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The non-hydrogen skeleton of the title compound, C8H8O2, is planar. The torsion angles HO-C-C=O and O=C-C(Ph)-C(Ph) are -0.9 (4) and 6.0 (4)°, respectively. The hydroxyl group participates in a bifurcated hydrogen bond, giving rise to infinite chains extended along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000760/ya6231sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000760/ya6231Isup2.hkl
Contains datablock I

CCDC reference: 263694

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.036
  • wR factor = 0.142
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.096 Value of mu given = 0.100 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 26.50 From the CIF: _reflns_number_total 855 Count of symmetry unique reflns 855 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 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, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-hydroxy-1-phenylethanone top
Crystal data top
C8H8O2Dx = 1.344 Mg m3
Mr = 136.14Melting point: 361 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1318 reflections
a = 4.8223 (15) Åθ = 3.2–23.5°
b = 5.4732 (16) ŵ = 0.10 mm1
c = 25.484 (7) ÅT = 293 K
V = 672.6 (3) Å3Block, colourless
Z = 40.20 × 0.16 × 0.12 mm
F(000) = 288
Data collection top
Bruker SMART CCD area-detector
diffractometer
650 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 26.5°, θmin = 1.6°
φ and ω scansh = 64
3890 measured reflectionsk = 65
855 independent reflectionsl = 3231
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.23 w = 1/[σ2(Fo2) + (0.0813P)2]
where P = (Fo2 + 2Fc2)/3
855 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.29 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
O10.2586 (5)0.2435 (4)0.17140 (9)0.0524 (7)
O20.3831 (6)0.5308 (5)0.25028 (10)0.0555 (7)
H20.453 (11)0.665 (9)0.2659 (15)0.084 (15)*
C10.1868 (7)0.6205 (6)0.21442 (12)0.0428 (8)
H1A0.01380.65330.23250.051*
H1B0.25290.77260.19940.051*
C20.1378 (6)0.4377 (5)0.17132 (12)0.0365 (7)
C30.0644 (7)0.5022 (5)0.12952 (11)0.0359 (7)
C40.2236 (6)0.7135 (6)0.13124 (13)0.0445 (8)
H40.20400.82180.15910.053*
C50.4114 (8)0.7631 (7)0.09163 (13)0.0540 (9)
H50.51900.90390.09320.065*
C60.4395 (8)0.6059 (7)0.05016 (14)0.0542 (9)
H60.56480.64050.02340.065*
C70.2824 (8)0.3972 (7)0.04818 (13)0.0533 (9)
H70.30250.28970.02020.064*
C80.0955 (7)0.3462 (6)0.08740 (11)0.0455 (8)
H80.01130.20500.08550.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0648 (15)0.0383 (12)0.0542 (13)0.0123 (13)0.0147 (12)0.0040 (11)
O20.0680 (17)0.0421 (14)0.0564 (14)0.0053 (12)0.0261 (14)0.0027 (11)
C10.0460 (18)0.0366 (17)0.0458 (16)0.0001 (14)0.0079 (14)0.0002 (14)
C20.0386 (16)0.0308 (15)0.0399 (16)0.0030 (13)0.0018 (13)0.0042 (12)
C30.0356 (15)0.0327 (16)0.0394 (15)0.0041 (12)0.0034 (13)0.0035 (13)
C40.0444 (18)0.0373 (17)0.0520 (17)0.0041 (15)0.0066 (16)0.0022 (14)
C50.0451 (19)0.0507 (19)0.066 (2)0.0047 (18)0.0046 (18)0.0111 (18)
C60.041 (2)0.069 (2)0.0518 (19)0.0070 (18)0.0105 (16)0.0173 (18)
C70.053 (2)0.064 (2)0.0431 (17)0.001 (2)0.0086 (16)0.0057 (17)
C80.0433 (18)0.0486 (18)0.0446 (17)0.0028 (16)0.0005 (15)0.0035 (15)
Geometric parameters (Å, º) top
O1—C21.212 (4)C4—C51.383 (5)
O2—C11.404 (4)C4—H40.9300
O2—H20.90 (5)C5—C61.369 (5)
C1—C21.504 (4)C5—H50.9300
C1—H1A0.9700C6—C71.371 (5)
C1—H1B0.9700C6—H60.9300
C2—C31.487 (4)C7—C81.375 (5)
C3—C81.380 (4)C7—H70.9300
C3—C41.389 (4)C8—H80.9300
C1—O2—H2105 (3)C5—C4—H4119.9
O2—C1—C2110.4 (3)C3—C4—H4119.9
O2—C1—H1A109.6C6—C5—C4120.3 (3)
C2—C1—H1A109.6C6—C5—H5119.8
O2—C1—H1B109.6C4—C5—H5119.8
C2—C1—H1B109.6C5—C6—C7119.8 (3)
H1A—C1—H1B108.1C5—C6—H6120.1
O1—C2—C3121.6 (3)C7—C6—H6120.1
O1—C2—C1120.4 (3)C6—C7—C8120.3 (3)
C3—C2—C1117.9 (2)C6—C7—H7119.8
C8—C3—C4118.7 (3)C8—C7—H7119.8
C8—C3—C2118.8 (3)C7—C8—C3120.7 (3)
C4—C3—C2122.5 (3)C7—C8—H8119.6
C5—C4—C3120.2 (3)C3—C8—H8119.6
O2—C1—C2—O10.9 (4)C2—C3—C4—C5179.2 (3)
O2—C1—C2—C3179.9 (3)C3—C4—C5—C60.7 (5)
O1—C2—C3—C86.0 (4)C4—C5—C6—C70.6 (5)
C1—C2—C3—C8174.7 (3)C5—C6—C7—C80.5 (6)
O1—C2—C3—C4173.9 (3)C6—C7—C8—C30.6 (6)
C1—C2—C3—C45.3 (4)C4—C3—C8—C70.7 (5)
C8—C3—C4—C50.8 (5)C2—C3—C8—C7179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.90 (5)2.16 (5)2.885 (3)137 (4)
O2—H2···O2i0.90 (5)2.19 (5)2.960 (2)143 (3)
Symmetry code: (i) x1, y+1/2, z+1/2.
 

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