1-(6-Methyl-3-phenyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl)ethanone

Garibov, E.N.; Gojayeva, S.S.; Allahverdiyev, M.A.; Gurbanov, A.V.G.; Brito, I.

doi:10.1107/S1600536811055309

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o276

doi:10.1107/S1600536811055309

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1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone

Emin N. Garibov,^a Sevinj S. Gojayeva,^a Mirze A. Allahverdiyev,^a Atash V. Gurbanov Gurbanov ^a and Iván Brito ^b ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and ^bDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
^*Correspondence e-mail: ivanbritob@yahoo.com

(Received 7 December 2011; accepted 23 December 2011; online 7 January 2012)

In the title compound, C₁₃H₁₄N₂OS, four C atoms of the phenyl ring are disordered over two sets of sites in a 0.60 (3):0.40 (3) ratio. The heterocyclic ring is essentially planar (r.m.s. deviation = 0.017 Å) and forms dihedral angles of 82.0 (2) and 79.3 (3)°, respectively, with the major and minor occupancy components of the phenyl ring. The crystal packing features N—H⋯O hydrogen bonds, which link the molecules into C(6) chains running parallel to the b axis.

Related literature

For synthetic methods, see: Kotharkar et al. (2006 ); Lu et al. (2000 ); Salehi et al. (2003 ); Srinivas & Das (2004 ). For pharmacological properties of related compounds, see: Dalinger et al. (2004 ). For graph-set notation see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₄N₂OS
M_r = 246.32
Orthorhombic, P n a 2₁
a = 24.3527 (10) Å
b = 7.2374 (3) Å
c = 7.0063 (3) Å
V = 1234.86 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.930, T_max = 0.930
13745 measured reflections
3089 independent reflections
2877 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.00
3089 reflections
150 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.88	2.05	2.920 (2)	168
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055309/lr2042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055309/lr2042Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055309/lr2042Isup3.cml

checkCIF report

Comment top

The dihydropyrimidinethiones display many pharmacological properties (Dalinger et al. 2004), as part of our interest in this kind of materials, we report here the synthesis and crystal structure determination of the title compound. Our synthesis is based in the Bidjinelli reaction, which consists on a three-component condensation of an aldehyde, a methylene active compound and an thiourea derivative in acidic media. This procedure is the most simple and useful for the preparation of 3,4-dihydropyrimidene-2(1H) thiones (Kotharkar et al. 2006; Lu et al. 2000; Srinivas & Das, 2004; Salehi et al. 2003).

In the compound, the C8, C9, C11 and C12 atoms of the phenyl ring are disordered over two sets of sites in a 0.60 (3):0.40 (3) ratio. The heterocycle ring is essentially planar (r.m.s.= 0.017 Å) and form a dihedral angle of 82.0 (2)° with the phenyl ring.The crystal packing is stabilized by intermolecular N3—H3N···O1 hydrogen bonds (Table 1), which link the molecules into chains running parallel to the b axis (Fig.2), with graph-set notation C(6), (Bernstein et al. 1995).

Related literature top

For synthetic methods, see: Kotharkar et al. (2006); Lu et al. (2000); Salehi et al. (2003); Srinivas & Das (2004). For pharmacological properties of related compounds, see: Dalinger et al. (2004). For graph-set notation see: Bernstein et al. (1995).

Experimental top

Phenylthiourea, 15.2 g (0.1 mol), 37% water solution of formaldehyde (formaline), 3 g (0.1 mol) and 13 g (0.1 mol) of acetoacetic ester were dissolved in 10 ml of ethanol and then 0.5 ml of trifluoroacetic was added. The mixture was vigorously stirred during 4–5 h at room temperature and then cooled and kept one day at 0°C. The white crystals of 1-(6-methyl-3-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl) ethanone were filtered and washed with dichloromethane. Suitable crystal for diffraction were obtained by slow evaporation from ethanol. The yield was of 19.2 g (70%). Mp 180°C. R_f = 0.35. Eluent- ethanol:hexane (5:2). ¹H NMR (300 MHz, DMSO-d6) δ 1.35 (s, 3H, CH₃), 6.8–7.1 (m, H, Ar), 7.4 (m, H, Ar), 9.35 (s, 1H, NH). ¹³C NMR (75 MHz, DMSO-d6) δ 24, 29, 37, 51, 86, 117, 122, 129, 132, 141, 151, 179 (C=S), 205 (C=O)

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, including disorder. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound. N—H···O hydrogen bonds are shown as dashed lines. For clarity only one of the disordered components of the phenyl ring is shown.

1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone top

Crystal data top

C₁₃H₁₄N₂OS	F(000) = 520
M_r = 246.32	D_x = 1.325 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7985 reflections
a = 24.3527 (10) Å	θ = 2.9–28.3°
b = 7.2374 (3) Å	µ = 0.25 mm⁻¹
c = 7.0063 (3) Å	T = 100 K
V = 1234.86 (9) Å³	Cube, colourless
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −32→32
T_min = 0.930, T_max = 0.930	k = −9→9
13745 measured reflections	l = −9→9

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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0713P)² + 0.8297P] where P = (F_o² + 2F_c²)/3
3089 reflections	(Δ/σ)_max = 0.001
150 parameters	Δρ_max = 0.40 e Å⁻³
19 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₁₄N₂OS	V = 1234.86 (9) Å³
M_r = 246.32	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 24.3527 (10) Å	µ = 0.25 mm⁻¹
b = 7.2374 (3) Å	T = 100 K
c = 7.0063 (3) Å	0.30 × 0.30 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	3089 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2877 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.930	R_int = 0.016
13745 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	19 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	Δρ_max = 0.40 e Å⁻³
3089 reflections	Δρ_min = −0.35 e Å⁻³
150 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.36824 (2)	1.18702 (7)	0.3739 (4)	0.04639 (18)
O1	0.51205 (7)	0.42042 (19)	0.3715 (9)	0.0661 (6)
N1	0.39774 (6)	0.8325 (2)	0.3725 (6)	0.0341 (3)
C2	0.41226 (7)	1.0102 (2)	0.3775 (7)	0.0314 (3)
N3	0.46747 (6)	1.04586 (19)	0.3735 (7)	0.0349 (3)
H3N	0.4761	1.1644	0.3753	0.042*
C4	0.50891 (7)	0.9147 (2)	0.3784 (6)	0.0280 (3)
C5	0.49517 (7)	0.7330 (2)	0.3726 (7)	0.0327 (4)
C6	0.43611 (8)	0.6775 (2)	0.3775 (11)	0.0512 (6)
H6A	0.4286	0.5959	0.2672	0.061*
H6B	0.4294	0.6051	0.4950	0.061*
C7	0.34084 (7)	0.7781 (2)	0.3747 (3)	0.0413 (4)
C8	0.3095 (2)	0.7676 (8)	0.2110 (7)	0.0577 (9)	0.60
H8A	0.3243	0.8010	0.0903	0.069*	0.60
C9	0.2556 (3)	0.7066 (7)	0.2280 (7)	0.0577 (9)	0.60
H9A	0.2329	0.6976	0.1182	0.069*	0.60
C8'	0.3160 (4)	0.7165 (12)	0.2081 (8)	0.0577 (9)	0.40
H8B	0.3344	0.7152	0.0885	0.069*	0.40
C9'	0.2620 (4)	0.6568 (13)	0.2298 (9)	0.0577 (9)	0.40
H9B	0.2427	0.6130	0.1210	0.069*	0.40
C10	0.23526 (11)	0.6591 (3)	0.4053 (5)	0.0833 (14)
H10A	0.1983	0.6178	0.4141	0.100*
C13	0.56501 (7)	0.9991 (3)	0.3745 (8)	0.0406 (4)
H13A	0.5881	0.9320	0.2833	0.061*
H13B	0.5814	0.9916	0.5020	0.061*
H13C	0.5622	1.1289	0.3358	0.061*
C14	0.53254 (8)	0.5753 (2)	0.3726 (8)	0.0386 (4)
C15	0.59377 (9)	0.5914 (3)	0.3708 (10)	0.0538 (6)
H15A	0.6101	0.4693	0.3909	0.081*
H15B	0.6055	0.6751	0.4729	0.081*
H15C	0.6058	0.6406	0.2473	0.081*
C11	0.2664 (2)	0.6689 (8)	0.5722 (7)	0.0577 (9)	0.60
H11A	0.2516	0.6354	0.6928	0.069*	0.60
C12	0.3200 (3)	0.7300 (7)	0.5526 (6)	0.0577 (9)	0.60
H12A	0.3428	0.7392	0.6622	0.069*	0.60
C11'	0.2596 (4)	0.7202 (12)	0.5726 (11)	0.0577 (9)	0.40
H11B	0.2413	0.7218	0.6924	0.069*	0.40
C12'	0.3133 (4)	0.7788 (13)	0.5473 (9)	0.0577 (9)	0.40
H12B	0.3325	0.8225	0.6563	0.069*	0.40

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0357 (3)	0.0330 (3)	0.0704 (4)	0.00649 (18)	0.0000 (5)	−0.0009 (5)
O1	0.0503 (9)	0.0230 (6)	0.1250 (17)	−0.0015 (6)	−0.014 (2)	0.006 (2)
N1	0.0267 (7)	0.0277 (7)	0.0480 (8)	−0.0031 (5)	0.0033 (14)	0.0073 (15)
C2	0.0321 (8)	0.0271 (7)	0.0351 (8)	0.0008 (6)	−0.0035 (14)	−0.0005 (15)
N3	0.0302 (7)	0.0208 (6)	0.0537 (9)	−0.0025 (5)	−0.0048 (14)	−0.0063 (15)
C4	0.0280 (7)	0.0246 (7)	0.0315 (8)	−0.0019 (6)	−0.0049 (12)	0.0061 (13)
C5	0.0305 (8)	0.0246 (7)	0.0429 (9)	−0.0021 (6)	0.0070 (16)	0.0091 (17)
C6	0.0315 (9)	0.0251 (8)	0.0970 (18)	−0.0036 (7)	−0.010 (2)	0.002 (2)
C7	0.0277 (8)	0.0310 (8)	0.0652 (12)	−0.0041 (7)	0.0077 (18)	0.000 (2)
C8	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C9	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C8'	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C9'	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C10	0.0341 (12)	0.0659 (17)	0.150 (4)	−0.0103 (12)	0.026 (2)	0.002 (3)
C13	0.0316 (8)	0.0301 (8)	0.0601 (12)	−0.0051 (7)	−0.0087 (17)	0.0104 (19)
C14	0.0399 (9)	0.0255 (8)	0.0502 (10)	0.0019 (7)	−0.0041 (17)	−0.0089 (17)
C15	0.0383 (10)	0.0368 (10)	0.0864 (17)	0.0087 (8)	0.012 (2)	0.016 (2)
C11	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C12	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C11'	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)
C12'	0.0353 (13)	0.052 (3)	0.0853 (11)	−0.0022 (15)	−0.0014 (10)	0.0077 (14)

Geometric parameters (Å, º) top

S1—C2	1.6694 (17)	C9—H9A	0.9500
O1—C14	1.227 (2)	C8'—C9'	1.393 (3)
N1—C2	1.334 (2)	C8'—H8B	0.9500
N1—C7	1.441 (2)	C9'—C10	1.391 (3)
N1—C6	1.460 (2)	C9'—H9B	0.9500
C2—N3	1.369 (2)	C10—C11'	1.386 (3)
N3—C4	1.386 (2)	C10—C11	1.395 (3)
N3—H3N	0.8834	C10—H10A	0.9500
C4—C5	1.357 (2)	C13—H13A	0.9800
C4—C13	1.497 (2)	C13—H13B	0.9800
C5—C14	1.460 (2)	C13—H13C	0.9800
C5—C6	1.494 (2)	C14—C15	1.496 (3)
C6—H6A	0.9900	C15—H15A	0.9800
C6—H6B	0.9900	C15—H15B	0.9800
C7—C8	1.380 (3)	C15—H15C	0.9800
C7—C12'	1.384 (3)	C11—C12	1.386 (3)
C7—C8'	1.389 (3)	C11—H11A	0.9500
C7—C12	1.390 (3)	C12—H12A	0.9500
C8—C9	1.391 (3)	C11'—C12'	1.385 (3)
C8—H8A	0.9500	C11'—H11B	0.9500
C9—C10	1.381 (3)	C12'—H12B	0.9500

C2—N1—C7	121.21 (14)	C10—C9'—C8'	122.3 (9)
C2—N1—C6	124.76 (15)	C10—C9'—H9B	118.8
C7—N1—C6	113.90 (14)	C8'—C9'—H9B	118.8
N1—C2—N3	116.18 (15)	C9—C10—C11'	121.9 (6)
N1—C2—S1	124.62 (13)	C9—C10—C9'	16.3 (4)
N3—C2—S1	119.08 (13)	C11'—C10—C9'	123.5 (6)
C2—N3—C4	125.84 (14)	C9—C10—C11	123.1 (4)
C2—N3—H3N	114.6	C11'—C10—C11	16.8 (4)
C4—N3—H3N	119.4	C9'—C10—C11	119.2 (6)
C5—C4—N3	118.90 (15)	C9—C10—H10A	118.4
C5—C4—C13	128.30 (16)	C11'—C10—H10A	116.8
N3—C4—C13	112.62 (14)	C9'—C10—H10A	119.7
C4—C5—C14	127.14 (16)	C11—C10—H10A	118.4
C4—C5—C6	119.80 (16)	C4—C13—H13A	109.5
C14—C5—C6	112.96 (15)	C4—C13—H13B	109.5
N1—C6—C5	114.15 (14)	H13A—C13—H13B	109.5
N1—C6—H6A	108.7	C4—C13—H13C	109.5
C5—C6—H6A	108.7	H13A—C13—H13C	109.5
N1—C6—H6B	108.7	H13B—C13—H13C	109.5
C5—C6—H6B	108.7	O1—C14—C5	117.44 (18)
H6A—C6—H6B	107.6	O1—C14—C15	118.47 (18)
C8—C7—C12'	117.3 (6)	C5—C14—C15	124.08 (16)
C8—C7—C8'	16.7 (4)	C14—C15—H15A	109.5
C12'—C7—C8'	121.6 (6)	C14—C15—H15B	109.5
C8—C7—C12	122.0 (4)	H15A—C15—H15B	109.5
C12'—C7—C12	16.2 (4)	C14—C15—H15C	109.5
C8'—C7—C12	121.0 (6)	H15A—C15—H15C	109.5
C8—C7—N1	122.5 (4)	H15B—C15—H15C	109.5
C12'—C7—N1	118.4 (5)	C12—C11—C10	116.4 (6)
C8'—C7—N1	119.9 (5)	C12—C11—H11A	121.8
C12—C7—N1	115.4 (4)	C10—C11—H11A	121.8
C7—C8—C9	117.9 (6)	C11—C12—C7	120.8 (6)
C7—C8—H8A	121.0	C11—C12—H12A	119.6
C9—C8—H8A	121.0	C7—C12—H12A	119.6
C10—C9—C8	119.7 (6)	C12'—C11'—C10	113.1 (9)
C10—C9—H9A	120.2	C12'—C11'—H11B	123.4
C8—C9—H9A	120.2	C10—C11'—H11B	123.4
C7—C8'—C9'	114.8 (9)	C7—C12'—C11'	124.7 (10)
C7—C8'—H8B	122.6	C7—C12'—H12B	117.7
C9'—C8'—H8B	122.6	C11'—C12'—H12B	117.7

C7—N1—C2—N3	−179.6 (3)	C12'—C7—C8'—C9'	0.01 (3)
C6—N1—C2—N3	4.8 (7)	C12—C7—C8'—C9'	19.0 (5)
C7—N1—C2—S1	−3.7 (6)	N1—C7—C8'—C9'	176.16 (17)
C6—N1—C2—S1	−179.4 (4)	C7—C8'—C9'—C10	0.00 (3)
N1—C2—N3—C4	−4.8 (6)	C8—C9—C10—C11'	19.9 (5)
S1—C2—N3—C4	179.1 (3)	C8—C9—C10—C9'	−81 (3)
C2—N3—C4—C5	5.2 (6)	C8—C9—C10—C11	−0.03 (7)
C2—N3—C4—C13	−179.3 (4)	C8'—C9'—C10—C9	90 (3)
N3—C4—C5—C14	178.7 (4)	C8'—C9'—C10—C11'	0.01 (7)
C13—C4—C5—C14	4.0 (7)	C8'—C9'—C10—C11	−19.1 (5)
N3—C4—C5—C6	−5.1 (6)	C4—C5—C14—O1	178.2 (5)
C13—C4—C5—C6	−179.8 (5)	C6—C5—C14—O1	1.8 (7)
C2—N1—C6—C5	−4.9 (8)	C4—C5—C14—C15	−2.7 (8)
C7—N1—C6—C5	179.2 (4)	C6—C5—C14—C15	−179.2 (5)
C4—C5—C6—N1	4.8 (7)	C9—C10—C11—C12	0.06 (9)
C14—C5—C6—N1	−178.4 (4)	C11'—C10—C11—C12	−91 (2)
C2—N1—C7—C8	85.5 (4)	C9'—C10—C11—C12	18.5 (5)
C6—N1—C7—C8	−98.5 (5)	C10—C11—C12—C7	−0.06 (8)
C2—N1—C7—C12'	−79.0 (5)	C8—C7—C12—C11	0.04 (7)
C6—N1—C7—C12'	97.1 (5)	C12'—C7—C12—C11	78 (3)
C2—N1—C7—C8'	104.8 (5)	C8'—C7—C12—C11	−19.5 (5)
C6—N1—C7—C8'	−79.2 (6)	N1—C7—C12—C11	−177.66 (16)
C2—N1—C7—C12	−96.8 (4)	C9—C10—C11'—C12'	−19.3 (5)
C6—N1—C7—C12	79.2 (5)	C9'—C10—C11'—C12'	−0.02 (8)
C12'—C7—C8—C9	−17.9 (5)	C11—C10—C11'—C12'	80 (2)
C8'—C7—C8—C9	92 (2)	C8—C7—C12'—C11'	18.5 (5)
C12—C7—C8—C9	−0.01 (3)	C8'—C7—C12'—C11'	−0.03 (7)
N1—C7—C8—C9	177.52 (17)	C12—C7—C12'—C11'	−93 (3)
C7—C8—C9—C10	0.01 (3)	N1—C7—C12'—C11'	−176.23 (17)
C8—C7—C8'—C9'	−80 (2)	C10—C11'—C12'—C7	0.04 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.88	2.05	2.920 (2)	168

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂OS
M_r	246.32
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	24.3527 (10), 7.2374 (3), 7.0063 (3)
V (Å³)	1234.86 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.930, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	13745, 3089, 2877
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.00
No. of reflections	3089
No. of parameters	150
No. of restraints	19
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.88	2.05	2.920 (2)	168

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors thank Baku State University and the Universidad de Antofagasta for supporting this study. Thanks are also given to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a license for the use of the Cambridge Structural Database (CSD).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SAINT-Plus. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Dalinger, D., Stadler, A. & Kappe, C. O. (2004). Pure Appl. Chem. 76, 1017–1024. Google Scholar
Kotharkar, S. A., Nagawade, R. R. & Shinde, D. B. (2006). Ukrainica Bioorg. Acta, 2, 17–21. Google Scholar
Lu, J., Bai, Y., Wang, Z., Yang, B. & Ma, H. (2000). Tetrahedron Lett. 41, 9075–9078. Web of Science CrossRef CAS Google Scholar
Salehi, P., Davizi, M., Zolfigol, A. M. & Fard, M. A. (2003). Tetrahedron Lett. 44, 2889–289. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS, Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srinivas, K. V. & Das, B. (2004). Synthesis, 13, 2091–2093. Google Scholar

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Volume 68| Part 2| February 2012| Page o276

doi:10.1107/S1600536811055309

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

1-(6-Methyl-3-phenyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl)ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone