The title compound, C
24H
26O
6·CHCl
3, which we named prunifloxanthone A, was isolated for the first time from the roots of
Cratoxylum formosum ssp.
pruniflorum and has never been isolated from any other natural resources as yet. The xanthone ring systems of the molecules are stacked along the
a axis, with significant π–π interactions. In addition, O—H
O hydrogen bonds link glide-related molecules into a chain along [201].
Supporting information
CCDC reference: 294139
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.063
- wR factor = 0.218
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
1,6,7-Trihydroxy-3-methoxy-2,8-bis(3-methyl-2-butenyl)-9
H-xanthen-9-one
chloroform solvate
top
Crystal data top
C24H26O6·CHCl3 | F(000) = 1104 |
Mr = 529.82 | Dx = 1.428 Mg m−3 |
Monoclinic, P21/c | Melting point = 395–397 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.9059 (1) Å | Cell parameters from 4316 reflections |
b = 23.3103 (3) Å | θ = 1.4–26.0° |
c = 18.4042 (2) Å | µ = 0.41 mm−1 |
β = 103.438 (1)° | T = 100 K |
V = 2464.31 (6) Å3 | Needle, yellow |
Z = 4 | 0.37 × 0.22 × 0.13 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 4316 independent reflections |
Radiation source: fine-focus sealed tube | 3713 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.4° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −27→27 |
Tmin = 0.897, Tmax = 0.948 | l = −21→21 |
38758 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.218 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1248P)2 + 5.5318P] where P = (Fo2 + 2Fc2)/3 |
4316 reflections | (Δ/σ)max = 0.001 |
315 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.74 e Å−3 |
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 | |
Cl1 | 1.0112 (3) | 0.48154 (5) | 0.40237 (7) | 0.0592 (4) | |
Cl2 | 1.0310 (3) | 0.36816 (6) | 0.46764 (7) | 0.0565 (4) | |
Cl3 | 0.5920 (2) | 0.42519 (7) | 0.41845 (8) | 0.0666 (5) | |
C25 | 0.8704 (8) | 0.41528 (19) | 0.4016 (2) | 0.0395 (10) | |
H25 | 0.8525 | 0.3981 | 0.3520 | 0.047* | |
O1 | 0.3494 (4) | 0.27247 (10) | 0.35848 (12) | 0.0188 (5) | |
H1 | 0.2439 | 0.2961 | 0.3478 | 0.028* | |
O2 | −0.0216 (4) | 0.31757 (10) | 0.28782 (12) | 0.0200 (5) | |
O3 | −0.0283 (4) | 0.20722 (10) | 0.11384 (12) | 0.0180 (5) | |
O4 | 0.7020 (4) | 0.13068 (10) | 0.23917 (13) | 0.0224 (5) | |
O5 | −0.7695 (4) | 0.27110 (11) | −0.01993 (13) | 0.0218 (5) | |
H5 | −0.7272 | 0.2582 | −0.0561 | 0.033* | |
O6 | −0.8149 (4) | 0.33811 (10) | 0.09166 (13) | 0.0217 (5) | |
H6 | −0.8992 | 0.3324 | 0.0502 | 0.033* | |
C1 | 0.3427 (6) | 0.23721 (14) | 0.29880 (17) | 0.0173 (7) | |
C2 | 0.5270 (6) | 0.20017 (14) | 0.29977 (18) | 0.0179 (7) | |
C3 | 0.5139 (6) | 0.16527 (14) | 0.23659 (19) | 0.0189 (7) | |
C4 | 0.3242 (6) | 0.16689 (14) | 0.17481 (18) | 0.0176 (7) | |
H4 | 0.3174 | 0.1429 | 0.1340 | 0.021* | |
C5 | 0.1483 (6) | 0.20511 (14) | 0.17650 (17) | 0.0169 (7) | |
C6 | 0.1479 (6) | 0.24141 (14) | 0.23682 (17) | 0.0168 (7) | |
C7 | −0.0363 (6) | 0.28225 (13) | 0.23531 (17) | 0.0166 (7) | |
C8 | −0.2331 (6) | 0.27977 (13) | 0.17045 (17) | 0.0163 (7) | |
C9 | −0.2171 (5) | 0.24270 (13) | 0.11215 (18) | 0.0157 (6) | |
C10 | −0.3900 (6) | 0.23814 (14) | 0.04687 (17) | 0.0180 (7) | |
H10 | −0.3730 | 0.2137 | 0.0086 | 0.022* | |
C11 | −0.5877 (6) | 0.27097 (14) | 0.04063 (18) | 0.0181 (7) | |
C12 | −0.6128 (5) | 0.30731 (14) | 0.09907 (18) | 0.0163 (7) | |
C13 | −0.4392 (6) | 0.31281 (14) | 0.16351 (17) | 0.0168 (7) | |
C14 | −0.4790 (6) | 0.35472 (14) | 0.22252 (18) | 0.0175 (7) | |
H14A | −0.6450 | 0.3596 | 0.2178 | 0.021* | |
H14B | −0.4122 | 0.3393 | 0.2718 | 0.021* | |
C15 | −0.3701 (6) | 0.41234 (14) | 0.21442 (17) | 0.0181 (7) | |
H15 | −0.2139 | 0.4124 | 0.2128 | 0.022* | |
C16 | −0.4763 (6) | 0.46262 (15) | 0.20939 (19) | 0.0222 (7) | |
C17 | −0.3506 (7) | 0.51769 (15) | 0.2028 (2) | 0.0296 (8) | |
H17A | −0.1957 | 0.5093 | 0.1979 | 0.044* | |
H17B | −0.3429 | 0.5405 | 0.2467 | 0.044* | |
H17C | −0.4327 | 0.5384 | 0.1596 | 0.044* | |
C18 | −0.7293 (6) | 0.46924 (17) | 0.2106 (2) | 0.0329 (9) | |
H18A | −0.8196 | 0.4406 | 0.1792 | 0.049* | |
H18B | −0.7824 | 0.5067 | 0.1926 | 0.049* | |
H18C | −0.7470 | 0.4647 | 0.2609 | 0.049* | |
C19 | 0.7080 (7) | 0.09709 (15) | 0.1750 (2) | 0.0269 (8) | |
H19A | 0.8546 | 0.0775 | 0.1828 | 0.040* | |
H19B | 0.6894 | 0.1216 | 0.1322 | 0.040* | |
H19C | 0.5840 | 0.0695 | 0.1669 | 0.040* | |
C20 | 0.7353 (6) | 0.19688 (14) | 0.36579 (18) | 0.0190 (7) | |
H20A | 0.8732 | 0.1876 | 0.3480 | 0.023* | |
H20B | 0.7597 | 0.2340 | 0.3901 | 0.023* | |
C21 | 0.7022 (6) | 0.15230 (14) | 0.42181 (18) | 0.0185 (7) | |
H21 | 0.5721 | 0.1572 | 0.4416 | 0.022* | |
C22 | 0.8338 (6) | 0.10712 (14) | 0.44667 (18) | 0.0210 (7) | |
C23 | 1.0530 (7) | 0.09147 (16) | 0.4224 (2) | 0.0306 (9) | |
H23A | 1.0705 | 0.1163 | 0.3824 | 0.046* | |
H23B | 1.0432 | 0.0524 | 0.4056 | 0.046* | |
H23C | 1.1849 | 0.0958 | 0.4638 | 0.046* | |
C24 | 0.7706 (7) | 0.06684 (17) | 0.5029 (2) | 0.0310 (9) | |
H24A | 0.6343 | 0.0808 | 0.5172 | 0.046* | |
H24B | 0.8974 | 0.0646 | 0.5462 | 0.046* | |
H24C | 0.7397 | 0.0294 | 0.4811 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0822 (10) | 0.0448 (7) | 0.0529 (7) | −0.0184 (6) | 0.0209 (7) | 0.0011 (5) |
Cl2 | 0.0770 (9) | 0.0522 (7) | 0.0349 (6) | 0.0067 (6) | 0.0020 (6) | 0.0122 (5) |
Cl3 | 0.0477 (8) | 0.0941 (11) | 0.0617 (9) | −0.0023 (7) | 0.0203 (6) | −0.0096 (7) |
C25 | 0.050 (3) | 0.039 (2) | 0.029 (2) | 0.000 (2) | 0.0079 (19) | 0.0008 (17) |
O1 | 0.0178 (12) | 0.0235 (12) | 0.0136 (11) | 0.0018 (9) | 0.0007 (9) | 0.0002 (9) |
O2 | 0.0211 (12) | 0.0210 (12) | 0.0163 (11) | 0.0031 (9) | 0.0009 (9) | −0.0027 (9) |
O3 | 0.0168 (11) | 0.0209 (12) | 0.0148 (11) | 0.0028 (9) | 0.0007 (9) | −0.0016 (9) |
O4 | 0.0186 (12) | 0.0221 (12) | 0.0249 (13) | 0.0056 (10) | 0.0015 (10) | 0.0007 (10) |
O5 | 0.0159 (12) | 0.0314 (13) | 0.0150 (11) | 0.0046 (10) | −0.0025 (9) | −0.0027 (10) |
O6 | 0.0170 (12) | 0.0282 (13) | 0.0182 (12) | 0.0050 (10) | 0.0006 (9) | −0.0014 (10) |
C1 | 0.0192 (16) | 0.0182 (15) | 0.0147 (15) | −0.0035 (13) | 0.0042 (13) | 0.0044 (12) |
C2 | 0.0165 (16) | 0.0192 (16) | 0.0166 (16) | −0.0003 (13) | 0.0009 (13) | 0.0070 (12) |
C3 | 0.0169 (16) | 0.0175 (16) | 0.0224 (17) | 0.0001 (13) | 0.0049 (13) | 0.0050 (13) |
C4 | 0.0189 (16) | 0.0169 (16) | 0.0167 (16) | −0.0015 (13) | 0.0035 (13) | −0.0004 (12) |
C5 | 0.0159 (16) | 0.0189 (16) | 0.0152 (15) | −0.0033 (13) | 0.0021 (12) | 0.0034 (12) |
C6 | 0.0191 (16) | 0.0176 (15) | 0.0142 (15) | −0.0035 (13) | 0.0050 (12) | 0.0020 (12) |
C7 | 0.0195 (16) | 0.0177 (15) | 0.0126 (15) | −0.0046 (13) | 0.0035 (12) | 0.0027 (12) |
C8 | 0.0167 (16) | 0.0175 (15) | 0.0143 (15) | −0.0019 (12) | 0.0032 (13) | 0.0014 (12) |
C9 | 0.0142 (15) | 0.0176 (15) | 0.0152 (15) | 0.0013 (12) | 0.0032 (12) | 0.0029 (12) |
C10 | 0.0201 (17) | 0.0202 (16) | 0.0131 (15) | −0.0001 (13) | 0.0026 (13) | −0.0011 (12) |
C11 | 0.0169 (16) | 0.0228 (17) | 0.0135 (15) | −0.0022 (13) | 0.0014 (12) | 0.0025 (12) |
C12 | 0.0132 (15) | 0.0187 (16) | 0.0170 (15) | 0.0000 (12) | 0.0037 (12) | 0.0021 (12) |
C13 | 0.0183 (16) | 0.0177 (15) | 0.0150 (15) | −0.0020 (12) | 0.0050 (13) | 0.0007 (12) |
C14 | 0.0166 (16) | 0.0189 (16) | 0.0173 (16) | 0.0015 (12) | 0.0049 (12) | −0.0026 (12) |
C15 | 0.0165 (16) | 0.0227 (17) | 0.0158 (15) | −0.0012 (13) | 0.0050 (12) | −0.0012 (12) |
C16 | 0.0218 (18) | 0.0231 (17) | 0.0210 (17) | 0.0014 (14) | 0.0032 (14) | 0.0006 (13) |
C17 | 0.0262 (19) | 0.0222 (18) | 0.040 (2) | 0.0012 (15) | 0.0076 (16) | 0.0041 (15) |
C18 | 0.0204 (19) | 0.0271 (19) | 0.049 (2) | 0.0037 (15) | 0.0042 (17) | −0.0041 (17) |
C19 | 0.0251 (19) | 0.0238 (18) | 0.032 (2) | 0.0047 (15) | 0.0074 (15) | −0.0002 (15) |
C20 | 0.0135 (15) | 0.0219 (16) | 0.0190 (16) | −0.0017 (13) | −0.0018 (13) | 0.0039 (13) |
C21 | 0.0142 (15) | 0.0244 (17) | 0.0153 (15) | 0.0011 (13) | 0.0003 (12) | 0.0013 (13) |
C22 | 0.0190 (17) | 0.0210 (17) | 0.0192 (17) | −0.0005 (13) | −0.0032 (13) | −0.0008 (13) |
C23 | 0.0239 (19) | 0.0280 (19) | 0.039 (2) | 0.0086 (15) | 0.0052 (16) | −0.0036 (16) |
C24 | 0.030 (2) | 0.0280 (19) | 0.030 (2) | 0.0005 (16) | −0.0017 (16) | 0.0109 (16) |
Geometric parameters (Å, º) top
Cl1—C25 | 1.753 (5) | C12—C13 | 1.382 (5) |
Cl2—C25 | 1.746 (4) | C13—C14 | 1.519 (4) |
Cl3—C25 | 1.758 (5) | C14—C15 | 1.512 (5) |
C25—H25 | 0.98 | C14—H14A | 0.97 |
O1—C1 | 1.365 (4) | C14—H14B | 0.97 |
O1—H1 | 0.82 | C15—C16 | 1.323 (5) |
O2—C7 | 1.257 (4) | C15—H15 | 0.93 |
O3—C5 | 1.364 (4) | C16—C17 | 1.502 (5) |
O3—C9 | 1.383 (4) | C16—C18 | 1.507 (5) |
O4—C3 | 1.364 (4) | C17—H17A | 0.96 |
O4—C19 | 1.424 (4) | C17—H17B | 0.96 |
O5—C11 | 1.356 (4) | C17—H17C | 0.96 |
O5—H5 | 0.82 | C18—H18A | 0.96 |
O6—C12 | 1.372 (4) | C18—H18B | 0.96 |
O6—H6 | 0.82 | C18—H18C | 0.96 |
C1—C2 | 1.386 (5) | C19—H19A | 0.96 |
C1—C6 | 1.423 (5) | C19—H19B | 0.96 |
C2—C3 | 1.407 (5) | C19—H19C | 0.96 |
C2—C20 | 1.517 (4) | C20—C21 | 1.508 (4) |
C3—C4 | 1.399 (5) | C20—H20A | 0.97 |
C4—C5 | 1.375 (5) | C20—H20B | 0.97 |
C4—H4 | 0.93 | C21—C22 | 1.326 (5) |
C5—C6 | 1.396 (5) | C21—H21 | 0.93 |
C6—C7 | 1.441 (5) | C22—C24 | 1.507 (5) |
C7—C8 | 1.461 (4) | C22—C23 | 1.509 (5) |
C8—C9 | 1.398 (5) | C23—H23A | 0.96 |
C8—C13 | 1.421 (5) | C23—H23B | 0.96 |
C9—C10 | 1.388 (5) | C23—H23C | 0.96 |
C10—C11 | 1.378 (5) | C24—H24A | 0.96 |
C10—H10 | 0.93 | C24—H24B | 0.96 |
C11—C12 | 1.404 (5) | C24—H24C | 0.96 |
| | | |
Cl2—C25—Cl1 | 111.6 (3) | C13—C14—H14A | 109.4 |
Cl2—C25—Cl3 | 109.8 (2) | C15—C14—H14B | 109.4 |
Cl1—C25—Cl3 | 110.1 (3) | C13—C14—H14B | 109.4 |
Cl2—C25—H25 | 108.4 | H14A—C14—H14B | 108.0 |
Cl1—C25—H25 | 108.4 | C16—C15—C14 | 126.1 (3) |
Cl3—C25—H25 | 108.4 | C16—C15—H15 | 117.0 |
C1—O1—H1 | 109.5 | C14—C15—H15 | 117.0 |
C5—O3—C9 | 119.6 (2) | C15—C16—C17 | 121.9 (3) |
C3—O4—C19 | 118.2 (3) | C15—C16—C18 | 123.0 (3) |
C11—O5—H5 | 109.5 | C17—C16—C18 | 115.1 (3) |
C12—O6—H6 | 109.5 | C16—C17—H17A | 109.5 |
O1—C1—C2 | 119.3 (3) | C16—C17—H17B | 109.5 |
O1—C1—C6 | 118.0 (3) | H17A—C17—H17B | 109.5 |
C2—C1—C6 | 122.7 (3) | C16—C17—H17C | 109.5 |
C1—C2—C3 | 117.2 (3) | H17A—C17—H17C | 109.5 |
C1—C2—C20 | 122.0 (3) | H17B—C17—H17C | 109.5 |
C3—C2—C20 | 120.7 (3) | C16—C18—H18A | 109.5 |
O4—C3—C4 | 122.4 (3) | C16—C18—H18B | 109.5 |
O4—C3—C2 | 115.2 (3) | H18A—C18—H18B | 109.5 |
C4—C3—C2 | 122.4 (3) | C16—C18—H18C | 109.5 |
C5—C4—C3 | 117.8 (3) | H18A—C18—H18C | 109.5 |
C5—C4—H4 | 121.1 | H18B—C18—H18C | 109.5 |
C3—C4—H4 | 121.1 | O4—C19—H19A | 109.5 |
O3—C5—C4 | 116.0 (3) | O4—C19—H19B | 109.5 |
O3—C5—C6 | 120.5 (3) | H19A—C19—H19B | 109.5 |
C4—C5—C6 | 123.5 (3) | O4—C19—H19C | 109.5 |
C5—C6—C1 | 116.4 (3) | H19A—C19—H19C | 109.5 |
C5—C6—C7 | 121.7 (3) | H19B—C19—H19C | 109.5 |
C1—C6—C7 | 121.8 (3) | C21—C20—C2 | 111.9 (3) |
O2—C7—C6 | 120.1 (3) | C21—C20—H20A | 109.2 |
O2—C7—C8 | 123.6 (3) | C2—C20—H20A | 109.2 |
C6—C7—C8 | 116.3 (3) | C21—C20—H20B | 109.2 |
C9—C8—C13 | 118.4 (3) | C2—C20—H20B | 109.2 |
C9—C8—C7 | 118.0 (3) | H20A—C20—H20B | 107.9 |
C13—C8—C7 | 123.7 (3) | C22—C21—C20 | 128.6 (3) |
O3—C9—C10 | 113.6 (3) | C22—C21—H21 | 115.7 |
O3—C9—C8 | 123.4 (3) | C20—C21—H21 | 115.7 |
C10—C9—C8 | 123.0 (3) | C21—C22—C24 | 120.8 (3) |
C11—C10—C9 | 117.9 (3) | C21—C22—C23 | 124.4 (3) |
C11—C10—H10 | 121.0 | C24—C22—C23 | 114.8 (3) |
C9—C10—H10 | 121.0 | C22—C23—H23A | 109.5 |
O5—C11—C10 | 124.3 (3) | C22—C23—H23B | 109.5 |
O5—C11—C12 | 115.1 (3) | H23A—C23—H23B | 109.5 |
C10—C11—C12 | 120.6 (3) | C22—C23—H23C | 109.5 |
O6—C12—C13 | 119.5 (3) | H23A—C23—H23C | 109.5 |
O6—C12—C11 | 118.9 (3) | H23B—C23—H23C | 109.5 |
C13—C12—C11 | 121.6 (3) | C22—C24—H24A | 109.5 |
C12—C13—C8 | 118.4 (3) | C22—C24—H24B | 109.5 |
C12—C13—C14 | 117.8 (3) | H24A—C24—H24B | 109.5 |
C8—C13—C14 | 123.8 (3) | C22—C24—H24C | 109.5 |
C15—C14—C13 | 111.1 (3) | H24A—C24—H24C | 109.5 |
C15—C14—H14A | 109.4 | H24B—C24—H24C | 109.5 |
| | | |
O1—C1—C2—C3 | −179.1 (3) | C5—O3—C9—C10 | −176.4 (3) |
C6—C1—C2—C3 | −1.0 (5) | C5—O3—C9—C8 | 3.7 (4) |
O1—C1—C2—C20 | 0.9 (5) | C13—C8—C9—O3 | −177.9 (3) |
C6—C1—C2—C20 | 179.0 (3) | C7—C8—C9—O3 | 2.0 (5) |
C19—O4—C3—C4 | 2.8 (4) | C13—C8—C9—C10 | 2.2 (5) |
C19—O4—C3—C2 | −175.8 (3) | C7—C8—C9—C10 | −177.9 (3) |
C1—C2—C3—O4 | 178.2 (3) | O3—C9—C10—C11 | 178.6 (3) |
C20—C2—C3—O4 | −1.7 (4) | C8—C9—C10—C11 | −1.4 (5) |
C1—C2—C3—C4 | −0.3 (5) | C9—C10—C11—O5 | 179.6 (3) |
C20—C2—C3—C4 | 179.7 (3) | C9—C10—C11—C12 | −0.6 (5) |
O4—C3—C4—C5 | −177.1 (3) | O5—C11—C12—O6 | 1.6 (4) |
C2—C3—C4—C5 | 1.3 (5) | C10—C11—C12—O6 | −178.2 (3) |
C9—O3—C5—C4 | 177.2 (3) | O5—C11—C12—C13 | −178.3 (3) |
C9—O3—C5—C6 | −4.6 (4) | C10—C11—C12—C13 | 2.0 (5) |
C3—C4—C5—O3 | 177.1 (3) | O6—C12—C13—C8 | 179.0 (3) |
C3—C4—C5—C6 | −1.1 (5) | C11—C12—C13—C8 | −1.2 (5) |
O3—C5—C6—C1 | −178.3 (3) | O6—C12—C13—C14 | −1.9 (4) |
C4—C5—C6—C1 | −0.2 (5) | C11—C12—C13—C14 | 178.0 (3) |
O3—C5—C6—C7 | −0.2 (5) | C9—C8—C13—C12 | −0.8 (4) |
C4—C5—C6—C7 | 177.9 (3) | C7—C8—C13—C12 | 179.3 (3) |
O1—C1—C6—C5 | 179.3 (3) | C9—C8—C13—C14 | −179.9 (3) |
C2—C1—C6—C5 | 1.2 (5) | C7—C8—C13—C14 | 0.2 (5) |
O1—C1—C6—C7 | 1.3 (4) | C12—C13—C14—C15 | −95.4 (3) |
C2—C1—C6—C7 | −176.8 (3) | C8—C13—C14—C15 | 83.7 (4) |
C5—C6—C7—O2 | −174.0 (3) | C13—C14—C15—C16 | 127.3 (3) |
C1—C6—C7—O2 | 3.9 (5) | C14—C15—C16—C17 | 178.9 (3) |
C5—C6—C7—C8 | 5.7 (4) | C14—C15—C16—C18 | −0.4 (5) |
C1—C6—C7—C8 | −176.4 (3) | C1—C2—C20—C21 | 91.1 (4) |
O2—C7—C8—C9 | 173.3 (3) | C3—C2—C20—C21 | −88.9 (4) |
C6—C7—C8—C9 | −6.4 (4) | C2—C20—C21—C22 | 122.1 (4) |
O2—C7—C8—C13 | −6.8 (5) | C20—C21—C22—C24 | −179.6 (3) |
C6—C7—C8—C13 | 173.5 (3) | C20—C21—C22—C23 | 0.4 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.77 | 2.505 (3) | 149 |
O5—H5···O1i | 0.82 | 1.88 | 2.695 (3) | 176 |
O6—H6···O5 | 0.82 | 2.18 | 2.643 (3) | 116 |
C14—H14A···O6 | 0.97 | 2.36 | 2.769 (4) | 105 |
C14—H14B···O2 | 0.97 | 2.31 | 2.825 (4) | 112 |
C25—H25···O2ii | 0.98 | 2.42 | 3.256 (5) | 142 |
Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) x+1, y, z. |