2-(4,6-Dimethyl­pyrimidin-2-ylsulfan­yl)-N-phenyl­acetamide

Gao, L.-X.; Fang, G.-J.; Feng, J.-G.; Liang, D.; Wang, W.

doi:10.1107/S1600536808007940

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o760

doi:10.1107/S1600536808007940

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2-(4,6-Dimethylpyrimidin-2-ylsulfanyl)-N-phenylacetamide

Li-Xin Gao,^a Guang-Jun Fang,^a Jin-Guo Feng,^a Dong Liang ^a and Wei Wang ^a ^*

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114002, People's Republic of China
^*Correspondence e-mail: tju_chemistry@yahoo.com.cn

(Received 11 March 2008; accepted 24 March 2008; online 29 March 2008)

In the title compound, C₁₄H₁₅N₃OS, the phenyl ring is almost perpendicular to the dimethylpyrimidine group, with a dihedral angle of 88.1 (3)°. The Csp²—S bond of 1.759 (3) Å is significantly shorter than the Csp³—S bond of 1.795 (3) Å due to the p–π conjugation.

Related literature

For related literature, see: Koike et al. (1999 ); Liang et al. (2008 ); Wang et al. (2004 , 2005 ).

Experimental

Crystal data

C₁₄H₁₅N₃OS
M_r = 273.35
Orthorhombic, P b c a
a = 9.1691 (17) Å
b = 15.485 (3) Å
c = 20.798 (4) Å
V = 2952.9 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 571 (2) K
0.28 × 0.24 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.942, T_max = 0.971
14235 measured reflections
2606 independent reflections
1494 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.01
2606 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007940/at2550sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007940/at2550Isup2.hkl

checkCIF report

Comment top

Acetamide is an important class of medical intermidate. Many biologically active compounds are synthesized by using acetamide (Koike et al., 1999). We have reported the synthesis and crystal structure of a acetamide compound, 1,1'-diphenyl-5,5'-[o-phenylenebis(methylenethio)]di-1H-tetrazole (Liang et al., 2008). Now, a new acetamide derivative, namely 2-(4,6-dimethylpyrimidin-2- ylsulfanyl)-N-phenylacetamide (I) are prepared from the reaction of 2-thio-4,6- dimethylpyrimidine with 2-chloro-N-phenylacetamide. We present its crystal structure here.

The title compound contains a benzene ring and a dimethylpyrimidine ring. The two methyl groups attached to the pyrimidine ring don't deviate from the pyrimidine ring, with an r.m.s. of 0.0082 (4) Å. The dihedral angle between the benzene ring and dimethylpyrimidine ring is 91.9 (3)°, which indicates that the two aromatic rings are almost perpendicular. The O1—C8—N3—C9 and C8—N3—C9—C14 torsion angles are 2.5 (4) and 164.3 (3)°, indicating that the acetamide is planar with the benzene ring.

Due to the p-π conjugation, the Csp²—S bond [S1—C1 = 1.759 (3) Å] is significantly shorter than the Csp³—S bond [C7—S1 = 1.795 (3) Å]. These values compare with the values reported in the literatures (Wang et al., 2004, 2005).

Related literature top

For related literature, see: Koike et al. (1999); Liang et al. (2008); Wang et al. (2004, 2005).

Experimental top

The title compound was synthesized by the reaction of 2-thio-4,6-dimethyl- pyrimidine(2 mmol) with 2-chloro-N-phenylacetamide (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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

2-(4,6-dimethylpyrimidin-2-ylsulfanyl)-N-phenylacetamide top

Crystal data top

C₁₄H₁₅N₃OS	F(000) = 1152
M_r = 273.35	D_x = 1.230 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2395 reflections
a = 9.1691 (17) Å	θ = 2.8–22.1°
b = 15.485 (3) Å	µ = 0.22 mm⁻¹
c = 20.798 (4) Å	T = 571 K
V = 2952.9 (9) Å³	Block, colourless
Z = 8	0.28 × 0.24 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2606 independent reflections
Radiation source: fine-focus sealed tube	1494 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
T_min = 0.942, T_max = 0.971	k = −18→18
14235 measured reflections	l = −22→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.044P)² + 0.9487P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2606 reflections	Δρ_max = 0.17 e Å⁻³
175 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0155 (11)

Crystal data top

C₁₄H₁₅N₃OS	V = 2952.9 (9) Å³
M_r = 273.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.1691 (17) Å	µ = 0.22 mm⁻¹
b = 15.485 (3) Å	T = 571 K
c = 20.798 (4) Å	0.28 × 0.24 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1494 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.971	R_int = 0.073
14235 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
2606 reflections	Δρ_min = −0.16 e Å⁻³
175 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	U_iso*/U_eq
S1	0.10446 (8)	0.82693 (5)	0.31856 (3)	0.0566 (3)
O1	0.08455 (18)	0.69624 (13)	0.20969 (9)	0.0658 (6)
N1	0.1800 (2)	0.67674 (14)	0.37036 (10)	0.0540 (6)
C8	0.2078 (3)	0.70685 (17)	0.23078 (12)	0.0498 (7)
C1	0.0880 (3)	0.74194 (16)	0.37418 (12)	0.0480 (7)
N3	0.3186 (2)	0.65184 (14)	0.22060 (10)	0.0539 (6)
H3A	0.4015	0.6669	0.2364	0.065*
C7	0.2494 (3)	0.78653 (16)	0.26898 (13)	0.0541 (7)
H7A	0.2793	0.8316	0.2394	0.065*
H7B	0.3324	0.7728	0.2961	0.065*
C9	0.3164 (3)	0.57251 (18)	0.18732 (13)	0.0538 (7)
N2	−0.0195 (3)	0.75292 (15)	0.41631 (11)	0.0665 (7)
C2	0.1643 (3)	0.61439 (19)	0.41447 (15)	0.0643 (8)
C14	0.4321 (4)	0.51737 (19)	0.19623 (14)	0.0703 (9)
H14	0.5079	0.5332	0.2235	0.084*
C10	0.2056 (3)	0.5472 (2)	0.14672 (15)	0.0779 (10)
H10	0.1266	0.5837	0.1396	0.093*
C3	0.0557 (4)	0.6186 (2)	0.45961 (14)	0.0707 (9)
H3	0.0440	0.5748	0.4898	0.085*
C4	−0.0353 (4)	0.6890 (2)	0.45926 (15)	0.0774 (10)
C13	0.4371 (5)	0.4388 (2)	0.16514 (18)	0.0922 (12)
H13	0.5167	0.4025	0.1712	0.111*
C12	0.3259 (6)	0.4141 (2)	0.12546 (18)	0.0939 (12)
H12	0.3289	0.3608	0.1048	0.113*
C6	0.2714 (4)	0.5413 (2)	0.41157 (19)	0.1032 (13)
H6A	0.2749	0.5188	0.3686	0.155*
H6B	0.2415	0.4965	0.4406	0.155*
H6C	0.3663	0.5618	0.4236	0.155*
C11	0.2113 (5)	0.4679 (3)	0.11651 (17)	0.0930 (12)
H11	0.1354	0.4512	0.0896	0.112*
C5	−0.1579 (6)	0.6993 (3)	0.5073 (2)	0.147 (2)
H5A	−0.1525	0.7555	0.5266	0.221*
H5B	−0.1491	0.6559	0.5400	0.221*
H5C	−0.2498	0.6929	0.4857	0.221*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0512 (4)	0.0549 (4)	0.0636 (5)	0.0038 (4)	0.0011 (4)	0.0005 (4)
O1	0.0307 (10)	0.0895 (15)	0.0773 (13)	−0.0027 (10)	−0.0043 (9)	−0.0168 (11)
N1	0.0526 (14)	0.0541 (13)	0.0554 (14)	0.0043 (12)	−0.0011 (11)	−0.0041 (12)
C8	0.0318 (15)	0.0690 (17)	0.0486 (16)	−0.0061 (14)	0.0067 (12)	0.0041 (14)
C1	0.0472 (16)	0.0529 (16)	0.0438 (15)	−0.0019 (14)	−0.0039 (13)	−0.0085 (12)
N3	0.0309 (12)	0.0714 (16)	0.0595 (14)	−0.0028 (11)	0.0009 (10)	−0.0078 (12)
C7	0.0362 (14)	0.0618 (16)	0.0641 (18)	−0.0076 (13)	−0.0001 (13)	0.0049 (14)
C9	0.0445 (16)	0.0656 (18)	0.0514 (17)	−0.0071 (15)	0.0112 (14)	0.0026 (15)
N2	0.0706 (17)	0.0670 (16)	0.0620 (16)	0.0121 (14)	0.0178 (14)	0.0002 (13)
C2	0.072 (2)	0.0547 (18)	0.066 (2)	0.0035 (16)	−0.0021 (18)	−0.0043 (16)
C14	0.075 (2)	0.069 (2)	0.067 (2)	−0.0001 (18)	−0.0013 (17)	0.0073 (16)
C10	0.059 (2)	0.101 (3)	0.073 (2)	−0.0015 (18)	0.0026 (17)	−0.026 (2)
C3	0.092 (2)	0.0622 (19)	0.0583 (19)	−0.0038 (19)	0.0064 (18)	0.0034 (15)
C4	0.089 (2)	0.078 (2)	0.065 (2)	0.009 (2)	0.0241 (19)	0.0003 (18)
C13	0.124 (4)	0.066 (2)	0.087 (3)	0.019 (2)	0.012 (2)	0.007 (2)
C12	0.137 (4)	0.071 (2)	0.074 (3)	−0.017 (3)	0.028 (3)	−0.013 (2)
C6	0.113 (3)	0.075 (2)	0.122 (3)	0.031 (2)	0.010 (3)	0.016 (2)
C11	0.091 (3)	0.109 (3)	0.079 (3)	−0.018 (3)	0.010 (2)	−0.030 (2)
C5	0.175 (5)	0.138 (4)	0.129 (4)	0.045 (3)	0.100 (3)	0.029 (3)

Geometric parameters (Å, º) top

S1—C1	1.759 (3)	C14—H14	0.9300
S1—C7	1.795 (3)	C10—C11	1.380 (4)
O1—C8	1.223 (3)	C10—H10	0.9300
N1—C1	1.318 (3)	C3—C4	1.373 (4)
N1—C2	1.340 (3)	C3—H3	0.9300
C8—N3	1.343 (3)	C4—C5	1.512 (5)
C8—C7	1.516 (3)	C13—C12	1.367 (5)
C1—N2	1.330 (3)	C13—H13	0.9300
N3—C9	1.410 (3)	C12—C11	1.354 (5)
N3—H3A	0.8600	C12—H12	0.9300
C7—H7A	0.9700	C6—H6A	0.9600
C7—H7B	0.9700	C6—H6B	0.9600
C9—C14	1.375 (4)	C6—H6C	0.9600
C9—C10	1.378 (4)	C11—H11	0.9300
N2—C4	1.341 (4)	C5—H5A	0.9600
C2—C3	1.370 (4)	C5—H5B	0.9600
C2—C6	1.500 (4)	C5—H5C	0.9600
C14—C13	1.378 (4)

C1—S1—C7	100.40 (13)	C11—C10—H10	119.9
C1—N1—C2	116.2 (2)	C2—C3—C4	118.4 (3)
O1—C8—N3	123.9 (2)	C2—C3—H3	120.8
O1—C8—C7	122.0 (2)	C4—C3—H3	120.8
N3—C8—C7	114.1 (2)	N2—C4—C3	121.6 (3)
N1—C1—N2	127.7 (2)	N2—C4—C5	116.3 (3)
N1—C1—S1	118.6 (2)	C3—C4—C5	122.1 (3)
N2—C1—S1	113.7 (2)	C12—C13—C14	120.4 (4)
C8—N3—C9	128.2 (2)	C12—C13—H13	119.8
C8—N3—H3A	115.9	C14—C13—H13	119.8
C9—N3—H3A	115.9	C11—C12—C13	119.3 (3)
C8—C7—S1	113.47 (17)	C11—C12—H12	120.4
C8—C7—H7A	108.9	C13—C12—H12	120.4
S1—C7—H7A	108.9	C2—C6—H6A	109.5
C8—C7—H7B	108.9	C2—C6—H6B	109.5
S1—C7—H7B	108.9	H6A—C6—H6B	109.5
H7A—C7—H7B	107.7	C2—C6—H6C	109.5
C14—C9—C10	118.4 (3)	H6A—C6—H6C	109.5
C14—C9—N3	117.6 (3)	H6B—C6—H6C	109.5
C10—C9—N3	124.0 (3)	C12—C11—C10	121.0 (4)
C1—N2—C4	115.1 (2)	C12—C11—H11	119.5
N1—C2—C3	120.9 (3)	C10—C11—H11	119.5
N1—C2—C6	116.5 (3)	C4—C5—H5A	109.5
C3—C2—C6	122.6 (3)	C4—C5—H5B	109.5
C9—C14—C13	120.7 (3)	H5A—C5—H5B	109.5
C9—C14—H14	119.6	C4—C5—H5C	109.5
C13—C14—H14	119.6	H5A—C5—H5C	109.5
C9—C10—C11	120.3 (3)	H5B—C5—H5C	109.5
C9—C10—H10	119.9

C2—N1—C1—N2	−0.7 (4)	C10—C9—C14—C13	0.1 (4)
C2—N1—C1—S1	178.98 (19)	N3—C9—C14—C13	−179.9 (3)
C7—S1—C1—N1	3.4 (2)	C14—C9—C10—C11	0.6 (5)
C7—S1—C1—N2	−176.94 (19)	N3—C9—C10—C11	−179.3 (3)
O1—C8—N3—C9	−2.5 (4)	N1—C2—C3—C4	−1.0 (4)
C7—C8—N3—C9	179.8 (2)	C6—C2—C3—C4	178.7 (3)
O1—C8—C7—S1	34.4 (3)	C1—N2—C4—C3	1.1 (4)
N3—C8—C7—S1	−147.93 (19)	C1—N2—C4—C5	−179.3 (3)
C1—S1—C7—C8	66.6 (2)	C2—C3—C4—N2	−0.3 (5)
C8—N3—C9—C14	−164.3 (3)	C2—C3—C4—C5	−179.9 (4)
C8—N3—C9—C10	15.6 (4)	C9—C14—C13—C12	−0.8 (5)
N1—C1—N2—C4	−0.6 (4)	C14—C13—C12—C11	0.6 (5)
S1—C1—N2—C4	179.7 (2)	C13—C12—C11—C10	0.1 (6)
C1—N1—C2—C3	1.5 (4)	C9—C10—C11—C12	−0.8 (5)
C1—N1—C2—C6	−178.3 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅N₃OS
M_r	273.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	571
a, b, c (Å)	9.1691 (17), 15.485 (3), 20.798 (4)
V (Å³)	2952.9 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.24 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.942, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	14235, 2606, 1494
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.01
No. of reflections	2606
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

O1—C8—C7

122.0 (2)

N3—C8—C7

114.1 (2)

Acknowledgements

We gratefully acknowledge the 05 L003 project supported by the Education Department of LiaoNing Province in China and the 2006 SH03 project supported by Anshan Municipal Science and Technology Commission.

References

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