6-Cyclo­hexyl­meth­yl-5-ethyl-2-[(2-oxo-2-phenyl­eth­yl)sulfan­yl]pyrimidin-4(3H)-one

Yan, W.-L.; Guo, Q.; Li, C.; Ji, X.-Y.; He, Y.-P.

doi:10.1107/S1600536811003175

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o534

doi:10.1107/S1600536811003175

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6-Cyclohexylmethyl-5-ethyl-2-[(2-oxo-2-phenylethyl)sulfanyl]pyrimidin-4(3H)-one

Wan-Lu Yan,^a Qiong Guo,^a Cong Li,^a Xiao-Ying Ji ^b and Yan-Ping He ^a ^*

^aSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resources (Ministry of Education), Yunnan University, Kunming 650091, People's Republic of China, and ^bLaboratory of Molecular Medicine, College of Pharmaceutical Science, Soochow University, Suzhou 215123, People's Republic of China
^*Correspondence e-mail: ypinghe@126.com

(Received 18 January 2011; accepted 24 January 2011; online 29 January 2011)

In the title compound, C₂₁H₂₆N₂O₂S, the cyclohexane ring adopts a chair conformation. The angle at the methylene bridge linking the pyrimidine and cyclohexane rings is 113.41 (13)°. This is in the range considered optimal for maximum activity of non-nucleoside reverse transcriptase inhibitors. In the crystal, molecules are connected into centrosymmetric dimers via pairs of N—H⋯O hydrogen bonds.

Related literature

For the biological activity of 2-alkylsulfanyl-6-benzyl-3,4-dihydropyrimidin-4(3H)-one derivatives, which show remarkable anti-HIV-1 activity, see: He et al. (2011 ); Ettorre et al. (1996 ). For related structures, see: Ettorre et al. (1998 ); Rao et al. (2007 ); Zhang et al. (2008 ).

Experimental

Crystal data

C₂₁H₂₆N₂O₂S
M_r = 370.50
Triclinic, $[P \overline 1]$
a = 7.516 (5) Å
b = 10.960 (5) Å
c = 12.490 (5) Å
α = 84.082 (5)°
β = 78.925 (5)°
γ = 80.267 (5)°
V = 992.5 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.46 × 0.23 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.944, T_max = 0.975
7097 measured reflections
4158 independent reflections
3203 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.129
S = 1.03
4158 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	1.90	2.743 (2)	168
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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/S1600536811003175/tk2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003175/tk2710Isup2.hkl

checkCIF report

Comment top

As part of on-going investigations of S-DABO analogues, e.g. 2-alkylsulfanyl-6-benzyl-3,4-dihydropyrimidin-4(3H) -one derivatives, which comprise a potent family of non-nucleoside reverse transcriptase inhibitors (NNRTI's), the title compound was synthesized as a novel inhibitor which shows remarkable anti-HIV-1 activity (He et al., 2011).

The molecular structure is shown in Fig. 1. The cyclohexane ring adopts a chair conformation. The C12—C15—C16 angle is 113.41 (13)°, which is in the range considered optimal for maximum activity of NNRTI's, viz. 110–115° (Ettorre et al., 1996).

A comparison of the molecular structure of the title compound with some reported S-DABO's show that their spatial arrangement are similar (Ettorre et al., 1998; Rao et al., 2007; Zhang et al., 2008). Although these molecules assume similar conformations, they show differences in their activities. Thus, further structural investigations are needed in order to establish a structure-activity relationship.

In the crystal, molecules are connected into centrosymmetric dimers via N—H···O hydrogen bonds, Table 1.

Related literature top

For the biological activity of 2-alkylsulfanyl-6-benzyl-3,4-dihydropyrimidin-4(3H)-one derivatives, see: He et al. (2011); Ettorre et al. (1996). For related structures, see: Ettorre et al. (1998); Rao et al. (2007); Zhang et al. (2008).

Experimental top

With 2-cyclohexylacetonitrile as the starting material, the title compound was synthesized according to the procedure of He et al. (2011). Single crystals of the title compound were obtained from the slow evaporation at room temperature of its ethyl acetate/petroleum ether solution.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 molecular structure of the title compound, showing the atom labelling scheme and 30% probability displacement ellipsoids.

6-Cyclohexylmethyl-5-ethyl-2-[(2-oxo-2-phenylethyl)sulfanyl]pyrimidin- 4(3H)-one top

Crystal data top

C₂₁H₂₆N₂O₂S	Z = 2
M_r = 370.50	F(000) = 396
Triclinic, P1	D_x = 1.240 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.516 (5) Å	Cell parameters from 2756 reflections
b = 10.960 (5) Å	θ = 2.4–27.3°
c = 12.490 (5) Å	µ = 0.18 mm⁻¹
α = 84.082 (5)°	T = 293 K
β = 78.925 (5)°	Block, colourless
γ = 80.267 (5)°	0.46 × 0.23 × 0.17 mm
V = 992.5 (9) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	3203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 28.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.944, T_max = 0.975	k = −14→14
7097 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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0735P)² + 0.0929P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4158 reflections	Δρ_max = 0.18 e Å⁻³
237 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

Crystal data top

C₂₁H₂₆N₂O₂S	γ = 80.267 (5)°
M_r = 370.50	V = 992.5 (9) Å³
Triclinic, P1	Z = 2
a = 7.516 (5) Å	Mo Kα radiation
b = 10.960 (5) Å	µ = 0.18 mm⁻¹
c = 12.490 (5) Å	T = 293 K
α = 84.082 (5)°	0.46 × 0.23 × 0.17 mm
β = 78.925 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4158 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3203 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.975	R_int = 0.019
7097 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
4158 reflections	Δρ_min = −0.18 e Å⁻³
237 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
C1	0.0651 (2)	0.34455 (19)	0.37479 (16)	0.0637 (5)
H1	0.0740	0.2786	0.4276	0.076*
C2	−0.0742 (3)	0.3611 (2)	0.31452 (19)	0.0768 (6)
H2	−0.1563	0.3044	0.3255	0.092*
C3	−0.0931 (3)	0.4597 (2)	0.23879 (17)	0.0735 (6)
H3	−0.1883	0.4709	0.1992	0.088*
C4	0.0298 (3)	0.5416 (2)	0.22211 (17)	0.0707 (6)
H4	0.0174	0.6092	0.1711	0.085*
C5	0.1713 (3)	0.52527 (17)	0.27987 (16)	0.0622 (5)
H5	0.2543	0.5815	0.2671	0.075*
C6	0.1917 (2)	0.42627 (15)	0.35661 (13)	0.0483 (4)
C7	0.3555 (2)	0.40826 (14)	0.41151 (14)	0.0490 (4)
C8	0.3441 (2)	0.33926 (16)	0.52377 (14)	0.0518 (4)
H8A	0.2644	0.2772	0.5284	0.062*
H8B	0.2876	0.3975	0.5784	0.062*
C9	0.6130 (2)	0.14968 (13)	0.46180 (12)	0.0409 (3)
C10	0.8364 (2)	−0.02021 (14)	0.39454 (12)	0.0451 (4)
C11	0.7259 (2)	−0.02517 (14)	0.31332 (12)	0.0436 (4)
C12	0.5655 (2)	0.05556 (14)	0.31667 (12)	0.0426 (4)
C13	0.8014 (3)	−0.12053 (17)	0.23150 (14)	0.0548 (4)
H13A	0.7058	−0.1299	0.1921	0.066*
H13B	0.8355	−0.1997	0.2704	0.066*
C14	0.9669 (3)	−0.0886 (2)	0.14963 (16)	0.0727 (6)
H14A	0.9352	−0.0095	0.1116	0.109*
H14B	1.0048	−0.1512	0.0980	0.109*
H14C	1.0655	−0.0849	0.1874	0.109*
C15	0.4356 (2)	0.06173 (16)	0.23778 (14)	0.0529 (4)
H15A	0.3134	0.0568	0.2789	0.063*
H15B	0.4723	−0.0096	0.1942	0.063*
C16	0.4293 (2)	0.18009 (16)	0.16104 (13)	0.0504 (4)
H16	0.3873	0.2507	0.2065	0.060*
C17	0.6149 (3)	0.19746 (19)	0.09419 (16)	0.0658 (5)
H17A	0.6629	0.1263	0.0514	0.079*
H17B	0.6992	0.2017	0.1431	0.079*
C18	0.6038 (4)	0.3151 (2)	0.0178 (2)	0.0849 (7)
H18A	0.5672	0.3869	0.0608	0.102*
H18B	0.7238	0.3211	−0.0259	0.102*
C19	0.4667 (4)	0.3152 (2)	−0.05721 (19)	0.0914 (8)
H19A	0.4570	0.3930	−0.1019	0.110*
H19B	0.5099	0.2485	−0.1057	0.110*
C20	0.2831 (4)	0.2987 (2)	0.00690 (19)	0.0825 (7)
H20A	0.2010	0.2931	−0.0430	0.099*
H20B	0.2335	0.3709	0.0481	0.099*
C21	0.2904 (3)	0.1827 (2)	0.08558 (17)	0.0692 (6)
H21A	0.3233	0.1098	0.0439	0.083*
H21B	0.1697	0.1797	0.1296	0.083*
N2	0.77310 (18)	0.07257 (11)	0.46550 (10)	0.0446 (3)
H2A	0.8372	0.0817	0.5134	0.054*
N1	0.50716 (18)	0.14361 (12)	0.39265 (10)	0.0448 (3)
O1	0.49051 (17)	0.45336 (12)	0.36902 (12)	0.0662 (4)
O2	0.98026 (18)	−0.09226 (11)	0.40372 (10)	0.0621 (4)
S1	0.56039 (6)	0.26398 (4)	0.55656 (3)	0.05176 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0452 (10)	0.0686 (12)	0.0717 (12)	−0.0097 (9)	−0.0091 (9)	0.0197 (9)
C2	0.0499 (11)	0.0943 (16)	0.0845 (14)	−0.0205 (11)	−0.0142 (10)	0.0214 (12)
C3	0.0470 (11)	0.0964 (16)	0.0684 (12)	0.0058 (11)	−0.0100 (9)	0.0057 (11)
C4	0.0724 (14)	0.0637 (12)	0.0646 (12)	0.0105 (11)	−0.0110 (10)	0.0120 (9)
C5	0.0633 (12)	0.0491 (10)	0.0674 (11)	−0.0028 (9)	−0.0045 (9)	0.0042 (8)
C6	0.0420 (9)	0.0427 (8)	0.0527 (9)	0.0021 (7)	0.0018 (7)	−0.0016 (7)
C7	0.0457 (9)	0.0372 (8)	0.0592 (10)	−0.0009 (7)	−0.0011 (7)	−0.0055 (7)
C8	0.0487 (10)	0.0530 (9)	0.0509 (9)	−0.0024 (8)	−0.0029 (7)	−0.0107 (7)
C9	0.0456 (9)	0.0369 (7)	0.0395 (7)	−0.0058 (6)	−0.0076 (6)	−0.0002 (6)
C10	0.0532 (10)	0.0387 (8)	0.0439 (8)	−0.0027 (7)	−0.0134 (7)	−0.0029 (6)
C11	0.0516 (9)	0.0411 (8)	0.0393 (8)	−0.0107 (7)	−0.0093 (6)	−0.0013 (6)
C12	0.0472 (9)	0.0437 (8)	0.0390 (7)	−0.0127 (7)	−0.0099 (6)	0.0015 (6)
C13	0.0617 (11)	0.0549 (10)	0.0488 (9)	−0.0067 (8)	−0.0091 (8)	−0.0131 (7)
C14	0.0771 (14)	0.0703 (13)	0.0607 (11)	−0.0026 (11)	0.0067 (10)	−0.0082 (9)
C15	0.0548 (10)	0.0564 (10)	0.0533 (9)	−0.0147 (8)	−0.0184 (8)	−0.0041 (8)
C16	0.0554 (10)	0.0515 (9)	0.0475 (9)	−0.0019 (8)	−0.0197 (7)	−0.0093 (7)
C17	0.0657 (12)	0.0642 (12)	0.0646 (11)	−0.0061 (10)	−0.0143 (9)	0.0076 (9)
C18	0.0946 (18)	0.0703 (14)	0.0837 (15)	−0.0142 (13)	−0.0134 (13)	0.0207 (12)
C19	0.134 (2)	0.0711 (15)	0.0622 (13)	0.0098 (15)	−0.0294 (14)	0.0062 (11)
C20	0.1008 (19)	0.0758 (14)	0.0750 (14)	0.0137 (13)	−0.0477 (14)	−0.0086 (11)
C21	0.0726 (14)	0.0746 (13)	0.0682 (12)	−0.0044 (11)	−0.0350 (10)	−0.0099 (10)
N2	0.0524 (8)	0.0418 (7)	0.0421 (7)	−0.0032 (6)	−0.0171 (6)	−0.0049 (5)
N1	0.0461 (8)	0.0456 (7)	0.0443 (7)	−0.0062 (6)	−0.0122 (6)	−0.0038 (5)
O1	0.0512 (8)	0.0637 (8)	0.0807 (9)	−0.0157 (6)	−0.0052 (6)	0.0069 (7)
O2	0.0699 (9)	0.0519 (7)	0.0667 (8)	0.0136 (6)	−0.0314 (6)	−0.0164 (6)
S1	0.0566 (3)	0.0501 (3)	0.0499 (3)	−0.00196 (19)	−0.01321 (19)	−0.01319 (18)

Geometric parameters (Å, º) top

C1—C2	1.380 (3)	C13—C14	1.516 (3)
C1—C6	1.386 (2)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.368 (3)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.368 (3)	C14—H14C	0.9600
C3—H3	0.9300	C15—C16	1.531 (2)
C4—C5	1.374 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.380 (3)	C16—C17	1.513 (3)
C5—H5	0.9300	C16—C21	1.530 (2)
C6—C7	1.497 (3)	C16—H16	0.9800
C7—O1	1.210 (2)	C17—C18	1.523 (3)
C7—C8	1.517 (2)	C17—H17A	0.9700
C8—S1	1.795 (2)	C17—H17B	0.9700
C8—H8A	0.9700	C18—C19	1.520 (3)
C8—H8B	0.9700	C18—H18A	0.9700
C9—N1	1.295 (2)	C18—H18B	0.9700
C9—N2	1.354 (2)	C19—C20	1.486 (4)
C9—S1	1.7563 (16)	C19—H19A	0.9700
C10—O2	1.243 (2)	C19—H19B	0.9700
C10—N2	1.381 (2)	C20—C21	1.524 (3)
C10—C11	1.440 (2)	C20—H20A	0.9700
C11—C12	1.366 (2)	C20—H20B	0.9700
C11—C13	1.502 (2)	C21—H21A	0.9700
C12—N1	1.382 (2)	C21—H21B	0.9700
C12—C15	1.504 (2)	N2—H2A	0.8600

C2—C1—C6	120.01 (18)	H14A—C14—H14C	109.5
C2—C1—H1	120.0	H14B—C14—H14C	109.5
C6—C1—H1	120.0	C12—C15—C16	113.41 (13)
C3—C2—C1	120.9 (2)	C12—C15—H15A	108.9
C3—C2—H2	119.5	C16—C15—H15A	108.9
C1—C2—H2	119.5	C12—C15—H15B	108.9
C4—C3—C2	119.1 (2)	C16—C15—H15B	108.9
C4—C3—H3	120.5	H15A—C15—H15B	107.7
C2—C3—H3	120.5	C17—C16—C21	110.13 (16)
C3—C4—C5	120.76 (19)	C17—C16—C15	113.00 (15)
C3—C4—H4	119.6	C21—C16—C15	110.86 (15)
C5—C4—H4	119.6	C17—C16—H16	107.5
C4—C5—C6	120.67 (19)	C21—C16—H16	107.5
C4—C5—H5	119.7	C15—C16—H16	107.5
C6—C5—H5	119.7	C16—C17—C18	111.75 (17)
C5—C6—C1	118.49 (18)	C16—C17—H17A	109.3
C5—C6—C7	118.30 (16)	C18—C17—H17A	109.3
C1—C6—C7	123.11 (16)	C16—C17—H17B	109.3
O1—C7—C6	120.20 (16)	C18—C17—H17B	109.3
O1—C7—C8	121.06 (16)	H17A—C17—H17B	107.9
C6—C7—C8	118.65 (14)	C19—C18—C17	111.2 (2)
C7—C8—S1	114.80 (12)	C19—C18—H18A	109.4
C7—C8—H8A	108.6	C17—C18—H18A	109.4
S1—C8—H8A	108.6	C19—C18—H18B	109.4
C7—C8—H8B	108.6	C17—C18—H18B	109.4
S1—C8—H8B	108.6	H18A—C18—H18B	108.0
H8A—C8—H8B	107.5	C20—C19—C18	111.0 (2)
N1—C9—N2	123.68 (14)	C20—C19—H19A	109.4
N1—C9—S1	121.55 (12)	C18—C19—H19A	109.4
N2—C9—S1	114.75 (11)	C20—C19—H19B	109.4
O2—C10—N2	119.81 (14)	C18—C19—H19B	109.4
O2—C10—C11	124.65 (14)	H19A—C19—H19B	108.0
N2—C10—C11	115.54 (14)	C19—C20—C21	112.29 (19)
C12—C11—C10	118.33 (14)	C19—C20—H20A	109.1
C12—C11—C13	126.18 (15)	C21—C20—H20A	109.1
C10—C11—C13	115.48 (15)	C19—C20—H20B	109.1
C11—C12—N1	122.99 (14)	C21—C20—H20B	109.1
C11—C12—C15	124.59 (14)	H20A—C20—H20B	107.9
N1—C12—C15	112.40 (14)	C20—C21—C16	112.09 (17)
C11—C13—C14	113.75 (15)	C20—C21—H21A	109.2
C11—C13—H13A	108.8	C16—C21—H21A	109.2
C14—C13—H13A	108.8	C20—C21—H21B	109.2
C11—C13—H13B	108.8	C16—C21—H21B	109.2
C14—C13—H13B	108.8	H21A—C21—H21B	107.9
H13A—C13—H13B	107.7	C9—N2—C10	121.91 (13)
C13—C14—H14A	109.5	C9—N2—H2A	119.0
C13—C14—H14B	109.5	C10—N2—H2A	119.0
H14A—C14—H14B	109.5	C9—N1—C12	117.43 (14)
C13—C14—H14C	109.5	C9—S1—C8	99.15 (8)

C6—C1—C2—C3	−2.0 (4)	C11—C12—C15—C16	−110.85 (18)
C1—C2—C3—C4	0.9 (4)	N1—C12—C15—C16	67.63 (19)
C2—C3—C4—C5	0.4 (3)	C12—C15—C16—C17	57.7 (2)
C3—C4—C5—C6	−0.5 (3)	C12—C15—C16—C21	−178.14 (15)
C4—C5—C6—C1	−0.6 (3)	C21—C16—C17—C18	54.8 (2)
C4—C5—C6—C7	175.91 (16)	C15—C16—C17—C18	179.37 (17)
C2—C1—C6—C5	1.9 (3)	C16—C17—C18—C19	−56.5 (3)
C2—C1—C6—C7	−174.50 (18)	C17—C18—C19—C20	55.8 (3)
C5—C6—C7—O1	−21.6 (2)	C18—C19—C20—C21	−54.8 (3)
C1—C6—C7—O1	154.81 (18)	C19—C20—C21—C16	54.2 (2)
C5—C6—C7—C8	154.89 (16)	C17—C16—C21—C20	−53.3 (2)
C1—C6—C7—C8	−28.7 (2)	C15—C16—C21—C20	−179.13 (18)
O1—C7—C8—S1	−29.6 (2)	N1—C9—N2—C10	−0.1 (2)
C6—C7—C8—S1	153.97 (12)	S1—C9—N2—C10	−178.32 (11)
O2—C10—C11—C12	176.35 (16)	O2—C10—N2—C9	−176.98 (14)
N2—C10—C11—C12	−3.6 (2)	C11—C10—N2—C9	3.0 (2)
O2—C10—C11—C13	−4.0 (2)	N2—C9—N1—C12	−2.1 (2)
N2—C10—C11—C13	176.04 (13)	S1—C9—N1—C12	175.98 (10)
C10—C11—C12—N1	1.7 (2)	C11—C12—N1—C9	1.3 (2)
C13—C11—C12—N1	−177.99 (14)	C15—C12—N1—C9	−177.25 (13)
C10—C11—C12—C15	179.99 (14)	N1—C9—S1—C8	2.47 (15)
C13—C11—C12—C15	0.3 (2)	N2—C9—S1—C8	−179.29 (11)
C12—C11—C13—C14	107.9 (2)	C7—C8—S1—C9	−67.38 (14)
C10—C11—C13—C14	−71.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	1.90	2.743 (2)	168

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₂S
M_r	370.50
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.516 (5), 10.960 (5), 12.490 (5)
α, β, γ (°)	84.082 (5), 78.925 (5), 80.267 (5)
V (Å³)	992.5 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.46 × 0.23 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.944, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	7097, 4158, 3203
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.129, 1.03
No. of reflections	4158
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), 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
N2—H2A···O2ⁱ	0.86	1.90	2.743 (2)	168

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 30960459).

References

Bruker (2004). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ettorre, A., Mai, A., Artico, M., Massa, S., De Montis, A. & La Colla, P. (1996). Acta Cryst. C52, 2115–2117. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Ettorre, A., Mai, A., Sbardella, G., Artico, M., La Colla, P. & Massa, S. (1998). Z. Kristallogr. New Cryst. Struct. 213, 593–595. CAS Google Scholar
He, Y. P., Long, J., Zhang, S. S., Li, C., Lai, C., Zhang, C. S., Li, D. X., Zhang, D. H., Wang, H., Cai, Q. Q. & Zheng, Y. T. (2011). Bioorg. Med. Chem. Lett. 21, 694–697. Web of Science CrossRef CAS PubMed Google Scholar
Rao, Z.-K., Zhang, S.-S., He, Y.-P., Zheng, Y.-T. & Li, C. (2007). Acta Cryst. E63, o3942. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, C.-S., Li, D.-X., Zhang, D.-H., He, Y.-P. & Li, C. (2008). Acta Cryst. E64, o1768. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o534

doi:10.1107/S1600536811003175

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

6-Cyclo­hexyl­meth­yl-5-ethyl-2-[(2-oxo-2-phenyl­eth­yl)sulfan­yl]pyrimidin-4(3H)-one

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Experimental

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organic compounds

6-Cyclohexylmethyl-5-ethyl-2-[(2-oxo-2-phenylethyl)sulfanyl]pyrimidin-4(3H)-one