The title compound (systematic name: 5-acetoxy-2-hydroxy-2,4,6-cycloheptatrien-1-one), C
9H
8O
4, 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
CCDC reference: 613701
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (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
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
C9H8O4 | F(000) = 376.00 |
Mr = 180.16 | Dx = 1.408 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54187 Å |
Hall symbol: -P 2ybc | Cell parameters from 7768 reflections |
a = 3.8076 (12) Å | θ = 4.0–68.1° |
b = 10.987 (3) Å | µ = 0.96 mm−1 |
c = 20.356 (6) Å | T = 153 K |
β = 93.576 (17)° | Prism, colourless |
V = 849.9 (4) Å3 | 0.33 × 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-1 | Rint = 0.033 |
ω scans | θmax = 68.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −4→4 |
Tmin = 0.656, Tmax = 0.909 | k = −12→12 |
7929 measured reflections | l = −24→24 |
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) = 0.104 | Δρmax = 0.38 e Å−3 |
S = 1.04 | Δρmin = −0.39 e Å−3 |
1512 reflections | Extinction correction: SHELXL97 (Sheldrick 1997) |
124 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.1422 (3) | −0.04362 (11) | 0.56906 (6) | 0.0357 (3) | |
O2 | −0.1489 (3) | 0.16647 (11) | 0.54664 (6) | 0.0331 (3) | |
O3 | 0.3438 (2) | 0.19672 (10) | 0.82194 (5) | 0.0276 (3) | |
O4 | 0.0353 (3) | 0.04061 (11) | 0.86142 (6) | 0.0335 (3) | |
C1 | 0.1591 (4) | 0.02698 (13) | 0.61685 (8) | 0.0248 (3) | |
C2 | −0.0026 (4) | 0.14717 (13) | 0.60713 (8) | 0.0248 (3) | |
C3 | −0.0247 (4) | 0.24044 (14) | 0.65143 (8) | 0.0266 (4) | |
C4 | 0.0850 (4) | 0.24602 (13) | 0.71843 (8) | 0.0257 (3) | |
C5 | 0.2555 (4) | 0.16019 (13) | 0.75662 (8) | 0.0237 (3) | |
C6 | 0.3803 (4) | 0.04525 (13) | 0.73769 (8) | 0.0237 (3) | |
C7 | 0.3394 (4) | −0.01023 (13) | 0.67796 (8) | 0.0237 (3) | |
C8 | 0.2210 (4) | 0.12773 (14) | 0.87186 (8) | 0.0266 (4) | |
C9 | 0.3463 (5) | 0.17711 (18) | 0.93708 (9) | 0.0378 (4) | |
H1 | 0.2618 | 0.1252 | 0.9719 | 0.045* | |
H2 | −0.100 (6) | 0.104 (2) | 0.5201 (11) | 0.057 (7)* | |
H3 | −0.1310 | 0.3127 | 0.6340 | 0.032* | |
H4 | 0.0331 | 0.3198 | 0.7401 | 0.031* | |
H5 | 0.5100 | 0.0008 | 0.7711 | 0.028* | |
H6 | 0.4498 | −0.0876 | 0.6762 | 0.028* | |
H7 | 0.2556 | 0.2599 | 0.9419 | 0.045* | |
H8 | 0.6041 | 0.1788 | 0.9404 | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0549 (8) | 0.0270 (6) | 0.0245 (6) | 0.0076 (5) | −0.0036 (5) | −0.0046 (4) |
O2 | 0.0468 (8) | 0.0280 (6) | 0.0238 (6) | 0.0080 (5) | −0.0029 (5) | 0.0008 (4) |
O3 | 0.0339 (6) | 0.0239 (6) | 0.0249 (6) | −0.0054 (4) | 0.0002 (4) | −0.0052 (4) |
O4 | 0.0407 (7) | 0.0291 (6) | 0.0307 (6) | −0.0063 (5) | 0.0026 (5) | −0.0016 (5) |
C1 | 0.0282 (8) | 0.0223 (8) | 0.0244 (8) | −0.0007 (6) | 0.0044 (6) | −0.0007 (6) |
C2 | 0.0253 (8) | 0.0240 (8) | 0.0252 (8) | −0.0003 (6) | 0.0021 (6) | 0.0041 (6) |
C3 | 0.0287 (9) | 0.0193 (8) | 0.0318 (9) | 0.0023 (6) | 0.0029 (7) | 0.0025 (6) |
C4 | 0.0269 (8) | 0.0190 (7) | 0.0316 (8) | −0.0012 (6) | 0.0052 (6) | −0.0032 (6) |
C5 | 0.0239 (8) | 0.0226 (8) | 0.0247 (8) | −0.0060 (6) | 0.0023 (6) | −0.0040 (6) |
C6 | 0.0241 (8) | 0.0216 (7) | 0.0254 (8) | −0.0015 (6) | 0.0008 (6) | 0.0014 (6) |
C7 | 0.0261 (8) | 0.0178 (7) | 0.0275 (8) | 0.0023 (6) | 0.0035 (6) | 0.0013 (6) |
C8 | 0.0276 (9) | 0.0245 (8) | 0.0275 (8) | 0.0037 (6) | 0.0011 (6) | −0.0026 (6) |
C9 | 0.0390 (11) | 0.0455 (11) | 0.0287 (9) | −0.0023 (8) | 0.0012 (7) | −0.0087 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.243 (2) | C7—C1 | 1.442 (2) |
O2—C2 | 1.3363 (19) | C8—C9 | 1.485 (2) |
O3—C5 | 1.4093 (18) | O2—H2 | 0.90 (2) |
O3—C8 | 1.3729 (19) | C3—H3 | 0.9500 |
O4—C8 | 1.201 (2) | C4—H4 | 0.9500 |
C1—C2 | 1.465 (2) | C6—H5 | 0.9499 |
C2—C3 | 1.371 (2) | C7—H6 | 0.9500 |
C3—C4 | 1.403 (2) | C9—H1 | 0.980 |
C4—C5 | 1.361 (2) | C9—H7 | 0.980 |
C5—C6 | 1.411 (2) | C9—H8 | 0.980 |
C6—C7 | 1.360 (2) | | |
| | | |
C5—O3—C8 | 117.97 (12) | O4—C8—C9 | 127.02 (16) |
O1—C1—C2 | 117.13 (14) | C2—O2—H2 | 110.2 (15) |
O1—C1—C7 | 119.79 (14) | C2—C3—H3 | 115.0 |
C2—C1—C7 | 123.06 (14) | C4—C3—H3 | 115.0 |
O2—C2—C1 | 114.51 (13) | C3—C4—H4 | 116.0 |
O2—C2—C3 | 116.64 (14) | C5—C4—H4 | 116.0 |
C1—C2—C3 | 128.85 (14) | C5—C6—H5 | 116.0 |
C2—C3—C4 | 130.20 (15) | C7—C6—H5 | 116.0 |
C3—C4—C5 | 128.88 (15) | C1—C7—H6 | 114.0 |
O3—C5—C4 | 114.75 (13) | C6—C7—H6 | 114.0 |
O3—C5—C6 | 116.61 (13) | C8—C9—H1 | 109.5 |
C4—C5—C6 | 128.37 (15) | C8—C9—H7 | 109.5 |
C5—C6—C7 | 128.56 (14) | C8—C9—H8 | 109.5 |
C1—C7—C6 | 131.74 (14) | H1—C9—H7 | 109.5 |
O3—C8—O4 | 122.20 (14) | H1—C9—H8 | 109.5 |
O3—C8—C9 | 110.78 (14) | H7—C9—H8 | 109.5 |
| | | |
C1—C2—C3—C4 | −3.2 (3) | C8—O3—C5—C4 | 122.98 (15) |
C2—C3—C4—C5 | 2.7 (3) | C8—O3—C5—C6 | −62.38 (19) |
C3—C4—C5—C6 | 3.2 (3) | O1—C1—C2—O2 | −0.5 (2) |
C4—C5—C6—C7 | −4.8 (3) | O1—C1—C2—C3 | 179.11 (17) |
C5—C6—C7—C1 | −1.0 (3) | O1—C1—C7—C6 | −176.05 (17) |
C6—C7—C1—C2 | 5.4 (2) | C7—C1—C2—O2 | 178.12 (15) |
C7—C1—C2—C3 | −2.3 (2) | O2—C2—C3—C4 | 176.41 (16) |
C5—O3—C8—O4 | −2.1 (2) | C3—C4—C5—O3 | 177.09 (15) |
C5—O3—C8—C9 | 178.46 (13) | O3—C5—C6—C7 | −178.60 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.90 (2) | 2.09 (2) | 2.589 (2) | 114.1 (18) |
O2—H2···O1i | 0.90 (2) | 1.93 (2) | 2.716 (2) | 145 (2) |
C3—H3···O4ii | 0.95 | 2.53 | 3.309 (2) | 139 |
C6—H5···O4iii | 0.95 | 2.67 | 3.433 (2) | 138 |
C7—H6···O3iv | 0.95 | 2.50 | 3.438 (2) | 171 |
C9—H7···O1ii | 0.98 | 2.64 | 3.586 (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, y−1/2, −z+3/2. |