Acta Cryst. (2007). E63, o3707 [ doi:10.1107/S1600536807037671 ]
In the title compound, C13H14O2, a derivative of isocoumarin, the packing is stabilized by intermolecular C-H
O interactions.
The title compound was synthesized from a mixture of homophthalic acid (1 mmol) and pentanoyl chloride (4 mmol)·The mixture was placed in a glass tube fitted with a tightened rubber septum and was refluxed at 393 K under a nitrogen atmosphere. The completion of the reaction was monitored by TLC using a hexane:ethylacetate (9:1 v/v) mixture. After the completion of reaction, the mixture was dissolved in dichloromethane and adsorbed on silica gel. The compound was purified by column chromatography using a mixture of hexane/ethyl acetate (9:1 v/v). Colourless blocks of (I) were recrystalized from ether.
All the H atoms were located and refined isotropically resulting in C—H bond lengths of 0.93 (3)–1.02 (3) Å.
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1999) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
![[Figure 1]](./hb2496fig1thm.gif)
| Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. |
![[Figure 2]](./hb2496fig2thm.gif)
| Fig. 2. Packing diagram of (I) viewed down the a axis. The dotted lines indicate intermolecular C—H···O interactions. |
| C13H14O2 | F000 = 432 |
| Mr = 202.24 | Dx = 1.218 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1190 reflections |
| a = 8.3929 (12) Å | θ = 2.5–24.4º |
| b = 14.862 (2) Å | µ = 0.08 mm−1 |
| c = 8.8880 (12) Å | T = 290 (2) K |
| β = 95.963 (2)º | Block, colourless |
| V = 1102.6 (3) Å3 | 0.47 × 0.42 × 0.30 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2161 independent reflections |
| Radiation source: fine-focus sealed tube | 1201 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.040 |
| T = 290(2) K | θmax = 26.0º |
| φ and ω scans | θmin = 2.4º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
| Tmin = 0.927, Tmax = 0.976 | k = −18→16 |
| 8442 measured reflections | l = −10→10 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0452P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.93 | (Δ/σ)max < 0.001 |
| 2161 reflections | Δρmax = 0.14 e Å−3 |
| 192 parameters | Δρmin = −0.14 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C13H14O2 | V = 1102.6 (3) Å3 |
| Mr = 202.24 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 8.3929 (12) Å | µ = 0.08 mm−1 |
| b = 14.862 (2) Å | T = 290 (2) K |
| c = 8.8880 (12) Å | 0.47 × 0.42 × 0.30 mm |
| β = 95.963 (2)º |
| Bruker SMART CCD area-detector diffractometer | 2161 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1201 reflections with I > 2σ(I) |
| Tmin = 0.927, Tmax = 0.976 | Rint = 0.040 |
| 8442 measured reflections |
| R[F2 > 2σ(F2)] = 0.043 | 192 parameters |
| wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
| S = 0.93 | Δρmax = 0.14 e Å−3 |
| 2161 reflections | Δρmin = −0.14 e Å−3 |
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 > 2sigma(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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.16015 (18) | 0.09619 (8) | −0.34990 (14) | 0.0868 (5) | |
| O2 | 0.27788 (14) | 0.10418 (7) | −0.11803 (13) | 0.0600 (4) | |
| C1 | 0.1839 (2) | 0.05878 (12) | −0.2290 (2) | 0.0596 (5) | |
| C2 | 0.12493 (18) | −0.02983 (11) | −0.19035 (17) | 0.0492 (4) | |
| C3 | 0.0271 (2) | −0.07876 (14) | −0.2979 (2) | 0.0599 (5) | |
| C4 | −0.0265 (2) | −0.16201 (14) | −0.2621 (2) | 0.0628 (5) | |
| C5 | 0.0146 (2) | −0.19757 (14) | −0.1198 (2) | 0.0622 (5) | |
| C6 | 0.1090 (2) | −0.15013 (12) | −0.0126 (2) | 0.0573 (5) | |
| C7 | 0.16625 (18) | −0.06484 (10) | −0.04574 (17) | 0.0457 (4) | |
| C8 | 0.2651 (2) | −0.01165 (11) | 0.06149 (19) | 0.0511 (4) | |
| C9 | 0.31617 (19) | 0.06910 (11) | 0.02615 (18) | 0.0501 (4) | |
| C10 | 0.4163 (2) | 0.13379 (13) | 0.1222 (2) | 0.0567 (5) | |
| C11 | 0.4656 (2) | 0.10221 (13) | 0.2824 (2) | 0.0575 (5) | |
| C12 | 0.5681 (3) | 0.16981 (14) | 0.3760 (2) | 0.0677 (6) | |
| C13 | 0.6172 (4) | 0.13693 (19) | 0.5347 (3) | 0.0868 (7) | |
| H3 | 0.0023 (19) | −0.0544 (11) | −0.398 (2) | 0.071 (5)* | |
| H4 | −0.0935 (19) | −0.1958 (11) | −0.3365 (17) | 0.065 (5)* | |
| H5 | −0.024 (2) | −0.2557 (12) | −0.0998 (17) | 0.073 (6)* | |
| H6 | 0.1368 (19) | −0.1730 (11) | 0.0846 (18) | 0.063 (5)* | |
| H8 | 0.2914 (16) | −0.0350 (10) | 0.1603 (16) | 0.052 (4)* | |
| H10A | 0.3558 (18) | 0.1912 (11) | 0.1235 (16) | 0.061 (5)* | |
| H10B | 0.514 (2) | 0.1494 (10) | 0.0729 (17) | 0.070 (5)* | |
| H11A | 0.370 (2) | 0.0877 (10) | 0.3357 (17) | 0.063 (5)* | |
| H11B | 0.5267 (18) | 0.0431 (11) | 0.2821 (16) | 0.062 (5)* | |
| H12A | 0.509 (2) | 0.2228 (13) | 0.3777 (19) | 0.079 (6)* | |
| H12B | 0.662 (2) | 0.1838 (12) | 0.3201 (19) | 0.081 (6)* | |
| H13A | 0.524 (3) | 0.1253 (14) | 0.587 (3) | 0.116 (9)* | |
| H13B | 0.676 (3) | 0.0771 (15) | 0.535 (2) | 0.106 (8)* | |
| H13C | 0.680 (2) | 0.1827 (14) | 0.593 (2) | 0.091 (7)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.1246 (13) | 0.0719 (9) | 0.0602 (9) | 0.0015 (8) | −0.0084 (8) | 0.0199 (7) |
| O2 | 0.0741 (9) | 0.0484 (7) | 0.0573 (7) | 0.0005 (6) | 0.0059 (6) | 0.0082 (6) |
| C1 | 0.0697 (13) | 0.0549 (12) | 0.0532 (11) | 0.0105 (9) | 0.0025 (9) | 0.0017 (9) |
| C2 | 0.0501 (11) | 0.0473 (11) | 0.0502 (10) | 0.0110 (8) | 0.0055 (8) | −0.0014 (8) |
| C3 | 0.0623 (12) | 0.0676 (14) | 0.0493 (12) | 0.0100 (10) | 0.0035 (9) | −0.0040 (10) |
