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The structure of the title mol­ecule, C10H12O3, is stabilized by an intramolecular O—H...O hydrogen bond. In the crystal structure, the glide-related mol­ecules are linked by O—H...O hydrogen bonds to form molecular chains along [201]. The structure is further stabilized by π...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301938X/ci6269sup1.cif
Contains datablocks I, lsy

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301938X/ci6269Isup2.hkl
Contains datablock I

CCDC reference: 225711

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.052
  • wR factor = 0.155
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.57 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-(2,4-Dihydroxy-3,5-dimethyl-phenyl)-ethanone top
Crystal data top
C10H12O3F(000) = 384
Mr = 180.20Dx = 1.324 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3017 reflections
a = 8.318 (1) Åθ = 2.4–28.0°
b = 15.200 (3) ŵ = 0.10 mm1
c = 7.204 (1) ÅT = 298 K
β = 96.896 (3)°Block, colorless
V = 904.2 (2) Å30.35 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
2078 independent reflections
Radiation source: fine-focus sealed tube1725 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scanθmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.947, Tmax = 0.983k = 1720
5370 measured reflectionsl = 89
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0945P)2 + 0.142P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2078 reflectionsΔρmax = 0.22 e Å3
125 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (8)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.69574 (13)0.24726 (7)0.17498 (18)0.0609 (4)
O20.51388 (12)0.37873 (7)0.08559 (18)0.0591 (4)
O30.01831 (11)0.32842 (7)0.17279 (16)0.0559 (3)
C10.42724 (15)0.22866 (9)0.04071 (18)0.0397 (3)
C20.39759 (14)0.31959 (9)0.02716 (18)0.0406 (3)
C30.24782 (15)0.35241 (9)0.04823 (18)0.0418 (3)
C40.12568 (14)0.29264 (10)0.10492 (18)0.0396 (3)
C50.14846 (15)0.20111 (9)0.09173 (17)0.0403 (3)
C60.29907 (15)0.17190 (9)0.02101 (18)0.0418 (3)
C70.58499 (15)0.19577 (10)0.11649 (19)0.0460 (4)
C80.61857 (19)0.09957 (12)0.1245 (3)0.0632 (5)
C90.2196 (2)0.44927 (11)0.0692 (3)0.0629 (5)
C100.01309 (18)0.13858 (11)0.1530 (2)0.0538 (4)
H20.59680.35270.12730.089*
H30.08260.28910.20710.084*
H60.31720.11160.01360.063*
H8A0.73020.08990.17130.095*
H8B0.59660.07490.00140.095*
H8C0.55060.07190.20610.095*
H9A0.15920.46110.18870.094*
H9B0.32190.47920.06080.094*
H9C0.15980.46970.02820.094*
H10A0.05070.07920.13380.081*
H10B0.02310.14760.28320.081*
H10C0.07510.14890.08110.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0290 (5)0.0665 (7)0.0808 (8)0.0049 (4)0.0191 (5)0.0076 (6)
O20.0332 (6)0.0524 (6)0.0862 (8)0.0120 (4)0.0159 (5)0.0016 (5)
O30.0268 (5)0.0630 (7)0.0733 (7)0.0035 (4)0.0130 (4)0.0029 (5)
C10.0264 (6)0.0510 (7)0.0395 (7)0.0041 (5)0.0053 (5)0.0043 (5)
C20.0268 (6)0.0499 (8)0.0432 (7)0.0080 (5)0.0042 (5)0.0007 (5)
C30.0295 (6)0.0479 (7)0.0464 (7)0.0021 (5)0.0022 (5)0.0009 (5)
C40.0240 (6)0.0546 (8)0.0384 (6)0.0009 (5)0.0032 (4)0.0015 (5)
C50.0281 (6)0.0528 (8)0.0383 (6)0.0070 (5)0.0031 (5)0.0013 (5)
C60.0314 (6)0.0470 (7)0.0447 (7)0.0046 (5)0.0047 (5)0.0022 (5)
C70.0278 (6)0.0589 (8)0.0485 (7)0.0029 (6)0.0064 (5)0.0086 (6)
C80.0394 (8)0.0595 (10)0.0862 (12)0.0038 (7)0.0112 (7)0.0134 (8)
C90.0422 (8)0.0495 (8)0.0934 (13)0.0006 (6)0.0067 (8)0.0017 (8)
C100.0342 (7)0.0587 (9)0.0648 (9)0.0115 (6)0.0087 (6)0.0035 (7)
Geometric parameters (Å, º) top
O1—C71.243 (2)O2—H20.82
O2—C21.350 (2)O3—H30.82
O3—C41.352 (2)C6—H60.93
C1—C61.402 (2)C8—H8A0.96
C1—C21.405 (2)C8—H8B0.96
C1—C71.448 (2)C8—H8C0.96
C2—C31.390 (2)C9—H9A0.96
C3—C41.387 (2)C9—H9B0.96
C3—C91.496 (2)C9—H9C0.96
C4—C51.406 (2)C10—H10A0.96
C5—C61.369 (2)C10—H10B0.96
C5—C101.499 (2)C10—H10C0.96
C7—C81.489 (2)
C2—O2—H2109.5C5—C6—H6118.5
C4—O3—H3109.5C1—C6—H6118.5
C6—C1—C2117.6 (1)C7—C8—H8A109.5
C6—C1—C7121.8 (1)C7—C8—H8B109.5
C2—C1—C7120.6 (1)H8A—C8—H8B109.5
O2—C2—C3117.2 (1)C7—C8—H8C109.5
O2—C2—C1121.3 (1)H8A—C8—H8C109.5
C3—C2—C1121.4 (1)H8B—C8—H8C109.5
C4—C3—C2118.1 (1)C3—C9—H9A109.5
C4—C3—C9121.0 (1)C3—C9—H9B109.5
C2—C3—C9121.0 (1)H9A—C9—H9B109.5
O3—C4—C3115.4 (1)C3—C9—H9C109.5
O3—C4—C5121.9 (1)H9A—C9—H9C109.5
C3—C4—C5122.7 (1)H9B—C9—H9C109.5
C6—C5—C4117.1 (1)C5—C10—H10A109.5
C6—C5—C10121.7 (1)C5—C10—H10B109.5
C4—C5—C10121.2 (1)C5—C10—H10C109.5
C5—C6—C1123.1 (1)H10A—C10—H10B109.5
O1—C7—C1120.8 (1)H10A—C10—H10C109.5
O1—C7—C8118.5 (1)H10B—C10—H10C109.5
C1—C7—C8120.7 (1)
C6—C1—C2—O2179.19 (12)O3—C4—C5—C6179.99 (12)
C7—C1—C2—O20.6 (2)C3—C4—C5—C60.6 (2)
C6—C1—C2—C31.3 (2)O3—C4—C5—C100.1 (2)
C7—C1—C2—C3178.85 (12)C3—C4—C5—C10179.48 (13)
O2—C2—C3—C4178.50 (12)C4—C5—C6—C11.3 (2)
C1—C2—C3—C42.0 (2)C2—C1—C6—C50.4 (2)
O2—C2—C3—C92.1 (2)C7—C1—C6—C5179.43 (12)
C1—C2—C3—C9177.45 (14)C6—C1—C7—O1178.10 (13)
C2—C3—C4—O3178.44 (12)C2—C1—C7—O11.7 (2)
C9—C3—C4—O32.1 (2)C6—C1—C7—C82.5 (2)
C2—C3—C4—C51.0 (2)C2—C1—C7—C8177.72 (14)
C9—C3—C4—C5178.42 (14)C10—C5—C6—C1178.76 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.822.542 (2)147
O3—H3···O1i0.822.012.749 (1)149
Symmetry code: (i) x1, y+1/2, z1/2.
 

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