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In the title compound, C14H22N4S2, a diethyl di­sulfide bridge containing an S—S bond of 2.0396 (6) Å connects two 3,5-di­methyl­pyrazole rings via the N1 atoms. The di­sulfide mol­ecules are linked by weak C—H...π(pyrazole) interactions into chains that propagate along the b direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803002289/om6128sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803002289/om6128Isup2.hkl
Contains datablock I

CCDC reference: 206749

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 19.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Bis[(3,5-dimethylpyrazol-1-yl)ethyl] disulfide top
Crystal data top
C14H22N4S2F(000) = 1328
Mr = 310.48Dx = 1.273 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 15586 reflections
a = 28.5692 (4) Åθ = 1.0–27.5°
b = 4.6529 (1) ŵ = 0.33 mm1
c = 26.4989 (4) ÅT = 150 K
β = 113.137 (1)°Needle, colourless
V = 3239.17 (10) Å30.69 × 0.15 × 0.12 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
2856 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.092
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
φ and ω scansh = 3636
16592 measured reflectionsk = 65
3686 independent reflectionsl = 3434
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0493P)2 + 1.361P]
where P = (Fo2 + 2Fc2)/3
3686 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.32 e Å3
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
S10.14264 (2)0.61861 (9)0.38634 (2)0.02903 (13)
N110.25940 (5)0.4226 (3)0.40475 (5)0.0237 (3)
N120.29367 (5)0.5698 (3)0.44833 (6)0.0269 (3)
C130.32252 (6)0.7107 (4)0.42727 (7)0.0283 (4)
C140.30687 (6)0.6545 (4)0.37101 (7)0.0294 (4)
H140.32130.72990.34700.035*
C150.26646 (6)0.4681 (4)0.35775 (6)0.0254 (3)
C160.22393 (6)0.2262 (3)0.41386 (6)0.0245 (3)
H16A0.24350.07910.44090.029*
H16B0.20410.12610.37900.029*
C170.18738 (6)0.3718 (3)0.43443 (6)0.0258 (4)
H17A0.20740.47860.46840.031*
H17B0.16790.22150.44420.031*
C180.36528 (7)0.8996 (4)0.46289 (8)0.0387 (5)
H18A0.35501.10150.45600.058*
H18B0.39530.86680.45440.058*
H18C0.37360.85400.50160.058*
C190.23507 (6)0.3249 (4)0.30469 (7)0.0322 (4)
H19A0.23990.11630.30870.048*
H19B0.24570.39350.27580.048*
H19C0.19910.37080.29480.048*
S20.10696 (1)0.38894 (10)0.31603 (2)0.02804 (13)
N210.02010 (5)0.2129 (3)0.34514 (5)0.0239 (3)
N220.05751 (5)0.0688 (3)0.30420 (5)0.0248 (3)
C230.08195 (6)0.0784 (3)0.32958 (7)0.0255 (4)
C240.05984 (6)0.0308 (4)0.38645 (7)0.0326 (4)
H240.07020.11100.41340.039*
C250.02017 (6)0.1552 (4)0.39525 (7)0.0287 (4)
