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The title compound, C7H6O3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003467/cv2189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003467/cv2189Isup2.hkl
Contains datablock I

CCDC reference: 636240

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](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

Computing details top

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
C7H6O3F(000) = 288.00
Mr = 138.12Dx = 1.482 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 1630 reflections
a = 4.9981 (19) Åθ = 3.1–27.5°
b = 9.395 (3) ŵ = 0.12 mm1
c = 13.279 (5) ÅT = 153 K
β = 96.9657 (19)°Prism, colourless
V = 618.9 (4) Å30.18 × 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-1Rint = 0.029
ω scansθmax = 27.5°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
h = 66
Tmin = 0.920, Tmax = 0.988k = 1012
4741 measured reflectionsl = 1616
1364 independent reflections
Refinement top
Refinement on F2H 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 = 1.01Δρmax = 0.23 e Å3
1364 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O10.38964 (19)0.48653 (10)0.10575 (7)0.0262 (2)
O20.2105 (2)0.34064 (11)0.05680 (7)0.0297 (2)
O30.2560 (2)0.46897 (10)0.28393 (7)0.0280 (2)
C10.2064 (2)0.39659 (12)0.11504 (9)0.0207 (2)
C20.0986 (2)0.31336 (13)0.02845 (9)0.0225 (2)
C30.0993 (2)0.21040 (14)0.02077 (10)0.0268 (3)
C40.2558 (2)0.16006 (14)0.09324 (10)0.0280 (3)
C50.2478 (2)0.19986 (14)0.19377 (10)0.0262 (3)
C60.0781 (2)0.29870 (13)0.24743 (10)0.0241 (3)
C70.1189 (2)0.38241 (13)0.21410 (9)0.0210 (2)
H10.341 (3)0.4102 (19)0.0457 (14)0.056 (5)*
H20.378 (3)0.514 (2)0.2492 (16)0.060 (6)*
H30.13460.16730.04420.032*
H40.38490.08920.07060.033*
H50.37320.15380.23120.032*
H60.10190.31020.31690.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0288 (5)0.0280 (4)0.0231 (4)0.0037 (3)0.0086 (3)0.0012 (3)
O20.0328 (5)0.0385 (5)0.0193 (4)0.0054 (4)0.0098 (3)0.0037 (3)
O30.0322 (5)0.0317 (5)0.0210 (4)0.0065 (4)0.0066 (3)0.0030 (3)
C10.0209 (5)0.0198 (5)0.0221 (6)0.0039 (4)0.0055 (4)0.0028 (4)
C20.0237 (6)0.0257 (6)0.0186 (5)0.0042 (4)0.0048 (4)0.0009 (4)
C30.0281 (6)0.0288 (6)0.0229 (6)0.0016 (5)0.0008 (5)0.0029 (4)
C40.0238 (6)0.0257 (6)0.0337 (7)0.0027 (5)0.0001 (5)0.0015 (5)
C50.0233 (6)0.0251 (6)0.0313 (6)0.0004 (4)0.0072 (5)0.0064 (5)
C60.0262 (6)0.0253 (6)0.0219 (6)0.0027 (5)0.0070 (4)0.0042 (4)
C70.0234 (6)0.0204 (5)0.0192 (5)0.0029 (4)0.0029 (4)0.0012 (4)
Geometric parameters (Å, º) top
O1—C11.2629 (15)C5—C61.3937 (17)
O2—C21.3466 (16)C6—C71.3746 (17)
O3—C71.3553 (14)O2—H10.923 (18)
C1—C21.4400 (16)O3—H20.91 (2)
C1—C71.4420 (17)C3—H30.950
C2—C31.3784 (17)C4—H40.950
C3—C41.3945 (19)C5—H50.950
C4—C51.3822 (18)C6—H60.950
O1···O1i3.1496 (13)C7···H5iii3.312
O1···O2ii3.4036 (13)C7···H5vii2.959
O1···O2i2.7144 (14)H1···O1i1.910 (19)
O1···C2ii3.4075 (14)H1···O2i3.408 (17)
O1···C3ii3.5278 (15)H1···C1ii3.319 (17)
O1···C4iii3.5563 (16)H1···C1i3.124 (18)
O1···C5iii3.3750 (15)H1···C2ii3.427 (18)
O1···C6iii3.5378 (15)H1···C3iii3.396 (17)
O1···C6iv3.5840 (15)H1···C4iii3.477 (17)
O2···O1ii3.4036 (13)H1···C5v3.586 (18)
O2···O1i2.7144 (14)H1···C6v3.439 (19)
O2···C1ii3.2627 (15)H1···C7ii3.582 (17)
O2···C4iii3.5599 (15)H1···H1i2.53 (2)
O2···C5v3.3654 (16)H1···H2i3.27 (2)
O2···C6v3.2021 (16)H1···H3iii3.473
O3···C3vi3.5640 (15)H1···H4iii3.584
O3···C4iv3.3372 (15)H1···H5v3.085
O3···C5vii3.3805 (16)H1···H6v2.798
