1-(4-Chloro-phen-yl)-4,4,6-trimethyl-3,4-dihydro-pyrimidine-2(1H)-thione.

The dihydro-pyrimidine ring of the title compound, C(13)H(15)ClN(2)S, adopts an envelope conformation with five almost coplanar atoms (r.m.s. deviation = 0.054 Å) and the C atom bearing the two methyl substituents deviating from this plane by 0.441 (2) Å. The best plane through the five almost coplanar atoms forms a dihedral angle of 89.56 (5)° with the benzene ring. The crystal packing is characterized by centrosymmetric dimers connected by pairs of N-H⋯S hydrogen bonds.

Related literature

For details of the biological activity of pyrimidine-2-thio­nes, see: Alam et al. (2005 ▶); Sriram et al. (2006 ▶); Leite et al. (2006 ▶); Kappe (2000 ▶); Rovnyak et al. (1995 ▶); Swamy et al. (2005 ▶). For a related structure, see: Yamin et al. (2005 ▶).

Experimental

Crystal data

C13H15ClN2S

M = 266.78

Monoclinic,

a = 20.6710 (18) Å

b = 10.8343 (10) Å

c = 14.8619 (13) Å

β = 126.026 (5)°

V = 2691.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 173 K

0.37 × 0.29 × 0.26 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.861, T max = 0.899

7624 measured reflections

2512 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.02

2512 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001777/zq2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001777/zq2028Isup2.hkl

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

C13H15ClN2S	F(000) = 1120
Mr = 266.78	Dx = 1.317 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6686 reflections
a = 20.6710 (18) Å	θ = 3.4–26.1°
b = 10.8343 (10) Å	µ = 0.42 mm−1
c = 14.8619 (13) Å	T = 173 K
β = 126.026 (5)°	Block, colourless
V = 2691.9 (4) Å3	0.37 × 0.29 × 0.26 mm
Z = 8

