supplementary materials
3-Benzylisochroman-1-one
In the molecule of the title compound, C16H14O2, the aromatic rings are oriented at a dihedral angle of 78.49 (3)°. The heterocyclic ring adopts a twist conformation. In the crystal structure, intermolecular C-H
O hydrogen bonds link the molecules into chains along the c axis.
As shown in Scheme 2, a mixture of homophthalic acid (1.98 g, 11.0 mmol) and
2-phenylacetyl chloride (7.08 g, 46 mmol) was heated under reflux for 6 h at
473 K. After concentration, the residue was chromatographed on silica gel
column
using petroleum ether (333–353 K) to give 3-benzyl-1H-isochromen-1-one.
2-(2-oxo-3-phenylpropyl) benzoic acid was obtained by refluxing a solution of
3-benzyl-1H-isochromen-1-one (4 g, 15.9 mmol) in ethanol (200 ml) and
potassium hydroxide (5%,200 ml) for 6 h. NaBH4 (1.6 g) was added to a solution
of 2-(2-oxo-3-phenylpropyl) benzoic acid (4.81 g, 17.8 mmol) in sodium
hydroxide
(1%, 180 ml) and the resulting solution was stirred overnight at room
temperature. After being acidified with HCl, the whole mixture was extracted
with dichloromethane (2 \ times 15 ml). Usual work-up gave crude racemic
hydroxy-acid, 2-(2-hydroxy-3-phenylpropyl)benzoic acid, which was dissolved in
acetic anhydride (5 ml) and heated under reflux for 2 h to get the title
compound (yield; 73%, m.p. 605-606 K). The crude compound was purified by
column chromatography on silica gel with petroleum ether and recrystallized in
ethanol.
H atoms were positioned geometrically, with C-H = 0.93, 0.98 and 0.97 Å for
aromatic, methine and methylene H, respectively, and constrained to ride on
their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
3-Benzylisochroman-1-one
top
Crystal data top
| C16H14O2 | F(000) = 504 |
| Mr = 238.27 | Dx = 1.254 Mg m−3 |
| Monoclinic, P21/c | Melting point: 332(1) K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 12.503 (5) Å | Cell parameters from 1316 reflections |
| b = 8.0200 (9) Å | θ = 5.3–25.2° |
| c = 12.892 (5) Å | µ = 0.08 mm−1 |
| β = 102.43 (2)° | T = 294 K |
| V = 1262.4 (7) Å3 | Block, colorless |
| Z = 4 | 0.32 × 0.26 × 0.21 mm |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 3024 independent reflections |
| Radiation source: fine-focus sealed tube | 2546 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| ω and φ scans | θmax = 28.5°, θmin = 3.0° |
Absorption correction: multi-scan
(SADABS; Bruker, 2001) | h = −16→16 |
| Tmin = 0.820, Tmax = 0.983 | k = −10→10 |
| 7148 measured reflections | l = −10→17 |
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)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.1131P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 3024 reflections | Δρmax = 0.18 e Å−3 |
