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

Wu, D.-H.; Zhang, Y.-H.; Li, Z.-F.

doi:10.1107/S1600536809024520

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1733

doi:10.1107/S1600536809024520

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

De-Hong Wu,^a ^* You-Hong Zhang ^a and Zhu-Feng Li ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, School of Materials Science and Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: wudehong@seu.edu.cn

(Received 24 June 2009; accepted 26 June 2009; online 1 July 2009)

The asymmetric unit of the title compound, C₁₅H₁₅N₃O₂S, contains two independent molecules corresponding to the R and S enantiomers. The dihydropyrimidinone rings adopt a flattened boat conformation. One of the ethyl groups is disordered over two orientations with occupancy factors of 0.700 (7) and 0.300 (7). In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen-bonding interactions into one-dimensional chains along the c-axis direction. The chains are further connected by N—H⋯S hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis and the pharmaceutical applications of pyrimidinones, see: Atwal (1990 ); Steele et al. (1998 ); Manjula et al. (2004 ); Matsuda & Hirao (1965 ).

Experimental

Crystal data

C₁₅H₁₅N₃O₂S
M_r = 301.37
Triclinic, $[P \overline 1]$
a = 9.2938 (19) Å
b = 13.277 (3) Å
c = 14.512 (3) Å
α = 101.247 (17)°
β = 108.442 (13)°
γ = 107.89 (3)°
V = 1529.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 291 K
0.50 × 0.48 × 0.47 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.898, T_max = 0.904
13899 measured reflections
5958 independent reflections
4590 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.151
S = 1.06
5958 reflections
386 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S2ⁱ	0.86	2.60	3.4612 (19)	174
N2—H2A⋯O3ⁱⁱ	0.86	2.14	2.843 (2)	138
N5—H5A⋯O1ⁱⁱⁱ	0.86	2.01	2.852 (2)	165
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024520/rz2341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024520/rz2341Isup2.hkl

checkCIF report

Comment top

The common synthetic routes to the synthesis of dihydropyrimidinone derivatives generally involve multi-step transformations that are essentially based on the Biginelli condensation methodology (Steele et al., 1998). 3,4-Dihydropyrimidinones are compounds which have drawn wide-spread attention due to their pharmaceutical applications. A variety of dihydropyrimidinone derivatives have been screened for antihypertension (Atwal, 1990), antibacterial (Matsuda & Hirao, 1965) and calcium channel blocking (Manjula et al., 2004) activities.We report herein the crystal structure of the title compound, ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate (Fig. 1).

The asymmetric unit of the title compound contains two independent molecules corresponding to the R- and S-enantiomers. One ethyl group (C6–C7) is disordered over two orientations with refined occupancy factors of 0.700 (7) and 0.300 (7). The dihydropyrimidinone rings adopt a flattened boat conformation. In the crystal structure, the molecules are linked by intermolecular N—H···O hydrogen bonding interactions (Table 1) into one-dimensional chains along the c direction (Fig. 2). The chains are further connected by N—H···S hydrogen bonds forming a three-dimensional network.

Related literature top

For the synthesis and the pharmaceutical applications of pyrimidinones, see: Atwal (1990); Steele et al. (1998); Manjula et al. (2004); Matsuda & Hirao (1965).

Experimental top

The title compound was synthesized by refluxing 4-cyanobenzaldehyde (2 mmol), ethyl acetoacetate (2 mmol), thiourea (3 mmol) and NH₄Cl (1 mmol) in acetic acid (10 ml) at 100 °C for 8 h. The reaction mixture was then allowed to stand at room temperature and the product formed was filtered, washed with ethanol followed by water and dried. Further purification was done by recrystallization from ethanol. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution for 4 weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The content of asymmetric unit of the title compound showing the atom numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity.
	Fig. 2. The crystal packing of the title compound, showing the chains along [001] formed by N—H···O hydrogen bonds (dashed lines). The minor component of disorder and H atoms not involved in hydrogen bonds are omitted for clarity.

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

Crystal data top

C₁₅H₁₅N₃O₂S	Z = 4
M_r = 301.37	F(000) = 632
Triclinic, P1	D_x = 1.309 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2938 (19) Å	Cell parameters from 4203 reflections
b = 13.277 (3) Å	θ = 2.4–27.5°
c = 14.512 (3) Å	µ = 0.22 mm⁻¹
α = 101.247 (17)°	T = 291 K
β = 108.442 (13)°	Block, yellow
γ = 107.89 (3)°	0.50 × 0.48 × 0.47 mm
V = 1529.6 (7) Å³

Data collection top

Rigaku SCXmini diffractometer	5958 independent reflections
Radiation source: fine-focus sealed tube	4590 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 13.6612 pixels mm^-1	θ_max = 26.0°, θ_min = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
T_min = 0.898, T_max = 0.904	l = −17→17
13899 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0841P)² + 0.2227P] where P = (F_o² + 2F_c²)/3
5958 reflections	(Δ/σ)_max < 0.001
386 parameters	Δρ_max = 0.32 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O₂S	γ = 107.89 (3)°
M_r = 301.37	V = 1529.6 (7) Å³
Triclinic, P1	Z = 4
a = 9.2938 (19) Å	Mo Kα radiation
b = 13.277 (3) Å	µ = 0.22 mm⁻¹
c = 14.512 (3) Å	T = 291 K
α = 101.247 (17)°	0.50 × 0.48 × 0.47 mm
β = 108.442 (13)°

Data collection top

Rigaku SCXmini diffractometer	5958 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	4590 reflections with I > 2σ(I)
T_min = 0.898, T_max = 0.904	R_int = 0.029
13899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
5958 reflections	Δρ_min = −0.30 e Å⁻³
386 parameters

Special details top

Experimental. 1H-NMR (d4-Methanol) δ (p.p.m.): 7.73 (d, 2H, J = 8 Hz), 7.50 (d, 2H, J = 8 Hz), 5.40 (s, 1H), 4.11 (q, 2H, J = 7 Hz), 2.37 (s, 3H), 1.19(t, 3H, J = 7 Hz). 13 C-NMR (d4-Methanol) δ(p.p.m.): 13.08 (–CH2—CH3), 16.33 (–CH3), 54.66 (C*), 60.03 (–CH2—CH3), 100.73 (C—C=O), 111.32 (C—CN), 118.08 (–CN), 127.46, 132.29 (CH in phenyl), 145.42 (C in phenyl), 148.56 (CH3—C—NH–), 165.53 (C=O), 175.35 (C=S).

