3-Isopropyl-2-p-tol­yloxy-5,6,7,8-tetra­hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Zeng, X.-H.; Deng, S.-H.; Qu, Y.-N.; Wang, H.-M.

doi:10.1107/S1600536809014962

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1142-o1143

doi:10.1107/S1600536809014962

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3-Isopropyl-2-p-tolyloxy-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Xiao-Hua Zeng,^a Shou-Heng Deng,^b ^* Yong-Nian Qu ^c and Hong-Mei Wang ^a

^aInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China, ^bCenter of Oncology, People's Hospital Affiliated with YunYang Medical College, Shi Yan 442000, People's Republic of China, and ^cDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: dengshouheng@yahoo.cn

(Received 13 April 2009; accepted 22 April 2009; online 30 April 2009)

In the title compound, C₂₀H₂₂N₂O₂S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.023 (2) Å. The attached cyclohexene ring is disordered over two possible conformations, with an occupancy ratio of 0.776 (12):0.224 (12). Neither intermolecular hydrogen-bonding interactions nor π–π stacking interactions are present in the crystal structure. The molecular conformation and crystal packing are stabilized by three intramolecular C—H⋯O hydrogen bonds and two C—H⋯π interactions.

Related literature

For the biological activity of thienopyrimidin-4(3H)-one derivatives, see: De Laszlo et al. (1992a ,b ); Taguchi et al. (1993a ,b ); Walter (1999a ,b ,c ,d ); Walter & Zeun (2004 ); Ding et al. (2004 ); Santagati et al. (2003 ); Abbott GmbH Co KG (2004a , 2004b ); Waehaelae et al. (2004a ,b ); Ford et al. (2004a ,b ); Duval et al. (2005 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For related structures, see: Xie et al. (2008 ); Xu et al. (2005 ); Zeng et al. (2005 , 2006 , 2007 , 2008 ); Wang et al. (2006 , 2007 , 2008 ); Zheng et al. (2007 ).

Experimental

Crystal data

C₂₀H₂₂N₂O₂S
M_r = 354.47
Monoclinic, P 2₁
a = 13.2367 (7) Å
b = 5.7493 (3) Å
c = 13.4306 (7) Å
β = 115.858 (4)°
V = 919.76 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.981
6373 measured reflections
3920 independent reflections
3370 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.141
S = 1.01
3920 reflections
248 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 1702 Freidel pairs
Flack parameter: 0.16 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13C⋯O2	0.96	2.41	2.959 (4)	116
C12—H12A⋯O2	0.96	2.31	2.871 (4)	117
C11—H11⋯O1	0.98	2.20	2.725 (3)	112
C12—H12C⋯Cg1ⁱ	0.96	2.94	3.838 (4)	156
C12—H12C⋯Cg2ⁱ	0.96	2.72	3.413 (4)	130
Symmetry code: (i) x, y-1, z. Cg1 and Cg2 are the centroids of the thiophene (S1/C1/C6–C8) and pyrimidine (N1/N2/C7–C10) rings, respectively.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014962/at2765sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014962/at2765Isup2.hkl

checkCIF report

Comment top

The derivatives of heterocycles containing thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (De Laszlo et al., 1992a,b; Walter, 1999a,b,c,d); Ding et al., 2004; Walter et al., 2004), significant 5-HT_1A and 5-HT_1B receptor activities (Taguchi et al., 1993a,b; Abbott GmbH & Co. KG., 2004a,b), potential selective COX-2 enzyme inhibitor activity (Santagati et al., 2003), 17beta-hydroxysteroid dehydrogenase inhibitor activity (Waehaelae et al., 2004a,b), potassium channel inhibitor activity (Ford et al., 2004a,b), and tissue transglutaminase inhibitor activity (Duval et al., 2005).

In recent years, we have been engaged in the preparation of the derivatives of heterocycles via aza-Wittig reaction. The title compound, (I), was synthesized and structurally characterized in this context.

The molecular structure indicates that the thieno[2,3-d]pyrimidine moiety is a conjugated system (Fig.1). All ring atoms in thieno[2,3-d]pyrimidine are essentially coplanar (Xu et al., 2005; Zeng et al., 2005, 2006, 2007, 2008; Wang et al., 2006, 2007, 2008; Zheng et al., 2007; Xie et al., 2008). The bond lengths and angles are within experimental error, in the ranges of values in previously reported structures in the Cambridge Structural Database (Version 5.26; Allen, 2002).

The attached cyclohexene ring is disordered. There are two possible conformations, C2—C5 and C2/C3'/C4'/C5, with an occupancy ratio of 0.77:0.23. There exists no intermolecular hydrogen bonding interaction and no π-π stacking. The molecular conformation and crystal packing are stabilized by three intramolecular C—H···O hydrogen bonds and two C—H···π interactions.

Related literature top

For the biological activity of thienopyrimidin-4(3H)-one derivatives, see: De Laszlo et al. (1992a,b); Taguchi et al. (1993a,b); Walter (1999a,b,c,d); Walter & Zeun (2004); Ding et al. (2004); Santagati et al. (2003); Abbott GmbH Co KG (2004a, 2004b); Waehaelae et al. (2004a,b); Ford et al. (2004a,b); Duval et al. (2005). For a description of the Cambridge Structural Database, see: Allen (2002). For related structures, see: Xie et al. (2008); Xu et al. (2005); Zeng et al. (2005, 2006, 2007, 2008); Wang et al. (2006, 2007, 2008); Zheng et al. (2007). Cg1 and Cg2 are the centroids of the thiophene (S1/C1/C6–C8) and pyrimidine (N1/N2/C7–C10) rings, respectively.

Experimental top

To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added iso-propyl isocyanate (3 mmol) under dry nitrogen at room temperature. After the reaction mixture was left unstirred for 48 h at room temperature, the solvent was removed off under reduced pressure and ether/petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solvent was removed, and the residue was dissolved in CH₃CN (15 ml). After adding 4-CH₃—PhOH (3.1 mmol) and excess K₂CO₃ to the solution of carbodiimide, the mixture was stirred for 15 h at room temperature. The solution was condensed and the residue was recrystallized by EtOH to give the title compound, (I), in yield of 65% (m.p. 436 K). Elemental analysis calculated for C₂₀H₂₂N₂O₂S: C 67.77, H 6.26, N 7.90%. Found: C 67.54, H 6.32, N 7.83%. Crystals suitable for single crystal X-ray diffraction were obtained by vapor diffusion of hexane and dichloromethane (1:3 v/v) at room temperature.

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size. Only the major component of the disordered cyclohexene ring is shown.

3-Isopropyl-2-p-tolyloxy-5,6,7,8-tetrahydro-1- benzothieno[2,3-d]pyrimidin-4(3H)-one top

Crystal data top

C₂₀H₂₂N₂O₂S	F(000) = 376
M_r = 354.47	D_x = 1.280 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2048 reflections
a = 13.2367 (7) Å	θ = 2.9–24.5°
b = 5.7493 (3) Å	µ = 0.19 mm⁻¹
c = 13.4306 (7) Å	T = 298 K
β = 115.858 (4)°	Block, colourless
V = 919.76 (8) Å³	0.20 × 0.10 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3920 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.963, T_max = 0.981	k = −7→7
6373 measured reflections	l = −17→15

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0798P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3920 reflections	Δρ_max = 0.20 e Å⁻³
248 parameters	Δρ_min = −0.32 e Å⁻³
16 restraints	Absolute structure: Flack (1983), 1702 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (10)

Crystal data top

C₂₀H₂₂N₂O₂S	V = 919.76 (8) Å³
M_r = 354.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 13.2367 (7) Å	µ = 0.19 mm⁻¹
b = 5.7493 (3) Å	T = 298 K
c = 13.4306 (7) Å	0.20 × 0.10 × 0.10 mm
β = 115.858 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3920 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3370 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.981	R_int = 0.079
6373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.141	Δρ_max = 0.20 e Å⁻³
S = 1.01	Δρ_min = −0.32 e Å⁻³
3920 reflections	Absolute structure: Flack (1983), 1702 Freidel pairs
248 parameters	Absolute structure parameter: 0.16 (10)
16 restraints

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	Occ. (<1)
C1	0.20878 (19)	0.6656 (5)	0.88050 (19)	0.0448 (6)
C2	0.0948 (2)	0.6877 (6)	0.8794 (2)	0.0563 (7)
H2A	0.0446	0.7700	0.8132	0.068*	0.776 (12)
H2B	0.0639	0.5339	0.8776	0.068*	0.776 (12)
H2C	0.0817	0.5593	0.9191	0.068*	0.224 (12)
H2D	0.0370	0.6849	0.8037	0.068*	0.224 (12)
C3	0.1018 (4)	0.8162 (11)	0.9796 (5)	0.0662 (16)	0.776 (12)
H3A	0.1348	0.7157	1.0439	0.079*	0.776 (12)
H3B	0.0268	0.8576	0.9693	0.079*	0.776 (12)
C4	0.1717 (4)	1.0336 (10)	0.9996 (6)	0.0690 (17)	0.776 (12)
H4A	0.1703	1.1175	1.0616	0.083*	0.776 (12)
H4B	0.1383	1.1329	0.9349	0.083*	0.776 (12)
C3'	0.0904 (12)	0.916 (2)	0.9334 (14)	0.061 (5)	0.224 (12)
H3'1	0.0829	1.0405	0.8817	0.073*	0.224 (12)
H3'2	0.0230	0.9169	0.9448	0.073*	0.224 (12)
C4'	0.1882 (9)	0.974 (5)	1.0420 (11)	0.068 (6)	0.224 (12)
H4'1	0.1965	0.8556	1.0964	0.081*	0.224 (12)
H4'2	0.1758	1.1224	1.0692	0.081*	0.224 (12)
C5	0.2932 (2)	0.9853 (6)	1.0236 (3)	0.0615 (8)
H5A	0.3283	1.1265	1.0144	0.074*	0.776 (12)
H5B	0.3346	0.9322	1.0993	0.074*	0.776 (12)
H5C	0.2996	1.1376	0.9958	0.074*	0.224 (12)
H5D	0.3578	0.9636	1.0943	0.074*	0.224 (12)
C6	0.2953 (2)	0.8022 (5)	0.9451 (2)	0.0489 (6)
C7	0.3471 (2)	0.5369 (5)	0.8298 (2)	0.0457 (6)
C8	0.23832 (18)	0.5102 (5)	0.81357 (19)	0.0419 (5)
C9	0.1665 (2)	0.3547 (5)	0.7278 (2)	0.0440 (5)
C10	0.33155 (19)	0.2882 (5)	0.6970 (2)	0.0472 (6)
C11	0.1476 (2)	0.1089 (5)	0.5680 (2)	0.0476 (6)
H11	0.0727	0.1104	0.5658	0.057*
C12	0.1818 (3)	−0.1432 (6)	0.5773 (3)	0.0763 (10)
H12A	0.2536	−0.1556	0.5760	0.114*
H12B	0.1269	−0.2287	0.5163	0.114*
H12C	0.1867	−0.2060	0.6455	0.114*
C13	0.1348 (3)	0.2214 (6)	0.4619 (2)	0.0640 (8)
H13A	0.1085	0.3781	0.4587	0.096*
H13B	0.0817	0.1349	0.4001	0.096*
H13C	0.2061	0.2229	0.4591	0.096*
C14	0.4833 (2)	0.1798 (5)	0.6585 (2)	0.0515 (7)
C15	0.5521 (3)	0.0051 (7)	0.7178 (3)	0.0704 (9)
H15	0.5252	−0.1141	0.7466	0.084*
C16	0.6628 (3)	0.0076 (7)	0.7348 (3)	0.0743 (9)
H16	0.7098	−0.1137	0.7741	0.089*
C17	0.7055 (2)	0.1829 (6)	0.6956 (2)	0.0592 (8)
C18	0.6321 (3)	0.3536 (7)	0.6344 (3)	0.0721 (9)
H18	0.6583	0.4727	0.6050	0.086*
C19	0.5207 (3)	0.3543 (6)	0.6149 (3)	0.0710 (9)
H19	0.4724	0.4715	0.5730	0.085*
C20	0.8275 (2)	0.1872 (10)	0.7183 (3)	0.0936 (15)
H20A	0.8639	0.3178	0.7646	0.140*
H20B	0.8332	0.2006	0.6496	0.140*
H20C	0.8632	0.0460	0.7549	0.140*
N1	0.22102 (15)	0.2496 (4)	0.66777 (15)	0.0435 (4)
N2	0.39874 (17)	0.4226 (4)	0.77485 (19)	0.0524 (6)
O2	0.36853 (15)	0.1676 (4)	0.63340 (17)	0.0689 (7)
O1	0.06852 (14)	0.3137 (4)	0.70296 (16)	0.0607 (6)
S1	0.41623 (5)	0.74703 (15)	0.92707 (6)	0.0585 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0409 (13)	0.0542 (15)	0.0392 (12)	0.0072 (10)	0.0172 (10)	0.0072 (11)
C2	0.0453 (14)	0.068 (2)	0.0600 (16)	0.0029 (12)	0.0267 (12)	−0.0012 (14)
C3	0.062 (3)	0.086 (4)	0.062 (3)	−0.003 (2)	0.038 (2)	−0.010 (3)
C4	0.075 (3)	0.074 (4)	0.070 (4)	0.005 (2)	0.042 (3)	−0.014 (3)
C3'	0.053 (7)	0.072 (8)	0.060 (8)	0.002 (6)	0.026 (6)	0.000 (6)
C4'	0.075 (9)	0.081 (10)	0.056 (9)	0.012 (6)	0.036 (7)	0.012 (7)
C5	0.0554 (16)	0.071 (2)	0.0553 (16)	0.0041 (14)	0.0213 (13)	−0.0128 (15)
C6	0.0409 (12)	0.0616 (17)	0.0410 (12)	0.0051 (11)	0.0149 (10)	−0.0014 (12)
C7	0.0371 (13)	0.0556 (15)	0.0383 (12)	0.0036 (11)	0.0107 (10)	−0.0022 (11)
C8	0.0347 (11)	0.0508 (13)	0.0373 (12)	0.0014 (10)	0.0130 (10)	0.0026 (10)
C9	0.0369 (12)	0.0502 (14)	0.0449 (13)	0.0016 (10)	0.0179 (10)	0.0058 (11)
C10	0.0360 (11)	0.0563 (16)	0.0490 (13)	0.0013 (11)	0.0182 (10)	−0.0032 (12)
C11	0.0381 (13)	0.0495 (15)	0.0485 (14)	−0.0052 (11)	0.0127 (11)	−0.0059 (12)
C12	0.095 (3)	0.0463 (17)	0.072 (2)	−0.0096 (16)	0.0220 (19)	0.0016 (16)
C13	0.0728 (18)	0.0565 (18)	0.0483 (15)	0.0039 (15)	0.0130 (13)	−0.0016 (14)
C14	0.0381 (13)	0.0631 (18)	0.0561 (15)	−0.0044 (11)	0.0232 (12)	−0.0184 (13)
C15	0.0602 (18)	0.075 (2)	0.082 (2)	−0.0034 (17)	0.0366 (17)	0.0130 (19)
C16	0.0570 (18)	0.083 (2)	0.077 (2)	0.0165 (17)	0.0243 (16)	0.0157 (19)
C17	0.0473 (14)	0.085 (2)	0.0514 (15)	−0.0026 (14)	0.0276 (12)	−0.0128 (15)
C18	0.0622 (19)	0.085 (2)	0.076 (2)	−0.0121 (18)	0.0372 (17)	0.0070 (18)
C19	0.0608 (18)	0.067 (2)	0.083 (2)	0.0070 (16)	0.0292 (17)	0.0075 (18)
C20	0.0496 (17)	0.166 (5)	0.073 (2)	0.002 (2)	0.0332 (16)	−0.020 (3)
N1	0.0338 (9)	0.0498 (11)	0.0439 (10)	−0.0019 (10)	0.0143 (8)	−0.0033 (10)
N2	0.0319 (10)	0.0662 (15)	0.0566 (13)	−0.0020 (10)	0.0169 (9)	−0.0152 (11)
O2	0.0398 (10)	0.0937 (17)	0.0744 (13)	−0.0097 (10)	0.0261 (9)	−0.0374 (12)
O1	0.0361 (9)	0.0808 (15)	0.0670 (11)	−0.0103 (9)	0.0242 (8)	−0.0142 (11)
S1	0.0359 (3)	0.0722 (5)	0.0603 (4)	−0.0040 (3)	0.0144 (3)	−0.0216 (4)

Geometric parameters (Å, º) top

C1—C6	1.347 (4)	C9—O1	1.213 (3)
C1—C8	1.437 (4)	C9—N1	1.429 (3)
C1—C2	1.508 (3)	C10—N2	1.292 (3)
C2—C3	1.502 (5)	C10—O2	1.348 (3)
C2—C3'	1.515 (10)	C10—N1	1.358 (3)
C2—H2A	0.9700	C11—N1	1.503 (3)
C2—H2B	0.9700	C11—C13	1.506 (4)
C2—H2C	0.9700	C11—C12	1.508 (5)
C2—H2D	0.9700	C11—H11	0.9800
C3—C4	1.508 (7)	C12—H12A	0.9600
C3—H3A	0.9700	C12—H12B	0.9600
C3—H3B	0.9700	C12—H12C	0.9600
C4—C5	1.521 (5)	C13—H13A	0.9600
C4—H4A	0.9700	C13—H13B	0.9600
C4—H4B	0.9700	C13—H13C	0.9600
C3'—C4'	1.505 (10)	C14—C15	1.356 (5)
C3'—H3'1	0.9700	C14—C19	1.359 (4)
C3'—H3'2	0.9700	C14—O2	1.407 (3)
C4'—C5	1.515 (9)	C15—C16	1.382 (4)
C4'—H4'1	0.9700	C15—H15	0.9300
C4'—H4'2	0.9700	C16—C17	1.368 (5)
C5—C6	1.499 (4)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.373 (5)
C5—H5B	0.9700	C17—C20	1.508 (4)
C5—H5C	0.9700	C18—C19	1.381 (4)
C5—H5D	0.9700	C18—H18	0.9300
C6—S1	1.749 (3)	C19—H19	0.9300
C7—C8	1.368 (3)	C20—H20A	0.9600
C7—N2	1.372 (3)	C20—H20B	0.9600
C7—S1	1.721 (3)	C20—H20C	0.9600
C8—C9	1.440 (4)

C6—C1—C8	112.2 (2)	H5A—C5—H5D	88.0
C6—C1—C2	121.6 (2)	H5B—C5—H5D	23.0
C8—C1—C2	126.2 (2)	H5C—C5—H5D	107.8
C3—C2—C1	111.2 (3)	C1—C6—C5	126.2 (2)
C3—C2—C3'	31.2 (6)	C1—C6—S1	112.19 (19)
C1—C2—C3'	108.4 (7)	C5—C6—S1	121.6 (2)
C3—C2—H2A	109.4	C8—C7—N2	126.7 (2)
C1—C2—H2A	109.4	C8—C7—S1	111.93 (19)
C3'—C2—H2A	82.1	N2—C7—S1	121.34 (18)
C3—C2—H2B	109.4	C7—C8—C1	112.7 (2)
C1—C2—H2B	109.4	C7—C8—C9	118.6 (2)
C3'—C2—H2B	134.4	C1—C8—C9	128.4 (2)
H2A—C2—H2B	108.0	O1—C9—N1	120.3 (2)
C3—C2—H2C	80.7	O1—C9—C8	126.4 (2)
C1—C2—H2C	110.4	N1—C9—C8	113.2 (2)
C3'—C2—H2C	110.1	N2—C10—O2	120.6 (2)
H2A—C2—H2C	131.4	N2—C10—N1	127.4 (2)
H2B—C2—H2C	31.3	O2—C10—N1	112.1 (2)
C3—C2—H2D	131.3	N1—C11—C13	112.0 (2)
C1—C2—H2D	109.7	N1—C11—C12	112.9 (2)
C3'—C2—H2D	109.9	C13—C11—C12	113.4 (3)
H2A—C2—H2D	30.2	N1—C11—H11	105.9
H2B—C2—H2D	80.0	C13—C11—H11	105.9
H2C—C2—H2D	108.4	C12—C11—H11	105.9
C2—C3—C4	111.1 (5)	C11—C12—H12A	109.5
C2—C3—H3A	109.4	C11—C12—H12B	109.5
C4—C3—H3A	109.4	H12A—C12—H12B	109.5
C2—C3—H3B	109.4	C11—C12—H12C	109.5
C4—C3—H3B	109.4	H12A—C12—H12C	109.5
H3A—C3—H3B	108.0	H12B—C12—H12C	109.5
C3—C4—C5	113.3 (4)	C11—C13—H13A	109.5
C3—C4—H4A	108.9	C11—C13—H13B	109.5
C5—C4—H4A	108.9	H13A—C13—H13B	109.5
C3—C4—H4B	108.9	C11—C13—H13C	109.5
C5—C4—H4B	108.9	H13A—C13—H13C	109.5
H4A—C4—H4B	107.7	H13B—C13—H13C	109.5
C4'—C3'—C2	117.3 (15)	C15—C14—C19	121.5 (3)
C4'—C3'—H3'1	108.0	C15—C14—O2	118.8 (3)
C2—C3'—H3'1	108.0	C19—C14—O2	119.4 (3)
C4'—C3'—H3'2	108.0	C14—C15—C16	118.8 (3)
C2—C3'—H3'2	108.0	C14—C15—H15	120.6
H3'1—C3'—H3'2	107.2	C16—C15—H15	120.6
C3'—C4'—C5	108.3 (10)	C17—C16—C15	122.0 (3)
C3'—C4'—H4'1	110.0	C17—C16—H16	119.0
C5—C4'—H4'1	110.0	C15—C16—H16	119.0
C3'—C4'—H4'2	110.0	C16—C17—C18	117.0 (3)
C5—C4'—H4'2	110.0	C16—C17—C20	121.3 (3)
H4'1—C4'—H4'2	108.4	C18—C17—C20	121.6 (3)
C6—C5—C4'	112.6 (9)	C17—C18—C19	122.2 (3)
C6—C5—C4	108.8 (3)	C17—C18—H18	118.9
C4'—C5—C4	23.5 (6)	C19—C18—H18	118.9
C6—C5—H5A	109.9	C14—C19—C18	118.4 (3)
C4'—C5—H5A	125.5	C14—C19—H19	120.8
C4—C5—H5A	109.9	C18—C19—H19	120.8
C6—C5—H5B	109.9	C17—C20—H20A	109.5
C4'—C5—H5B	87.4	C17—C20—H20B	109.5
C4—C5—H5B	109.9	H20A—C20—H20B	109.5
H5A—C5—H5B	108.3	C17—C20—H20C	109.5
C6—C5—H5C	109.4	H20A—C20—H20C	109.5
C4'—C5—H5C	110.0	H20B—C20—H20C	109.5
C4—C5—H5C	90.9	C10—N1—C9	120.8 (2)
H5A—C5—H5C	21.3	C10—N1—C11	122.9 (2)
H5B—C5—H5C	125.7	C9—N1—C11	116.21 (18)
C6—C5—H5D	108.6	C10—N2—C7	113.1 (2)
C4'—C5—H5D	108.3	C10—O2—C14	118.4 (2)
C4—C5—H5D	129.0	C7—S1—C6	90.97 (12)

C6—C1—C2—C3	−17.9 (5)	C19—C14—C15—C16	0.6 (5)
C8—C1—C2—C3	164.4 (4)	O2—C14—C15—C16	174.8 (3)
C6—C1—C2—C3'	15.2 (8)	C14—C15—C16—C17	1.4 (5)
C8—C1—C2—C3'	−162.5 (8)	C15—C16—C17—C18	−2.5 (5)
C1—C2—C3—C4	46.7 (6)	C15—C16—C17—C20	177.8 (3)
C3'—C2—C3—C4	−44.0 (11)	C16—C17—C18—C19	1.7 (5)
C2—C3—C4—C5	−62.5 (8)	C20—C17—C18—C19	−178.6 (3)
C3—C2—C3'—C4'	53.3 (13)	C15—C14—C19—C18	−1.4 (5)
C1—C2—C3'—C4'	−47.5 (19)	O2—C14—C19—C18	−175.5 (3)
C2—C3'—C4'—C5	61 (3)	C17—C18—C19—C14	0.2 (5)
C3'—C4'—C5—C6	−39 (2)	N2—C10—N1—C9	−2.7 (4)
C3'—C4'—C5—C4	46.5 (12)	O2—C10—N1—C9	177.7 (2)
C3—C4—C5—C6	43.0 (7)	N2—C10—N1—C11	173.4 (3)
C3—C4—C5—C4'	−61 (2)	O2—C10—N1—C11	−6.3 (4)
C8—C1—C6—C5	179.2 (3)	O1—C9—N1—C10	−177.9 (3)
C2—C1—C6—C5	1.2 (4)	C8—C9—N1—C10	3.8 (3)
C8—C1—C6—S1	0.0 (3)	O1—C9—N1—C11	5.8 (4)
C2—C1—C6—S1	−178.0 (2)	C8—C9—N1—C11	−172.6 (2)
C4'—C5—C6—C1	11.4 (9)	C13—C11—N1—C10	−64.3 (3)
C4—C5—C6—C1	−13.4 (5)	C12—C11—N1—C10	65.2 (3)
C4'—C5—C6—S1	−169.5 (9)	C13—C11—N1—C9	112.0 (3)
C4—C5—C6—S1	165.8 (3)	C12—C11—N1—C9	−118.6 (3)
N2—C7—C8—C1	−176.8 (3)	O2—C10—N2—C7	178.4 (3)
S1—C7—C8—C1	0.7 (3)	N1—C10—N2—C7	−1.2 (4)
N2—C7—C8—C9	−2.7 (4)	C8—C7—N2—C10	4.0 (4)
S1—C7—C8—C9	174.81 (19)	S1—C7—N2—C10	−173.3 (2)
C6—C1—C8—C7	−0.4 (3)	N2—C10—O2—C14	4.1 (4)
C2—C1—C8—C7	177.4 (2)	N1—C10—O2—C14	−176.3 (2)
C6—C1—C8—C9	−173.8 (2)	C15—C14—O2—C10	98.6 (3)
C2—C1—C8—C9	4.1 (4)	C19—C14—O2—C10	−87.0 (3)
C7—C8—C9—O1	−179.5 (3)	C8—C7—S1—C6	−0.6 (2)
C1—C8—C9—O1	−6.5 (4)	N2—C7—S1—C6	177.0 (2)
C7—C8—C9—N1	−1.3 (3)	C1—C6—S1—C7	0.4 (2)
C1—C8—C9—N1	171.7 (2)	C5—C6—S1—C7	−178.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O2	0.96	2.41	2.959 (4)	116
C12—H12A···O2	0.96	2.31	2.871 (4)	117
C11—H11···O1	0.98	2.20	2.725 (3)	112
C12—H12C···Cg1ⁱ	0.96	2.94	3.838 (4)	156
C12—H12C···Cg2ⁱ	0.96	2.72	3.413 (4)	130

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₂S
M_r	354.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	13.2367 (7), 5.7493 (3), 13.4306 (7)
β (°)	115.858 (4)
V (Å³)	919.76 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	6373, 3920, 3370
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.141, 1.01
No. of reflections	3920
No. of parameters	248
No. of restraints	16
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32
Absolute structure	Flack (1983), 1702 Freidel pairs
Absolute structure parameter	0.16 (10)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···O2	0.96	2.41	2.959 (4)	115.9
C12—H12A···O2	0.96	2.31	2.871 (4)	116.6
C11—H11···O1	0.98	2.20	2.725 (3)	112.0
C12—H12C···Cg1ⁱ	0.96	2.94	3.838 (4)	156
C12—H12C···Cg2ⁱ	0.96	2.72	3.413 (4)	130

Symmetry code: (i) x, y−1, z.

Acknowledgements

We gratefully acknowledge financial support of this work by the Education Commission of Hubei Province of China (grant Nos. B200624004, B20092412), Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

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Volume 65| Part 5| May 2009| Pages o1142-o1143

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

3-Iso­propyl-2-p-tol­yl­oxy-5,6,7,8-tetra­hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Isopropyl-2-p-tolyloxy-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one