(E)-1-(1,3-Benzodioxol-5-yl)-4,4-di-methyl-pent-1-en-3-one.

In the mol-ecule of the title compound, C(14)H(16)O(3), all non-H atoms except for one methyl C atom lie on a crystallographic mirror plane. The conformation with respect to the C=C bond [1.3465 (12) Å] is trans. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into C(5) chains propagating along [100].

Related literature

For general background to and the pharmacological activities of the title compound, see: Pessah et al. (2009 ▶); Jain (2005 ▶); Medina et al. (2005 ▶). For the preparation of the title compound, see: Aboul-Enein et al. (2012 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H16O3

M = 232.27

Monoclinic,

a = 6.5305 (1) Å

b = 6.6798 (1) Å

c = 13.7264 (2) Å

β = 96.676 (1)°

V = 594.72 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.42 × 0.32 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.978

8645 measured reflections

2336 independent reflections

2117 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.05

2336 reflections

138 parameters

All H-atom parameters refined

Δρmax = 0.48 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004242/hb6621sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004242/hb6621Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004242/hb6621Isup3.cml

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

C14H16O3	F(000) = 248
Mr = 232.27	Dx = 1.297 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 4988 reflections
a = 6.5305 (1) Å	θ = 3.0–32.7°
b = 6.6798 (1) Å	µ = 0.09 mm−1
c = 13.7264 (2) Å	T = 100 K
β = 96.676 (1)°	Block, colourless
V = 594.72 (2) Å3	0.42 × 0.32 × 0.25 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	2336 independent reflections
Radiation source: fine-focus sealed tube	2117 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 32.7°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.963, Tmax = 0.978	k = −9→10
8645 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.0862P] where P = (Fo2 + 2Fc2)/3
2336 reflections	(Δ/σ)max = 0.001
138 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.08309 (10)	0.7500	0.73220 (5)	0.01756 (15)
O2	0.23387 (11)	0.7500	0.67099 (5)	0.02109 (16)
O3	−0.10343 (12)	0.7500	0.11962 (5)	0.0284 (2)
C1	−0.27995 (14)	0.7500	0.46990 (7)	0.01734 (18)
C2	−0.29527 (14)	0.7500	0.57113 (7)	0.01815 (18)
C3	−0.11215 (14)	0.7500	0.63184 (6)	0.01431 (16)
C4	0.13580 (14)	0.7500	0.75950 (6)	0.01731 (17)
C5	0.07776 (13)	0.7500	0.59505 (6)	0.01401 (16)
C6	0.09473 (13)	0.7500	0.49674 (6)	0.01446 (16)
C7	−0.08980 (13)	0.7500	0.43188 (6)	0.01338 (16)
C8	−0.08717 (14)	0.7500	0.32577 (6)	0.01474 (16)
C9	0.08137 (14)	0.7500	0.27781 (6)	0.01558 (17)
C10	0.06467 (14)	0.7500	0.16901 (6)	0.01549 (17)
C11	0.26558 (13)	0.7500	0.12174 (6)	0.01458 (16)
C12	0.21897 (17)	0.7500	0.01018 (7)	0.0271 (2)
C13	0.39093 (12)	0.56198 (11)	0.15410 (6)	0.02431 (16)
H1A	−0.406 (3)	0.7500	0.4256 (12)	0.032 (4)*
H2A	−0.424 (3)	0.7500	0.5974 (12)	0.031 (4)*
H4A	0.1728 (15)	0.6272 (15)	0.7976 (7)	0.018 (2)*
H6A	0.239 (2)	0.7500	0.4738 (11)	0.025 (4)*
H8A	−0.220 (3)	0.7500	0.2883 (12)	0.034 (4)*
H9A	0.218 (3)	0.7500	0.3117 (12)	0.032 (4)*
H12A	0.138 (2)	0.631 (2)	−0.0117 (9)	0.041 (3)*
H12B	0.350 (3)	0.7500	−0.0180 (12)	0.030 (4)*
H13A	0.4241 (18)	0.5522 (18)	0.2246 (9)	0.034 (3)*
H13B	0.3154 (19)	0.4437 (18)	0.1331 (8)	0.033 (3)*
H13C	0.5215 (17)	0.5639 (16)	0.1247 (8)	0.026 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0164 (3)	0.0258 (3)	0.0112 (3)	0.000	0.0045 (2)	0.000
O2	0.0137 (3)	0.0385 (4)	0.0113 (3)	0.000	0.0022 (2)	0.000
O3	0.0141 (3)	0.0557 (6)	0.0153 (3)	0.000	0.0012 (2)	0.000
C1	0.0124 (4)	0.0258 (4)	0.0141 (4)	0.000	0.0029 (3)	0.000
C2	0.0133 (4)	0.0272 (4)	0.0149 (4)	0.000	0.0054 (3)	0.000
C3	0.0147 (4)	0.0167 (4)	0.0122 (3)	0.000	0.0046 (3)	0.000
C4	0.0173 (4)	0.0231 (4)	0.0119 (3)	0.000	0.0032 (3)	0.000
C5	0.0123 (3)	0.0173 (4)	0.0127 (3)	0.000	0.0027 (3)	0.000
C6	0.0127 (3)	0.0187 (4)	0.0126 (3)	0.000	0.0040 (3)	0.000
C7	0.0127 (3)	0.0157 (4)	0.0123 (3)	0.000	0.0034 (3)	0.000
C8	0.0142 (3)	0.0180 (4)	0.0123 (3)	0.000	0.0030 (3)	0.000
C9	0.0142 (4)	0.0210 (4)	0.0119 (3)	0.000	0.0029 (3)	0.000
C10	0.0136 (4)	0.0206 (4)	0.0127 (3)	0.000	0.0036 (3)	0.000
C11	0.0137 (3)	0.0178 (4)	0.0130 (3)	0.000	0.0045 (3)	0.000
C12	0.0222 (5)	0.0465 (7)	0.0136 (4)	0.000	0.0065 (3)	0.000
C13	0.0235 (3)	0.0215 (3)	0.0302 (3)	0.0061 (3)	0.0129 (3)	0.0056 (3)

O1—C3	1.3685 (10)	C7—C8	1.4587 (12)
O1—C4	1.4350 (11)	C8—C9	1.3465 (12)
O2—C5	1.3706 (11)	C8—H8A	0.956 (18)
O2—C4	1.4378 (11)	C9—C10	1.4848 (12)
O3—C10	1.2214 (11)	C9—H9A	0.960 (17)
C1—C7	1.4018 (12)	C10—C11	1.5298 (12)
C1—C2	1.4046 (12)	C11—C12	1.5262 (13)
C1—H1A	0.967 (17)	C11—C13i	1.5363 (9)
C2—C3	1.3758 (13)	C11—C13	1.5363 (9)
C2—H2A	0.952 (17)	C12—H12A	0.985 (13)
C3—C5	1.3924 (11)	C12—H12B	0.980 (17)
C4—H4A	0.988 (10)	C13—H13A	0.969 (12)
C5—C6	1.3668 (11)	C13—H13B	0.958 (12)
C6—C7	1.4125 (12)	C13—H13C	0.985 (11)
C6—H6A	1.026 (16)
C3—O1—C4	106.27 (6)	C9—C8—H8A	118.6 (10)
C5—O2—C4	106.12 (7)	C7—C8—H8A	115.0 (10)
C7—C1—C2	122.43 (8)	C8—C9—C10	121.54 (8)
C7—C1—H1A	119.6 (10)	C8—C9—H9A	122.2 (10)
C2—C1—H1A	117.9 (10)	C10—C9—H9A	116.3 (10)
C3—C2—C1	116.25 (8)	O3—C10—C9	120.97 (8)
C3—C2—H2A	120.9 (10)	O3—C10—C11	121.63 (8)
C1—C2—H2A	122.9 (10)	C9—C10—C11	117.40 (7)
O1—C3—C2	128.23 (8)	C12—C11—C10	110.16 (8)
O1—C3—C5	109.87 (8)	C12—C11—C13i	109.12 (5)
C2—C3—C5	121.90 (8)	C10—C11—C13i	109.38 (5)
O1—C4—O2	107.90 (7)	C12—C11—C13	109.12 (5)
O1—C4—H4A	108.2 (6)	C10—C11—C13	109.38 (5)
O2—C4—H4A	110.0 (6)	C13i—C11—C13	109.67 (8)
C6—C5—O2	127.76 (8)	C11—C12—H12A	110.1 (7)
C6—C5—C3	122.41 (8)	C11—C12—H12B	108.4 (10)
O2—C5—C3	109.83 (7)	H12A—C12—H12B	110.1 (9)
C5—C6—C7	117.46 (8)	C11—C13—H13A	113.2 (7)
C5—C6—H6A	119.0 (9)	C11—C13—H13B	110.4 (7)
C7—C6—H6A	123.5 (9)	H13A—C13—H13B	107.0 (10)
C1—C7—C6	119.55 (8)	C11—C13—H13C	109.2 (6)
C1—C7—C8	119.05 (8)	H13A—C13—H13C	107.8 (9)
C6—C7—C8	121.41 (7)	H13B—C13—H13C	109.1 (9)
C9—C8—C7	126.39 (8)
C7—C1—C2—C3	0.0	C2—C1—C7—C6	0.0
C4—O1—C3—C2	180.0	C2—C1—C7—C8	180.0
C4—O1—C3—C5	0.0	C5—C6—C7—C1	0.0
C1—C2—C3—O1	180.0	C5—C6—C7—C8	180.0
C1—C2—C3—C5	0.0	C1—C7—C8—C9	180.0
C3—O1—C4—O2	0.0	C6—C7—C8—C9	0.0
C5—O2—C4—O1	0.0	C7—C8—C9—C10	180.0
C4—O2—C5—C6	180.0	C8—C9—C10—O3	0.0
C4—O2—C5—C3	0.0	C8—C9—C10—C11	180.0
O1—C3—C5—C6	180.0	O3—C10—C11—C12	0.0
C2—C3—C5—C6	0.0	C9—C10—C11—C12	180.0
O1—C3—C5—O2	0.0	O3—C10—C11—C13i	119.93 (5)
C2—C3—C5—O2	180.0	C9—C10—C11—C13i	−60.07 (5)
O2—C5—C6—C7	180.0	O3—C10—C11—C13	−119.93 (5)
C3—C5—C6—C7	0.0	C9—C10—C11—C13	60.07 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ii	0.95 (2)	2.56 (2)	3.5092 (12)	179 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.95 (2)	2.56 (2)	3.5092 (12)	179 (1)

Symmetry code: (i) .