Acta Cryst. (2010). E66, o1412 [ doi:10.1107/S1600536810018106 ]
In the title chalcone derivative, C17H15BrO, the dihedral angle between the two benzene rings is 48.13 (4)°. In the crystal, a short Br
Br contact of 3.5052 (10) Å occurs.
A mixture of 4-bromohypnone (0.02 mol) and 3,4-dimethylbenzaldehyde (0.02 mol) and 10%NaOH (5 ml) was stirred in ethanol (30 ml) for 1.5 h to afford the title compound (yield 73%). Yellow blocks of (I) were obtailed by recrystallization from ethyl acetate at room temperature.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93-0.96 Å, and with Uiso(H) = 1.2Ueq of the parent atoms.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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]](./hb5445fig1thm.gif)
| Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at the 30% probability level. |
| C17H15BrO | Z = 2 |
| Mr = 315.20 | F(000) = 320 |
| Triclinic, P1 | Dx = 1.468 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.9786 (14) Å | Cell parameters from 2198 reflections |
| b = 7.8437 (19) Å | θ = 1.3–25.5° |
| c = 15.744 (4) Å | µ = 2.87 mm−1 |
| α = 99.054 (4)° | T = 298 K |
| β = 99.602 (4)° | Bar, yellow |
| γ = 95.659 (4)° | 0.25 × 0.22 × 0.20 mm |
| V = 713.0 (3) Å3 |
| Bruker SMART CCD diffractometer | 2198 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.019 |
| graphite | θmax = 25.5°, θmin = 1.3° |
| phi and ω scans | h = −7→7 |
| 3911 measured reflections | k = −9→6 |
| 2620 independent reflections | l = −18→19 |
| 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)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.2458P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max < 0.001 |
| 2620 reflections | Δρmax = 0.45 e Å−3 |
| 173 parameters | Δρmin = −0.60 e Å−3 |
| 0 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: 0.048 (4) |
| C17H15BrO | γ = 95.659 (4)° |
| Mr = 315.20 | V = 713.0 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 5.9786 (14) Å | Mo Kα radiation |
| b = 7.8437 (19) Å | µ = 2.87 mm−1 |
| c = 15.744 (4) Å | T = 298 K |
| α = 99.054 (4)° | 0.25 × 0.22 × 0.20 mm |
| β = 99.602 (4)° |
| Bruker SMART CCD diffractometer | 2198 reflections with I > 2σ(I) |
| 3911 measured reflections | Rint = 0.019 |
| 2620 independent reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.095 | Δρmax = 0.45 e Å−3 |
| S = 1.09 | Δρmin = −0.60 e Å−3 |
| 2620 reflections | Absolute structure: ? |
| 173 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 > 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 | ||
| Br | 0.57731 (6) | 0.43242 (4) | 0.100602 (19) | 0.06655 (18) | |
| C11 | 0.5449 (5) | 0.3857 (3) | 0.21288 (17) | 0.0440 (6) | |
| O | 0.2750 (3) | 0.2761 (3) | 0.48223 (13) | 0.0628 (6) | |
| C10 | 0.7328 (5) | 0.4220 (4) | 0.27985 (18) | 0.0482 (6) | |
| H10A | 0.8724 | 0.4717 | 0.2706 | 0.058* | |
| C17 | 0.4645 (5) | 0.2760 (4) | 0.46327 (17) | 0.0455 (6) | |
| C12 | 0.3349 (5) | 0.3142 (4) | 0.22550 (18) | 0.0506 (7) | |
| H12A | 0.2100 | 0.2898 | 0.1796 | 0.061* | |
| C9 | 0.7107 (4) | 0.3834 (3) | 0.36099 (17) | 0.0448 (6) | |
| H9A | 0.8374 | 0.4048 | 0.4061 | 0.054* | |
| C8 | 0.5010 (4) | 0.3129 (3) | 0.37593 (16) | 0.0395 (5) | |
| C6 | 1.1464 (4) | 0.0981 (3) | 0.80706 (18) | 0.0453 (6) | |
| C5 | 0.9589 (4) | 0.1781 (4) | 0.82839 (17) | 0.0448 (6) | |
| C3 | 0.8289 (4) | 0.1904 (3) | 0.67426 (17) | 0.0408 (6) | |
| C4 | 0.8024 (4) | 0.2208 (3) | 0.76150 (17) | 0.0437 (6) | |
| H4A | 0.6759 | 0.2714 | 0.7755 | 0.052* | |
| C16 | 0.6528 (5) | 0.2356 (3) | 0.60745 (17) | 0.0437 (6) | |
| H16A | 0.5194 | 0.2656 | 0.6256 | 0.052* | |
| C2 | 1.0206 (5) | 0.1157 (3) | 0.65442 (18) | 0.0459 (6) | |
| H2A | 1.0448 | 0.0967 | 0.5970 | 0.055* | |
| C7 | 0.3131 (5) | 0.2796 (4) | 0.30725 (17) | 0.0464 (6) | |
| H7A | 0.1717 | 0.2335 | 0.3167 | 0.056* | |
| C15 | 0.6631 (5) | 0.2384 (4) | 0.52402 (18) | 0.0477 (6) | |
| H15A | 0.7966 | 0.2164 | 0.5036 | 0.057* | |
| C1 | 1.1749 (5) | 0.0697 (3) | 0.72054 (19) | 0.0474 (6) | |
| H1A | 1.3008 | 0.0184 | 0.7064 | 0.057* | |
| C14 | 0.9249 (6) | 0.2180 (5) | 0.9221 (2) | 0.0674 (9) | |
| H14A | 0.7885 | 0.2726 | 0.9242 | 0.101* | |
| H14B | 1.0541 | 0.2950 | 0.9567 | 0.101* | |
| H14C | 0.9103 | 0.1119 | 0.9450 | 0.101* | |
| C13 | 1.3147 (6) | 0.0413 (4) | 0.8765 (2) | 0.0635 (8) | |
| H13A | 1.4312 | −0.0106 | 0.8501 | 0.095* | |
| H13B | 1.2362 | −0.0421 | 0.9034 | 0.095* | |
| H13C | 1.3838 | 0.1406 | 0.9201 | 0.095* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br | 0.0949 (3) | 0.0686 (3) | 0.0421 (2) | 0.01006 (17) | 0.01910 (16) | 0.02128 (15) |
| C11 | 0.0583 (16) | 0.0408 (13) | 0.0358 (13) | 0.0098 (12) | 0.0132 (12) | 0.0091 (11) |
| O | 0.0507 (12) | 0.0955 (16) | 0.0468 (11) | 0.0114 (11) | 0.0174 (9) | 0.0161 (11) |
| C10 | 0.0477 (15) | 0.0507 (15) | 0.0470 (15) | 0.0019 (12) | 0.0133 (12) | 0.0092 (12) |
| C17 | 0.0508 (16) | 0.0485 (15) | 0.0367 (13) | 0.0058 (12) | 0.0101 (11) | 0.0043 (11) |
| C12 | 0.0514 (16) | 0.0571 (17) | 0.0394 (14) | 0.0025 (13) | −0.0017 (12) | 0.0104 (12) |
| C9 | 0.0420 (14) | 0.0502 (15) | 0.0387 (14) | 0.0038 (11) | 0.0027 (11) | 0.0042 (11) |
| C8 | 0.0449 (14) | 0.0387 (13) | 0.0361 (13) | 0.0085 (10) | 0.0108 (10) | 0.0052 (10) |
| C6 | 0.0446 (14) | 0.0401 (13) | 0.0501 (15) | 0.0030 (11) | 0.0045 (12) | 0.0112 (12) |
| C5 | 0.0434 (14) | 0.0507 (15) | 0.0403 (14) | 0.0011 (11) | 0.0081 (11) | 0.0106 (12) |
| C3 | 0.0434 (14) | 0.0406 (13) | 0.0395 (13) | 0.0027 (10) | 0.0096 (11) | 0.0104 (11) |
| C4 | 0.0417 (14) | 0.0500 (15) | 0.0421 (14) | 0.0088 (11) | 0.0120 (11) | 0.0098 (12) |
| C16 | 0.0459 (14) | 0.0452 (14) | 0.0413 (14) | 0.0061 (11) | 0.0113 (11) | 0.0086 (11) |
| C2 | 0.0528 (15) | 0.0460 (14) | 0.0401 (14) | 0.0052 (12) | 0.0147 (12) | 0.0052 (11) |
| C7 | 0.0423 (14) | 0.0534 (16) | 0.0428 (15) | 0.0010 (12) | 0.0067 (11) | 0.0107 (12) |
| C15 | 0.0525 (16) | 0.0562 (16) | 0.0389 (14) | 0.0138 (13) | 0.0139 (12) | 0.0120 (12) |
| C1 | 0.0432 (14) | 0.0430 (14) | 0.0580 (17) | 0.0092 (11) | 0.0149 (12) | 0.0071 (12) |
| C14 | 0.0606 (19) | 0.103 (3) | 0.0422 (17) | 0.0175 (17) | 0.0120 (14) | 0.0157 (17) |
| C13 | 0.0604 (19) | 0.067 (2) | 0.064 (2) | 0.0181 (15) | 0.0032 (15) | 0.0181 (16) |
| Br—C11 | 1.898 (3) | C3—C2 | 1.396 (4) |
| C11—C10 | 1.379 (4) | C3—C4 | 1.395 (4) |
| C11—C12 | 1.382 (4) | C3—C16 | 1.470 (4) |
| O—C17 | 1.219 (3) | C4—H4A | 0.9300 |
| C10—C9 | 1.382 (4) | C16—C15 | 1.329 (4) |
| C10—H10A | 0.9300 | C16—H16A | 0.9300 |
| C17—C15 | 1.480 (4) | C2—C1 | 1.389 (4) |
| C17—C8 | 1.495 (4) | C2—H2A | 0.9300 |
| C12—C7 | 1.381 (4) | C7—H7A | 0.9300 |
| C12—H12A | 0.9300 | C15—H15A | 0.9300 |
| C9—C8 | 1.391 (4) | C1—H1A | 0.9300 |
| C9—H9A | 0.9300 | C14—H14A | 0.9600 |
| C8—C7 | 1.396 (4) | C14—H14B | 0.9600 |
| C6—C1 | 1.387 (4) | C14—H14C | 0.9600 |
| C6—C5 | 1.400 (4) | C13—H13A | 0.9600 |
| C6—C13 | 1.510 (4) | C13—H13B | 0.9600 |
| C5—C4 | 1.393 (4) | C13—H13C | 0.9600 |
| C5—C14 | 1.512 (4) | ||
| C10—C11—C12 | 121.5 (2) | C3—C4—H4A | 118.9 |
| C10—C11—Br | 119.1 (2) | C15—C16—C3 | 127.2 (3) |
| C12—C11—Br | 119.4 (2) | C15—C16—H16A | 116.4 |
| C11—C10—C9 | 119.1 (2) | C3—C16—H16A | 116.4 |
| C11—C10—H10A | 120.5 | C1—C2—C3 | 119.9 (2) |
| C9—C10—H10A | 120.5 | C1—C2—H2A | 120.1 |
| O—C17—C15 | 122.0 (3) | C3—C2—H2A | 120.1 |
| O—C17—C8 | 119.9 (2) | C12—C7—C8 | 120.7 (2) |
| C15—C17—C8 | 118.0 (2) | C12—C7—H7A | 119.7 |
| C11—C12—C7 | 119.1 (2) | C8—C7—H7A | 119.7 |
| C11—C12—H12A | 120.5 | C16—C15—C17 | 120.7 (3) |
| C7—C12—H12A | 120.5 | C16—C15—H15A | 119.6 |
| C10—C9—C8 | 120.8 (2) | C17—C15—H15A | 119.6 |
| C10—C9—H9A | 119.6 | C6—C1—C2 | 121.8 (2) |
| C8—C9—H9A | 119.6 | C6—C1—H1A | 119.1 |
| C9—C8—C7 | 118.9 (2) | C2—C1—H1A | 119.1 |
| C9—C8—C17 | 123.1 (2) | C5—C14—H14A | 109.5 |
| C7—C8—C17 | 117.9 (2) | C5—C14—H14B | 109.5 |
| C1—C6—C5 | 119.0 (2) | H14A—C14—H14B | 109.5 |
| C1—C6—C13 | 120.0 (3) | C5—C14—H14C | 109.5 |
| C5—C6—C13 | 121.0 (3) | H14A—C14—H14C | 109.5 |
| C4—C5—C6 | 118.9 (2) | H14B—C14—H14C | 109.5 |
| C4—C5—C14 | 120.0 (2) | C6—C13—H13A | 109.5 |
| C6—C5—C14 | 121.1 (3) | C6—C13—H13B | 109.5 |
| C2—C3—C4 | 118.2 (2) | H13A—C13—H13B | 109.5 |
| C2—C3—C16 | 123.1 (2) | C6—C13—H13C | 109.5 |
| C4—C3—C16 | 118.8 (2) | H13A—C13—H13C | 109.5 |
| C5—C4—C3 | 122.3 (2) | H13B—C13—H13C | 109.5 |
| C5—C4—H4A | 118.9 |
Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
Fun, H.-K., Chantrapromma, S., Patil, P. S., D'Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954–o955.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
As part of our search for new biologically active compounds we synthesized the title compound(I) and report its crystal structure herein.
In the crystal structure of compound(I)(fig.1),the dihedral angle between the two benzene rings(C1—C6) and (C7—C12) is 48.13 (4)°. All of the bond lengths and bond angles are in normal ranges and comparable to those in related structure (Fun et al., 2008).