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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o201.
Published online 2007 December 6. doi:  10.1107/S1600536807064082
PMCID: PMC2915263

2-(4,6-Dimethyl­pyrimidin-2-ylsulfan­yl)-N-(4-methyl­pyridin-2-yl)acetamide

Abstract

The non-H atoms of the title mol­ecule, C14H16N4OS, are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two aromatic rings is 2.4 (2)°. An intra­molecular C—H(...)O hydrogen bond is observed. The mol­ecules exist as N—H(...)N hydrogen-bonded centrosymmetric dimers.

Related literature

For related literature, see: Koike et al. (1999 [triangle]).

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Object name is e-64-0o201-scheme1.jpg

Experimental

Crystal data

  • C14H16N4OS
  • M r = 288.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o201-efi1.jpg
  • a = 5.1924 (19) Å
  • b = 15.423 (5) Å
  • c = 18.121 (6) Å
  • β = 91.678 (6)°
  • V = 1450.5 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 293 (2) K
  • 0.40 × 0.24 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.916, T max = 0.957
  • 8084 measured reflections
  • 2970 independent reflections
  • 1582 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.144
  • S = 0.98
  • 2970 reflections
  • 184 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064082/ci2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064082/ci2528Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Acetamide is an important class of medical intermediate. Many biologically active compounds are prepared by using acetamide (Koike et al., 1999). The title compound was prepared from the reaction of 2-thio-4,6-dimethylpyrimidine with 2-chloro-N-(5-methylpyridin-2-yl)acetamide. We report here the crystal structure of the title compound.

The non-hydrogen atoms of the title molecule are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two heterocyclic rings is 2.4 (2)°. The O1—C8—N3 [124.3 (2)°] and N3—C8—C7 [113.9 (2)°] angles deviate significantly from the ideal value of 120°. Due to the p-π conjugation bwtween the S atom and the pyrimidine ring, the S1—C1 bond distance [1.756 (3) Å] is slightly shorter than the S1—C7 bond distance [1.794 (3) Å]. An intramolecular C—H···O hydrogen bond is observed. The molecules exist as N—H···O hydrogen-bonded centrosymmetric dimer (Table 1).

Experimental

The title compound was synthesized by the reaction of 2-thio-4,6-dimethylpyrimidine (2 mmol) with 2-chloro-N-(5-methylpyridin-2-yl)acetamide (2 mmol) in refluxing ethanol (40 ml). Single crystals suitable for X-ray analysis were grown by slow evaporation of a chloroform-acetone (1:5 v/v) solution.

Refinement

All H atoms were positioned geometrically and refined as riding (N—H = 0.86 Å and C—H = 0.93–0.97 Å). For the CH and CH2 groups, Uiso(H) values were set equal to 1.2Ueq(C) and for the methyl groups they were set equal to 1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

Crystal data

C14H16N4OSF000 = 608
Mr = 288.37Dx = 1.320 Mg m3
Monoclinic, P21/cMelting point: 418 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 5.1924 (19) ÅCell parameters from 1663 reflections
b = 15.423 (5) Åθ = 2.6–22.2º
c = 18.121 (6) ŵ = 0.22 mm1
β = 91.678 (6)ºT = 293 (2) K
V = 1450.5 (9) Å3Plate, colourless
Z = 40.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer2970 independent reflections
Radiation source: fine-focus sealed tube1582 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
T = 293(2) Kθmax = 26.4º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −6→4
Tmin = 0.916, Tmax = 0.957k = −17→19
8084 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.004
2970 reflectionsΔρmax = 0.27 e Å3
184 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
S10.19772 (16)0.06150 (5)0.30190 (4)0.0565 (3)
O10.4584 (4)0.17627 (12)0.39721 (11)0.0629 (6)
C80.5502 (6)0.10500 (16)0.40685 (14)0.0424 (7)
N30.7497 (4)0.08705 (13)0.45581 (11)0.0437 (6)
H3A0.79290.03340.46030.052*
N1−0.0905 (5)−0.02849 (15)0.21206 (12)0.0526 (6)
N20.2279 (4)−0.11038 (14)0.28121 (12)0.0487 (6)
N41.0824 (5)0.11059 (13)0.54011 (12)0.0471 (6)
C70.4517 (5)0.02656 (16)0.36422 (15)0.0466 (7)
H7A0.3873−0.01660.39800.056*
H7B0.59010.00080.33690.056*
C10.1057 (6)−0.03772 (17)0.26160 (15)0.0464 (7)
C90.8914 (5)0.14679 (15)0.49939 (13)0.0390 (7)
C100.8368 (6)0.23511 (16)0.50028 (15)0.0493 (7)
H100.70060.25720.47160.059*
C3−0.0551 (6)−0.18068 (19)0.19480 (16)0.0566 (8)
H3−0.1119−0.23100.17120.068*
C121.1828 (6)0.25295 (18)0.58610 (17)0.0580 (8)
H121.28710.28740.61670.070*
C40.1449 (6)−0.18362 (18)0.24637 (16)0.0502 (7)
C2−0.1703 (6)−0.1016 (2)0.17864 (15)0.0535 (8)
C50.2828 (6)−0.26511 (18)0.26755 (19)0.0677 (9)
H5A0.4476−0.26630.24490.102*
H5B0.1828−0.31420.25110.102*
H5C0.3067−0.26730.32020.102*
C131.2229 (6)0.16531 (18)0.58239 (17)0.0611 (9)
H131.35700.14210.61120.073*
C6−0.3885 (7)−0.0931 (2)0.12243 (18)0.0747 (10)
H6A−0.5028−0.04780.13720.112*
H6B−0.4812−0.14690.11910.112*
H6C−0.3205−0.07920.07520.112*
C110.9856 (6)0.28937 (17)0.54384 (15)0.0507 (8)
C140.9279 (7)0.38546 (17)0.54669 (19)0.0782 (11)
H14A0.82680.39770.58900.117*
H14B0.83370.40230.50260.117*
H14C1.08660.41730.55030.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0590 (5)0.0408 (4)0.0681 (5)0.0027 (4)−0.0256 (4)−0.0038 (4)
O10.0813 (16)0.0368 (11)0.0683 (13)0.0118 (10)−0.0348 (12)−0.0053 (9)
C80.0517 (18)0.0305 (15)0.0445 (16)0.0044 (13)−0.0055 (14)−0.0006 (12)
N30.0501 (15)0.0285 (11)0.0516 (14)0.0060 (10)−0.0152 (12)−0.0033 (10)
N10.0499 (16)0.0553 (15)0.0518 (15)−0.0103 (12)−0.0128 (12)0.0042 (12)
N20.0498 (16)0.0438 (14)0.0521 (14)−0.0044 (11)−0.0070 (12)−0.0049 (11)
N40.0469 (15)0.0359 (13)0.0574 (14)0.0054 (11)−0.0174 (12)−0.0049 (11)
C70.0497 (18)0.0393 (16)0.0502 (17)0.0008 (13)−0.0118 (14)−0.0047 (13)
C10.0471 (18)0.0445 (17)0.0476 (17)−0.0084 (13)−0.0029 (14)0.0002 (13)
C90.0419 (17)0.0334 (14)0.0414 (15)0.0019 (12)−0.0031 (13)−0.0014 (12)
C100.0582 (19)0.0341 (15)0.0546 (18)0.0111 (13)−0.0154 (15)−0.0024 (13)
C30.060 (2)0.0498 (19)0.0594 (19)−0.0169 (16)−0.0021 (16)−0.0065 (15)
C120.062 (2)0.0379 (17)0.072 (2)−0.0005 (14)−0.0252 (17)−0.0088 (14)
C40.0496 (19)0.0465 (17)0.0544 (18)−0.0109 (14)−0.0015 (15)−0.0074 (14)
C20.0496 (19)0.063 (2)0.0477 (18)−0.0202 (16)−0.0086 (15)0.0012 (14)
C50.075 (2)0.0444 (18)0.083 (2)−0.0057 (16)−0.0081 (19)−0.0105 (16)
C130.057 (2)0.0455 (18)0.079 (2)0.0046 (15)−0.0272 (17)−0.0055 (15)
C60.071 (2)0.081 (2)0.070 (2)−0.0275 (19)−0.0276 (19)0.0112 (18)
C110.062 (2)0.0339 (15)0.0554 (18)0.0007 (14)−0.0062 (16)−0.0046 (13)
C140.104 (3)0.0346 (17)0.094 (3)0.0064 (17)−0.028 (2)−0.0098 (16)

Geometric parameters (Å, °)

S1—C11.756 (3)C3—C21.386 (4)
S1—C71.794 (3)C3—H30.93
O1—C81.209 (3)C12—C131.369 (4)
C8—N31.372 (3)C12—C111.380 (4)
C8—C71.516 (3)C12—H120.93
N3—C91.407 (3)C4—C51.491 (4)
N3—H3A0.86C2—C61.507 (4)
N1—C21.340 (3)C5—H5A0.96
N1—C11.346 (3)C5—H5B0.96
N2—C11.331 (3)C5—H5C0.96
N2—C41.358 (3)C13—H130.93
N4—C91.341 (3)C6—H6A0.96
N4—C131.341 (3)C6—H6B0.96
C7—H7A0.97C6—H6C0.96
C7—H7B0.97C11—C141.513 (4)
C9—C101.391 (3)C14—H14A0.96
C10—C111.373 (4)C14—H14B0.96
C10—H100.93C14—H14C0.96
C3—C41.377 (4)
C1—S1—C7100.72 (13)N2—C4—C3120.7 (3)
O1—C8—N3124.3 (2)N2—C4—C5116.0 (3)
O1—C8—C7121.8 (3)C3—C4—C5123.3 (3)
N3—C8—C7113.9 (2)N1—C2—C3121.3 (3)
C8—N3—C9127.1 (2)N1—C2—C6116.6 (3)
C8—N3—H3A116.5C3—C2—C6122.1 (3)
C9—N3—H3A116.5C4—C5—H5A109.5
C2—N1—C1115.5 (2)C4—C5—H5B109.5
C1—N2—C4115.7 (2)H5A—C5—H5B109.5
C9—N4—C13115.7 (2)C4—C5—H5C109.5
C8—C7—S1108.17 (18)H5A—C5—H5C109.5
C8—C7—H7A110.1H5B—C5—H5C109.5
S1—C7—H7A110.1N4—C13—C12124.6 (3)
C8—C7—H7B110.1N4—C13—H13117.7
S1—C7—H7B110.1C12—C13—H13117.7
H7A—C7—H7B108.4C2—C6—H6A109.5
N2—C1—N1127.8 (2)C2—C6—H6B109.5
N2—C1—S1120.1 (2)H6A—C6—H6B109.5
N1—C1—S1112.1 (2)C2—C6—H6C109.5
N4—C9—C10123.3 (2)H6A—C6—H6C109.5
N4—C9—N3113.7 (2)H6B—C6—H6C109.5
C10—C9—N3123.0 (2)C10—C11—C12117.8 (2)
C11—C10—C9119.5 (2)C10—C11—C14120.5 (3)
C11—C10—H10120.3C12—C11—C14121.6 (3)
C9—C10—H10120.3C11—C14—H14A109.5
C4—C3—C2119.0 (3)C11—C14—H14B109.5
C4—C3—H3120.5H14A—C14—H14B109.5
C2—C3—H3120.5C11—C14—H14C109.5
C13—C12—C11119.1 (3)H14A—C14—H14C109.5
C13—C12—H12120.5H14B—C14—H14C109.5
C11—C12—H12120.5
O1—C8—N3—C9−4.1 (5)N3—C9—C10—C11−179.4 (2)
C7—C8—N3—C9175.6 (2)C1—N2—C4—C3−0.5 (4)
O1—C8—C7—S10.8 (4)C1—N2—C4—C5179.4 (3)
N3—C8—C7—S1−178.85 (19)C2—C3—C4—N20.2 (4)
C1—S1—C7—C8−177.95 (19)C2—C3—C4—C5−179.7 (3)
C4—N2—C1—N10.6 (4)C1—N1—C2—C3−0.1 (4)
C4—N2—C1—S1−179.3 (2)C1—N1—C2—C6−179.5 (3)
C2—N1—C1—N2−0.2 (4)C4—C3—C2—N10.1 (5)
C2—N1—C1—S1179.6 (2)C4—C3—C2—C6179.5 (3)
C7—S1—C1—N2−1.0 (3)C9—N4—C13—C120.1 (4)
C7—S1—C1—N1179.1 (2)C11—C12—C13—N4−0.1 (5)
C13—N4—C9—C10−0.5 (4)C9—C10—C11—C12−0.9 (4)
C13—N4—C9—N3179.8 (2)C9—C10—C11—C14−179.1 (3)
C8—N3—C9—N4−177.6 (2)C13—C12—C11—C100.5 (5)
C8—N3—C9—C102.8 (4)C13—C12—C11—C14178.7 (3)
N4—C9—C10—C110.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···N4i0.862.313.171 (3)174
C10—H10···O10.932.202.821 (4)123

Symmetry codes: (i) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2528).

References

  • Bruker (1997). SMART (Version 5.611), SAINT (Version 6.0), SADABS (Version 2.03) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Koike, K., Jia, Z., Nikaido, T., Liu, Y., Zhao, Y. & Guo, D. (1999). Org. Lett.1, 197–198.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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