| 164 parameters | Δρmin = −0.14 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.058 (7) |
Crystal data top
| C16H14O2 | V = 1262.4 (7) Å3 |
| Mr = 238.27 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.503 (5) Å | µ = 0.08 mm−1 |
| b = 8.0200 (9) Å | T = 294 K |
| c = 12.892 (5) Å | 0.32 × 0.26 × 0.21 mm |
| β = 102.43 (2)° | |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 3024 independent reflections |
Absorption correction: multi-scan
(SADABS; Bruker, 2001) | 2546 reflections with I > 2σ(I) |
| Tmin = 0.820, Tmax = 0.983 | Rint = 0.021 |
| 7148 measured reflections | θmax = 28.5° |
Refinement top
| R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.136 | Δρmax = 0.18 e Å−3 |
| S = 1.02 | Δρmin = −0.14 e Å−3 |
| 3024 reflections | Absolute structure: ? |
| 164 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | |
| O1 | −0.00370 (8) | 0.34647 (13) | −0.09298 (6) | 0.0694 (3) | |
| O2 | 0.04862 (6) | 0.20854 (10) | 0.05531 (6) | 0.0513 (2) | |
| C1 | −0.27750 (10) | 0.22424 (17) | 0.10333 (11) | 0.0614 (3) | |
| H1A | −0.2984 | 0.1604 | 0.1558 | 0.074* | |
| C2 | −0.35219 (11) | 0.3310 (2) | 0.04219 (14) | 0.0770 (4) | |
| H2A | −0.4230 | 0.3383 | 0.0536 | 0.092* | |
| C3 | −0.32221 (12) | 0.4264 (2) | −0.03548 (14) | 0.0793 (4) | |
| H3A | −0.3728 | 0.4978 | −0.0766 | 0.095* | |
| C4 | −0.21631 (11) | 0.41640 (17) | −0.05268 (11) | 0.0653 (3) | |
| H4A | −0.1961 | 0.4815 | −0.1050 | 0.078* | |
| C5 | −0.14040 (9) | 0.30857 (13) | 0.00867 (8) | 0.0481 (3) | |
| C6 | −0.17032 (8) | 0.21122 (13) | 0.08690 (8) | 0.0461 (2) | |
| C7 | −0.02835 (9) | 0.29314 (14) | −0.01389 (8) | 0.0495 (3) | |
| C8 | 0.02859 (8) | 0.16880 (12) | 0.15967 (7) | 0.0439 (2) | |
| H8A | 0.0341 | 0.2713 | 0.2019 | 0.053* | |
| C9 | −0.08557 (9) | 0.09595 (13) | 0.14927 (8) | 0.0484 (3) | |
| H9A | −0.0896 | −0.0113 | 0.1138 | 0.058* | |
| H9B | −0.1002 | 0.0786 | 0.2194 | 0.058* | |
| C10 | 0.11974 (9) | 0.05047 (14) | 0.21118 (9) | 0.0528 (3) | |
| H10A | 0.1079 | 0.0185 | 0.2804 | 0.063* | |
| H10B | 0.1147 | −0.0498 | 0.1683 | 0.063* | |
| C11 | 0.23470 (9) | 0.12051 (13) | 0.22511 (9) | 0.0506 (3) | |
| C12 | 0.30019 (11) | 0.08497 (17) | 0.15378 (11) | 0.0647 (3) | |
| H12A | 0.2725 | 0.0181 | 0.0952 | 0.078* | |
| C13 | 0.40664 (12) | 0.1470 (2) | 0.16750 (15) | 0.0809 (4) | |
| H13A | 0.4488 | 0.1209 | 0.1185 | 0.097* | |
| C14 | 0.44906 (13) | 0.2457 (2) | 0.25261 (17) | 0.0870 (5) | |
| H14A | 0.5200 | 0.2870 | 0.2622 | 0.104* | |
| C15 | 0.38502 (15) | 0.2832 (2) | 0.32398 (15) | 0.0894 (5) | |
| H15A | 0.4131 | 0.3509 | 0.3820 | 0.107* | |
| C16 | 0.27839 (13) | 0.22086 (18) | 0.31051 (11) | 0.0708 (4) | |
| H16A | 0.2365 | 0.2475 | 0.3597 | 0.085* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0738 (6) | 0.0907 (7) | 0.0453 (4) | −0.0159 (5) | 0.0161 (4) | 0.0086 (4) |
