3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetra­hydro-4H-thio­pyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one

Xie, H.; Meng, S.-M.; Fan, Y.-Q.; Guo, Y.

doi:10.1107/S1600536808038683

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2434

doi:10.1107/S1600536808038683

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3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetrahydro-4H-thiopyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one

Hai Xie,^a ^* Shuang-Ming Meng,^a Yue-Qin Fan ^a and Yong Guo ^a

^aCollege of Chemistry and Chemical Engineering, ShanXi Datong University, Datong, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: haixiedt@126.com

(Received 13 November 2008; accepted 19 November 2008; online 26 November 2008)

In the title compound, C₂₀H₂₁N₃OS₂, the piperidinyl ring has a distorted chair conformation. Weak intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing exhibits short intermolecular 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_r = 383.52
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.146
S = 1.08
3203 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038683/cv2480sup1.cif

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

checkCIF report

Comment top

The derivatives of heterocycles containing the thienopyrimidine system have proved to show significant antifungal, antibacterical, anticonvulsant and angiotensin antagonistic activities(Muller et al.,2002; Chambhare et al.2003). Recently, we have focused on the synthesis of fused heterocyclic systems containing thienopyrimidine via aza-wittig reaction at room temperature. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Xie et al., 2007; Hu et al., 2007). The title compound (I) can be used as a new precursor for obtaining of bioactive molecules with fluorescence properties.

In (I) (Fig. 1), the piperidinyl ring has a distored chair conformation. The weak intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2). The crystal packing exhibits relatively short intermolecular S···S distances of 3.590 (2) Å (Table 1), which is shorter than the sum of the van der Waals radii of the relevent atoms.

Related literature top

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 top

To a solution of iminophosphorane(2mmol) in anhyd.CH₂Cl₂(10ml)aromatic isocyanate(2mmol)was added under nitrogen atmosphere at room temperature.After the reaction mixture was left unstirred for 6-12h at 0-5°C,the iminophosphorane had disappeared (TLC monitored).The solvent was removed off under redunced pressure and Et₂O/petroleum ether (1:2,20ml) was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimides,which were used directly without further purification. To a solution of carbodiimides in CH₂Cl₂(10ml)dialkylamine(2mmol). After the reaction mixture was left unstirred for 4-6h. The solvent was removed and anhyd.EtOH(10ml)with several drops of EtONa in EtOH was added. The mixture was stirred for 6-12h at room temperature. The solution was condensed and residue was recrystallized from EtOH to give the expected title compound in a good yield.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A portion of the crystal packing showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetrahydro-4H- thiopyrano[3',4':2,3]thieno[5,4-d]pyrimidin-4-one top

Crystal data top

C₂₀H₂₁N₃OS₂	Z = 2
M_r = 383.52	F(000) = 404
Triclinic, P1	D_x = 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 = 2.2–27.6°
c = 10.864 (3) Å	µ = 0.30 mm⁻¹
α = 117.573 (4)°	T = 298 K
β = 106.099 (4)°	Block, red
γ = 97.322 (4)°	0.26 × 0.12 × 0.06 mm
V = 935.0 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.2°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→12
T_min = 0.926, T_max = 0.982	l = −12→12
4908 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0458P)² + 1.1731P] where P = (F_o² + 2F_c²)/3
3203 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₂₁N₃OS₂	γ = 97.322 (4)°
M_r = 383.52	V = 935.0 (4) Å³
Triclinic, P1	Z = 2
a = 9.851 (2) Å	Mo Kα radiation
b = 10.755 (3) Å	µ = 0.30 mm⁻¹
c = 10.864 (3) Å	T = 298 K
α = 117.573 (4)°	0.26 × 0.12 × 0.06 mm
β = 106.099 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3203 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2739 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.982	R_int = 0.020
4908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.08	Δρ_max = 0.29 e Å⁻³
3203 reflections	Δρ_min = −0.35 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z−1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃OS₂
M_r	383.52
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.851 (2), 10.755 (3), 10.864 (3)
α, β, γ (°)	117.573 (4), 106.099 (4), 97.322 (4)
V (Å³)	935.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.26 × 0.12 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.926, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4908, 3203, 2739
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.146, 1.08
No. of reflections	3203
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.35

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
C7—H7B···O1ⁱ	0.97	2.56	3.321 (5)	136

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

We gratefully acknowledge financial support of this work by a key grant (No. 2008K1) from the Shanxi Datong University Foundation of Shanxi Province.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chambhare, R. V., Khadse, B. G., Bobde, A. S. & Bahekr, R. H. (2003). Eur. J. Med. Chem. 38, 89–100. Web of Science CrossRef PubMed CAS Google Scholar
Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Muller, K., Knauf-Beiter, G., Hermann, D. & Walter, H. (2002). US Patent No. 6 432 965. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xie, H., Peng, X. & Hu, Y. (2007). Acta Cryst. E63, o4700. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2434

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

3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetra­hydro-4H-thio­pyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetrahydro-4H-thiopyrano[3′,4′:2,3]thieno[5,4-d]pyrimidin-4-one