1-[4-(4-Isopropyl-phen-yl)-6-methyl-2-sulfanyl-idene-1,2,3,4-tetra-hydro-pyrimidin-5-yl]ethanone.

In the title mol-ecule, C(16)H(20)N(2)OS, the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms makes a dihedral angle of 86.98 (6)° with the benzene ring. The thione, acetyl and methyl groups lie on the opposite side of the heterocyclic mean plane to the isopropylphenyl group which has an axial orientation. A weak intra-molecular C-H⋯O hydrogen bond is observed. In the crystal, molecules are linked via N-H⋯O, N-H⋯S and C-H⋯S hydrogen bonds.

Related literature

For chemical and biological applications and for the closely related crystal structures of the chloro and fluoro derivatives, see: Anuradha et al. (2009 ▶, 2012 ▶).

Experimental

Crystal data

C16H20N2OS

M = 288.41

Monoclinic,

a = 26.8413 (5) Å

b = 9.5657 (2) Å

c = 12.0764 (2) Å

β = 90.370 (2)°

V = 3100.62 (10) Å3

Z = 8

Cu Kα radiation

μ = 1.83 mm−1

T = 123 K

0.49 × 0.23 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.831, T max = 1.000

5607 measured reflections

3042 independent reflections

2776 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.05

3042 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034046/wn2487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034046/wn2487Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034046/wn2487Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812034046/wn2487Isup4.cml

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

C16H20N2OS	F(000) = 1232
Mr = 288.41	Dx = 1.236 Mg m−3
Monoclinic, C2/c	Melting point: 486 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54184 Å
a = 26.8413 (5) Å	Cell parameters from 3841 reflections
b = 9.5657 (2) Å	θ = 3.3–73.5°
c = 12.0764 (2) Å	µ = 1.83 mm−1
β = 90.370 (2)°	T = 123 K
V = 3100.62 (10) Å3	Prism, colourless
Z = 8	0.49 × 0.23 × 0.18 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3042 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 73.6°, θmin = 3.3°
ω scans	h = −30→33
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→10
Tmin = 0.831, Tmax = 1.000	l = −10→14
5607 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0684P)2 + 1.9078P] where P = (Fo2 + 2Fc2)/3
3042 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
S2	0.02408 (1)	0.17969 (4)	−0.10663 (3)	0.0195 (1)
O51	0.05759 (4)	0.41789 (12)	0.40606 (9)	0.0236 (3)
N1	0.05834 (5)	0.34011 (14)	0.05675 (10)	0.0163 (3)
N3	0.04445 (5)	0.11271 (13)	0.10324 (10)	0.0174 (3)
C2	0.04342 (5)	0.20984 (16)	0.02461 (12)	0.0157 (4)
C4	0.07362 (5)	0.12832 (15)	0.20639 (12)	0.0163 (4)
C5	0.06781 (5)	0.27819 (15)	0.24566 (12)	0.0148 (4)
C6	0.06273 (5)	0.37919 (15)	0.16783 (12)	0.0154 (4)
C14	0.27761 (7)	−0.0514 (2)	0.10895 (16)	0.0335 (6)
C15	0.28259 (8)	−0.0600 (2)	−0.01678 (18)	0.0417 (7)
C16	0.31816 (8)	0.0428 (3)	0.1572 (2)	0.0553 (8)
C41	0.12759 (6)	0.08478 (16)	0.18712 (12)	0.0184 (4)
C42	0.14242 (7)	−0.05178 (17)	0.20769 (14)	0.0255 (5)
C43	0.19116 (7)	−0.09414 (18)	0.18449 (15)	0.0294 (5)
C44	0.22550 (6)	−0.00268 (19)	0.14005 (14)	0.0268 (5)
C45	0.21077 (7)	0.1352 (2)	0.12272 (17)	0.0336 (6)
C46	0.16255 (7)	0.17846 (18)	0.14600 (16)	0.0295 (5)
C51	0.07174 (5)	0.30757 (16)	0.36521 (12)	0.0172 (4)
C52	0.09518 (7)	0.19628 (17)	0.43753 (13)	0.0238 (4)
C61	0.06312 (6)	0.53426 (16)	0.18341 (13)	0.0205 (4)
H1	0.0578 (8)	0.404 (2)	0.0103 (18)	0.027 (5)*
H3	0.0331 (8)	0.033 (2)	0.0883 (16)	0.022 (5)*
H4	0.05908	0.06499	0.26360	0.0195*
H14	0.28252	−0.14749	0.13978	0.0401*
H15A	0.25674	−0.12199	−0.04673	0.0625*
H15B	0.31551	−0.09716	−0.03547	0.0625*
H15C	0.27872	0.03349	−0.04881	0.0625*
H16A	0.31439	0.13744	0.12736	0.0829*
H16B	0.35096	0.00585	0.13732	0.0829*
H16C	0.31517	0.04545	0.23804	0.0829*
H42	0.11939	−0.11679	0.23764	0.0305*
H43	0.20084	−0.18777	0.19963	0.0353*
H45	0.23407	0.20068	0.09452	0.0403*
H46	0.15335	0.27312	0.13370	0.0353*
H52A	0.09405	0.22594	0.51515	0.0357*
H52B	0.12992	0.18230	0.41561	0.0357*
H52C	0.07678	0.10845	0.42872	0.0357*
H61A	0.07008	0.55610	0.26127	0.0308*
H61B	0.03056	0.57263	0.16234	0.0308*
H61C	0.08898	0.57568	0.13681	0.0308*

	U11	U22	U33	U12	U13	U23
S2	0.0271 (2)	0.0143 (2)	0.0171 (2)	0.0000 (1)	−0.0027 (1)	−0.0011 (1)
O51	0.0312 (6)	0.0183 (6)	0.0212 (5)	0.0007 (5)	0.0029 (4)	−0.0047 (4)
N1	0.0205 (6)	0.0117 (6)	0.0168 (6)	0.0001 (5)	0.0005 (5)	0.0016 (5)
N3	0.0226 (6)	0.0101 (6)	0.0194 (6)	−0.0027 (5)	−0.0022 (5)	−0.0006 (5)
C2	0.0159 (7)	0.0132 (7)	0.0181 (7)	0.0017 (5)	0.0011 (5)	−0.0003 (5)
C4	0.0190 (7)	0.0129 (7)	0.0169 (7)	−0.0008 (5)	−0.0005 (5)	0.0009 (5)
C5	0.0143 (6)	0.0123 (7)	0.0179 (7)	0.0000 (5)	0.0005 (5)	−0.0011 (5)
C6	0.0123 (6)	0.0145 (7)	0.0195 (7)	0.0000 (5)	0.0009 (5)	−0.0023 (5)
C14	0.0285 (9)	0.0315 (10)	0.0404 (10)	0.0150 (8)	0.0036 (7)	−0.0022 (8)
C15	0.0407 (11)	0.0405 (12)	0.0440 (11)	0.0109 (9)	0.0115 (9)	−0.0081 (9)
C16	0.0253 (10)	0.0666 (16)	0.0738 (16)	0.0188 (10)	−0.0064 (10)	−0.0274 (13)
C41	0.0212 (7)	0.0157 (7)	0.0183 (7)	0.0032 (6)	−0.0008 (5)	−0.0001 (5)
C42	0.0310 (8)	0.0164 (8)	0.0291 (8)	0.0032 (7)	0.0035 (6)	0.0025 (6)
C43	0.0355 (9)	0.0177 (8)	0.0351 (9)	0.0121 (7)	0.0026 (7)	0.0021 (7)
C44	0.0258 (8)	0.0260 (9)	0.0286 (8)	0.0099 (7)	0.0008 (6)	−0.0015 (7)
C45	0.0250 (8)	0.0262 (10)	0.0497 (11)	0.0050 (7)	0.0091 (7)	0.0095 (8)
C46	0.0240 (8)	0.0187 (9)	0.0458 (11)	0.0059 (7)	0.0065 (7)	0.0080 (7)
C51	0.0154 (7)	0.0163 (7)	0.0198 (7)	−0.0041 (5)	0.0014 (5)	0.0006 (5)
C52	0.0312 (8)	0.0216 (8)	0.0186 (7)	0.0011 (7)	−0.0026 (6)	0.0019 (6)
C61	0.0268 (8)	0.0130 (7)	0.0218 (7)	0.0025 (6)	−0.0021 (6)	0.0001 (6)

S2—C2	1.6894 (15)	C45—C46	1.389 (3)
O51—C51	1.2262 (19)	C51—C52	1.512 (2)
N1—C2	1.365 (2)	C4—H4	1.0000
N1—C6	1.3968 (19)	C14—H14	1.0000
N3—C2	1.3287 (19)	C15—H15A	0.9800
N3—C4	1.4746 (19)	C15—H15B	0.9800
N1—H1	0.83 (2)	C15—H15C	0.9800
N3—H3	0.840 (19)	C16—H16A	0.9800
C4—C41	1.527 (2)	C16—H16B	0.9800
C4—C5	1.518 (2)	C16—H16C	0.9800
C5—C51	1.474 (2)	C42—H42	0.9500
C5—C6	1.354 (2)	C43—H43	0.9500
C6—C61	1.495 (2)	C45—H45	0.9500
C14—C44	1.524 (2)	C46—H46	0.9500
C14—C15	1.527 (3)	C52—H52A	0.9800
C14—C16	1.526 (3)	C52—H52B	0.9800
C41—C46	1.392 (2)	C52—H52C	0.9800
C41—C42	1.388 (2)	C61—H61A	0.9800
C42—C43	1.400 (3)	C61—H61B	0.9800
C43—C44	1.382 (2)	C61—H61C	0.9800
C44—C45	1.392 (3)
C2—N1—C6	122.71 (13)	C41—C4—H4	108.00
C2—N3—C4	122.78 (12)	C15—C14—H14	108.00
C6—N1—H1	117.0 (14)	C16—C14—H14	108.00
C2—N1—H1	118.5 (14)	C44—C14—H14	108.00
C2—N3—H3	118.4 (13)	C14—C15—H15A	109.00
C4—N3—H3	117.6 (14)	C14—C15—H15B	109.00
N1—C2—N3	115.51 (13)	C14—C15—H15C	109.00
S2—C2—N3	123.78 (12)	H15A—C15—H15B	109.00
S2—C2—N1	120.71 (11)	H15A—C15—H15C	109.00
N3—C4—C41	110.05 (12)	H15B—C15—H15C	109.00
C5—C4—C41	113.87 (12)	C14—C16—H16A	109.00
N3—C4—C5	107.72 (11)	C14—C16—H16B	109.00
C4—C5—C6	117.84 (13)	C14—C16—H16C	109.00
C4—C5—C51	118.63 (12)	H16A—C16—H16B	110.00
C6—C5—C51	123.37 (13)	H16A—C16—H16C	109.00
N1—C6—C61	112.76 (13)	H16B—C16—H16C	109.00
C5—C6—C61	128.30 (14)	C41—C42—H42	120.00
N1—C6—C5	118.89 (13)	C43—C42—H42	120.00
C15—C14—C16	110.16 (17)	C42—C43—H43	119.00
C15—C14—C44	110.36 (16)	C44—C43—H43	119.00
C16—C14—C44	112.27 (16)	C44—C45—H45	119.00
C42—C41—C46	118.48 (16)	C46—C45—H45	120.00
C4—C41—C42	120.06 (14)	C41—C46—H46	120.00
C4—C41—C46	121.43 (14)	C45—C46—H46	120.00
C41—C42—C43	120.28 (16)	C51—C52—H52A	109.00
C42—C43—C44	121.41 (16)	C51—C52—H52B	109.00
C14—C44—C43	121.18 (16)	C51—C52—H52C	109.00
C14—C44—C45	120.86 (16)	H52A—C52—H52B	109.00
C43—C44—C45	117.95 (16)	H52A—C52—H52C	109.00
C44—C45—C46	121.05 (17)	H52B—C52—H52C	109.00
C41—C46—C45	120.78 (16)	C6—C61—H61A	109.00
O51—C51—C52	120.17 (13)	C6—C61—H61B	109.00
C5—C51—C52	117.29 (13)	C6—C61—H61C	109.00
O51—C51—C5	122.53 (13)	H61A—C61—H61B	109.00
N3—C4—H4	108.00	H61A—C61—H61C	109.00
C5—C4—H4	108.00	H61B—C61—H61C	109.00
C6—N1—C2—S2	163.66 (11)	C51—C5—C6—C61	4.0 (2)
C6—N1—C2—N3	−15.1 (2)	C4—C5—C51—O51	−164.54 (13)
C2—N1—C6—C5	21.1 (2)	C4—C5—C51—C52	16.63 (19)
C2—N1—C6—C61	−161.20 (13)	C6—C5—C51—O51	20.2 (2)
C4—N3—C2—S2	162.66 (11)	C6—C5—C51—C52	−158.59 (14)
C4—N3—C2—N1	−18.6 (2)	C15—C14—C44—C43	107.02 (19)
C2—N3—C4—C5	41.10 (18)	C15—C14—C44—C45	−71.9 (2)
C2—N3—C4—C41	−83.58 (17)	C16—C14—C44—C43	−129.67 (19)
N3—C4—C5—C6	−32.96 (17)	C16—C14—C44—C45	51.4 (2)
N3—C4—C5—C51	151.56 (12)	C4—C41—C42—C43	176.53 (15)
C41—C4—C5—C6	89.38 (16)	C46—C41—C42—C43	−1.7 (2)
C41—C4—C5—C51	−86.10 (15)	C4—C41—C46—C45	−176.17 (16)
N3—C4—C41—C42	−92.42 (16)	C42—C41—C46—C45	2.0 (3)
N3—C4—C41—C46	85.75 (17)	C41—C42—C43—C44	−0.5 (3)
C5—C4—C41—C42	146.53 (14)	C42—C43—C44—C14	−176.54 (16)
C5—C4—C41—C46	−35.3 (2)	C42—C43—C44—C45	2.4 (3)
C4—C5—C6—N1	5.98 (19)	C14—C44—C45—C46	176.88 (18)
C4—C5—C6—C61	−171.27 (13)	C43—C44—C45—C46	−2.1 (3)
C51—C5—C6—N1	−178.77 (13)	C44—C45—C46—C41	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O51i	0.83 (2)	2.12 (2)	2.9445 (17)	174 (2)
N3—H3···S2ii	0.840 (19)	2.56 (2)	3.3481 (13)	156.9 (18)
C61—H61A···O51	0.98	2.22	2.9148 (19)	127
C61—H61B···S2iii	0.98	2.86	3.7145 (16)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O51i	0.83 (2)	2.12 (2)	2.9445 (17)	174 (2)
N3—H3⋯S2ii	0.840 (19)	2.56 (2)	3.3481 (13)	156.9 (18)
C61—H61A⋯O51	0.98	2.22	2.9148 (19)	127
C61—H61B⋯S2iii	0.98	2.86	3.7145 (16)	146

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