3,3-Dimethyl-2-benzofuran-1(3H)-one

Siddegowda, M.S.; Butcher, R.J.; Yıldırım, S.O.; Akkurt, M.; Yathirajan, H.S.; Ramesha, A.R.

doi:10.1107/S1600536811052913

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o113

doi:10.1107/S1600536811052913

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3,3-Dimethyl-2-benzofuran-1(3H)-one

M. S. Siddegowda,^a Ray J. Butcher,^b Sema Ozturk Yıldırım,^b,^c Mehmet Akkurt,^c ^* H. S. Yathirajan ^a and A. R. Ramesha ^d

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dR. L. Fine Chem, Bengaluru 560 064, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 December 2011; accepted 8 December 2011; online 14 December 2011)

In the title compound, C₁₀H₁₀O₂, all the non-H atoms except the methyl C atoms lie on a crystallographic mirror plane. In the crystal, C—H⋯O hydrogen bonds link the molecules into zigzag chains running parallel to [100]. Weak π–π stacking interactions between the benzene rings [centroid–centroid distance = 3.9817 (5) Å] link the chains in the [010] direction.

Related literature

For related structures, see: Fun et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₀H₁₀O₂
M_r = 162.18
Orthorhombic, P n m a
a = 14.3537 (9) Å
b = 7.0069 (5) Å
c = 8.2605 (5) Å
V = 830.80 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.55 × 0.44 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ) T_min = 0.952, T_max = 0.974
1840 measured reflections
1840 independent reflections
1454 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.133
S = 1.09
1840 reflections
71 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.43	3.3072 (17)	158
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811052913/hb6560sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052913/hb6560Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052913/hb6560Isup3.cml

checkCIF report

Comment top

3,3-Dimethylisobenzofuran-1(3H)-one, (I), is used to synthesize 10,10-dimethylanthrone (Fun et al., 2010). It is a one of the intermediate for melitracenium chloride (Fun et al., 2011). We now report its stucture.

In the title molecule (I), (Fig. 1), a mirror plane passes through the remaining atoms of the molecule, except the atoms of two methyl groups which are mirror images of each other.

In the crystal, intermolecular C—H ··· O hydrogen bonds link molecules forming zigzag chains in the layer parallel to the (101) plane and along the a axis (Table 1, Fig. 2a,b,c). Furthermore, there exist weak π-π stacking interactions [Cg2···Cg2(2 - x, -1/2 + y, -z) = 3.9817 (5) Å, Cg2···Cg2(2 - x, 1/2 + y, -z) = 3.9817 (5) Å, Cg2···Cg2(2 - x, -y, -z) = 3.9817 (5) Å, Cg2···Cg2(2 - x, 1 - y, -z) = 3.9817 (5) Å] between the C1–C6 benzene rings along the [010] direction.

Related literature top

For related structures, see: Fun et al. (2010, 2011).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chemicals, Bengaluru, India. Colourless prisms of (I) were grown from toluene solution by slow evaporation (m.p.: 337–340 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule (I) showing displacement ellipsoids for non-H atoms drawn at the 50% probability level.
	Fig. 2. View of the packing and hydrogen bonding of (I) down a axis.
	Fig. 3. View of the packing and hydrogen bonding of (I) down b axis.
	Fig. 4. View of the packing and hydrogen bonding of (I) down c axis.

3,3-Dimethyl-2-benzofuran-1(3H)-one top

Crystal data top

C₁₀H₁₀O₂	F(000) = 344
M_r = 162.18	D_x = 1.297 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1444 reflections
a = 14.3537 (9) Å	θ = 2.8–35.2°
b = 7.0069 (5) Å	µ = 0.09 mm⁻¹
c = 8.2605 (5) Å	T = 123 K
V = 830.80 (9) Å³	Prism, colourless
Z = 4	0.55 × 0.44 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1840 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 10.5081 pixels mm^-1	θ_max = 35.2°, θ_min = 2.8°
ω scans	h = 0→22
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→11
T_min = 0.952, T_max = 0.974	l = 0→13
1840 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0591P)² + 0.0987P] where P = (F_o² + 2F_c²)/3
1840 reflections	(Δ/σ)_max < 0.001
71 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₀H₁₀O₂	V = 830.80 (9) Å³
M_r = 162.18	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 14.3537 (9) Å	µ = 0.09 mm⁻¹
b = 7.0069 (5) Å	T = 123 K
c = 8.2605 (5) Å	0.55 × 0.44 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1840 independent reflections
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	1454 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.974	R_int = 0.000
1840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.09	Δρ_max = 0.34 e Å⁻³
1840 reflections	Δρ_min = −0.30 e Å⁻³
71 parameters

Special details top

Experimental. Absorption correction: XABS2 (Parkin et al., 1995); cubic fit to sinθ/λ - 24 parameters

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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.99217 (7)	0.25000	0.38584 (11)	0.0216 (3)
O2	1.13652 (7)	0.25000	0.28045 (13)	0.0260 (3)
C1	0.90567 (9)	0.25000	0.14603 (15)	0.0159 (3)
C2	0.83829 (9)	0.25000	0.02623 (16)	0.0193 (3)
C3	0.86910 (10)	0.25000	−0.13404 (16)	0.0211 (3)
C4	0.96384 (10)	0.25000	−0.17273 (16)	0.0208 (3)
C5	1.03071 (9)	0.25000	−0.05143 (16)	0.0192 (3)
C6	0.99948 (9)	0.25000	0.10807 (15)	0.0165 (3)
C7	1.05334 (9)	0.25000	0.25962 (15)	0.0189 (3)
C8	0.89464 (9)	0.25000	0.32851 (15)	0.0175 (3)
C9	0.84773 (7)	0.07067 (15)	0.39183 (12)	0.0229 (3)
H2	0.77510	0.25000	0.05140	0.0230*
H3	0.82540	0.25000	−0.21720	0.0250*
H4	0.98220	0.25000	−0.28070	0.0250*
H5	1.09400	0.25000	−0.07580	0.0230*
H9A	0.88010	−0.03960	0.35190	0.0340*
H9B	0.78420	0.06740	0.35560	0.0340*
H9C	0.84920	0.07080	0.50800	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0185 (4)	0.0326 (5)	0.0136 (4)	0.0000	−0.0019 (4)	0.0000
O2	0.0169 (4)	0.0368 (6)	0.0242 (5)	0.0000	−0.0042 (4)	0.0000
C1	0.0169 (5)	0.0170 (5)	0.0137 (5)	0.0000	0.0004 (4)	0.0000
C2	0.0176 (5)	0.0251 (6)	0.0153 (5)	0.0000	−0.0002 (5)	0.0000
C3	0.0220 (6)	0.0270 (6)	0.0143 (5)	0.0000	−0.0021 (5)	0.0000
C4	0.0246 (6)	0.0248 (6)	0.0131 (5)	0.0000	0.0025 (5)	0.0000
C5	0.0185 (5)	0.0213 (5)	0.0177 (5)	0.0000	0.0031 (5)	0.0000
C6	0.0176 (5)	0.0173 (5)	0.0147 (5)	0.0000	0.0003 (4)	0.0000
C7	0.0182 (6)	0.0214 (5)	0.0172 (5)	0.0000	−0.0011 (5)	0.0000
C8	0.0164 (5)	0.0232 (6)	0.0130 (5)	0.0000	−0.0007 (4)	0.0000
C9	0.0259 (5)	0.0244 (4)	0.0185 (4)	−0.0011 (4)	0.0028 (3)	0.0028 (3)

Geometric parameters (Å, º) top

O1—C7	1.3631 (16)	C6—C7	1.4714 (18)
O1—C8	1.4779 (16)	C8—C9	1.5185 (13)
O2—C7	1.2063 (16)	C8—C9ⁱ	1.5185 (13)
C1—C2	1.3837 (18)	C2—H2	0.9300
C1—C6	1.3826 (18)	C3—H3	0.9300
C1—C8	1.5157 (18)	C4—H4	0.9300
C2—C3	1.3958 (19)	C5—H5	0.9300
C3—C4	1.397 (2)	C9—H9A	0.9600
C4—C5	1.3875 (19)	C9—H9B	0.9600
C5—C6	1.3917 (18)	C9—H9C	0.9600

C7—O1—C8	111.41 (9)	C1—C8—C9	112.89 (7)
C2—C1—C6	121.23 (12)	C1—C8—C9ⁱ	112.89 (7)
C2—C1—C8	129.66 (12)	C9—C8—C9ⁱ	111.68 (10)
C6—C1—C8	109.11 (11)	C1—C2—H2	121.00
C1—C2—C3	117.19 (12)	C3—C2—H2	121.00
C2—C3—C4	121.70 (12)	C2—C3—H3	119.00
C3—C4—C5	120.54 (12)	C4—C3—H3	119.00
C4—C5—C6	117.44 (12)	C3—C4—H4	120.00
C1—C6—C5	121.90 (12)	C5—C4—H4	120.00
C1—C6—C7	108.59 (11)	C4—C5—H5	121.00
C5—C6—C7	129.51 (12)	C6—C5—H5	121.00
O1—C7—O2	121.90 (12)	C8—C9—H9A	109.00
O1—C7—C6	108.20 (11)	C8—C9—H9B	109.00
O2—C7—C6	129.90 (12)	C8—C9—H9C	110.00
O1—C8—C1	102.69 (10)	H9A—C9—H9B	109.00
O1—C8—C9	108.04 (7)	H9A—C9—H9C	109.00
O1—C8—C9ⁱ	108.04 (7)	H9B—C9—H9C	109.00

C7—O1—C8—C9	119.51 (7)	C8—C1—C6—C5	180.00
C8—O1—C7—O2	180.00	C2—C1—C8—C9	63.92 (8)
C8—O1—C7—C6	0.00	C1—C2—C3—C4	0.00
C7—O1—C8—C1	0.00	C2—C3—C4—C5	0.00
C8—C1—C2—C3	180.00	C3—C4—C5—C6	0.00
C2—C1—C6—C5	0.00	C4—C5—C6—C1	0.00
C2—C1—C6—C7	180.00	C4—C5—C6—C7	180.00
C6—C1—C2—C3	0.00	C1—C6—C7—O2	180.00
C6—C1—C8—O1	0.00	C5—C6—C7—O1	180.00
C6—C1—C8—C9	−116.08 (8)	C5—C6—C7—O2	0.00
C8—C1—C6—C7	0.00	C1—C6—C7—O1	0.00
C2—C1—C8—O1	180.00

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱⁱ	0.93	2.43	3.3072 (17)	158

Symmetry code: (ii) x−1/2, −y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₂
M_r	162.18
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	123
a, b, c (Å)	14.3537 (9), 7.0069 (5), 8.2605 (5)
V (Å³)	830.80 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.55 × 0.44 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)
T_min, T_max	0.952, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	1840, 1840, 1454
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.812

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.133, 1.09
No. of reflections	1840
No. of parameters	71
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.43	3.3072 (17)	158

Symmetry code: (i) x−1/2, −y+1/2, −z+1/2.

Acknowledgements

MSS thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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