Stoe IPDS II two-circle diffractometer	2512 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −25→24
Tmin = 0.861, Tmax = 0.899	k = −13→13
7624 measured reflections	l = −16→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0634P)2] where P = (Fo2 + 2Fc2)/3
2512 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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	0.57142 (2)	0.69991 (4)	0.42770 (3)	0.02504 (14)
Cl1	0.68751 (3)	0.59306 (4)	0.93548 (3)	0.03636 (15)
N1	0.47205 (7)	0.78438 (12)	0.47357 (11)	0.0219 (3)
H1	0.4318 (11)	0.7666 (19)	0.2421 (18)	0.027 (5)*
C2	0.48383 (9)	0.75825 (14)	0.39373 (13)	0.0202 (3)
N3	0.42364 (8)	0.78513 (13)	0.28874 (12)	0.0239 (3)
C4	0.33943 (9)	0.80299 (15)	0.24811 (13)	0.0240 (4)
C5	0.34219 (9)	0.86623 (15)	0.34036 (14)	0.0251 (3)
H5	0.2983	0.9165	0.3221	0.030*
C6	0.40392 (9)	0.85420 (15)	0.44661 (14)	0.0238 (3)
C7	0.29744 (11)	0.67811 (18)	0.21978 (17)	0.0364 (4)
H7A	0.3015	0.6356	0.1651	0.055*
H7B	0.2410	0.6907	0.1886	0.055*
H7C	0.3229	0.6280	0.2874	0.055*
C8	0.29878 (10)	0.88397 (18)	0.14363 (15)	0.0348 (4)
H9A	0.3273	0.9627	0.1621	0.052*
H9B	0.2432	0.8993	0.1157	0.052*
H9C	0.2999	0.8416	0.0863	0.052*
C9	0.40992 (11)	0.91451 (18)	0.54228 (15)	0.0342 (4)
H8A	0.3607	0.9608	0.5143	0.051*
H8B	0.4557	0.9710	0.5804	0.051*
H8C	0.4173	0.8511	0.5946	0.051*
C11	0.52708 (9)	0.73685 (15)	0.58519 (12)	0.0209 (3)
C12	0.51342 (9)	0.62101 (15)	0.60981 (13)	0.0236 (3)
H12	0.4698	0.5727	0.5531	0.028*
C13	0.56377 (9)	0.57500 (15)	0.71809 (14)	0.0251 (3)
H13	0.5550	0.4955	0.7359	0.030*
C14	0.62664 (9)	0.64743 (15)	0.79878 (13)	0.0237 (3)
C15	0.64175 (9)	0.76243 (16)	0.77479 (14)	0.0271 (4)
H15	0.6859	0.8099	0.8313	0.033*
C16	0.59136 (10)	0.80791 (15)	0.66666 (14)	0.0260 (4)
H16	0.6009	0.8869	0.6488	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0186 (2)	0.0362 (3)	0.0192 (2)	0.00399 (14)	0.01047 (17)	0.00264 (15)
Cl1	0.0372 (2)	0.0389 (3)	0.0182 (2)	0.00307 (17)	0.00804 (19)	0.00696 (16)
N1	0.0217 (6)	0.0262 (7)	0.0175 (7)	0.0037 (5)	0.0114 (6)	0.0023 (5)
C2	0.0220 (7)	0.0197 (7)	0.0190 (7)	−0.0011 (6)	0.0120 (6)	0.0013 (6)
N3	0.0193 (6)	0.0360 (8)	0.0162 (7)	0.0046 (5)	0.0104 (6)	0.0030 (5)
C4	0.0182 (7)	0.0276 (8)	0.0213 (8)	0.0039 (6)	0.0089 (7)	0.0023 (6)
C5	0.0230 (7)	0.0254 (8)	0.0273 (8)	0.0045 (6)	0.0151 (7)	0.0027 (6)
C6	0.0252 (7)	0.0233 (8)	0.0264 (8)	0.0024 (6)	0.0172 (7)	0.0022 (6)
C7	0.0299 (9)	0.0330 (9)	0.0442 (11)	−0.0031 (7)	0.0206 (9)	−0.0078 (8)
C8	0.0298 (9)	0.0410 (10)	0.0232 (9)	0.0098 (7)	0.0097 (8)	0.0067 (8)
C9	0.0365 (9)	0.0395 (10)	0.0301 (9)	0.0075 (7)	0.0216 (8)	−0.0014 (8)
C11	0.0222 (7)	0.0256 (8)	0.0157 (7)	0.0024 (6)	0.0116 (6)	0.0015 (6)
C12	0.0222 (7)	0.0234 (8)	0.0223 (8)	−0.0024 (6)	0.0114 (7)	−0.0016 (6)
C13	0.0270 (8)	0.0230 (8)	0.0246 (8)	0.0004 (6)	0.0148 (7)	0.0034 (6)
C14	0.0244 (7)	0.0286 (8)	0.0153 (7)	0.0039 (6)	0.0101 (6)	0.0024 (6)
C15	0.0259 (8)	0.0291 (8)	0.0198 (8)	−0.0044 (6)	0.0097 (7)	−0.0026 (7)
C16	0.0294 (8)	0.0248 (8)	0.0226 (8)	−0.0040 (6)	0.0146 (7)	0.0006 (6)

S1—C2	1.6904 (15)	C8—H9A	0.9800
Cl1—C14	1.7465 (16)	C8—H9B	0.9800
N1—C2	1.374 (2)	C8—H9C	0.9800
N1—C6	1.4327 (19)	C9—H8A	0.9800
N1—C11	1.4462 (19)	C9—H8B	0.9800
C2—N3	1.336 (2)	C9—H8C	0.9800
N3—C4	1.482 (2)	C11—C12	1.382 (2)
N3—H1	0.83 (2)	C11—C16	1.390 (2)
C4—C5	1.504 (2)	C12—C13	1.397 (2)
C4—C7	1.527 (2)	C12—H12	0.9500
C4—C8	1.534 (2)	C13—C14	1.382 (2)
C5—C6	1.330 (2)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.381 (2)
C6—C9	1.502 (2)	C15—C16	1.393 (2)
C7—H7A	0.9800	C15—H15	0.9500
C7—H7B	0.9800	C16—H16	0.9500
C7—H7C	0.9800
C2—N1—C6	120.78 (13)	H9A—C8—H9B	109.5
C2—N1—C11	119.87 (12)	C4—C8—H9C	109.5
C6—N1—C11	119.30 (13)	H9A—C8—H9C	109.5
N3—C2—N1	116.59 (13)	H9B—C8—H9C	109.5
N3—C2—S1	121.92 (13)	C6—C9—H8A	109.5
N1—C2—S1	121.46 (11)	C6—C9—H8B	109.5
C2—N3—C4	124.65 (15)	H8A—C9—H8B	109.5
C2—N3—H1	114.6 (14)	C6—C9—H8C	109.5
C4—N3—H1	117.4 (13)	H8A—C9—H8C	109.5
N3—C4—C5	106.41 (13)	H8B—C9—H8C	109.5
N3—C4—C7	109.73 (13)	C12—C11—C16	120.79 (14)
C5—C4—C7	111.46 (15)	C12—C11—N1	118.79 (13)
N3—C4—C8	107.47 (14)	C16—C11—N1	120.40 (14)
C5—C4—C8	111.52 (14)	C11—C12—C13	119.95 (14)
C7—C4—C8	110.09 (14)	C11—C12—H12	120.0
C6—C5—C4	122.23 (14)	C13—C12—H12	120.0
C6—C5—H5	118.9	C14—C13—C12	118.71 (15)
C4—C5—H5	118.9	C14—C13—H13	120.6
C5—C6—N1	118.87 (15)	C12—C13—H13	120.6
C5—C6—C9	124.65 (15)	C15—C14—C13	121.88 (14)
N1—C6—C9	116.40 (13)	C15—C14—Cl1	119.14 (12)
C4—C7—H7A	109.5	C13—C14—Cl1	118.97 (13)
C4—C7—H7B	109.5	C14—C15—C16	119.19 (14)
H7A—C7—H7B	109.5	C14—C15—H15	120.4
C4—C7—H7C	109.5	C16—C15—H15	120.4
H7A—C7—H7C	109.5	C11—C16—C15	119.47 (15)
H7B—C7—H7C	109.5	C11—C16—H16	120.3
C4—C8—H9A	109.5	C15—C16—H16	120.3
C4—C8—H9B	109.5
C6—N1—C2—N3	−9.4 (2)	C2—N1—C6—C9	−159.70 (15)
C11—N1—C2—N3	168.04 (14)	C11—N1—C6—C9	22.8 (2)
C6—N1—C2—S1	168.43 (11)	C2—N1—C11—C12	−87.68 (19)
C11—N1—C2—S1	−14.1 (2)	C6—N1—C11—C12	89.81 (18)
N1—C2—N3—C4	−19.9 (2)	C2—N1—C11—C16	93.85 (19)
S1—C2—N3—C4	162.28 (12)	C6—N1—C11—C16	−88.66 (19)
C2—N3—C4—C5	36.3 (2)	C16—C11—C12—C13	1.1 (2)
C2—N3—C4—C7	−84.4 (2)	N1—C11—C12—C13	−177.39 (14)
C2—N3—C4—C8	155.86 (16)	C11—C12—C13—C14	0.1 (2)
N3—C4—C5—C6	−26.8 (2)	C12—C13—C14—C15	−1.2 (3)
C7—C4—C5—C6	92.80 (19)	C12—C13—C14—Cl1	177.54 (13)
C8—C4—C5—C6	−143.71 (17)	C13—C14—C15—C16	1.2 (3)
C4—C5—C6—N1	3.6 (2)	Cl1—C14—C15—C16	−177.54 (13)
C4—C5—C6—C9	−179.71 (16)	C12—C11—C16—C15	−1.1 (3)
C2—N1—C6—C5	17.2 (2)	N1—C11—C16—C15	177.36 (15)
C11—N1—C6—C5	−160.24 (15)	C14—C15—C16—C11	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···S1i	0.83 (2)	2.59 (2)	3.4054 (16)	169.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯S1i	0.83 (2)	2.59 (2)	3.4054 (16)	169.1 (17)

Symmetry code: (i) .