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ISSN: 2056-9890

Benzyl N′-(4,6-dimeth­­oxy-2-methyl-3-phenyl-1H-indol-7-ylmethyl­ene)hydrazinecarbodi­thio­ate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 November 2008; accepted 19 November 2008; online 26 November 2008)

The asymmetric unit of the title compound, C26H25N3O2S2, contains two independent mol­ecules, which are linked by a pair of N—H⋯S hydrogen bonds, forming a dimer.

Related literature

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2430.]). For further synthetic details, see: Ali & Tarafder (1977[Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1788.]); Jones et al. (2005[Jones, A. W., Wahyuningsih, T. W., Pchalek, K., Kumar, N. & Black, D. S. C. (2005). Tetrahedron, 61. 10490-10500.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25N3O2S2

  • Mr = 475.61

  • Triclinic, [P \overline 1]

  • a = 10.0913 (2) Å

  • b = 12.8541 (3) Å

  • c = 18.9232 (4) Å

  • α = 90.461 (1)°

  • β = 103.960 (1)°

  • γ = 93.944 (1)°

  • V = 2375.71 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 100 (2) K

  • 0.40 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.906, Tmax = 0.975

  • 22819 measured reflections

  • 10887 independent reflections

  • 7429 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.145

  • S = 1.01

  • 10887 reflections

  • 601 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S4 0.88 2.47 3.330 (2) 164
N4—H4⋯S2 0.88 2.50 3.368 (2) 170

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: pubCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005).

Related literature top

For a list of references of the benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008). For further synthetic details, see: Ali & Tarafder (1977); Jones et al. (2005).

Experimental top

4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde was prepared by using a literature method (Jones et al., 2005) as was S-benzyl dithiocarbazate (Ali & Tarafder, 1977). 4,6-Dimethoxy-2-methyl-3-phenylindole-7-carbaldehyde (0.59 g, 2 mmol) and S-benzyl dithiocarbazate (0.40 g, 2 mmol) were refluxed in ethanol (40 ml) for 6 h. About 1 ml acetic acid was also added. The precipitate was filtered, washed with cold ethanol and dried. Yellow prisms of (I) were grown by slow evaporation of a DMF solution at room temperature

Refinement top

Hydrogen atoms were placed at calculated positions (C–H = 0.95–0.99, N–H = 0.88Å) and refined as riding with U(H) = 1.2–1.5 times Ueq(C,N).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.
Benzyl N'-(4,6-dimethoxy-2-methyl-3-phenyl-1H- indol-7-ylmethylene)hydrazinecarbodithioate top
Crystal data top
C26H25N3O2S2Z = 4
Mr = 475.61F(000) = 1000
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.0913 (2) ÅCell parameters from 3627 reflections
b = 12.8541 (3) Åθ = 2.2–27.9°
c = 18.9232 (4) ŵ = 0.25 mm1
α = 90.461 (1)°T = 100 K
β = 103.960 (1)°Prism, yellow
γ = 93.944 (1)°0.40 × 0.15 × 0.10 mm
V = 2375.71 (9) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
10887 independent reflections
Radiation source: fine-focus sealed tube7429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.906, Tmax = 0.975k = 1616
22819 measured reflectionsl = 2423
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0761P)2]
where P = (Fo2 + 2Fc2)/3
10887 reflections(Δ/σ)max = 0.001
601 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C26H25N3O2S2γ = 93.944 (1)°
Mr = 475.61V = 2375.71 (9) Å3
Triclinic, P1Z = 4
a = 10.0913 (2) ÅMo Kα radiation
b = 12.8541 (3) ŵ = 0.25 mm1
c = 18.9232 (4) ÅT = 100 K
α = 90.461 (1)°0.40 × 0.15 × 0.10 mm
β = 103.960 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
10887 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7429 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.975Rint = 0.037
22819 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.01Δρmax = 0.38 e Å3
10887 reflectionsΔρmin = 0.33 e Å3
601 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.70730 (6)0.77337 (4)0.38863 (3)0.02192 (14)
S20.86760 (6)0.64215 (4)0.50774 (3)0.02258 (14)
S30.76473 (6)0.21326 (4)0.59896 (3)0.02381 (15)
S40.61229 (6)0.34616 (5)0.47915 (3)0.02475 (15)
N10.62636 (18)0.58880 (14)0.41970 (10)0.0203 (4)
H10.62320.53090.44390.024*
N20.52245 (19)0.60752 (14)0.35981 (10)0.0193 (4)
N30.41658 (18)0.70701 (13)0.23268 (9)0.0168 (4)
H30.48720.72060.27000.020*
N40.84585 (19)0.40040 (14)0.57324 (10)0.0214 (4)
H40.84990.45950.55040.026*
N50.94526 (19)0.38083 (14)0.63461 (9)0.0199 (4)
N61.04365 (18)0.27207 (13)0.75800 (9)0.0173 (4)
H60.97260.26280.72050.021*
O10.18934 (16)0.40290 (12)0.31166 (8)0.0241 (4)
O20.01662 (15)0.56662 (12)0.08209 (8)0.0211 (3)
O31.27723 (16)0.58543 (12)0.69482 (8)0.0249 (4)
O41.44777 (15)0.39642 (12)0.91349 (8)0.0204 (3)
C10.8502 (2)0.95402 (18)0.38428 (13)0.0234 (5)
C20.8241 (3)0.95499 (19)0.30847 (14)0.0301 (6)
H20.81660.89110.28170.036*
C30.8088 (3)1.0478 (2)0.27173 (15)0.0346 (6)
H3A0.78981.04760.22010.042*
C40.8215 (3)1.1411 (2)0.31081 (16)0.0365 (7)
H4A0.81291.20500.28580.044*
C50.8463 (3)1.1416 (2)0.38548 (16)0.0362 (7)
H50.85401.20570.41200.043*
C60.8600 (2)1.04831 (19)0.42195 (14)0.0301 (6)
H6A0.87641.04900.47350.036*
C70.8656 (2)0.85233 (17)0.42390 (13)0.0240 (5)
H7A0.88070.86480.47700.029*
H7B0.94420.81710.41460.029*
C80.7315 (2)0.66011 (17)0.44022 (11)0.0181 (5)
C90.4171 (2)0.54120 (17)0.34579 (12)0.0192 (5)
H90.41010.48620.37820.023*
C100.3103 (2)0.55083 (17)0.28101 (11)0.0170 (4)
C110.1969 (2)0.47839 (17)0.26171 (12)0.0191 (5)
C120.0981 (2)0.48203 (17)0.19613 (11)0.0187 (5)
H120.02280.43110.18520.022*
C130.1091 (2)0.55997 (17)0.14656 (11)0.0176 (5)
C140.2202 (2)0.63542 (16)0.16222 (11)0.0165 (4)
C150.3166 (2)0.62922 (16)0.22955 (11)0.0163 (4)
C160.3911 (2)0.76147 (16)0.16888 (11)0.0166 (4)
C170.4871 (2)0.85195 (17)0.16129 (12)0.0218 (5)
H17A0.45000.88760.11600.033*
H17B0.57620.82700.16020.033*
H17C0.49830.90070.20280.033*
C180.2714 (2)0.72033 (16)0.12301 (11)0.0173 (4)
C190.2177 (2)0.75254 (17)0.04715 (11)0.0189 (5)
C200.3054 (2)0.76263 (17)0.00017 (12)0.0228 (5)
H200.39860.74830.01720.027*
C210.2575 (2)0.79344 (19)0.07118 (12)0.0271 (5)
H210.31790.79930.10270.033*
C220.1218 (3)0.81568 (19)0.09653 (13)0.0285 (6)
H220.08920.83760.14510.034*
C230.0345 (2)0.80567 (18)0.05034 (12)0.0252 (5)
H230.05850.82070.06740.030*
C240.0814 (2)0.77397 (17)0.02037 (12)0.0203 (5)
H240.01980.76670.05120.024*
C250.0776 (2)0.32470 (17)0.29397 (13)0.0256 (5)
H25A0.08250.27770.33490.038*
H25B0.08300.28470.25060.038*
H25C0.00910.35820.28430.038*
C260.0941 (2)0.48780 (17)0.06387 (12)0.0214 (5)
H26A0.15080.50000.01520.032*
H26B0.14990.49030.09960.032*
H26C0.05750.41910.06430.032*
C270.6207 (2)0.03069 (18)0.59376 (13)0.0245 (5)
C280.5762 (3)0.0196 (2)0.65644 (16)0.0462 (8)
H280.53810.07640.67500.056*
C290.5862 (4)0.0736 (2)0.69306 (18)0.0581 (10)
H290.55480.08010.73640.070*
C300.6409 (3)0.1562 (2)0.66741 (16)0.0391 (7)
H300.65010.21910.69360.047*
C310.6823 (3)0.1476 (2)0.60373 (15)0.0362 (6)
H310.71760.20540.58470.043*
C320.6726 (3)0.0545 (2)0.56714 (14)0.0310 (6)
H320.70190.04890.52320.037*
C330.6132 (2)0.13207 (18)0.55449 (13)0.0240 (5)
H33A0.52950.16600.55760.029*
H33B0.61120.12000.50250.029*
C340.7437 (2)0.32828 (17)0.54922 (12)0.0202 (5)
C351.1528 (2)0.43417 (16)0.71813 (11)0.0179 (5)
C361.0496 (2)0.44792 (17)0.65222 (11)0.0193 (5)
H361.05830.50560.62210.023*
C371.2684 (2)0.50485 (17)0.74051 (12)0.0200 (5)
C381.3671 (2)0.49319 (17)0.80491 (12)0.0191 (5)
H381.44460.54200.81790.023*
C391.3533 (2)0.41075 (17)0.85036 (11)0.0176 (4)
C401.2386 (2)0.33879 (16)0.83225 (11)0.0161 (4)
C411.1435 (2)0.35199 (16)0.76586 (11)0.0160 (4)
C421.0701 (2)0.20814 (16)0.81719 (12)0.0178 (5)
C430.9715 (2)0.11756 (17)0.82004 (12)0.0229 (5)
H43A0.99750.08520.86770.034*
H43B0.97310.06640.78160.034*
H43C0.87910.14140.81270.034*
C441.1897 (2)0.24588 (16)0.86497 (11)0.0166 (4)
C451.2495 (2)0.20264 (17)0.93687 (12)0.0195 (5)
C461.2650 (2)0.09692 (18)0.94606 (13)0.0270 (5)
H461.23900.05070.90480.032*
C471.3176 (3)0.0574 (2)1.01393 (14)0.0383 (7)
H471.32660.01551.01880.046*
C481.3569 (3)0.1223 (2)1.07449 (14)0.0367 (7)
H481.39310.09491.12110.044*
C491.3433 (2)0.2282 (2)1.06674 (13)0.0279 (6)
H491.37080.27401.10820.033*
C501.2897 (2)0.26779 (18)0.99898 (12)0.0219 (5)
H501.28000.34060.99450.026*
C511.3965 (2)0.65652 (17)0.71292 (13)0.0248 (5)
H51A1.39280.70720.67420.037*
H51B1.47850.61780.71800.037*
H51C1.39990.69330.75900.037*
C521.5632 (2)0.47112 (18)0.93250 (13)0.0233 (5)
H52A1.62370.45220.97860.035*
H52B1.53160.54050.93780.035*
H52C1.61320.47180.89410.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0212 (3)0.0182 (3)0.0231 (3)0.0008 (2)0.0005 (2)0.0060 (2)
S20.0217 (3)0.0223 (3)0.0195 (3)0.0002 (2)0.0030 (2)0.0042 (2)
S30.0245 (3)0.0190 (3)0.0235 (3)0.0007 (2)0.0023 (2)0.0060 (2)
S40.0255 (3)0.0232 (3)0.0202 (3)0.0007 (2)0.0042 (2)0.0051 (2)
N10.0210 (10)0.0183 (10)0.0185 (10)0.0001 (8)0.0009 (8)0.0070 (8)
N20.0209 (10)0.0190 (10)0.0161 (9)0.0012 (8)0.0004 (7)0.0031 (7)
N30.0159 (9)0.0170 (9)0.0156 (9)0.0008 (7)0.0006 (7)0.0035 (7)
N40.0241 (10)0.0185 (10)0.0193 (10)0.0005 (8)0.0011 (8)0.0067 (8)
N50.0210 (10)0.0213 (10)0.0142 (9)0.0016 (8)0.0019 (7)0.0035 (8)
N60.0179 (9)0.0152 (9)0.0164 (9)0.0003 (7)0.0001 (7)0.0008 (7)
O10.0255 (9)0.0217 (8)0.0206 (8)0.0073 (7)0.0008 (7)0.0080 (7)
O20.0172 (8)0.0232 (8)0.0181 (8)0.0041 (6)0.0038 (6)0.0021 (6)
O30.0262 (9)0.0205 (8)0.0244 (9)0.0060 (7)0.0007 (7)0.0077 (7)
O40.0156 (8)0.0208 (8)0.0214 (8)0.0027 (6)0.0011 (6)0.0017 (6)
C10.0164 (11)0.0212 (12)0.0325 (13)0.0000 (9)0.0059 (10)0.0007 (10)
C20.0337 (14)0.0232 (13)0.0379 (15)0.0024 (11)0.0172 (12)0.0036 (11)
C30.0397 (16)0.0309 (15)0.0378 (15)0.0023 (12)0.0180 (12)0.0100 (12)
C40.0293 (14)0.0256 (14)0.0568 (19)0.0000 (11)0.0149 (13)0.0158 (13)
C50.0280 (14)0.0189 (13)0.0583 (19)0.0038 (11)0.0059 (13)0.0034 (12)
C60.0244 (13)0.0258 (13)0.0362 (15)0.0052 (10)0.0021 (11)0.0013 (11)
C70.0190 (12)0.0205 (12)0.0299 (13)0.0001 (9)0.0011 (10)0.0026 (10)
C80.0200 (11)0.0173 (11)0.0169 (11)0.0009 (9)0.0041 (9)0.0022 (9)
C90.0221 (11)0.0166 (11)0.0181 (11)0.0006 (9)0.0038 (9)0.0037 (9)
C100.0181 (11)0.0183 (11)0.0140 (10)0.0009 (9)0.0030 (8)0.0010 (8)
C110.0193 (11)0.0175 (11)0.0205 (11)0.0002 (9)0.0050 (9)0.0044 (9)
C120.0182 (11)0.0196 (11)0.0171 (11)0.0020 (9)0.0027 (9)0.0001 (9)
C130.0170 (11)0.0207 (11)0.0145 (11)0.0030 (9)0.0021 (8)0.0010 (9)
C140.0160 (11)0.0175 (11)0.0160 (11)0.0024 (9)0.0034 (8)0.0003 (8)
C150.0172 (11)0.0152 (11)0.0162 (11)0.0005 (8)0.0041 (8)0.0006 (8)
C160.0170 (11)0.0170 (11)0.0162 (11)0.0035 (9)0.0045 (8)0.0047 (8)
C170.0240 (12)0.0210 (12)0.0185 (11)0.0012 (9)0.0021 (9)0.0052 (9)
C180.0190 (11)0.0159 (11)0.0169 (11)0.0028 (9)0.0036 (8)0.0035 (8)
C190.0208 (11)0.0173 (11)0.0165 (11)0.0029 (9)0.0019 (9)0.0020 (9)
C200.0217 (12)0.0230 (12)0.0220 (12)0.0010 (9)0.0025 (9)0.0032 (10)
C210.0299 (13)0.0311 (14)0.0198 (12)0.0049 (11)0.0067 (10)0.0056 (10)
C220.0335 (14)0.0278 (14)0.0188 (12)0.0073 (11)0.0017 (10)0.0078 (10)
C230.0245 (12)0.0217 (12)0.0248 (13)0.0013 (10)0.0026 (10)0.0040 (10)
C240.0216 (12)0.0188 (12)0.0191 (11)0.0005 (9)0.0028 (9)0.0024 (9)
C250.0278 (13)0.0189 (12)0.0268 (13)0.0069 (10)0.0022 (10)0.0049 (10)
C260.0179 (11)0.0219 (12)0.0216 (12)0.0025 (9)0.0005 (9)0.0005 (9)
C270.0241 (12)0.0207 (12)0.0272 (13)0.0010 (10)0.0042 (10)0.0003 (10)
C280.072 (2)0.0321 (16)0.0483 (18)0.0202 (15)0.0366 (16)0.0111 (13)
C290.087 (3)0.0443 (19)0.061 (2)0.0224 (18)0.048 (2)0.0269 (16)
C300.0377 (16)0.0240 (14)0.0577 (19)0.0025 (12)0.0152 (14)0.0150 (13)
C310.0368 (15)0.0245 (14)0.0447 (17)0.0063 (12)0.0036 (13)0.0018 (12)
C320.0305 (14)0.0316 (14)0.0304 (14)0.0048 (11)0.0058 (11)0.0009 (11)
C330.0205 (12)0.0227 (12)0.0262 (13)0.0032 (9)0.0018 (10)0.0025 (10)
C340.0228 (12)0.0206 (12)0.0164 (11)0.0023 (9)0.0030 (9)0.0026 (9)
C350.0198 (11)0.0158 (11)0.0175 (11)0.0027 (9)0.0027 (9)0.0017 (9)
C360.0231 (12)0.0171 (11)0.0179 (11)0.0029 (9)0.0047 (9)0.0030 (9)
C370.0226 (12)0.0150 (11)0.0237 (12)0.0028 (9)0.0079 (9)0.0031 (9)
C380.0172 (11)0.0162 (11)0.0229 (12)0.0020 (9)0.0042 (9)0.0003 (9)
C390.0166 (11)0.0179 (11)0.0175 (11)0.0031 (9)0.0024 (8)0.0017 (9)
C400.0172 (11)0.0151 (11)0.0158 (11)0.0024 (8)0.0034 (8)0.0005 (8)
C410.0169 (11)0.0139 (10)0.0166 (11)0.0005 (8)0.0031 (8)0.0002 (8)
C420.0193 (11)0.0158 (11)0.0180 (11)0.0011 (9)0.0042 (9)0.0012 (9)
C430.0248 (12)0.0187 (12)0.0222 (12)0.0038 (9)0.0017 (9)0.0005 (9)
C440.0186 (11)0.0139 (10)0.0172 (11)0.0011 (8)0.0041 (8)0.0007 (8)
C450.0169 (11)0.0212 (12)0.0201 (11)0.0000 (9)0.0041 (9)0.0050 (9)
C460.0335 (14)0.0222 (13)0.0228 (12)0.0041 (11)0.0014 (10)0.0027 (10)
C470.0569 (18)0.0223 (14)0.0312 (15)0.0051 (13)0.0008 (13)0.0099 (11)
C480.0413 (16)0.0384 (16)0.0261 (14)0.0029 (13)0.0006 (12)0.0151 (12)
C490.0273 (13)0.0331 (14)0.0195 (12)0.0048 (11)0.0003 (10)0.0010 (10)
C500.0206 (12)0.0218 (12)0.0220 (12)0.0015 (9)0.0035 (9)0.0007 (9)
C510.0277 (13)0.0185 (12)0.0278 (13)0.0036 (10)0.0073 (10)0.0043 (10)
C520.0181 (11)0.0234 (12)0.0260 (13)0.0036 (9)0.0016 (9)0.0017 (10)
Geometric parameters (Å, º) top
S1—C81.758 (2)C20—H200.9500
S1—C71.811 (2)C21—C221.388 (3)
S2—C81.666 (2)C21—H210.9500
S3—C341.757 (2)C22—C231.384 (3)
S3—C331.812 (2)C22—H220.9500
S4—C341.664 (2)C23—C241.382 (3)
N1—C81.333 (3)C23—H230.9500
N1—N21.381 (2)C24—H240.9500
N1—H10.8800C25—H25A0.9800
N2—C91.290 (3)C25—H25B0.9800
N3—C151.361 (3)C25—H25C0.9800
N3—C161.379 (3)C26—H26A0.9800
N3—H30.8800C26—H26B0.9800
N4—C341.328 (3)C26—H26C0.9800
N4—N51.377 (2)C27—C281.371 (3)
N4—H40.8800C27—C321.387 (3)
N5—C361.290 (3)C27—C331.503 (3)
N6—C411.370 (3)C28—C291.386 (4)
N6—C421.379 (3)C28—H280.9500
N6—H60.8800C29—C301.367 (4)
O1—C111.371 (2)C29—H290.9500
O1—C251.432 (3)C30—C311.370 (4)
O2—C131.353 (2)C30—H300.9500
O2—C261.431 (2)C31—C321.384 (3)
O3—C371.367 (3)C31—H310.9500
O3—C511.430 (3)C32—H320.9500
O4—C391.360 (2)C33—H33A0.9900
O4—C521.430 (3)C33—H33B0.9900
C1—C61.386 (3)C35—C371.405 (3)
C1—C21.395 (3)C35—C411.408 (3)
C1—C71.511 (3)C35—C361.440 (3)
C2—C31.385 (3)C36—H360.9500
C2—H20.9500C37—C381.392 (3)
C3—C41.385 (4)C38—C391.391 (3)
C3—H3A0.9500C38—H380.9500
C4—C51.374 (4)C39—C401.404 (3)
C4—H4A0.9500C40—C411.404 (3)
C5—C61.387 (3)C40—C441.460 (3)
C5—H50.9500C42—C441.377 (3)
C6—H6A0.9500C42—C431.489 (3)
C7—H7A0.9900C43—H43A0.9800
C7—H7B0.9900C43—H43B0.9800
C9—C101.436 (3)C43—H43C0.9800
C9—H90.9500C44—C451.479 (3)
C10—C111.398 (3)C45—C461.386 (3)
C10—C151.416 (3)C45—C501.398 (3)
C11—C121.395 (3)C46—C471.381 (3)
C12—C131.395 (3)C46—H460.9500
C12—H120.9500C47—C481.374 (4)
C13—C141.404 (3)C47—H470.9500
C14—C151.410 (3)C48—C491.383 (4)
C14—C181.459 (3)C48—H480.9500
C16—C181.375 (3)C49—C501.382 (3)
C16—C171.492 (3)C49—H490.9500
C17—H17A0.9800C50—H500.9500
C17—H17B0.9800C51—H51A0.9800
C17—H17C0.9800C51—H51B0.9800
C18—C191.480 (3)C51—H51C0.9800
C19—C241.394 (3)C52—H52A0.9800
C19—C201.398 (3)C52—H52B0.9800
C20—C211.390 (3)C52—H52C0.9800
C8—S1—C7102.87 (10)H25A—C25—H25B109.5
C34—S3—C33102.23 (11)O1—C25—H25C109.5
C8—N1—N2118.81 (17)H25A—C25—H25C109.5
C8—N1—H1120.6H25B—C25—H25C109.5
N2—N1—H1120.6O2—C26—H26A109.5
C9—N2—N1116.74 (18)O2—C26—H26B109.5
C15—N3—C16110.09 (17)H26A—C26—H26B109.5
C15—N3—H3125.0O2—C26—H26C109.5
C16—N3—H3125.0H26A—C26—H26C109.5
C34—N4—N5118.62 (18)H26B—C26—H26C109.5
C34—N4—H4120.7C28—C27—C32118.3 (2)
N5—N4—H4120.7C28—C27—C33121.1 (2)
C36—N5—N4116.84 (18)C32—C27—C33120.6 (2)
C41—N6—C42110.47 (17)C27—C28—C29120.7 (3)
C41—N6—H6124.8C27—C28—H28119.7
C42—N6—H6124.8C29—C28—H28119.7
C11—O1—C25117.96 (17)C30—C29—C28120.6 (3)
C13—O2—C26117.78 (17)C30—C29—H29119.7
C37—O3—C51117.87 (17)C28—C29—H29119.7
C39—O4—C52117.16 (17)C29—C30—C31119.5 (3)
C6—C1—C2118.3 (2)C29—C30—H30120.2
C6—C1—C7121.1 (2)C31—C30—H30120.2
C2—C1—C7120.5 (2)C30—C31—C32119.9 (2)
C3—C2—C1120.9 (2)C30—C31—H31120.0
C3—C2—H2119.6C32—C31—H31120.0
C1—C2—H2119.6C31—C32—C27121.0 (2)
C2—C3—C4119.6 (3)C31—C32—H32119.5
C2—C3—H3A120.2C27—C32—H32119.5
C4—C3—H3A120.2C27—C33—S3106.50 (15)
C5—C4—C3120.4 (2)C27—C33—H33A110.4
C5—C4—H4A119.8S3—C33—H33A110.4
C3—C4—H4A119.8C27—C33—H33B110.4
C4—C5—C6119.8 (2)S3—C33—H33B110.4
C4—C5—H5120.1H33A—C33—H33B108.6
C6—C5—H5120.1N4—C34—S4123.02 (17)
C1—C6—C5121.0 (2)N4—C34—S3112.47 (16)
C1—C6—H6A119.5S4—C34—S3124.51 (14)
C5—C6—H6A119.5C37—C35—C41115.23 (19)
C1—C7—S1106.11 (15)C37—C35—C36121.77 (19)
C1—C7—H7A110.5C41—C35—C36123.0 (2)
S1—C7—H7A110.5N5—C36—C35119.0 (2)
C1—C7—H7B110.5N5—C36—H36120.5
S1—C7—H7B110.5C35—C36—H36120.5
H7A—C7—H7B108.7O3—C37—C38122.4 (2)
N1—C8—S2122.94 (16)O3—C37—C35115.52 (19)
N1—C8—S1112.08 (15)C38—C37—C35122.1 (2)
S2—C8—S1124.97 (13)C39—C38—C37120.6 (2)
N2—C9—C10119.78 (19)C39—C38—H38119.7
N2—C9—H9120.1C37—C38—H38119.7
C10—C9—H9120.1O4—C39—C38122.33 (19)
C11—C10—C15115.09 (19)O4—C39—C40117.33 (18)
C11—C10—C9121.99 (19)C38—C39—C40120.34 (19)
C15—C10—C9122.76 (19)C39—C40—C41117.10 (19)
O1—C11—C12121.99 (19)C39—C40—C44135.86 (19)
O1—C11—C10115.42 (18)C41—C40—C44107.02 (18)
C12—C11—C10122.6 (2)N6—C41—C40107.34 (18)
C13—C12—C11120.5 (2)N6—C41—C35128.02 (19)
C13—C12—H12119.8C40—C41—C35124.64 (19)
C11—C12—H12119.8C44—C42—N6108.84 (19)
O2—C13—C12122.81 (19)C44—C42—C43132.2 (2)
O2—C13—C14117.04 (19)N6—C42—C43118.92 (18)
C12—C13—C14120.16 (19)C42—C43—H43A109.5
C13—C14—C15117.29 (19)C42—C43—H43B109.5
C13—C14—C18135.7 (2)H43A—C43—H43B109.5
C15—C14—C18106.84 (18)C42—C43—H43C109.5
N3—C15—C14107.63 (18)H43A—C43—H43C109.5
N3—C15—C10127.87 (19)H43B—C43—H43C109.5
C14—C15—C10124.39 (19)C42—C44—C40106.34 (18)
C18—C16—N3109.44 (18)C42—C44—C45125.6 (2)
C18—C16—C17131.52 (19)C40—C44—C45127.95 (19)
N3—C16—C17119.00 (18)C46—C45—C50117.4 (2)
C16—C17—H17A109.5C46—C45—C44122.1 (2)
C16—C17—H17B109.5C50—C45—C44120.6 (2)
H17A—C17—H17B109.5C47—C46—C45121.3 (2)
C16—C17—H17C109.5C47—C46—H46119.3
H17A—C17—H17C109.5C45—C46—H46119.3
H17B—C17—H17C109.5C48—C47—C46120.7 (2)
C16—C18—C14105.94 (18)C48—C47—H47119.7
C16—C18—C19124.81 (19)C46—C47—H47119.7
C14—C18—C19129.0 (2)C47—C48—C49119.1 (2)
C24—C19—C20118.1 (2)C47—C48—H48120.4
C24—C19—C18122.2 (2)C49—C48—H48120.4
C20—C19—C18119.7 (2)C50—C49—C48120.3 (2)
C21—C20—C19120.7 (2)C50—C49—H49119.9
C21—C20—H20119.6C48—C49—H49119.9
C19—C20—H20119.6C49—C50—C45121.2 (2)
C22—C21—C20120.2 (2)C49—C50—H50119.4
C22—C21—H21119.9C45—C50—H50119.4
C20—C21—H21119.9O3—C51—H51A109.5
C23—C22—C21119.3 (2)O3—C51—H51B109.5
C23—C22—H22120.3H51A—C51—H51B109.5
C21—C22—H22120.3O3—C51—H51C109.5
C24—C23—C22120.6 (2)H51A—C51—H51C109.5
C24—C23—H23119.7H51B—C51—H51C109.5
C22—C23—H23119.7O4—C52—H52A109.5
C23—C24—C19121.0 (2)O4—C52—H52B109.5
C23—C24—H24119.5H52A—C52—H52B109.5
C19—C24—H24119.5O4—C52—H52C109.5
O1—C25—H25A109.5H52A—C52—H52C109.5
O1—C25—H25B109.5H52B—C52—H52C109.5
C8—N1—N2—C9173.9 (2)C18—C19—C24—C23178.9 (2)
C34—N4—N5—C36173.4 (2)C32—C27—C28—C291.6 (5)
C6—C1—C2—C30.3 (4)C33—C27—C28—C29178.7 (3)
C7—C1—C2—C3179.5 (2)C27—C28—C29—C300.1 (5)
C1—C2—C3—C40.8 (4)C28—C29—C30—C312.0 (5)
C2—C3—C4—C51.3 (4)C29—C30—C31—C322.1 (4)
C3—C4—C5—C60.6 (4)C30—C31—C32—C270.3 (4)
C2—C1—C6—C51.0 (4)C28—C27—C32—C311.5 (4)
C7—C1—C6—C5179.8 (2)C33—C27—C32—C31178.8 (2)
C4—C5—C6—C10.5 (4)C28—C27—C33—S383.8 (3)
C6—C1—C7—S1120.9 (2)C32—C27—C33—S396.5 (2)
C2—C1—C7—S158.3 (3)C34—S3—C33—C27179.61 (16)
C8—S1—C7—C1177.53 (16)N5—N4—C34—S4175.72 (15)
N2—N1—C8—S2175.46 (15)N5—N4—C34—S34.9 (3)
N2—N1—C8—S15.2 (2)C33—S3—C34—N4179.96 (17)
C7—S1—C8—N1177.14 (16)C33—S3—C34—S40.65 (18)
C7—S1—C8—S23.54 (18)N4—N5—C36—C35176.60 (18)
N1—N2—C9—C10174.83 (18)C37—C35—C36—N5179.6 (2)
N2—C9—C10—C11177.1 (2)C41—C35—C36—N51.9 (3)
N2—C9—C10—C151.9 (3)C51—O3—C37—C383.2 (3)
C25—O1—C11—C121.6 (3)C51—O3—C37—C35176.68 (19)
C25—O1—C11—C10178.21 (19)C41—C35—C37—O3179.32 (18)
C15—C10—C11—O1179.30 (18)C36—C35—C37—O31.4 (3)
C9—C10—C11—O15.1 (3)C41—C35—C37—C380.8 (3)
C15—C10—C11—C120.8 (3)C36—C35—C37—C38178.7 (2)
C9—C10—C11—C12174.7 (2)O3—C37—C38—C39179.2 (2)
O1—C11—C12—C13180.0 (2)C35—C37—C38—C390.9 (3)
C10—C11—C12—C130.2 (3)C52—O4—C39—C380.8 (3)
C26—O2—C13—C122.0 (3)C52—O4—C39—C40178.75 (18)
C26—O2—C13—C14177.40 (18)C37—C38—C39—O4179.69 (19)
C11—C12—C13—O2179.58 (19)C37—C38—C39—C400.7 (3)
C11—C12—C13—C140.2 (3)O4—C39—C40—C41178.01 (18)
O2—C13—C14—C15179.65 (18)C38—C39—C40—C412.4 (3)
C12—C13—C14—C150.9 (3)O4—C39—C40—C440.3 (4)
O2—C13—C14—C185.7 (4)C38—C39—C40—C44179.9 (2)
C12—C13—C14—C18173.8 (2)C42—N6—C41—C400.5 (2)
C16—N3—C15—C141.9 (2)C42—N6—C41—C35179.0 (2)
C16—N3—C15—C10174.5 (2)C39—C40—C41—N6177.86 (18)
C13—C14—C15—N3178.33 (18)C44—C40—C41—N60.5 (2)
C18—C14—C15—N32.2 (2)C39—C40—C41—C352.6 (3)
C13—C14—C15—C101.7 (3)C44—C40—C41—C35179.0 (2)
C18—C14—C15—C10174.39 (19)C37—C35—C41—N6179.6 (2)
C11—C10—C15—N3177.6 (2)C36—C35—C41—N62.6 (3)
C9—C10—C15—N32.0 (3)C37—C35—C41—C401.1 (3)
C11—C10—C15—C141.7 (3)C36—C35—C41—C40176.8 (2)
C9—C10—C15—C14173.9 (2)C41—N6—C42—C440.3 (2)
C15—N3—C16—C180.9 (2)C41—N6—C42—C43178.61 (19)
C15—N3—C16—C17178.78 (19)N6—C42—C44—C400.0 (2)
N3—C16—C18—C140.5 (2)C43—C42—C44—C40178.7 (2)
C17—C16—C18—C14177.0 (2)N6—C42—C44—C45176.58 (19)
N3—C16—C18—C19174.34 (19)C43—C42—C44—C452.1 (4)
C17—C16—C18—C198.1 (4)C39—C40—C44—C42177.6 (2)
C13—C14—C18—C16176.7 (2)C41—C40—C44—C420.3 (2)
C15—C14—C18—C161.7 (2)C39—C40—C44—C455.9 (4)
C13—C14—C18—C192.1 (4)C41—C40—C44—C45176.2 (2)
C15—C14—C18—C19172.9 (2)C42—C44—C45—C4648.5 (3)
C16—C18—C19—C24133.1 (2)C40—C44—C45—C46135.6 (2)
C14—C18—C19—C2453.3 (3)C42—C44—C45—C50129.9 (2)
C16—C18—C19—C2046.6 (3)C40—C44—C45—C5046.0 (3)
C14—C18—C19—C20127.0 (2)C50—C45—C46—C470.3 (4)
C24—C19—C20—C210.1 (3)C44—C45—C46—C47178.2 (2)
C18—C19—C20—C21179.6 (2)C45—C46—C47—C480.4 (4)
C19—C20—C21—C220.7 (4)C46—C47—C48—C490.0 (4)
C20—C21—C22—C230.8 (4)C47—C48—C49—C500.5 (4)
C21—C22—C23—C240.1 (4)C48—C49—C50—C450.6 (4)
C22—C23—C24—C190.8 (3)C46—C45—C50—C490.3 (3)
C20—C19—C24—C230.9 (3)C44—C45—C50—C49178.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S40.882.473.330 (2)164
N4—H4···S20.882.503.368 (2)170

Experimental details

Crystal data
Chemical formulaC26H25N3O2S2
Mr475.61
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.0913 (2), 12.8541 (3), 18.9232 (4)
α, β, γ (°)90.461 (1), 103.960 (1), 93.944 (1)
V3)2375.71 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.40 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.906, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
22819, 10887, 7429
Rint0.037
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.146, 1.01
No. of reflections10887
No. of parameters601
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S40.882.473.330 (2)164
N4—H4···S20.882.503.368 (2)170
 

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

First citationAli, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1788.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJones, A. W., Wahyuningsih, T. W., Pchalek, K., Kumar, N. & Black, D. S. C. (2005). Tetrahedron, 61. 10490–10500.  Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2430.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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