The title compound, C13H16O3, crystallizes in space group Pna21 with Z = 8. The two independent molecules are related by pseudosymmetry elements. The structure can be derived from the higher symmetric space group Pnam by translating the x coordinates of molecule 2 by -1/4 with respect to those of molecule 1.
Supporting information
CCDC reference: 203010
Key indicators
- Single-crystal X-ray study
- T = 142 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.099
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ C5C6
H18 C5C6
PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ C5C6
C18 C5C6
PLAT_718 Alert C D-H..A Unknown or Inconsistent Label ........ C5C6
C18 H18 C5C6
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 32.00
From the CIF: _reflns_number_total 3878
Count of symmetry unique reflns 4027
Completeness (_total/calc) 96.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.
2-cyclopentyl-2-hydroxy-2-phenylacetic acid
top
Crystal data top
C13H16O3 | Dx = 1.291 Mg m−3 |
Mr = 220.26 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 194 reflections |
a = 11.1981 (14) Å | θ = 3–23° |
b = 8.4864 (15) Å | µ = 0.09 mm−1 |
c = 23.853 (3) Å | T = 142 K |
V = 2266.8 (6) Å3 | Rod, colorless |
Z = 8 | 0.50 × 0.45 × 0.40 mm |
F(000) = 944 | |
Data collection top
Siemens SMART 1K CCD diffractometer | 3878 independent reflections |
Radiation source: normal-focus sealed tube | 3597 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 32.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS, Sheldrick, 2000) | h = −16→16 |
Tmin = 0.935, Tmax = 0.964 | k = −11→10 |
37645 measured reflections | l = −34→35 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.35P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3878 reflections | Δρmax = 0.39 e Å−3 |
294 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (10) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.24292 (9) | 0.69776 (13) | 0.17541 (4) | 0.0154 (2) | |
H01 | 0.2528 | 0.6966 | 0.2103 | 0.023* | |
O2 | 0.45966 (13) | 0.74955 (15) | 0.21656 (7) | 0.0219 (3) | |
O3 | 0.54776 (10) | 0.65491 (15) | 0.13892 (5) | 0.0217 (2) | |
H03 | 0.6086 | 0.6972 | 0.1530 | 0.033* | |
C1 | 0.33693 (12) | 0.61250 (17) | 0.14912 (6) | 0.0127 (2) | |
C2 | 0.45484 (13) | 0.67984 (17) | 0.17180 (6) | 0.0149 (3) | |
C3 | 0.32922 (12) | 0.43588 (18) | 0.16329 (6) | 0.0144 (3) | |
C4 | 0.22992 (14) | 0.37631 (19) | 0.19160 (7) | 0.0188 (3) | |
H4 | 0.1696 | 0.4461 | 0.2046 | 0.023* | |
C5 | 0.21889 (17) | 0.2151 (2) | 0.20089 (8) | 0.0243 (3) | |
H5 | 0.1510 | 0.1755 | 0.2201 | 0.029* | |
C6 | 0.30667 (16) | 0.1115 (2) | 0.18220 (8) | 0.0242 (3) | |
H6 | 0.2986 | 0.0014 | 0.1883 | 0.029* | |
C7 | 0.40616 (17) | 0.1710 (2) | 0.15460 (8) | 0.0241 (4) | |
H7 | 0.4667 | 0.1010 | 0.1420 | 0.029* | |
C8 | 0.41818 (15) | 0.3315 (2) | 0.14521 (7) | 0.0188 (3) | |
H8 | 0.4869 | 0.3708 | 0.1265 | 0.023* | |
C9 | 0.32624 (12) | 0.63599 (18) | 0.08517 (6) | 0.0147 (3) | |
H9 | 0.3945 | 0.5790 | 0.0673 | 0.018* | |
C10 | 0.33064 (15) | 0.8069 (2) | 0.06504 (7) | 0.0205 (3) | |
H10A | 0.4133 | 0.8482 | 0.0655 | 0.025* | |
H10B | 0.2793 | 0.8755 | 0.0884 | 0.025* | |
C11 | 0.28261 (16) | 0.7941 (2) | 0.00491 (7) | 0.0258 (3) | |
H11A | 0.2552 | 0.8978 | −0.0091 | 0.031* | |
H11B | 0.3443 | 0.7522 | −0.0208 | 0.031* | |
C12 | 0.17788 (17) | 0.6789 (3) | 0.01058 (8) | 0.0307 (4) | |
H12A | 0.1675 | 0.6176 | −0.0244 | 0.037* | |
H12B | 0.1029 | 0.7366 | 0.0185 | 0.037* | |
C13 | 0.20974 (14) | 0.56852 (19) | 0.05992 (7) | 0.0193 (3) | |
H13A | 0.2223 | 0.4594 | 0.0465 | 0.023* | |
H13B | 0.1451 | 0.5681 | 0.0882 | 0.023* | |
O4 | 0.49603 (9) | 0.70593 (14) | 0.33005 (5) | 0.0166 (2) | |
H04 | 0.5120 | 0.7185 | 0.2959 | 0.025* | |
O5 | 0.71172 (13) | 0.76173 (17) | 0.29073 (7) | 0.0259 (3) | |
O6 | 0.80046 (9) | 0.65735 (15) | 0.36578 (5) | 0.0211 (2) | |
H06 | 0.8617 | 0.6994 | 0.3520 | 0.032* | |
C14 | 0.58966 (12) | 0.62003 (17) | 0.35621 (6) | 0.0131 (2) | |
C15 | 0.70774 (13) | 0.68780 (17) | 0.33365 (6) | 0.0154 (3) | |
C16 | 0.58168 (13) | 0.44424 (18) | 0.34164 (6) | 0.0148 (3) | |
C17 | 0.48114 (14) | 0.3864 (2) | 0.31417 (7) | 0.0208 (3) | |
H17 | 0.4204 | 0.4569 | 0.3022 | 0.025* | |
C18 | 0.46937 (18) | 0.2252 (2) | 0.30409 (9) | 0.0267 (4) | |
H18 | 0.3999 | 0.1865 | 0.2859 | 0.032* | |
C19 | 0.55790 (18) | 0.1214 (2) | 0.32034 (8) | 0.0278 (4) | |
H19 | 0.5495 | 0.0118 | 0.3133 | 0.033* | |
C20 | 0.65948 (18) | 0.1786 (2) | 0.34717 (8) | 0.0244 (4) | |
H20 | 0.7212 | 0.1082 | 0.3581 | 0.029* | |
C21 | 0.67044 (15) | 0.3392 (2) | 0.35795 (7) | 0.0191 (3) | |
H21 | 0.7394 | 0.3776 | 0.3767 | 0.023* | |
C22 | 0.57962 (13) | 0.64235 (18) | 0.42003 (6) | 0.0149 (3) | |
H22 | 0.6481 | 0.5853 | 0.4377 | 0.018* | |
C23 | 0.58391 (15) | 0.81390 (19) | 0.44056 (7) | 0.0199 (3) | |
H23A | 0.6666 | 0.8551 | 0.4404 | 0.024* | |
H23B | 0.5329 | 0.8829 | 0.4172 | 0.024* | |
C24 | 0.53540 (16) | 0.8007 (2) | 0.50029 (8) | 0.0259 (3) | |
H24A | 0.5087 | 0.9045 | 0.5145 | 0.031* | |
H24B | 0.5964 | 0.7573 | 0.5261 | 0.031* | |
C25 | 0.42991 (17) | 0.6874 (3) | 0.49392 (8) | 0.0309 (4) | |
H25A | 0.3560 | 0.7461 | 0.4849 | 0.037* | |
H25B | 0.4170 | 0.6276 | 0.5291 | 0.037* | |
C26 | 0.46313 (14) | 0.5749 (2) | 0.44566 (7) | 0.0194 (3) | |
H26A | 0.3988 | 0.5719 | 0.4172 | 0.023* | |
H26B | 0.4764 | 0.4669 | 0.4600 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0132 (4) | 0.0205 (5) | 0.0126 (4) | 0.0039 (4) | −0.0003 (4) | −0.0014 (4) |
O2 | 0.0177 (6) | 0.0313 (7) | 0.0167 (7) | −0.0036 (4) | −0.0023 (5) | −0.0053 (4) |
O3 | 0.0122 (5) | 0.0303 (6) | 0.0226 (5) | −0.0049 (4) | 0.0015 (4) | −0.0062 (5) |
C1 | 0.0106 (5) | 0.0151 (6) | 0.0123 (6) | −0.0002 (4) | 0.0000 (4) | −0.0005 (4) |
C2 | 0.0138 (6) | 0.0165 (6) | 0.0144 (6) | −0.0011 (4) | −0.0014 (5) | 0.0017 (5) |
C3 | 0.0134 (6) | 0.0161 (6) | 0.0139 (6) | −0.0006 (4) | −0.0018 (5) | −0.0003 (5) |
C4 | 0.0157 (6) | 0.0201 (7) | 0.0206 (7) | −0.0024 (5) | 0.0016 (5) | 0.0021 (6) |
C5 | 0.0237 (8) | 0.0240 (8) | 0.0252 (9) | −0.0074 (7) | 0.0006 (7) | 0.0046 (8) |
C6 | 0.0306 (8) | 0.0159 (7) | 0.0260 (8) | −0.0025 (6) | −0.0029 (7) | 0.0008 (6) |
C7 | 0.0268 (8) | 0.0213 (8) | 0.0242 (8) | 0.0043 (6) | −0.0023 (7) | −0.0044 (6) |
C8 | 0.0179 (7) | 0.0213 (8) | 0.0171 (7) | 0.0020 (5) | 0.0009 (5) | −0.0014 (6) |
C9 | 0.0148 (6) | 0.0179 (7) | 0.0115 (6) | −0.0005 (4) | −0.0005 (5) | −0.0005 (5) |
C10 | 0.0230 (7) | 0.0206 (8) | 0.0181 (7) | −0.0020 (5) | 0.0006 (6) | 0.0037 (6) |
C11 | 0.0254 (8) | 0.0345 (9) | 0.0175 (7) | 0.0001 (7) | −0.0008 (6) | 0.0088 (7) |
C12 | 0.0249 (8) | 0.0446 (11) | 0.0225 (8) | −0.0054 (7) | −0.0086 (6) | 0.0126 (7) |
C13 | 0.0196 (6) | 0.0219 (7) | 0.0165 (6) | −0.0023 (5) | −0.0056 (5) | −0.0013 (6) |
O4 | 0.0132 (5) | 0.0220 (5) | 0.0146 (5) | 0.0040 (4) | 0.0001 (4) | 0.0025 (4) |
O5 | 0.0201 (7) | 0.0402 (8) | 0.0173 (7) | −0.0031 (5) | 0.0030 (6) | 0.0088 (5) |
O6 | 0.0111 (4) | 0.0294 (6) | 0.0228 (5) | −0.0038 (4) | −0.0013 (4) | 0.0068 (5) |
C14 | 0.0106 (5) | 0.0172 (7) | 0.0116 (6) | 0.0009 (4) | 0.0002 (4) | −0.0002 (5) |
C15 | 0.0133 (6) | 0.0175 (7) | 0.0153 (6) | −0.0007 (4) | 0.0017 (5) | −0.0015 (5) |
C16 | 0.0139 (6) | 0.0179 (7) | 0.0125 (5) | −0.0015 (5) | 0.0014 (4) | −0.0013 (5) |
C17 | 0.0174 (7) | 0.0243 (8) | 0.0208 (7) | −0.0040 (5) | −0.0012 (5) | −0.0034 (6) |
C18 | 0.0254 (8) | 0.0280 (9) | 0.0267 (9) | −0.0082 (7) | 0.0007 (7) | −0.0058 (8) |
C19 | 0.0370 (10) | 0.0176 (7) | 0.0287 (8) | −0.0058 (6) | 0.0074 (8) | −0.0030 (6) |
C20 | 0.0276 (8) | 0.0188 (8) | 0.0270 (9) | 0.0034 (6) | 0.0036 (7) | 0.0007 (6) |
C21 | 0.0184 (7) | 0.0178 (7) | 0.0210 (7) | 0.0017 (5) | 0.0001 (6) | 0.0009 (6) |
C22 | 0.0146 (6) | 0.0177 (7) | 0.0124 (6) | −0.0005 (5) | 0.0004 (5) | −0.0001 (5) |
C23 | 0.0247 (7) | 0.0186 (8) | 0.0165 (7) | −0.0008 (5) | 0.0004 (6) | −0.0033 (6) |
C24 | 0.0272 (8) | 0.0332 (9) | 0.0175 (7) | −0.0005 (7) | 0.0023 (6) | −0.0084 (7) |
C25 | 0.0249 (8) | 0.0467 (12) | 0.0211 (7) | −0.0049 (7) | 0.0079 (7) | −0.0111 (7) |
C26 | 0.0188 (6) | 0.0232 (7) | 0.0163 (6) | −0.0019 (5) | 0.0042 (5) | 0.0006 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.4230 (16) | O4—C14 | 1.4213 (16) |
O1—H01 | 0.8400 | O4—H04 | 0.8400 |
O2—C2 | 1.222 (2) | O5—C15 | 1.201 (2) |
O3—C2 | 1.3200 (18) | O6—C15 | 1.3163 (18) |
O3—H03 | 0.8400 | O6—H06 | 0.8400 |
C1—C2 | 1.5371 (19) | C14—C16 | 1.534 (2) |
C1—C3 | 1.539 (2) | C14—C22 | 1.5380 (19) |
C1—C9 | 1.543 (2) | C14—C15 | 1.5391 (19) |
C3—C4 | 1.396 (2) | C16—C21 | 1.390 (2) |
C3—C8 | 1.401 (2) | C16—C17 | 1.392 (2) |
C4—C5 | 1.391 (2) | C17—C18 | 1.395 (3) |
C4—H4 | 0.9500 | C17—H17 | 0.9500 |
C5—C6 | 1.392 (3) | C18—C19 | 1.382 (3) |
C5—H5 | 0.9500 | C18—H18 | 0.9500 |
C6—C7 | 1.389 (3) | C19—C20 | 1.393 (3) |
C6—H6 | 0.9500 | C19—H19 | 0.9500 |
C7—C8 | 1.387 (3) | C20—C21 | 1.393 (2) |
C7—H7 | 0.9500 | C20—H20 | 0.9500 |
C8—H8 | 0.9500 | C21—H21 | 0.9500 |
C9—C10 | 1.528 (2) | C22—C23 | 1.537 (2) |
C9—C13 | 1.547 (2) | C22—C26 | 1.550 (2) |
C9—H9 | 1.0000 | C22—H22 | 1.0000 |
C10—C11 | 1.536 (2) | C23—C24 | 1.529 (2) |
C10—H10A | 0.9900 | C23—H23A | 0.9900 |
C10—H10B | 0.9900 | C23—H23B | 0.9900 |
C11—C12 | 1.533 (3) | C24—C25 | 1.531 (3) |
C11—H11A | 0.9900 | C24—H24A | 0.9900 |
C11—H11B | 0.9900 | C24—H24B | 0.9900 |
C12—C13 | 1.546 (2) | C25—C26 | 1.541 (2) |
C12—H12A | 0.9900 | C25—H25A | 0.9900 |
C12—H12B | 0.9900 | C25—H25B | 0.9900 |
C13—H13A | 0.9900 | C26—H26A | 0.9900 |
C13—H13B | 0.9900 | C26—H26B | 0.9900 |
| | | |
C1—O1—H01 | 109.5 | C14—O4—H04 | 109.5 |
C2—O3—H03 | 109.5 | C15—O6—H06 | 109.5 |
O1—C1—C2 | 106.94 (11) | O4—C14—C16 | 110.87 (11) |
O1—C1—C3 | 110.91 (11) | O4—C14—C22 | 108.51 (11) |
C2—C1—C3 | 109.44 (11) | C16—C14—C22 | 109.85 (12) |
O1—C1—C9 | 108.22 (11) | O4—C14—C15 | 106.77 (11) |
C2—C1—C9 | 111.51 (12) | C16—C14—C15 | 109.52 (11) |
C3—C1—C9 | 109.79 (12) | C22—C14—C15 | 111.28 (12) |
O2—C2—O3 | 124.19 (14) | O5—C15—O6 | 124.71 (15) |
O2—C2—C1 | 121.70 (14) | O5—C15—C14 | 121.67 (14) |
O3—C2—C1 | 114.10 (12) | O6—C15—C14 | 113.62 (12) |
C4—C3—C8 | 119.10 (15) | C21—C16—C17 | 118.94 (15) |
C4—C3—C1 | 120.25 (13) | C21—C16—C14 | 121.21 (13) |
C8—C3—C1 | 120.55 (13) | C17—C16—C14 | 119.76 (13) |
C5—C4—C3 | 120.26 (15) | C16—C17—C18 | 120.21 (16) |
C5—C4—H4 | 119.9 | C16—C17—H17 | 119.9 |
C3—C4—H4 | 119.9 | C18—C17—H17 | 119.9 |
C4—C5—C6 | 120.49 (16) | C19—C18—C17 | 120.60 (17) |
C4—C5—H5 | 119.8 | C19—C18—H18 | 119.7 |
C6—C5—H5 | 119.8 | C17—C18—H18 | 119.7 |
C7—C6—C5 | 119.22 (16) | C18—C19—C20 | 119.51 (17) |
C7—C6—H6 | 120.4 | C18—C19—H19 | 120.2 |
C5—C6—H6 | 120.4 | C20—C19—H19 | 120.2 |
C8—C7—C6 | 120.76 (16) | C19—C20—C21 | 119.88 (17) |
C8—C7—H7 | 119.6 | C19—C20—H20 | 120.1 |
C6—C7—H7 | 119.6 | C21—C20—H20 | 120.1 |
C7—C8—C3 | 120.15 (16) | C16—C21—C20 | 120.84 (16) |
C7—C8—H8 | 119.9 | C16—C21—H21 | 119.6 |
C3—C8—H8 | 119.9 | C20—C21—H21 | 119.6 |
C10—C9—C1 | 115.51 (12) | C23—C22—C14 | 115.45 (13) |
C10—C9—C13 | 104.83 (12) | C23—C22—C26 | 104.49 (13) |
C1—C9—C13 | 113.74 (12) | C14—C22—C26 | 113.99 (12) |
C10—C9—H9 | 107.4 | C23—C22—H22 | 107.5 |
C1—C9—H9 | 107.4 | C14—C22—H22 | 107.5 |
C13—C9—H9 | 107.4 | C26—C22—H22 | 107.5 |
C9—C10—C11 | 102.43 (14) | C24—C23—C22 | 102.51 (14) |
C9—C10—H10A | 111.3 | C24—C23—H23A | 111.3 |
C11—C10—H10A | 111.3 | C22—C23—H23A | 111.3 |
C9—C10—H10B | 111.3 | C24—C23—H23B | 111.3 |
C11—C10—H10B | 111.3 | C22—C23—H23B | 111.3 |
H10A—C10—H10B | 109.2 | H23A—C23—H23B | 109.2 |
C12—C11—C10 | 103.34 (14) | C23—C24—C25 | 103.16 (14) |
C12—C11—H11A | 111.1 | C23—C24—H24A | 111.1 |
C10—C11—H11A | 111.1 | C25—C24—H24A | 111.1 |
C12—C11—H11B | 111.1 | C23—C24—H24B | 111.1 |
C10—C11—H11B | 111.1 | C25—C24—H24B | 111.1 |
H11A—C11—H11B | 109.1 | H24A—C24—H24B | 109.1 |
C11—C12—C13 | 106.08 (14) | C24—C25—C26 | 106.07 (14) |
C11—C12—H12A | 110.5 | C24—C25—H25A | 110.5 |
C13—C12—H12A | 110.5 | C26—C25—H25A | 110.5 |
C11—C12—H12B | 110.5 | C24—C25—H25B | 110.5 |
C13—C12—H12B | 110.5 | C26—C25—H25B | 110.5 |
H12A—C12—H12B | 108.7 | H25A—C25—H25B | 108.7 |
C12—C13—C9 | 105.48 (13) | C25—C26—C22 | 105.63 (13) |
C12—C13—H13A | 110.6 | C25—C26—H26A | 110.6 |
C9—C13—H13A | 110.6 | C22—C26—H26A | 110.6 |
C12—C13—H13B | 110.6 | C25—C26—H26B | 110.6 |
C9—C13—H13B | 110.6 | C22—C26—H26B | 110.6 |
H13A—C13—H13B | 108.8 | H26A—C26—H26B | 108.7 |
| | | |
O1—C1—C2—O2 | 22.53 (19) | O4—C14—C15—O5 | −19.94 (19) |
C3—C1—C2—O2 | −97.68 (17) | C16—C14—C15—O5 | 100.16 (17) |
C9—C1—C2—O2 | 140.65 (15) | C22—C14—C15—O5 | −138.19 (16) |
O1—C1—C2—O3 | −157.62 (13) | O4—C14—C15—O6 | 159.70 (13) |
C3—C1—C2—O3 | 82.16 (15) | C16—C14—C15—O6 | −80.20 (15) |
C9—C1—C2—O3 | −39.51 (17) | C22—C14—C15—O6 | 41.45 (17) |
O1—C1—C3—C4 | 8.44 (18) | O4—C14—C16—C21 | 173.64 (14) |
C2—C1—C3—C4 | 126.19 (14) | C22—C14—C16—C21 | −66.43 (17) |
C9—C1—C3—C4 | −111.11 (15) | C15—C14—C16—C21 | 56.08 (18) |
O1—C1—C3—C8 | −175.23 (13) | O4—C14—C16—C17 | −9.75 (19) |
C2—C1—C3—C8 | −57.48 (18) | C22—C14—C16—C17 | 110.18 (15) |
C9—C1—C3—C8 | 65.22 (17) | C15—C14—C16—C17 | −127.31 (14) |
C8—C3—C4—C5 | −1.0 (2) | C21—C16—C17—C18 | 1.0 (2) |
C1—C3—C4—C5 | 175.40 (15) | C14—C16—C17—C18 | −175.68 (16) |
C3—C4—C5—C6 | 0.1 (3) | C16—C17—C18—C19 | −1.1 (3) |
C4—C5—C6—C7 | 0.6 (3) | C17—C18—C19—C20 | 0.2 (3) |
C5—C6—C7—C8 | −0.5 (3) | C18—C19—C20—C21 | 0.7 (3) |
C6—C7—C8—C3 | −0.4 (3) | C17—C16—C21—C20 | −0.1 (2) |
C4—C3—C8—C7 | 1.1 (2) | C14—C16—C21—C20 | 176.56 (15) |
C1—C3—C8—C7 | −175.27 (14) | C19—C20—C21—C16 | −0.8 (3) |
O1—C1—C9—C10 | 57.96 (16) | O4—C14—C22—C23 | −57.56 (16) |
C2—C1—C9—C10 | −59.38 (16) | C16—C14—C22—C23 | −178.91 (12) |
C3—C1—C9—C10 | 179.15 (11) | C15—C14—C22—C23 | 59.63 (16) |
O1—C1—C9—C13 | −63.36 (16) | O4—C14—C22—C26 | 63.44 (16) |
C2—C1—C9—C13 | 179.30 (12) | C16—C14—C22—C26 | −57.91 (16) |
C3—C1—C9—C13 | 57.83 (15) | C15—C14—C22—C26 | −179.37 (12) |
C1—C9—C10—C11 | −164.35 (13) | C14—C22—C23—C24 | 163.72 (13) |
C13—C9—C10—C11 | −38.34 (16) | C26—C22—C23—C24 | 37.71 (16) |
C9—C10—C11—C12 | 41.92 (17) | C22—C23—C24—C25 | −42.55 (17) |
C10—C11—C12—C13 | −29.6 (2) | C23—C24—C25—C26 | 31.3 (2) |
C11—C12—C13—C9 | 6.00 (19) | C24—C25—C26—C22 | −7.86 (19) |
C10—C9—C13—C12 | 20.07 (17) | C23—C22—C26—C25 | −18.42 (17) |
C1—C9—C13—C12 | 147.17 (14) | C14—C22—C26—C25 | −145.35 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H01···O5i | 0.84 | 2.00 | 2.794 (2) | 156 |
O3—H03···O1ii | 0.84 | 1.83 | 2.664 (2) | 173 |
O4—H04···O2 | 0.84 | 2.00 | 2.762 (2) | 151 |
O6—H06···O4ii | 0.84 | 1.78 | 2.621 (2) | 174 |
C5—H5···Cg2iii | 0.95 | 2.82 | 3.521 (2) | 132 |
C18—H18···C5C6 | 0.95 | 2.73 | 3.582 (2) | 150 |
C6—H6···O1iv | 0.95 | 2.67 | 3.587 (2) | 163 |
C19—H19···O4iv | 0.95 | 2.69 | 3.601 (2) | 160 |
Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x+1/2, −y+3/2, z; (iii) x−1/2, −y+1/2, z; (iv) x, y−1, z. |