In the title compound, C
14H
22N
4S
2, 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
CCDC reference: 206749
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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
C14H22N4S2 | F(000) = 1328 |
Mr = 310.48 | Dx = 1.273 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 15586 reflections |
a = 28.5692 (4) Å | θ = 1.0–27.5° |
b = 4.6529 (1) Å | µ = 0.33 mm−1 |
c = 26.4989 (4) Å | T = 150 K |
β = 113.137 (1)° | Needle, colourless |
V = 3239.17 (10) Å3 | 0.69 × 0.15 × 0.12 mm |
Z = 8 | |
Data collection top
Nonius KappaCCD diffractometer | 2856 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.092 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
φ and ω scans | h = −36→36 |
16592 measured reflections | k = −6→5 |
3686 independent reflections | l = −34→34 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.14264 (2) | 0.61861 (9) | 0.38634 (2) | 0.02903 (13) | |
N11 | 0.25940 (5) | 0.4226 (3) | 0.40475 (5) | 0.0237 (3) | |
N12 | 0.29367 (5) | 0.5698 (3) | 0.44833 (6) | 0.0269 (3) | |
C13 | 0.32252 (6) | 0.7107 (4) | 0.42727 (7) | 0.0283 (4) | |
C14 | 0.30687 (6) | 0.6545 (4) | 0.37101 (7) | 0.0294 (4) | |
H14 | 0.3213 | 0.7299 | 0.3470 | 0.035* | |
C15 | 0.26646 (6) | 0.4681 (4) | 0.35775 (6) | 0.0254 (3) | |
C16 | 0.22393 (6) | 0.2262 (3) | 0.41386 (6) | 0.0245 (3) | |
H16A | 0.2435 | 0.0791 | 0.4409 | 0.029* | |
H16B | 0.2041 | 0.1261 | 0.3790 | 0.029* | |
C17 | 0.18738 (6) | 0.3718 (3) | 0.43443 (6) | 0.0258 (4) | |
H17A | 0.2074 | 0.4786 | 0.4684 | 0.031* | |
H17B | 0.1679 | 0.2215 | 0.4442 | 0.031* | |
C18 | 0.36528 (7) | 0.8996 (4) | 0.46289 (8) | 0.0387 (5) | |
H18A | 0.3550 | 1.1015 | 0.4560 | 0.058* | |
H18B | 0.3953 | 0.8668 | 0.4544 | 0.058* | |
H18C | 0.3736 | 0.8540 | 0.5016 | 0.058* | |
C19 | 0.23507 (6) | 0.3249 (4) | 0.30469 (7) | 0.0322 (4) | |
H19A | 0.2399 | 0.1163 | 0.3087 | 0.048* | |
H19B | 0.2457 | 0.3935 | 0.2758 | 0.048* | |
H19C | 0.1991 | 0.3708 | 0.2948 | 0.048* | |
S2 | 0.10696 (1) | 0.38894 (10) | 0.31603 (2) | 0.02804 (13) | |
N21 | −0.02010 (5) | 0.2129 (3) | 0.34514 (5) | 0.0239 (3) | |
N22 | −0.05751 (5) | 0.0688 (3) | 0.30420 (5) | 0.0248 (3) | |
C23 | −0.08195 (6) | −0.0784 (3) | 0.32958 (7) | 0.0255 (4) | |
C24 | −0.05984 (6) | −0.0308 (4) | 0.38645 (7) | 0.0326 (4) | |
H24 | −0.0702 | −0.1110 | 0.4134 | 0.039* | |
C25 | −0.02017 (6) | 0.1552 (4) | 0.39525 (7) | 0.0287 (4) | |
C26 | 0.01606 (6) | 0.3825 (3) | 0.33189 (7) | 0.0259 (4) | |
H26A | 0.0311 | 0.5315 | 0.3604 | 0.031* | |
H26B | −0.0017 | 0.4805 | 0.2963 | 0.031* | |
C27 | 0.05796 (6) | 0.1925 (3) | 0.32865 (7) | 0.0256 (4) | |
H27A | 0.0426 | 0.0502 | 0.2989 | 0.031* | |
H27B | 0.0738 | 0.0854 | 0.3636 | 0.031* | |
C28 | −0.12671 (6) | −0.2628 (4) | 0.29742 (8) | 0.0352 (4) | |
H28A | −0.1416 | −0.1959 | 0.2593 | 0.053* | |
H28B | −0.1522 | −0.2505 | 0.3135 | 0.053* | |
H28C | −0.1156 | −0.4627 | 0.2984 | 0.053* | |
C29 | 0.01798 (8) | 0.2836 (5) | 0.44671 (7) | 0.0474 (5) | |
H29A | 0.0520 | 0.2116 | 0.4528 | 0.071* | |
H29B | 0.0095 | 0.2299 | 0.4779 | 0.071* | |
H29C | 0.0175 | 0.4933 | 0.4432 | 0.071* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0208 (2) | 0.0240 (2) | 0.0379 (3) | −0.00120 (16) | 0.00672 (18) | 0.00146 (17) |
N11 | 0.0191 (6) | 0.0256 (7) | 0.0241 (7) | −0.0018 (5) | 0.0062 (5) | −0.0005 (5) |
N12 | 0.0211 (7) | 0.0279 (8) | 0.0287 (7) | −0.0021 (6) | 0.0066 (6) | −0.0043 (6) |
C13 | 0.0215 (8) | 0.0233 (9) | 0.0408 (10) | 0.0011 (7) | 0.0131 (7) | −0.0019 (7) |
C14 | 0.0251 (8) | 0.0300 (10) | 0.0376 (10) | 0.0013 (7) | 0.0169 (7) | 0.0036 (7) |
C15 | 0.0229 (8) | 0.0279 (9) | 0.0249 (8) | 0.0060 (7) | 0.0090 (7) | 0.0037 (7) |
C16 | 0.0223 (8) | 0.0238 (8) | 0.0247 (8) | −0.0015 (7) | 0.0063 (6) | 0.0038 (7) |
C17 | 0.0226 (8) | 0.0283 (9) | 0.0245 (8) | −0.0033 (7) | 0.0073 (7) | 0.0024 (7) |
C18 | 0.0278 (9) | 0.0364 (11) | 0.0530 (12) | −0.0079 (8) | 0.0171 (9) | −0.0121 (9) |
C19 | 0.0271 (9) | 0.0432 (11) | 0.0257 (9) | 0.0015 (8) | 0.0096 (7) | 0.0013 (8) |
S2 | 0.0187 (2) | 0.0391 (3) | 0.0254 (2) | −0.00171 (17) | 0.00767 (16) | 0.00647 (17) |
N21 | 0.0181 (6) | 0.0276 (7) | 0.0249 (7) | −0.0028 (5) | 0.0072 (5) | −0.0013 (6) |
N22 | 0.0190 (6) | 0.0281 (8) | 0.0254 (7) | −0.0028 (5) | 0.0068 (5) | −0.0043 (6) |
C23 | 0.0200 (8) | 0.0254 (9) | 0.0326 (9) | −0.0003 (6) | 0.0120 (7) | −0.0040 (7) |
C24 | 0.0334 (9) | 0.0386 (10) | 0.0308 (9) | −0.0062 (8) | 0.0178 (8) | 0.0001 (8) |
C25 | 0.0266 (8) | 0.0350 (10) | 0.0244 (8) | −0.0028 (7) | 0.0099 (7) | −0.0021 (7) |
C26 | 0.0210 (8) | 0.0263 (9) | 0.0297 (8) | −0.0030 (7) | 0.0092 (7) | 0.0021 (7) |
C27 | 0.0203 (7) | 0.0266 (9) | 0.0286 (8) | −0.0023 (6) | 0.0084 (7) | 0.0022 (7) |
C28 | 0.0253 (9) | 0.0356 (10) | 0.0471 (11) | −0.0060 (8) | 0.0169 (8) | −0.0114 (8) |
C29 | 0.0444 (11) | 0.0637 (14) | 0.0285 (10) | −0.0173 (11) | 0.0085 (9) | −0.0070 (9) |
Geometric parameters (Å, º) top
S1—C17 | 1.8156 (16) | S2—C27 | 1.8097 (15) |
S1—S2 | 2.0396 (6) | N21—C25 | 1.355 (2) |
N11—C15 | 1.354 (2) | N21—N22 | 1.3628 (17) |
N11—N12 | 1.3683 (18) | N21—C26 | 1.4488 (19) |
N11—C16 | 1.4537 (19) | N22—C23 | 1.333 (2) |
N12—C13 | 1.335 (2) | C23—C24 | 1.404 (2) |
C13—C14 | 1.402 (2) | C23—C28 | 1.497 (2) |
C13—C18 | 1.500 (2) | C24—C25 | 1.371 (2) |
C14—C15 | 1.375 (2) | C24—H24 | 0.9500 |
C14—H14 | 0.9500 | C25—C29 | 1.495 (2) |
C15—C19 | 1.495 (2) | C26—C27 | 1.517 (2) |
C16—C17 | 1.514 (2) | C26—H26A | 0.9900 |
C16—H16A | 0.9900 | C26—H26B | 0.9900 |
C16—H16B | 0.9900 | C27—H27A | 0.9900 |
C17—H17A | 0.9900 | C27—H27B | 0.9900 |
C17—H17B | 0.9900 | C28—H28A | 0.9800 |
C18—H18A | 0.9800 | C28—H28B | 0.9800 |
C18—H18B | 0.9800 | C28—H28C | 0.9800 |
C18—H18C | 0.9800 | C29—H29A | 0.9800 |
C19—H19A | 0.9800 | C29—H29B | 0.9800 |
C19—H19B | 0.9800 | C29—H29C | 0.9800 |
C19—H19C | 0.9800 | | |
| | | |
C17—S1—S2 | 105.73 (6) | C27—S2—S1 | 103.95 (6) |
C15—N11—N12 | 112.48 (13) | C25—N21—N22 | 112.32 (13) |
C15—N11—C16 | 128.06 (13) | C25—N21—C26 | 128.39 (13) |
N12—N11—C16 | 119.25 (13) | N22—N21—C26 | 119.08 (12) |
C13—N12—N11 | 104.33 (13) | C23—N22—N21 | 104.68 (13) |
N12—C13—C14 | 111.19 (15) | N22—C23—C24 | 110.87 (14) |
N12—C13—C18 | 120.59 (16) | N22—C23—C28 | 120.45 (15) |
C14—C13—C18 | 128.22 (16) | C24—C23—C28 | 128.68 (16) |
C15—C14—C13 | 105.92 (15) | C25—C24—C23 | 105.98 (15) |
C15—C14—H14 | 127.0 | C25—C24—H24 | 127.0 |
C13—C14—H14 | 127.0 | C23—C24—H24 | 127.0 |
N11—C15—C14 | 106.08 (14) | N21—C25—C24 | 106.13 (14) |
N11—C15—C19 | 122.97 (14) | N21—C25—C29 | 122.21 (15) |
C14—C15—C19 | 130.92 (15) | C24—C25—C29 | 131.66 (16) |
N11—C16—C17 | 113.75 (13) | N21—C26—C27 | 110.47 (13) |
N11—C16—H16A | 108.8 | N21—C26—H26A | 109.6 |
C17—C16—H16A | 108.8 | C27—C26—H26A | 109.6 |
N11—C16—H16B | 108.8 | N21—C26—H26B | 109.6 |
C17—C16—H16B | 108.8 | C27—C26—H26B | 109.6 |
H16A—C16—H16B | 107.7 | H26A—C26—H26B | 108.1 |
C16—C17—S1 | 115.16 (11) | C26—C27—S2 | 113.63 (11) |
C16—C17—H17A | 108.5 | C26—C27—H27A | 108.8 |
S1—C17—H17A | 108.5 | S2—C27—H27A | 108.8 |
C16—C17—H17B | 108.5 | C26—C27—H27B | 108.8 |
S1—C17—H17B | 108.5 | S2—C27—H27B | 108.8 |
H17A—C17—H17B | 107.5 | H27A—C27—H27B | 107.7 |
C13—C18—H18A | 109.5 | C23—C28—H28A | 109.5 |
C13—C18—H18B | 109.5 | C23—C28—H28B | 109.5 |
H18A—C18—H18B | 109.5 | H28A—C28—H28B | 109.5 |
C13—C18—H18C | 109.5 | C23—C28—H28C | 109.5 |
H18A—C18—H18C | 109.5 | H28A—C28—H28C | 109.5 |
H18B—C18—H18C | 109.5 | H28B—C28—H28C | 109.5 |
C15—C19—H19A | 109.5 | C25—C29—H29A | 109.5 |
C15—C19—H19B | 109.5 | C25—C29—H29B | 109.5 |
H19A—C19—H19B | 109.5 | H29A—C29—H29B | 109.5 |
C15—C19—H19C | 109.5 | C25—C29—H29C | 109.5 |
H19A—C19—H19C | 109.5 | H29A—C29—H29C | 109.5 |
H19B—C19—H19C | 109.5 | H29B—C29—H29C | 109.5 |
| | | |
C15—N11—N12—C13 | 0.22 (17) | C25—N21—N22—C23 | 1.05 (17) |
C16—N11—N12—C13 | 175.39 (13) | C26—N21—N22—C23 | 176.20 (13) |
N11—N12—C13—C14 | 0.05 (18) | N21—N22—C23—C24 | −0.69 (17) |
N11—N12—C13—C18 | −179.96 (14) | N21—N22—C23—C28 | 179.18 (14) |
N12—C13—C14—C15 | −0.29 (19) | N22—C23—C24—C25 | 0.1 (2) |
C18—C13—C14—C15 | 179.73 (16) | C28—C23—C24—C25 | −179.74 (16) |
N12—N11—C15—C14 | −0.40 (18) | N22—N21—C25—C24 | −1.00 (19) |
C16—N11—C15—C14 | −175.05 (14) | C26—N21—C25—C24 | −175.59 (15) |
N12—N11—C15—C19 | 178.00 (14) | N22—N21—C25—C29 | 178.79 (16) |
C16—N11—C15—C19 | 3.3 (2) | C26—N21—C25—C29 | 4.2 (3) |
C13—C14—C15—N11 | 0.40 (18) | C23—C24—C25—N21 | 0.52 (19) |
C13—C14—C15—C19 | −177.82 (16) | C23—C24—C25—C29 | −179.24 (19) |
C15—N11—C16—C17 | −122.35 (16) | C25—N21—C26—C27 | 92.16 (19) |
N12—N11—C16—C17 | 63.32 (17) | N22—N21—C26—C27 | −82.11 (17) |
N11—C16—C17—S1 | 65.69 (16) | N21—C26—C27—S2 | −176.75 (10) |
S2—S1—C17—C16 | 54.12 (12) | S1—S2—C27—C26 | 68.12 (12) |
C17—S1—S2—C27 | 81.87 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···Cg1i | 0.98 | 2.84 | 3.757 (2) | 156 |
C28—H28A···Cg2ii | 0.98 | 2.90 | 3.791 (2) | 151 |
C27—H27B···S1ii | 0.99 | 2.83 | 3.5233 (17) | 127 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |