Ethyl 4-(4-chloro­phen­yl)-6-methyl-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Nayak, S.K.; Venugopala, K.N.; Chopra, D.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.; Guru Row, T.N.

doi:10.1107/S1600536809037453

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2518

doi:10.1107/S1600536809037453

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Ethyl 4-(4-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Susanta K. Nayak,^a K. N. Venugopala,^b Deepak Chopra,^c ^* Thavendran Govender,^d Hendrik G. Kruger,^b Glenn E. M. Maguire ^b and T. N. Guru Row ^a

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, ^bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, ^cDepartment of Chemistry, Indian Institute of Science Education and Research, Bhopal 462 023, India, and ^dSchool of Pharmacy and Pharmacology, University of Kwazulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: dchopra@iiserbhopal.ac.in

(Received 14 September 2009; accepted 16 September 2009; online 26 September 2009)

In the title compound, C₁₄H₁₅ClN₂O₂S, the tetrahydropyrimidine ring adopts a twisted boat conformation with the carbonyl group in an s-trans conformation with respect to the C=C double bond of the six-membered tetrahydropyrimidine ring. The molecular conformation is determined by an intramolecular C—H⋯π interaction. The crystal structure is further stabilized by intermolecular N—H⋯O molecular chains and centrosymmetric N—H⋯S dimers.

Related literature

For background to the applications of poly-functionalized dihydropyrimidines, see: Corey & Cheng (1995 ); Hurst & Hull (1961 ); Jauk et al. (2000 ); Kappe (2000 ); Mayer et al. (1999 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₄H₁₅ClN₂O₂S
M_r = 310.80
Triclinic, $[P \overline 1]$
a = 7.3420 (3) Å
b = 9.4895 (4) Å
c = 12.0425 (5) Å
α = 73.823 (4)°
β = 88.512 (3)°
γ = 70.264 (4)°
V = 756.32 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 292 K
0.24 × 0.22 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Eos (Nova) detector
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.902, T_max = 0.933
16944 measured reflections
2960 independent reflections
2232 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.161
S = 1.09
2960 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.25	3.077 (3)	161
N2—H2⋯S1ⁱⁱ	0.86	2.49	3.323 (3)	164
C14—H14⋯Cg1	0.93	2.67	3.146 (4)	113
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1. Cg1 is the centroid of the C2=C3 double bond.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037453/sj2653sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037453/sj2653Isup2.hkl

checkCIF report

Comment top

The logic of chemical reactivity (Corey & Cheng, 1995) has found application in the rational design of a variety of drug molecules. One such class of compounds is the "Bignelli compounds". These are poly-functionalized dihydropyrimidine (DHPM's) exhibiting a broad range of therapeutic and pharmacological properties (Kappe, 2000) namely, antiviral (Hurst et al., 1961), antimimotic (Mayer et al.,1999) and calcium channel modulators (Jauk et al., 2000). In view of immense range of applications of this class of compounds we have undertaken a single-crystal determination of the title compound.

The tetrahydropyrimidine ring adopts a twist boat conformation. The puckering parameters (Cremer & Pople 1975) are Q = 0.277 (3) Å, θ(2) = 108.1 (3)° and ϕ(2) = 349.1 (6)° respectively. The orientation of the chloro-phenyl moiety is such that it bisects the twist boat conformation of the tetrahydropyrimidine ring, the C9—C4—C3—C5 torsion angle being 77.4 (3)°. The molecular conformation is stabilized by an intramolecular C—H···π interaction (2.67 Å, 113°) wherein the aryl hydrogen H14 is oriented towards the π electrons of the C2=C3 double bond (Figure 1). The crystal structure is further stabilized by centrosymmetric N—H···S dimers and N—H···O hydrogen bonds forming molecular chains along the crystallographic a axis (Figure 2).

Related literature top

For background to the applications of poly-functionalized dihydropyrimidines, see: Corey & Cheng (1995); Hurst & Hull (1961); Jauk et al. (2000); Kappe (2000); Mayer et al. (1999). For ring puckering parameters, see: Cremer & Pople (1975). Cg1 is the centroid of the C2=C3 double bond.

