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The title compound, C7H6O4, crystallizes with two independent mol­ecules in the asymmetric unit and forms a two-dimensional structure in the solid state. This is facilitated by a network of hydrogen-bonding interactions. There are two intramolecular hydrogen bonds, one between adjacent hydroxyl groups and the other between between the hydroxyl group and the carbonyl O atom. The crystal structure is stabilized both by carboxyl­ic acid dimer formation and by interactions between the carboxyl and hydroxyl groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018682/tk6035sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018682/tk6035Isup2.hkl
Contains datablock I

CCDC reference: 177228

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.175
  • Data-to-parameter ratio = 8.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6497 Proportion of unique data used 0.5805 Ratio reflections to parameters 8.8593
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation & Rigaku, 1999a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN ((Molecular Structure Corporation & Rigaku, 1999b); program(s) used to solve structure: SIR88 (Burla et al., 1989) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C7H6O4Z = 4
Mr = 154.12F(000) = 320
Triclinic, P1Dx = 1.546 Mg m3
a = 9.431 (2) ÅMo Kα radiation, λ = 0.7107 Å
b = 10.307 (2) ÅCell parameters from 25 reflections
c = 8.291 (1) Åθ = 14.3–15.0°
α = 110.29 (1)°µ = 0.13 mm1
β = 113.75 (1)°T = 296 K
γ = 67.10 (2)°Plate, light brown
V = 662.0 (2) Å30.30 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC-5R
diffractometer
θmax = 27.5°
ω–2θ scansh = 012
3221 measured reflectionsk = 1213
3037 independent reflectionsl = 109
1763 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.020 intensity decay: 1.0%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max < 0.001
wR(F2) = 0.175Δρmax = 0.26 e Å3
S = 1.07Δρmin = 0.26 e Å3
1763 reflectionsExtinction correction: SHELXL97
199 parametersExtinction coefficient: none
H-atom parameters not refined
Special details top

Refinement. Refinement using reflections with F2 > -10.0 σ(F2). 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
O10.0186 (2)0.5143 (2)0.2991 (2)0.0507 (5)
O20.2021 (2)0.4296 (2)0.5401 (2)0.0468 (5)
O30.5067 (2)0.3084 (2)0.5433 (2)0.0452 (5)
O40.7254 (2)0.2519 (2)0.3772 (2)0.0502 (5)
O51.1566 (2)0.1113 (2)0.3088 (2)0.0573 (6)
O60.9101 (2)0.1966 (2)0.2777 (2)0.0478 (5)
O70.8820 (2)0.2281 (2)0.0372 (2)0.0417 (4)
O81.0278 (2)0.1671 (2)0.3654 (2)0.0500 (5)
C10.2881 (3)0.4160 (3)0.3002 (3)0.0359 (5)
C20.4500 (3)0.3474 (2)0.3829 (3)0.0330 (5)
C30.5647 (3)0.3157 (3)0.2977 (3)0.0366 (5)
C40.5190 (3)0.3485 (3)0.1332 (3)0.0444 (6)
C50.3584 (3)0.4144 (3)0.0505 (3)0.0474 (6)
C60.2432 (3)0.4484 (3)0.1325 (3)0.0421 (6)
C70.1670 (3)0.4539 (3)0.3904 (3)0.0386 (5)
C81.1353 (3)0.1117 (2)0.0369 (3)0.0327 (5)
C91.0423 (2)0.1556 (2)0.0786 (3)0.0307 (5)
C101.1170 (3)0.1240 (3)0.2497 (3)0.0339 (5)
C111.2781 (3)0.0504 (3)0.3034 (3)0.0441 (6)
C121.3695 (3)0.0070 (3)0.1889 (3)0.0457 (6)
C131.2987 (3)0.0377 (3)0.0198 (3)0.0396 (5)
C141.0555 (3)0.1442 (3)0.2170 (3)0.0357 (5)
H10.04850.52620.34930.0625*
H20.41190.33960.58360.0625*
H30.73970.24280.48470.0625*
H40.59500.32530.07660.0513*
H50.32860.43630.05910.0552*
H60.13700.49160.07680.0505*
H71.11310.13050.41060.0625*
H80.84680.23300.06870.0612*
H90.93140.18860.30870.0744*
H101.32460.02800.41470.0515*
H111.47810.04200.22600.0539*
H121.36150.01020.05470.0467*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0286 (9)0.076 (1)0.050 (1)0.0069 (8)0.0162 (8)0.0223 (9)
O20.0335 (9)0.068 (1)0.0443 (10)0.0083 (8)0.0188 (8)0.0185 (8)
O30.0364 (9)0.064 (1)0.0387 (9)0.0054 (8)0.0152 (7)0.0219 (8)
O40.0306 (9)0.076 (1)0.0425 (10)0.0023 (9)0.0163 (8)0.0260 (9)
O50.048 (1)0.094 (2)0.0362 (9)0.005 (1)0.0222 (8)0.0289 (10)
O60.0420 (10)0.066 (1)0.0350 (9)0.0055 (9)0.0106 (7)0.0246 (8)
O70.0303 (8)0.059 (1)0.0366 (9)0.0011 (7)0.0152 (7)0.0192 (8)
O80.0373 (9)0.088 (1)0.0295 (8)0.0085 (9)0.0170 (7)0.0217 (8)
C10.030 (1)0.041 (1)0.038 (1)0.0091 (9)0.0140 (9)0.0065 (10)
C20.032 (1)0.038 (1)0.030 (1)0.0088 (9)0.0127 (9)0.0067 (9)
C30.029 (1)0.044 (1)0.038 (1)0.0070 (10)0.0138 (9)0.0096 (10)
C40.040 (1)0.058 (2)0.041 (1)0.008 (1)0.022 (1)0.013 (1)
C50.040 (1)0.067 (2)0.036 (1)0.008 (1)0.012 (1)0.019 (1)
C60.031 (1)0.052 (1)0.043 (1)0.008 (1)0.011 (1)0.016 (1)
C70.032 (1)0.042 (1)0.042 (1)0.0093 (10)0.016 (1)0.007 (1)
C80.035 (1)0.042 (1)0.0245 (10)0.0105 (10)0.0119 (9)0.0093 (9)
C90.026 (1)0.040 (1)0.029 (1)0.0095 (9)0.0107 (8)0.0081 (9)
C100.030 (1)0.049 (1)0.028 (1)0.0112 (10)0.0133 (9)0.0093 (9)
C110.037 (1)0.068 (2)0.029 (1)0.009 (1)0.0102 (9)0.019 (1)
C120.025 (1)0.072 (2)0.036 (1)0.005 (1)0.0091 (9)0.018 (1)
C130.032 (1)0.057 (2)0.034 (1)0.009 (1)0.0168 (10)0.011 (1)
C140.037 (1)0.044 (1)0.030 (1)0.0071 (10)0.0155 (9)0.0118 (9)
Geometric parameters (Å, º) top
O1—C71.310 (2)C2—C31.399 (4)
O1—H10.839C3—C41.375 (4)
O2—C71.238 (4)C4—C51.382 (3)
O3—C21.359 (3)C4—H40.922
O3—H20.978C5—C61.378 (4)
O4—C31.372 (2)C5—H50.918
O4—H30.879C6—H60.915
O5—C141.325 (4)C8—C91.399 (4)
O5—H70.833C8—C131.389 (3)
O6—C141.217 (3)C8—C141.468 (3)
O7—C91.357 (2)C9—C101.397 (3)
O7—H80.816C10—C111.369 (3)
O8—C101.375 (3)C11—C121.382 (4)
O8—H90.817C11—H100.916
C1—C21.398 (3)C12—C131.379 (4)
C1—C61.401 (4)C12—H110.922
C1—C71.468 (4)C13—H120.924
O1···O2i2.685 (3)O5···C10viii3.571 (3)
O1···O7ii3.367 (3)O6···C6iii3.340 (3)
O1···O6iii3.374 (4)O6···O8vii3.415 (3)
O1···C9ii3.473 (3)O6···O8viii3.441 (3)
O1···C6iv3.485 (3)O6···C10vii3.504 (4)
O1···O8v3.498 (2)O6···C11vii3.537 (4)
O1···C7i3.521 (4)O7···C13vii3.567 (4)
O1···O5iii3.543 (3)O7···C8vii3.569 (4)
O1···C14iii3.564 (4)O7···C12vii3.572 (4)
O1···C5iv3.567 (3)O7···C9vii3.577 (3)
O2···O8ii3.309 (3)O7···C11vii3.580 (3)
O2···O2i3.377 (3)O7···C10vii3.583 (3)
O2···C10ii3.393 (3)O8···C14vii3.297 (4)
O2···O4v3.394 (3)O8···C14vi3.450 (3)
O2···C7i3.431 (3)O8···C8vii3.561 (3)
O3···O6vi3.352 (2)O8···C7ix3.589 (4)
O3···C3v3.513 (3)C2···C2v3.339 (5)
O3···C2v3.541 (3)C2···C3v3.554 (3)
O4···O6vi2.809 (2)C2···C12ii3.557 (4)
O4···C7v3.271 (3)C7···C10ii3.346 (4)
O4···O5vii3.372 (3)C7···C9ii3.518 (3)
O4···C1v3.532 (3)C8···C10vii3.581 (4)
O4···C13vii3.592 (3)C9···C9vii3.298 (5)
O5···O8viii2.645 (3)C9···C10vii3.551 (3)
C7—O1—H1111.9O1—C7—O2122.7 (3)
C2—O3—H2105.2O1—C7—C1114.6 (2)
C3—O4—H3109.8O2—C7—C1122.7 (2)
C14—O5—H7114.8C9—C8—C13119.7 (2)
C9—O7—H8109.4C9—C8—C14118.5 (2)
C10—O8—H9109.4C13—C8—C14121.8 (2)
C2—C1—C6119.7 (3)O7—C9—C8124.7 (2)
C2—C1—C7119.6 (2)O7—C9—C10116.5 (2)
C6—C1—C7120.7 (2)C8—C9—C10118.8 (2)
O3—C2—C1124.7 (3)O8—C10—C9119.6 (2)
O3—C2—C3116.3 (2)O8—C10—C11119.6 (2)
C1—C2—C3119.0 (2)C9—C10—C11120.8 (2)
O4—C3—C2120.6 (2)C10—C11—C12120.2 (2)
O4—C3—C4118.7 (3)C10—C11—H10119.7
C2—C3—C4120.7 (2)C12—C11—H10120.0
C3—C4—C5120.2 (3)C11—C12—C13120.0 (2)
C3—C4—H4120.2C11—C12—H11119.9
C5—C4—H4119.6C13—C12—H11120.1
C4—C5—C6120.3 (3)C8—C13—C12120.4 (3)
C4—C5—H5119.8C8—C13—H12120.3
C6—C5—H5119.9C12—C13—H12119.3
C1—C6—C5120.1 (2)O5—C14—O6122.6 (2)
C1—C6—H6119.9O5—C14—C8113.8 (2)
C5—C6—H6120.0O6—C14—C8123.6 (3)
O1—C7—C1—C2178.3 (2)O8—C10—C9—C8179.6 (2)
O1—C7—C1—C62.0 (4)O8—C10—C11—C12179.7 (3)
O2—C7—C1—C21.1 (4)C1—C2—C3—C41.3 (4)
O2—C7—C1—C6178.6 (3)C1—C6—C5—C40.2 (4)
O3—C2—C1—C6178.7 (2)C2—C1—C6—C50.7 (4)
O3—C2—C1—C71.6 (4)C2—C3—C4—C50.4 (4)
O3—C2—C3—O41.6 (3)C3—C2—C1—C61.5 (4)
O3—C2—C3—C4178.8 (2)C3—C2—C1—C7178.2 (2)
O4—C3—C2—C1178.3 (2)C3—C4—C5—C60.4 (4)
O4—C3—C4—C5179.2 (2)C5—C6—C1—C7179.0 (3)
O5—C14—C8—C9173.6 (2)C8—C9—C10—C110.5 (4)
O5—C14—C8—C137.2 (4)C8—C13—C12—C110.3 (4)
O6—C14—C8—C96.3 (4)C9—C8—C13—C120.1 (4)
O6—C14—C8—C13172.9 (3)C9—C10—C11—C120.4 (4)
O7—C9—C8—C13179.9 (2)C10—C9—C8—C130.3 (4)
O7—C9—C8—C140.7 (4)C10—C9—C8—C14179.5 (2)
O7—C9—C10—O80.3 (4)C10—C11—C12—C130.0 (5)
O7—C9—C10—C11179.6 (2)C12—C13—C8—C14179.1 (3)
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y, z; (iii) x+1, y+1, z; (iv) x, y+1, z; (v) x+1, y+1, z+1; (vi) x, y, z+1; (vii) x+2, y, z; (viii) x, y, z1; (ix) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H3···O30.882.242.700 (3)113
O3—H2···O20.981.772.642 (2)147
O8—H9···O70.822.262.682 (2)113
O7—H8···O60.821.932.625 (2)143
O1—H1···O2i0.841.852.685 (3)175
O5—H7···O8viii0.831.812.645 (2)177
O4—H3···O6vi0.882.052.809 (2)144
O8—H9···O40.822.042.670 (2)134
Symmetry codes: (i) x, y+1, z+1; (vi) x, y, z+1; (viii) x, y, z1.
 

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