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The xanthone skeleton of the title compound, C13H8O4·3H2O, exhibits a planar conformation, with the hydroxy H atoms lying in the plane. In the crystal structure, the molecules are packed into columns with their planar skeletons parallel to one another.
Supporting information
CCDC reference: 277731
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.151
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.20 Deg.
| Author Response: The crystals were very thin plates which did not diffract
very well and therefore reflections could only be measured
up to \Qmax=24.20\%.
|
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
| Author Response: The crystals were very thin plates which did not diffract
very well and therefore reflections could only be measured
up to \Qmax=24.20\%.
|
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 24.20
From the CIF: _diffrn_reflns_theta_full 24.20
From the CIF: _reflns_number_total 1882
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2032
Completeness (_total/calc) 92.62%
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
centrosymmetric structure
sine(theta)/lambda 0.5768
Proportion of unique data used 1.0000
Ratio reflections to parameters 8.8357
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5768
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.20 Deg.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.84
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22W .. O4 .. 2.66 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4
H2 O
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
11 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
8 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: IPDS1 (Stoe & Cie, 1994); cell refinement: IPDS1; data reduction: IPDS1; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
3,4-Dihydroxy-9
H-xanthen-9-one trihydrate
top
Crystal data top
C13H8O4·3H2O | Z = 2 |
Mr = 282.24 | F(000) = 296 |
Triclinic, P1 | Dx = 1.488 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 6.838 (3) Å | Cell parameters from 34 reflections |
b = 9.946 (4) Å | θ = 6.5–16.7° |
c = 10.087 (4) Å | µ = 0.12 mm−1 |
α = 105.94 (5)° | T = 291 K |
β = 96.54 (5)° | Parallelepiped, colorless |
γ = 103.44 (5)° | 0.4 × 0.15 × 0.08 mm |
V = 629.9 (5) Å3 | |
Data collection top
Stoe IPDS-1 diffractometer | 1270 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 24.2°, θmin = 3.9° |
φ scans | h = −7→7 |
4054 measured reflections | k = −11→11 |
1882 independent reflections | l = −11→11 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0902P)2 + 0.0203P] where P = (Fo2 + 2Fc2)/3 |
1882 reflections | (Δ/σ)max < 0.001 |
213 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.16 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 | |
O4A | 0.2065 (3) | 0.90327 (17) | 0.14611 (17) | 0.0569 (5) | |
O4 | 0.1636 (3) | 0.65204 (19) | −0.0421 (2) | 0.0673 (6) | |
O9 | 0.3109 (3) | 1.29123 (18) | 0.05629 (19) | 0.0703 (6) | |
O3 | 0.1979 (3) | 0.63422 (18) | −0.3166 (2) | 0.0679 (6) | |
C4A | 0.2235 (4) | 0.9069 (3) | 0.0132 (2) | 0.0507 (6) | |
C9A | 0.2613 (4) | 1.0361 (2) | −0.0224 (2) | 0.0497 (6) | |
C8A | 0.2688 (4) | 1.1666 (2) | 0.2256 (2) | 0.0519 (6) | |
C4 | 0.2025 (4) | 0.7723 (2) | −0.0861 (2) | 0.0524 (6) | |
C2 | 0.2594 (4) | 0.8963 (3) | −0.2602 (3) | 0.0564 (7) | |
H2 | 0.2726 | 0.8927 | −0.3517 | 0.068* | |
C1 | 0.2801 (4) | 1.0271 (3) | −0.1613 (2) | 0.0544 (7) | |
H1 | 0.3070 | 1.1117 | −0.1869 | 0.065* | |
C10A | 0.2333 (4) | 1.0325 (3) | 0.2514 (2) | 0.0538 (7) | |
C3 | 0.2182 (4) | 0.7671 (3) | −0.2234 (2) | 0.0537 (7) | |
C9 | 0.2823 (4) | 1.1736 (3) | 0.0844 (2) | 0.0525 (7) | |
C5 | 0.2221 (5) | 1.0225 (3) | 0.3850 (3) | 0.0656 (8) | |
H5 | 0.1992 | 0.9326 | 0.4006 | 0.079* | |
C8 | 0.2913 (4) | 1.2916 (3) | 0.3399 (3) | 0.0606 (7) | |
H8 | 0.3136 | 1.3819 | 0.3253 | 0.073* | |
C7 | 0.2809 (5) | 1.2828 (3) | 0.4721 (3) | 0.0688 (8) | |
H7 | 0.2973 | 1.3664 | 0.5469 | 0.083* | |
C6 | 0.2453 (5) | 1.1462 (3) | 0.4934 (3) | 0.0719 (9) | |
H6 | 0.2373 | 1.1398 | 0.5830 | 0.086* | |
O1W | 0.4180 (4) | 1.5930 (3) | 0.1866 (2) | 0.0857 (7) | |
O2W | 0.1472 (5) | 0.3763 (2) | −0.1879 (2) | 0.0820 (8) | |
O3W | 0.1913 (5) | 0.6550 (3) | −0.5800 (2) | 0.0841 (7) | |
H11W | 0.356 (7) | 1.623 (5) | 0.128 (5) | 0.109 (14)* | |
H12W | 0.373 (7) | 1.495 (5) | 0.142 (5) | 0.122 (14)* | |
H3 | 0.200 (6) | 0.642 (4) | −0.412 (4) | 0.097 (11)* | |
H4 | 0.163 (7) | 0.571 (5) | −0.124 (5) | 0.127 (14)* | |
H31W | 0.073 (9) | 0.624 (5) | −0.633 (6) | 0.14 (2)* | |
H21W | 0.294 (7) | 0.386 (4) | −0.176 (4) | 0.100 (14)* | |
H32W | 0.270 (8) | 0.642 (5) | −0.644 (6) | 0.142 (19)* | |
H22W | 0.116 (9) | 0.349 (6) | −0.120 (6) | 0.16 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4A | 0.0708 (12) | 0.0485 (9) | 0.0507 (9) | 0.0138 (8) | 0.0151 (8) | 0.0150 (7) |
O4 | 0.0940 (15) | 0.0474 (10) | 0.0619 (11) | 0.0176 (9) | 0.0188 (10) | 0.0195 (8) |
O9 | 0.0997 (15) | 0.0487 (10) | 0.0633 (11) | 0.0185 (9) | 0.0151 (10) | 0.0205 (8) |
O3 | 0.0917 (15) | 0.0490 (10) | 0.0580 (11) | 0.0176 (9) | 0.0154 (10) | 0.0099 (8) |
C4A | 0.0510 (15) | 0.0514 (13) | 0.0474 (13) | 0.0111 (11) | 0.0096 (10) | 0.0144 (10) |
C9A | 0.0498 (15) | 0.0457 (13) | 0.0522 (13) | 0.0122 (11) | 0.0086 (11) | 0.0142 (10) |
C8A | 0.0517 (15) | 0.0495 (13) | 0.0528 (14) | 0.0131 (11) | 0.0091 (11) | 0.0144 (11) |
C4 | 0.0571 (16) | 0.0434 (12) | 0.0552 (14) | 0.0112 (11) | 0.0083 (11) | 0.0165 (10) |
C2 | 0.0630 (17) | 0.0561 (14) | 0.0512 (13) | 0.0148 (12) | 0.0126 (12) | 0.0191 (11) |
C1 | 0.0619 (16) | 0.0488 (13) | 0.0512 (13) | 0.0131 (11) | 0.0092 (11) | 0.0159 (11) |
C10A | 0.0565 (16) | 0.0505 (14) | 0.0503 (14) | 0.0126 (11) | 0.0083 (11) | 0.0118 (11) |
C3 | 0.0531 (16) | 0.0502 (13) | 0.0539 (14) | 0.0140 (11) | 0.0093 (11) | 0.0107 (11) |
C9 | 0.0559 (16) | 0.0490 (13) | 0.0515 (13) | 0.0129 (11) | 0.0079 (11) | 0.0163 (10) |
C5 | 0.083 (2) | 0.0595 (15) | 0.0556 (15) | 0.0153 (14) | 0.0158 (14) | 0.0222 (12) |
C8 | 0.0710 (18) | 0.0513 (13) | 0.0551 (14) | 0.0152 (12) | 0.0106 (12) | 0.0116 (11) |
C7 | 0.084 (2) | 0.0617 (16) | 0.0541 (15) | 0.0197 (14) | 0.0132 (14) | 0.0074 (12) |
C6 | 0.092 (2) | 0.0710 (18) | 0.0513 (15) | 0.0184 (15) | 0.0173 (14) | 0.0191 (13) |
O1W | 0.124 (2) | 0.0606 (13) | 0.0636 (13) | 0.0204 (12) | 0.0035 (12) | 0.0156 (10) |
O2W | 0.120 (2) | 0.0589 (12) | 0.0674 (13) | 0.0248 (12) | 0.0165 (13) | 0.0210 (10) |
O3W | 0.0938 (19) | 0.0874 (15) | 0.0601 (13) | 0.0213 (13) | 0.0105 (13) | 0.0102 (11) |
Geometric parameters (Å, º) top
O4A—C4A | 1.369 (3) | C2—H2 | 0.9300 |
O4A—C10A | 1.382 (3) | C1—H1 | 0.9300 |
O4—C4 | 1.367 (3) | C10A—C5 | 1.388 (3) |
O4—H4 | 0.98 (5) | C5—C6 | 1.366 (4) |
O9—C9 | 1.255 (3) | C5—H5 | 0.9300 |
O3—C3 | 1.361 (3) | C8—C7 | 1.369 (4) |
O3—H3 | 0.99 (4) | C8—H8 | 0.9300 |
C4A—C4 | 1.399 (4) | C7—C6 | 1.404 (4) |
C4A—C9A | 1.402 (3) | C7—H7 | 0.9300 |
C9A—C1 | 1.403 (3) | C6—H6 | 0.9300 |
C9A—C9 | 1.455 (4) | O1W—H11W | 0.85 (5) |
C8A—C10A | 1.400 (3) | O1W—H12W | 0.92 (5) |
C8A—C8 | 1.408 (4) | O2W—H21W | 0.98 (5) |
C8A—C9 | 1.457 (3) | O2W—H22W | 0.84 (6) |
C4—C3 | 1.388 (4) | O3W—H31W | 0.85 (6) |
C2—C1 | 1.370 (4) | O3W—H32W | 0.89 (6) |
C2—C3 | 1.409 (4) | | |
| | | |
C4A—O4A—C10A | 118.98 (19) | C5—C10A—C8A | 121.4 (2) |
C4—O4—H4 | 105 (3) | O3—C3—C4 | 117.1 (2) |
C3—O3—H3 | 110 (2) | O3—C3—C2 | 122.8 (2) |
O4A—C4A—C4 | 115.5 (2) | C4—C3—C2 | 120.1 (2) |
O4A—C4A—C9A | 122.8 (2) | O9—C9—C9A | 121.8 (2) |
C4—C4A—C9A | 121.7 (2) | O9—C9—C8A | 122.2 (2) |
C4A—C9A—C1 | 117.9 (2) | C9A—C9—C8A | 116.0 (2) |
C4A—C9A—C9 | 119.8 (2) | C6—C5—C10A | 119.1 (2) |
C1—C9A—C9 | 122.3 (2) | C6—C5—H5 | 120.4 |
C10A—C8A—C8 | 117.7 (2) | C10A—C5—H5 | 120.4 |
C10A—C8A—C9 | 120.1 (2) | C7—C8—C8A | 121.2 (2) |
C8—C8A—C9 | 122.2 (2) | C7—C8—H8 | 119.4 |
O4—C4—C3 | 123.6 (2) | C8A—C8—H8 | 119.4 |
O4—C4—C4A | 117.5 (2) | C8—C7—C6 | 119.2 (2) |
C3—C4—C4A | 118.9 (2) | C8—C7—H7 | 120.4 |
C1—C2—C3 | 120.1 (2) | C6—C7—H7 | 120.4 |
C1—C2—H2 | 119.9 | C5—C6—C7 | 121.3 (2) |
C3—C2—H2 | 119.9 | C5—C6—H6 | 119.4 |
C2—C1—C9A | 121.3 (2) | C7—C6—H6 | 119.4 |
C2—C1—H1 | 119.4 | H11W—O1W—H12W | 100 (4) |
C9A—C1—H1 | 119.4 | H21W—O2W—H22W | 102 (5) |
O4A—C10A—C5 | 116.3 (2) | H31W—O3W—H32W | 101 (4) |
O4A—C10A—C8A | 122.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O3W | 0.99 (4) | 1.73 (4) | 2.717 (3) | 177 (3) |
O4—H4···O2W | 0.98 (5) | 1.84 (5) | 2.702 (3) | 145 (4) |
O1W—H11W···O4i | 0.85 (5) | 2.17 (5) | 2.999 (4) | 168 (4) |
O1W—H12W···O9 | 0.92 (5) | 1.89 (5) | 2.805 (3) | 174 (4) |
O2W—H21W···O1Wii | 0.98 (5) | 1.95 (5) | 2.915 (5) | 170 (3) |
O2W—H22W···O4iii | 0.84 (6) | 2.66 (6) | 3.343 (4) | 141 (5) |
O3W—H31W···O2Wiv | 0.85 (6) | 2.21 (6) | 2.994 (4) | 152 (5) |
O3W—H32W···O1Wv | 0.89 (6) | 2.09 (6) | 2.968 (4) | 172 (5) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+2, −z; (iii) −x, −y+1, −z; (iv) −x, −y+1, −z−1; (v) x, y−1, z−1. |
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