The geometric parameters of the title molecule, C
15H
10Cl
2O
2, 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
CCDC reference: 636738
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.032
- wR factor = 0.084
- Data-to-parameter ratio = 21.1
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.
(2E)-1-(2,4-Dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
top
Crystal data top
C15H10Cl2O2 | F(000) = 1200 |
Mr = 293.13 | Dx = 1.467 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 50392 reflections |
a = 14.5702 (5) Å | θ = 2.8–28.9° |
b = 8.8146 (4) Å | µ = 0.48 mm−1 |
c = 20.6699 (7) Å | T = 173 K |
V = 2654.65 (18) Å3 | Block, orange |
Z = 8 | 0.36 × 0.33 × 0.32 mm |
Data collection top
Stoe IPDS-II two-circle diffractometer | 3736 independent reflections |
Radiation source: fine-focus sealed tube | 3486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 29.7°, θmin = 2.8° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −19→20 |
Tmin = 0.846, Tmax = 0.861 | k = −12→12 |
47302 measured reflections | l = −28→28 |
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)] = 0.032 | H 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 reflections | Δρmax = 0.36 e Å−3 |
177 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.74623 (2) | 0.29091 (4) | 0.223353 (15) | 0.03212 (10) | |
Cl2 | 1.07277 (2) | 0.57695 (4) | 0.213640 (18) | 0.03754 (10) | |
O1 | 0.73437 (6) | 0.28622 (11) | 0.02984 (4) | 0.02824 (19) | |
O2 | 0.39744 (6) | 0.27875 (10) | 0.03016 (5) | 0.02800 (19) | |
H2 | 0.3456 (14) | 0.261 (2) | 0.0129 (10) | 0.049 (5)* | |
C1 | 0.72896 (7) | 0.37001 (13) | 0.07746 (5) | 0.0206 (2) | |
C2 | 0.64258 (7) | 0.43662 (13) | 0.09997 (5) | 0.0226 (2) | |
H2A | 0.6433 | 0.5019 | 0.1365 | 0.027* | |
C3 | 0.56209 (7) | 0.40777 (12) | 0.07022 (5) | 0.0200 (2) | |
H3 | 0.5628 | 0.3384 | 0.0351 | 0.024* | |
C11 | 0.81515 (7) | 0.41533 (12) | 0.11295 (5) | 0.0199 (2) | |
C12 | 0.82791 (7) | 0.39183 (12) | 0.17911 (5) | 0.0211 (2) | |
C13 | 0.90662 (8) | 0.44059 (13) | 0.21128 (6) | 0.0242 (2) | |
H13 | 0.9143 | 0.4245 | 0.2564 | 0.029* | |
C14 | 0.97356 (8) | 0.51376 (13) | 0.17488 (6) | 0.0248 (2) | |
C15 | 0.96494 (8) | 0.53649 (13) | 0.10865 (6) | 0.0264 (2) | |
H15 | 1.0123 | 0.5849 | 0.0848 | 0.032* | |
C16 | 0.88531 (8) | 0.48685 (14) | 0.07805 (6) | 0.0244 (2) | |
H16 | 0.8784 | 0.5017 | 0.0328 | 0.029* | |
C21 | 0.47392 (7) | 0.47499 (12) | 0.08784 (5) | 0.0197 (2) | |
C22 | 0.39134 (7) | 0.40636 (12) | 0.06703 (5) | 0.0209 (2) | |
C23 | 0.30627 (8) | 0.46780 (13) | 0.08488 (6) | 0.0254 (2) | |
H23 | 0.2511 | 0.4192 | 0.0719 | 0.030* | |
C24 | 0.30274 (8) | 0.59963 (15) | 0.12152 (6) | 0.0282 (2) | |
H24 | 0.2450 | 0.6407 | 0.1337 | 0.034* | |
C25 | 0.38357 (8) | 0.67231 (14) | 0.14066 (6) | 0.0287 (2) | |
H25 | 0.3809 | 0.7638 | 0.1649 | 0.034* | |
C26 | 0.46771 (8) | 0.60980 (13) | 0.12402 (6) | 0.0244 (2) | |
H26 | 0.5225 | 0.6592 | 0.1374 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.02169 (14) | 0.04302 (19) | 0.03164 (15) | −0.00460 (11) | 0.00240 (11) | 0.01186 (12) |
Cl2 | 0.02207 (15) | 0.04266 (19) | 0.0479 (2) | −0.00749 (12) | −0.00676 (12) | −0.01225 (14) |
O1 | 0.0189 (4) | 0.0374 (5) | 0.0284 (4) | 0.0016 (3) | 0.0016 (3) | −0.0096 (4) |
O2 | 0.0197 (4) | 0.0260 (4) | 0.0383 (5) | 0.0019 (3) | −0.0087 (3) | −0.0091 (3) |
C1 | 0.0157 (4) | 0.0231 (5) | 0.0232 (5) | −0.0002 (4) | 0.0004 (4) | 0.0008 (4) |
C2 | 0.0168 (5) | 0.0270 (5) | 0.0241 (5) | 0.0018 (4) | −0.0005 (4) | −0.0041 (4) |
C3 | 0.0167 (5) | 0.0215 (5) | 0.0216 (5) | 0.0007 (4) | 0.0005 (4) | −0.0001 (4) |
C11 | 0.0147 (4) | 0.0200 (4) | 0.0251 (5) | 0.0016 (4) | 0.0004 (4) | 0.0000 (4) |
C12 | 0.0164 (5) | 0.0207 (5) | 0.0263 (5) | 0.0007 (4) | 0.0010 (4) | 0.0015 (4) |
C13 | 0.0207 (5) | 0.0248 (5) | 0.0270 (5) | 0.0017 (4) | −0.0027 (4) | −0.0018 (4) |
C14 | 0.0165 (5) | 0.0215 (5) | 0.0364 (6) | −0.0003 (4) | −0.0033 (4) | −0.0055 (4) |
C15 | 0.0188 (5) | 0.0239 (5) | 0.0364 (6) | −0.0038 (4) | 0.0027 (4) | 0.0002 (4) |
C16 | 0.0198 (5) | 0.0267 (5) | 0.0266 (5) | −0.0009 (4) | 0.0020 (4) | 0.0023 (4) |
C21 | 0.0154 (4) | 0.0224 (5) | 0.0212 (5) | 0.0006 (4) | −0.0009 (3) | 0.0006 (4) |
C22 | 0.0177 (5) | 0.0208 (5) | 0.0243 (5) | 0.0009 (4) | −0.0029 (4) | 0.0010 (4) |
C23 | 0.0162 (5) | 0.0270 (5) | 0.0329 (6) | 0.0001 (4) | −0.0016 (4) | 0.0023 (4) |
C24 | 0.0193 (5) | 0.0303 (6) | 0.0348 (6) | 0.0047 (4) | 0.0049 (4) | 0.0003 (5) |
C25 | 0.0258 (6) | 0.0268 (6) | 0.0335 (6) | 0.0027 (4) | 0.0034 (5) | −0.0070 (5) |
C26 | 0.0197 (5) | 0.0255 (5) | 0.0278 (5) | −0.0013 (4) | −0.0004 (4) | −0.0036 (4) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.7446 (11) | C13—H13 | 0.9500 |
Cl2—C14 | 1.7440 (11) | C14—C15 | 1.3893 (18) |
O1—C1 | 1.2331 (14) | C15—C16 | 1.3920 (16) |
O2—C22 | 1.3616 (14) | C15—H15 | 0.9500 |
O2—H2 | 0.85 (2) | C16—H16 | 0.9500 |
C1—C2 | 1.4646 (15) | C21—C26 | 1.4069 (15) |
C1—C11 | 1.5082 (14) | C21—C22 | 1.4137 (14) |
C2—C3 | 1.3484 (15) | C22—C23 | 1.4021 (15) |
C2—H2A | 0.9500 | C23—C24 | 1.3880 (17) |
C3—C21 | 1.4609 (14) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.3979 (17) |
C11—C12 | 1.3956 (15) | C24—H24 | 0.9500 |
C11—C16 | 1.4010 (15) | C25—C26 | 1.3874 (16) |
C12—C13 | 1.3936 (15) | C25—H25 | 0.9500 |
C13—C14 | 1.3905 (17) | C26—H26 | 0.9500 |
| | | |
C22—O2—H2 | 109.2 (13) | C14—C15—H15 | 120.7 |
O1—C1—C2 | 123.27 (10) | C16—C15—H15 | 120.7 |
O1—C1—C11 | 119.58 (9) | C15—C16—C11 | 121.05 (11) |
C2—C1—C11 | 117.05 (9) | C15—C16—H16 | 119.5 |
C3—C2—C1 | 121.79 (10) | C11—C16—H16 | 119.5 |
C3—C2—H2A | 119.1 | C26—C21—C22 | 117.93 (10) |
C1—C2—H2A | 119.1 | C26—C21—C3 | 122.12 (10) |
C2—C3—C21 | 125.07 (10) | C22—C21—C3 | 119.93 (10) |
C2—C3—H3 | 117.5 | O2—C22—C23 | 121.60 (10) |
C21—C3—H3 | 117.5 | O2—C22—C21 | 117.92 (10) |
C12—C11—C16 | 118.30 (10) | C23—C22—C21 | 120.47 (10) |
C12—C11—C1 | 123.25 (9) | C24—C23—C22 | 119.98 (11) |
C16—C11—C1 | 118.44 (10) | C24—C23—H23 | 120.0 |
C13—C12—C11 | 122.10 (10) | C22—C23—H23 | 120.0 |
C13—C12—Cl1 | 117.94 (9) | C23—C24—C25 | 120.46 (11) |
C11—C12—Cl1 | 119.89 (8) | C23—C24—H24 | 119.8 |
C14—C13—C12 | 117.52 (11) | C25—C24—H24 | 119.8 |
C14—C13—H13 | 121.2 | C26—C25—C24 | 119.49 (11) |
C12—C13—H13 | 121.2 | C26—C25—H25 | 120.3 |
C15—C14—C13 | 122.46 (10) | C24—C25—H25 | 120.3 |
C15—C14—Cl2 | 118.78 (9) | C25—C26—C21 | 121.60 (11) |
C13—C14—Cl2 | 118.75 (9) | C25—C26—H26 | 119.2 |
C14—C15—C16 | 118.54 (11) | C21—C26—H26 | 119.2 |
| | | |
O1—C1—C2—C3 | 1.23 (18) | C14—C15—C16—C11 | −0.06 (18) |
C11—C1—C2—C3 | 177.66 (10) | C12—C11—C16—C15 | −1.43 (17) |
C1—C2—C3—C21 | −177.07 (10) | C1—C11—C16—C15 | 177.52 (10) |
O1—C1—C11—C12 | −124.71 (12) | C2—C3—C21—C26 | 20.03 (17) |
C2—C1—C11—C12 | 58.72 (15) | C2—C3—C21—C22 | −161.58 (11) |
O1—C1—C11—C16 | 56.40 (15) | C26—C21—C22—O2 | 177.81 (10) |
C2—C1—C11—C16 | −120.17 (12) | C3—C21—C22—O2 | −0.64 (15) |
C16—C11—C12—C13 | 1.69 (16) | C26—C21—C22—C23 | −3.02 (16) |
C1—C11—C12—C13 | −177.21 (10) | C3—C21—C22—C23 | 178.53 (10) |
C16—C11—C12—Cl1 | −175.29 (9) | O2—C22—C23—C24 | −178.82 (11) |
C1—C11—C12—Cl1 | 5.81 (15) | C21—C22—C23—C24 | 2.05 (17) |
C11—C12—C13—C14 | −0.42 (17) | C22—C23—C24—C25 | 0.24 (19) |
Cl1—C12—C13—C14 | 176.61 (9) | C23—C24—C25—C26 | −1.47 (19) |
C12—C13—C14—C15 | −1.17 (17) | C24—C25—C26—C21 | 0.42 (19) |
C12—C13—C14—Cl2 | 179.76 (8) | C22—C21—C26—C25 | 1.80 (17) |
C13—C14—C15—C16 | 1.40 (18) | C3—C21—C26—C25 | −179.79 (11) |
Cl2—C14—C15—C16 | −179.52 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.85 (2) | 1.89 (2) | 2.7408 (12) | 176 (2) |
C15—H15···O2ii | 0.95 | 2.43 | 3.3485 (15) | 162 |
Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+3/2, y+1/2, z. |