1-(2-Hy-droxy-5-methyl-phen-yl)-3-(2-methyl-phen-yl)prop-2-en-1-one.

In the title compound, C(17)H(16)O(2), the dihedral angle between the aromatic rings is 5.12 (13)° and an intra-molecular 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 = 252.30

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.209

S = 1.15

2422 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811018381/hb5868Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H16O2	F(000) = 1072
Mr = 252.30	Dx = 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

MacScience DIPLabo 32001 diffractometer	1654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 25.0°, θmin = 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 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(Fo2) + (0.1131P)2 + 0.2932P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.009
2422 reflections	Δρmax = 0.37 e Å−3
175 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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