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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
CCDC reference: 193773
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
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).
Crystal data top
C11H8O3 | F(000) = 392 |
Mr = 188.17 | Dx = 1.451 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9942 (10) Å | Cell parameters from 9721 reflections |
b = 11.6591 (11) Å | θ = 3.5–29.8° |
c = 7.6298 (9) Å | µ = 0.11 mm−1 |
β = 104.392 (9)° | T = 173 K |
V = 861.15 (16) Å3 | Plate, light yellow |
Z = 4 | 0.36 × 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 tube | Rint = 0.041 |
Graphite monochromator | θmax = 29.8°, θmin = 3.5° |
ω scans | h = −13→13 |
12620 measured reflections | k = −16→16 |
2450 independent reflections | l = −10→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H 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 reflections | Δρmax = 0.27 e Å−3 |
136 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.82168 (8) | 0.45835 (7) | 0.95777 (11) | 0.03035 (19) | |
H11 | 0.912 (2) | 0.4432 (16) | 1.026 (2) | 0.066 (5)* | |
O2 | 0.92942 (7) | 0.59777 (7) | 0.84544 (11) | 0.02966 (18) | |
O3 | 0.78125 (8) | 0.74533 (7) | 0.61593 (12) | 0.0319 (2) | |
H10 | 0.8578 (18) | 0.7081 (15) | 0.687 (2) | 0.061 (5)* | |
C1 | 0.56778 (10) | 0.52640 (8) | 0.76526 (13) | 0.0215 (2) | |
H1 | 0.5781 | 0.4596 | 0.8388 | 0.026* | |
C2 | 0.68403 (10) | 0.58568 (9) | 0.75048 (13) | 0.02125 (19) | |
C3 | 0.66969 (10) | 0.68466 (8) | 0.63684 (14) | 0.0230 (2) | |
C4 | 0.54041 (10) | 0.72066 (9) | 0.54475 (14) | 0.0247 (2) | |
H4 | 0.5316 | 0.7861 | 0.4685 | 0.030* | |
C5 | 0.42051 (11) | 0.66216 (9) | 0.56132 (14) | 0.0225 (2) | |
C6 | 0.28540 (11) | 0.69925 (10) | 0.46950 (15) | 0.0278 (2) | |
H6 | 0.2744 | 0.7645 | 0.3926 | 0.033* | |
C7 | 0.17178 (11) | 0.64170 (10) | 0.49141 (16) | 0.0311 (3) | |
H7 | 0.0823 | 0.6679 | 0.4304 | 0.037* | |
C8 | 0.18510 (11) | 0.54371 (10) | 0.60344 (15) | 0.0298 (2) | |
H8 | 0.1049 | 0.5049 | 0.6176 | 0.036* | |
C9 | 0.31331 (11) | 0.50458 (9) | 0.69161 (14) | 0.0255 (2) | |
H9 | 0.3217 | 0.4380 | 0.7654 | 0.031* | |
C10 | 0.43369 (10) | 0.56278 (8) | 0.67349 (13) | 0.0215 (2) | |
C11 | 0.82153 (10) | 0.54808 (9) | 0.85444 (13) | 0.0226 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0210 (4) | 0.0334 (4) | 0.0338 (4) | 0.0010 (3) | 0.0014 (3) | 0.0118 (3) |
O2 | 0.0196 (3) | 0.0331 (4) | 0.0346 (4) | 0.0003 (3) | 0.0037 (3) | 0.0075 (3) |
O3 | 0.0234 (4) | 0.0318 (4) | 0.0393 (5) | −0.0026 (3) | 0.0058 (3) | 0.0108 (4) |
C1 | 0.0213 (4) | 0.0208 (5) | 0.0215 (5) | 0.0014 (4) | 0.0038 (3) | 0.0000 (4) |
C2 | 0.0203 (4) | 0.0220 (4) | 0.0207 (4) | 0.0014 (4) | 0.0037 (3) | −0.0009 (3) |
C3 | 0.0228 (5) | 0.0218 (5) | 0.0244 (5) | −0.0010 (4) | 0.0058 (4) | 0.0000 (4) |
C4 | 0.0263 (5) | 0.0220 (5) | 0.0247 (5) | 0.0019 (4) | 0.0043 (4) | 0.0038 (4) |
C5 | 0.0227 (5) | 0.0224 (5) | 0.0210 (5) | 0.0024 (4) | 0.0029 (4) | −0.0024 (4) |
C6 | 0.0251 (5) | 0.0280 (5) | 0.0274 (5) | 0.0060 (4) | 0.0010 (4) | 0.0003 (4) |
C7 | 0.0217 (5) | 0.0372 (6) | 0.0308 (6) | 0.0050 (4) | −0.0003 (4) | −0.0029 (5) |
C8 | 0.0208 (5) | 0.0359 (6) | 0.0316 (6) | −0.0028 (4) | 0.0046 (4) | −0.0041 (5) |
C9 | 0.0235 (5) | 0.0272 (5) | 0.0255 (5) | −0.0016 (4) | 0.0052 (4) | −0.0011 (4) |
C10 | 0.0203 (4) | 0.0226 (5) | 0.0205 (4) | 0.0006 (4) | 0.0032 (3) | −0.0028 (4) |
C11 | 0.0215 (5) | 0.0242 (5) | 0.0216 (4) | 0.0019 (4) | 0.0042 (3) | 0.0002 (4) |
Geometric parameters (Å, º) top
O1—C11 | 1.3098 (12) | C4—H4 | 0.9500 |
O1—H11 | 0.936 (19) | C5—C6 | 1.4251 (14) |
O2—C11 | 1.2410 (13) | C5—C10 | 1.4270 (14) |
O3—C3 | 1.3628 (13) | C6—C7 | 1.3646 (17) |
O3—H10 | 0.929 (18) | C6—H6 | 0.9500 |
C1—C2 | 1.3803 (14) | C7—C8 | 1.4132 (17) |
C1—C10 | 1.4141 (13) | C7—H7 | 0.9500 |
C1—H1 | 0.9500 | C8—C9 | 1.3690 (15) |
C2—C3 | 1.4291 (14) | C8—H8 | 0.9500 |
C2—C11 | 1.4724 (13) | C9—C10 | 1.4177 (15) |
C3—C4 | 1.3741 (14) | C9—H9 | 0.9500 |
C4—C5 | 1.4115 (15) | | |
| | | |
C11—O1—H11 | 110.0 (12) | C7—C6—H6 | 119.8 |
C3—O3—H10 | 105.5 (11) | C5—C6—H6 | 119.8 |
C2—C1—C10 | 121.51 (9) | C6—C7—C8 | 121.03 (10) |
C2—C1—H1 | 119.2 | C6—C7—H7 | 119.5 |
C10—C1—H1 | 119.2 | C8—C7—H7 | 119.5 |
C1—C2—C3 | 119.63 (9) | C9—C8—C7 | 120.17 (11) |
C1—C2—C11 | 119.91 (9) | C9—C8—H8 | 119.9 |
C3—C2—C11 | 120.44 (9) | C7—C8—H8 | 119.9 |
O3—C3—C4 | 118.31 (9) | C8—C9—C10 | 120.39 (10) |
O3—C3—C2 | 121.91 (9) | C8—C9—H9 | 119.8 |
C4—C3—C2 | 119.78 (9) | C10—C9—H9 | 119.8 |
C3—C4—C5 | 121.19 (10) | C1—C10—C9 | 122.07 (9) |
C3—C4—H4 | 119.4 | C1—C10—C5 | 118.38 (9) |
C5—C4—H4 | 119.4 | C9—C10—C5 | 119.54 (9) |
C4—C5—C6 | 122.08 (10) | O2—C11—O1 | 122.36 (9) |
C4—C5—C10 | 119.49 (9) | O2—C11—C2 | 122.59 (9) |
C6—C5—C10 | 118.44 (10) | O1—C11—C2 | 115.05 (9) |
C7—C6—C5 | 120.41 (11) | | |
| | | |
C10—C1—C2—C3 | −1.46 (15) | C7—C8—C9—C10 | 0.90 (17) |
C10—C1—C2—C11 | 177.30 (9) | C2—C1—C10—C9 | −178.16 (10) |
C1—C2—C3—O3 | −179.20 (10) | C2—C1—C10—C5 | 1.04 (14) |
C11—C2—C3—O3 | 2.05 (15) | C8—C9—C10—C1 | 178.68 (10) |
C1—C2—C3—C4 | 0.65 (15) | C8—C9—C10—C5 | −0.51 (15) |
C11—C2—C3—C4 | −178.11 (10) | C4—C5—C10—C1 | 0.18 (14) |
O3—C3—C4—C5 | −179.58 (10) | C6—C5—C10—C1 | −179.68 (10) |
C2—C3—C4—C5 | 0.57 (15) | C4—C5—C10—C9 | 179.41 (10) |
C3—C4—C5—C6 | 178.88 (11) | C6—C5—C10—C9 | −0.46 (14) |
C3—C4—C5—C10 | −0.98 (15) | C1—C2—C11—O2 | 179.57 (10) |
C4—C5—C6—C7 | −178.80 (11) | C3—C2—C11—O2 | −1.68 (16) |
C10—C5—C6—C7 | 1.06 (15) | C1—C2—C11—O1 | −0.62 (14) |
C5—C6—C7—C8 | −0.70 (17) | C3—C2—C11—O1 | 178.13 (9) |
C6—C7—C8—C9 | −0.29 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O2i | 0.936 (19) | 1.715 (19) | 2.6484 (11) | 174.3 (18) |
O3—H10···O2 | 0.929 (18) | 1.787 (18) | 2.6326 (11) | 149.9 (16) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
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