= (2) V = (3) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN (3-Fluorobenzyl)isochroman-1-one Tariq Mahmood Babar, a Ghulam Qadeer, a * Nasim Hasan Rama, a Javeed Akhtar b and Madeleine Helliwell b a Department of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan, and b Manchester Materials Science Centre and Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England Correspondence qadeerqau@yahoo.com Received 22 January 2009; accepted 27 January 2009 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.042; wr factor = 0.096; data-to-parameter ratio = In the molecule of the title compound, C 16 H 13 FO 2, the aromatic rings are oriented at a dihedral angle of (4). The heterocyclic ring adopts a twisted conformation. In the crystal structure, there is a weak C H interaction. Related literature For related structures, see: Schmalle et al. (1982); Schnebel et al. (2003). For bond-length data, see: Allen et al. (1987). For ring-puckering parameters, see: Cremer & Pople (1975). For details of the Cambridge Structural Database, see: Allen (2002). = (2) V = (3) Å 3 Z =4 Mo K radiation Data collection Bruker SMART CCD area-detector diffractometer Absorption correction: none 6739 measured reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Hydrogen-bond geometry (Å, ). Cg1 is the centroid of the C3 C8 ring. = 0.10 mm 1 T = 100 (2) K mm 2501 independent reflections 1805 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.24 e Å 3 min = 0.19 e Å 3 D HA D H HA DA D HA C12 H12Cg1 i (3) 151 Symmetry code: (i) x þ 1; y þ 1 2 ; z þ 3 2. Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2616). Experimental Crystal data C 16 H 13 FO 2 M r = Monoclinic, P2 1 =c a = (16) Å b = (10) Å c = (17) Å References Allen, F. H. (2002). Acta Cryst. B58, 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. 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, Schmalle, H. W., Jarchow, O. H., Hausen, B. M. & Schulz, K.-H. (1982). Acta Cryst. B38, Schnebel, M., Weidner, I., Wartchow, R. & Butenschon, H. (2003). Eur. J. Org. Chem. pp Sheldrick, G. M. (2008). Acta Cryst. A64, o418 Babar et al. doi: /s

2 supporting information [doi: /s ] 3-(3-Fluorobenzyl)isochroman-1-one Tariq Mahmood Babar, Ghulam Qadeer, Nasim Hasan Rama, Javeed Akhtar and Madeleine Helliwell S1. Comment 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-hydroxyphenyl)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 (C3 C8) and C (C11 C16) are, of course, planar, and they are oriented at a dihedral angle of (4). Ring B (O1/C1 C3/C8/C9) is not planar, having total puckering amplitude, Q T, of (3) Å and twisted conformation [φ = (3) and θ = (3) ] (Cremer & Pople, 1975). In the crystal structure, there is a C H π interaction (Table 1). S2. Experimental As shown in Scheme 2, a mixture of homophthalic acid (1.98 g, 11.0 mmol) and 2-(3-fluorophenyl) acetyl chloride (7.91 g, 46 mmol) was heated under reflux at 473 K. After concentration, the residue was chromatographed on silica gel column using petroleum ether ( K) to give 3-(3-fluorobenzyl)-1H-isochromen-1-one. 2-(3-(3-fluorophenyl)-2- oxopropyl)benzoic acid was obtained by refluxing a solution of 3-(3-fluorobenzyl)-1H-isochromen-1-one (3.6 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-(3-(3-fluorophenyl)-2-oxopropyl)benzoic acid (4.23 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 15 ml). Usual work-up gave crude racemic hydroxy-acid, 2-(3-(3-fluorophenyl)-2-hydroxy propyl)- benzoic acid, which was dissolved in acetic anhydride (5 ml) and heated under reflux for 2 h to get the title compound (yield; 81%, m.p, ). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol. S3. Refinement H atoms were positioned geometrically, with C H = 0.95, 1.00 and 0.99 Å for aromatic, methine and methylene H, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C). sup-1

3 Figure 1 The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Figure 2 The formation of the title compound. 3-(3-Fluorobenzyl)isochroman-1-one Crystal data C 16 H 13 FO 2 M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (16) Å b = (10) Å c = (17) Å β = (2) V = (3) Å 3 Z = 4 F(000) = 536 D x = Mg m 3 Melting point: 374(1) K Mo Kα radiation, λ = Å Cell parameters from 1804 reflections θ = µ = 0.10 mm 1 T = 100 K Plate, colourless mm sup-2

4 Data collection Bruker SMART CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans 6739 measured reflections 2501 independent reflections Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 172 parameters 0 restraints Primary atom site location: structure-invariant direct methods 1805 reflections with I > 2σ(I) R int = θ max = 26.4, θ min = 1.7 h = k = 8 9 l = 16 9 Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0463P) 2 ] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.24 e Å 3 Δρ min = 0.19 e Å 3 Special details 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq F (8) (13) (8) (3) O (8) (13) (8) (3) O (9) (14) (9) (3) C (12) (2) (12) (4) H * C (12) (2) (13) (4) H2A * H2B * C (12) (19) (12) (4) C (12) (2) (13) (4) H * C (13) (2) (14) (4) H * C (13) (2) (14) (4) H * C (13) (2) (14) (4) H * sup-3

5 C (12) (19) (13) (4) C (13) (19) (13) (4) C (12) (2) (13) (4) H10A * H10B * C (12) (2) (13) (4) C (12) (2) (13) (4) H * C (13) (2) (14) (4) C (14) (2) (15) (4) H * C (13) (2) (15) (4) H * C (13) (2) (14) (4) H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 F (6) (7) (7) (5) (5) (5) O (6) (6) (6) (5) (5) (5) O (7) (6) (7) (5) (6) (5) C (8) (8) (8) (6) (7) (7) C (9) (8) (9) (7) (7) (7) C (8) (8) (9) (6) (7) (7) C (9) (8) (10) (7) (8) (7) C (9) (9) (11) (7) (8) (8) C (9) (9) (11) (7) (8) (8) C (9) (9) (10) (7) (8) (7) C (8) (8) (9) (6) (7) (7) C (9) (8) (9) (7) (8) (7) C (9) (8) (9) (6) (8) (7) C (9) (8) (9) (6) (7) (7) C (9) (8) (9) (7) (8) (7) C (9) (9) (10) (7) (8) (8) C (9) (9) (12) (7) (8) (8) C (10) (9) (11) (7) (9) (8) C (9) (9) (10) (7) (8) (8) Geometric parameters (Å, º) F1 C (19) C6 H O1 C (18) C7 C (2) O1 C (19) C7 H O2 C (19) C8 C (2) C1 C (2) C10 C (2) C1 C (2) C10 H10A C1 H C10 H10B sup-4

6 C2 C (2) C11 C (2) C2 H2A C11 C (2) C2 H2B C12 C (2) C3 C (2) C12 H C3 C (2) C13 C (3) C4 C (2) C14 C (2) C4 H C14 H C5 C (2) C15 C (2) C5 H C15 H C6 C (2) C16 H C9 O1 C (12) C7 C8 C (14) O1 C1 C (13) C3 C8 C (14) O1 C1 C (12) O2 C9 O (14) C2 C1 C (13) O2 C9 C (15) O1 C1 H O1 C9 C (14) C2 C1 H C11 C10 C (13) C10 C1 H C11 C10 H10A C3 C2 C (12) C1 C10 H10A C3 C2 H2A C11 C10 H10B C1 C2 H2A C1 C10 H10B C3 C2 H2B H10A C10 H10B C1 C2 H2B C12 C11 C (15) H2A C2 H2B C12 C11 C (15) C4 C3 C (15) C16 C11 C (15) C4 C3 C (14) C13 C12 C (16) C8 C3 C (14) C13 C12 H C5 C4 C (15) C11 C12 H C5 C4 H F1 C13 C (16) C3 C4 H F1 C13 C (15) C4 C5 C (15) C12 C13 C (17) C4 C5 H C13 C14 C (15) C6 C5 H C13 C14 H C7 C6 C (16) C15 C14 H C7 C6 H C14 C15 C (17) C5 C6 H C14 C15 H C6 C7 C (16) C16 C15 H C6 C7 H C15 C16 C (16) C8 C7 H C15 C16 H C7 C8 C (15) C11 C16 H C9 O1 C1 C (17) C7 C8 C9 O (2) C9 O1 C1 C (12) C3 C8 C9 O (15) O1 C1 C2 C (16) C7 C8 C9 O (14) C10 C1 C2 C (13) C3 C8 C9 O (2) C1 C2 C3 C (15) O1 C1 C10 C (17) C1 C2 C3 C (2) C2 C1 C10 C (14) C8 C3 C4 C5 0.5 (2) C1 C10 C11 C (17) sup-5

7 C2 C3 C4 C (15) C1 C10 C11 C (19) C3 C4 C5 C6 0.5 (2) C16 C11 C12 C (2) C4 C5 C6 C7 0.1 (3) C10 C11 C12 C (14) C5 C6 C7 C8 0.3 (3) C11 C12 C13 F (13) C6 C7 C8 C3 0.3 (2) C11 C12 C13 C (2) C6 C7 C8 C (14) F1 C13 C14 C (14) C4 C3 C8 C7 0.1 (2) C12 C13 C14 C (3) C2 C3 C8 C (14) C13 C14 C15 C (2) C4 C3 C8 C (14) C14 C15 C16 C (2) C2 C3 C8 C9 2.7 (2) C12 C11 C16 C (2) C1 O1 C9 O (13) C10 C11 C16 C (14) C1 O1 C9 C (19) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C12 H12 Cg1 i (3) 151 Symmetry code: (i) x+1, y+1/2, z+3/2. sup-6