N-(2-Chloro-phen-yl)-2-(4,6-dimethyl-pyrimidin-2-ylsulfan-yl)acetamide.

In the title compound, C(14)H(14)ClN(3)OS, the 4,6-dimethyl-pyrimidine ring and the chloro-benzene ring subtend a dihedral angle of 80.0 (2)°. The length of the Csp(2)-S bond is significantly shorter than that of the Csp(3)-S bond. The crystal structure is stabilized by inter-molecular N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonding, and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Gao et al. (2007 ▶). For heteroatom-rich compounds as effective precursors for active mol­ecules, see: Huynh et al. (2005 ▶); Ye et al. (2006 ▶).

Experimental

Crystal data

C14H14ClN3OS

M = 307.79

Orthorhombic,

a = 26.494 (5) Å

b = 4.6736 (9) Å

c = 11.931 (2) Å

V = 1477.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 113 K

0.30 × 0.26 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.890, T max = 0.925

8870 measured reflections

2573 independent reflections

2445 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.061

S = 1.07

2573 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1199 Freidel pairs

Flack parameter: 0.00 (5)

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999 ▶); cell refinement: CrystalClear ; data reduction: CrystalClear; 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/S1600536809011520/at2755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011520/at2755Isup2.hkl

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

C14H14ClN3OS	F(000) = 640
Mr = 307.79	Dx = 1.384 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4682 reflections
a = 26.494 (5) Å	θ = 1.5–27.9°
b = 4.6736 (9) Å	µ = 0.40 mm−1
c = 11.931 (2) Å	T = 113 K
V = 1477.3 (5) Å3	Prism, colourless
Z = 4	0.30 × 0.26 × 0.20 mm

Rigaku Saturn diffractometer	2573 independent reflections
Radiation source: rotating anode	2445 reflections with I > 2σ(I)
confocal	Rint = 0.031
ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→31
Tmin = 0.890, Tmax = 0.925	k = −5→5
8870 measured reflections	l = −14→14

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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2573 reflections	Δρmax = 0.17 e Å−3
187 parameters	Δρmin = −0.20 e Å−3
2 restraints	Absolute structure: Flack (1983), 1199 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (5)

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	0.689926 (15)	1.07672 (8)	0.28992 (4)	0.02168 (11)
Cl1	0.53054 (2)	1.55461 (10)	0.63460 (4)	0.03848 (14)
O1	0.58637 (4)	0.8871 (2)	0.35668 (11)	0.0216 (3)
N1	0.55577 (5)	1.3204 (3)	0.40980 (12)	0.0193 (3)
N2	0.67886 (5)	1.0007 (3)	0.51049 (13)	0.0216 (3)
N3	0.74415 (5)	0.7412 (3)	0.41469 (12)	0.0198 (3)
C1	0.49282 (7)	1.3208 (4)	0.55761 (16)	0.0250 (4)
C2	0.44695 (7)	1.2326 (4)	0.60204 (17)	0.0353 (5)
H2	0.4361	1.3025	0.6710	0.042*
C3	0.41781 (7)	1.0427 (5)	0.5439 (2)	0.0403 (6)
H3	0.3873	0.9816	0.5740	0.048*
C4	0.43334 (7)	0.9406 (4)	0.44072 (19)	0.0350 (5)
H4	0.4134	0.8106	0.4017	0.042*
C5	0.47894 (6)	1.0334 (4)	0.39558 (18)	0.0254 (4)
H5	0.4891	0.9674	0.3256	0.031*
C6	0.50924 (6)	1.2233 (3)	0.45406 (14)	0.0204 (4)
C7	0.59151 (6)	1.1465 (3)	0.36648 (14)	0.0171 (3)
C8	0.63851 (6)	1.3054 (4)	0.32946 (15)	0.0233 (4)
H8A	0.6495	1.4287	0.3901	0.028*
H8B	0.6300	1.4267	0.2663	0.028*
C9	0.70557 (6)	0.9262 (3)	0.42103 (14)	0.0179 (3)
C10	0.75680 (6)	0.6156 (3)	0.51203 (15)	0.0201 (4)
C11	0.73123 (6)	0.6745 (4)	0.61057 (15)	0.0238 (4)
H11	0.7400	0.5841	0.6772	0.029*
C12	0.69218 (6)	0.8721 (4)	0.60723 (16)	0.0231 (4)
C13	0.80089 (7)	0.4138 (4)	0.50769 (18)	0.0280 (4)
H13A	0.8046	0.3412	0.4329	0.042*
H13B	0.7952	0.2576	0.5584	0.042*
H13C	0.8311	0.5135	0.5291	0.042*
C14	0.66199 (8)	0.9520 (5)	0.70853 (18)	0.0363 (5)
H14A	0.6604	1.1567	0.7146	0.054*
H14B	0.6778	0.8745	0.7743	0.054*
H14C	0.6285	0.8762	0.7016	0.054*
H1	0.5635 (7)	1.500 (2)	0.4204 (17)	0.027 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.02112 (19)	0.0217 (2)	0.0222 (2)	0.00522 (16)	0.00482 (17)	0.0057 (2)
Cl1	0.0551 (3)	0.0323 (3)	0.0280 (3)	0.0023 (2)	0.0035 (2)	−0.0090 (2)
O1	0.0241 (6)	0.0138 (6)	0.0270 (7)	0.0011 (5)	0.0005 (5)	−0.0002 (5)
N1	0.0224 (7)	0.0105 (7)	0.0249 (8)	−0.0024 (5)	0.0059 (6)	−0.0004 (6)
N2	0.0201 (7)	0.0226 (7)	0.0221 (8)	−0.0003 (6)	0.0016 (6)	−0.0034 (7)
N3	0.0188 (7)	0.0180 (7)	0.0224 (8)	−0.0013 (5)	0.0005 (6)	0.0008 (6)
C1	0.0303 (9)	0.0197 (9)	0.0251 (9)	0.0060 (7)	0.0049 (7)	0.0054 (8)
C2	0.0357 (11)	0.0317 (10)	0.0386 (12)	0.0123 (8)	0.0153 (9)	0.0113 (9)
C3	0.0226 (9)	0.0422 (13)	0.0560 (15)	0.0027 (9)	0.0127 (9)	0.0221 (11)
C4	0.0235 (10)	0.0342 (11)	0.0474 (14)	−0.0054 (8)	−0.0060 (9)	0.0125 (10)
C5	0.0239 (9)	0.0234 (9)	0.0290 (10)	0.0000 (7)	−0.0017 (8)	0.0070 (8)
C6	0.0206 (9)	0.0163 (9)	0.0243 (9)	0.0042 (6)	0.0028 (7)	0.0052 (7)
C7	0.0207 (8)	0.0157 (8)	0.0150 (8)	0.0016 (6)	−0.0026 (6)	0.0016 (7)
C8	0.0232 (8)	0.0168 (8)	0.0299 (10)	0.0042 (7)	0.0048 (7)	0.0043 (7)
C9	0.0179 (8)	0.0157 (8)	0.0203 (9)	−0.0031 (6)	0.0001 (7)	−0.0007 (7)
C10	0.0203 (9)	0.0171 (8)	0.0230 (10)	−0.0046 (6)	−0.0050 (7)	0.0011 (7)
C11	0.0256 (9)	0.0255 (9)	0.0203 (10)	−0.0056 (7)	−0.0047 (7)	0.0038 (8)
C12	0.0219 (9)	0.0282 (9)	0.0192 (10)	−0.0072 (7)	0.0004 (6)	−0.0042 (8)
C13	0.0269 (9)	0.0276 (10)	0.0294 (11)	0.0031 (7)	−0.0037 (8)	0.0038 (8)
C14	0.0322 (11)	0.0547 (13)	0.0220 (11)	0.0013 (9)	0.0024 (8)	−0.0055 (9)

