Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620005550/wp3006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006Val143cCuLTsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val143ccultsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006Val120CuLTsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val120cultsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006madiha48CuLTsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006madiha48cultsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val3hsup5.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620005550/wp3006sup9.pdf |
CCDC references: 1998087; 1998086; 1998085; 1998084
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for val143ccult, madiha48cult, val3h; olex2.solve (Bourhis et al., 2015) for val120cult. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C16H12O5 | F(000) = 592 |
Mr = 284.26 | Dx = 1.530 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 3.8224 (2) Å | Cell parameters from 2316 reflections |
b = 19.5339 (7) Å | θ = 3.5–70.7° |
c = 16.5360 (6) Å | µ = 0.96 mm−1 |
β = 91.604 (4)° | T = 100 K |
V = 1234.19 (9) Å3 | Block, clear light yellow |
Z = 4 | 0.1 × 0.1 × 0.02 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 2231 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 1797 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 5.1788 pixels mm-1 | θmax = 67.5°, θmin = 3.5° |
ω scans | h = −4→3 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020) | k = −22→23 |
Tmin = 0.837, Tmax = 1.000 | l = −19→18 |
6384 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0549P)2 + 0.331P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2231 reflections | Δρmax = 0.19 e Å−3 |
199 parameters | Δρmin = −0.19 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0710 (4) | 0.85831 (6) | 0.93733 (7) | 0.0267 (3) | |
C11 | 0.1867 (5) | 0.94300 (10) | 0.84057 (11) | 0.0282 (4) | |
C2 | 0.0486 (5) | 0.87404 (10) | 0.85750 (11) | 0.0264 (4) | |
O4 | −0.3429 (4) | 0.72141 (7) | 0.77398 (7) | 0.0335 (3) | |
C12 | 0.2584 (5) | 0.98879 (10) | 0.90363 (11) | 0.0304 (4) | |
H12 | 0.2224 | 0.9752 | 0.9579 | 0.036* | |
O5 | −0.4662 (4) | 0.63786 (7) | 0.89289 (9) | 0.0325 (3) | |
C3 | −0.0900 (5) | 0.82992 (10) | 0.80206 (11) | 0.0285 (4) | |
H3 | −0.1039 | 0.8431 | 0.7468 | 0.034* | |
C13 | 0.3821 (6) | 1.05406 (10) | 0.88758 (12) | 0.0334 (4) | |
H13 | 0.4304 | 1.0849 | 0.9309 | 0.040* | |
O6 | −0.4387 (4) | 0.61621 (7) | 1.05694 (8) | 0.0319 (3) | |
C4 | −0.2158 (5) | 0.76388 (10) | 0.82508 (11) | 0.0278 (4) | |
C14 | 0.4353 (6) | 1.07446 (10) | 0.80887 (12) | 0.0340 (4) | |
H14 | 0.5153 | 1.1195 | 0.7979 | 0.041* | |
C5 | −0.3225 (5) | 0.68599 (10) | 0.94187 (11) | 0.0272 (4) | |
O7 | −0.1352 (4) | 0.70700 (7) | 1.15476 (8) | 0.0350 (3) | |
C15 | 0.3709 (6) | 1.02868 (11) | 0.74573 (13) | 0.0382 (5) | |
H15 | 0.4123 | 1.0422 | 0.6917 | 0.046* | |
C6 | −0.3025 (5) | 0.67443 (10) | 1.02413 (11) | 0.0281 (4) | |
C16 | 0.2465 (6) | 0.96327 (10) | 0.76126 (12) | 0.0345 (5) | |
H16 | 0.2022 | 0.9323 | 0.7178 | 0.041* | |
C7 | −0.1492 (5) | 0.72355 (10) | 1.07638 (11) | 0.0284 (4) | |
C8 | −0.0253 (5) | 0.78535 (9) | 1.04667 (11) | 0.0269 (4) | |
H8 | 0.0746 | 0.8188 | 1.0820 | 0.032* | |
C9 | −0.0517 (5) | 0.79662 (9) | 0.96438 (11) | 0.0254 (4) | |
C10 | −0.1960 (5) | 0.74853 (10) | 0.90979 (11) | 0.0266 (4) | |
C17 | −0.2142 (6) | 0.55817 (10) | 1.04909 (12) | 0.0350 (5) | |
H17A | −0.1534 | 0.5527 | 0.9923 | 0.053* | |
H17B | −0.3351 | 0.5170 | 1.0674 | 0.053* | |
H17C | −0.0004 | 0.5651 | 1.0822 | 0.053* | |
H5 | −0.467 (6) | 0.6517 (12) | 0.8461 (15) | 0.025 (5)* | |
H7 | −0.022 (9) | 0.7401 (18) | 1.186 (2) | 0.063 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0373 (7) | 0.0201 (6) | 0.0226 (6) | −0.0005 (5) | −0.0007 (5) | 0.0004 (5) |
C11 | 0.0322 (10) | 0.0240 (9) | 0.0283 (9) | 0.0036 (7) | −0.0018 (7) | −0.0003 (7) |
C2 | 0.0324 (9) | 0.0238 (9) | 0.0230 (8) | 0.0049 (7) | 0.0004 (7) | 0.0004 (7) |
O4 | 0.0507 (9) | 0.0253 (7) | 0.0244 (6) | −0.0008 (6) | −0.0038 (6) | −0.0038 (5) |
C12 | 0.0373 (10) | 0.0260 (10) | 0.0279 (9) | 0.0026 (8) | 0.0004 (8) | 0.0008 (7) |
O5 | 0.0450 (8) | 0.0252 (7) | 0.0271 (7) | −0.0039 (6) | −0.0036 (6) | −0.0024 (5) |
C3 | 0.0394 (11) | 0.0250 (10) | 0.0210 (8) | 0.0030 (8) | −0.0003 (7) | 0.0001 (7) |
C13 | 0.0412 (11) | 0.0245 (10) | 0.0343 (10) | 0.0020 (8) | −0.0039 (8) | −0.0031 (8) |
O6 | 0.0380 (8) | 0.0235 (7) | 0.0345 (7) | −0.0017 (5) | 0.0044 (6) | 0.0025 (5) |
C4 | 0.0336 (10) | 0.0253 (9) | 0.0242 (9) | 0.0039 (7) | −0.0024 (7) | −0.0035 (7) |
C14 | 0.0413 (11) | 0.0216 (9) | 0.0391 (11) | −0.0009 (8) | −0.0013 (8) | 0.0036 (8) |
C5 | 0.0283 (9) | 0.0232 (9) | 0.0300 (9) | 0.0023 (7) | −0.0004 (7) | −0.0026 (7) |
O7 | 0.0510 (9) | 0.0302 (7) | 0.0237 (7) | −0.0048 (6) | −0.0020 (6) | 0.0028 (5) |
C15 | 0.0533 (13) | 0.0304 (11) | 0.0307 (10) | −0.0031 (9) | −0.0009 (9) | 0.0068 (8) |
C6 | 0.0313 (10) | 0.0225 (9) | 0.0305 (9) | 0.0016 (7) | 0.0029 (7) | 0.0007 (7) |
C16 | 0.0502 (12) | 0.0272 (10) | 0.0261 (9) | −0.0006 (8) | −0.0012 (8) | −0.0009 (7) |
C7 | 0.0331 (10) | 0.0271 (9) | 0.0249 (9) | 0.0035 (7) | 0.0007 (7) | 0.0003 (7) |
C8 | 0.0326 (10) | 0.0223 (9) | 0.0255 (9) | 0.0018 (7) | −0.0020 (7) | −0.0027 (7) |
C9 | 0.0292 (9) | 0.0212 (9) | 0.0259 (9) | 0.0037 (7) | 0.0008 (7) | −0.0002 (7) |
C10 | 0.0290 (9) | 0.0238 (9) | 0.0268 (9) | 0.0041 (7) | 0.0002 (7) | −0.0012 (7) |
C17 | 0.0471 (12) | 0.0223 (10) | 0.0357 (10) | 0.0011 (8) | 0.0027 (9) | 0.0013 (8) |
O1—C2 | 1.356 (2) | C14—H14 | 0.9500 |
O1—C9 | 1.373 (2) | C14—C15 | 1.391 (3) |
C11—C2 | 1.476 (3) | C5—C6 | 1.379 (3) |
C11—C12 | 1.395 (3) | C5—C10 | 1.422 (3) |
C11—C16 | 1.395 (3) | O7—C7 | 1.335 (2) |
C2—C3 | 1.355 (3) | O7—H7 | 0.93 (4) |
O4—C4 | 1.271 (2) | C15—H15 | 0.9500 |
C12—H12 | 0.9500 | C15—C16 | 1.390 (3) |
C12—C13 | 1.388 (3) | C6—C7 | 1.408 (3) |
O5—C5 | 1.348 (2) | C16—H16 | 0.9500 |
O5—H5 | 0.82 (3) | C7—C8 | 1.392 (3) |
C3—H3 | 0.9500 | C8—H8 | 0.9500 |
C3—C4 | 1.432 (3) | C8—C9 | 1.379 (3) |
C13—H13 | 0.9500 | C9—C10 | 1.405 (3) |
C13—C14 | 1.382 (3) | C17—H17A | 0.9800 |
O6—C6 | 1.369 (2) | C17—H17B | 0.9800 |
O6—C17 | 1.430 (2) | C17—H17C | 0.9800 |
C4—C10 | 1.432 (3) | ||
C2—O1—C9 | 120.22 (14) | C14—C15—H15 | 119.8 |
C12—C11—C2 | 120.47 (17) | C16—C15—C14 | 120.43 (19) |
C16—C11—C2 | 120.40 (17) | C16—C15—H15 | 119.8 |
C16—C11—C12 | 119.13 (18) | O6—C6—C5 | 121.03 (17) |
O1—C2—C11 | 112.22 (15) | O6—C6—C7 | 118.64 (16) |
C3—C2—O1 | 121.83 (17) | C5—C6—C7 | 120.31 (18) |
C3—C2—C11 | 125.95 (17) | C11—C16—H16 | 120.0 |
C11—C12—H12 | 119.8 | C15—C16—C11 | 120.04 (18) |
C13—C12—C11 | 120.46 (18) | C15—C16—H16 | 120.0 |
C13—C12—H12 | 119.8 | O7—C7—C6 | 115.80 (17) |
C5—O5—H5 | 109.1 (16) | O7—C7—C8 | 123.23 (17) |
C2—C3—H3 | 119.3 | C8—C7—C6 | 120.96 (17) |
C2—C3—C4 | 121.40 (17) | C7—C8—H8 | 121.0 |
C4—C3—H3 | 119.3 | C9—C8—C7 | 118.07 (17) |
C12—C13—H13 | 119.8 | C9—C8—H8 | 121.0 |
C14—C13—C12 | 120.33 (18) | O1—C9—C8 | 116.44 (16) |
C14—C13—H13 | 119.8 | O1—C9—C10 | 120.62 (16) |
C6—O6—C17 | 112.76 (15) | C8—C9—C10 | 122.94 (17) |
O4—C4—C3 | 122.42 (17) | C5—C10—C4 | 122.36 (17) |
O4—C4—C10 | 121.50 (18) | C9—C10—C4 | 119.83 (17) |
C3—C4—C10 | 116.07 (16) | C9—C10—C5 | 117.80 (16) |
C13—C14—H14 | 120.2 | O6—C17—H17A | 109.5 |
C13—C14—C15 | 119.60 (19) | O6—C17—H17B | 109.5 |
C15—C14—H14 | 120.2 | O6—C17—H17C | 109.5 |
O5—C5—C6 | 119.28 (17) | H17A—C17—H17B | 109.5 |
O5—C5—C10 | 120.82 (16) | H17A—C17—H17C | 109.5 |
C6—C5—C10 | 119.90 (17) | H17B—C17—H17C | 109.5 |
C7—O7—H7 | 112 (2) | ||
O1—C2—C3—C4 | −0.8 (3) | C13—C14—C15—C16 | 1.4 (3) |
O1—C9—C10—C4 | 0.0 (3) | O6—C6—C7—O7 | 3.2 (3) |
O1—C9—C10—C5 | −179.20 (16) | O6—C6—C7—C8 | −176.22 (17) |
C11—C2—C3—C4 | 179.81 (18) | C14—C15—C16—C11 | −0.3 (3) |
C11—C12—C13—C14 | 0.1 (3) | C5—C6—C7—O7 | −178.60 (18) |
C2—O1—C9—C8 | −178.71 (16) | C5—C6—C7—C8 | 2.0 (3) |
C2—O1—C9—C10 | 1.2 (3) | O7—C7—C8—C9 | 179.61 (18) |
C2—C11—C12—C13 | −178.80 (18) | C6—C5—C10—C4 | −178.83 (19) |
C2—C11—C16—C15 | 178.91 (19) | C6—C5—C10—C9 | 0.3 (3) |
C2—C3—C4—O4 | −179.13 (19) | C6—C7—C8—C9 | −1.1 (3) |
C2—C3—C4—C10 | 1.9 (3) | C16—C11—C2—O1 | 167.96 (18) |
O4—C4—C10—C5 | −1.3 (3) | C16—C11—C2—C3 | −12.6 (3) |
O4—C4—C10—C9 | 179.58 (17) | C16—C11—C12—C13 | 1.1 (3) |
C12—C11—C2—O1 | −12.2 (3) | C7—C8—C9—O1 | 179.58 (16) |
C12—C11—C2—C3 | 167.2 (2) | C7—C8—C9—C10 | −0.3 (3) |
C12—C11—C16—C15 | −1.0 (3) | C8—C9—C10—C4 | 179.82 (18) |
C12—C13—C14—C15 | −1.3 (3) | C8—C9—C10—C5 | 0.7 (3) |
O5—C5—C6—O6 | −2.7 (3) | C9—O1—C2—C11 | 178.71 (15) |
O5—C5—C6—C7 | 179.13 (17) | C9—O1—C2—C3 | −0.7 (3) |
O5—C5—C10—C4 | 0.4 (3) | C10—C5—C6—O6 | 176.59 (16) |
O5—C5—C10—C9 | 179.55 (17) | C10—C5—C6—C7 | −1.6 (3) |
C3—C4—C10—C5 | 177.72 (17) | C17—O6—C6—C5 | 79.6 (2) |
C3—C4—C10—C9 | −1.4 (3) | C17—O6—C6—C7 | −102.1 (2) |
C16H12O5 | F(000) = 592 |
Mr = 284.26 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 9.78509 (13) Å | Cell parameters from 4050 reflections |
b = 15.8032 (2) Å | θ = 4.5–72.5° |
c = 8.33104 (11) Å | µ = 0.92 mm−1 |
β = 91.3453 (11)° | T = 100 K |
V = 1287.92 (3) Å3 | Needle, clear whiteish yellow |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 2329 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2073 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.017 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 68.0°, θmin = 4.5° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO: Rigaku OD, 2020) | k = −15→18 |
Tmin = 0.764, Tmax = 1.000 | l = −9→9 |
7020 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.416P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.20 e Å−3 |
2329 reflections | Δρmin = −0.17 e Å−3 |
200 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0018 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.35638 (8) | 0.36946 (5) | 0.31509 (9) | 0.0179 (2) | |
C2 | 0.23257 (11) | 0.40587 (7) | 0.28256 (13) | 0.0170 (2) | |
C3 | 0.17172 (11) | 0.45781 (7) | 0.38872 (14) | 0.0194 (3) | |
H3 | 0.0841 | 0.4806 | 0.3628 | 0.023* | |
O4 | 0.18595 (8) | 0.52927 (5) | 0.63906 (10) | 0.0229 (2) | |
C4 | 0.23687 (11) | 0.47912 (7) | 0.53970 (13) | 0.0180 (2) | |
O5 | 0.39369 (9) | 0.50619 (5) | 0.82813 (9) | 0.0214 (2) | |
H5 | 0.309 (2) | 0.5233 (13) | 0.782 (2) | 0.064 (6)* | |
C5 | 0.44147 (12) | 0.45137 (7) | 0.71706 (13) | 0.0174 (2) | |
O6 | 0.63767 (9) | 0.41813 (6) | 0.88626 (10) | 0.0242 (2) | |
H6 | 0.599 (2) | 0.4507 (12) | 0.952 (2) | 0.054 (6)* | |
C6 | 0.56201 (12) | 0.40888 (7) | 0.74836 (13) | 0.0188 (2) | |
O7 | 0.73099 (9) | 0.31461 (5) | 0.67570 (10) | 0.0269 (2) | |
C7 | 0.61241 (11) | 0.35288 (7) | 0.63173 (14) | 0.0197 (3) | |
C8 | 0.54327 (12) | 0.34008 (7) | 0.48629 (14) | 0.0193 (3) | |
H8 | 0.5783 | 0.3029 | 0.4075 | 0.023* | |
C9 | 0.42139 (11) | 0.38330 (7) | 0.45978 (13) | 0.0166 (2) | |
C10 | 0.36711 (11) | 0.43830 (7) | 0.57208 (13) | 0.0168 (2) | |
C11 | 0.18037 (12) | 0.38185 (7) | 0.12189 (13) | 0.0176 (2) | |
C12 | 0.26478 (12) | 0.33922 (7) | 0.01501 (14) | 0.0205 (3) | |
H12 | 0.3553 | 0.3242 | 0.0475 | 0.025* | |
C13 | 0.21661 (13) | 0.31889 (7) | −0.13807 (14) | 0.0229 (3) | |
H13 | 0.2741 | 0.2897 | −0.2098 | 0.027* | |
C14 | 0.08494 (13) | 0.34091 (8) | −0.18687 (14) | 0.0237 (3) | |
H14 | 0.0529 | 0.3276 | −0.2924 | 0.028* | |
C15 | −0.00004 (12) | 0.38244 (7) | −0.08137 (14) | 0.0226 (3) | |
H15 | −0.0906 | 0.3970 | −0.1144 | 0.027* | |
C16 | 0.04708 (12) | 0.40260 (7) | 0.07203 (14) | 0.0197 (3) | |
H16 | −0.0116 | 0.4308 | 0.1439 | 0.024* | |
C17 | 0.79121 (14) | 0.25907 (9) | 0.56115 (18) | 0.0372 (4) | |
H17A | 0.8735 | 0.2331 | 0.6089 | 0.056* | |
H17B | 0.8157 | 0.2914 | 0.4657 | 0.056* | |
H17C | 0.7256 | 0.2147 | 0.5306 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0157 (4) | 0.0207 (4) | 0.0171 (4) | 0.0019 (3) | −0.0052 (3) | −0.0025 (3) |
C2 | 0.0144 (5) | 0.0175 (6) | 0.0190 (6) | −0.0009 (4) | −0.0035 (4) | 0.0027 (4) |
C3 | 0.0151 (5) | 0.0232 (6) | 0.0195 (6) | 0.0016 (4) | −0.0038 (4) | 0.0014 (4) |
O4 | 0.0199 (4) | 0.0288 (5) | 0.0198 (4) | 0.0054 (3) | −0.0023 (3) | −0.0048 (3) |
C4 | 0.0167 (5) | 0.0197 (6) | 0.0177 (6) | 0.0001 (4) | −0.0003 (4) | 0.0011 (4) |
O5 | 0.0206 (4) | 0.0270 (5) | 0.0163 (4) | 0.0054 (3) | −0.0041 (3) | −0.0052 (3) |
C5 | 0.0186 (6) | 0.0177 (5) | 0.0157 (5) | −0.0006 (4) | −0.0008 (4) | −0.0006 (4) |
O6 | 0.0244 (5) | 0.0295 (5) | 0.0181 (4) | 0.0082 (4) | −0.0097 (3) | −0.0062 (4) |
C6 | 0.0198 (6) | 0.0201 (6) | 0.0163 (5) | −0.0003 (4) | −0.0056 (4) | −0.0007 (4) |
O7 | 0.0241 (5) | 0.0287 (5) | 0.0272 (5) | 0.0123 (4) | −0.0128 (4) | −0.0103 (4) |
C7 | 0.0167 (6) | 0.0186 (6) | 0.0235 (6) | 0.0027 (4) | −0.0054 (4) | −0.0003 (4) |
C8 | 0.0191 (6) | 0.0190 (6) | 0.0196 (6) | 0.0019 (4) | −0.0029 (4) | −0.0039 (4) |
C9 | 0.0168 (5) | 0.0177 (5) | 0.0152 (5) | −0.0026 (4) | −0.0042 (4) | 0.0001 (4) |
C10 | 0.0159 (5) | 0.0170 (5) | 0.0173 (5) | −0.0010 (4) | −0.0020 (4) | 0.0015 (4) |
C11 | 0.0197 (6) | 0.0154 (5) | 0.0175 (6) | −0.0033 (4) | −0.0040 (4) | 0.0028 (4) |
C12 | 0.0213 (6) | 0.0193 (6) | 0.0208 (6) | 0.0004 (4) | −0.0038 (4) | 0.0014 (4) |