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)
C1	0.2143 (2)	−0.01219 (17)	0.21806 (15)	0.0419 (4)
C2	0.2370 (2)	0.03499 (16)	0.06791 (14)	0.0398 (4)
C3	0.2591 (3)	−0.0104 (2)	−0.02697 (17)	0.0561 (6)
H3A	0.2465	0.0359	−0.0696	0.084*
H3B	0.1776	−0.0852	−0.0639	0.084*
H3C	0.3675	−0.0110	−0.0084	0.084*
C4	0.2051 (2)	0.12633 (16)	0.09358 (13)	0.0374 (4)
C5	0.1790 (3)	0.19201 (18)	0.02444 (15)	0.0454 (5)
C6	0.1450 (8)	0.3589 (6)	0.0092 (7)	0.082 (2)	0.700 (7)
H6A	0.0435	0.3271	−0.0523	0.098*	0.700 (7)
H6B	0.2375	0.3768	−0.0108	0.098*	0.700 (7)
C7	0.1533 (8)	0.4606 (4)	0.0772 (5)	0.1006 (17)	0.700 (7)
H7A	0.1462	0.5134	0.0410	0.151*	0.700 (7)
H7B	0.2560	0.4930	0.1366	0.151*	0.700 (7)
H7C	0.0632	0.4415	0.0983	0.151*	0.700 (7)
C8	0.2021 (2)	0.16692 (16)	0.19771 (13)	0.0368 (4)
H8A	0.1093	0.1899	0.1884	0.044*
C9	0.3609 (2)	0.26699 (16)	0.27233 (14)	0.0387 (4)
C10	0.5112 (3)	0.25592 (17)	0.30151 (16)	0.0474 (5)
H10A	0.5152	0.1881	0.2735	0.057*
C11	0.6553 (3)	0.34466 (18)	0.37184 (17)	0.0510 (5)
H11A	0.7548	0.3357	0.3922	0.061*
C12	0.6507 (3)	0.44634 (17)	0.41161 (15)	0.0461 (5)
C13	0.8014 (3)	0.53885 (19)	0.48441 (17)	0.0554 (6)
C14	0.5017 (3)	0.45957 (19)	0.38096 (17)	0.0554 (6)
H14A	0.4989	0.5286	0.4064	0.067*
C15	0.3576 (3)	0.36968 (18)	0.31243 (16)	0.0495 (5)
H15A	0.2578	0.3782	0.2931	0.059*
C16	0.5233 (3)	0.77227 (17)	0.18205 (15)	0.0451 (5)
C17	0.5666 (3)	0.77320 (17)	0.35679 (15)	0.0436 (5)
C18	0.4795 (3)	0.7769 (2)	0.42837 (19)	0.0603 (6)
H18A	0.5549	0.7901	0.4967	0.091*
H18B	0.3873	0.7069	0.4060	0.091*
H18C	0.4408	0.8362	0.4280	0.091*
C19	0.7254 (2)	0.78795 (16)	0.38041 (14)	0.0384 (4)
C20	0.8419 (3)	0.82399 (17)	0.48790 (15)	0.0439 (5)
C21	1.1249 (3)	0.9003 (2)	0.60221 (18)	0.0630 (6)
H21A	1.1071	0.8446	0.6364	0.076*
H21B	1.1211	0.9669	0.6412	0.076*
C22	1.2875 (3)	0.9271 (3)	0.5945 (3)	0.0823 (9)
H22A	1.3741	0.9563	0.6621	0.123*
H22B	1.3032	0.9818	0.5601	0.123*
H22C	1.2900	0.8604	0.5562	0.123*
C23	0.7893 (2)	0.77481 (16)	0.29625 (14)	0.0382 (4)
H23A	0.9001	0.8337	0.3216	0.046*
C24	0.8018 (2)	0.66181 (16)	0.26707 (14)	0.0381 (4)
C25	0.9496 (3)	0.65221 (18)	0.31451 (17)	0.0488 (5)
H25A	1.0406	0.7151	0.3626	0.059*
C26	0.9640 (3)	0.5505 (2)	0.29138 (18)	0.0556 (6)
H26A	1.0641	0.5455	0.3238	0.067*
C27	0.8294 (3)	0.45617 (18)	0.21999 (16)	0.0504 (5)
C28	0.6818 (3)	0.4646 (2)	0.17110 (18)	0.0591 (6)
H28A	0.5913	0.4017	0.1226	0.071*
C29	0.6684 (3)	0.56674 (19)	0.19433 (17)	0.0538 (5)
H29A	0.5687	0.5718	0.1608	0.065*
C30	0.8447 (4)	0.3498 (2)	0.20089 (19)	0.0659 (7)
C6'	0.070 (2)	0.3356 (16)	−0.0032 (18)	0.082 (2)	0.300 (7)
H6'A	0.0324	0.2960	−0.0756	0.098*	0.300 (7)
H6'B	−0.0202	0.3477	0.0105	0.098*	0.300 (7)
C7'	0.2159 (17)	0.4385 (11)	0.0334 (12)	0.1006 (17)	0.300 (7)
H7'A	0.1932	0.4860	−0.0063	0.151*	0.300 (7)
H7'B	0.3057	0.4212	0.0264	0.151*	0.300 (7)
H7'C	0.2453	0.4762	0.1043	0.151*	0.300 (7)
N1	0.2529 (2)	−0.02691 (14)	0.13483 (13)	0.0448 (4)
H1A	0.2896	−0.0779	0.1228	0.054*
N2	0.1754 (2)	0.07505 (14)	0.24092 (12)	0.0416 (4)
H2A	0.1310	0.0779	0.2846	0.050*
N3	0.9225 (3)	0.60999 (18)	0.54293 (17)	0.0738 (6)
N4	0.4650 (2)	0.75428 (16)	0.25562 (13)	0.0516 (4)
H4A	0.3600	0.7300	0.2385	0.062*
N5	0.6813 (2)	0.79053 (14)	0.20621 (12)	0.0441 (4)
H5A	0.7242	0.8135	0.1658	0.053*
N6	0.8613 (4)	0.2675 (2)	0.1898 (2)	0.0943 (9)
O1	0.1803 (2)	0.17349 (17)	−0.06000 (12)	0.0695 (5)
O2	0.1501 (3)	0.27880 (16)	0.06545 (13)	0.0776 (6)
O3	0.8045 (2)	0.82617 (18)	0.56068 (12)	0.0720 (5)
O4	0.99902 (18)	0.85749 (13)	0.49825 (11)	0.0513 (4)
S1	0.21451 (8)	−0.10085 (6)	0.28636 (5)	0.0632 (2)
S2	0.39778 (8)	0.77075 (5)	0.06890 (4)	0.0592 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0376 (10)	0.0473 (11)	0.0412 (10)	0.0142 (8)	0.0170 (9)	0.0176 (9)
C2	0.0396 (10)	0.0435 (10)	0.0339 (9)	0.0131 (8)	0.0160 (8)	0.0111 (8)
C3	0.0722 (15)	0.0587 (13)	0.0437 (11)	0.0300 (12)	0.0304 (11)	0.0110 (10)
C4	0.0373 (9)	0.0438 (10)	0.0305 (9)	0.0142 (8)	0.0148 (8)	0.0124 (8)
C5	0.0460 (11)	0.0568 (12)	0.0369 (10)	0.0220 (9)	0.0173 (9)	0.0190 (9)
C6	0.119 (6)	0.075 (4)	0.075 (3)	0.057 (5)	0.035 (5)	0.048 (3)
C7	0.114 (4)	0.074 (3)	0.136 (5)	0.051 (3)	0.050 (3)	0.055 (3)
C8	0.0386 (10)	0.0442 (10)	0.0329 (9)	0.0192 (8)	0.0169 (8)	0.0148 (8)
C9	0.0448 (10)	0.0440 (10)	0.0309 (9)	0.0189 (9)	0.0181 (8)	0.0131 (8)
C10	0.0467 (11)	0.0404 (10)	0.0530 (12)	0.0197 (9)	0.0173 (10)	0.0116 (9)
C11	0.0435 (11)	0.0491 (12)	0.0551 (13)	0.0174 (10)	0.0147 (10)	0.0161 (10)
C12	0.0517 (12)	0.0451 (11)	0.0353 (10)	0.0122 (9)	0.0166 (9)	0.0130 (8)
C13	0.0643 (14)	0.0469 (12)	0.0485 (12)	0.0175 (11)	0.0198 (12)	0.0145 (10)
C14	0.0690 (15)	0.0440 (12)	0.0513 (12)	0.0263 (11)	0.0225 (11)	0.0079 (9)
C15	0.0513 (12)	0.0517 (12)	0.0448 (11)	0.0264 (10)	0.0163 (10)	0.0094 (9)
C16	0.0611 (13)	0.0422 (11)	0.0392 (10)	0.0269 (10)	0.0216 (10)	0.0157 (8)
C17	0.0533 (12)	0.0497 (11)	0.0409 (10)	0.0265 (9)	0.0260 (9)	0.0204 (9)
C18	0.0621 (14)	0.0887 (18)	0.0607 (14)	0.0418 (13)	0.0427 (12)	0.0379 (13)
C19	0.0518 (11)	0.0390 (10)	0.0373 (10)	0.0246 (9)	0.0247 (9)	0.0166 (8)
C20	0.0581 (12)	0.0448 (11)	0.0386 (10)	0.0285 (10)	0.0237 (10)	0.0138 (8)
C21	0.0676 (15)	0.0553 (14)	0.0467 (12)	0.0228 (12)	0.0068 (11)	0.0058 (10)
C22	0.0594 (16)	0.0692 (17)	0.095 (2)	0.0237 (13)	0.0063 (15)	0.0221 (15)
C23	0.0468 (10)	0.0412 (10)	0.0361 (9)	0.0211 (8)	0.0222 (8)	0.0168 (8)
C24	0.0490 (11)	0.0434 (10)	0.0343 (9)	0.0236 (9)	0.0247 (9)	0.0161 (8)
C25	0.0502 (12)	0.0504 (12)	0.0488 (12)	0.0250 (10)	0.0195 (10)	0.0152 (9)
C26	0.0582 (13)	0.0606 (14)	0.0585 (13)	0.0369 (12)	0.0233 (11)	0.0197 (11)
C27	0.0710 (14)	0.0501 (12)	0.0446 (11)	0.0367 (11)	0.0286 (11)	0.0159 (9)
C28	0.0675 (15)	0.0488 (13)	0.0532 (13)	0.0262 (11)	0.0187 (12)	0.0043 (10)
C29	0.0532 (12)	0.0535 (12)	0.0537 (13)	0.0290 (10)	0.0160 (11)	0.0114 (10)
C30	0.0886 (18)	0.0633 (15)	0.0518 (13)	0.0462 (14)	0.0248 (13)	0.0111 (11)
C6'	0.119 (6)	0.075 (4)	0.075 (3)	0.057 (5)	0.035 (5)	0.048 (3)
C7'	0.114 (4)	0.074 (3)	0.136 (5)	0.051 (3)	0.050 (3)	0.055 (3)
N1	0.0559 (10)	0.0441 (9)	0.0463 (9)	0.0253 (8)	0.0274 (8)	0.0189 (7)
N2	0.0458 (9)	0.0482 (9)	0.0372 (8)	0.0181 (8)	0.0237 (7)	0.0162 (7)
N3	0.0695 (14)	0.0556 (12)	0.0631 (13)	0.0094 (11)	0.0093 (12)	0.0049 (10)
N4	0.0486 (10)	0.0679 (12)	0.0459 (10)	0.0265 (9)	0.0219 (8)	0.0240 (9)
N5	0.0591 (10)	0.0524 (10)	0.0398 (9)	0.0317 (8)	0.0288 (8)	0.0238 (8)
N6	0.134 (2)	0.0732 (16)	0.0725 (15)	0.0687 (17)	0.0222 (16)	0.0050 (12)
O1	0.0948 (13)	0.1007 (14)	0.0499 (9)	0.0593 (11)	0.0437 (9)	0.0432 (9)
O2	0.1407 (18)	0.0738 (12)	0.0546 (10)	0.0714 (13)	0.0467 (11)	0.0369 (9)
O3	0.0800 (12)	0.1160 (15)	0.0370 (8)	0.0530 (11)	0.0314 (8)	0.0239 (9)
O4	0.0519 (9)	0.0556 (9)	0.0404 (8)	0.0189 (7)	0.0153 (7)	0.0122 (6)
S1	0.0743 (4)	0.0735 (4)	0.0747 (4)	0.0400 (3)	0.0448 (4)	0.0500 (4)
S2	0.0743 (4)	0.0698 (4)	0.0399 (3)	0.0421 (3)	0.0167 (3)	0.0196 (3)

Geometric parameters (Å, º) top

C1—N2	1.329 (3)	C18—H18A	0.9600
C1—N1	1.361 (2)	C18—H18B	0.9600
C1—S1	1.680 (2)	C18—H18C	0.9600
C2—C4	1.346 (3)	C19—C20	1.469 (3)
C2—N1	1.391 (3)	C19—C23	1.521 (2)
C2—C3	1.494 (3)	C20—O3	1.210 (2)
C3—H3A	0.9600	C20—O4	1.337 (3)
C3—H3B	0.9600	C21—O4	1.452 (3)
C3—H3C	0.9600	C21—C22	1.489 (4)
C4—C5	1.464 (3)	C21—H21A	0.9700
C4—C8	1.514 (2)	C21—H21B	0.9700
C5—O1	1.206 (2)	C22—H22A	0.9600
C5—O2	1.333 (3)	C22—H22B	0.9600
C6—O2	1.464 (8)	C22—H22C	0.9600
C6—C7	1.473 (9)	C23—N5	1.471 (2)
C6—H6A	0.9700	C23—C24	1.528 (3)
C6—H6B	0.9700	C23—H23A	0.9800
C7—H7A	0.9600	C24—C25	1.386 (3)
C7—H7B	0.9600	C24—C29	1.391 (3)
C7—H7C	0.9600	C25—C26	1.385 (3)
C8—N2	1.467 (2)	C25—H25A	0.9300
C8—C9	1.529 (3)	C26—C27	1.385 (3)
C8—H8A	0.9800	C26—H26A	0.9300
C9—C15	1.388 (3)	C27—C28	1.381 (3)
C9—C10	1.389 (3)	C27—C30	1.445 (3)
C10—C11	1.386 (3)	C28—C29	1.385 (3)
C10—H10A	0.9300	C28—H28A	0.9300
C11—C12	1.380 (3)	C29—H29A	0.9300
C11—H11A	0.9300	C30—N6	1.137 (3)
C12—C14	1.391 (3)	C6'—C7'	1.453 (16)
C12—C13	1.445 (3)	C6'—O2	1.51 (2)
C13—N3	1.144 (3)	C6'—H6'A	0.9700
C14—C15	1.386 (3)	C6'—H6'B	0.9700
C14—H14A	0.9300	C7'—H7'A	0.9600
C15—H15A	0.9300	C7'—H7'B	0.9600
C16—N5	1.327 (3)	C7'—H7'C	0.9600
C16—N4	1.370 (3)	N1—H1A	0.8600
C16—S2	1.679 (2)	N2—H2A	0.8600
C17—C19	1.345 (3)	N4—H4A	0.8600
C17—N4	1.394 (3)	N5—H5A	0.8600
C17—C18	1.508 (3)

N2—C1—N1	116.14 (17)	C20—C19—C23	118.95 (17)
N2—C1—S1	122.57 (15)	O3—C20—O4	122.34 (19)
N1—C1—S1	121.29 (16)	O3—C20—C19	125.4 (2)
C4—C2—N1	118.89 (17)	O4—C20—C19	112.29 (16)
C4—C2—C3	127.33 (19)	O4—C21—C22	107.1 (2)
N1—C2—C3	113.77 (18)	O4—C21—H21A	110.3
C2—C3—H3A	109.5	C22—C21—H21A	110.3
C2—C3—H3B	109.5	O4—C21—H21B	110.3
H3A—C3—H3B	109.5	C22—C21—H21B	110.3
C2—C3—H3C	109.5	H21A—C21—H21B	108.5
H3A—C3—H3C	109.5	C21—C22—H22A	109.5
H3B—C3—H3C	109.5	C21—C22—H22B	109.5
C2—C4—C5	121.66 (17)	H22A—C22—H22B	109.5
C2—C4—C8	120.44 (17)	C21—C22—H22C	109.5
C5—C4—C8	117.85 (17)	H22A—C22—H22C	109.5
O1—C5—O2	121.6 (2)	H22B—C22—H22C	109.5
O1—C5—C4	126.9 (2)	N5—C23—C19	109.13 (15)
O2—C5—C4	111.51 (17)	N5—C23—C24	110.81 (15)
O2—C6—C7	108.0 (6)	C19—C23—C24	112.27 (15)
O2—C6—H6A	110.1	N5—C23—H23A	108.2
C7—C6—H6A	110.1	C19—C23—H23A	108.2
O2—C6—H6B	110.1	C24—C23—H23A	108.2
C7—C6—H6B	110.1	C25—C24—C29	118.28 (19)
H6A—C6—H6B	108.4	C25—C24—C23	119.63 (18)
C6—C7—H7A	109.5	C29—C24—C23	122.09 (18)
C6—C7—H7B	109.5	C26—C25—C24	121.0 (2)
H7A—C7—H7B	109.5	C26—C25—H25A	119.5
C6—C7—H7C	109.5	C24—C25—H25A	119.5
H7A—C7—H7C	109.5	C25—C26—C27	120.0 (2)
H7B—C7—H7C	109.5	C25—C26—H26A	120.0
N2—C8—C4	109.60 (15)	C27—C26—H26A	120.0
N2—C8—C9	109.97 (15)	C28—C27—C26	119.6 (2)
C4—C8—C9	112.24 (15)	C28—C27—C30	121.2 (2)
N2—C8—H8A	108.3	C26—C27—C30	119.1 (2)
C4—C8—H8A	108.3	C27—C28—C29	120.0 (2)
C9—C8—H8A	108.3	C27—C28—H28A	120.0
C15—C9—C10	118.92 (18)	C29—C28—H28A	120.0
C15—C9—C8	120.95 (17)	C28—C29—C24	121.0 (2)
C10—C9—C8	120.14 (17)	C28—C29—H29A	119.5
C11—C10—C9	120.83 (19)	C24—C29—H29A	119.5
C11—C10—H10A	119.6	N6—C30—C27	177.3 (3)
C9—C10—H10A	119.6	C7'—C6'—O2	95.9 (11)
C12—C11—C10	119.8 (2)	C7'—C6'—H6'A	112.6
C12—C11—H11A	120.1	O2—C6'—H6'A	112.6
C10—C11—H11A	120.1	C7'—C6'—H6'B	112.6
C11—C12—C14	119.99 (19)	O2—C6'—H6'B	112.6
C11—C12—C13	119.6 (2)	H6'A—C6'—H6'B	110.1
C14—C12—C13	120.4 (2)	C6'—C7'—H7'A	109.5
N3—C13—C12	178.1 (3)	C6'—C7'—H7'B	109.5
C15—C14—C12	119.8 (2)	H7'A—C7'—H7'B	109.5
C15—C14—H14A	120.1	C6'—C7'—H7'C	109.5
C12—C14—H14A	120.1	H7'A—C7'—H7'C	109.5
C14—C15—C9	120.6 (2)	H7'B—C7'—H7'C	109.5
C14—C15—H15A	119.7	C1—N1—C2	124.43 (17)
C9—C15—H15A	119.7	C1—N1—H1A	117.8
N5—C16—N4	116.15 (18)	C2—N1—H1A	117.8
N5—C16—S2	123.41 (16)	C1—N2—C8	125.33 (15)
N4—C16—S2	120.44 (17)	C1—N2—H2A	117.3
C19—C17—N4	119.20 (17)	C8—N2—H2A	117.3
C19—C17—C18	127.79 (19)	C16—N4—C17	123.55 (18)
N4—C17—C18	113.00 (18)	C16—N4—H4A	118.2
C17—C18—H18A	109.5	C17—N4—H4A	118.2
C17—C18—H18B	109.5	C16—N5—C23	125.58 (16)
H18A—C18—H18B	109.5	C16—N5—H5A	117.2
C17—C18—H18C	109.5	C23—N5—H5A	117.2
H18A—C18—H18C	109.5	C5—O2—C6	116.0 (4)
H18B—C18—H18C	109.5	C5—O2—C6'	119.6 (10)
C17—C19—C20	120.67 (17)	C20—O4—C21	116.71 (17)
C17—C19—C23	120.26 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S2ⁱ	0.86	2.60	3.4612 (19)	174
N2—H2A···O3ⁱⁱ	0.86	2.14	2.843 (2)	138
N5—H5A···O1ⁱⁱⁱ	0.86	2.01	2.852 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O₂S
M_r	301.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	9.2938 (19), 13.277 (3), 14.512 (3)
α, β, γ (°)	101.247 (17), 108.442 (13), 107.89 (3)
V (Å³)	1529.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.50 × 0.48 × 0.47

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.898, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	13899, 5958, 4590
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.151, 1.06
No. of reflections	5958
No. of parameters	386
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.30

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S2ⁱ	0.86	2.60	3.4612 (19)	174.3
N2—H2A···O3ⁱⁱ	0.86	2.14	2.843 (2)	138.4
N5—H5A···O1ⁱⁱⁱ	0.86	2.01	2.852 (2)	165.2

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

Acknowledgements

The authors thank the Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0802003B) and Professor Dr Rengen Xiong.

References

Atwal, K. S. (1990). J. Med. Chem. 33, 1510–1515. CSD CrossRef CAS PubMed Web of Science Google Scholar
Manjula, A., Rao, B. V. & Neelakantan, P. (2004). Synth. Commun. 34, 2665–2671. Web of Science CrossRef CAS Google Scholar
Matsuda, T. & Hirao, I. (1965). Nippon Kagaku Zasshi, 86, 1195–1197. CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steele, T. G., Coburn, C. A., Patane, M. A. & Bock, M. G. (1998). Tetrahedron Lett. 39, 9315–9318. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page o1733

doi:10.1107/S1600536809024520

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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