S1—C9	1.7646 (17)	C4—H4	0.9300
S1—C8	1.7947 (17)	C5—C6	1.385 (3)
Cl1—C1	1.742 (2)	C5—H5	0.9300
O1—C7	1.2252 (19)	C7—C8	1.516 (2)
N1—C7	1.351 (2)	C8—H8A	0.9700
N1—C6	1.416 (2)	C8—H8B	0.9700
N1—H1	0.874 (9)	C10—C11	1.385 (3)
N2—C9	1.327 (2)	C10—C13	1.502 (3)
N2—C12	1.348 (2)	C11—C12	1.387 (2)
N3—C9	1.341 (2)	C11—H11	0.9300
N3—C10	1.344 (2)	C12—C14	1.497 (3)
C1—C6	1.387 (2)	C13—H13A	0.9600
C1—C2	1.388 (3)	C13—H13B	0.9600
C2—C3	1.365 (3)	C13—H13C	0.9600
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.383 (3)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.392 (3)
C9—S1—C8	100.53 (8)	S1—C8—H8A	108.7
C7—N1—C6	124.06 (14)	C7—C8—H8B	108.7
C7—N1—H1	117.9 (13)	S1—C8—H8B	108.7
C6—N1—H1	117.4 (13)	H8A—C8—H8B	107.6
C9—N2—C12	115.58 (14)	N2—C9—N3	128.40 (15)
C9—N3—C10	115.01 (14)	N2—C9—S1	118.89 (12)
C6—C1—C2	121.14 (18)	N3—C9—S1	112.71 (12)
C6—C1—Cl1	119.72 (14)	N3—C10—C11	121.67 (15)
C2—C1—Cl1	119.13 (16)	N3—C10—C13	116.00 (15)
C3—C2—C1	119.6 (2)	C11—C10—C13	122.32 (16)
C3—C2—H2	120.2	C10—C11—C12	118.23 (16)
C1—C2—H2	120.2	C10—C11—H11	120.9
C2—C3—C4	120.55 (19)	C12—C11—H11	120.9
C2—C3—H3	119.7	N2—C12—C11	121.10 (16)
C4—C3—H3	119.7	N2—C12—C14	116.10 (16)
C3—C4—C5	119.7 (2)	C11—C12—C14	122.79 (17)
C3—C4—H4	120.2	C10—C13—H13A	109.5
C5—C4—H4	120.2	C10—C13—H13B	109.5
C6—C5—C4	120.50 (19)	H13A—C13—H13B	109.5
C6—C5—H5	119.8	C10—C13—H13C	109.5
C4—C5—H5	119.8	H13A—C13—H13C	109.5
C5—C6—C1	118.53 (16)	H13B—C13—H13C	109.5
C5—C6—N1	121.47 (16)	C12—C14—H14A	109.5
C1—C6—N1	120.00 (16)	C12—C14—H14B	109.5
O1—C7—N1	123.63 (14)	H14A—C14—H14B	109.5
O1—C7—C8	123.26 (14)	C12—C14—H14C	109.5
N1—C7—C8	113.10 (14)	H14A—C14—H14C	109.5
C7—C8—S1	114.09 (12)	H14B—C14—H14C	109.5
C7—C8—H8A	108.7
C6—C1—C2—C3	1.2 (3)	N1—C7—C8—S1	171.73 (12)
Cl1—C1—C2—C3	−178.03 (15)	C9—S1—C8—C7	−68.05 (14)
C1—C2—C3—C4	−0.8 (3)	C12—N2—C9—N3	−0.4 (3)
C2—C3—C4—C5	−0.3 (3)	C12—N2—C9—S1	178.49 (12)
C3—C4—C5—C6	1.1 (3)	C10—N3—C9—N2	0.4 (2)
C4—C5—C6—C1	−0.7 (3)	C10—N3—C9—S1	−178.57 (11)
C4—C5—C6—N1	179.97 (16)	C8—S1—C9—N2	0.91 (15)
C2—C1—C6—C5	−0.4 (3)	C8—S1—C9—N3	179.98 (11)
Cl1—C1—C6—C5	178.80 (13)	C9—N3—C10—C11	0.4 (2)
C2—C1—C6—N1	178.91 (16)	C9—N3—C10—C13	−178.32 (14)
Cl1—C1—C6—N1	−1.9 (2)	N3—C10—C11—C12	−1.0 (2)
C7—N1—C6—C5	−48.9 (2)	C13—C10—C11—C12	177.59 (16)
C7—N1—C6—C1	131.82 (18)	C9—N2—C12—C11	−0.3 (2)
C6—N1—C7—O1	3.2 (3)	C9—N2—C12—C14	−179.39 (16)
C6—N1—C7—C8	−177.61 (15)	C10—C11—C12—N2	1.0 (2)
O1—C7—C8—S1	−9.1 (2)	C10—C11—C12—C14	179.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (1)	2.05 (1)	2.8414 (18)	150 (2)
C2—H2···O1ii	0.93	2.46	3.213 (2)	138
C8—H8A···Cg1i	0.97	2.92	3.832 (2)	157
C13—H13B···Cg1iii	0.96	2.99	3.592 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.873 (11)	2.054 (12)	2.8414 (18)	149.6 (18)
C2—H2⋯O1ii	0.93	2.46	3.213 (2)	138
C8—H8A⋯Cg1i	0.97	2.92	3.832 (2)	157
C13—H13B⋯Cg1iii	0.96	2.99	3.592 (2)	122

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the N2/N3/C9–C12 ring.