Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043152/er2031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043152/er2031Isup2.hkl |
CCDC reference: 663727
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.053
- wR factor = 0.148
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C55
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.78 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.45 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C46 - C51 .. 5.13 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C55 - C56 .. 5.72 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C32 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C40 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C46 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C47 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C43 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C50 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C51 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C58 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.30 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 6858 Count of symmetry unique reflns 6883 Completeness (_total/calc) 99.64% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C26 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C35 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C36 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C41 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C49 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C50 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C51 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C56 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 21 ALERT level C = Check and explain 18 ALERT level G = General alerts; check 17 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 18 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The air-dried aerial parts of the Laggera pterodonta (2 kg) was powered and extracted twice with water at 100 centigrade, 2 h each time. The water extracts was combined and concentrated to half of the original volume. Then it was partitioned with EtOAc and BuOH, respectively. The EtOAc and n-BuOH extracts were concentrated in vacuo to afford 20 g and 22 g of residue. The EtOAc portion was subjected to column chromgraphy over 200 g silica gel, using petrol ether/acetone gradients (from 9:1 to 0:1) as eluents. Combining the fractions with TLC (GF254) monitoring, eight fractions were obtained and compound (I) (2.0 g) was crystallized from the fraction 4 (3.5 g). 1H-NMR (300 MHz, CDCl3) δ: 1.27(s, H15), 1.26(s, H14), 1.08(s, H7), 0.89(s, H8). 13C-NMR (125 MHz, CDCl3) δ: 34.32(C1), 20.24(C2), 43.67(C3), 72.69(C4), 48.99(C5), 41.60(C6), 21.99(C7), 18.64(C8), 41.60(C9), 21.32(C10), 41.89(C11), 20.72(C12), 74.79(C13), 29.68(C14), 29.73(C15).
The hydrogen atoms were geometrically placed and constrained to ride on the parent atom. The C—H bond distances are 0.96 Å for CH3, 0.97 Å for CH2, 0.98 Å for CH and 0.82 Å for the OH groups. The Uiso(H) = 1.5 Ueq(C,O) for the CH3 and the OH groups. For all other H atoms Uiso(H) = 1.2 Ueq(C). The Flack (1983) parameter could not be reliable determined due to insufficient anomalous scattering effects from the title compound as it only contains C, H and O atoms. Thus the reflection data were merged.
Laggera pterodonta (DC) Benth (Compositae) has been used as traditional herbal medicine for its anti-inflammatory and anti-bacterial activities (Jiangsu New Medical College, 1977) in the South-West of China. Some eudesmane sesquiterpenes isolated from this plant showed cytotoxicity on tumor cells (Xiao et al., 2003) and antibacterial activities (Wei et al., 1995). These interesting activities on eudesmane sesquiterpenes have prompted us to isolate more sesquiterpenes to evaluate their biological activities. Earlier, we have reported the structure of pterodontic acid which was obtained from this plant (Mei et al., 2006). Following our work, the structure of pterodondiol (I) (Li & Ding, 1993) is confirmed by X-ray analysis.
The molecular structure of (I) is shown in Fig. 1 and the molecular packing is shown in Fig. 2. The title compound crystallizes with four molecules in the asymmetric unit. These molecules are linked by O—H···O, C—H···O intermolecular hydrogen bonds and C—H···O intramolecular hydrogen bonds to form a continuous chain, which runs parallel to the a axis. The hydrogen bond of C5···O4 [3.422 (3) Å] is the longest among all the hydrogen bonds, as listed in the table 1.
For related literature, see: Jiangsu New Medical College (1977); Li & Ding (1993); Mei et al. (2006); Wei et al. (1995); Xiao et al. (2003); Flack (1983).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).
Fig. 1. The asymmetric unit, with atom labels and 50% probability displacement ellipsoids. | |
Fig. 2. The crystal packing, viewed along the b axis. |
C15H28O2 | F(000) = 1072 |
Mr = 240.37 | Dx = 1.063 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 7823 reflections |
a = 15.9298 (16) Å | θ = 2.2–22.1° |
b = 11.8296 (12) Å | µ = 0.07 mm−1 |
c = 16.8033 (17) Å | T = 298 K |
β = 108.502 (2)° | Block, colorless |
V = 3002.8 (5) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART 1K CCD diffractometer | 6858 independent reflections |
Radiation source: fine-focus sealed tube | 4838 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10 pixels mm-1 | θmax = 27.0°, θmin = 1.3° |
φ and ω scans | h = −20→20 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −15→15 |
Tmin = 0.980, Tmax = 0.993 | l = −21→21 |
25093 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0832P)2 + 0.0769P] where P = (Fo2 + 2Fc2)/3 |
6858 reflections | (Δ/σ)max = 0.002 |
637 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
C15H28O2 | V = 3002.8 (5) Å3 |
Mr = 240.37 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.9298 (16) Å | µ = 0.07 mm−1 |
b = 11.8296 (12) Å | T = 298 K |
c = 16.8033 (17) Å | 0.30 × 0.20 × 0.10 mm |
β = 108.502 (2)° |
Bruker SMART 1K CCD diffractometer | 6858 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 4838 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.993 | Rint = 0.031 |
25093 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
6858 reflections | Δρmin = −0.15 e Å−3 |
637 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6805 (3) | 0.3024 (4) | 0.2988 (2) | 0.0806 (11) | |
H1A | 0.6821 | 0.2445 | 0.3401 | 0.097* | |
H1B | 0.7020 | 0.3720 | 0.3288 | 0.097* | |
C2 | 0.5859 (3) | 0.3193 (4) | 0.2443 (2) | 0.0861 (11) | |
H2A | 0.5507 | 0.3436 | 0.2789 | 0.103* | |
H2B | 0.5620 | 0.2481 | 0.2183 | 0.103* | |
C3 | 0.5797 (2) | 0.4065 (3) | 0.1772 (2) | 0.0708 (9) | |
H3A | 0.5973 | 0.4794 | 0.2036 | 0.085* | |
H3B | 0.5185 | 0.4124 | 0.1416 | 0.085* | |
C4 | 0.63714 (18) | 0.3786 (3) | 0.12292 (18) | 0.0519 (7) | |
C5 | 0.73213 (17) | 0.3553 (2) | 0.17900 (16) | 0.0446 (6) | |
H5 | 0.7513 | 0.4268 | 0.2086 | 0.053* | |
C6 | 0.7430 (2) | 0.2680 (3) | 0.25008 (19) | 0.0621 (8) | |
C7 | 0.5957 (2) | 0.2864 (4) | 0.0592 (2) | 0.0773 (10) | |
H7A | 0.5399 | 0.3123 | 0.0221 | 0.116* | |
H7B | 0.5866 | 0.2198 | 0.0881 | 0.116* | |
H7C | 0.6346 | 0.2690 | 0.0274 | 0.116* | |
C8 | 0.7250 (3) | 0.1439 (3) | 0.2202 (3) | 0.0982 (13) | |
H8A | 0.7532 | 0.1286 | 0.1787 | 0.147* | |
H8B | 0.6623 | 0.1323 | 0.1963 | 0.147* | |
H8C | 0.7481 | 0.0940 | 0.2671 | 0.147* | |
C9 | 0.8393 (2) | 0.2776 (3) | 0.3068 (2) | 0.0764 (10) | |
H9A | 0.8483 | 0.3519 | 0.3325 | 0.092* | |
H9B | 0.8496 | 0.2221 | 0.3515 | 0.092* | |
C10 | 0.9063 (2) | 0.2598 (4) | 0.2613 (3) | 0.0874 (12) | |
H10A | 0.9023 | 0.1821 | 0.2419 | 0.105* | |
H10B | 0.9652 | 0.2706 | 0.3008 | 0.105* | |
C11 | 0.89499 (19) | 0.3381 (3) | 0.1865 (2) | 0.0608 (8) | |
H11 | 0.9280 | 0.3023 | 0.1530 | 0.073* | |
C12 | 0.79764 (18) | 0.3360 (3) | 0.13096 (18) | 0.0558 (7) | |
H12A | 0.7887 | 0.3938 | 0.0881 | 0.067* | |
H12B | 0.7852 | 0.2634 | 0.1028 | 0.067* | |
C13 | 0.93593 (18) | 0.4575 (3) | 0.2081 (2) | 0.0611 (8) | |
C14 | 0.9266 (3) | 0.5266 (4) | 0.1300 (3) | 0.1029 (14) | |
H14A | 0.8649 | 0.5385 | 0.1003 | 0.154* | |
H14B | 0.9535 | 0.4869 | 0.0946 | 0.154* | |
H14C | 0.9553 | 0.5983 | 0.1456 | 0.154* | |
C15 | 1.0335 (2) | 0.4493 (4) | 0.2604 (3) | 0.1044 (16) | |
H15A | 1.0596 | 0.5232 | 0.2671 | 0.157* | |
H15B | 1.0637 | 0.4010 | 0.2325 | 0.157* | |
H15C | 1.0385 | 0.4184 | 0.3146 | 0.157* | |
C16 | 0.8048 (2) | 0.5992 (3) | 0.4825 (2) | 0.0690 (9) | |
H16A | 0.7688 | 0.5910 | 0.5191 | 0.083* | |
H16B | 0.7925 | 0.5354 | 0.4443 | 0.083* | |
C17 | 0.9016 (2) | 0.5968 (3) | 0.5351 (2) | 0.0717 (9) | |
H17A | 0.9139 | 0.6579 | 0.5757 | 0.086* | |
H17B | 0.9150 | 0.5260 | 0.5656 | 0.086* | |
C18 | 0.9593 (2) | 0.6092 (3) | 0.47947 (19) | 0.0574 (7) | |
H18A | 0.9511 | 0.5433 | 0.4434 | 0.069* | |
H18B | 1.0208 | 0.6106 | 0.5146 | 0.069* | |
C19 | 0.94041 (17) | 0.7153 (2) | 0.42449 (16) | 0.0476 (6) | |
C20 | 0.84052 (17) | 0.7243 (2) | 0.37757 (16) | 0.0456 (6) | |
H20 | 0.8276 | 0.6592 | 0.3395 | 0.055* | |
C21 | 0.77886 (19) | 0.7086 (3) | 0.4319 (2) | 0.0594 (7) | |
C22 | 0.9817 (2) | 0.8201 (3) | 0.4745 (2) | 0.0705 (9) | |
H22A | 1.0448 | 0.8113 | 0.4955 | 0.106* | |
H22B | 0.9590 | 0.8296 | 0.5206 | 0.106* | |
H22C | 0.9672 | 0.8854 | 0.4388 | 0.106* | |
C23 | 0.7795 (3) | 0.8068 (4) | 0.4923 (3) | 0.0900 (12) | |
H23A | 0.7298 | 0.7995 | 0.5126 | 0.135* | |
H23B | 0.7757 | 0.8773 | 0.4631 | 0.135* | |
H23C | 0.8334 | 0.8046 | 0.5388 | 0.135* | |
C24 | 0.6855 (2) | 0.6953 (4) | 0.3698 (3) | 0.0812 (10) | |
H24A | 0.6835 | 0.6275 | 0.3367 | 0.097* | |
H24B | 0.6441 | 0.6854 | 0.4009 | 0.097* | |
C25 | 0.6566 (2) | 0.7945 (4) | 0.3115 (3) | 0.0945 (13) | |
H25A | 0.6514 | 0.8600 | 0.3443 | 0.113* | |
H25B | 0.5982 | 0.7786 | 0.2727 | 0.113* | |
C26 | 0.7180 (2) | 0.8245 (3) | 0.2608 (2) | 0.0716 (10) | |
H26 | 0.7040 | 0.9034 | 0.2437 | 0.086* | |
C27 | 0.8146 (2) | 0.8267 (2) | 0.3195 (2) | 0.0621 (8) | |
H27A | 0.8537 | 0.8308 | 0.2856 | 0.075* | |
H27B | 0.8236 | 0.8947 | 0.3535 | 0.075* | |
C28 | 0.7042 (2) | 0.7594 (3) | 0.1781 (2) | 0.0740 (10) | |
C29 | 0.6073 (3) | 0.7624 (5) | 0.1230 (3) | 0.139 (2) | |
H29A | 0.6005 | 0.7202 | 0.0725 | 0.208* | |
H29B | 0.5896 | 0.8394 | 0.1089 | 0.208* | |
H29C | 0.5710 | 0.7296 | 0.1529 | 0.208* | |
C30 | 0.7626 (4) | 0.8073 (5) | 0.1290 (3) | 0.1244 (19) | |
H30A | 0.8238 | 0.7966 | 0.1609 | 0.187* | |
H30B | 0.7507 | 0.8866 | 0.1193 | 0.187* | |
H30C | 0.7497 | 0.7688 | 0.0762 | 0.187* | |
C31 | 0.5705 (3) | 0.2571 (5) | 0.5550 (3) | 0.0961 (14) | |
H31A | 0.5696 | 0.3206 | 0.5912 | 0.115* | |
H31B | 0.5098 | 0.2406 | 0.5218 | 0.115* | |
C32 | 0.6228 (3) | 0.2903 (5) | 0.4959 (3) | 0.1102 (16) | |
H32A | 0.6173 | 0.2311 | 0.4546 | 0.132* | |
H32B | 0.5982 | 0.3592 | 0.4663 | 0.132* | |
C33 | 0.7199 (3) | 0.3087 (4) | 0.5443 (3) | 0.0888 (12) | |
H33A | 0.7252 | 0.3750 | 0.5795 | 0.107* | |
H33B | 0.7513 | 0.3243 | 0.5046 | 0.107* | |
C34 | 0.76484 (19) | 0.2101 (3) | 0.59922 (19) | 0.0596 (8) | |
C35 | 0.70828 (17) | 0.1758 (2) | 0.65495 (17) | 0.0493 (6) | |
H35 | 0.7098 | 0.2418 | 0.6906 | 0.059* | |
C36 | 0.60917 (19) | 0.1551 (3) | 0.6090 (2) | 0.0704 (9) | |
C37 | 0.7850 (2) | 0.1154 (3) | 0.5466 (2) | 0.0733 (10) | |
H37A | 0.8272 | 0.1414 | 0.5208 | 0.110* | |
H37B | 0.7315 | 0.0932 | 0.5040 | 0.110* | |
H37C | 0.8090 | 0.0518 | 0.5820 | 0.110* | |
C38 | 0.5891 (3) | 0.0470 (4) | 0.5538 (3) | 0.0970 (13) | |
H38A | 0.5277 | 0.0277 | 0.5409 | 0.146* | |
H38B | 0.6250 | −0.0142 | 0.5837 | 0.146* | |
H38C | 0.6022 | 0.0607 | 0.5027 | 0.146* | |
C39 | 0.5660 (2) | 0.1415 (4) | 0.6782 (3) | 0.0887 (12) | |
H39A | 0.5739 | 0.2112 | 0.7102 | 0.106* | |
H39B | 0.5029 | 0.1301 | 0.6521 | 0.106* | |
C40 | 0.6021 (3) | 0.0460 (4) | 0.7373 (3) | 0.0980 (13) | |
H40A | 0.5883 | −0.0245 | 0.7064 | 0.118* | |
H40B | 0.5726 | 0.0451 | 0.7797 | 0.118* | |
C41 | 0.7014 (2) | 0.0517 (3) | 0.7807 (2) | 0.0723 (9) | |
H41 | 0.7186 | −0.0266 | 0.7971 | 0.087* | |
C42 | 0.7486 (2) | 0.0802 (3) | 0.7161 (2) | 0.0638 (8) | |
H42A | 0.8095 | 0.0998 | 0.7463 | 0.077* | |
H42B | 0.7497 | 0.0126 | 0.6837 | 0.077* | |
C43 | 0.7321 (3) | 0.1185 (3) | 0.8639 (2) | 0.0728 (9) | |
C44 | 0.6778 (4) | 0.0904 (4) | 0.9203 (3) | 0.1142 (16) | |
H44A | 0.7029 | 0.1270 | 0.9736 | 0.171* | |
H44B | 0.6777 | 0.0101 | 0.9284 | 0.171* | |
H44C | 0.6181 | 0.1162 | 0.8948 | 0.171* | |
C45 | 0.8294 (3) | 0.0932 (5) | 0.9099 (3) | 0.1106 (16) | |
H45A | 0.8644 | 0.1141 | 0.8750 | 0.166* | |
H45B | 0.8366 | 0.0139 | 0.9224 | 0.166* | |
H45C | 0.8486 | 0.1357 | 0.9612 | 0.166* | |
C46 | 0.6265 (5) | 0.5741 (5) | 0.6761 (2) | 0.130 (2) | |
H46A | 0.6138 | 0.6261 | 0.6292 | 0.156* | |
H46B | 0.6359 | 0.4999 | 0.6558 | 0.156* | |
C47 | 0.5472 (4) | 0.5689 (5) | 0.7069 (3) | 0.129 (2) | |
H47A | 0.5324 | 0.6446 | 0.7201 | 0.155* | |
H47B | 0.4968 | 0.5391 | 0.6627 | 0.155* | |
C48 | 0.5651 (3) | 0.4957 (4) | 0.7832 (3) | 0.0962 (13) | |
H48A | 0.5706 | 0.4180 | 0.7671 | 0.115* | |
H48B | 0.5145 | 0.4997 | 0.8034 | 0.115* | |
C49 | 0.6481 (2) | 0.5269 (3) | 0.85516 (19) | 0.0652 (8) | |
C50 | 0.7261 (2) | 0.5344 (3) | 0.82020 (17) | 0.0591 (8) | |
H50 | 0.7304 | 0.4582 | 0.7989 | 0.071* | |
C51 | 0.7113 (4) | 0.6115 (3) | 0.7429 (3) | 0.0961 (14) | |
C52 | 0.6325 (3) | 0.6311 (4) | 0.9024 (2) | 0.0878 (12) | |
H52A | 0.5882 | 0.6144 | 0.9283 | 0.132* | |
H52B | 0.6128 | 0.6927 | 0.8638 | 0.132* | |
H52C | 0.6867 | 0.6516 | 0.9448 | 0.132* | |
C53 | 0.7060 (6) | 0.7397 (4) | 0.7617 (4) | 0.163 (3) | |
H53A | 0.6483 | 0.7570 | 0.7649 | 0.245* | |
H53B | 0.7165 | 0.7833 | 0.7176 | 0.245* | |
H53C | 0.7500 | 0.7578 | 0.8141 | 0.245* | |
C54 | 0.7915 (5) | 0.5928 (4) | 0.7114 (4) | 0.132 (2) | |
H54A | 0.7904 | 0.5156 | 0.6918 | 0.158* | |
H54B | 0.7860 | 0.6425 | 0.6642 | 0.158* | |
C55 | 0.8803 (6) | 0.6148 (5) | 0.7786 (6) | 0.170 (4) | |
H55A | 0.9275 | 0.6012 | 0.7548 | 0.205* | |
H55B | 0.8832 | 0.6936 | 0.7952 | 0.205* | |
C56 | 0.8955 (3) | 0.5416 (5) | 0.8557 (4) | 0.1105 (17) | |
H56 | 0.9443 | 0.5779 | 0.8991 | 0.133* | |
C57 | 0.8148 (2) | 0.5528 (4) | 0.8868 (2) | 0.0848 (11) | |
H57A | 0.8209 | 0.4985 | 0.9316 | 0.102* | |
H57B | 0.8153 | 0.6277 | 0.9104 | 0.102* | |
C58 | 0.9275 (3) | 0.4200 (4) | 0.8492 (3) | 0.1035 (17) | |
C59 | 0.9977 (3) | 0.4144 (6) | 0.8058 (4) | 0.157 (3) | |
H59A | 1.0236 | 0.3403 | 0.8130 | 0.236* | |
H59B | 1.0427 | 0.4696 | 0.8300 | 0.236* | |
H59C | 0.9710 | 0.4297 | 0.7471 | 0.236* | |
C60 | 0.9640 (3) | 0.3690 (6) | 0.9367 (3) | 0.140 (2) | |
H60A | 0.9175 | 0.3635 | 0.9615 | 0.210* | |
H60B | 1.0105 | 0.4163 | 0.9709 | 0.210* | |
H60C | 0.9871 | 0.2949 | 0.9328 | 0.210* | |
O1 | 0.63823 (14) | 0.48147 (18) | 0.07659 (12) | 0.0608 (5) | |
H1 | 0.6558 | 0.4674 | 0.0367 | 0.091* | |
O2 | 0.89726 (12) | 0.52150 (18) | 0.26048 (12) | 0.0569 (5) | |
H2 | 0.8502 | 0.5489 | 0.2315 | 0.085* | |
O3 | 0.98669 (12) | 0.70426 (19) | 0.36327 (12) | 0.0591 (5) | |
H3 | 0.9632 | 0.6546 | 0.3295 | 0.089* | |
O4 | 0.72952 (14) | 0.64359 (17) | 0.19505 (14) | 0.0673 (6) | |
H4 | 0.7039 | 0.6049 | 0.1540 | 0.101* | |
O5 | 0.84756 (14) | 0.2485 (3) | 0.65677 (15) | 0.0839 (8) | |
H5A | 0.8875 | 0.2360 | 0.6370 | 0.126* | |
O6 | 0.72197 (16) | 0.23920 (18) | 0.84929 (16) | 0.0717 (6) | |
H6 | 0.7670 | 0.2649 | 0.8424 | 0.108* | |
O7 | 0.66567 (19) | 0.4394 (2) | 0.91711 (16) | 0.0796 (7) | |
H7 | 0.6803 | 0.3815 | 0.8980 | 0.119* | |
O8 | 0.85525 (14) | 0.3481 (2) | 0.80475 (16) | 0.0792 (7) | |
H8 | 0.8661 | 0.3190 | 0.7648 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.100 (3) | 0.082 (2) | 0.066 (2) | −0.026 (2) | 0.036 (2) | 0.0105 (19) |
C2 | 0.085 (3) | 0.098 (3) | 0.089 (2) | −0.031 (2) | 0.048 (2) | −0.010 (2) |
C3 | 0.0474 (16) | 0.087 (2) | 0.080 (2) | −0.0109 (16) | 0.0222 (16) | −0.011 (2) |
C4 | 0.0459 (15) | 0.0559 (17) | 0.0508 (15) | −0.0113 (13) | 0.0109 (13) | −0.0053 (13) |
C5 | 0.0455 (14) | 0.0396 (13) | 0.0458 (14) | −0.0085 (11) | 0.0105 (12) | −0.0073 (11) |
C6 | 0.074 (2) | 0.0465 (16) | 0.0602 (18) | −0.0123 (14) | 0.0130 (16) | 0.0069 (14) |
C7 | 0.0642 (19) | 0.086 (2) | 0.0674 (19) | −0.0232 (18) | 0.0012 (16) | −0.0189 (19) |
C8 | 0.123 (3) | 0.0460 (19) | 0.113 (3) | −0.020 (2) | 0.020 (3) | 0.006 (2) |
C9 | 0.085 (2) | 0.062 (2) | 0.065 (2) | 0.0019 (17) | 0.0003 (18) | 0.0194 (17) |
C10 | 0.068 (2) | 0.065 (2) | 0.108 (3) | 0.0126 (17) | −0.003 (2) | 0.002 (2) |
C11 | 0.0465 (15) | 0.0650 (19) | 0.0682 (19) | 0.0054 (13) | 0.0144 (14) | −0.0217 (16) |
C12 | 0.0502 (15) | 0.0601 (18) | 0.0539 (16) | −0.0048 (13) | 0.0119 (13) | −0.0182 (14) |
C13 | 0.0458 (16) | 0.070 (2) | 0.0690 (19) | −0.0069 (14) | 0.0209 (14) | −0.0200 (16) |
C14 | 0.138 (4) | 0.096 (3) | 0.096 (3) | −0.030 (3) | 0.068 (3) | −0.017 (3) |
C15 | 0.0429 (18) | 0.112 (3) | 0.151 (4) | −0.006 (2) | 0.021 (2) | −0.049 (3) |
C16 | 0.081 (2) | 0.067 (2) | 0.073 (2) | −0.0101 (17) | 0.0434 (18) | −0.0032 (17) |
C17 | 0.099 (3) | 0.0596 (19) | 0.0579 (17) | 0.0069 (18) | 0.0263 (18) | 0.0043 (15) |
C18 | 0.0574 (17) | 0.0544 (17) | 0.0552 (16) | 0.0063 (13) | 0.0104 (14) | 0.0034 (14) |
C19 | 0.0460 (14) | 0.0456 (14) | 0.0477 (14) | −0.0060 (12) | 0.0098 (12) | −0.0042 (12) |
C20 | 0.0473 (14) | 0.0309 (12) | 0.0545 (15) | −0.0034 (10) | 0.0105 (12) | −0.0076 (11) |
C21 | 0.0536 (16) | 0.0560 (17) | 0.0737 (19) | −0.0022 (13) | 0.0275 (15) | −0.0146 (16) |
C22 | 0.0639 (19) | 0.066 (2) | 0.071 (2) | −0.0212 (16) | 0.0058 (16) | −0.0146 (17) |
C23 | 0.102 (3) | 0.082 (3) | 0.097 (3) | 0.015 (2) | 0.048 (2) | −0.023 (2) |
C24 | 0.0501 (18) | 0.092 (3) | 0.104 (3) | 0.0003 (17) | 0.0271 (19) | −0.005 (2) |
C25 | 0.057 (2) | 0.100 (3) | 0.115 (3) | 0.021 (2) | 0.011 (2) | −0.010 (3) |
C26 | 0.068 (2) | 0.0409 (16) | 0.084 (2) | 0.0126 (14) | −0.0068 (18) | −0.0010 (15) |
C27 | 0.0660 (18) | 0.0385 (15) | 0.0683 (19) | −0.0035 (13) | 0.0020 (15) | 0.0011 (14) |
C28 | 0.074 (2) | 0.0449 (16) | 0.078 (2) | 0.0087 (15) | −0.0107 (18) | 0.0028 (16) |
C29 | 0.106 (3) | 0.106 (4) | 0.134 (4) | 0.053 (3) | −0.059 (3) | −0.037 (3) |
C30 | 0.199 (6) | 0.079 (3) | 0.087 (3) | −0.030 (3) | 0.032 (3) | 0.003 (2) |
C31 | 0.071 (2) | 0.126 (4) | 0.086 (3) | 0.039 (2) | 0.016 (2) | 0.009 (3) |
C32 | 0.116 (4) | 0.122 (4) | 0.090 (3) | 0.050 (3) | 0.029 (3) | 0.024 (3) |
C33 | 0.128 (4) | 0.071 (2) | 0.082 (2) | 0.000 (2) | 0.053 (3) | −0.001 (2) |
C34 | 0.0525 (16) | 0.0662 (19) | 0.0636 (17) | −0.0063 (14) | 0.0234 (14) | −0.0188 (16) |
C35 | 0.0414 (14) | 0.0494 (15) | 0.0576 (15) | 0.0016 (11) | 0.0164 (12) | −0.0145 (13) |
C36 | 0.0435 (16) | 0.089 (3) | 0.077 (2) | 0.0035 (16) | 0.0166 (15) | −0.0115 (19) |
C37 | 0.0618 (19) | 0.090 (3) | 0.071 (2) | 0.0029 (18) | 0.0251 (16) | −0.0288 (19) |
C38 | 0.069 (2) | 0.115 (3) | 0.101 (3) | −0.032 (2) | 0.017 (2) | −0.037 (3) |
C39 | 0.0396 (16) | 0.124 (3) | 0.107 (3) | −0.011 (2) | 0.0286 (18) | −0.017 (3) |
C40 | 0.098 (3) | 0.100 (3) | 0.109 (3) | −0.033 (3) | 0.051 (3) | −0.007 (3) |
C41 | 0.090 (2) | 0.0442 (16) | 0.087 (2) | 0.0043 (16) | 0.036 (2) | 0.0007 (17) |
C42 | 0.0597 (18) | 0.0579 (19) | 0.077 (2) | 0.0112 (14) | 0.0257 (16) | −0.0063 (16) |
C43 | 0.094 (3) | 0.0521 (18) | 0.082 (2) | 0.0096 (17) | 0.041 (2) | 0.0029 (17) |
C44 | 0.172 (5) | 0.089 (3) | 0.109 (3) | −0.001 (3) | 0.083 (4) | 0.003 (3) |
C45 | 0.125 (4) | 0.100 (3) | 0.088 (3) | 0.038 (3) | 0.007 (3) | 0.004 (3) |
C46 | 0.227 (6) | 0.106 (4) | 0.052 (2) | 0.084 (4) | 0.038 (3) | 0.018 (2) |
C47 | 0.149 (5) | 0.134 (5) | 0.081 (3) | 0.076 (4) | 0.002 (3) | −0.011 (3) |
C48 | 0.080 (3) | 0.097 (3) | 0.103 (3) | 0.029 (2) | 0.017 (2) | −0.019 (3) |
C49 | 0.081 (2) | 0.0581 (18) | 0.0635 (18) | 0.0217 (16) | 0.0325 (17) | 0.0076 (15) |
C50 | 0.091 (2) | 0.0457 (15) | 0.0494 (15) | 0.0049 (15) | 0.0338 (16) | −0.0045 (13) |
C51 | 0.187 (5) | 0.0460 (19) | 0.075 (2) | 0.019 (2) | 0.070 (3) | 0.0106 (17) |
C52 | 0.124 (3) | 0.078 (2) | 0.073 (2) | 0.039 (2) | 0.047 (2) | 0.0021 (19) |
C53 | 0.333 (10) | 0.045 (2) | 0.164 (5) | 0.025 (4) | 0.154 (6) | 0.020 (3) |
C54 | 0.254 (8) | 0.071 (3) | 0.127 (4) | 0.002 (4) | 0.141 (5) | 0.018 (3) |
C55 | 0.233 (8) | 0.093 (4) | 0.267 (9) | −0.069 (5) | 0.195 (8) | −0.056 (5) |
C56 | 0.099 (3) | 0.102 (3) | 0.147 (4) | −0.048 (3) | 0.063 (3) | −0.068 (3) |
C57 | 0.092 (3) | 0.084 (3) | 0.088 (2) | −0.013 (2) | 0.041 (2) | −0.041 (2) |
C58 | 0.068 (2) | 0.119 (4) | 0.131 (4) | −0.033 (2) | 0.042 (3) | −0.076 (3) |
C59 | 0.090 (3) | 0.170 (6) | 0.248 (7) | −0.058 (4) | 0.104 (4) | −0.110 (6) |
C60 | 0.094 (3) | 0.173 (6) | 0.129 (4) | 0.001 (3) | 0.000 (3) | −0.071 (4) |
O1 | 0.0598 (12) | 0.0645 (13) | 0.0505 (11) | −0.0003 (9) | 0.0068 (10) | 0.0008 (10) |
O2 | 0.0439 (10) | 0.0599 (12) | 0.0641 (11) | −0.0045 (9) | 0.0132 (9) | −0.0191 (10) |
O3 | 0.0461 (11) | 0.0701 (14) | 0.0595 (12) | −0.0143 (9) | 0.0146 (9) | −0.0058 (10) |
O4 | 0.0627 (12) | 0.0423 (11) | 0.0757 (14) | 0.0066 (9) | −0.0081 (10) | −0.0071 (10) |
O5 | 0.0597 (13) | 0.120 (2) | 0.0855 (15) | −0.0316 (14) | 0.0418 (12) | −0.0509 (16) |
O6 | 0.0820 (16) | 0.0516 (13) | 0.0906 (16) | 0.0060 (10) | 0.0403 (13) | −0.0088 (11) |
O7 | 0.1116 (19) | 0.0693 (15) | 0.0801 (16) | 0.0293 (13) | 0.0617 (15) | 0.0197 (12) |
O8 | 0.0658 (13) | 0.0847 (17) | 0.0968 (18) | −0.0201 (12) | 0.0395 (13) | −0.0470 (14) |
C1—C2 | 1.508 (5) | C32—C33 | 1.517 (6) |
C1—C6 | 1.531 (5) | C32—H32A | 0.9700 |
C1—H1A | 0.9700 | C32—H32B | 0.9700 |
C1—H1B | 0.9700 | C33—C34 | 1.518 (5) |
C2—C3 | 1.509 (6) | C33—H33A | 0.9700 |
C2—H2A | 0.9700 | C33—H33B | 0.9700 |
C2—H2B | 0.9700 | C34—O5 | 1.438 (4) |
C3—C4 | 1.519 (4) | C34—C37 | 1.523 (4) |
C3—H3A | 0.9700 | C34—C35 | 1.546 (4) |
C3—H3B | 0.9700 | C35—C42 | 1.525 (4) |
C4—O1 | 1.447 (4) | C35—C36 | 1.541 (4) |
C4—C7 | 1.524 (4) | C35—H35 | 0.9800 |
C4—C5 | 1.533 (4) | C36—C39 | 1.537 (5) |
C5—C12 | 1.526 (4) | C36—C38 | 1.551 (6) |
C5—C6 | 1.547 (4) | C37—H37A | 0.9600 |
C5—H5 | 0.9800 | C37—H37B | 0.9600 |
C6—C9 | 1.531 (5) | C37—H37C | 0.9600 |
C6—C8 | 1.548 (5) | C38—H38A | 0.9600 |
C7—H7A | 0.9600 | C38—H38B | 0.9600 |
C7—H7B | 0.9600 | C38—H38C | 0.9600 |
C7—H7C | 0.9600 | C39—C40 | 1.494 (7) |
C8—H8A | 0.9600 | C39—H39A | 0.9700 |
C8—H8B | 0.9600 | C39—H39B | 0.9700 |
C8—H8C | 0.9600 | C40—C41 | 1.518 (5) |
C9—C10 | 1.513 (5) | C40—H40A | 0.9700 |
C9—H9A | 0.9700 | C40—H40B | 0.9700 |
C9—H9B | 0.9700 | C41—C42 | 1.542 (5) |
C10—C11 | 1.526 (5) | C41—C43 | 1.544 (5) |
C10—H10A | 0.9700 | C41—H41 | 0.9800 |
C10—H10B | 0.9700 | C42—H42A | 0.9700 |
C11—C12 | 1.535 (4) | C42—H42B | 0.9700 |
C11—C13 | 1.550 (5) | C43—O6 | 1.449 (4) |
C11—H11 | 0.9800 | C43—C44 | 1.510 (6) |
C12—H12A | 0.9700 | C43—C45 | 1.526 (6) |
C12—H12B | 0.9700 | C44—H44A | 0.9600 |
C13—O2 | 1.439 (4) | C44—H44B | 0.9600 |
C13—C14 | 1.512 (5) | C44—H44C | 0.9600 |
C13—C15 | 1.527 (5) | C45—H45A | 0.9600 |
C14—H14A | 0.9600 | C45—H45B | 0.9600 |
C14—H14B | 0.9600 | C45—H45C | 0.9600 |
C14—H14C | 0.9600 | C46—C47 | 1.511 (8) |
C15—H15A | 0.9600 | C46—C51 | 1.522 (8) |
C15—H15B | 0.9600 | C46—H46A | 0.9700 |
C15—H15C | 0.9600 | C46—H46B | 0.9700 |
C16—C17 | 1.514 (5) | C47—C48 | 1.498 (7) |
C16—C21 | 1.531 (5) | C47—H47A | 0.9700 |
C16—H16A | 0.9700 | C47—H47B | 0.9700 |
C16—H16B | 0.9700 | C48—C49 | 1.526 (5) |
C17—C18 | 1.512 (5) | C48—H48A | 0.9700 |
C17—H17A | 0.9700 | C48—H48B | 0.9700 |
C17—H17B | 0.9700 | C49—O7 | 1.431 (4) |
C18—C19 | 1.531 (4) | C49—C52 | 1.529 (5) |
C18—H18A | 0.9700 | C49—C50 | 1.536 (4) |
C18—H18B | 0.9700 | C50—C57 | 1.515 (5) |
C19—O3 | 1.449 (3) | C50—C51 | 1.542 (5) |
C19—C22 | 1.524 (4) | C50—H50 | 0.9800 |
C19—C20 | 1.539 (4) | C51—C54 | 1.546 (7) |
C20—C27 | 1.528 (4) | C51—C53 | 1.557 (6) |
C20—C21 | 1.550 (4) | C52—H52A | 0.9600 |
C20—H20 | 0.9800 | C52—H52B | 0.9600 |
C21—C24 | 1.529 (5) | C52—H52C | 0.9600 |
C21—C23 | 1.541 (5) | C53—H53A | 0.9600 |
C22—H22A | 0.9600 | C53—H53B | 0.9600 |
C22—H22B | 0.9600 | C53—H53C | 0.9600 |
C22—H22C | 0.9600 | C54—C55 | 1.526 (9) |
C23—H23A | 0.9600 | C54—H54A | 0.9700 |
C23—H23B | 0.9600 | C54—H54B | 0.9700 |
C23—H23C | 0.9600 | C55—C56 | 1.513 (10) |
C24—C25 | 1.505 (6) | C55—H55A | 0.9700 |
C24—H24A | 0.9700 | C55—H55B | 0.9700 |
C24—H24B | 0.9700 | C56—C57 | 1.539 (6) |
C25—C26 | 1.529 (6) | C56—C58 | 1.541 (7) |
C25—H25A | 0.9700 | C56—H56 | 0.9800 |
C25—H25B | 0.9700 | C57—H57A | 0.9700 |
C26—C28 | 1.542 (5) | C57—H57B | 0.9700 |
C26—C27 | 1.543 (4) | C58—O8 | 1.435 (4) |
C26—H26 | 0.9800 | C58—C59 | 1.519 (6) |
C27—H27A | 0.9700 | C58—C60 | 1.523 (8) |
C27—H27B | 0.9700 | C59—H59A | 0.9600 |
C28—O4 | 1.431 (4) | C59—H59B | 0.9600 |
C28—C29 | 1.528 (5) | C59—H59C | 0.9600 |
C28—C30 | 1.533 (7) | C60—H60A | 0.9600 |
C29—H29A | 0.9600 | C60—H60B | 0.9600 |
C29—H29B | 0.9600 | C60—H60C | 0.9600 |
C29—H29C | 0.9600 | O1—H1 | 0.8200 |
C30—H30A | 0.9600 | O2—H2 | 0.8200 |
C30—H30B | 0.9600 | O3—H3 | 0.8200 |
C30—H30C | 0.9600 | O4—H4 | 0.8200 |
C31—C36 | 1.517 (6) | O5—H5A | 0.8200 |
C31—C32 | 1.536 (6) | O6—H6 | 0.8200 |
C31—H31A | 0.9700 | O7—H7 | 0.8200 |
C31—H31B | 0.9700 | O8—H8 | 0.8200 |
C2—C1—C6 | 113.9 (3) | C32—C31—H31B | 109.0 |
C2—C1—H1A | 108.8 | H31A—C31—H31B | 107.8 |
C6—C1—H1A | 108.8 | C33—C32—C31 | 111.1 (3) |
C2—C1—H1B | 108.8 | C33—C32—H32A | 109.4 |
C6—C1—H1B | 108.8 | C31—C32—H32A | 109.4 |
H1A—C1—H1B | 107.7 | C33—C32—H32B | 109.4 |
C1—C2—C3 | 111.1 (3) | C31—C32—H32B | 109.4 |
C1—C2—H2A | 109.4 | H32A—C32—H32B | 108.0 |
C3—C2—H2A | 109.4 | C32—C33—C34 | 114.8 (4) |
C1—C2—H2B | 109.4 | C32—C33—H33A | 108.6 |
C3—C2—H2B | 109.4 | C34—C33—H33A | 108.6 |
H2A—C2—H2B | 108.0 | C32—C33—H33B | 108.6 |
C2—C3—C4 | 113.1 (3) | C34—C33—H33B | 108.6 |
C2—C3—H3A | 109.0 | H33A—C33—H33B | 107.5 |
C4—C3—H3A | 109.0 | O5—C34—C33 | 108.7 (3) |
C2—C3—H3B | 109.0 | O5—C34—C37 | 107.8 (2) |
C4—C3—H3B | 109.0 | C33—C34—C37 | 111.0 (3) |
H3A—C3—H3B | 107.8 | O5—C34—C35 | 105.2 (2) |
O1—C4—C3 | 104.7 (2) | C33—C34—C35 | 108.5 (3) |
O1—C4—C7 | 107.5 (2) | C37—C34—C35 | 115.4 (3) |
C3—C4—C7 | 111.6 (2) | C42—C35—C36 | 111.4 (3) |
O1—C4—C5 | 107.7 (2) | C42—C35—C34 | 113.6 (2) |
C3—C4—C5 | 109.6 (2) | C36—C35—C34 | 116.1 (2) |
C7—C4—C5 | 115.2 (3) | C42—C35—H35 | 104.8 |
C12—C5—C4 | 114.2 (2) | C36—C35—H35 | 104.8 |
C12—C5—C6 | 112.4 (2) | C34—C35—H35 | 104.8 |
C4—C5—C6 | 116.2 (2) | C31—C36—C39 | 110.0 (3) |
C12—C5—H5 | 104.1 | C31—C36—C35 | 109.3 (3) |
C4—C5—H5 | 104.1 | C39—C36—C35 | 105.7 (3) |
C6—C5—H5 | 104.1 | C31—C36—C38 | 109.3 (3) |
C1—C6—C9 | 109.9 (3) | C39—C36—C38 | 108.0 (3) |
C1—C6—C5 | 107.6 (3) | C35—C36—C38 | 114.5 (3) |
C9—C6—C5 | 106.0 (2) | C34—C37—H37A | 109.5 |
C1—C6—C8 | 109.9 (3) | C34—C37—H37B | 109.5 |
C9—C6—C8 | 108.6 (3) | H37A—C37—H37B | 109.5 |
C5—C6—C8 | 114.8 (3) | C34—C37—H37C | 109.5 |
C4—C7—H7A | 109.5 | H37A—C37—H37C | 109.5 |
C4—C7—H7B | 109.5 | H37B—C37—H37C | 109.5 |
H7A—C7—H7B | 109.5 | C36—C38—H38A | 109.5 |
C4—C7—H7C | 109.5 | C36—C38—H38B | 109.5 |
H7A—C7—H7C | 109.5 | H38A—C38—H38B | 109.5 |
H7B—C7—H7C | 109.5 | C36—C38—H38C | 109.5 |
C6—C8—H8A | 109.5 | H38A—C38—H38C | 109.5 |
C6—C8—H8B | 109.5 | H38B—C38—H38C | 109.5 |
H8A—C8—H8B | 109.5 | C40—C39—C36 | 114.3 (3) |
C6—C8—H8C | 109.5 | C40—C39—H39A | 108.7 |
H8A—C8—H8C | 109.5 | C36—C39—H39A | 108.7 |
H8B—C8—H8C | 109.5 | C40—C39—H39B | 108.7 |
C10—C9—C6 | 113.8 (3) | C36—C39—H39B | 108.7 |
C10—C9—H9A | 108.8 | H39A—C39—H39B | 107.6 |
C6—C9—H9A | 108.8 | C39—C40—C41 | 114.1 (3) |
C10—C9—H9B | 108.8 | C39—C40—H40A | 108.7 |
C6—C9—H9B | 108.8 | C41—C40—H40A | 108.7 |
H9A—C9—H9B | 107.7 | C39—C40—H40B | 108.7 |
C9—C10—C11 | 114.5 (3) | C41—C40—H40B | 108.7 |
C9—C10—H10A | 108.6 | H40A—C40—H40B | 107.6 |
C11—C10—H10A | 108.6 | C40—C41—C42 | 109.7 (3) |
C9—C10—H10B | 108.6 | C40—C41—C43 | 116.1 (3) |
C11—C10—H10B | 108.6 | C42—C41—C43 | 116.1 (3) |
H10A—C10—H10B | 107.6 | C40—C41—H41 | 104.4 |
C10—C11—C12 | 108.9 (3) | C42—C41—H41 | 104.4 |
C10—C11—C13 | 115.4 (3) | C43—C41—H41 | 104.4 |
C12—C11—C13 | 115.2 (3) | C35—C42—C41 | 116.2 (2) |
C10—C11—H11 | 105.4 | C35—C42—H42A | 108.2 |
C12—C11—H11 | 105.4 | C41—C42—H42A | 108.2 |
C13—C11—H11 | 105.4 | C35—C42—H42B | 108.2 |
C5—C12—C11 | 113.9 (2) | C41—C42—H42B | 108.2 |
C5—C12—H12A | 108.8 | H42A—C42—H42B | 107.4 |
C11—C12—H12A | 108.8 | O6—C43—C44 | 105.6 (3) |
C5—C12—H12B | 108.8 | O6—C43—C45 | 108.7 (3) |
C11—C12—H12B | 108.8 | C44—C43—C45 | 109.4 (4) |
H12A—C12—H12B | 107.7 | O6—C43—C41 | 111.4 (3) |
O2—C13—C14 | 107.6 (3) | C44—C43—C41 | 112.1 (3) |
O2—C13—C15 | 103.7 (3) | C45—C43—C41 | 109.7 (3) |
C14—C13—C15 | 109.6 (3) | C43—C44—H44A | 109.5 |
O2—C13—C11 | 113.1 (2) | C43—C44—H44B | 109.5 |
C14—C13—C11 | 111.8 (3) | H44A—C44—H44B | 109.5 |
C15—C13—C11 | 110.6 (3) | C43—C44—H44C | 109.5 |
C13—C14—H14A | 109.5 | H44A—C44—H44C | 109.5 |
C13—C14—H14B | 109.5 | H44B—C44—H44C | 109.5 |
H14A—C14—H14B | 109.5 | C43—C45—H45A | 109.5 |
C13—C14—H14C | 109.5 | C43—C45—H45B | 109.5 |
H14A—C14—H14C | 109.5 | H45A—C45—H45B | 109.5 |
H14B—C14—H14C | 109.5 | C43—C45—H45C | 109.5 |
C13—C15—H15A | 109.5 | H45A—C45—H45C | 109.5 |
C13—C15—H15B | 109.5 | H45B—C45—H45C | 109.5 |
H15A—C15—H15B | 109.5 | C47—C46—C51 | 113.7 (3) |
C13—C15—H15C | 109.5 | C47—C46—H46A | 108.8 |
H15A—C15—H15C | 109.5 | C51—C46—H46A | 108.8 |
H15B—C15—H15C | 109.5 | C47—C46—H46B | 108.8 |
C17—C16—C21 | 112.7 (3) | C51—C46—H46B | 108.8 |
C17—C16—H16A | 109.1 | H46A—C46—H46B | 107.7 |
C21—C16—H16A | 109.1 | C48—C47—C46 | 111.3 (4) |
C17—C16—H16B | 109.1 | C48—C47—H47A | 109.4 |
C21—C16—H16B | 109.1 | C46—C47—H47A | 109.4 |
H16A—C16—H16B | 107.8 | C48—C47—H47B | 109.4 |
C18—C17—C16 | 110.1 (2) | C46—C47—H47B | 109.4 |
C18—C17—H17A | 109.6 | H47A—C47—H47B | 108.0 |
C16—C17—H17A | 109.6 | C47—C48—C49 | 114.9 (4) |
C18—C17—H17B | 109.6 | C47—C48—H48A | 108.5 |
C16—C17—H17B | 109.6 | C49—C48—H48A | 108.5 |
H17A—C17—H17B | 108.2 | C47—C48—H48B | 108.5 |
C17—C18—C19 | 114.3 (2) | C49—C48—H48B | 108.5 |
C17—C18—H18A | 108.7 | H48A—C48—H48B | 107.5 |
C19—C18—H18A | 108.7 | O7—C49—C48 | 108.8 (3) |
C17—C18—H18B | 108.7 | O7—C49—C52 | 103.4 (2) |
C19—C18—H18B | 108.7 | C48—C49—C52 | 111.3 (3) |
H18A—C18—H18B | 107.6 | O7—C49—C50 | 108.9 (2) |
O3—C19—C22 | 103.7 (2) | C48—C49—C50 | 108.2 (3) |
O3—C19—C18 | 107.9 (2) | C52—C49—C50 | 115.9 (3) |
C22—C19—C18 | 111.5 (2) | C57—C50—C49 | 113.8 (2) |
O3—C19—C20 | 108.6 (2) | C57—C50—C51 | 113.3 (3) |
C22—C19—C20 | 114.9 (2) | C49—C50—C51 | 115.5 (3) |
C18—C19—C20 | 109.8 (2) | C57—C50—H50 | 104.2 |
C27—C20—C19 | 114.1 (2) | C49—C50—H50 | 104.2 |
C27—C20—C21 | 112.2 (2) | C51—C50—H50 | 104.2 |
C19—C20—C21 | 115.8 (2) | C46—C51—C50 | 108.2 (4) |
C27—C20—H20 | 104.4 | C46—C51—C54 | 110.0 (4) |
C19—C20—H20 | 104.4 | C50—C51—C54 | 106.3 (4) |
C21—C20—H20 | 104.4 | C46—C51—C53 | 109.9 (5) |
C24—C21—C16 | 109.0 (3) | C50—C51—C53 | 114.1 (3) |
C24—C21—C23 | 109.2 (3) | C54—C51—C53 | 108.2 (4) |
C16—C21—C23 | 109.1 (3) | C49—C52—H52A | 109.5 |
C24—C21—C20 | 105.7 (2) | C49—C52—H52B | 109.5 |
C16—C21—C20 | 108.6 (2) | H52A—C52—H52B | 109.5 |
C23—C21—C20 | 115.1 (3) | C49—C52—H52C | 109.5 |
C19—C22—H22A | 109.5 | H52A—C52—H52C | 109.5 |
C19—C22—H22B | 109.5 | H52B—C52—H52C | 109.5 |
H22A—C22—H22B | 109.5 | C51—C53—H53A | 109.5 |
C19—C22—H22C | 109.5 | C51—C53—H53B | 109.5 |
H22A—C22—H22C | 109.5 | H53A—C53—H53B | 109.5 |
H22B—C22—H22C | 109.5 | C51—C53—H53C | 109.5 |
C21—C23—H23A | 109.5 | H53A—C53—H53C | 109.5 |
C21—C23—H23B | 109.5 | H53B—C53—H53C | 109.5 |
H23A—C23—H23B | 109.5 | C55—C54—C51 | 113.3 (4) |
C21—C23—H23C | 109.5 | C55—C54—H54A | 108.9 |
H23A—C23—H23C | 109.5 | C51—C54—H54A | 108.9 |
H23B—C23—H23C | 109.5 | C55—C54—H54B | 108.9 |
C25—C24—C21 | 113.3 (3) | C51—C54—H54B | 108.9 |
C25—C24—H24A | 108.9 | H54A—C54—H54B | 107.7 |
C21—C24—H24A | 108.9 | C56—C55—C54 | 113.3 (4) |
C25—C24—H24B | 108.9 | C56—C55—H55A | 108.9 |
C21—C24—H24B | 108.9 | C54—C55—H55A | 108.9 |
H24A—C24—H24B | 107.7 | C56—C55—H55B | 108.9 |
C24—C25—C26 | 115.2 (3) | C54—C55—H55B | 108.9 |
C24—C25—H25A | 108.5 | H55A—C55—H55B | 107.7 |
C26—C25—H25A | 108.5 | C55—C56—C57 | 108.5 (5) |
C24—C25—H25B | 108.5 | C55—C56—C58 | 116.1 (4) |
C26—C25—H25B | 108.5 | C57—C56—C58 | 115.8 (4) |
H25A—C25—H25B | 107.5 | C55—C56—H56 | 105.1 |
C25—C26—C28 | 116.9 (3) | C57—C56—H56 | 105.1 |
C25—C26—C27 | 109.4 (3) | C58—C56—H56 | 105.1 |
C28—C26—C27 | 114.3 (3) | C50—C57—C56 | 114.9 (3) |
C25—C26—H26 | 105.0 | C50—C57—H57A | 108.5 |
C28—C26—H26 | 105.0 | C56—C57—H57A | 108.5 |
C27—C26—H26 | 105.0 | C50—C57—H57B | 108.5 |
C20—C27—C26 | 114.1 (2) | C56—C57—H57B | 108.5 |
C20—C27—H27A | 108.7 | H57A—C57—H57B | 107.5 |
C26—C27—H27A | 108.7 | O8—C58—C59 | 108.3 (3) |
C20—C27—H27B | 108.7 | O8—C58—C60 | 105.4 (4) |
C26—C27—H27B | 108.7 | C59—C58—C60 | 109.4 (5) |
H27A—C27—H27B | 107.6 | O8—C58—C56 | 111.2 (4) |
O4—C28—C29 | 108.0 (3) | C59—C58—C56 | 112.6 (5) |
O4—C28—C30 | 106.3 (4) | C60—C58—C56 | 109.6 (4) |
C29—C28—C30 | 109.5 (4) | C58—C59—H59A | 109.5 |
O4—C28—C26 | 110.4 (3) | C58—C59—H59B | 109.5 |
C29—C28—C26 | 111.2 (3) | H59A—C59—H59B | 109.5 |
C30—C28—C26 | 111.2 (3) | C58—C59—H59C | 109.5 |
C28—C29—H29A | 109.5 | H59A—C59—H59C | 109.5 |
C28—C29—H29B | 109.5 | H59B—C59—H59C | 109.5 |
H29A—C29—H29B | 109.5 | C58—C60—H60A | 109.5 |
C28—C29—H29C | 109.5 | C58—C60—H60B | 109.5 |
H29A—C29—H29C | 109.5 | H60A—C60—H60B | 109.5 |
H29B—C29—H29C | 109.5 | C58—C60—H60C | 109.5 |
C28—C30—H30A | 109.5 | H60A—C60—H60C | 109.5 |
C28—C30—H30B | 109.5 | H60B—C60—H60C | 109.5 |
H30A—C30—H30B | 109.5 | C4—O1—H1 | 109.5 |
C28—C30—H30C | 109.5 | C13—O2—H2 | 109.5 |
H30A—C30—H30C | 109.5 | C19—O3—H3 | 109.5 |
H30B—C30—H30C | 109.5 | C28—O4—H4 | 109.5 |
C36—C31—C32 | 112.9 (3) | C34—O5—H5A | 109.5 |
C36—C31—H31A | 109.0 | C43—O6—H6 | 109.5 |
C32—C31—H31A | 109.0 | C49—O7—H7 | 109.5 |
C36—C31—H31B | 109.0 | C58—O8—H8 | 109.5 |
C6—C1—C2—C3 | −57.0 (4) | C36—C31—C32—C33 | −54.6 (6) |
C1—C2—C3—C4 | 55.8 (4) | C31—C32—C33—C34 | 54.4 (5) |
C2—C3—C4—O1 | −167.4 (3) | C32—C33—C34—O5 | −165.2 (3) |
C2—C3—C4—C7 | 76.7 (3) | C32—C33—C34—C37 | 76.4 (4) |
C2—C3—C4—C5 | −52.1 (3) | C32—C33—C34—C35 | −51.4 (4) |
O1—C4—C5—C12 | −61.9 (3) | O5—C34—C35—C42 | −61.4 (3) |
C3—C4—C5—C12 | −175.2 (3) | C33—C34—C35—C42 | −177.6 (3) |
C7—C4—C5—C12 | 58.1 (3) | C37—C34—C35—C42 | 57.2 (3) |
O1—C4—C5—C6 | 164.8 (2) | O5—C34—C35—C36 | 167.5 (3) |
C3—C4—C5—C6 | 51.5 (3) | C33—C34—C35—C36 | 51.3 (4) |
C7—C4—C5—C6 | −75.3 (3) | C37—C34—C35—C36 | −73.9 (3) |
C2—C1—C6—C9 | 167.9 (3) | C32—C31—C36—C39 | 168.4 (4) |
C2—C1—C6—C5 | 52.9 (4) | C32—C31—C36—C35 | 52.9 (5) |
C2—C1—C6—C8 | −72.7 (4) | C32—C31—C36—C38 | −73.1 (5) |
C12—C5—C6—C1 | 174.7 (2) | C42—C35—C36—C31 | 175.0 (3) |
C4—C5—C6—C1 | −51.2 (3) | C34—C35—C36—C31 | −52.9 (4) |
C12—C5—C6—C9 | 57.1 (3) | C42—C35—C36—C39 | 56.7 (4) |
C4—C5—C6—C9 | −168.7 (3) | C34—C35—C36—C39 | −171.1 (3) |
C12—C5—C6—C8 | −62.7 (4) | C42—C35—C36—C38 | −62.0 (4) |
C4—C5—C6—C8 | 71.4 (4) | C34—C35—C36—C38 | 70.1 (4) |
C1—C6—C9—C10 | −172.6 (3) | C31—C36—C39—C40 | −177.6 (4) |
C5—C6—C9—C10 | −56.6 (4) | C35—C36—C39—C40 | −59.8 (4) |
C8—C6—C9—C10 | 67.2 (4) | C38—C36—C39—C40 | 63.2 (4) |
C6—C9—C10—C11 | 55.8 (4) | C36—C39—C40—C41 | 56.7 (5) |
C9—C10—C11—C12 | −49.1 (4) | C39—C40—C41—C42 | −45.7 (4) |
C9—C10—C11—C13 | 82.2 (4) | C39—C40—C41—C43 | 88.5 (4) |
C4—C5—C12—C11 | 167.5 (2) | C36—C35—C42—C41 | −53.8 (3) |
C6—C5—C12—C11 | −57.4 (3) | C34—C35—C42—C41 | 172.8 (3) |
C10—C11—C12—C5 | 50.2 (3) | C40—C41—C42—C35 | 45.6 (4) |
C13—C11—C12—C5 | −81.3 (4) | C43—C41—C42—C35 | −88.6 (4) |
C10—C11—C13—O2 | −61.9 (3) | C40—C41—C43—O6 | −73.2 (4) |
C12—C11—C13—O2 | 66.4 (4) | C42—C41—C43—O6 | 58.0 (4) |
C10—C11—C13—C14 | 176.5 (3) | C40—C41—C43—C44 | 44.7 (4) |
C12—C11—C13—C14 | −55.3 (4) | C42—C41—C43—C44 | 176.0 (3) |
C10—C11—C13—C15 | 54.0 (4) | C40—C41—C43—C45 | 166.4 (4) |
C12—C11—C13—C15 | −177.8 (3) | C42—C41—C43—C45 | −62.3 (4) |
C21—C16—C17—C18 | −58.9 (4) | C51—C46—C47—C48 | −54.7 (6) |
C16—C17—C18—C19 | 56.1 (4) | C46—C47—C48—C49 | 53.8 (5) |
C17—C18—C19—O3 | −168.4 (2) | C47—C48—C49—O7 | −169.8 (3) |
C17—C18—C19—C22 | 78.3 (3) | C47—C48—C49—C52 | 76.8 (4) |
C17—C18—C19—C20 | −50.2 (3) | C47—C48—C49—C50 | −51.6 (4) |
O3—C19—C20—C27 | −61.2 (3) | O7—C49—C50—C57 | −55.8 (4) |
C22—C19—C20—C27 | 54.4 (3) | C48—C49—C50—C57 | −174.0 (3) |
C18—C19—C20—C27 | −179.0 (2) | C52—C49—C50—C57 | 60.2 (4) |
O3—C19—C20—C21 | 166.2 (2) | O7—C49—C50—C51 | 170.7 (3) |
C22—C19—C20—C21 | −78.2 (3) | C48—C49—C50—C51 | 52.5 (4) |
C18—C19—C20—C21 | 48.5 (3) | C52—C49—C50—C51 | −73.3 (4) |
C17—C16—C21—C24 | 170.2 (3) | C47—C46—C51—C50 | 53.6 (5) |
C17—C16—C21—C23 | −70.7 (3) | C47—C46—C51—C54 | 169.4 (4) |
C17—C16—C21—C20 | 55.5 (3) | C47—C46—C51—C53 | −71.6 (5) |
C27—C20—C21—C24 | 58.6 (3) | C57—C50—C51—C46 | 172.3 (3) |
C19—C20—C21—C24 | −168.0 (2) | C49—C50—C51—C46 | −53.9 (4) |
C27—C20—C21—C16 | 175.5 (2) | C57—C50—C51—C54 | 54.1 (4) |
C19—C20—C21—C16 | −51.2 (3) | C49—C50—C51—C54 | −172.1 (4) |
C27—C20—C21—C23 | −62.0 (3) | C57—C50—C51—C53 | −65.1 (6) |
C19—C20—C21—C23 | 71.4 (3) | C49—C50—C51—C53 | 68.7 (6) |
C16—C21—C24—C25 | −174.9 (3) | C46—C51—C54—C55 | −173.0 (4) |
C23—C21—C24—C25 | 66.0 (4) | C50—C51—C54—C55 | −56.1 (5) |
C20—C21—C24—C25 | −58.4 (4) | C53—C51—C54—C55 | 66.9 (6) |
C21—C24—C25—C26 | 55.8 (4) | C51—C54—C55—C56 | 58.4 (6) |
C24—C25—C26—C28 | 85.0 (4) | C54—C55—C56—C57 | −51.9 (5) |
C24—C25—C26—C27 | −47.0 (4) | C54—C55—C56—C58 | 80.5 (6) |
C19—C20—C27—C26 | 169.5 (3) | C49—C50—C57—C56 | 170.6 (4) |
C21—C20—C27—C26 | −56.2 (3) | C51—C50—C57—C56 | −54.8 (5) |
C25—C26—C27—C20 | 47.3 (4) | C55—C56—C57—C50 | 50.9 (5) |
C28—C26—C27—C20 | −86.1 (4) | C58—C56—C57—C50 | −81.7 (6) |
C25—C26—C28—O4 | −68.8 (4) | C55—C56—C58—O8 | −79.6 (5) |
C27—C26—C28—O4 | 60.9 (4) | C57—C56—C58—O8 | 49.3 (6) |
C25—C26—C28—C29 | 51.1 (5) | C55—C56—C58—C59 | 42.2 (6) |
C27—C26—C28—C29 | −179.2 (4) | C57—C56—C58—C59 | 171.2 (4) |
C25—C26—C28—C30 | 173.4 (3) | C55—C56—C58—C60 | 164.2 (5) |
C27—C26—C28—C30 | −56.9 (4) | C57—C56—C58—C60 | −66.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7i | 0.82 | 2.09 | 2.892 (3) | 165 |
O5—H5A···O3ii | 0.82 | 2.04 | 2.815 (3) | 158 |
O2—H2···O4 | 0.82 | 2.14 | 2.927 (3) | 161 |
O3—H3···O2 | 0.82 | 2.04 | 2.851 (3) | 171 |
O4—H4···O1 | 0.82 | 2.01 | 2.814 (3) | 165 |
O6—H6···O8 | 0.82 | 1.98 | 2.782 (3) | 166 |
O7—H7···O6 | 0.82 | 2.07 | 2.891 (3) | 178 |
O8—H8···O5 | 0.82 | 1.93 | 2.719 (3) | 160 |
C5—H5···O2 | 0.98 | 2.48 | 3.221 (3) | 132 |
C5—H5···O4 | 0.98 | 2.59 | 3.422 (3) | 143 |
C9—H9A···O2 | 0.97 | 2.59 | 3.201 (4) | 121 |
C50—H50···O8 | 0.98 | 2.35 | 3.081 (4) | 131 |
C20—H20···O4 | 0.98 | 2.44 | 3.163 (3) | 130 |
Symmetry codes: (i) x, y, z−1; (ii) −x+2, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H28O2 |
Mr | 240.37 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 15.9298 (16), 11.8296 (12), 16.8033 (17) |
β (°) | 108.502 (2) |
V (Å3) | 3002.8 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.980, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25093, 6858, 4838 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.148, 1.05 |
No. of reflections | 6858 |
No. of parameters | 637 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.15 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O7i | 0.82 | 2.09 | 2.892 (3) | 164.9 |
O5—H5A···O3ii | 0.82 | 2.04 | 2.815 (3) | 157.5 |
O2—H2···O4 | 0.82 | 2.14 | 2.927 (3) | 161.1 |
O3—H3···O2 | 0.82 | 2.04 | 2.851 (3) | 170.6 |
O4—H4···O1 | 0.82 | 2.01 | 2.814 (3) | 165.0 |
O6—H6···O8 | 0.82 | 1.98 | 2.782 (3) | 166.3 |
O7—H7···O6 | 0.82 | 2.07 | 2.891 (3) | 177.5 |
O8—H8···O5 | 0.82 | 1.93 | 2.719 (3) | 160.1 |
C5—H5···O2 | 0.98 | 2.48 | 3.221 (3) | 132.4 |
C5—H5···O4 | 0.98 | 2.59 | 3.422 (3) | 143.1 |
C9—H9A···O2 | 0.97 | 2.59 | 3.201 (4) | 121.2 |
C50—H50···O8 | 0.98 | 2.35 | 3.081 (4) | 130.5 |
C20—H20···O4 | 0.98 | 2.44 | 3.163 (3) | 130.0 |
Symmetry codes: (i) x, y, z−1; (ii) −x+2, y−1/2, −z+1. |
Laggera pterodonta (DC) Benth (Compositae) has been used as traditional herbal medicine for its anti-inflammatory and anti-bacterial activities (Jiangsu New Medical College, 1977) in the South-West of China. Some eudesmane sesquiterpenes isolated from this plant showed cytotoxicity on tumor cells (Xiao et al., 2003) and antibacterial activities (Wei et al., 1995). These interesting activities on eudesmane sesquiterpenes have prompted us to isolate more sesquiterpenes to evaluate their biological activities. Earlier, we have reported the structure of pterodontic acid which was obtained from this plant (Mei et al., 2006). Following our work, the structure of pterodondiol (I) (Li & Ding, 1993) is confirmed by X-ray analysis.
The molecular structure of (I) is shown in Fig. 1 and the molecular packing is shown in Fig. 2. The title compound crystallizes with four molecules in the asymmetric unit. These molecules are linked by O—H···O, C—H···O intermolecular hydrogen bonds and C—H···O intramolecular hydrogen bonds to form a continuous chain, which runs parallel to the a axis. The hydrogen bond of C5···O4 [3.422 (3) Å] is the longest among all the hydrogen bonds, as listed in the table 1.