(E)-4-(1,3-Benzodioxol-5-yl)but-3-en-2-one.

In the title compound, C(11)H(10)O(3), the benzodioxole ring adopts a flattened [puckering parameters: q(2) = 0.107 (2) Å, ϕ(2) = 160 (1)°] envelope conformation with the methylene C atom as the flap. The crystal packing features chains, parallel to the c axis, composed of dimers connected by weak C-H-O hydrogen bonds and extending in layers in the bc plane.

Related literature

For the synthesis of chalcones, see: Loh et al. (2010 ▶). For a related structure, see: Gao & Ng (2006 ▶).

Experimental

Crystal data

C11H10O3

M = 190.19

Monoclinic,

a = 5.3469 (3) Å

b = 16.4849 (8) Å

c = 10.5475 (6) Å

β = 99.183 (5)°

V = 917.77 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.83 mm−1

T = 293 K

0.18 × 0.11 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.950, T max = 1.000

5375 measured reflections

1737 independent reflections

1121 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 0.92

1737 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.12 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004077/ng5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004077/ng5110Isup2.hkl

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

C11H10O3	F(000) = 400
Mr = 190.19	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Melting point: 413 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 5.3469 (3) Å	Cell parameters from 1941 reflections
b = 16.4849 (8) Å	θ = 4.2–70.6°
c = 10.5475 (6) Å	µ = 0.83 mm−1
β = 99.183 (5)°	T = 293 K
V = 917.77 (9) Å3	Prismatic, yellow
Z = 4	0.18 × 0.11 × 0.09 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1737 independent reflections
Radiation source: fine-focus sealed tube	1121 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.2673 pixels mm-1	θmax = 70.5°, θmin = 5.0°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→19
Tmin = 0.950, Tmax = 1.000	l = −12→11
5375 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	All H-atom parameters refined
S = 0.92	w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
1737 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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
O2	0.5552 (2)	0.23540 (7)	−0.17522 (12)	0.0686 (3)
O1	0.5790 (2)	0.09846 (7)	−0.13128 (11)	0.0669 (4)
C2	0.4130 (3)	0.13463 (9)	−0.06159 (15)	0.0528 (4)
C6	0.1246 (3)	0.14906 (9)	0.08521 (14)	0.0528 (4)
C5	0.1132 (3)	0.23186 (10)	0.05728 (16)	0.0597 (4)
C7	0.2809 (3)	0.09884 (10)	0.02303 (16)	0.0556 (4)
C3	0.3994 (3)	0.21645 (9)	−0.08768 (15)	0.0557 (4)
C8	−0.0220 (3)	0.11602 (10)	0.17895 (16)	0.0563 (4)
C4	0.2514 (3)	0.26731 (10)	−0.02911 (17)	0.0627 (4)
C9	−0.0146 (3)	0.04080 (10)	0.22361 (17)	0.0591 (4)
O3	−0.1186 (3)	−0.06111 (8)	0.35856 (14)	0.0857 (4)
C10	−0.1536 (3)	0.00895 (11)	0.32109 (16)	0.0632 (4)
C11	−0.3362 (5)	0.06204 (16)	0.3750 (3)	0.0802 (6)
C1	0.6491 (4)	0.16001 (11)	−0.2141 (2)	0.0683 (5)
H8	−0.129 (3)	0.1522 (10)	0.2107 (17)	0.065 (5)*
H7	0.295 (3)	0.0424 (10)	0.0405 (15)	0.058 (4)*
H4	0.242 (3)	0.3245 (11)	−0.0461 (17)	0.074 (5)*
H9	0.085 (3)	0.0018 (11)	0.1929 (15)	0.069 (5)*
H5	0.007 (3)	0.2651 (10)	0.0987 (15)	0.061 (4)*
H1A	0.567 (3)	0.1472 (11)	−0.304 (2)	0.079 (6)*
H1B	0.839 (4)	0.1638 (11)	−0.2067 (17)	0.078 (5)*
H11A	−0.415 (6)	0.0290 (19)	0.423 (3)	0.156 (12)*
H11C	−0.247 (5)	0.1005 (18)	0.433 (3)	0.148 (12)*
H11B	−0.442 (6)	0.0918 (19)	0.316 (3)	0.147 (12)*

	U11	U22	U33	U12	U13	U23
O2	0.0755 (7)	0.0532 (7)	0.0818 (8)	0.0007 (5)	0.0272 (6)	0.0100 (6)
O1	0.0752 (8)	0.0532 (7)	0.0789 (8)	0.0086 (5)	0.0323 (6)	0.0055 (6)
C2	0.0533 (8)	0.0466 (8)	0.0587 (9)	0.0033 (7)	0.0092 (7)	−0.0001 (7)
C6	0.0540 (8)	0.0482 (9)	0.0560 (9)	0.0025 (7)	0.0082 (7)	−0.0004 (7)
C5	0.0658 (10)	0.0485 (9)	0.0663 (10)	0.0081 (8)	0.0148 (8)	−0.0030 (8)
C7	0.0602 (9)	0.0430 (9)	0.0643 (10)	0.0042 (7)	0.0121 (7)	0.0024 (8)
C3	0.0569 (9)	0.0497 (9)	0.0605 (10)	−0.0023 (7)	0.0090 (7)	0.0046 (7)
C8	0.0565 (9)	0.0530 (10)	0.0594 (9)	0.0041 (7)	0.0094 (7)	−0.0033 (8)
C4	0.0719 (10)	0.0427 (9)	0.0745 (11)	0.0031 (8)	0.0144 (8)	0.0047 (8)
C9	0.0610 (9)	0.0497 (10)	0.0684 (10)	0.0019 (7)	0.0153 (8)	−0.0020 (8)
O3	0.1042 (10)	0.0586 (8)	0.0963 (10)	−0.0024 (7)	0.0216 (8)	0.0171 (7)
C10	0.0642 (10)	0.0564 (10)	0.0673 (10)	−0.0067 (8)	0.0048 (8)	0.0047 (8)
C11	0.0771 (13)	0.0829 (15)	0.0875 (16)	0.0063 (12)	0.0340 (12)	0.0146 (14)
C1	0.0753 (12)	0.0575 (10)	0.0766 (13)	0.0014 (9)	0.0260 (10)	0.0071 (9)

O2—C3	1.3746 (19)	C8—C9	1.325 (2)
O2—C1	1.425 (2)	C8—H8	0.926 (18)
O1—C2	1.3755 (18)	C4—H4	0.960 (18)
O1—C1	1.428 (2)	C9—C10	1.459 (2)
C2—C7	1.358 (2)	C9—H9	0.927 (18)
C2—C3	1.376 (2)	O3—C10	1.225 (2)
C6—C5	1.396 (2)	C10—C11	1.490 (3)
C6—C7	1.410 (2)	C11—H11A	0.90 (3)
C6—C8	1.462 (2)	C11—H11C	0.95 (3)
C5—C4	1.390 (2)	C11—H11B	0.92 (3)
C5—H5	0.944 (17)	C1—H1A	1.005 (19)
C7—H7	0.948 (17)	C1—H1B	1.009 (19)
C3—C4	1.366 (2)
C3—O2—C1	105.93 (12)	C3—C4—H4	122.5 (11)
C2—O1—C1	105.90 (12)	C5—C4—H4	121.1 (11)
C7—C2—O1	127.63 (14)	C8—C9—C10	126.69 (16)
C7—C2—C3	122.73 (14)	C8—C9—H9	120.7 (11)
O1—C2—C3	109.63 (13)	C10—C9—H9	112.6 (11)
C5—C6—C7	119.01 (14)	O3—C10—C9	119.83 (17)
C5—C6—C8	119.81 (14)	O3—C10—C11	120.43 (17)
C7—C6—C8	121.17 (14)	C9—C10—C11	119.74 (17)
C4—C5—C6	122.66 (16)	C10—C11—H11A	105 (2)
C4—C5—H5	118.7 (10)	C10—C11—H11C	110.3 (18)
C6—C5—H5	118.6 (10)	H11A—C11—H11C	106 (2)
C2—C7—C6	117.36 (15)	C10—C11—H11B	115.3 (19)
C2—C7—H7	121.4 (9)	H11A—C11—H11B	115 (3)
C6—C7—H7	121.3 (9)	H11C—C11—H11B	106 (3)
C4—C3—O2	128.40 (14)	O2—C1—O1	107.73 (14)
C4—C3—C2	121.79 (15)	O2—C1—H1A	109.7 (11)
O2—C3—C2	109.80 (13)	O1—C1—H1A	108.3 (11)
C9—C8—C6	126.90 (16)	O2—C1—H1B	108.7 (10)
C9—C8—H8	117.3 (11)	O1—C1—H1B	110.9 (10)
C6—C8—H8	115.8 (11)	H1A—C1—H1B	111.5 (15)
C3—C4—C5	116.44 (16)
C1—O1—C2—C7	174.79 (18)	C7—C2—C3—O2	179.18 (15)
C1—O1—C2—C3	−6.33 (18)	O1—C2—C3—O2	0.24 (18)
C7—C6—C5—C4	−0.4 (3)	C5—C6—C8—C9	−173.77 (17)
C8—C6—C5—C4	178.81 (16)	C7—C6—C8—C9	5.4 (3)
O1—C2—C7—C6	178.83 (15)	O2—C3—C4—C5	−179.36 (16)
C3—C2—C7—C6	0.1 (2)	C2—C3—C4—C5	−0.6 (3)
C5—C6—C7—C2	0.0 (2)	C6—C5—C4—C3	0.7 (3)
C8—C6—C7—C2	−179.22 (15)	C6—C8—C9—C10	177.30 (16)
C1—O2—C3—C4	−175.19 (18)	C8—C9—C10—O3	−176.10 (17)
C1—O2—C3—C2	5.96 (19)	C8—C9—C10—C11	3.5 (3)
C7—C2—C3—C4	0.3 (3)	C3—O2—C1—O1	−9.8 (2)
O1—C2—C3—C4	−178.69 (15)	C2—O1—C1—O2	9.91 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.95 (2)	2.56 (2)	3.489 (2)	166 (1)
C9—H9···O1i	0.93 (2)	2.60 (2)	3.517 (2)	171 (1)
C8—H8···O2ii	0.93 (2)	2.90 (2)	3.819 (2)	177 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.95 (2)	2.56 (2)	3.489 (2)	166 (1)
C9—H9⋯O1i	0.93 (2)	2.60 (2)	3.517 (2)	171 (1)
C8—H8⋯O2ii	0.93 (2)	2.90 (2)	3.819 (2)	177 (1)

Symmetry codes: (i) ; (ii) .