Experimental top

A mixture of ethylacetoacetate (0.1 mol), para chlorosubstituted benzaldehyde (0.1 mol) and thiourea was refluxed in 50.0 mL of ethanol for 2.0 hrs in presence of concentrated hydrochloric acid as catalyst. The reaction completion was monitored through thin layer chromatography and and, on completion, the products were poured into ice cold water. The precipitate obtained was filtered, dried and crystallized from methanol to obtain the title compound.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. : The structure of the title compound showing the atom labelling Scheme with displacement ellipsoids for non-H atoms at the 50% probability level. The dotted line shows the C—H···π intramolecular interactions. Cg1 (the orange open circle) denotes the center of gravity of the C2=C3 bond.
	Fig. 2. : The crystal packing showing the molecular chains of N—H···O hydrogen bonds and N—H···S centrosymmetric dimers. Molecules at # and * have the symmetry codes (- x + 1, - y + 1, - z + 1) and (x - 1, y, z) respectively.

Ethyl 4-(4-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₄H₁₅ClN₂O₂S	Z = 2
M_r = 310.80	F(000) = 324
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.3420 (3) Å	Cell parameters from 340 reflections
b = 9.4895 (4) Å	θ = 1.0–28.0°
c = 12.0425 (5) Å	µ = 0.39 mm⁻¹
α = 73.823 (4)°	T = 292 K
β = 88.512 (3)°	Block, colorless
γ = 70.264 (4)°	0.24 × 0.22 × 0.18 mm
V = 756.32 (6) Å³

Data collection top

Oxford Diffraction Xcalibur with Eos (Nova) detector diffractometer	2960 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 16.0839 pixels mm^-1	θ_max = 26.0°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
T_min = 0.902, T_max = 0.933	l = −14→14
16944 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.094P)² + 0.1394P] where P = (F_o² + 2F_c²)/3
2960 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₄H₁₅ClN₂O₂S	γ = 70.264 (4)°
M_r = 310.80	V = 756.32 (6) Å³
Triclinic, P1	Z = 2
a = 7.3420 (3) Å	Mo Kα radiation
b = 9.4895 (4) Å	µ = 0.39 mm⁻¹
c = 12.0425 (5) Å	T = 292 K
α = 73.823 (4)°	0.24 × 0.22 × 0.18 mm
β = 88.512 (3)°

Data collection top

Oxford Diffraction Xcalibur with Eos (Nova) detector diffractometer	2960 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2232 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.933	R_int = 0.040
16944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.09	Δρ_max = 0.48 e Å⁻³
2960 reflections	Δρ_min = −0.37 e Å⁻³
183 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
S1	0.19746 (10)	0.59669 (9)	0.54217 (7)	0.0474 (3)
Cl1	0.98420 (16)	0.22640 (13)	1.09156 (8)	0.0841 (4)
N2	0.5115 (3)	0.6617 (3)	0.57987 (18)	0.0368 (5)
H2	0.5687	0.6038	0.5368	0.044*
C3	0.5079 (4)	0.8759 (3)	0.6529 (2)	0.0337 (6)
N1	0.2287 (3)	0.8143 (3)	0.6307 (2)	0.0395 (5)
H1	0.1099	0.8288	0.6463	0.047*
C4	0.6301 (4)	0.7183 (3)	0.6403 (2)	0.0343 (6)
H4	0.7360	0.7320	0.5922	0.041*
O2	0.5259 (3)	1.0762 (3)	0.7252 (2)	0.0562 (6)
O1	0.7882 (3)	0.9466 (2)	0.64949 (19)	0.0501 (5)
C1	0.3222 (4)	0.6937 (3)	0.5869 (2)	0.0352 (6)
C9	0.7198 (3)	0.5977 (3)	0.7561 (2)	0.0330 (6)
C2	0.3137 (4)	0.9158 (3)	0.6519 (2)	0.0352 (6)
C5	0.6218 (4)	0.9691 (3)	0.6732 (2)	0.0373 (6)
C14	0.6506 (4)	0.6140 (4)	0.8616 (2)	0.0467 (7)
H14	0.5469	0.7027	0.8633	0.056*
C6	0.6261 (5)	1.1724 (4)	0.7526 (3)	0.0571 (8)
H6A	0.7528	1.1073	0.7916	0.069*
H6B	0.6434	1.2452	0.6821	0.069*
C8	0.1693 (4)	1.0610 (4)	0.6676 (3)	0.0520 (8)
H8A	0.2170	1.1461	0.6395	0.078*
H8B	0.1488	1.0468	0.7485	0.078*
H8C	0.0490	1.0840	0.6251	0.078*
C10	0.8750 (4)	0.4642 (4)	0.7572 (3)	0.0472 (7)
H10	0.9247	0.4523	0.6873	0.057*
C12	0.8839 (4)	0.3695 (4)	0.9625 (3)	0.0499 (7)
C11	0.9569 (4)	0.3507 (4)	0.8560 (3)	0.0489 (7)
H11	1.0597	0.2617	0.8539	0.059*
C13	0.7329 (5)	0.5008 (4)	0.9644 (3)	0.0532 (8)
H13	0.6856	0.5140	1.0345	0.064*
C7	0.5083 (6)	1.2561 (6)	0.8271 (5)	0.1004 (17)
H7A	0.5077	1.1839	0.9009	0.151*
H7B	0.3781	1.3084	0.7922	0.151*
H7C	0.5608	1.3317	0.8379	0.151*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0396 (4)	0.0547 (5)	0.0629 (5)	−0.0215 (3)	0.0076 (3)	−0.0340 (4)
Cl1	0.0859 (7)	0.0806 (7)	0.0595 (6)	−0.0202 (6)	−0.0165 (5)	0.0120 (5)
N2	0.0311 (12)	0.0444 (13)	0.0402 (11)	−0.0104 (10)	0.0019 (9)	−0.0236 (10)
C3	0.0304 (13)	0.0358 (14)	0.0366 (13)	−0.0117 (11)	0.0014 (10)	−0.0124 (11)
N1	0.0330 (12)	0.0468 (13)	0.0508 (13)	−0.0190 (10)	0.0131 (10)	−0.0271 (11)
C4	0.0300 (13)	0.0409 (14)	0.0386 (13)	−0.0156 (11)	0.0079 (10)	−0.0179 (11)
O2	0.0448 (12)	0.0589 (14)	0.0878 (16)	−0.0276 (10)	0.0155 (11)	−0.0453 (13)
O1	0.0322 (11)	0.0551 (13)	0.0722 (14)	−0.0202 (9)	0.0073 (9)	−0.0265 (11)
C1	0.0369 (14)	0.0388 (14)	0.0316 (12)	−0.0127 (11)	0.0040 (10)	−0.0134 (11)
C9	0.0277 (13)	0.0393 (14)	0.0378 (13)	−0.0141 (11)	0.0041 (10)	−0.0171 (11)
C2	0.0341 (14)	0.0353 (14)	0.0376 (13)	−0.0123 (11)	0.0015 (10)	−0.0121 (11)
C5	0.0404 (16)	0.0338 (14)	0.0371 (13)	−0.0120 (12)	0.0017 (11)	−0.0098 (11)
C14	0.0449 (17)	0.0473 (16)	0.0463 (16)	−0.0090 (13)	0.0060 (13)	−0.0195 (14)
C6	0.056 (2)	0.0570 (19)	0.079 (2)	−0.0327 (16)	0.0092 (17)	−0.0356 (18)
C8	0.0314 (15)	0.0469 (17)	0.082 (2)	−0.0096 (13)	0.0046 (14)	−0.0304 (17)
C10	0.0379 (15)	0.0524 (18)	0.0508 (17)	−0.0091 (13)	0.0088 (13)	−0.0224 (15)
C12	0.0429 (16)	0.0570 (18)	0.0457 (16)	−0.0185 (14)	−0.0079 (13)	−0.0056 (14)
C11	0.0324 (15)	0.0459 (17)	0.0593 (18)	−0.0023 (13)	0.0021 (13)	−0.0147 (15)
C13	0.060 (2)	0.062 (2)	0.0397 (16)	−0.0214 (16)	0.0062 (14)	−0.0179 (15)
C7	0.079 (3)	0.130 (4)	0.152 (4)	−0.063 (3)	0.045 (3)	−0.103 (4)

Geometric parameters (Å, º) top

S1—C1	1.688 (3)	C2—C8	1.486 (4)
Cl1—C12	1.735 (3)	C14—C13	1.382 (4)
N2—C1	1.324 (3)	C14—H14	0.9300
N2—C4	1.464 (3)	C6—C7	1.441 (5)
N2—H2	0.8600	C6—H6A	0.9700
C3—C2	1.345 (3)	C6—H6B	0.9700
C3—C5	1.474 (4)	C8—H8A	0.9600
C3—C4	1.510 (3)	C8—H8B	0.9600
N1—C1	1.359 (3)	C8—H8C	0.9600
N1—C2	1.390 (3)	C10—C11	1.349 (4)
N1—H1	0.8600	C10—H10	0.9300
C4—C9	1.528 (4)	C12—C13	1.365 (5)
C4—H4	0.9800	C12—C11	1.411 (4)
O2—C5	1.330 (3)	C11—H11	0.9300
O2—C6	1.455 (3)	C13—H13	0.9300
O1—C5	1.208 (3)	C7—H7A	0.9600
C9—C14	1.386 (4)	C7—H7B	0.9600
C9—C10	1.386 (4)	C7—H7C	0.9600

C1—N2—C4	124.5 (2)	C7—C6—O2	107.4 (3)
C1—N2—H2	117.7	C7—C6—H6A	110.2
C4—N2—H2	117.7	O2—C6—H6A	110.2
C2—C3—C5	126.0 (2)	C7—C6—H6B	110.2
C2—C3—C4	119.9 (2)	O2—C6—H6B	110.2
C5—C3—C4	113.9 (2)	H6A—C6—H6B	108.5
C1—N1—C2	123.8 (2)	C2—C8—H8A	109.5
C1—N1—H1	118.1	C2—C8—H8B	109.5
C2—N1—H1	118.1	H8A—C8—H8B	109.5
N2—C4—C3	109.1 (2)	C2—C8—H8C	109.5
N2—C4—C9	110.3 (2)	H8A—C8—H8C	109.5
C3—C4—C9	113.21 (19)	H8B—C8—H8C	109.5
N2—C4—H4	108.0	C11—C10—C9	122.5 (3)
C3—C4—H4	108.0	C11—C10—H10	118.7
C9—C4—H4	108.0	C9—C10—H10	118.7
C5—O2—C6	118.1 (2)	C13—C12—C11	120.0 (3)
N2—C1—N1	116.0 (2)	C13—C12—Cl1	119.6 (2)
N2—C1—S1	123.59 (19)	C11—C12—Cl1	120.5 (2)
N1—C1—S1	120.36 (19)	C10—C11—C12	118.9 (3)
C14—C9—C10	117.7 (3)	C10—C11—H11	120.6
C14—C9—C4	122.9 (2)	C12—C11—H11	120.6
C10—C9—C4	119.5 (2)	C12—C13—C14	119.8 (3)
C3—C2—N1	118.7 (2)	C12—C13—H13	120.1
C3—C2—C8	128.3 (2)	C14—C13—H13	120.1
N1—C2—C8	112.9 (2)	C6—C7—H7A	109.5
O1—C5—O2	123.2 (2)	C6—C7—H7B	109.5
O1—C5—C3	123.5 (2)	H7A—C7—H7B	109.5
O2—C5—C3	113.2 (2)	C6—C7—H7C	109.5
C13—C14—C9	121.2 (3)	H7A—C7—H7C	109.5
C13—C14—H14	119.4	H7B—C7—H7C	109.5
C9—C14—H14	119.4

C1—N2—C4—C3	−31.3 (3)	C1—N1—C2—C8	163.8 (3)
C1—N2—C4—C9	93.6 (3)	C6—O2—C5—O1	1.1 (4)
C2—C3—C4—N2	24.4 (3)	C6—O2—C5—C3	178.3 (2)
C5—C3—C4—N2	−159.3 (2)	C2—C3—C5—O1	−163.6 (3)
C2—C3—C4—C9	−98.8 (3)	C4—C3—C5—O1	20.4 (4)
C5—C3—C4—C9	77.4 (3)	C2—C3—C5—O2	19.2 (4)
C4—N2—C1—N1	15.8 (4)	C4—C3—C5—O2	−156.7 (2)
C4—N2—C1—S1	−165.7 (2)	C10—C9—C14—C13	−0.3 (4)
C2—N1—C1—N2	9.3 (4)	C4—C9—C14—C13	178.6 (3)
C2—N1—C1—S1	−169.2 (2)	C5—O2—C6—C7	−169.1 (3)
N2—C4—C9—C14	−103.7 (3)	C14—C9—C10—C11	1.1 (4)
C3—C4—C9—C14	18.9 (3)	C4—C9—C10—C11	−177.8 (3)
N2—C4—C9—C10	75.2 (3)	C9—C10—C11—C12	−1.0 (5)
C3—C4—C9—C10	−162.3 (2)	C13—C12—C11—C10	0.0 (5)
C5—C3—C2—N1	179.7 (2)	Cl1—C12—C11—C10	179.8 (2)
C4—C3—C2—N1	−4.6 (4)	C11—C12—C13—C14	0.8 (5)
C5—C3—C2—C8	1.6 (5)	Cl1—C12—C13—C14	−179.0 (2)
C4—C3—C2—C8	177.3 (3)	C9—C14—C13—C12	−0.7 (5)
C1—N1—C2—C3	−14.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.25	3.077 (3)	161
N2—H2···S1ⁱⁱ	0.86	2.49	3.323 (3)	164
C14—H14···Cg1	0.93	2.67	3.146 (4)	113

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅ClN₂O₂S
M_r	310.80
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.3420 (3), 9.4895 (4), 12.0425 (5)
α, β, γ (°)	73.823 (4), 88.512 (3), 70.264 (4)
V (Å³)	756.32 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur with Eos (Nova) detector diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.902, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	16944, 2960, 2232
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.161, 1.09
No. of reflections	2960
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.37

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.8600	2.2500	3.077 (3)	161.00
N2—H2···S1ⁱⁱ	0.8600	2.4900	3.323 (3)	164.00
C14—H14···Cg1	0.93	2.67	3.146 (4)	113.0

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

Acknowledgements

We are grateful for funding under DST–FIST (Level II) for the Oxford Diffraction facility at SSCU. SKN thanks CSIR (SRF), India, for financial support.

References

Corey, E. J. & Cheng, X.-M. (1995). The Logic of Chemical Synthesis. New York: John Wiley & Sons Australia Ltd. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hurst, E. W. & Hull, R. (1961). J. Med. Pharm. Chem. 3, 215–229. CrossRef PubMed CAS Web of Science Google Scholar
Jauk, B., Pernat, T. & Kappe, C. O. (2000). Molecules, 5, 227–239 and references therein. Google Scholar
Kappe, C. O. (2000). Eur. J. Med. Chem. 4835, 1043–1052. Web of Science CrossRef Google Scholar
Mayer, T. U., Kapoor, T. M., Haggarty, S. J., King, R. W., Schreiber, S. I. & Mitchison, T. J. (1999). Science, 286, 971–974. Web of Science CrossRef PubMed CAS Google Scholar
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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 65| Part 10| October 2009| Page o2518

doi:10.1107/S1600536809037453

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

Ethyl 4-(4-chloro­phen­yl)-6-methyl-2-thioxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

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Ethyl 4-(4-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate