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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
CCDC reference: 177228
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
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.
Crystal data top
C7H6O4 | Z = 4 |
Mr = 154.12 | F(000) = 320 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
a = 9.431 (2) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 10.307 (2) Å | Cell parameters from 25 reflections |
c = 8.291 (1) Å | θ = 14.3–15.0° |
α = 110.29 (1)° | µ = 0.13 mm−1 |
β = 113.75 (1)° | T = 296 K |
γ = 67.10 (2)° | Plate, light brown |
V = 662.0 (2) Å3 | 0.30 × 0.20 × 0.10 mm |
Data collection top
Rigaku AFC-5R diffractometer | θmax = 27.5° |
ω–2θ scans | h = 0→12 |
3221 measured reflections | k = −12→13 |
3037 independent reflections | l = −10→9 |
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) = 0.175 | Δρmax = 0.26 e Å−3 |
S = 1.07 | Δρmin = −0.26 e Å−3 |
1763 reflections | Extinction correction: SHELXL97 |
199 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0186 (2) | 0.5143 (2) | 0.2991 (2) | 0.0507 (5) | |
O2 | 0.2021 (2) | 0.4296 (2) | 0.5401 (2) | 0.0468 (5) | |
O3 | 0.5067 (2) | 0.3084 (2) | 0.5433 (2) | 0.0452 (5) | |
O4 | 0.7254 (2) | 0.2519 (2) | 0.3772 (2) | 0.0502 (5) | |
O5 | 1.1566 (2) | 0.1113 (2) | −0.3088 (2) | 0.0573 (6) | |
O6 | 0.9101 (2) | 0.1966 (2) | −0.2777 (2) | 0.0478 (5) | |
O7 | 0.8820 (2) | 0.2281 (2) | 0.0372 (2) | 0.0417 (4) | |
O8 | 1.0278 (2) | 0.1671 (2) | 0.3654 (2) | 0.0500 (5) | |
C1 | 0.2881 (3) | 0.4160 (3) | 0.3002 (3) | 0.0359 (5) | |
C2 | 0.4500 (3) | 0.3474 (2) | 0.3829 (3) | 0.0330 (5) | |
C3 | 0.5647 (3) | 0.3157 (3) | 0.2977 (3) | 0.0366 (5) | |
C4 | 0.5190 (3) | 0.3485 (3) | 0.1332 (3) | 0.0444 (6) | |
C5 | 0.3584 (3) | 0.4144 (3) | 0.0505 (3) | 0.0474 (6) | |
C6 | 0.2432 (3) | 0.4484 (3) | 0.1325 (3) | 0.0421 (6) | |
C7 | 0.1670 (3) | 0.4539 (3) | 0.3904 (3) | 0.0386 (5) | |
C8 | 1.1353 (3) | 0.1117 (2) | −0.0369 (3) | 0.0327 (5) | |
C9 | 1.0423 (2) | 0.1556 (2) | 0.0786 (3) | 0.0307 (5) | |
C10 | 1.1170 (3) | 0.1240 (3) | 0.2497 (3) | 0.0339 (5) | |
C11 | 1.2781 (3) | 0.0504 (3) | 0.3034 (3) | 0.0441 (6) | |
C12 | 1.3695 (3) | 0.0070 (3) | 0.1889 (3) | 0.0457 (6) | |
C13 | 1.2987 (3) | 0.0377 (3) | 0.0198 (3) | 0.0396 (5) | |
C14 | 1.0555 (3) | 0.1442 (3) | −0.2170 (3) | 0.0357 (5) | |
H1 | −0.0485 | 0.5262 | 0.3493 | 0.0625* | |
H2 | 0.4119 | 0.3396 | 0.5836 | 0.0625* | |
H3 | 0.7397 | 0.2428 | 0.4847 | 0.0625* | |
H4 | 0.5950 | 0.3253 | 0.0766 | 0.0513* | |
H5 | 0.3286 | 0.4363 | −0.0591 | 0.0552* | |
H6 | 0.1370 | 0.4916 | 0.0768 | 0.0505* | |
H7 | 1.1131 | 0.1305 | −0.4106 | 0.0625* | |
H8 | 0.8468 | 0.2330 | −0.0687 | 0.0612* | |
H9 | 0.9314 | 0.1886 | 0.3087 | 0.0744* | |
H10 | 1.3246 | 0.0280 | 0.4147 | 0.0515* | |
H11 | 1.4781 | −0.0420 | 0.2260 | 0.0539* | |
H12 | 1.3615 | 0.0102 | −0.0547 | 0.0467* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0286 (9) | 0.076 (1) | 0.050 (1) | −0.0069 (8) | 0.0162 (8) | 0.0223 (9) |
O2 | 0.0335 (9) | 0.068 (1) | 0.0443 (10) | −0.0083 (8) | 0.0188 (8) | 0.0185 (8) |
O3 | 0.0364 (9) | 0.064 (1) | 0.0387 (9) | −0.0054 (8) | 0.0152 (7) | 0.0219 (8) |
O4 | 0.0306 (9) | 0.076 (1) | 0.0425 (10) | 0.0023 (9) | 0.0163 (8) | 0.0260 (9) |
O5 | 0.048 (1) | 0.094 (2) | 0.0362 (9) | −0.005 (1) | 0.0222 (8) | 0.0289 (10) |
O6 | 0.0420 (10) | 0.066 (1) | 0.0350 (9) | −0.0055 (9) | 0.0106 (7) | 0.0246 (8) |
O7 | 0.0303 (8) | 0.059 (1) | 0.0366 (9) | −0.0011 (7) | 0.0152 (7) | 0.0192 (8) |
O8 | 0.0373 (9) | 0.088 (1) | 0.0295 (8) | −0.0085 (9) | 0.0170 (7) | 0.0217 (8) |
C1 | 0.030 (1) | 0.041 (1) | 0.038 (1) | −0.0091 (9) | 0.0140 (9) | 0.0065 (10) |
C2 | 0.032 (1) | 0.038 (1) | 0.030 (1) | −0.0088 (9) | 0.0127 (9) | 0.0067 (9) |
C3 | 0.029 (1) | 0.044 (1) | 0.038 (1) | −0.0070 (10) | 0.0138 (9) | 0.0096 (10) |
C4 | 0.040 (1) | 0.058 (2) | 0.041 (1) | −0.008 (1) | 0.022 (1) | 0.013 (1) |
C5 | 0.040 (1) | 0.067 (2) | 0.036 (1) | −0.008 (1) | 0.012 (1) | 0.019 (1) |
C6 | 0.031 (1) | 0.052 (1) | 0.043 (1) | −0.008 (1) | 0.011 (1) | 0.016 (1) |
C7 | 0.032 (1) | 0.042 (1) | 0.042 (1) | −0.0093 (10) | 0.016 (1) | 0.007 (1) |
C8 | 0.035 (1) | 0.042 (1) | 0.0245 (10) | −0.0105 (10) | 0.0119 (9) | 0.0093 (9) |
C9 | 0.026 (1) | 0.040 (1) | 0.029 (1) | −0.0095 (9) | 0.0107 (8) | 0.0081 (9) |
C10 | 0.030 (1) | 0.049 (1) | 0.028 (1) | −0.0112 (10) | 0.0133 (9) | 0.0093 (9) |
C11 | 0.037 (1) | 0.068 (2) | 0.029 (1) | −0.009 (1) | 0.0102 (9) | 0.019 (1) |
C12 | 0.025 (1) | 0.072 (2) | 0.036 (1) | −0.005 (1) | 0.0091 (9) | 0.018 (1) |
C13 | 0.032 (1) | 0.057 (2) | 0.034 (1) | −0.009 (1) | 0.0168 (10) | 0.011 (1) |
C14 | 0.037 (1) | 0.044 (1) | 0.030 (1) | −0.0071 (10) | 0.0155 (9) | 0.0118 (9) |
Geometric parameters (Å, º) top
O1—C7 | 1.310 (2) | C2—C3 | 1.399 (4) |
O1—H1 | 0.839 | C3—C4 | 1.375 (4) |
O2—C7 | 1.238 (4) | C4—C5 | 1.382 (3) |
O3—C2 | 1.359 (3) | C4—H4 | 0.922 |
O3—H2 | 0.978 | C5—C6 | 1.378 (4) |
O4—C3 | 1.372 (2) | C5—H5 | 0.918 |
O4—H3 | 0.879 | C6—H6 | 0.915 |
O5—C14 | 1.325 (4) | C8—C9 | 1.399 (4) |
O5—H7 | 0.833 | C8—C13 | 1.389 (3) |
O6—C14 | 1.217 (3) | C8—C14 | 1.468 (3) |
O7—C9 | 1.357 (2) | C9—C10 | 1.397 (3) |
O7—H8 | 0.816 | C10—C11 | 1.369 (3) |
O8—C10 | 1.375 (3) | C11—C12 | 1.382 (4) |
O8—H9 | 0.817 | C11—H10 | 0.916 |
C1—C2 | 1.398 (3) | C12—C13 | 1.379 (4) |
C1—C6 | 1.401 (4) | C12—H11 | 0.922 |
C1—C7 | 1.468 (4) | C13—H12 | 0.924 |
| | | |
O1···O2i | 2.685 (3) | O5···C10viii | 3.571 (3) |
O1···O7ii | 3.367 (3) | O6···C6iii | 3.340 (3) |
O1···O6iii | 3.374 (4) | O6···O8vii | 3.415 (3) |
O1···C9ii | 3.473 (3) | O6···O8viii | 3.441 (3) |
O1···C6iv | 3.485 (3) | O6···C10vii | 3.504 (4) |
O1···O8v | 3.498 (2) | O6···C11vii | 3.537 (4) |
O1···C7i | 3.521 (4) | O7···C13vii | 3.567 (4) |
O1···O5iii | 3.543 (3) | O7···C8vii | 3.569 (4) |
O1···C14iii | 3.564 (4) | O7···C12vii | 3.572 (4) |
O1···C5iv | 3.567 (3) | O7···C9vii | 3.577 (3) |
O2···O8ii | 3.309 (3) | O7···C11vii | 3.580 (3) |
O2···O2i | 3.377 (3) | O7···C10vii | 3.583 (3) |
O2···C10ii | 3.393 (3) | O8···C14vii | 3.297 (4) |
O2···O4v | 3.394 (3) | O8···C14vi | 3.450 (3) |
O2···C7i | 3.431 (3) | O8···C8vii | 3.561 (3) |
O3···O6vi | 3.352 (2) | O8···C7ix | 3.589 (4) |
O3···C3v | 3.513 (3) | C2···C2v | 3.339 (5) |
O3···C2v | 3.541 (3) | C2···C3v | 3.554 (3) |
O4···O6vi | 2.809 (2) | C2···C12ii | 3.557 (4) |
O4···C7v | 3.271 (3) | C7···C10ii | 3.346 (4) |
O4···O5vii | 3.372 (3) | C7···C9ii | 3.518 (3) |
O4···C1v | 3.532 (3) | C8···C10vii | 3.581 (4) |
O4···C13vii | 3.592 (3) | C9···C9vii | 3.298 (5) |
O5···O8viii | 2.645 (3) | C9···C10vii | 3.551 (3) |
| | | |
C7—O1—H1 | 111.9 | O1—C7—O2 | 122.7 (3) |
C2—O3—H2 | 105.2 | O1—C7—C1 | 114.6 (2) |
C3—O4—H3 | 109.8 | O2—C7—C1 | 122.7 (2) |
C14—O5—H7 | 114.8 | C9—C8—C13 | 119.7 (2) |
C9—O7—H8 | 109.4 | C9—C8—C14 | 118.5 (2) |
C10—O8—H9 | 109.4 | C13—C8—C14 | 121.8 (2) |
C2—C1—C6 | 119.7 (3) | O7—C9—C8 | 124.7 (2) |
C2—C1—C7 | 119.6 (2) | O7—C9—C10 | 116.5 (2) |
C6—C1—C7 | 120.7 (2) | C8—C9—C10 | 118.8 (2) |
O3—C2—C1 | 124.7 (3) | O8—C10—C9 | 119.6 (2) |
O3—C2—C3 | 116.3 (2) | O8—C10—C11 | 119.6 (2) |
C1—C2—C3 | 119.0 (2) | C9—C10—C11 | 120.8 (2) |
O4—C3—C2 | 120.6 (2) | C10—C11—C12 | 120.2 (2) |
O4—C3—C4 | 118.7 (3) | C10—C11—H10 | 119.7 |
C2—C3—C4 | 120.7 (2) | C12—C11—H10 | 120.0 |
C3—C4—C5 | 120.2 (3) | C11—C12—C13 | 120.0 (2) |
C3—C4—H4 | 120.2 | C11—C12—H11 | 119.9 |
C5—C4—H4 | 119.6 | C13—C12—H11 | 120.1 |
C4—C5—C6 | 120.3 (3) | C8—C13—C12 | 120.4 (3) |
C4—C5—H5 | 119.8 | C8—C13—H12 | 120.3 |
C6—C5—H5 | 119.9 | C12—C13—H12 | 119.3 |
C1—C6—C5 | 120.1 (2) | O5—C14—O6 | 122.6 (2) |
C1—C6—H6 | 119.9 | O5—C14—C8 | 113.8 (2) |
C5—C6—H6 | 120.0 | O6—C14—C8 | 123.6 (3) |
| | | |
O1—C7—C1—C2 | −178.3 (2) | O8—C10—C9—C8 | 179.6 (2) |
O1—C7—C1—C6 | 2.0 (4) | O8—C10—C11—C12 | −179.7 (3) |
O2—C7—C1—C2 | 1.1 (4) | C1—C2—C3—C4 | −1.3 (4) |
O2—C7—C1—C6 | −178.6 (3) | C1—C6—C5—C4 | −0.2 (4) |
O3—C2—C1—C6 | −178.7 (2) | C2—C1—C6—C5 | −0.7 (4) |
O3—C2—C1—C7 | 1.6 (4) | C2—C3—C4—C5 | 0.4 (4) |
O3—C2—C3—O4 | −1.6 (3) | C3—C2—C1—C6 | 1.5 (4) |
O3—C2—C3—C4 | 178.8 (2) | C3—C2—C1—C7 | −178.2 (2) |
O4—C3—C2—C1 | 178.3 (2) | C3—C4—C5—C6 | 0.4 (4) |
O4—C3—C4—C5 | −179.2 (2) | C5—C6—C1—C7 | 179.0 (3) |
O5—C14—C8—C9 | 173.6 (2) | C8—C9—C10—C11 | −0.5 (4) |
O5—C14—C8—C13 | −7.2 (4) | C8—C13—C12—C11 | −0.3 (4) |
O6—C14—C8—C9 | −6.3 (4) | C9—C8—C13—C12 | 0.1 (4) |
O6—C14—C8—C13 | 172.9 (3) | C9—C10—C11—C12 | 0.4 (4) |
O7—C9—C8—C13 | −179.9 (2) | C10—C9—C8—C13 | 0.3 (4) |
O7—C9—C8—C14 | −0.7 (4) | C10—C9—C8—C14 | 179.5 (2) |
O7—C9—C10—O8 | −0.3 (4) | C10—C11—C12—C13 | 0.0 (5) |
O7—C9—C10—C11 | 179.6 (2) | C12—C13—C8—C14 | −179.1 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, 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, z−1; (ix) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H3···O3 | 0.88 | 2.24 | 2.700 (3) | 113 |
O3—H2···O2 | 0.98 | 1.77 | 2.642 (2) | 147 |
O8—H9···O7 | 0.82 | 2.26 | 2.682 (2) | 113 |
O7—H8···O6 | 0.82 | 1.93 | 2.625 (2) | 143 |
O1—H1···O2i | 0.84 | 1.85 | 2.685 (3) | 175 |
O5—H7···O8viii | 0.83 | 1.81 | 2.645 (2) | 177 |
O4—H3···O6vi | 0.88 | 2.05 | 2.809 (2) | 144 |
O8—H9···O4 | 0.82 | 2.04 | 2.670 (2) | 134 |
Symmetry codes: (i) −x, −y+1, −z+1; (vi) x, y, z+1; (viii) x, y, z−1. |
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