In the title biologically active compound, C17H13Cl2FO3, the central C=C double bond is trans configured. The molecule consists of two essentially planar parts which are twisted by 67.06 (2)° with respect to each other.
Supporting information
CCDC reference: 621404
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.030
- wR factor = 0.078
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
1-(2,4-Dichloro-5-fluorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
top
Crystal data top
C17H13Cl2FO3 | F(000) = 728 |
Mr = 355.17 | Dx = 1.492 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11877 reflections |
a = 6.8572 (5) Å | θ = 3.7–25.8° |
b = 16.7211 (11) Å | µ = 0.43 mm−1 |
c = 13.9299 (12) Å | T = 173 K |
β = 98.173 (6)° | Block, colourless |
V = 1581.0 (2) Å3 | 0.48 × 0.46 × 0.43 mm |
Z = 4 | |
Data collection top
Stoe IPDS II two-circle diffractometer | 2940 independent reflections |
Radiation source: fine-focus sealed tube | 2728 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 25.6°, θmin = 3.7° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −8→8 |
Tmin = 0.819, Tmax = 0.836 | k = −20→20 |
11672 measured reflections | l = −16→14 |
Refinement top
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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.078 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.6433P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2940 reflections | Δρmax = 0.25 e Å−3 |
211 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0178 (15) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6296 (2) | 0.77074 (6) | 0.28042 (8) | 0.0381 (3) | |
C1 | 0.6169 (2) | 0.69789 (8) | 0.27130 (10) | 0.0231 (3) | |
C2 | 0.6617 (2) | 0.64396 (8) | 0.35428 (10) | 0.0227 (3) | |
H2 | 0.6880 | 0.6671 | 0.4171 | 0.027* | |
C3 | 0.66825 (19) | 0.56360 (8) | 0.34741 (10) | 0.0209 (3) | |
H3 | 0.6387 | 0.5419 | 0.2840 | 0.025* | |
C11 | 0.5477 (2) | 0.66259 (8) | 0.17172 (9) | 0.0202 (3) | |
C12 | 0.6519 (2) | 0.67201 (8) | 0.09323 (10) | 0.0220 (3) | |
Cl12 | 0.87494 (6) | 0.72414 (3) | 0.10673 (3) | 0.03626 (14) | |
C13 | 0.5843 (2) | 0.64029 (8) | 0.00189 (10) | 0.0251 (3) | |
H13 | 0.6581 | 0.6469 | −0.0504 | 0.030* | |
C14 | 0.4066 (2) | 0.59884 (8) | −0.01101 (10) | 0.0247 (3) | |
Cl14 | 0.31409 (7) | 0.55880 (2) | −0.12331 (3) | 0.03771 (14) | |
C15 | 0.3011 (2) | 0.59011 (9) | 0.06595 (11) | 0.0271 (3) | |
F15 | 0.12876 (16) | 0.55009 (6) | 0.05296 (8) | 0.0459 (3) | |
C16 | 0.3693 (2) | 0.62082 (8) | 0.15687 (10) | 0.0248 (3) | |
H16 | 0.2953 | 0.6135 | 0.2089 | 0.030* | |
C21 | 0.71543 (18) | 0.50595 (8) | 0.42613 (10) | 0.0192 (3) | |
C22 | 0.76240 (19) | 0.52988 (8) | 0.52448 (10) | 0.0189 (3) | |
H22 | 0.7641 | 0.5851 | 0.5406 | 0.023* | |
C23 | 0.80558 (18) | 0.47377 (8) | 0.59676 (10) | 0.0184 (3) | |
C24 | 0.80408 (18) | 0.39091 (8) | 0.57349 (10) | 0.0189 (3) | |
C25 | 0.7561 (2) | 0.36685 (8) | 0.47734 (10) | 0.0218 (3) | |
H25 | 0.7527 | 0.3116 | 0.4613 | 0.026* | |
C26 | 0.71280 (19) | 0.42423 (8) | 0.40452 (10) | 0.0222 (3) | |
H26 | 0.6810 | 0.4074 | 0.3390 | 0.027* | |
O27 | 0.85085 (15) | 0.49003 (6) | 0.69379 (7) | 0.0241 (2) | |
C27 | 0.8323 (2) | 0.57144 (8) | 0.72334 (11) | 0.0275 (3) | |
H27A | 0.9285 | 0.6046 | 0.6959 | 0.041* | |
H27B | 0.8568 | 0.5747 | 0.7943 | 0.041* | |
H27C | 0.6990 | 0.5907 | 0.7001 | 0.041* | |
O28 | 0.84959 (15) | 0.34136 (6) | 0.65125 (7) | 0.0236 (2) | |
C28 | 0.8443 (3) | 0.25682 (8) | 0.63327 (12) | 0.0311 (3) | |
H28A | 0.7119 | 0.2414 | 0.6030 | 0.047* | |
H28B | 0.8775 | 0.2281 | 0.6947 | 0.047* | |
H28C | 0.9400 | 0.2433 | 0.5898 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0688 (8) | 0.0230 (6) | 0.0234 (6) | −0.0100 (5) | 0.0094 (5) | −0.0022 (4) |
C1 | 0.0278 (7) | 0.0249 (7) | 0.0175 (7) | −0.0050 (5) | 0.0063 (5) | −0.0012 (5) |
C2 | 0.0255 (7) | 0.0281 (7) | 0.0143 (6) | −0.0043 (5) | 0.0026 (5) | −0.0009 (5) |
C3 | 0.0184 (6) | 0.0291 (7) | 0.0155 (6) | −0.0011 (5) | 0.0033 (5) | −0.0019 (5) |
C11 | 0.0267 (7) | 0.0181 (6) | 0.0157 (6) | 0.0008 (5) | 0.0023 (5) | 0.0022 (5) |
C12 | 0.0252 (7) | 0.0219 (7) | 0.0190 (7) | 0.0008 (5) | 0.0037 (5) | 0.0028 (5) |
Cl12 | 0.0319 (2) | 0.0480 (3) | 0.0309 (2) | −0.01281 (16) | 0.01128 (16) | −0.00367 (16) |
C13 | 0.0348 (8) | 0.0250 (7) | 0.0164 (7) | 0.0058 (6) | 0.0069 (6) | 0.0025 (5) |
C14 | 0.0374 (8) | 0.0192 (6) | 0.0153 (7) | 0.0064 (6) | −0.0042 (6) | −0.0006 (5) |
Cl14 | 0.0590 (3) | 0.0301 (2) | 0.0196 (2) | 0.00643 (17) | −0.00987 (17) | −0.00625 (14) |
C15 | 0.0285 (7) | 0.0243 (7) | 0.0269 (8) | −0.0038 (6) | −0.0020 (6) | −0.0013 (6) |
F15 | 0.0404 (6) | 0.0536 (6) | 0.0419 (6) | −0.0224 (5) | −0.0002 (5) | −0.0099 (5) |
C16 | 0.0286 (7) | 0.0258 (7) | 0.0206 (7) | −0.0032 (6) | 0.0059 (6) | 0.0010 (6) |
C21 | 0.0149 (6) | 0.0253 (7) | 0.0178 (6) | −0.0010 (5) | 0.0039 (5) | −0.0009 (5) |
C22 | 0.0177 (6) | 0.0208 (6) | 0.0184 (7) | −0.0012 (5) | 0.0034 (5) | −0.0015 (5) |
C23 | 0.0174 (6) | 0.0231 (6) | 0.0153 (6) | −0.0024 (5) | 0.0041 (5) | −0.0030 (5) |
C24 | 0.0169 (6) | 0.0212 (6) | 0.0193 (7) | −0.0009 (5) | 0.0048 (5) | 0.0006 (5) |
C25 | 0.0226 (6) | 0.0211 (6) | 0.0222 (7) | −0.0004 (5) | 0.0046 (5) | −0.0052 (5) |
C26 | 0.0215 (6) | 0.0277 (7) | 0.0173 (7) | 0.0000 (5) | 0.0029 (5) | −0.0052 (5) |
O27 | 0.0368 (6) | 0.0206 (5) | 0.0144 (5) | −0.0010 (4) | 0.0026 (4) | −0.0022 (4) |
C27 | 0.0378 (8) | 0.0228 (7) | 0.0213 (7) | −0.0004 (6) | 0.0017 (6) | −0.0066 (6) |
O28 | 0.0322 (5) | 0.0181 (5) | 0.0203 (5) | −0.0010 (4) | 0.0033 (4) | −0.0001 (4) |
C28 | 0.0433 (9) | 0.0178 (7) | 0.0310 (8) | −0.0004 (6) | 0.0010 (7) | 0.0001 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2266 (18) | C21—C22 | 1.4196 (19) |
C1—C2 | 1.4638 (19) | C22—C23 | 1.3773 (19) |
C1—C11 | 1.5201 (18) | C22—H22 | 0.9500 |
C2—C3 | 1.348 (2) | C23—O27 | 1.3704 (16) |
C2—H2 | 0.9500 | C23—C24 | 1.4225 (19) |
C3—C21 | 1.4612 (19) | C24—O28 | 1.3643 (16) |
C3—H3 | 0.9500 | C24—C25 | 1.3924 (19) |
C11—C12 | 1.3975 (19) | C25—C26 | 1.397 (2) |
C11—C16 | 1.398 (2) | C25—H25 | 0.9500 |
C12—C13 | 1.396 (2) | C26—H26 | 0.9500 |
C12—Cl12 | 1.7471 (14) | O27—C27 | 1.4329 (16) |
C13—C14 | 1.391 (2) | C27—H27A | 0.9800 |
C13—H13 | 0.9500 | C27—H27B | 0.9800 |
C14—C15 | 1.384 (2) | C27—H27C | 0.9800 |
C14—Cl14 | 1.7365 (14) | O28—C28 | 1.4352 (17) |
C15—F15 | 1.3479 (18) | C28—H28A | 0.9800 |
C15—C16 | 1.385 (2) | C28—H28B | 0.9800 |
C16—H16 | 0.9500 | C28—H28C | 0.9800 |
C21—C26 | 1.3988 (19) | | |
| | | |
O1—C1—C2 | 121.74 (13) | C23—C22—C21 | 120.62 (12) |
O1—C1—C11 | 119.24 (13) | C23—C22—H22 | 119.7 |
C2—C1—C11 | 119.00 (12) | C21—C22—H22 | 119.7 |
C3—C2—C1 | 124.28 (13) | O27—C23—C22 | 125.51 (12) |
C3—C2—H2 | 117.9 | O27—C23—C24 | 114.29 (12) |
C1—C2—H2 | 117.9 | C22—C23—C24 | 120.20 (12) |
C2—C3—C21 | 127.60 (13) | O28—C24—C25 | 125.76 (12) |
C2—C3—H3 | 116.2 | O28—C24—C23 | 114.65 (11) |
C21—C3—H3 | 116.2 | C25—C24—C23 | 119.59 (12) |
C12—C11—C16 | 118.33 (13) | C24—C25—C26 | 119.78 (12) |
C12—C11—C1 | 122.81 (12) | C24—C25—H25 | 120.1 |
C16—C11—C1 | 118.83 (12) | C26—C25—H25 | 120.1 |
C13—C12—C11 | 121.99 (13) | C25—C26—C21 | 121.32 (12) |
C13—C12—Cl12 | 117.39 (11) | C25—C26—H26 | 119.3 |
C11—C12—Cl12 | 120.62 (11) | C21—C26—H26 | 119.3 |
C14—C13—C12 | 118.59 (13) | C23—O27—C27 | 117.06 (11) |
C14—C13—H13 | 120.7 | O27—C27—H27A | 109.5 |
C12—C13—H13 | 120.7 | O27—C27—H27B | 109.5 |
C15—C14—C13 | 119.82 (13) | H27A—C27—H27B | 109.5 |
C15—C14—Cl14 | 119.53 (12) | O27—C27—H27C | 109.5 |
C13—C14—Cl14 | 120.65 (11) | H27A—C27—H27C | 109.5 |
F15—C15—C14 | 119.56 (13) | H27B—C27—H27C | 109.5 |
F15—C15—C16 | 118.86 (14) | C24—O28—C28 | 117.54 (11) |
C14—C15—C16 | 121.58 (13) | O28—C28—H28A | 109.5 |
C15—C16—C11 | 119.67 (13) | O28—C28—H28B | 109.5 |
C15—C16—H16 | 120.2 | H28A—C28—H28B | 109.5 |
C11—C16—H16 | 120.2 | O28—C28—H28C | 109.5 |
C26—C21—C22 | 118.50 (12) | H28A—C28—H28C | 109.5 |
C26—C21—C3 | 119.23 (12) | H28B—C28—H28C | 109.5 |
C22—C21—C3 | 122.28 (12) | | |
| | | |
O1—C1—C2—C3 | −173.54 (14) | C12—C11—C16—C15 | 0.0 (2) |
C11—C1—C2—C3 | 8.1 (2) | C1—C11—C16—C15 | 178.24 (13) |
C1—C2—C3—C21 | 178.68 (13) | C2—C3—C21—C26 | 179.42 (13) |
O1—C1—C11—C12 | 63.1 (2) | C2—C3—C21—C22 | 0.0 (2) |
C2—C1—C11—C12 | −118.54 (15) | C26—C21—C22—C23 | 0.41 (19) |
O1—C1—C11—C16 | −115.03 (16) | C3—C21—C22—C23 | 179.82 (12) |
C2—C1—C11—C16 | 63.35 (18) | C21—C22—C23—O27 | −179.32 (12) |
C16—C11—C12—C13 | −0.8 (2) | C21—C22—C23—C24 | 0.18 (19) |
C1—C11—C12—C13 | −178.91 (13) | O27—C23—C24—O28 | −0.57 (16) |
C16—C11—C12—Cl12 | 179.59 (10) | C22—C23—C24—O28 | 179.88 (11) |
C1—C11—C12—Cl12 | 1.47 (19) | O27—C23—C24—C25 | 178.67 (12) |
C11—C12—C13—C14 | 0.7 (2) | C22—C23—C24—C25 | −0.88 (19) |
Cl12—C12—C13—C14 | −179.69 (10) | O28—C24—C25—C26 | −179.87 (12) |
C12—C13—C14—C15 | 0.2 (2) | C23—C24—C25—C26 | 1.0 (2) |
C12—C13—C14—Cl14 | 179.44 (10) | C24—C25—C26—C21 | −0.4 (2) |
C13—C14—C15—F15 | 179.81 (13) | C22—C21—C26—C25 | −0.30 (19) |
Cl14—C14—C15—F15 | 0.55 (19) | C3—C21—C26—C25 | −179.73 (12) |
C13—C14—C15—C16 | −0.9 (2) | C22—C23—O27—C27 | 6.65 (19) |
Cl14—C14—C15—C16 | 179.81 (11) | C24—C23—O27—C27 | −172.87 (11) |
F15—C15—C16—C11 | −179.92 (13) | C25—C24—O28—C28 | −1.2 (2) |
C14—C15—C16—C11 | 0.8 (2) | C23—C24—O28—C28 | 177.96 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O27i | 0.95 | 2.50 | 3.3067 (17) | 143 |
C16—H16···O28i | 0.95 | 2.43 | 3.3072 (17) | 154 |
Symmetry code: (i) −x+1, −y+1, −z+1. |