(1E,4E)-1-(Thio-phen-2-yl)-5-(2,6,6-trimethyl-cyclo-hex-1-en-1-yl)penta-1,4-dien-3-one.

In the title curcumin-ionone derivative, C(18)H(22)OS, the dihedral angle between the thia-zole ring and the mean plane through the cyclo-hexene ring is 5.16 (10)°. The mol-ecule has an E conformation for each of the olefinic bonds.

Related literature

For related structures, see: Liang et al. (2007 ▶); Zou et al. (2012 ▶). For background to the biological properties of curcumin–ionone derivatives, see: Anand et al. (2008 ▶); Zhao et al. (2010a ▶,b ▶); Zhou et al. (2009a ▶,b ▶).

Experimental

Crystal data

C18H22OS

M = 286.42

Monoclinic,

a = 8.3401 (17) Å

b = 6.9084 (14) Å

c = 13.994 (3) Å

β = 96.082 (4)°

V = 801.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.36 × 0.30 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.674, T max = 1.000

4888 measured reflections

1711 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.05

1711 reflections

145 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022465/ng5270sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022465/ng5270Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022465/ng5270Isup3.cml

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

C18H22OS	F(000) = 308
Mr = 286.42	Dx = 1.186 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 8.3401 (17) Å	Cell parameters from 2746 reflections
b = 6.9084 (14) Å	θ = 4.9–56.5°
c = 13.994 (3) Å	µ = 0.20 mm−1
β = 96.082 (4)°	T = 293 K
V = 801.7 (3) Å3	Prismatic, colorless
Z = 2	0.36 × 0.30 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	1711 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→8
Tmin = 0.674, Tmax = 1.000	k = −8→8
4888 measured reflections	l = −17→16

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.091P)2 + 0.1463P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
1711 reflections	Δρmax = 0.32 e Å−3
145 parameters	Δρmin = −0.17 e Å−3
4 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: 0.013 (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	Occ. (<1)
S1	1.08493 (6)	0.2500	0.58526 (4)	0.0487 (3)
O1	0.4327 (2)	0.2500	0.53246 (12)	0.0817 (7)
C1	1.2154 (3)	0.2500	0.68697 (16)	0.0521 (6)
H1	1.3270	0.2500	0.6874	0.063*
C2	1.1384 (3)	0.2500	0.76737 (16)	0.0533 (6)
H2	1.1919	0.2500	0.8292	0.064*
C3	0.9688 (3)	0.2500	0.74818 (15)	0.0464 (5)
H3	0.8982	0.2500	0.7954	0.056*
C4	0.9204 (3)	0.2500	0.65023 (14)	0.0416 (5)
C5	0.7575 (3)	0.2500	0.60586 (16)	0.0463 (5)
H5	0.6772	0.2500	0.6472	0.056*
C6	0.7078 (3)	0.2500	0.51249 (15)	0.0504 (6)
H6	0.7839	0.2500	0.4685	0.060*
C7	0.5361 (3)	0.2500	0.47694 (16)	0.0525 (6)
C8	0.4939 (3)	0.2500	0.37222 (15)	0.0537 (6)
H8	0.5754	0.2500	0.3317	0.064*
C9	0.3412 (3)	0.2500	0.33499 (15)	0.0478 (5)
H9	0.2683	0.2500	0.3809	0.057*
C10	0.2646 (3)	0.2500	0.23645 (14)	0.0442 (5)
C11	0.1024 (3)	0.2500	0.22224 (15)	0.0439 (5)
C12	0.0090 (3)	0.2500	0.12463 (18)	0.0631 (7)
C13	0.1137 (5)	0.3120 (7)	0.0454 (2)	0.0749 (18)	0.50
C14	0.2610 (5)	0.1876 (8)	0.0579 (2)	0.0745 (19)	0.50
C15	0.3698 (3)	0.2500	0.15222 (17)	0.0624 (7)
C16	−0.0078 (3)	0.2500	0.30125 (17)	0.0516 (6)
H16A	−0.0320	0.3810	0.3175	0.077*	0.50
H16B	0.0445	0.1857	0.3569	0.077*	0.50
H16C	−0.1060	0.1833	0.2796	0.077*	0.50
C17	0.4761 (3)	0.0695 (4)	0.15515 (17)	0.0931 (8)
H17A	0.5515	0.0723	0.2119	0.140*
H17B	0.5338	0.0669	0.0993	0.140*
H17C	0.4099	−0.0440	0.1560	0.140*
H14A	0.317 (4)	0.2500	0.005 (2)	0.091 (11)*
H12A	−0.061 (3)	0.137 (3)	0.1184 (16)	0.077 (6)*
H14B	0.253 (8)	0.046 (3)	0.061 (5)	0.13 (3)*	0.50
H13A	0.060 (4)	0.2500	−0.0122 (18)	0.096 (11)*
H13B	0.159 (5)	0.445 (3)	0.048 (3)	0.052 (11)*	0.50

	U11	U22	U33	U12	U13	U23
S1	0.0413 (4)	0.0712 (4)	0.0340 (3)	0.000	0.0062 (2)	0.000
O1	0.0398 (9)	0.168 (2)	0.0387 (9)	0.000	0.0092 (7)	0.000
C1	0.0394 (11)	0.0740 (16)	0.0423 (11)	0.000	0.0013 (9)	0.000
C2	0.0513 (13)	0.0721 (15)	0.0351 (11)	0.000	−0.0017 (9)	0.000
C3	0.0454 (12)	0.0565 (13)	0.0375 (10)	0.000	0.0053 (9)	0.000
C4	0.0409 (11)	0.0488 (11)	0.0356 (10)	0.000	0.0065 (8)	0.000
C5	0.0399 (11)	0.0601 (13)	0.0398 (11)	0.000	0.0088 (8)	0.000
C6	0.0403 (12)	0.0745 (16)	0.0372 (11)	0.000	0.0085 (9)	0.000
C7	0.0407 (12)	0.0787 (16)	0.0388 (11)	0.000	0.0069 (9)	0.000
C8	0.0451 (12)	0.0802 (17)	0.0364 (11)	0.000	0.0075 (9)	0.000
C9	0.0437 (11)	0.0646 (14)	0.0357 (10)	0.000	0.0066 (8)	0.000
C10	0.0453 (11)	0.0540 (12)	0.0333 (10)	0.000	0.0043 (8)	0.000
C11	0.0469 (11)	0.0470 (11)	0.0374 (10)	0.000	0.0026 (9)	0.000
C12	0.0506 (14)	0.093 (2)	0.0437 (13)	0.000	−0.0045 (11)	0.000
C13	0.071 (2)	0.115 (6)	0.0359 (15)	0.016 (2)	−0.0032 (14)	0.0065 (18)
C14	0.069 (2)	0.121 (6)	0.0340 (15)	0.018 (2)	0.0062 (14)	−0.0074 (17)
C15	0.0488 (13)	0.103 (2)	0.0362 (11)	0.000	0.0087 (10)	0.000
C16	0.0444 (12)	0.0626 (14)	0.0486 (12)	0.000	0.0089 (9)	0.000
C17	0.0879 (16)	0.113 (2)	0.0838 (15)	0.0131 (14)	0.0331 (12)	−0.0305 (14)

