1-[4-(4-Isopropyl­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl]ethanone

Anuradha, N.; Thiruvalluvar, A.; Chitra, S.; Devanathan, D.; Falola, O.O.; Butcher, R.J.

doi:10.1107/S1600536812034046

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2641

doi:10.1107/S1600536812034046

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1-[4-(4-Isopropylphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone

N. Anuradha,^a A. Thiruvalluvar,^a ^* S. Chitra,^b D. Devanathan,^c Oluwaseun O. Falola ^d and R.J. Butcher ^d

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, K.S.R. College of Engineering, K.S.R. Kalvi Nagar, Tiruchengode 637 215, Tamilnadu, India, ^cDepartment of Chemistry, Government Arts College, C. Mutlur 608 102, Chidambaram, Tamilnadu, India, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 29 July 2012; accepted 30 July 2012; online 4 August 2012)

In the title molecule, C₁₆H₂₀N₂OS, 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 intramolecular 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_r = 288.41
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.05
3042 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) -x, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034046/wn2487sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812034046/wn2487Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812034046/wn2487Isup4.cml

checkCIF report

Comment top

As part of our investigations of dihydropyrimidine derivatives (Anuradha et al., 2009, 2012) to compare their chemical and biological activities, we have undertaken the X-ray crystal structure analysis of the title compound.

In the title molecule, C₁₆H₂₀N₂OS (Fig.1), the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms( C2, N3, C5 and C6) makes a dihedral angle of 86.98 (6)° with the benzene ring. The thione, acetyl and methyl groups have equatorial orientations with respect to the attached heterocyclic ring, whereas the isopropylphenyl group has an axial orientation.

Intermolecular N1—H1···O51, N3—H3···S2 and C61—H61B···S2 hydrogen bonds are found in the crystal structure. A weak intramolecular C61—H61A···O51 hydrogen bond is also observed (Fig. 2, Table 1).

Related literature top

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 top

A solution of acetylacetone (1.0012 g, 0.01 mol), 4-isopropylbenzaldehyde (1.48 g, 0.01 mol) and thiourea (1.14 g, 0.015 mol) was heated under reflux in the presence of calcium fluoride (0.07 g, 0.001 mol) for 2 h (monitored by TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and poured into crushed ice. The solid product was filtered under suction and purified by recrystallization from hot methanol to give the product in pure form. Yield 1.86 g (93%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. Dashed lines indicate the intramolecular C—H···O hydrogen bond.
	Fig. 2. The packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-[4-(4-Isopropylphenyl)-6-methyl-2-sulfanylidene-1,2,3,4- tetrahydropyrimidin-5-yl]ethanone top

Crystal data top

C₁₆H₂₀N₂OS	F(000) = 1232
M_r = 288.41	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0684P)² + 1.9078P] where P = (F_o² + 2F_c²)/3
3042 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₂₀N₂OS	V = 3100.62 (10) Å³
M_r = 288.41	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 26.8413 (5) Å	µ = 1.83 mm⁻¹
b = 9.5657 (2) Å	T = 123 K
c = 12.0764 (2) Å	0.49 × 0.23 × 0.18 mm
β = 90.370 (2)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3042 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2776 reflections with I > 2σ(I)
T_min = 0.831, T_max = 1.000	R_int = 0.024
5607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.42 e Å⁻³
3042 reflections	Δρ_min = −0.39 e Å⁻³
193 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2; (ii) −x, −y, −z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₂OS
M_r	288.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	26.8413 (5), 9.5657 (2), 12.0764 (2)
β (°)	90.370 (2)
V (Å³)	3100.62 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.83
Crystal size (mm)	0.49 × 0.23 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.831, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5607, 3042, 2776
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.05
No. of reflections	3042
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2; (ii) −x, −y, −z; (iii) −x, −y+1, −z.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Anuradha, N., Thiruvalluvar, A., Chitra, S., Devanathan, D. & Butcher, R. J. (2012). Acta Cryst. E68, o2625. CSD CrossRef IUCr Journals Google Scholar
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o564–o565. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page o2641

doi:10.1107/S1600536812034046

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[4-(4-Iso­propyl­phen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl]ethanone

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Acknowledgements

References

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1-[4-(4-Isopropylphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone