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access(E)-1-(1,3-Benzodioxol-5-yl)-3-(3-bromophenyl)prop-2-en-1-one
aKey Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, cDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: hongqili@dhu.edu.cn
In the title compound, C16H11BrO3, the molecules adopt an E configuration with respect to the C=C double bond of the propenone unit. The 13 non-H atoms of the benzodioxole and propenone units are approximately coplanar (r.m.s. deviation = 0.027 Å) and the bromobenzene ring plane forms a dihedral angle of 10.8 (1)° to this plane. The structure is layered, with the molecules forming a herring-bone arrangement within each layer.
Related literature
For the use of as starting materials in the preparation of various molecules including fused see: Insuasty et al. (1997![[Insuasty, B., Quiroga, J. & Meier, H. (1997). Trends Heterocycl. Chem. 5, 83-89.]](../../../../../../logos/arrows/e_arr.gif "Insuasty, B., Quiroga, J. & Meier, H. (1997). Trends Heterocycl. Chem. 5, 83-89.")
). For related structures, see: Butcher et al. (2007a,b,c); Low et al. (2002).
![[Scheme 1]](bi2315scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); 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.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808037446/bi2315sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808037446/bi2315Isup2.hkl
To a mixture of 1-(1,3-benzodioxol-5-yl)ethanone (1.64 g, 0.01 mol) and 3-bromobenzaldehyde (1.86 g, 0.01 mol) in 25 ml of ethanol, 50% KOH(aq) was added. The mixture was stirred for one hour at room temperature then the precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from toluene by slow evaporation. Yield: 82 %, m.p. 393–395 K. Elemental analysis calculated: C 58.03, H 3.35%; found: C 58.12, H 3.21%.
H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).
![[Figure 1]](./bi2315fig1thm.gif) | Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms. |
| C16H11BrO3 | F(000) = 664 |
| Mr = 331.16 | Dx = 1.640 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3007 reflections |
| a = 14.237 (3) Å | θ = 2.9–28.0° |
| b = 8.1811 (17) Å | µ = 3.07 mm−1 |
| c = 11.717 (2) Å | T = 273 K |
| β = 100.658 (3)° | Block, colorless |
| V = 1341.1 (5) Å3 | 0.12 × 0.10 × 0.06 mm |
| Z = 4 |
| Bruker SMART APEXII CCD diffractometer | 2362 independent reflections |
| Radiation source: fine-focus sealed tube | 1869 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.021 |
| ϕ and ω scans | θmax = 25.0°, θmin = 2.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −16→16 |
| Tmin = 0.710, Tmax = 0.837 | k = −9→9 |
| 6752 measured reflections | l = −13→9 |
| 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)] = 0.026 | H-atom parameters constrained |
| wR(F2) = 0.073 | w = 1/[σ2(Fo2) + (0.0383P)2 + 0.3973P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 2362 reflections | Δρmax = 0.35 e Å−3 |
| 182 parameters | Δρmin = −0.30 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008) |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0063 (7) |
| C16H11BrO3 | V = 1341.1 (5) Å3 |
| Mr = 331.16 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 14.237 (3) Å | µ = 3.07 mm−1 |
| b = 8.1811 (17) Å | T = 273 K |
| c = 11.717 (2) Å | 0.12 × 0.10 × 0.06 mm |
| β = 100.658 (3)° |
| Bruker SMART APEXII CCD diffractometer | 2362 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1869 reflections with I > 2σ(I) |
| Tmin = 0.710, Tmax = 0.837 | Rint = 0.021 |
| 6752 measured reflections |
| R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
| wR(F2) = 0.073 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.35 e Å−3 |
| 2362 reflections | Δρmin = −0.30 e Å−3 |
| 182 parameters |
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 | ||
| Br1 | 0.489230 (17) | 1.25202 (3) | 0.29468 (2) | 0.05206 (13) | |
| O1 | 0.93644 (14) | 0.7277 (2) | 0.27018 (16) | 0.0622 (6) | |
| O2 | 1.29937 (12) | 0.4896 (2) | 0.61302 (13) | 0.0541 (5) | |
| O3 | 1.26700 (12) | 0.4663 (3) | 0.41361 (14) | 0.0599 (5) | |
| C1 | 0.58905 (15) | 1.1426 (3) | 0.39752 (18) | 0.0360 (5) | |
| C2 | 0.65910 (15) | 1.0623 (3) | 0.35360 (18) | 0.0368 (5) | |
| H2 | 0.6575 | 1.0608 | 0.2739 | 0.044* | |
| C3 | 0.73304 (16) | 0.9827 (3) | 0.42861 (18) | 0.0370 (5) | |
| C4 | 0.73303 (17) | 0.9887 (3) | 0.54787 (19) | 0.0433 (6) | |
| H4 | 0.7819 | 0.9381 | 0.5994 | 0.052* | |
| C5 | 0.66100 (17) | 1.0691 (3) | 0.58983 (19) | 0.0455 (6) | |
| H5 | 0.6615 | 1.0709 | 0.6693 | 0.055* | |
| C6 | 0.58831 (16) | 1.1468 (3) | 0.51479 (19) | 0.0427 (6) | |
| H6 | 0.5399 | 1.2009 | 0.5430 | 0.051* | |
| C7 | 0.80648 (16) | 0.8953 (3) | 0.3795 (2) | 0.0424 (6) | |
| H7 | 0.7946 | 0.8819 | 0.2993 | 0.051* | |
| C8 | 0.88707 (17) | 0.8340 (3) | 0.4361 (2) | 0.0464 (6) | |
| H8 | 0.9018 | 0.8455 | 0.5164 | 0.056* | |
| C9 | 0.95504 (19) | 0.7472 (3) | 0.3760 (2) | 0.0431 (6) | |
| C10 | 1.04589 (16) | 0.6841 (3) | 0.44539 (18) | 0.0355 (5) | |
| C11 | 1.11052 (16) | 0.6051 (3) | 0.38609 (19) | 0.0427 (6) | |
| H11 | 1.0972 | 0.5928 | 0.3058 | 0.051* | |
| C12 | 1.19286 (16) | 0.5475 (3) | 0.45046 (18) | 0.0386 (5) | |
| C13 | 1.21294 (16) | 0.5615 (3) | 0.56996 (19) | 0.0394 (5) | |
| C14 | 1.15146 (17) | 0.6343 (3) | 0.6304 (2) | 0.0493 (6) | |
| H14 | 1.1650 | 0.6418 | 0.7109 | 0.059* | |
| C15 | 1.06741 (18) | 0.6969 (3) | 0.5658 (2) | 0.0418 (6) | |
| H15 | 1.0242 | 0.7489 | 0.6042 | 0.050* | |
| C16 | 1.33689 (17) | 0.4360 (3) | 0.5143 (2) | 0.0473 (6) | |
| H16A | 1.3952 | 0.4951 | 0.5098 | 0.057* | |
| H16B | 1.3516 | 0.3203 | 0.5208 | 0.057* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.03784 (17) | 0.0701 (2) | 0.04670 (18) | 0.00990 (12) | 0.00367 (11) | 0.00788 (12) |
| O1 | 0.0524 (12) | 0.0986 (16) | 0.0368 (11) | 0.0217 (10) | 0.0111 (8) | 0.0093 (9) |
| O2 | 0.0400 (10) | 0.0774 (12) | 0.0419 (9) | 0.0128 (9) | −0.0005 (7) | −0.0046 (9) |
| O3 | 0.0465 (10) | 0.0928 (14) | 0.0404 (9) | 0.0245 (10) | 0.0086 (8) | −0.0085 (9) |
| C1 | 0.0279 (11) | 0.0424 (13) | 0.0372 (12) | −0.0039 (9) | 0.0045 (9) | 0.0031 (9) |
| C2 | 0.0360 (12) | 0.0434 (13) | 0.0317 (11) | −0.0044 (10) | 0.0080 (9) | 0.0011 (9) |
| C3 | 0.0351 (12) | 0.0400 (12) | 0.0361 (12) | −0.0047 (10) | 0.0069 (9) | 0.0021 (10) |
| C4 | 0.0381 (13) | 0.0520 (14) | 0.0383 (12) | 0.0012 (11) | 0.0034 (10) | 0.0063 (11) |
| C5 | 0.0462 (14) | 0.0609 (16) | 0.0301 (12) | −0.0019 (12) | 0.0090 (10) | −0.0019 (11) |
| C6 | 0.0352 (13) | 0.0548 (15) | 0.0403 (13) | 0.0008 (11) | 0.0128 (10) | −0.0035 (11) |
| C7 | 0.0419 (14) | 0.0489 (14) | 0.0382 (13) | 0.0028 (11) | 0.0127 (10) | 0.0068 (10) |
| C8 | 0.0439 (14) | 0.0554 (15) | 0.0406 (13) | 0.0076 (12) | 0.0101 (11) | −0.0007 (11) |
| C9 | 0.0440 (14) | 0.0498 (14) | 0.0375 (14) | 0.0025 (11) | 0.0129 (10) | 0.0058 (10) |
| C10 | 0.0352 (12) | 0.0384 (11) | 0.0347 (12) | −0.0018 (10) | 0.0113 (9) | 0.0034 (10) |
| C11 | 0.0437 (14) | 0.0549 (15) | 0.0300 (12) | 0.0041 (11) | 0.0081 (10) | 0.0013 (10) |
| C12 | 0.0352 (12) | 0.0470 (13) | 0.0356 (12) | 0.0019 (10) | 0.0115 (10) | −0.0016 (10) |
| C13 | 0.0329 (12) | 0.0474 (13) | 0.0367 (12) | −0.0029 (10) | 0.0031 (9) | −0.0013 (10) |
| C14 | 0.0473 (15) | 0.0695 (17) | 0.0300 (12) | 0.0052 (13) | 0.0042 (11) | −0.0067 (11) |
| C15 | 0.0412 (14) | 0.0499 (13) | 0.0369 (13) | 0.0013 (11) | 0.0142 (10) | −0.0034 (10) |
| C16 | 0.0366 (13) | 0.0539 (15) | 0.0504 (14) | 0.0058 (11) | 0.0056 (11) | −0.0028 (11) |
| Br1—C1 | 1.908 (2) | C7—C8 | 1.314 (3) |
| O1—C9 | 1.230 (3) | C7—H7 | 0.930 |
| O2—C13 | 1.373 (3) | C8—C9 | 1.479 (3) |
| O2—C16 | 1.429 (3) | C8—H8 | 0.930 |
| O3—C12 | 1.382 (3) | C9—C10 | 1.487 (3) |
| O3—C16 | 1.418 (3) | C10—C15 | 1.391 (3) |
| C1—C2 | 1.371 (3) | C10—C11 | 1.408 (3) |
| C1—C6 | 1.376 (3) | C11—C12 | 1.356 (3) |
| C2—C3 | 1.401 (3) | C11—H11 | 0.930 |
| C2—H2 | 0.930 | C12—C13 | 1.381 (3) |
| C3—C4 | 1.398 (3) | C13—C14 | 1.360 (3) |
| C3—C7 | 1.469 (3) | C14—C15 | 1.390 (3) |
| C4—C5 | 1.383 (3) | C14—H14 | 0.930 |
| C4—H4 | 0.930 | C15—H15 | 0.930 |
| C5—C6 | 1.383 (3) | C16—H16A | 0.970 |
| C5—H5 | 0.930 | C16—H16B | 0.970 |
| C6—H6 | 0.930 | ||
| C13—O2—C16 | 106.13 (17) | O1—C9—C10 | 120.6 (2) |
| C12—O3—C16 | 106.43 (17) | C8—C9—C10 | 119.1 (2) |
| C2—C1—C6 | 121.8 (2) | C15—C10—C11 | 119.6 (2) |
| C2—C1—Br1 | 119.75 (16) | C15—C10—C9 | 122.3 (2) |
| C6—C1—Br1 | 118.45 (17) | C11—C10—C9 | 118.13 (19) |
| C1—C2—C3 | 120.1 (2) | C12—C11—C10 | 117.5 (2) |
| C1—C2—H2 | 119.9 | C12—C11—H11 | 121.3 |
| C3—C2—H2 | 119.9 | C10—C11—H11 | 121.3 |
| C4—C3—C2 | 118.1 (2) | C11—C12—C13 | 122.1 (2) |
| C4—C3—C7 | 122.7 (2) | C11—C12—O3 | 128.7 (2) |
| C2—C3—C7 | 119.15 (19) | C13—C12—O3 | 109.26 (19) |
| C5—C4—C3 | 120.6 (2) | C14—C13—O2 | 128.0 (2) |
| C5—C4—H4 | 119.7 | C14—C13—C12 | 122.1 (2) |
| C3—C4—H4 | 119.7 | O2—C13—C12 | 109.89 (19) |
| C6—C5—C4 | 120.7 (2) | C13—C14—C15 | 116.7 (2) |
| C6—C5—H5 | 119.7 | C13—C14—H14 | 121.6 |
| C4—C5—H5 | 119.7 | C15—C14—H14 | 121.6 |
| C1—C6—C5 | 118.7 (2) | C14—C15—C10 | 122.0 (2) |
| C1—C6—H6 | 120.7 | C14—C15—H15 | 119.0 |
| C5—C6—H6 | 120.7 | C10—C15—H15 | 119.0 |
| C8—C7—C3 | 127.3 (2) | O3—C16—O2 | 108.07 (18) |
| C8—C7—H7 | 116.3 | O3—C16—H16A | 110.1 |
| C3—C7—H7 | 116.3 | O2—C16—H16A | 110.1 |
| C7—C8—C9 | 122.0 (2) | O3—C16—H16B | 110.1 |
| C7—C8—H8 | 119.0 | O2—C16—H16B | 110.1 |
| C9—C8—H8 | 119.0 | H16A—C16—H16B | 108.4 |
| O1—C9—C8 | 120.3 (2) | ||
| C6—C1—C2—C3 | −0.5 (3) | C15—C10—C11—C12 | −1.4 (3) |
| Br1—C1—C2—C3 | 179.54 (16) | C9—C10—C11—C12 | −179.7 (2) |
| C1—C2—C3—C4 | −0.3 (3) | C10—C11—C12—C13 | 1.4 (4) |
| C1—C2—C3—C7 | 179.0 (2) | C10—C11—C12—O3 | 179.9 (2) |
| C2—C3—C4—C5 | 1.0 (4) | C16—O3—C12—C11 | 178.7 (2) |
| C7—C3—C4—C5 | −178.4 (2) | C16—O3—C12—C13 | −2.6 (3) |
| C3—C4—C5—C6 | −0.8 (4) | C16—O2—C13—C14 | −178.3 (3) |
| C2—C1—C6—C5 | 0.7 (3) | C16—O2—C13—C12 | 3.2 (3) |
| Br1—C1—C6—C5 | −179.37 (17) | C11—C12—C13—C14 | −0.2 (4) |
| C4—C5—C6—C1 | 0.0 (4) | O3—C12—C13—C14 | −179.0 (2) |
| C4—C3—C7—C8 | −10.9 (4) | C11—C12—C13—O2 | 178.4 (2) |
| C2—C3—C7—C8 | 169.8 (2) | O3—C12—C13—O2 | −0.4 (3) |
| C3—C7—C8—C9 | 179.6 (2) | O2—C13—C14—C15 | −179.3 (2) |
| C7—C8—C9—O1 | −1.4 (4) | C12—C13—C14—C15 | −1.0 (4) |
| C7—C8—C9—C10 | 178.7 (2) | C13—C14—C15—C10 | 1.0 (4) |
| O1—C9—C10—C15 | −176.9 (2) | C11—C10—C15—C14 | 0.2 (4) |
| C8—C9—C10—C15 | 3.1 (3) | C9—C10—C15—C14 | 178.5 (2) |
| O1—C9—C10—C11 | 1.4 (4) | C12—O3—C16—O2 | 4.5 (3) |
| C8—C9—C10—C11 | −178.6 (2) | C13—O2—C16—O3 | −4.7 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C16H11BrO3 |
| Mr | 331.16 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 273 |
| a, b, c (Å) | 14.237 (3), 8.1811 (17), 11.717 (2) |
| β (°) | 100.658 (3) |
| V (Å3) | 1341.1 (5) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 3.07 |
| Crystal size (mm) | 0.12 × 0.10 × 0.06 |
| Data collection | |
| Diffractometer | Bruker SMART APEXII CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
| Tmin, Tmax | 0.710, 0.837 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 6752, 2362, 1869 |
| Rint | 0.021 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.073, 1.04 |
| No. of reflections | 2362 |
| No. of parameters | 182 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.35, −0.30 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
TVS thanks Mangalore University for research facilities.
References
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Chalcones have been widely used as starting materials in preparation of various molecules including fused heterocyclic compounds (Insuasty et al., 1997). Chalcones are also finding application as organic nonlinear optical (NLO) materials because of their SHG conversion efficiency. The crystal structures of some benzodioxol- and bromo-substituted chalcones have been studied (Butcher et al., 2007a,b,c). In continuation of this theme, and also owing to the general importance of these flavanoid analogues, we report herein the synthesis and crystal structure of a new chalcone, namely (2E)-1-(1,3-benzodioxol-5-yl)- 3-(3-bromophenyl)prop-2-en-1-one.