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Acta Cryst. (2008). E64, o2111    [ doi:10.1107/S1600536808032625 ]

3-(4-Methoxyphenyl)isochroman-1-one

M. T. Hussain, M. N. Tahir, A. Adnan, A. Hanif Ch and N. H. Rama

Abstract top

In the molecule of the title compound, C16H14O3, the aromatic rings are oriented at a dihedral angle of 72.02 (6)°. The heterocyclic ring adopts a twisted conformation. In the crystal structure, there are C-H...[pi] contacts between the heterocyclic and phenyl rings, and between the methyl group and methoxyphenyl ring.

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-phenylisochromanone)-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.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2–C7) and C (C10–C15) are, of course, planar, and they are oriented at a dihedral angle of 72.02 (6)°. Ring B (O2/C1/C2/C7–C9) is not planar, having total puckering amplitude, QT, of 0.483 (2) Å and twisted conformation [φ = 41.63 (3)° and θ = 116.64 (3)°] (Cremer & Pople, 1975).

In the crystal structure, there are C—H···π contacts (Table 1) between the heterocyclic and phenyl rings and the methyl group and methoxyphenyl ring, in which they may be effective in the stabilization of the structure.

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 a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

As shown in Fig. 3, a mixture of homophthalic acid, (1), (1.98 g, 11.0 mmol) and 4-methoxybenzoyl chloride, (2), (7.85 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-(4-methoxyphenyl)isocoumarin, (3). 2-[2'-Oxoethyl-2'-(4'-methoxyphenyl)]benzoic acid, (4), was obtained by refluxing a solution of (3) (4 g, 15.9 mmol) in ethanol (200 ml) and potassium hydroxide (5%, 200 ml) for 4 h. NaBH4 (1.6 g) was added to a solution of (4) (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 × 15 ml). Usual work-up gave crude racemic hydroxy-acid, (5), which was dissolved in acetic anhydride (5 ml) and heated under reflux for 2 h to get the title compound (6). The crude compound was purified by column chromatography on silica gel with petroleum ether and recrystallized in ethanol.

Refinement top

H9 atom was located in difference syntheses and refined as [C—H = 0.968 (15) Å; Uiso(H) = 0.0527 A2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

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. A packing diagram of the title compound.
[Figure 3] Fig. 3. Preparation of the title compound.
3-(4-Methoxyphenyl)isochroman-1-one top
Crystal data top
C16H14O3F(000) = 536
Mr = 254.27Dx = 1.332 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3302 reflections
a = 11.8933 (7) Åθ = 2.2–28.8°
b = 14.6874 (9) ŵ = 0.09 mm−1
c = 7.4521 (4) ÅT = 296 K
β = 101.040 (2)°Prismatic, yellow
V = 1277.66 (13) Å30.24 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker KappaAPEXII CCD
diffractometer		3302 independent reflections
Radiation source: fine-focus sealed tube2275 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 7.40 pixels mm-1θmax = 28.8°, θmin = 2.2°
ω scansh = −16→16
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		k = −19→19
Tmin = 0.980, Tmax = 0.996l = −9→10
12426 measured reflections
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) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2427P]
where P = (Fo2 + 2Fc2)/3
3302 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C16H14O3V = 1277.66 (13) Å3
Mr = 254.27Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8933 (7) ŵ = 0.09 mm−1
b = 14.6874 (9) ÅT = 296 K
c = 7.4521 (4) Å0.24 × 0.16 × 0.12 mm
β = 101.040 (2)°
Data collection top
Bruker KappaAPEXII CCD
diffractometer		3302 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2275 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.996Rint = 0.023
12426 measured reflectionsθmax = 28.8°
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117Δρmax = 0.14 e Å−3
S = 1.01Δρmin = −0.22 e Å−3
3302 reflectionsAbsolute structure: ?
175 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.56862 (10)0.12610 (9)−0.37797 (13)0.0668 (4)
O20.68506 (8)0.13694 (7)−0.11396 (12)0.0495 (3)
O31.15702 (8)0.09384 (8)0.43236 (15)0.0642 (4)
C10.57829 (12)0.13397 (9)−0.21507 (18)0.0460 (4)
C20.48087 (11)0.13874 (8)−0.11934 (17)0.0421 (4)
C30.37156 (12)0.15327 (9)−0.2200 (2)0.0512 (5)
C40.27961 (12)0.15613 (10)−0.1325 (2)0.0575 (5)
C50.29633 (12)0.14322 (10)0.0534 (2)0.0576 (5)
C60.40443 (12)0.12764 (10)0.1541 (2)0.0519 (5)
C70.49834 (11)0.12588 (8)0.06918 (17)0.0422 (4)
C80.61822 (11)0.11135 (10)0.17022 (17)0.0465 (4)
C90.70140 (11)0.16318 (9)0.07877 (17)0.0440 (4)
C100.82407 (11)0.14481 (9)0.16272 (17)0.0438 (4)
C110.88770 (12)0.20841 (10)0.27598 (19)0.0525 (5)
C120.99780 (12)0.18919 (11)0.3646 (2)0.0573 (5)
C131.04728 (11)0.10621 (10)0.34024 (18)0.0484 (4)
C140.98541 (12)0.04249 (10)0.2268 (2)0.0542 (5)
C150.87482 (12)0.06259 (10)0.1397 (2)0.0529 (5)
C161.20764 (14)0.00719 (12)0.4207 (2)0.0664 (6)
H30.360430.16105−0.345990.0615*
H40.206310.16679−0.199030.0690*
H50.233960.145010.111860.0691*
H60.414380.118260.279550.0623*
H8A0.625020.131970.295490.0558*
H8B0.636410.046930.172370.0558*
H90.6859 (12)0.2278 (10)0.0814 (19)0.0527*
H110.855770.264870.292520.0630*
H121.039080.232450.441480.0687*
H141.01772−0.013640.208920.0651*
H150.833510.019220.063190.0635*
H16A1.284120.007330.491430.0995*
H16B1.16306−0.038390.467490.0995*
H16C1.21001−0.006050.295340.0995*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0692 (7)0.0953 (8)0.0350 (5)0.0026 (6)0.0079 (5)−0.0001 (5)
O20.0472 (5)0.0654 (6)0.0364 (5)−0.0014 (4)0.0096 (4)0.0001 (4)
O30.0460 (6)0.0818 (8)0.0601 (6)0.0054 (5)−0.0018 (5)−0.0082 (5)
C10.0519 (8)0.0472 (7)0.0378 (6)0.0003 (6)0.0062 (6)0.0032 (5)
C20.0466 (7)0.0375 (6)0.0410 (7)−0.0019 (5)0.0057 (5)0.0020 (5)
C30.0539 (8)0.0477 (8)0.0480 (8)−0.0011 (6)−0.0003 (6)0.0040 (6)
C40.0443 (8)0.0557 (8)0.0688 (10)0.0005 (6)0.0013 (7)0.0014 (7)
C50.0464 (8)0.0594 (9)0.0694 (10)−0.0051 (6)0.0170 (7)−0.0047 (7)
C60.0513 (8)0.0585 (8)0.0477 (8)−0.0056 (6)0.0138 (6)−0.0006 (6)
C70.0446 (7)0.0408 (6)0.0409 (7)−0.0030 (5)0.0072 (5)0.0008 (5)
C80.0465 (7)0.0574 (8)0.0351 (6)0.0001 (6)0.0064 (5)0.0041 (5)
C90.0465 (7)0.0474 (7)0.0375 (6)−0.0012 (6)0.0069 (5)−0.0026 (5)
C100.0435 (7)0.0493 (7)0.0396 (6)−0.0033 (5)0.0106 (5)−0.0023 (5)
C110.0501 (8)0.0503 (8)0.0565 (8)−0.0003 (6)0.0089 (6)−0.0116 (6)
C120.0514 (8)0.0615 (9)0.0561 (9)−0.0065 (7)0.0033 (7)−0.0168 (7)
C130.0416 (7)0.0636 (9)0.0401 (7)−0.0007 (6)0.0079 (5)−0.0026 (6)
C140.0522 (8)0.0547 (8)0.0547 (8)0.0056 (6)0.0074 (7)−0.0085 (7)
C150.0514 (8)0.0522 (8)0.0525 (8)−0.0039 (6)0.0033 (6)−0.0126 (6)
C160.0561 (9)0.0836 (12)0.0574 (9)0.0146 (8)0.0060 (7)0.0092 (8)
Geometric parameters (Å, °) top
O1—C11.2028 (16)C12—C131.380 (2)
O2—C11.3475 (17)C13—C141.376 (2)
O2—C91.4636 (15)C14—C151.383 (2)
O3—C131.3655 (17)C3—H30.9300
O3—C161.418 (2)C4—H40.9300
C1—C21.4741 (19)C5—H50.9300
C2—C31.387 (2)C6—H60.9300
C2—C71.3931 (18)C8—H8A0.9700
C3—C41.377 (2)C8—H8B0.9700
C4—C51.375 (2)C9—H90.968 (15)
C5—C61.378 (2)C11—H110.9300
C6—C71.385 (2)C12—H120.9300
C7—C81.4947 (19)C14—H140.9300
C8—C91.5102 (19)C15—H150.9300
C9—C101.4977 (19)C16—H16A0.9600
C10—C111.3831 (19)C16—H16B0.9600
C10—C151.375 (2)C16—H16C0.9600
C11—C121.378 (2)
O1···C16i3.367 (2)C16···H142.5100
O3···C4ii3.4157 (18)H3···O12.5800
O3···C3ii3.3841 (18)H3···O3vi2.8300
O1···H32.5800H3···C5iv3.0300
O1···H6iii2.8500H4···O3vi2.9000
O1···H9iv2.608 (15)H5···O3x2.8200
O1···H8Aiii2.6500H5···C13x3.1000
O1···H16Ai2.8600H6···O1xi2.8500
O2···H11iv2.6900H6···H8A2.4900
O2···H152.6400H8A···O1xi2.6500
O2···H16Ci2.7800H8A···H62.4900
O3···H3ii2.8300H8B···C152.9000
O3···H4ii2.9000H8B···C2viii3.0500
O3···H5v2.8200H8B···C3viii2.9700
C3···C6iv3.395 (2)H9···C22.915 (14)
C3···O3vi3.3841 (18)H9···H112.3700
C3···C5iv3.465 (2)H9···O1vii2.608 (15)
C4···O3vi3.4157 (18)H9···C1vii2.967 (15)
C5···C3vii3.465 (2)H11···H92.3700
C6···C3vii3.395 (2)H11···O2vii2.6900
C16···O1i3.367 (2)H14···C162.5100
C1···H9iv2.967 (15)H14···H16B2.3600
C2···H8Bviii3.0500H14···H16C2.2600
C2···H92.915 (14)H15···O22.6400
C3···H16Avi3.0700H15···C4viii3.0000
C3···H8Bviii2.9700H15···C5viii2.8800
C4···H15viii3.0000H16A···C3ii3.0700
C5···H3vii3.0300H16A···O1i2.8600
C5···H15viii2.8800H16B···C142.7600
C13···H5v3.1000H16B···H142.3600
C14···H16B2.7600H16B···C15ix3.0700
C14···H16C2.7200H16C···C142.7200
C15···H16Bix3.0700H16C···H142.2600
C15···H8B2.9000H16C···O2i2.7800
C1—O2—C9119.41 (10)C4—C3—H3120.00
C13—O3—C16117.70 (12)C3—C4—H4120.00
O1—C1—O2117.72 (13)C5—C4—H4120.00
O1—C1—C2124.12 (13)C4—C5—H5120.00
O2—C1—C2118.15 (11)C6—C5—H5120.00
C1—C2—C3119.19 (12)C5—C6—H6120.00
C1—C2—C7120.16 (12)C7—C6—H6120.00
C3—C2—C7120.63 (12)C7—C8—H8A110.00
C2—C3—C4119.71 (13)C7—C8—H8B110.00
C3—C4—C5119.89 (14)C9—C8—H8A110.00
C4—C5—C6120.77 (14)C9—C8—H8B110.00
C5—C6—C7120.27 (13)H8A—C8—H8B108.00
C2—C7—C6118.72 (12)O2—C9—H9106.7 (8)
C2—C7—C8118.10 (12)C8—C9—H9110.0 (9)
C6—C7—C8123.18 (12)C10—C9—H9110.0 (9)
C7—C8—C9110.17 (11)C10—C11—H11120.00
O2—C9—C8109.56 (10)C12—C11—H11120.00
O2—C9—C10107.35 (10)C11—C12—H12120.00
C8—C9—C10112.99 (11)C13—C12—H12120.00
C9—C10—C11120.57 (12)C13—C14—H14120.00
C9—C10—C15121.45 (12)C15—C14—H14120.00
C11—C10—C15117.85 (13)C10—C15—H15119.00
C10—C11—C12120.85 (14)C14—C15—H15119.00
C11—C12—C13120.51 (14)O3—C16—H16A109.00
O3—C13—C12116.22 (13)O3—C16—H16B109.00
O3—C13—C14124.44 (13)O3—C16—H16C109.00
C12—C13—C14119.34 (13)H16A—C16—H16B109.00
C13—C14—C15119.47 (13)H16A—C16—H16C109.00
C10—C15—C14121.98 (13)H16B—C16—H16C109.00
C2—C3—H3120.00
C9—O2—C1—O1168.75 (13)C5—C6—C7—C8178.66 (13)
C9—O2—C1—C2−12.42 (17)C2—C7—C8—C932.06 (16)
C1—O2—C9—C847.27 (15)C6—C7—C8—C9−147.57 (13)
C1—O2—C9—C10170.31 (11)C7—C8—C9—O2−55.05 (14)
C16—O3—C13—C12175.67 (13)C7—C8—C9—C10−174.68 (11)
C16—O3—C13—C14−4.8 (2)O2—C9—C10—C11134.82 (12)
O1—C1—C2—C3−13.4 (2)O2—C9—C10—C15−49.38 (16)
O1—C1—C2—C7164.54 (14)C8—C9—C10—C11−104.28 (15)
O2—C1—C2—C3167.82 (12)C8—C9—C10—C1571.51 (16)
O2—C1—C2—C7−14.21 (18)C9—C10—C11—C12175.05 (13)
C1—C2—C3—C4178.77 (12)C15—C10—C11—C12−0.9 (2)
C7—C2—C3—C40.81 (19)C9—C10—C15—C14−175.39 (13)
C1—C2—C7—C6−177.78 (12)C11—C10—C15—C140.5 (2)
C1—C2—C7—C82.58 (17)C10—C11—C12—C130.8 (2)
C3—C2—C7—C60.17 (18)C11—C12—C13—O3179.38 (13)
C3—C2—C7—C8−179.48 (12)C11—C12—C13—C14−0.2 (2)
C2—C3—C4—C5−1.0 (2)O3—C13—C14—C15−179.72 (13)
C3—C4—C5—C60.2 (2)C12—C13—C14—C15−0.2 (2)
C4—C5—C6—C70.8 (2)C13—C14—C15—C100.0 (2)
C5—C6—C7—C2−1.0 (2)
Symmetry codes: (i) −x+2, −y, −z; (ii) x+1, y, z+1; (iii) x, y, z−1; (iv) x, −y+1/2, z−1/2; (v) x+1, y, z; (vi) x−1, y, z−1; (vii) x, −y+1/2, z+1/2; (viii) −x+1, −y, −z; (ix) −x+2, −y, −z+1; (x) x−1, y, z; (xi) x, y, z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···Cg2viii0.972.943.8398 (16)154
C16—H16B···Cg3ix0.962.893.7804 (17)154
Symmetry codes: (viii) −x+1, −y, −z; (ix) −x+2, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···Cg2i0.972.943.8398 (16)154
C16—H16B···Cg3ii0.962.893.7804 (17)154
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z+1.
Acknowledgements top

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

references
References top

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