1-(2-Hy­droxy-5-methyl­phen­yl)-3-(2-methyl­phen­yl)prop-2-en-1-one

Vijay Kumar, D.; Thippeswamy, G.B.; Jayashree, B.S.; Sridhar, M.A.

doi:10.1107/S1600536811018381

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1492

doi:10.1107/S1600536811018381

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1-(2-Hydroxy-5-methylphenyl)-3-(2-methylphenyl)prop-2-en-1-one

D. Vijay Kumar,^a G. B. Thippeswamy,^b B. S. Jayashree ^a and M. A. Sridhar ^b ^*

^aDepartment of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal 576 104, India, and ^bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 1 May 2011; accepted 15 May 2011; online 25 May 2011)

In the title compound, C₁₇H₁₆O₂, the dihedral angle between the aromatic rings is 5.12 (13)° and an intramolecular O—H⋯O hydrogen bond generates an S(6) ring.

Related literature

For a related structure and background references to chalcones, see: Thippeswamy et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₆O₂
M_r = 252.30
Orthorhombic, P b c a
a = 13.3930 (11) Å
b = 14.1740 (16) Å
c = 14.5710 (15) Å
V = 2766.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.29 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer
8036 measured reflections
2422 independent reflections
1654 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.209
S = 1.15
2422 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O18—H18⋯O11	0.82	1.89	2.608 (3)	146

Data collection: XPRESS (MacScience, 2002 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018381/hb5868sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018381/hb5868Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018381/hb5868Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of chalcones (Thippeswamy et al., 2011), we now report the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The title compound, C₁₇H₁₆O₂, consists of two methylphenyl rings attached at ei-ther sides of the propanone chain. The propanone unit is planar, which is confirmed by the r.m.s. deviation of 0.003 (3)Å from the mean plane. The dihedral angle between the least squares planes of 5-methylphenyl ring and 2-methylphenyl ring is 5.93 (13)° which indicates that 5-methylphenyl ring in +Syn-periplanar conformation with 2-methylphenyl ring. The bond lengths C1—O11, C1—C12, C1—C2, C2—C3, C3—C4 and bond angles C1—C2—C12,C1—C2—C3 are in good agreement with these of a similar compound reported earlier (Thippeswamy et al., 2011). The angles C2—C1—O11, C12—C1—O11 and C2—C1—C12 are 119.5 (2)°, 119.4 (2)° and 121.1 (2)° respectively which indicate that the position of C1 atom is nearly in trigonal geometry. An intramolecular O—H···O hydrogen bond occurs (Table 1).

Related literature top

For a related structure and background references to chalcones, see: Thippeswamy et al. (2011).

Experimental top

The title compound was prepared by dissolving 2-hydroxy-5- methoxyacetophenone 0.05 m mol in 15 ml of ethanol taken in a conical flask. To this 5 ml of 20° aqueous sodium hydroxide was added and kept for stirring at room temperature. To this mixture, 4-methylbenzaldehyde 0.05 m mol was added and continued stirring till the completion of reaction. The progress of the reaction was monitored by TLC using n-hexane and ethylacetate as solvent system. After completion of the reaction, the mixture was poured into ice cold water, mixed properly and acidified with dilute hydrochloric acid. The title compound separates as precipitate which was collected by filtration and crystallized from methanol as orange blocks of (I).

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I) with 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram for (I).

1-(2-Hydroxy-5-methylphenyl)-3-(2-methylphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₆O₂	F(000) = 1072
M_r = 252.30	D_x = 1.212 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8036 reflections
a = 13.3930 (11) Å	θ = 2.4–25.0°
b = 14.1740 (16) Å	µ = 0.08 mm⁻¹
c = 14.5710 (15) Å	T = 293 K
V = 2766.0 (5) Å³	Block, orange
Z = 8	0.29 × 0.27 × 0.25 mm

Data collection top

MacScience DIPLabo 32001 diffractometer	1654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.0°, θ_min = 2.5°
Detector resolution: 10.0 pixels mm^-1	h = −15→15
ω scans	k = −15→16
8036 measured reflections	l = −17→17
2422 independent 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)] = 0.073	H-atom parameters constrained
wR(F²) = 0.209	w = 1/[σ²(F_o²) + (0.1131P)² + 0.2932P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.009
2422 reflections	Δρ_max = 0.37 e Å⁻³
175 parameters	Δρ_min = −0.38 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: 0.025 (4)

Crystal data top

C₁₇H₁₆O₂	V = 2766.0 (5) Å³
M_r = 252.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.3930 (11) Å	µ = 0.08 mm⁻¹
b = 14.1740 (16) Å	T = 293 K
c = 14.5710 (15) Å	0.29 × 0.27 × 0.25 mm

Data collection top

MacScience DIPLabo 32001 diffractometer	1654 reflections with I > 2σ(I)
8036 measured reflections	R_int = 0.044
2422 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.209	H-atom parameters constrained
S = 1.15	Δρ_max = 0.37 e Å⁻³
2422 reflections	Δρ_min = −0.38 e Å⁻³
175 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
C1	0.93869 (16)	0.33849 (16)	0.36305 (17)	0.0641 (7)
C2	0.91789 (15)	0.39731 (16)	0.44755 (17)	0.0667 (7)
H2	0.9447	0.3787	0.5036	0.080*
C3	0.86192 (16)	0.47546 (16)	0.44390 (17)	0.0657 (7)
H3	0.8382	0.4919	0.3861	0.079*
C4	0.83271 (15)	0.53964 (17)	0.52070 (17)	0.0686 (7)
C5	0.8504 (2)	0.5140 (2)	0.6137 (2)	0.0882 (9)
H5	0.8804	0.4563	0.6266	0.106*
C6	0.8230 (3)	0.5747 (3)	0.6874 (2)	0.1102 (11)
H6	0.8356	0.5570	0.7477	0.132*
C7	0.7767 (3)	0.6617 (3)	0.6682 (3)	0.1179 (14)
H7	0.7587	0.7019	0.7159	0.141*
C8	0.7581 (2)	0.6874 (2)	0.5779 (3)	0.1063 (12)
H8	0.7271	0.7449	0.5665	0.128*
C9	0.78464 (17)	0.62923 (19)	0.5019 (2)	0.0812 (8)
C10	0.7635 (2)	0.6625 (2)	0.4032 (3)	0.1076 (11)
H10A	0.7293	0.7220	0.4048	0.161*
H10B	0.7225	0.6167	0.3725	0.161*
H10C	0.8254	0.6695	0.3707	0.161*
O11	0.91143 (13)	0.36828 (12)	0.28533 (12)	0.0830 (6)
C12	0.98967 (15)	0.24407 (16)	0.37022 (17)	0.0626 (6)
C13	1.02359 (15)	0.20750 (17)	0.45520 (17)	0.0673 (7)
H13	1.0135	0.2428	0.5082	0.081*
C14	1.07221 (17)	0.11945 (19)	0.4623 (2)	0.0772 (8)
C15	1.0858 (2)	0.0661 (2)	0.3793 (2)	0.0908 (9)
H15	1.1180	0.0081	0.3825	0.109*
C16	1.0530 (2)	0.0979 (2)	0.2950 (2)	0.0924 (9)
H16	1.0623	0.0611	0.2429	0.111*
C17	1.00483 (19)	0.18723 (18)	0.2883 (2)	0.0749 (7)
O18	0.97406 (16)	0.21620 (15)	0.20261 (13)	0.1000 (7)
H18	0.9475	0.2682	0.2066	0.150*
C19	1.1099 (2)	0.0842 (2)	0.5547 (2)	0.0995 (10)
H19A	1.1807	0.0944	0.5588	0.149*
H19B	1.0960	0.0181	0.5605	0.149*
H19C	1.0770	0.1180	0.6031	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0505 (11)	0.0700 (14)	0.0717 (16)	−0.0065 (10)	−0.0030 (10)	−0.0002 (12)
C2	0.0521 (12)	0.0733 (14)	0.0748 (17)	0.0036 (11)	−0.0079 (11)	−0.0016 (12)
C3	0.0485 (11)	0.0733 (14)	0.0754 (16)	−0.0053 (11)	0.0020 (10)	0.0045 (12)
C4	0.0436 (11)	0.0783 (15)	0.0837 (19)	−0.0045 (11)	0.0050 (11)	−0.0046 (12)
C5	0.0648 (15)	0.109 (2)	0.091 (2)	−0.0065 (14)	0.0051 (14)	−0.0096 (17)
C6	0.0821 (19)	0.159 (3)	0.089 (2)	−0.025 (2)	0.0116 (17)	−0.026 (2)
C7	0.081 (2)	0.140 (3)	0.133 (3)	−0.025 (2)	0.036 (2)	−0.057 (3)
C8	0.0632 (16)	0.095 (2)	0.161 (4)	−0.0030 (15)	0.030 (2)	−0.030 (2)
C9	0.0486 (13)	0.0778 (16)	0.117 (2)	−0.0026 (12)	0.0137 (13)	−0.0063 (16)
C10	0.0789 (18)	0.094 (2)	0.150 (3)	0.0232 (17)	0.0071 (19)	0.0232 (19)
O11	0.0850 (12)	0.0894 (12)	0.0746 (13)	0.0041 (10)	−0.0114 (9)	0.0032 (9)
C12	0.0476 (11)	0.0683 (13)	0.0721 (16)	−0.0059 (10)	0.0035 (10)	−0.0023 (11)
C13	0.0451 (11)	0.0729 (14)	0.0839 (18)	0.0025 (11)	0.0032 (11)	−0.0028 (12)
C14	0.0506 (13)	0.0789 (16)	0.102 (2)	0.0035 (12)	0.0047 (12)	0.0072 (15)
C15	0.0686 (16)	0.0779 (17)	0.126 (3)	0.0118 (14)	0.0164 (17)	−0.0007 (17)
C16	0.0861 (18)	0.0858 (19)	0.105 (2)	0.0037 (15)	0.0221 (17)	−0.0233 (16)
C17	0.0698 (15)	0.0801 (16)	0.0749 (18)	−0.0078 (13)	0.0117 (12)	−0.0047 (13)
O18	0.1154 (16)	0.1075 (15)	0.0771 (14)	0.0001 (12)	0.0056 (11)	−0.0128 (11)
C19	0.0693 (16)	0.103 (2)	0.126 (3)	0.0179 (16)	−0.0041 (16)	0.0227 (18)

Geometric parameters (Å, º) top

C1—O11	1.263 (3)	C10—H10A	0.9600
C1—C12	1.506 (3)	C10—H10B	0.9600
C1—C2	1.513 (3)	C10—H10C	0.9600
C2—C3	1.339 (3)	C12—C13	1.417 (3)
C2—H2	0.9300	C12—C17	1.454 (4)
C3—C4	1.494 (3)	C13—C14	1.411 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.423 (4)	C14—C15	1.438 (4)
C4—C9	1.450 (4)	C14—C19	1.523 (4)
C5—C6	1.423 (4)	C15—C16	1.379 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.409 (5)	C16—C17	1.425 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.387 (5)	C17—O18	1.378 (3)
C7—H7	0.9300	O18—H18	0.8200
C8—C9	1.425 (4)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—C10	1.541 (4)	C19—H19C	0.9600

O11—C1—C12	119.4 (2)	H10A—C10—H10B	109.5
O11—C1—C2	119.5 (2)	C9—C10—H10C	109.5
C12—C1—C2	121.1 (2)	H10A—C10—H10C	109.5
C3—C2—C1	121.8 (2)	H10B—C10—H10C	109.5
C3—C2—H2	119.1	C13—C12—C17	118.0 (2)
C1—C2—H2	119.1	C13—C12—C1	122.1 (2)
C2—C3—C4	128.4 (2)	C17—C12—C1	119.9 (2)
C2—C3—H3	115.8	C14—C13—C12	122.4 (2)
C4—C3—H3	115.8	C14—C13—H13	118.8
C5—C4—C9	118.5 (2)	C12—C13—H13	118.8
C5—C4—C3	120.9 (2)	C13—C14—C15	117.5 (3)
C9—C4—C3	120.6 (2)	C13—C14—C19	120.5 (3)
C4—C5—C6	121.4 (3)	C15—C14—C19	122.0 (2)
C4—C5—H5	119.3	C16—C15—C14	122.4 (3)
C6—C5—H5	119.3	C16—C15—H15	118.8
C7—C6—C5	119.6 (3)	C14—C15—H15	118.8
C7—C6—H6	120.2	C15—C16—C17	119.7 (3)
C5—C6—H6	120.2	C15—C16—H16	120.1
C8—C7—C6	119.7 (3)	C17—C16—H16	120.1
C8—C7—H7	120.1	O18—C17—C16	117.6 (3)
C6—C7—H7	120.1	O18—C17—C12	122.5 (2)
C7—C8—C9	122.7 (3)	C16—C17—C12	119.9 (3)
C7—C8—H8	118.6	C17—O18—H18	109.5
C9—C8—H8	118.6	C14—C19—H19A	109.5
C8—C9—C4	118.1 (3)	C14—C19—H19B	109.5
C8—C9—C10	120.2 (3)	H19A—C19—H19B	109.5
C4—C9—C10	121.7 (2)	C14—C19—H19C	109.5
C9—C10—H10A	109.5	H19A—C19—H19C	109.5
C9—C10—H10B	109.5	H19B—C19—H19C	109.5

O11—C1—C2—C3	7.3 (3)	C2—C1—C12—C13	−2.3 (3)
C12—C1—C2—C3	−171.5 (2)	O11—C1—C12—C17	−1.5 (3)
C1—C2—C3—C4	178.5 (2)	C2—C1—C12—C17	177.34 (19)
C2—C3—C4—C5	−10.4 (3)	C17—C12—C13—C14	0.9 (3)
C2—C3—C4—C9	170.3 (2)	C1—C12—C13—C14	−179.4 (2)
C9—C4—C5—C6	−0.8 (4)	C12—C13—C14—C15	−0.6 (3)
C3—C4—C5—C6	179.9 (2)	C12—C13—C14—C19	178.3 (2)
C4—C5—C6—C7	0.5 (4)	C13—C14—C15—C16	−0.3 (4)
C5—C6—C7—C8	0.1 (4)	C19—C14—C15—C16	−179.2 (2)
C6—C7—C8—C9	−0.4 (5)	C14—C15—C16—C17	0.9 (4)
C7—C8—C9—C4	0.2 (4)	C15—C16—C17—O18	179.5 (2)
C7—C8—C9—C10	−179.0 (3)	C15—C16—C17—C12	−0.6 (4)
C5—C4—C9—C8	0.4 (3)	C13—C12—C17—O18	179.6 (2)
C3—C4—C9—C8	179.8 (2)	C1—C12—C17—O18	−0.1 (3)
C5—C4—C9—C10	179.6 (2)	C13—C12—C17—C16	−0.3 (3)
C3—C4—C9—C10	−1.0 (3)	C1—C12—C17—C16	−180.0 (2)
O11—C1—C12—C13	178.86 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11	0.82	1.89	2.608 (3)	146

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₂
M_r	252.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	13.3930 (11), 14.1740 (16), 14.5710 (15)
V (Å³)	2766.0 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.27 × 0.25

Data collection
Diffractometer	MacScience DIPLabo 32001 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8036, 2422, 1654
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.209, 1.15
No. of reflections	2422
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.38

Computer programs: XPRESS (MacScience, 2002), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11	0.82	1.89	2.608 (3)	146

Acknowledgements

The authors are grateful to the DST/CSIR, New Delhi, and the University of Mysore for financial support and duly acknowledge Manipal College of Pharmaceutical Sciences for providing facilities to carry out the synthetic work.

References

Johnson, C. K. (1976). ORTEPII. Report ORNL–5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
MacScience (2002). XPRESS. MacScience Co. Ltd, Yokohama, Japan. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thippeswamy, G. B., Vijay Kumar, D., Jayashree, B. S., Sridhar, M. A. & Shashidhara Prasad, J. (2011). Acta Cryst. E67, o829. Web of Science CSD CrossRef IUCr Journals Google Scholar