(2E)-2-(Thio-phen-2-yl-methyl-idene)-1,2,3,4-tetra-hydro-naphthalen-1-one.

In the title compound, C(15)H(12)OS, the cyclo-hexene ring has a twisted boat conformation with the C atom between the ketone and methyl-ene atom and this methyl-ene C atom lying 0.280 (3) and 0.760 (3) Å, respectively, from the plane through the remaining four atoms (r.m.s. deviation = 0.004 Å). The dihedral angle between the benzene and thio-phene rings [21.64 (9)°] indicates an overall twist in the mol-ecule. The thio-phene S and ketone O atoms are anti, an orientation that allows the close approach of these atoms [3.3116 (17) Å] in the crystal structure and which leads to the formation of helical supra-molecular chains along the c axis.

Related literature

For the activity of related species developed for the treatment of Chagas disease, see: Vera-DiVaio et al. (2009 ▶). For a related structure, see: Asiri et al. (2012 ▶).

Experimental

Crystal data

C15H12OS

M = 240.31

Orthorhombic,

a = 24.7989 (10) Å

b = 3.9976 (2) Å

c = 11.3163 (5) Å

V = 1121.85 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.812, T max = 1.000

7054 measured reflections

2528 independent reflections

2383 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.03

2528 reflections

154 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1171 Friedel pairs

Flack parameter: 0.07 (10)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029169/gg2087sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029169/gg2087Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029169/gg2087Isup3.cml

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

C15H12OS	Dx = 1.423 Mg m−3
Mr = 240.31	Melting point: 351 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3882 reflections
a = 24.7989 (10) Å	θ = 2.4–27.5°
b = 3.9976 (2) Å	µ = 0.27 mm−1
c = 11.3163 (5) Å	T = 100 K
V = 1121.85 (9) Å3	Prism, light-brown
Z = 4	0.35 × 0.30 × 0.25 mm
F(000) = 504

Agilent SuperNova Dual diffractometer with an Atlas detector	2528 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2383 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −32→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −5→4
Tmin = 0.812, Tmax = 1.000	l = −14→14
7054 measured 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.206P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2528 reflections	Δρmax = 0.32 e Å−3
154 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1171 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (10)

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	0.538955 (17)	0.26862 (11)	0.50161 (7)	0.01740 (13)
O1	0.36843 (6)	0.5071 (4)	0.19698 (15)	0.0251 (4)
C1	0.59800 (8)	0.0731 (5)	0.4638 (2)	0.0201 (4)
H1	0.6276	0.0445	0.5161	0.024*
C2	0.59738 (8)	−0.0357 (5)	0.3506 (2)	0.0201 (4)
H2	0.6268	−0.1480	0.3143	0.024*
C3	0.54817 (8)	0.0355 (5)	0.2914 (2)	0.0173 (4)
H3	0.5412	−0.0249	0.2117	0.021*
C4	0.51135 (8)	0.2025 (5)	0.36246 (19)	0.0153 (4)
C5	0.45890 (8)	0.3086 (5)	0.32082 (19)	0.0152 (4)
H5	0.4519	0.2571	0.2403	0.018*
C6	0.41829 (8)	0.4681 (4)	0.37662 (18)	0.0149 (4)
C7	0.36964 (8)	0.5503 (5)	0.30417 (19)	0.0157 (4)
C8	0.32189 (8)	0.6897 (4)	0.36676 (19)	0.0149 (4)
C9	0.27955 (8)	0.8271 (5)	0.3005 (2)	0.0170 (4)
H9	0.2824	0.8382	0.2168	0.020*
C10	0.23379 (8)	0.9464 (5)	0.35577 (19)	0.0177 (4)
H10	0.2053	1.0389	0.3103	0.021*
C11	0.22952 (8)	0.9309 (5)	0.47876 (19)	0.0179 (4)
H11	0.1979	1.0100	0.5171	0.022*
C12	0.27162 (9)	0.7996 (5)	0.5445 (2)	0.0176 (4)
H12	0.2688	0.7920	0.6282	0.021*
C13	0.31817 (7)	0.6783 (4)	0.4900 (2)	0.0140 (4)
C14	0.36339 (8)	0.5298 (5)	0.56230 (18)	0.0149 (4)
H14A	0.3570	0.2872	0.5728	0.018*
H14B	0.3637	0.6348	0.6415	0.018*
C15	0.41813 (7)	0.5824 (4)	0.5033 (2)	0.0150 (4)
H15A	0.4276	0.8228	0.5064	0.018*
H15B	0.4460	0.4573	0.5477	0.018*

	U11	U22	U33	U12	U13	U23
S1	0.0148 (2)	0.0213 (2)	0.0160 (2)	0.00044 (16)	−0.0005 (2)	−0.0013 (2)
O1	0.0217 (9)	0.0398 (9)	0.0137 (8)	0.0081 (6)	−0.0021 (6)	−0.0022 (7)
C1	0.0132 (9)	0.0204 (9)	0.0267 (12)	−0.0002 (7)	−0.0007 (8)	0.0033 (8)
C2	0.0145 (10)	0.0212 (10)	0.0247 (12)	0.0020 (7)	0.0048 (9)	0.0030 (9)
C3	0.0195 (10)	0.0168 (9)	0.0156 (10)	−0.0027 (7)	−0.0009 (8)	0.0041 (8)
C4	0.0174 (10)	0.0145 (8)	0.0139 (10)	−0.0021 (7)	−0.0012 (8)	0.0017 (8)
C5	0.0164 (10)	0.0178 (9)	0.0113 (10)	−0.0016 (7)	−0.0012 (7)	0.0011 (8)
C6	0.0162 (9)	0.0147 (9)	0.0137 (10)	−0.0011 (7)	−0.0007 (8)	0.0028 (8)
C7	0.0156 (10)	0.0168 (9)	0.0147 (10)	0.0009 (7)	−0.0004 (8)	0.0008 (8)
C8	0.0143 (9)	0.0138 (8)	0.0167 (10)	−0.0021 (7)	−0.0014 (8)	0.0012 (8)
C9	0.0182 (10)	0.0175 (9)	0.0153 (10)	−0.0021 (8)	−0.0019 (8)	0.0016 (8)
C10	0.0130 (9)	0.0177 (9)	0.0226 (12)	−0.0019 (7)	−0.0046 (8)	0.0028 (8)
C11	0.0150 (9)	0.0172 (9)	0.0216 (12)	−0.0008 (7)	0.0035 (8)	0.0002 (7)
C12	0.0173 (10)	0.0186 (10)	0.0169 (10)	−0.0033 (7)	0.0032 (8)	0.0012 (8)
C13	0.0155 (9)	0.0119 (8)	0.0147 (10)	−0.0029 (6)	−0.0001 (8)	0.0007 (8)
C14	0.0166 (9)	0.0152 (9)	0.0129 (10)	−0.0012 (7)	0.0010 (8)	0.0001 (8)
C15	0.0138 (8)	0.0187 (8)	0.0125 (9)	0.0005 (7)	−0.0006 (9)	−0.0001 (9)

S1—C1	1.714 (2)	C8—C9	1.403 (3)
S1—C4	1.737 (2)	C9—C10	1.381 (3)
O1—C7	1.226 (3)	C9—H9	0.9500
C1—C2	1.353 (3)	C10—C11	1.397 (3)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.421 (3)	C11—C12	1.385 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.388 (3)	C12—C13	1.396 (3)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.447 (3)	C13—C14	1.510 (3)
C5—C6	1.349 (3)	C14—C15	1.527 (3)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.495 (3)	C14—H14B	0.9900
C6—C15	1.504 (3)	C15—H15A	0.9900
C7—C8	1.488 (3)	C15—H15B	0.9900
C8—C13	1.399 (3)
C1—S1—C4	92.35 (10)	C10—C9—H9	119.7
C2—C1—S1	111.91 (16)	C8—C9—H9	119.7
C2—C1—H1	124.0	C9—C10—C11	119.89 (19)
S1—C1—H1	124.0	C9—C10—H10	120.1
C1—C2—C3	113.1 (2)	C11—C10—H10	120.1
C1—C2—H2	123.5	C12—C11—C10	119.65 (19)
C3—C2—H2	123.5	C12—C11—H11	120.2
C4—C3—C2	112.9 (2)	C10—C11—H11	120.2
C4—C3—H3	123.6	C11—C12—C13	121.2 (2)
C2—C3—H3	123.6	C11—C12—H12	119.4
C3—C4—C5	122.9 (2)	C13—C12—H12	119.4
C3—C4—S1	109.82 (15)	C12—C13—C8	118.9 (2)
C5—C4—S1	127.21 (16)	C12—C13—C14	120.8 (2)
C6—C5—C4	131.1 (2)	C8—C13—C14	120.26 (17)
C6—C5—H5	114.5	C13—C14—C15	111.67 (17)
C4—C5—H5	114.5	C13—C14—H14A	109.3
C5—C6—C7	116.72 (18)	C15—C14—H14A	109.3
C5—C6—C15	126.27 (18)	C13—C14—H14B	109.3
C7—C6—C15	116.97 (16)	C15—C14—H14B	109.3
O1—C7—C8	120.28 (18)	H14A—C14—H14B	107.9
O1—C7—C6	122.11 (18)	C6—C15—C14	112.16 (16)
C8—C7—C6	117.60 (18)	C6—C15—H15A	109.2
C13—C8—C9	119.78 (19)	C14—C15—H15A	109.2
C13—C8—C7	121.00 (18)	C6—C15—H15B	109.2
C9—C8—C7	119.20 (19)	C14—C15—H15B	109.2
C10—C9—C8	120.5 (2)	H15A—C15—H15B	107.9
C4—S1—C1—C2	0.54 (16)	C6—C7—C8—C9	168.28 (17)
S1—C1—C2—C3	−0.5 (2)	C13—C8—C9—C10	−1.1 (3)
C1—C2—C3—C4	0.2 (3)	C7—C8—C9—C10	177.44 (17)
C2—C3—C4—C5	178.49 (17)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—S1	0.2 (2)	C9—C10—C11—C12	0.8 (3)
C1—S1—C4—C3	−0.40 (15)	C10—C11—C12—C13	−0.8 (3)
C1—S1—C4—C5	−178.62 (18)	C11—C12—C13—C8	−0.2 (3)
C3—C4—C5—C6	179.2 (2)	C11—C12—C13—C14	−178.85 (17)
S1—C4—C5—C6	−2.8 (3)	C9—C8—C13—C12	1.1 (3)
C4—C5—C6—C7	177.95 (19)	C7—C8—C13—C12	−177.36 (16)
C4—C5—C6—C15	0.4 (3)	C9—C8—C13—C14	179.76 (16)
C5—C6—C7—O1	−7.2 (3)	C7—C8—C13—C14	1.3 (3)
C15—C6—C7—O1	170.53 (18)	C12—C13—C14—C15	−150.02 (17)
C5—C6—C7—C8	172.98 (17)	C8—C13—C14—C15	31.4 (2)
C15—C6—C7—C8	−9.3 (2)	C5—C6—C15—C14	−140.98 (19)
O1—C7—C8—C13	166.95 (18)	C7—C6—C15—C14	41.5 (2)
C6—C7—C8—C13	−13.2 (3)	C13—C14—C15—C6	−51.7 (2)
O1—C7—C8—C9	−11.5 (3)