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The geometric parameters of the title mol­ecule, C15H10Cl2O2, are in the ususal ranges. The central double bond is trans configured. The dihedral angle between the dichloro­phenyl and hydroxy­phenyl rings is 71.38 (3)°. The crystal packing is stabilized by O—H...O hydrogen bonds and C—H...O contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055024/lh2280sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055024/lh2280Isup2.hkl
Contains datablock I

CCDC reference: 636738

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.032
  • wR factor = 0.084
  • Data-to-parameter ratio = 21.1

checkCIF/PLATON results

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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.

(2E)-1-(2,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C15H10Cl2O2F(000) = 1200
Mr = 293.13Dx = 1.467 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 50392 reflections
a = 14.5702 (5) Åθ = 2.8–28.9°
b = 8.8146 (4) ŵ = 0.48 mm1
c = 20.6699 (7) ÅT = 173 K
V = 2654.65 (18) Å3Block, orange
Z = 80.36 × 0.33 × 0.32 mm
Data collection top
Stoe IPDS-II two-circle
diffractometer
3736 independent reflections
Radiation source: fine-focus sealed tube3486 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 29.7°, θmin = 2.8°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1920
Tmin = 0.846, Tmax = 0.861k = 1212
47302 measured reflectionsl = 2828
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.2454P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3736 reflectionsΔρmax = 0.36 e Å3
177 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0073 (7)
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
Cl10.74623 (2)0.29091 (4)0.223353 (15)0.03212 (10)
Cl21.07277 (2)0.57695 (4)0.213640 (18)0.03754 (10)
O10.73437 (6)0.28622 (11)0.02984 (4)0.02824 (19)
O20.39744 (6)0.27875 (10)0.03016 (5)0.02800 (19)
H20.3456 (14)0.261 (2)0.0129 (10)0.049 (5)*
C10.72896 (7)0.37001 (13)0.07746 (5)0.0206 (2)
C20.64258 (7)0.43662 (13)0.09997 (5)0.0226 (2)
H2A0.64330.50190.13650.027*
C30.56209 (7)0.40777 (12)0.07022 (5)0.0200 (2)
H30.56280.33840.03510.024*
C110.81515 (7)0.41533 (12)0.11295 (5)0.0199 (2)
C120.82791 (7)0.39183 (12)0.17911 (5)0.0211 (2)
C130.90662 (8)0.44059 (13)0.21128 (6)0.0242 (2)
H130.91430.42450.25640.029*
C140.97356 (8)0.51376 (13)0.17488 (6)0.0248 (2)
C150.96494 (8)0.53649 (13)0.10865 (6)0.0264 (2)
H151.01230.58490.08480.032*
C160.88531 (8)0.48685 (14)0.07805 (6)0.0244 (2)
H160.87840.50170.03280.029*
C210.47392 (7)0.47499 (12)0.08784 (5)0.0197 (2)
C220.39134 (7)0.40636 (12)0.06703 (5)0.0209 (2)
C230.30627 (8)0.46780 (13)0.08488 (6)0.0254 (2)
H230.25110.41920.07190.030*
C240.30274 (8)0.59963 (15)0.12152 (6)0.0282 (2)
H240.24500.64070.13370.034*
C250.38357 (8)0.67231 (14)0.14066 (6)0.0287 (2)
H250.38090.76380.16490.034*
C260.46771 (8)0.60980 (13)0.12402 (6)0.0244 (2)
H260.52250.65920.13740.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02169 (14)0.04302 (19)0.03164 (15)0.00460 (11)0.00240 (11)0.01186 (12)
Cl20.02207 (15)0.04266 (19)0.0479 (2)0.00749 (12)0.00676 (12)0.01225 (14)
O10.0189 (4)0.0374 (5)0.0284 (4)0.0016 (3)0.0016 (3)0.0096 (4)
O20.0197 (4)0.0260 (4)0.0383 (5)0.0019 (3)0.0087 (3)0.0091 (3)
C10.0157 (4)0.0231 (5)0.0232 (5)0.0002 (4)0.0004 (4)0.0008 (4)
C20.0168 (5)0.0270 (5)0.0241 (5)0.0018 (4)0.0005 (4)0.0041 (4)
C30.0167 (5)0.0215 (5)0.0216 (5)0.0007 (4)0.0005 (4)0.0001 (4)
C110.0147 (4)0.0200 (4)0.0251 (5)0.0016 (4)0.0004 (4)0.0000 (4)
C120.0164 (5)0.0207 (5)0.0263 (5)0.0007 (4)0.0010 (4)0.0015 (4)
C130.0207 (5)0.0248 (5)0.0270 (5)0.0017 (4)0.0027 (4)0.0018 (4)
C140.0165 (5)0.0215 (5)0.0364 (6)0.0003 (4)0.0033 (4)0.0055 (4)
C150.0188 (5)0.0239 (5)0.0364 (6)0.0038 (4)0.0027 (4)0.0002 (4)
C160.0198 (5)0.0267 (5)0.0266 (5)0.0009 (4)0.0020 (4)0.0023 (4)
C210.0154 (4)0.0224 (5)0.0212 (5)0.0006 (4)0.0009 (3)0.0006 (4)
C220.0177 (5)0.0208 (5)0.0243 (5)0.0009 (4)0.0029 (4)0.0010 (4)
C230.0162 (5)0.0270 (5)0.0329 (6)0.0001 (4)0.0016 (4)0.0023 (4)
C240.0193 (5)0.0303 (6)0.0348 (6)0.0047 (4)0.0049 (4)0.0003 (5)
C250.0258 (6)0.0268 (6)0.0335 (6)0.0027 (4)0.0034 (5)0.0070 (5)
C260.0197 (5)0.0255 (5)0.0278 (5)0.0013 (4)0.0004 (4)0.0036 (4)
Geometric parameters (Å, º) top
Cl1—C121.7446 (11)C13—H130.9500
Cl2—C141.7440 (11)C14—C151.3893 (18)
O1—C11.2331 (14)C15—C161.3920 (16)
O2—C221.3616 (14)C15—H150.9500
O2—H20.85 (2)C16—H160.9500
C1—C21.4646 (15)C21—C261.4069 (15)
C1—C111.5082 (14)C21—C221.4137 (14)
C2—C31.3484 (15)C22—C231.4021 (15)
C2—H2A0.9500C23—C241.3880 (17)
C3—C211.4609 (14)C23—H230.9500
C3—H30.9500C24—C251.3979 (17)
C11—C121.3956 (15)C24—H240.9500
C11—C161.4010 (15)C25—C261.3874 (16)
C12—C131.3936 (15)C25—H250.9500
C13—C141.3905 (17)C26—H260.9500
C22—O2—H2109.2 (13)C14—C15—H15120.7
O1—C1—C2123.27 (10)C16—C15—H15120.7
O1—C1—C11119.58 (9)C15—C16—C11121.05 (11)
C2—C1—C11117.05 (9)C15—C16—H16119.5
C3—C2—C1121.79 (10)C11—C16—H16119.5
C3—C2—H2A119.1C26—C21—C22117.93 (10)
C1—C2—H2A119.1C26—C21—C3122.12 (10)
C2—C3—C21125.07 (10)C22—C21—C3119.93 (10)
C2—C3—H3117.5O2—C22—C23121.60 (10)
C21—C3—H3117.5O2—C22—C21117.92 (10)
C12—C11—C16118.30 (10)C23—C22—C21120.47 (10)
C12—C11—C1123.25 (9)C24—C23—C22119.98 (11)
C16—C11—C1118.44 (10)C24—C23—H23120.0
C13—C12—C11122.10 (10)C22—C23—H23120.0
C13—C12—Cl1117.94 (9)C23—C24—C25120.46 (11)
C11—C12—Cl1119.89 (8)C23—C24—H24119.8
C14—C13—C12117.52 (11)C25—C24—H24119.8
C14—C13—H13121.2C26—C25—C24119.49 (11)
C12—C13—H13121.2C26—C25—H25120.3
C15—C14—C13122.46 (10)C24—C25—H25120.3
C15—C14—Cl2118.78 (9)C25—C26—C21121.60 (11)
C13—C14—Cl2118.75 (9)C25—C26—H26119.2
C14—C15—C16118.54 (11)C21—C26—H26119.2
O1—C1—C2—C31.23 (18)C14—C15—C16—C110.06 (18)
C11—C1—C2—C3177.66 (10)C12—C11—C16—C151.43 (17)
C1—C2—C3—C21177.07 (10)C1—C11—C16—C15177.52 (10)
O1—C1—C11—C12124.71 (12)C2—C3—C21—C2620.03 (17)
C2—C1—C11—C1258.72 (15)C2—C3—C21—C22161.58 (11)
O1—C1—C11—C1656.40 (15)C26—C21—C22—O2177.81 (10)
C2—C1—C11—C16120.17 (12)C3—C21—C22—O20.64 (15)
C16—C11—C12—C131.69 (16)C26—C21—C22—C233.02 (16)
C1—C11—C12—C13177.21 (10)C3—C21—C22—C23178.53 (10)
C16—C11—C12—Cl1175.29 (9)O2—C22—C23—C24178.82 (11)
C1—C11—C12—Cl15.81 (15)C21—C22—C23—C242.05 (17)
C11—C12—C13—C140.42 (17)C22—C23—C24—C250.24 (19)
Cl1—C12—C13—C14176.61 (9)C23—C24—C25—C261.47 (19)
C12—C13—C14—C151.17 (17)C24—C25—C26—C210.42 (19)
C12—C13—C14—Cl2179.76 (8)C22—C21—C26—C251.80 (17)
C13—C14—C15—C161.40 (18)C3—C21—C26—C25179.79 (11)
Cl2—C14—C15—C16179.52 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.85 (2)1.89 (2)2.7408 (12)176 (2)
C15—H15···O2ii0.952.433.3485 (15)162
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x+3/2, y+1/2, z.
 

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