
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104012686/na5013sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108768104012686/na50131sup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S0108768104012686/na50132sup3.hkl |
CCDC references: 248464; 248465
All H atoms for (1) were found in electron-density difference maps. The C-bound Hs were allowed to refine. The phenolic H and the ordered carboxyl H (on O2) were allowed to vary positionally and their displacement parameters were fixed at 0.080 Å2. The disordered carboxyl Hs were set at 50% occupancy (after allowing this occupancy to vary and finding 50%) and were placed at 0.82 Å from O4 and O5 and allowed to refine as riding atoms with displacement parameters fixed at 0.080 Å2. Water Hs calculated using the program HYDROGEN (Nardelli, 1999) were allowed to ride on the water O and their displacement parameters were fixed at 0.080 Å2. The observed disorder of the C8 carboxyl is reflected by the high values of the Uequiv parameters and the Rmax/Rmin ratios for atoms O4 & O5. The high Uequiv and Rmax/Rmin ratios for atom O6 may be attributable to the electron density of the inadequately modeled H atoms.
For both compounds, data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXP-97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C8H6O5·H2O | Z = 2 |
Mr = 200.14 | F(000) = 208 |
Triclinic, P1 | Dx = 1.610 Mg m−3 Dm = 1.60 Mg m−3 Dm measured by flotation in BrCCl3/cyclohexane |
Hall symbol: -P 1 | Melting point: 373 K |
a = 3.6673 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7608 (19) Å | Cell parameters from 24 reflections |
c = 11.8421 (15) Å | θ = 8.7–19.7° |
α = 97.647 (13)° | µ = 0.14 mm−1 |
β = 90.219 (13)° | T = 296 K |
γ = 100.537 (16)° | Square prism, pale yellow |
V = 412.87 (15) Å3 | 0.40 × 0.30 × 0.20 mm |
Siemens P4 diffractometer | 1574 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 30.0°, θmin = 1.7° |
2θ/θ scans | h = −1→5 |
Absorption correction: numerical Sheldrick (1997) | k = −13→13 |
Tmin = 0.95, Tmax = 0.98 | l = −16→16 |
3409 measured reflections | 3 standard reflections every 97 reflections |
2400 independent reflections | intensity decay: variation <2.0% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.186 | w = 1/[σ2(Fo2) + (0.1001P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.46 |
2400 reflections | Δρmax = 0.39 e Å−3 |
148 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00 (3) |
C8H6O5·H2O | γ = 100.537 (16)° |
Mr = 200.14 | V = 412.87 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 3.6673 (6) Å | Mo Kα radiation |
b = 9.7608 (19) Å | µ = 0.14 mm−1 |
c = 11.8421 (15) Å | T = 296 K |
α = 97.647 (13)° | 0.40 × 0.30 × 0.20 mm |
β = 90.219 (13)° |
Siemens P4 diffractometer | 1574 reflections with I > 2σ(I) |
Absorption correction: numerical Sheldrick (1997) | Rint = 0.059 |
Tmin = 0.95, Tmax = 0.98 | 3 standard reflections every 97 reflections |
3409 measured reflections | intensity decay: variation <2.0% |
2400 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.186 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | (Δ/σ)max = 0.46 |
2400 reflections | Δρmax = 0.39 e Å−3 |
148 parameters | Δρmin = −0.42 e Å−3 |
Experimental. 'crystal mounted on glass fiber using epoxy resin' |
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 statisticallyabout twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.3605 (5) | 0.11802 (13) | 0.48484 (10) | 0.0500 (4) | |
O2 | 0.2067 (4) | 0.31251 (14) | 0.43745 (11) | 0.0487 (4) | |
H2 | 0.220 (8) | 0.259 (3) | 0.365 (3) | 0.080* | |
O3 | 0.3721 (4) | 0.07821 (11) | 0.69435 (9) | 0.0390 (4) | |
H3 | 0.410 (8) | 0.073 (3) | 0.617 (3) | 0.080* | |
O4 | 0.2829 (6) | 0.25056 (17) | 1.03056 (11) | 0.0667 (6) | |
H4 | 0.2884 | 0.1960 | 1.0773 | 0.080* | 0.50 |
O5 | 0.4104 (5) | 0.06883 (14) | 0.91522 (10) | 0.0549 (5) | |
H5 | 0.4471 | 0.0428 | 0.9766 | 0.080* | 0.50 |
O6 | 0.2622 (8) | 0.1569 (2) | 0.23472 (14) | 0.0933 (8) | |
H106 | 0.3356 | 0.0770 | 0.2206 | 0.080* | |
H206 | 0.0751 | 0.1497 | 0.1878 | 0.080* | |
C1 | 0.2465 (4) | 0.29125 (16) | 0.63348 (12) | 0.0288 (3) | |
C2 | 0.3000 (5) | 0.20891 (15) | 0.72026 (12) | 0.0279 (4) | |
C3 | 0.2761 (5) | 0.26611 (16) | 0.83498 (12) | 0.0306 (4) | |
C4 | 0.2062 (5) | 0.40280 (18) | 0.85941 (14) | 0.0362 (4) | |
H4A | 0.191 (7) | 0.445 (3) | 0.940 (2) | 0.056 (6)* | |
C5 | 0.1559 (6) | 0.48321 (18) | 0.77515 (15) | 0.0391 (4) | |
H5A | 0.095 (6) | 0.572 (3) | 0.7961 (19) | 0.050 (6)* | |
C6 | 0.1750 (5) | 0.42655 (17) | 0.66251 (14) | 0.0347 (4) | |
H6 | 0.136 (7) | 0.477 (2) | 0.6001 (19) | 0.050 (6)* | |
C7 | 0.2765 (5) | 0.23265 (16) | 0.51308 (13) | 0.0324 (4) | |
C8 | 0.3257 (5) | 0.18936 (18) | 0.93217 (13) | 0.0363 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0899 (12) | 0.0398 (7) | 0.0278 (6) | 0.0307 (7) | 0.0055 (6) | 0.0052 (5) |
O2 | 0.0799 (11) | 0.0426 (7) | 0.0309 (6) | 0.0239 (7) | 0.0025 (6) | 0.0143 (5) |
O3 | 0.0697 (9) | 0.0271 (6) | 0.0251 (5) | 0.0211 (6) | 0.0028 (5) | 0.0040 (4) |
O4 | 0.1230 (16) | 0.0604 (9) | 0.0241 (6) | 0.0384 (10) | 0.0058 (7) | 0.0027 (6) |
O5 | 0.0967 (13) | 0.0471 (8) | 0.0299 (6) | 0.0341 (8) | 0.0008 (7) | 0.0087 (5) |
O6 | 0.173 (2) | 0.0796 (13) | 0.0370 (8) | 0.0383 (14) | 0.0075 (10) | 0.0219 (7) |
C1 | 0.0323 (8) | 0.0284 (7) | 0.0278 (7) | 0.0093 (6) | 0.0023 (6) | 0.0059 (5) |
C2 | 0.0342 (8) | 0.0244 (6) | 0.0263 (6) | 0.0089 (6) | 0.0019 (6) | 0.0028 (5) |
C3 | 0.0354 (9) | 0.0320 (7) | 0.0249 (7) | 0.0088 (7) | 0.0010 (6) | 0.0018 (5) |
C4 | 0.0393 (10) | 0.0361 (8) | 0.0329 (8) | 0.0117 (7) | 0.0030 (7) | −0.0035 (6) |
C5 | 0.0451 (10) | 0.0281 (7) | 0.0456 (9) | 0.0145 (7) | 0.0021 (8) | 0.0001 (6) |
C6 | 0.0385 (10) | 0.0298 (7) | 0.0389 (8) | 0.0119 (7) | 0.0024 (7) | 0.0078 (6) |
C7 | 0.0420 (9) | 0.0312 (7) | 0.0266 (7) | 0.0104 (7) | 0.0021 (6) | 0.0082 (5) |
C8 | 0.0455 (10) | 0.0391 (8) | 0.0245 (7) | 0.0095 (7) | 0.0010 (6) | 0.0028 (6) |
O1—C7 | 1.219 (2) | C1—C6 | 1.392 (2) |
O2—C7 | 1.3163 (18) | C1—C2 | 1.420 (2) |
O2—H2 | 0.95 (3) | C1—C7 | 1.476 (2) |
O3—C2 | 1.3459 (17) | C2—C3 | 1.408 (2) |
O3—H3 | 0.92 (3) | C3—C4 | 1.397 (2) |
O4—C8 | 1.261 (2) | C3—C8 | 1.482 (2) |
O4—H4 | 0.8200 | C4—C5 | 1.380 (2) |
O5—C8 | 1.262 (2) | C4—H4A | 0.99 (2) |
O5—H5 | 0.8200 | C5—C6 | 1.382 (2) |
O6—H106 | 0.8668 | C5—H5A | 0.93 (2) |
O6—H206 | 0.8677 | C6—H6 | 0.97 (2) |
C7—O2—H2 | 106.2 (19) | C5—C4—H4A | 117.6 (15) |
C2—O3—H3 | 102.1 (18) | C3—C4—H4A | 120.0 (15) |
C8—O4—H4 | 109.5 | C4—C5—C6 | 118.86 (14) |
C8—O5—H5 | 109.5 | C4—C5—H5A | 118.8 (14) |
H106—O6—H206 | 104.6 | C6—C5—H5A | 122.2 (14) |
C6—C1—C2 | 120.01 (14) | C5—C6—C1 | 121.07 (15) |
C6—C1—C7 | 120.84 (13) | C5—C6—H6 | 122.3 (14) |
C2—C1—C7 | 119.13 (13) | C1—C6—H6 | 116.7 (14) |
O3—C2—C3 | 120.02 (13) | O1—C7—O2 | 121.81 (14) |
O3—C2—C1 | 121.11 (13) | O1—C7—C1 | 122.61 (13) |
C3—C2—C1 | 118.87 (13) | O2—C7—C1 | 115.58 (14) |
C4—C3—C2 | 118.77 (14) | O4—C8—O5 | 122.56 (16) |
C4—C3—C8 | 117.85 (13) | O4—C8—C3 | 116.99 (15) |
C2—C3—C8 | 123.38 (14) | O5—C8—C3 | 120.45 (13) |
C5—C4—C3 | 122.41 (14) | ||
C6—C1—C2—O3 | −179.51 (16) | C4—C5—C6—C1 | −0.5 (3) |
C7—C1—C2—O3 | −0.9 (2) | C2—C1—C6—C5 | 0.2 (3) |
C6—C1—C2—C3 | 0.6 (2) | C7—C1—C6—C5 | −178.34 (16) |
C7—C1—C2—C3 | 179.14 (15) | C6—C1—C7—O1 | 175.52 (18) |
O3—C2—C3—C4 | 179.09 (15) | C2—C1—C7—O1 | −3.0 (3) |
C1—C2—C3—C4 | −1.0 (2) | C6—C1—C7—O2 | −4.4 (3) |
O3—C2—C3—C8 | −0.1 (3) | C2—C1—C7—O2 | 177.02 (15) |
C1—C2—C3—C8 | 179.77 (15) | C4—C3—C8—O4 | 3.4 (3) |
C2—C3—C4—C5 | 0.7 (3) | C2—C3—C8—O4 | −177.32 (19) |
C8—C3—C4—C5 | 179.98 (17) | C4—C3—C8—O5 | −175.92 (18) |
C3—C4—C5—C6 | 0.1 (3) | C2—C3—C8—O5 | 3.3 (3) |
C24H20P·C8H5O5 | F(000) = 1088 |
Mr = 520.49 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/c | Melting point: 446 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.287 (5) Å | Cell parameters from 22 reflections |
b = 8.027 (3) Å | θ = 4.1–10.5° |
c = 22.144 (7) Å | µ = 0.14 mm−1 |
β = 101.15 (2)° | T = 296 K |
V = 2665.7 (15) Å3 | Prism, colourless |
Z = 4 | 0.50 × 0.44 × 0.26 mm |
Siemens P4 diffractometer | 2544 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
2θ/θ scans | h = −18→1 |
Absorption correction: numerical Sheldrick (1997) | k = −9→1 |
Tmin = 0.94, Tmax = 0.97 | l = −26→26 |
6087 measured reflections | 3 standard reflections every 97 reflections |
4707 independent reflections | intensity decay: variation <1.3% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.5629P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4707 reflections | Δρmax = 0.17 e Å−3 |
350 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0030 (5) |
C24H20P·C8H5O5 | V = 2665.7 (15) Å3 |
Mr = 520.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.287 (5) Å | µ = 0.14 mm−1 |
b = 8.027 (3) Å | T = 296 K |
c = 22.144 (7) Å | 0.50 × 0.44 × 0.26 mm |
β = 101.15 (2)° |
Siemens P4 diffractometer | 2544 reflections with I > 2σ(I) |
Absorption correction: numerical Sheldrick (1997) | Rint = 0.031 |
Tmin = 0.94, Tmax = 0.97 | 3 standard reflections every 97 reflections |
6087 measured reflections | intensity decay: variation <1.3% |
4707 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.17 e Å−3 |
4707 reflections | Δρmin = −0.24 e Å−3 |
350 parameters |
Experimental. 'crystal mounted on glass fiber using cyanoacrylate cement' |
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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.27966 (6) | 0.37526 (11) | 0.83276 (4) | 0.0446 (3) | |
O1 | 0.0967 (3) | 0.0399 (4) | 0.66868 (17) | 0.0991 (11) | |
H1A | 0.161 (3) | 0.045 (5) | 0.6667 (17) | 0.080* | |
O2 | −0.0272 (2) | 0.1402 (4) | 0.61367 (18) | 0.1194 (13) | |
O3 | 0.24116 (17) | 0.0958 (3) | 0.63760 (12) | 0.0666 (7) | |
O4 | 0.3879 (2) | 0.3074 (4) | 0.52447 (14) | 0.0986 (11) | |
O5 | 0.38415 (19) | 0.1569 (4) | 0.60659 (16) | 0.0882 (10) | |
H5A | 0.341 (3) | 0.125 (5) | 0.6295 (17) | 0.080* | |
C1 | 0.1064 (3) | 0.1942 (5) | 0.57844 (19) | 0.0620 (10) | |
C2 | 0.1990 (2) | 0.1788 (4) | 0.58979 (17) | 0.0517 (9) | |
C3 | 0.2475 (3) | 0.2559 (4) | 0.54914 (17) | 0.0544 (9) | |
C4 | 0.2016 (3) | 0.3465 (5) | 0.50000 (18) | 0.0780 (13) | |
H4 | 0.2334 | 0.3992 | 0.4736 | 0.094* | |
C5 | 0.1106 (4) | 0.3608 (7) | 0.4891 (2) | 0.1013 (16) | |
H5 | 0.0809 | 0.4216 | 0.4556 | 0.122* | |
C6 | 0.0641 (3) | 0.2841 (6) | 0.5284 (2) | 0.0898 (14) | |
H6 | 0.0023 | 0.2932 | 0.5210 | 0.108* | |
C7 | 0.0525 (3) | 0.1218 (6) | 0.6208 (3) | 0.0800 (13) | |
C8 | 0.3446 (3) | 0.2421 (6) | 0.5582 (2) | 0.0694 (12) | |
C9 | 0.1854 (2) | 0.2413 (4) | 0.82796 (14) | 0.0450 (9) | |
C10 | 0.1966 (2) | 0.0710 (4) | 0.83535 (16) | 0.0537 (9) | |
H10A | 0.2537 | 0.0261 | 0.8434 | 0.064* | |
C11 | 0.1242 (3) | −0.0319 (5) | 0.83094 (17) | 0.0680 (11) | |
H11A | 0.1323 | −0.1463 | 0.8357 | 0.082* | |
C12 | 0.0402 (3) | 0.0330 (5) | 0.81962 (17) | 0.0672 (11) | |
H12A | −0.0087 | −0.0372 | 0.8170 | 0.081* | |
C13 | 0.0277 (2) | 0.2005 (6) | 0.81215 (18) | 0.0662 (11) | |
H13A | −0.0299 | 0.2437 | 0.8042 | 0.079* | |
C14 | 0.0992 (2) | 0.3055 (5) | 0.81623 (15) | 0.0548 (10) | |
H14A | 0.0901 | 0.4196 | 0.8112 | 0.066* | |
C15 | 0.2614 (2) | 0.5114 (4) | 0.76774 (15) | 0.0435 (8) | |
C16 | 0.2138 (2) | 0.4571 (4) | 0.71155 (16) | 0.0560 (10) | |
H16A | 0.1873 | 0.3523 | 0.7083 | 0.067* | |
C17 | 0.2056 (3) | 0.5579 (5) | 0.66057 (17) | 0.0634 (11) | |
H17A | 0.1742 | 0.5206 | 0.6228 | 0.076* | |
C18 | 0.2433 (3) | 0.7121 (5) | 0.66521 (19) | 0.0677 (12) | |
H18A | 0.2375 | 0.7800 | 0.6306 | 0.081* | |
C19 | 0.2901 (3) | 0.7676 (5) | 0.72092 (19) | 0.0757 (12) | |
H19A | 0.3155 | 0.8732 | 0.7240 | 0.091* | |
C20 | 0.2992 (2) | 0.6675 (5) | 0.77176 (17) | 0.0634 (11) | |
H20A | 0.3313 | 0.7052 | 0.8093 | 0.076* | |
C21 | 0.2995 (2) | 0.4990 (4) | 0.90088 (14) | 0.0459 (9) | |
C22 | 0.3843 (2) | 0.5639 (5) | 0.92279 (16) | 0.0618 (10) | |
H22A | 0.4318 | 0.5338 | 0.9045 | 0.074* | |
C23 | 0.3971 (3) | 0.6721 (5) | 0.97144 (19) | 0.0751 (12) | |
H23A | 0.4536 | 0.7156 | 0.9862 | 0.090* | |
C24 | 0.3273 (3) | 0.7167 (5) | 0.99850 (19) | 0.0780 (13) | |
H24A | 0.3365 | 0.7902 | 1.0316 | 0.094* | |
C25 | 0.2446 (3) | 0.6542 (5) | 0.97720 (18) | 0.0738 (12) | |
H25A | 0.1974 | 0.6856 | 0.9956 | 0.089* | |
C26 | 0.2301 (2) | 0.5444 (5) | 0.92848 (16) | 0.0568 (10) | |
H26A | 0.1734 | 0.5012 | 0.9143 | 0.068* | |
C27 | 0.3749 (2) | 0.2488 (4) | 0.83079 (15) | 0.0458 (9) | |
C28 | 0.4169 (2) | 0.1701 (5) | 0.88372 (16) | 0.0594 (10) | |
H28A | 0.3984 | 0.1902 | 0.9207 | 0.071* | |
C29 | 0.4862 (3) | 0.0619 (5) | 0.8822 (2) | 0.0731 (12) | |
H29A | 0.5141 | 0.0074 | 0.9178 | 0.088* | |
C30 | 0.5133 (3) | 0.0354 (5) | 0.8277 (2) | 0.0805 (13) | |
H30A | 0.5609 | −0.0361 | 0.8268 | 0.097* | |
C31 | 0.4723 (3) | 0.1111 (6) | 0.77465 (19) | 0.0764 (12) | |
H31A | 0.4914 | 0.0909 | 0.7379 | 0.092* | |
C32 | 0.4024 (2) | 0.2178 (4) | 0.77606 (17) | 0.0572 (10) | |
H32A | 0.3735 | 0.2692 | 0.7400 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0440 (5) | 0.0427 (5) | 0.0463 (5) | 0.0021 (5) | 0.0073 (4) | 0.0012 (5) |
O1 | 0.095 (2) | 0.094 (3) | 0.119 (3) | −0.016 (2) | 0.048 (2) | 0.015 (2) |
O2 | 0.064 (2) | 0.106 (3) | 0.197 (4) | −0.015 (2) | 0.049 (2) | −0.018 (3) |
O3 | 0.0685 (17) | 0.0592 (17) | 0.0729 (17) | 0.0042 (14) | 0.0150 (15) | 0.0173 (15) |
O4 | 0.096 (2) | 0.126 (3) | 0.085 (2) | −0.046 (2) | 0.0452 (19) | −0.023 (2) |
O5 | 0.0615 (18) | 0.114 (3) | 0.088 (2) | −0.0055 (19) | 0.0113 (16) | −0.003 (2) |
C1 | 0.057 (2) | 0.055 (2) | 0.075 (3) | −0.002 (2) | 0.012 (2) | −0.005 (2) |
C2 | 0.059 (2) | 0.040 (2) | 0.055 (2) | −0.0043 (18) | 0.0089 (19) | −0.0057 (19) |
C3 | 0.065 (2) | 0.049 (2) | 0.052 (2) | −0.008 (2) | 0.018 (2) | −0.009 (2) |
C4 | 0.111 (4) | 0.073 (3) | 0.052 (3) | −0.003 (3) | 0.020 (3) | 0.003 (2) |
C5 | 0.108 (4) | 0.115 (4) | 0.070 (3) | 0.024 (4) | −0.010 (3) | 0.011 (3) |
C6 | 0.068 (3) | 0.098 (4) | 0.096 (4) | 0.011 (3) | −0.002 (3) | −0.004 (3) |
C7 | 0.063 (3) | 0.065 (3) | 0.117 (4) | −0.010 (3) | 0.031 (3) | −0.013 (3) |
C8 | 0.076 (3) | 0.071 (3) | 0.065 (3) | −0.027 (3) | 0.024 (3) | −0.032 (3) |
C9 | 0.047 (2) | 0.043 (2) | 0.044 (2) | −0.0011 (17) | 0.0075 (16) | 0.0013 (17) |
C10 | 0.054 (2) | 0.047 (2) | 0.061 (2) | 0.0003 (18) | 0.0110 (19) | 0.0024 (19) |
C11 | 0.073 (3) | 0.050 (2) | 0.081 (3) | −0.009 (2) | 0.014 (2) | −0.003 (2) |
C12 | 0.064 (3) | 0.066 (3) | 0.070 (3) | −0.020 (2) | 0.009 (2) | −0.005 (2) |
C13 | 0.044 (2) | 0.076 (3) | 0.078 (3) | −0.006 (2) | 0.011 (2) | −0.007 (2) |
C14 | 0.052 (2) | 0.049 (2) | 0.061 (2) | 0.0015 (19) | 0.0046 (18) | 0.0032 (19) |
C15 | 0.046 (2) | 0.036 (2) | 0.046 (2) | 0.0014 (16) | 0.0057 (16) | 0.0047 (17) |
C16 | 0.068 (2) | 0.040 (2) | 0.057 (2) | 0.001 (2) | 0.004 (2) | 0.004 (2) |
C17 | 0.084 (3) | 0.050 (2) | 0.053 (2) | 0.010 (2) | 0.006 (2) | 0.000 (2) |
C18 | 0.099 (3) | 0.048 (2) | 0.060 (3) | 0.007 (2) | 0.025 (2) | 0.012 (2) |
C19 | 0.100 (3) | 0.048 (3) | 0.075 (3) | −0.013 (2) | 0.009 (3) | 0.007 (2) |
C20 | 0.070 (3) | 0.054 (3) | 0.060 (2) | −0.007 (2) | −0.002 (2) | 0.006 (2) |
C21 | 0.0427 (19) | 0.048 (2) | 0.045 (2) | 0.0021 (17) | 0.0044 (16) | 0.0031 (17) |
C22 | 0.052 (2) | 0.071 (3) | 0.060 (2) | −0.002 (2) | 0.0046 (19) | −0.009 (2) |
C23 | 0.063 (3) | 0.085 (3) | 0.072 (3) | −0.017 (2) | −0.001 (2) | −0.018 (3) |
C24 | 0.084 (3) | 0.081 (3) | 0.064 (3) | −0.002 (3) | 0.003 (3) | −0.026 (2) |
C25 | 0.071 (3) | 0.084 (3) | 0.067 (3) | 0.005 (3) | 0.015 (2) | −0.021 (3) |
C26 | 0.050 (2) | 0.060 (2) | 0.058 (2) | 0.0020 (19) | 0.0057 (18) | −0.004 (2) |
C27 | 0.0435 (19) | 0.045 (2) | 0.048 (2) | 0.0048 (17) | 0.0069 (17) | 0.0022 (18) |
C28 | 0.058 (2) | 0.068 (3) | 0.053 (2) | 0.015 (2) | 0.0127 (19) | 0.002 (2) |
C29 | 0.065 (3) | 0.075 (3) | 0.074 (3) | 0.023 (2) | 0.001 (2) | 0.007 (2) |
C30 | 0.067 (3) | 0.076 (3) | 0.097 (4) | 0.027 (2) | 0.013 (3) | −0.005 (3) |
C31 | 0.071 (3) | 0.092 (3) | 0.070 (3) | 0.023 (3) | 0.024 (2) | −0.005 (3) |
C32 | 0.057 (2) | 0.058 (2) | 0.058 (2) | 0.006 (2) | 0.0160 (19) | 0.011 (2) |
P1—C27 | 1.783 (3) | C15—C20 | 1.376 (4) |
P1—C21 | 1.783 (3) | C15—C16 | 1.385 (4) |
P1—C9 | 1.785 (3) | C16—C17 | 1.375 (4) |
P1—C15 | 1.786 (3) | C16—H16A | 0.9300 |
O1—C7 | 1.318 (5) | C17—C18 | 1.361 (5) |
O1—H1A | 1.00 (4) | C17—H17A | 0.9300 |
O2—C7 | 1.206 (5) | C18—C19 | 1.375 (5) |
O3—C2 | 1.310 (4) | C18—H18A | 0.9300 |
O4—C8 | 1.209 (4) | C19—C20 | 1.368 (5) |
O5—C8 | 1.315 (5) | C19—H19A | 0.9300 |
O5—H5A | 0.94 (4) | C20—H20A | 0.9300 |
C1—C6 | 1.375 (5) | C21—C26 | 1.372 (4) |
C1—C2 | 1.395 (5) | C21—C22 | 1.395 (4) |
C1—C7 | 1.482 (6) | C22—C23 | 1.368 (5) |
C2—C3 | 1.414 (5) | C22—H22A | 0.9300 |
C3—C4 | 1.382 (5) | C23—C24 | 1.370 (5) |
C3—C8 | 1.463 (5) | C23—H23A | 0.9300 |
C4—C5 | 1.369 (6) | C24—C25 | 1.357 (5) |
C4—H4 | 0.9300 | C24—H24A | 0.9300 |
C5—C6 | 1.371 (6) | C25—C26 | 1.377 (5) |
C5—H5 | 0.9300 | C25—H25A | 0.9300 |
C6—H6 | 0.9300 | C26—H26A | 0.9300 |
C9—C10 | 1.383 (5) | C27—C28 | 1.376 (4) |
C9—C14 | 1.392 (4) | C27—C32 | 1.379 (4) |
C10—C11 | 1.369 (5) | C28—C29 | 1.374 (5) |
C10—H10A | 0.9300 | C28—H28A | 0.9300 |
C11—C12 | 1.363 (5) | C29—C30 | 1.367 (5) |
C11—H11A | 0.9300 | C29—H29A | 0.9300 |
C12—C13 | 1.363 (5) | C30—C31 | 1.363 (5) |
C12—H12A | 0.9300 | C30—H30A | 0.9300 |
C13—C14 | 1.369 (5) | C31—C32 | 1.374 (5) |
C13—H13A | 0.9300 | C31—H31A | 0.9300 |
C14—H14A | 0.9300 | C32—H32A | 0.9300 |
C27—P1—C21 | 109.41 (16) | C16—C15—P1 | 120.3 (3) |
C27—P1—C9 | 108.05 (16) | C17—C16—C15 | 120.1 (3) |
C21—P1—C9 | 112.90 (16) | C17—C16—H16A | 120.0 |
C27—P1—C15 | 109.27 (16) | C15—C16—H16A | 120.0 |
C21—P1—C15 | 108.40 (15) | C18—C17—C16 | 120.2 (4) |
C9—P1—C15 | 108.77 (16) | C18—C17—H17A | 119.9 |
C7—O1—H1A | 108 (2) | C16—C17—H17A | 119.9 |
C8—O5—H5A | 109 (2) | C17—C18—C19 | 120.1 (4) |
C6—C1—C2 | 119.6 (4) | C17—C18—H18A | 120.0 |
C6—C1—C7 | 118.9 (4) | C19—C18—H18A | 120.0 |
C2—C1—C7 | 121.4 (4) | C20—C19—C18 | 120.1 (4) |
O3—C2—C1 | 120.9 (3) | C20—C19—H19A | 120.0 |
O3—C2—C3 | 120.1 (3) | C18—C19—H19A | 120.0 |
C1—C2—C3 | 119.0 (4) | C19—C20—C15 | 120.4 (4) |
C4—C3—C2 | 118.9 (4) | C19—C20—H20A | 119.8 |
C4—C3—C8 | 119.7 (4) | C15—C20—H20A | 119.8 |
C2—C3—C8 | 121.5 (4) | C26—C21—C22 | 119.5 (3) |
C5—C4—C3 | 121.8 (4) | C26—C21—P1 | 120.4 (3) |
C5—C4—H4 | 119.1 | C22—C21—P1 | 119.8 (3) |
C3—C4—H4 | 119.1 | C23—C22—C21 | 119.5 (4) |
C4—C5—C6 | 118.9 (5) | C23—C22—H22A | 120.2 |
C4—C5—H5 | 120.5 | C21—C22—H22A | 120.2 |
C6—C5—H5 | 120.5 | C22—C23—C24 | 120.4 (4) |
C5—C6—C1 | 121.8 (4) | C22—C23—H23A | 119.8 |
C5—C6—H6 | 119.1 | C24—C23—H23A | 119.8 |
C1—C6—H6 | 119.1 | C25—C24—C23 | 120.3 (4) |
O2—C7—O1 | 121.0 (5) | C25—C24—H24A | 119.9 |
O2—C7—C1 | 122.7 (5) | C23—C24—H24A | 119.9 |
O1—C7—C1 | 116.3 (4) | C24—C25—C26 | 120.5 (4) |
O4—C8—O5 | 120.5 (4) | C24—C25—H25A | 119.8 |
O4—C8—C3 | 123.0 (5) | C26—C25—H25A | 119.8 |
O5—C8—C3 | 116.5 (4) | C21—C26—C25 | 119.8 (4) |
C10—C9—C14 | 118.6 (3) | C21—C26—H26A | 120.1 |
C10—C9—P1 | 120.6 (3) | C25—C26—H26A | 120.1 |
C14—C9—P1 | 120.8 (3) | C28—C27—C32 | 119.6 (3) |
C11—C10—C9 | 120.6 (4) | C28—C27—P1 | 119.3 (3) |
C11—C10—H10A | 119.7 | C32—C27—P1 | 120.9 (3) |
C9—C10—H10A | 119.7 | C29—C28—C27 | 120.3 (3) |
C12—C11—C10 | 120.1 (4) | C29—C28—H28A | 119.9 |
C12—C11—H11A | 119.9 | C27—C28—H28A | 119.9 |
C10—C11—H11A | 120.0 | C30—C29—C28 | 119.1 (4) |
C11—C12—C13 | 120.3 (4) | C30—C29—H29A | 120.4 |
C11—C12—H12A | 119.8 | C28—C29—H29A | 120.4 |
C13—C12—H12A | 119.8 | C31—C30—C29 | 121.6 (4) |
C12—C13—C14 | 120.5 (4) | C31—C30—H30A | 119.2 |
C12—C13—H13A | 119.8 | C29—C30—H30A | 119.2 |
C14—C13—H13A | 119.8 | C30—C31—C32 | 119.2 (4) |
C13—C14—C9 | 120.0 (3) | C30—C31—H31A | 120.4 |
C13—C14—H14A | 120.0 | C32—C31—H31A | 120.4 |
C9—C14—H14A | 120.0 | C31—C32—C27 | 120.1 (3) |
C20—C15—C16 | 119.1 (3) | C31—C32—H32A | 119.9 |
C20—C15—P1 | 120.4 (3) | C27—C32—H32A | 119.9 |
C6—C1—C2—O3 | 179.0 (4) | C27—P1—C15—C16 | 84.5 (3) |
C7—C1—C2—O3 | 1.8 (6) | C21—P1—C15—C16 | −156.3 (3) |
C6—C1—C2—C3 | −0.3 (6) | C9—P1—C15—C16 | −33.2 (3) |
C7—C1—C2—C3 | −177.5 (3) | C20—C15—C16—C17 | 0.7 (5) |
O3—C2—C3—C4 | −178.3 (3) | P1—C15—C16—C17 | −175.1 (3) |
C1—C2—C3—C4 | 1.1 (5) | C15—C16—C17—C18 | −0.7 (6) |
O3—C2—C3—C8 | 1.5 (5) | C16—C17—C18—C19 | 0.2 (6) |
C1—C2—C3—C8 | −179.2 (3) | C17—C18—C19—C20 | 0.4 (6) |
C2—C3—C4—C5 | −1.2 (6) | C18—C19—C20—C15 | −0.5 (6) |
C8—C3—C4—C5 | 179.0 (4) | C16—C15—C20—C19 | −0.1 (6) |
C3—C4—C5—C6 | 0.6 (8) | P1—C15—C20—C19 | 175.7 (3) |
C4—C5—C6—C1 | 0.3 (8) | C27—P1—C21—C26 | −149.3 (3) |
C2—C1—C6—C5 | −0.4 (7) | C9—P1—C21—C26 | −29.0 (3) |
C7—C1—C6—C5 | 176.9 (5) | C15—P1—C21—C26 | 91.6 (3) |
C6—C1—C7—O2 | −1.0 (7) | C27—P1—C21—C22 | 37.1 (3) |
C2—C1—C7—O2 | 176.3 (4) | C9—P1—C21—C22 | 157.4 (3) |
C6—C1—C7—O1 | −178.6 (4) | C15—P1—C21—C22 | −82.0 (3) |
C2—C1—C7—O1 | −1.3 (6) | C26—C21—C22—C23 | −0.1 (5) |
C4—C3—C8—O4 | 0.2 (6) | P1—C21—C22—C23 | 173.6 (3) |
C2—C3—C8—O4 | −179.6 (4) | C21—C22—C23—C24 | −0.1 (6) |
C4—C3—C8—O5 | 178.7 (4) | C22—C23—C24—C25 | −0.1 (7) |
C2—C3—C8—O5 | −1.1 (5) | C23—C24—C25—C26 | 0.4 (7) |
C27—P1—C9—C10 | 12.3 (3) | C22—C21—C26—C25 | 0.4 (5) |
C21—P1—C9—C10 | −108.8 (3) | P1—C21—C26—C25 | −173.2 (3) |
C15—P1—C9—C10 | 130.8 (3) | C24—C25—C26—C21 | −0.6 (6) |
C27—P1—C9—C14 | −167.2 (3) | C21—P1—C27—C28 | 42.9 (3) |
C21—P1—C9—C14 | 71.7 (3) | C9—P1—C27—C28 | −80.3 (3) |
C15—P1—C9—C14 | −48.7 (3) | C15—P1—C27—C28 | 161.5 (3) |
C14—C9—C10—C11 | 0.3 (5) | C21—P1—C27—C32 | −142.6 (3) |
P1—C9—C10—C11 | −179.2 (3) | C9—P1—C27—C32 | 94.2 (3) |
C9—C10—C11—C12 | −0.5 (6) | C15—P1—C27—C32 | −24.0 (3) |
C10—C11—C12—C13 | 0.5 (6) | C32—C27—C28—C29 | 0.4 (6) |
C11—C12—C13—C14 | −0.3 (6) | P1—C27—C28—C29 | 174.9 (3) |
C12—C13—C14—C9 | 0.1 (6) | C27—C28—C29—C30 | 0.8 (6) |
C10—C9—C14—C13 | −0.1 (5) | C28—C29—C30—C31 | −1.3 (7) |
P1—C9—C14—C13 | 179.4 (3) | C29—C30—C31—C32 | 0.5 (7) |
C27—P1—C15—C20 | −91.2 (3) | C30—C31—C32—C27 | 0.7 (6) |
C21—P1—C15—C20 | 28.0 (3) | C28—C27—C32—C31 | −1.2 (5) |
C9—P1—C15—C20 | 151.1 (3) | P1—C27—C32—C31 | −175.6 (3) |
Experimental details
(1) | (2) | |
Crystal data | ||
Chemical formula | C8H6O5·H2O | C24H20P·C8H5O5 |
Mr | 200.14 | 520.49 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 296 | 296 |
a, b, c (Å) | 3.6673 (6), 9.7608 (19), 11.8421 (15) | 15.287 (5), 8.027 (3), 22.144 (7) |
α, β, γ (°) | 97.647 (13), 90.219 (13), 100.537 (16) | 90, 101.15 (2), 90 |
V (Å3) | 412.87 (15) | 2665.7 (15) |
Z | 2 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.14 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 | 0.50 × 0.44 × 0.26 |
Data collection | ||
Diffractometer | Siemens P4 diffractometer | Siemens P4 diffractometer |
Absorption correction | Numerical Sheldrick (1997) | Numerical Sheldrick (1997) |
Tmin, Tmax | 0.95, 0.98 | 0.94, 0.97 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3409, 2400, 1574 | 6087, 4707, 2544 |
Rint | 0.059 | 0.031 |
(sin θ/λ)max (Å−1) | 0.703 | 0.595 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.186, 1.11 | 0.063, 0.137, 1.01 |
No. of reflections | 2400 | 4707 |
No. of parameters | 148 | 350 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.46 | < 0.001 |
Δρmax, Δρmin (e Å−3) | 0.39, −0.42 | 0.17, −0.24 |
Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXP-97 (Sheldrick, 1997).
O1—C7 | 1.318 (5) | O4—C8 | 1.209 (4) |
O2—C7 | 1.206 (5) | O5—C8 | 1.315 (5) |
O3—C2 | 1.310 (4) | ||
O2—C7—C1 | 122.7 (5) | O4—C8—C3 | 123.0 (5) |
O1—C7—C1 | 116.3 (4) | O5—C8—C3 | 116.5 (4) |