3-Benzyl­isochroman-1-one

Babar, T.M.; Qadeer, G.; Rama, N.H.; Khawar Rauf, M.; Wong, W.-Y.

doi:10.1107/S1600536809004164

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o498

doi:10.1107/S1600536809004164

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3-Benzylisochroman-1-one

Tariq Mahmood Babar,^a Ghulam Qadeer,^a ^* Nasim Hasan Rama,^a ‡ Muhammad Khawar Rauf ^a and Wai-Yeung Wong ^b §

^aDepartment of Chemistry, Quaid-i-azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong, People's Republic of China
^*Correspondence e-mail: qadeerqau@yahoo.com

(Received 22 January 2009; accepted 4 February 2009; online 11 February 2009)

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.

Related literature

For related structures, see: Schmalle et al. (1982 ); Schnebel et al. (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For bond-length data, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₄O₂
M_r = 238.27
Monoclinic, P 2₁ /c
a = 12.503 (5) Å
b = 8.0200 (9) Å
c = 12.892 (5) Å
β = 102.43 (2)°
V = 1262.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.32 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.820, T_max = 0.983
7148 measured reflections
3024 independent reflections
2546 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.136
S = 1.03
3024 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1ⁱ	0.97	2.53	3.2922 (18)	135
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004164/hk2615sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004164/hk2615Isup2.hkl

checkCIF report

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-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, Q_T, 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.

Related literature top

For related structures, see: Schmalle et al. (1982); Schnebel et al. (2003). For a description of the Cambridge Structural Database, see: Allen (2002). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

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.

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
	Fig. 3. The formation of the title compound.

3-Benzylisochroman-1-one top

Crystal data top

C₁₆H₁₄O₂	F(000) = 504
M_r = 238.27	D_x = 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 monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 28.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
T_min = 0.820, T_max = 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(F_o²) + (0.0818P)² + 0.1131P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3024 reflections	Δρ_max = 0.18 e Å⁻³
164 parameters	Δρ_min = −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
M_r = 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)
T_min = 0.820, T_max = 0.983	R_int = 0.021
7148 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
3024 reflections	Δρ_min = −0.14 e Å⁻³
164 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

	x	y	z	U_iso*/U_eq
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, º) 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, º) 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 code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₂
M_r	238.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.503 (5), 8.0200 (9), 12.892 (5)
β (°)	102.43 (2)
V (Å³)	1262.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.26 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.820, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7148, 3024, 2546
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 1.03
No. of reflections	3024
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) 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 code: (i) x, −y+1/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail nasimhrama@yahoo.com.

§Additional correspondence author, e-mail rwywong@hkbu.edu.hk.

Acknowledgements

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

References

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