S1—C1	1.698 (2)	C12—C13	1.543 (5)
S1—C4	1.724 (2)	C12—C13i	1.543 (5)
O1—C7	1.220 (3)	C12—H12A	0.97 (2)
C1—C2	1.353 (3)	C13—C13i	0.856 (10)
C1—H1	0.9300	C13—C14i	1.222 (6)
C2—C3	1.411 (3)	C13—C14	1.494 (6)
C2—H2	0.9300	C13—H13A	0.979 (18)
C3—C4	1.387 (3)	C13—H13B	0.994 (19)
C3—H3	0.9300	C14—C14i	0.862 (11)
C4—C5	1.433 (3)	C14—C13i	1.222 (6)
C5—C6	1.328 (3)	C14—C15	1.580 (4)
C5—H5	0.9300	C14—H14A	1.015 (18)
C6—C7	1.465 (3)	C14—H14B	0.99 (2)
C6—H6	0.9300	C15—C17	1.528 (3)
C7—C8	1.470 (3)	C15—C17i	1.528 (3)
C8—C9	1.324 (3)	C15—C14i	1.580 (4)
C8—H8	0.9300	C16—H16A	0.9600
C9—C10	1.457 (3)	C16—H16B	0.9600
C9—H9	0.9300	C16—H16C	0.9600
C10—C11	1.346 (3)	C17—H17A	0.9600
C10—C15	1.542 (3)	C17—H17B	0.9600
C11—C12	1.499 (3)	C17—H17C	0.9600
C11—C16	1.511 (3)
C1—S1—C4	91.89 (10)	C13i—C13—H13A	64.1 (7)
C2—C1—S1	112.24 (18)	C14i—C13—H13A	119 (2)
C2—C1—H1	123.9	C14—C13—H13A	98.3 (16)
S1—C1—H1	123.9	C12—C13—H13A	103 (2)
C1—C2—C3	113.3 (2)	C13i—C13—H13B	158 (3)
C1—C2—H2	123.3	C14i—C13—H13B	68 (3)
C3—C2—H2	123.3	C14—C13—H13B	103 (3)
C4—C3—C2	111.63 (19)	C12—C13—H13B	118 (2)
C4—C3—H3	124.2	H13A—C13—H13B	125 (3)
C2—C3—H3	124.2	C14i—C14—C13i	89.9 (3)
C3—C4—C5	126.24 (19)	C14i—C14—C13	54.9 (3)
C3—C4—S1	110.90 (16)	C13i—C14—C13	35.0 (4)
C5—C4—S1	122.86 (16)	C14i—C14—C15	74.18 (19)
C6—C5—C4	127.5 (2)	C13i—C14—C15	126.7 (3)
C6—C5—H5	116.2	C13—C14—C15	109.5 (3)
C4—C5—H5	116.2	C14i—C14—H14A	64.9 (6)
C5—C6—C7	121.74 (19)	C13i—C14—H14A	115 (2)
C5—C6—H6	119.1	C13—C14—H14A	96.0 (16)
C7—C6—H6	119.1	C15—C14—H14A	103 (2)
O1—C7—C6	121.0 (2)	C14i—C14—H14B	175 (4)
O1—C7—C8	121.6 (2)	C13i—C14—H14B	86 (4)
C6—C7—C8	117.42 (19)	C13—C14—H14B	121 (4)
C9—C8—C7	120.7 (2)	C15—C14—H14B	106 (4)
C9—C8—H8	119.6	H14A—C14—H14B	119 (4)
C7—C8—H8	119.6	C17—C15—C17i	109.3 (3)
C8—C9—C10	132.8 (2)	C17—C15—C10	110.80 (14)
C8—C9—H9	113.6	C17i—C15—C10	110.80 (14)
C10—C9—H9	113.6	C17—C15—C14i	121.7 (2)
C11—C10—C9	118.22 (19)	C17i—C15—C14i	94.6 (2)
C11—C10—C15	122.08 (19)	C10—C15—C14i	108.4 (2)
C9—C10—C15	119.7 (2)	C17—C15—C14	94.6 (2)
C10—C11—C12	123.5 (2)	C17i—C15—C14	121.7 (2)
C10—C11—C16	124.87 (19)	C10—C15—C14	108.4 (2)
C12—C11—C16	111.65 (19)	C14i—C15—C14	31.6 (4)
C11—C12—C13	112.1 (2)	C11—C16—H16A	109.5
C11—C12—C13i	112.1 (2)	C11—C16—H16B	109.5
C13—C12—C13i	32.2 (4)	H16A—C16—H16B	109.5
C11—C12—H12A	109.2 (14)	C11—C16—H16C	109.5
C13—C12—H12A	122.5 (13)	H16A—C16—H16C	109.5
C13i—C12—H12A	95.3 (13)	H16B—C16—H16C	109.5
C13i—C13—C14i	90.1 (3)	C15—C17—H17A	109.5
C13i—C13—C14	54.9 (3)	C15—C17—H17B	109.5
C14i—C13—C14	35.2 (5)	H17A—C17—H17B	109.5
C13i—C13—C12	73.90 (18)	C15—C17—H17C	109.5
C14i—C13—C12	122.3 (3)	H17A—C17—H17C	109.5
C14—C13—C12	106.1 (3)	H17B—C17—H17C	109.5
C4—S1—C1—C2	0.0	C11—C12—C13—C14	51.6 (4)
S1—C1—C2—C3	0.0	C13i—C12—C13—C14	−45.1 (3)
C1—C2—C3—C4	0.0	C13i—C13—C14—C14i	180.0
C2—C3—C4—C5	180.0	C12—C13—C14—C14i	−123.8 (3)
C2—C3—C4—S1	0.0	C14i—C13—C14—C13i	180.0
C1—S1—C4—C3	0.0	C12—C13—C14—C13i	56.2 (3)
C1—S1—C4—C5	180.0	C13i—C13—C14—C15	−127.0 (4)
C3—C4—C5—C6	180.0	C14i—C13—C14—C15	53.0 (4)
S1—C4—C5—C6	0.0	C12—C13—C14—C15	−70.7 (4)
C4—C5—C6—C7	180.0	C11—C10—C15—C17	−119.22 (17)
C5—C6—C7—O1	0.0	C9—C10—C15—C17	60.78 (17)
C5—C6—C7—C8	180.0	C11—C10—C15—C17i	119.22 (17)
O1—C7—C8—C9	0.0	C9—C10—C15—C17i	−60.78 (17)
C6—C7—C8—C9	180.0	C11—C10—C15—C14i	16.7 (2)
C7—C8—C9—C10	180.0	C9—C10—C15—C14i	−163.3 (2)
C8—C9—C10—C11	180.0	C11—C10—C15—C14	−16.7 (2)
C8—C9—C10—C15	0.0	C9—C10—C15—C14	163.3 (2)
C9—C10—C11—C12	180.0	C14i—C14—C15—C17	−150.87 (16)
C15—C10—C11—C12	0.0	C13i—C14—C15—C17	131.5 (6)
C9—C10—C11—C16	0.0	C13—C14—C15—C17	166.3 (3)
C15—C10—C11—C16	180.0	C14i—C14—C15—C17i	−34.77 (18)
C10—C11—C12—C13	−17.4 (2)	C13i—C14—C15—C17i	−112.4 (5)
C16—C11—C12—C13	162.6 (2)	C13—C14—C15—C17i	−77.6 (4)
C10—C11—C12—C13i	17.4 (2)	C14i—C14—C15—C10	95.42 (9)
C16—C11—C12—C13i	−162.6 (2)	C13i—C14—C15—C10	17.8 (6)
C11—C12—C13—C13i	96.72 (10)	C13—C14—C15—C10	52.6 (4)
C11—C12—C13—C14i	17.1 (6)	C13i—C14—C15—C14i	−77.6 (6)
C13i—C12—C13—C14i	−79.6 (5)	C13—C14—C15—C14i	−42.8 (4)