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organic compounds
The title compound, C15H9N9S3, was synthesized by the reaction of cyanuric chloride with the potassium salt of 2-mercaptopyrimidine. The dihedral angles between the three pyrimidinyl rings and the central triazine plane are 94.1 (4), 105.5 (3) and 126.6 (5)°. The three S atoms are essentially coplanar with the triazine ring, while the orientations of the three pyrimidinyl rings are different, with one ring twisting in the opposite direction to the other two.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008901/hg6159sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008901/hg6159Isup2.hkl |
CCDC reference: 270451
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.004 Å - R factor = 0.035
- wR factor = 0.090
- Data-to-parameter ratio = 12.7
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.004 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
2,4,6-tris(pyrimidin-2-ylsulfanyl)-1,3,5-triazine top
Crystal data top
| C15H9N9S3 | F(000) = 840 |
| Mr = 411.49 | Dx = 1.557 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1536 reflections |
| a = 9.020 (1) Å | θ = 2.6–22.5° |
| b = 18.233 (3) Å | µ = 0.44 mm−1 |
| c = 11.219 (2) Å | T = 293 K |
| β = 107.908 (2)° | Plate, colourless |
| V = 1755.7 (5) Å3 | 0.42 × 0.20 × 0.04 mm |
| Z = 4 |
Data collection top
| Bruker SMART CCD area-detector diffractometer | 3110 independent reflections |
| Radiation source: fine-focus sealed tube | 2177 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| φ and ω scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→9 |
| Tmin = 0.845, Tmax = 0.978 | k = −21→21 |
| 9470 measured reflections | l = −7→13 |
Refinement top
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0309P)2 + 0.2133P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.090 | (Δ/σ)max = 0.001 |
| S = 1.08 | Δρmax = 0.21 e Å−3 |
| 3110 reflections | Δρmin = −0.25 e Å−3 |
| 244 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
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.77586 (8) | 0.01474 (4) | 1.03672 (6) | 0.0507 (2) | |
| S2 | 1.08865 (8) | 0.26117 (4) | 1.06110 (7) | 0.0564 (2) | |
| S3 | 0.93995 (8) | 0.11367 (4) | 0.64794 (6) | 0.0555 (2) | |
| N1 | 0.8560 (2) | 0.06905 (10) | 0.84431 (18) | 0.0395 (5) | |
| N2 | 0.9960 (2) | 0.18121 (10) | 0.86156 (18) | 0.0424 (5) | |
| N3 | 0.9280 (2) | 0.13492 (10) | 1.03606 (18) | 0.0432 (5) | |
| N4 | 0.5224 (3) | 0.01067 (12) | 0.8402 (2) | 0.0548 (6) | |
| N5 | 0.6692 (3) | −0.09927 (11) | 0.8906 (2) | 0.0581 (6) | |
| N6 | 0.7258 (2) | 0.01102 (11) | 0.5618 (2) | 0.0545 (6) | |
| N7 | 0.9866 (2) | −0.02890 (12) | 0.6531 (2) | 0.0567 (6) | |
| N8 | 1.1053 (2) | 0.28886 (11) | 1.2938 (2) | 0.0517 (5) | |
| N9 | 0.8510 (2) | 0.26506 (11) | 1.1554 (2) | 0.0505 (5) | |
| C1 | 0.4180 (3) | −0.02472 (19) | 0.7484 (3) | 0.0656 (8) | |
| H1 | 0.3306 | 0.0005 | 0.7000 | 0.079* | |
| C2 | 0.4351 (4) | −0.0969 (2) | 0.7229 (3) | 0.0744 (9) | |
| H2 | 0.3622 | −0.1207 | 0.6574 | 0.089* | |
| C3 | 0.5615 (4) | −0.13216 (17) | 0.7963 (3) | 0.0751 (9) | |
| H3 | 0.5745 | −0.1815 | 0.7807 | 0.090* | |
| C4 | 0.6423 (3) | −0.02933 (13) | 0.9052 (2) | 0.0430 (6) | |
| C5 | 0.8607 (2) | 0.07946 (12) | 0.9621 (2) | 0.0373 (5) | |
| C6 | 0.9910 (2) | 0.18408 (12) | 0.9786 (2) | 0.0422 (6) | |
| C7 | 1.0048 (3) | 0.27115 (12) | 1.1844 (2) | 0.0420 (6) | |
| C8 | 0.7952 (3) | 0.27607 (14) | 1.2508 (3) | 0.0563 (7) | |
| H8 | 0.6888 | 0.2701 | 1.2372 | 0.068* | |
| C9 | 0.8860 (3) | 0.29559 (14) | 1.3670 (3) | 0.0611 (7) | |
| H9 | 0.8438 | 0.3043 | 1.4316 | 0.073* | |
| C10 | 1.0417 (3) | 0.30189 (15) | 1.3848 (3) | 0.0642 (8) | |
| H10 | 1.1063 | 0.3158 | 1.4633 | 0.077* | |
| C11 | 0.9286 (2) | 0.12106 (12) | 0.8007 (2) | 0.0389 (5) | |
| C12 | 0.8766 (3) | 0.02106 (13) | 0.6174 (2) | 0.0439 (6) | |
| C13 | 0.6825 (3) | −0.05894 (16) | 0.5448 (3) | 0.0641 (8) | |
| H13 | 0.5780 | −0.0695 | 0.5052 | 0.077* | |
| C14 | 0.7835 (3) | −0.11567 (15) | 0.5824 (3) | 0.0644 (8) | |
| H14 | 0.7499 | −0.1642 | 0.5721 | 0.077* | |
| C15 | 0.9358 (3) | −0.09824 (16) | 0.6359 (3) | 0.0661 (8) | |
| H15 | 1.0078 | −0.1360 | 0.6617 | 0.079* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0534 (4) | 0.0590 (4) | 0.0418 (4) | −0.0152 (3) | 0.0179 (3) | 0.0023 (3) |
| S2 | 0.0562 (4) | 0.0555 (4) | 0.0674 (5) | −0.0183 (3) | 0.0335 (4) | −0.0181 (4) |
| S3 | 0.0730 (5) | 0.0536 (4) | 0.0475 (4) | −0.0110 (3) | 0.0300 (4) | 0.0001 (3) |
| N1 | 0.0396 (11) | 0.0410 (11) | 0.0420 (12) | −0.0032 (8) | 0.0189 (9) | −0.0002 (9) |
| N2 | 0.0397 (11) | 0.0444 (12) | 0.0481 (13) | −0.0041 (9) | 0.0208 (9) | −0.0029 (10) |
| N3 | 0.0424 (11) | 0.0465 (12) | 0.0455 (13) | −0.0057 (9) | 0.0203 (10) | −0.0041 (10) |
| N4 | 0.0477 (13) | 0.0655 (14) | 0.0505 (14) | 0.0007 (11) | 0.0144 (11) | 0.0041 (12) |
| N5 | 0.0719 (15) | 0.0459 (13) | 0.0537 (15) | −0.0032 (11) | 0.0153 (12) | 0.0003 (11) |
| N6 | 0.0476 (13) | 0.0578 (14) | 0.0540 (14) | 0.0002 (10) | 0.0097 (11) | 0.0018 (11) |
| N7 | 0.0502 (13) | 0.0591 (15) | 0.0583 (15) | 0.0059 (11) | 0.0129 (11) | 0.0005 (11) |
| N8 | 0.0422 (12) | 0.0568 (13) | 0.0559 (14) | −0.0096 (9) | 0.0146 (11) | −0.0119 (11) |
| N9 | 0.0377 (11) | 0.0599 (13) | 0.0541 (14) | 0.0053 (9) | 0.0146 (10) | −0.0033 (11) |
| C1 | 0.0499 (17) | 0.102 (3) | 0.0449 (18) | −0.0030 (16) | 0.0151 (14) | 0.0052 (17) |
| C2 | 0.076 (2) | 0.092 (2) | 0.0511 (19) | −0.0314 (19) | 0.0129 (17) | −0.0112 (18) |
| C3 | 0.100 (3) | 0.0556 (18) | 0.067 (2) | −0.0150 (18) | 0.021 (2) | −0.0108 (16) |
| C4 | 0.0439 (14) | 0.0507 (16) | 0.0402 (15) | −0.0082 (11) | 0.0214 (12) | 0.0053 (12) |
| C5 | 0.0321 (12) | 0.0416 (13) | 0.0402 (15) | 0.0005 (10) | 0.0143 (10) | 0.0001 (11) |
| C6 | 0.0364 (13) | 0.0430 (14) | 0.0501 (16) | 0.0000 (10) | 0.0175 (12) | −0.0057 (12) |
| C7 | 0.0421 (13) | 0.0336 (13) | 0.0516 (16) | −0.0015 (10) | 0.0163 (12) | −0.0044 (11) |
| C8 | 0.0423 (14) | 0.0581 (16) | 0.072 (2) | 0.0060 (12) | 0.0235 (15) | −0.0048 (15) |
| C9 | 0.0662 (19) | 0.0632 (18) | 0.0646 (19) | −0.0074 (14) | 0.0360 (16) | −0.0174 (15) |
| C10 | 0.0634 (19) | 0.075 (2) | 0.0532 (18) | −0.0159 (14) | 0.0174 (15) | −0.0155 (15) |
| C11 | 0.0347 (12) | 0.0430 (13) | 0.0418 (14) | 0.0036 (10) | 0.0159 (11) | 0.0023 (11) |
| C12 | 0.0499 (15) | 0.0537 (15) | 0.0309 (14) | −0.0013 (12) | 0.0167 (12) | −0.0019 (11) |
| C13 | 0.0537 (17) | 0.0687 (19) | 0.063 (2) | −0.0089 (15) | 0.0077 (14) | 0.0003 (16) |
| C14 | 0.073 (2) | 0.0528 (17) | 0.065 (2) | −0.0057 (15) | 0.0163 (16) | −0.0076 (15) |
| C15 | 0.068 (2) | 0.0547 (18) | 0.074 (2) | 0.0121 (14) | 0.0194 (16) | 0.0013 (15) |
Geometric parameters (Å, º) top
| S1—C5 | 1.753 (2) | N8—C7 | 1.323 (3) |
| S1—C4 | 1.783 (2) | N8—C10 | 1.337 (3) |
| S2—C6 | 1.763 (2) | N9—C7 | 1.328 (3) |
| S2—C7 | 1.778 (2) | N9—C8 | 1.331 (3) |
| S3—C11 | 1.754 (2) | C1—C2 | 1.365 (4) |
| S3—C12 | 1.782 (2) | C1—H1 | 0.9300 |
| N1—C5 | 1.323 (3) | C2—C3 | 1.347 (4) |
| N1—C11 | 1.328 (3) | C2—H2 | 0.9300 |
| N2—C6 | 1.329 (3) | C3—H3 | 0.9300 |
| N2—C11 | 1.335 (3) | C8—C9 | 1.357 (4) |
| N3—C6 | 1.329 (3) | C8—H8 | 0.9300 |
| N3—C5 | 1.330 (3) | C9—C10 | 1.361 (4) |
| N4—C4 | 1.322 (3) | C9—H9 | 0.9300 |
| N4—C1 | 1.330 (3) | C10—H10 | 0.9300 |
| N5—C4 | 1.318 (3) | C13—C14 | 1.357 (4) |
| N5—C3 | 1.338 (4) | C13—H13 | 0.9300 |
| N6—C12 | 1.323 (3) | C14—C15 | 1.357 (4) |
| N6—C13 | 1.330 (3) | C14—H14 | 0.9300 |
| N7—C12 | 1.316 (3) | C15—H15 | 0.9300 |
| N7—C15 | 1.338 (3) | ||
| C5—S1—C4 | 101.04 (11) | N2—C6—S2 | 112.75 (17) |
| C6—S2—C7 | 103.08 (11) | N8—C7—N9 | 127.9 (2) |
| C11—S3—C12 | 98.56 (11) | N8—C7—S2 | 114.38 (17) |
| C5—N1—C11 | 113.39 (19) | N9—C7—S2 | 117.58 (18) |
| C6—N2—C11 | 112.86 (19) | N9—C8—C9 | 123.1 (2) |
| C6—N3—C5 | 113.0 (2) | N9—C8—H8 | 118.4 |
| C4—N4—C1 | 115.1 (2) | C9—C8—H8 | 118.4 |
| C4—N5—C3 | 114.6 (2) | C8—C9—C10 | 117.0 (3) |
| C12—N6—C13 | 114.5 (2) | C8—C9—H9 | 121.5 |
| C12—N7—C15 | 114.7 (2) | C10—C9—H9 | 121.5 |
| C7—N8—C10 | 114.8 (2) | N8—C10—C9 | 122.6 (3) |
| C7—N9—C8 | 114.6 (2) | N8—C10—H10 | 118.7 |
| N4—C1—C2 | 122.1 (3) | C9—C10—H10 | 118.7 |
| N4—C1—H1 | 118.9 | N1—C11—N2 | 126.7 (2) |
| C2—C1—H1 | 118.9 | N1—C11—S3 | 119.24 (17) |
| C3—C2—C1 | 117.5 (3) | N2—C11—S3 | 114.09 (16) |
| C3—C2—H2 | 121.3 | N7—C12—N6 | 128.1 (2) |
| C1—C2—H2 | 121.3 | N7—C12—S3 | 115.48 (19) |
| N5—C3—C2 | 122.8 (3) | N6—C12—S3 | 116.38 (18) |
| N5—C3—H3 | 118.6 | N6—C13—C14 | 123.2 (3) |
| C2—C3—H3 | 118.6 | N6—C13—H13 | 118.4 |
| N5—C4—N4 | 128.0 (2) | C14—C13—H13 | 118.4 |
| N5—C4—S1 | 115.82 (19) | C15—C14—C13 | 116.8 (3) |
| N4—C4—S1 | 115.95 (19) | C15—C14—H14 | 121.6 |
| N1—C5—N3 | 126.9 (2) | C13—C14—H14 | 121.6 |
| N1—C5—S1 | 119.72 (16) | N7—C15—C14 | 122.7 (3) |
| N3—C5—S1 | 113.35 (17) | N7—C15—H15 | 118.6 |
| N3—C6—N2 | 127.0 (2) | C14—C15—H15 | 118.6 |
| N3—C6—S2 | 120.16 (18) | ||
| C4—N4—C1—C2 | −0.7 (4) | C8—N9—C7—N8 | −2.4 (4) |
| N4—C1—C2—C3 | 1.2 (4) | C8—N9—C7—S2 | −177.37 (18) |
| C4—N5—C3—C2 | −0.6 (4) | C6—S2—C7—N8 | 139.84 (18) |
| C1—C2—C3—N5 | −0.6 (5) | C6—S2—C7—N9 | −44.5 (2) |
| C3—N5—C4—N4 | 1.3 (4) | C7—N9—C8—C9 | 3.2 (4) |
| C3—N5—C4—S1 | 175.8 (2) | N9—C8—C9—C10 | −1.8 (4) |
| C1—N4—C4—N5 | −0.7 (4) | C7—N8—C10—C9 | 1.6 (4) |
| C1—N4—C4—S1 | −175.16 (18) | C8—C9—C10—N8 | −0.8 (4) |
| C5—S1—C4—N5 | 115.77 (19) | C5—N1—C11—N2 | −3.0 (3) |
| C5—S1—C4—N4 | −69.05 (19) | C5—N1—C11—S3 | 177.48 (15) |
| C11—N1—C5—N3 | 0.3 (3) | C6—N2—C11—N1 | 2.9 (3) |
| C11—N1—C5—S1 | −178.09 (15) | C6—N2—C11—S3 | −177.59 (15) |
| C6—N3—C5—N1 | 2.0 (3) | C12—S3—C11—N1 | −11.97 (19) |
| C6—N3—C5—S1 | −179.47 (15) | C12—S3—C11—N2 | 168.48 (17) |
| C4—S1—C5—N1 | −21.7 (2) | C15—N7—C12—N6 | −3.8 (4) |
| C4—S1—C5—N3 | 159.71 (16) | C15—N7—C12—S3 | 176.4 (2) |
| C5—N3—C6—N2 | −2.2 (3) | C13—N6—C12—N7 | 2.5 (4) |
| C5—N3—C6—S2 | −179.02 (15) | C13—N6—C12—S3 | −177.74 (19) |
| C11—N2—C6—N3 | 0.0 (3) | C11—S3—C12—N7 | −87.3 (2) |
| C11—N2—C6—S2 | 177.00 (15) | C11—S3—C12—N6 | 92.90 (19) |
| C7—S2—C6—N3 | −24.0 (2) | C12—N6—C13—C14 | 0.8 (4) |
| C7—S2—C6—N2 | 158.74 (16) | N6—C13—C14—C15 | −2.3 (4) |
| C10—N8—C7—N9 | 0.1 (4) | C12—N7—C15—C14 | 2.0 (4) |
| C10—N8—C7—S2 | 175.19 (18) | C13—C14—C15—N7 | 0.8 (4) |
