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

Fathima, N.; Nagarajaiah, H.; Begum, N.S.

doi:10.1107/S1600536812017679

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1555

doi:10.1107/S1600536812017679

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

Nikhath Fathima,^a H Nagarajaiah ^a and Noor Shahina Begum ^a ^*

^aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 31 March 2012; accepted 20 April 2012; online 28 April 2012)

In the title compound, C₁₇H₂₀N₂O₄S, the aryl ring is positioned perpendicular to the dihydropyrimidine ring, the dihedral angle between the ring planes being 77.48 (9)°. The carboxylate and methyl groups are in a cis conformation with respect to the C=C bond. The dihydropyrimidine ring adopts a twist-boat conformation. The crystal structure is stabilized by N—H⋯O and C—H⋯O interactions, the former resulting in molecular chains along the b axis and the latter forming inversion dimers.

Related literature

For the biological activity of dihydropyrimidines, see: Kappe (2000 ). For a related structure, see: Begum & Vasundhara (2009 ).

Experimental

Crystal data

C₁₇H₂₀N₂O₄S
M_r = 348.41
Monoclinic, P 2₁ /n
a = 11.515 (2) Å
b = 7.3687 (16) Å
c = 20.049 (4) Å
β = 90.960 (4)°
V = 1701.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.963, T_max = 0.967
10054 measured reflections
3707 independent reflections
2545 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.204
S = 1.03
3707 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.86	2.07	2.907 (3)	164
C3—H3B⋯O1ⁱⁱ	0.96	2.60	3.393 (4)	140
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812017679/pv2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017679/pv2529Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017679/pv2529Isup3.cml

checkCIF report

Comment top

Dihydropyrimidines have remarkable potency with antiviral, antitumor, antibacterial and anti-inflammatory activities, and are used as antihypertensive agents and calcium channel modulators (Kappe, 2000). In the structure of the title compound, the aryl ring substituted to chiral carbon atom (C4) is positioned axially to the dihydropyrimidine ring, whereas the carboxylate, methyl, acetyl and the thioxo groups are attached on the either sides of the ring. The dihedral angle between the planes of the aryl and dihydropyrimidine rings is 77.48 (9)°. The exocyclic ester at C5 adopts a cis orientation with respect to C5═C6 double bond. The central dihydropyrimidine ring is significantly puckered, assuming a conformation of twisted boat with the atoms N1 and C1 displaced from the mean plane of the remaining ring atoms (C4/C5/C6/N2) by 0.806 (4) Å and 0.517 (4) Å, respectively. The crystal structure is stabilized by intermolecular interactions N—H···O resulting in molecular chains along the crystallographic b-axis. The structure is further consolidated by intermolecular C—H···O interactions resulting in the formation of centrosymmetric dimers about inversion centers (Fig 2.) For a crystal structure related to the title compound, see: Begum & Vasundhara (2009).

Related literature top

For the biological activity of dihydropyrimidines, see: Kappe (2000). For a related structure, see: Begum & Vasundhara (2009).

Experimental top

4-(3-Methoxy-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5 carboxylic acid ethyl ester (3.06 g, 10 mmol) was mixed with acetic anhydride (20 ml) and refluxed for about 4 h. The reaction mixture was cooled and diluted by addition of water (20 ml). The solid separated, washed with water, filtered and dried (Yield: 1.92 g, 85% and mp 430-432 K). Pale yellow crystals of the title compound were obtained for diffraction by slow evaporation from a solution in chloroform.

Computing details top

Data collection: SMART (Bruker,1998); cell refinement: SAINT-Plus (Bruker,1998); data reduction: SAINT-Plus (Bruker, 1998); 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 CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the intermolecular hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non participating in H-bonding were ommitted for clarity.

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

Crystal data top

C₁₇H₂₀N₂O₄S	F(000) = 736
M_r = 348.41	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3707 reflections
a = 11.515 (2) Å	θ = 2.0–27.0°
b = 7.3687 (16) Å	µ = 0.21 mm⁻¹
c = 20.049 (4) Å	T = 296 K
β = 90.960 (4)°	Block, yellow
V = 1701.0 (6) Å³	0.18 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	3707 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→14
T_min = 0.963, T_max = 0.967	k = −9→9
10054 measured reflections	l = −23→25

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1146P)² + 0.3834P] where P = (F_o² + 2F_c²)/3
3707 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₇H₂₀N₂O₄S	V = 1701.0 (6) Å³
M_r = 348.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.515 (2) Å	µ = 0.21 mm⁻¹
b = 7.3687 (16) Å	T = 296 K
c = 20.049 (4) Å	0.18 × 0.16 × 0.16 mm
β = 90.960 (4)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	3707 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2545 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.967	R_int = 0.042
10054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
3707 reflections	Δρ_min = −0.43 e Å⁻³
221 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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
C1	0.6452 (2)	0.0344 (3)	0.14742 (12)	0.0409 (6)
C2	0.6628 (2)	−0.3005 (3)	0.13502 (13)	0.0425 (6)
C3	0.7912 (2)	−0.2995 (4)	0.12735 (17)	0.0603 (8)
H3A	0.8280	−0.2751	0.1697	0.090*
H3B	0.8123	−0.2072	0.0960	0.090*
H3C	0.8162	−0.4157	0.1113	0.090*
C4	0.4706 (2)	−0.1548 (3)	0.13863 (12)	0.0362 (5)
H4	0.4507	−0.2765	0.1224	0.043*
C5	0.4207 (2)	−0.0197 (3)	0.08906 (11)	0.0377 (5)
C6	0.4725 (2)	0.1430 (3)	0.08596 (12)	0.0392 (6)
C7	0.4401 (3)	0.3040 (4)	0.04509 (14)	0.0525 (7)
H7A	0.3746	0.2748	0.0169	0.079*
H7B	0.5045	0.3383	0.0180	0.079*
H7C	0.4204	0.4029	0.0740	0.079*
C8	0.3207 (2)	−0.0652 (4)	0.04555 (13)	0.0485 (7)
C9	0.1922 (3)	−0.2962 (5)	0.00900 (18)	0.0734 (10)
H9A	0.1954	−0.4267	0.0031	0.088*
H9B	0.1998	−0.2402	−0.0345	0.088*
C10	0.0772 (3)	−0.2451 (7)	0.0375 (2)	0.0975 (14)
H10A	0.0713	−0.2945	0.0817	0.146*
H10B	0.0158	−0.2929	0.0098	0.146*
H10C	0.0709	−0.1153	0.0395	0.146*
C11	0.4234 (2)	−0.1375 (3)	0.20943 (12)	0.0380 (5)
C12	0.4961 (2)	−0.1400 (4)	0.26504 (13)	0.0481 (6)
H12	0.5763	−0.1422	0.2603	0.058*
C13	0.4480 (3)	−0.1390 (4)	0.32820 (14)	0.0586 (8)
H13	0.4968	−0.1423	0.3656	0.070*
C14	0.3303 (3)	−0.1334 (4)	0.33644 (14)	0.0575 (8)
H14	0.2998	−0.1332	0.3791	0.069*
C15	0.2568 (2)	−0.1281 (4)	0.28122 (14)	0.0480 (6)
C16	0.3032 (2)	−0.1295 (3)	0.21776 (13)	0.0428 (6)
H16	0.2540	−0.1251	0.1805	0.051*
C17	0.0614 (3)	−0.1270 (5)	0.23868 (15)	0.0603 (8)
H17A	0.0741	−0.0239	0.2105	0.090*
H17B	−0.0168	−0.1248	0.2544	0.090*
H17C	0.0737	−0.2365	0.2138	0.090*
O1	0.2712 (2)	0.0368 (4)	0.00752 (12)	0.0801 (8)
O2	0.28828 (17)	−0.2390 (3)	0.05194 (10)	0.0567 (5)
O3	0.60926 (17)	−0.4423 (3)	0.13563 (11)	0.0606 (6)
O4	0.14055 (17)	−0.1211 (3)	0.29420 (10)	0.0607 (6)
N1	0.59906 (16)	−0.1391 (3)	0.13862 (10)	0.0368 (5)
N2	0.57304 (19)	0.1684 (3)	0.12438 (11)	0.0434 (5)
H2	0.5913	0.2783	0.1345	0.052*
S1	0.76922 (7)	0.08775 (12)	0.18297 (5)	0.0651 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0441 (13)	0.0361 (13)	0.0426 (13)	−0.0028 (10)	0.0040 (10)	−0.0003 (10)
C2	0.0491 (14)	0.0370 (14)	0.0413 (13)	0.0064 (11)	−0.0005 (11)	−0.0020 (10)
C3	0.0470 (16)	0.0604 (19)	0.073 (2)	0.0127 (14)	−0.0017 (14)	−0.0011 (15)
C4	0.0344 (12)	0.0333 (12)	0.0408 (13)	−0.0016 (9)	0.0001 (10)	−0.0020 (9)
C5	0.0386 (12)	0.0397 (13)	0.0349 (12)	0.0014 (10)	0.0043 (10)	−0.0005 (10)
C6	0.0426 (13)	0.0398 (14)	0.0353 (12)	0.0066 (10)	0.0037 (10)	0.0016 (10)
C7	0.0661 (18)	0.0433 (15)	0.0484 (16)	0.0069 (13)	0.0059 (13)	0.0105 (12)
C8	0.0436 (14)	0.0605 (18)	0.0414 (14)	−0.0028 (13)	0.0010 (11)	0.0043 (12)
C9	0.073 (2)	0.080 (2)	0.066 (2)	−0.0215 (18)	−0.0174 (17)	−0.0050 (18)
C10	0.059 (2)	0.134 (4)	0.099 (3)	−0.022 (2)	−0.010 (2)	0.016 (3)
C11	0.0412 (13)	0.0338 (13)	0.0391 (13)	0.0014 (10)	−0.0008 (10)	0.0037 (10)
C12	0.0457 (14)	0.0522 (16)	0.0464 (15)	−0.0006 (12)	−0.0009 (11)	0.0042 (12)
C13	0.0581 (18)	0.077 (2)	0.0406 (15)	−0.0021 (15)	−0.0058 (12)	0.0020 (14)
C14	0.0617 (18)	0.072 (2)	0.0388 (15)	−0.0040 (15)	0.0076 (13)	−0.0009 (13)
C15	0.0484 (15)	0.0483 (16)	0.0476 (15)	0.0005 (12)	0.0083 (12)	0.0007 (12)
C16	0.0445 (14)	0.0444 (15)	0.0395 (13)	0.0005 (11)	0.0018 (11)	0.0033 (11)
C17	0.0472 (16)	0.075 (2)	0.0592 (18)	0.0029 (14)	0.0061 (13)	0.0026 (15)
O1	0.0780 (16)	0.0834 (17)	0.0776 (16)	−0.0116 (13)	−0.0360 (13)	0.0318 (13)
O2	0.0535 (12)	0.0591 (13)	0.0570 (12)	−0.0108 (9)	−0.0138 (9)	−0.0023 (9)
O3	0.0610 (13)	0.0308 (10)	0.0900 (17)	0.0025 (9)	−0.0015 (11)	−0.0033 (9)
O4	0.0478 (11)	0.0860 (16)	0.0487 (12)	−0.0003 (10)	0.0123 (9)	−0.0003 (10)
N1	0.0379 (11)	0.0323 (11)	0.0403 (11)	−0.0005 (8)	0.0005 (8)	−0.0009 (8)
N2	0.0506 (12)	0.0293 (11)	0.0504 (13)	−0.0006 (9)	0.0024 (10)	−0.0021 (9)
S1	0.0572 (5)	0.0578 (5)	0.0797 (6)	−0.0096 (4)	−0.0160 (4)	−0.0046 (4)

