7-Meth­oxy-3,4-dihydro­naphthalen-1(2H)-one

Jasinski, J.P.; Golen, J.A.; Sekar, S.; Yathirajan, H.S.; Naik, N.

doi:10.1107/S1600536811020174

organic compounds

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Volume 67| Part 7| July 2011| Page o1646

doi:10.1107/S1600536811020174

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7-Methoxy-3,4-dihydronaphthalen-1(2H)-one

Jerry P. Jasinski,^a ^* James A. Golen,^a S. Sekar,^b H. S. Yathirajan ^b and Nagaraja Naik ^b

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 25 May 2011; accepted 26 May 2011; online 11 June 2011)

In the title compound, C₁₁H₁₂O₂, the six-membered ketone ring fused to the 7-methoxy benzene ring adopts a slightly distorted envelope configuration with the central methylene C atom being the flap. The crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯π interactions, which lead to supramolecular layers in the bc plane.

Related literature

For the synthesis of steroid estrogens, see: Belov et al. (2007 ). For the manufacture of important antidepressant drugs, see: Shum et al. (2000 ). For multi-functional scaffolds of tetralone, see: Mahapatra et al. (2008 ). For related structures, see: Barcon et al. (2001 ); Haddad (1986 ); Orlov et al. (1996 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₁H₁₂O₂
M_r = 176.21
Monoclinic, P 2₁ /c
a = 7.4303 (4) Å
b = 7.4614 (4) Å
c = 16.4393 (8) Å
β = 90.976 (4)°
V = 911.27 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 170 K
0.35 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.970, T_max = 0.991
8750 measured reflections
2345 independent reflections
1959 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.04
2345 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C3,C8–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯O1ⁱ	0.98	2.38	3.3095 (18)	157
C5—H5A⋯Cg1ⁱⁱ	0.99	2.77	3.6730 (14)	152
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020174/tk2750sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020174/tk2750Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020174/tk2750Isup3.cml

checkCIF report

Comment top

The structural and therapeutic diversity of small heterocyclic molecules continue to attract the attention of organic and medicinal chemists. Tetralones are emerging prominently as pharmacologically important bioactive molecules. Tetralone is an important and common intermediate in organic synthesis and is a ketone derivative of tetralin. The title compound (Systematic name: 3 ,4-Dihydro-7-methoxy-2(1H)-naphthalenone), (I), C₁₁H₁₂O₂, is used in the preparation of agomelatine, which is an antidepressant. The importance of tetralone and its substituted derivatives as building blocks in the synthesis of steroid estrogens via isothiuronium salts is reported (Belov et al., 2007). Tetralones are also important intermediates for the manufacturing of various serotonin inhibitor compounds having antidepressant activity, particularly sertraline, an important antidepressant drug (Shum et al., 2000). Multi functional scaffolds of tetralone to generate further diversity with different functionalities is reported (Mahapatra et al., 2008). The crystal structures of some related compounds, viz., 2,2-dibromo-3,4-dihydro-1(2H)-naphthalenone (Haddad et al., 1986), 2-(4-nitrobenzylidene)-1-tetralone (Orlov et al., 1996), (±)-1-tetralone-3-carboxylic acid and (±)-1-tetralone-2-acetic acid (Barcon et al., 2001),have been reported. In view of the importance of tetralones, this paper reports the crystal structure of the title compound, (I).

In the title compound, C₁₁H₁₂O₂, the six-membered ketone ring fused to the benzene ring adopts a slightly distorted envelope configuration (Cremer & Pople, 1975) with puckering parameters Q, θ and ϕ of 0.4869 (14) Å, 56.33 (15) ° and 185.10 (18) °, respectively (Fig. 1). For an ideal envelope θ and ϕ have values of 54.7° and 180°. Crystal packing is stabilized by weak C—H···O and C—H···π (Table 1) intermolecular interactions.

Related literature top

For the synthesis of steroid estrogens, see: Belov et al. (2007). For the manufacture of important antidepressant drugs, see: Shum et al. (2000). For multi-functional scaffolds of tetralone, see: Mahapatra et al. (2008). For related structures, see: Barcon et al. (2001); Haddad (1986); Orlov et al. (1996). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Anisole (4.3 ml, 0.040 mol) is acylated with succinic anhydride (4.2 g, 0.042 mol) in the presence of anhydrous aluminium chloride and nitrobenzene as solvent to give the intermediate keto acid. The keto group is reduced by hydrogenation with Pd/C as catalyst at 2-3 kgs pressure and 343-348 K for 2 -3 hours. Further work up, isolation and cyclization with poly phosphoric acid (PPA) gives 7-methoxy-1-tetralone (Fig. 1). X-ray quality crystals of (I) were obtained by slow evaporation from isopropyl alcohol (M.pt.: 333-336 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); 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

	Fig. 1. Reaction scheme for the title compound.
	Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.

7-Methoxy-3,4-dihydronaphthalen-1(2H)-one top

Crystal data top

C₁₁H₁₂O₂	F(000) = 376
M_r = 176.21	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4312 reflections
a = 7.4303 (4) Å	θ = 3.7–32.3°
b = 7.4614 (4) Å	µ = 0.09 mm⁻¹
c = 16.4393 (8) Å	T = 170 K
β = 90.976 (4)°	Block, colorless
V = 911.27 (8) Å³	0.35 × 0.25 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2345 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1959 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.1500 pixels mm^-1	θ_max = 28.7°, θ_min = 3.7°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −9→10
T_min = 0.970, T_max = 0.991	l = −21→22
8750 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0642P)² + 0.1602P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2345 reflections	Δρ_max = 0.26 e Å⁻³
120 parameters	Δρ_min = −0.17 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: 0.053 (7)

Crystal data top

C₁₁H₁₂O₂	V = 911.27 (8) Å³
M_r = 176.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4303 (4) Å	µ = 0.09 mm⁻¹
b = 7.4614 (4) Å	T = 170 K
c = 16.4393 (8) Å	0.35 × 0.25 × 0.10 mm
β = 90.976 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2345 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	1959 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.991	R_int = 0.023
8750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
2345 reflections	Δρ_min = −0.17 e Å⁻³
120 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.62487 (12)	0.84217 (13)	0.45326 (5)	0.0466 (3)
O2	0.87018 (12)	0.68273 (16)	0.72482 (6)	0.0553 (3)
C1	0.70272 (16)	0.66013 (17)	0.69096 (7)	0.0380 (3)
C2	0.67929 (14)	0.72639 (15)	0.61301 (6)	0.0335 (3)
H2A	0.7769	0.7829	0.5867	0.040*
C3	0.51381 (14)	0.71094 (14)	0.57282 (6)	0.0307 (2)
C4	0.49582 (15)	0.78093 (15)	0.48827 (7)	0.0336 (3)
C5	0.31401 (17)	0.77041 (18)	0.44739 (7)	0.0418 (3)
H5A	0.3094	0.6623	0.4125	0.050*
H5B	0.2977	0.8763	0.4117	0.050*
C6	0.15984 (16)	0.76306 (18)	0.50688 (8)	0.0447 (3)
H6A	0.1523	0.8781	0.5366	0.054*
H6B	0.0449	0.7447	0.4767	0.054*
C7	0.18949 (16)	0.61092 (18)	0.56688 (8)	0.0440 (3)
H7A	0.0917	0.6112	0.6070	0.053*
H7B	0.1850	0.4952	0.5375	0.053*
C8	0.36834 (15)	0.62853 (15)	0.61076 (7)	0.0355 (3)
C9	0.39581 (17)	0.56299 (18)	0.68908 (8)	0.0449 (3)
H9A	0.2986	0.5063	0.7157	0.054*
C10	0.55946 (18)	0.57744 (19)	0.72955 (7)	0.0457 (3)
H10A	0.5742	0.5315	0.7831	0.055*
C11	0.9071 (2)	0.6037 (3)	0.80161 (9)	0.0775 (6)
H11A	1.0326	0.6270	0.8176	0.116*
H11B	0.8871	0.4741	0.7982	0.116*
H11C	0.8271	0.6553	0.8422	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (5)	0.0552 (6)	0.0401 (5)	−0.0057 (4)	0.0086 (4)	0.0067 (4)
O2	0.0402 (5)	0.0863 (8)	0.0392 (5)	0.0017 (5)	−0.0064 (4)	0.0004 (5)
C1	0.0357 (6)	0.0438 (6)	0.0344 (6)	0.0044 (5)	0.0005 (4)	−0.0048 (4)
C2	0.0312 (5)	0.0358 (6)	0.0338 (5)	−0.0018 (4)	0.0044 (4)	−0.0026 (4)
C3	0.0312 (5)	0.0288 (5)	0.0322 (5)	−0.0006 (4)	0.0033 (4)	−0.0018 (4)
C4	0.0368 (5)	0.0300 (5)	0.0341 (5)	0.0001 (4)	0.0032 (4)	−0.0031 (4)
C5	0.0452 (7)	0.0409 (6)	0.0390 (6)	−0.0030 (5)	−0.0065 (5)	−0.0005 (5)
C6	0.0332 (6)	0.0463 (7)	0.0542 (7)	−0.0003 (5)	−0.0063 (5)	−0.0041 (5)
C7	0.0320 (6)	0.0476 (7)	0.0524 (7)	−0.0083 (5)	0.0029 (5)	−0.0002 (5)
C8	0.0326 (6)	0.0342 (6)	0.0399 (6)	−0.0025 (4)	0.0052 (4)	−0.0010 (4)
C9	0.0423 (7)	0.0485 (7)	0.0442 (6)	−0.0052 (5)	0.0116 (5)	0.0080 (5)
C10	0.0506 (7)	0.0534 (8)	0.0332 (6)	0.0034 (6)	0.0060 (5)	0.0074 (5)
C11	0.0548 (9)	0.1375 (18)	0.0399 (7)	0.0233 (10)	−0.0073 (6)	0.0056 (9)

Geometric parameters (Å, º) top

O1—C4	1.2159 (14)	C6—C7	1.5175 (19)
O2—C1	1.3649 (14)	C6—H6A	0.9900
O2—C11	1.4159 (19)	C6—H6B	0.9900
C1—C2	1.3818 (16)	C7—C8	1.5070 (16)
C1—C10	1.3925 (18)	C7—H7A	0.9900
C2—C3	1.3907 (15)	C7—H7B	0.9900
C2—H2A	0.9500	C8—C9	1.3891 (17)
C3—C8	1.3994 (15)	C9—C10	1.3804 (19)
C3—C4	1.4887 (15)	C9—H9A	0.9500
C4—C5	1.5006 (16)	C10—H10A	0.9500
C5—C6	1.5198 (18)	C11—H11A	0.9800
C5—H5A	0.9900	C11—H11B	0.9800
C5—H5B	0.9900	C11—H11C	0.9800

C1—O2—C11	118.26 (12)	C5—C6—H6B	109.7
O2—C1—C2	115.69 (10)	H6A—C6—H6B	108.2
O2—C1—C10	124.58 (11)	C8—C7—C6	111.28 (10)
C2—C1—C10	119.73 (11)	C8—C7—H7A	109.4
C1—C2—C3	120.49 (10)	C6—C7—H7A	109.4
C1—C2—H2A	119.8	C8—C7—H7B	109.4
C3—C2—H2A	119.8	C6—C7—H7B	109.4
C2—C3—C8	120.53 (10)	H7A—C7—H7B	108.0
C2—C3—C4	118.63 (9)	C9—C8—C3	117.73 (11)
C8—C3—C4	120.83 (10)	C9—C8—C7	121.83 (10)
O1—C4—C3	120.99 (10)	C3—C8—C7	120.43 (10)
O1—C4—C5	121.25 (10)	C10—C9—C8	122.25 (11)
C3—C4—C5	117.75 (10)	C10—C9—H9A	118.9
C4—C5—C6	113.35 (10)	C8—C9—H9A	118.9
C4—C5—H5A	108.9	C9—C10—C1	119.27 (11)
C6—C5—H5A	108.9	C9—C10—H10A	120.4
C4—C5—H5B	108.9	C1—C10—H10A	120.4
C6—C5—H5B	108.9	O2—C11—H11A	109.5
H5A—C5—H5B	107.7	O2—C11—H11B	109.5
C7—C6—C5	110.04 (10)	H11A—C11—H11B	109.5
C7—C6—H6A	109.7	O2—C11—H11C	109.5
C5—C6—H6A	109.7	H11A—C11—H11C	109.5
C7—C6—H6B	109.7	H11B—C11—H11C	109.5

C11—O2—C1—C2	−174.47 (13)	C5—C6—C7—C8	56.14 (14)
C11—O2—C1—C10	5.8 (2)	C2—C3—C8—C9	−0.25 (17)
O2—C1—C2—C3	−179.84 (10)	C4—C3—C8—C9	178.68 (10)
C10—C1—C2—C3	−0.07 (18)	C2—C3—C8—C7	−179.62 (10)
C1—C2—C3—C8	0.18 (17)	C4—C3—C8—C7	−0.69 (16)
C1—C2—C3—C4	−178.76 (10)	C6—C7—C8—C9	150.91 (12)
C2—C3—C4—O1	3.71 (16)	C6—C7—C8—C3	−29.74 (16)
C8—C3—C4—O1	−175.24 (11)	C3—C8—C9—C10	0.20 (19)
C2—C3—C4—C5	−177.30 (10)	C7—C8—C9—C10	179.56 (12)
C8—C3—C4—C5	3.75 (15)	C8—C9—C10—C1	−0.1 (2)
O1—C4—C5—C6	−156.85 (12)	O2—C1—C10—C9	179.77 (12)
C3—C4—C5—C6	24.16 (15)	C2—C1—C10—C9	0.02 (19)
C4—C5—C6—C7	−53.97 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C3,C8–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O1ⁱ	0.98	2.38	3.3095 (18)	157
C5—H5A···Cg1ⁱⁱ	0.99	2.77	3.6730 (14)	152

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂O₂
M_r	176.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	170
a, b, c (Å)	7.4303 (4), 7.4614 (4), 16.4393 (8)
β (°)	90.976 (4)
V (Å³)	911.27 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.25 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.970, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8750, 2345, 1959
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.04
No. of reflections	2345
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C3,C8–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O1ⁱ	0.98	2.38	3.3095 (18)	157
C5—H5A···Cg1ⁱⁱ	0.99	2.77	3.6730 (14)	152

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1.

Acknowledgements

SS thanks the UOM for the research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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