6-Cyclo-hexyl-meth-yl-5-ethyl-2-[(2-oxo-2-phenyl-eth-yl)sulfan-yl]pyrimidin-4(3H)-one.

In the title compound, C(21)H(26)N(2)O(2)S, the cyclo-hexane ring adopts a chair conformation. The angle at the methyl-ene bridge linking the pyrimidine and cyclo-hexane rings is 113.41 (13)°. This is in the range considered optimal for maximum activity of non-nucleoside reverse transcriptase inhibitors. In the crystal, mol-ecules 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 = 370.50

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.129

S = 1.03

4158 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003175/tk2710sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H26N2O2S	Z = 2
Mr = 370.50	F(000) = 396
Triclinic, P1	Dx = 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

Bruker SMART CCD area-detector diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	3203 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 28.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
Tmin = 0.944, Tmax = 0.975	k = −14→14
7097 measured reflections	l = −16→16

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(Fo2) + (0.0735P)2 + 0.0929P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4158 reflections	Δρmax = 0.18 e Å−3
237 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .