organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3-(3-Fluoro­benz­yl)isochroman-1-one

aDepartment of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan, and bManchester Materials Science Centre and Department of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England
*Correspondence e-mail: qadeerqau@yahoo.com

(Received 22 January 2009; accepted 27 January 2009; online 31 January 2009)

In the mol­ecule of the title compound, C16H13FO2, the aromatic rings are oriented at a dihedral angle of 74.46 (4)°. The heterocyclic ring adopts a twisted conformation. In the crystal structure, there is a weak C—H⋯π inter­action.

Related literature

For related structures, see: Schmalle et al. (1982[Schmalle, H. W., Jarchow, O. H., Hausen, B. M. & Schulz, K.-H. (1982). Acta Cryst. B38, 2938-2941.]); Schnebel et al. (2003[Schnebel, M., Weidner, I., Wartchow, R. & Butenschon, H. (2003). Eur. J. Org. Chem. pp. 4363-4372.]). For bond-length data, see: Allen et al. (1987[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.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For details of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13FO2

  • Mr = 256.26

  • Monoclinic, P 21 /c

  • a = 12.6154 (16) Å

  • b = 7.6918 (10) Å

  • c = 13.0532 (17) Å

  • β = 103.705 (2)°

  • V = 1230.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 (2) K

  • 0.50 × 0.40 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 6739 measured reflections

  • 2501 independent reflections

  • 1805 reflections with I > 2σ(I)

  • Rint = 0.055

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.096

  • S = 0.93

  • 2501 reflections

  • 172 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯Cg1i 0.95 2.95 3.806 (3) 151
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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 74.46 (4)°. Ring B (O1/C1–C3/C8/C9) is not planar, having total puckering amplitude, QT, of 0.467 (3) Å and twisted conformation [ϕ = -105.12 (3)° and θ = 118.02 (3)°] (Cremer & Pople, 1975).

In the crystal structure, there is a C—H···π interaction (Table 1).

Related literature top

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).

Experimental top

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 (333–353 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, 374–375 °). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol.

Refinement top

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 Uiso(H) = 1.2Ueq(C).

Computing details top

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The formation of the title compound.
3-(3-Fluorobenzyl)isochroman-1-one top
Crystal data top
C16H13FO2F(000) = 536
Mr = 256.26Dx = 1.383 Mg m3
Monoclinic, P21/cMelting point: 374(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.6154 (16) ÅCell parameters from 1804 reflections
b = 7.6918 (10) Åθ = 3.2–26.2°
c = 13.0532 (17) ŵ = 0.10 mm1
β = 103.705 (2)°T = 100 K
V = 1230.6 (3) Å3Plate, colourless
Z = 40.50 × 0.40 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1805 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 26.4°, θmin = 1.7°
ϕ and ω scansh = 1515
6739 measured reflectionsk = 89
2501 independent reflectionsl = 169
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0463P)2]
where P = (Fo2 + 2Fc2)/3
2501 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C16H13FO2V = 1230.6 (3) Å3
Mr = 256.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.6154 (16) ŵ = 0.10 mm1
b = 7.6918 (10) ÅT = 100 K
c = 13.0532 (17) Å0.50 × 0.40 × 0.10 mm
β = 103.705 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1805 reflections with I > 2σ(I)
6739 measured reflectionsRint = 0.055
2501 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 0.93Δρmax = 0.24 e Å3
2501 reflectionsΔρmin = 0.19 e Å3
172 parameters
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
xyzUiso*/Ueq
F10.04488 (8)0.11657 (13)0.39583 (8)0.0386 (3)
O10.45079 (8)0.20180 (13)0.44056 (8)0.0218 (3)
O20.50042 (9)0.34257 (14)0.59049 (9)0.0268 (3)
C10.47167 (12)0.1662 (2)0.33687 (12)0.0196 (4)
H10.46660.27760.29640.024*
C20.58453 (12)0.0910 (2)0.34910 (13)0.0212 (4)
H2A0.58770.02580.38150.025*
H2B0.60050.07830.27880.025*
C30.66870 (12)0.20666 (19)0.41701 (12)0.0200 (4)
C40.77528 (12)0.2189 (2)0.40595 (13)0.0241 (4)
H40.79720.15320.35290.029*
C50.84964 (13)0.3259 (2)0.47153 (14)0.0288 (4)
H50.92250.33250.46360.035*
C60.81851 (13)0.4239 (2)0.54894 (14)0.0295 (4)
H60.86990.49740.59380.035*
C70.71298 (13)0.4138 (2)0.56045 (14)0.0259 (4)
H70.69150.48110.61310.031*
C80.63765 (12)0.30552 (19)0.49515 (13)0.0206 (4)
C90.52632 (13)0.28886 (19)0.51240 (13)0.0214 (4)
C100.38215 (12)0.0446 (2)0.28054 (13)0.0219 (4)
H10A0.39480.01620.21040.026*
H10B0.38720.06510.32110.026*
C110.26821 (12)0.1165 (2)0.26575 (13)0.0209 (4)
C120.20723 (12)0.0833 (2)0.33946 (13)0.0230 (4)
H120.23680.01550.40030.028*
C130.10394 (13)0.1499 (2)0.32292 (14)0.0256 (4)
C140.05618 (14)0.2488 (2)0.23648 (15)0.0301 (4)
H140.01590.29230.22720.036*
C150.11730 (13)0.2824 (2)0.16351 (15)0.0310 (4)
H150.08710.35070.10300.037*
C160.22210 (13)0.2173 (2)0.17798 (14)0.0263 (4)
H160.26310.24170.12730.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0329 (6)0.0451 (7)0.0432 (7)0.0007 (5)0.0195 (5)0.0039 (5)
O10.0239 (6)0.0238 (6)0.0181 (6)0.0009 (5)0.0059 (5)0.0008 (5)
O20.0334 (7)0.0281 (6)0.0203 (7)0.0060 (5)0.0091 (6)0.0012 (5)
C10.0257 (8)0.0187 (8)0.0150 (8)0.0008 (6)0.0058 (7)0.0018 (7)
C20.0258 (9)0.0201 (8)0.0189 (9)0.0005 (7)0.0079 (7)0.0004 (7)
C30.0242 (8)0.0161 (8)0.0189 (9)0.0045 (6)0.0038 (7)0.0046 (7)
C40.0251 (9)0.0212 (8)0.0262 (10)0.0028 (7)0.0065 (8)0.0008 (7)
C50.0221 (9)0.0258 (9)0.0380 (11)0.0020 (7)0.0063 (8)0.0015 (8)
C60.0271 (9)0.0229 (9)0.0341 (11)0.0002 (7)0.0016 (8)0.0044 (8)
C70.0311 (9)0.0210 (9)0.0236 (10)0.0053 (7)0.0028 (8)0.0020 (7)
C80.0241 (8)0.0175 (8)0.0191 (9)0.0043 (6)0.0028 (7)0.0029 (7)
C90.0286 (9)0.0163 (8)0.0190 (9)0.0046 (7)0.0052 (8)0.0041 (7)
C100.0263 (9)0.0183 (8)0.0218 (9)0.0005 (6)0.0070 (8)0.0004 (7)
C110.0238 (9)0.0157 (8)0.0220 (9)0.0038 (6)0.0031 (7)0.0029 (7)
C120.0255 (9)0.0198 (8)0.0221 (9)0.0009 (7)0.0028 (8)0.0002 (7)
C130.0248 (9)0.0247 (9)0.0293 (10)0.0048 (7)0.0100 (8)0.0063 (8)
C140.0219 (9)0.0236 (9)0.0409 (12)0.0016 (7)0.0002 (8)0.0077 (8)
C150.0314 (10)0.0248 (9)0.0312 (11)0.0001 (7)0.0039 (9)0.0033 (8)
C160.0290 (9)0.0249 (9)0.0232 (10)0.0051 (7)0.0030 (8)0.0013 (8)
Geometric parameters (Å, º) top
F1—C131.3648 (19)C6—H60.9500
O1—C11.4646 (18)C7—C81.393 (2)
O1—C91.3461 (19)C7—H70.9500
O2—C91.2141 (19)C8—C91.480 (2)
C1—C21.510 (2)C10—C111.509 (2)
C1—C101.516 (2)C10—H10A0.9900
C1—H11.0000C10—H10B0.9900
C2—C31.503 (2)C11—C121.391 (2)
C2—H2A0.9900C11—C161.391 (2)
C2—H2B0.9900C12—C131.369 (2)
C3—C41.389 (2)C12—H120.9500
C3—C81.400 (2)C13—C141.376 (3)
C4—C51.382 (2)C14—C151.384 (2)
C4—H40.9500C14—H140.9500
C5—C61.390 (2)C15—C161.384 (2)
C5—H50.9500C15—H150.9500
C6—C71.377 (2)C16—H160.9500
C9—O1—C1118.95 (12)C7—C8—C9119.56 (14)
O1—C1—C2110.20 (13)C3—C8—C9120.21 (14)
O1—C1—C10106.69 (12)O2—C9—O1117.85 (14)
C2—C1—C10112.96 (13)O2—C9—C8123.52 (15)
O1—C1—H1109.0O1—C9—C8118.54 (14)
C2—C1—H1109.0C11—C10—C1114.41 (13)
C10—C1—H1109.0C11—C10—H10A108.7
C3—C2—C1110.62 (12)C1—C10—H10A108.7
C3—C2—H2A109.5C11—C10—H10B108.7
C1—C2—H2A109.5C1—C10—H10B108.7
C3—C2—H2B109.5H10A—C10—H10B107.6
C1—C2—H2B109.5C12—C11—C16118.69 (15)
H2A—C2—H2B108.1C12—C11—C10120.69 (15)
C4—C3—C8118.91 (15)C16—C11—C10120.61 (15)
C4—C3—C2123.01 (14)C13—C12—C11118.96 (16)
C8—C3—C2118.07 (14)C13—C12—H12120.5
C5—C4—C3120.51 (15)C11—C12—H12120.5
C5—C4—H4119.7F1—C13—C12118.44 (16)
C3—C4—H4119.7F1—C13—C14118.07 (15)
C4—C5—C6120.40 (15)C12—C13—C14123.49 (17)
C4—C5—H5119.8C13—C14—C15117.42 (15)
C6—C5—H5119.8C13—C14—H14121.3
C7—C6—C5119.75 (16)C15—C14—H14121.3
C7—C6—H6120.1C14—C15—C16120.54 (17)
C5—C6—H6120.1C14—C15—H15119.7
C6—C7—C8120.26 (16)C16—C15—H15119.7
C6—C7—H7119.9C15—C16—C11120.89 (16)
C8—C7—H7119.9C15—C16—H16119.6
C7—C8—C3120.17 (15)C11—C16—H16119.6
C9—O1—C1—C248.49 (17)C7—C8—C9—O212.0 (2)
C9—O1—C1—C10171.47 (12)C3—C8—C9—O2164.92 (15)
O1—C1—C2—C353.65 (16)C7—C8—C9—O1171.54 (14)
C10—C1—C2—C3172.87 (13)C3—C8—C9—O111.5 (2)
C1—C2—C3—C4150.46 (15)O1—C1—C10—C1159.46 (17)
C1—C2—C3—C829.9 (2)C2—C1—C10—C11179.30 (14)
C8—C3—C4—C50.5 (2)C1—C10—C11—C1292.74 (17)
C2—C3—C4—C5179.19 (15)C1—C10—C11—C1687.32 (19)
C3—C4—C5—C60.5 (2)C16—C11—C12—C130.4 (2)
C4—C5—C6—C70.1 (3)C10—C11—C12—C13179.59 (14)
C5—C6—C7—C80.3 (3)C11—C12—C13—F1179.96 (13)
C6—C7—C8—C30.3 (2)C11—C12—C13—C140.1 (2)
C6—C7—C8—C9176.63 (14)F1—C13—C14—C15179.63 (14)
C4—C3—C8—C70.1 (2)C12—C13—C14—C150.5 (3)
C2—C3—C8—C7179.61 (14)C13—C14—C15—C160.3 (2)
C4—C3—C8—C9176.99 (14)C14—C15—C16—C110.1 (2)
C2—C3—C8—C92.7 (2)C12—C11—C16—C150.5 (2)
C1—O1—C9—O2167.83 (13)C10—C11—C16—C15179.45 (14)
C1—O1—C9—C815.51 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg1i0.952.953.806 (3)151
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC16H13FO2
Mr256.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.6154 (16), 7.6918 (10), 13.0532 (17)
β (°) 103.705 (2)
V3)1230.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.50 × 0.40 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6739, 2501, 1805
Rint0.055
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.096, 0.93
No. of reflections2501
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg1i0.952.953.806 (3)151
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

Acknowledgements

The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationSchmalle, H. W., Jarchow, O. H., Hausen, B. M. & Schulz, K.-H. (1982). Acta Cryst. B38, 2938–2941.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSchnebel, M., Weidner, I., Wartchow, R. & Butenschon, H. (2003). Eur. J. Org. Chem. pp. 4363–4372.  Web of Science CSD CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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