C13 | 0.0299 (7) | 0.0202 (6) | 0.0185 (6) | −0.0015 (5) | −0.0012 (5) | −0.0006 (4) |
C14 | 0.0313 (7) | 0.0220 (6) | 0.0175 (6) | −0.0080 (5) | −0.0080 (5) | 0.0021 (4) |
C15 | 0.0212 (6) | 0.0226 (6) | 0.0237 (6) | −0.0043 (5) | −0.0074 (5) | 0.0054 (5) |
C16 | 0.0188 (6) | 0.0198 (6) | 0.0203 (6) | −0.0028 (4) | −0.0033 (4) | 0.0019 (4) |
C17 | 0.0297 (7) | 0.0383 (8) | 0.0429 (8) | 0.0179 (6) | −0.0170 (6) | −0.0226 (6) |
O1—C2 | 1.3626 (13) | O7—C7 | 1.3514 (14) |
O1—C9 | 1.3674 (13) | O7—C17 | 1.4334 (15) |
C2—C3 | 1.3547 (16) | C7—C8 | 1.3885 (16) |
C2—C11 | 1.4713 (15) | C8—C9 | 1.3876 (16) |
C3—C4 | 1.4367 (16) | C9—C10 | 1.3914 (16) |
O4—C4 | 1.2573 (14) | C11—C12 | 1.4012 (16) |
C4—C10 | 1.4480 (15) | C11—C16 | 1.3984 (16) |
O5—C5 | 1.3586 (14) | C12—C13 | 1.3869 (17) |
C5—C6 | 1.3768 (16) | C13—C14 | 1.3863 (18) |
C5—C10 | 1.4105 (16) | C14—C15 | 1.3889 (18) |
O6—C6 | 1.3599 (13) | C15—C16 | 1.3856 (16) |
C6—C7 | 1.4118 (16) | ||
C2—O1—C9 | 120.06 (9) | C8—C7—C6 | 121.40 (10) |
O1—C2—C11 | 111.10 (9) | C9—C8—C7 | 117.80 (10) |
C3—C2—O1 | 121.90 (10) | O1—C9—C8 | 116.22 (10) |
C3—C2—C11 | 126.99 (10) | O1—C9—C10 | 121.04 (10) |
C2—C3—C4 | 121.38 (10) | C8—C9—C10 | 122.73 (10) |
C3—C4—C10 | 115.42 (10) | C5—C10—C4 | 121.89 (10) |
O4—C4—C3 | 123.33 (10) | C9—C10—C4 | 120.08 (10) |
O4—C4—C10 | 121.25 (10) | C9—C10—C5 | 118.02 (10) |
O5—C5—C6 | 119.27 (10) | C12—C11—C2 | 120.33 (10) |
O5—C5—C10 | 119.85 (10) | C16—C11—C2 | 120.74 (10) |
C6—C5—C10 | 120.88 (10) | C16—C11—C12 | 118.92 (10) |
C5—C6—C7 | 119.13 (10) | C13—C12—C11 | 120.20 (11) |
O6—C6—C5 | 123.68 (10) | C14—C13—C12 | 120.33 (11) |
O6—C6—C7 | 117.18 (10) | C13—C14—C15 | 119.94 (11) |
C7—O7—C17 | 117.21 (9) | C16—C15—C14 | 120.08 (11) |
O7—C7—C6 | 113.92 (10) | C15—C16—C11 | 120.52 (11) |
O7—C7—C8 | 124.68 (10) | ||
O1—C2—C3—C4 | 1.84 (17) | O6—C6—C7—O7 | 0.79 (15) |
O1—C2—C11—C12 | −10.02 (14) | O6—C6—C7—C8 | −179.17 (10) |
O1—C2—C11—C16 | 171.33 (10) | C6—C5—C10—C4 | 176.98 (10) |
O1—C9—C10—C4 | 2.72 (16) | C6—C5—C10—C9 | −1.99 (16) |
O1—C9—C10—C5 | −178.30 (10) | C6—C7—C8—C9 | −0.92 (17) |
C2—O1—C9—C8 | 176.54 (9) | O7—C7—C8—C9 | 179.13 (11) |
C2—O1—C9—C10 | −3.85 (15) | C7—C8—C9—O1 | 179.74 (10) |
C2—C3—C4—O4 | 177.53 (11) | C7—C8—C9—C10 | 0.13 (17) |
C2—C3—C4—C10 | −2.79 (16) | C8—C9—C10—C4 | −177.69 (10) |
C2—C11—C12—C13 | −178.07 (10) | C8—C9—C10—C5 | 1.29 (17) |
C2—C11—C16—C15 | 177.74 (10) | C9—O1—C2—C3 | 1.57 (16) |
C3—C2—C11—C12 | 169.12 (11) | C9—O1—C2—C11 | −179.25 (9) |
C3—C2—C11—C16 | −9.54 (18) | C10—C5—C6—O6 | −179.38 (10) |
C3—C4—C10—C5 | −178.39 (10) | C10—C5—C6—C7 | 1.25 (17) |
C3—C4—C10—C9 | 0.55 (16) | C11—C2—C3—C4 | −177.21 (11) |
O4—C4—C10—C5 | 1.29 (17) | C11—C12—C13—C14 | 0.33 (17) |
O4—C4—C10—C9 | −179.76 (10) | C12—C11—C16—C15 | −0.93 (17) |
O5—C5—C6—O6 | 0.27 (17) | C12—C13—C14—C15 | −0.95 (18) |
O5—C5—C6—C7 | −179.10 (10) | C13—C14—C15—C16 | 0.62 (18) |
O5—C5—C10—C4 | −2.67 (17) | C14—C15—C16—C11 | 0.32 (17) |
O5—C5—C10—C9 | 178.36 (10) | C16—C11—C12—C13 | 0.60 (17) |
C5—C6—C7—O7 | −179.80 (10) | C17—O7—C7—C6 | −177.82 (11) |
C5—C6—C7—C8 | 0.24 (18) | C17—O7—C7—C8 | 2.14 (18) |
C16H12O5·H2O | Dx = 1.436 Mg m−3 |
Mr = 302.27 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 3063 reflections |
a = 4.64835 (6) Å | θ = 5.9–75.5° |
b = 16.4123 (2) Å | µ = 0.94 mm−1 |
c = 18.3290 (3) Å | T = 100 K |
V = 1398.32 (3) Å3 | Block, yellow |
Z = 4 | 0.3 × 0.3 × 0.15 mm |
F(000) = 632 |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 2486 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2433 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.011 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 67.5°, θmin = 7.2° |
ω scans | h = −3→5 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020) | k = −19→13 |
Tmin = 0.884, Tmax = 1.000 | l = −21→21 |
3792 measured reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.038P)2 + 0.130P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.022 | (Δ/σ)max < 0.001 |
wR(F2) = 0.059 | Δρmax = 0.14 e Å−3 |
S = 1.03 | Δρmin = −0.13 e Å−3 |
2486 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
217 parameters | Extinction coefficient: 0.0038 (5) |
0 restraints | Absolute structure: Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Hydrogen site location: mixed | Absolute structure parameter: 0.05 (6) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5540 (2) | 0.57179 (6) | 0.22376 (5) | 0.0159 (2) | |
C2 | 0.6132 (3) | 0.53999 (9) | 0.15689 (8) | 0.0158 (3) | |
C3 | 0.4816 (3) | 0.47174 (9) | 0.13186 (8) | 0.0170 (3) | |
H3 | 0.5327 | 0.4508 | 0.0853 | 0.020* | |
O4 | 0.1384 (2) | 0.36789 (6) | 0.15132 (6) | 0.0203 (3) | |
C4 | 0.2671 (3) | 0.43068 (9) | 0.17412 (8) | 0.0163 (3) | |
O5 | −0.1549 (2) | 0.36529 (7) | 0.27217 (6) | 0.0213 (3) | |
H5 | −0.086 (6) | 0.3513 (17) | 0.2306 (16) | 0.056 (8)* | |
C5 | −0.0049 (3) | 0.43234 (9) | 0.29236 (8) | 0.0168 (3) | |
C6 | −0.0574 (3) | 0.46767 (10) | 0.35926 (8) | 0.0178 (3) | |
H6 | −0.1968 | 0.4448 | 0.3912 | 0.021* | |
O7 | 0.0424 (3) | 0.56936 (7) | 0.44646 (6) | 0.0212 (3) | |
H7 | 0.163 (5) | 0.6117 (15) | 0.4551 (13) | 0.039 (6)* | |
C7 | 0.0955 (3) | 0.53744 (9) | 0.38004 (8) | 0.0170 (3) | |
O8 | 0.4543 (2) | 0.63908 (6) | 0.35711 (6) | 0.0189 (2) | |
C8 | 0.3008 (3) | 0.57230 (9) | 0.33407 (8) | 0.0162 (3) | |
C9 | 0.3508 (3) | 0.53563 (9) | 0.26700 (8) | 0.0148 (3) | |
C10 | 0.2027 (3) | 0.46562 (9) | 0.24440 (8) | 0.0153 (3) | |
C11 | 0.8294 (3) | 0.58814 (9) | 0.11764 (8) | 0.0161 (3) | |
C12 | 0.9489 (3) | 0.65811 (10) | 0.14900 (8) | 0.0193 (3) | |
H12 | 0.8885 | 0.6750 | 0.1962 | 0.023* | |
C13 | 1.1543 (3) | 0.70295 (10) | 0.11190 (9) | 0.0217 (3) | |
H13 | 1.2354 | 0.7501 | 0.1339 | 0.026* | |
C14 | 1.2420 (3) | 0.67930 (10) | 0.04282 (9) | 0.0217 (3) | |
H14 | 1.3842 | 0.7099 | 0.0176 | 0.026* | |
C15 | 1.1213 (3) | 0.61064 (10) | 0.01052 (9) | 0.0214 (3) | |
H15 | 1.1788 | 0.5951 | −0.0372 | 0.026* | |
C16 | 0.9188 (3) | 0.56505 (10) | 0.04729 (8) | 0.0193 (3) | |
H16 | 0.8394 | 0.5179 | 0.0250 | 0.023* | |
C17 | 0.3416 (4) | 0.71412 (10) | 0.32867 (10) | 0.0273 (4) | |
H17A | 0.3639 | 0.7149 | 0.2755 | 0.041* | |
H17B | 0.4468 | 0.7601 | 0.3500 | 0.041* | |
H17C | 0.1372 | 0.7186 | 0.3411 | 0.041* | |
O1W | 0.2807 (3) | 0.70168 (7) | 0.51350 (6) | 0.0214 (3) | |
H1WA | 0.430 (7) | 0.7262 (16) | 0.5025 (16) | 0.055 (8)* | |
H1WB | 0.312 (5) | 0.6794 (13) | 0.5572 (14) | 0.037 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0176 (5) | 0.0176 (5) | 0.0125 (5) | −0.0004 (4) | 0.0014 (4) | −0.0007 (4) |
C2 | 0.0152 (7) | 0.0197 (7) | 0.0127 (7) | 0.0042 (6) | −0.0022 (6) | −0.0008 (6) |
C3 | 0.0183 (7) | 0.0190 (7) | 0.0136 (7) | 0.0022 (6) | −0.0003 (6) | −0.0009 (5) |
O4 | 0.0248 (5) | 0.0173 (5) | 0.0186 (5) | −0.0019 (5) | 0.0007 (4) | −0.0034 (4) |
C4 | 0.0176 (7) | 0.0148 (7) | 0.0164 (7) | 0.0045 (6) | −0.0029 (6) | 0.0005 (6) |
O5 | 0.0273 (6) | 0.0184 (5) | 0.0182 (6) | −0.0055 (5) | 0.0020 (5) | −0.0009 (4) |
C5 | 0.0187 (7) | 0.0143 (7) | 0.0174 (7) | 0.0021 (6) | −0.0024 (6) | 0.0016 (6) |
C6 | 0.0190 (6) | 0.0196 (7) | 0.0148 (7) | 0.0003 (6) | 0.0014 (6) | 0.0032 (5) |
O7 | 0.0279 (6) | 0.0227 (6) | 0.0129 (5) | −0.0025 (5) | 0.0040 (4) | −0.0021 (4) |
C7 | 0.0204 (7) | 0.0180 (7) | 0.0126 (7) | 0.0038 (6) | −0.0008 (6) | 0.0010 (6) |
O8 | 0.0232 (5) | 0.0170 (5) | 0.0167 (5) | −0.0013 (5) | −0.0025 (4) | −0.0015 (4) |
C8 | 0.0189 (7) | 0.0145 (7) | 0.0152 (7) | 0.0024 (6) | −0.0015 (6) | 0.0009 (6) |
C9 | 0.0144 (7) | 0.0151 (7) | 0.0149 (7) | 0.0020 (6) | −0.0008 (6) | 0.0035 (5) |
C10 | 0.0172 (7) | 0.0153 (7) | 0.0134 (7) | 0.0039 (6) | −0.0013 (6) | 0.0014 (5) |
C11 | 0.0142 (6) | 0.0181 (7) | 0.0158 (7) | 0.0039 (5) | −0.0021 (6) | 0.0016 (6) |
C12 | 0.0207 (7) | 0.0219 (7) | 0.0151 (7) | 0.0013 (6) | 0.0005 (6) | −0.0005 (6) |
C13 | 0.0215 (7) | 0.0202 (7) | 0.0235 (8) | −0.0015 (6) | −0.0016 (7) | 0.0004 (6) |
C14 | 0.0185 (7) | 0.0243 (8) | 0.0224 (8) | 0.0020 (6) | 0.0029 (6) | 0.0064 (6) |
C15 | 0.0222 (8) | 0.0256 (7) | 0.0163 (7) | 0.0049 (6) | 0.0037 (6) | 0.0006 (6) |
C16 | 0.0190 (7) | 0.0216 (7) | 0.0172 (7) | 0.0022 (6) | 0.0002 (6) | −0.0003 (6) |
C17 | 0.0395 (10) | 0.0160 (8) | 0.0265 (9) | −0.0011 (7) | −0.0059 (8) | 0.0001 (6) |
O1W | 0.0249 (6) | 0.0235 (6) | 0.0157 (6) | −0.0014 (5) | −0.0010 (5) | 0.0025 (5) |
O1—C2 | 1.3602 (18) | C8—C9 | 1.388 (2) |
O1—C9 | 1.3682 (18) | C9—C10 | 1.402 (2) |
C2—C3 | 1.356 (2) | C11—C12 | 1.399 (2) |
C2—C11 | 1.467 (2) | C11—C16 | 1.407 (2) |
C3—H3 | 0.9500 | C12—H12 | 0.9500 |
C3—C4 | 1.431 (2) | C12—C13 | 1.384 (2) |
O4—C4 | 1.2626 (19) | C13—H13 | 0.9500 |
C4—C10 | 1.442 (2) | C13—C14 | 1.386 (2) |
O5—H5 | 0.86 (3) | C14—H14 | 0.9500 |
O5—C5 | 1.3540 (19) | C14—C15 | 1.391 (2) |
C5—C6 | 1.378 (2) | C15—H15 | 0.9500 |
C5—C10 | 1.415 (2) | C15—C16 | 1.378 (2) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C6—C7 | 1.401 (2) | C17—H17A | 0.9800 |
O7—H7 | 0.91 (3) | C17—H17B | 0.9800 |
O7—C7 | 1.3481 (18) | C17—H17C | 0.9800 |
C7—C8 | 1.396 (2) | O1W—H1WA | 0.83 (3) |
O8—C8 | 1.3743 (19) | O1W—H1WB | 0.89 (3) |
O8—C17 | 1.4363 (19) | ||
C2—O1—C9 | 119.69 (12) | C5—C10—C4 | 122.89 (14) |
O1—C2—C11 | 111.96 (12) | C9—C10—C4 | 119.22 (14) |
C3—C2—O1 | 122.02 (14) | C9—C10—C5 | 117.89 (13) |
C3—C2—C11 | 126.01 (14) | C12—C11—C2 | 120.83 (14) |
C2—C3—H3 | 119.3 | C12—C11—C16 | 118.70 (14) |
C2—C3—C4 | 121.34 (14) | C16—C11—C2 | 120.47 (14) |
C4—C3—H3 | 119.3 | C11—C12—H12 | 119.7 |
C3—C4—C10 | 116.17 (14) | C13—C12—C11 | 120.56 (14) |
O4—C4—C3 | 122.36 (14) | C13—C12—H12 | 119.7 |
O4—C4—C10 | 121.47 (14) | C12—C13—H13 | 119.9 |
C5—O5—H5 | 105.6 (19) | C12—C13—C14 | 120.20 (15) |
O5—C5—C6 | 119.60 (14) | C14—C13—H13 | 119.9 |
O5—C5—C10 | 119.67 (13) | C13—C14—H14 | 120.1 |
C6—C5—C10 | 120.72 (14) | C13—C14—C15 | 119.80 (15) |
C5—C6—H6 | 120.1 | C15—C14—H14 | 120.1 |
C5—C6—C7 | 119.75 (14) | C14—C15—H15 | 119.8 |
C7—C6—H6 | 120.1 | C16—C15—C14 | 120.47 (15) |
C7—O7—H7 | 110.1 (16) | C16—C15—H15 | 119.8 |
O7—C7—C6 | 118.06 (13) | C11—C16—H16 | 119.9 |
O7—C7—C8 | 120.73 (14) | C15—C16—C11 | 120.25 (15) |
C8—C7—C6 | 121.20 (14) | C15—C16—H16 | 119.9 |
C8—O8—C17 | 112.52 (12) | O8—C17—H17A | 109.5 |
O8—C8—C7 | 119.77 (13) | O8—C17—H17B | 109.5 |
O8—C8—C9 | 122.06 (13) | O8—C17—H17C | 109.5 |
C9—C8—C7 | 118.12 (14) | H17A—C17—H17B | 109.5 |
O1—C9—C8 | 116.14 (13) | H17A—C17—H17C | 109.5 |
O1—C9—C10 | 121.54 (13) | H17B—C17—H17C | 109.5 |
C8—C9—C10 | 122.32 (14) | H1WA—O1W—H1WB | 106 (3) |
O1—C2—C3—C4 | 1.6 (2) | C6—C5—C10—C9 | −0.4 (2) |
O1—C2—C11—C12 | −0.35 (19) | C6—C7—C8—O8 | −177.74 (13) |
O1—C2—C11—C16 | −179.84 (13) | C6—C7—C8—C9 | −0.3 (2) |
O1—C9—C10—C4 | 0.3 (2) | O7—C7—C8—O8 | 1.1 (2) |
O1—C9—C10—C5 | −179.72 (13) | O7—C7—C8—C9 | 178.54 (13) |
C2—O1—C9—C8 | −179.33 (12) | C7—C8—C9—O1 | −179.93 (12) |
C2—O1—C9—C10 | 0.6 (2) | C7—C8—C9—C10 | 0.1 (2) |
C2—C3—C4—O4 | 178.77 (14) | O8—C8—C9—O1 | −2.6 (2) |
C2—C3—C4—C10 | −0.5 (2) | O8—C8—C9—C10 | 177.47 (13) |
C2—C11—C12—C13 | 179.52 (14) | C8—C9—C10—C4 | −179.70 (14) |
C2—C11—C16—C15 | 179.78 (14) | C8—C9—C10—C5 | 0.2 (2) |
C3—C2—C11—C12 | 179.48 (15) | C9—O1—C2—C3 | −1.6 (2) |
C3—C2—C11—C16 | 0.0 (2) | C9—O1—C2—C11 | 178.23 (12) |
C3—C4—C10—C5 | 179.68 (13) | C10—C5—C6—C7 | 0.2 (2) |
C3—C4—C10—C9 | −0.37 (19) | C11—C2—C3—C4 | −178.24 (13) |
O4—C4—C10—C5 | 0.4 (2) | C11—C12—C13—C14 | 0.6 (2) |
O4—C4—C10—C9 | −179.69 (14) | C12—C11—C16—C15 | 0.3 (2) |
O5—C5—C6—C7 | −179.45 (13) | C12—C13—C14—C15 | 0.5 (2) |
O5—C5—C10—C4 | −0.8 (2) | C13—C14—C15—C16 | −1.2 (2) |
O5—C5—C10—C9 | 179.26 (13) | C14—C15—C16—C11 | 0.8 (2) |
C5—C6—C7—O7 | −178.71 (14) | C16—C11—C12—C13 | −1.0 (2) |
C5—C6—C7—C8 | 0.2 (2) | C17—O8—C8—C7 | −99.41 (17) |
C6—C5—C10—C4 | 179.55 (13) | C17—O8—C8—C9 | 83.26 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.86 (3) | 1.81 (3) | 2.6013 (15) | 153 (3) |
O7—H7···O8 | 0.91 (3) | 2.29 (2) | 2.7673 (16) | 112.2 (19) |
O7—H7···O1W | 0.91 (3) | 1.90 (2) | 2.7301 (16) | 151 (2) |
O1W—H1WA···O1Wi | 0.83 (3) | 2.04 (3) | 2.8570 (13) | 172 (3) |
O1W—H1WB···O4ii | 0.89 (3) | 1.91 (3) | 2.7976 (15) | 178 (2) |
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1/2, −y+1, z+1/2. |
C16H12O5·1.25H2O | F(000) = 642 |
Mr = 306.78 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 4.39382 (9) Å | Cell parameters from 4183 reflections |
b = 18.7848 (3) Å | θ = 3.5–74.3° |
c = 16.8308 (3) Å | µ = 0.97 mm−1 |
β = 96.5918 (19)° | T = 100 K |
V = 1379.98 (5) Å3 | Plate, yellow |
Z = 4 | 0.4 × 0.08 × 0.05 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | Rint = 0.019 |
ω scans | θmax = 67.5°, θmin = 7.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020) | h = −3→5 |
Tmin = 0.818, Tmax = 1.000 | k = −21→22 |
7256 measured reflections | l = −20→20 |
2416 independent reflections | 3 standard reflections every 30 min |
2173 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.643P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2416 reflections | Δρmax = 0.29 e Å−3 |
223 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.5558 (2) | 0.76190 (5) | 0.18290 (6) | 0.0235 (3) | |
O4 | 0.2880 (3) | 0.84255 (8) | 0.38900 (7) | 0.0502 (4) | |
O5 | −0.0181 (3) | 0.72740 (9) | 0.40586 (8) | 0.0547 (4) | |
H5 | 0.0171 | 0.7712 | 0.4110 | 0.082* | |
O7 | 0.0203 (4) | 0.54743 (7) | 0.21340 (9) | 0.0601 (5) | |
H7 | 0.0847 | 0.5393 | 0.1692 | 0.090* | |
O8 | 0.4021 (3) | 0.62888 (6) | 0.12845 (6) | 0.0360 (3) | |
C2 | 0.6428 (3) | 0.82849 (8) | 0.20820 (9) | 0.0257 (3) | |
C3 | 0.5591 (4) | 0.85584 (9) | 0.27672 (10) | 0.0324 (4) | |
H3 | 0.6278 | 0.9021 | 0.2931 | 0.039* | |
C4 | 0.3708 (4) | 0.81719 (9) | 0.32510 (9) | 0.0322 (4) | |
C5 | 0.0852 (4) | 0.70379 (10) | 0.33789 (10) | 0.0362 (4) | |
C6 | 0.0029 (4) | 0.63732 (11) | 0.30907 (11) | 0.0414 (5) | |
H6 | −0.1235 | 0.6078 | 0.3373 | 0.050* | |
C7 | 0.1051 (4) | 0.61308 (9) | 0.23829 (10) | 0.0380 (4) | |
C8 | 0.2905 (4) | 0.65540 (8) | 0.19546 (9) | 0.0284 (3) | |
C9 | 0.3729 (3) | 0.72211 (8) | 0.22582 (8) | 0.0230 (3) | |
C10 | 0.2746 (3) | 0.74783 (9) | 0.29687 (9) | 0.0281 (3) | |
C17 | 0.2384 (5) | 0.65378 (9) | 0.05454 (10) | 0.0372 (4) | |
H17A | 0.0199 | 0.6431 | 0.0540 | 0.056* | |
H17B | 0.3177 | 0.6299 | 0.0094 | 0.056* | |
H17C | 0.2665 | 0.7053 | 0.0500 | 0.056* | |
C11 | 0.8273 (3) | 0.86362 (8) | 0.15237 (11) | 0.0306 (4) | |
C12 | 0.8860 (4) | 0.82958 (9) | 0.08227 (11) | 0.0350 (4) | |
H12 | 0.8047 | 0.7834 | 0.0706 | 0.042* | |
C13 | 1.0614 (4) | 0.86210 (11) | 0.02931 (13) | 0.0453 (5) | |
H13 | 1.1004 | 0.8382 | −0.0182 | 0.054* | |
C14 | 1.1796 (4) | 0.92934 (12) | 0.04586 (15) | 0.0524 (6) | |
H14 | 1.3020 | 0.9516 | 0.0100 | 0.063* | |
C15 | 1.1187 (4) | 0.96427 (11) | 0.11507 (16) | 0.0554 (6) | |
H15 | 1.1974 | 1.0108 | 0.1259 | 0.066* | |
C16 | 0.9449 (4) | 0.93205 (9) | 0.16824 (13) | 0.0425 (5) | |
H16 | 0.9053 | 0.9563 | 0.2155 | 0.051* | |
O1W | 0.2844 (10) | 0.47744 (16) | 0.0807 (2) | 0.0736 (11) | 0.5 |
H1WA | 0.3395 | 0.4794 | 0.0328 | 0.110* | 0.5 |
H1WB | 0.2718 | 0.4321 | 0.0906 | 0.110* | 0.5 |
O2W | 0.9631 (8) | 0.48649 (13) | 0.07684 (15) | 0.0452 (7) | 0.5 |
H2WA | 1.0454 | 0.4953 | 0.0333 | 0.068* | 0.5 |
H2WB | 0.7786 | 0.4720 | 0.0602 | 0.068* | 0.5 |
O3W | 0.3848 (16) | 0.5034 (3) | −0.0616 (4) | 0.0568 (15) | 0.25 |
H3WA | 0.4666 | 0.4618 | −0.0670 | 0.085* | 0.25 |
H3WB | 0.2256 | 0.5042 | −0.0974 | 0.085* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0265 (5) | 0.0189 (5) | 0.0249 (5) | 0.0014 (4) | 0.0026 (4) | −0.0038 (4) |
O4 | 0.0599 (8) | 0.0635 (9) | 0.0253 (6) | 0.0337 (7) | −0.0040 (5) | −0.0164 (6) |
O5 | 0.0568 (8) | 0.0797 (10) | 0.0310 (7) | 0.0364 (8) | 0.0201 (6) | 0.0209 (7) |
O7 | 0.0895 (12) | 0.0323 (7) | 0.0521 (9) | −0.0260 (7) | −0.0197 (8) | 0.0205 (6) |
O8 | 0.0628 (8) | 0.0210 (5) | 0.0225 (6) | 0.0056 (5) | −0.0031 (5) | −0.0018 (4) |
C2 | 0.0205 (7) | 0.0195 (7) | 0.0347 (8) | 0.0045 (5) | −0.0068 (6) | −0.0034 (6) |
C3 | 0.0313 (8) | 0.0263 (8) | 0.0366 (9) | 0.0090 (6) | −0.0088 (6) | −0.0120 (6) |
C4 | 0.0320 (8) | 0.0401 (9) | 0.0224 (7) | 0.0180 (7) | −0.0060 (6) | −0.0083 (6) |
C5 | 0.0306 (8) | 0.0525 (11) | 0.0257 (8) | 0.0168 (7) | 0.0038 (6) | 0.0146 (7) |
C6 | 0.0338 (9) | 0.0520 (11) | 0.0383 (10) | 0.0034 (8) | 0.0028 (7) | 0.0253 (8) |
C7 | 0.0432 (9) | 0.0317 (9) | 0.0353 (9) | −0.0054 (7) | −0.0120 (7) | 0.0146 (7) |
C8 | 0.0381 (8) | 0.0234 (7) | 0.0219 (7) | 0.0003 (6) | −0.0039 (6) | 0.0029 (6) |
C9 | 0.0237 (7) | 0.0239 (7) | 0.0204 (7) | 0.0032 (5) | −0.0013 (5) | 0.0020 (6) |
C10 | 0.0256 (7) | 0.0372 (8) | 0.0203 (7) | 0.0117 (6) | −0.0023 (6) | 0.0013 (6) |
C17 | 0.0613 (11) | 0.0260 (8) | 0.0226 (8) | −0.0032 (7) | −0.0022 (7) | 0.0023 (6) |
C11 | 0.0190 (7) | 0.0250 (8) | 0.0454 (9) | 0.0036 (6) | −0.0064 (6) | 0.0043 (7) |
C12 | 0.0252 (8) | 0.0330 (9) | 0.0473 (10) | 0.0007 (6) | 0.0055 (7) | 0.0049 (7) |
C13 | 0.0276 (8) | 0.0525 (11) | 0.0565 (12) | 0.0022 (8) | 0.0074 (8) | 0.0178 (9) |
C14 | 0.0252 (8) | 0.0527 (12) | 0.0767 (15) | −0.0059 (8) | −0.0053 (9) | 0.0348 (11) |
C15 | 0.0375 (10) | 0.0358 (10) | 0.0860 (17) | −0.0124 (8) | −0.0219 (10) | 0.0247 (11) |
C16 | 0.0352 (9) | 0.0259 (8) | 0.0617 (12) | −0.0033 (7) | −0.0148 (8) | 0.0066 (8) |
O1W | 0.134 (4) | 0.0287 (15) | 0.062 (2) | −0.0152 (18) | 0.027 (2) | −0.0054 (13) |
O2W | 0.084 (2) | 0.0237 (12) | 0.0266 (12) | −0.0049 (12) | −0.0021 (12) | −0.0031 (9) |
O3W | 0.062 (4) | 0.042 (3) | 0.069 (4) | 0.010 (3) | 0.015 (3) | −0.010 (3) |
O1—C2 | 1.3619 (18) | C17—H17A | 0.9800 |
O1—C9 | 1.3637 (18) | C17—H17B | 0.9800 |
O4—C4 | 1.267 (2) | C17—H17C | 0.9800 |
O5—H5 | 0.8400 | C11—C12 | 1.392 (3) |
O5—C5 | 1.353 (2) | C11—C16 | 1.400 (2) |
O7—H7 | 0.8400 | C12—H12 | 0.9500 |
O7—C7 | 1.341 (2) | C12—C13 | 1.385 (3) |
O8—C8 | 1.374 (2) | C13—H13 | 0.9500 |
O8—C17 | 1.442 (2) | C13—C14 | 1.382 (3) |
C2—C3 | 1.351 (2) | C14—H14 | 0.9500 |
C2—C11 | 1.467 (2) | C14—C15 | 1.389 (4) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C3—C4 | 1.425 (3) | C15—C16 | 1.381 (3) |
C4—C10 | 1.434 (2) | C16—H16 | 0.9500 |
C5—C6 | 1.373 (3) | O1W—H1WA | 0.8699 |
C5—C10 | 1.409 (2) | O1W—H1WB | 0.8700 |
C6—H6 | 0.9500 | O2W—H2WA | 0.8691 |
C6—C7 | 1.397 (3) | O2W—H2WB | 0.8704 |
C7—C8 | 1.397 (2) | O3W—H3WA | 0.8701 |
C8—C9 | 1.386 (2) | O3W—H3WB | 0.8699 |
C9—C10 | 1.403 (2) | ||
C2—O1—C9 | 119.93 (12) | C9—C10—C4 | 119.18 (15) |
C5—O5—H5 | 109.5 | C9—C10—C5 | 118.18 (15) |
C7—O7—H7 | 109.5 | O8—C17—H17A | 109.5 |
C8—O8—C17 | 113.64 (13) | O8—C17—H17B | 109.5 |
O1—C2—C11 | 111.64 (13) | O8—C17—H17C | 109.5 |
C3—C2—O1 | 121.47 (15) | H17A—C17—H17B | 109.5 |
C3—C2—C11 | 126.89 (15) | H17A—C17—H17C | 109.5 |
C2—C3—H3 | 119.1 | H17B—C17—H17C | 109.5 |
C2—C3—C4 | 121.78 (15) | C12—C11—C2 | 120.42 (14) |
C4—C3—H3 | 119.1 | C12—C11—C16 | 118.90 (17) |
O4—C4—C3 | 122.38 (17) | C16—C11—C2 | 120.68 (17) |
O4—C4—C10 | 121.37 (17) | C11—C12—H12 | 119.5 |
C3—C4—C10 | 116.23 (14) | C13—C12—C11 | 120.91 (17) |
O5—C5—C6 | 119.77 (17) | C13—C12—H12 | 119.5 |
O5—C5—C10 | 119.75 (18) | C12—C13—H13 | 120.1 |
C6—C5—C10 | 120.48 (16) | C14—C13—C12 | 119.8 (2) |
C5—C6—H6 | 120.0 | C14—C13—H13 | 120.1 |
C5—C6—C7 | 120.03 (16) | C13—C14—H14 | 120.1 |
C7—C6—H6 | 120.0 | C13—C14—C15 | 119.77 (19) |
O7—C7—C6 | 117.47 (17) | C15—C14—H14 | 120.1 |
O7—C7—C8 | 121.31 (18) | C14—C15—H15 | 119.7 |
C8—C7—C6 | 121.22 (16) | C16—C15—C14 | 120.69 (19) |
O8—C8—C7 | 120.11 (14) | C16—C15—H15 | 119.7 |
O8—C8—C9 | 121.87 (14) | C11—C16—H16 | 120.1 |
C9—C8—C7 | 117.88 (15) | C15—C16—C11 | 119.9 (2) |
O1—C9—C8 | 116.44 (13) | C15—C16—H16 | 120.1 |
O1—C9—C10 | 121.37 (14) | H1WA—O1W—H1WB | 104.5 |
C8—C9—C10 | 122.19 (14) | H2WA—O2W—H2WB | 104.5 |
C5—C10—C4 | 122.63 (15) | H3WA—O3W—H3WB | 104.5 |
O1—C2—C3—C4 | −1.3 (2) | C3—C4—C10—C9 | 1.0 (2) |
O1—C2—C11—C12 | 1.85 (19) | C5—C6—C7—O7 | 179.31 (15) |
O1—C2—C11—C16 | −178.69 (13) | C5—C6—C7—C8 | −0.2 (3) |
O1—C9—C10—C4 | −0.5 (2) | C6—C5—C10—C4 | −179.03 (14) |
O1—C9—C10—C5 | 179.82 (12) | C6—C5—C10—C9 | 0.6 (2) |
O4—C4—C10—C5 | −0.2 (2) | C6—C7—C8—O8 | 176.35 (14) |
O4—C4—C10—C9 | −179.90 (14) | C6—C7—C8—C9 | 0.6 (2) |
O5—C5—C6—C7 | 179.02 (15) | C7—C8—C9—O1 | 179.55 (13) |
O5—C5—C10—C4 | 1.5 (2) | C7—C8—C9—C10 | −0.5 (2) |
O5—C5—C10—C9 | −178.85 (13) | C8—C9—C10—C4 | 179.52 (13) |
O7—C7—C8—O8 | −3.1 (2) | C8—C9—C10—C5 | −0.2 (2) |
O7—C7—C8—C9 | −178.83 (15) | C9—O1—C2—C3 | 1.94 (19) |
O8—C8—C9—O1 | 3.9 (2) | C9—O1—C2—C11 | −177.57 (11) |
O8—C8—C9—C10 | −176.09 (13) | C10—C5—C6—C7 | −0.5 (2) |
C2—O1—C9—C8 | 178.99 (12) | C17—O8—C8—C7 | 102.11 (17) |
C2—O1—C9—C10 | −1.01 (19) | C17—O8—C8—C9 | −82.35 (18) |
C2—C3—C4—O4 | −179.21 (14) | C11—C2—C3—C4 | 178.08 (13) |
C2—C3—C4—C10 | −0.2 (2) | C11—C12—C13—C14 | −0.2 (3) |
C2—C11—C12—C13 | −179.64 (15) | C12—C11—C16—C15 | −0.7 (2) |
C2—C11—C16—C15 | 179.88 (15) | C12—C13—C14—C15 | −0.8 (3) |
C3—C2—C11—C12 | −177.62 (15) | C13—C14—C15—C16 | 1.0 (3) |
C3—C2—C11—C16 | 1.8 (2) | C14—C15—C16—C11 | −0.3 (3) |
C3—C4—C10—C5 | −179.28 (14) | C16—C11—C12—C13 | 0.9 (2) |
Bond | 1 | 2 | 3a |
O1—C2 | 1.356 (2) | 1.3625 (13) | 1.3602 (18) |
O1—C9 | 1.373 (2) | 1.3674 (13) | 1.3682 (18) |
C4—O4 | 1.271 (2) | 1.2573 (14) | 1.2626 (19) |
C5—O5 | 1.348 (2) | 1.3586 (14) | 1.3540 (19) |
C6—O6 | 1.369 (2) | 1.3599 (13) | - |
C7—O7 | 1.335 (2) | 1.3514 (14) | 1.3481 (18) |
C8—O8 | - | - | 1.3743 (19) |
O—C17 | 1.430 (2) | 1.4334 (15) | 1.4363 (19) |
C2—C11 | 1.476 (3) | 1.4713 (15) | 1.467 (2) |
C2—C3 | 1.355 (3) | 1.3547 (16) | 1.356 (2) |
C3—C4 | 1.432 (3) | 1.4367 (16) | 1.431 (2) |
C4—C10 | 1.432 (3) | 1.4480 (15) | 1.442 (2) |
C5—C10 | 1.422 (3) | 1.4105 (16) | 1.415 (2) |
C5—C6 | 1.379 (3) | 1.3768 (16) | 1.378 (2) |
C6–C7 | 1.408 (3) | 1.4118 (16) | 1.401 (2) |
C7—C8 | 1.392 (3) | 1.3885 (16) | 1.396 (2) |
C8—C9 | 1.379 (3) | 1.3876 (16) | 1.388 (2) |
C9–C10 | 1.405 (3) | 1.3914 (16) | 1.402 (2) |
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