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The title compound (systematic name: 5-acetoxy-2-hydroxy-2,4,6-cyclo­hepta­trien-1-one), C9H8O4, contains intra- and inter­molecular O—H...O hydrogen bonds, resulting in centrosymmetric dimers. The acet­oxy group makes an angle of 59.86 (5)° with the seven-membered tropolone ring system. The crystal packing is consolidated by π–π and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023294/hb2086sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023294/hb2086Isup2.hkl
Contains datablock I

CCDC reference: 613701

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.104
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged .... H2 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O4 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O1 .. 2.64 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

5-acetoxy-2-hydroxy-2,4,6-cycloheptatrien-1-one top
Crystal data top
C9H8O4F(000) = 376.00
Mr = 180.16Dx = 1.408 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybcCell parameters from 7768 reflections
a = 3.8076 (12) Åθ = 4.0–68.1°
b = 10.987 (3) ŵ = 0.96 mm1
c = 20.356 (6) ÅT = 153 K
β = 93.576 (17)°Prism, colourless
V = 849.9 (4) Å30.33 × 0.26 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1407 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.033
ω scansθmax = 68.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 44
Tmin = 0.656, Tmax = 0.909k = 1212
7929 measured reflectionsl = 2424
1512 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0452P)2 + 0.5664P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max < 0.001
wR(F2) = 0.104Δρmax = 0.38 e Å3
S = 1.04Δρmin = 0.39 e Å3
1512 reflectionsExtinction correction: SHELXL97 (Sheldrick 1997)
124 parametersExtinction coefficient: 0.0126 (11)
H atoms treated by a mixture of independent and constrained refinement
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1422 (3)0.04362 (11)0.56906 (6)0.0357 (3)
O20.1489 (3)0.16647 (11)0.54664 (6)0.0331 (3)
O30.3438 (2)0.19672 (10)0.82194 (5)0.0276 (3)
O40.0353 (3)0.04061 (11)0.86142 (6)0.0335 (3)
C10.1591 (4)0.02698 (13)0.61685 (8)0.0248 (3)
C20.0026 (4)0.14717 (13)0.60713 (8)0.0248 (3)
C30.0247 (4)0.24044 (14)0.65143 (8)0.0266 (4)
C40.0850 (4)0.24602 (13)0.71843 (8)0.0257 (3)
C50.2555 (4)0.16019 (13)0.75662 (8)0.0237 (3)
C60.3803 (4)0.04525 (13)0.73769 (8)0.0237 (3)
C70.3394 (4)0.01023 (13)0.67796 (8)0.0237 (3)
C80.2210 (4)0.12773 (14)0.87186 (8)0.0266 (4)
C90.3463 (5)0.17711 (18)0.93708 (9)0.0378 (4)
H10.26180.12520.97190.045*
H20.100 (6)0.104 (2)0.5201 (11)0.057 (7)*
H30.13100.31270.63400.032*
H40.03310.31980.74010.031*
H50.51000.00080.77110.028*
H60.44980.08760.67620.028*
H70.25560.25990.94190.045*
H80.60410.17880.94040.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0549 (8)0.0270 (6)0.0245 (6)0.0076 (5)0.0036 (5)0.0046 (4)
O20.0468 (8)0.0280 (6)0.0238 (6)0.0080 (5)0.0029 (5)0.0008 (4)
O30.0339 (6)0.0239 (6)0.0249 (6)0.0054 (4)0.0002 (4)0.0052 (4)
O40.0407 (7)0.0291 (6)0.0307 (6)0.0063 (5)0.0026 (5)0.0016 (5)
C10.0282 (8)0.0223 (8)0.0244 (8)0.0007 (6)0.0044 (6)0.0007 (6)
C20.0253 (8)0.0240 (8)0.0252 (8)0.0003 (6)0.0021 (6)0.0041 (6)
C30.0287 (9)0.0193 (8)0.0318 (9)0.0023 (6)0.0029 (7)0.0025 (6)
C40.0269 (8)0.0190 (7)0.0316 (8)0.0012 (6)0.0052 (6)0.0032 (6)
C50.0239 (8)0.0226 (8)0.0247 (8)0.0060 (6)0.0023 (6)0.0040 (6)
C60.0241 (8)0.0216 (7)0.0254 (8)0.0015 (6)0.0008 (6)0.0014 (6)
C70.0261 (8)0.0178 (7)0.0275 (8)0.0023 (6)0.0035 (6)0.0013 (6)
C80.0276 (9)0.0245 (8)0.0275 (8)0.0037 (6)0.0011 (6)0.0026 (6)
C90.0390 (11)0.0455 (11)0.0287 (9)0.0023 (8)0.0012 (7)0.0087 (8)
Geometric parameters (Å, º) top
O1—C11.243 (2)C7—C11.442 (2)
O2—C21.3363 (19)C8—C91.485 (2)
O3—C51.4093 (18)O2—H20.90 (2)
O3—C81.3729 (19)C3—H30.9500
O4—C81.201 (2)C4—H40.9500
C1—C21.465 (2)C6—H50.9499
C2—C31.371 (2)C7—H60.9500
C3—C41.403 (2)C9—H10.980
C4—C51.361 (2)C9—H70.980
C5—C61.411 (2)C9—H80.980
C6—C71.360 (2)
C5—O3—C8117.97 (12)O4—C8—C9127.02 (16)
O1—C1—C2117.13 (14)C2—O2—H2110.2 (15)
O1—C1—C7119.79 (14)C2—C3—H3115.0
C2—C1—C7123.06 (14)C4—C3—H3115.0
O2—C2—C1114.51 (13)C3—C4—H4116.0
O2—C2—C3116.64 (14)C5—C4—H4116.0
C1—C2—C3128.85 (14)C5—C6—H5116.0
C2—C3—C4130.20 (15)C7—C6—H5116.0
C3—C4—C5128.88 (15)C1—C7—H6114.0
O3—C5—C4114.75 (13)C6—C7—H6114.0
O3—C5—C6116.61 (13)C8—C9—H1109.5
C4—C5—C6128.37 (15)C8—C9—H7109.5
C5—C6—C7128.56 (14)C8—C9—H8109.5
C1—C7—C6131.74 (14)H1—C9—H7109.5
O3—C8—O4122.20 (14)H1—C9—H8109.5
O3—C8—C9110.78 (14)H7—C9—H8109.5
C1—C2—C3—C43.2 (3)C8—O3—C5—C4122.98 (15)
C2—C3—C4—C52.7 (3)C8—O3—C5—C662.38 (19)
C3—C4—C5—C63.2 (3)O1—C1—C2—O20.5 (2)
C4—C5—C6—C74.8 (3)O1—C1—C2—C3179.11 (17)
C5—C6—C7—C11.0 (3)O1—C1—C7—C6176.05 (17)
C6—C7—C1—C25.4 (2)C7—C1—C2—O2178.12 (15)
C7—C1—C2—C32.3 (2)O2—C2—C3—C4176.41 (16)
C5—O3—C8—O42.1 (2)C3—C4—C5—O3177.09 (15)
C5—O3—C8—C9178.46 (13)O3—C5—C6—C7178.60 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.90 (2)2.09 (2)2.589 (2)114.1 (18)
O2—H2···O1i0.90 (2)1.93 (2)2.716 (2)145 (2)
C3—H3···O4ii0.952.533.309 (2)139
C6—H5···O4iii0.952.673.433 (2)138
C7—H6···O3iv0.952.503.438 (2)171
C9—H7···O1ii0.982.643.586 (2)163
Symmetry codes: (i) x, y, z+1; (ii) x, y+1/2, z+3/2; (iii) x+1, y, z; (iv) x+1, y1/2, z+3/2.
 

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