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The asymmetric unit of the title compound, C9H10O6·H2O, consists of one 3-carboxyphenoxyacetic acid (3-CPOAH2) and one water molecule. The intermolecular interactions link symmetry-related molecules into hydrogen-bonded dimers. A supramolecular hydrogen-bonding network structure is formed via further intermolecular hydrogen bonds involving the water molecule.
Supporting information
CCDC reference: 239141
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.117
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.132
Value of mu given = 0.130
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C9 H8 O5
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
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
3-carboxylphenoxyacetic acid monohydrate
top
Crystal data top
C9H8O5·H2O | F(000) = 448 |
Mr = 214.17 | Dx = 1.545 Mg m−3 |
Monoclinic, P21/n | Melting point: not measured K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.728 (2) Å | Cell parameters from 6464 reflections |
b = 4.847 (1) Å | θ = 3.9–27.4° |
c = 21.935 (4) Å | µ = 0.13 mm−1 |
β = 97.22 (3)° | T = 293 K |
V = 920.6 (3) Å3 | Plate, colorless |
Z = 4 | 0.38 × 0.26 × 0.11 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2097 independent reflections |
Radiation source: fine-focus sealed tube | 1403 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −6→6 |
Tmin = 0.960, Tmax = 0.986 | l = −28→28 |
3435 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3 |
2097 reflections | (Δ/σ)max < 0.001 |
152 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.18 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6169 (2) | 0.5669 (3) | 0.12001 (6) | 0.0491 (3) | |
O2 | 0.7714 (2) | 0.9306 (3) | 0.13044 (5) | 0.0491 (3) | |
O3 | 0.7568 (2) | 0.9910 (3) | 0.01102 (5) | 0.0485 (4) | |
O4 | 1.0468 (1) | 1.6457 (3) | −0.09513 (5) | 0.0467 (3) | |
O5 | 0.9775 (2) | 1.5923 (3) | −0.19571 (6) | 0.0569 (4) | |
O1W | 0.6439 (2) | 0.5666 (4) | 0.23774 (7) | 0.0723 (5) | |
C1 | 0.6935 (2) | 0.7679 (4) | 0.09922 (8) | 0.0390 (4) | |
C2 | 0.6724 (2) | 0.7693 (4) | 0.03005 (7) | 0.0415 (4) | |
C3 | 0.7544 (2) | 1.0394 (4) | −0.05081 (7) | 0.0396 (4) | |
C4 | 0.6579 (2) | 0.9097 (4) | −0.09631 (8) | 0.0422 (4) | |
C5 | 0.6627 (2) | 0.9830 (4) | −0.15686 (8) | 0.0467 (4) | |
C6 | 0.7617 (2) | 1.1832 (4) | −0.17202 (7) | 0.0441 (4) | |
C7 | 0.8592 (2) | 1.3125 (3) | −0.12620 (7) | 0.0369 (4) | |
C8 | 0.8553 (2) | 1.2405 (4) | −0.06552 (7) | 0.0395 (4) | |
C9 | 0.9658 (2) | 1.5287 (4) | −0.14309 (7) | 0.0398 (4) | |
H2A | 0.7093 | 0.5974 | 0.0146 | 0.050* | |
H2B | 0.5639 | 0.7896 | 0.0145 | 0.050* | |
H4 | 0.5900 | 0.7739 | −0.0864 | 0.051* | |
H5 | 0.5979 | 0.8950 | −0.1877 | 0.056* | |
H6 | 0.7634 | 1.2321 | −0.2129 | 0.053* | |
H8 | 0.9206 | 1.3274 | −0.0346 | 0.047* | |
H11 | 1.102 (2) | 1.773 (4) | −0.1062 (9) | 0.060 (6)* | |
H10 | 0.627 (3) | 0.565 (5) | 0.1594 (7) | 0.073 (7)* | |
H12B | 0.587 (3) | 0.651 (5) | 0.260 (1) | 0.096 (9)* | |
H12A | 0.684 (3) | 0.439 (5) | 0.258 (1) | 0.100 (1)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0604 (8) | 0.0487 (8) | 0.0399 (7) | −0.0132 (6) | 0.0132 (6) | 0.0024 (6) |
O2 | 0.0620 (8) | 0.0468 (8) | 0.0392 (7) | −0.0123 (6) | 0.0084 (6) | −0.0005 (6) |
O3 | 0.0684 (9) | 0.0650 (9) | 0.0323 (7) | −0.0344 (7) | 0.0083 (6) | 0.0033 (6) |
O4 | 0.0555 (8) | 0.0442 (8) | 0.0410 (6) | −0.0129 (6) | 0.0086 (5) | 0.0000 (6) |
O5 | 0.0705 (9) | 0.065 (1) | 0.0368 (7) | −0.0167 (7) | 0.0109 (6) | 0.0073 (6) |
O1W | 0.101 (1) | 0.079 (1) | 0.0414 (8) | 0.0336 (10) | 0.0241 (8) | 0.0122 (8) |
C1 | 0.0407 (8) | 0.038 (1) | 0.0397 (9) | −0.0002 (7) | 0.0104 (7) | 0.0011 (8) |
C2 | 0.0469 (9) | 0.040 (1) | 0.0381 (9) | −0.0057 (8) | 0.0083 (7) | 0.0012 (8) |
C3 | 0.0453 (9) | 0.042 (1) | 0.0324 (8) | −0.0026 (7) | 0.0075 (7) | −0.0007 (7) |
C4 | 0.0449 (9) | 0.041 (1) | 0.0415 (9) | −0.0078 (8) | 0.0080 (7) | −0.0023 (8) |
C5 | 0.050 (1) | 0.0512 (1) | 0.0374 (9) | −0.0068 (8) | 0.0002 (7) | −0.0058 (8) |
C6 | 0.053 (1) | 0.049 (1) | 0.0306 (8) | −0.0038 (8) | 0.0056 (7) | 0.0014 (8) |
C7 | 0.0411 (8) | 0.0352 (9) | 0.0351 (8) | 0.0015 (7) | 0.0078 (6) | −0.0016 (7) |
C8 | 0.0442 (9) | 0.042 (1) | 0.0320 (8) | −0.0044 (7) | 0.0049 (7) | −0.0027 (7) |
C9 | 0.0433 (9) | 0.041 (1) | 0.0355 (8) | 0.0023 (7) | 0.0073 (7) | 0.0002 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.296 (2) | C2—H2B | 0.9700 |
O1—H10 | 0.86 (2) | C3—C4 | 1.374 (2) |
O2—C1 | 1.199 (2) | C3—C8 | 1.379 (2) |
O3—C3 | 1.374 (2) | C4—C5 | 1.381 (2) |
O3—C2 | 1.396 (2) | C4—H4 | 0.9300 |
O4—C9 | 1.319 (2) | C5—C6 | 1.367 (2) |
O4—H11 | 0.84 (2) | C5—H5 | 0.9300 |
O5—C9 | 1.211 (2) | C6—C7 | 1.383 (2) |
O1W—H12B | 0.84 (2) | C6—H6 | 0.9300 |
O1W—H12A | 0.82 (2) | C7—C8 | 1.380 (2) |
C1—C2 | 1.505 (2) | C7—C9 | 1.479 (2) |
C2—H2A | 0.9700 | C8—H8 | 0.9300 |
| | | |
O1—C1—C2 | 110.8 (1) | C3—C8—H8 | 120.1 |
O2—C1—O1 | 125.0 (2) | C3—O3—C2 | 118.9 (1) |
O2—C1—C2 | 124.2 (2) | C4—C3—C8 | 120.3 (2) |
O3—C2—C1 | 107.6 (1) | C4—C5—H5 | 119.6 |
O3—C2—H2A | 110.2 | C5—C4—H4 | 120.3 |
O3—C2—H2B | 110.2 | C5—C6—C7 | 119.6 (2) |
O3—C3—C4 | 124.8 (2) | C5—C6—H6 | 120.2 |
O3—C3—C8 | 114.9 (1) | C6—C5—C4 | 120.9 (2) |
O4—C9—C7 | 113.3 (1) | C6—C5—H5 | 119.6 |
O5—C9—O4 | 123.4 (2) | C6—C7—C9 | 119.2 (2) |
O5—C9—C7 | 123.3 (2) | C7—C6—H6 | 120.2 |
C1—C2—H2A | 110.2 | C7—C8—H8 | 120.1 |
C1—C2—H2B | 110.2 | C8—C7—C6 | 119.9 (2) |
C1—O1—H10 | 112 (2) | C8—C7—C9 | 120.9 (2) |
C3—C4—C5 | 119.4 (2) | C9—O4—H11 | 111 (1) |
C3—C4—H4 | 120.3 | H2A—C2—H2B | 108.5 |
C3—C8—C7 | 119.9 (2) | H12B—O1W—H12A | 108 (3) |
| | | |
O1—C1—C2—O3 | 179.6 (1) | C4—C5—C6—C7 | 0.6 (3) |
O2—C1—C2—O3 | −0.7 (2) | C5—C6—C7—C8 | −0.5 (3) |
O3—C3—C4—C5 | 177.8 (2) | C6—C7—C8—C3 | 0.1 (3) |
O3—C3—C8—C7 | −177.9 (2) | C6—C7—C9—O4 | 176.7 (2) |
C2—O3—C3—C4 | 9.5 (3) | C6—C7—C9—O5 | −3.2 (3) |
C2—O3—C3—C8 | −172.5 (2) | C8—C3—C4—C5 | −0.1 (3) |
C3—O3—C2—C1 | −179.1 (2) | C8—C7—C9—O4 | −2.8 (2) |
C3—C4—C5—C6 | −0.2 (3) | C8—C7—C9—O5 | 177.3 (2) |
C4—C3—C8—C7 | 0.2 (3) | C9—C7—C8—C3 | 179.6 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H10···O1W | 0.86 (2) | 1.71 (2) | 2.563 (2) | 179 (3) |
O4—H11···O2i | 0.84 (2) | 1.93 (2) | 2.765 (2) | 179 (2) |
O1W—H12A···O2ii | 0.82 (2) | 2.43 (3) | 2.967 (2) | 124 (2) |
O1W—H12A···O1Wii | 0.82 (2) | 2.34 (2) | 3.057 (2) | 147 (2) |
O1W—H12B···O5iii | 0.84 (2) | 1.91 (2) | 2.740 (2) | 169 (3) |
Symmetry codes: (i) −x+2, −y+3, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x−1/2, −y+5/2, z+1/2. |
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