The title compound, C
40H
58O
4.CH
2Cl
2, was isolated for the first time from
Bruguiera cylindrica (
Rhizophoraceae), and for the first time from natural product resources. The structure contains five fused six-membered rings, with two rings in chair, two in twist-boat and one in a slightly twisted boat conformation. The
D and
E rings are
cis-fused. The feruloyl substituent group is axially attached to the skeleton. O—H
O hydrogen bonds and C—H
O interactions are observed in the structure. The absolute configuration was established on the basis of anomalous scattering effects of the solvent.
Supporting information
CCDC reference: 227781
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.062
- wR factor = 0.152
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT214_ALERT_2_C Atom Cl2A (Anion/Solvent) ADP max/min Ratio 4.60 prolat
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.94 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C22
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C20
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C41
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.00
From the CIF: _reflns_number_total 7198
Count of symmetry unique reflns 4046
Completeness (_total/calc) 177.90%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3152
Fraction of Friedel pairs measured 0.779
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
3
α-feruloyltaraxerol dicholomethane
top
Crystal data top
C40H58O4·CH2Cl2 | F(000) = 744 |
Mr = 687.79 | Dx = 1.188 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4263 reflections |
a = 12.5558 (10) Å | θ = 2.3–26.0° |
b = 8.5131 (7) Å | µ = 0.21 mm−1 |
c = 18.6076 (15) Å | T = 293 K |
β = 104.834 (1)° | Needle, colourless |
V = 1922.7 (3) Å3 | 0.48 × 0.18 × 0.14 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 7198 independent reflections |
Radiation source: fine-focus sealed tube | 5897 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.3° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→10 |
Tmin = 0.907, Tmax = 0.972 | l = −14→22 |
10423 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.5197P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.002 |
7198 reflections | Δρmax = 0.34 e Å−3 |
445 parameters | Δρmin = −0.48 e Å−3 |
5 restraints | Absolute structure: Flack (1983), 3171 Friedel pairs' |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (13) |
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 | Occ. (<1) |
O1 | 0.35353 (18) | −0.2592 (3) | 0.22768 (11) | 0.0382 (5) | |
O2 | 0.37018 (19) | −0.4218 (3) | 0.32612 (12) | 0.0450 (6) | |
O3 | 0.5202 (2) | −0.7599 (3) | 0.51810 (13) | 0.0522 (7) | |
O4 | 0.7350 (2) | −0.8035 (4) | 0.57168 (13) | 0.0607 (8) | |
H4 | 0.6827 | −0.8231 | 0.5891 | 0.091* | |
C1 | 0.1745 (3) | −0.1292 (4) | 0.10527 (17) | 0.0340 (7) | |
H1A | 0.1105 | −0.1507 | 0.0646 | 0.041* | |
H1B | 0.2387 | −0.1702 | 0.0917 | 0.041* | |
C2 | 0.1617 (3) | −0.2137 (4) | 0.17470 (17) | 0.0407 (8) | |
H2A | 0.0938 | −0.1796 | 0.1856 | 0.049* | |
H2B | 0.1558 | −0.3257 | 0.1649 | 0.049* | |
C3 | 0.2569 (2) | −0.1840 (4) | 0.24230 (16) | 0.0346 (7) | |
H3 | 0.2406 | −0.2332 | 0.2859 | 0.042* | |