O3···C5iv3.2648 (16)H2···C4iv2.976 (19)
O3···C6iv3.5391 (15)H2···C5iv2.59 (2)
C1···O2ii3.2627 (15)H2···C6iii3.39 (2)
C1···C2ii3.5605 (16)H2···C6iv2.85 (2)
C1···C4iii3.5262 (17)H2···C7iv3.49 (2)
C1···C5iii3.3554 (16)H2···H1i3.27 (2)
C2···O1ii3.4075 (14)H2···H3vi3.239
C2···C1ii3.5605 (16)H2···H4iv3.342
C2···C4iii3.5428 (17)H2···H5vii2.882
C3···O1ii3.5278 (15)H2···H5iv2.785
C3···O3viii3.5640 (15)H2···H6iii3.269
C4···O1ix3.5563 (16)H2···H6iv3.159
C4···O2ix3.5599 (15)H3···O1ii3.552
C4···O3x3.3372 (15)H3···O3viii2.616
C4···C1ix3.5262 (17)H3···C6viii3.344
C4···C2ix3.5428 (17)H3···C7viii3.328
C5···O1ix3.3750 (15)H3···H1ix3.473
C5···O2xi3.3654 (16)H3···H2viii3.239
C5···O3xii3.3805 (16)H3···H3xiv3.563
C5···O3x3.2648 (16)H3···H4xiii3.391
C5···C1ix3.3554 (16)H3···H4xiv3.591
C6···O1ix3.5378 (15)H3···H6viii2.803
C6···O1x3.5840 (15)H3···H6v3.425
C6···O2xi3.2021 (16)H4···O2ix3.421
C6···O3x3.5391 (15)H4···O3xii3.053
O1···H1i1.910 (19)H4···C2ix3.326
O1···H3ii3.552H4···C4xiii3.535
O1···H5iv3.425H4···H1ix3.584
O1···H6iv3.342H4···H2x3.342
O2···H1i3.408 (17)H4···H3xiii3.391
O2···H4iii3.421H4···H3xiv3.591
O2···H5v2.796H4···H4xiii2.669
O2···H6v2.466H4···H6xii3.022
O3···H3vi2.616H4···H6viii3.540
O3···H4vii3.053H5···O1x3.425
O3···H5vii2.573H5···O2xi2.796
O3···H5iv3.567H5···O3xii2.573
O3···H6iii3.518H5···O3x3.567
C1···H1ii3.319 (17)H5···C1ix3.348
C1···H1i3.124 (18)H5···C6xii3.360
C1···H5iii3.348H5···C7ix3.312
C2···H1ii3.427 (18)H5···C7xii2.959
C2···H4iii3.326H5···H1xi3.085
C2···H6v3.536H5···H2xii2.882
C3···H1ix3.396 (17)H5···H2x2.785
C3···H6viii3.469H5···H6xii3.290
C4···H1ix3.477 (17)H6···O1x3.342
C4···H2x2.98 (2)H6···O2xi2.466
C4···H4xiii3.535H6···O3ix3.518
C4···H6xii3.597H6···C2xi3.536
C5···H1xi3.586 (18)H6···C3vi3.469
C5···H2x2.59 (2)H6···C4vii3.597
C6···H1xi3.439 (19)H6···H1xi2.798
C6···H2ix3.39 (2)H6···H2ix3.269
C6···H2x2.85 (2)H6···H2x3.159
C6···H3vi3.344H6···H3xi3.425
C6···H5vii3.360H6···H3vi2.803
C7···H1ii3.582 (17)H6···H4vii3.022
C7···H2x3.49 (2)H6···H4vi3.540
C7···H3vi3.328H6···H5vii3.290
O1—C1—C2119.40 (11)C1—C7—C6130.93 (11)
O1—C1—C7117.05 (10)C2—O2—H1111.0 (11)
C2—C1—C7123.55 (10)C7—O3—H2104.4 (13)
O2—C2—C1114.49 (10)C2—C3—H3114.8
O2—C2—C3116.03 (10)C4—C3—H3115.1
C1—C2—C3129.48 (11)C3—C4—H4115.8
C2—C3—C4130.14 (12)C5—C4—H4115.8
C3—C4—C5128.44 (12)C4—C5—H5116.0
C4—C5—C6128.22 (12)C6—C5—H5115.8
C5—C6—C7129.18 (12)C5—C6—H6115.6
O3—C7—C1112.61 (10)C7—C6—H6115.2
O3—C7—C6116.46 (11)
O1—C1—C2—O20.45 (16)O2—C2—C3—C4178.58 (12)
O1—C1—C2—C3179.99 (9)C1—C2—C3—C41.9 (2)
O1—C1—C7—O31.26 (15)C2—C3—C4—C51.4 (2)
O1—C1—C7—C6177.85 (12)C3—C4—C5—C61.0 (2)
C2—C1—C7—O3178.03 (10)C4—C5—C6—C71.2 (2)
C2—C1—C7—C62.9 (2)C5—C6—C7—O3179.39 (12)
C7—C1—C2—O2178.82 (10)C5—C6—C7—C11.5 (2)
C7—C1—C2—C30.7 (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, z1/2; (vi) x+1/2, y+1/2, z+1/2; (vii) x1/2, y+1/2, z+1/2; (viii) x1/2, y+1/2, z1/2; (ix) x1, y, z; (x) x+1/2, y1/2, z+1/2; (xi) x1/2, y+1/2, z+1/2; (xii) x1/2, y1/2, z+1/2; (xiii) x1, y, z; (xiv) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O10.923 (18)2.121 (18)2.6212 (13)112.8 (15)
O2—H1···O1i0.923 (18)1.910 (19)2.7144 (14)144.5 (16)
O3—H2···O10.91 (2)1.93 (2)2.5406 (13)122.4 (16)
C3—H3···O3viii0.952.623.5640 (15)176
C5—H5···O3xii0.952.573.3805 (16)143
C6—H6···O2xi0.952.473.2021 (16)134
Symmetry codes: (i) x+1, y+1, z; (viii) x1/2, y+1/2, z1/2; (xi) x1/2, y+1/2, z+1/2; (xii) x1/2, y1/2, z+1/2.
 

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