Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050167/fj2044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050167/fj2044Isup2.hkl |
CCDC reference: 667380
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.003 Å
- R factor = 0.040
- wR factor = 0.123
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For related literature, see: Allen et al. (1987); Bu et al. (2002); Raper (1997).
A solution of 1,3-dibromopropane (1.01 g, 5 mmol) in ethanol(10 ml) was slowly dripped into a refluxing solution of 2-thiol-4,6-dimethylpyrimidine (1.40 g, 10 mmol) and powdered NaOH (0.4 g, 10 mmol) in ethanol. The reaction mixture was refluxed for 5 h with stirring and cool to room temperature. The white powder of title compound was filtered and washed thoroughly with water and then air dried (yield 65%). Single crystals suitable for X-ray analysis were obtained by slow evaporation from a dichloromethane/2-propanol (3:1) solution.
The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 - 0.97 Å and Uiso = 1.2 or 1.5 Ueq(parent atom).
Previous studies have shown that flexible thioethers are well -established ligands in coordination and metallosupramolecular chemistry (Bu et al., 2002; Raper, 1997). Therefore we pay our attention to the pyrimidine dithioethers, which has well known reactivity in the pyrimidine ring (positions 2, 4 and 6). As part of our ongoing investigtion on pyrimidine derivatives, the title compound, has been prepared and its crystal structure is presented here.
The molecular structure shown in Fig. 1. The bond lengths and angles are generally within normal ranges (Allen et al., 1987). A view of the packing diagram is given in Fig. 2. The dihedral angle between two pyrimidine rings is 72.9 (1) °. The crystal packing (Fig. 2) is mainly stabilized by van der Waals forces.
For related literature, see: Allen et al. (1987); Bu et al. (2002); Raper (1997).
Data collection: APEX2 SMART (Bruker, ????); cell refinement: APEX2 SMART (Bruker, ????); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C15H20N4S2 | F(000) = 680 |
Mr = 320.47 | Dx = 1.285 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2114 reflections |
a = 13.4654 (14) Å | θ = 2.8–27.6° |
b = 8.8808 (9) Å | µ = 0.32 mm−1 |
c = 14.2371 (16) Å | T = 298 K |
β = 103.340 (2)° | Block, pale-yellow |
V = 1656.6 (3) Å3 | 0.52 × 0.50 × 0.45 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 1461 independent reflections |
Radiation source: fine-focus sealed tube | 1174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→9 |
Tmin = 0.851, Tmax = 0.869 | k = −10→10 |
4000 measured reflections | l = −16→16 |
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) = 0.123 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0756P)2 + 0.7397P] where P = (Fo2 + 2Fc2)/3 |
1461 reflections | (Δ/σ)max < 0.001 |
98 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C15H20N4S2 | V = 1656.6 (3) Å3 |
Mr = 320.47 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.4654 (14) Å | µ = 0.32 mm−1 |
b = 8.8808 (9) Å | T = 298 K |
c = 14.2371 (16) Å | 0.52 × 0.50 × 0.45 mm |
β = 103.340 (2)° |
Bruker APEXII CCD area-detector diffractometer | 1461 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1174 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 0.869 | Rint = 0.029 |
4000 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.16 e Å−3 |
1461 reflections | Δρmin = −0.29 e Å−3 |
98 parameters |
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 | Occ. (<1) | |
N1 | 0.41047 (13) | 0.20385 (19) | 0.45126 (11) | 0.0418 (4) | |
N2 | 0.24595 (13) | 0.0889 (2) | 0.40016 (12) | 0.0471 (5) | |
S1 | 0.29908 (4) | 0.25812 (7) | 0.27214 (4) | 0.0571 (3) | |
C1 | 0.32337 (15) | 0.1745 (2) | 0.38755 (13) | 0.0409 (5) | |
C2 | 0.25732 (15) | 0.0265 (2) | 0.48815 (15) | 0.0441 (5) | |
C3 | 0.34420 (16) | 0.0511 (2) | 0.55924 (14) | 0.0455 (5) | |
H3 | 0.3514 | 0.0080 | 0.6200 | 0.055* | |
C4 | 0.42034 (15) | 0.1404 (2) | 0.53904 (14) | 0.0427 (5) | |
C5 | 0.17108 (18) | −0.0686 (3) | 0.50475 (18) | 0.0618 (6) | |
H5A | 0.1094 | −0.0104 | 0.4918 | 0.093* | |
H5B | 0.1861 | −0.1023 | 0.5706 | 0.093* | |
H5C | 0.1625 | −0.1543 | 0.4625 | 0.093* | |
C6 | 0.51623 (18) | 0.1744 (3) | 0.61268 (15) | 0.0604 (6) | |
H6A | 0.5737 | 0.1645 | 0.5839 | 0.091* | |
H6B | 0.5232 | 0.1050 | 0.6655 | 0.091* | |
H6C | 0.5133 | 0.2753 | 0.6359 | 0.091* | |
C7 | 0.41447 (15) | 0.3608 (2) | 0.27135 (14) | 0.0463 (5) | |
H7A | 0.3985 | 0.4400 | 0.2233 | 0.056* | |
H7B | 0.4385 | 0.4084 | 0.3338 | 0.056* | |
C8 | 0.5000 | 0.2651 (3) | 0.2500 | 0.0448 (7) | |
H8A | 0.4729 | 0.2008 | 0.1950 | 0.054* | 0.50 |
H8B | 0.5271 | 0.2008 | 0.3050 | 0.054* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0414 (9) | 0.0490 (9) | 0.0372 (8) | −0.0040 (8) | 0.0140 (7) | 0.0000 (7) |
N2 | 0.0423 (10) | 0.0542 (10) | 0.0480 (10) | −0.0044 (8) | 0.0170 (8) | −0.0052 (8) |
S1 | 0.0414 (4) | 0.0905 (5) | 0.0399 (4) | −0.0004 (3) | 0.0102 (3) | 0.0100 (3) |
C1 | 0.0399 (11) | 0.0473 (11) | 0.0389 (10) | 0.0022 (9) | 0.0161 (9) | −0.0032 (8) |
C2 | 0.0415 (11) | 0.0435 (11) | 0.0522 (11) | −0.0022 (9) | 0.0207 (10) | −0.0030 (9) |
C3 | 0.0520 (12) | 0.0457 (11) | 0.0430 (11) | −0.0003 (9) | 0.0194 (10) | 0.0047 (9) |
C4 | 0.0457 (11) | 0.0442 (11) | 0.0407 (10) | −0.0012 (9) | 0.0150 (9) | −0.0014 (8) |
C5 | 0.0560 (14) | 0.0636 (14) | 0.0709 (15) | −0.0157 (12) | 0.0251 (12) | −0.0003 (12) |
C6 | 0.0615 (15) | 0.0731 (16) | 0.0444 (12) | −0.0164 (13) | 0.0074 (11) | 0.0045 (11) |
C7 | 0.0484 (12) | 0.0551 (13) | 0.0386 (10) | 0.0044 (10) | 0.0167 (9) | 0.0070 (9) |
C8 | 0.0460 (17) | 0.0470 (16) | 0.0443 (16) | 0.000 | 0.0162 (13) | 0.000 |
N1—C1 | 1.332 (2) | C5—H5B | 0.9600 |
N1—C4 | 1.349 (2) | C5—H5C | 0.9600 |
N2—C1 | 1.335 (3) | C6—H6A | 0.9600 |
N2—C2 | 1.346 (3) | C6—H6B | 0.9600 |
S1—C1 | 1.7634 (19) | C6—H6C | 0.9600 |
S1—C7 | 1.804 (2) | C7—C8 | 1.518 (2) |
C2—C3 | 1.376 (3) | C7—H7A | 0.9700 |
C2—C5 | 1.499 (3) | C7—H7B | 0.9700 |
C3—C4 | 1.378 (3) | C8—C7i | 1.518 (2) |
C3—H3 | 0.9300 | C8—H8A | 0.9700 |
C4—C6 | 1.494 (3) | C8—H8B | 0.9700 |
C5—H5A | 0.9600 | ||
C1—N1—C4 | 115.61 (16) | H5B—C5—H5C | 109.5 |
C1—N2—C2 | 115.78 (17) | C4—C6—H6A | 109.5 |
C1—S1—C7 | 104.11 (10) | C4—C6—H6B | 109.5 |
N1—C1—N2 | 127.70 (18) | H6A—C6—H6B | 109.5 |
N1—C1—S1 | 119.80 (15) | C4—C6—H6C | 109.5 |
N2—C1—S1 | 112.47 (14) | H6A—C6—H6C | 109.5 |
N2—C2—C3 | 120.95 (18) | H6B—C6—H6C | 109.5 |
N2—C2—C5 | 116.95 (18) | C8—C7—S1 | 114.38 (15) |
C3—C2—C5 | 122.10 (19) | C8—C7—H7A | 108.7 |
C2—C3—C4 | 118.99 (18) | S1—C7—H7A | 108.7 |
C2—C3—H3 | 120.5 | C8—C7—H7B | 108.7 |
C4—C3—H3 | 120.5 | S1—C7—H7B | 108.7 |
N1—C4—C3 | 120.97 (18) | H7A—C7—H7B | 107.6 |
N1—C4—C6 | 116.77 (17) | C7—C8—C7i | 111.9 (2) |
C3—C4—C6 | 122.25 (18) | C7—C8—H8A | 109.2 |
C2—C5—H5A | 109.5 | C7i—C8—H8A | 109.2 |
C2—C5—H5B | 109.5 | C7—C8—H8B | 109.2 |
H5A—C5—H5B | 109.5 | C7i—C8—H8B | 109.2 |
C2—C5—H5C | 109.5 | H8A—C8—H8B | 107.9 |
H5A—C5—H5C | 109.5 | ||
C4—N1—C1—N2 | −0.8 (3) | N2—C2—C3—C4 | −0.3 (3) |
C4—N1—C1—S1 | 177.08 (14) | C5—C2—C3—C4 | −179.7 (2) |
C2—N2—C1—N1 | 0.8 (3) | C1—N1—C4—C3 | 0.3 (3) |
C2—N2—C1—S1 | −177.29 (14) | C1—N1—C4—C6 | −178.60 (19) |
C7—S1—C1—N1 | 3.68 (19) | C2—C3—C4—N1 | 0.2 (3) |
C7—S1—C1—N2 | −178.10 (15) | C2—C3—C4—C6 | 179.1 (2) |
C1—N2—C2—C3 | −0.1 (3) | C1—S1—C7—C8 | 81.15 (13) |
C1—N2—C2—C5 | 179.30 (18) | S1—C7—C8—C7i | 167.50 (15) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H20N4S2 |
Mr | 320.47 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.4654 (14), 8.8808 (9), 14.2371 (16) |
β (°) | 103.340 (2) |
V (Å3) | 1656.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.52 × 0.50 × 0.45 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.851, 0.869 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4000, 1461, 1174 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.123, 1.01 |
No. of reflections | 1461 |
No. of parameters | 98 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.29 |
Computer programs: APEX2 SMART (Bruker, ????), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
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Previous studies have shown that flexible thioethers are well -established ligands in coordination and metallosupramolecular chemistry (Bu et al., 2002; Raper, 1997). Therefore we pay our attention to the pyrimidine dithioethers, which has well known reactivity in the pyrimidine ring (positions 2, 4 and 6). As part of our ongoing investigtion on pyrimidine derivatives, the title compound, has been prepared and its crystal structure is presented here.
The molecular structure shown in Fig. 1. The bond lengths and angles are generally within normal ranges (Allen et al., 1987). A view of the packing diagram is given in Fig. 2. The dihedral angle between two pyrimidine rings is 72.9 (1) °. The crystal packing (Fig. 2) is mainly stabilized by van der Waals forces.