3-Butyl-2-(piperidin-1-yl)-5,6,7,8-tetra­hydro­benzothieno[2,3-d]pyrimidin-4(3H)-one

Wang, H.-M.; Zeng, X.-H.; Zheng, A.-H.; Tian, J.-H.; He, T.-Y.

doi:10.1107/S160053680705026X

3-Butyl-2-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one

H.-M. Wang, X.-H. Zeng, A.-H. Zheng, J.-H. Tian and T.-Y. He

In the title compound, C₁₉H₂₇N₃OS, the central thienopyrimidine ring system is essentially planar. The cyclohexene ring adopts a half-chair conformation, while the piperidine ring is in a standard chair conformation. There is an intramolecular C—H

O hydrogen bond, which stabilizes the molecular structure. The crystal packing is stabilized by C—H

π interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705026X/is2220sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705026X/is2220Isup2.hkl Contains datablock I

CCDC reference: 667392

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.059
wR factor = 0.184
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C3     -   C4     ...       1.42 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrimidine derivatives are attracting the increasing attention of the synthetic community because of the important role played by such systems in many natural products, antibiotics and drugs (Ding et al., 2004). In recent years, we have been engaged in the preparation of derivatives of heterocycles via the aza-Wittig reaction. The title compound, (I), was synthesized and structurally characterized in this context.

In the fused heterobicyclic ring of (I), bond lengths and angles are similar to those observed in closely related structures (Zeng et al., 2007). All ring atoms in the thienopyrimidine system are essentially coplanar. The cyclohexene ring adopts a half-chair conformation, while the piperidine ring is in a standard chair conformation. There is one intramolecular C—H···O hydrogen bond which stabilizes the molecular structure (Table 1). The crystal packing is stabilized by C—H···π interactions (Table 1). There exists no intermolecular hydrogen bond nor π-π stacking interaction.

Related literature top

For related literature, see: Ding et al. (2004); Zeng et al. (2007).

Experimental top

To a solution of iminophosphorane (a) (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added butyl isocyanate (3 mmol) under dry nitrogen at room temperature (Fig. 2). The reaction mixture was left unstirred for 48 h at room temperature, then the solvent was removed under reduced pressure and an ether/petroleum ether (1:3 v/v, 20 ml) mixture was added to precipitate triphenylphosphine oxide. After filtration the solvent was removed to give carbodiimide, which was used directly without further purification. To the solution of carbodiimide (15 ml), piperidine (3 mmol) was added. After the mixture was stirred for 6 h, the solvent was removed and anhydrous ethanol (10 ml) containing several drops of EtONa in EtOH was added. The mixture was stirred for 12 h at room temperature. The solution was condensed and the residue was recrystallized from ethanol to give the title compound, (I), in a yield of 47% (m.p. 362 K). Spectroscopic analysis: IR (KBr, cm^-1): 1655 (C=O); ¹H NMR (CDCl₃, 400 MHz): δ 4.07–4.04 (t, J=7.2 Hz, 2H, NCH₂), 3.06–2.72 (m, 8H, 4CH₂), 1.85–1.63 (m, 12H, 6CH₂), 1.36–1.31 (m, 2H, CH₂), 0.96–0.92 (t, J=7.4 Hz, 3H, CH₃); MS (EI, 70 eV) m/z(%): 349 (21), 345 (M+, 94), 328 (42), 289 (100), 261 (99), 205 (92), 179 (69), 83 (97); Anal. Calcd. for C₁₉H₂₇N₃OS: C 66.05, H 7.88, N 12.16; Found: C 66.31, H 6.23, N 9.41%. Crystals suitable for single-crystal X-ray diffraction analysis were obtained by vapour diffusion of a hexane/dichloromethane solution (1:3 v/v) at room temperature.

Structure description top

For related literature, see: Ding et al. (2004); Zeng et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H-atoms are represented by circles of arbitrary size.
	Fig. 2. Reaction scheme of the title compound, (I).

3-Butyl-2-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin- 4(3H)-one top

Crystal data top

C₁₉H₂₇N₃OS	Z = 2
M_r = 345.50	F(000) = 372
Triclinic, P1	D_x = 1.242 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8979 (8) Å	Cell parameters from 1934 reflections
b = 10.3679 (9) Å	θ = 2.2–22.4°
c = 10.9645 (9) Å	µ = 0.19 mm⁻¹
α = 113.537 (1)°	T = 292 K
β = 107.679 (1)°	Block, colorless
γ = 100.167 (1)°	0.40 × 0.06 × 0.02 mm
V = 923.97 (13) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
φ and ω scans	h = −11→12
7700 measured reflections	k = −12→9
3587 independent reflections	l = −13→13

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0975P)²] where P = (F_o² + 2F_c²)/3
3587 reflections	(Δ/σ)_max = 0.002
217 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₂₇N₃OS	γ = 100.167 (1)°
M_r = 345.50	V = 923.97 (13) Å³
Triclinic, P1	Z = 2
a = 9.8979 (8) Å	Mo Kα radiation
b = 10.3679 (9) Å	µ = 0.19 mm⁻¹
c = 10.9645 (9) Å	T = 292 K
α = 113.537 (1)°	0.40 × 0.06 × 0.02 mm
β = 107.679 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2271 reflections with I > 2σ(I)
7700 measured reflections	R_int = 0.044
3587 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
3587 reflections	Δρ_min = −0.29 e Å⁻³
217 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
S1	0.40177 (10)	0.46312 (8)	0.21177 (8)	0.0609 (3)
N1	0.3069 (2)	0.1715 (2)	0.1435 (2)	0.0465 (6)
N2	0.1870 (2)	0.1033 (2)	0.2765 (2)	0.0434 (5)
C8	0.2699 (3)	0.3619 (3)	0.3400 (3)	0.0439 (7)
N3	0.2303 (2)	−0.0775 (2)	0.0898 (2)	0.0456 (6)
O1	0.1534 (3)	0.2739 (2)	0.4653 (2)	0.0698 (7)
C16	0.1233 (3)	−0.0109 (3)	0.3111 (3)	0.0484 (7)
H16A	0.1728	0.0261	0.4155	0.058*
H16B	0.1451	−0.1005	0.2622	0.058*
C9	0.1995 (3)	0.2514 (3)	0.3694 (3)	0.0486 (7)
C10	0.2415 (3)	0.0708 (3)	0.1690 (3)	0.0417 (6)
C1	0.2966 (3)	0.5199 (3)	0.4082 (3)	0.0453 (7)
C7	0.3202 (3)	0.3150 (3)	0.2314 (3)	0.0456 (7)
C6	0.3667 (3)	0.5875 (3)	0.3505 (3)	0.0494 (7)
C11	0.0765 (3)	−0.1862 (3)	−0.0144 (3)	0.0496 (7)
H11A	0.0417	−0.1704	−0.0984	0.060*
H11B	0.0077	−0.1703	0.0325	0.060*
C17	−0.0465 (3)	−0.0517 (3)	0.2656 (3)	0.0520 (7)
H17A	−0.0666	0.0299	0.3320	0.062*
H17B	−0.0941	−0.0642	0.1683	0.062*
C2	0.2488 (4)	0.6038 (3)	0.5266 (3)	0.0595 (8)
H2A	0.3113	0.6105	0.6178	0.071*
H2B	0.1449	0.5502	0.5003	0.071*
C15	0.3358 (3)	−0.0959 (3)	0.0196 (3)	0.0571 (8)
H15A	0.4361	−0.0251	0.0891	0.069*
H15B	0.3044	−0.0759	−0.0620	0.069*
C12	0.0763 (4)	−0.3444 (3)	−0.0643 (3)	0.0644 (9)
H12A	−0.0248	−0.4141	−0.1324	0.077*
H12B	0.1072	−0.3617	0.0190	0.077*
C18	−0.1149 (3)	−0.1924 (4)	0.2660 (4)	0.0645 (9)
H18A	−0.0679	−0.1798	0.3635	0.077*
H18B	−0.0941	−0.2739	0.2002	0.077*
C5	0.4085 (4)	0.7505 (3)	0.3967 (3)	0.0626 (8)
H5A	0.5133	0.7899	0.4151	0.075*
H5B	0.3472	0.7643	0.3183	0.075*
C14	0.3392 (4)	−0.2539 (4)	−0.0343 (4)	0.0725 (10)
H14A	0.3794	−0.2700	0.0488	0.087*
H14B	0.4061	−0.2661	−0.0838	0.087*
C13	0.1840 (4)	−0.3699 (4)	−0.1381 (4)	0.0768 (10)
H13A	0.1892	−0.4695	−0.1644	0.092*
H13B	0.1478	−0.3622	−0.2268	0.092*
C3	0.2643 (5)	0.7599 (4)	0.5461 (5)	0.1045 (15)
H3A	0.1719	0.7538	0.4765	0.125*
H3B	0.2716	0.8223	0.6431	0.125*
C4	0.3868 (5)	0.8343 (4)	0.5298 (4)	0.0913 (13)
H4A	0.4786	0.8629	0.6139	0.110*
H4B	0.3737	0.9257	0.5323	0.110*
C19	−0.2845 (4)	−0.2338 (4)	0.2196 (4)	0.0811 (11)
H19A	−0.3059	−0.1533	0.2839	0.122*
H19B	−0.3224	−0.3228	0.2242	0.122*
H19C	−0.3323	−0.2514	0.1212	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0750 (6)	0.0451 (5)	0.0729 (5)	0.0160 (4)	0.0478 (5)	0.0270 (4)
N1	0.0518 (14)	0.0402 (13)	0.0494 (12)	0.0145 (11)	0.0279 (11)	0.0187 (11)
N2	0.0454 (13)	0.0426 (13)	0.0483 (11)	0.0153 (11)	0.0250 (10)	0.0232 (10)
C8	0.0480 (17)	0.0401 (16)	0.0414 (13)	0.0137 (13)	0.0174 (12)	0.0189 (12)
N3	0.0401 (13)	0.0422 (13)	0.0517 (12)	0.0151 (11)	0.0219 (10)	0.0177 (10)
O1	0.1052 (18)	0.0561 (13)	0.0683 (12)	0.0268 (12)	0.0617 (13)	0.0296 (11)
C16	0.0526 (18)	0.0486 (17)	0.0551 (15)	0.0170 (14)	0.0280 (14)	0.0311 (14)
C9	0.0568 (19)	0.0464 (17)	0.0439 (13)	0.0192 (14)	0.0244 (13)	0.0198 (13)
C10	0.0381 (15)	0.0428 (16)	0.0439 (13)	0.0150 (12)	0.0187 (12)	0.0192 (12)
C1	0.0423 (16)	0.0420 (16)	0.0427 (13)	0.0126 (13)	0.0145 (12)	0.0156 (12)
C7	0.0472 (17)	0.0401 (16)	0.0469 (13)	0.0130 (13)	0.0212 (12)	0.0182 (12)
C6	0.0464 (17)	0.0389 (16)	0.0548 (15)	0.0097 (13)	0.0203 (14)	0.0178 (13)
C11	0.0431 (17)	0.0446 (17)	0.0525 (15)	0.0118 (13)	0.0159 (13)	0.0197 (13)
C17	0.0505 (18)	0.0549 (19)	0.0659 (17)	0.0218 (15)	0.0342 (15)	0.0341 (15)
C2	0.070 (2)	0.0511 (19)	0.0530 (15)	0.0242 (16)	0.0302 (15)	0.0163 (14)
C15	0.0510 (18)	0.0562 (19)	0.0608 (16)	0.0195 (15)	0.0310 (15)	0.0190 (15)
C12	0.063 (2)	0.0397 (18)	0.0693 (18)	0.0085 (15)	0.0203 (16)	0.0165 (15)
C18	0.054 (2)	0.070 (2)	0.086 (2)	0.0175 (16)	0.0401 (17)	0.0470 (18)
C5	0.063 (2)	0.0448 (19)	0.0776 (19)	0.0149 (16)	0.0323 (17)	0.0268 (16)
C14	0.074 (2)	0.063 (2)	0.085 (2)	0.0379 (19)	0.0450 (19)	0.0251 (18)
C13	0.085 (3)	0.046 (2)	0.088 (2)	0.0257 (19)	0.040 (2)	0.0170 (17)
C3	0.129 (4)	0.057 (2)	0.139 (3)	0.038 (2)	0.095 (3)	0.026 (2)
C4	0.130 (4)	0.053 (2)	0.095 (3)	0.033 (2)	0.060 (3)	0.029 (2)
C19	0.062 (2)	0.082 (3)	0.100 (3)	0.014 (2)	0.042 (2)	0.042 (2)

Geometric parameters (Å, º) top

S1—C7	1.728 (3)	C2—H2A	0.9700
S1—C6	1.735 (3)	C2—H2B	0.9700
N1—C10	1.302 (3)	C15—C14	1.513 (4)
N1—C7	1.367 (3)	C15—H15A	0.9700
N2—C10	1.388 (3)	C15—H15B	0.9700
N2—C9	1.420 (3)	C12—C13	1.521 (5)
N2—C16	1.477 (3)	C12—H12A	0.9700
C8—C7	1.373 (3)	C12—H12B	0.9700
C8—C9	1.433 (4)	C18—C19	1.521 (4)
C8—C1	1.436 (4)	C18—H18A	0.9700
N3—C10	1.394 (3)	C18—H18B	0.9700
N3—C15	1.470 (3)	C5—C4	1.475 (4)
N3—C11	1.485 (3)	C5—H5A	0.9700
O1—C9	1.225 (3)	C5—H5B	0.9700
C16—C17	1.524 (4)	C14—C13	1.515 (5)
C16—H16A	0.9700	C14—H14A	0.9700
C16—H16B	0.9700	C14—H14B	0.9700
C1—C6	1.350 (4)	C13—H13A	0.9700
C1—C2	1.510 (3)	C13—H13B	0.9700
C6—C5	1.492 (4)	C3—C4	1.417 (5)
C11—C12	1.506 (4)	C3—H3A	0.9700
C11—H11A	0.9700	C3—H3B	0.9700
C11—H11B	0.9700	C4—H4A	0.9700
C17—C18	1.498 (4)	C4—H4B	0.9700
C17—H17A	0.9700	C19—H19A	0.9600
C17—H17B	0.9700	C19—H19B	0.9600
C2—C3	1.518 (5)	C19—H19C	0.9600

C7—S1—C6	91.25 (13)	C14—C15—H15A	109.7
C10—N1—C7	115.3 (2)	N3—C15—H15B	109.7
C10—N2—C9	122.3 (2)	C14—C15—H15B	109.7
C10—N2—C16	122.7 (2)	H15A—C15—H15B	108.2
C9—N2—C16	114.9 (2)	C11—C12—C13	109.7 (3)
C7—C8—C9	117.7 (2)	C11—C12—H12A	109.7
C7—C8—C1	113.0 (2)	C13—C12—H12A	109.7
C9—C8—C1	129.3 (2)	C11—C12—H12B	109.7
C10—N3—C15	114.1 (2)	C13—C12—H12B	109.7
C10—N3—C11	116.6 (2)	H12A—C12—H12B	108.2
C15—N3—C11	110.6 (2)	C17—C18—C19	112.7 (3)
N2—C16—C17	113.6 (2)	C17—C18—H18A	109.1
N2—C16—H16A	108.8	C19—C18—H18A	109.1
C17—C16—H16A	108.8	C17—C18—H18B	109.1
N2—C16—H16B	108.8	C19—C18—H18B	109.1
C17—C16—H16B	108.8	H18A—C18—H18B	107.8
H16A—C16—H16B	107.7	C4—C5—C6	111.5 (3)
O1—C9—N2	119.4 (3)	C4—C5—H5A	109.3
O1—C9—C8	126.5 (2)	C6—C5—H5A	109.3
N2—C9—C8	114.1 (2)	C4—C5—H5B	109.3
N1—C10—N2	123.5 (2)	C6—C5—H5B	109.3
N1—C10—N3	119.2 (2)	H5A—C5—H5B	108.0
N2—C10—N3	117.2 (2)	C15—C14—C13	112.1 (3)
C6—C1—C8	111.9 (2)	C15—C14—H14A	109.2
C6—C1—C2	122.5 (3)	C13—C14—H14A	109.2
C8—C1—C2	125.6 (3)	C15—C14—H14B	109.2
N1—C7—C8	127.0 (3)	C13—C14—H14B	109.2
N1—C7—S1	121.77 (19)	H14A—C14—H14B	107.9
C8—C7—S1	111.2 (2)	C14—C13—C12	109.3 (3)
C1—C6—C5	124.8 (3)	C14—C13—H13A	109.8
C1—C6—S1	112.6 (2)	C12—C13—H13A	109.8
C5—C6—S1	122.5 (2)	C14—C13—H13B	109.8
N3—C11—C12	110.6 (2)	C12—C13—H13B	109.8
N3—C11—H11A	109.5	H13A—C13—H13B	108.3
C12—C11—H11A	109.5	C4—C3—C2	117.9 (3)
N3—C11—H11B	109.5	C4—C3—H3A	107.8
C12—C11—H11B	109.5	C2—C3—H3A	107.8
H11A—C11—H11B	108.1	C4—C3—H3B	107.8
C18—C17—C16	112.7 (2)	C2—C3—H3B	107.8
C18—C17—H17A	109.1	H3A—C3—H3B	107.2
C16—C17—H17A	109.1	C3—C4—C5	116.9 (3)
C18—C17—H17B	109.1	C3—C4—H4A	108.1
C16—C17—H17B	109.1	C5—C4—H4A	108.1
H17A—C17—H17B	107.8	C3—C4—H4B	108.1
C1—C2—C3	110.0 (3)	C5—C4—H4B	108.1
C1—C2—H2A	109.7	H4A—C4—H4B	107.3
C3—C2—H2A	109.7	C18—C19—H19A	109.5
C1—C2—H2B	109.7	C18—C19—H19B	109.5
C3—C2—H2B	109.7	H19A—C19—H19B	109.5
H2A—C2—H2B	108.2	C18—C19—H19C	109.5
N3—C15—C14	109.8 (3)	H19A—C19—H19C	109.5
N3—C15—H15A	109.7	H19B—C19—H19C	109.5

C10—N2—C16—C17	−110.2 (3)	C9—C8—C7—S1	−179.9 (2)
C9—N2—C16—C17	74.5 (3)	C1—C8—C7—S1	0.4 (3)
C10—N2—C9—O1	−177.9 (2)	C6—S1—C7—N1	178.1 (2)
C16—N2—C9—O1	−2.6 (4)	C6—S1—C7—C8	−0.1 (2)
C10—N2—C9—C8	1.2 (4)	C8—C1—C6—C5	179.3 (3)
C16—N2—C9—C8	176.4 (2)	C2—C1—C6—C5	1.4 (4)
C7—C8—C9—O1	177.1 (3)	C8—C1—C6—S1	0.4 (3)
C1—C8—C9—O1	−3.2 (5)	C2—C1—C6—S1	−177.6 (2)
C7—C8—C9—N2	−1.8 (4)	C7—S1—C6—C1	−0.1 (2)
C1—C8—C9—N2	177.9 (2)	C7—S1—C6—C5	−179.1 (3)
C7—N1—C10—N2	0.4 (4)	C10—N3—C11—C12	−166.3 (2)
C7—N1—C10—N3	−176.6 (2)	C15—N3—C11—C12	61.1 (3)
C9—N2—C10—N1	−0.5 (4)	N2—C16—C17—C18	165.4 (2)
C16—N2—C10—N1	−175.4 (2)	C6—C1—C2—C3	10.6 (4)
C9—N2—C10—N3	176.6 (2)	C8—C1—C2—C3	−167.1 (3)
C16—N2—C10—N3	1.7 (4)	C10—N3—C15—C14	167.6 (2)
C15—N3—C10—N1	18.8 (3)	C11—N3—C15—C14	−58.6 (3)
C11—N3—C10—N1	−112.1 (3)	N3—C11—C12—C13	−59.2 (3)
C15—N3—C10—N2	−158.4 (2)	C16—C17—C18—C19	−179.6 (2)
C11—N3—C10—N2	70.7 (3)	C1—C6—C5—C4	9.4 (5)
C7—C8—C1—C6	−0.5 (3)	S1—C6—C5—C4	−171.8 (3)
C9—C8—C1—C6	179.8 (3)	N3—C15—C14—C13	56.7 (4)
C7—C8—C1—C2	177.4 (2)	C15—C14—C13—C12	−55.1 (4)
C9—C8—C1—C2	−2.3 (5)	C11—C12—C13—C14	55.6 (4)
C10—N1—C7—C8	−1.2 (4)	C1—C2—C3—C4	−35.9 (5)
C10—N1—C7—S1	−179.1 (2)	C2—C3—C4—C5	50.3 (6)
C9—C8—C7—N1	2.0 (4)	C6—C5—C4—C3	−34.3 (5)
C1—C8—C7—N1	−177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1	0.97	2.54	3.035 (4)	112
C4—H4A···Cg2ⁱ	0.97	3.00	3.854 (5)	148
C11—H11A···Cg2ⁱⁱ	0.97	2.76	3.408 (3)	125
C12—H12A···Cg1ⁱⁱ	0.97	2.92	3.764 (4)	146

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₇N₃OS
M_r	345.50
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	9.8979 (8), 10.3679 (9), 10.9645 (9)
α, β, γ (°)	113.537 (1), 107.679 (1), 100.167 (1)
V (Å³)	923.97 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.40 × 0.06 × 0.02

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7700, 3587, 2271
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.184, 1.03
No. of reflections	3587
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).