Presented here are the synthesis, characterization and study (using single crystal X-ray diffraction, Raman scattering, quantum mechanics calculations) of the structures of a series of biphenyls substituted in positions 3, 3′, 4 and 4′ with a variety of R (R = methyl, acetyl, hexyl) groups connected to the biphenyl core through oxygen atoms. The molecular conformation, particularly the torsion angle between aromatic rings has been extensively studied both in the solid as well as in the liquid state. The results show that the compounds appearing as rigorously planar in the solid present instead a twisted conformation in the melt. The solid versus melt issue strongly suggests that the reasons for planarity are to be found in the packing restraints. A `rule of thumb' is suggested for the design of biphenyls with different molecular conformations, based on the selection of the OR substituent.
Supporting information
CCDC references: 1992376; 1992377; 1992378; 1992379
Data collection: Bruker APEX2 for (I), (IV); CrysAlis PRO (Oxford Diffraction, 2009) for (II), (Vb). Cell refinement: Bruker SAINT for (I), (IV); CrysAlis PRO for (II), (Vb). Data reduction: Bruker SAINT for (I), (IV); CrysAlis PRO for (II), (Vb). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick 2008). Program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015) for (I), (IV); SHELXL2018/1 (Sheldrick, 2015) for (II), (Vb). For all structures, molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2018, PLATON (Spek, 2009).
Crystal data top
C36H58O4 | F(000) = 612 |
Mr = 554.82 | Dx = 1.109 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.486 (2) Å | Cell parameters from 8395 reflections |
b = 8.8585 (9) Å | θ = 2.5–30.2° |
c = 8.3874 (8) Å | µ = 0.07 mm−1 |
β = 96.221 (3)° | T = 150 K |
V = 1660.8 (3) Å3 | Fragment, colourless |
Z = 2 | 0.22 × 0.16 × 0.12 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3347 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.084 |
Absorption correction: multi-scan Bruker SAINT | θmax = 31.6°, θmin = 2.5° |
Tmin = 0.90, Tmax = 0.96 | h = −32→31 |
26569 measured reflections | k = −13→12 |
4907 independent reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0362P)2 + 0.4066P] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max < 0.001 |
4907 reflections | Δρmax = 0.34 e Å−3 |
183 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.62808 (4) | 0.53454 (12) | 0.56014 (11) | 0.0255 (3) | |
O2 | 0.66405 (4) | 0.37790 (12) | 0.81108 (11) | 0.0271 (3) | |
C1 | 0.50070 (6) | 0.59344 (17) | 0.79638 (16) | 0.0235 (3) | |
H1A | 0.463691 | 0.646004 | 0.790133 | 0.028* | |
C2 | 0.53584 (6) | 0.60466 (17) | 0.66974 (16) | 0.0233 (3) | |
H2A | 0.522363 | 0.663905 | 0.578510 | 0.028* | |
C3 | 0.58986 (6) | 0.53073 (16) | 0.67563 (15) | 0.0202 (3) | |
C4 | 0.60933 (6) | 0.44426 (16) | 0.81256 (16) | 0.0206 (3) | |
C5 | 0.57385 (6) | 0.43294 (16) | 0.93620 (16) | 0.0214 (3) | |
H5A | 0.587275 | 0.373179 | 1.027070 | 0.026* | |
C6 | 0.51860 (6) | 0.50686 (16) | 0.93197 (15) | 0.0191 (3) | |
C7 | 0.61685 (6) | 0.64258 (17) | 0.43261 (16) | 0.0240 (3) | |
H7A | 0.612290 | 0.745040 | 0.476845 | 0.029* | |
H7B | 0.579765 | 0.616410 | 0.363526 | 0.029* | |
C8 | 0.67018 (7) | 0.63693 (19) | 0.33730 (16) | 0.0268 (3) | |
H8A | 0.664135 | 0.710594 | 0.248258 | 0.032* | |
H8B | 0.672609 | 0.535146 | 0.289684 | 0.032* | |
C9 | 0.72899 (7) | 0.67160 (19) | 0.43771 (17) | 0.0286 (3) | |
H9A | 0.733554 | 0.602253 | 0.530794 | 0.034* | |
H9B | 0.727322 | 0.775802 | 0.479661 | 0.034* | |
C10 | 0.78390 (7) | 0.6569 (2) | 0.34676 (18) | 0.0305 (4) | |
H10A | 0.780598 | 0.562808 | 0.282761 | 0.037* | |
H10B | 0.784702 | 0.742704 | 0.271369 | 0.037* | |
C11 | 0.84186 (7) | 0.6543 (2) | 0.4562 (2) | 0.0417 (4) | |
H11A | 0.839488 | 0.573880 | 0.537245 | 0.050* | |
H11B | 0.846450 | 0.751823 | 0.513919 | 0.050* | |
C12 | 0.89717 (8) | 0.6275 (3) | 0.3699 (2) | 0.0491 (5) | |
H12A | 0.932599 | 0.621468 | 0.448711 | 0.074* | |
H12B | 0.901868 | 0.711043 | 0.295708 | 0.074* | |
H12C | 0.892598 | 0.532577 | 0.309666 | 0.074* | |
C13 | 0.68889 (7) | 0.30644 (19) | 0.95673 (17) | 0.0271 (3) | |
H13A | 0.663522 | 0.220440 | 0.982681 | 0.032* | |
H13B | 0.691264 | 0.379189 | 1.046794 | 0.032* | |
C14 | 0.75054 (7) | 0.25185 (19) | 0.93039 (18) | 0.0297 (4) | |
H14A | 0.747335 | 0.188915 | 0.832296 | 0.036* | |
H14B | 0.765587 | 0.186434 | 1.021653 | 0.036* | |
C15 | 0.79601 (7) | 0.3752 (2) | 0.91342 (19) | 0.0323 (4) | |
H15A | 0.801348 | 0.435073 | 1.013610 | 0.039* | |
H15B | 0.780646 | 0.443657 | 0.825147 | 0.039* | |
C16 | 0.85627 (7) | 0.3125 (2) | 0.8791 (2) | 0.0383 (4) | |
H16A | 0.869997 | 0.238658 | 0.963735 | 0.046* | |
H16B | 0.850988 | 0.257684 | 0.775665 | 0.046* | |
C17 | 0.90438 (8) | 0.4308 (3) | 0.8712 (2) | 0.0518 (5) | |
H17A | 0.911482 | 0.481910 | 0.976531 | 0.062* | |
H17B | 0.890033 | 0.507698 | 0.790418 | 0.062* | |
C18 | 0.96299 (9) | 0.3659 (4) | 0.8282 (3) | 0.0780 (8) | |
H18A | 0.991880 | 0.447818 | 0.820919 | 0.117* | |
H18B | 0.956223 | 0.313838 | 0.724760 | 0.117* | |
H18C | 0.978748 | 0.294190 | 0.911253 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0282 (6) | 0.0292 (6) | 0.0209 (5) | 0.0066 (4) | 0.0110 (4) | 0.0056 (4) |
O2 | 0.0227 (5) | 0.0386 (7) | 0.0214 (5) | 0.0095 (5) | 0.0079 (4) | 0.0075 (4) |
C1 | 0.0195 (7) | 0.0287 (8) | 0.0227 (7) | 0.0030 (6) | 0.0039 (5) | 0.0013 (6) |
C2 | 0.0237 (7) | 0.0274 (8) | 0.0188 (6) | 0.0032 (6) | 0.0025 (5) | 0.0041 (6) |
C3 | 0.0216 (7) | 0.0217 (7) | 0.0180 (6) | −0.0019 (6) | 0.0055 (5) | −0.0015 (5) |
C4 | 0.0188 (7) | 0.0221 (7) | 0.0212 (6) | 0.0012 (5) | 0.0034 (5) | −0.0011 (5) |
C5 | 0.0225 (7) | 0.0232 (7) | 0.0187 (6) | −0.0002 (6) | 0.0026 (5) | 0.0024 (5) |
C6 | 0.0186 (7) | 0.0196 (7) | 0.0193 (6) | −0.0026 (5) | 0.0035 (5) | −0.0015 (5) |
C7 | 0.0263 (7) | 0.0289 (8) | 0.0173 (6) | 0.0037 (6) | 0.0047 (5) | 0.0035 (6) |
C8 | 0.0281 (8) | 0.0361 (9) | 0.0171 (6) | 0.0040 (7) | 0.0065 (5) | 0.0040 (6) |
C9 | 0.0289 (8) | 0.0361 (9) | 0.0221 (7) | −0.0008 (7) | 0.0082 (6) | 0.0009 (6) |
C10 | 0.0285 (8) | 0.0401 (10) | 0.0243 (7) | −0.0021 (7) | 0.0097 (6) | 0.0031 (7) |
C11 | 0.0286 (9) | 0.0635 (13) | 0.0338 (9) | −0.0032 (8) | 0.0078 (7) | 0.0019 (8) |
C12 | 0.0275 (9) | 0.0708 (15) | 0.0503 (11) | −0.0006 (9) | 0.0104 (8) | 0.0022 (10) |
C13 | 0.0259 (8) | 0.0332 (9) | 0.0228 (7) | 0.0056 (6) | 0.0059 (6) | 0.0078 (6) |
C14 | 0.0270 (8) | 0.0347 (9) | 0.0278 (7) | 0.0077 (7) | 0.0043 (6) | 0.0044 (6) |
C15 | 0.0247 (8) | 0.0411 (10) | 0.0309 (8) | 0.0030 (7) | 0.0025 (6) | −0.0017 (7) |
C16 | 0.0257 (8) | 0.0562 (12) | 0.0332 (8) | 0.0049 (8) | 0.0041 (7) | −0.0015 (8) |
C17 | 0.0291 (9) | 0.0788 (16) | 0.0473 (11) | −0.0053 (10) | 0.0032 (8) | 0.0021 (10) |
C18 | 0.0297 (11) | 0.136 (3) | 0.0700 (15) | −0.0082 (14) | 0.0141 (10) | −0.0142 (16) |
Geometric parameters (Å, º) top
O1—C3 | 1.3633 (16) | C10—H10B | 0.9900 |
O1—C7 | 1.4371 (16) | C11—C12 | 1.524 (2) |
O2—C4 | 1.3649 (17) | C11—H11A | 0.9900 |
O2—C13 | 1.4342 (17) | C11—H11B | 0.9900 |
C1—C2 | 1.3945 (19) | C12—H12A | 0.9801 |
C1—C6 | 1.3944 (19) | C12—H12B | 0.9801 |
C1—H1A | 0.9500 | C12—H12C | 0.9801 |
C2—C3 | 1.376 (2) | C13—C14 | 1.507 (2) |
C2—H2A | 0.9500 | C13—H13A | 0.9900 |
C3—C4 | 1.4101 (19) | C13—H13B | 0.9900 |
C4—C5 | 1.3788 (19) | C14—C15 | 1.514 (2) |
C5—C6 | 1.4013 (19) | C14—H14A | 0.9900 |
C5—H5A | 0.9500 | C14—H14B | 0.9900 |
C6—C6i | 1.491 (3) | C15—C16 | 1.520 (2) |
C7—C8 | 1.5125 (19) | C15—H15A | 0.9900 |
C7—H7A | 0.9900 | C15—H15B | 0.9900 |
C7—H7B | 0.9900 | C16—C17 | 1.512 (3) |
C8—C9 | 1.520 (2) | C16—H16A | 0.9900 |
C8—H8A | 0.9900 | C16—H16B | 0.9900 |
C8—H8B | 0.9900 | C17—C18 | 1.517 (3) |
C9—C10 | 1.526 (2) | C17—H17A | 0.9900 |
C9—H9A | 0.9900 | C17—H17B | 0.9900 |
C9—H9B | 0.9900 | C18—H18A | 0.9801 |
C10—C11 | 1.511 (2) | C18—H18B | 0.9801 |
C10—H10A | 0.9900 | C18—H18C | 0.9801 |
| | | |
C3—O1—C7 | 118.15 (11) | C12—C11—H11A | 108.7 |
C4—O2—C13 | 116.79 (10) | C10—C11—H11B | 108.7 |
C2—C1—C6 | 121.54 (13) | C12—C11—H11B | 108.7 |
C2—C1—H1A | 119.2 | H11A—C11—H11B | 107.6 |
C6—C1—H1A | 119.2 | C11—C12—H12A | 109.5 |
C3—C2—C1 | 120.64 (13) | C11—C12—H12B | 109.5 |
C3—C2—H2A | 119.7 | H12A—C12—H12B | 109.5 |
C1—C2—H2A | 119.7 | C11—C12—H12C | 109.5 |
O1—C3—C2 | 125.78 (12) | H12A—C12—H12C | 109.5 |
O1—C3—C4 | 115.36 (12) | H12B—C12—H12C | 109.5 |
C2—C3—C4 | 118.86 (12) | O2—C13—C14 | 107.24 (11) |
O2—C4—C5 | 124.83 (12) | O2—C13—H13A | 110.3 |
O2—C4—C3 | 115.28 (11) | C14—C13—H13A | 110.3 |
C5—C4—C3 | 119.88 (13) | O2—C13—H13B | 110.3 |
C4—C5—C6 | 122.04 (13) | C14—C13—H13B | 110.3 |
C4—C5—H5A | 119.0 | H13A—C13—H13B | 108.5 |
C6—C5—H5A | 119.0 | C13—C14—C15 | 115.07 (14) |
C1—C6—C5 | 117.03 (12) | C13—C14—H14A | 108.5 |
C1—C6—C6i | 122.18 (15) | C15—C14—H14A | 108.5 |
C5—C6—C6i | 120.79 (15) | C13—C14—H14B | 108.5 |
O1—C7—C8 | 106.61 (11) | C15—C14—H14B | 108.5 |
O1—C7—H7A | 110.4 | H14A—C14—H14B | 107.5 |
C8—C7—H7A | 110.4 | C14—C15—C16 | 112.29 (15) |
O1—C7—H7B | 110.4 | C14—C15—H15A | 109.1 |
C8—C7—H7B | 110.4 | C16—C15—H15A | 109.1 |
H7A—C7—H7B | 108.6 | C14—C15—H15B | 109.1 |
C7—C8—C9 | 113.11 (11) | C16—C15—H15B | 109.1 |
C7—C8—H8A | 109.0 | H15A—C15—H15B | 107.9 |
C9—C8—H8A | 109.0 | C17—C16—C15 | 114.31 (17) |
C7—C8—H8B | 109.0 | C17—C16—H16A | 108.7 |
C9—C8—H8B | 109.0 | C15—C16—H16A | 108.7 |
H8A—C8—H8B | 107.8 | C17—C16—H16B | 108.7 |
C8—C9—C10 | 114.10 (12) | C15—C16—H16B | 108.7 |
C8—C9—H9A | 108.7 | H16A—C16—H16B | 107.6 |
C10—C9—H9A | 108.7 | C16—C17—C18 | 113.1 (2) |
C8—C9—H9B | 108.7 | C16—C17—H17A | 109.0 |
C10—C9—H9B | 108.7 | C18—C17—H17A | 109.0 |
H9A—C9—H9B | 107.6 | C16—C17—H17B | 109.0 |
C11—C10—C9 | 112.89 (12) | C18—C17—H17B | 109.0 |
C11—C10—H10A | 109.0 | H17A—C17—H17B | 107.8 |
C9—C10—H10A | 109.0 | C17—C18—H18A | 109.5 |
C11—C10—H10B | 109.0 | C17—C18—H18B | 109.5 |
C9—C10—H10B | 109.0 | H18A—C18—H18B | 109.5 |
H10A—C10—H10B | 107.8 | C17—C18—H18C | 109.5 |
C10—C11—C12 | 114.09 (14) | H18A—C18—H18C | 109.5 |
C10—C11—H11A | 108.7 | H18B—C18—H18C | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1ii | 0.99 | 2.50 | 3.4645 (19) | 163 |
Symmetry code: (ii) x, −y+1/2, z+1/2. |
Crystal data top
C28H38O6 | Z = 1 |
Mr = 470.58 | F(000) = 254 |
Triclinic, P1 | Dx = 1.194 Mg m−3 |
a = 8.554 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6844 (17) Å | Cell parameters from 706 reflections |
c = 9.810 (3) Å | θ = 3.7–26.2° |
α = 100.26 (2)° | µ = 0.08 mm−1 |
β = 109.10 (3)° | T = 294 K |
γ = 100.53 (2)° | Fragment, colourless |
V = 654.4 (3) Å3 | 0.28 × 0.18 × 0.14 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 1554 reflections with I > 2σ(I) |
ω scans, thick slices | Rint = 0.146 |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009) | θmax = 29.0°, θmin = 3.6° |
Tmin = 0.96, Tmax = 0.99 | h = −11→11 |
4799 measured reflections | k = −8→11 |
2919 independent reflections | l = −13→11 |
Refinement top
Refinement on F2 | Primary atom site location: direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2919 reflections | Δρmax = 0.28 e Å−3 |
154 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.70994 (19) | 0.57970 (17) | 0.73363 (17) | 0.0500 (5) | |
O2 | 0.5616 (2) | 0.78025 (17) | 0.86529 (17) | 0.0519 (5) | |
O3 | 0.3331 (2) | 0.5636 (2) | 0.7495 (2) | 0.0625 (5) | |
C1 | 0.6055 (3) | 0.8298 (2) | 0.4675 (3) | 0.0493 (6) | |
H1A | 0.615786 | 0.839868 | 0.375759 | 0.059* | |
C2 | 0.6652 (3) | 0.7110 (3) | 0.5291 (3) | 0.0500 (6) | |
H2A | 0.716344 | 0.643038 | 0.480093 | 0.060* | |
C3 | 0.6512 (3) | 0.6900 (3) | 0.6611 (3) | 0.0441 (6) | |
C4 | 0.5718 (3) | 0.7916 (3) | 0.7265 (3) | 0.0428 (6) | |
C5 | 0.5139 (3) | 0.9086 (3) | 0.6652 (3) | 0.0453 (6) | |
H5A | 0.459982 | 0.974163 | 0.713264 | 0.054* | |
C6 | 0.5308 (3) | 0.9361 (2) | 0.5333 (3) | 0.0415 (5) | |
C7 | 0.7953 (3) | 0.4775 (3) | 0.6664 (3) | 0.0479 (6) | |
H7A | 0.895059 | 0.545241 | 0.655960 | 0.058* | |
H7B | 0.715571 | 0.411779 | 0.565905 | 0.058* | |
C8 | 0.8530 (3) | 0.3692 (3) | 0.7643 (3) | 0.0496 (6) | |
H8A | 0.752030 | 0.303283 | 0.774489 | 0.060* | |
H8B | 0.930365 | 0.436713 | 0.864875 | 0.060* | |
C9 | 0.9458 (3) | 0.2565 (3) | 0.7048 (3) | 0.0489 (6) | |
H9A | 0.870233 | 0.192240 | 0.602490 | 0.059* | |
H9B | 1.049443 | 0.322470 | 0.698516 | 0.059* | |
C10 | 0.9983 (3) | 0.1416 (3) | 0.8006 (3) | 0.0497 (6) | |
H10A | 1.079320 | 0.206224 | 0.901028 | 0.060* | |
H10B | 0.895489 | 0.081116 | 0.812170 | 0.060* | |
C11 | 1.0812 (3) | 0.0213 (3) | 0.7385 (3) | 0.0601 (7) | |
H11A | 1.002203 | −0.040478 | 0.636505 | 0.072* | |
H11B | 1.186836 | 0.081545 | 0.730988 | 0.072* | |
C12 | 1.1264 (3) | −0.0968 (3) | 0.8322 (3) | 0.0668 (8) | |
H12A | 1.179948 | −0.171670 | 0.785776 | 0.100* | |
H12B | 1.207678 | −0.036300 | 0.933906 | 0.100* | |
H12C | 1.021008 | −0.159660 | 0.838196 | 0.100* | |
C13 | 0.4325 (4) | 0.6594 (3) | 0.8625 (3) | 0.0539 (7) | |
C14 | 0.4350 (4) | 0.6716 (3) | 1.0175 (3) | 0.0681 (8) | |
H14A | 0.342355 | 0.584833 | 1.015274 | 0.102* | |
H14B | 0.545305 | 0.660803 | 1.081744 | 0.102* | |
H14C | 0.418795 | 0.776913 | 1.056754 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0578 (10) | 0.0510 (9) | 0.0627 (12) | 0.0233 (8) | 0.0431 (9) | 0.0178 (8) |
O2 | 0.0647 (10) | 0.0506 (9) | 0.0563 (12) | 0.0177 (8) | 0.0406 (9) | 0.0152 (8) |
O3 | 0.0712 (12) | 0.0572 (10) | 0.0725 (14) | 0.0099 (9) | 0.0505 (11) | 0.0109 (10) |
C1 | 0.0570 (14) | 0.0469 (12) | 0.0641 (17) | 0.0159 (11) | 0.0450 (14) | 0.0179 (12) |
C2 | 0.0504 (13) | 0.0472 (13) | 0.0692 (18) | 0.0149 (11) | 0.0427 (13) | 0.0142 (12) |
C3 | 0.0494 (13) | 0.0412 (11) | 0.0546 (16) | 0.0144 (10) | 0.0324 (12) | 0.0159 (11) |
C4 | 0.0507 (13) | 0.0440 (11) | 0.0437 (15) | 0.0134 (10) | 0.0298 (12) | 0.0111 (11) |
C5 | 0.0471 (13) | 0.0415 (11) | 0.0593 (17) | 0.0150 (10) | 0.0351 (13) | 0.0096 (11) |
C6 | 0.0423 (12) | 0.0414 (11) | 0.0487 (15) | 0.0074 (10) | 0.0292 (12) | 0.0106 (10) |
C7 | 0.0472 (13) | 0.0480 (12) | 0.0640 (17) | 0.0182 (11) | 0.0385 (13) | 0.0118 (12) |
C8 | 0.0532 (14) | 0.0512 (13) | 0.0587 (17) | 0.0202 (11) | 0.0346 (13) | 0.0153 (12) |
C9 | 0.0481 (13) | 0.0520 (13) | 0.0633 (17) | 0.0162 (11) | 0.0386 (13) | 0.0181 (12) |
C10 | 0.0458 (12) | 0.0564 (13) | 0.0628 (17) | 0.0201 (11) | 0.0343 (13) | 0.0199 (13) |
C11 | 0.0578 (15) | 0.0585 (14) | 0.089 (2) | 0.0257 (12) | 0.0508 (15) | 0.0255 (14) |
C12 | 0.0590 (15) | 0.0601 (15) | 0.094 (2) | 0.0286 (13) | 0.0374 (16) | 0.0203 (15) |
C13 | 0.0710 (17) | 0.0515 (14) | 0.067 (2) | 0.0322 (13) | 0.0492 (16) | 0.0218 (14) |
C14 | 0.103 (2) | 0.0689 (16) | 0.071 (2) | 0.0439 (16) | 0.0617 (18) | 0.0336 (15) |
Geometric parameters (Å, º) top
O1—C3 | 1.364 (3) | C8—H8A | 0.9900 |
O1—C7 | 1.448 (2) | C8—H8B | 0.9900 |
O2—C13 | 1.367 (3) | C9—C10 | 1.517 (3) |
O2—C4 | 1.412 (2) | C9—H9A | 0.9900 |
O3—C13 | 1.200 (3) | C9—H9B | 0.9900 |
C1—C2 | 1.379 (3) | C10—C11 | 1.514 (3) |
C1—C6 | 1.397 (3) | C10—H10A | 0.9900 |
C1—H1A | 0.9500 | C10—H10B | 0.9900 |
C2—C3 | 1.379 (3) | C11—C12 | 1.515 (3) |
C2—H2A | 0.9500 | C11—H11A | 0.9900 |
C3—C4 | 1.398 (3) | C11—H11B | 0.9900 |
C4—C5 | 1.359 (3) | C12—H12A | 0.9901 |
C5—C6 | 1.404 (3) | C12—H12B | 0.9900 |
C5—H5A | 0.9500 | C12—H12C | 0.9900 |
C6—C6i | 1.477 (4) | C13—C14 | 1.498 (3) |
C7—C8 | 1.494 (3) | C14—H14A | 0.9800 |
C7—H7A | 0.9900 | C14—H14B | 0.9800 |
C7—H7B | 0.9900 | C14—H14C | 0.9800 |
C8—C9 | 1.520 (3) | | |
| | | |
C3—O1—C7 | 116.94 (17) | C10—C9—H9A | 108.9 |
C13—O2—C4 | 116.82 (19) | C8—C9—H9A | 108.9 |
C2—C1—C6 | 123.3 (2) | C10—C9—H9B | 108.9 |
C2—C1—H1A | 118.4 | C8—C9—H9B | 108.9 |
C6—C1—H1A | 118.4 | H9A—C9—H9B | 107.7 |
C3—C2—C1 | 120.6 (2) | C11—C10—C9 | 114.2 (2) |
C3—C2—H2A | 119.7 | C11—C10—H10A | 108.7 |
C1—C2—H2A | 119.7 | C9—C10—H10A | 108.7 |
O1—C3—C2 | 125.46 (19) | C11—C10—H10B | 108.7 |
O1—C3—C4 | 117.5 (2) | C9—C10—H10B | 108.7 |
C2—C3—C4 | 117.1 (2) | H10A—C10—H10B | 107.6 |
C5—C4—C3 | 121.8 (2) | C12—C11—C10 | 113.6 (2) |
C5—C4—O2 | 118.71 (19) | C12—C11—H11A | 108.9 |
C3—C4—O2 | 119.31 (19) | C10—C11—H11A | 108.9 |
C4—C5—C6 | 122.4 (2) | C12—C11—H11B | 108.9 |
C4—C5—H5A | 118.8 | C10—C11—H11B | 108.9 |
C6—C5—H5A | 118.8 | H11A—C11—H11B | 107.7 |
C1—C6—C5 | 114.7 (2) | C11—C12—H12A | 109.5 |
C1—C6—C6i | 122.6 (3) | C11—C12—H12B | 109.5 |
C5—C6—C6i | 122.7 (2) | H12A—C12—H12B | 109.5 |
O1—C7—C8 | 108.50 (18) | C11—C12—H12C | 109.4 |
O1—C7—H7A | 110.0 | H12A—C12—H12C | 109.5 |
C8—C7—H7A | 110.0 | H12B—C12—H12C | 109.5 |
O1—C7—H7B | 110.0 | O3—C13—O2 | 122.9 (2) |
C8—C7—H7B | 110.0 | O3—C13—C14 | 127.5 (2) |
H7A—C7—H7B | 108.4 | O2—C13—C14 | 109.5 (2) |
C7—C8—C9 | 113.11 (19) | C13—C14—H14A | 109.4 |
C7—C8—H8A | 109.0 | C13—C14—H14B | 109.5 |
C9—C8—H8A | 109.0 | H14A—C14—H14B | 109.5 |
C7—C8—H8B | 109.0 | C13—C14—H14C | 109.5 |
C9—C8—H8B | 109.0 | H14A—C14—H14C | 109.5 |
H8A—C8—H8B | 107.8 | H14B—C14—H14C | 109.5 |
C10—C9—C8 | 113.2 (2) | | |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O3ii | 0.95 | 2.48 | 3.298 (3) | 145 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Crystal data top
C18H18O6 | F(000) = 696 |
Mr = 330.32 | Dx = 1.398 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.304 (2) Å | Cell parameters from 6780 reflections |
b = 10.064 (2) Å | θ = 3.1–29.8° |
c = 14.496 (3) Å | µ = 0.11 mm−1 |
β = 107.822 (10)° | T = 150 K |
V = 1570.0 (6) Å3 | Fragment, colourless |
Z = 4 | 0.28 × 0.18 × 0.10 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 7986 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.030 |
Absorption correction: multi-scan Bruker SAINT | θmax = 32.8°, θmin = 2.7° |
Tmin = 0.90, Tmax = 0.96 | h = −16→16 |
25745 measured reflections | k = −15→14 |
9921 independent reflections | l = −22→20 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.0853P)2 + 1.1735P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.179 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.65 e Å−3 |
9921 reflections | Δρmin = −0.40 e Å−3 |
440 parameters | Absolute structure: Flack x determined using 3206 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
355 restraints | Absolute structure parameter: 0.0 (2) |
Primary atom site location: direct methods | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 1.0052 (2) | 0.8249 (3) | 0.45851 (17) | 0.0385 (7) | |
O2A | 0.8332 (4) | 0.9299 (4) | 0.3706 (2) | 0.0522 (8) | |
O3A | 0.8249 (2) | 0.6430 (2) | 0.44977 (16) | 0.0244 (5) | |
C1A | 0.9678 (3) | 0.8630 (5) | 0.6991 (2) | 0.0375 (9) | |
H1AA | 1.003185 | 0.913795 | 0.756159 | 0.045* | |
C2A | 1.0025 (4) | 0.8909 (5) | 0.6161 (3) | 0.0391 (9) | |
H2AA | 1.054370 | 0.964414 | 0.614062 | 0.047* | |
C3A | 0.9582 (3) | 0.8075 (4) | 0.5375 (2) | 0.0257 (6) | |
C4A | 0.8692 (3) | 0.7097 (3) | 0.53479 (19) | 0.0158 (5) | |
C5A | 0.8277 (3) | 0.6915 (3) | 0.6143 (2) | 0.0156 (5) | |
H5AA | 0.761967 | 0.630856 | 0.610492 | 0.019* | |
C6A | 0.8816 (2) | 0.7615 (3) | 0.70047 (18) | 0.0148 (5) | |
C7A | 0.9328 (4) | 0.8848 (4) | 0.3781 (3) | 0.0379 (7) | |
C8A | 0.9925 (5) | 0.8791 (6) | 0.2989 (3) | 0.0566 (14) | |
H8AA | 0.996457 | 0.968838 | 0.273608 | 0.085* | |
H8AB | 0.943345 | 0.821753 | 0.246488 | 0.085* | |
H8AC | 1.076818 | 0.843175 | 0.324737 | 0.085* | |
C9A | 0.7317 (4) | 0.5446 (4) | 0.4460 (3) | 0.0330 (8) | |
H9AA | 0.696987 | 0.512521 | 0.379271 | 0.049* | |
H9AB | 0.665366 | 0.584041 | 0.467508 | 0.049* | |
H9AC | 0.769065 | 0.470164 | 0.488469 | 0.049* | |
O1A' | 0.71824 (19) | 0.6785 (2) | 1.02983 (14) | 0.0172 (4) | |
O2A' | 0.9005 (2) | 0.5937 (3) | 1.12222 (15) | 0.0271 (5) | |
O3A' | 0.8857 (2) | 0.8711 (2) | 1.03354 (14) | 0.0214 (4) | |
C1A' | 0.7579 (2) | 0.6341 (3) | 0.78943 (18) | 0.0143 (5) | |
H1AB | 0.728312 | 0.577401 | 0.734787 | 0.017* | |
C2A' | 0.7192 (3) | 0.6138 (3) | 0.87088 (19) | 0.0166 (5) | |
H2AB | 0.661205 | 0.545525 | 0.870872 | 0.020* | |
C3A' | 0.7653 (2) | 0.6930 (3) | 0.95128 (18) | 0.0129 (4) | |
C4A' | 0.8476 (2) | 0.7969 (2) | 0.95118 (18) | 0.0115 (4) | |
C5A' | 0.8852 (2) | 0.8172 (2) | 0.86969 (17) | 0.0116 (4) | |
H5AB | 0.942452 | 0.886383 | 0.869869 | 0.014* | |
C6A' | 0.8405 (2) | 0.7377 (2) | 0.78759 (16) | 0.0103 (4) | |
C7A' | 0.7966 (3) | 0.6300 (3) | 1.1138 (2) | 0.0190 (5) | |
C8A' | 0.7327 (4) | 0.6280 (4) | 1.1897 (2) | 0.0312 (7) | |
H8AD | 0.783324 | 0.578332 | 1.246133 | 0.047* | |
H8AE | 0.651454 | 0.585084 | 1.163808 | 0.047* | |
H8AF | 0.721435 | 0.719299 | 1.208961 | 0.047* | |
C9A' | 0.9809 (3) | 0.9653 (3) | 1.03937 (19) | 0.0213 (5) | |
H9AD | 1.009331 | 1.002815 | 1.104861 | 0.032* | |
H9AE | 0.948578 | 1.036560 | 0.992340 | 0.032* | |
H9AF | 1.050701 | 0.921545 | 1.024932 | 0.032* | |
O1B | 0.4505 (4) | 0.3141 (5) | 0.5243 (2) | 0.0737 (14) | |
O2B | 0.6190 (2) | 0.4214 (3) | 0.61168 (17) | 0.0299 (5) | |
O3B | 0.6257 (4) | 0.1488 (4) | 0.5262 (3) | 0.0656 (10) | |
C1B | 0.4834 (3) | 0.3818 (4) | 0.2824 (3) | 0.0344 (7) | |
H1BA | 0.451078 | 0.439087 | 0.228446 | 0.041* | |
C2B | 0.4429 (4) | 0.3932 (6) | 0.3643 (3) | 0.0458 (10) | |
H2BA | 0.380953 | 0.456329 | 0.365516 | 0.055* | |
C3B | 0.4939 (4) | 0.3117 (5) | 0.4432 (3) | 0.0447 (8) | |
C4B | 0.5827 (5) | 0.2226 (5) | 0.4456 (3) | 0.0468 (9) | |
C5B | 0.6210 (5) | 0.2085 (4) | 0.3616 (3) | 0.0414 (9) | |
H5BA | 0.682291 | 0.144253 | 0.360996 | 0.050* | |
C6B | 0.5707 (3) | 0.2865 (3) | 0.2807 (2) | 0.0273 (6) | |
C7B | 0.5261 (4) | 0.3632 (5) | 0.6074 (3) | 0.0409 (9) | |
C8B | 0.4681 (4) | 0.3427 (7) | 0.6864 (3) | 0.0566 (15) | |
H8BA | 0.510761 | 0.398194 | 0.742247 | 0.085* | |
H8BB | 0.475491 | 0.249044 | 0.705851 | 0.085* | |
H8BC | 0.380085 | 0.367509 | 0.662822 | 0.085* | |
C9B | 0.7420 (8) | 0.0805 (8) | 0.5416 (6) | 0.094 (2) | |
H9BA | 0.788160 | 0.079461 | 0.610928 | 0.141* | |
H9BB | 0.728376 | −0.010946 | 0.517456 | 0.141* | |
H9BC | 0.789922 | 0.128967 | 0.506470 | 0.141* | |
O1B' | 0.7652 (2) | 0.2704 (2) | −0.03688 (16) | 0.0282 (5) | |
O2B' | 0.6418 (4) | 0.1059 (3) | −0.1127 (2) | 0.0526 (9) | |
O3B' | 0.5377 (2) | 0.3698 (2) | −0.06364 (14) | 0.0222 (4) | |
C1B' | 0.7365 (3) | 0.2234 (4) | 0.2059 (2) | 0.0307 (6) | |
H1BB | 0.785264 | 0.191667 | 0.267520 | 0.037* | |
C2B' | 0.7831 (3) | 0.2164 (4) | 0.1278 (2) | 0.0317 (7) | |
H2BB | 0.862009 | 0.177582 | 0.134938 | 0.038* | |
C3B' | 0.7121 (3) | 0.2672 (3) | 0.0391 (2) | 0.0225 (5) | |
C4B' | 0.5955 (3) | 0.3233 (3) | 0.0264 (2) | 0.0181 (5) | |
C5B' | 0.5499 (3) | 0.3284 (3) | 0.1049 (2) | 0.0191 (5) | |
H5BB | 0.471035 | 0.367615 | 0.097367 | 0.023* | |
C6B' | 0.6184 (3) | 0.2766 (3) | 0.1950 (2) | 0.0222 (5) | |
C7B' | 0.7195 (4) | 0.1861 (4) | −0.1104 (3) | 0.0320 (6) | |
C8B' | 0.7793 (5) | 0.2072 (5) | −0.1882 (3) | 0.0483 (11) | |
H8BD | 0.742120 | 0.146784 | −0.242384 | 0.072* | |
H8BE | 0.868631 | 0.189263 | −0.162179 | 0.072* | |
H8BF | 0.766436 | 0.299305 | −0.211040 | 0.072* | |
C9B' | 0.4328 (3) | 0.4554 (3) | −0.0724 (2) | 0.0289 (7) | |
H9BD | 0.403254 | 0.491418 | −0.138302 | 0.043* | |
H9BE | 0.457756 | 0.528543 | −0.025847 | 0.043* | |
H9BF | 0.366000 | 0.404431 | −0.058993 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0292 (12) | 0.073 (2) | 0.0197 (10) | −0.0189 (12) | 0.0173 (9) | −0.0055 (11) |
O2A | 0.0733 (19) | 0.0501 (17) | 0.0391 (16) | −0.0001 (16) | 0.0258 (15) | 0.0126 (14) |
O3A | 0.0380 (12) | 0.0247 (10) | 0.0166 (9) | −0.0080 (9) | 0.0172 (9) | −0.0063 (8) |
C1A | 0.0357 (17) | 0.058 (2) | 0.0219 (14) | −0.0286 (17) | 0.0134 (13) | −0.0123 (15) |
C2A | 0.0377 (18) | 0.059 (2) | 0.0251 (14) | −0.0262 (17) | 0.0162 (14) | −0.0102 (14) |
C3A | 0.0218 (13) | 0.0430 (17) | 0.0167 (12) | −0.0097 (12) | 0.0126 (10) | −0.0026 (11) |
C4A | 0.0166 (11) | 0.0203 (12) | 0.0113 (10) | 0.0018 (9) | 0.0053 (8) | −0.0007 (8) |
C5A | 0.0187 (11) | 0.0150 (11) | 0.0146 (10) | −0.0023 (9) | 0.0073 (9) | 0.0009 (8) |
C6A | 0.0108 (10) | 0.0253 (12) | 0.0085 (9) | −0.0003 (9) | 0.0033 (8) | 0.0005 (8) |
C7A | 0.0536 (17) | 0.0408 (19) | 0.0225 (13) | −0.0267 (14) | 0.0162 (13) | −0.0038 (13) |
C8A | 0.069 (3) | 0.082 (4) | 0.0286 (18) | −0.040 (3) | 0.0292 (19) | −0.009 (2) |
C9A | 0.050 (2) | 0.0270 (15) | 0.0301 (16) | −0.0158 (14) | 0.0240 (16) | −0.0157 (13) |
O1A' | 0.0200 (9) | 0.0238 (9) | 0.0105 (8) | −0.0015 (7) | 0.0085 (7) | 0.0006 (7) |
O2A' | 0.0317 (11) | 0.0374 (12) | 0.0122 (9) | 0.0088 (10) | 0.0068 (8) | 0.0058 (9) |
O3A' | 0.0347 (11) | 0.0225 (9) | 0.0122 (8) | −0.0063 (8) | 0.0151 (8) | −0.0060 (7) |
C1A' | 0.0149 (11) | 0.0184 (11) | 0.0096 (10) | −0.0011 (9) | 0.0039 (8) | 0.0016 (9) |
C2A' | 0.0162 (11) | 0.0230 (12) | 0.0113 (10) | −0.0038 (10) | 0.0054 (8) | 0.0016 (9) |
C3A' | 0.0140 (10) | 0.0166 (10) | 0.0089 (9) | 0.0010 (8) | 0.0050 (8) | 0.0028 (8) |
C4A' | 0.0149 (10) | 0.0110 (9) | 0.0096 (9) | 0.0034 (8) | 0.0050 (8) | 0.0006 (7) |
C5A' | 0.0155 (10) | 0.0119 (9) | 0.0084 (9) | 0.0015 (8) | 0.0053 (8) | 0.0013 (7) |
C6A' | 0.0099 (9) | 0.0129 (9) | 0.0078 (9) | 0.0021 (7) | 0.0020 (7) | 0.0017 (7) |
C7A' | 0.0292 (12) | 0.0203 (12) | 0.0095 (10) | −0.0009 (10) | 0.0086 (9) | 0.0030 (9) |
C8A' | 0.0448 (19) | 0.0382 (18) | 0.0170 (13) | −0.0014 (15) | 0.0190 (13) | 0.0025 (12) |
C9A' | 0.0295 (14) | 0.0263 (13) | 0.0102 (10) | −0.0053 (11) | 0.0094 (10) | −0.0034 (10) |
O1B | 0.064 (2) | 0.129 (4) | 0.0337 (15) | −0.053 (2) | 0.0245 (14) | −0.0229 (19) |
O2B | 0.0371 (12) | 0.0355 (12) | 0.0205 (11) | −0.0113 (10) | 0.0137 (10) | −0.0084 (9) |
O3B | 0.104 (3) | 0.051 (2) | 0.0499 (19) | −0.0019 (19) | 0.036 (2) | 0.0040 (15) |
C1B | 0.0298 (16) | 0.052 (2) | 0.0228 (14) | −0.0043 (14) | 0.0107 (12) | −0.0032 (14) |
C2B | 0.0358 (19) | 0.077 (3) | 0.0292 (16) | −0.0054 (18) | 0.0172 (14) | −0.0074 (16) |
C3B | 0.047 (2) | 0.061 (2) | 0.0283 (15) | −0.0242 (15) | 0.0162 (14) | −0.0101 (15) |
C4B | 0.061 (2) | 0.044 (2) | 0.0372 (17) | −0.0223 (16) | 0.0186 (17) | −0.0050 (15) |
C5B | 0.062 (2) | 0.0302 (17) | 0.0354 (17) | −0.0059 (16) | 0.0199 (17) | −0.0009 (13) |
C6B | 0.0358 (15) | 0.0262 (14) | 0.0217 (12) | −0.0141 (11) | 0.0117 (11) | −0.0100 (10) |
C7B | 0.0372 (16) | 0.062 (2) | 0.0286 (15) | −0.0162 (17) | 0.0173 (13) | −0.0120 (16) |
C8B | 0.037 (2) | 0.111 (5) | 0.0258 (17) | −0.024 (3) | 0.0158 (15) | −0.014 (2) |
C9B | 0.136 (5) | 0.079 (5) | 0.080 (5) | 0.036 (4) | 0.053 (4) | 0.034 (4) |
O1B' | 0.0371 (12) | 0.0339 (11) | 0.0223 (10) | 0.0046 (10) | 0.0220 (9) | 0.0027 (8) |
O2B' | 0.082 (2) | 0.0435 (15) | 0.0485 (18) | −0.0115 (15) | 0.0439 (17) | −0.0187 (14) |
O3B' | 0.0364 (11) | 0.0215 (9) | 0.0144 (8) | 0.0028 (8) | 0.0161 (8) | −0.0008 (7) |
C1B' | 0.0396 (16) | 0.0359 (16) | 0.0190 (12) | 0.0035 (13) | 0.0125 (12) | −0.0006 (12) |
C2B' | 0.0353 (16) | 0.0416 (18) | 0.0224 (13) | 0.0079 (14) | 0.0152 (12) | 0.0010 (12) |
C3B' | 0.0329 (13) | 0.0211 (12) | 0.0203 (11) | 0.0012 (10) | 0.0183 (10) | −0.0001 (10) |
C4B' | 0.0289 (12) | 0.0145 (10) | 0.0163 (10) | −0.0039 (9) | 0.0149 (9) | −0.0016 (8) |
C5B' | 0.0298 (13) | 0.0168 (11) | 0.0150 (11) | −0.0057 (10) | 0.0132 (10) | −0.0029 (9) |
C6B' | 0.0342 (13) | 0.0170 (11) | 0.0190 (11) | −0.0081 (10) | 0.0133 (10) | −0.0033 (9) |
C7B' | 0.0481 (18) | 0.0303 (14) | 0.0242 (13) | 0.0133 (12) | 0.0209 (13) | 0.0037 (11) |
C8B' | 0.067 (3) | 0.063 (3) | 0.0269 (17) | 0.028 (2) | 0.0314 (18) | 0.0138 (17) |
C9B' | 0.0425 (17) | 0.0292 (15) | 0.0236 (14) | 0.0067 (12) | 0.0228 (13) | 0.0005 (11) |
Geometric parameters (Å, º) top
O1A—C7A | 1.345 (5) | O1B—C7B | 1.340 (5) |
O1A—C3A | 1.412 (3) | O1B—C3B | 1.405 (5) |
O2A—C7A | 1.187 (6) | O2B—C7B | 1.188 (5) |
O3A—C4A | 1.357 (3) | O3B—C4B | 1.344 (6) |
O3A—C9A | 1.434 (4) | O3B—C9B | 1.440 (9) |
C1A—C2A | 1.404 (5) | C1B—C6B | 1.381 (5) |
C1A—C6A | 1.415 (4) | C1B—C2B | 1.402 (5) |
C1A—H1AA | 0.9500 | C1B—H1BA | 0.9500 |
C2A—C3A | 1.380 (5) | C2B—C3B | 1.382 (7) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.400 (4) | C3B—C4B | 1.338 (7) |
C4A—C5A | 1.384 (4) | C4B—C5B | 1.418 (6) |
C5A—C6A | 1.400 (4) | C5B—C6B | 1.381 (5) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C6A' | 1.493 (3) | C6B—C6B' | 1.502 (4) |
C7A—C8A | 1.502 (5) | C7B—C8B | 1.497 (5) |
C8A—H8AA | 0.9801 | C8B—H8BA | 0.9801 |
C8A—H8AB | 0.9801 | C8B—H8BB | 0.9801 |
C8A—H8AC | 0.9801 | C8B—H8BC | 0.9801 |
C9A—H9AA | 0.9801 | C9B—H9BA | 0.9800 |
C9A—H9AB | 0.9801 | C9B—H9BB | 0.9800 |
C9A—H9AC | 0.9801 | C9B—H9BC | 0.9800 |
O1A'—C7A' | 1.358 (3) | O1B'—C7B' | 1.337 (4) |
O1A'—C3A' | 1.404 (3) | O1B'—C3B' | 1.407 (3) |
O2A'—C7A' | 1.200 (4) | O2B'—C7B' | 1.186 (5) |
O3A'—C4A' | 1.362 (3) | O3B'—C4B' | 1.351 (3) |
O3A'—C9A' | 1.417 (4) | O3B'—C9B' | 1.439 (4) |
C1A'—C2A' | 1.394 (4) | C1B'—C2B' | 1.389 (4) |
C1A'—C6A' | 1.406 (4) | C1B'—C6B' | 1.401 (5) |
C1A'—H1AB | 0.9500 | C1B'—H1BB | 0.9500 |
C2A'—C3A' | 1.376 (4) | C2B'—C3B' | 1.388 (4) |
C2A'—H2AB | 0.9500 | C2B'—H2BB | 0.9500 |
C3A'—C4A' | 1.400 (4) | C3B'—C4B' | 1.393 (4) |
C4A'—C5A' | 1.388 (3) | C4B'—C5B' | 1.387 (3) |
C5A'—C6A' | 1.394 (3) | C5B'—C6B' | 1.400 (4) |
C5A'—H5AB | 0.9500 | C5B'—H5BB | 0.9500 |
C7A'—C8A' | 1.489 (4) | C7B'—C8B' | 1.497 (5) |
C8A'—H8AD | 0.9801 | C8B'—H8BD | 0.9801 |
C8A'—H8AE | 0.9801 | C8B'—H8BE | 0.9801 |
C8A'—H8AF | 0.9801 | C8B'—H8BF | 0.9801 |
C9A'—H9AD | 0.9801 | C9B'—H9BD | 0.9801 |
C9A'—H9AE | 0.9801 | C9B'—H9BE | 0.9801 |
C9A'—H9AF | 0.9801 | C9B'—H9BF | 0.9801 |
| | | |
C7A—O1A—C3A | 118.5 (3) | C7B—O1B—C3B | 118.0 (3) |
C4A—O3A—C9A | 116.0 (2) | C4B—O3B—C9B | 118.0 (4) |
C2A—C1A—C6A | 122.0 (3) | C6B—C1B—C2B | 119.5 (4) |
C2A—C1A—H1AA | 119.0 | C6B—C1B—H1BA | 120.3 |
C6A—C1A—H1AA | 119.0 | C2B—C1B—H1BA | 120.3 |
C3A—C2A—C1A | 117.4 (3) | C3B—C2B—C1B | 119.4 (4) |
C3A—C2A—H2AA | 121.3 | C3B—C2B—H2BA | 120.3 |
C1A—C2A—H2AA | 121.3 | C1B—C2B—H2BA | 120.3 |
C2A—C3A—C4A | 121.8 (3) | C4B—C3B—C2B | 122.5 (4) |
C2A—C3A—O1A | 117.6 (3) | C4B—C3B—O1B | 116.2 (5) |
C4A—C3A—O1A | 120.7 (3) | C2B—C3B—O1B | 121.2 (5) |
O3A—C4A—C5A | 124.5 (3) | C3B—C4B—O3B | 117.5 (4) |
O3A—C4A—C3A | 115.8 (2) | C3B—C4B—C5B | 117.9 (4) |
C5A—C4A—C3A | 119.6 (3) | O3B—C4B—C5B | 124.5 (5) |
C4A—C5A—C6A | 120.7 (2) | C6B—C5B—C4B | 121.1 (4) |
C4A—C5A—H5AA | 119.7 | C6B—C5B—H5BA | 119.4 |
C6A—C5A—H5AA | 119.7 | C4B—C5B—H5BA | 119.4 |
C5A—C6A—C1A | 117.7 (2) | C1B—C6B—C5B | 119.4 (3) |
C5A—C6A—C6A' | 120.7 (2) | C1B—C6B—C6B' | 120.0 (3) |
C1A—C6A—C6A' | 121.4 (2) | C5B—C6B—C6B' | 120.4 (3) |
O2A—C7A—O1A | 124.1 (3) | O2B—C7B—O1B | 122.6 (3) |
O2A—C7A—C8A | 125.4 (4) | O2B—C7B—C8B | 128.0 (4) |
O1A—C7A—C8A | 110.4 (4) | O1B—C7B—C8B | 109.3 (3) |
C7A—C8A—H8AA | 109.5 | C7B—C8B—H8BA | 109.5 |
C7A—C8A—H8AB | 109.5 | C7B—C8B—H8BB | 109.5 |
H8AA—C8A—H8AB | 109.5 | H8BA—C8B—H8BB | 109.5 |
C7A—C8A—H8AC | 109.5 | C7B—C8B—H8BC | 109.5 |
H8AA—C8A—H8AC | 109.5 | H8BA—C8B—H8BC | 109.5 |
H8AB—C8A—H8AC | 109.5 | H8BB—C8B—H8BC | 109.5 |
O3A—C9A—H9AA | 109.5 | O3B—C9B—H9BA | 109.8 |
O3A—C9A—H9AB | 109.5 | O3B—C9B—H9BB | 110.9 |
H9AA—C9A—H9AB | 109.5 | H9BA—C9B—H9BB | 109.4 |
O3A—C9A—H9AC | 109.5 | O3B—C9B—H9BC | 107.8 |
H9AA—C9A—H9AC | 109.5 | H9BA—C9B—H9BC | 109.4 |
H9AB—C9A—H9AC | 109.5 | H9BB—C9B—H9BC | 109.4 |
C7A'—O1A'—C3A' | 117.3 (2) | C7B'—O1B'—C3B' | 117.2 (3) |
C4A'—O3A'—C9A' | 116.7 (2) | C4B'—O3B'—C9B' | 115.7 (2) |
C2A'—C1A'—C6A' | 120.5 (2) | C2B'—C1B'—C6B' | 120.9 (3) |
C2A'—C1A'—H1AB | 119.8 | C2B'—C1B'—H1BB | 119.6 |
C6A'—C1A'—H1AB | 119.8 | C6B'—C1B'—H1BB | 119.6 |
C3A'—C2A'—C1A' | 119.8 (2) | C3B'—C2B'—C1B' | 118.7 (3) |
C3A'—C2A'—H2AB | 120.1 | C3B'—C2B'—H2BB | 120.7 |
C1A'—C2A'—H2AB | 120.1 | C1B'—C2B'—H2BB | 120.7 |
C2A'—C3A'—C4A' | 120.8 (2) | C2B'—C3B'—C4B' | 121.8 (3) |
C2A'—C3A'—O1A' | 119.2 (2) | C2B'—C3B'—O1B' | 118.0 (3) |
C4A'—C3A'—O1A' | 119.7 (2) | C4B'—C3B'—O1B' | 120.0 (3) |
O3A'—C4A'—C5A' | 124.6 (2) | O3B'—C4B'—C5B' | 126.0 (3) |
O3A'—C4A'—C3A' | 116.2 (2) | O3B'—C4B'—C3B' | 115.3 (2) |
C5A'—C4A'—C3A' | 119.2 (2) | C5B'—C4B'—C3B' | 118.7 (3) |
C4A'—C5A'—C6A' | 121.1 (2) | C4B'—C5B'—C6B' | 120.9 (3) |
C4A'—C5A'—H5AB | 119.4 | C4B'—C5B'—H5BB | 119.6 |
C6A'—C5A'—H5AB | 119.4 | C6B'—C5B'—H5BB | 119.6 |
C5A'—C6A'—C1A' | 118.6 (2) | C5B'—C6B'—C1B' | 118.9 (3) |
C5A'—C6A'—C6A | 120.3 (2) | C5B'—C6B'—C6B | 120.7 (3) |
C1A'—C6A'—C6A | 121.0 (2) | C1B'—C6B'—C6B | 120.2 (3) |
O2A'—C7A'—O1A' | 123.4 (3) | O2B'—C7B'—O1B' | 123.8 (3) |
O2A'—C7A'—C8A' | 126.9 (3) | O2B'—C7B'—C8B' | 125.2 (4) |
O1A'—C7A'—C8A' | 109.6 (3) | O1B'—C7B'—C8B' | 110.9 (4) |
C7A'—C8A'—H8AD | 109.5 | C7B'—C8B'—H8BD | 109.5 |
C7A'—C8A'—H8AE | 109.5 | C7B'—C8B'—H8BE | 109.5 |
H8AD—C8A'—H8AE | 109.5 | H8BD—C8B'—H8BE | 109.5 |
C7A'—C8A'—H8AF | 109.5 | C7B'—C8B'—H8BF | 109.5 |
H8AD—C8A'—H8AF | 109.5 | H8BD—C8B'—H8BF | 109.5 |
H8AE—C8A'—H8AF | 109.5 | H8BE—C8B'—H8BF | 109.5 |
O3A'—C9A'—H9AD | 109.5 | O3B'—C9B'—H9BD | 109.5 |
O3A'—C9A'—H9AE | 109.5 | O3B'—C9B'—H9BE | 109.5 |
H9AD—C9A'—H9AE | 109.5 | H9BD—C9B'—H9BE | 109.5 |
O3A'—C9A'—H9AF | 109.5 | O3B'—C9B'—H9BF | 109.5 |
H9AD—C9A'—H9AF | 109.5 | H9BD—C9B'—H9BF | 109.5 |
H9AE—C9A'—H9AF | 109.5 | H9BE—C9B'—H9BF | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2AA···O3Ai | 0.95 | 2.59 | 3.506 (5) | 162 |
C5A—H5AA···O2B | 0.95 | 2.66 | 3.592 (4) | 167 |
C2A′—H2AB···O3B′ii | 0.95 | 2.61 | 3.512 (4) | 160 |
C9A′—H9AF···O1B′i | 0.98 | 2.54 | 3.485 (4) | 162 |
C2B—H2BA···O3Biii | 0.95 | 2.51 | 3.240 (6) | 134 |
C8B—H8BC···O2Aiv | 0.98 | 2.39 | 3.366 (6) | 172 |
C9B—H9BB···O1Biv | 0.98 | 2.61 | 3.401 (11) | 138 |
C9B′—H9BF···O1A′iv | 0.98 | 2.55 | 3.421 (4) | 148 |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) x, y, z+1; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1. |
Crystal data top
C16H18O4 | F(000) = 584 |
Mr = 274.30 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1000 (7) Å | Cell parameters from 2116 reflections |
b = 7.6709 (3) Å | θ = 4.1–26.7° |
c = 15.2881 (7) Å | µ = 0.09 mm−1 |
β = 110.181 (5)° | T = 294 K |
V = 1441.97 (12) Å3 | Fragment, colourless |
Z = 4 | 0.48 × 0.18 × 0.14 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 2334 reflections with I > 2σ(I) |
ω scans, thick slices | Rint = 0.055 |
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 29.5°, θmin = 3.8° |
Tmin = 0.92, Tmax = 0.99 | h = −17→17 |
42671 measured reflections | k = −10→10 |
3773 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | Primary atom site location: direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3773 reflections | Δρmax = 0.17 e Å−3 |
185 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.08189 (8) | 0.39901 (16) | 0.36020 (8) | 0.0599 (3) | |
O2 | 0.96587 (9) | 0.26155 (18) | 0.44747 (8) | 0.0683 (4) | |
O1' | 0.28686 (8) | 0.38500 (17) | 0.07344 (9) | 0.0679 (4) | |
O2' | 0.38943 (9) | 0.65661 (15) | 0.05161 (8) | 0.0582 (3) | |
C1 | 0.80803 (12) | 0.4743 (2) | 0.18792 (10) | 0.0483 (4) | |
H1A | 0.774002 | 0.524808 | 0.128166 | 0.058* | |
C2 | 0.92069 (12) | 0.4789 (2) | 0.22853 (11) | 0.0495 (4) | |
H2A | 0.962711 | 0.532951 | 0.196415 | 0.059* | |
C3 | 0.97181 (11) | 0.40596 (19) | 0.31468 (10) | 0.0460 (4) | |
C4 | 0.90877 (12) | 0.3293 (2) | 0.36221 (10) | 0.0469 (4) | |
C5 | 0.79721 (11) | 0.3254 (2) | 0.32164 (10) | 0.0444 (3) | |
H5A | 0.755064 | 0.273051 | 0.354161 | 0.053* | |
C6 | 0.74482 (11) | 0.39729 (19) | 0.23318 (9) | 0.0421 (3) | |
C7 | 1.14949 (14) | 0.4649 (3) | 0.31293 (15) | 0.0749 (6) | |
H7A | 1.225908 | 0.446381 | 0.351206 | 0.112* | |
H7B | 1.135931 | 0.589989 | 0.301545 | 0.112* | |
H7C | 1.133435 | 0.404089 | 0.253308 | 0.112* | |
C8 | 0.90805 (15) | 0.2138 (3) | 0.50611 (12) | 0.0756 (6) | |
H8A | 0.959412 | 0.179015 | 0.567120 | 0.113* | |
H8B | 0.859641 | 0.115859 | 0.478316 | 0.113* | |
H8C | 0.864814 | 0.313100 | 0.513742 | 0.113* | |
C1' | 0.56716 (12) | 0.24702 (19) | 0.20493 (10) | 0.0471 (4) | |
H1A' | 0.605421 | 0.151710 | 0.241286 | 0.057* | |
C2' | 0.45432 (12) | 0.2410 (2) | 0.16667 (10) | 0.0498 (4) | |
H2A' | 0.416481 | 0.141748 | 0.176797 | 0.060* | |
C3' | 0.39705 (12) | 0.3781 (2) | 0.11418 (10) | 0.0472 (4) | |
C4' | 0.45376 (12) | 0.52447 (19) | 0.10073 (9) | 0.0440 (3) | |
C5' | 0.56553 (12) | 0.52812 (19) | 0.13789 (9) | 0.0432 (3) | |
H5A' | 0.603399 | 0.626952 | 0.127304 | 0.052* | |
C6' | 0.62470 (11) | 0.38892 (18) | 0.19108 (9) | 0.0415 (3) | |
C7' | 0.22693 (15) | 0.2363 (3) | 0.08319 (17) | 0.0845 (7) | |
H7A' | 0.149758 | 0.253081 | 0.046717 | 0.127* | |
H7B' | 0.235743 | 0.220460 | 0.149015 | 0.127* | |
H7C' | 0.253983 | 0.132739 | 0.060555 | 0.127* | |
C8' | 0.44236 (15) | 0.8102 (2) | 0.03905 (14) | 0.0682 (5) | |
H8A' | 0.388087 | 0.894378 | 0.002435 | 0.102* | |
H8B' | 0.492443 | 0.782116 | 0.006013 | 0.102* | |
H8C' | 0.483249 | 0.860776 | 0.099983 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0405 (6) | 0.0703 (8) | 0.0650 (7) | −0.0062 (5) | 0.0133 (5) | 0.0046 (6) |
O2 | 0.0438 (6) | 0.1016 (10) | 0.0524 (6) | 0.0013 (6) | 0.0074 (5) | 0.0265 (6) |
O1' | 0.0390 (6) | 0.0774 (8) | 0.0770 (8) | 0.0020 (6) | 0.0071 (6) | 0.0186 (6) |
O2' | 0.0542 (7) | 0.0550 (7) | 0.0608 (7) | 0.0140 (5) | 0.0140 (5) | 0.0149 (5) |
C1 | 0.0518 (9) | 0.0499 (9) | 0.0414 (8) | 0.0026 (7) | 0.0137 (7) | 0.0053 (6) |
C2 | 0.0506 (9) | 0.0503 (9) | 0.0504 (8) | −0.0057 (7) | 0.0208 (7) | 0.0015 (7) |
C3 | 0.0384 (8) | 0.0467 (8) | 0.0507 (8) | −0.0019 (6) | 0.0125 (6) | −0.0029 (6) |
C4 | 0.0427 (8) | 0.0522 (9) | 0.0417 (8) | 0.0023 (6) | 0.0094 (6) | 0.0034 (6) |
C5 | 0.0413 (8) | 0.0514 (8) | 0.0411 (8) | 0.0015 (6) | 0.0149 (6) | 0.0030 (6) |
C6 | 0.0417 (8) | 0.0435 (8) | 0.0386 (7) | 0.0031 (6) | 0.0107 (6) | −0.0011 (6) |
C7 | 0.0509 (10) | 0.0881 (14) | 0.0892 (14) | −0.0103 (9) | 0.0288 (10) | 0.0068 (11) |
C8 | 0.0613 (11) | 0.1097 (16) | 0.0494 (10) | −0.0029 (11) | 0.0111 (9) | 0.0236 (10) |
C1' | 0.0476 (9) | 0.0471 (8) | 0.0418 (7) | 0.0052 (6) | 0.0093 (7) | 0.0083 (6) |
C2' | 0.0485 (9) | 0.0522 (9) | 0.0464 (8) | −0.0028 (7) | 0.0136 (7) | 0.0067 (7) |
C3' | 0.0403 (8) | 0.0576 (9) | 0.0403 (7) | 0.0037 (7) | 0.0096 (6) | 0.0021 (7) |
C4' | 0.0458 (8) | 0.0474 (8) | 0.0365 (7) | 0.0090 (6) | 0.0115 (6) | 0.0031 (6) |
C5' | 0.0470 (8) | 0.0423 (7) | 0.0398 (7) | 0.0017 (6) | 0.0144 (6) | 0.0009 (6) |
C6' | 0.0421 (8) | 0.0461 (8) | 0.0344 (7) | 0.0035 (6) | 0.0109 (6) | −0.0008 (6) |
C7' | 0.0482 (10) | 0.0937 (16) | 0.1006 (16) | −0.0128 (10) | 0.0118 (10) | 0.0129 (12) |
C8' | 0.0758 (12) | 0.0496 (10) | 0.0760 (12) | 0.0140 (9) | 0.0223 (10) | 0.0168 (9) |
Geometric parameters (Å, º) top
O1—C3 | 1.3689 (17) | C7—H7C | 0.9801 |
O1—C7 | 1.416 (2) | C8—H8A | 0.9801 |
O2—C4 | 1.3625 (17) | C8—H8B | 0.9801 |
O2—C8 | 1.407 (2) | C8—H8C | 0.9801 |
O1'—C3' | 1.3616 (17) | C1'—C6' | 1.381 (2) |
O1'—C7' | 1.422 (2) | C1'—C2' | 1.390 (2) |
O2'—C4' | 1.3656 (17) | C1'—H1A' | 0.9500 |
O2'—C8' | 1.414 (2) | C2'—C3' | 1.377 (2) |
C1—C6 | 1.381 (2) | C2'—H2A' | 0.9500 |
C1—C2 | 1.390 (2) | C3'—C4' | 1.400 (2) |
C1—H1A | 0.9500 | C4'—C5' | 1.376 (2) |
C2—C3 | 1.374 (2) | C5'—C6' | 1.4026 (19) |
C2—H2A | 0.9500 | C5'—H5A' | 0.9500 |
C3—C4 | 1.403 (2) | C7'—H7A' | 0.9801 |
C4—C5 | 1.3770 (19) | C7'—H7B' | 0.9801 |
C5—C6 | 1.4014 (19) | C7'—H7C' | 0.9801 |
C5—H5A | 0.9500 | C8'—H8A' | 0.9801 |
C6—C6' | 1.4818 (19) | C8'—H8B' | 0.9801 |
C7—H7A | 0.9801 | C8'—H8C' | 0.9801 |
C7—H7B | 0.9801 | | |
| | | |
C3—O1—C7 | 117.48 (13) | H8A—C8—H8C | 109.5 |
C4—O2—C8 | 118.06 (12) | H8B—C8—H8C | 109.5 |
C3'—O1'—C7' | 117.22 (13) | C6'—C1'—C2' | 121.26 (13) |
C4'—O2'—C8' | 117.06 (12) | C6'—C1'—H1A' | 119.4 |
C6—C1—C2 | 120.97 (13) | C2'—C1'—H1A' | 119.4 |
C6—C1—H1A | 119.5 | C3'—C2'—C1' | 120.41 (14) |
C2—C1—H1A | 119.5 | C3'—C2'—H2A' | 119.8 |
C3—C2—C1 | 120.60 (14) | C1'—C2'—H2A' | 119.8 |
C3—C2—H2A | 119.7 | O1'—C3'—C2' | 125.07 (14) |
C1—C2—H2A | 119.7 | O1'—C3'—C4' | 115.73 (13) |
O1—C3—C2 | 125.64 (14) | C2'—C3'—C4' | 119.20 (13) |
O1—C3—C4 | 115.17 (13) | O2'—C4'—C5' | 125.37 (14) |
C2—C3—C4 | 119.18 (13) | O2'—C4'—C3' | 114.71 (13) |
O2—C4—C5 | 124.71 (14) | C5'—C4'—C3' | 119.91 (13) |
O2—C4—C3 | 115.36 (13) | C4'—C5'—C6' | 121.36 (14) |
C5—C4—C3 | 119.92 (13) | C4'—C5'—H5A' | 119.3 |
C4—C5—C6 | 121.08 (14) | C6'—C5'—H5A' | 119.3 |
C4—C5—H5A | 119.5 | C1'—C6'—C5' | 117.85 (13) |
C6—C5—H5A | 119.5 | C1'—C6'—C6 | 121.43 (12) |
C1—C6—C5 | 118.23 (13) | C5'—C6'—C6 | 120.70 (13) |
C1—C6—C6' | 122.08 (12) | O1'—C7'—H7A' | 109.5 |
C5—C6—C6' | 119.69 (13) | O1'—C7'—H7B' | 109.5 |
O1—C7—H7A | 109.5 | H7A'—C7'—H7B' | 109.5 |
O1—C7—H7B | 109.5 | O1'—C7'—H7C' | 109.5 |
H7A—C7—H7B | 109.5 | H7A'—C7'—H7C' | 109.5 |
O1—C7—H7C | 109.5 | H7B'—C7'—H7C' | 109.5 |
H7A—C7—H7C | 109.5 | O2'—C8'—H8A' | 109.5 |
H7B—C7—H7C | 109.5 | O2'—C8'—H8B' | 109.5 |
O2—C8—H8A | 109.5 | H8A'—C8'—H8B' | 109.5 |
O2—C8—H8B | 109.5 | O2'—C8'—H8C' | 109.5 |
H8A—C8—H8B | 109.5 | H8A'—C8'—H8C' | 109.5 |
O2—C8—H8C | 109.5 | H8B'—C8'—H8C' | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O1′i | 0.98 | 2.53 | 3.495 (2) | 168 |
C7′—H7A′···O2ii | 0.98 | 2.37 | 3.332 (2) | 169 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, −y+1/2, z−1/2. |