9-Isopropenyl-4-methyl-2H-thieno[2,3-h]chromen-2-one.

The title compound, C(15)H(12)O(2)S, features three fused rings with a dihedral angle of 79.6 (2)° between the isopropenyl group and the thio-phene ring. In the crystal, mol-ecules are connected into a supra-molecular helical chain via C-H⋯O contacts.

Related literature

The title compound was obtained unexpectedly during an attempt to prepare 4-methyl-7-(2-methyl­but-3-yn-2-ylthio)-2H-chromen-2-one, a key inter­mediate in our study of the synthesis of potential anti-HIV heterocyclic agents (Chen et al., 2004 ▶)

Experimental

Crystal data

C15H12O2S

M = 256.31

Monoclinic,

a = 8.547 (2) Å

b = 11.425 (3) Å

c = 13.641 (4) Å

β = 108.259 (19)°

V = 1265.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.50 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.887, T max = 0.971

5816 measured reflections

2698 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.177

S = 0.99

2698 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017930/tk2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017930/tk2449Isup2.hkl

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

C15H12O2S	F(000) = 536
Mr = 256.31	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 812 reflections
a = 8.547 (2) Å	θ = 3.1–27.4°
b = 11.425 (3) Å	µ = 0.25 mm−1
c = 13.641 (4) Å	T = 293 K
β = 108.259 (19)°	Block, yellow
V = 1265.0 (6) Å3	0.50 × 0.15 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2698 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
graphite	Rint = 0.091
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.887, Tmax = 0.971	k = −11→14
5816 measured reflections	l = −14→17

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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.177	w = 1/[σ2(Fo2) + (0.1022P)2P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2698 reflections	Δρmax = 0.37 e Å−3
166 parameters	Δρmin = −0.44 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (5)

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
S1	0.97805 (8)	−0.09812 (6)	0.19803 (5)	0.0637 (3)
O1	0.65111 (17)	0.10433 (13)	0.38658 (11)	0.0495 (4)
O2	0.4812 (2)	0.18035 (18)	0.46125 (14)	0.0719 (6)
C1	0.6213 (3)	0.1761 (2)	0.45948 (18)	0.0526 (6)
C2	0.7579 (3)	0.2386 (2)	0.52571 (17)	0.0563 (6)
H2	0.7401	0.2892	0.5745	0.068*
C3	0.9108 (3)	0.22726 (19)	0.52044 (17)	0.0486 (6)
C4	0.9398 (3)	0.14773 (18)	0.44540 (15)	0.0411 (5)
C5	1.0960 (3)	0.12728 (19)	0.43491 (17)	0.0464 (5)
H5	1.1872	0.1650	0.4793	0.056*
C6	1.1173 (3)	0.0535 (2)	0.36125 (17)	0.0498 (6)
H6	1.2213	0.0407	0.3552	0.060*
C7	0.9796 (3)	−0.0016 (2)	0.29585 (16)	0.0457 (5)
C8	0.8207 (2)	0.01396 (19)	0.30220 (15)	0.0431 (5)
C9	0.8056 (3)	0.09080 (17)	0.37904 (16)	0.0415 (5)
C10	0.6986 (3)	−0.0519 (2)	0.22558 (17)	0.0520 (6)
C11	0.7694 (3)	−0.1131 (2)	0.1659 (2)	0.0627 (7)
H11	0.7089	−0.1598	0.1114	0.075*
C12	0.5195 (3)	−0.0597 (2)	0.21115 (19)	0.0587 (7)
C13	0.4143 (4)	−0.0004 (4)	0.1349 (3)	0.1030 (12)
H13A	0.3015	−0.0075	0.1233	0.124*
H13B	0.4534	0.0484	0.0931	0.124*
C14	0.4693 (4)	−0.1369 (3)	0.2794 (3)	0.0912 (10)
H14A	0.3512	−0.1377	0.2605	0.137*
H14B	0.5147	−0.1099	0.3492	0.137*
H14C	0.5084	−0.2146	0.2738	0.137*
C15	1.0528 (3)	0.2947 (2)	0.5901 (2)	0.0675 (8)
H15A	1.0157	0.3400	0.6378	0.101*
H15B	1.0967	0.3460	0.5496	0.101*
H15C	1.1369	0.2412	0.6277	0.101*

	U11	U22	U33	U12	U13	U23
S1	0.0501 (5)	0.0779 (5)	0.0685 (5)	−0.0039 (3)	0.0261 (4)	−0.0209 (3)
O1	0.0338 (9)	0.0599 (10)	0.0531 (9)	0.0017 (7)	0.0113 (7)	−0.0063 (7)
O2	0.0453 (11)	0.0963 (14)	0.0778 (12)	0.0071 (9)	0.0246 (10)	−0.0110 (10)
C1	0.0417 (14)	0.0603 (14)	0.0555 (13)	0.0080 (11)	0.0149 (11)	0.0032 (11)
C2	0.0582 (16)	0.0567 (14)	0.0545 (13)	0.0085 (12)	0.0184 (12)	−0.0063 (11)
C3	0.0488 (14)	0.0448 (12)	0.0494 (12)	0.0008 (10)	0.0114 (11)	0.0021 (10)
C4	0.0392 (12)	0.0405 (10)	0.0426 (10)	−0.0018 (9)	0.0112 (9)	0.0036 (9)
C5	0.0368 (12)	0.0475 (11)	0.0524 (12)	−0.0077 (10)	0.0102 (10)	0.0029 (10)
C6	0.0350 (12)	0.0567 (13)	0.0595 (13)	−0.0025 (11)	0.0177 (10)	0.0033 (11)
C7	0.0408 (12)	0.0519 (12)	0.0465 (11)	−0.0004 (10)	0.0168 (10)	0.0007 (10)
C8	0.0358 (11)	0.0476 (12)	0.0450 (11)	0.0003 (9)	0.0112 (10)	0.0023 (9)
C9	0.0339 (12)	0.0459 (11)	0.0453 (11)	0.0026 (9)	0.0134 (10)	0.0059 (9)
C10	0.0409 (13)	0.0607 (14)	0.0498 (12)	0.0034 (11)	0.0078 (10)	−0.0060 (11)
C11	0.0472 (15)	0.0769 (17)	0.0603 (14)	0.0012 (12)	0.0114 (12)	−0.0201 (13)
C12	0.0366 (13)	0.0708 (16)	0.0617 (14)	0.0009 (12)	0.0054 (12)	−0.0187 (13)
C13	0.0510 (18)	0.118 (3)	0.121 (3)	0.0160 (19)	−0.0002 (18)	0.019 (2)
C14	0.0461 (17)	0.118 (3)	0.111 (2)	−0.0068 (18)	0.0273 (18)	0.012 (2)
C15	0.0649 (18)	0.0664 (16)	0.0681 (16)	−0.0130 (13)	0.0165 (14)	−0.0224 (13)

S1—C11	1.706 (3)	C7—C8	1.399 (3)
S1—C7	1.728 (2)	C8—C9	1.404 (3)
O1—C9	1.365 (2)	C8—C10	1.437 (3)
O1—C1	1.373 (3)	C10—C11	1.351 (3)
O2—C1	1.205 (3)	C10—C12	1.484 (3)
C1—C2	1.424 (3)	C11—H11	0.9300
C2—C3	1.338 (3)	C12—C13	1.328 (4)
C2—H2	0.9300	C12—C14	1.442 (4)
C3—C4	1.447 (3)	C13—H13A	0.9300
C3—C15	1.499 (3)	C13—H13B	0.9300
C4—C9	1.381 (3)	C14—H14A	0.9600
C4—C5	1.406 (3)	C14—H14B	0.9600
C5—C6	1.367 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.385 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C11—S1—C7	90.94 (11)	O1—C9—C8	116.39 (18)
C9—O1—C1	121.72 (17)	C4—C9—C8	122.13 (19)
O2—C1—O1	116.7 (2)	C11—C10—C8	110.4 (2)
O2—C1—C2	126.1 (2)	C11—C10—C12	121.8 (2)
O1—C1—C2	117.21 (19)	C8—C10—C12	127.7 (2)
C3—C2—C1	122.6 (2)	C10—C11—S1	115.0 (2)
C3—C2—H2	118.7	C10—C11—H11	122.5
C1—C2—H2	118.7	S1—C11—H11	122.5
C2—C3—C4	119.1 (2)	C13—C12—C14	123.5 (3)
C2—C3—C15	121.8 (2)	C13—C12—C10	119.4 (3)
C4—C3—C15	119.1 (2)	C14—C12—C10	117.0 (2)
C9—C4—C5	118.38 (19)	C12—C13—H13A	120.0
C9—C4—C3	117.90 (19)	C12—C13—H13B	120.0
C5—C4—C3	123.7 (2)	H13A—C13—H13B	120.0
C6—C5—C4	121.8 (2)	C12—C14—H14A	109.5
C6—C5—H5	119.1	C12—C14—H14B	109.5
C4—C5—H5	119.1	H14A—C14—H14B	109.5
C5—C6—C7	118.1 (2)	C12—C14—H14C	109.5
C5—C6—H6	120.9	H14A—C14—H14C	109.5
C7—C6—H6	120.9	H14B—C14—H14C	109.5
C6—C7—C8	123.2 (2)	C3—C15—H15A	109.5
C6—C7—S1	125.92 (17)	C3—C15—H15B	109.5
C8—C7—S1	110.87 (16)	H15A—C15—H15B	109.5
C7—C8—C9	116.35 (19)	C3—C15—H15C	109.5
C7—C8—C10	112.72 (19)	H15A—C15—H15C	109.5
C9—C8—C10	130.9 (2)	H15B—C15—H15C	109.5
O1—C9—C4	121.46 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.93	2.44	3.293 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.93	2.44	3.293 (3)	153

Symmetry code: (i) .