| O2 | 0.0496 (4) | 0.0622 (5) | 0.0443 (4) | −0.0036 (3) | 0.0148 (3) | 0.0004 (3) |
| C1 | 0.0497 (6) | 0.0677 (7) | 0.0686 (7) | −0.0063 (5) | 0.0169 (5) | −0.0006 (6) |
| C2 | 0.0477 (6) | 0.0826 (9) | 0.0997 (11) | 0.0023 (6) | 0.0136 (7) | 0.0030 (8) |
| C3 | 0.0588 (7) | 0.0751 (9) | 0.0955 (10) | 0.0062 (6) | −0.0020 (7) | 0.0134 (8) |
| C4 | 0.0631 (7) | 0.0630 (7) | 0.0640 (7) | −0.0052 (6) | 0.0008 (5) | 0.0107 (6) |
| C5 | 0.0504 (6) | 0.0486 (5) | 0.0430 (5) | −0.0087 (4) | 0.0045 (4) | −0.0041 (4) |
| C6 | 0.0464 (5) | 0.0478 (5) | 0.0438 (5) | −0.0073 (4) | 0.0086 (4) | −0.0074 (4) |
| C7 | 0.0566 (6) | 0.0529 (6) | 0.0387 (5) | −0.0123 (4) | 0.0098 (4) | −0.0043 (4) |
| C8 | 0.0483 (5) | 0.0457 (5) | 0.0380 (5) | −0.0015 (4) | 0.0100 (4) | −0.0036 (4) |
| C9 | 0.0506 (5) | 0.0508 (5) | 0.0453 (5) | −0.0044 (4) | 0.0138 (4) | 0.0014 (4) |
| C10 | 0.0533 (6) | 0.0488 (6) | 0.0564 (6) | 0.0023 (4) | 0.0121 (4) | 0.0014 (5) |
| C11 | 0.0500 (5) | 0.0460 (5) | 0.0527 (6) | 0.0073 (4) | 0.0047 (4) | 0.0031 (4) |
| C12 | 0.0598 (7) | 0.0671 (7) | 0.0680 (7) | 0.0025 (6) | 0.0152 (6) | −0.0048 (6) |
| C13 | 0.0600 (8) | 0.0819 (9) | 0.1042 (11) | 0.0051 (7) | 0.0252 (8) | 0.0072 (9) |
| C14 | 0.0520 (7) | 0.0795 (10) | 0.1203 (14) | −0.0013 (7) | −0.0019 (8) | 0.0093 (10) |
| C15 | 0.0777 (10) | 0.0835 (10) | 0.0908 (11) | −0.0065 (8) | −0.0181 (8) | −0.0153 (8) |
| C16 | 0.0699 (8) | 0.0730 (8) | 0.0633 (8) | 0.0056 (6) | 0.0009 (6) | −0.0116 (6) |
Geometric parameters (Å, °) top
| C1—C2 | 1.382 (2) | C8—H8A | 0.9800 |
| C1—C6 | 1.405 (2) | C9—H9A | 0.9700 |
| C1—H1A | 0.9300 | C9—H9B | 0.9700 |
| C2—C3 | 1.375 (3) | C10—C11 | 1.517 (2) |
| C2—H2A | 0.9300 | C10—H10A | 0.9700 |
| C3—C4 | 1.391 (3) | C10—H10B | 0.9700 |
| C3—H3A | 0.9300 | C11—C16 | 1.378 (2) |
| C4—C5 | 1.3968 (19) | C11—C12 | 1.386 (2) |
| C4—H4A | 0.9300 | C12—C13 | 1.396 (2) |
| C5—C6 | 1.3889 (18) | C12—H12A | 0.9300 |
| C5—C7 | 1.496 (2) | C13—C14 | 1.365 (3) |
| C6—C9 | 1.5023 (19) | C13—H13A | 0.9300 |
| C7—O1 | 1.2054 (17) | C14—C15 | 1.377 (3) |
| C7—O2 | 1.3463 (17) | C14—H14A | 0.9300 |
| C8—O2 | 1.4559 (19) | C15—C16 | 1.399 (3) |
| C8—C9 | 1.521 (2) | C15—H15A | 0.9300 |
| C8—C10 | 1.5214 (19) | C16—H16A | 0.9300 |
| | | |
| C2—C1—C6 | 120.63 (13) | C8—C9—H9A | 109.5 |
| C2—C1—H1A | 119.7 | C6—C9—H9B | 109.5 |
| C6—C1—H1A | 119.7 | C8—C9—H9B | 109.5 |
| C3—C2—C1 | 120.23 (14) | H9A—C9—H9B | 108.1 |
| C3—C2—H2A | 119.9 | C11—C10—C8 | 114.97 (12) |
| C1—C2—H2A | 119.9 | C11—C10—H10A | 108.5 |
| C2—C3—C4 | 120.14 (13) | C8—C10—H10A | 108.5 |
| C2—C3—H3A | 119.9 | C11—C10—H10B | 108.5 |
| C4—C3—H3A | 119.9 | C8—C10—H10B | 108.5 |
| C3—C4—C5 | 119.97 (13) | H10A—C10—H10B | 107.5 |
