Crystal structure of ethyl 4-(2-meth­oxy­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Khodairy, A.; Ahmed, E.A.

doi:10.1107/S2056989015010026

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o444-o445

doi:10.1107/S2056989015010026

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Crystal structure of ethyl 4-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Ahmed Khodairy ^e and Eman A. Ahmed ^e ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt
^*Correspondence e-mail: abdala_15@yahoo.com

Edited by H. Ishida, Okayama University, Japan (Received 13 May 2015; accepted 23 May 2015; online 3 June 2015)

In the title compound, C₁₅H₁₈N₂O₃S, the hydropyrimidine ring adopts a sofa conformation with the methine C atom as the flap. The benzene ring is almost perpendicular to the mean plane of the hydropyrimidine ring, making a dihedral angle of 85.51 (8)°, and the methoxy O atom lies over the centre of the pyrimidine ring. In the crystal, weak N—H⋯S interactions form a zigzag chain running along the b-axis direction.

Keywords: crystal structure; Biginelli reactions; dihyropyrimidinones; three-component reactions; N—H⋯S interactions.

CCDC reference: 1402530

1. Related literature

For syntheses of dihydropyrimidinones and their analogous, see: Biginelli (1893 ); Varala et al. (2003 ); Gohain et al. (2004 ); Ahmed et al. (2009 ). For biological activities of hydropyrimidinones, see: Salehi et al. (2006 ); Singh et al. (2010 ); Hed et al. (2009 ); Russowsky et al. (2007 ); Shah et al. (2009 ). For the synthesis of the title compound, see: Ahmed et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₅H₁₈N₂O₃S
M_r = 306.37
Triclinic, $[P \overline 1]$
a = 7.9791 (2) Å
b = 8.2031 (2) Å
c = 11.8405 (3) Å
α = 81.987 (1)°
β = 87.975 (1)°
γ = 80.850 (1)°
V = 757.60 (3) Å³
Z = 2
Cu Kα radiation
μ = 2.00 mm⁻¹
T = 150 K
0.25 × 0.21 × 0.12 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.73, T_max = 0.79
9145 measured reflections
2929 independent reflections
2773 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.08
2929 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1ⁱ	0.91	2.46	3.3539 (13)	167
N2—H2A⋯S1ⁱⁱ	0.91	2.58	3.4327 (14)	157
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1402530

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015010026/is5401sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010026/is5401Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010026/is5401Isup3.cml

checkCIF report

Comment top

Dihydropyrimidin-2(1H)-one scaffold compounds are an important class of substances in organic and medicinal chemistry. Aryl-substituted 3, 4-dihydropyrimidin-2(1H)-ones and their sulfur analogue have been reported to possess diverse range of pharmacological activity (Salehi et al., 2006) such as anticancer, anti HIV, antibacterial, antimalarial, antihypertensive, sedative, hypnotics, anticonvulsant, antithyroid,antihistaminic agents and antibiotics (Singh et al., 2010; Hed et al., 2009; Russowsky et al., 2007; Shah et al., 2009). This stimulated the invention of a wide range of synthetic methods for their preparation and chemical transformations. In recent years, several modified procedures have been reported to improve the efficiency of the Biginelli dihydropyrimidine synthesis (Biginelli, 1893) by using different catalysts e.g. Lewis acids (Varala et al., 2003; Gohain et al., 2004) or by using basic condition via phase transfer catalysis (Ahmed et al., 2009). In this context, we report in this study the crystal structure of the title compound.

In the title compound (Fig. 1), the plane of the benzene ring is almost parallel to the C1···N2 vector with the methoxy oxygen atom (O1) lying over the centre of the pyrimidine ring. The pyrimidine ring has Cremer-Pople puckering parameters Q = 0.201 (2) Å, θ = 62.2 (5)° and ϕ = 42.9 (2)°. In the crystal, weak N—H···S interactions (Table 1) form a chain running parallel to the b axis (Figs. 2 & 3).

Related literature top

For syntheses of dihydropyrimidinones and their analogous, see: Biginelli (1893); Varala et al. (2003); Gohain et al. (2004); Ahmed et al. (2009). For biological activities of hydropyrimidinones, see: Salehi et al. (2006); Singh et al. (2010); Hed et al. (2009); Russowsky et al. (2007); Shah et al. (2009). For the synthesis of the title compound, see: Ahmed et al. (2012).

Experimental top

The title compound was prepared according to our reported method (Ahmed et al., 2012). Colourless crystals suitable for X-ray analysis were grown from ethanol (m.p. 473–475 K, yield 98%).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

Figures top

	Fig. 1. The molecular structure of the title compound showing labeling scheme and 50% probability ellipsoids.
	Fig. 2. A section of the chain formed by N—H···S hydrogen bonds (dashed lines).
	Fig. 3. A packing diagram viewed along the b axis. N—H···S interactions are shown as dotted lines.

Ethyl 4-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₅H₁₈N₂O₃S	Z = 2
M_r = 306.37	F(000) = 324
Triclinic, P1	D_x = 1.343 Mg m⁻³
a = 7.9791 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.2031 (2) Å	Cell parameters from 7936 reflections
c = 11.8405 (3) Å	θ = 3.8–72.2°
α = 81.987 (1)°	µ = 2.00 mm⁻¹
β = 87.975 (1)°	T = 150 K
γ = 80.850 (1)°	Thick plate, colourless
V = 757.60 (3) Å³	0.25 × 0.21 × 0.12 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2929 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2773 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.2°, θ_min = 3.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→10
T_min = 0.73, T_max = 0.79	l = −14→14
9145 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)] = 0.039	Hydrogen site location: mixed
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0487P)² + 0.4254P] where P = (F_o² + 2F_c²)/3
2929 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₈N₂O₃S	γ = 80.850 (1)°
M_r = 306.37	V = 757.60 (3) Å³
Triclinic, P1	Z = 2
a = 7.9791 (2) Å	Cu Kα radiation
b = 8.2031 (2) Å	µ = 2.00 mm⁻¹
c = 11.8405 (3) Å	T = 150 K
α = 81.987 (1)°	0.25 × 0.21 × 0.12 mm
β = 87.975 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2929 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2773 reflections with I > 2σ(I)
T_min = 0.73, T_max = 0.79	R_int = 0.021
9145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 0.43 e Å⁻³
2929 reflections	Δρ_min = −0.26 e Å⁻³
193 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
S1	1.08339 (5)	0.22865 (4)	1.02799 (3)	0.02400 (13)
O1	0.64475 (15)	0.28798 (15)	0.86937 (10)	0.0312 (3)
O2	0.8568 (2)	0.26940 (18)	0.47910 (11)	0.0494 (4)
O3	0.75790 (16)	0.52294 (15)	0.52331 (9)	0.0304 (3)
N1	0.96037 (16)	0.42742 (15)	0.84338 (11)	0.0213 (3)
H1A	0.9617	0.5109	0.8864	0.026*
N2	0.99441 (17)	0.14788 (16)	0.83198 (11)	0.0240 (3)
H2A	1.0080	0.0431	0.8710	0.029*
C1	0.85934 (19)	0.47576 (19)	0.73835 (13)	0.0216 (3)
H1	0.9084	0.5685	0.6916	0.026*
C2	1.00503 (19)	0.27318 (19)	0.89394 (13)	0.0209 (3)
C3	0.9414 (2)	0.1739 (2)	0.71936 (13)	0.0247 (3)
C4	0.9585 (3)	0.0158 (2)	0.66684 (15)	0.0351 (4)
H4A	0.8722	0.0271	0.6082	0.053*
H4B	0.9429	−0.0770	0.7259	0.053*
H4C	1.0717	−0.0061	0.6320	0.053*
C5	0.88282 (19)	0.3296 (2)	0.66990 (13)	0.0230 (3)
C6	0.8339 (2)	0.3648 (2)	0.54883 (14)	0.0277 (3)
C7	0.6888 (2)	0.5701 (2)	0.40933 (14)	0.0331 (4)
H7A	0.6051	0.4980	0.3959	0.040*
H7B	0.7806	0.5588	0.3512	0.040*
C8	0.6050 (3)	0.7480 (3)	0.40272 (18)	0.0486 (5)
H8A	0.5172	0.7580	0.4625	0.073*
H8B	0.5529	0.7841	0.3278	0.073*
H8C	0.6900	0.8183	0.4136	0.073*
C9	0.6761 (2)	0.5437 (2)	0.76670 (13)	0.0255 (3)
C10	0.6100 (2)	0.7098 (2)	0.72635 (15)	0.0304 (4)
H10	0.6797	0.7785	0.6817	0.036*
C11	0.4425 (3)	0.7744 (2)	0.75156 (17)	0.0382 (4)
H11	0.3972	0.8861	0.7228	0.046*
C12	0.3434 (2)	0.6753 (2)	0.81827 (16)	0.0370 (4)
H12	0.2298	0.7205	0.8357	0.044*
C13	0.4043 (2)	0.5117 (2)	0.86057 (15)	0.0320 (4)
H13	0.3342	0.4452	0.9068	0.038*
C14	0.5720 (2)	0.4459 (2)	0.83384 (13)	0.0269 (3)
C15	0.5435 (2)	0.1762 (2)	0.93170 (16)	0.0361 (4)
H15A	0.4988	0.2205	1.0013	0.054*
H15B	0.6133	0.0671	0.9521	0.054*
H15C	0.4489	0.1642	0.8845	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0304 (2)	0.0195 (2)	0.0222 (2)	−0.00308 (15)	−0.00427 (14)	−0.00340 (14)
O1	0.0296 (6)	0.0277 (6)	0.0355 (6)	−0.0073 (5)	0.0044 (5)	0.0011 (5)
O2	0.0744 (10)	0.0443 (8)	0.0274 (7)	0.0095 (7)	−0.0101 (6)	−0.0165 (6)
O3	0.0391 (7)	0.0314 (6)	0.0209 (6)	−0.0055 (5)	−0.0058 (5)	−0.0026 (5)
N1	0.0255 (6)	0.0180 (6)	0.0217 (6)	−0.0048 (5)	−0.0032 (5)	−0.0046 (5)
N2	0.0309 (7)	0.0181 (6)	0.0238 (6)	−0.0034 (5)	−0.0014 (5)	−0.0056 (5)
C1	0.0237 (7)	0.0218 (7)	0.0202 (7)	−0.0052 (6)	−0.0020 (6)	−0.0033 (6)
C2	0.0202 (7)	0.0206 (7)	0.0227 (7)	−0.0045 (6)	0.0013 (6)	−0.0044 (6)
C3	0.0261 (8)	0.0261 (8)	0.0241 (8)	−0.0069 (6)	0.0019 (6)	−0.0084 (6)
C4	0.0497 (11)	0.0273 (9)	0.0309 (9)	−0.0059 (8)	−0.0026 (8)	−0.0121 (7)
C5	0.0235 (7)	0.0256 (8)	0.0217 (7)	−0.0063 (6)	0.0014 (6)	−0.0067 (6)
C6	0.0278 (8)	0.0332 (9)	0.0233 (8)	−0.0059 (7)	0.0010 (6)	−0.0066 (6)
C7	0.0370 (9)	0.0430 (10)	0.0199 (8)	−0.0104 (8)	−0.0046 (7)	0.0000 (7)
C8	0.0683 (14)	0.0410 (11)	0.0346 (10)	−0.0088 (10)	−0.0160 (10)	0.0062 (8)
C9	0.0268 (8)	0.0292 (8)	0.0222 (7)	−0.0048 (6)	−0.0031 (6)	−0.0081 (6)
C10	0.0335 (9)	0.0276 (8)	0.0289 (8)	0.0007 (7)	−0.0053 (7)	−0.0055 (7)
C11	0.0398 (10)	0.0284 (9)	0.0436 (10)	0.0035 (8)	−0.0066 (8)	−0.0041 (8)
C12	0.0352 (9)	0.0377 (10)	0.0367 (9)	0.0019 (8)	0.0000 (7)	−0.0094 (8)
C13	0.0320 (9)	0.0368 (9)	0.0278 (8)	−0.0069 (7)	−0.0017 (7)	−0.0049 (7)
C14	0.0294 (8)	0.0286 (8)	0.0233 (8)	−0.0044 (7)	−0.0036 (6)	−0.0049 (6)
C15	0.0366 (10)	0.0323 (9)	0.0386 (10)	−0.0106 (8)	0.0047 (8)	0.0033 (8)

Geometric parameters (Å, º) top

S1—C2	1.6969 (15)	C5—C6	1.476 (2)
O1—C14	1.349 (2)	C7—C8	1.498 (3)
O1—C15	1.430 (2)	C7—H7A	0.9900
O2—C6	1.205 (2)	C7—H7B	0.9900
O3—C6	1.340 (2)	C8—H8A	0.9800
O3—C7	1.4541 (19)	C8—H8B	0.9800
N1—C2	1.322 (2)	C8—H8C	0.9800
N1—C1	1.4783 (18)	C9—C14	1.397 (2)
N1—H1A	0.9098	C9—C10	1.403 (2)
N2—C2	1.3580 (19)	C10—C11	1.395 (3)
N2—C3	1.391 (2)	C10—H10	0.9500
N2—H2A	0.9098	C11—C12	1.376 (3)
C1—C5	1.522 (2)	C11—H11	0.9500
C1—C9	1.523 (2)	C12—C13	1.382 (3)
C1—H1	1.0000	C12—H12	0.9500
C3—C5	1.347 (2)	C13—C14	1.403 (2)
C3—C4	1.501 (2)	C13—H13	0.9500
C4—H4A	0.9800	C15—H15A	0.9800
C4—H4B	0.9800	C15—H15B	0.9800
C4—H4C	0.9800	C15—H15C	0.9800

C14—O1—C15	118.77 (14)	C8—C7—H7A	110.4
C6—O3—C7	116.45 (13)	O3—C7—H7B	110.4
C2—N1—C1	125.30 (12)	C8—C7—H7B	110.4
C2—N1—H1A	117.1	H7A—C7—H7B	108.6
C1—N1—H1A	114.7	C7—C8—H8A	109.5
C2—N2—C3	123.59 (14)	C7—C8—H8B	109.5
C2—N2—H2A	116.2	H8A—C8—H8B	109.5
C3—N2—H2A	119.5	C7—C8—H8C	109.5
N1—C1—C5	108.79 (12)	H8A—C8—H8C	109.5
N1—C1—C9	110.68 (12)	H8B—C8—H8C	109.5
C5—C1—C9	115.38 (12)	C14—C9—C10	118.77 (16)
N1—C1—H1	107.2	C14—C9—C1	121.76 (15)
C5—C1—H1	107.2	C10—C9—C1	119.46 (15)
C9—C1—H1	107.2	C11—C10—C9	120.32 (17)
N1—C2—N2	117.28 (14)	C11—C10—H10	119.8
N1—C2—S1	122.70 (11)	C9—C10—H10	119.8
N2—C2—S1	119.94 (12)	C12—C11—C10	119.55 (17)
C5—C3—N2	119.62 (14)	C12—C11—H11	120.2
C5—C3—C4	127.50 (15)	C10—C11—H11	120.2
N2—C3—C4	112.89 (14)	C11—C12—C13	121.84 (17)
C3—C4—H4A	109.5	C11—C12—H12	119.1
C3—C4—H4B	109.5	C13—C12—H12	119.1
H4A—C4—H4B	109.5	C12—C13—C14	118.62 (17)
C3—C4—H4C	109.5	C12—C13—H13	120.7
H4A—C4—H4C	109.5	C14—C13—H13	120.7
H4B—C4—H4C	109.5	O1—C14—C9	115.19 (15)
C3—C5—C6	121.63 (14)	O1—C14—C13	123.92 (15)
C3—C5—C1	120.93 (14)	C9—C14—C13	120.89 (16)
C6—C5—C1	117.42 (14)	O1—C15—H15A	109.5
O2—C6—O3	122.34 (16)	O1—C15—H15B	109.5
O2—C6—C5	126.96 (16)	H15A—C15—H15B	109.5
O3—C6—C5	110.70 (13)	O1—C15—H15C	109.5
O3—C7—C8	106.67 (14)	H15A—C15—H15C	109.5
O3—C7—H7A	110.4	H15B—C15—H15C	109.5

C2—N1—C1—C5	−25.4 (2)	C3—C5—C6—O3	171.37 (14)
C2—N1—C1—C9	102.32 (16)	C1—C5—C6—O3	−6.8 (2)
C1—N1—C2—N2	16.9 (2)	C6—O3—C7—C8	177.69 (16)
C1—N1—C2—S1	−166.47 (11)	N1—C1—C9—C14	−61.89 (18)
C3—N2—C2—N1	0.7 (2)	C5—C1—C9—C14	62.18 (19)
C3—N2—C2—S1	−176.02 (12)	N1—C1—C9—C10	116.92 (15)
C2—N2—C3—C5	−6.0 (2)	C5—C1—C9—C10	−119.01 (16)
C2—N2—C3—C4	173.96 (15)	C14—C9—C10—C11	−1.1 (2)
N2—C3—C5—C6	176.60 (14)	C1—C9—C10—C11	−179.90 (15)
C4—C3—C5—C6	−3.3 (3)	C9—C10—C11—C12	1.3 (3)
N2—C3—C5—C1	−5.3 (2)	C10—C11—C12—C13	−0.7 (3)
C4—C3—C5—C1	174.72 (16)	C11—C12—C13—C14	−0.3 (3)
N1—C1—C5—C3	18.7 (2)	C15—O1—C14—C9	−175.65 (14)
C9—C1—C5—C3	−106.35 (17)	C15—O1—C14—C13	4.3 (2)
N1—C1—C5—C6	−163.15 (13)	C10—C9—C14—O1	−179.93 (14)
C9—C1—C5—C6	71.79 (18)	C1—C9—C14—O1	−1.1 (2)
C7—O3—C6—O2	5.8 (2)	C10—C9—C14—C13	0.1 (2)
C7—O3—C6—C5	−174.41 (13)	C1—C9—C14—C13	178.93 (14)
C3—C5—C6—O2	−8.9 (3)	C12—C13—C14—O1	−179.41 (16)
C1—C5—C6—O2	172.98 (18)	C12—C13—C14—C9	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.91	2.46	3.3539 (13)	167
N2—H2A···S1ⁱⁱ	0.91	2.58	3.4327 (14)	157

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.91	2.46	3.3539 (13)	167
N2—H2A···S1ⁱⁱ	0.91	2.58	3.4327 (14)	157

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+2.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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Volume 71| Part 7| July 2015| Pages o444-o445

doi:10.1107/S2056989015010026

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

Crystal structure of ethyl 4-(2-meth­­oxy­phen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of ethyl 4-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate