) for C32A/C33A:C32B/C33B ratios and they were refined isotropicaly for a stable refinement. The S (S8A:S8B) atom with the third ethyl group (C32A/C33A:C32B/C33B) and the C atom (C27A:C27B) of the pyrrole ring attached to are also disorder over two sites in a 0.457 (13):0.543 (13) ratio. In the disorder segments of (I), the DFIX instructions were used to constrain the bond lengths to reasonable values.

Structure description top

The synthesis and characterization of porphyrazines (tetrapyrrole macrocycles) and their metal complexes are a topic of growing interest (Schramm & Hoffman, 1980). They have high symmetry, planarity, thermal stability and electronic delocalization. So, these types of compounds have potential applications for interesting optical, electrical, medical and catalytic properties. One synthetic route to octakis-functionalized porphyrazine is the cyclization of the functionalized dicyano precursor in the presence of magnesium alkoxide (Sakellariou et al., 2000; Ramirez et al., 2004). Their properties can be easily modified by attachment of diverse peripheral substituents, heteroatoms or alternation of the cetral metal ion.

The Zr(IV), Mn(III), Fe(III), Cu(II), Ni(II) and some lantanides complexes of (ethylsulfanyl) porphyrazines have been investigated (Ricciardi et al., 1996a,b; 1998; 1999). In this present work, we report the crystal structure of the title compound (I).

In the molecule of (I) shown in Fig. 1, the Zn—N bond distances range from from 1.994 (2) to 2.004 (2) Å. The intermolecular Zn—S distance [2.6364 (9) Å] which leads to a pseudo-square-pyramidal coordination around the ZnII ion, is shorter than the Co—S distances [alternatively 2.789 (5) and 2.842 (5) Å] in ((ethylsulfanyl)porphyrazinato)cobalt(II) (Ricciardi et al., 1999).

The molecular conformation of (I) is stabilized by weak intramolecular C—H···N and C—H···S interactions. In the crystal structure, intermolecular C—H···S contacts (Fig. 2), weak C—H···π interactions and π-π stacking interactions [Cg3···Cg4ii = 3.832 (4) Å and Cg3···Cg5ii = 3.850 (5) Å; symmetry code: (ii) 1/2 + x, y, 1/2 - z; Cg3, Cg4 and Cg5 are the centroids of the N5/C17–C20, N7/C25/C26/C27B/C28 and N7/C25/C26/C27A/C28 rings, respectively] contribute to the stabilization of the crystal structure.

For the synthesis of the title complex, see: Ricciardi et al. (2000); Belviso et al. (2000). For the synthesis and characterization of porphyrazines and their metal complexes, see: Schramm & Hoffman (1980); Sakellariou et al. (2000); Ramirez et al. (2004). For the Zr(IV), Mn(III), Fe(III), Cu(II), Ni(II) and some lantanides complexes of (ethylsulfanyl) porphyrazines, see: Ricciardi et al.(1996a,b, 1998, 1999).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. The minor occupied sites of the disordered atoms and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the major component of (I) viewed down the a axis. All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
[2,3,7,8,13,14,17,18-Octakis(ethylsulfanyl)-5,10,15,20-porphyrazinato]zinc(II) top
Crystal data top
[Zn(C32H40N8S8)]F(000) = 3568
Mr = 858.67Dx = 1.481 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 86381 reflections
a = 8.7973 (1) Åθ = 1.3–26.2°
b = 27.2813 (3) ŵ = 1.11 mm−1
c = 32.0903 (6) ÅT = 295 K
V = 7701.73 (19) Å3Prism, black
Z = 80.60 × 0.37 × 0.13 mm
Data collection top
Stoe IPDS 2
diffractometer		7282 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus5696 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.000
Detector resolution: 6.67 pixels mm-1θmax = 25.7°, θmin = 1.3°
ω scansh = 0→10
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)		k = 0→33
Tmin = 0.620, Tmax = 0.866l = 0→38
7282 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0526P)2 + 1.401P]
