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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 290-292
doi:10.1107/S2056989016001857

Crystal structure of S-hexyl (E)-3-(2-hy­dr­oxy­benzyl­­idene)di­thio­carbazate

CROSSMARK_Color_square_no_text.svg
M. S. Begum,a M. B. H. Howlader,b* M. C. Sheikh,c R. Miyataked and E. Zangrandoe

aDepartment of Chemistry, Shahjalal University of Science and Technology, Sylhet 3114, Bangladesh, bDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, cDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, dCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and eDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127 Trieste, Italy
*Correspondence e-mail: mbhhowlader@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 27 January 2016; accepted 31 January 2016; online 6 February 2016)

The title compound, C14H20N2OS2 [systematic name: S-hexyl (E)-2-(2-hy­droxy­benzyl­idene)hydrazine-1-carbodi­thio­ate], crystallizes with four independent mol­ecules (A–D) in the asymmetric unit. All four mol­ecules adopt an E conformation with respect to the C=N bond of the benzyl­idene moiety and have an intra­molecular O—H⋯N hydrogen bond generating an S(6) ring motif. In the crystal, the A and D mol­ecules are connected by a pair N—H⋯S hydrogen bonds, forming a dimer with an R22(8) ring motif. In the case of mol­ecules B and C, they are linked to themselves by pairs of N—H⋯S hydrogen bonds, forming B–B and C–C inversion dimers with R22(8) ring motifs.

CCDC reference: 1451068

1. Chemical context

Bidentate Schiff bases of S-methyl or S-benzyl di­thio­carbaza­tes and their metal complexes have received considerable attention for their possible bioactivities (Chan et al., 2008[Chan, M. E., Crouse, K. A., Tahir, M. I. M., Rosli, R., Umar-Tsafe, N. & Cowley, A. R. (2008). Polyhedron, 27, 1141-1149.]; How et al., 2008[How, F. N. F., Crouse, K. A., Tahir, M. I. M., Tarafder, M. T. H. & Cowley, A. R. (2008). Polyhedron, 27, 3325-3329.]; Zangrando et al., 2015[Zangrando, E., Islam, M. T., Islam, M. A. A. A., Sheikh, M. C., Tarafder, M. T. H., Miyatake, R., Zahan, R. & Hossain, M. A. (2015). Inorg. Chim. Acta, 427, 278-284.]; Ali et al., 2002[Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B. & Ali Manaf, A. (2002). J. Inorg. Biochem. 92, 141-148.]; Chew et al., 2004[Chew, K. B., Tarafder, M. T. H., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 1385-1392.]; Crouse et al., 2004[Crouse, K. A., Chew, K. B., Tarafder, M. T. H., Kasbollah, A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 161-168.]). As part of our ongoing structural studies of S-containing Schiff bases, we report herein on the structure of a mol­ecule having a hexyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015[Begum, M. S., Zangrando, E., Sheikh, M. C., Miyatake, R. & Hossain, M. M. (2015). Acta Cryst. E71, o265-o266.]; Begum, Howlader, Miyatake et al., 2015[Begum, M. S., Howlader, M. B. H., Miyatake, R., Zangrando, E. & Sheikh, M. C. (2015). Acta Cryst. E71, o199.]; Howlader et al., 2015[Howlader, M. B. H., Begum, M. S., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, o103-o104.]) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015[Begum, M. S., Howlader, M. B. H., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, m249-m250.]).

[Scheme 1]

2. Structural commentary

The four independent mol­ecules (A--D) of the title compound are shown in Figs. 1[link] and 2[link]. The Schiff base exists in its thione tautomeric form with the di­thio­carbazate fragment adopting an E conformation with respect to the C=N bond of the benzyl­idene moiety. The β-nitro­gen and the thio­keto sulfur are trans located with respect to bond C8—N2 bond in mol­ecule A (and similarly for mol­ecules B, C and D). All non-H atoms in the mol­ecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thio­ketone atoms S1, S3, S5 and S7 in the four independent mol­ecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015[Howlader, M. B. H., Begum, M. S., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, o103-o104.]) and S-hexyl (E)-3-(4-meth­oxy­benzyl­idene)di­thio­carbazate (Begum, Howlader, Miyatake et al., 2015[Begum, M. S., Howlader, M. B. H., Miyatake, R., Zangrando, E. & Sheikh, M. C. (2015). Acta Cryst. E71, o199.]). The hexyl chain in all four mol­ecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiol­ate form has been reported to act as a tridentate ligand through N-, S- and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015[Begum, M. S., Howlader, M. B. H., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, m249-m250.]).

[Figure 1]
Figure 1
The mol­ecular structure of mol­ecules A and C of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
The mol­ecular structure of mol­ecules B and D of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

The crystal packing of the title compound (Fig. 3[link]), indicates that the mol­ecules are connected by pairs of N—H⋯S hydrogen bonds (Table 1[link]) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯N1 0.73 (3) 2.13 (3) 2.684 (3) 135 (3)
O2—H2O⋯N3 0.78 (3) 2.09 (3) 2.685 (3) 133 (3)
O3—H3O⋯N5 0.84 (3) 1.91 (3) 2.662 (3) 148 (3)
O4—H4O⋯N7 0.75 (3) 2.00 (3) 2.663 (3) 146 (3)
N2—H2N⋯S7i 0.86 (3) 2.58 (3) 3.430 (3) 169 (3)
N4—H4N⋯S3ii 0.81 (3) 2.64 (3) 3.439 (3) 171 (2)
N6—H6N⋯S5iii 0.84 (3) 2.59 (3) 3.398 (3) 162 (2)
N8—H8N⋯S1iv 0.83 (3) 2.61 (3) 3.403 (3) 160 (2)
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+2, -z+2; (iv) [x, -y+1, z-{\script{1\over 2}}].
[Figure 3]
Figure 3
Crystal packing of the title compound, viewed along the c axis, showing pairs of mol­ecules connected by N—H.·S hydrogen bonds (dashed lines; see Table 1[link]). H atoms not involved in hydrogen bonds have been omitted for clarity.

4. Synthesis and crystallization

To an ethano­lic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon di­sulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then, 1-bromo­hexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hy­droxy­benzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/aceto­nitrile (3:1) [m.p. 364 K].

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The hydrogen atoms of NH and OH groups were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).

Table 2
Experimental details

Crystal data
Chemical formula C14H20N2OS2
Mr 296.44
Crystal system, space group Monoclinic, P2/c
Temperature (K) 173
a, b, c (Å) 18.9744 (4), 16.0269 (3), 21.1146 (4)
β (°) 100.808 (1)
V (Å3) 6307.1 (2)
Z 16
Radiation type Cu Kα
μ (mm−1) 3.01
Crystal size (mm) 0.50 × 0.35 × 0.34
 
Data collection
Diffractometer Rigaku R-AXIS RAPID
No. of measured, independent and observed [I > 2σ(I)] reflections 10367, 10367, 6152
Rint 0.072
(sin θ/λ)max (Å−1) 0.581
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.176, 0.93
No. of reflections 10367
No. of parameters 713
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.02, −0.46
Computer programs: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information

CCDC reference: 1451068

Crystal structure: contains datablocks General, I. DOI: 10.1107/S2056989016001857/su5276sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016001857/su5276Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989016001857/su5276Isup3.cml

checkCIF report


Chemical context top

Bidentate Schiff bases of S-methyl or S-benzyl di­thio­carbaza­tes and their metal complexes have received considerable attention for their possible bioactivities (Chan et al., 2008; How et al., 2008; Zangrando et al., 2015; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing Schiff bases, we report herein on the structure of a molecule having a hexyl alkyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015; Begum, Howlader, Miyatake et al., 2015; Howlader et al., 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015).

Structural commentary top

The four independent molecules (A--D) of the title compound are shown in Figs. 1 and 2. The Schiff base exists in its thione tautomeric form with the di­thio­carbazate fragment adopting an E conformation with respect to the C═N bond of the benzyl­idene moiety. The β-nitro­gen and the thio­keto sulfur are trans located with respect to bond C8—N2 bond in molecule A (and similarly for molecules B, C and D). All non-H atoms in the molecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thio­ketone atoms S1, S3, S5 and S7 in the four independent molecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015) and S-hexyl (E)-3-(4-meth­oxy­benzyl­idene)di­thio­carbazate (Begum, Howlader, Miyatake et al., 2015). The hexyl chain in all four molecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiol­ate form has been reported to act as a tridentate ligand through N–, S– and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015).

Supra­molecular features top

The crystal packing of the title compound (Fig. 2), indicates that the molecules are connected by pairs of N—H···S hydrogen bonds (Table 1) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.

Synthesis and crystallization top

To an ethano­lic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon di­sulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then 1-bromo­hexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hy­droxy­benzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/aceto­nitrile (3:1) [m.p. 364 K].

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The NH and OH H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).

Structure description top

Bidentate Schiff bases of S-methyl or S-benzyl di­thio­carbaza­tes and their metal complexes have received considerable attention for their possible bioactivities (Chan et al., 2008; How et al., 2008; Zangrando et al., 2015; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing Schiff bases, we report herein on the structure of a molecule having a hexyl alkyl chain, similar to other ligands reported by our group (Begum, Zangrando et al., 2015; Begum, Howlader, Miyatake et al., 2015; Howlader et al., 2015) but differing in their ability to act as tridentate ligands in metal coordination (Begum, Howlader, Sheikh et al., 2015).

The four independent molecules (A--D) of the title compound are shown in Figs. 1 and 2. The Schiff base exists in its thione tautomeric form with the di­thio­carbazate fragment adopting an E conformation with respect to the C═N bond of the benzyl­idene moiety. The β-nitro­gen and the thio­keto sulfur are trans located with respect to bond C8—N2 bond in molecule A (and similarly for molecules B, C and D). All non-H atoms in the molecules are almost co-planar indicating, except for the alkyl chain, electron delocalization within them. The maximum deviation from the mean plane is shown by the thio­ketone atoms S1, S3, S5 and S7 in the four independent molecules (r.m.s deviations of 0.086, 0.118, 0.138 and 0.183 Å, respectively). The bond lengths and angles are comparable to those reported for S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015) and S-hexyl (E)-3-(4-meth­oxy­benzyl­idene)di­thio­carbazate (Begum, Howlader, Miyatake et al., 2015). The hexyl chain in all four molecules has an extended anti-zigzag conformation. This compound in its deprotonated imino thiol­ate form has been reported to act as a tridentate ligand through N–, S– and O-donors to form a binuclear copper(II) complex (Begum, Howlader, Sheikh et al., 2015).

The crystal packing of the title compound (Fig. 2), indicates that the molecules are connected by pairs of N—H···S hydrogen bonds (Table 1) to form A–D dimers, and B–B and C–C inversion dimers, all with R22(8) ring motifs.

Synthesis and crystallization top

To an ethano­lic solution of KOH (2.81 g, 0.05 mol), hydrazine hydrate (2.50 g, 0.05 mol, 99%) was added and the mixture stirred at 273 K. To this solution carbon di­sulfide (3.81 g, 0.05 mol) was added drop wise with constant stirring for 1 h. Then 1-bromo­hexane (8.25 g, 0.05 mol) was added drop wise with vigorous stirring at 273 K for an additional hour. Finally, 2-hy­droxy­benzaldehyde (6.10 g, 0.05 mol) in ethanol was added and the mixture refluxed for 30 min. The mixture was filtered while hot and then the filtrate was cooled to 273 K giving a precipitate of the Schiff base product. It was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals of the title compound were obtained by slow evaporation of a solution in methanol/aceto­nitrile (3:1) [m.p. 364 K].

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The NH and OH H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N,O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of molecules A and C of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of molecules B and D of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. Crystal packing of the title compound, viewed along the c axis, showing pairs of molecules connected by N—H.·S hydrogen bonds (dashed lines; see Table 1). H atoms not involved in hydrogen bonds have been omitted for clarity.
S-Hexyl (E)-3-(2-hydroxybenzylidene)dithiocarbazate top
Crystal data top
C14H20N2OS2F(000) = 2528
Mr = 296.44Dx = 1.249 Mg m−3
Monoclinic, P2/cCu Kα radiation, λ = 1.54187 Å
a = 18.9744 (4) ÅCell parameters from 48491 reflections
b = 16.0269 (3) Åθ = 3.5–68.2°
c = 21.1146 (4) ŵ = 3.01 mm−1
β = 100.808 (1)°T = 173 K
V = 6307.1 (2) Å3Block, colourless
Z = 160.50 × 0.35 × 0.34 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		Rint = 0.072
Detector resolution: 10.000 pixels mm-1θmax = 63.7°, θmin = 3.5°
ω scansh = −22→22
10367 measured reflectionsk = −19→19
10367 independent reflectionsl = −25→25
6152 reflections with I > 2σ(I)
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)] = 0.065Hydrogen site location: mixed
wR(F2) = 0.176H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.1083P)2]
where P = (Fo2 + 2Fc2)/3
10367 reflections(Δ/σ)max = 0.001
713 parametersΔρmax = 1.01 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C14H20N2OS2V = 6307.1 (2) Å3
Mr = 296.44Z = 16
Monoclinic, P2/cCu Kα radiation
a = 18.9744 (4) ŵ = 3.01 mm−1
b = 16.0269 (3) ÅT = 173 K
c = 21.1146 (4) Å0.50 × 0.35 × 0.34 mm
β = 100.808 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6152 reflections with I > 2σ(I)
10367 measured reflectionsRint = 0.072
10367 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.176H-atom parameters constrained
S = 0.93Δρmax = 1.01 e Å−3
10367 reflectionsΔρmin = −0.46 e Å−3
713 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.25358 (4)0.59787 (5)1.25919 (4)0.0533 (2)
S20.10299 (4)0.66115 (5)1.21116 (4)0.0461 (2)
O1−0.06852 (11)0.53508 (15)1.15318 (11)0.0557 (6)
H1O−0.0321 (17)0.550 (2)1.1640 (16)0.067*
N10.06892 (12)0.49125 (15)1.19459 (10)0.0410 (6)
N20.14075 (12)0.50536 (15)1.21817 (11)0.0417 (6)
H2N0.1694 (15)0.4634 (17)1.2249 (13)0.050*
C1−0.08129 (16)0.4524 (2)1.14951 (13)0.0447 (7)
C2−0.15168 (17)0.4254 (2)1.13090 (14)0.0570 (9)
H2−0.18930.46511.12120.068*
C3−0.16709 (17)0.3420 (2)1.12649 (15)0.0617 (9)
H3−0.21550.32471.11360.074*
C4−0.11444 (17)0.2829 (2)1.14023 (14)0.0584 (9)
H4−0.12610.22521.13690.070*
C5−0.04406 (16)0.30837 (19)1.15911 (13)0.0508 (8)
H5−0.00730.26751.16880.061*
C6−0.02564 (15)0.39267 (19)1.16431 (12)0.0418 (7)
C70.04852 (14)0.41577 (18)1.18721 (12)0.0409 (7)
H70.08330.37281.19710.049*
C80.16649 (15)0.58236 (18)1.22957 (13)0.0410 (7)
C90.15769 (15)0.75494 (17)1.22512 (14)0.0445 (7)
H9A0.18190.75791.27090.053*
H9B0.19490.75421.19790.053*
C100.10842 (14)0.83027 (17)1.20813 (13)0.0434 (7)
H10A0.08400.82641.16250.052*
H10B0.07120.83001.23530.052*
C110.15059 (15)0.91139 (17)1.21864 (13)0.0420 (7)
H11A0.17560.91431.26420.050*
H11B0.18750.91151.19110.050*
C120.10336 (14)0.98812 (18)1.20317 (13)0.0437 (7)
H12A0.06430.98571.22830.052*
H12B0.08110.98711.15680.052*
C130.14401 (15)1.06987 (18)1.21809 (14)0.0474 (8)
H13A0.16641.07101.26440.057*
H13B0.18301.07261.19280.057*
C140.09630 (16)1.14567 (19)1.20269 (16)0.0633 (10)
H14A0.07371.14481.15700.095*
H14B0.12521.19641.21190.095*
H14C0.05911.14491.22920.095*
S3−0.00414 (4)0.86442 (5)0.98657 (4)0.0615 (3)
S40.14581 (4)0.80245 (5)1.04021 (4)0.0527 (2)
O20.31627 (12)0.92929 (17)1.09819 (11)0.0628 (7)
H2O0.2772 (18)0.913 (2)1.0877 (17)0.075*
N30.17915 (13)0.97231 (16)1.05390 (10)0.0453 (6)
N40.10796 (14)0.95825 (16)1.02840 (12)0.0483 (7)
H4N0.0804 (16)0.997 (2)1.0216 (14)0.058*
C150.32870 (17)1.0119 (2)1.10127 (13)0.0511 (8)
C160.39934 (17)1.0388 (3)1.12158 (15)0.0620 (10)
H160.43670.99901.13290.074*
C170.41471 (19)1.1219 (3)1.12517 (15)0.0678 (10)
H170.46321.13901.13840.081*
C180.36200 (18)1.1823 (2)1.11015 (15)0.0640 (10)
H180.37361.24001.11390.077*
C190.29206 (18)1.1563 (2)1.08951 (14)0.0581 (9)
H190.25551.19701.07840.070*
C200.27352 (16)1.0720 (2)1.08446 (13)0.0461 (8)
C210.19920 (16)1.0485 (2)1.06038 (13)0.0467 (8)
H210.16441.09121.04910.056*
C220.08232 (16)0.8808 (2)1.01810 (14)0.0484 (8)
C230.09183 (16)0.70822 (19)1.02657 (14)0.0519 (8)
H23A0.05510.70841.05430.062*
H23B0.06700.70550.98100.062*
C240.14087 (15)0.63370 (19)1.04250 (14)0.0509 (8)
H24A0.16500.63651.08830.061*
H24B0.17830.63501.01560.061*
C250.09880 (15)0.55256 (19)1.03051 (14)0.0516 (8)
H25A0.06330.55041.05940.062*
H25B0.07200.55220.98550.062*
C260.14574 (16)0.4750 (2)1.04161 (15)0.0540 (8)
H26A0.16960.47301.08750.065*
H26B0.18360.47911.01520.065*
C270.10385 (17)0.3945 (2)1.02465 (16)0.0613 (9)
H27A0.06520.39121.05020.074*
H27B0.08100.39600.97850.074*
C280.15007 (18)0.3170 (2)1.03720 (17)0.0776 (11)
H28A0.18790.31921.01140.116*
H28B0.12030.26741.02530.116*
H28C0.17190.31431.08300.116*
S50.50812 (4)0.86393 (5)1.02000 (4)0.0560 (3)
S60.36038 (4)0.79983 (5)0.96181 (4)0.0481 (2)
O30.19255 (11)0.91698 (14)0.90094 (10)0.0553 (6)
H3O0.2367 (16)0.913 (2)0.9149 (15)0.066*
N50.32576 (12)0.96786 (14)0.94728 (10)0.0384 (6)
N60.39644 (12)0.95587 (15)0.97387 (11)0.0425 (6)
H6N0.4245 (15)0.9962 (19)0.9840 (13)0.051*
C290.17628 (15)0.9992 (2)0.89769 (12)0.0433 (7)
C300.10555 (16)1.0218 (2)0.87630 (14)0.0541 (8)
H300.07030.97970.86400.065*
C310.08572 (17)1.1037 (2)0.87262 (14)0.0573 (9)
H310.03651.11760.85900.069*
C320.13576 (17)1.1674 (2)0.88835 (14)0.0565 (9)
H320.12151.22430.88480.068*
C330.20673 (16)1.14573 (19)0.90922 (13)0.0476 (8)
H330.24141.18860.92020.057*
C340.22898 (15)1.06259 (19)0.91474 (12)0.0399 (7)
C350.30375 (15)1.04327 (18)0.94067 (12)0.0397 (7)
H350.33681.08750.95290.048*
C360.42271 (15)0.87873 (19)0.98566 (13)0.0428 (7)
C370.41480 (15)0.70616 (18)0.97630 (14)0.0460 (7)
H37A0.45350.70760.95080.055*
H37B0.43700.70201.02250.055*
C380.36595 (15)0.63222 (17)0.95638 (13)0.0446 (7)
H38A0.34480.63690.91000.053*
H38B0.32620.63320.98080.053*
C390.40588 (14)0.54952 (17)0.96853 (13)0.0433 (7)
H39A0.42750.54511.01490.052*
H39B0.44530.54830.94370.052*
C400.35648 (15)0.47508 (18)0.94918 (14)0.0456 (7)
H40A0.33580.47920.90260.055*
H40B0.31640.47750.97310.055*
C410.39454 (16)0.39093 (18)0.96230 (15)0.0525 (8)
H41A0.43250.38680.93610.063*
H41B0.41790.38811.00830.063*
C420.34353 (17)0.31711 (19)0.94668 (16)0.0638 (9)
H42A0.30580.32080.97250.096*
H42B0.37030.26500.95670.096*
H42C0.32180.31820.90080.096*
S70.24114 (4)0.67360 (5)0.72575 (4)0.0532 (2)
S80.38731 (4)0.73717 (5)0.78991 (4)0.0467 (2)
O40.55528 (11)0.61947 (14)0.85012 (11)0.0557 (6)
H4O0.5165 (16)0.625 (2)0.8343 (15)0.067*
N70.42251 (12)0.56890 (14)0.80139 (10)0.0384 (6)
N80.35164 (13)0.58122 (15)0.77368 (11)0.0406 (6)
H8N0.3267 (15)0.5403 (17)0.7596 (13)0.049*
C430.57105 (15)0.5377 (2)0.85318 (12)0.0423 (7)
C440.64194 (16)0.5149 (2)0.87552 (14)0.0518 (8)
H440.67710.55690.88800.062*
C450.66183 (17)0.4330 (2)0.87981 (15)0.0579 (9)
H450.71070.41900.89520.069*
C460.61212 (17)0.3694 (2)0.86216 (14)0.0534 (8)
H460.62650.31250.86520.064*
C470.54122 (16)0.39123 (19)0.84007 (13)0.0465 (8)
H470.50660.34850.82830.056*
C480.51916 (15)0.47465 (18)0.83465 (12)0.0384 (7)
C490.44460 (14)0.49335 (18)0.80773 (12)0.0385 (7)
H490.41190.44900.79470.046*
C500.32545 (15)0.65816 (17)0.76239 (13)0.0406 (7)
C510.33330 (15)0.83076 (17)0.77494 (14)0.0448 (7)
H51A0.31050.83410.72880.054*
H51B0.29500.83010.80100.054*
C520.38231 (15)0.90513 (18)0.79341 (13)0.0445 (7)
H52A0.40350.90180.83990.053*
H52B0.42200.90300.76900.053*
C530.34310 (14)0.98712 (17)0.77993 (13)0.0424 (7)
H53A0.30510.99040.80610.051*
H53B0.31960.98890.73390.051*
C540.39254 (15)1.06271 (19)0.79491 (14)0.0503 (8)
H54A0.41571.06100.84100.060*
H54B0.43081.05900.76900.060*
C550.35385 (16)1.14549 (18)0.78102 (16)0.0558 (8)
H55A0.32901.14640.73540.067*
H55B0.31701.15040.80830.067*
C560.40366 (17)1.2195 (2)0.79334 (17)0.0731 (11)
H56A0.42891.21870.83830.110*
H56B0.37581.27110.78510.110*
H56C0.43861.21680.76460.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0338 (4)0.0394 (5)0.0820 (6)0.0012 (3)−0.0012 (4)−0.0004 (4)
S20.0352 (4)0.0406 (5)0.0594 (5)0.0030 (3)0.0010 (4)0.0001 (3)
O10.0457 (14)0.0542 (16)0.0627 (15)0.0107 (12)−0.0012 (12)0.0022 (11)
N10.0363 (14)0.0479 (16)0.0359 (13)0.0039 (12)−0.0004 (10)0.0023 (11)
N20.0328 (15)0.0369 (16)0.0521 (15)0.0001 (11)−0.0009 (12)0.0001 (12)
C10.0446 (19)0.0429 (19)0.0439 (17)0.0016 (15)0.0013 (14)−0.0036 (14)
C20.0351 (19)0.085 (3)0.0477 (19)0.0163 (18)−0.0011 (15)0.0004 (17)
C30.043 (2)0.079 (3)0.060 (2)−0.012 (2)0.0005 (16)−0.0065 (19)
C40.050 (2)0.062 (2)0.059 (2)−0.0170 (18)−0.0012 (16)−0.0047 (17)
C50.0436 (19)0.0424 (19)0.063 (2)−0.0008 (15)0.0013 (16)−0.0044 (15)
C60.0374 (17)0.052 (2)0.0343 (15)0.0055 (15)0.0029 (13)0.0006 (13)
C70.0365 (17)0.0345 (17)0.0490 (17)−0.0019 (14)0.0010 (14)−0.0019 (13)
C80.0379 (17)0.048 (2)0.0360 (15)0.0048 (14)0.0049 (13)0.0039 (13)
C90.0395 (17)0.0316 (16)0.0600 (18)−0.0020 (13)0.0028 (14)−0.0030 (14)
C100.0420 (18)0.0375 (18)0.0498 (17)0.0052 (14)0.0063 (14)−0.0042 (13)
C110.0392 (17)0.0379 (18)0.0473 (17)0.0023 (14)0.0042 (14)−0.0006 (13)
C120.0376 (17)0.0402 (18)0.0507 (18)0.0040 (14)0.0014 (14)0.0000 (14)
C130.0400 (18)0.0416 (19)0.0580 (19)−0.0014 (14)0.0026 (15)−0.0004 (14)
C140.060 (2)0.040 (2)0.084 (2)0.0006 (17)0.0009 (19)−0.0033 (17)
S30.0391 (5)0.0544 (6)0.0868 (6)0.0014 (4)0.0009 (4)0.0056 (4)
S40.0424 (5)0.0528 (6)0.0598 (5)0.0060 (4)0.0017 (4)0.0058 (4)
O20.0508 (15)0.0648 (18)0.0687 (16)0.0107 (14)0.0011 (13)0.0046 (12)
N30.0386 (15)0.0561 (18)0.0402 (14)0.0042 (13)0.0048 (11)0.0042 (12)
N40.0410 (17)0.0464 (18)0.0548 (16)0.0038 (13)0.0021 (13)0.0060 (13)
C150.048 (2)0.065 (2)0.0386 (17)0.0035 (18)0.0051 (15)−0.0020 (16)
C160.040 (2)0.088 (3)0.054 (2)0.0099 (19)0.0001 (16)−0.0031 (19)
C170.049 (2)0.094 (3)0.057 (2)−0.015 (2)0.0015 (17)−0.013 (2)
C180.053 (2)0.070 (3)0.066 (2)−0.010 (2)0.0029 (18)−0.0135 (18)
C190.053 (2)0.059 (2)0.060 (2)−0.0014 (18)0.0036 (17)−0.0041 (17)
C200.0395 (18)0.059 (2)0.0387 (16)0.0057 (16)0.0040 (14)0.0013 (14)
C210.0424 (19)0.053 (2)0.0440 (17)0.0034 (16)0.0072 (14)0.0014 (15)
C220.0444 (19)0.056 (2)0.0442 (17)0.0032 (16)0.0061 (14)0.0035 (15)
C230.0451 (19)0.054 (2)0.0563 (19)0.0072 (16)0.0082 (15)0.0068 (15)
C240.045 (2)0.055 (2)0.0524 (19)0.0034 (16)0.0092 (15)0.0016 (15)
C250.0440 (19)0.060 (2)0.0486 (18)0.0092 (17)0.0041 (15)0.0039 (15)
C260.045 (2)0.057 (2)0.059 (2)0.0062 (17)0.0073 (16)0.0005 (16)
C270.048 (2)0.065 (2)0.070 (2)0.0042 (18)0.0062 (17)0.0011 (18)
C280.073 (3)0.062 (3)0.093 (3)0.005 (2)0.004 (2)−0.007 (2)
S50.0355 (5)0.0451 (5)0.0812 (6)−0.0009 (4)−0.0053 (4)−0.0014 (4)
S60.0391 (5)0.0375 (5)0.0627 (5)−0.0030 (3)−0.0036 (4)−0.0002 (3)
O30.0466 (13)0.0426 (13)0.0691 (15)−0.0093 (11)−0.0084 (12)0.0045 (10)
N50.0343 (14)0.0380 (15)0.0404 (13)−0.0031 (11)0.0002 (11)−0.0025 (10)
N60.0307 (15)0.0404 (16)0.0518 (15)−0.0038 (11)−0.0043 (12)−0.0035 (12)
C290.0376 (18)0.052 (2)0.0373 (16)−0.0075 (15)−0.0005 (13)0.0028 (14)
C300.0400 (19)0.063 (2)0.0559 (19)−0.0093 (17)−0.0001 (15)0.0054 (16)
C310.0375 (19)0.076 (3)0.056 (2)0.0070 (18)0.0017 (15)0.0084 (18)
C320.050 (2)0.058 (2)0.058 (2)0.0107 (18)0.0020 (16)0.0035 (16)
C330.0447 (19)0.043 (2)0.0521 (18)0.0003 (15)0.0022 (15)−0.0013 (14)
C340.0355 (17)0.0462 (19)0.0357 (15)−0.0020 (14)0.0010 (13)0.0014 (13)
C350.0367 (17)0.0412 (19)0.0401 (16)−0.0071 (14)0.0045 (13)−0.0032 (13)
C360.0389 (18)0.0433 (19)0.0444 (16)0.0014 (14)0.0030 (13)−0.0003 (14)
C370.0410 (18)0.0420 (18)0.0518 (18)0.0007 (14)0.0008 (14)0.0037 (14)
C380.0439 (18)0.0402 (18)0.0466 (17)0.0000 (14)0.0007 (14)0.0054 (13)
C390.0371 (17)0.047 (2)0.0438 (17)−0.0035 (14)0.0030 (14)0.0008 (14)
C400.0393 (18)0.0438 (19)0.0519 (18)−0.0031 (14)0.0041 (14)−0.0016 (14)
C410.0446 (19)0.048 (2)0.064 (2)0.0002 (16)0.0060 (16)−0.0003 (16)
C420.058 (2)0.043 (2)0.088 (2)−0.0056 (17)0.0053 (19)−0.0039 (17)
S70.0354 (5)0.0434 (5)0.0758 (6)0.0005 (3)−0.0025 (4)0.0030 (4)
S80.0410 (5)0.0362 (5)0.0580 (5)−0.0009 (3)−0.0035 (4)−0.0021 (3)
O40.0502 (14)0.0400 (13)0.0693 (15)−0.0074 (12)−0.0082 (12)0.0024 (11)
N70.0349 (14)0.0360 (14)0.0420 (13)−0.0009 (11)0.0015 (11)−0.0006 (10)
N80.0346 (15)0.0361 (16)0.0475 (14)−0.0028 (11)−0.0016 (12)−0.0048 (11)
C430.0374 (18)0.054 (2)0.0348 (15)−0.0084 (15)0.0040 (13)0.0003 (13)
C440.0380 (18)0.059 (2)0.0554 (19)−0.0058 (16)0.0021 (15)0.0042 (16)
C450.0395 (19)0.083 (3)0.0508 (19)0.0036 (19)0.0078 (15)0.0061 (18)
C460.048 (2)0.053 (2)0.057 (2)0.0119 (17)0.0044 (16)0.0045 (16)
C470.0459 (19)0.046 (2)0.0471 (17)−0.0016 (15)0.0068 (15)−0.0045 (14)
C480.0350 (16)0.0413 (17)0.0385 (16)−0.0005 (14)0.0056 (13)0.0019 (13)
C490.0366 (17)0.0423 (18)0.0357 (15)−0.0079 (14)0.0048 (13)−0.0045 (13)
C500.0388 (17)0.0366 (17)0.0461 (16)0.0003 (14)0.0068 (13)0.0013 (13)
C510.0382 (17)0.0439 (19)0.0482 (17)0.0006 (14)−0.0023 (14)0.0003 (14)
C520.0456 (18)0.0446 (19)0.0408 (16)−0.0044 (15)0.0014 (14)−0.0005 (13)
C530.0424 (18)0.0390 (18)0.0439 (16)−0.0013 (14)0.0031 (14)−0.0011 (13)
C540.0434 (19)0.044 (2)0.061 (2)−0.0043 (15)0.0049 (16)−0.0016 (15)
C550.046 (2)0.0397 (19)0.081 (2)−0.0017 (15)0.0100 (17)−0.0015 (16)
C560.063 (2)0.044 (2)0.111 (3)−0.0017 (18)0.012 (2)0.006 (2)
Geometric parameters (Å, º) top
S1—C81.672 (3)S5—C361.664 (3)
S2—C81.738 (3)S6—C361.740 (3)
S2—C91.819 (3)S6—C371.815 (3)
O1—C11.347 (4)O3—C291.353 (4)
O1—H1O0.73 (3)O3—H3O0.84 (3)
N1—C71.271 (3)N5—C351.278 (3)
N1—N21.379 (3)N5—N61.367 (3)
N2—C81.332 (3)N6—C361.339 (4)
N2—H2N0.86 (3)N6—H6N0.84 (3)
C1—C21.389 (4)C29—C301.381 (4)
C1—C61.416 (4)C29—C341.423 (4)
C2—C31.368 (5)C30—C311.364 (4)
C2—H20.9500C30—H300.9500
C3—C41.368 (4)C31—C321.392 (4)
C3—H30.9500C31—H310.9500
C4—C51.382 (4)C32—C331.380 (4)
C4—H40.9500C32—H320.9500
C5—C61.395 (4)C33—C341.396 (4)
C5—H50.9500C33—H330.9500
C6—C71.448 (4)C34—C351.455 (4)
C7—H70.9500C35—H350.9500
C9—C101.528 (4)C37—C381.515 (4)
C9—H9A0.9900C37—H37A0.9900
C9—H9B0.9900C37—H37B0.9900
C10—C111.521 (4)C38—C391.524 (4)
C10—H10A0.9900C38—H38A0.9900
C10—H10B0.9900C38—H38B0.9900
C11—C121.521 (4)C39—C401.525 (4)
C11—H11A0.9900C39—H39A0.9900
C11—H11B0.9900C39—H39B0.9900
C12—C131.523 (4)C40—C411.530 (4)
C12—H12A0.9900C40—H40A0.9900
C12—H12B0.9900C40—H40B0.9900
C13—C141.513 (4)C41—C421.525 (4)
C13—H13A0.9900C41—H41A0.9900
C13—H13B0.9900C41—H41B0.9900
C14—H14A0.9800C42—H42A0.9800
C14—H14B0.9800C42—H42B0.9800
C14—H14C0.9800C42—H42C0.9800
S3—C221.672 (3)S7—C501.660 (3)
S4—C221.742 (3)S8—C501.750 (3)
S4—C231.817 (3)S8—C511.811 (3)
O2—C151.344 (4)O4—C431.343 (4)
O2—H2O0.78 (3)O4—H4O0.76 (3)
N3—C211.278 (3)N7—C491.280 (3)
N3—N41.376 (3)N7—N81.376 (3)
N4—C221.336 (4)N8—C501.334 (3)
N4—H4N0.81 (3)N8—H8N0.83 (3)
C15—C161.397 (4)C43—C441.388 (4)
C15—C201.418 (4)C43—C481.414 (4)
C16—C171.363 (5)C44—C451.364 (4)
C16—H160.9500C44—H440.9500
C17—C181.385 (5)C45—C461.391 (4)
C17—H170.9500C45—H450.9500
C18—C191.381 (4)C46—C471.384 (4)
C18—H180.9500C46—H460.9500
C19—C201.395 (4)C47—C481.399 (4)
C19—H190.9500C47—H470.9500
C20—C211.456 (4)C48—C491.453 (4)
C21—H210.9500C49—H490.9500
C23—C241.513 (4)C51—C521.517 (4)
C23—H23A0.9900C51—H51A0.9900
C23—H23B0.9900C51—H51B0.9900
C24—C251.522 (4)C52—C531.511 (4)
C24—H24A0.9900C52—H52A0.9900
C24—H24B0.9900C52—H52B0.9900
C25—C261.521 (4)C53—C541.529 (4)
C25—H25A0.9900C53—H53A0.9900
C25—H25B0.9900C53—H53B0.9900
C26—C271.522 (4)C54—C551.518 (4)
C26—H26A0.9900C54—H54A0.9900
C26—H26B0.9900C54—H54B0.9900
C27—C281.515 (4)C55—C561.509 (4)
C27—H27A0.9900C55—H55A0.9900
C27—H27B0.9900C55—H55B0.9900
C28—H28A0.9800C56—H56A0.9800
C28—H28B0.9800C56—H56B0.9800
C28—H28C0.9800C56—H56C0.9800
C8—S2—C9102.33 (13)C36—S6—C37102.60 (14)
C1—O1—H1O119 (3)C29—O3—H3O107 (2)
C7—N1—N2117.3 (2)C35—N5—N6116.9 (2)
C8—N2—N1121.4 (2)C36—N6—N5120.6 (2)
C8—N2—H2N119.8 (19)C36—N6—H6N118 (2)
N1—N2—H2N118.8 (19)N5—N6—H6N122 (2)
O1—C1—C2118.4 (3)O3—C29—C30118.0 (3)
O1—C1—C6122.3 (3)O3—C29—C34122.7 (3)
C2—C1—C6119.3 (3)C30—C29—C34119.3 (3)
C3—C2—C1120.4 (3)C31—C30—C29120.7 (3)
C3—C2—H2119.8C31—C30—H30119.6
C1—C2—H2119.8C29—C30—H30119.6
C2—C3—C4121.6 (3)C30—C31—C32121.6 (3)
C2—C3—H3119.2C30—C31—H31119.2
C4—C3—H3119.2C32—C31—H31119.2
C3—C4—C5118.9 (3)C33—C32—C31118.2 (3)
C3—C4—H4120.5C33—C32—H32120.9
C5—C4—H4120.5C31—C32—H32120.9
C4—C5—C6121.6 (3)C32—C33—C34121.9 (3)
C4—C5—H5119.2C32—C33—H33119.0
C6—C5—H5119.2C34—C33—H33119.0
C5—C6—C1118.2 (3)C33—C34—C29118.2 (3)
C5—C6—C7119.2 (3)C33—C34—C35119.5 (3)
C1—C6—C7122.6 (3)C29—C34—C35122.2 (3)
N1—C7—C6122.6 (3)N5—C35—C34121.2 (3)
N1—C7—H7118.7N5—C35—H35119.4
C6—C7—H7118.7C34—C35—H35119.4
N2—C8—S1120.6 (2)N6—C36—S5120.7 (2)
N2—C8—S2114.7 (2)N6—C36—S6114.1 (2)
S1—C8—S2124.79 (18)S5—C36—S6125.18 (18)
C10—C9—S2108.02 (19)C38—C37—S6107.53 (19)
C10—C9—H9A110.1C38—C37—H37A110.2
S2—C9—H9A110.1S6—C37—H37A110.2
C10—C9—H9B110.1C38—C37—H37B110.2
S2—C9—H9B110.1S6—C37—H37B110.2
H9A—C9—H9B108.4H37A—C37—H37B108.5
C11—C10—C9111.0 (2)C37—C38—C39112.0 (2)
C11—C10—H10A109.4C37—C38—H38A109.2
C9—C10—H10A109.4C39—C38—H38A109.2
C11—C10—H10B109.4C37—C38—H38B109.2
C9—C10—H10B109.4C39—C38—H38B109.2
H10A—C10—H10B108.0H38A—C38—H38B107.9
C12—C11—C10112.8 (2)C38—C39—C40112.0 (2)
C12—C11—H11A109.0C38—C39—H39A109.2
C10—C11—H11A109.0C40—C39—H39A109.2
C12—C11—H11B109.0C38—C39—H39B109.2
C10—C11—H11B109.0C40—C39—H39B109.2
H11A—C11—H11B107.8H39A—C39—H39B107.9
C11—C12—C13113.3 (2)C39—C40—C41113.3 (2)
C11—C12—H12A108.9C39—C40—H40A108.9
C13—C12—H12A108.9C41—C40—H40A108.9
C11—C12—H12B108.9C39—C40—H40B108.9
C13—C12—H12B108.9C41—C40—H40B108.9
H12A—C12—H12B107.7H40A—C40—H40B107.7
C14—C13—C12112.7 (2)C42—C41—C40112.7 (2)
C14—C13—H13A109.0C42—C41—H41A109.1
C12—C13—H13A109.0C40—C41—H41A109.1
C14—C13—H13B109.0C42—C41—H41B109.1
C12—C13—H13B109.0C40—C41—H41B109.1
H13A—C13—H13B107.8H41A—C41—H41B107.8
C13—C14—H14A109.5C41—C42—H42A109.5
C13—C14—H14B109.5C41—C42—H42B109.5
H14A—C14—H14B109.5H42A—C42—H42B109.5
C13—C14—H14C109.5C41—C42—H42C109.5
H14A—C14—H14C109.5H42A—C42—H42C109.5
H14B—C14—H14C109.5H42B—C42—H42C109.5
C22—S4—C23102.46 (15)C50—S8—C51102.66 (13)
C15—O2—H2O119 (3)C43—O4—H4O109 (3)
C21—N3—N4116.7 (3)C49—N7—N8117.1 (2)
C22—N4—N3121.1 (3)C50—N8—N7120.7 (2)
C22—N4—H4N119 (2)C50—N8—H8N120 (2)
N3—N4—H4N120 (2)N7—N8—H8N119 (2)
O2—C15—C16117.9 (3)O4—C43—C44117.8 (3)
O2—C15—C20122.8 (3)O4—C43—C48123.1 (3)
C16—C15—C20119.2 (3)C44—C43—C48119.1 (3)
C17—C16—C15120.1 (3)C45—C44—C43121.0 (3)
C17—C16—H16119.9C45—C44—H44119.5
C15—C16—H16119.9C43—C44—H44119.5
C16—C17—C18122.2 (3)C44—C45—C46121.5 (3)
C16—C17—H17118.9C44—C45—H45119.3
C18—C17—H17118.9C46—C45—H45119.3
C19—C18—C17118.1 (3)C47—C46—C45118.2 (3)
C19—C18—H18120.9C47—C46—H46120.9
C17—C18—H18120.9C45—C46—H46120.9
C18—C19—C20122.0 (3)C46—C47—C48121.8 (3)
C18—C19—H19119.0C46—C47—H47119.1
C20—C19—H19119.0C48—C47—H47119.1
C19—C20—C15118.4 (3)C47—C48—C43118.6 (3)
C19—C20—C21119.4 (3)C47—C48—C49118.9 (3)
C15—C20—C21122.2 (3)C43—C48—C49122.5 (3)
N3—C21—C20122.3 (3)N7—C49—C48120.8 (3)
N3—C21—H21118.9N7—C49—H49119.6
C20—C21—H21118.9C48—C49—H49119.6
N4—C22—S3120.7 (2)N8—C50—S7121.0 (2)
N4—C22—S4114.4 (2)N8—C50—S8113.9 (2)
S3—C22—S4124.8 (2)S7—C50—S8125.07 (17)
C24—C23—S4108.4 (2)C52—C51—S8107.84 (19)
C24—C23—H23A110.0C52—C51—H51A110.1
S4—C23—H23A110.0S8—C51—H51A110.1
C24—C23—H23B110.0C52—C51—H51B110.1
S4—C23—H23B110.0S8—C51—H51B110.1
H23A—C23—H23B108.4H51A—C51—H51B108.5
C23—C24—C25110.9 (2)C53—C52—C51112.2 (2)
C23—C24—H24A109.5C53—C52—H52A109.2
C25—C24—H24A109.5C51—C52—H52A109.2
C23—C24—H24B109.5C53—C52—H52B109.2
C25—C24—H24B109.5C51—C52—H52B109.2
H24A—C24—H24B108.1H52A—C52—H52B107.9
C26—C25—C24113.5 (2)C52—C53—C54112.9 (2)
C26—C25—H25A108.9C52—C53—H53A109.0
C24—C25—H25A108.9C54—C53—H53A109.0
C26—C25—H25B108.9C52—C53—H53B109.0
C24—C25—H25B108.9C54—C53—H53B109.0
H25A—C25—H25B107.7H53A—C53—H53B107.8
C25—C26—C27113.0 (3)C55—C54—C53113.4 (2)
C25—C26—H26A109.0C55—C54—H54A108.9
C27—C26—H26A109.0C53—C54—H54A108.9
C25—C26—H26B109.0C55—C54—H54B108.9
C27—C26—H26B109.0C53—C54—H54B108.9
H26A—C26—H26B107.8H54A—C54—H54B107.7
C28—C27—C26113.2 (3)C56—C55—C54112.9 (2)
C28—C27—H27A108.9C56—C55—H55A109.0
C26—C27—H27A108.9C54—C55—H55A109.0
C28—C27—H27B108.9C56—C55—H55B109.0
C26—C27—H27B108.9C54—C55—H55B109.0
H27A—C27—H27B107.8H55A—C55—H55B107.8
C27—C28—H28A109.5C55—C56—H56A109.5
C27—C28—H28B109.5C55—C56—H56B109.5
H28A—C28—H28B109.5H56A—C56—H56B109.5
C27—C28—H28C109.5C55—C56—H56C109.5
H28A—C28—H28C109.5H56A—C56—H56C109.5
H28B—C28—H28C109.5H56B—C56—H56C109.5
C7—N1—N2—C8−177.6 (2)C35—N5—N6—C36176.3 (2)
O1—C1—C2—C3179.9 (3)O3—C29—C30—C31179.3 (3)
C6—C1—C2—C3−0.4 (4)C34—C29—C30—C31−1.3 (4)
C1—C2—C3—C40.2 (5)C29—C30—C31—C321.8 (5)
C2—C3—C4—C50.1 (5)C30—C31—C32—C33−1.2 (5)
C3—C4—C5—C6−0.1 (5)C31—C32—C33—C340.1 (4)
C4—C5—C6—C1−0.1 (4)C32—C33—C34—C290.5 (4)
C4—C5—C6—C7177.1 (3)C32—C33—C34—C35−176.3 (3)
O1—C1—C6—C5−180.0 (3)O3—C29—C34—C33179.5 (2)
C2—C1—C6—C50.4 (4)C30—C29—C34—C330.1 (4)
O1—C1—C6—C72.9 (4)O3—C29—C34—C35−3.8 (4)
C2—C1—C6—C7−176.8 (3)C30—C29—C34—C35176.8 (2)
N2—N1—C7—C6178.5 (2)N6—N5—C35—C34−178.1 (2)
C5—C6—C7—N1−178.3 (3)C33—C34—C35—N5179.0 (2)
C1—C6—C7—N1−1.2 (4)C29—C34—C35—N52.3 (4)
N1—N2—C8—S1179.09 (18)N5—N6—C36—S5−178.17 (19)
N1—N2—C8—S2−1.0 (3)N5—N6—C36—S62.1 (3)
C9—S2—C8—N2−174.8 (2)C37—S6—C36—N6174.1 (2)
C9—S2—C8—S15.1 (2)C37—S6—C36—S5−5.6 (2)
C8—S2—C9—C10177.90 (19)C36—S6—C37—C38−179.37 (19)
S2—C9—C10—C11−179.99 (19)S6—C37—C38—C39−178.21 (19)
C9—C10—C11—C12−179.2 (2)C37—C38—C39—C40179.3 (2)
C10—C11—C12—C13175.8 (2)C38—C39—C40—C41−178.6 (2)
C11—C12—C13—C14−179.8 (2)C39—C40—C41—C42176.4 (2)
C21—N3—N4—C22178.1 (3)C49—N7—N8—C50−176.6 (2)
O2—C15—C16—C17179.7 (3)O4—C43—C44—C45−179.9 (3)
C20—C15—C16—C170.1 (4)C48—C43—C44—C45−0.1 (4)
C15—C16—C17—C181.0 (5)C43—C44—C45—C46−0.1 (5)
C16—C17—C18—C19−1.5 (5)C44—C45—C46—C47−0.2 (4)
C17—C18—C19—C201.0 (5)C45—C46—C47—C480.7 (4)
C18—C19—C20—C150.1 (4)C46—C47—C48—C43−0.8 (4)
C18—C19—C20—C21−178.0 (3)C46—C47—C48—C49176.6 (2)
O2—C15—C20—C19179.8 (3)O4—C43—C48—C47−179.7 (2)
C16—C15—C20—C19−0.6 (4)C44—C43—C48—C470.5 (4)
O2—C15—C20—C21−2.2 (4)O4—C43—C48—C493.0 (4)
C16—C15—C20—C21177.4 (3)C44—C43—C48—C49−176.8 (2)
N4—N3—C21—C20−177.6 (2)N8—N7—C49—C48178.1 (2)
C19—C20—C21—N3179.1 (3)C47—C48—C49—N7−179.3 (2)
C15—C20—C21—N31.1 (4)C43—C48—C49—N7−1.9 (4)
N3—N4—C22—S3−179.53 (19)N7—N8—C50—S7176.98 (18)
N3—N4—C22—S40.6 (4)N7—N8—C50—S8−3.4 (3)
C23—S4—C22—N4175.2 (2)C51—S8—C50—N8−174.4 (2)
C23—S4—C22—S3−4.7 (2)C51—S8—C50—S75.2 (2)
C22—S4—C23—C24178.7 (2)C50—S8—C51—C52−176.75 (19)
S4—C23—C24—C25−178.71 (19)S8—C51—C52—C53177.41 (19)
C23—C24—C25—C26176.4 (2)C51—C52—C53—C54−176.9 (2)
C24—C25—C26—C27−175.7 (2)C52—C53—C54—C55179.5 (2)
C25—C26—C27—C28−178.6 (3)C53—C54—C55—C56−177.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.73 (3)2.13 (3)2.684 (3)135 (3)
O2—H2O···N30.78 (3)2.09 (3)2.685 (3)133 (3)
O3—H3O···N50.84 (3)1.91 (3)2.662 (3)148 (3)
O4—H4O···N70.75 (3)2.00 (3)2.663 (3)146 (3)
N2—H2N···S7i0.86 (3)2.58 (3)3.430 (3)169 (3)
N4—H4N···S3ii0.81 (3)2.64 (3)3.439 (3)171 (2)
N6—H6N···S5iii0.84 (3)2.59 (3)3.398 (3)162 (2)
N8—H8N···S1iv0.83 (3)2.61 (3)3.403 (3)160 (2)
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x, −y+1, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.73 (3)2.13 (3)2.684 (3)135 (3)
O2—H2O···N30.78 (3)2.09 (3)2.685 (3)133 (3)
O3—H3O···N50.84 (3)1.91 (3)2.662 (3)148 (3)
O4—H4O···N70.75 (3)2.00 (3)2.663 (3)146 (3)
N2—H2N···S7i0.86 (3)2.58 (3)3.430 (3)169 (3)
N4—H4N···S3ii0.81 (3)2.64 (3)3.439 (3)171 (2)
N6—H6N···S5iii0.84 (3)2.59 (3)3.398 (3)162 (2)
N8—H8N···S1iv0.83 (3)2.61 (3)3.403 (3)160 (2)
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formulaC14H20N2OS2
Mr296.44
Crystal system, space groupMonoclinic, P2/c
Temperature (K)173
a, b, c (Å)18.9744 (4), 16.0269 (3), 21.1146 (4)
β (°) 100.808 (1)
V (Å3)6307.1 (2)
Z16
Radiation typeCu Kα
µ (mm−1)3.01
Crystal size (mm)0.50 × 0.35 × 0.34
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		10367, 10367, 6152
Rint0.072
(sin θ/λ)max (Å−1)0.581
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.176, 0.93
No. of reflections10367
No. of parameters713
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.01, −0.46

Computer programs: RAPID-AUTO (Rigaku, 2001), SIR92 (Altomare et al., 1994), SHELXL2014 (Sheldrick, 2015), CrystalStructure (Rigaku, 2010).

 

Acknowledgements

MBHH and MSB are grateful to the Department of Chemistry, Rajshahi University, for the provision of laboratory facilities. MCS acknowledges the Department of Applied Chemistry,Toyama University, for providing funds for single-crystal X-ray analyses.

References

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 First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
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 First citationChan, M. E., Crouse, K. A., Tahir, M. I. M., Rosli, R., Umar-Tsafe, N. & Cowley, A. R. (2008). Polyhedron, 27, 1141–1149.  Web of Science CSD CrossRef CAS Google Scholar
 First citationChew, K. B., Tarafder, M. T. H., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 1385–1392.  Web of Science CSD CrossRef CAS Google Scholar
 First citationCrouse, K. A., Chew, K. B., Tarafder, M. T. H., Kasbollah, A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 161–168.  Web of Science CSD CrossRef CAS Google Scholar
 First citationHow, F. N. F., Crouse, K. A., Tahir, M. I. M., Tarafder, M. T. H. & Cowley, A. R. (2008). Polyhedron, 27, 3325–3329.  Web of Science CSD CrossRef CAS Google Scholar
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 First citationRigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationZangrando, E., Islam, M. T., Islam, M. A. A. A., Sheikh, M. C., Tarafder, M. T. H., Miyatake, R., Zahan, R. & Hossain, M. A. (2015). Inorg. Chim. Acta, 427, 278–284.  Web of Science CSD CrossRef CAS 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 72| Part 3| March 2016| Pages 290-292
doi:10.1107/S2056989016001857
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