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In the crystal structure of the title compound, C16H12O5·H2O, the water O atom is involved in intermolecular hydrogen bonds which link the molecules into a three-dimensional network.
Supporting information
CCDC reference: 298564
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.135
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C16 H14 O6
Atom count from _chemical_formula_moiety:C16 H32 O5
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.30
From the CIF: _reflns_number_total 1825
Count of symmetry unique reflns 1915
Completeness (_total/calc) 95.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97.
5,7-Dihydroxy-8-methoxy-2-phenyl-4
H-chromen-4-one monohydrate
top
Crystal data top
C16H12O5·H2O | F(000) = 632 |
Mr = 302.27 | Dx = 1.393 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1825 reflections |
a = 4.7160 (9) Å | θ = 3.5–27.3° |
b = 16.551 (3) Å | µ = 0.11 mm−1 |
c = 18.466 (4) Å | T = 298 K |
V = 1441.4 (5) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.10 × 0.10 mm |
Data collection top
MAC DIP 2030K diffractometer | 1801 reflections with I > 2σ(I) |
Radiation source: rotate anode | Rint = 0.040 |
Graphite monochromator | θmax = 27.3°, θmin = 3.5° |
Detector resolution: 0 pixels mm-1 | h = 0→5 |
ω scans | k = −21→21 |
4404 measured reflections | l = −23→23 |
1825 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom & difmap |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.6551P] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max = 0.001 |
1825 reflections | Δρmax = 0.16 e Å−3 |
208 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.059 (11) |
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 | 0.0501 (5) | 0.42824 (13) | 0.27703 (10) | 0.0429 (5) | |
O2 | −0.3595 (6) | 0.63101 (13) | 0.34772 (12) | 0.0561 (7) | |
O3 | −0.6468 (6) | 0.63385 (14) | 0.22700 (13) | 0.0596 (7) | |
H3A | −0.5969 | 0.6487 | 0.2674 | 0.089* | |
O4 | −0.4502 (7) | 0.43054 (15) | 0.05499 (11) | 0.0585 (7) | |
H4A | −0.3521 | 0.3902 | 0.0491 | 0.088* | |
O5 | −0.0475 (6) | 0.36079 (13) | 0.14443 (11) | 0.0496 (6) | |
C2 | 0.1091 (7) | 0.46033 (18) | 0.34343 (15) | 0.0420 (7) | |
C3 | −0.0228 (8) | 0.52753 (19) | 0.36774 (17) | 0.0468 (8) | |
H3B | 0.0241 | 0.5476 | 0.4132 | 0.056* | |
C4 | −0.2323 (8) | 0.56867 (18) | 0.32559 (15) | 0.0437 (7) | |
C5 | −0.4966 (8) | 0.56685 (19) | 0.20767 (16) | 0.0455 (8) | |
C6 | −0.5487 (9) | 0.5315 (2) | 0.14144 (16) | 0.0483 (8) | |
H6A | −0.6834 | 0.5535 | 0.1104 | 0.058* | |
C7 | −0.3976 (8) | 0.46241 (18) | 0.12123 (15) | 0.0462 (8) | |
C8 | −0.1989 (8) | 0.42744 (17) | 0.16707 (15) | 0.0419 (7) | |
C9 | −0.1491 (7) | 0.46422 (17) | 0.23386 (15) | 0.0405 (7) | |
C10 | −0.2958 (7) | 0.53364 (17) | 0.25578 (15) | 0.0404 (7) | |
C11 | −0.1547 (13) | 0.2863 (2) | 0.1725 (2) | 0.0723 (13) | |
H11A | −0.0413 | 0.2424 | 0.1549 | 0.108* | |
H11B | −0.3475 | 0.2792 | 0.1571 | 0.108* | |
H11C | −0.1473 | 0.2874 | 0.2245 | 0.108* | |
C1' | 0.3207 (7) | 0.41227 (18) | 0.38255 (16) | 0.0426 (7) | |
C2' | 0.4376 (9) | 0.3426 (2) | 0.35233 (17) | 0.0526 (8) | |
H2'A | 0.3800 | 0.3260 | 0.3065 | 0.063* | |
C3' | 0.6377 (9) | 0.2980 (2) | 0.3895 (2) | 0.0576 (9) | |
H3'A | 0.7145 | 0.2518 | 0.3685 | 0.069* | |
C4' | 0.7243 (9) | 0.3219 (2) | 0.4580 (2) | 0.0590 (9) | |
H4'A | 0.8602 | 0.2922 | 0.4830 | 0.071* | |
C5' | 0.6069 (9) | 0.3903 (2) | 0.4889 (2) | 0.0603 (10) | |
H5'A | 0.6628 | 0.4058 | 0.5351 | 0.072* | |
C6' | 0.4088 (9) | 0.4356 (2) | 0.45236 (17) | 0.0533 (8) | |
H6'A | 0.3332 | 0.4817 | 0.4737 | 0.064* | |
OW | −0.2104 (7) | 0.29879 (17) | −0.01382 (14) | 0.0599 (7) | |
HWA | −0.183 (12) | 0.322 (3) | −0.057 (3) | 0.093 (16)* | |
HWB | −0.043 (19) | 0.278 (4) | 0.001 (4) | 0.16 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0503 (12) | 0.0458 (11) | 0.0325 (9) | 0.0020 (11) | −0.0042 (10) | −0.0013 (8) |
O2 | 0.0729 (17) | 0.0454 (12) | 0.0500 (12) | 0.0076 (13) | −0.0032 (13) | −0.0104 (9) |
O3 | 0.0764 (18) | 0.0509 (13) | 0.0515 (13) | 0.0176 (14) | −0.0060 (14) | −0.0017 (10) |
O4 | 0.0801 (19) | 0.0601 (13) | 0.0353 (10) | 0.0070 (15) | −0.0104 (13) | −0.0050 (10) |
O5 | 0.0637 (15) | 0.0444 (11) | 0.0406 (11) | 0.0031 (12) | 0.0058 (11) | −0.0037 (9) |
C2 | 0.0449 (17) | 0.0485 (15) | 0.0327 (13) | −0.0058 (14) | 0.0011 (13) | −0.0008 (11) |
C3 | 0.0536 (19) | 0.0497 (16) | 0.0370 (14) | −0.0043 (16) | −0.0023 (14) | −0.0039 (12) |
C4 | 0.0522 (19) | 0.0401 (14) | 0.0389 (14) | −0.0037 (15) | 0.0050 (14) | −0.0040 (12) |
C5 | 0.0548 (19) | 0.0412 (15) | 0.0403 (14) | 0.0008 (16) | 0.0037 (15) | 0.0064 (12) |
C6 | 0.058 (2) | 0.0505 (17) | 0.0361 (14) | −0.0010 (17) | −0.0056 (15) | 0.0061 (12) |
C7 | 0.064 (2) | 0.0430 (14) | 0.0317 (13) | −0.0058 (16) | −0.0006 (15) | 0.0025 (11) |
C8 | 0.0528 (19) | 0.0379 (13) | 0.0349 (13) | −0.0048 (14) | 0.0041 (13) | −0.0010 (11) |
C9 | 0.0460 (17) | 0.0410 (14) | 0.0346 (13) | −0.0022 (14) | 0.0035 (13) | 0.0023 (11) |
C10 | 0.0489 (17) | 0.0373 (13) | 0.0348 (13) | −0.0040 (13) | 0.0024 (13) | −0.0002 (11) |
C11 | 0.108 (4) | 0.0390 (16) | 0.070 (2) | 0.003 (2) | 0.015 (3) | −0.0006 (16) |
C1' | 0.0432 (16) | 0.0474 (15) | 0.0372 (13) | −0.0048 (14) | 0.0030 (14) | 0.0015 (12) |
C2' | 0.058 (2) | 0.0568 (18) | 0.0431 (16) | 0.0051 (17) | −0.0029 (17) | −0.0031 (14) |
C3' | 0.059 (2) | 0.0553 (18) | 0.0583 (19) | 0.0081 (19) | −0.0004 (19) | 0.0004 (16) |
C4' | 0.050 (2) | 0.068 (2) | 0.060 (2) | 0.0011 (19) | −0.0085 (18) | 0.0135 (17) |
C5' | 0.064 (3) | 0.070 (2) | 0.0468 (17) | −0.009 (2) | −0.0136 (18) | 0.0026 (16) |
C6' | 0.058 (2) | 0.0592 (18) | 0.0428 (15) | −0.0012 (18) | −0.0041 (16) | −0.0025 (15) |
OW | 0.0726 (19) | 0.0657 (15) | 0.0413 (12) | 0.0046 (15) | 0.0042 (14) | 0.0036 (11) |
Geometric parameters (Å, º) top
O1—C2 | 1.365 (3) | C8—C9 | 1.395 (4) |
O1—C9 | 1.369 (4) | C9—C10 | 1.401 (4) |
O2—C4 | 1.262 (4) | C11—H11A | 0.9600 |
O3—C5 | 1.363 (4) | C11—H11B | 0.9600 |
O3—H3A | 0.8200 | C11—H11C | 0.9600 |
O4—C7 | 1.355 (3) | C1'—C2' | 1.394 (5) |
O4—H4A | 0.8200 | C1'—C6' | 1.409 (4) |
O5—C8 | 1.379 (4) | C2'—C3' | 1.381 (5) |
O5—C11 | 1.429 (4) | C2'—H2'A | 0.9300 |
C2—C3 | 1.351 (4) | C3'—C4' | 1.388 (5) |
C2—C1' | 1.466 (4) | C3'—H3'A | 0.9300 |
C3—C4 | 1.430 (5) | C4'—C5' | 1.383 (5) |
C3—H3B | 0.9300 | C4'—H4'A | 0.9300 |
C4—C10 | 1.445 (4) | C5'—C6' | 1.376 (5) |
C5—C6 | 1.378 (4) | C5'—H5'A | 0.9300 |
C5—C10 | 1.410 (4) | C6'—H6'A | 0.9300 |
C6—C7 | 1.398 (5) | OW—HWA | 0.90 (5) |
C6—H6A | 0.9300 | OW—HWB | 0.90 (9) |
C7—C8 | 1.389 (5) | | |
| | | |
C2—O1—C9 | 119.6 (2) | C9—C10—C5 | 118.0 (3) |
C5—O3—H3A | 109.5 | C9—C10—C4 | 119.0 (3) |
C7—O4—H4A | 109.5 | C5—C10—C4 | 123.0 (3) |
C8—O5—C11 | 113.4 (3) | O5—C11—H11A | 109.5 |
C3—C2—O1 | 121.7 (3) | O5—C11—H11B | 109.5 |
C3—C2—C1' | 126.6 (3) | H11A—C11—H11B | 109.5 |
O1—C2—C1' | 111.7 (3) | O5—C11—H11C | 109.5 |
C2—C3—C4 | 121.9 (3) | H11A—C11—H11C | 109.5 |
C2—C3—H3B | 119.0 | H11B—C11—H11C | 109.5 |
C4—C3—H3B | 119.0 | C2'—C1'—C6' | 118.5 (3) |
O2—C4—C3 | 122.8 (3) | C2'—C1'—C2 | 121.4 (3) |
O2—C4—C10 | 121.2 (3) | C6'—C1'—C2 | 120.2 (3) |
C3—C4—C10 | 116.0 (3) | C3'—C2'—C1' | 120.9 (3) |
O3—C5—C6 | 119.0 (3) | C3'—C2'—H2'A | 119.5 |
O3—C5—C10 | 120.1 (3) | C1'—C2'—H2'A | 119.5 |
C6—C5—C10 | 120.9 (3) | C2'—C3'—C4' | 120.1 (4) |
C5—C6—C7 | 119.6 (3) | C2'—C3'—H3'A | 119.9 |
C5—C6—H6A | 120.2 | C4'—C3'—H3'A | 119.9 |
C7—C6—H6A | 120.2 | C5'—C4'—C3' | 119.4 (4) |
O4—C7—C8 | 120.8 (3) | C5'—C4'—H4'A | 120.3 |
O4—C7—C6 | 117.8 (3) | C3'—C4'—H4'A | 120.3 |
C8—C7—C6 | 121.5 (3) | C6'—C5'—C4' | 121.1 (3) |
O5—C8—C7 | 119.9 (3) | C6'—C5'—H5'A | 119.4 |
O5—C8—C9 | 122.0 (3) | C4'—C5'—H5'A | 119.4 |
C7—C8—C9 | 118.1 (3) | C5'—C6'—C1' | 120.0 (3) |
O1—C9—C8 | 116.2 (3) | C5'—C6'—H6'A | 120.0 |
O1—C9—C10 | 121.8 (3) | C1'—C6'—H6'A | 120.0 |
C8—C9—C10 | 122.0 (3) | HWA—OW—HWB | 108 (6) |
| | | |
C9—O1—C2—C3 | −0.6 (4) | C8—C9—C10—C5 | −0.8 (4) |
C9—O1—C2—C1' | 178.2 (3) | O1—C9—C10—C4 | 0.8 (4) |
O1—C2—C3—C4 | 0.3 (5) | C8—C9—C10—C4 | −179.7 (3) |
C1'—C2—C3—C4 | −178.3 (3) | O3—C5—C10—C9 | 179.3 (3) |
C2—C3—C4—O2 | 179.3 (3) | C6—C5—C10—C9 | 0.7 (5) |
C2—C3—C4—C10 | 0.5 (5) | O3—C5—C10—C4 | −1.8 (5) |
O3—C5—C6—C7 | −179.5 (3) | C6—C5—C10—C4 | 179.6 (3) |
C10—C5—C6—C7 | −0.9 (5) | O2—C4—C10—C9 | −179.8 (3) |
C5—C6—C7—O4 | −178.5 (3) | C3—C4—C10—C9 | −1.0 (4) |
C5—C6—C7—C8 | 1.2 (5) | O2—C4—C10—C5 | 1.3 (5) |
C11—O5—C8—C7 | −100.4 (4) | C3—C4—C10—C5 | −179.9 (3) |
C11—O5—C8—C9 | 83.0 (4) | C3—C2—C1'—C2' | 178.5 (4) |
O4—C7—C8—O5 | 1.7 (5) | O1—C2—C1'—C2' | −0.3 (4) |
C6—C7—C8—O5 | −178.0 (3) | C3—C2—C1'—C6' | −1.1 (5) |
O4—C7—C8—C9 | 178.4 (3) | O1—C2—C1'—C6' | −179.8 (3) |
C6—C7—C8—C9 | −1.3 (5) | C6'—C1'—C2'—C3' | −0.8 (5) |
C2—O1—C9—C8 | −179.5 (3) | C2—C1'—C2'—C3' | 179.7 (3) |
C2—O1—C9—C10 | 0.0 (4) | C1'—C2'—C3'—C4' | 0.3 (6) |
O5—C8—C9—O1 | −2.8 (4) | C2'—C3'—C4'—C5' | 0.5 (6) |
C7—C8—C9—O1 | −179.4 (3) | C3'—C4'—C5'—C6' | −1.0 (6) |
O5—C8—C9—C10 | 177.7 (3) | C4'—C5'—C6'—C1' | 0.6 (6) |
C7—C8—C9—C10 | 1.1 (5) | C2'—C1'—C6'—C5' | 0.3 (5) |
O1—C9—C10—C5 | 179.7 (3) | C2—C1'—C6'—C5' | 179.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2 | 0.82 | 1.88 | 2.609 (3) | 147 |
O4—H4A···OW | 0.82 | 2.02 | 2.766 (4) | 151 |
OW—HWA···O2i | 0.90 (5) | 1.93 (5) | 2.828 (3) | 177 (5) |
OW—HWB···OWii | 0.90 (9) | 2.03 (8) | 2.903 (3) | 161 (7) |
Symmetry codes: (i) −x−1/2, −y+1, z−1/2; (ii) x+1/2, −y+1/2, −z. |
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