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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-(1-Adamant­yl)-1-{[4-(2-meth­­oxy­phen­yl)piperazin-1-yl]meth­yl}-4-methyl-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
*Correspondence e-mail: elemam5@hotmail.com

(Received 24 May 2010; accepted 13 June 2010; online 23 June 2010)

The title compound, C25H35N5OS, is a functionalized triazoline-3-thione with substituted piperazine and adamantyl substituents attached at the 2- and 5-positions, respectively, of a triazole spacer with an approximately C-shaped conformation of the mol­ecule. The piperazine ring adopts a chair conformation.

Related literature

For the anti­viral activity of adamantane derviatives, see: Vernier et al. (1969[Vernier, V. G., Harmon, J. B., Stump, J. M., Lynes, T. L., Marvel, M. P. & Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642-665.]); Balzarini et al. (2007[Balzarini, J., Orzeszko, B., Mauri, J. K. & Orzeszko, A. (2007). Eur. J. Med. Chem. 42, 993-1003.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]). For our study of the chemical and pharmacological properties of adamantane derivatives, see: Al-Omar et al. (2010[Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, I. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.]); Al-Abdullah et al. (2007[Al-Abdullah, E. S., Shehata, I. A., Al-Deeb, O. A. & El-Emam, A. A. (2007). Heterocycles, 71, 379-388.]); Al-Deeb et al. (2006[Al-Deeb, O. A., Al-Omar, M. A., El-Brollosy, N. R., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2006). Arzneim. Forsch. Drug Res. 56, 40-47.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]). For related structures, see: Hayden et al. (1981[Hayden, F. G., Gwaltney, J. M. I., Van, C. R. L., Adam, K. F. & Giordani, B. (1981). Antimicrob. Agents Chemother. 19, 226-233.]); Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]); Khan et al. (2009[Khan, M.-H., Hameed, S., Tahir, M. N., Bokhari, T. H. & Khan, I. U. (2009). Acta Cryst. E65, o1437.]); Smith (1969[Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642-665.]).

[Scheme 1]

Experimental

Crystal data
  • C25H35N5OS

  • Mr = 453.64

  • Monoclinic, P 21 /n

  • a = 11.0203 (2) Å

  • b = 12.1148 (2) Å

  • c = 18.7624 (4) Å

  • β = 103.473 (1)°

  • V = 2436.01 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 220 K

  • 0.49 × 0.45 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.657, Tmax = 0.746

  • 24895 measured reflections

  • 5620 independent reflections

  • 3796 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.110

  • S = 1.03

  • 5620 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Derivatives of adamantane have long been known for their antiviral activity against the influenza (Vernier et al., 1969) and HIV viruses (Balzarini et al., 2007; El-Emam et al., 2004). In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives (Al-Omar et al., 2010; Al-Abdullah et al., 2007; Al-Deeb et al., 2006; El-Emam et al., 2004), we synthesized the title compound as potential chemotherapeutic agent.

Related literature top

For the antiviral activity of adamantane derviatives, see: Vernier et al. (1969); Balzarini et al. (2007); El-Emam et al. (2004). For our study of the chemical and pharmacological properties of adamantane derivatives, see: Al-Omar et al. (2010); Al-Abdullah et al. (2007); Al-Deeb et al. (2006); El-Emam et al. (2004). For related literature [on what subject?], see: Hayden et al. (1981); Kadi et al. (2007); Khan et al. (2009); Smith (1969).

