1,4-Dihydr­oxy-4-phenyl­butan-2-one

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.

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

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Computing details

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

Crystal data

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) Å^3	0.25 × 0.18 × 0.18 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0873P)^2 + 0.0008P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3^i	0.82	1.94	2.759 (4)	175
O3—H3O···O1^ii	0.82	2.02	2.790 (4)	157

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1.