4-(4-Chloro-phen-yl)-6-(methyl-sulfan-yl)pyrimidin-2-amine.

In the title compound, C(11)H(10)ClN(3)S, the dihedral angle between the benzene and pyrimidine rings is 3.99 (4)°. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into ribbons of R(2) (2)(8) rings parallel to [100]. Weak C-H⋯S contacts connect adjacent ribbons into a two-dimensional undulating layer-like structure extending parallel to (110). The benzene and pyrimidine rings of adjacent mol-ecules have the offset face-to-face π-π stacking inter-actions in a zigzag fashion along the c axis, with perpendicular ring distances of 3.463 and 3.639 Å, and a dihedral angle between the planes of 3.99 (2)°. The distance between the ring centroids is 4.420 (2) Å.

Related literature

For the synthesis of pyrimidine-5-carbaldehydes from α-formyl­aroylketene dithio­acetals, see: Mathews & Asokan (2007 ▶). For the synthesis of a 6-aryl amino­pyrimidine compound, see: Lin et al. (2008 ▶). For the application of organic compounds as ligands, see: Li et al. (2007 ▶). For the importance amino­pyrimidine compounds in the synthesis of complexes, see: Cui & Lan (2007 ▶). For a review of inter­molecular C—H⋯S contacts, see: Taylor & Kennard (1982 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H10ClN3S

M = 251.73

Orthorhombic,

a = 6.8148 (11) Å

b = 10.6107 (16) Å

c = 16.509 (3) Å

V = 1193.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.25 × 0.14 × 0.08 mm

Data collection

Bruker APEXII 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.925, T max = 0.964

7825 measured reflections

2800 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.096

S = 1.01

2800 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1061 Friedel pairs

Flack parameter: 0.02 (10)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024891/si2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024891/si2183Isup2.hkl

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

C11H10ClN3S	F(000) = 520
Mr = 251.73	Dx = 1.401 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3984 reflections
a = 6.8148 (11) Å	θ = 2.3–28.4°
b = 10.6107 (16) Å	µ = 0.47 mm−1
c = 16.509 (3) Å	T = 293 K
V = 1193.7 (3) Å3	Block, yellow
Z = 4	0.25 × 0.14 × 0.08 mm

Bruker APEXII 1K CCD area-detector diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	1841 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.925, Tmax = 0.964	k = −13→11
7825 measured reflections	l = −21→22

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2800 reflections	Δρmax = 0.19 e Å−3
145 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1061 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (10)

Experimental. 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.

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl1	1.15208 (14)	1.01534 (10)	0.62970 (5)	0.0694 (3)
S1	−0.01688 (13)	0.85410 (8)	0.91781 (5)	0.0522 (2)
N1	0.4426 (3)	1.1541 (2)	0.89640 (13)	0.0357 (6)
N2	0.1442 (4)	1.0763 (2)	0.95722 (13)	0.0338 (6)
N3	0.2824 (4)	1.2627 (2)	0.99649 (16)	0.0423 (6)
H3A	0.3713	1.3201	0.9931	0.051*
H3B	0.1880	1.2708	1.0307	0.051*
C1	0.9466 (5)	1.0272 (3)	0.69138 (17)	0.0454 (8)
C2	0.8052 (5)	0.9354 (3)	0.68825 (18)	0.0508 (9)
H2B	0.8186	0.8682	0.6526	0.061*
C3	0.6427 (5)	0.9430 (3)	0.73817 (19)	0.0473 (8)
H3C	0.5474	0.8803	0.7359	0.057*
C4	0.6197 (4)	1.0437 (3)	0.79209 (16)	0.0359 (7)
C5	0.7638 (5)	1.1359 (3)	0.79272 (17)	0.0427 (8)
H5A	0.7502	1.2044	0.8274	0.051*
C6	0.9275 (5)	1.1292 (3)	0.74324 (18)	0.0484 (9)
H6A	1.0228	1.1919	0.7448	0.058*
C7	0.4499 (4)	1.0503 (3)	0.84876 (16)	0.0343 (7)
C8	0.3107 (5)	0.9576 (3)	0.85466 (18)	0.0438 (8)
H8A	0.3171	0.8859	0.8224	0.053*
C9	0.1589 (4)	0.9737 (3)	0.91043 (17)	0.0366 (7)
C10	0.2911 (4)	1.1611 (3)	0.94864 (16)	0.0333 (7)
C11	−0.1656 (6)	0.9020 (4)	1.0015 (2)	0.0811 (13)
H11A	−0.2674	0.8410	1.0102	0.122*
H11B	−0.2235	0.9826	0.9900	0.122*
H11C	−0.0858	0.9083	1.0493	0.122*

	U11	U22	U33	U12	U13	U23
Cl1	0.0647 (6)	0.0800 (7)	0.0634 (6)	0.0144 (6)	0.0276 (5)	−0.0046 (5)
S1	0.0488 (5)	0.0391 (4)	0.0686 (5)	−0.0083 (5)	0.0010 (5)	−0.0064 (5)
N1	0.0339 (13)	0.0370 (14)	0.0361 (13)	0.0013 (12)	0.0010 (10)	−0.0044 (12)
N2	0.0334 (13)	0.0344 (14)	0.0336 (13)	0.0003 (12)	−0.0039 (11)	−0.0010 (12)
N3	0.0381 (16)	0.0411 (16)	0.0476 (14)	−0.0054 (12)	0.0095 (13)	−0.0139 (13)
C1	0.048 (2)	0.053 (2)	0.0349 (16)	0.0154 (18)	0.0071 (15)	0.0003 (16)
C2	0.056 (2)	0.049 (2)	0.0468 (19)	0.0101 (18)	0.0025 (18)	−0.0163 (17)
C3	0.045 (2)	0.046 (2)	0.0516 (19)	0.0008 (17)	−0.0012 (17)	−0.0137 (17)
C4	0.0367 (18)	0.0368 (18)	0.0344 (15)	0.0061 (14)	−0.0056 (13)	−0.0035 (14)
C5	0.0501 (19)	0.0398 (19)	0.0381 (17)	0.0023 (18)	0.0065 (15)	−0.0044 (16)
C6	0.051 (2)	0.049 (2)	0.0446 (18)	−0.0049 (17)	0.0095 (16)	−0.0024 (17)
C7	0.0310 (17)	0.0373 (18)	0.0347 (15)	0.0058 (14)	−0.0033 (12)	−0.0044 (14)
C8	0.044 (2)	0.0382 (19)	0.0489 (19)	−0.0005 (16)	0.0015 (15)	−0.0105 (15)
C9	0.0346 (16)	0.0341 (17)	0.0411 (16)	0.0000 (14)	−0.0101 (15)	0.0027 (15)
C10	0.0319 (16)	0.0346 (18)	0.0334 (15)	0.0036 (14)	−0.0043 (12)	−0.0021 (14)
C11	0.077 (3)	0.065 (3)	0.101 (3)	−0.021 (2)	0.037 (3)	−0.001 (2)

Cl1—C1	1.736 (3)	C3—C4	1.400 (4)
S1—C9	1.750 (3)	C3—H3C	0.9300
S1—C11	1.788 (4)	C4—C5	1.387 (4)
N1—C10	1.347 (3)	C4—C7	1.490 (4)
N1—C7	1.354 (3)	C5—C6	1.384 (4)
N2—C9	1.339 (3)	C5—H5A	0.9300
N2—C10	1.353 (4)	C6—H6A	0.9300
N3—C10	1.338 (4)	C7—C8	1.370 (4)
N3—H3A	0.8600	C8—C9	1.395 (4)
N3—H3B	0.8600	C8—H8A	0.9300
C1—C2	1.371 (5)	C11—H11A	0.9600
C1—C6	1.386 (4)	C11—H11B	0.9600
C2—C3	1.383 (4)	C11—H11C	0.9600
C2—H2B	0.9300
C9—S1—C11	103.63 (16)	C5—C6—C1	118.7 (3)
C10—N1—C7	116.4 (2)	C5—C6—H6A	120.6
C9—N2—C10	115.1 (2)	C1—C6—H6A	120.6
C10—N3—H3A	120.0	N1—C7—C8	121.1 (3)
C10—N3—H3B	120.0	N1—C7—C4	115.6 (2)
H3A—N3—H3B	120.0	C8—C7—C4	123.3 (3)
C2—C1—C6	120.8 (3)	C7—C8—C9	118.2 (3)
C2—C1—Cl1	119.6 (3)	C7—C8—H8A	120.9
C6—C1—Cl1	119.7 (3)	C9—C8—H8A	120.9
C1—C2—C3	120.0 (3)	N2—C9—C8	122.4 (3)
C1—C2—H2B	120.0	N2—C9—S1	119.9 (2)
C3—C2—H2B	120.0	C8—C9—S1	117.7 (2)
C2—C3—C4	120.8 (3)	N3—C10—N1	117.1 (3)
C2—C3—H3C	119.6	N3—C10—N2	116.2 (2)
C4—C3—H3C	119.6	N1—C10—N2	126.7 (3)
C5—C4—C3	117.7 (3)	S1—C11—H11A	109.5
C5—C4—C7	120.8 (3)	S1—C11—H11B	109.5
C3—C4—C7	121.4 (3)	H11A—C11—H11B	109.5
C6—C5—C4	122.0 (3)	S1—C11—H11C	109.5
C6—C5—H5A	119.0	H11A—C11—H11C	109.5
C4—C5—H5A	119.0	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2i	0.86	2.31	3.095 (3)	152
N3—H3B···N1ii	0.86	2.21	3.045 (3)	164
C11—H11A···S1iii	0.96	2.93	3.859 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2i	0.86	2.31	3.095 (3)	152
N3—H3B⋯N1ii	0.86	2.21	3.045 (3)	164
C11—H11A⋯S1iii	0.96	2.93	3.859 (4)	163

Symmetry codes: (i) ; (ii) ; (iii) .