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

Wang, H.-M.; Chen, L.-L.; Hu, T.; Zeng, X.-H.

doi:10.1107/S160053680803732X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2404

doi:10.1107/S160053680803732X

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

Hong-Mei Wang,^a Li-Li Chen,^a Ting Hu ^a and Xiao-Hua Zeng ^a ^*

^aDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: zengken@126.com

(Received 9 November 2008; accepted 11 November 2008; online 22 November 2008)

In the title compound, C₁₉H₁₉BrN₂O₂S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å. The attached cyclohexene ring adopts a half-chair conformation. 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 background to the use of pyrimidine derivatives as drugs, see: Ding et al. (2004 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For a related structure, see: Zeng et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₉BrN₂O₂S
M_r = 418.32
Monoclinic, P 2₁
a = 13.3957 (7) Å
b = 5.7366 (3) Å
c = 13.3956 (7) Å
β = 115.5410 (10)°
V = 928.81 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 298 (2) 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 = 0.652, T_max = 0.800
5798 measured reflections
3228 independent reflections
2346 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.204
S = 1.07
3228 reflections
228 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 7.69 e Å⁻³
Δρ_min = −2.63 e Å⁻³
Absolute structure: Flack (1983 ), 1424 Freidel pairs
Flack parameter: 0.00 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1	0.98	2.20	2.726 (10)	112
C12—H12B⋯O2	0.96	2.43	2.915 (13)	111
C13—H13A⋯O2	0.96	2.38	2.951 (10)	117
C12—H12A⋯Cg1ⁱ	0.96	2.92	3.854 (11)	165
C12—H12A⋯Cg2ⁱ	0.96	2.71	3.434 (11)	133
Symmetry code: (i) x, y-1, z. Cg1 and Cg2 are the centroids of the thiophene (S1/C5–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, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803732X/at2674sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803732X/at2674Isup2.hkl

checkCIF report

Comment top

Pyrimidine derivatives are attracting the increasing attention of 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 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 (Zeng et al., 2006). 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 cyclohexene ring adopts a half-chair conformation. The crystal packing is stabilized by three intramolecular C—H···O hydrogen bonds and two C—H···π interactions (Table 1). There exist no intermolecular hydrogen bonding interactions and no π-π stackings.

Related literature top

For background to the use of pyrimidine derivatives as drugs, see: Ding et al. (2004). For bond-length data, see: Allen (2002). For a related structure, see: Zeng et al. (2006).

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-Br-PhOH (3.1 mmol) and excess K₂CO₃ to the solution of carbodiimide, The mixture was stirred for 24 h at room temperature, the solution was condensed and the residue was recrystallized by EtOH to give the title compound, (I), in yield of 80% (m.p. 478 K). Elemental analysis calculated for C₁₉H₁₉BrN₂O₂S: C 54.42, H 4.57, N 6.68. Found: C 54.56, H 4.42, N 6.53. 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 1997).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.

2-(4-Bromo-phenoxy)-3-isopropyl-5,6,7,8-tetrahydro -benzothieno[2,3-d]pyrimidin-4(3H)-one top

Crystal data top

C₁₉H₁₉BrN₂O₂S	F(000) = 428
M_r = 419.33	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁	Melting point: 478K K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 13.3957 (7) Å	Cell parameters from 2048 reflections
b = 5.7366 (3) Å	θ = 2.9–24.5°
c = 13.3956 (7) Å	µ = 2.34 mm⁻¹
β = 115.541 (1)°	T = 298 K
V = 928.81 (8) Å³	Block, colorless
Z = 2	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2346 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→15
T_min = 0.652, T_max = 0.800	k = −6→6
5798 measured reflections	l = −15→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)] = 0.067	H-atom parameters constrained
wR(F²) = 0.204	w = 1/[σ²(F_o²) + (0.1151P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3228 reflections	Δρ_max = 0.67 e Å⁻³
228 parameters	Δρ_min = −0.63 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1424 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₉H₁₉BrN₂O₂S	V = 928.81 (8) Å³
M_r = 419.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 13.3957 (7) Å	µ = 2.34 mm⁻¹
b = 5.7366 (3) Å	T = 298 K
c = 13.3956 (7) Å	0.20 × 0.10 × 0.10 mm
β = 115.541 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3228 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2346 reflections with I > 2σ(I)
T_min = 0.652, T_max = 0.800	R_int = 0.106
5798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.204	Δρ_max = 0.67 e Å⁻³
S = 1.07	Δρ_min = −0.63 e Å⁻³
3228 reflections	Absolute structure: Flack (1983), 1424 Friedel pairs
228 parameters	Absolute structure parameter: 0.00 (8)
1 restraint

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
Br1	0.84533 (6)	0.7555 (2)	0.71718 (7)	0.0762 (4)
C1	0.0942 (6)	1.2447 (18)	0.8813 (6)	0.0534 (18)
H1A	0.0444	1.3157	0.8118	0.064*
H1B	0.0650	1.0921	0.8853	0.064*
C2	0.0967 (9)	1.390 (3)	0.9738 (10)	0.103 (5)
H2A	0.0231	1.4514	0.9536	0.124*
H2B	0.1152	1.2908	1.0380	0.124*
C3	0.1719 (9)	1.578 (2)	1.0038 (11)	0.093 (4)
H3A	0.1730	1.6464	1.0704	0.111*
H3B	0.1416	1.6942	0.9459	0.111*
C4	0.2917 (7)	1.537 (2)	1.0246 (7)	0.067 (3)
H4A	0.3234	1.6797	1.0119	0.081*
H4B	0.3351	1.4885	1.1006	0.081*
C5	0.2930 (6)	1.3513 (13)	0.9472 (6)	0.0460 (19)
C6	0.2071 (5)	1.2157 (15)	0.8824 (5)	0.046 (2)
C7	0.2363 (6)	1.0548 (14)	0.8163 (6)	0.0405 (16)
C8	0.3446 (6)	1.0816 (16)	0.8335 (6)	0.052 (2)
C9	0.1666 (6)	0.9073 (15)	0.7312 (6)	0.0457 (18)
C10	0.3302 (6)	0.8295 (14)	0.7015 (6)	0.047 (2)
C11	0.1472 (6)	0.6545 (14)	0.5719 (6)	0.0459 (18)
H11	0.0726	0.6617	0.5683	0.055*
C12	0.1754 (9)	0.3997 (19)	0.5775 (8)	0.079 (3)
H12A	0.1906	0.3406	0.6497	0.119*
H12B	0.2395	0.3796	0.5638	0.119*
H12C	0.1142	0.3161	0.5228	0.119*
C13	0.1386 (8)	0.767 (2)	0.4657 (6)	0.071 (2)
H13A	0.2104	0.7707	0.4661	0.107*
H13B	0.1112	0.9233	0.4608	0.107*
H13C	0.0889	0.6784	0.4033	0.107*
C14	0.4794 (6)	0.7242 (18)	0.6612 (7)	0.055 (2)
C15	0.5512 (8)	0.553 (2)	0.7233 (8)	0.073 (3)
H15	0.5268	0.4320	0.7536	0.087*
C16	0.6596 (8)	0.563 (2)	0.7394 (9)	0.074 (3)
H16	0.7096	0.4498	0.7815	0.088*
C17	0.6938 (5)	0.741 (2)	0.6934 (6)	0.061 (2)
C18	0.6221 (7)	0.9049 (19)	0.6317 (8)	0.066 (2)
H18	0.6458	1.0245	0.6002	0.079*
C19	0.5134 (8)	0.895 (2)	0.6152 (9)	0.073 (3)
H19	0.4634	1.0073	0.5720	0.088*
N1	0.3955 (5)	0.9634 (13)	0.7793 (6)	0.0527 (17)
N2	0.2193 (4)	0.7931 (13)	0.6717 (4)	0.0415 (13)
O1	0.0683 (4)	0.8637 (12)	0.7061 (5)	0.0664 (19)
O2	0.3666 (4)	0.7053 (13)	0.6384 (5)	0.072 (2)
S1	0.41333 (15)	1.2916 (5)	0.93045 (17)	0.0604 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0420 (4)	0.1275 (10)	0.0622 (5)	−0.0010 (6)	0.0253 (4)	−0.0105 (6)
C1	0.048 (4)	0.055 (5)	0.061 (4)	−0.001 (5)	0.027 (3)	0.001 (5)
C2	0.063 (6)	0.162 (13)	0.089 (8)	−0.006 (7)	0.037 (6)	−0.052 (8)
C3	0.079 (7)	0.105 (10)	0.106 (9)	−0.008 (7)	0.051 (7)	−0.036 (8)
C4	0.059 (5)	0.090 (7)	0.043 (4)	0.009 (5)	0.013 (4)	−0.009 (5)
C5	0.045 (4)	0.050 (5)	0.038 (4)	0.004 (3)	0.014 (3)	0.001 (3)
C6	0.039 (4)	0.057 (6)	0.036 (3)	0.007 (4)	0.011 (3)	0.004 (4)
C7	0.032 (3)	0.052 (4)	0.033 (3)	0.007 (3)	0.010 (3)	0.002 (3)
C8	0.033 (4)	0.070 (6)	0.043 (4)	−0.004 (4)	0.006 (3)	−0.002 (4)
C9	0.037 (4)	0.055 (5)	0.040 (4)	−0.004 (4)	0.012 (3)	0.006 (3)
C10	0.038 (4)	0.053 (5)	0.049 (4)	0.004 (3)	0.018 (3)	−0.006 (3)
C11	0.037 (4)	0.053 (5)	0.044 (4)	−0.009 (3)	0.013 (3)	−0.004 (3)
C12	0.100 (8)	0.058 (6)	0.061 (6)	−0.002 (6)	0.016 (6)	0.001 (5)
C13	0.083 (6)	0.069 (6)	0.044 (4)	0.001 (6)	0.011 (4)	0.007 (5)
C14	0.039 (4)	0.068 (6)	0.061 (4)	−0.009 (4)	0.024 (3)	−0.022 (5)
C15	0.054 (5)	0.088 (8)	0.076 (7)	−0.002 (5)	0.028 (5)	0.010 (6)
C16	0.050 (5)	0.093 (8)	0.076 (6)	0.004 (5)	0.027 (5)	0.019 (6)
C17	0.034 (3)	0.106 (7)	0.043 (4)	0.005 (6)	0.016 (3)	−0.019 (6)
C18	0.049 (5)	0.072 (6)	0.074 (6)	0.000 (5)	0.023 (5)	0.016 (5)
C19	0.048 (5)	0.077 (7)	0.084 (7)	0.011 (5)	0.019 (5)	0.009 (5)
N1	0.034 (3)	0.063 (5)	0.057 (4)	−0.007 (3)	0.016 (3)	−0.022 (4)
N2	0.031 (3)	0.049 (4)	0.043 (3)	−0.005 (3)	0.013 (2)	0.002 (3)
O1	0.033 (3)	0.103 (6)	0.062 (3)	−0.012 (3)	0.018 (2)	−0.019 (3)
O2	0.039 (3)	0.098 (6)	0.079 (4)	−0.011 (3)	0.025 (3)	−0.041 (4)
S1	0.0373 (9)	0.0736 (16)	0.0600 (11)	−0.0053 (11)	0.0114 (8)	−0.0194 (12)

Geometric parameters (Å, º) top

Br1—C17	1.916 (7)	C10—O2	1.347 (9)
C1—C2	1.481 (14)	C10—N2	1.378 (8)
C1—C6	1.515 (9)	C11—N2	1.497 (9)
C1—H1A	0.9700	C11—C12	1.504 (14)
C1—H1B	0.9700	C11—C13	1.521 (12)
C2—C3	1.410 (18)	C11—H11	0.9800
C2—H2A	0.9700	C12—H12A	0.9600
C2—H2B	0.9700	C12—H12B	0.9600
C3—C4	1.523 (14)	C12—H12C	0.9600
C3—H3A	0.9700	C13—H13A	0.9600
C3—H3B	0.9700	C13—H13B	0.9600
C4—C5	1.492 (12)	C13—H13C	0.9600
C4—H4A	0.9700	C14—C19	1.336 (15)
C4—H4B	0.9700	C14—C15	1.377 (15)
C5—C6	1.350 (11)	C14—O2	1.412 (9)
C5—S1	1.754 (8)	C15—C16	1.374 (13)
C6—C7	1.445 (10)	C15—H15	0.9300
C7—C8	1.375 (10)	C16—C17	1.370 (15)
C7—C9	1.404 (11)	C16—H16	0.9300
C8—N1	1.370 (10)	C17—C18	1.342 (14)
C8—S1	1.719 (9)	C18—C19	1.377 (12)
C9—O1	1.236 (9)	C18—H18	0.9300
C9—N2	1.431 (10)	C19—H19	0.9300
C10—N1	1.287 (10)

C2—C1—C6	113.0 (7)	N2—C11—C12	114.8 (7)
C2—C1—H1A	109.0	N2—C11—C13	111.6 (7)
C6—C1—H1A	109.0	C12—C11—C13	112.1 (8)
C2—C1—H1B	109.0	N2—C11—H11	105.8
C6—C1—H1B	109.0	C12—C11—H11	105.8
H1A—C1—H1B	107.8	C13—C11—H11	105.8
C3—C2—C1	115.1 (10)	C11—C12—H12A	109.5
C3—C2—H2A	108.5	C11—C12—H12B	109.5
C1—C2—H2A	108.5	H12A—C12—H12B	109.5
C3—C2—H2B	108.5	C11—C12—H12C	109.5
C1—C2—H2B	108.5	H12A—C12—H12C	109.5
H2A—C2—H2B	107.5	H12B—C12—H12C	109.5
C2—C3—C4	120.1 (11)	C11—C13—H13A	109.5
C2—C3—H3A	107.3	C11—C13—H13B	109.5
C4—C3—H3A	107.3	H13A—C13—H13B	109.5
C2—C3—H3B	107.3	C11—C13—H13C	109.5
C4—C3—H3B	107.3	H13A—C13—H13C	109.5
H3A—C3—H3B	106.9	H13B—C13—H13C	109.5
C5—C4—C3	108.0 (8)	C19—C14—C15	121.0 (8)
C5—C4—H4A	110.1	C19—C14—O2	120.1 (9)
C3—C4—H4A	110.1	C15—C14—O2	118.6 (9)
C5—C4—H4B	110.1	C16—C15—C14	118.6 (10)
C3—C4—H4B	110.1	C16—C15—H15	120.7
H4A—C4—H4B	108.4	C14—C15—H15	120.7
C6—C5—C4	126.6 (7)	C17—C16—C15	119.9 (10)
C6—C5—S1	112.4 (5)	C17—C16—H16	120.1
C4—C5—S1	121.0 (6)	C15—C16—H16	120.1
C5—C6—C7	112.3 (6)	C18—C17—C16	120.6 (7)
C5—C6—C1	120.9 (7)	C18—C17—Br1	119.9 (8)
C7—C6—C1	126.7 (7)	C16—C17—Br1	119.5 (8)
C8—C7—C9	119.2 (7)	C17—C18—C19	119.7 (10)
C8—C7—C6	111.8 (7)	C17—C18—H18	120.1
C9—C7—C6	128.4 (6)	C19—C18—H18	120.1
N1—C8—C7	125.8 (7)	C14—C19—C18	120.2 (9)
N1—C8—S1	121.3 (5)	C14—C19—H19	119.9
C7—C8—S1	112.8 (6)	C18—C19—H19	119.9
O1—C9—C7	126.9 (7)	C10—N1—C8	113.9 (6)
O1—C9—N2	118.7 (7)	C10—N2—C9	119.9 (6)
C7—C9—N2	114.4 (6)	C10—N2—C11	122.7 (6)
N1—C10—O2	121.4 (6)	C9—N2—C11	117.2 (5)
N1—C10—N2	126.6 (7)	C10—O2—C14	117.8 (6)
O2—C10—N2	112.0 (6)	C8—S1—C5	90.6 (4)

C6—C1—C2—C3	36.3 (16)	Br1—C17—C18—C19	−179.7 (8)
C1—C2—C3—C4	−50.1 (18)	C15—C14—C19—C18	−1.6 (16)
C2—C3—C4—C5	34.6 (16)	O2—C14—C19—C18	−175.9 (9)
C3—C4—C5—C6	−9.8 (13)	C17—C18—C19—C14	0.5 (16)
C3—C4—C5—S1	169.1 (8)	O2—C10—N1—C8	178.4 (7)
C4—C5—C6—C7	179.3 (8)	N2—C10—N1—C8	−1.7 (13)
S1—C5—C6—C7	0.4 (8)	C7—C8—N1—C10	4.8 (13)
C4—C5—C6—C1	1.0 (12)	S1—C8—N1—C10	−173.3 (6)
S1—C5—C6—C1	−177.9 (6)	N1—C10—N2—C9	−1.2 (12)
C2—C1—C6—C5	−13.3 (13)	O2—C10—N2—C9	178.8 (7)
C2—C1—C6—C7	168.6 (10)	N1—C10—N2—C11	173.0 (8)
C5—C6—C7—C8	−1.3 (10)	O2—C10—N2—C11	−7.0 (10)
C1—C6—C7—C8	176.9 (7)	O1—C9—N2—C10	−176.8 (7)
C5—C6—C7—C9	−172.1 (8)	C7—C9—N2—C10	1.2 (10)
C1—C6—C7—C9	6.1 (13)	O1—C9—N2—C11	8.7 (10)
C9—C7—C8—N1	−4.8 (13)	C7—C9—N2—C11	−173.3 (7)
C6—C7—C8—N1	−176.6 (8)	C12—C11—N2—C10	66.0 (10)
C9—C7—C8—S1	173.4 (6)	C13—C11—N2—C10	−63.0 (10)
C6—C7—C8—S1	1.6 (9)	C12—C11—N2—C9	−119.6 (9)
C8—C7—C9—O1	179.4 (8)	C13—C11—N2—C9	111.4 (8)
C6—C7—C9—O1	−10.4 (14)	N1—C10—O2—C14	0.8 (13)
C8—C7—C9—N2	1.5 (11)	N2—C10—O2—C14	−179.2 (7)
C6—C7—C9—N2	171.7 (7)	C19—C14—O2—C10	−86.5 (11)
C19—C14—C15—C16	1.5 (15)	C15—C14—O2—C10	99.1 (10)
O2—C14—C15—C16	175.9 (9)	N1—C8—S1—C5	177.1 (8)
C14—C15—C16—C17	−0.4 (16)	C7—C8—S1—C5	−1.2 (7)
C15—C16—C17—C18	−0.6 (16)	C6—C5—S1—C8	0.4 (6)
C15—C16—C17—Br1	179.7 (8)	C4—C5—S1—C8	−178.6 (7)
C16—C17—C18—C19	0.6 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.98	2.20	2.726 (10)	112
C12—H12B···O2	0.96	2.43	2.915 (13)	111
C13—H13A···O2	0.96	2.38	2.951 (10)	117
C12—H12B···Cg1	0.96	2.92	3.854 (11)	165
C12—H12B···Cg2	0.96	2.71	3.434 (11)	133

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉BrN₂O₂S
M_r	419.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	13.3957 (7), 5.7366 (3), 13.3956 (7)
β (°)	115.541 (1)
V (Å³)	928.81 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
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	0.652, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	5798, 3228, 2346
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.204, 1.07
No. of reflections	3228
No. of parameters	228
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.63
Absolute structure	Flack (1983), 1424 Friedel pairs
Absolute structure parameter	0.00 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1	0.98	2.20	2.726 (10)	112.1
C12—H12B···O2	0.96	2.43	2.915 (13)	110.7
C13—H13A···O2	0.96	2.38	2.951 (10)	117.4
C12—H12B···Cg1	0.96	2.92	3.854 (11)	165
C12—H12B···Cg2	0.96	2.71	3.434 (11)	133

Acknowledgements

We gratefully acknowledge financial support of this work by the Research Foundation for Students and Teachers of Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366–8371. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, X.-H., Ding, M.-W. & He, H.-W. (2006). Acta Cryst. E62, o731–o732. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2404

doi:10.1107/S160053680803732X

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

2-(4-Bromo­phen­­oxy)-3-iso­propyl-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

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