Download citation
Download citation
link to html
In the title compound, C10H12O3, the butyl chain shows an extended planar conformation, and makes a dihedral angle of 73.98 (16)° with the benzene plane. The crystal packing is stabilized by O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048549/xu2144sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048549/xu2144Isup2.hkl
Contains datablock I

CCDC reference: 630513

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.125
  • Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.71 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.50 From the CIF: _reflns_number_total 941 Count of symmetry unique reflns 943 Completeness (_total/calc) 99.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: SHELXL97.

1,4-Dihydroxy-4-phenylbutan-2-one top
Crystal data top
C10H12O3F(000) = 192
Mr = 180.20Dx = 1.319 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 24 reflections
a = 7.9573 (13) Åθ = 4.6–9.3°
b = 5.4679 (15) ŵ = 0.10 mm1
c = 11.043 (3) ÅT = 293 K
β = 109.173 (16)°Block, colourless
V = 453.83 (19) Å30.25 × 0.18 × 0.18 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.039
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 1.9°
Graphite monochromatorh = 99
ω/2θ scansk = 66
1714 measured reflectionsl = 1313
941 independent reflections3 standard reflections every 250 reflections
709 reflections with I > 2σ(I) intensity decay: 1.7%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0873P)2 + 0.0008P]
where P = (Fo2 + 2Fc2)/3
941 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.20 e Å3
Special details top

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 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
xyzUiso*/Ueq
O10.2213 (3)0.9969 (5)0.5885 (2)0.0436 (7)
H1O0.12141.02660.59080.054 (5)*
O20.5841 (4)1.2761 (6)0.6274 (3)0.0538 (8)
O30.8883 (3)1.1251 (7)0.5935 (3)0.0554 (8)
H3O0.82831.21630.53680.054 (5)*
C10.2801 (4)0.8563 (6)0.8080 (3)0.0360 (8)
C20.3173 (5)0.9392 (7)0.9331 (3)0.0411 (8)
H20.38401.08090.95930.067 (6)*
C30.2561 (5)0.8126 (9)1.0192 (4)0.0502 (10)
H30.28310.86851.10300.067 (6)*
C40.1553 (5)0.6043 (8)0.9806 (4)0.0521 (11)
H40.11150.52141.03750.067 (6)*
C50.1201 (5)0.5200 (8)0.8577 (4)0.0519 (10)
H50.05390.37770.83200.067 (6)*
C60.1811 (5)0.6428 (7)0.7724 (3)0.0438 (9)
H60.15600.58270.68960.067 (6)*
C70.3454 (4)0.9979 (7)0.7156 (3)0.0360 (8)
H70.36581.16760.74530.054 (5)*
C80.5187 (4)0.8945 (7)0.7077 (3)0.0368 (8)
H820.59420.85100.79350.054 (5)*
H810.49250.74540.65740.054 (5)*
C90.6201 (4)1.0629 (7)0.6502 (3)0.0361 (8)
C100.7768 (4)0.9520 (8)0.6235 (4)0.0482 (10)
H1010.84620.85950.69810.054 (5)*
H1020.73380.83850.55250.054 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0358 (11)0.0548 (17)0.0451 (13)0.0086 (13)0.0200 (10)0.0085 (13)
O20.0551 (16)0.0429 (17)0.0747 (19)0.0060 (14)0.0364 (15)0.0115 (14)
O30.0343 (12)0.071 (2)0.0689 (18)0.0060 (14)0.0272 (12)0.0182 (15)
C10.0317 (15)0.036 (2)0.0440 (17)0.0070 (15)0.0178 (13)0.0025 (16)
C20.0430 (17)0.039 (2)0.0469 (18)0.0009 (17)0.0231 (15)0.0001 (16)
C30.053 (2)0.059 (3)0.0438 (19)0.006 (2)0.0239 (17)0.0066 (19)
C40.051 (2)0.055 (3)0.059 (2)0.006 (2)0.0284 (19)0.022 (2)
C50.050 (2)0.0378 (19)0.070 (2)0.0039 (19)0.0227 (18)0.008 (2)
C60.0480 (19)0.036 (2)0.0492 (19)0.0021 (18)0.0186 (16)0.0015 (17)
C70.0353 (15)0.0353 (18)0.0425 (16)0.0047 (16)0.0197 (13)0.0029 (16)
C80.0350 (16)0.0362 (17)0.0409 (16)0.0046 (15)0.0150 (13)0.0006 (16)
C90.0323 (15)0.037 (2)0.0401 (16)0.0009 (14)0.0139 (14)0.0039 (14)
C100.0402 (17)0.051 (2)0.059 (2)0.0043 (18)0.0251 (16)0.0058 (19)
Geometric parameters (Å, º) top
O1—C71.427 (4)C4—H40.9300
O1—H1O0.8200C5—C61.369 (5)
O2—C91.207 (5)C5—H50.9300
O3—C101.409 (5)C6—H60.9300
O3—H3O0.8200C7—C81.519 (4)
C1—C21.390 (5)C7—H70.9800
C1—C61.391 (5)C8—C91.497 (5)
C1—C71.502 (4)C8—H820.9700
C2—C31.388 (5)C8—H810.9700
C2—H20.9300C9—C101.500 (5)
C3—C41.378 (6)C10—H1010.9700
C3—H30.9300C10—H1020.9700
C4—C51.373 (5)
C7—O1—H1O109.5O1—C7—C8106.9 (2)
C10—O3—H3O109.5C1—C7—C8111.7 (3)
C2—C1—C6118.1 (3)O1—C7—H7108.5
C2—C1—C7119.9 (3)C1—C7—H7108.5
C6—C1—C7122.1 (3)C8—C7—H7108.5
C3—C2—C1120.7 (4)C9—C8—C7115.0 (3)
C3—C2—H2119.7C9—C8—H82108.5
C1—C2—H2119.7C7—C8—H82108.5
C4—C3—C2120.0 (4)C9—C8—H81108.5
C4—C3—H3120.0C7—C8—H81108.5
C2—C3—H3120.0H82—C8—H81107.5
C5—C4—C3119.5 (4)O2—C9—C8123.9 (3)
C5—C4—H4120.2O2—C9—C10120.4 (4)
C3—C4—H4120.2C8—C9—C10115.7 (3)
C6—C5—C4120.8 (4)O3—C10—C9113.7 (3)
C6—C5—H5119.6O3—C10—H101108.8
C4—C5—H5119.6C9—C10—H101108.8
C5—C6—C1120.9 (4)O3—C10—H102108.8
C5—C6—H6119.6C9—C10—H102108.8
C1—C6—H6119.6H101—C10—H102107.7
O1—C7—C1112.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.821.942.759 (4)175
O3—H3O···O1ii0.822.022.790 (4)157
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1/2, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds