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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o265-o266
doi:10.1107/S205698901500568X

Crystal structure of S-octyl (E)-3-(4-meth­­oxy­benzyl­­idene)di­thio­carbazate

CROSSMARK_Color_square_no_text.svg
M. S. Begum,a* E. Zangrando,b M. C. Sheikh,c R. Miyataked and M. M. Hossaina

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

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 5 March 2015; accepted 19 March 2015; online 28 March 2015)

As already observed in similar mol­ecules, the di­thio­carbazate group in the title compound, C17H26N2OS2, adopts an EE configuration with respect to the C=N bond of the benzyl­idene moiety. In the crystal, mol­ecules are connected into inversion dimers by pairs of N—H⋯S hydrogen bonds. The dimers are linked by weak π–π inter­actions, with centroid-to-centroid distances of 3.723 (11) Å, forming chains parallel to [110].

CCDC reference: 1044476

Similar articles

1. Related literature

For the structures of related compounds, see: Howlader et al. (2015[Howlader, M. B. H., Begum, M. S., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, o103-o104.]); Begum et al. (2015[Begum, M. S., Howlader, M. B. H., Miyatake, R., Zangrando, E. & Sheikh, M. C. (2015). Acta Cryst. E71, o199.]). For metal complexes containing similar ligands, see: Chan et al. (2008[Chan, M. H. 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.]); Tarafder et al. (2002[Tarafder, M. T. H., Chew, K. B., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2683-2690.]); 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.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H26N2OS2

  • Mr = 338.53

  • Monoclinic, C 2/c

  • a = 28.7970 (6) Å

  • b = 8.37150 (15) Å

  • c = 15.6207 (3) Å

  • β = 104.2210 (7)°

  • V = 3650.36 (12) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.66 mm−1

  • T = 173 K

  • 0.32 × 0.21 × 0.13 mm

2.2. Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.581, Tmax = 0.708

  • 20438 measured reflections

  • 3333 independent reflections

  • 3140 reflections with F2 > 2σ(F2)

  • Rint = 0.056

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.096

  • S = 1.06

  • 3333 reflections

  • 205 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H9⋯S1i 0.86 (2) 2.536 (18) 3.3870 (11) 170.9 (16)
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: 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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1044476

Crystal structure: contains datablocks General, I. DOI: 10.1107/S205698901500568X/rz5151sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500568X/rz5151Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500568X/rz5151Isup3.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; Tarafder et al., 2002; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing Schiff bases (Howlader et al., 2015; Begum et al., 2015), we report herein the structure of the title compound having a long alkyl chain.

Structural commentary top

The molecule of the title compound is shown in Fig. 1. The Schiff base exists in thione tautomeric form with the di­thio­carbazate fragment adopting an EE configuration with respect to the C═N bond of the benzyl­idene moiety. The β-nitro­gen and the thio­keto sulphur are trans located with respect to the C9–N2 bond. With the exception of the S-octyl chain, the atoms of the 3-(4-meth­oxy­benzyl­idene)di­thio­carbazate group are approximately co-planar (r.m.s. deviation = 0.253 Å) indicating electron delocalization within it. The bond lengths and angles are closely comparable to those detected in S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015) and in the S-hexyl analogue (Begum et al., 2015), characterized by a shorter alkyl chain.

Supra­molecular features top

The crystal packing of the title compound evidences molecules connected into centrosymmetric dimers (Fig. 2) by pairs of N—H···S hydrogen bonds (Table 1), which are further linked by weak π-π stacking inter­actions (centroid-to-centroid distances of 3.723 (11) Å) to form chains parallel to the [1 1 0] direction.

Database survey top

The octyl chain shows the typical all-anti conformation with a S(2)—C(10)—C(11)—C(12) torsion angle of 169.73 (9)°, which differs from that of 66.6 (2)° measured in the corresponding S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015), but comparable to the value of 173.99 (13)° found in the hexyl derivative (Begum et al., 2015) .

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 was stirred at 273 K. To this solution carbon di­sulfide (3.81 g, 0.05 mol) was added dropwise with constant stirring for one hour. Then 1-bromo­octane (9.65 g, 0.05 mol) was added dropwise with vigorous stirring at 273 K for an additional hour. Finally, 4-meth­oxy­benzaldehyde (6.81 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, which was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals, suitable for X-ray diffraction of the compound were obtained by slow evaporation of an ethanol/aceto­nitrile (2:1 v/v) solution after 19 days (m. p. 355 K).

Refinement top

Hydrogen atoms were located geometrically and treated as riding atoms with C—H = 0.98–0.99 Å and Uĩso(H) = 1.2Ueq(C). The hydrogen atom at N2 was located on the difference Fourier map and freely refined.

Related literature top

For the structures of related compounds, see: Howlader et al. (2015); Begum et al. (2015). For metal complexes containing similar ligands, see: Chan et al. (2008); How et al. (2008); Tarafder et al. (2002); Ali et al. (2002); Chew et al. (2004); Crouse et al. (2004).

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; Tarafder et al., 2002; Ali et al., 2002; Chew et al., 2004; Crouse et al., 2004). As part of our ongoing structural studies of S-containing Schiff bases (Howlader et al., 2015; Begum et al., 2015), we report herein the structure of the title compound having a long alkyl chain.

The molecule of the title compound is shown in Fig. 1. The Schiff base exists in thione tautomeric form with the di­thio­carbazate fragment adopting an EE configuration with respect to the C═N bond of the benzyl­idene moiety. The β-nitro­gen and the thio­keto sulphur are trans located with respect to the C9–N2 bond. With the exception of the S-octyl chain, the atoms of the 3-(4-meth­oxy­benzyl­idene)di­thio­carbazate group are approximately co-planar (r.m.s. deviation = 0.253 Å) indicating electron delocalization within it. The bond lengths and angles are closely comparable to those detected in S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015) and in the S-hexyl analogue (Begum et al., 2015), characterized by a shorter alkyl chain.

The crystal packing of the title compound evidences molecules connected into centrosymmetric dimers (Fig. 2) by pairs of N—H···S hydrogen bonds (Table 1), which are further linked by weak π-π stacking inter­actions (centroid-to-centroid distances of 3.723 (11) Å) to form chains parallel to the [1 1 0] direction.

The octyl chain shows the typical all-anti conformation with a S(2)—C(10)—C(11)—C(12) torsion angle of 169.73 (9)°, which differs from that of 66.6 (2)° measured in the corresponding S-hexyl (E)-3-(4-methyl­benzyl­idene)di­thio­carbazate (Howlader et al., 2015), but comparable to the value of 173.99 (13)° found in the hexyl derivative (Begum et al., 2015) .

For the structures of related compounds, see: Howlader et al. (2015); Begum et al. (2015). For metal complexes containing similar ligands, see: Chan et al. (2008); How et al. (2008); Tarafder et al. (2002); Ali et al. (2002); Chew et al. (2004); Crouse et al. (2004).

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 was stirred at 273 K. To this solution carbon di­sulfide (3.81 g, 0.05 mol) was added dropwise with constant stirring for one hour. Then 1-bromo­octane (9.65 g, 0.05 mol) was added dropwise with vigorous stirring at 273 K for an additional hour. Finally, 4-meth­oxy­benzaldehyde (6.81 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, which was recrystallized from ethanol at room temperature and dried in a vacuum desiccator over anhydrous CaCl2. Colourless crystals, suitable for X-ray diffraction of the compound were obtained by slow evaporation of an ethanol/aceto­nitrile (2:1 v/v) solution after 19 days (m. p. 355 K).

Refinement details top

Hydrogen atoms were located geometrically and treated as riding atoms with C—H = 0.98–0.99 Å and Uĩso(H) = 1.2Ueq(C). The hydrogen atom at N2 was located on the difference Fourier map and freely refined.

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: SHELXL97 (Sheldrick, 2008); 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 the title compound with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound showing pairs of molecules connected by N—H···S hydrogen interactions (dashed lines). H atoms not involved in hydrogen bonding are omitted.
S-Octyl (E)-3-(4-methoxybenzylidene)dithiocarbazate top
Crystal data top
C17H26N2OS2F(000) = 1456.00
Mr = 338.53Dx = 1.232 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -C 2ycCell parameters from 19039 reflections
a = 28.7970 (6) Åθ = 3.2–68.2°
b = 8.37150 (15) ŵ = 2.66 mm−1
c = 15.6207 (3) ÅT = 173 K
β = 104.2210 (7)°Prism, colorless
V = 3650.36 (12) Å30.32 × 0.21 × 0.13 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3140 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.056
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)		h = −34→34
Tmin = 0.581, Tmax = 0.708k = −10→9
20438 measured reflectionsl = −18→18
3333 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0604P)2 + 1.4685P]
where P = (Fo2 + 2Fc2)/3
3333 reflections(Δ/σ)max = 0.002
205 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C17H26N2OS2V = 3650.36 (12) Å3
Mr = 338.53Z = 8
Monoclinic, C2/cCu Kα radiation
a = 28.7970 (6) ŵ = 2.66 mm−1
b = 8.37150 (15) ÅT = 173 K
c = 15.6207 (3) Å0.32 × 0.21 × 0.13 mm
β = 104.2210 (7)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3333 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)		3140 reflections with F2 > 2σ(F2)
Tmin = 0.581, Tmax = 0.708Rint = 0.056
20438 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.37 e Å−3
3333 reflectionsΔρmin = −0.33 e Å−3
205 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S20.807022 (11)0.14416 (4)0.28621 (2)0.03085 (13)
S10.719578 (11)0.16904 (4)0.36276 (2)0.03091 (13)
O11.08208 (4)0.33645 (14)0.60247 (7)0.0427 (3)
N10.85671 (4)0.24695 (14)0.45179 (7)0.0295 (3)
N20.80783 (4)0.24227 (14)0.44385 (7)0.0290 (3)
C11.10812 (5)0.4216 (3)0.67848 (11)0.0535 (5)
C21.03338 (5)0.33880 (18)0.58554 (9)0.0331 (4)
C31.00927 (5)0.24210 (19)0.51590 (9)0.0376 (4)
C40.96000 (5)0.23336 (18)0.49421 (9)0.0349 (4)
C50.93337 (5)0.32172 (16)0.54197 (9)0.0288 (3)
C60.95789 (5)0.41699 (18)0.61083 (9)0.0327 (3)
C71.00768 (5)0.42693 (18)0.63288 (9)0.0344 (4)
C80.88118 (5)0.31449 (17)0.52194 (9)0.0298 (3)
C90.77823 (5)0.18870 (16)0.36983 (9)0.0272 (3)
C100.75805 (5)0.08849 (17)0.19384 (8)0.0304 (3)
C110.73334 (5)0.23027 (17)0.14066 (9)0.0315 (3)
C120.69859 (5)0.17876 (17)0.05459 (9)0.0312 (3)
C130.67214 (5)0.32009 (17)0.00317 (9)0.0335 (4)
C140.63553 (5)0.27125 (18)−0.08091 (9)0.0342 (3)
C150.61160 (5)0.41321 (19)−0.13503 (9)0.0362 (4)
C160.57411 (6)0.3675 (2)−0.21842 (10)0.0405 (4)
C170.55655 (6)0.5106 (3)−0.27733 (11)0.0526 (5)
H11.09740.38710.73040.0641*
H21.10240.53640.66940.0641*
H31.14240.39950.68780.0641*
H41.02700.18190.48320.0451*
H50.94390.16720.44670.0419*
H60.94030.47700.64380.0393*
H71.02380.49370.68000.0413*
H80.86500.36100.56190.0358*
H90.7974 (6)0.265 (2)0.4894 (12)0.034 (5)*
H100.77050.01700.15420.0365*
H110.73410.02760.21640.0365*
H120.75790.30200.12690.0378*
H130.71560.29120.17670.0378*
H140.71660.12210.01730.0374*
H150.67490.10320.06820.0374*
H160.65550.37970.04170.0402*
H170.69580.3930−0.01260.0402*
H180.65170.2055−0.11770.0410*
H190.61060.2043−0.06490.0410*
H200.63660.4788−0.15180.0434*
H210.59620.4801−0.09760.0434*
H220.58800.2879−0.25190.0486*
H230.54650.3170−0.20170.0486*
H240.54550.5939−0.24290.0631*
H250.53000.4779−0.32650.0631*
H260.58280.5524−0.30060.0631*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0245 (2)0.0413 (3)0.0272 (2)−0.00063 (13)0.00700 (14)−0.00084 (12)
S10.02225 (19)0.0414 (3)0.0290 (2)−0.00425 (12)0.00629 (14)−0.00176 (13)
O10.0221 (5)0.0673 (8)0.0384 (6)0.0004 (5)0.0065 (5)0.0005 (5)
N10.0217 (6)0.0356 (7)0.0302 (6)−0.0007 (5)0.0047 (5)0.0028 (5)
N20.0218 (6)0.0381 (7)0.0271 (6)−0.0021 (5)0.0058 (5)−0.0005 (5)
C10.0243 (7)0.0921 (15)0.0420 (9)−0.0058 (8)0.0044 (7)−0.0050 (9)
C20.0230 (7)0.0447 (9)0.0309 (8)0.0007 (6)0.0053 (6)0.0091 (6)
C30.0313 (8)0.0473 (9)0.0353 (8)0.0050 (7)0.0105 (6)−0.0007 (7)
C40.0306 (7)0.0411 (9)0.0318 (7)−0.0000 (6)0.0052 (6)−0.0029 (6)
C50.0243 (7)0.0332 (8)0.0279 (7)−0.0010 (6)0.0044 (5)0.0052 (6)
C60.0259 (7)0.0420 (9)0.0299 (7)0.0018 (6)0.0060 (6)−0.0009 (6)
C70.0266 (7)0.0433 (9)0.0306 (7)−0.0024 (6)0.0018 (6)−0.0012 (6)
C80.0254 (7)0.0347 (8)0.0295 (7)−0.0004 (6)0.0068 (6)0.0031 (6)
C90.0260 (7)0.0273 (7)0.0282 (7)−0.0002 (5)0.0069 (5)0.0037 (5)
C100.0310 (7)0.0329 (8)0.0271 (7)−0.0015 (6)0.0064 (6)−0.0030 (6)
C110.0338 (7)0.0318 (8)0.0278 (7)−0.0028 (6)0.0056 (6)−0.0008 (6)
C120.0313 (7)0.0349 (8)0.0272 (7)−0.0016 (6)0.0070 (6)−0.0024 (6)
C130.0331 (7)0.0360 (8)0.0302 (7)−0.0017 (6)0.0055 (6)−0.0016 (6)
C140.0335 (8)0.0366 (8)0.0311 (7)−0.0005 (6)0.0053 (6)−0.0021 (6)
C150.0347 (8)0.0376 (9)0.0351 (8)0.0016 (6)0.0064 (6)−0.0009 (6)
C160.0372 (9)0.0445 (9)0.0360 (8)0.0041 (7)0.0020 (7)0.0003 (7)
C170.0503 (10)0.0593 (12)0.0443 (9)0.0100 (9)0.0043 (8)0.0105 (8)
Geometric parameters (Å, º) top
S2—C91.7506 (16)C1—H20.980
S2—C101.8133 (13)C1—H30.980
S1—C91.6734 (15)C3—H40.950
O1—C11.429 (2)C4—H50.950
O1—C21.3619 (19)C6—H60.950
N1—N21.3829 (17)C7—H70.950
N1—C81.2797 (17)C8—H80.950
N2—C91.3343 (16)C10—H100.990
C2—C31.396 (2)C10—H110.990
C2—C71.381 (3)C11—H120.990
C3—C41.377 (2)C11—H130.990
C4—C51.405 (3)C12—H140.990
C5—C61.3851 (19)C12—H150.990
C5—C81.459 (2)C13—H160.990
C6—C71.392 (2)C13—H170.990
C10—C111.5214 (19)C14—H180.990
C11—C121.5277 (18)C14—H190.990
C12—C131.525 (2)C15—H200.990
C13—C141.5242 (18)C15—H210.990
C14—C151.522 (2)C16—H220.990
C15—C161.5224 (19)C16—H230.990
C16—C171.520 (3)C17—H240.980
N2—H90.860 (19)C17—H250.980
C1—H10.980C17—H260.980
S2···N12.7676 (11)C17···H1viii3.3558
S1···C103.1750 (15)C17···H5x3.0329
N1···C42.8863 (18)C17···H23ix3.3270
C1···C72.804 (2)C17···H24ix3.1111
C2···C52.796 (2)C17···H25ix3.3030
C3···C62.759 (3)H1···C6xii3.2687
C4···C72.7824 (19)H1···C17iii3.3558
C8···C93.4760 (18)H1···H6xii2.5789
C9···C113.5119 (19)H1···H8xii3.1650
S1···N2i3.3870 (13)H1···H22xiii3.3830
O1···C13ii3.581 (2)H1···H24iii2.9558
O1···C17iii3.490 (3)H1···H26iii2.8571
N2···S1i3.3870 (13)H2···N1iv3.0576
C2···C17iii3.447 (3)H2···C4iv3.3491
C3···C7iv3.572 (2)H2···C5iv3.4202
C7···C3iv3.572 (2)H2···C8iv3.3768
C9···C10v3.574 (2)H2···C16xiii3.4817
C10···C9vi3.574 (2)H2···H5iv3.1680
C13···O1vii3.581 (2)H2···H6xii3.4703
C17···O1viii3.490 (3)H2···H15ii3.1378
C17···C2viii3.447 (3)H2···H18xiii3.5729
C17···C17ix3.564 (3)H2···H22xiii2.5239
S2···H93.408 (19)H3···S1ii3.1229
S2···H122.8652H3···C10ii3.3094
S2···H133.0259H3···C11ii3.0861
S1···H92.721 (15)H3···C12ii3.0047
S1···H112.6961H3···H11ii2.6381
S1···H133.0558H3···H13ii2.6829
O1···H42.4918H3···H15ii2.2865
O1···H72.6484H3···H16ii3.3522
N1···H52.6194H3···H26iii3.4022
N2···H82.3679H4···C4xiv3.5050
C1···H72.5074H4···C14ii3.5310
C2···H12.5754H4···C15ii3.4923
C2···H22.6692H4···H4xiv3.5163
C2···H33.1945H4···H5xiv3.1607
C2···H53.2641H4···H19ii2.8569
C2···H63.2480H4···H21ii2.9400
C3···H73.2645H4···H23ii3.0754
C4···H63.2549H4···H25iii3.4102
C4···H83.3422H4···H25x2.9160
C5···H43.2702H4···H26iii3.5353
C5···H73.2784H5···C16x3.4872
C6···H53.2558H5···C17x3.0329
C6···H82.6377H5···H2iv3.1680
C7···H12.6779H5···H4xiv3.1607
C7···H22.8008H5···H21vi3.2685
C7···H43.2588H5···H22x2.9783
C8···H52.6856H5···H25x2.5007
C8···H62.6043H5···H26x2.8847
C8···H92.378 (17)H6···C1xii3.4304
C9···H112.7711H6···C7xii3.4668
C9···H133.2268H6···C14v3.2785
C10···H142.7366H6···C16v3.5292
C10···H152.6996H6···H1xii2.5789
C11···H162.6966H6···H2xii3.4703
C11···H172.7354H6···H7xii2.6947
C12···H102.6384H6···H18v3.2113
C12···H112.7870H6···H19v2.5304
C12···H182.7073H6···H22v3.3118
C12···H192.7613H6···H23v2.9820
C13···H122.7405H6···H24vi3.5408
C13···H132.7037H7···C6xii3.2430
C13···H202.7310H7···C7xii3.3134
C13···H212.7136H7···H6xii2.6947
C14···H142.7571H7···H7xii2.8520
C14···H152.7190H7···H22xiii3.1062
C14···H222.6894H7···H23xiii3.2518
C14···H232.8104H7···H23v3.4467
C15···H162.7538H7···H24iii3.5593
C15···H172.6999H8···S1i2.9639
C15···H242.6788H8···C12v3.4787
C15···H253.3623H8···C14v3.4473
C15···H262.7709H8···H1xii3.1650
C16···H182.7528H8···H14v3.2245
C16···H192.7357H8···H15v2.9005
C17···H202.6466H8···H18v3.0839
C17···H212.7707H8···H19v2.9561
H1···H72.2546H8···H20vi3.4994
H2···H72.3376H8···H21vi3.3796
H3···H73.4782H9···S1i2.535 (19)
H4···H52.3211H9···N2i3.437 (19)
H6···H72.3355H9···C9i3.47 (2)
H6···H82.4334H9···C12v3.537 (17)
H8···H92.1528H9···H9i2.84 (3)
H10···H122.4347H9···H10v3.3375
H10···H132.8577H9···H14v3.0126
H10···H142.4748H9···H15v3.1308
H10···H152.8433H9···H16vi3.5803
H11···H122.8584H9···H17vi3.1377
H11···H132.3179H10···S1vi2.9452
H11···H143.1276H10···N2vi3.3208
H11···H152.5935H10···C9vi3.0670
H12···H142.3686H10···C13x3.5527
H12···H152.8703H10···C15x3.5289
H12···H162.9920H10···H9vi3.3375
H12···H172.5710H10···H13vi3.1923
H13···H142.8703H10···H17x2.7303
H13···H152.3976H10···H18x3.3717
H13···H162.4898H10···H20x2.6850
H13···H172.9949H11···S2vi3.4182
H14···H162.8655H11···N2vi3.4566
H14···H172.3627H11···C1vii3.5543
H14···H182.5479H11···C9vi3.1237
H14···H193.0838H11···C11vi3.3213
H15···H162.3932H11···H3vii2.6381
H15···H172.8657H11···H12vi3.0549
H15···H182.9420H11···H13vi2.7593
H15···H192.5646H12···S1v3.1369
H16···H182.8632H12···C9v3.4048
H16···H192.3543H12···C12x3.3737
H16···H203.0518H12···C13x3.3534
H16···H212.5562H12···C14x3.3760
H17···H182.3977H12···H11v3.0549
H17···H192.8632H12···H14x2.6147
H17···H202.5169H12···H17x2.9670
H17···H212.9414H12···H18x2.6443
H18···H202.3650H13···S2v3.1108
H18···H212.8604H13···C1vii3.5770
H18···H222.5195H13···C9v3.4204
H18···H233.1319H13···C10v3.1786
H19···H202.8604H13···H3vii2.6829
H19···H212.3792H13···H10v3.1923
H19···H222.9180H13···H11v2.7593
H19···H232.6311H14···S1xvi3.4469
H20···H222.4246H14···N2vi3.3440
H20···H232.8587H14···C11x3.3834
H20···H242.8280H14···C12x3.3701
H20···H253.5700H14···C13x3.3332
H20···H262.5311H14···H8vi3.2245
H21···H222.8594H14···H9vi3.0126
H21···H232.3264H14···H12x2.6147
H21···H242.5621H14···H14x3.0159
H21···H263.1570H14···H17x2.5454
H22···H242.8570H15···O1vii2.8977
H22···H252.3908H15···N1vi3.1115
H22···H262.3335H15···N2vi3.0750
H23···H242.4045H15···C1vii2.8884
H23···H252.3211H15···C8vi3.0523
H23···H262.8557H15···H2vii3.1378
S2···H11v3.4182H15···H3vii2.2865
S2···H13vi3.1108H15···H8vi2.9005
S2···H16vi3.4450H15···H9vi3.1308
S2···H18x3.3864H16···S2v3.4450
S2···H20x3.1271H16···O1vii3.1046
S2···H22x3.2475H16···N1v3.0993
S2···H26x3.5318H16···N2v3.2031
S1···H3vii3.1229H16···C9v3.3082
S1···H8i2.9639H16···H3vii3.3522
S1···H9i2.535 (19)H16···H9v3.5803
S1···H10v2.9452H17···N1v3.5600
S1···H12vi3.1369H17···N2v3.1252
S1···H14xi3.4469H17···C9v3.2922
O1···H15ii2.8977H17···C10x3.4140
O1···H16ii3.1046H17···C11x3.3522
O1···H19ii2.9464H17···C12x3.3197
O1···H24iii3.5092H17···H9v3.1377
O1···H26iii2.8166H17···H10x2.7303
N1···H2iv3.0576H17···H12x2.9670
N1···H15v3.1115H17···H14x2.5454
N1···H16vi3.0993H18···S2x3.3864
N1···H17vi3.5600H18···C10x3.5590
N1···H21vi3.2400H18···C11x3.4591
N2···H9i3.437 (19)H18···H2xv3.5729
N2···H10v3.3208H18···H6vi3.2113
N2···H11v3.4566H18···H8vi3.0839
N2···H14v3.3440H18···H10x3.3717
N2···H15v3.0750H18···H12x2.6443
N2···H16vi3.2031H19···O1vii2.9464
N2···H17vi3.1252H19···C3vii3.4814
C1···H6xii3.4304H19···C5vi3.4947
C1···H11ii3.5543H19···C6vi3.0816
C1···H13ii3.5770H19···C8vi3.3283
C1···H15ii2.8884H19···H4vii2.8569
C1···H22xiii3.3520H19···H6vi2.5304
C1···H26iii3.2103H19···H8vi2.9561
C2···H24iii3.3234H20···S2x3.1271
C2···H25iii3.3303H20···C8v3.5758
C2···H26iii3.1138H20···C10x3.3068
C3···H19ii3.4814H20···H8v3.4994
C3···H25iii3.2537H20···H10x2.6850
C3···H25x3.4321H21···N1v3.2400
C3···H26iii3.4990H21···C4v3.3174
C4···H2iv3.3491H21···C5v3.1656
C4···H4xiv3.5050H21···C8v3.0459
C4···H21vi3.3174H21···H4vii2.9400
C4···H25x3.2313H21···H5v3.2685
C5···H2iv3.4202H21···H8v3.3796
C5···H19v3.4947H21···H25ix3.5358
C5···H21vi3.1656H22···S2x3.2475
C5···H24vi3.5947H22···C1xv3.3520
C6···H1xii3.2687H22···H1xv3.3830
C6···H7xii3.2430H22···H2xv2.5239
C6···H19v3.0816H22···H5x2.9783
C6···H24vi3.4177H22···H6vi3.3118
C7···H6xii3.4668H22···H7xv3.1062
C7···H7xii3.3134H23···C16ix3.4170
C7···H24iii3.4181H23···C17ix3.3270
C8···H2iv3.3768H23···H4vii3.0754
C8···H15v3.0523H23···H6vi2.9820
C8···H19v3.3283H23···H7xv3.2518
C8···H20vi3.5758H23···H7vi3.4467
C8···H21vi3.0459H23···H23ix2.7337
C9···H9i3.47 (2)H23···H24ix3.4671
C9···H10v3.0670H23···H25ix2.7103
C9···H11v3.1237H24···O1viii3.5092
C9···H12vi3.4048H24···C2viii3.3234
C9···H13vi3.4204H24···C5v3.5947
C9···H16vi3.3082H24···C6v3.4177
C9···H17vi3.2922H24···C7viii3.4181
C10···H3vii3.3094H24···C17ix3.1111
C10···H13vi3.1786H24···H1viii2.9558
C10···H17x3.4140H24···H6v3.5408
C10···H18x3.5590H24···H7viii3.5593
C10···H20x3.3068H24···H23ix3.4671
C11···H3vii3.0861H24···H24ix2.5751
C11···H11v3.3213H24···H25ix2.8301
C11···H14x3.3834H25···C2viii3.3303
C11···H17x3.3522H25···C3viii3.2537
C11···H18x3.4591H25···C3x3.4321
C12···H3vii3.0047H25···C4x3.2313
C12···H8vi3.4787H25···C16ix3.3726
C12···H9vi3.537 (17)H25···C17ix3.3030
C12···H12x3.3737H25···H4viii3.4102
C12···H14x3.3701H25···H4x2.9160
C12···H17x3.3197H25···H5x2.5007
C13···H10x3.5527H25···H21ix3.5358
C13···H12x3.3534H25···H23ix2.7103
C13···H14x3.3332H25···H24ix2.8301
C14···H4vii3.5310H25···H25ix3.2766
C14···H6vi3.2785H26···S2x3.5318
C14···H8vi3.4473H26···O1viii2.8166
C14···H12x3.3760H26···C1viii3.2103
C15···H4vii3.4923H26···C2viii3.1138
C15···H10x3.5289H26···C3viii3.4990
C16···H2xv3.4817H26···H1viii2.8571
C16···H5x3.4872H26···H3viii3.4022
C16···H6vi3.5292H26···H4viii3.5353
C16···H23ix3.4170H26···H5x2.8847
C16···H25ix3.3726
C9—S2—C10103.31 (7)C5—C8—H8119.226
C1—O1—C2117.34 (13)S2—C10—H10108.816
N2—N1—C8115.06 (13)S2—C10—H11108.818
N1—N2—C9120.45 (12)C11—C10—H10108.829
O1—C2—C3115.73 (14)C11—C10—H11108.819
O1—C2—C7124.43 (13)H10—C10—H11107.692
C3—C2—C7119.84 (13)C10—C11—H12109.164
C2—C3—C4120.49 (15)C10—C11—H13109.167
C3—C4—C5120.34 (13)C12—C11—H12109.165
C4—C5—C6118.36 (13)C12—C11—H13109.183
C4—C5—C8122.16 (12)H12—C11—H13107.873
C6—C5—C8119.48 (14)C11—C12—H14109.164
C5—C6—C7121.60 (15)C11—C12—H15109.150
C2—C7—C6119.36 (13)C13—C12—H14109.145
N1—C8—C5121.56 (14)C13—C12—H15109.144
S2—C9—S1125.81 (8)H14—C12—H15107.864
S2—C9—N2113.54 (11)C12—C13—H16108.911
S1—C9—N2120.65 (12)C12—C13—H17108.908
S2—C10—C11113.70 (10)C14—C13—H16108.897
C10—C11—C12112.19 (12)C14—C13—H17108.910
C11—C12—C13112.27 (12)H16—C13—H17107.734
C12—C13—C14113.33 (12)C13—C14—H18108.957
C13—C14—C15113.09 (12)C13—C14—H19108.962
C14—C15—C16114.09 (13)C15—C14—H18108.966
C15—C16—C17112.36 (14)C15—C14—H19108.970
N1—N2—H9118.4 (11)H18—C14—H19107.759
C9—N2—H9120.9 (11)C14—C15—H20108.728
O1—C1—H1109.474C14—C15—H21108.736
O1—C1—H2109.472C16—C15—H20108.725
O1—C1—H3109.468C16—C15—H21108.741
H1—C1—H2109.473H20—C15—H21107.632
H1—C1—H3109.468C15—C16—H22109.138
H2—C1—H3109.472C15—C16—H23109.119
C2—C3—H4119.755C17—C16—H22109.139
C4—C3—H4119.750C17—C16—H23109.125
C3—C4—H5119.819H22—C16—H23107.857
C5—C4—H5119.836C16—C17—H24109.476
C5—C6—H6119.199C16—C17—H25109.469
C7—C6—H6119.198C16—C17—H26109.467
C2—C7—H7120.319H24—C17—H25109.485
C6—C7—H7120.323H24—C17—H26109.469
N1—C8—H8119.213H25—C17—H26109.462
C9—S2—C10—C1183.88 (10)C3—C4—C5—C60.0 (2)
C10—S2—C9—S13.71 (11)C3—C4—C5—C8−179.23 (12)
C10—S2—C9—N2−176.36 (9)C4—C5—C6—C70.3 (2)
C1—O1—C2—C3−174.08 (13)C4—C5—C8—N1−10.9 (2)
C1—O1—C2—C75.0 (2)C6—C5—C8—N1169.89 (13)
N2—N1—C8—C5176.89 (11)C8—C5—C6—C7179.53 (12)
C8—N1—N2—C9173.58 (11)C5—C6—C7—C2−0.5 (3)
N1—N2—C9—S2−4.84 (16)S2—C10—C11—C12169.73 (9)
N1—N2—C9—S1175.10 (10)C10—C11—C12—C13177.45 (11)
O1—C2—C3—C4178.82 (12)C11—C12—C13—C14−177.31 (12)
O1—C2—C7—C6−178.47 (12)C12—C13—C14—C15−176.22 (12)
C3—C2—C7—C60.5 (2)C13—C14—C15—C16−178.79 (12)
C7—C2—C3—C4−0.3 (3)C14—C15—C16—C17−171.39 (12)
C2—C3—C4—C5−0.0 (3)
Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x+1/2, y−1/2, z+1; (iv) −x+2, −y+1, −z+1; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x−1/2, y+1/2, z−1; (ix) −x+1, y, −z−1/2; (x) −x+3/2, −y+1/2, −z; (xi) x, −y, z+1/2; (xii) −x+2, y, −z+3/2; (xiii) x+1/2, y+1/2, z+1; (xiv) −x+2, −y, −z+1; (xv) x−1/2, y−1/2, z−1; (xvi) x, −y, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H9···S1i0.86 (2)2.536 (18)3.3870 (11)170.9 (16)
Symmetry code: (i) −x+3/2, −y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H9···S1i0.86 (2)2.536 (18)3.3870 (11)170.9 (16)
Symmetry code: (i) −x+3/2, −y+1/2, −z+1.
 

Acknowledgements

MMH 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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ISSN: 2056-9890
Volume 71| Part 4| April 2015| Pages o265-o266
doi:10.1107/S205698901500568X
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