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The title compound, C13H10Cl2O3, was synthesized by the Reformatsky reaction of 2,4-dichlorobenzaldehyde and 2-(bromoacetyl)furan in an aqueous medium. Two intermolecular O—H
O hydrogen bonds are formed between the hydroxy and carbonyl groups of two molecules related by a center of symmetry.
O hydrogen bonds are formed between the hydroxy and carbonyl groups of two molecules related by a center of symmetry. Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029568/ww6151sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029568/ww6151Isup2.hkl |
CCDC reference: 234854
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.003 Å
Computing details top
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
3-(2,4-Dichlorophenyl)-1-(2-furyl)-3-hydroxypropan-1-one top
Crystal data top
| C13H10Cl2O3 | Z = 2 |
| Mr = 285.11 | F(000) = 292 |
| Triclinic, P1 | Dx = 1.482 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 340 K |
| a = 7.933 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.737 (3) Å | Cell parameters from 989 reflections |
| c = 9.907 (3) Å | θ = 2.7–26.3° |
| α = 79.464 (4)° | µ = 0.50 mm−1 |
| β = 72.596 (4)° | T = 293 K |
| γ = 79.918 (5)° | Plate, colorless |
| V = 638.9 (3) Å3 | 0.22 × 0.20 × 0.14 mm |
Data collection top
| Bruker SMART CCD area-detector diffractometer | 2246 independent reflections |
| Radiation source: fine-focus sealed tube | 1808 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.016 |
| ψ and ω scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
| Tmin = 0.882, Tmax = 0.932 | k = −10→9 |
| 3322 measured reflections | l = −11→11 |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.1932P] where P = (Fo2 + 2Fc2)/3 |
| 2246 reflections | (Δ/σ)max = 0.004 |
| 164 parameters | Δρmax = 0.32 e Å−3 |
| 0 restraints | Δρmin = −0.44 e Å−3 |
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 | 0.43230 (8) | 0.14544 (9) | 0.77489 (7) | 0.0706 (3) | |
| Cl2 | −0.17314 (9) | −0.08303 (9) | 0.84055 (8) | 0.0758 (3) | |
| O1 | 0.3100 (2) | 0.46997 (19) | 0.41418 (17) | 0.0588 (4) | |
| H1 | 0.2657 | 0.5367 | 0.4675 | 0.088* | |
| O2 | 0.7640 (2) | 0.3692 (2) | 0.34604 (18) | 0.0656 (5) | |
| O3 | 0.8364 (2) | 0.4239 (2) | 0.05729 (18) | 0.0687 (5) | |
| C1 | 0.0880 (3) | 0.2283 (3) | 0.5397 (2) | 0.0512 (6) | |
| H1A | 0.0737 | 0.2896 | 0.4557 | 0.061* | |
| C2 | −0.0390 (3) | 0.1325 (3) | 0.6170 (2) | 0.0535 (6) | |
| H2 | −0.1371 | 0.1285 | 0.5854 | 0.064* | |
| C3 | −0.0178 (3) | 0.0426 (3) | 0.7423 (2) | 0.0483 (5) | |
| C4 | 0.1239 (3) | 0.0486 (3) | 0.7919 (2) | 0.0466 (5) | |
| H4 | 0.1356 | −0.0109 | 0.8774 | 0.056* | |
| C5 | 0.2496 (3) | 0.1456 (3) | 0.7117 (2) | 0.0436 (5) | |
| C6 | 0.2371 (3) | 0.2358 (2) | 0.5837 (2) | 0.0411 (5) | |
| C7 | 0.3811 (3) | 0.3332 (3) | 0.4909 (2) | 0.0460 (5) | |
| H7 | 0.4445 | 0.3635 | 0.5510 | 0.055* | |
| C8 | 0.5123 (3) | 0.2362 (3) | 0.3812 (2) | 0.0569 (6) | |
| H8A | 0.5584 | 0.1389 | 0.4304 | 0.068* | |
| H8B | 0.4503 | 0.2100 | 0.3194 | 0.068* | |
| C9 | 0.6662 (3) | 0.3234 (3) | 0.2911 (2) | 0.0499 (5) | |
| C10 | 0.6960 (3) | 0.3472 (3) | 0.1375 (2) | 0.0473 (5) | |
| C11 | 0.6134 (3) | 0.3081 (3) | 0.0499 (3) | 0.0561 (6) | |
| H11 | 0.5142 | 0.2548 | 0.0773 | 0.067* | |
| C12 | 0.7062 (4) | 0.3635 (3) | −0.0913 (3) | 0.0663 (7) | |
| H12 | 0.6802 | 0.3541 | −0.1747 | 0.080* | |
| C13 | 0.8379 (4) | 0.4317 (4) | −0.0811 (3) | 0.0732 (8) | |
| H13 | 0.9203 | 0.4788 | −0.1586 | 0.088* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0547 (4) | 0.1037 (6) | 0.0590 (4) | −0.0306 (3) | −0.0275 (3) | 0.0139 (3) |
| Cl2 | 0.0567 (4) | 0.0902 (5) | 0.0782 (5) | −0.0356 (4) | −0.0115 (3) | 0.0075 (4) |
| O1 | 0.0757 (12) | 0.0515 (9) | 0.0461 (9) | −0.0115 (8) | −0.0158 (8) | 0.0025 (7) |
| O2 | 0.0646 (11) | 0.0862 (13) | 0.0510 (10) | −0.0243 (10) | −0.0096 (8) | −0.0190 (9) |
| O3 | 0.0678 (11) | 0.0902 (13) | 0.0469 (10) | −0.0369 (10) | −0.0017 (8) | −0.0050 (9) |
| C1 | 0.0560 (13) | 0.0611 (14) | 0.0385 (11) | −0.0097 (11) | −0.0174 (10) | −0.0021 (10) |
| C2 | 0.0459 (13) | 0.0686 (15) | 0.0513 (13) | −0.0121 (11) | −0.0169 (10) | −0.0114 (11) |
| C3 | 0.0392 (11) | 0.0540 (13) | 0.0493 (13) | −0.0106 (10) | −0.0058 (10) | −0.0077 (10) |
| C4 | 0.0426 (12) | 0.0525 (13) | 0.0406 (11) | −0.0061 (10) | −0.0090 (9) | 0.0001 (9) |
| C5 | 0.0381 (11) | 0.0533 (12) | 0.0400 (11) | −0.0065 (9) | −0.0112 (9) | −0.0064 (9) |
| C6 | 0.0451 (11) | 0.0448 (11) | 0.0330 (10) | −0.0075 (9) | −0.0074 (9) | −0.0083 (9) |
| C7 | 0.0539 (13) | 0.0489 (12) | 0.0350 (11) | −0.0139 (10) | −0.0086 (9) | −0.0048 (9) |
| C8 | 0.0634 (15) | 0.0554 (14) | 0.0474 (13) | −0.0200 (12) | 0.0018 (11) | −0.0127 (11) |
| C9 | 0.0507 (13) | 0.0507 (13) | 0.0460 (12) | −0.0087 (10) | −0.0045 (10) | −0.0137 (10) |
| C10 | 0.0466 (12) | 0.0481 (12) | 0.0439 (12) | −0.0109 (10) | −0.0046 (10) | −0.0063 (10) |
| C11 | 0.0556 (14) | 0.0597 (14) | 0.0545 (14) | −0.0095 (11) | −0.0147 (11) | −0.0105 (11) |
| C12 | 0.0792 (19) | 0.0743 (18) | 0.0461 (14) | −0.0050 (15) | −0.0202 (13) | −0.0096 (12) |
| C13 | 0.084 (2) | 0.085 (2) | 0.0413 (14) | −0.0208 (16) | −0.0020 (13) | −0.0025 (13) |
Geometric parameters (Å, º) top
| Cl1—C5 | 1.742 (2) | C5—C6 | 1.386 (3) |
| Cl2—C3 | 1.743 (2) | C6—C7 | 1.516 (3) |
| O1—C7 | 1.418 (3) | C7—C8 | 1.528 (3) |
| O1—H1 | 0.8200 | C7—H7 | 0.9800 |