C260.01606 (6)0.3825 (3)0.33189 (7)0.0259 (4)
H26A0.03110.53150.36040.031*
H26B0.00170.48050.29630.031*
C270.05796 (6)0.1925 (3)0.32865 (7)0.0256 (4)
H27A0.04260.05020.29890.031*
H27B0.07380.08540.36360.031*
C280.12671 (6)0.2628 (4)0.29742 (8)0.0352 (4)
H28A0.14160.19590.25930.053*
H28B0.15220.25050.31350.053*
H28C0.11560.46270.29840.053*
C290.01798 (8)0.2836 (5)0.44671 (7)0.0474 (5)
H29A0.05200.21160.45280.071*
H29B0.00950.22990.47790.071*
H29C0.01750.49330.44320.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0208 (2)0.0240 (2)0.0379 (3)0.00120 (16)0.00672 (18)0.00146 (17)
N110.0191 (6)0.0256 (7)0.0241 (7)0.0018 (5)0.0062 (5)0.0005 (5)
N120.0211 (7)0.0279 (8)0.0287 (7)0.0021 (6)0.0066 (6)0.0043 (6)
C130.0215 (8)0.0233 (9)0.0408 (10)0.0011 (7)0.0131 (7)0.0019 (7)
C140.0251 (8)0.0300 (10)0.0376 (10)0.0013 (7)0.0169 (7)0.0036 (7)
C150.0229 (8)0.0279 (9)0.0249 (8)0.0060 (7)0.0090 (7)0.0037 (7)
C160.0223 (8)0.0238 (8)0.0247 (8)0.0015 (7)0.0063 (6)0.0038 (7)
C170.0226 (8)0.0283 (9)0.0245 (8)0.0033 (7)0.0073 (7)0.0024 (7)
C180.0278 (9)0.0364 (11)0.0530 (12)0.0079 (8)0.0171 (9)0.0121 (9)
C190.0271 (9)0.0432 (11)0.0257 (9)0.0015 (8)0.0096 (7)0.0013 (8)
S20.0187 (2)0.0391 (3)0.0254 (2)0.00171 (17)0.00767 (16)0.00647 (17)
N210.0181 (6)0.0276 (7)0.0249 (7)0.0028 (5)0.0072 (5)0.0013 (6)
N220.0190 (6)0.0281 (8)0.0254 (7)0.0028 (5)0.0068 (5)0.0043 (6)
C230.0200 (8)0.0254 (9)0.0326 (9)0.0003 (6)0.0120 (7)0.0040 (7)
C240.0334 (9)0.0386 (10)0.0308 (9)0.0062 (8)0.0178 (8)0.0001 (8)
C250.0266 (8)0.0350 (10)0.0244 (8)0.0028 (7)0.0099 (7)0.0021 (7)
C260.0210 (8)0.0263 (9)0.0297 (8)0.0030 (7)0.0092 (7)0.0021 (7)
C270.0203 (7)0.0266 (9)0.0286 (8)0.0023 (6)0.0084 (7)0.0022 (7)
C280.0253 (9)0.0356 (10)0.0471 (11)0.0060 (8)0.0169 (8)0.0114 (8)
C290.0444 (11)0.0637 (14)0.0285 (10)0.0173 (11)0.0085 (9)0.0070 (9)
Geometric parameters (Å, º) top
S1—C171.8156 (16)S2—C271.8097 (15)
S1—S22.0396 (6)N21—C251.355 (2)
N11—C151.354 (2)N21—N221.3628 (17)
N11—N121.3683 (18)N21—C261.4488 (19)
N11—C161.4537 (19)N22—C231.333 (2)
N12—C131.335 (2)C23—C241.404 (2)
C13—C141.402 (2)C23—C281.497 (2)
C13—C181.500 (2)C24—C251.371 (2)
C14—C151.375 (2)C24—H240.9500
C14—H140.9500C25—C291.495 (2)
C15—C191.495 (2)C26—C271.517 (2)
C16—C171.514 (2)C26—H26A0.9900
C16—H16A0.9900C26—H26B0.9900
C16—H16B0.9900C27—H27A0.9900
C17—H17A0.9900C27—H27B0.9900
C17—H17B0.9900C28—H28A0.9800
C18—H18A0.9800C28—H28B0.9800
C18—H18B0.9800C28—H28C0.9800
C18—H18C0.9800C29—H29A0.9800
C19—H19A0.9800C29—H29B0.9800
C19—H19B0.9800C29—H29C0.9800
C19—H19C0.9800
C17—S1—S2105.73 (6)C27—S2—S1103.95 (6)
C15—N11—N12112.48 (13)C25—N21—N22112.32 (13)
C15—N11—C16128.06 (13)C25—N21—C26128.39 (13)
N12—N11—C16119.25 (13)N22—N21—C26119.08 (12)
C13—N12—N11104.33 (13)C23—N22—N21104.68 (13)
N12—C13—C14111.19 (15)N22—C23—C24110.87 (14)
N12—C13—C18120.59 (16)N22—C23—C28120.45 (15)
C14—C13—C18128.22 (16)C24—C23—C28128.68 (16)
C15—C14—C13105.92 (15)C25—C24—C23105.98 (15)
C15—C14—H14127.0C25—C24—H24127.0
C13—C14—H14127.0C23—C24—H24127.0
N11—C15—C14106.08 (14)N21—C25—C24106.13 (14)
N11—C15—C19122.97 (14)N21—C25—C29122.21 (15)
C14—C15—C19130.92 (15)C24—C25—C29131.66 (16)
N11—C16—C17113.75 (13)N21—C26—C27110.47 (13)
N11—C16—H16A108.8N21—C26—H26A109.6
C17—C16—H16A108.8C27—C26—H26A109.6
N11—C16—H16B108.8N21—C26—H26B109.6
C17—C16—H16B108.8C27—C26—H26B109.6
H16A—C16—H16B107.7H26A—C26—H26B108.1
C16—C17—S1115.16 (11)C26—C27—S2113.63 (11)
C16—C17—H17A108.5C26—C27—H27A108.8
S1—C17—H17A108.5S2—C27—H27A108.8
C16—C17—H17B108.5C26—C27—H27B108.8
S1—C17—H17B108.5S2—C27—H27B108.8
H17A—C17—H17B107.5H27A—C27—H27B107.7
C13—C18—H18A109.5C23—C28—H28A109.5
C13—C18—H18B109.5C23—C28—H28B109.5
H18A—C18—H18B109.5H28A—C28—H28B109.5
C13—C18—H18C109.5C23—C28—H28C109.5
H18A—C18—H18C109.5H28A—C28—H28C109.5
H18B—C18—H18C109.5H28B—C28—H28C109.5
C15—C19—H19A109.5C25—C29—H29A109.5
C15—C19—H19B109.5C25—C29—H29B109.5
H19A—C19—H19B109.5H29A—C29—H29B109.5
C15—C19—H19C109.5C25—C29—H29C109.5
H19A—C19—H19C109.5H29A—C29—H29C109.5
H19B—C19—H19C109.5H29B—C29—H29C109.5
C15—N11—N12—C130.22 (17)C25—N21—N22—C231.05 (17)
C16—N11—N12—C13175.39 (13)C26—N21—N22—C23176.20 (13)
N11—N12—C13—C140.05 (18)N21—N22—C23—C240.69 (17)
N11—N12—C13—C18179.96 (14)N21—N22—C23—C28179.18 (14)
N12—C13—C14—C150.29 (19)N22—C23—C24—C250.1 (2)
C18—C13—C14—C15179.73 (16)C28—C23—C24—C25179.74 (16)
N12—N11—C15—C140.40 (18)N22—N21—C25—C241.00 (19)
C16—N11—C15—C14175.05 (14)C26—N21—C25—C24175.59 (15)
N12—N11—C15—C19178.00 (14)N22—N21—C25—C29178.79 (16)
C16—N11—C15—C193.3 (2)C26—N21—C25—C294.2 (3)
C13—C14—C15—N110.40 (18)C23—C24—C25—N210.52 (19)
C13—C14—C15—C19177.82 (16)C23—C24—C25—C29179.24 (19)
C15—N11—C16—C17122.35 (16)C25—N21—C26—C2792.16 (19)
N12—N11—C16—C1763.32 (17)N22—N21—C26—C2782.11 (17)
N11—C16—C17—S165.69 (16)N21—C26—C27—S2176.75 (10)
S2—S1—C17—C1654.12 (12)S1—S2—C27—C2668.12 (12)
C17—S1—S2—C2781.87 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···Cg1i0.982.843.757 (2)156
C28—H28A···Cg2ii0.982.903.791 (2)151
C27—H27B···S1ii0.992.833.5233 (17)127
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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