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

He, Q.-P.; Wang, J.-Y.; Feng, R.-K.

doi:10.1107/S160053680706730X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o352

doi:10.1107/S160053680706730X

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

Qing-Peng He,^a ^* Jian-Yong Wang ^a and Ruo-Kun Feng ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: hxqqxh2008@yahoo.com.cn

(Received 5 December 2007; accepted 17 December 2007; online 4 January 2008)

In the title molecule, C₁₈H₂₁ClN₂O₃S, the pyrimidine ring exhibits a half-chair conformation. The ethyl group is disordered between two positions in a ratio 0.74:0.26. In the crystal structure, the molecules are linked into chains along the a axis by N—H⋯O hydrogen bonds.

Related literature

For the crystal structure of a related compound, see Jiang et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₁ClN₂O₃S
M_r = 380.88
Triclinic, $[P \overline 1]$
a = 7.5227 (12) Å
b = 9.7163 (15) Å
c = 14.122 (2) Å
α = 72.617 (6)°
β = 87.300 (6)°
γ = 71.296 (6)°
V = 931.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 273 (2) K
0.14 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.954, T_max = 0.967
10470 measured reflections
3233 independent reflections
2743 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.166
S = 1.00
3233 reflections
242 parameters
63 restraints
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.71 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	2.16	2.984 (3)	160
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706730X/cv2372sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680706730X/cv2372Isup2.hkl

checkCIF report

Comment top

Herewith we present the crystal strusture of the title compound, (I), which was synthesized through the reaction of 2-chlorobenzaldehyde and ethyl acetoacetate with urea derivative under solvent-free conditions.

In (I) (Fig. 1), bond lengths and angles are normal and comparable with those observed in reported compound (Jiang et al., 2007). The pyrimidine ring exhibits a half-chair conformation with the maximal deviation of 0.168 Å for C6 from mean plane.

In the crystal, the molecules related by translation along axis a are linked into chains by N—H···O hydrogen bonds (Table 1).

Related literature top

For the crystal structure of a related compound, see Jiang et al. (2007).

Experimental top

2-Chlorobenzaldehyde (2 mmol), ethyl acetoacetate (2 mmol), urea derivatives (2.4 mmol) and H₃BO₃(0.4 mmol), in glacial acetic acid (10 ml) was heated at 373 K, while stirring for 1 h, then cooled to room temperature, and poured into ice water (50 ml), and recrystallized from EtOH, affording the title compound as a colourless crystalline solid. Elemental analysis: calculated for C₁₈H₂₁ClN₂O₃S: C 56.76, H 5.56, N 7.35%; found: C 56.68, H 5.45, N 7.44%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. Only major parts of disordered atoms is shown. H atoms omitted for clarity.

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

Crystal data top

C₁₈H₂₁ClN₂O₃S	Z = 2
M_r = 380.88	F(000) = 400
Triclinic, P1	D_x = 1.358 Mg m⁻³
a = 7.5227 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7163 (15) Å	Cell parameters from 5002 reflections
c = 14.122 (2) Å	θ = 2.3–27.4°
α = 72.617 (6)°	µ = 0.34 mm⁻¹
β = 87.300 (6)°	T = 273 K
γ = 71.296 (6)°	Block, colourless
V = 931.7 (3) Å³	0.14 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.954, T_max = 0.967	k = −11→10
10470 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.0856P)² + 1.0486P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.002
3233 reflections	Δρ_max = 0.92 e Å⁻³
242 parameters	Δρ_min = −0.71 e Å⁻³
63 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (5)

Crystal data top

C₁₈H₂₁ClN₂O₃S	γ = 71.296 (6)°
M_r = 380.88	V = 931.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.5227 (12) Å	Mo Kα radiation
b = 9.7163 (15) Å	µ = 0.34 mm⁻¹
c = 14.122 (2) Å	T = 273 K
α = 72.617 (6)°	0.14 × 0.12 × 0.10 mm
β = 87.300 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3233 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2743 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.967	R_int = 0.021
10470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	63 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.00	Δρ_max = 0.92 e Å⁻³
3233 reflections	Δρ_min = −0.71 e Å⁻³
242 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	0.25980 (13)	0.52300 (10)	0.37239 (6)	0.0576 (3)
C1	0.7929 (7)	0.7860 (5)	0.2049 (3)	0.0787 (12)
H1A	0.8645	0.7990	0.1467	0.094*
H1B	0.8473	0.8105	0.2553	0.094*
H1C	0.6657	0.8523	0.1885	0.094*
O2	0.8603 (4)	0.1939 (5)	0.0855 (2)	0.0915 (11)
O3	0.5995 (5)	0.2294 (6)	0.0050 (3)	0.1280 (14)
N1	0.3010 (3)	0.4024 (3)	0.22578 (18)	0.0459 (6)
H1	0.1819	0.4188	0.2294	0.055*
N2	0.5778 (3)	0.3881 (3)	0.29602 (17)	0.0409 (6)
O1	0.8827 (3)	0.5317 (3)	0.2018 (2)	0.0647 (7)
C2	0.7951 (4)	0.6252 (4)	0.2424 (2)	0.0507 (7)
C3	0.6906 (5)	0.5828 (4)	0.3335 (2)	0.0505 (7)
H3A	0.5621	0.6511	0.3218	0.061*
H3B	0.7468	0.5994	0.3878	0.061*
C4	0.6868 (5)	0.4201 (3)	0.3659 (2)	0.0465 (7)
H4A	0.8148	0.3511	0.3731	0.056*
H4B	0.6334	0.3999	0.4305	0.056*
C5	0.3905 (4)	0.4316 (3)	0.2963 (2)	0.0419 (6)
C6	0.6877 (4)	0.2778 (3)	0.2446 (2)	0.0378 (6)
H6	0.8002	0.3050	0.2211	0.045*
C7	0.5756 (4)	0.2894 (3)	0.1548 (2)	0.0431 (7)
C8	0.3869 (4)	0.3488 (3)	0.1493 (2)	0.0437 (7)
C9	0.7520 (4)	0.1183 (3)	0.3179 (2)	0.0388 (6)
C10	0.9389 (4)	0.0353 (3)	0.3472 (2)	0.0445 (7)
C11	0.9927 (5)	−0.1094 (4)	0.4150 (3)	0.0569 (8)
H11	1.1193	−0.1625	0.4324	0.068*
C12	0.8590 (6)	−0.1737 (4)	0.4562 (3)	0.0592 (9)
H12	0.8942	−0.2705	0.5020	0.071*
C13	0.6714 (5)	−0.0942 (4)	0.4295 (3)	0.0574 (8)
H13	0.5800	−0.1373	0.4575	0.069*
C14	0.6196 (4)	0.0488 (4)	0.3613 (2)	0.0483 (7)
H14	0.4928	0.1006	0.3438	0.058*
C15	0.6932 (5)	0.2335 (5)	0.0802 (3)	0.0619 (9)
C16	0.7016 (11)	0.2217 (13)	−0.0899 (6)	0.1280 (14)	0.740 (10)
H16A	0.6253	0.2918	−0.1489	0.154*	0.740 (10)
H16B	0.8211	0.2397	−0.0892	0.154*	0.740 (10)
C17	0.7244 (13)	0.0688 (10)	−0.0813 (8)	0.119 (3)	0.740 (10)
H17A	0.8124	0.0031	−0.0268	0.178*	0.740 (10)
H17B	0.7708	0.0476	−0.1417	0.178*	0.740 (10)
H17C	0.6055	0.0515	−0.0696	0.178*	0.740 (10)
C16'	0.719 (3)	0.101 (2)	−0.0367 (13)	0.124 (4)	0.260 (10)
H16C	0.8434	0.0499	−0.0034	0.148*	0.260 (10)
H16D	0.6574	0.0267	−0.0349	0.148*	0.260 (10)
C17'	0.725 (3)	0.195 (3)	−0.1337 (12)	0.119 (5)	0.260 (10)
H17D	0.6047	0.2722	−0.1532	0.179*	0.260 (10)
H17E	0.7526	0.1341	−0.1786	0.179*	0.260 (10)
H17F	0.8200	0.2412	−0.1354	0.179*	0.260 (10)
C18	0.2497 (5)	0.3678 (5)	0.0689 (3)	0.0608 (9)
H18A	0.3170	0.3401	0.0144	0.073*
H18B	0.1703	0.4721	0.0464	0.073*
H18C	0.1740	0.3033	0.0946	0.073*
Cl1	1.11696 (11)	0.11095 (11)	0.30061 (7)	0.0646 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0587 (5)	0.0578 (5)	0.0593 (5)	−0.0108 (4)	0.0111 (4)	−0.0317 (4)
C1	0.097 (3)	0.060 (2)	0.081 (3)	−0.031 (2)	0.015 (2)	−0.019 (2)
O2	0.0477 (15)	0.158 (3)	0.0847 (19)	−0.0197 (17)	0.0138 (13)	−0.074 (2)
O3	0.0798 (19)	0.245 (4)	0.096 (2)	−0.039 (2)	0.0175 (16)	−0.120 (3)
N1	0.0346 (12)	0.0521 (15)	0.0538 (14)	−0.0099 (11)	0.0009 (10)	−0.0243 (12)
N2	0.0438 (13)	0.0361 (12)	0.0431 (12)	−0.0083 (10)	−0.0040 (10)	−0.0165 (10)
O1	0.0564 (14)	0.0666 (16)	0.0822 (17)	−0.0224 (12)	0.0144 (12)	−0.0371 (14)
C2	0.0461 (17)	0.0491 (18)	0.0602 (18)	−0.0144 (14)	−0.0057 (14)	−0.0209 (15)
C3	0.0572 (19)	0.0451 (17)	0.0556 (18)	−0.0152 (14)	−0.0027 (14)	−0.0247 (14)
C4	0.0529 (17)	0.0434 (16)	0.0436 (15)	−0.0117 (13)	−0.0077 (13)	−0.0163 (13)
C5	0.0437 (16)	0.0353 (14)	0.0448 (15)	−0.0093 (12)	0.0011 (12)	−0.0130 (12)
C6	0.0353 (14)	0.0370 (14)	0.0429 (14)	−0.0095 (11)	0.0003 (11)	−0.0164 (12)
C7	0.0427 (16)	0.0487 (17)	0.0416 (15)	−0.0152 (13)	0.0013 (12)	−0.0180 (13)
C8	0.0432 (16)	0.0476 (17)	0.0433 (15)	−0.0154 (13)	0.0017 (12)	−0.0169 (13)
C9	0.0405 (15)	0.0351 (14)	0.0444 (14)	−0.0097 (11)	0.0008 (11)	−0.0197 (12)
C10	0.0410 (15)	0.0432 (16)	0.0527 (17)	−0.0110 (12)	−0.0025 (12)	−0.0210 (13)
C11	0.0548 (19)	0.0435 (18)	0.065 (2)	−0.0028 (15)	−0.0165 (16)	−0.0176 (15)
C12	0.077 (2)	0.0376 (17)	0.0578 (19)	−0.0124 (16)	−0.0051 (17)	−0.0123 (14)
C13	0.069 (2)	0.0486 (19)	0.0612 (19)	−0.0262 (17)	0.0147 (16)	−0.0200 (16)
C14	0.0410 (16)	0.0449 (17)	0.0612 (18)	−0.0123 (13)	0.0065 (13)	−0.0216 (14)
C15	0.049 (2)	0.093 (3)	0.0526 (19)	−0.0214 (18)	0.0071 (15)	−0.0365 (19)
C16	0.0798 (19)	0.245 (4)	0.096 (2)	−0.039 (2)	0.0175 (16)	−0.120 (3)
C17	0.115 (5)	0.119 (6)	0.129 (7)	−0.028 (5)	0.036 (5)	−0.063 (5)
C16'	0.095 (6)	0.222 (8)	0.081 (6)	−0.025 (6)	0.020 (6)	−0.116 (6)
C17'	0.104 (9)	0.196 (10)	0.076 (8)	−0.034 (9)	0.028 (7)	−0.088 (8)
C18	0.0491 (19)	0.079 (2)	0.0567 (19)	−0.0157 (17)	−0.0071 (15)	−0.0273 (18)
Cl1	0.0387 (5)	0.0689 (6)	0.0853 (6)	−0.0185 (4)	−0.0042 (4)	−0.0190 (5)

Geometric parameters (Å, º) top

S1—C5	1.680 (3)	C8—C18	1.500 (4)
C1—C2	1.487 (5)	C9—C10	1.388 (4)
C1—H1A	0.9600	C9—C14	1.396 (4)
C1—H1B	0.9600	C10—C11	1.387 (5)
C1—H1C	0.9600	C10—Cl1	1.740 (3)
O2—C15	1.189 (4)	C11—C12	1.368 (5)
O3—C15	1.318 (5)	C11—H11	0.9300
O3—C16	1.523 (7)	C12—C13	1.381 (5)
O3—C16'	1.545 (10)	C12—H12	0.9300
N1—C5	1.371 (4)	C13—C14	1.378 (5)
N1—C8	1.382 (4)	C13—H13	0.9300
N1—H1	0.8600	C14—H14	0.9300
N2—C5	1.335 (4)	C16—C17	1.408 (11)
N2—C4	1.472 (4)	C16—H16A	0.9700
N2—C6	1.483 (3)	C16—H16B	0.9700
O1—C2	1.215 (4)	C17—H17A	0.9600
C2—C3	1.497 (5)	C17—H17B	0.9600
C3—C4	1.519 (4)	C17—H17C	0.9600
C3—H3A	0.9700	C16'—C17'	1.407 (13)
C3—H3B	0.9700	C16'—H16C	0.9700
C4—H4A	0.9700	C16'—H16D	0.9700
C4—H4B	0.9700	C17'—H17D	0.9600
C6—C7	1.512 (4)	C17'—H17E	0.9600
C6—C9	1.521 (4)	C17'—H17F	0.9600
C6—H6	0.9800	C18—H18A	0.9600
C7—C8	1.346 (4)	C18—H18B	0.9600
C7—C15	1.461 (4)	C18—H18C	0.9600

C2—C1—H1A	109.5	C10—C9—C14	116.3 (3)
C2—C1—H1B	109.5	C10—C9—C6	123.7 (3)
H1A—C1—H1B	109.5	C14—C9—C6	120.0 (2)
C2—C1—H1C	109.5	C11—C10—C9	122.3 (3)
H1A—C1—H1C	109.5	C11—C10—Cl1	117.0 (2)
H1B—C1—H1C	109.5	C9—C10—Cl1	120.8 (2)
C15—O3—C16	117.8 (4)	C12—C11—C10	119.8 (3)
C15—O3—C16'	109.7 (9)	C12—C11—H11	120.1
C16—O3—C16'	44.4 (9)	C10—C11—H11	120.1
C5—N1—C8	125.2 (2)	C11—C12—C13	119.6 (3)
C5—N1—H1	117.4	C11—C12—H12	120.2
C8—N1—H1	117.4	C13—C12—H12	120.2
C5—N2—C4	120.3 (2)	C14—C13—C12	120.1 (3)
C5—N2—C6	122.7 (2)	C14—C13—H13	120.0
C4—N2—C6	115.6 (2)	C12—C13—H13	120.0
O1—C2—C1	121.0 (3)	C13—C14—C9	121.9 (3)
O1—C2—C3	121.7 (3)	C13—C14—H14	119.0
C1—C2—C3	117.2 (3)	C9—C14—H14	119.0
C2—C3—C4	115.6 (3)	O2—C15—O3	121.8 (3)
C2—C3—H3A	108.4	O2—C15—C7	123.6 (3)
C4—C3—H3A	108.4	O3—C15—C7	114.6 (3)
C2—C3—H3B	108.4	C17—C16—O3	97.9 (7)
C4—C3—H3B	108.4	C17—C16—H16A	112.2
H3A—C3—H3B	107.4	O3—C16—H16A	112.2
N2—C4—C3	113.4 (2)	C17—C16—H16B	112.2
N2—C4—H4A	108.9	O3—C16—H16B	112.2
C3—C4—H4A	108.9	H16A—C16—H16B	109.8
N2—C4—H4B	108.9	C17'—C16'—O3	96.5 (10)
C3—C4—H4B	108.9	C17'—C16'—H16C	112.5
H4A—C4—H4B	107.7	O3—C16'—H16C	112.5
N2—C5—N1	116.0 (2)	C17'—C16'—H16D	112.5
N2—C5—S1	125.3 (2)	O3—C16'—H16D	112.5
N1—C5—S1	118.7 (2)	H16C—C16'—H16D	110.0
N2—C6—C7	110.4 (2)	C16'—C17'—H17D	109.5
N2—C6—C9	109.7 (2)	C16'—C17'—H17E	109.5
C7—C6—C9	113.2 (2)	H17D—C17'—H17E	109.5
N2—C6—H6	107.8	C16'—C17'—H17F	109.5
C7—C6—H6	107.8	H17D—C17'—H17F	109.5
C9—C6—H6	107.8	H17E—C17'—H17F	109.5
C8—C7—C15	126.8 (3)	C8—C18—H18A	109.5
C8—C7—C6	120.1 (3)	C8—C18—H18B	109.5
C15—C7—C6	113.1 (2)	H18A—C18—H18B	109.5
C7—C8—N1	118.3 (3)	C8—C18—H18C	109.5
C7—C8—C18	128.8 (3)	H18A—C18—H18C	109.5
N1—C8—C18	112.9 (3)	H18B—C18—H18C	109.5

O1—C2—C3—C4	−5.4 (4)	C7—C6—C9—C10	122.2 (3)
C1—C2—C3—C4	176.6 (3)	N2—C6—C9—C14	64.6 (3)
C5—N2—C4—C3	−79.4 (3)	C7—C6—C9—C14	−59.2 (3)
C6—N2—C4—C3	114.0 (3)	C14—C9—C10—C11	0.7 (4)
C2—C3—C4—N2	−67.4 (4)	C6—C9—C10—C11	179.3 (3)
C4—N2—C5—N1	177.4 (2)	C14—C9—C10—Cl1	−178.5 (2)
C6—N2—C5—N1	−17.0 (4)	C6—C9—C10—Cl1	0.1 (4)
C4—N2—C5—S1	−0.3 (4)	C9—C10—C11—C12	−0.8 (5)
C6—N2—C5—S1	165.4 (2)	Cl1—C10—C11—C12	178.4 (3)
C8—N1—C5—N2	−7.7 (4)	C10—C11—C12—C13	0.3 (5)
C8—N1—C5—S1	170.1 (2)	C11—C12—C13—C14	0.3 (5)
C5—N2—C6—C7	30.6 (4)	C12—C13—C14—C9	−0.4 (5)
C4—N2—C6—C7	−163.1 (2)	C10—C9—C14—C13	−0.1 (4)
C5—N2—C6—C9	−94.8 (3)	C6—C9—C14—C13	−178.7 (3)
C4—N2—C6—C9	71.4 (3)	C16—O3—C15—O2	−19.1 (9)
N2—C6—C7—C8	−22.2 (4)	C16'—O3—C15—O2	28.9 (11)
C9—C6—C7—C8	101.3 (3)	C16—O3—C15—C7	161.1 (6)
N2—C6—C7—C15	156.9 (3)	C16'—O3—C15—C7	−150.9 (10)
C9—C6—C7—C15	−79.7 (3)	C8—C7—C15—O2	173.4 (4)
C15—C7—C8—N1	−176.9 (3)	C6—C7—C15—O2	−5.5 (6)
C6—C7—C8—N1	2.0 (4)	C8—C7—C15—O3	−6.8 (6)
C15—C7—C8—C18	2.5 (6)	C6—C7—C15—O3	174.3 (4)
C6—C7—C8—C18	−178.6 (3)	C15—O3—C16—C17	107.2 (7)
C5—N1—C8—C7	15.2 (4)	C16'—O3—C16—C17	16.9 (14)
C5—N1—C8—C18	−164.4 (3)	C15—O3—C16'—C17'	−120.7 (15)
N2—C6—C9—C10	−114.0 (3)	C16—O3—C16'—C17'	−10.6 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.16	2.984 (3)	160

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁ClN₂O₃S
M_r	380.88
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.5227 (12), 9.7163 (15), 14.122 (2)
α, β, γ (°)	72.617 (6), 87.300 (6), 71.296 (6)
V (Å³)	931.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	10470, 3233, 2743
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.166, 1.00
No. of reflections	3233
No. of parameters	242
No. of restraints	63
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.71

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.16	2.984 (3)	160.4

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (No. X051040).

References

Jiang, H., Yu, C.-X., Tu, S.-J., Wang, X.-S. & Yao, C.-S. (2007). Acta Cryst. E63, o298–o299. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 2| February 2008| Page o352

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

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

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References

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