Geometric parameters (Å, º) top

C1—N2	1.366 (3)	C9—C10	1.500 (6)
C1—N1	1.395 (3)	C9—H9A	0.9700
C1—S1	1.633 (3)	C9—H9B	0.9700
C2—O3	1.213 (3)	C10—H10A	0.9600
C2—N1	1.400 (3)	C10—H10B	0.9600
C2—C3	1.489 (4)	C10—H10C	0.9600
C3—H3A	0.9600	C11—C12	1.383 (4)
C3—H3B	0.9600	C11—C16	1.398 (3)
C3—H3C	0.9600	C12—C13	1.391 (4)
C4—N1	1.484 (3)	C12—H12	0.9300
C4—C5	1.513 (3)	C13—C14	1.369 (4)
C4—C11	1.534 (3)	C13—H13	0.9300
C4—H4	0.9800	C14—C15	1.383 (4)
C5—C6	1.341 (3)	C14—H14	0.9300
C5—C8	1.471 (3)	C15—O4	1.369 (3)
C6—N2	1.393 (3)	C15—C16	1.388 (4)
C6—C7	1.486 (4)	C16—H16	0.9300
C7—H7A	0.9600	C17—O4	1.427 (4)
C7—H7B	0.9600	C17—H17A	0.9600
C7—H7C	0.9600	C17—H17B	0.9600
C8—O1	1.207 (3)	C17—H17C	0.9600
C8—O2	1.341 (4)	N2—H2	0.8600
C9—O2	1.453 (4)

N2—C1—N1	113.0 (2)	C9—C10—H10A	109.5
N2—C1—S1	119.74 (19)	C9—C10—H10B	109.5
N1—C1—S1	127.20 (19)	H10A—C10—H10B	109.5
O3—C2—N1	117.6 (2)	C9—C10—H10C	109.5
O3—C2—C3	120.7 (2)	H10A—C10—H10C	109.5
N1—C2—C3	121.6 (2)	H10B—C10—H10C	109.5
C2—C3—H3A	109.5	C12—C11—C16	119.4 (2)
C2—C3—H3B	109.5	C12—C11—C4	121.7 (2)
H3A—C3—H3B	109.5	C16—C11—C4	118.7 (2)
C2—C3—H3C	109.5	C11—C12—C13	119.3 (3)
H3A—C3—H3C	109.5	C11—C12—H12	120.4
H3B—C3—H3C	109.5	C13—C12—H12	120.4
N1—C4—C5	108.44 (18)	C14—C13—C12	121.4 (3)
N1—C4—C11	111.24 (19)	C14—C13—H13	119.3
C5—C4—C11	114.62 (19)	C12—C13—H13	119.3
N1—C4—H4	107.4	C13—C14—C15	119.9 (3)
C5—C4—H4	107.4	C13—C14—H14	120.1
C11—C4—H4	107.4	C15—C14—H14	120.1
C6—C5—C8	121.3 (2)	O4—C15—C14	115.9 (2)
C6—C5—C4	117.0 (2)	O4—C15—C16	124.6 (3)
C8—C5—C4	121.6 (2)	C14—C15—C16	119.6 (3)
C5—C6—N2	117.5 (2)	C15—C16—C11	120.5 (2)
C5—C6—C7	129.2 (2)	C15—C16—H16	119.8
N2—C6—C7	113.3 (2)	C11—C16—H16	119.8
C6—C7—H7A	109.5	O4—C17—H17A	109.5
C6—C7—H7B	109.5	O4—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
C6—C7—H7C	109.5	O4—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
O1—C8—O2	121.7 (3)	C8—O2—C9	115.5 (2)
O1—C8—C5	126.1 (3)	C15—O4—C17	117.6 (2)
O2—C8—C5	112.2 (2)	C1—N1—C2	125.9 (2)
O2—C9—C10	111.7 (3)	C1—N1—C4	116.71 (19)
O2—C9—H9A	109.3	C2—N1—C4	117.22 (19)
C10—C9—H9A	109.3	C1—N2—C6	125.8 (2)
O2—C9—H9B	109.3	C1—N2—H2	117.1
C10—C9—H9B	109.3	C6—N2—H2	117.1
H9A—C9—H9B	107.9

N1—C4—C5—C6	−38.9 (3)	C12—C11—C16—C15	−1.4 (4)
C11—C4—C5—C6	86.0 (3)	C4—C11—C16—C15	175.0 (2)
N1—C4—C5—C8	140.3 (2)	O1—C8—O2—C9	1.5 (4)
C11—C4—C5—C8	−94.7 (3)	C5—C8—O2—C9	−178.2 (2)
C8—C5—C6—N2	−174.1 (2)	C10—C9—O2—C8	−82.3 (4)
C4—C5—C6—N2	5.2 (3)	C14—C15—O4—C17	−176.1 (2)
C8—C5—C6—C7	3.9 (4)	C16—C15—O4—C17	4.1 (4)
C4—C5—C6—C7	−176.8 (2)	N2—C1—N1—C2	156.5 (2)
C6—C5—C8—O1	−5.4 (4)	S1—C1—N1—C2	−25.5 (4)
C4—C5—C8—O1	175.4 (3)	N2—C1—N1—C4	−28.8 (3)
C6—C5—C8—O2	174.3 (2)	S1—C1—N1—C4	149.21 (19)
C4—C5—C8—O2	−4.9 (3)	O3—C2—N1—C1	171.0 (2)
N1—C4—C11—C12	−10.5 (3)	C3—C2—N1—C1	−12.0 (4)
C5—C4—C11—C12	−134.0 (2)	O3—C2—N1—C4	−3.7 (3)
N1—C4—C11—C16	173.2 (2)	C3—C2—N1—C4	173.4 (2)
C5—C4—C11—C16	49.7 (3)	C5—C4—N1—C1	52.0 (3)
C16—C11—C12—C13	1.6 (4)	C11—C4—N1—C1	−75.0 (2)
C4—C11—C12—C13	−174.7 (3)	C5—C4—N1—C2	−132.9 (2)
C11—C12—C13—C14	−0.8 (5)	C11—C4—N1—C2	100.2 (2)
C12—C13—C14—C15	−0.2 (5)	N1—C1—N2—C6	−10.4 (3)
C13—C14—C15—O4	−179.5 (3)	S1—C1—N2—C6	171.47 (19)
C13—C14—C15—C16	0.4 (4)	C5—C6—N2—C1	22.8 (4)
O4—C15—C16—C11	−179.8 (2)	C7—C6—N2—C1	−155.5 (2)
C14—C15—C16—C11	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.86	2.07	2.907 (3)	164
C3—H3B···O1ⁱⁱ	0.96	2.60	3.393 (4)	140

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀N₂O₄S
M_r	348.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.515 (2), 7.3687 (16), 20.049 (4)
β (°)	90.960 (4)
V (Å³)	1701.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.963, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	10054, 3707, 2545
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.204, 1.03
No. of reflections	3707
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.43

Computer programs: SMART (Bruker,1998), SAINT-Plus (Bruker,1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.860	2.070	2.907 (3)	164
C3—H3B···O1ⁱⁱ	0.960	2.597	3.393 (4)	140

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

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Begum, N. S. & Vasundhara, D. E. (2009). J. Chem. Res. 4, 201–204. Web of Science CrossRef Google Scholar
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

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Volume 68| Part 5| May 2012| Page o1555

doi:10.1107/S1600536812017679

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

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References

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