2-(4,6-Dimethyl-pyrimidin-2-ylsulfan-yl)-N-phenyl-acetamide.

In the title compound, C(14)H(15)N(3)OS, the phenyl ring is almost perpendicular to the dimethyl-pyrimidine group, with a dihedral angle of 88.1 (3)°. The Csp(2)-S bond of 1.759 (3) Å is significantly shorter than the Csp(3)-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 = 273.35

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.01

2606 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −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.

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

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

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

C14H15N3OS	F000 = 1152
Mr = 273.35	Dx = 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 = 2.8–22.1º
b = 15.485 (3) Å	µ = 0.22 mm−1
c = 20.798 (4) Å	T = 571 (2) K
V = 2952.9 (9) Å3	Block, colourless
Z = 8	0.28 × 0.24 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	2606 independent reflections
Radiation source: fine-focus sealed tube	1494 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.073
T = 571(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.942, Tmax = 0.971	k = −18→18
14235 measured reflections	l = −22→24

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.044P)2 + 0.9487P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.17 e Å−3
2606 reflections	Δρmin = −0.16 e Å−3
175 parameters	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)
Secondary atom site location: difference Fourier map

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
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*

	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)

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)