The title compound, C
7H
6O
3, exists in the crystalline state as the 2,7-dihydroxycyclohepta-2,4,6-trien-1-one tautomer rather than as 2,3-dihydroxycyclohepta-2,4,6-trien-1-one. Intermolecular O—H
O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing is further stabilized by π–π interactions and weak intermolecular C—H
O hydrogen bonds.
Supporting information
CCDC reference: 636240
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.107
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O3 .. 2.62 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Bruno et
al., 2002); software used to prepare material for publication: CrystalStructure 3.8 (Rigaku/MSC, 2006).
2,7-dihydroxycyclohepta-2,4,6-trien-1-one
top
Crystal data top
C7H6O3 | F(000) = 288.00 |
Mr = 138.12 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2yn | Cell parameters from 1630 reflections |
a = 4.9981 (19) Å | θ = 3.1–27.5° |
b = 9.395 (3) Å | µ = 0.12 mm−1 |
c = 13.279 (5) Å | T = 153 K |
β = 96.9657 (19)° | Prism, colourless |
V = 618.9 (4) Å3 | 0.18 × 0.15 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku Saturn diffractometer | 1109 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.029 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (REQAB; Jacobson, 1998) | h = −6→6 |
Tmin = 0.920, Tmax = 0.988 | k = −10→12 |
4741 measured reflections | l = −16→16 |
1364 independent reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[0.0011Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.107 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.23 e Å−3 |
1364 reflections | Δρmin = −0.18 e Å−3 |
103 parameters | |
Special details top
Refinement. Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on 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 | 0.38964 (19) | 0.48653 (10) | 0.10575 (7) | 0.0262 (2) | |
O2 | 0.2105 (2) | 0.34064 (11) | −0.05680 (7) | 0.0297 (2) | |
O3 | 0.2560 (2) | 0.46897 (10) | 0.28393 (7) | 0.0280 (2) | |
C1 | 0.2064 (2) | 0.39659 (12) | 0.11504 (9) | 0.0207 (2) | |
C2 | 0.0986 (2) | 0.31336 (13) | 0.02845 (9) | 0.0225 (2) | |
C3 | −0.0993 (2) | 0.21040 (14) | 0.02077 (10) | 0.0268 (3) | |
C4 | −0.2558 (2) | 0.16006 (14) | 0.09324 (10) | 0.0280 (3) | |
C5 | −0.2478 (2) | 0.19986 (14) | 0.19377 (10) | 0.0262 (3) | |
C6 | −0.0781 (2) | 0.29870 (13) | 0.24743 (10) | 0.0241 (3) | |
C7 | 0.1189 (2) | 0.38241 (13) | 0.21410 (9) | 0.0210 (2) | |
H1 | 0.341 (3) | 0.4102 (19) | −0.0457 (14) | 0.056 (5)* | |
H2 | 0.378 (3) | 0.514 (2) | 0.2492 (16) | 0.060 (6)* | |
H3 | −0.1346 | 0.1673 | −0.0442 | 0.032* | |
H4 | −0.3849 | 0.0892 | 0.0706 | 0.033* | |
H5 | −0.3732 | 0.1538 | 0.2312 | 0.032* | |
H6 | −0.1019 | 0.3102 | 0.3169 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0288 (5) | 0.0280 (4) | 0.0231 (4) | −0.0037 (3) | 0.0086 (3) | 0.0012 (3) |
O2 | 0.0328 (5) | 0.0385 (5) | 0.0193 (4) | −0.0054 (4) | 0.0098 (3) | −0.0037 (3) |
O3 | 0.0322 (5) | 0.0317 (5) | 0.0210 (4) | −0.0065 (4) | 0.0066 (3) | −0.0030 (3) |
C1 | 0.0209 (5) | 0.0198 (5) | 0.0221 (6) | 0.0039 (4) | 0.0055 (4) | 0.0028 (4) |
C2 | 0.0237 (6) | 0.0257 (6) | 0.0186 (5) | 0.0042 (4) | 0.0048 (4) | 0.0009 (4) |
C3 | 0.0281 (6) | 0.0288 (6) | 0.0229 (6) | 0.0016 (5) | 0.0008 (5) | −0.0029 (4) |
C4 | 0.0238 (6) | 0.0257 (6) | 0.0337 (7) | −0.0027 (5) | −0.0001 (5) | 0.0015 (5) |
C5 | 0.0233 (6) | 0.0251 (6) | 0.0313 (6) | −0.0004 (4) | 0.0072 (5) | 0.0064 (5) |
C6 | 0.0262 (6) | 0.0253 (6) | 0.0219 (6) | 0.0027 (5) | 0.0070 (4) | 0.0042 (4) |
C7 | 0.0234 (6) | 0.0204 (5) | 0.0192 (5) | 0.0029 (4) | 0.0029 (4) | 0.0012 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.2629 (15) | C5—C6 | 1.3937 (17) |
O2—C2 | 1.3466 (16) | C6—C7 | 1.3746 (17) |
O3—C7 | 1.3553 (14) | O2—H1 | 0.923 (18) |
C1—C2 | 1.4400 (16) | O3—H2 | 0.91 (2) |
C1—C7 | 1.4420 (17) | C3—H3 | 0.950 |
C2—C3 | 1.3784 (17) | C4—H4 | 0.950 |
C3—C4 | 1.3945 (19) | C5—H5 | 0.950 |
C4—C5 | 1.3822 (18) | C6—H6 | 0.950 |
| | | |
O1···O1i | 3.1496 (13) | C7···H5iii | 3.312 |
O1···O2ii | 3.4036 (13) | C7···H5vii | 2.959 |
O1···O2i | 2.7144 (14) | H1···O1i | 1.910 (19) |
O1···C2ii | 3.4075 (14) | H1···O2i | 3.408 (17) |
O1···C3ii | 3.5278 (15) | H1···C1ii | 3.319 (17) |
O1···C4iii | 3.5563 (16) | H1···C1i | 3.124 (18) |
O1···C5iii | 3.3750 (15) | H1···C2ii | 3.427 (18) |
O1···C6iii | 3.5378 (15) | H1···C3iii | 3.396 (17) |
O1···C6iv | 3.5840 (15) | H1···C4iii | 3.477 (17) |
O2···O1ii | 3.4036 (13) | H1···C5v | 3.586 (18) |
O2···O1i | 2.7144 (14) | H1···C6v | 3.439 (19) |
O2···C1ii | 3.2627 (15) | H1···C7ii | 3.582 (17) |
O2···C4iii | 3.5599 (15) | H1···H1i | 2.53 (2) |
O2···C5v | 3.3654 (16) | H1···H2i | 3.27 (2) |
O2···C6v | 3.2021 (16) | H1···H3iii | 3.473 |
O3···C3vi | 3.5640 (15) | H1···H4iii | 3.584 |
O3···C4iv | 3.3372 (15) | H1···H5v | 3.085 |
O3···C5vii | 3.3805 (16) | H1···H6v | 2.798 |
O3···C5iv | 3.2648 (16) | H2···C4iv | 2.976 (19) |
O3···C6iv | 3.5391 (15) | H2···C5iv | 2.59 (2) |
C1···O2ii | 3.2627 (15) | H2···C6iii | 3.39 (2) |
C1···C2ii | 3.5605 (16) | H2···C6iv | 2.85 (2) |
C1···C4iii | 3.5262 (17) | H2···C7iv | 3.49 (2) |
C1···C5iii | 3.3554 (16) | H2···H1i | 3.27 (2) |
C2···O1ii | 3.4075 (14) | H2···H3vi | 3.239 |
C2···C1ii | 3.5605 (16) | H2···H4iv | 3.342 |
C2···C4iii | 3.5428 (17) | H2···H5vii | 2.882 |
C3···O1ii | 3.5278 (15) | H2···H5iv | 2.785 |
C3···O3viii | 3.5640 (15) | H2···H6iii | 3.269 |
C4···O1ix | 3.5563 (16) | H2···H6iv | 3.159 |
C4···O2ix | 3.5599 (15) | H3···O1ii | 3.552 |
C4···O3x | 3.3372 (15) | H3···O3viii | 2.616 |
C4···C1ix | 3.5262 (17) | H3···C6viii | 3.344 |
C4···C2ix | 3.5428 (17) | H3···C7viii | 3.328 |
C5···O1ix | 3.3750 (15) | H3···H1ix | 3.473 |
C5···O2xi | 3.3654 (16) | H3···H2viii | 3.239 |
C5···O3xii | 3.3805 (16) | H3···H3xiv | 3.563 |
C5···O3x | 3.2648 (16) | H3···H4xiii | 3.391 |
C5···C1ix | 3.3554 (16) | H3···H4xiv | 3.591 |
C6···O1ix | 3.5378 (15) | H3···H6viii | 2.803 |
C6···O1x | 3.5840 (15) | H3···H6v | 3.425 |
C6···O2xi | 3.2021 (16) | H4···O2ix | 3.421 |
C6···O3x | 3.5391 (15) | H4···O3xii | 3.053 |
O1···H1i | 1.910 (19) | H4···C2ix | 3.326 |
O1···H3ii | 3.552 | H4···C4xiii | 3.535 |
O1···H5iv | 3.425 | H4···H1ix | 3.584 |
O1···H6iv | 3.342 | H4···H2x | 3.342 |
O2···H1i | 3.408 (17) | H4···H3xiii | 3.391 |
O2···H4iii | 3.421 | H4···H3xiv | 3.591 |
O2···H5v | 2.796 | H4···H4xiii | 2.669 |
O2···H6v | 2.466 | H4···H6xii | 3.022 |
O3···H3vi | 2.616 | H4···H6viii | 3.540 |
O3···H4vii | 3.053 | H5···O1x | 3.425 |
O3···H5vii | 2.573 | H5···O2xi | 2.796 |
O3···H5iv | 3.567 | H5···O3xii | 2.573 |
O3···H6iii | 3.518 | H5···O3x | 3.567 |
C1···H1ii | 3.319 (17) | H5···C1ix | 3.348 |
C1···H1i | 3.124 (18) | H5···C6xii | 3.360 |
C1···H5iii | 3.348 | H5···C7ix | 3.312 |
C2···H1ii | 3.427 (18) | H5···C7xii | 2.959 |
C2···H4iii | 3.326 | H5···H1xi | 3.085 |
C2···H6v | 3.536 | H5···H2xii | 2.882 |
C3···H1ix | 3.396 (17) | H5···H2x | 2.785 |
C3···H6viii | 3.469 | H5···H6xii | 3.290 |
C4···H1ix | 3.477 (17) | H6···O1x | 3.342 |
C4···H2x | 2.98 (2) | H6···O2xi | 2.466 |
C4···H4xiii | 3.535 | H6···O3ix | 3.518 |
C4···H6xii | 3.597 | H6···C2xi | 3.536 |
C5···H1xi | 3.586 (18) | H6···C3vi | 3.469 |
C5···H2x | 2.59 (2) | H6···C4vii | 3.597 |
C6···H1xi | 3.439 (19) | H6···H1xi | 2.798 |
C6···H2ix | 3.39 (2) | H6···H2ix | 3.269 |
C6···H2x | 2.85 (2) | H6···H2x | 3.159 |
C6···H3vi | 3.344 | H6···H3xi | 3.425 |
C6···H5vii | 3.360 | H6···H3vi | 2.803 |
C7···H1ii | 3.582 (17) | H6···H4vii | 3.022 |
C7···H2x | 3.49 (2) | H6···H4vi | 3.540 |
C7···H3vi | 3.328 | H6···H5vii | 3.290 |
| | | |
O1—C1—C2 | 119.40 (11) | C1—C7—C6 | 130.93 (11) |
O1—C1—C7 | 117.05 (10) | C2—O2—H1 | 111.0 (11) |
C2—C1—C7 | 123.55 (10) | C7—O3—H2 | 104.4 (13) |
O2—C2—C1 | 114.49 (10) | C2—C3—H3 | 114.8 |
O2—C2—C3 | 116.03 (10) | C4—C3—H3 | 115.1 |
C1—C2—C3 | 129.48 (11) | C3—C4—H4 | 115.8 |
C2—C3—C4 | 130.14 (12) | C5—C4—H4 | 115.8 |
C3—C4—C5 | 128.44 (12) | C4—C5—H5 | 116.0 |
C4—C5—C6 | 128.22 (12) | C6—C5—H5 | 115.8 |
C5—C6—C7 | 129.18 (12) | C5—C6—H6 | 115.6 |
O3—C7—C1 | 112.61 (10) | C7—C6—H6 | 115.2 |
O3—C7—C6 | 116.46 (11) | | |
| | | |
O1—C1—C2—O2 | 0.45 (16) | O2—C2—C3—C4 | −178.58 (12) |
O1—C1—C2—C3 | −179.99 (9) | C1—C2—C3—C4 | 1.9 (2) |
O1—C1—C7—O3 | −1.26 (15) | C2—C3—C4—C5 | −1.4 (2) |
O1—C1—C7—C6 | 177.85 (12) | C3—C4—C5—C6 | −1.0 (2) |
C2—C1—C7—O3 | 178.03 (10) | C4—C5—C6—C7 | 1.2 (2) |
C2—C1—C7—C6 | −2.9 (2) | C5—C6—C7—O3 | −179.39 (12) |
C7—C1—C2—O2 | −178.82 (10) | C5—C6—C7—C1 | 1.5 (2) |
C7—C1—C2—C3 | 0.7 (2) | | |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) x+1/2, −y+1/2, z−1/2; (vi) x+1/2, −y+1/2, z+1/2; (vii) −x−1/2, y+1/2, −z+1/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) x−1, y, z; (x) −x+1/2, y−1/2, −z+1/2; (xi) x−1/2, −y+1/2, z+1/2; (xii) −x−1/2, y−1/2, −z+1/2; (xiii) −x−1, −y, −z; (xiv) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 0.923 (18) | 2.121 (18) | 2.6212 (13) | 112.8 (15) |
O2—H1···O1i | 0.923 (18) | 1.910 (19) | 2.7144 (14) | 144.5 (16) |
O3—H2···O1 | 0.91 (2) | 1.93 (2) | 2.5406 (13) | 122.4 (16) |
C3—H3···O3viii | 0.95 | 2.62 | 3.5640 (15) | 176 |
C5—H5···O3xii | 0.95 | 2.57 | 3.3805 (16) | 143 |
C6—H6···O2xi | 0.95 | 2.47 | 3.2021 (16) | 134 |
Symmetry codes: (i) −x+1, −y+1, −z; (viii) x−1/2, −y+1/2, z−1/2; (xi) x−1/2, −y+1/2, z+1/2; (xii) −x−1/2, y−1/2, −z+1/2. |