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The crystal structure of the title compound, C15H20N4S2, is mainly stabilized by van der Waals forces. The mol­ecule resides on a twofold axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050167/fj2044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050167/fj2044Isup2.hkl
Contains datablock I

CCDC reference: 667380

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For related literature, see: Allen et al. (1987); Bu et al. (2002); Raper (1997).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids. Symmetry operation: 1 - x, y, 1/2 - z.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the b axis. Hydrogen atoms are omitted for clarity.
4,4',6,6'-Tetramethyl-2,2'-(propyldithio)dipyrimidine top
Crystal data top
C15H20N4S2F(000) = 680
Mr = 320.47Dx = 1.285 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2114 reflections
a = 13.4654 (14) Åθ = 2.8–27.6°
b = 8.8808 (9) ŵ = 0.32 mm1
c = 14.2371 (16) ÅT = 298 K
β = 103.340 (2)°Block, pale-yellow
V = 1656.6 (3) Å30.52 × 0.50 × 0.45 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1461 independent reflections
Radiation source: fine-focus sealed tube1174 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 169
Tmin = 0.851, Tmax = 0.869k = 1010
4000 measured reflectionsl = 1616
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-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 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C15H20N4S2V = 1656.6 (3) Å3
Mr = 320.47Z = 4
Monoclinic, C2/cMo Kα radiation
a = 13.4654 (14) ŵ = 0.32 mm1
b = 8.8808 (9) ÅT = 298 K
c = 14.2371 (16) Å0.52 × 0.50 × 0.45 mm
β = 103.340 (2)°
Data collection top
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 = 0.869Rint = 0.029
4000 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.01Δρmax = 0.16 e Å3
1461 reflectionsΔρmin = 0.29 e Å3
98 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
xyzUiso*/UeqOcc. (<1)
N10.41047 (13)0.20385 (19)0.45126 (11)0.0418 (4)
N20.24595 (13)0.0889 (2)0.40016 (12)0.0471 (5)
S10.29908 (4)0.25812 (7)0.27214 (4)0.0571 (3)
C10.32337 (15)0.1745 (2)0.38755 (13)0.0409 (5)
C20.25732 (15)0.0265 (2)0.48815 (15)0.0441 (5)
C30.34420 (16)0.0511 (2)0.55924 (14)0.0455 (5)
H30.35140.00800.62000.055*
C40.42034 (15)0.1404 (2)0.53904 (14)0.0427 (5)
C50.17108 (18)0.0686 (3)0.50475 (18)0.0618 (6)
H5A0.10940.01040.49180.093*
H5B0.18610.10230.57060.093*
H5C0.16250.15430.46250.093*
C60.51623 (18)0.1744 (3)0.61268 (15)0.0604 (6)
H6A0.57370.16450.58390.091*
H6B0.52320.10500.66550.091*
H6C0.51330.27530.63590.091*
C70.41447 (15)0.3608 (2)0.27135 (14)0.0463 (5)
H7A0.39850.44000.22330.056*
H7B0.43850.40840.33380.056*
C80.50000.2651 (3)0.25000.0448 (7)
H8A0.47290.20080.19500.054*0.50
H8B0.52710.20080.30500.054*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0414 (9)0.0490 (9)0.0372 (8)0.0040 (8)0.0140 (7)0.0000 (7)
N20.0423 (10)0.0542 (10)0.0480 (10)0.0044 (8)0.0170 (8)0.0052 (8)
S10.0414 (4)0.0905 (5)0.0399 (4)0.0004 (3)0.0102 (3)0.0100 (3)
C10.0399 (11)0.0473 (11)0.0389 (10)0.0022 (9)0.0161 (9)0.0032 (8)
C20.0415 (11)0.0435 (11)0.0522 (11)0.0022 (9)0.0207 (10)0.0030 (9)
C30.0520 (12)0.0457 (11)0.0430 (11)0.0003 (9)0.0194 (10)0.0047 (9)
C40.0457 (11)0.0442 (11)0.0407 (10)0.0012 (9)0.0150 (9)0.0014 (8)
C50.0560 (14)0.0636 (14)0.0709 (15)0.0157 (12)0.0251 (12)0.0003 (12)
C60.0615 (15)0.0731 (16)0.0444 (12)0.0164 (13)0.0074 (11)0.0045 (11)
C70.0484 (12)0.0551 (13)0.0386 (10)0.0044 (10)0.0167 (9)0.0070 (9)
C80.0460 (17)0.0470 (16)0.0443 (16)0.0000.0162 (13)0.000
Geometric parameters (Å, º) top
N1—C11.332 (2)C5—H5B0.9600
N1—C41.349 (2)C5—H5C0.9600
N2—C11.335 (3)C6—H6A0.9600
N2—C21.346 (3)C6—H6B0.9600
S1—C11.7634 (19)C6—H6C0.9600
S1—C71.804 (2)C7—C81.518 (2)
C2—C31.376 (3)C7—H7A0.9700
C2—C51.499 (3)C7—H7B0.9700
C3—C41.378 (3)C8—C7i1.518 (2)
C3—H30.9300C8—H8A0.9700
C4—C61.494 (3)C8—H8B0.9700
C5—H5A0.9600
C1—N1—C4115.61 (16)H5B—C5—H5C109.5
C1—N2—C2115.78 (17)C4—C6—H6A109.5
C1—S1—C7104.11 (10)C4—C6—H6B109.5
N1—C1—N2127.70 (18)H6A—C6—H6B109.5
N1—C1—S1119.80 (15)C4—C6—H6C109.5
N2—C1—S1112.47 (14)H6A—C6—H6C109.5
N2—C2—C3120.95 (18)H6B—C6—H6C109.5
N2—C2—C5116.95 (18)C8—C7—S1114.38 (15)
C3—C2—C5122.10 (19)C8—C7—H7A108.7
C2—C3—C4118.99 (18)S1—C7—H7A108.7
C2—C3—H3120.5C8—C7—H7B108.7
C4—C3—H3120.5S1—C7—H7B108.7
N1—C4—C3120.97 (18)H7A—C7—H7B107.6
N1—C4—C6116.77 (17)C7—C8—C7i111.9 (2)
C3—C4—C6122.25 (18)C7—C8—H8A109.2
C2—C5—H5A109.5C7i—C8—H8A109.2
C2—C5—H5B109.5C7—C8—H8B109.2
H5A—C5—H5B109.5C7i—C8—H8B109.2
C2—C5—H5C109.5H8A—C8—H8B107.9
H5A—C5—H5C109.5
C4—N1—C1—N20.8 (3)N2—C2—C3—C40.3 (3)
C4—N1—C1—S1177.08 (14)C5—C2—C3—C4179.7 (2)
C2—N2—C1—N10.8 (3)C1—N1—C4—C30.3 (3)
C2—N2—C1—S1177.29 (14)C1—N1—C4—C6178.60 (19)
C7—S1—C1—N13.68 (19)C2—C3—C4—N10.2 (3)
C7—S1—C1—N2178.10 (15)C2—C3—C4—C6179.1 (2)
C1—N2—C2—C30.1 (3)C1—S1—C7—C881.15 (13)
C1—N2—C2—C5179.30 (18)S1—C7—C8—C7i167.50 (15)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H20N4S2
Mr320.47
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)13.4654 (14), 8.8808 (9), 14.2371 (16)
β (°) 103.340 (2)
V3)1656.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.52 × 0.50 × 0.45
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.851, 0.869
No. of measured, independent and
observed [I > 2σ(I)] reflections
4000, 1461, 1174
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.123, 1.01
No. of reflections1461
No. of parameters98
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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