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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602770X/lh2145sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602770X/lh2145Isup2.hkl
Contains datablock I

CCDC reference: 621404

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C17H13Cl2FO3F(000) = 728
Mr = 355.17Dx = 1.492 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11877 reflections
a = 6.8572 (5) Åθ = 3.7–25.8°
b = 16.7211 (11) ŵ = 0.43 mm1
c = 13.9299 (12) ÅT = 173 K
β = 98.173 (6)°Block, colourless
V = 1581.0 (2) Å30.48 × 0.46 × 0.43 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
2940 independent reflections
Radiation source: fine-focus sealed tube2728 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 88
Tmin = 0.819, Tmax = 0.836k = 2020
11672 measured reflectionsl = 1614
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-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 reflectionsΔρmax = 0.25 e Å3
211 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.6296 (2)0.77074 (6)0.28042 (8)0.0381 (3)
C10.6169 (2)0.69789 (8)0.27130 (10)0.0231 (3)
C20.6617 (2)0.64396 (8)0.35428 (10)0.0227 (3)
H20.68800.66710.41710.027*
C30.66825 (19)0.56360 (8)0.34741 (10)0.0209 (3)
H30.63870.54190.28400.025*
C110.5477 (2)0.66259 (8)0.17172 (9)0.0202 (3)
C120.6519 (2)0.67201 (8)0.09323 (10)0.0220 (3)
Cl120.87494 (6)0.72414 (3)0.10673 (3)0.03626 (14)
C130.5843 (2)0.64029 (8)0.00189 (10)0.0251 (3)
H130.65810.64690.05040.030*
C140.4066 (2)0.59884 (8)0.01101 (10)0.0247 (3)
Cl140.31409 (7)0.55880 (2)0.12331 (3)0.03771 (14)
C150.3011 (2)0.59011 (9)0.06595 (11)0.0271 (3)
F150.12876 (16)0.55009 (6)0.05296 (8)0.0459 (3)
C160.3693 (2)0.62082 (8)0.15687 (10)0.0248 (3)
H160.29530.61350.20890.030*
C210.71543 (18)0.50595 (8)0.42613 (10)0.0192 (3)
C220.76240 (19)0.52988 (8)0.52448 (10)0.0189 (3)
H220.76410.58510.54060.023*
C230.80558 (18)0.47377 (8)0.59676 (10)0.0184 (3)
C240.80408 (18)0.39091 (8)0.57349 (10)0.0189 (3)
C250.7561 (2)0.36685 (8)0.47734 (10)0.0218 (3)
H250.75270.31160.46130.026*
C260.71280 (19)0.42423 (8)0.40452 (10)0.0222 (3)
H260.68100.40740.33900.027*
O270.85085 (15)0.49003 (6)0.69379 (7)0.0241 (2)
C270.8323 (2)0.57144 (8)0.72334 (11)0.0275 (3)
H27A0.92850.60460.69590.041*
H27B0.85680.57470.79430.041*
H27C0.69900.59070.70010.041*
O280.84959 (15)0.34136 (6)0.65125 (7)0.0236 (2)
C280.8443 (3)0.25682 (8)0.63327 (12)0.0311 (3)
H28A0.71190.24140.60300.047*
H28B0.87750.22810.69470.047*
H28C0.94000.24330.58980.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0688 (8)0.0230 (6)0.0234 (6)0.0100 (5)0.0094 (5)0.0022 (4)
C10.0278 (7)0.0249 (7)0.0175 (7)0.0050 (5)0.0063 (5)0.0012 (5)
C20.0255 (7)0.0281 (7)0.0143 (6)0.0043 (5)0.0026 (5)0.0009 (5)
C30.0184 (6)0.0291 (7)0.0155 (6)0.0011 (5)0.0033 (5)0.0019 (5)
C110.0267 (7)0.0181 (6)0.0157 (6)0.0008 (5)0.0023 (5)0.0022 (5)
C120.0252 (7)0.0219 (7)0.0190 (7)0.0008 (5)0.0037 (5)0.0028 (5)
Cl120.0319 (2)0.0480 (3)0.0309 (2)0.01281 (16)0.01128 (16)0.00367 (16)
C130.0348 (8)0.0250 (7)0.0164 (7)0.0058 (6)0.0069 (6)0.0025 (5)
C140.0374 (8)0.0192 (6)0.0153 (7)0.0064 (6)0.0042 (6)0.0006 (5)
Cl140.0590 (3)0.0301 (2)0.0196 (2)0.00643 (17)0.00987 (17)0.00625 (14)
C150.0285 (7)0.0243 (7)0.0269 (8)0.0038 (6)0.0020 (6)0.0013 (6)
F150.0404 (6)0.0536 (6)0.0419 (6)0.0224 (5)0.0002 (5)0.0099 (5)
C160.0286 (7)0.0258 (7)0.0206 (7)0.0032 (6)0.0059 (6)0.0010 (6)
C210.0149 (6)0.0253 (7)0.0178 (6)0.0010 (5)0.0039 (5)0.0009 (5)
C220.0177 (6)0.0208 (6)0.0184 (7)0.0012 (5)0.0034 (5)0.0015 (5)
C230.0174 (6)0.0231 (6)0.0153 (6)0.0024 (5)0.0041 (5)0.0030 (5)
C240.0169 (6)0.0212 (6)0.0193 (7)0.0009 (5)0.0048 (5)0.0006 (5)
C250.0226 (6)0.0211 (6)0.0222 (7)0.0004 (5)0.0046 (5)0.0052 (5)
C260.0215 (6)0.0277 (7)0.0173 (7)0.0000 (5)0.0029 (5)0.0052 (5)
O270.0368 (6)0.0206 (5)0.0144 (5)0.0010 (4)0.0026 (4)0.0022 (4)
C270.0378 (8)0.0228 (7)0.0213 (7)0.0004 (6)0.0017 (6)0.0066 (6)
O280.0322 (5)0.0181 (5)0.0203 (5)0.0010 (4)0.0033 (4)0.0001 (4)
C280.0433 (9)0.0178 (7)0.0310 (8)0.0004 (6)0.0010 (7)0.0001 (6)
Geometric parameters (Å, º) top
O1—C11.2266 (18)C21—C221.4196 (19)
C1—C21.4638 (19)C22—C231.3773 (19)
C1—C111.5201 (18)C22—H220.9500
C2—C31.348 (2)C23—O271.3704 (16)
C2—H20.9500C23—C241.4225 (19)
C3—C211.4612 (19)C24—O281.3643 (16)
C3—H30.9500C24—C251.3924 (19)
C11—C121.3975 (19)C25—C261.397 (2)
C11—C161.398 (2)C25—H250.9500
C12—C131.396 (2)C26—H260.9500
C12—Cl121.7471 (14)O27—C271.4329 (16)
C13—C141.391 (2)C27—H27A0.9800
C13—H130.9500C27—H27B0.9800
C14—C151.384 (2)C27—H27C0.9800
C14—Cl141.7365 (14)O28—C281.4352 (17)
C15—F151.3479 (18)C28—H28A0.9800
C15—C161.385 (2)C28—H28B0.9800
C16—H160.9500C28—H28C0.9800
C21—C261.3988 (19)
O1—C1—C2121.74 (13)C23—C22—C21120.62 (12)
O1—C1—C11119.24 (13)C23—C22—H22119.7
C2—C1—C11119.00 (12)C21—C22—H22119.7
C3—C2—C1124.28 (13)O27—C23—C22125.51 (12)
C3—C2—H2117.9O27—C23—C24114.29 (12)
C1—C2—H2117.9C22—C23—C24120.20 (12)
C2—C3—C21127.60 (13)O28—C24—C25125.76 (12)
C2—C3—H3116.2O28—C24—C23114.65 (11)
C21—C3—H3116.2C25—C24—C23119.59 (12)
C12—C11—C16118.33 (13)C24—C25—C26119.78 (12)
C12—C11—C1122.81 (12)C24—C25—H25120.1
C16—C11—C1118.83 (12)C26—C25—H25120.1
C13—C12—C11121.99 (13)C25—C26—C21121.32 (12)
C13—C12—Cl12117.39 (11)C25—C26—H26119.3
C11—C12—Cl12120.62 (11)C21—C26—H26119.3
C14—C13—C12118.59 (13)C23—O27—C27117.06 (11)
C14—C13—H13120.7O27—C27—H27A109.5
C12—C13—H13120.7O27—C27—H27B109.5
C15—C14—C13119.82 (13)H27A—C27—H27B109.5
C15—C14—Cl14119.53 (12)O27—C27—H27C109.5
C13—C14—Cl14120.65 (11)H27A—C27—H27C109.5
F15—C15—C14119.56 (13)H27B—C27—H27C109.5
F15—C15—C16118.86 (14)C24—O28—C28117.54 (11)
C14—C15—C16121.58 (13)O28—C28—H28A109.5
C15—C16—C11119.67 (13)O28—C28—H28B109.5
C15—C16—H16120.2H28A—C28—H28B109.5
C11—C16—H16120.2O28—C28—H28C109.5
C26—C21—C22118.50 (12)H28A—C28—H28C109.5
C26—C21—C3119.23 (12)H28B—C28—H28C109.5
C22—C21—C3122.28 (12)
O1—C1—C2—C3173.54 (14)C12—C11—C16—C150.0 (2)
C11—C1—C2—C38.1 (2)C1—C11—C16—C15178.24 (13)
C1—C2—C3—C21178.68 (13)C2—C3—C21—C26179.42 (13)
O1—C1—C11—C1263.1 (2)C2—C3—C21—C220.0 (2)
C2—C1—C11—C12118.54 (15)C26—C21—C22—C230.41 (19)
O1—C1—C11—C16115.03 (16)C3—C21—C22—C23179.82 (12)
C2—C1—C11—C1663.35 (18)C21—C22—C23—O27179.32 (12)
C16—C11—C12—C130.8 (2)C21—C22—C23—C240.18 (19)
C1—C11—C12—C13178.91 (13)O27—C23—C24—O280.57 (16)
C16—C11—C12—Cl12179.59 (10)C22—C23—C24—O28179.88 (11)
C1—C11—C12—Cl121.47 (19)O27—C23—C24—C25178.67 (12)
C11—C12—C13—C140.7 (2)C22—C23—C24—C250.88 (19)
Cl12—C12—C13—C14179.69 (10)O28—C24—C25—C26179.87 (12)
C12—C13—C14—C150.2 (2)C23—C24—C25—C261.0 (2)
C12—C13—C14—Cl14179.44 (10)C24—C25—C26—C210.4 (2)
C13—C14—C15—F15179.81 (13)C22—C21—C26—C250.30 (19)
Cl14—C14—C15—F150.55 (19)C3—C21—C26—C25179.73 (12)
C13—C14—C15—C160.9 (2)C22—C23—O27—C276.65 (19)
Cl14—C14—C15—C16179.81 (11)C24—C23—O27—C27172.87 (11)
F15—C15—C16—C11179.92 (13)C25—C24—O28—C281.2 (2)
C14—C15—C16—C110.8 (2)C23—C24—O28—C28177.96 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O27i0.952.503.3067 (17)143
C16—H16···O28i0.952.433.3072 (17)154
Symmetry code: (i) x+1, y+1, z+1.
 

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