2-(1H-Imidazol-1-yl)-3-isopropyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one.

In the title compound, C(16)H(14)N(4)OS, the three fused rings of the benzothieno[3,2-d]pyrimidinone unit are essentially coplanar, the maximum deviation from the mean plane being 0.067 (3) Å. The dihedral angle between the mean plane of the fused rings and the imidazole ring is 72.00 (3)°. Offset π-π stacking inter-actions involving the fused rings are effective in the stabilization of the crystal structure. The centroid-centroid distances between the thienophene and benzene rings, and between the pyrimidine and benzene rings are 3.67 (1) and 3.93 (1) Å, respectively. There are two intramolecular C-H⋯O interactions.

Related literature

For related literature, see: Chambhare et al. (2003 ▶); Ding et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Cao (2007 ▶); Xu et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

C16H14N4OS

M = 310.37

Monoclinic,

a = 15.2759 (16) Å

b = 12.1387 (12) Å

c = 8.0172 (8) Å

β = 97.439 (2)°

V = 1474.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.36 × 0.23 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

8864 measured reflections

3216 independent reflections

2657 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.132

S = 1.08

3216 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 (Bruker, 2001 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064598/is2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064598/is2265Isup2.hkl

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

C16H14N4OS	F000 = 648
Mr = 310.37	Dx = 1.398 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3860 reflections
a = 15.2759 (16) Å	θ = 2.7–28.0º
b = 12.1387 (12) Å	µ = 0.23 mm−1
c = 8.0172 (8) Å	T = 298 (2) K
β = 97.439 (2)º	Block, colorless
V = 1474.1 (3) Å3	0.36 × 0.23 × 0.20 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	2657 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Monochromator: graphite	θmax = 27.0º
T = 298(2) K	θmin = 2.2º
φ and ω scans	h = −19→16
Absorption correction: none	k = −14→15
8864 measured reflections	l = −7→10
3216 independent reflections

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0813P)2 + 0.01P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.017
3216 reflections	Δρmax = 0.31 e Å−3
201 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C1	0.01352 (10)	0.41878 (12)	0.82291 (18)	0.0377 (3)
C2	−0.04456 (11)	0.48730 (14)	0.7227 (2)	0.0477 (4)
H2	−0.0232	0.5438	0.6608	0.057*
C3	−0.13345 (12)	0.47032 (16)	0.7166 (3)	0.0591 (5)
H3	−0.1728	0.5158	0.6504	0.071*
C4	−0.16574 (12)	0.38522 (16)	0.8090 (3)	0.0641 (5)
H4	−0.2264	0.3750	0.8029	0.077*
C5	−0.10994 (12)	0.31650 (15)	0.9083 (3)	0.0567 (5)
H5	−0.1320	0.2601	0.9695	0.068*
C6	−0.01944 (11)	0.33330 (12)	0.9151 (2)	0.0435 (4)
C7	0.10839 (10)	0.41943 (11)	0.84835 (18)	0.0357 (3)
C8	0.14306 (10)	0.33777 (12)	0.95497 (19)	0.0404 (4)
C9	0.23580 (11)	0.32519 (13)	1.0012 (2)	0.0455 (4)
C10	0.24368 (10)	0.47907 (11)	0.81241 (18)	0.0368 (3)
C11	0.30832 (14)	0.65924 (14)	0.7549 (3)	0.0616 (5)
H11	0.2832	0.6983	0.8365	0.074*
C12	0.34470 (12)	0.52387 (15)	0.5998 (2)	0.0520 (4)
H12	0.3505	0.4548	0.5521	0.062*
C13	0.37967 (12)	0.61901 (15)	0.5549 (2)	0.0544 (4)
H13	0.4149	0.6261	0.4692	0.065*
C14	0.38228 (10)	0.41578 (14)	0.9892 (2)	0.0459 (4)
H14	0.4043	0.4766	0.9259	0.055*
C15	0.39582 (13)	0.44994 (16)	1.1717 (3)	0.0630 (5)
H15A	0.3672	0.3980	1.2370	0.095*
H15B	0.3710	0.5218	1.1827	0.095*
H15C	0.4579	0.4518	1.2114	0.095*
C16	0.43350 (13)	0.31491 (17)	0.9501 (3)	0.0676 (6)
H16A	0.4157	0.2533	1.0128	0.101*
H16B	0.4955	0.3281	0.9805	0.101*
H16C	0.4220	0.2991	0.8319	0.101*
N1	0.16018 (8)	0.48993 (10)	0.77008 (16)	0.0375 (3)
N2	0.28561 (8)	0.40583 (10)	0.92822 (16)	0.0402 (3)
N3	0.29862 (8)	0.54942 (10)	0.73057 (16)	0.0397 (3)
N4	0.35659 (12)	0.70387 (13)	0.6517 (2)	0.0699 (5)
O1	0.27164 (10)	0.25478 (10)	1.09671 (19)	0.0662 (4)
S1	0.06414 (3)	0.25652 (3)	1.02987 (6)	0.05010 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0434 (8)	0.0343 (7)	0.0358 (8)	−0.0020 (6)	0.0073 (6)	−0.0069 (6)
C2	0.0488 (9)	0.0438 (8)	0.0502 (10)	0.0038 (7)	0.0054 (7)	−0.0002 (7)
C3	0.0465 (10)	0.0589 (11)	0.0709 (13)	0.0070 (8)	0.0035 (9)	−0.0047 (9)
C4	0.0433 (10)	0.0640 (11)	0.0865 (15)	−0.0031 (9)	0.0140 (10)	−0.0157 (11)
C5	0.0538 (11)	0.0523 (10)	0.0672 (12)	−0.0111 (8)	0.0201 (9)	−0.0072 (9)
C6	0.0501 (9)	0.0383 (7)	0.0433 (9)	−0.0063 (7)	0.0112 (7)	−0.0071 (7)
C7	0.0438 (8)	0.0309 (7)	0.0317 (7)	−0.0031 (6)	0.0024 (6)	−0.0017 (6)
C8	0.0501 (9)	0.0343 (7)	0.0359 (8)	−0.0054 (6)	0.0022 (6)	0.0029 (6)
C9	0.0505 (9)	0.0401 (8)	0.0435 (9)	−0.0035 (7)	−0.0021 (7)	0.0067 (7)
C10	0.0447 (8)	0.0313 (7)	0.0337 (8)	−0.0021 (6)	0.0025 (6)	0.0000 (6)
C11	0.0814 (14)	0.0351 (8)	0.0741 (13)	−0.0054 (8)	0.0322 (11)	−0.0024 (8)
C12	0.0597 (11)	0.0528 (10)	0.0457 (10)	−0.0058 (8)	0.0147 (8)	−0.0054 (8)
C13	0.0521 (10)	0.0655 (11)	0.0472 (10)	−0.0090 (9)	0.0123 (8)	0.0030 (8)
C14	0.0402 (8)	0.0494 (9)	0.0459 (9)	0.0004 (7)	−0.0033 (7)	0.0003 (7)
C15	0.0559 (10)	0.0709 (12)	0.0573 (12)	0.0044 (9)	−0.0118 (9)	−0.0140 (9)
C16	0.0576 (11)	0.0676 (13)	0.0756 (14)	0.0157 (9)	0.0014 (10)	−0.0118 (10)
N1	0.0406 (7)	0.0349 (6)	0.0363 (7)	−0.0002 (5)	0.0029 (5)	0.0040 (5)
N2	0.0423 (7)	0.0381 (6)	0.0381 (7)	−0.0013 (5)	−0.0030 (5)	0.0029 (5)
N3	0.0409 (7)	0.0369 (6)	0.0411 (7)	−0.0022 (5)	0.0044 (5)	0.0016 (5)
N4	0.0847 (13)	0.0507 (9)	0.0801 (12)	−0.0141 (8)	0.0333 (10)	0.0046 (8)
O1	0.0630 (9)	0.0585 (8)	0.0717 (10)	−0.0013 (6)	−0.0118 (7)	0.0320 (6)
S1	0.0584 (3)	0.0417 (3)	0.0497 (3)	−0.01108 (17)	0.0051 (2)	0.01099 (17)

