Crystal structure of 3-[2-(thio-phen-3-yl)ethyn-yl]-2H-chromen-2-one.

In the title compound, C15H8O2S, the coumarin moiety is approximately planar (r.m.s. deviation of the 11 non-H atoms = 0.025 Å) and is slightly inclined with respect to the plane of the thio-phen-3-yl ring, forming a dihedral angle of 11.75 (8)°. In the crystal, the three-dimensional architecture features a combination of coumarin-thio-phene C-H⋯π and π-π [inter-centroid distance = 3.6612 (12) Å] inter-actions.

Related literature

For the wide range of different biological activities of coumarins, see: Wu et al. (2009 ▸); Roussaki et al. (2014 ▸). For background to our ongoing inter­est in the synthesis and crystal structures of coumarin derivatives, see: Stefani et al. (2012 ▸); Caracelli et al. (2015 ▸). For the synthesis of the title compound, see: Gueogjian (2011 ▸).

Experimental

Crystal data

C15H8O2S

M = 252.27

Monoclinic,

a = 10.7726 (6) Å

b = 9.7572 (3) Å

c = 12.2084 (5) Å

β = 115.547 (6)°

V = 1157.77 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.40 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Agilent CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T min = 0.338, T max = 1.000

4511 measured reflections

2373 independent reflections

2108 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.156

S = 1.06

2373 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.57 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015002157/su5073sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002157/su5073Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002157/su5073Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002157/su5073fig1.tif

Mol­ecular structure of the title compound showing atom labelling and displacement ellipsoids at the 70% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015002157/su5073fig2.tif

A view in projection down the b axis of the unit-cell contents. The π–π and C—H⋯π inter­actions are shown as purple and orange dashed lines, respectively.

CCDC reference: 1046686

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H8O2S	F(000) = 520
Mr = 252.27	Dx = 1.447 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.7726 (6) Å	Cell parameters from 2362 reflections
b = 9.7572 (3) Å	θ = 4.0–76.0°
c = 12.2084 (5) Å	µ = 2.40 mm−1
β = 115.547 (6)°	T = 100 K
V = 1157.77 (11) Å3	Prism, dark yellow
Z = 4	0.25 × 0.15 × 0.05 mm

Agilent CCD diffractometer	2108 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	Rint = 0.023
ω scans	θmax = 76.2°, θmin = 4.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −13→11
Tmin = 0.338, Tmax = 1.000	k = −12→10
4511 measured reflections	l = −15→14
2373 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.1031P)2 + 0.5663P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2373 reflections	Δρmax = 0.42 e Å−3
163 parameters	Δρmin = −0.57 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
S1	1.08150 (6)	0.79946 (6)	0.56811 (5)	0.0338 (2)
O1	0.47823 (14)	0.23152 (14)	0.60599 (12)	0.0194 (3)
O2	0.62583 (14)	0.39103 (15)	0.71228 (12)	0.0236 (3)
C1	1.0505 (2)	0.80962 (19)	0.69506 (19)	0.0225 (4)
H1	1.0976	0.8684	0.7624	0.027*
C2	0.9466 (2)	0.7191 (2)	0.68413 (19)	0.0236 (4)
H2	0.9143	0.7081	0.7448	0.028*
C3	0.8928 (2)	0.64361 (19)	0.57262 (18)	0.0204 (4)
C4	0.9581 (2)	0.6785 (2)	0.50099 (19)	0.0274 (5)
H4	0.9368	0.6396	0.4236	0.033*
C5	0.7859 (2)	0.5442 (2)	0.54250 (17)	0.0207 (4)
C6	0.69803 (19)	0.4614 (2)	0.52352 (16)	0.0198 (4)
C11	0.57073 (19)	0.3326 (2)	0.61608 (17)	0.0186 (4)
C7	0.59579 (19)	0.35987 (19)	0.50841 (17)	0.0183 (4)
C8	0.5239 (2)	0.29061 (19)	0.40315 (18)	0.0194 (4)
H8	0.5380	0.3115	0.3334	0.023*
C9	0.4272 (2)	0.18649 (19)	0.39642 (18)	0.0183 (4)
C15	0.3539 (2)	0.1072 (2)	0.29190 (17)	0.0211 (4)
H15	0.3642	0.1249	0.2198	0.025*
C14	0.2672 (2)	0.00402 (19)	0.29346 (18)	0.0216 (4)
H14	0.2187	−0.0497	0.2229	0.026*
C13	0.2510 (2)	−0.0214 (2)	0.39989 (18)	0.0224 (4)
H13	0.1905	−0.0920	0.4004	0.027*
C12	0.3219 (2)	0.0550 (2)	0.50393 (18)	0.0218 (4)
H12	0.3114	0.0371	0.5759	0.026*
C10	0.40856 (19)	0.1581 (2)	0.50072 (17)	0.0185 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0356 (4)	0.0357 (4)	0.0303 (4)	−0.0118 (2)	0.0144 (3)	0.0005 (2)
O1	0.0231 (7)	0.0234 (7)	0.0148 (6)	−0.0009 (5)	0.0109 (5)	0.0002 (5)
O2	0.0262 (7)	0.0299 (8)	0.0159 (7)	−0.0019 (6)	0.0102 (6)	−0.0023 (6)
C1	0.0212 (9)	0.0219 (9)	0.0222 (10)	0.0033 (7)	0.0072 (8)	−0.0011 (7)
C2	0.0254 (10)	0.0257 (9)	0.0209 (10)	0.0022 (8)	0.0112 (8)	−0.0019 (7)
C3	0.0221 (9)	0.0205 (9)	0.0182 (9)	0.0010 (7)	0.0082 (7)	0.0021 (7)
C4	0.0334 (11)	0.0304 (10)	0.0194 (10)	−0.0080 (9)	0.0122 (9)	−0.0008 (8)
C5	0.0244 (9)	0.0241 (9)	0.0154 (8)	0.0034 (8)	0.0104 (7)	0.0018 (7)
C6	0.0246 (10)	0.0218 (9)	0.0142 (8)	0.0040 (7)	0.0096 (7)	0.0005 (7)
C11	0.0211 (9)	0.0202 (9)	0.0159 (9)	0.0030 (7)	0.0092 (7)	0.0009 (7)
C7	0.0208 (9)	0.0197 (9)	0.0164 (9)	0.0016 (7)	0.0099 (7)	0.0016 (7)
C8	0.0228 (9)	0.0226 (9)	0.0160 (9)	0.0000 (7)	0.0113 (8)	0.0006 (7)
C9	0.0207 (9)	0.0183 (8)	0.0174 (9)	0.0011 (7)	0.0098 (7)	0.0002 (7)
C15	0.0245 (9)	0.0255 (9)	0.0146 (8)	0.0006 (7)	0.0097 (7)	−0.0003 (7)
C14	0.0238 (9)	0.0213 (9)	0.0194 (9)	0.0002 (7)	0.0092 (7)	−0.0020 (7)
C13	0.0227 (9)	0.0230 (9)	0.0224 (10)	−0.0020 (7)	0.0105 (8)	0.0014 (7)
C12	0.0255 (10)	0.0235 (9)	0.0198 (9)	0.0026 (8)	0.0130 (8)	0.0048 (7)
C10	0.0210 (9)	0.0200 (9)	0.0148 (9)	0.0019 (7)	0.0081 (7)	−0.0008 (7)

S1—C4	1.701 (2)	C11—C7	1.476 (3)
S1—C1	1.723 (2)	C7—C8	1.360 (3)
O1—C11	1.369 (2)	C8—C9	1.432 (3)
O1—C10	1.377 (2)	C8—H8	0.9500
O2—C11	1.206 (2)	C9—C10	1.400 (3)
C1—C2	1.387 (3)	C9—C15	1.408 (3)
C1—H1	0.9500	C15—C14	1.378 (3)
C2—C3	1.432 (3)	C15—H15	0.9500
C2—H2	0.9500	C14—C13	1.406 (3)
C3—C4	1.381 (3)	C14—H14	0.9500
C3—C5	1.426 (3)	C13—C12	1.384 (3)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.189 (3)	C12—C10	1.384 (3)
C6—C7	1.433 (3)	C12—H12	0.9500
C4—S1—C1	93.39 (10)	C7—C8—C9	120.69 (18)
C11—O1—C10	122.76 (15)	C7—C8—H8	119.7
C2—C1—S1	109.76 (15)	C9—C8—H8	119.7
C2—C1—H1	125.1	C10—C9—C15	118.13 (18)
S1—C1—H1	125.1	C10—C9—C8	118.32 (18)
C1—C2—C3	113.49 (19)	C15—C9—C8	123.50 (18)
C1—C2—H2	123.3	C14—C15—C9	120.50 (17)
C3—C2—H2	123.3	C14—C15—H15	119.8
C4—C3—C5	125.39 (18)	C9—C15—H15	119.8
C4—C3—C2	111.53 (18)	C15—C14—C13	119.78 (18)
C5—C3—C2	123.08 (18)	C15—C14—H14	120.1
C3—C4—S1	111.83 (16)	C13—C14—H14	120.1
C3—C4—H4	124.1	C12—C13—C14	120.90 (18)
S1—C4—H4	124.1	C12—C13—H13	119.6
C6—C5—C3	176.60 (19)	C14—C13—H13	119.6
C5—C6—C7	176.52 (19)	C13—C12—C10	118.53 (17)
O2—C11—O1	117.48 (17)	C13—C12—H12	120.7
O2—C11—C7	125.43 (18)	C10—C12—H12	120.7
O1—C11—C7	117.09 (16)	O1—C10—C12	117.02 (16)
C8—C7—C6	123.92 (17)	O1—C10—C9	120.80 (17)
C8—C7—C11	120.25 (17)	C12—C10—C9	122.17 (18)
C6—C7—C11	115.83 (16)
C4—S1—C1—C2	0.47 (17)	C7—C8—C9—C10	0.1 (3)
S1—C1—C2—C3	−0.5 (2)	C7—C8—C9—C15	−177.24 (18)
C1—C2—C3—C4	0.3 (3)	C10—C9—C15—C14	−0.5 (3)
C1—C2—C3—C5	179.59 (18)	C8—C9—C15—C14	176.84 (18)
C5—C3—C4—S1	−179.21 (16)	C9—C15—C14—C13	0.6 (3)
C2—C3—C4—S1	0.1 (2)	C15—C14—C13—C12	−0.6 (3)
C1—S1—C4—C3	−0.30 (18)	C14—C13—C12—C10	0.5 (3)
C10—O1—C11—O2	179.74 (16)	C11—O1—C10—C12	177.52 (16)
C10—O1—C11—C7	−0.9 (3)	C11—O1—C10—C9	−1.6 (3)
O2—C11—C7—C8	−177.71 (19)	C13—C12—C10—O1	−179.57 (16)
O1—C11—C7—C8	3.0 (3)	C13—C12—C10—C9	−0.5 (3)
O2—C11—C7—C6	2.3 (3)	C15—C9—C10—O1	179.50 (16)
O1—C11—C7—C6	−177.02 (15)	C8—C9—C10—O1	2.0 (3)
C6—C7—C8—C9	177.45 (17)	C15—C9—C10—C12	0.5 (3)
C11—C7—C8—C9	−2.6 (3)	C8—C9—C10—C12	−177.01 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg1i	0.95	2.89	3.701 (2)	144

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of ring S1,C1C4.

DHA	DH	HA	D A	DHA
C14H14Cg1i	0.95	2.89	3.701(2)	144

Symmetry code: (i) .