| O2—C9 | 1.224 (3) | C8—C9 | 1.514 (3) |
| O3—C13 | 1.357 (3) | C8—H8A | 0.9700 |
| O3—C10 | 1.363 (3) | C8—H8B | 0.9700 |
| C1—C2 | 1.379 (3) | C9—C10 | 1.449 (3) |
| C1—C6 | 1.393 (3) | C10—C11 | 1.352 (3) |
| C1—H1A | 0.9300 | C11—C12 | 1.412 (4) |
| C2—C3 | 1.381 (3) | C11—H11 | 0.9300 |
| C2—H2 | 0.9300 | C12—C13 | 1.326 (4) |
| C3—C4 | 1.367 (3) | C12—H12 | 0.9300 |
| C4—C5 | 1.386 (3) | C13—H13 | 0.9300 |
| C4—H4 | 0.9300 | ||
| C7—O1—H1 | 109.5 | C6—C7—H7 | 109.4 |
| C13—O3—C10 | 106.5 (2) | C8—C7—H7 | 109.4 |
| C2—C1—C6 | 121.9 (2) | C9—C8—C7 | 111.98 (18) |
| C2—C1—H1A | 119.0 | C9—C8—H8A | 109.2 |
| C6—C1—H1A | 119.0 | C7—C8—H8A | 109.2 |
| C1—C2—C3 | 118.8 (2) | C9—C8—H8B | 109.2 |
| C1—C2—H2 | 120.6 | C7—C8—H8B | 109.2 |
| C3—C2—H2 | 120.6 | H8A—C8—H8B | 107.9 |
| C4—C3—C2 | 121.6 (2) | O2—C9—C10 | 121.3 (2) |
| C4—C3—Cl2 | 118.45 (17) | O2—C9—C8 | 121.1 (2) |
| C2—C3—Cl2 | 119.98 (17) | C10—C9—C8 | 117.6 (2) |
| C3—C4—C5 | 118.3 (2) | C11—C10—O3 | 109.1 (2) |
| C3—C4—H4 | 120.8 | C11—C10—C9 | 133.8 (2) |
| C5—C4—H4 | 120.8 | O3—C10—C9 | 117.1 (2) |
| C6—C5—C4 | 122.57 (19) | C10—C11—C12 | 107.1 (2) |
| C6—C5—Cl1 | 120.29 (16) | C10—C11—H11 | 126.5 |
| C4—C5—Cl1 | 117.11 (16) | C12—C11—H11 | 126.5 |
| C5—C6—C1 | 116.80 (19) | C13—C12—C11 | 106.2 (2) |
| C5—C6—C7 | 122.51 (19) | C13—C12—H12 | 126.9 |
| C1—C6—C7 | 120.63 (18) | C11—C12—H12 | 126.9 |
| O1—C7—C6 | 111.93 (18) | C12—C13—O3 | 111.1 (2) |
| O1—C7—C8 | 107.32 (18) | C12—C13—H13 | 124.4 |
| C6—C7—C8 | 109.40 (17) | O3—C13—H13 | 124.4 |
| O1—C7—H7 | 109.4 | ||
| C6—C1—C2—C3 | 0.5 (4) | C1—C6—C7—C8 | −85.0 (3) |
| C1—C2—C3—C4 | 1.1 (4) | O1—C7—C8—C9 | 62.0 (3) |
| C1—C2—C3—Cl2 | −178.54 (17) | C6—C7—C8—C9 | −176.37 (19) |
| C2—C3—C4—C5 | −1.3 (3) | C7—C8—C9—O2 | 58.6 (3) |
| Cl2—C3—C4—C5 | 178.37 (16) | C7—C8—C9—C10 | −122.8 (2) |
| C3—C4—C5—C6 | −0.1 (3) | C13—O3—C10—C11 | 0.3 (3) |
| C3—C4—C5—Cl1 | −177.88 (17) | C13—O3—C10—C9 | 179.8 (2) |
| C4—C5—C6—C1 | 1.6 (3) | O2—C9—C10—C11 | 178.9 (3) |
| Cl1—C5—C6—C1 | 179.31 (16) | C8—C9—C10—C11 | 0.3 (4) |
| C4—C5—C6—C7 | −175.64 (19) | O2—C9—C10—O3 | −0.5 (3) |
| Cl1—C5—C6—C7 | 2.0 (3) | C8—C9—C10—O3 | −179.1 (2) |
| C2—C1—C6—C5 | −1.8 (3) | O3—C10—C11—C12 | −0.2 (3) |
| C2—C1—C6—C7 | 175.5 (2) | C9—C10—C11—C12 | −179.7 (3) |
| C5—C6—C7—O1 | −149.0 (2) | C10—C11—C12—C13 | 0.1 (3) |
| C1—C6—C7—O1 | 33.8 (3) | C11—C12—C13—O3 | 0.1 (3) |
| C5—C6—C7—C8 | 92.2 (2) | C10—O3—C13—C12 | −0.2 (3) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 0.82 | 2.09 | 2.839 (3) | 152 |
| C7—H7···Cl1 | 0.98 | 2.64 | 3.088 (2) | 108 |
| C12—H12···O1ii | 0.93 | 2.57 | 3.293 (3) | 135 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