| C3—C4—H4A | 120.0 | C16—C11—C12 | 117.44 (14) |
| C5—C4—H4A | 120.0 | C16—C11—C10 | 120.88 (11) |
| C6—C5—C4 | 120.18 (13) | C12—C11—C10 | 121.68 (12) |
| C6—C5—C7 | 120.30 (10) | C11—C12—C13 | 121.74 (15) |
| C4—C5—C7 | 119.46 (12) | C11—C12—H12A | 119.1 |
| C5—C6—C1 | 118.84 (11) | C13—C12—H12A | 119.1 |
| C5—C6—C9 | 117.73 (11) | C14—C13—C12 | 120.23 (15) |
| C1—C6—C9 | 123.42 (11) | C14—C13—H13A | 119.9 |
| O1—C7—O2 | 117.57 (12) | C12—C13—H13A | 119.9 |
| O1—C7—C5 | 123.76 (11) | C13—C14—C15 | 118.86 (16) |
| O2—C7—C5 | 118.59 (11) | C13—C14—H14A | 120.6 |
| O2—C8—C9 | 110.33 (8) | C15—C14—H14A | 120.6 |
| O2—C8—C10 | 106.16 (9) | C14—C15—C16 | 120.99 (16) |
| C9—C8—C10 | 113.54 (11) | C14—C15—H15A | 119.5 |
| O2—C8—H8A | 108.9 | C16—C15—H15A | 119.5 |
| C9—C8—H8A | 108.9 | C11—C16—C15 | 120.73 (15) |
| C10—C8—H8A | 108.9 | C11—C16—H16A | 119.6 |
| C6—C9—C8 | 110.56 (11) | C15—C16—H16A | 119.6 |
| C6—C9—H9A | 109.5 | C7—O2—C8 | 118.82 (10) |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9B···O1i | 0.97 | 2.53 | 3.2922 (18) | 135 |
| Symmetry codes: (i) x, −y+1/2, z+1/2. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9B···O1i | 0.97 | 2.53 | 3.2922 (18) | 135 |
| Symmetry codes: (i) x, −y+1/2, z+1/2. |
The authors gratefully acknowledge the financial support of the Higher Education
Commission, Islamabad, Pakistan.
Allen, F. H. (2002). Acta Cryst. B58, 380–388.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Schmalle, H. W., Jarchow, O. H., Hausen, B. M. & Schulz, K.-H. (1982). Acta Cryst. B38, 2938–2941.
Schnebel, M., Weidner, I., Wartchow, R. & Butenschon, H. (2003). Eur. J. Org. Chem. pp. 4363–4372.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
![[Figure 1]](./hk2615fig1thm.gif)
![[Figure 2]](./hk2615fig2thm.gif)
![[Figure 3]](./hk2615fig3thm.gif)
The title compound was prepared in order to evalute its potential as antibacterial and antifungal agents. The CCDC search (Allen, 2002) showed that the crystal structures of rac-exo-tricarbonyl-(h6-3-phenyl isochromanone) -chromium (Schnebel et al., 2003) and 3,4-dihydro-8-hydroxy-3-(4-hydroxy- phenyl)-isocoumarin (Schmalle et al., 1982) have been reported, which have close resemblance as far as isochromane and attached phenyl ring is considered. We report herein the synthesis and crystal structure of the title compound.
In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and C (C11-C16) are, of course, planar, and they are oriented at a dihedral angle of 78.49 (3)°. Ring B (O2/C5-C9) is not planar, having total puckering amplitude, QT, of 2.420 (3) Å and twisted conformation [φ = 151.98 (3)° and θ = 88.50 (3)°] (Cremer & Pople, 1975).
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis, in which they may be effective in the stabilization of the structure.