where P = (Fo2 + 2Fc2)/3
7282 reflections(Δ/σ)max = 0.001
466 parametersΔρmax = 0.44 e Å−3
16 restraintsΔρmin = −0.30 e Å−3
Crystal data top
[Zn(C32H40N8S8)]V = 7701.73 (19) Å3
Mr = 858.67Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.7973 (1) ŵ = 1.11 mm−1
b = 27.2813 (3) ÅT = 295 K
c = 32.0903 (6) Å0.60 × 0.37 × 0.13 mm
Data collection top
Stoe IPDS 2
diffractometer		7282 independent reflections
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)		5696 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.866Rint = 0.000
7282 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04016 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.05Δρmax = 0.44 e Å−3
7282 reflectionsΔρmin = −0.30 e Å−3
466 parameters
Special details top

Experimental. (XABS2; Parkin et al., 1995; Cubic fit to sin(theta)/lambda - 24 parameters)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
Zn10.62155 (4)0.18388 (1)0.32349 (1)0.0401 (1)
S10.56218 (12)0.06894 (3)0.47611 (3)0.0617 (3)
S20.79562 (12)0.16274 (3)0.50015 (2)0.0623 (3)
S31.05348 (11)0.31228 (3)0.40786 (3)0.0598 (3)
S41.05456 (10)0.34318 (3)0.30195 (3)0.0579 (3)
S50.88817 (9)0.24250 (3)0.16339 (2)0.0441 (2)
S60.60435 (10)0.14544 (3)0.14841 (2)0.0541 (3)
S70.27372 (11)0.03081 (3)0.23777 (3)0.0579 (3)
S8B0.3114 (11)−0.0068 (2)0.33482 (16)0.0732 (15)0.543 (13)
N10.6525 (3)0.15882 (8)0.38158 (7)0.0413 (8)
N20.8203 (3)0.22106 (8)0.40843 (7)0.0410 (8)
N30.7915 (3)0.23069 (8)0.33388 (7)0.0389 (7)
N40.8438 (3)0.25778 (8)0.26365 (7)0.0385 (7)
N50.6573 (3)0.19305 (8)0.26230 (7)0.0381 (7)
N60.5007 (3)0.12757 (8)0.23537 (7)0.0400 (7)
N70.5143 (3)0.12142 (8)0.31024 (7)0.0406 (7)
N80.4965 (3)0.08565 (8)0.37884 (7)0.0433 (8)
C10.5853 (3)0.11832 (10)0.39820 (9)0.0418 (9)
C20.7336 (3)0.18153 (10)0.41229 (9)0.0421 (9)
C30.7156 (3)0.15368 (11)0.45124 (9)0.0446 (9)
C40.6246 (4)0.11465 (11)0.44202 (8)0.0451 (9)
C5A0.6702 (6)0.01709 (18)0.45794 (17)0.0751 (18)*0.841 (10)
C6A0.8372 (8)0.0233 (3)0.4623 (3)0.120 (3)*0.841 (10)
C70.8662 (6)0.22413 (16)0.50147 (13)0.0883 (18)
C80.9413 (6)0.2340 (2)0.54207 (13)0.101 (2)
C90.8469 (3)0.24323 (10)0.37194 (9)0.0407 (9)
C100.8562 (3)0.26070 (10)0.30526 (9)0.0389 (8)
C110.9524 (3)0.29630 (10)0.32636 (9)0.0424 (9)
C120.9476 (3)0.28539 (10)0.36767 (9)0.0438 (9)
C13A0.9045 (6)0.33738 (18)0.44078 (16)0.0690 (17)*0.802 (10)
C14A0.8356 (9)0.3835 (3)0.4200 (3)0.107 (2)*0.802 (10)
C150.9011 (4)0.37875 (13)0.27885 (13)0.0690 (14)
C160.9640 (6)0.41584 (14)0.24931 (16)0.092 (2)
C170.7582 (3)0.22486 (10)0.24441 (8)0.0372 (8)
C180.5973 (3)0.16502 (10)0.23179 (8)0.0387 (8)
C190.6603 (3)0.17977 (10)0.19120 (8)0.0384 (8)
C200.7609 (3)0.21698 (10)0.19924 (8)0.0385 (8)
C210.9468 (4)0.30188 (11)0.18359 (11)0.0552 (11)
C221.0154 (5)0.33019 (14)0.14801 (12)0.0753 (16)
C230.6966 (4)0.17078 (13)0.10339 (10)0.0573 (11)
C240.6649 (5)0.13667 (17)0.06641 (12)0.0817 (16)
C250.4650 (3)0.10740 (10)0.27176 (9)0.0394 (9)
C260.4646 (3)0.08733 (10)0.33842 (9)0.0403 (9)
C27B0.364 (3)0.0494 (5)0.3159 (4)0.041 (4)0.543 (13)
C280.3731 (3)0.06272 (10)0.27547 (9)0.0416 (9)
C290.3727 (5)0.03955 (17)0.18997 (12)0.0837 (16)
C300.3176 (6)0.00225 (19)0.15882 (14)0.0970 (19)
C31B0.3468 (12)−0.0166 (3)0.3838 (2)0.080 (3)*0.543 (13)
C32B0.2550 (14)−0.0561 (4)0.4038 (3)0.085 (3)*0.543 (13)
C31A0.2574 (14)0.0014 (4)0.3878 (3)0.076 (3)*0.457 (13)
C32A0.1888 (19)−0.0470 (5)0.4029 (4)0.103 (4)*0.457 (13)
C13B0.960 (3)0.3675 (9)0.4188 (14)0.174 (18)*0.198 (10)
C5B0.721 (3)0.0346 (12)0.4914 (8)0.112 (14)*0.159 (10)
C6B0.815 (4)0.0050 (19)0.4767 (16)0.145 (19)*0.159 (10)
S8A0.2570 (7)0.0047 (3)0.3375 (2)0.0643 (14)0.457 (13)
C14B0.804 (2)0.3711 (8)0.4367 (7)0.062 (6)*0.198 (10)
C27A0.386 (3)0.0512 (7)0.3183 (4)0.044 (5)0.457 (13)
H6A10.88780−0.005500.452200.1800*0.841 (10)
H8B0.990200.265400.541100.1520*
H6A20.862200.028400.491100.1800*0.841 (10)
H6A30.869400.051200.446300.1800*0.841 (10)
H7A0.938600.228900.479000.1060*
H7B0.782900.246900.497500.1060*
H8A0.866500.233900.563800.1520*
H5A10.63920−0.011800.473400.0900*0.841 (10)
H5A20.646200.011400.428800.0900*0.841 (10)
H15B0.844100.395200.300600.0820*
H16A1.031700.437400.264000.1380*
H16B0.882300.434500.237500.1380*
H16C1.018600.399400.227500.1380*
H21A0.859900.319300.194800.0660*
H21B1.020900.297700.205700.0660*
H22A1.097900.311800.136300.1130*
H22B1.052500.361100.158000.1130*
H22C0.939400.335700.127100.1130*
H23A0.657400.203300.097700.0690*
H23B0.805200.173300.108200.0690*
H24A0.712000.105500.071300.1230*
H24B0.705600.150900.041400.1230*
H24C0.557200.132300.063400.1230*
H29A0.354300.072400.179500.1000*
H29B0.481100.035700.194400.1000*
H30A0.34790−0.029900.167600.1450*
H30B0.361000.009200.132000.1450*
H30C0.208800.003700.157000.1450*
H31C0.45350−0.024900.386700.0950*0.543 (13)
H31D0.329700.013700.399000.0950*0.543 (13)
H32D0.15860−0.043100.412400.1280*0.543 (13)
H32E0.30830−0.068500.427700.1280*0.543 (13)
H32F0.23910−0.082200.384200.1280*0.543 (13)
H8C1.015600.209000.547500.1520*
H13A0.825700.313000.444900.0830*0.802 (10)
H13B0.946200.345900.467800.0830*0.802 (10)
H14A0.910200.409200.419400.1610*0.802 (10)
H14B0.748600.394200.435700.1610*0.802 (10)
H14C0.805100.375800.392000.1610*0.802 (10)
H15A0.832300.357000.264100.0820*
H5B10.786100.059500.503300.1350*0.159 (10)
H5B20.681400.016700.515200.1350*0.159 (10)
H6B10.88970−0.002500.497400.2170*0.159 (10)
H6B20.863000.019300.452800.2170*0.159 (10)
H6B30.76310−0.024500.468600.2170*0.159 (10)
H13C1.025600.385600.437600.2080*0.198 (10)
H13D0.957500.385800.392900.2080*0.198 (10)
H14D0.780100.341200.451200.0930*0.198 (10)
H14E0.731900.376100.414700.0930*0.198 (10)
H14F0.799600.398100.455800.0930*0.198 (10)
H31A0.360900.004100.397900.0920*0.457 (13)
H31B0.199400.028500.399200.0920*0.457 (13)
H32A0.09080−0.051500.390300.1550*0.457 (13)
H32B0.17820−0.046200.432600.1550*0.457 (13)
H32C0.25440−0.073600.395100.1550*0.457 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0468 (2)0.0382 (2)0.0354 (2)−0.0078 (2)−0.0025 (1)0.0019 (1)
S10.0823 (6)0.0590 (5)0.0437 (4)−0.0114 (5)0.0107 (4)0.0101 (4)
S20.0815 (7)0.0699 (6)0.0356 (4)−0.0123 (5)−0.0052 (4)0.0005 (4)
S30.0621 (5)0.0587 (5)0.0586 (5)−0.0113 (4)−0.0147 (4)−0.0084 (4)
S40.0507 (5)0.0533 (5)0.0696 (5)−0.0140 (4)−0.0031 (4)0.0120 (4)
S50.0476 (4)0.0468 (4)0.0379 (3)−0.0042 (3)0.0024 (3)0.0048 (3)
S60.0644 (5)0.0564 (5)0.0416 (4)−0.0071 (4)−0.0033 (4)−0.0026 (3)
S70.0627 (5)0.0569 (5)0.0542 (5)−0.0169 (4)−0.0044 (4)−0.0068 (4)
S8B0.115 (4)0.0484 (19)0.0562 (13)−0.032 (2)0.008 (2)−0.0002 (13)
N10.0487 (15)0.0380 (13)0.0371 (12)−0.0066 (11)−0.0021 (11)0.0024 (10)
N20.0461 (14)0.0394 (13)0.0375 (12)−0.0025 (11)−0.0038 (11)−0.0004 (10)
N30.0404 (14)0.0378 (12)0.0385 (12)−0.0053 (10)−0.0021 (10)0.0020 (10)
N40.0402 (13)0.0365 (12)0.0389 (12)−0.0016 (10)0.0015 (10)0.0020 (9)
N50.0409 (13)0.0369 (12)0.0365 (12)−0.0035 (10)0.0002 (10)0.0004 (9)
N60.0431 (13)0.0378 (12)0.0390 (13)−0.0019 (11)−0.0014 (10)−0.0007 (10)
N70.0483 (14)0.0354 (12)0.0380 (12)−0.0060 (11)0.0005 (11)0.0008 (10)
N80.0494 (15)0.0392 (13)0.0414 (13)−0.0053 (11)0.0014 (11)0.0021 (10)
C10.0440 (17)0.0424 (16)0.0389 (14)0.0007 (13)0.0022 (12)0.0033 (12)
C20.0455 (17)0.0425 (16)0.0382 (14)0.0020 (13)−0.0013 (12)−0.0011 (12)
C30.0503 (18)0.0477 (16)0.0359 (15)0.0008 (14)0.0029 (13)−0.0002 (12)
C40.0557 (18)0.0447 (16)0.0349 (14)−0.0032 (14)0.0040 (14)0.0034 (12)
C70.123 (4)0.082 (3)0.060 (2)−0.027 (3)−0.024 (2)−0.004 (2)
C80.105 (4)0.133 (4)0.066 (3)−0.039 (3)−0.008 (3)−0.020 (3)
C90.0412 (16)0.0390 (15)0.0418 (15)−0.0005 (12)−0.0030 (12)−0.0025 (12)
C100.0366 (15)0.0373 (14)0.0429 (15)0.0003 (12)−0.0003 (12)0.0022 (12)
C110.0407 (16)0.0375 (14)0.0491 (17)−0.0036 (13)−0.0026 (13)0.0031 (13)
C120.0434 (17)0.0410 (16)0.0471 (16)−0.0044 (13)−0.0080 (14)−0.0040 (12)
C150.072 (2)0.052 (2)0.083 (3)0.0030 (18)0.005 (2)0.0121 (18)
C160.106 (4)0.060 (2)0.109 (4)0.005 (2)0.012 (3)0.026 (2)
C170.0372 (15)0.0372 (14)0.0373 (14)0.0019 (12)0.0020 (12)0.0051 (11)
C180.0392 (16)0.0392 (14)0.0376 (14)0.0037 (12)−0.0016 (12)0.0006 (12)
C190.0423 (16)0.0403 (15)0.0325 (13)0.0042 (12)−0.0015 (11)0.0013 (11)
C200.0395 (15)0.0390 (15)0.0371 (14)0.0010 (12)0.0007 (12)0.0033 (11)
C210.063 (2)0.0427 (17)0.060 (2)−0.0037 (16)0.0114 (17)−0.0012 (14)
C220.098 (3)0.055 (2)0.073 (3)−0.013 (2)0.014 (2)0.0118 (18)
C230.062 (2)0.067 (2)0.0428 (17)0.0045 (17)0.0014 (15)−0.0003 (15)
C240.088 (3)0.105 (3)0.052 (2)0.001 (3)−0.010 (2)−0.017 (2)
C250.0410 (16)0.0350 (14)0.0423 (15)0.0007 (12)−0.0010 (12)−0.0026 (12)
C260.0427 (16)0.0365 (15)0.0418 (15)−0.0008 (13)0.0006 (13)0.0010 (12)
C27B0.034 (6)0.033 (6)0.057 (7)−0.004 (4)−0.010 (4)−0.016 (5)
C280.0418 (16)0.0386 (15)0.0445 (17)−0.0021 (13)−0.0020 (13)−0.0014 (12)
C290.091 (3)0.101 (3)0.059 (2)−0.031 (3)0.007 (2)−0.021 (2)
C300.100 (3)0.117 (4)0.074 (3)−0.020 (3)−0.006 (3)−0.033 (3)
S8A0.063 (2)0.058 (3)0.072 (2)−0.0233 (17)−0.0153 (19)0.021 (2)
C27A0.043 (9)0.048 (8)0.040 (7)−0.017 (5)0.002 (6)0.021 (6)
Geometric parameters (Å, º) top
Zn1—N12.004 (2)C27A—C281.415 (14)
Zn1—N31.994 (2)C27B—C281.350 (13)
Zn1—N52.004 (2)C29—C301.507 (7)
Zn1—N71.994 (2)C31A—C32A1.531 (18)
Zn1—S5i2.6364 (9)C31B—C32B1.492 (14)
S1—C41.747 (3)C5A—H5A10.9700
S1—C5A1.801 (5)C5A—H5A20.9700
S1—C5B1.75 (3)C5B—H5B10.9700
S2—C31.738 (3)C5B—H5B20.9700
S2—C71.787 (5)C6A—H6A30.9600
S3—C121.752 (3)C6A—H6A10.9600
S3—C13A1.817 (5)C6A—H6A20.9600
S3—C13B1.75 (3)C6B—H6B20.9600
S4—C111.748 (3)C6B—H6B10.9600
S4—C151.820 (4)C6B—H6B30.9600
S5—C201.750 (3)C7—H7B0.9700
S5—C211.820 (3)C7—H7A0.9700
S6—C191.734 (3)C8—H8B0.9600
S6—C231.796 (3)C8—H8A0.9600
S7—C281.728 (3)C8—H8C0.9600
S7—C291.780 (4)C13A—H13B0.9700
S8A—C27A1.81 (2)C13A—H13A0.9700
S8A—C31A1.617 (12)C13B—H13C0.9700
S8B—C27B1.713 (16)C13B—H13D0.9700
S8B—C31B1.625 (9)C14A—H14C0.9600
N1—C21.365 (4)C14A—H14A0.9600
N1—C11.362 (4)C14A—H14B0.9600
N2—C21.327 (4)C14B—H14E0.9600
N2—C91.339 (4)C14B—H14D0.9600
N3—C101.356 (4)C14B—H14F0.9600
N3—C91.359 (4)C15—H15A0.9700
N4—C171.325 (4)C15—H15B0.9700
N4—C101.342 (4)C16—H16B0.9600
N5—C171.368 (4)C16—H16C0.9600
N5—C181.350 (3)C16—H16A0.9600
N6—C251.329 (4)C21—H21B0.9700
N6—C181.334 (4)C21—H21A0.9700
N7—C251.364 (4)C22—H22A0.9600
N7—C261.369 (4)C22—H22B0.9600
N8—C11.338 (4)C22—H22C0.9600
N8—C261.328 (4)C23—H23B0.9700
C1—C41.452 (4)C23—H23A0.9700
C2—C31.471 (4)C24—H24B0.9600
C3—C41.365 (4)C24—H24A0.9600
C5A—C6A1.486 (9)C24—H24C0.9600
C5B—C6B1.25 (5)C29—H29B0.9700
C7—C81.485 (6)C29—H29A0.9700
C9—C121.458 (4)C30—H30C0.9600
C10—C111.455 (4)C30—H30A0.9600
C11—C121.359 (4)C30—H30B0.9600
C13A—C14A1.548 (10)C31A—H31B0.9700
C13B—C14B1.49 (3)C31A—H31A0.9700
C15—C161.493 (6)C31B—H31D0.9700
C17—C201.466 (4)C31B—H31C0.9700
C18—C191.472 (4)C32A—H32B0.9600
C19—C201.371 (4)C32A—H32C0.9600
C21—C221.505 (5)C32A—H32A0.9600
C23—C241.534 (5)C32B—H32D0.9600
C25—C281.468 (4)C32B—H32E0.9600
C26—C27B1.542 (19)C32B—H32F0.9600
C26—C27A1.37 (2)
Zn1···H23Bi3.5500C21···N42.978 (4)
S1···S23.3706 (13)C21···S4i3.660 (4)
S1···N83.207 (2)C23···S53.221 (4)
S2···C5B3.57 (3)C25···S7iv3.440 (3)
S2···S3ii3.7036 (13)C25···C18i3.598 (4)
S2···N23.353 (2)C25···C19i3.535 (4)
S2···S13.3706 (13)C26···S6i3.569 (3)
S3···S43.5017 (14)C27B···S6i3.66 (2)
S3···N23.225 (3)C28···S7iv3.655 (3)
S3···S2iii3.7036 (13)C29···S8Aiv3.621 (8)
S4···C21iv3.660 (4)C29···N63.026 (5)
S4···S33.5017 (14)C31A···N83.129 (12)
S4···N43.221 (3)C31B···N83.089 (9)
S5···C233.221 (4)C32B···C13Bvi3.30 (3)
S5···N43.268 (2)C32B···C5Bv3.42 (3)
S5···S63.6711 (12)C1···H23Bi2.8900
S6···S53.6711 (12)C2···H8Bii2.9900
S6···C27Biv3.66 (2)C2···H7A3.0800
S6···N62.976 (2)C3···H24Civ3.1000
S6···C26iv3.569 (3)C3···H8Bii2.9800
S6···C9i3.560 (3)C4···H6A32.7700
S7···C25i3.440 (3)C5B···H32Ev2.7700
S7···S8A3.282 (7)C6A···H30Biv3.0600
S7···S8B3.296 (5)C6B···H6B1viii2.7300
S7···N63.311 (3)C7···H13A3.0500
S7···C28i3.655 (3)C9···H23Aiv3.1000
S8A···S73.282 (7)C9···H13A3.0200
S8A···N83.328 (8)C9···H22Ai2.8900
S8A···C29i3.621 (8)C10···H15A2.9500
S8B···S73.296 (5)C12···H14C2.8700
S8B···N83.318 (7)C13B···H32Eix2.7000
S1···H13Bii3.1100C14A···H6B3ix3.0800
S1···H5A1v2.8600C21···H16C3.0800
S1···H5B2v3.1800C22···H14Eiv3.0400
S1···H13Cii3.0500C26···H31D3.0400
S2···H5B12.8200C32B···H5B2v2.8700
S2···H24Civ3.1800C32B···H13Cvi2.7300
S3···H23Aiv3.1200C32B···H5B1v3.0000
S3···H8Aiii3.1600C32B···H13Dvi3.0100
S4···H21Aiv2.7700H5A1···S1v2.8600
S5···H23A3.1200H5A2···N82.9000
S5···H23B2.6900H6A3···C42.7700
S6···H29A3.1300H5B1···C32Bv3.0000
S7···H16Avi3.1800H5B1···S22.8200
S7···H16Bvii3.0700H5B1···H32Ev2.3800
S8A···H29Bi2.7700H5B2···C32Bv2.8700
S8B···H16Avi3.0600H5B2···H32Ev2.3200
N1···N32.772 (3)H5B2···S1v3.1800
N1···N72.786 (3)H7A···N22.5000
N1···C92.885 (4)H7A···C23.0800
N1···C262.908 (4)H7B···H13A2.5000
N2···S33.225 (3)H6B1···H6B1viii1.9500
N2···C73.014 (5)H6B1···C6Bviii2.7300
N2···S23.353 (2)H8A···S3ii3.1600
N2···C13A3.420 (5)H8B···C3iii2.9800
N3···N52.779 (3)H8B···C2iii2.9900
N3···C22.896 (4)H6B3···H14Bvi2.4600
N3···C172.890 (3)H6B3···C14Avi3.0800
N3···N12.772 (3)H13A···C73.0500
N4···S43.221 (3)H13A···N22.7700
N4···S53.268 (2)H13A···C93.0200
N4···C212.978 (4)H13A···H7B2.5000
N4···C18iv3.376 (4)H13B···S1iii3.1100
N4···C153.374 (4)H13C···S1iii3.0500
N5···C252.901 (4)H13C···C32Bix2.7300
N5···N32.779 (3)H13C···H32Eix1.9500
N5···C102.893 (4)H13D···C32Bix3.0100
N5···N72.787 (3)H13D···H31Cix2.5700
N6···S73.311 (3)H14B···H6B3ix2.4600
N6···S62.976 (2)H14C···C122.8700
N6···C293.026 (5)H14E···C22i3.0400
N7···C182.879 (3)H15A···C102.9500
N7···N52.787 (3)H15A···N42.7100
N7···C12.892 (4)H15A···H21A2.4600
N7···N12.786 (3)H16A···S8Bix3.0600
N7···C20i3.444 (4)H16A···S7ix3.1800
N8···S8B3.318 (7)H16B···S7x3.0700
N8···S8A3.328 (8)H16C···C213.0800
N8···S13.207 (2)H16C···H22B2.4800
N8···C31B3.089 (9)H21A···N42.7800
N8···C31A3.129 (12)H21A···H15A2.4600
N2···H13A2.7700H21A···S4i2.7700
N2···H7A2.5000H21B···N42.6600
N4···H15A2.7100H22A···C9iv2.8900
N4···H21B2.6600H22B···H16C2.4800
N4···H21A2.7800H23A···S3i3.1200
N6···H29B2.8400H23A···C9i3.1000
N6···H29A2.6700H23A···S53.1200
N8···H31D2.5300H23B···Zn1iv3.5500
N8···H5A22.9000H23B···C1iv2.8900
N8···H31A2.6000H23B···S52.6900
C5B···C32Bv3.42 (3)H24A···H31Biv2.3100
C5B···S23.57 (3)H24C···S2i3.1800
C6B···C6Bviii3.59 (5)H24C···C3i3.1000
C7···N23.014 (5)H29A···S63.1300
C9···S6iv3.560 (3)H29A···N62.6700
C10···C18iv3.567 (4)H29B···N62.8400
C10···C19iv3.471 (4)H29B···S8Aiv2.7700
C11···C20iv3.567 (4)H30B···C6Ai3.0600
C13A···N23.420 (5)H31A···N82.6000
C13B···C32Bix3.30 (3)H31B···H24Ai2.3100
C15···N43.374 (4)H31C···H13Dvi2.5700
C17···C18iv3.485 (4)H31D···N82.5300
C18···C17i3.485 (4)H31D···C263.0400
C18···C25iv3.598 (4)H32E···H5B1v2.3800
C18···C10i3.567 (4)H32E···H5B2v2.3200
C18···N4i3.376 (4)H32E···C13Bvi2.7000
C19···C25iv3.535 (4)H32E···H13Cvi1.9500
C19···C10i3.471 (4)H32E···C5Bv2.7700
C20···C11i3.567 (4)
N1—Zn1—N387.77 (10)S1—C5B—H5B2102.00
N1—Zn1—N5158.84 (10)S1—C5B—H5B1102.00
N1—Zn1—N788.35 (9)H6A1—C6A—H6A3109.00
S5i—Zn1—N199.45 (7)H6A1—C6A—H6A2110.00
N3—Zn1—N588.07 (10)C5A—C6A—H6A1109.00
N3—Zn1—N7159.68 (10)C5A—C6A—H6A2109.00
S5i—Zn1—N399.71 (7)C5A—C6A—H6A3109.00
N5—Zn1—N788.40 (9)H6A2—C6A—H6A3109.00
S5i—Zn1—N5101.71 (7)C5B—C6B—H6B2109.00
S5i—Zn1—N7100.60 (8)C5B—C6B—H6B3109.00
C4—S1—C5A101.1 (2)C5B—C6B—H6B1109.00
C4—S1—C5B107.8 (9)H6B1—C6B—H6B3110.00
C3—S2—C7107.19 (17)H6B2—C6B—H6B3109.00
C12—S3—C13A101.67 (19)H6B1—C6B—H6B2110.00
C12—S3—C13B105.0 (12)C8—C7—H7A110.00
C11—S4—C15101.02 (15)H7A—C7—H7B108.00
C20—S5—C21107.54 (15)S2—C7—H7B110.00
Zn1iv—S5—C2098.74 (9)C8—C7—H7B110.00
Zn1iv—S5—C21105.22 (11)S2—C7—H7A110.00
C19—S6—C23107.52 (15)C7—C8—H8A109.00
C28—S7—C29106.76 (17)H8B—C8—H8C110.00
C27A—S8A—C31A112.2 (7)C7—C8—H8B109.00
C27B—S8B—C31B116.0 (7)C7—C8—H8C109.00
Zn1—N1—C2125.99 (18)H8A—C8—H8B110.00
C1—N1—C2108.2 (2)H8A—C8—H8C109.00
Zn1—N1—C1125.59 (19)S3—C13A—H13B110.00
C2—N2—C9123.3 (2)C14A—C13A—H13A110.00
Zn1—N3—C9125.48 (19)S3—C13A—H13A110.00
Zn1—N3—C10126.03 (19)H13A—C13A—H13B108.00
C9—N3—C10107.8 (2)C14A—C13A—H13B110.00
C10—N4—C17123.4 (2)S3—C13B—H13D106.00
Zn1—N5—C17126.32 (18)C14B—C13B—H13C106.00
Zn1—N5—C18125.35 (19)H13C—C13B—H13D107.00
C17—N5—C18108.0 (2)C14B—C13B—H13D106.00
C18—N6—C25122.9 (2)S3—C13B—H13C106.00
Zn1—N7—C25125.69 (18)H14A—C14A—H14C109.00
C25—N7—C26107.8 (2)C13A—C14A—H14A110.00
Zn1—N7—C26126.23 (19)C13A—C14A—H14B109.00
C1—N8—C26123.6 (2)C13A—C14A—H14C110.00
N1—C1—C4109.4 (2)H14A—C14A—H14B109.00
N8—C1—C4122.9 (3)H14B—C14A—H14C110.00
N1—C1—N8127.7 (3)C13B—C14B—H14D109.00
N1—C2—N2127.0 (3)C13B—C14B—H14E110.00
N2—C2—C3124.1 (3)C13B—C14B—H14F110.00
N1—C2—C3108.8 (2)H14D—C14B—H14E109.00
S2—C3—C2130.6 (2)H14D—C14B—H14F109.00
C2—C3—C4106.4 (2)H14E—C14B—H14F110.00
S2—C3—C4123.0 (2)S4—C15—H15B110.00
S1—C4—C1125.5 (2)C16—C15—H15A110.00
S1—C4—C3127.3 (2)S4—C15—H15A110.00
C1—C4—C3107.2 (2)H15A—C15—H15B108.00
S1—C5A—C6A113.7 (4)C16—C15—H15B110.00
S1—C5B—C6B140 (3)C15—C16—H16B109.00
S2—C7—C8110.2 (3)C15—C16—H16A109.00
N3—C9—C12109.4 (2)C15—C16—H16C109.00
N2—C9—C12123.0 (3)H16A—C16—H16B109.00
N2—C9—N3127.6 (2)H16A—C16—H16C109.00
N3—C10—C11109.4 (2)H16B—C16—H16C110.00
N3—C10—N4127.2 (2)H21A—C21—H21B108.00
N4—C10—C11123.4 (2)C22—C21—H21A110.00
S4—C11—C12127.8 (2)C22—C21—H21B110.00
S4—C11—C10125.4 (2)S5—C21—H21A110.00
C10—C11—C12106.8 (2)S5—C21—H21B110.00
S3—C12—C11127.6 (2)C21—C22—H22A109.00
C9—C12—C11106.5 (2)C21—C22—H22B110.00
S3—C12—C9125.7 (2)C21—C22—H22C109.00
S3—C13A—C14A109.8 (4)H22A—C22—H22B109.00
S3—C13B—C14B124.5 (18)H22A—C22—H22C110.00
S4—C15—C16110.2 (3)H22B—C22—H22C109.00
N4—C17—N5127.1 (2)S6—C23—H23A110.00
N5—C17—C20109.4 (2)S6—C23—H23B110.00
N4—C17—C20123.5 (2)C24—C23—H23B110.00
N6—C18—C19121.7 (2)H23A—C23—H23B108.00
N5—C18—N6128.4 (2)C24—C23—H23A110.00
N5—C18—C19109.9 (2)H24A—C24—H24B110.00
S6—C19—C18116.5 (2)H24A—C24—H24C109.00
S6—C19—C20137.1 (2)C23—C24—H24A109.00
C18—C19—C20106.2 (2)C23—C24—H24B109.00
S5—C20—C17127.0 (2)C23—C24—H24C109.00
S5—C20—C19125.7 (2)H24B—C24—H24C110.00
C17—C20—C19106.5 (2)S7—C29—H29B110.00
S5—C21—C22107.5 (2)S7—C29—H29A110.00
S6—C23—C24107.9 (3)H29A—C29—H29B108.00
N6—C25—N7127.2 (2)C30—C29—H29A110.00
N6—C25—C28123.1 (3)C30—C29—H29B110.00
N7—C25—C28109.6 (2)C29—C30—H30A109.00
N8—C26—C27B123.8 (5)C29—C30—H30C109.00
N8—C26—C27A122.9 (7)H30A—C30—H30B109.00
N7—C26—N8127.0 (2)C29—C30—H30B109.00
N7—C26—C27B109.3 (5)H30B—C30—H30C109.00
N7—C26—C27A109.9 (7)H30A—C30—H30C109.00
S8A—C27A—C28115.9 (14)S8A—C31A—H31B109.00
S8A—C27A—C26131.5 (10)S8A—C31A—H31A109.00
C26—C27A—C28109.9 (13)C32A—C31A—H31B109.00
C26—C27B—C28103.6 (11)H31A—C31A—H31B108.00
S8B—C27B—C28126.7 (10)C32A—C31A—H31A109.00
S8B—C27B—C26126.2 (10)S8B—C31B—H31C108.00
S7—C28—C27A127.5 (9)S8B—C31B—H31D108.00
S7—C28—C25129.8 (2)H31C—C31B—H31D107.00
S7—C28—C27B120.5 (8)C32B—C31B—H31C108.00
C25—C28—C27B109.5 (8)C32B—C31B—H31D108.00
C25—C28—C27A102.7 (9)C31A—C32A—H32A109.00
S7—C29—C30108.9 (3)C31A—C32A—H32B109.00
S8A—C31A—C32A111.3 (9)C31A—C32A—H32C109.00
S8B—C31B—C32B115.6 (7)H32A—C32A—H32B110.00
S1—C5A—H5A1109.00H32B—C32A—H32C110.00
S1—C5A—H5A2109.00H32A—C32A—H32C109.00
C6A—C5A—H5A1109.00C31B—C32B—H32E109.00
C6A—C5A—H5A2109.00C31B—C32B—H32F109.00
H5A1—C5A—H5A2108.00H32D—C32B—H32F109.00
C6B—C5B—H5B1102.00H32E—C32B—H32F109.00
C6B—C5B—H5B2102.00H32D—C32B—H32E109.00
H5B1—C5B—H5B2105.00C31B—C32B—H32D110.00
N1iv—Zn1iv—S5—C20123.48 (11)C9—N3—C10—N4173.3 (3)
N3iv—Zn1iv—S5—C20−147.19 (11)Zn1—N3—C10—C11167.87 (18)
N5iv—Zn1iv—S5—C20−57.16 (12)Zn1—N3—C10—N4−15.6 (4)
N7iv—Zn1iv—S5—C2033.40 (11)Zn1—N3—C9—N213.3 (4)
N1iv—Zn1iv—S5—C21−125.55 (14)C9—N3—C10—C11−3.2 (3)
N3iv—Zn1iv—S5—C21−36.22 (13)C10—N4—C17—N58.1 (5)
N5iv—Zn1iv—S5—C2153.81 (14)C17—N4—C10—N32.8 (5)
N7iv—Zn1iv—S5—C21144.37 (13)C17—N4—C10—C11178.9 (3)
N3—Zn1—N1—C1−170.8 (2)C10—N4—C17—C20−171.0 (3)
N5—Zn1—N1—C1−92.0 (4)C17—N5—C18—N6176.0 (3)
N7—Zn1—N1—C1−10.8 (2)Zn1—N5—C17—C20174.37 (18)
S5i—Zn1—N1—C189.7 (2)Zn1—N5—C17—N4−4.8 (4)
N3—Zn1—N1—C215.2 (2)Zn1—N5—C18—N62.4 (4)
N5—Zn1—N1—C294.0 (3)C18—N5—C17—C200.9 (3)
N7—Zn1—N1—C2175.3 (2)C18—N5—C17—N4−178.3 (3)
S5i—Zn1—N1—C2−84.2 (2)C17—N5—C18—C19−1.1 (3)
N1—Zn1—N3—C9−17.4 (2)Zn1—N5—C18—C19−174.63 (18)
N5—Zn1—N3—C9−176.7 (2)C18—N6—C25—C28−172.6 (3)
N7—Zn1—N3—C9−96.6 (3)C18—N6—C25—N72.0 (5)
S5i—Zn1—N3—C981.8 (2)C25—N6—C18—C19166.6 (3)
N1—Zn1—N3—C10173.0 (2)C25—N6—C18—N5−10.2 (5)
N5—Zn1—N3—C1013.7 (2)C26—N7—C25—N6−172.9 (3)
N7—Zn1—N3—C1093.9 (3)Zn1—N7—C25—N612.7 (4)
S5i—Zn1—N3—C10−87.8 (2)Zn1—N7—C26—N8−10.3 (4)
N1—Zn1—N5—C17−83.4 (3)C25—N7—C26—C27B−4.2 (9)
N3—Zn1—N5—C17−4.6 (2)Zn1—N7—C25—C28−172.11 (19)
N7—Zn1—N5—C17−164.6 (2)Zn1—N7—C26—C27B170.3 (9)
S5i—Zn1—N5—C1794.9 (2)C25—N7—C26—N8175.3 (3)
N1—Zn1—N5—C1889.1 (4)C26—N7—C25—C282.3 (3)
N3—Zn1—N5—C18167.8 (2)C26—N8—C1—C4−177.1 (3)
N7—Zn1—N5—C187.8 (2)C1—N8—C26—N7−0.1 (5)
S5i—Zn1—N5—C18−92.7 (2)C26—N8—C1—N12.7 (5)
N1—Zn1—N7—C25−173.6 (2)C1—N8—C26—C27B179.2 (11)
N3—Zn1—N7—C25−94.6 (3)N1—C1—C4—C30.3 (3)
N5—Zn1—N7—C25−14.5 (2)N8—C1—C4—S1−1.1 (4)
S5i—Zn1—N7—C2587.1 (2)N1—C1—C4—S1179.1 (2)
N1—Zn1—N7—C2613.0 (2)N8—C1—C4—C3−179.9 (3)
N3—Zn1—N7—C2692.0 (3)N1—C2—C3—C40.6 (3)
N5—Zn1—N7—C26172.1 (2)N1—C2—C3—S2177.3 (2)
S5i—Zn1—N7—C26−86.3 (2)N2—C2—C3—C4−177.0 (3)
C4—S1—C5A—C6A62.8 (5)N2—C2—C3—S2−0.3 (4)
C5A—S1—C4—C172.1 (3)C2—C3—C4—S1−179.4 (2)
C5A—S1—C4—C3−109.2 (3)S2—C3—C4—S13.6 (4)
C3—S2—C7—C8−178.1 (3)S2—C3—C4—C1−177.5 (2)
C7—S2—C3—C4−166.6 (3)C2—C3—C4—C1−0.5 (3)
C7—S2—C3—C217.2 (3)N2—C9—C12—C11177.1 (3)
C13A—S3—C12—C11119.6 (3)N3—C9—C12—S3−176.2 (2)
C12—S3—C13A—C14A−74.0 (4)N2—C9—C12—S32.4 (4)
C13A—S3—C12—C9−66.8 (3)N3—C9—C12—C11−1.4 (3)
C15—S4—C11—C1062.0 (3)N3—C10—C11—S4−178.3 (2)
C11—S4—C15—C16−169.2 (3)N4—C10—C11—C12−174.3 (3)
C15—S4—C11—C12−118.8 (3)N3—C10—C11—C122.4 (3)
Zn1iv—S5—C20—C19−89.6 (2)N4—C10—C11—S45.0 (4)
C21—S5—C20—C19161.3 (3)C10—C11—C12—C9−0.5 (3)
Zn1iv—S5—C20—C1779.2 (2)C10—C11—C12—S3174.1 (2)
C20—S5—C21—C22−162.9 (2)S4—C11—C12—S3−5.2 (4)
C21—S5—C20—C17−29.9 (3)S4—C11—C12—C9−179.8 (2)
Zn1iv—S5—C21—C2292.6 (2)N5—C17—C20—C19−0.4 (3)
C23—S6—C19—C20−6.1 (4)N5—C17—C20—S5−170.9 (2)
C23—S6—C19—C18−179.9 (2)N4—C17—C20—S58.3 (4)
C19—S6—C23—C24172.6 (2)N4—C17—C20—C19178.9 (3)
C28—S7—C29—C30164.8 (3)N6—C18—C19—C20−176.5 (3)
C29—S7—C28—C27B−154.9 (11)N5—C18—C19—C200.8 (3)
C29—S7—C28—C2530.2 (3)N5—C18—C19—S6176.49 (19)
C27B—S8B—C31B—C32B158.9 (12)N6—C18—C19—S6−0.8 (4)
C31B—S8B—C27B—C2611 (2)C18—C19—C20—C17−0.3 (3)
C31B—S8B—C27B—C28166.6 (17)S6—C19—C20—S5−3.8 (5)
C2—N1—C1—C40.2 (3)C18—C19—C20—S5170.4 (2)
Zn1—N1—C2—N2−8.1 (4)S6—C19—C20—C17−174.6 (2)
Zn1—N1—C1—N85.5 (4)N7—C25—C28—C27B0.7 (11)
Zn1—N1—C1—C4−174.7 (2)N7—C25—C28—S7176.0 (2)
C2—N1—C1—N8−179.6 (3)N6—C25—C28—C27B176.1 (11)
Zn1—N1—C2—C3174.35 (19)N6—C25—C28—S7−8.6 (4)
C1—N1—C2—N2177.1 (3)N7—C26—C27B—C284.5 (15)
C1—N1—C2—C3−0.5 (3)N8—C26—C27B—C28−175.0 (7)
C2—N2—C9—N31.0 (5)N8—C26—C27B—S8B−15 (2)
C9—N2—C2—C3173.4 (3)N7—C26—C27B—S8B164.4 (13)
C9—N2—C2—N1−3.8 (5)S8B—C27B—C28—C25−162.7 (16)
C2—N2—C9—C12−177.3 (3)C26—C27B—C28—S7−178.8 (6)
Zn1—N3—C9—C12−168.27 (18)C26—C27B—C28—C25−3.0 (15)
C10—N3—C9—C122.9 (3)S8B—C27B—C28—S722 (2)
C10—N3—C9—N2−175.6 (3)
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1; (iv) x+1/2, y, −z+1/2; (v) −x+1, −y, −z+1; (vi) −x+3/2, y−1/2, z; (vii) −x+1, y−1/2, −z+1/2; (viii) −x+2, −y, −z+1; (ix) −x+3/2, y+1/2, z; (x) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N3/C9–C12, Zn1/N1/N7/N8/C1/C26 and Zn1/N3/N4/N5/C10/C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5A—H5A1···S1v0.972.863.764 (5)155
C7—H7A···N20.972.503.014 (5)113
C21—H21A···S4i0.972.773.660 (4)154
C23—H23B···S50.972.693.221 (4)115
C31B—H31D···N80.972.533.089 (9)116
C21—H21B···Cg3iv0.972.863.536 (3)128
C22—H22A···Cg1iv0.962.903.699 (4)142
C23—H23B···Cg2iv0.972.813.641 (4)144
Symmetry codes: (i) x−1/2, y, −z+1/2; (iv) x+1/2, y, −z+1/2; (v) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula[Zn(C32H40N8S8)]
Mr858.67
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)295
a, b, c (Å)8.7973 (1), 27.2813 (3), 32.0903 (6)
V (Å3)7701.73 (19)
Z8
Radiation typeMo Kα
µ (mm−1)1.11
Crystal size (mm)0.60 × 0.37 × 0.13
Data collection
DiffractometerStoe IPDS 2
Absorption correctionPart of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
Tmin, Tmax0.620, 0.866
No. of measured, independent and
observed [I > 2σ(I)] reflections		7282, 7282, 5696
Rint0.000
(sin θ/λ)max (Å−1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.097, 1.05
No. of reflections7282
No. of parameters466
No. of restraints16
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.44, −0.30

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Zn1—N12.004 (2)Zn1—N71.994 (2)
Zn1—N31.994 (2)Zn1—S5i2.6364 (9)
Zn1—N52.004 (2)
Symmetry code: (i) x−1/2, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N3/C9–C12, Zn1/N1/N7/N8/C1/C26 and Zn1/N3/N4/N5/C10/C17 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C5A—H5A1···S1ii0.972.863.764 (5)155
C7—H7A···N20.972.503.014 (5)113
C21—H21A···S4i0.972.773.660 (4)154
C23—H23B···S50.972.693.221 (4)115
C31B—H31D···N80.972.533.089 (9)116
C21—H21B···Cg3iii0.972.863.536 (3)128
C22—H22A···Cg1iii0.962.903.699 (4)142
C23—H23B···Cg2iii0.972.813.641 (4)144
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+1, −y, −z+1; (iii) x+1/2, y, −z+1/2.
 

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBelviso, S., Ricciardi, G. & Lelj, F. (2000). J. Mater. Chem. 10, 297–304.  Web of Science CrossRef CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationParkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationRamirez, C., Antonacci, C., Ferraira, J. & Sheardy, R. D. (2004). Synth. Commun. 34, 3373–3379.  Web of Science CrossRef CAS Google Scholar
 First citationRicciardi, G., Alfonso, B., Alessandro, B., Angela, R., Francesco, L. & Francesca, B. (1996a). J. Chem. Soc. Dalton Trans. 13, 2799–2807.  CSD CrossRef Web of Science Google Scholar
 First citationRicciardi, G., Belviso, S. & Lelj, F. (2000). Inorg. Chem. 39, 1618–1620.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRicciardi, G., Belviso, S., Lelj, F. & Ristori, S. (1998). J. Porphyrins Phthalocyanins, 2, 177–188.  CrossRef CAS Google Scholar
 First citationRicciardi, G., De Benedetto, L. & Lelj, F. (1996b). Polyhedron, 15, 3183–3191.  CrossRef CAS Web of Science Google Scholar
 First citationRicciardi, G., Rosa, A., Ciofini, I. & Bencini, A. (1999). Inorg. Chem. 38, 1422–1431.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSakellariou, E. G., Montalban, A. G., Meunier, H. G., Ostler, R. B., Rumbles, G., Baret, A. G. M. & Hoffman, B. M. (2000). J. Photochem. Photobiol. A, 136, 185–187.  Web of Science CrossRef CAS Google Scholar
 First citationSchramm, C. J. & Hoffman, B. M. (1980). Inorg. Chem. 19, 383–385.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Pages m998-m999
https://doi.org/10.1107/S1600536810028588
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS