2-(4-Bromo-phen-oxy)-3-isopropyl-5,6,7,8-tetra-hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one.

In the title compound, C(19)H(19)BrN(2)O(2)S, the central thieno-pyrim-idine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å. The attached cyclo-hexene ring adopts a half-chair conformation. The molecular conformation and crystal packing are stabilized by three intra-molecular C-H⋯O hydrogen bonds and two C-H⋯π inter-actions.

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 = 418.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.204

S = 1.07

3228 reflections

228 parameters

1 restraint

H-atom parameters constrained

Δρmax = 7.69 e Å−3

Δρmin = −2.63 e Å−3

Absolute structure: Flack (1983 ▶), 1424 Freidel pairs

Flack parameter: 0.00 (8)

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 ▶).

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

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

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

C19H19BrN2O2S	F000 = 428
Mr = 419.33	Dx = 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 = 2.9–24.5º
c = 13.3956 (7) Å	µ = 2.34 mm−1
β = 115.5410 (10)º	T = 298 (2) K
V = 928.81 (8) Å3	Block, colorless
Z = 2	0.20 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2346 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.106
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→15
Tmin = 0.652, Tmax = 0.800	k = −6→6
5798 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067	w = 1/[σ2(Fo2) + (0.1151P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.204	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.67 e Å−3
3228 reflections	Δρmin = −0.62 e Å−3
228 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1424 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)
Secondary atom site location: difference Fourier map

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
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)

	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)

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)

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

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) . Cg1 and Cg2 are the centroids of the thiophene (S1/C5–C8) and pyrimidine (N1/N2/C7–C10) rings, respectively.