| C4 | 0.0615 (13) | 0.0656 (14) | 0.0605 (12) | −0.0002 (10) | 0.0036 (10) | −0.0188 (11) |
| C5 | 0.0647 (13) | 0.0522 (12) | 0.0706 (13) | −0.0034 (10) | 0.0102 (10) | −0.0076 (11) |
| C6 | 0.0650 (12) | 0.0506 (12) | 0.0558 (12) | −0.0003 (9) | 0.0040 (9) | 0.0029 (9) |
| C7 | 0.0450 (10) | 0.0431 (10) | 0.0490 (10) | 0.0073 (8) | 0.0054 (8) | −0.0013 (8) |
| C8 | 0.0572 (11) | 0.0499 (11) | 0.0457 (10) | 0.0032 (9) | 0.0034 (8) | 0.0067 (8) |
| C9 | 0.0522 (11) | 0.0480 (11) | 0.0505 (10) | 0.0050 (8) | 0.0068 (8) | 0.0015 (8) |
| C10 | 0.0556 (12) | 0.0474 (11) | 0.0674 (12) | 0.0015 (10) | 0.0077 (10) | −0.0006 (9) |
| C11 | 0.0537 (12) | 0.0542 (12) | 0.0641 (12) | −0.0035 (10) | 0.0031 (10) | −0.0026 (9) |
| C12 | 0.0726 (15) | 0.0592 (14) | 0.0701 (14) | −0.0040 (12) | 0.0012 (12) | −0.0074 (10) |
| C13 | 0.103 (2) | 0.0798 (18) | 0.0735 (16) | −0.0185 (17) | −0.0112 (15) | −0.0058 (13) |
| O1—C1 | 1.2079 (18) | C8—C9 | 1.323 (2) |
| O2—C1 | 1.374 (2) | C8—H8 | 0.949 (14) |
| O2—C9 | 1.3899 (18) | C9—C10 | 1.487 (2) |
| C1—C2 | 1.460 (2) | C10—C11 | 1.516 (2) |
| C2—C7 | 1.397 (2) | C10—H10A | 0.994 (16) |
| C2—C3 | 1.398 (2) | C10—H10B | 0.993 (17) |
| C3—C4 | 1.365 (2) | C11—C12 | 1.514 (3) |
| C3—H3 | 0.960 (17) | C11—H11A | 0.996 (16) |
| C4—C5 | 1.381 (2) | C11—H11B | 1.018 (16) |
| C4—H4 | 0.963 (16) | C12—C13 | 1.509 (3) |
| C5—C6 | 1.370 (2) | C12—H12A | 0.934 (18) |
| C5—H5 | 0.947 (18) | C12—H12B | 0.998 (19) |
| C6—C7 | 1.398 (2) | C13—H13A | 0.97 (2) |
| C6—H6 | 0.935 (15) | C13—H13B | 1.02 (2) |
| C7—C8 | 1.435 (2) | C13—H13C | 0.97 (2) |
| C1—O2—C9 | 122.55 (13) | C8—C9—C10 | 128.90 (16) |
| O1—C1—O2 | 116.22 (16) | O2—C9—C10 | 110.46 (14) |
| O1—C1—C2 | 126.57 (17) | C9—C10—C11 | 114.96 (15) |
| O2—C1—C2 | 117.21 (15) | C9—C10—H10A | 107.7 (9) |
| C7—C2—C3 | 120.52 (16) | C11—C10—H10A | 110.2 (8) |
| C7—C2—C1 | 119.65 (15) | C9—C10—H10B | 109.8 (9) |
| C3—C2—C1 | 119.83 (16) | C11—C10—H10B | 109.3 (9) |
| C4—C3—C2 | 119.74 (18) | H10A—C10—H10B | 104.4 (13) |
| C4—C3—H3 | 120.8 (10) | C12—C11—C10 | 113.25 (16) |
| C2—C3—H3 | 119.4 (10) | C12—C11—H11A | 108.8 (9) |
| C3—C4—C5 | 120.2 (2) | C10—C11—H11A | 111.1 (9) |
| C3—C4—H4 | 119.7 (9) | C12—C11—H11B | 108.5 (9) |
| C5—C4—H4 | 120.1 (9) | C10—C11—H11B | 110.7 (8) |
| C6—C5—C4 | 120.8 (2) | H11A—C11—H11B | 104.2 (12) |
| C6—C5—H5 | 121.7 (10) | C13—C12—C11 | 112.52 (18) |
| C4—C5—H5 | 117.6 (10) | C13—C12—H12A | 110.6 (11) |
| C5—C6—C7 | 120.44 (18) | C11—C12—H12A | 107.2 (11) |
| C5—C6—H6 | 121.8 (10) | C13—C12—H12B | 112.3 (10) |
| C7—C6—H6 | 117.8 (10) | C11—C12—H12B | 107.4 (10) |
| C2—C7—C6 | 118.29 (16) | H12A—C12—H12B | 106.5 (15) |
| C2—C7—C8 | 118.51 (15) | C12—C13—H13A | 110.8 (14) |
| C6—C7—C8 | 123.20 (15) | C12—C13—H13B | 111.5 (12) |
| C9—C8—C7 | 121.43 (16) | H13A—C13—H13B | 105.1 (19) |
| C9—C8—H8 | 120.1 (9) | C12—C13—H13C | 110.5 (11) |
| C7—C8—H8 | 118.4 (9) | H13A—C13—H13C | 106.7 (17) |
| C8—C9—O2 | 120.64 (16) | H13B—C13—H13C | 112.0 (17) |
| C9—O2—C1—O1 | −179.52 (14) | C1—C2—C7—C8 | 0.5 (2) |
| C9—O2—C1—C2 | −0.4 (2) | C5—C6—C7—C2 | −0.1 (2) |
| O1—C1—C2—C7 | 178.47 (17) | C5—C6—C7—C8 | 179.83 (16) |
| O2—C1—C2—C7 | −0.5 (2) | C2—C7—C8—C9 | 0.4 (2) |
| O1—C1—C2—C3 | −1.8 (3) | C6—C7—C8—C9 | −179.56 (15) |
| O2—C1—C2—C3 | 179.20 (14) | C7—C8—C9—O2 | −1.4 (2) |
| C7—C2—C3—C4 | −1.0 (2) | C7—C8—C9—C10 | 178.95 (16) |
| C1—C2—C3—C4 | 179.31 (15) | C1—O2—C9—C8 | 1.4 (2) |
| C2—C3—C4—C5 | 0.5 (3) | C1—O2—C9—C10 | −178.86 (14) |
| C3—C4—C5—C6 | 0.2 (3) | C8—C9—C10—C11 | −0.2 (3) |
| C4—C5—C6—C7 | −0.3 (3) | O2—C9—C10—C11 | −179.87 (15) |
| C3—C2—C7—C6 | 0.8 (2) | C9—C10—C11—C12 | 179.66 (18) |
| C1—C2—C7—C6 | −179.50 (14) | C10—C11—C12—C13 | −179.5 (2) |
| C3—C2—C7—C8 | −179.17 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O1i | 0.952 (18) | 2.584 (18) | 3.363 (2) | 139.2 (13) |
| C5—H5···O1ii | 0.949 (19) | 2.496 (19) | 3.397 (2) | 158.5 (13) |
| Symmetry codes: (i) −x, −y, −z−1; (ii) −x, y−1/2, −z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O1i | 0.952 (18) | 2.584 (18) | 3.363 (2) | 139.2 (13) |
| C5—H5···O1ii | 0.949 (19) | 2.496 (19) | 3.397 (2) | 158.5 (13) |
| Symmetry codes: (i) −x, −y, −z−1; (ii) −x, y−1/2, −z−1/2. |
We thank the Department of Science and Technology, India, for use of the CCD facility setup under the IRHPA-DST program at IISc.
Barry, R. D. (1964). Chem. Rev. 64 , 229–260.
Bruker (2000). SHELXTL. Version ???. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). SMART (Version 5.628) and SAINT (Version 6.45a). BrukerAXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Napolitano, E. (1997). Org. Prep. Proced. Int. 29, 631–664.
Saeed, A., Ritch, J. S. & Parvez, M. (2007). Acta Cryst. E63, o1701–o1703.
Saeed, A., van der Eide, E. F. & Parvez, M. (2006). Acta Cryst. E62, o3262–o3263.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Compounds containing the isocoumarin moiety show strong antifungal, antibacterial activity and are commonly found in higher plants,marine organisms and in variety of fungi,lichens and bacteria (Barry, 1964, Napolitano, 1997).
The structure of the title compound, (I) (Fig. 1), contains an n-butyl unit attached to the isocoumarin frame at the carbon atom C9.T he angle between the isocoumarin moiety and the n butyl side chain is 0.67° indicating that the entire molecule is almost planar. The n-butyl group adopts an all trans configuration.
The packing for (I) (Fig. 2) is consolidated by C—H···O interactions (Table 1).