3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetra-hydro-4H-thio-pyrano[3',4':2,3]thieno[5,4-d]pyrimidin-4-one.

In the title compound, C(20)H(21)N(3)OS(2), the piperidinyl ring has a distorted chair conformation. Weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. The crystal packing exhibits short inter-molecular S⋯S distances of 3.590 (2) Å.

Related literature

For properties of the compounds containing th thienopyrimidine system, see: Muller et al. (2002 ▶); Chambhare et al. (2003 ▶). For related crystal structures, see: Hu et al. (2007 ▶); Xie et al. (2007 ▶).

Experimental

Crystal data

C20H21N3OS2

M = 383.52

Triclinic,

a = 9.851 (2) Å

b = 10.755 (3) Å

c = 10.864 (3) Å

α = 117.573 (4)°

β = 106.099 (4)°

γ = 97.322 (4)°

V = 935.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 298 (2) K

0.26 × 0.12 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.982

4908 measured reflections

3203 independent reflections

2739 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.146

S = 1.08

3203 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 global, I. DOI: 10.1107/S1600536808038683/cv2480sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038683/cv2480Isup2.hkl

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

C20H21N3OS2	Z = 2
Mr = 383.52	F000 = 404
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.851 (2) Å	Cell parameters from 2241 reflections
b = 10.755 (3) Å	θ = 2.2–27.6º
c = 10.864 (3) Å	µ = 0.30 mm−1
α = 117.573 (4)º	T = 298 (2) K
β = 106.099 (4)º	Block, red
γ = 97.322 (4)º	0.26 × 0.12 × 0.06 mm
V = 935.0 (4) Å3

Bruker SMART CCD area-detector diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2739 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 0 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 2.2º
φ and ω scans	h = −11→11
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −6→12
Tmin = 0.926, Tmax = 0.982	l = −12→12
4908 measured reflections

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) = 0.146	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.1731P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3203 reflections	Δρmax = 0.29 e Å−3
235 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.4581 (3)	0.6122 (3)	0.2373 (3)	0.0512 (6)
S1	0.01324 (10)	0.73341 (11)	0.03936 (9)	0.0504 (3)
S2	0.11865 (11)	0.48110 (13)	−0.35508 (10)	0.0600 (3)
N1	0.1593 (3)	0.8366 (3)	0.3342 (3)	0.0427 (6)
N2	0.3694 (3)	0.7625 (3)	0.4072 (3)	0.0365 (6)
N3	0.2786 (3)	0.9126 (3)	0.5845 (3)	0.0425 (6)
C1	0.2676 (3)	0.8387 (3)	0.4386 (3)	0.0376 (7)
C2	0.3656 (3)	0.6767 (3)	0.2579 (3)	0.0355 (7)
C3	0.2474 (3)	0.6762 (3)	0.1466 (3)	0.0365 (7)
C4	0.1518 (3)	0.7530 (3)	0.1913 (3)	0.0392 (7)
C5	0.2090 (3)	0.5983 (3)	−0.0135 (3)	0.0383 (7)
C6	0.2920 (4)	0.5025 (4)	−0.0928 (4)	0.0468 (8)
H6A	0.3231	0.4483	−0.0449	0.056*
H6B	0.3803	0.5643	−0.0824	0.056*
C7	0.2004 (4)	0.3946 (4)	−0.2580 (4)	0.0543 (9)
H7A	0.1223	0.3216	−0.2682	0.065*
H7B	0.2629	0.3440	−0.3053	0.065*
C8	0.0051 (4)	0.5529 (4)	−0.2501 (4)	0.0485 (8)
H8A	−0.0263	0.6272	−0.2677	0.058*
H8B	−0.0830	0.4741	−0.2862	0.058*
C9	0.0850 (3)	0.6190 (4)	−0.0851 (3)	0.0417 (7)
C10	0.1465 (4)	0.9449 (5)	0.6117 (4)	0.0597 (10)
H10A	0.0584	0.8670	0.5301	0.072*
H10B	0.1404	1.0364	0.6168	0.072*
C11	0.1558 (5)	0.9573 (5)	0.7584 (5)	0.0766 (13)
H11A	0.0709	0.9837	0.7797	0.092*
H11B	0.1519	0.8624	0.7485	0.092*
C12	0.2958 (5)	1.0705 (5)	0.8881 (4)	0.0795 (14)
H12A	0.3021	1.0675	0.9774	0.095*
H12B	0.2931	1.1679	0.9086	0.095*
C13	0.4306 (5)	1.0415 (5)	0.8524 (4)	0.0651 (11)
H13A	0.5185	1.1213	0.9317	0.078*
H13B	0.4420	0.9512	0.8475	0.078*
C14	0.4149 (4)	1.0284 (4)	0.7049 (4)	0.0490 (8)
H14A	0.4121	1.1215	0.7127	0.059*
H14B	0.4998	1.0054	0.6812	0.059*
C15	0.4696 (3)	0.7434 (3)	0.5194 (3)	0.0385 (7)
C16	0.4120 (4)	0.6656 (4)	0.5735 (4)	0.0446 (8)
H16A	0.3100	0.6287	0.5416	0.053*
C17	0.5068 (5)	0.6429 (4)	0.6754 (4)	0.0562 (10)
H17A	0.4684	0.5906	0.7127	0.067*
C18	0.6570 (5)	0.6964 (5)	0.7224 (4)	0.0635 (11)
H18A	0.7202	0.6793	0.7904	0.076*
C19	0.7144 (4)	0.7753 (5)	0.6691 (4)	0.0643 (11)
H19A	0.8165	0.8127	0.7021	0.077*
C20	0.6205 (4)	0.7991 (4)	0.5661 (4)	0.0515 (9)
H20A	0.6588	0.8519	0.5291	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0471 (14)	0.0719 (16)	0.0425 (13)	0.0345 (13)	0.0203 (11)	0.0300 (12)
S1	0.0461 (5)	0.0677 (6)	0.0376 (5)	0.0310 (4)	0.0126 (4)	0.0261 (4)
S2	0.0618 (6)	0.0872 (8)	0.0411 (5)	0.0310 (5)	0.0237 (4)	0.0367 (5)
N1	0.0430 (15)	0.0485 (16)	0.0358 (14)	0.0220 (13)	0.0143 (12)	0.0199 (13)
N2	0.0329 (13)	0.0464 (15)	0.0336 (13)	0.0116 (12)	0.0110 (11)	0.0244 (12)
N3	0.0432 (15)	0.0450 (16)	0.0313 (13)	0.0145 (13)	0.0140 (12)	0.0137 (12)
C1	0.0368 (16)	0.0380 (17)	0.0366 (16)	0.0102 (14)	0.0130 (13)	0.0193 (14)
C2	0.0355 (16)	0.0433 (17)	0.0346 (16)	0.0123 (14)	0.0131 (13)	0.0256 (14)
C3	0.0319 (16)	0.0394 (17)	0.0366 (16)	0.0078 (13)	0.0124 (13)	0.0196 (14)
C4	0.0403 (17)	0.0434 (18)	0.0362 (16)	0.0170 (15)	0.0115 (14)	0.0233 (14)
C5	0.0342 (16)	0.0437 (18)	0.0369 (16)	0.0110 (14)	0.0121 (13)	0.0219 (14)
C6	0.0426 (18)	0.056 (2)	0.0397 (18)	0.0184 (16)	0.0161 (15)	0.0229 (16)
C7	0.052 (2)	0.065 (2)	0.0411 (19)	0.0272 (19)	0.0196 (16)	0.0212 (18)
C8	0.0454 (19)	0.064 (2)	0.0355 (17)	0.0203 (17)	0.0105 (15)	0.0270 (17)
C9	0.0394 (17)	0.0490 (19)	0.0356 (17)	0.0146 (15)	0.0129 (14)	0.0217 (15)
C10	0.050 (2)	0.063 (2)	0.049 (2)	0.0232 (19)	0.0186 (17)	0.0146 (18)
C11	0.084 (3)	0.083 (3)	0.061 (3)	0.025 (3)	0.048 (2)	0.026 (2)
C12	0.101 (4)	0.087 (3)	0.040 (2)	0.035 (3)	0.031 (2)	0.021 (2)
C13	0.073 (3)	0.064 (3)	0.0358 (19)	0.020 (2)	0.0086 (18)	0.0164 (18)
C14	0.052 (2)	0.0406 (19)	0.0397 (18)	0.0122 (16)	0.0104 (16)	0.0147 (15)
C15	0.0372 (17)	0.0429 (18)	0.0314 (15)	0.0153 (14)	0.0097 (13)	0.0176 (14)
C16	0.0477 (19)	0.0467 (19)	0.0401 (18)	0.0159 (16)	0.0159 (15)	0.0234 (16)
C17	0.078 (3)	0.064 (2)	0.044 (2)	0.037 (2)	0.0265 (19)	0.0366 (19)
C18	0.072 (3)	0.084 (3)	0.041 (2)	0.047 (2)	0.0161 (19)	0.034 (2)
C19	0.038 (2)	0.085 (3)	0.056 (2)	0.021 (2)	0.0055 (17)	0.033 (2)
C20	0.0413 (19)	0.065 (2)	0.048 (2)	0.0136 (17)	0.0137 (16)	0.0320 (18)

O1—C2	1.221 (4)	C10—C11	1.512 (6)
S1—C4	1.729 (3)	C10—H10A	0.9700
S1—C9	1.748 (3)	C10—H10B	0.9700
S2—C7	1.804 (4)	C11—C12	1.508 (6)
S2—C8	1.806 (3)	C11—H11A	0.9700
N1—C1	1.313 (4)	C11—H11B	0.9700
N1—C4	1.361 (4)	C12—C13	1.514 (6)
N2—C1	1.390 (4)	C12—H12A	0.9700
N2—C2	1.433 (4)	C12—H12B	0.9700
N2—C15	1.456 (4)	C13—C14	1.503 (5)
N3—C1	1.369 (4)	C13—H13A	0.9700
N3—C10	1.462 (4)	C13—H13B	0.9700
N3—C14	1.468 (4)	C14—H14A	0.9700
C2—C3	1.426 (4)	C14—H14B	0.9700
C3—C4	1.372 (4)	C15—C16	1.374 (5)
C3—C5	1.440 (4)	C15—C20	1.379 (5)
C5—C9	1.360 (4)	C16—C17	1.375 (5)
C5—C6	1.502 (4)	C16—H16A	0.9300
C6—C7	1.513 (5)	C17—C18	1.369 (6)
C6—H6A	0.9700	C17—H17A	0.9300
C6—H6B	0.9700	C18—C19	1.375 (6)
C7—H7A	0.9700	C18—H18A	0.9300
C7—H7B	0.9700	C19—C20	1.388 (5)
C8—C9	1.495 (4)	C19—H19A	0.9300
C8—H8A	0.9700	C20—H20A	0.9300
C8—H8B	0.9700
S2···S2i	3.590 (2)
C4—S1—C9	91.31 (15)	C11—C10—H10A	109.9
C7—S2—C8	97.82 (16)	N3—C10—H10B	109.9
C1—N1—C4	115.4 (3)	C11—C10—H10B	109.9
C1—N2—C2	122.6 (2)	H10A—C10—H10B	108.3
C1—N2—C15	121.4 (2)	C12—C11—C10	112.3 (4)
C2—N2—C15	115.1 (2)	C12—C11—H11A	109.1
C1—N3—C10	117.7 (3)	C10—C11—H11A	109.1
C1—N3—C14	120.9 (3)	C12—C11—H11B	109.1
C10—N3—C14	111.8 (3)	C10—C11—H11B	109.1
N1—C1—N3	119.5 (3)	H11A—C11—H11B	107.9
N1—C1—N2	122.9 (3)	C11—C12—C13	110.6 (3)
N3—C1—N2	117.5 (3)	C11—C12—H12A	109.5
O1—C2—C3	126.9 (3)	C13—C12—H12A	109.5
O1—C2—N2	119.6 (3)	C11—C12—H12B	109.5
C3—C2—N2	113.5 (3)	C13—C12—H12B	109.5
C4—C3—C2	118.4 (3)	H12A—C12—H12B	108.1
C4—C3—C5	113.6 (3)	C14—C13—C12	110.4 (3)
C2—C3—C5	127.9 (3)	C14—C13—H13A	109.6
N1—C4—C3	127.1 (3)	C12—C13—H13A	109.6
N1—C4—S1	121.6 (2)	C14—C13—H13B	109.6
C3—C4—S1	111.2 (2)	C12—C13—H13B	109.6
C9—C5—C3	111.4 (3)	H13A—C13—H13B	108.1
C9—C5—C6	123.9 (3)	N3—C14—C13	110.4 (3)
C3—C5—C6	124.7 (3)	N3—C14—H14A	109.6
C5—C6—C7	112.8 (3)	C13—C14—H14A	109.6
C5—C6—H6A	109.0	N3—C14—H14B	109.6
C7—C6—H6A	109.0	C13—C14—H14B	109.6
C5—C6—H6B	109.0	H14A—C14—H14B	108.1
C7—C6—H6B	109.0	C16—C15—C20	121.0 (3)
H6A—C6—H6B	107.8	C16—C15—N2	119.3 (3)
C6—C7—S2	113.1 (3)	C20—C15—N2	119.7 (3)
C6—C7—H7A	109.0	C15—C16—C17	119.3 (3)
S2—C7—H7A	109.0	C15—C16—H16A	120.4
C6—C7—H7B	109.0	C17—C16—H16A	120.4
S2—C7—H7B	109.0	C18—C17—C16	120.7 (4)
H7A—C7—H7B	107.8	C18—C17—H17A	119.6
C9—C8—S2	112.4 (2)	C16—C17—H17A	119.6
C9—C8—H8A	109.1	C17—C18—C19	119.9 (3)
S2—C8—H8A	109.1	C17—C18—H18A	120.1
C9—C8—H8B	109.1	C19—C18—H18A	120.1
S2—C8—H8B	109.1	C18—C19—C20	120.2 (4)
H8A—C8—H8B	107.9	C18—C19—H19A	119.9
C5—C9—C8	128.4 (3)	C20—C19—H19A	119.9
C5—C9—S1	112.4 (2)	C15—C20—C19	118.9 (4)
C8—C9—S1	119.1 (2)	C15—C20—H20A	120.5
N3—C10—C11	108.7 (3)	C19—C20—H20A	120.5
N3—C10—H10A	109.9
C4—N1—C1—N3	−176.1 (3)	C5—C6—C7—S2	52.2 (4)
C4—N1—C1—N2	0.6 (5)	C8—S2—C7—C6	−61.9 (3)
C10—N3—C1—N1	19.5 (5)	C7—S2—C8—C9	42.6 (3)
C14—N3—C1—N1	−124.1 (3)	C3—C5—C9—C8	−177.1 (3)
C10—N3—C1—N2	−157.4 (3)	C6—C5—C9—C8	1.1 (6)
C14—N3—C1—N2	59.1 (4)	C3—C5—C9—S1	0.3 (4)
C2—N2—C1—N1	0.9 (5)	C6—C5—C9—S1	178.6 (3)
C15—N2—C1—N1	−167.9 (3)	S2—C8—C9—C5	−18.4 (5)
C2—N2—C1—N3	177.6 (3)	S2—C8—C9—S1	164.27 (19)
C15—N2—C1—N3	8.9 (4)	C4—S1—C9—C5	−0.5 (3)
C1—N2—C2—O1	179.9 (3)	C4—S1—C9—C8	177.2 (3)
C15—N2—C2—O1	−10.6 (4)	C1—N3—C10—C11	153.3 (3)
C1—N2—C2—C3	−0.7 (4)	C14—N3—C10—C11	−60.0 (4)
C15—N2—C2—C3	168.7 (3)	N3—C10—C11—C12	56.0 (5)
O1—C2—C3—C4	178.4 (3)	C10—C11—C12—C13	−53.2 (5)
N2—C2—C3—C4	−0.9 (4)	C11—C12—C13—C14	52.7 (5)
O1—C2—C3—C5	1.4 (5)	C1—N3—C14—C13	−153.0 (3)
N2—C2—C3—C5	−177.9 (3)	C10—N3—C14—C13	61.5 (4)
C1—N1—C4—C3	−2.5 (5)	C12—C13—C14—N3	−56.6 (4)
C1—N1—C4—S1	178.2 (2)	C1—N2—C15—C16	62.8 (4)
C2—C3—C4—N1	2.7 (5)	C2—N2—C15—C16	−106.7 (3)
C5—C3—C4—N1	−179.9 (3)	C1—N2—C15—C20	−119.3 (3)
C2—C3—C4—S1	−177.9 (2)	C2—N2—C15—C20	71.1 (4)
C5—C3—C4—S1	−0.5 (4)	C20—C15—C16—C17	−0.2 (5)
C9—S1—C4—N1	−180.0 (3)	N2—C15—C16—C17	177.6 (3)
C9—S1—C4—C3	0.6 (3)	C15—C16—C17—C18	−0.3 (5)
C4—C3—C5—C9	0.1 (4)	C16—C17—C18—C19	0.8 (6)
C2—C3—C5—C9	177.2 (3)	C17—C18—C19—C20	−0.9 (6)
C4—C3—C5—C6	−178.2 (3)	C16—C15—C20—C19	0.1 (5)
C2—C3—C5—C6	−1.1 (5)	N2—C15—C20—C19	−177.7 (3)
C9—C5—C6—C7	−18.4 (5)	C18—C19—C20—C15	0.4 (6)
C3—C5—C6—C7	159.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1ii	0.97	2.56	3.321 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.97	2.56	3.321 (5)	136

Symmetry code: (i) .