Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015953/ob6523sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015953/ob6523Isup2.hkl |
CCDC reference: 274609
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
C15H19N5OS | Z = 2 |
Mr = 317.41 | F(000) = 336 |
Triclinic, P1 | Dx = 1.242 Mg m−3 |
Hall symbol: -P 1 | Melting point: 407 K |
a = 8.9387 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1043 (7) Å | Cell parameters from 11208 reflections |
c = 10.6069 (8) Å | θ = 1.9–29.0° |
α = 88.509 (6)° | µ = 0.20 mm−1 |
β = 85.498 (6)° | T = 296 K |
γ = 80.661 (6)° | Prism, colourless |
V = 849.05 (11) Å3 | 0.62 × 0.42 × 0.20 mm |
Stoe IPDS-2 diffractometer | 4462 independent reflections |
Radiation source: sealed X-ray tube | 3716 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.034 |
Detector resolution: 6.67 pixels mm-1 | θmax = 29.0°, θmin = 1.9° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.886, Tmax = 0.967 | l = −14→13 |
11655 measured reflections |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.0942P] where P = (Fo2 + 2Fc2)/3 |
4462 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Experimental. Melting points were determined in open capillary tubes on a digital Gallenkamp melting point apparatus and are uncorrected. The IR spectra were recorded for KBr disks with a Mattson 1000 F T—IR spectrometer. 1H-NMR spectra were recorded at room temperature on a Varian-Mercury-Plus 400 MHz 1H-NMR, 100 MHz 13C-NMR spectrometer in DMSO-d6 with TMS as an internal standard. Starting materials was obtained from Fluka or Aldrich. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.03503 (4) | 0.27711 (4) | 0.37723 (3) | 0.05186 (11) | |
O1 | 0.66113 (13) | −0.04294 (12) | 0.33480 (15) | 0.0767 (4) | |
N1 | 0.32526 (11) | 0.39491 (11) | 0.59419 (9) | 0.0406 (2) | |
N2 | 0.27940 (11) | 0.35900 (11) | 0.48007 (9) | 0.0392 (2) | |
N3 | 0.49030 (11) | 0.24709 (11) | 0.33066 (10) | 0.0437 (2) | |
N4 | 0.09693 (11) | 0.33029 (10) | 0.61769 (9) | 0.0391 (2) | |
N5 | 0.23554 (18) | 0.4652 (2) | 1.06510 (12) | 0.0739 (4) | |
C1 | 0.13896 (13) | 0.32053 (12) | 0.49046 (11) | 0.0392 (2) | |
C2 | 0.21296 (13) | 0.37622 (12) | 0.67545 (11) | 0.0394 (2) | |
C3 | 0.37869 (13) | 0.37358 (13) | 0.36387 (11) | 0.0416 (2) | |
H3A | 0.3148 | 0.3967 | 0.2939 | 0.050* | |
H3B | 0.4307 | 0.4578 | 0.3734 | 0.050* | |
C4 | 0.42821 (17) | 0.11901 (16) | 0.29056 (16) | 0.0574 (3) | |
H4A | 0.3602 | 0.1489 | 0.2243 | 0.069* | |
H4B | 0.3706 | 0.0797 | 0.3613 | 0.069* | |
C5 | 0.5569 (2) | 0.0006 (2) | 0.2421 (2) | 0.0767 (5) | |
H5A | 0.5157 | −0.0855 | 0.2171 | 0.092* | |
H5B | 0.6097 | 0.0385 | 0.1680 | 0.092* | |
C6 | 0.72175 (17) | 0.08196 (18) | 0.37334 (19) | 0.0657 (4) | |
H6A | 0.7775 | 0.1213 | 0.3015 | 0.079* | |
H6B | 0.7925 | 0.0507 | 0.4373 | 0.079* | |
C7 | 0.59922 (15) | 0.20232 (16) | 0.42568 (14) | 0.0527 (3) | |
H7A | 0.5477 | 0.1660 | 0.5012 | 0.063* | |
H7B | 0.6438 | 0.2873 | 0.4484 | 0.063* | |
C8 | 0.21695 (14) | 0.40488 (14) | 0.81040 (11) | 0.0437 (3) | |
C9 | 0.28993 (17) | 0.51899 (18) | 0.84571 (13) | 0.0560 (3) | |
H9 | 0.3330 | 0.5785 | 0.7851 | 0.067* | |
C10 | 0.2971 (2) | 0.5420 (2) | 0.97280 (15) | 0.0702 (4) | |
H10 | 0.3489 | 0.6169 | 0.9954 | 0.084* | |
C11 | 0.1662 (2) | 0.3566 (2) | 1.02984 (14) | 0.0698 (4) | |
H11 | 0.1220 | 0.3009 | 1.0928 | 0.084* | |
C12 | 0.15527 (18) | 0.32091 (18) | 0.90553 (13) | 0.0579 (3) | |
H12 | 0.1074 | 0.2419 | 0.8861 | 0.070* | |
C13 | −0.05649 (14) | 0.31609 (15) | 0.67084 (13) | 0.0474 (3) | |
H13A | −0.1292 | 0.3571 | 0.6108 | 0.057* | |
H13B | −0.0792 | 0.3742 | 0.7473 | 0.057* | |
C14 | −0.07525 (16) | 0.15867 (17) | 0.70120 (16) | 0.0576 (3) | |
H14 | −0.0363 | 0.0874 | 0.6409 | 0.069* | |
C15 | −0.1411 (3) | 0.1136 (3) | 0.8043 (2) | 0.1020 (8) | |
H15A | −0.1815 | 0.1814 | 0.8669 | 0.122* | |
H15B | −0.1481 | 0.0133 | 0.8159 | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04829 (19) | 0.0632 (2) | 0.04683 (18) | −0.01327 (14) | −0.00996 (13) | −0.00649 (14) |
O1 | 0.0574 (6) | 0.0486 (6) | 0.1213 (11) | 0.0014 (5) | −0.0083 (7) | −0.0083 (6) |
N1 | 0.0417 (5) | 0.0438 (5) | 0.0370 (5) | −0.0085 (4) | −0.0034 (4) | −0.0035 (4) |
N2 | 0.0399 (5) | 0.0430 (5) | 0.0353 (4) | −0.0080 (4) | −0.0023 (4) | −0.0027 (4) |
N3 | 0.0414 (5) | 0.0424 (5) | 0.0467 (5) | −0.0054 (4) | −0.0006 (4) | −0.0029 (4) |
N4 | 0.0371 (5) | 0.0402 (5) | 0.0396 (5) | −0.0055 (4) | 0.0000 (4) | −0.0025 (4) |
N5 | 0.0766 (9) | 0.1045 (11) | 0.0407 (6) | −0.0132 (8) | −0.0049 (6) | −0.0106 (7) |
C1 | 0.0387 (5) | 0.0379 (5) | 0.0403 (5) | −0.0042 (4) | −0.0025 (4) | −0.0014 (4) |
C2 | 0.0414 (5) | 0.0384 (5) | 0.0381 (5) | −0.0054 (4) | −0.0024 (4) | −0.0020 (4) |
C3 | 0.0440 (6) | 0.0417 (6) | 0.0381 (5) | −0.0063 (4) | 0.0009 (4) | 0.0010 (4) |
C4 | 0.0507 (7) | 0.0509 (7) | 0.0712 (9) | −0.0062 (6) | −0.0082 (6) | −0.0125 (6) |
C5 | 0.0652 (10) | 0.0601 (9) | 0.1039 (14) | −0.0037 (7) | −0.0046 (9) | −0.0315 (9) |
C6 | 0.0453 (7) | 0.0587 (8) | 0.0920 (12) | −0.0033 (6) | −0.0077 (7) | −0.0038 (8) |
C7 | 0.0459 (7) | 0.0524 (7) | 0.0601 (8) | −0.0066 (5) | −0.0086 (6) | −0.0014 (6) |
C8 | 0.0437 (6) | 0.0486 (6) | 0.0374 (5) | −0.0040 (5) | −0.0015 (4) | −0.0027 (5) |
C9 | 0.0603 (8) | 0.0658 (8) | 0.0445 (7) | −0.0189 (6) | 0.0016 (6) | −0.0089 (6) |
C10 | 0.0722 (10) | 0.0910 (12) | 0.0521 (8) | −0.0246 (9) | −0.0034 (7) | −0.0221 (8) |
C11 | 0.0779 (11) | 0.0904 (12) | 0.0405 (7) | −0.0148 (9) | −0.0007 (7) | 0.0071 (7) |
C12 | 0.0680 (9) | 0.0637 (8) | 0.0437 (7) | −0.0164 (7) | −0.0033 (6) | 0.0049 (6) |
C13 | 0.0383 (6) | 0.0507 (7) | 0.0515 (7) | −0.0048 (5) | 0.0045 (5) | −0.0054 (5) |
C14 | 0.0505 (7) | 0.0555 (8) | 0.0681 (9) | −0.0156 (6) | 0.0050 (6) | −0.0061 (6) |
C15 | 0.1258 (19) | 0.0818 (13) | 0.1032 (16) | −0.0520 (13) | 0.0373 (14) | −0.0088 (11) |
S1—C1 | 1.6676 (12) | C5—H5B | 0.9700 |
O1—C5 | 1.413 (2) | C6—C7 | 1.502 (2) |
O1—C6 | 1.419 (2) | C6—H6A | 0.9700 |
N1—C2 | 1.3006 (15) | C6—H6B | 0.9700 |
N1—N2 | 1.3719 (13) | C7—H7A | 0.9700 |
N2—C1 | 1.3526 (15) | C7—H7B | 0.9700 |
N2—C3 | 1.4773 (15) | C8—C12 | 1.3841 (19) |
N3—C3 | 1.4278 (15) | C8—C9 | 1.3870 (19) |
N3—C4 | 1.4566 (17) | C9—C10 | 1.378 (2) |
N3—C7 | 1.4607 (16) | C9—H9 | 0.9300 |
N4—C2 | 1.3711 (14) | C10—H10 | 0.9300 |
N4—C1 | 1.3734 (15) | C11—C12 | 1.381 (2) |
N4—C13 | 1.4654 (15) | C11—H11 | 0.9300 |
N5—C10 | 1.325 (2) | C12—H12 | 0.9300 |
N5—C11 | 1.325 (2) | C13—C14 | 1.494 (2) |
C2—C8 | 1.4658 (16) | C13—H13A | 0.9700 |
C3—H3A | 0.9700 | C13—H13B | 0.9700 |
C3—H3B | 0.9700 | C14—C15 | 1.290 (3) |
C4—C5 | 1.511 (2) | C14—H14 | 0.9300 |
C4—H4A | 0.9700 | C15—H15A | 0.9300 |
C4—H4B | 0.9700 | C15—H15B | 0.9300 |
C5—H5A | 0.9700 | ||
C5—O1—C6 | 110.12 (13) | C7—C6—H6A | 109.3 |
C2—N1—N2 | 104.48 (9) | O1—C6—H6B | 109.3 |
C1—N2—N1 | 112.54 (9) | C7—C6—H6B | 109.3 |
C1—N2—C3 | 128.11 (10) | H6A—C6—H6B | 107.9 |
N1—N2—C3 | 119.25 (9) | N3—C7—C6 | 109.42 (13) |
C3—N3—C4 | 114.41 (10) | N3—C7—H7A | 109.8 |
C3—N3—C7 | 114.45 (10) | C6—C7—H7A | 109.8 |
C4—N3—C7 | 110.46 (11) | N3—C7—H7B | 109.8 |
C2—N4—C1 | 107.67 (9) | C6—C7—H7B | 109.8 |
C2—N4—C13 | 128.90 (10) | H7A—C7—H7B | 108.2 |
C1—N4—C13 | 122.71 (10) | C12—C8—C9 | 117.78 (12) |
C10—N5—C11 | 116.20 (14) | C12—C8—C2 | 123.39 (12) |
N2—C1—N4 | 103.84 (10) | C9—C8—C2 | 118.81 (12) |
N2—C1—S1 | 129.21 (9) | C10—C9—C8 | 118.33 (14) |
N4—C1—S1 | 126.92 (9) | C10—C9—H9 | 120.8 |
N1—C2—N4 | 111.46 (10) | C8—C9—H9 | 120.8 |
N1—C2—C8 | 121.61 (11) | N5—C10—C9 | 124.72 (16) |
N4—C2—C8 | 126.92 (11) | N5—C10—H10 | 117.6 |
N3—C3—N2 | 116.37 (9) | C9—C10—H10 | 117.6 |
N3—C3—H3A | 108.2 | N5—C11—C12 | 124.15 (16) |
N2—C3—H3A | 108.2 | N5—C11—H11 | 117.9 |
N3—C3—H3B | 108.2 | C12—C11—H11 | 117.9 |
N2—C3—H3B | 108.2 | C11—C12—C8 | 118.78 (15) |
H3A—C3—H3B | 107.3 | C11—C12—H12 | 120.6 |
N3—C4—C5 | 109.31 (12) | C8—C12—H12 | 120.6 |
N3—C4—H4A | 109.8 | N4—C13—C14 | 112.99 (11) |
C5—C4—H4A | 109.8 | N4—C13—H13A | 109.0 |
N3—C4—H4B | 109.8 | C14—C13—H13A | 109.0 |
C5—C4—H4B | 109.8 | N4—C13—H13B | 109.0 |
H4A—C4—H4B | 108.3 | C14—C13—H13B | 109.0 |
O1—C5—C4 | 111.61 (15) | H13A—C13—H13B | 107.8 |
O1—C5—H5A | 109.3 | C15—C14—C13 | 125.31 (17) |
C4—C5—H5A | 109.3 | C15—C14—H14 | 117.3 |
O1—C5—H5B | 109.3 | C13—C14—H14 | 117.3 |
C4—C5—H5B | 109.3 | C14—C15—H15A | 120.0 |
H5A—C5—H5B | 108.0 | C14—C15—H15B | 120.0 |
O1—C6—C7 | 111.77 (12) | H15A—C15—H15B | 120.0 |
O1—C6—H6A | 109.3 | ||
C2—N1—N2—C1 | 0.90 (13) | C6—O1—C5—C4 | −58.5 (2) |
C2—N1—N2—C3 | 177.63 (10) | N3—C4—C5—O1 | 57.8 (2) |
N1—N2—C1—N4 | −1.19 (12) | C5—O1—C6—C7 | 58.5 (2) |
C3—N2—C1—N4 | −177.56 (10) | C3—N3—C7—C6 | −172.69 (11) |
N1—N2—C1—S1 | 176.71 (9) | C4—N3—C7—C6 | 56.45 (15) |
C3—N2—C1—S1 | 0.35 (18) | O1—C6—C7—N3 | −57.51 (18) |
C2—N4—C1—N2 | 1.00 (12) | N1—C2—C8—C12 | −143.98 (14) |
C13—N4—C1—N2 | 172.10 (10) | N4—C2—C8—C12 | 36.94 (19) |
C2—N4—C1—S1 | −176.97 (9) | N1—C2—C8—C9 | 34.04 (18) |
C13—N4—C1—S1 | −5.87 (16) | N4—C2—C8—C9 | −145.04 (13) |
N2—N1—C2—N4 | −0.21 (12) | C12—C8—C9—C10 | 0.1 (2) |
N2—N1—C2—C8 | −179.43 (10) | C2—C8—C9—C10 | −178.02 (14) |
C1—N4—C2—N1 | −0.51 (13) | C11—N5—C10—C9 | 1.8 (3) |
C13—N4—C2—N1 | −170.88 (11) | C8—C9—C10—N5 | −1.9 (3) |
C1—N4—C2—C8 | 178.65 (11) | C10—N5—C11—C12 | 0.0 (3) |
C13—N4—C2—C8 | 8.28 (19) | N5—C11—C12—C8 | −1.6 (3) |
C4—N3—C3—N2 | 68.69 (15) | C9—C8—C12—C11 | 1.5 (2) |
C7—N3—C3—N2 | −60.22 (14) | C2—C8—C12—C11 | 179.51 (14) |
C1—N2—C3—N3 | −95.79 (14) | C2—N4—C13—C14 | −102.89 (15) |
N1—N2—C3—N3 | 88.06 (13) | C1—N4—C13—C14 | 88.03 (15) |
C3—N3—C4—C5 | 172.69 (13) | N4—C13—C14—C15 | 134.8 (2) |
C7—N3—C4—C5 | −56.43 (17) |