In the title compound, C
10H
12O
3, 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
CCDC reference: 630513
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C10H12O3 | F(000) = 192 |
Mr = 180.20 | Dx = 1.319 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 24 reflections |
a = 7.9573 (13) Å | θ = 4.6–9.3° |
b = 5.4679 (15) Å | µ = 0.10 mm−1 |
c = 11.043 (3) Å | T = 293 K |
β = 109.173 (16)° | Block, colourless |
V = 453.83 (19) Å3 | 0.25 × 0.18 × 0.18 mm |
Z = 2 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.039 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 1.9° |
Graphite monochromator | h = −9→9 |
ω/2θ scans | k = −6→6 |
1714 measured reflections | l = −13→13 |
941 independent reflections | 3 standard reflections every 250 reflections |
709 reflections with I > 2σ(I) | intensity decay: 1.7% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-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 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2213 (3) | 0.9969 (5) | 0.5885 (2) | 0.0436 (7) | |
H1O | 0.1214 | 1.0266 | 0.5908 | 0.054 (5)* | |
O2 | 0.5841 (4) | 1.2761 (6) | 0.6274 (3) | 0.0538 (8) | |
O3 | 0.8883 (3) | 1.1251 (7) | 0.5935 (3) | 0.0554 (8) | |
H3O | 0.8283 | 1.2163 | 0.5368 | 0.054 (5)* | |
C1 | 0.2801 (4) | 0.8563 (6) | 0.8080 (3) | 0.0360 (8) | |
C2 | 0.3173 (5) | 0.9392 (7) | 0.9331 (3) | 0.0411 (8) | |
H2 | 0.3840 | 1.0809 | 0.9593 | 0.067 (6)* | |
C3 | 0.2561 (5) | 0.8126 (9) | 1.0192 (4) | 0.0502 (10) | |
H3 | 0.2831 | 0.8685 | 1.1030 | 0.067 (6)* | |
C4 | 0.1553 (5) | 0.6043 (8) | 0.9806 (4) | 0.0521 (11) | |
H4 | 0.1115 | 0.5214 | 1.0375 | 0.067 (6)* | |
C5 | 0.1201 (5) | 0.5200 (8) | 0.8577 (4) | 0.0519 (10) | |
H5 | 0.0539 | 0.3777 | 0.8320 | 0.067 (6)* | |
C6 | 0.1811 (5) | 0.6428 (7) | 0.7724 (3) | 0.0438 (9) | |
H6 | 0.1560 | 0.5827 | 0.6896 | 0.067 (6)* | |
C7 | 0.3454 (4) | 0.9979 (7) | 0.7156 (3) | 0.0360 (8) | |
H7 | 0.3658 | 1.1676 | 0.7453 | 0.054 (5)* | |
C8 | 0.5187 (4) | 0.8945 (7) | 0.7077 (3) | 0.0368 (8) | |
H82 | 0.5942 | 0.8510 | 0.7935 | 0.054 (5)* | |
H81 | 0.4925 | 0.7454 | 0.6574 | 0.054 (5)* | |
C9 | 0.6201 (4) | 1.0629 (7) | 0.6502 (3) | 0.0361 (8) | |
C10 | 0.7768 (4) | 0.9520 (8) | 0.6235 (4) | 0.0482 (10) | |
H101 | 0.8462 | 0.8595 | 0.6981 | 0.054 (5)* | |
H102 | 0.7338 | 0.8385 | 0.5525 | 0.054 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0358 (11) | 0.0548 (17) | 0.0451 (13) | 0.0086 (13) | 0.0200 (10) | 0.0085 (13) |
O2 | 0.0551 (16) | 0.0429 (17) | 0.0747 (19) | 0.0060 (14) | 0.0364 (15) | 0.0115 (14) |
O3 | 0.0343 (12) | 0.071 (2) | 0.0689 (18) | 0.0060 (14) | 0.0272 (12) | 0.0182 (15) |
C1 | 0.0317 (15) | 0.036 (2) | 0.0440 (17) | 0.0070 (15) | 0.0178 (13) | 0.0025 (16) |
C2 | 0.0430 (17) | 0.039 (2) | 0.0469 (18) | −0.0009 (17) | 0.0231 (15) | −0.0001 (16) |
C3 | 0.053 (2) | 0.059 (3) | 0.0438 (19) | 0.006 (2) | 0.0239 (17) | 0.0066 (19) |
C4 | 0.051 (2) | 0.055 (3) | 0.059 (2) | 0.006 (2) | 0.0284 (19) | 0.022 (2) |
C5 | 0.050 (2) | 0.0378 (19) | 0.070 (2) | −0.0039 (19) | 0.0227 (18) | 0.008 (2) |
C6 | 0.0480 (19) | 0.036 (2) | 0.0492 (19) | −0.0021 (18) | 0.0186 (16) | −0.0015 (17) |
C7 | 0.0353 (15) | 0.0353 (18) | 0.0425 (16) | 0.0047 (16) | 0.0197 (13) | 0.0029 (16) |
C8 | 0.0350 (16) | 0.0362 (17) | 0.0409 (16) | 0.0046 (15) | 0.0150 (13) | 0.0006 (16) |
C9 | 0.0323 (15) | 0.037 (2) | 0.0401 (16) | 0.0009 (14) | 0.0139 (14) | −0.0039 (14) |
C10 | 0.0402 (17) | 0.051 (2) | 0.059 (2) | 0.0043 (18) | 0.0251 (16) | −0.0058 (19) |
Geometric parameters (Å, º) top
O1—C7 | 1.427 (4) | C4—H4 | 0.9300 |
O1—H1O | 0.8200 | C5—C6 | 1.369 (5) |
O2—C9 | 1.207 (5) | C5—H5 | 0.9300 |
O3—C10 | 1.409 (5) | C6—H6 | 0.9300 |
O3—H3O | 0.8200 | C7—C8 | 1.519 (4) |
C1—C2 | 1.390 (5) | C7—H7 | 0.9800 |
C1—C6 | 1.391 (5) | C8—C9 | 1.497 (5) |
C1—C7 | 1.502 (4) | C8—H82 | 0.9700 |
C2—C3 | 1.388 (5) | C8—H81 | 0.9700 |
C2—H2 | 0.9300 | C9—C10 | 1.500 (5) |
C3—C4 | 1.378 (6) | C10—H101 | 0.9700 |
C3—H3 | 0.9300 | C10—H102 | 0.9700 |
C4—C5 | 1.373 (5) | | |
| | | |
C7—O1—H1O | 109.5 | O1—C7—C8 | 106.9 (2) |
C10—O3—H3O | 109.5 | C1—C7—C8 | 111.7 (3) |
C2—C1—C6 | 118.1 (3) | O1—C7—H7 | 108.5 |
C2—C1—C7 | 119.9 (3) | C1—C7—H7 | 108.5 |
C6—C1—C7 | 122.1 (3) | C8—C7—H7 | 108.5 |
C3—C2—C1 | 120.7 (4) | C9—C8—C7 | 115.0 (3) |
C3—C2—H2 | 119.7 | C9—C8—H82 | 108.5 |
C1—C2—H2 | 119.7 | C7—C8—H82 | 108.5 |
C4—C3—C2 | 120.0 (4) | C9—C8—H81 | 108.5 |
C4—C3—H3 | 120.0 | C7—C8—H81 | 108.5 |
C2—C3—H3 | 120.0 | H82—C8—H81 | 107.5 |
C5—C4—C3 | 119.5 (4) | O2—C9—C8 | 123.9 (3) |
C5—C4—H4 | 120.2 | O2—C9—C10 | 120.4 (4) |
C3—C4—H4 | 120.2 | C8—C9—C10 | 115.7 (3) |
C6—C5—C4 | 120.8 (4) | O3—C10—C9 | 113.7 (3) |
C6—C5—H5 | 119.6 | O3—C10—H101 | 108.8 |
C4—C5—H5 | 119.6 | C9—C10—H101 | 108.8 |
C5—C6—C1 | 120.9 (4) | O3—C10—H102 | 108.8 |
C5—C6—H6 | 119.6 | C9—C10—H102 | 108.8 |
C1—C6—H6 | 119.6 | H101—C10—H102 | 107.7 |
O1—C7—C1 | 112.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3i | 0.82 | 1.94 | 2.759 (4) | 175 |
O3—H3O···O1ii | 0.82 | 2.02 | 2.790 (4) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1. |