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The title compound, C11H8O3, previously reported by Gupta & Dutta [Cryst. Struct. Commun. (1975), 4, 37-40] has been rerefined against new intensity data. Geometric parameters of the C and O atoms agree quite well. However, the positions of the hydroxyl H atoms differ slightly. Furthermore, the results of the present structure determination are of significantly higher precision.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012667/ob6154sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012667/ob6154Isup2.hkl
Contains datablock I

CCDC reference: 193773

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.070
  • Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
DIFF_019 Alert A _diffrn_standards_number is missing Number of standards used in measurement. DIFF_020 Alert A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF_022 Alert A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
3 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

(I) top
Crystal data top
C11H8O3F(000) = 392
Mr = 188.17Dx = 1.451 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.9942 (10) ÅCell parameters from 9721 reflections
b = 11.6591 (11) Åθ = 3.5–29.8°
c = 7.6298 (9) ŵ = 0.11 mm1
β = 104.392 (9)°T = 173 K
V = 861.15 (16) Å3Plate, light yellow
Z = 40.36 × 0.34 × 0.15 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1540 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 29.8°, θmin = 3.5°
ω scansh = 1313
12620 measured reflectionsk = 1616
2450 independent reflectionsl = 1010
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)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0414P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
2450 reflectionsΔρmax = 0.27 e Å3
136 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (2)
Special details top

Experimental. ;

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
O10.82168 (8)0.45835 (7)0.95777 (11)0.03035 (19)
H110.912 (2)0.4432 (16)1.026 (2)0.066 (5)*
O20.92942 (7)0.59777 (7)0.84544 (11)0.02966 (18)
O30.78125 (8)0.74533 (7)0.61593 (12)0.0319 (2)
H100.8578 (18)0.7081 (15)0.687 (2)0.061 (5)*
C10.56778 (10)0.52640 (8)0.76526 (13)0.0215 (2)
H10.57810.45960.83880.026*
C20.68403 (10)0.58568 (9)0.75048 (13)0.02125 (19)
C30.66969 (10)0.68466 (8)0.63684 (14)0.0230 (2)
C40.54041 (10)0.72066 (9)0.54475 (14)0.0247 (2)
H40.53160.78610.46850.030*
C50.42051 (11)0.66216 (9)0.56132 (14)0.0225 (2)
C60.28540 (11)0.69925 (10)0.46950 (15)0.0278 (2)
H60.27440.76450.39260.033*
C70.17178 (11)0.64170 (10)0.49141 (16)0.0311 (3)
H70.08230.66790.43040.037*
C80.18510 (11)0.54371 (10)0.60344 (15)0.0298 (2)
H80.10490.50490.61760.036*
C90.31331 (11)0.50458 (9)0.69161 (14)0.0255 (2)
H90.32170.43800.76540.031*
C100.43369 (10)0.56278 (8)0.67349 (13)0.0215 (2)
C110.82153 (10)0.54808 (9)0.85444 (13)0.0226 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0210 (4)0.0334 (4)0.0338 (4)0.0010 (3)0.0014 (3)0.0118 (3)
O20.0196 (3)0.0331 (4)0.0346 (4)0.0003 (3)0.0037 (3)0.0075 (3)
O30.0234 (4)0.0318 (4)0.0393 (5)0.0026 (3)0.0058 (3)0.0108 (4)
C10.0213 (4)0.0208 (5)0.0215 (5)0.0014 (4)0.0038 (3)0.0000 (4)
C20.0203 (4)0.0220 (4)0.0207 (4)0.0014 (4)0.0037 (3)0.0009 (3)
C30.0228 (5)0.0218 (5)0.0244 (5)0.0010 (4)0.0058 (4)0.0000 (4)
C40.0263 (5)0.0220 (5)0.0247 (5)0.0019 (4)0.0043 (4)0.0038 (4)
C50.0227 (5)0.0224 (5)0.0210 (5)0.0024 (4)0.0029 (4)0.0024 (4)
C60.0251 (5)0.0280 (5)0.0274 (5)0.0060 (4)0.0010 (4)0.0003 (4)
C70.0217 (5)0.0372 (6)0.0308 (6)0.0050 (4)0.0003 (4)0.0029 (5)
C80.0208 (5)0.0359 (6)0.0316 (6)0.0028 (4)0.0046 (4)0.0041 (5)
C90.0235 (5)0.0272 (5)0.0255 (5)0.0016 (4)0.0052 (4)0.0011 (4)
C100.0203 (4)0.0226 (5)0.0205 (4)0.0006 (4)0.0032 (3)0.0028 (4)
C110.0215 (5)0.0242 (5)0.0216 (4)0.0019 (4)0.0042 (3)0.0002 (4)
Geometric parameters (Å, º) top
O1—C111.3098 (12)C4—H40.9500
O1—H110.936 (19)C5—C61.4251 (14)
O2—C111.2410 (13)C5—C101.4270 (14)
O3—C31.3628 (13)C6—C71.3646 (17)
O3—H100.929 (18)C6—H60.9500
C1—C21.3803 (14)C7—C81.4132 (17)
C1—C101.4141 (13)C7—H70.9500
C1—H10.9500C8—C91.3690 (15)
C2—C31.4291 (14)C8—H80.9500
C2—C111.4724 (13)C9—C101.4177 (15)
C3—C41.3741 (14)C9—H90.9500
C4—C51.4115 (15)
C11—O1—H11110.0 (12)C7—C6—H6119.8
C3—O3—H10105.5 (11)C5—C6—H6119.8
C2—C1—C10121.51 (9)C6—C7—C8121.03 (10)
C2—C1—H1119.2C6—C7—H7119.5
C10—C1—H1119.2C8—C7—H7119.5
C1—C2—C3119.63 (9)C9—C8—C7120.17 (11)
C1—C2—C11119.91 (9)C9—C8—H8119.9
C3—C2—C11120.44 (9)C7—C8—H8119.9
O3—C3—C4118.31 (9)C8—C9—C10120.39 (10)
O3—C3—C2121.91 (9)C8—C9—H9119.8
C4—C3—C2119.78 (9)C10—C9—H9119.8
C3—C4—C5121.19 (10)C1—C10—C9122.07 (9)
C3—C4—H4119.4C1—C10—C5118.38 (9)
C5—C4—H4119.4C9—C10—C5119.54 (9)
C4—C5—C6122.08 (10)O2—C11—O1122.36 (9)
C4—C5—C10119.49 (9)O2—C11—C2122.59 (9)
C6—C5—C10118.44 (10)O1—C11—C2115.05 (9)
C7—C6—C5120.41 (11)
C10—C1—C2—C31.46 (15)C7—C8—C9—C100.90 (17)
C10—C1—C2—C11177.30 (9)C2—C1—C10—C9178.16 (10)
C1—C2—C3—O3179.20 (10)C2—C1—C10—C51.04 (14)
C11—C2—C3—O32.05 (15)C8—C9—C10—C1178.68 (10)
C1—C2—C3—C40.65 (15)C8—C9—C10—C50.51 (15)
C11—C2—C3—C4178.11 (10)C4—C5—C10—C10.18 (14)
O3—C3—C4—C5179.58 (10)C6—C5—C10—C1179.68 (10)
C2—C3—C4—C50.57 (15)C4—C5—C10—C9179.41 (10)
C3—C4—C5—C6178.88 (11)C6—C5—C10—C90.46 (14)
C3—C4—C5—C100.98 (15)C1—C2—C11—O2179.57 (10)
C4—C5—C6—C7178.80 (11)C3—C2—C11—O21.68 (16)
C10—C5—C6—C71.06 (15)C1—C2—C11—O10.62 (14)
C5—C6—C7—C80.70 (17)C3—C2—C11—O1178.13 (9)
C6—C7—C8—C90.29 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O2i0.936 (19)1.715 (19)2.6484 (11)174.3 (18)
O3—H10···O20.929 (18)1.787 (18)2.6326 (11)149.9 (16)
Symmetry code: (i) x+2, y+1, z+2.
 

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