C1—C2	1.393 (2)	C10—N3	1.4166 (18)
C1—C6	1.405 (2)	C11—N4	1.296 (2)
C1—C7	1.437 (2)	C11—N3	1.353 (2)
C2—C3	1.368 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.341 (2)
C3—C4	1.397 (3)	C12—N3	1.372 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.371 (3)	C13—N4	1.363 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.392 (2)	C14—N2	1.499 (2)
C5—H5	0.9300	C14—C16	1.508 (2)
C6—S1	1.7437 (18)	C14—C15	1.509 (3)
C7—C8	1.370 (2)	C14—H14	0.9800
C7—N1	1.3713 (18)	C15—H15A	0.9600
C8—C9	1.425 (2)	C15—H15B	0.9600
C8—S1	1.7247 (15)	C15—H15C	0.9600
C9—O1	1.2279 (19)	C16—H16A	0.9600
C9—N2	1.4126 (19)	C16—H16B	0.9600
C10—N1	1.2835 (19)	C16—H16C	0.9600
C10—N2	1.3816 (18)
C2—C1—C6	119.98 (14)	C13—C12—N3	105.79 (15)
C2—C1—C7	129.35 (14)	C13—C12—H12	127.1
C6—C1—C7	110.66 (13)	N3—C12—H12	127.1
C3—C2—C1	119.07 (16)	C12—C13—N4	110.89 (16)
C3—C2—H2	120.5	C12—C13—H13	124.6
C1—C2—H2	120.5	N4—C13—H13	124.6
C2—C3—C4	120.61 (18)	N2—C14—C16	112.49 (14)
C2—C3—H3	119.7	N2—C14—C15	110.11 (14)
C4—C3—H3	119.7	C16—C14—C15	114.53 (15)
C5—C4—C3	121.45 (17)	N2—C14—H14	106.4
C5—C4—H4	119.3	C16—C14—H14	106.4
C3—C4—H4	119.3	C15—C14—H14	106.4
C4—C5—C6	118.25 (17)	C14—C15—H15A	109.5
C4—C5—H5	120.9	C14—C15—H15B	109.5
C6—C5—H5	120.9	H15A—C15—H15B	109.5
C5—C6—C1	120.63 (16)	C14—C15—H15C	109.5
C5—C6—S1	126.75 (14)	H15A—C15—H15C	109.5
C1—C6—S1	112.62 (12)	H15B—C15—H15C	109.5
C8—C7—N1	122.53 (14)	C14—C16—H16A	109.5
C8—C7—C1	112.70 (13)	C14—C16—H16B	109.5
N1—C7—C1	124.70 (13)	H16A—C16—H16B	109.5
C7—C8—C9	122.07 (14)	C14—C16—H16C	109.5
C7—C8—S1	113.57 (12)	H16A—C16—H16C	109.5
C9—C8—S1	124.34 (11)	H16B—C16—H16C	109.5
O1—C9—N2	121.34 (15)	C10—N1—C7	115.30 (12)
O1—C9—C8	125.79 (15)	C10—N2—C9	119.78 (12)
N2—C9—C8	112.86 (12)	C10—N2—C14	121.25 (12)
N1—C10—N2	127.02 (13)	C9—N2—C14	118.78 (12)
N1—C10—N3	116.35 (12)	C11—N3—C12	106.00 (14)
N2—C10—N3	116.63 (12)	C11—N3—C10	125.99 (14)
N4—C11—N3	112.37 (17)	C12—N3—C10	127.67 (13)
N4—C11—H11	123.8	C11—N4—C13	104.96 (15)
N3—C11—H11	123.8	C8—S1—C6	90.44 (8)
C6—C1—C2—C3	0.4 (2)	C1—C7—N1—C10	178.52 (13)
C7—C1—C2—C3	179.29 (16)	N1—C10—N2—C9	6.4 (2)
C1—C2—C3—C4	−0.3 (3)	N3—C10—N2—C9	−173.15 (12)
C2—C3—C4—C5	0.1 (3)	N1—C10—N2—C14	−168.50 (14)
C3—C4—C5—C6	−0.1 (3)	N3—C10—N2—C14	11.9 (2)
C4—C5—C6—C1	0.2 (2)	O1—C9—N2—C10	175.54 (16)
C4—C5—C6—S1	−179.33 (14)	C8—C9—N2—C10	−5.9 (2)
C2—C1—C6—C5	−0.3 (2)	O1—C9—N2—C14	−9.4 (2)
C7—C1—C6—C5	−179.46 (14)	C8—C9—N2—C14	169.11 (13)
C2—C1—C6—S1	179.26 (12)	C16—C14—N2—C10	−119.77 (17)
C7—C1—C6—S1	0.14 (15)	C15—C14—N2—C10	111.16 (16)
C2—C1—C7—C8	−179.09 (15)	C16—C14—N2—C9	65.26 (19)
C6—C1—C7—C8	−0.07 (17)	C15—C14—N2—C9	−63.80 (18)
C2—C1—C7—N1	−1.9 (2)	N4—C11—N3—C12	−0.4 (2)
C6—C1—C7—N1	177.12 (13)	N4—C11—N3—C10	−174.04 (16)
N1—C7—C8—C9	4.5 (2)	C13—C12—N3—C11	0.6 (2)
C1—C7—C8—C9	−178.29 (13)	C13—C12—N3—C10	174.10 (15)
N1—C7—C8—S1	−177.29 (11)	N1—C10—N3—C11	70.9 (2)
C1—C7—C8—S1	−0.03 (17)	N2—C10—N3—C11	−109.48 (18)
C7—C8—C9—O1	179.45 (17)	N1—C10—N3—C12	−101.43 (18)
S1—C8—C9—O1	1.4 (3)	N2—C10—N3—C12	78.2 (2)
C7—C8—C9—N2	1.0 (2)	N3—C11—N4—C13	0.0 (2)
S1—C8—C9—N2	−177.07 (11)	C12—C13—N4—C11	0.4 (2)
N3—C12—C13—N4	−0.6 (2)	C7—C8—S1—C6	0.09 (12)
N2—C10—N1—C7	−0.9 (2)	C9—C8—S1—C6	178.31 (14)
N3—C10—N1—C7	178.70 (12)	C5—C6—S1—C8	179.44 (16)
C8—C7—N1—C10	−4.6 (2)	C1—C6—S1—C8	−0.14 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1	0.96	2.38	2.963 (3)	119
C15—H15A···O1	0.96	2.45	3.046 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O1	0.96	2.38	2.963 (3)	119
C15—H15A⋯O1	0.96	2.45	3.046 (2)	120