1-(2-Hydroxy-4,6-di­methyl­phenyl)­ethanone

In the crystal of the title compound, C₁₀H₁₂O₂, there are two symmetry-independent mol­ecules, which are essentially superimposable. Each mol­ecule exhibits an intramolecular O-H...O hydrogen bond, with O...O separations of 2.483 (4) and 2.468 (4) Å.

Computing details

Data collection: P3/P4-PC Diffractometer Control Program(Siemens, 1991); cell refinement: P3/P4-PC Diffractometer Control Program; data reduction: P3/P4-PC Diffractometer Control Program; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1994); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

2-hydroxy-4,6-dimethylphenylethanone

Crystal data

C10H12O2	F(000) = 352
Mr = 164.20	Dx = 1.234 Mg m^−3
Triclinic, P1	Melting point: 328 K
a = 7.431 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.604 (3) Å	Cell parameters from 50 reflections
c = 16.007 (6) Å	θ = 8.1–13.3°
α = 93.61 (3)°	µ = 0.09 mm^−1
β = 95.50 (4)°	T = 293 K
γ = 99.89 (4)°	Parallelepiped, pale yellow
V = 884.0 (7) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Nicolet R3m/V diffractometer	Rint = 0.004
Radiation source: fine-focus sealed tube	θmax = 25.6°, θmin = 2.6°
Graphite monochromator	h = 0→8
ω–2θ scans	k = −8→8
2932 measured reflections	l = −19→19
2917 independent reflections	2 standard reflections every 150 reflections
1334 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.1115P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
2917 reflections	Δρmax = 0.27 e Å^−3
218 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: direct methods	Extinction coefficient: 0.0725 (89)

Special details

Experimental. The data completeness is affected by the omission of the very negative intensities, which generally lie in the outer shell of the data.

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 on F² for ALL reflections except for 0 with very negative F² or 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 > 2σ(F²) is used only for calculating the R factors for observed reflections 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.1494 (4)	0.1435 (4)	−0.0420 (2)	0.0925 (10)
O2	0.2942 (4)	0.2305 (3)	0.1044 (2)	0.0785 (9)
H2A	0.2454 (4)	0.1626 (3)	0.0636 (2)	0.118*
C1	0.2465 (4)	0.4467 (4)	0.0032 (2)	0.0494 (9)
C2	0.3099 (5)	0.4015 (4)	0.0839 (2)	0.0538 (9)
C3	0.3904 (5)	0.5317 (5)	0.1472 (2)	0.0581 (10)
H3A	0.4294 (5)	0.4978 (5)	0.1998 (2)	0.070*
C4	0.4133 (5)	0.7091 (5)	0.1333 (2)	0.0581 (10)
C5	0.3550 (5)	0.7559 (4)	0.0548 (2)	0.0572 (9)
H5A	0.3718 (5)	0.8767 (4)	0.0453 (2)	0.069*
C6	0.2729 (4)	0.6320 (4)	−0.0107 (2)	0.0503 (9)
C7	0.1599 (5)	0.3000 (5)	−0.0605 (2)	0.0609 (10)
C8	0.0814 (6)	0.3244 (6)	−0.1471 (2)	0.0829 (13)
H8A	0.0332 (6)	0.2094 (6)	−0.1764 (2)	0.124*
H8B	0.1758 (6)	0.3870 (6)	−0.1767 (2)	0.124*
H8C	−0.0156 (6)	0.3926 (6)	−0.1440 (2)	0.124*
C9	0.2185 (6)	0.7077 (5)	−0.0924 (2)	0.0730 (12)
H9A	0.1631 (6)	0.6115 (5)	−0.1336 (2)	0.109*
H9B	0.3256 (6)	0.7740 (5)	−0.1124 (2)	0.109*
H9C	0.1321 (6)	0.7856 (5)	−0.0833 (2)	0.109*
C10	0.4975 (6)	0.8525 (6)	0.2016 (3)	0.0897 (14)
H10A	0.5020 (6)	0.9680 (6)	0.1800 (3)	0.135*
H10B	0.6198 (6)	0.8365 (6)	0.2203 (3)	0.135*
H10C	0.4245 (6)	0.8448 (6)	0.2480 (3)	0.135*
O1'	−0.2981 (4)	−0.4972 (4)	−0.6728 (2)	0.0899 (10)
O2'	−0.1634 (4)	−0.2149 (3)	−0.5879 (2)	0.0765 (9)
H2'A	−0.2048 (4)	−0.2811 (3)	−0.6303 (2)	0.115*
C1'	−0.2504 (4)	−0.4940 (4)	−0.5254 (2)	0.0493 (9)
C2'	−0.1758 (4)	−0.3095 (4)	−0.5195 (2)	0.0507 (9)
C3'	−0.1112 (5)	−0.2154 (4)	−0.4435 (2)	0.0550 (9)
H3'A	−0.0606 (5)	−0.0945 (4)	−0.4422 (2)	0.066*
C4'	−0.1196 (5)	−0.2961 (5)	−0.3693 (2)	0.0602 (10)
C5'	−0.1900 (5)	−0.4783 (5)	−0.3742 (2)	0.0647 (10)
H5'A	−0.1937 (5)	−0.5353 (5)	−0.3246 (2)	0.078*
C6'	−0.2547 (5)	−0.5791 (5)	−0.4493 (2)	0.0548 (9)
C7'	−0.3147 (5)	−0.5818 (5)	−0.6111 (3)	0.0652 (11)
C8'	−0.4068 (6)	−0.7731 (5)	−0.6289 (3)	0.0939 (15)
H8'A	−0.4359 (6)	−0.7998 (5)	−0.6886 (3)	0.141*
H8'B	−0.5177 (6)	−0.7929 (5)	−0.6020 (3)	0.141*
H8'C	−0.3258 (6)	−0.8496 (5)	−0.6076 (3)	0.141*
C9'	−0.3248 (6)	−0.7755 (5)	−0.4426 (3)	0.0904 (14)
H9'A	−0.3664 (6)	−0.8334 (5)	−0.4977 (3)	0.136*
H9'B	−0.4250 (6)	−0.7886 (5)	−0.4084 (3)	0.136*
H9'C	−0.2276 (6)	−0.8295 (5)	−0.4172 (3)	0.136*
C10'	−0.0510 (7)	−0.1904 (6)	−0.2870 (2)	0.0950 (15)
H10D	−0.0672 (7)	−0.2673 (6)	−0.2419 (2)	0.142*
H10E	−0.1188 (7)	−0.0949 (6)	−0.2796 (2)	0.142*
H10F	0.0771 (7)	−0.1413 (6)	−0.2865 (2)	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.118 (3)	0.050 (2)	0.104 (2)	0.006 (2)	0.012 (2)	−0.007 (2)
O2	0.101 (2)	0.055 (2)	0.086 (2)	0.0216 (14)	0.016 (2)	0.0219 (14)
C1	0.046 (2)	0.050 (2)	0.055 (2)	0.012 (2)	0.009 (2)	0.005 (2)
C2	0.056 (2)	0.048 (2)	0.062 (2)	0.016 (2)	0.011 (2)	0.013 (2)
C3	0.059 (2)	0.074 (3)	0.046 (2)	0.024 (2)	0.009 (2)	0.009 (2)
C4	0.054 (2)	0.064 (2)	0.058 (2)	0.016 (2)	0.006 (2)	−0.005 (2)
C5	0.065 (2)	0.044 (2)	0.065 (2)	0.013 (2)	0.011 (2)	0.002 (2)
C6	0.046 (2)	0.053 (2)	0.056 (2)	0.015 (2)	0.010 (2)	0.010 (2)
C7	0.053 (2)	0.061 (2)	0.070 (3)	0.011 (2)	0.014 (2)	−0.005 (2)
C8	0.078 (3)	0.095 (3)	0.069 (3)	0.012 (2)	−0.003 (2)	−0.022 (2)
C9	0.089 (3)	0.072 (3)	0.061 (2)	0.023 (2)	0.001 (2)	0.015 (2)
C10	0.103 (4)	0.082 (3)	0.076 (3)	0.009 (3)	−0.003 (3)	−0.019 (2)
O1'	0.107 (2)	0.092 (2)	0.058 (2)	−0.003 (2)	−0.013 (2)	0.000 (2)
O2'	0.102 (2)	0.061 (2)	0.061 (2)	0.0018 (14)	−0.0032 (14)	0.0190 (13)
C1'	0.036 (2)	0.051 (2)	0.059 (2)	0.006 (2)	0.002 (2)	0.004 (2)
C2'	0.049 (2)	0.048 (2)	0.055 (2)	0.008 (2)	0.003 (2)	0.010 (2)
C3'	0.057 (2)	0.045 (2)	0.059 (2)	0.003 (2)	0.003 (2)	0.000 (2)
C4'	0.058 (2)	0.070 (3)	0.053 (2)	0.014 (2)	0.003 (2)	0.002 (2)
C5'	0.067 (3)	0.075 (3)	0.058 (2)	0.016 (2)	0.016 (2)	0.025 (2)
C6'	0.044 (2)	0.052 (2)	0.072 (3)	0.010 (2)	0.014 (2)	0.014 (2)
C7'	0.047 (2)	0.066 (3)	0.077 (3)	0.008 (2)	−0.007 (2)	−0.009 (2)
C8'	0.081 (3)	0.070 (3)	0.115 (4)	−0.006 (2)	−0.012 (3)	−0.023 (3)
C9'	0.088 (3)	0.061 (3)	0.123 (4)	0.004 (2)	0.020 (3)	0.028 (3)
C10'	0.104 (4)	0.114 (4)	0.063 (3)	0.017 (3)	0.007 (3)	−0.010 (3)

Geometric parameters (Å, º)

O1—C7	1.236 (4)	O1'—C7'	1.217 (4)
O2—C2	1.350 (4)	O2'—C2'	1.349 (4)
C1—C2	1.414 (4)	C1'—C2'	1.411 (4)
C1—C6	1.423 (4)	C1'—C6'	1.415 (5)
C1—C7	1.478 (5)	C1'—C7'	1.485 (5)
C2—C3	1.386 (5)	C2'—C3'	1.373 (5)
C3—C4	1.366 (5)	C3'—C4'	1.372 (5)
C4—C5	1.378 (5)	C4'—C5'	1.389 (5)
C4—C10	1.503 (5)	C4'—C10'	1.497 (5)
C5—C6	1.383 (5)	C5'—C6'	1.382 (5)
C6—C9	1.510 (4)	C6'—C9'	1.509 (5)
C7—C8	1.486 (5)	C7'—C8'	1.495 (5)
C2—C1—C6	117.1 (3)	C2'—C1'—C6'	117.1 (3)
C2—C1—C7	118.3 (3)	C2'—C1'—C7'	116.9 (3)
C6—C1—C7	124.7 (3)	C6'—C1'—C7'	125.9 (3)
O2—C2—C3	115.8 (3)	O2'—C2'—C3'	116.0 (3)
O2—C2—C1	122.5 (3)	O2'—C2'—C1'	122.3 (3)
C3—C2—C1	121.6 (3)	C3'—C2'—C1'	121.8 (3)
C4—C3—C2	120.7 (3)	C4'—C3'—C2'	121.4 (3)
C3—C4—C5	118.5 (3)	C3'—C4'—C5'	117.5 (4)
C3—C4—C10	121.6 (4)	C3'—C4'—C10'	120.5 (4)
C5—C4—C10	119.8 (4)	C5'—C4'—C10'	122.0 (4)
C4—C5—C6	123.3 (3)	C6'—C5'—C4'	123.2 (3)
C5—C6—C1	118.7 (3)	C5'—C6'—C1'	119.0 (3)
C5—C6—C9	116.0 (3)	C5'—C6'—C9'	115.9 (4)
C1—C6—C9	125.3 (3)	C1'—C6'—C9'	125.1 (4)
O1—C7—C1	119.0 (4)	O1'—C7'—C1'	120.6 (4)
O1—C7—C8	115.9 (4)	O1'—C7'—C8'	115.1 (4)
C1—C7—C8	125.1 (3)	C1'—C7'—C8'	124.3 (4)