Experimental top

A mixture of the 5-(1-adamantyl)-4-methyl-3-mercapto-1,2,4-triazole (0.25 g, 1.0 mmol), 1-(2-methoxyphenyl)-piperazine (0.192 g, 1.0 mmol), and 37% formaldehyde solution (1 ml), in ethanol (8 ml), was heated under reflux for 15 and the mixture was stirred for 12 h at room temperature. The precipitated crude product was filtered, washed with water, dried, and crystallized from ethanol to yield the title compound as colourless crystals.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93–0.99 Å, Uiso(H) = Ueq(C) where x = 1.2 or 1.5.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
3-(1-Adamantyl)-1-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-methyl- 1H-1,2,4-triazole-5(4H)-thione top
Crystal data top
C25H35N5OSDx = 1.237 Mg m3
Mr = 453.64Melting point: 368 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.0203 (2) ÅCell parameters from 3554 reflections
b = 12.1148 (2) Åθ = 2.2–23.1°
c = 18.7624 (4) ŵ = 0.16 mm1
β = 103.473 (1)°T = 220 K
V = 2436.01 (8) Å3Irregular, colourless
Z = 40.49 × 0.45 × 0.30 mm
F(000) = 976
Data collection top
Bruker APEXII CCD
diffractometer
5620 independent reflections
Radiation source: fine-focus sealed tube3796 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ϕ and ω scansθmax = 27.8°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1412
Tmin = 0.657, Tmax = 0.746k = 1515
24895 measured reflectionsl = 2324
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0401P)2 + 0.5413P]
where P = (Fo2 + 2Fc2)/3
5620 reflections(Δ/σ)max = 0.005
291 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C25H35N5OSV = 2436.01 (8) Å3
Mr = 453.64Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.0203 (2) ŵ = 0.16 mm1
b = 12.1148 (2) ÅT = 220 K
c = 18.7624 (4) Å0.49 × 0.45 × 0.30 mm
β = 103.473 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
5620 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
3796 reflections with I > 2σ(I)
Tmin = 0.657, Tmax = 0.746Rint = 0.051
24895 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
5620 reflectionsΔρmin = 0.28 e Å3
291 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.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.85940 (5)0.86853 (4)0.53498 (3)0.05000 (16)
N10.62964 (13)0.78915 (11)0.47013 (7)0.0332 (3)
N20.66463 (13)0.94832 (11)0.42976 (7)0.0339 (3)
N30.52327 (12)0.81656 (11)0.41781 (7)0.0324 (3)
N40.66353 (13)0.58757 (11)0.48190 (7)0.0332 (3)
N50.72913 (12)0.44922 (11)0.37340 (7)0.0308 (3)
O10.59370 (11)0.40994 (10)0.23430 (6)0.0389 (3)
C10.71784 (16)0.86777 (14)0.47860 (9)0.0338 (4)
C20.54684 (15)0.91303 (13)0.39379 (9)0.0300 (4)
C30.45836 (15)0.97132 (13)0.33195 (9)0.0295 (4)
C40.34127 (17)0.89905 (14)0.30667 (11)0.0440 (5)
H4A0.36530.82640.29150.053*
H4B0.30070.88840.34740.053*
C50.24998 (18)0.95439 (15)0.24238 (11)0.0478 (5)
H50.17550.90690.22630.057*
C60.3130 (2)0.96989 (18)0.17898 (11)0.0579 (6)
H6A0.25471.00410.13740.069*
H6B0.33830.89810.16320.069*
C70.21012 (17)1.06595 (15)0.26620 (11)0.0445 (5)
H7A0.15181.10140.22510.053*
H7B0.16771.05620.30620.053*
C80.32449 (17)1.13792 (14)0.29152 (10)0.0393 (4)
H80.29871.21040.30730.047*
C90.38859 (18)1.15499 (16)0.22891 (11)0.0492 (5)
H9A0.46241.20170.24520.059*
H9B0.33161.19210.18800.059*
C100.42699 (19)1.04324 (18)0.20391 (10)0.0510 (5)
H100.46741.05440.16250.061*
C110.51956 (17)0.98754 (16)0.26713 (9)0.0410 (4)
H11A0.59431.03350.28230.049*
H11B0.54470.91590.25110.049*
C120.41605 (16)1.08353 (14)0.35596 (9)0.0369 (4)
H12A0.37561.07300.39680.044*
H12B0.48871.13150.37280.044*
C130.63210 (17)0.68799 (14)0.51391 (9)0.0364 (4)
H13A0.69220.69880.56090.044*
H13B0.54970.67860.52440.044*
C140.78816 (15)0.59036 (14)0.46694 (9)0.0350 (4)
H14A0.84970.60980.51190.042*
H14B0.79060.64730.43020.042*
C150.82185 (16)0.48005 (14)0.43932 (9)0.0355 (4)
H15A0.90440.48450.42830.043*
H15B0.82510.42370.47720.043*
C160.60608 (15)0.44145 (14)0.39088 (9)0.0349 (4)
H16A0.60860.38570.42900.042*
H16B0.54360.41860.34720.042*
C170.56982 (15)0.55202 (14)0.41724 (9)0.0345 (4)
H17A0.56310.60700.37820.041*
H17B0.48830.54600.42950.041*
C180.76033 (15)0.35869 (13)0.33294 (9)0.0299 (4)
C190.86273 (16)0.29100 (14)0.35965 (10)0.0367 (4)
H190.91210.30340.40700.044*
C200.89376 (18)0.20552 (15)0.31792 (11)0.0431 (4)
H200.96470.16210.33670.052*
C210.82146 (18)0.18439 (15)0.24975 (10)0.0438 (5)
H210.84030.12440.22240.053*
C220.72050 (17)0.25144 (14)0.22101 (10)0.0387 (4)
H220.67180.23770.17360.046*
C230.69049 (15)0.33847 (13)0.26127 (9)0.0315 (4)
C240.53309 (18)0.39994 (16)0.15850 (9)0.0433 (5)
H24A0.59490.40260.12920.065*
H24B0.47440.46020.14450.065*
H24C0.48880.33020.15030.065*
C250.72686 (18)1.05429 (15)0.42605 (12)0.0517 (5)
H25A0.68801.11070.45000.077*
H25B0.71941.07440.37520.077*
H25C0.81441.04800.45060.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0391 (3)0.0588 (3)0.0435 (3)0.0019 (2)0.0079 (2)0.0074 (2)
N10.0324 (8)0.0346 (8)0.0308 (7)0.0048 (6)0.0038 (6)0.0019 (6)
N20.0307 (8)0.0320 (7)0.0367 (8)0.0009 (6)0.0034 (6)0.0031 (6)
N30.0290 (8)0.0325 (8)0.0341 (8)0.0021 (6)0.0042 (6)0.0016 (6)
N40.0351 (8)0.0360 (8)0.0285 (7)0.0052 (6)0.0077 (6)0.0022 (6)
N50.0266 (7)0.0322 (7)0.0329 (7)0.0009 (6)0.0056 (6)0.0018 (6)
O10.0372 (7)0.0397 (7)0.0358 (7)0.0074 (5)0.0005 (5)0.0026 (5)
C10.0338 (9)0.0376 (9)0.0297 (9)0.0024 (8)0.0068 (7)0.0052 (7)
C20.0282 (9)0.0280 (8)0.0334 (9)0.0008 (7)0.0062 (7)0.0036 (7)
C30.0285 (9)0.0252 (8)0.0332 (9)0.0012 (7)0.0042 (7)0.0012 (6)
C40.0360 (10)0.0292 (9)0.0589 (12)0.0035 (8)0.0049 (9)0.0027 (8)
C50.0369 (10)0.0348 (10)0.0601 (13)0.0035 (8)0.0121 (9)0.0012 (9)
C60.0633 (14)0.0568 (13)0.0414 (11)0.0224 (11)0.0125 (10)0.0106 (10)
C70.0310 (10)0.0440 (11)0.0561 (12)0.0064 (8)0.0054 (8)0.0091 (9)
C80.0411 (10)0.0250 (9)0.0502 (11)0.0090 (7)0.0075 (8)0.0002 (8)
C90.0431 (11)0.0433 (11)0.0582 (13)0.0015 (9)0.0059 (9)0.0194 (9)
C100.0482 (12)0.0716 (14)0.0349 (10)0.0174 (10)0.0129 (9)0.0109 (9)
C110.0378 (10)0.0494 (11)0.0370 (10)0.0110 (9)0.0109 (8)0.0007 (8)
C120.0369 (10)0.0331 (9)0.0404 (10)0.0040 (8)0.0086 (8)0.0062 (7)
C130.0432 (10)0.0400 (10)0.0273 (8)0.0064 (8)0.0108 (7)0.0046 (7)
C140.0313 (9)0.0407 (10)0.0309 (9)0.0010 (8)0.0028 (7)0.0005 (7)
C150.0282 (9)0.0408 (10)0.0348 (9)0.0037 (7)0.0020 (7)0.0003 (7)
C160.0294 (9)0.0387 (10)0.0376 (9)0.0021 (7)0.0100 (7)0.0007 (8)
C170.0291 (9)0.0409 (10)0.0334 (9)0.0029 (7)0.0074 (7)0.0028 (7)
C180.0283 (9)0.0278 (8)0.0351 (9)0.0012 (7)0.0103 (7)0.0024 (7)
C190.0369 (10)0.0350 (9)0.0371 (9)0.0036 (8)0.0066 (8)0.0032 (7)
C200.0418 (11)0.0361 (10)0.0510 (11)0.0136 (8)0.0098 (9)0.0046 (8)
C210.0515 (12)0.0342 (10)0.0483 (11)0.0071 (9)0.0172 (9)0.0046 (8)
C220.0406 (10)0.0367 (10)0.0386 (10)0.0005 (8)0.0089 (8)0.0054 (8)
C230.0277 (9)0.0296 (9)0.0377 (9)0.0000 (7)0.0088 (7)0.0019 (7)
C240.0473 (11)0.0431 (11)0.0362 (10)0.0027 (9)0.0032 (8)0.0049 (8)
C250.0412 (11)0.0404 (11)0.0662 (14)0.0129 (9)0.0020 (10)0.0013 (10)
Geometric parameters (Å, º) top
S1—C11.6684 (17)C9—H9A0.9800
N1—C11.344 (2)C9—H9B0.9800
N1—N31.3827 (18)C10—C111.529 (2)
N1—C131.472 (2)C10—H100.9900
N2—C11.373 (2)C11—H11A0.9800
N2—C21.384 (2)C11—H11B0.9800
N2—C251.465 (2)C12—H12A0.9800
N3—C21.300 (2)C12—H12B0.9800
N4—C131.434 (2)C13—H13A0.9800
N4—C141.465 (2)C13—H13B0.9800
N4—C171.463 (2)C14—C151.511 (2)
N5—C181.421 (2)C14—H14A0.9800
N5—C151.458 (2)C14—H14B0.9800
N5—C161.471 (2)C15—H15A0.9800
O1—C231.3755 (19)C15—H15B0.9800
O1—C241.429 (2)C16—C171.514 (2)
C2—C31.506 (2)C16—H16A0.9800
C3—C111.534 (2)C16—H16B0.9800
C3—C41.540 (2)C17—H17A0.9800
C3—C121.538 (2)C17—H17B0.9800
C4—C51.533 (2)C18—C191.390 (2)
C4—H4A0.9800C18—C231.406 (2)
C4—H4B0.9800C19—C201.388 (2)
C5—C61.523 (3)C19—H190.9400
C5—C71.520 (3)C20—C211.364 (3)
C5—H50.9900C20—H200.9400
C6—C101.520 (3)C21—C221.382 (2)
C6—H6A0.9800C21—H210.9400
C6—H6B0.9800C22—C231.381 (2)
C7—C81.515 (3)C22—H220.9400
C7—H7A0.9800C24—H24A0.9700
C7—H7B0.9800C24—H24B0.9700
C8—C91.519 (3)C24—H24C0.9700
C8—C121.532 (2)C25—H25A0.9700
C8—H80.9900C25—H25B0.9700
C9—C101.525 (3)C25—H25C0.9700
C1—N1—N3112.58 (13)C3—C11—H11A109.8
C1—N1—C13127.26 (14)C10—C11—H11B109.8
N3—N1—C13119.89 (14)C3—C11—H11B109.8
C1—N2—C2108.19 (13)H11A—C11—H11B108.2
C1—N2—C25121.52 (14)C8—C12—C3109.75 (13)
C2—N2—C25130.09 (14)C8—C12—H12A109.7
C2—N3—N1104.90 (13)C3—C12—H12A109.7
C13—N4—C14112.91 (14)C8—C12—H12B109.7
C13—N4—C17113.84 (13)C3—C12—H12B109.7
C14—N4—C17111.10 (13)H12A—C12—H12B108.2
C18—N5—C15116.23 (13)N4—C13—N1116.57 (13)
C18—N5—C16114.85 (13)N4—C13—H13A108.2
C15—N5—C16109.13 (13)N1—C13—H13A108.2
C23—O1—C24117.10 (13)N4—C13—H13B108.2
N1—C1—N2103.90 (14)N1—C13—H13B108.2
N1—C1—S1128.52 (13)H13A—C13—H13B107.3
N2—C1—S1127.59 (13)N4—C14—C15111.20 (14)
N3—C2—N2110.43 (14)N4—C14—H14A109.4
N3—C2—C3122.86 (14)C15—C14—H14A109.4
N2—C2—C3126.59 (14)N4—C14—H14B109.4
C2—C3—C11110.21 (13)C15—C14—H14B109.4
C2—C3—C4108.44 (13)H14A—C14—H14B108.0
C11—C3—C4108.67 (15)N5—C15—C14109.76 (13)
C2—C3—C12112.01 (13)N5—C15—H15A109.7
C11—C3—C12109.77 (14)C14—C15—H15A109.7
C4—C3—C12107.65 (14)N5—C15—H15B109.7
C5—C4—C3110.05 (14)C14—C15—H15B109.7
C5—C4—H4A109.7H15A—C15—H15B108.2
C3—C4—H4A109.7N5—C16—C17110.09 (13)
C5—C4—H4B109.7N5—C16—H16A109.6
C3—C4—H4B109.7C17—C16—H16A109.6
H4A—C4—H4B108.2N5—C16—H16B109.6
C6—C5—C7109.61 (16)C17—C16—H16B109.6
C6—C5—C4109.47 (17)H16A—C16—H16B108.2
C7—C5—C4109.82 (16)N4—C17—C16110.03 (13)
C6—C5—H5109.3N4—C17—H17A109.7
C7—C5—H5109.3C16—C17—H17A109.7
C4—C5—H5109.3N4—C17—H17B109.7
C5—C6—C10109.05 (16)C16—C17—H17B109.7
C5—C6—H6A109.9H17A—C17—H17B108.2
C10—C6—H6A109.9C19—C18—C23117.34 (15)
C5—C6—H6B109.9C19—C18—N5122.67 (15)
C10—C6—H6B109.9C23—C18—N5119.90 (14)
H6A—C6—H6B108.3C20—C19—C18121.50 (16)
C8—C7—C5109.12 (15)C20—C19—H19119.2
C8—C7—H7A109.9C18—C19—H19119.2
C5—C7—H7A109.9C21—C20—C19120.12 (17)
C8—C7—H7B109.9C21—C20—H20119.9
C5—C7—H7B109.9C19—C20—H20119.9
H7A—C7—H7B108.3C20—C21—C22119.80 (17)
C7—C8—C9109.79 (16)C20—C21—H21120.1
C7—C8—C12110.30 (15)C22—C21—H21120.1
C9—C8—C12109.24 (15)C23—C22—C21120.59 (17)
C7—C8—H8109.2C23—C22—H22119.7
C9—C8—H8109.2C21—C22—H22119.7
C12—C8—H8109.2O1—C23—C22122.90 (15)
C8—C9—C10109.23 (15)O1—C23—C18116.54 (14)
C8—C9—H9A109.8C22—C23—C18120.55 (15)
C10—C9—H9A109.8O1—C24—H24A109.5
C8—C9—H9B109.8O1—C24—H24B109.5
C10—C9—H9B109.8H24A—C24—H24B109.5
H9A—C9—H9B108.3O1—C24—H24C109.5
C6—C10—C9110.18 (16)H24A—C24—H24C109.5
C6—C10—C11109.55 (17)H24B—C24—H24C109.5
C9—C10—C11109.63 (16)N2—C25—H25A109.5
C6—C10—H10109.2N2—C25—H25B109.5
C9—C10—H10109.2H25A—C25—H25B109.5
C11—C10—H10109.2N2—C25—H25C109.5
C10—C11—C3109.53 (14)H25A—C25—H25C109.5
C10—C11—H11A109.8H25B—C25—H25C109.5
C1—N1—N3—C20.20 (18)C9—C10—C11—C359.7 (2)
C13—N1—N3—C2174.73 (14)C2—C3—C11—C10178.08 (15)
N3—N1—C1—N20.23 (17)C4—C3—C11—C1059.39 (19)
C13—N1—C1—N2173.81 (14)C12—C3—C11—C1058.10 (19)
N3—N1—C1—S1179.72 (12)C7—C8—C12—C360.79 (19)
C13—N1—C1—S16.2 (3)C9—C8—C12—C359.97 (19)
C2—N2—C1—N10.56 (17)C2—C3—C12—C8178.88 (14)
C25—N2—C1—N1174.65 (16)C11—C3—C12—C858.36 (18)
C2—N2—C1—S1179.39 (13)C4—C3—C12—C859.76 (18)
C25—N2—C1—S15.4 (2)C14—N4—C13—N160.62 (19)
N1—N3—C2—N20.56 (17)C17—N4—C13—N167.27 (19)
N1—N3—C2—C3175.85 (14)C1—N1—C13—N4101.45 (19)
C1—N2—C2—N30.73 (19)N3—N1—C13—N484.90 (19)
C25—N2—C2—N3173.93 (18)C13—N4—C14—C15175.19 (13)
C1—N2—C2—C3175.51 (15)C17—N4—C14—C1555.49 (17)
C25—N2—C2—C39.8 (3)C18—N5—C15—C14168.11 (13)
N3—C2—C3—C11117.37 (17)C16—N5—C15—C1460.06 (17)
N2—C2—C3—C1158.4 (2)N4—C14—C15—N557.71 (18)
N3—C2—C3—C41.5 (2)C18—N5—C16—C17166.47 (13)
N2—C2—C3—C4177.26 (16)C15—N5—C16—C1760.98 (17)
N3—C2—C3—C12120.12 (17)C13—N4—C17—C16175.66 (13)
N2—C2—C3—C1264.1 (2)C14—N4—C17—C1655.52 (17)
C2—C3—C4—C5178.66 (15)N5—C16—C17—N458.50 (17)
C11—C3—C4—C558.86 (19)C15—N5—C18—C1910.3 (2)
C12—C3—C4—C560.0 (2)C16—N5—C18—C19118.81 (17)
C3—C4—C5—C659.8 (2)C15—N5—C18—C23166.10 (15)
C3—C4—C5—C760.6 (2)C16—N5—C18—C2364.78 (19)
C7—C5—C6—C1060.0 (2)C23—C18—C19—C201.2 (2)
C4—C5—C6—C1060.5 (2)N5—C18—C19—C20177.64 (16)
C6—C5—C7—C860.8 (2)C18—C19—C20—C211.7 (3)
C4—C5—C7—C859.5 (2)C19—C20—C21—C222.9 (3)
C5—C7—C8—C960.68 (19)C20—C21—C22—C231.3 (3)
C5—C7—C8—C1259.7 (2)C24—O1—C23—C227.7 (2)
C7—C8—C9—C1059.67 (19)C24—O1—C23—C18171.55 (15)
C12—C8—C9—C1061.40 (19)C21—C22—C23—O1177.68 (16)
C5—C6—C10—C959.3 (2)C21—C22—C23—C181.6 (3)
C5—C6—C10—C1161.4 (2)C19—C18—C23—O1176.55 (14)
C8—C9—C10—C659.1 (2)N5—C18—C23—O10.0 (2)
C8—C9—C10—C1161.5 (2)C19—C18—C23—C222.8 (2)
C6—C10—C11—C361.3 (2)N5—C18—C23—C22179.35 (15)

Experimental details

Crystal data
Chemical formulaC25H35N5OS
Mr453.64
Crystal system, space groupMonoclinic, P21/n
Temperature (K)220
a, b, c (Å)11.0203 (2), 12.1148 (2), 18.7624 (4)
β (°) 103.473 (1)
V3)2436.01 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.49 × 0.45 × 0.30
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.657, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
24895, 5620, 3796
Rint0.051
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.110, 1.03
No. of reflections5620
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.28

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors thank Dr Frank W. Heinemann, University of Erlangen-Nurnberg, Germany, for providing technical assistance.

References

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