C4 | 0.2830 (2) | −0.0088 (4) | 0.25879 (16) | 0.0336 (7) | |
C5 | 0.2854 (2) | 0.0794 (4) | 0.18556 (16) | 0.0290 (6) | |
H5 | 0.3495 | 0.0362 | 0.1716 | 0.035* | |
C6 | 0.3094 (3) | 0.2554 (4) | 0.19597 (16) | 0.0353 (7) | |
H6A | 0.3689 | 0.2719 | 0.2402 | 0.042* | |
H6B | 0.2446 | 0.3092 | 0.2028 | 0.042* | |
C7 | 0.3416 (3) | 0.3240 (4) | 0.12843 (16) | 0.0332 (7) | |
H7A | 0.4106 | 0.2771 | 0.1253 | 0.040* | |
H7B | 0.3539 | 0.4360 | 0.1361 | 0.040* | |
C8 | 0.2554 (2) | 0.2984 (3) | 0.05384 (15) | 0.0266 (6) | |
C9 | 0.2221 (2) | 0.1219 (3) | 0.04805 (16) | 0.0263 (6) | |
H9 | 0.2901 | 0.0661 | 0.0473 | 0.032* | |
C10 | 0.1871 (2) | 0.0505 (3) | 0.11636 (15) | 0.0278 (6) | |
C11 | 0.1411 (2) | 0.0815 (4) | −0.02777 (16) | 0.0328 (7) | |
H11A | 0.1584 | −0.0228 | −0.0426 | 0.039* | |
H11B | 0.0670 | 0.0782 | −0.0212 | 0.039* | |
C12 | 0.1430 (2) | 0.1963 (4) | −0.09079 (16) | 0.0299 (7) | |
H12A | 0.0917 | 0.2810 | −0.0898 | 0.036* | |
H12B | 0.1172 | 0.1419 | −0.1378 | 0.036* | |
C13 | 0.2565 (2) | 0.2677 (3) | −0.08733 (16) | 0.0279 (6) | |
C14 | 0.3061 (2) | 0.3385 (3) | −0.01079 (16) | 0.0280 (6) | |
C15 | 0.3909 (3) | 0.4357 (4) | −0.00383 (18) | 0.0411 (8) | |
H15 | 0.4276 | 0.4718 | 0.0431 | 0.049* | |
C16 | 0.4284 (3) | 0.4882 (5) | −0.0698 (2) | 0.0533 (10) | |
H16A | 0.4691 | 0.4043 | −0.0860 | 0.064* | |
H16B | 0.4770 | 0.5780 | −0.0565 | 0.064* | |
C17 | 0.3276 (3) | 0.5333 (4) | −0.1335 (2) | 0.0465 (9) | |
C18 | 0.2424 (2) | 0.3949 (4) | −0.15068 (16) | 0.0298 (7) | |
H18 | 0.1703 | 0.4432 | −0.1547 | 0.036* | |
C19 | 0.2360 (3) | 0.3231 (4) | −0.22709 (17) | 0.0388 (8) | |
H19A | 0.1815 | 0.2397 | −0.2358 | 0.047* | |
H19B | 0.3066 | 0.2755 | −0.2259 | 0.047* | |
C20 | 0.2065 (3) | 0.4376 (5) | −0.29293 (19) | 0.0439 (8) | |
C21 | 0.2732 (4) | 0.5895 (6) | −0.2726 (2) | 0.0744 (14) | |
H21A | 0.3026 | 0.6203 | −0.3139 | 0.089* | |
H21B | 0.2247 | 0.6726 | −0.2646 | 0.089* | |
C22 | 0.3681 (4) | 0.5714 (7) | −0.2030 (2) | 0.0775 (15) | |
H22A | 0.4104 | 0.6681 | −0.1945 | 0.093* | |
H22B | 0.4166 | 0.4881 | −0.2109 | 0.093* | |
C23 | 0.3955 (3) | 0.0039 (4) | 0.31497 (17) | 0.0424 (8) | |
H23A | 0.4516 | −0.0352 | 0.2929 | 0.064* | |
H23B | 0.3952 | −0.0571 | 0.3583 | 0.064* | |
H23C | 0.4104 | 0.1118 | 0.3289 | 0.064* | |
C24 | 0.1978 (3) | 0.0574 (5) | 0.29771 (18) | 0.0480 (9) | |
H24A | 0.2124 | 0.1668 | 0.3084 | 0.072* | |
H24B | 0.2030 | 0.0012 | 0.3432 | 0.072* | |
H24C | 0.1250 | 0.0453 | 0.2657 | 0.072* | |
C25 | 0.1580 (3) | 0.4133 (4) | 0.05062 (18) | 0.0384 (7) | |
H25A | 0.1795 | 0.5177 | 0.0406 | 0.058* | |
H25B | 0.1390 | 0.4120 | 0.0974 | 0.058* | |
H25C | 0.0955 | 0.3813 | 0.0118 | 0.058* | |
C26 | 0.0757 (3) | 0.1179 (4) | 0.12368 (18) | 0.0383 (8) | |
H26A | 0.0306 | 0.1443 | 0.0753 | 0.057* | |
H26B | 0.0889 | 0.2104 | 0.1542 | 0.057* | |
H26C | 0.0387 | 0.0407 | 0.1461 | 0.057* | |
C27 | 0.3332 (3) | 0.1314 (4) | −0.09778 (18) | 0.0355 (7) | |
H27A | 0.3399 | 0.0567 | −0.0582 | 0.053* | |
H27B | 0.4047 | 0.1725 | −0.0970 | 0.053* | |
H27C | 0.3026 | 0.0806 | −0.1446 | 0.053* | |
C28 | 0.2731 (5) | 0.6777 (5) | −0.1092 (3) | 0.0795 (15) | |
H28A | 0.2104 | 0.7079 | −0.1483 | 0.119* | |
H28B | 0.3251 | 0.7627 | −0.0989 | 0.119* | |
H28C | 0.2498 | 0.6531 | −0.0652 | 0.119* | |
C29 | 0.0843 (3) | 0.4737 (7) | −0.3137 (3) | 0.0842 (17) | |
H29A | 0.0674 | 0.5449 | −0.3550 | 0.126* | |
H29B | 0.0645 | 0.5210 | −0.2720 | 0.126* | |
H29C | 0.0434 | 0.3782 | −0.3270 | 0.126* | |
C30 | 0.2361 (5) | 0.3619 (6) | −0.3595 (2) | 0.0795 (15) | |
H30A | 0.3132 | 0.3367 | −0.3467 | 0.119* | |
H30B | 0.2199 | 0.4337 | −0.4006 | 0.119* | |
H30C | 0.1937 | 0.2676 | −0.3730 | 0.119* | |
C31 | 0.4049 (3) | −0.3703 (4) | 0.27585 (17) | 0.0341 (7) | |
C32 | 0.5073 (3) | −0.4164 (4) | 0.25695 (17) | 0.0362 (7) | |
H32 | 0.5120 | −0.3863 | 0.2098 | 0.043* | |
C33 | 0.5938 (3) | −0.4943 (4) | 0.29666 (17) | 0.0376 (8) | |
H33 | 0.6493 | −0.5026 | 0.2720 | 0.045* | |
C34 | 0.6243 (3) | −0.5710 (4) | 0.36997 (17) | 0.0349 (7) | |
C35 | 0.7353 (3) | −0.5997 (4) | 0.40096 (19) | 0.0445 (8) | |
H35 | 0.7862 | −0.5682 | 0.3753 | 0.053* | |
C36 | 0.7722 (3) | −0.6734 (5) | 0.46841 (19) | 0.0505 (9) | |
H36 | 0.8474 | −0.6872 | 0.4887 | 0.061* | |
C37 | 0.6985 (3) | −0.7267 (4) | 0.50606 (18) | 0.0433 (8) | |
C38 | 0.5856 (3) | −0.6998 (4) | 0.47619 (17) | 0.0388 (8) | |
C39 | 0.5490 (3) | −0.6232 (4) | 0.40924 (17) | 0.0372 (7) | |
H39 | 0.4740 | −0.6058 | 0.3898 | 0.045* | |
C40 | 0.4073 (3) | −0.7209 (5) | 0.4989 (2) | 0.0575 (11) | |
H40A | 0.3722 | −0.7689 | 0.5335 | 0.086* | |
H40B | 0.3735 | −0.7584 | 0.4496 | 0.086* | |
H40C | 0.3992 | −0.6089 | 0.5003 | 0.086* | |
Cl1 | −0.00947 (18) | 0.4337 (3) | 0.27051 (12) | 0.1425 (7) | |
Cl2A | 0.0589 (19) | 0.449 (3) | 0.4384 (5) | 0.27 (2) | 0.216 (4) |
Cl2B | 0.0808 (7) | 0.3423 (8) | 0.4237 (3) | 0.159 (3) | 0.529 (11) |
Cl2C | 0.0216 (11) | 0.481 (4) | 0.4253 (5) | 0.194 (11) | 0.255 (12) |
C41 | 0.0800 (6) | 0.4714 (10) | 0.3480 (5) | 0.155 (3) | |
H41A | 0.1015 | 0.5801 | 0.3447 | 0.186* | 0.216 (4) |
H41B | 0.1443 | 0.4086 | 0.3476 | 0.186* | 0.216 (4) |
H41C | 0.0659 | 0.5740 | 0.3649 | 0.186* | 0.529 (11) |
H41D | 0.1515 | 0.4736 | 0.3384 | 0.186* | 0.529 (11) |
H41E | 0.1225 | 0.5608 | 0.3405 | 0.186* | 0.255 (12) |
H41F | 0.1293 | 0.3836 | 0.3605 | 0.186* | 0.255 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0467 (13) | 0.0375 (13) | 0.0336 (11) | 0.0013 (10) | 0.0162 (10) | 0.0088 (10) |
O2 | 0.0572 (14) | 0.0483 (14) | 0.0362 (12) | 0.0027 (12) | 0.0242 (11) | 0.0074 (11) |
O3 | 0.0522 (15) | 0.0652 (17) | 0.0427 (14) | 0.0070 (13) | 0.0183 (12) | 0.0202 (13) |
O4 | 0.0567 (16) | 0.089 (2) | 0.0383 (14) | 0.0168 (15) | 0.0154 (12) | 0.0181 (14) |
C1 | 0.0339 (16) | 0.0370 (19) | 0.0294 (16) | −0.0116 (14) | 0.0050 (13) | −0.0033 (13) |
C2 | 0.0471 (19) | 0.0376 (19) | 0.0380 (17) | −0.0115 (16) | 0.0118 (15) | 0.0045 (15) |
C3 | 0.0397 (17) | 0.0418 (19) | 0.0253 (15) | −0.0027 (15) | 0.0134 (13) | 0.0032 (14) |
C4 | 0.0327 (16) | 0.0405 (19) | 0.0277 (15) | −0.0027 (14) | 0.0079 (13) | −0.0008 (14) |
C5 | 0.0289 (15) | 0.0286 (16) | 0.0315 (15) | −0.0025 (13) | 0.0113 (12) | −0.0023 (13) |
C6 | 0.0381 (17) | 0.0357 (19) | 0.0286 (15) | −0.0060 (14) | 0.0021 (13) | −0.0106 (14) |
C7 | 0.0380 (16) | 0.0254 (16) | 0.0344 (16) | −0.0083 (13) | 0.0058 (13) | −0.0047 (13) |
C8 | 0.0278 (14) | 0.0218 (15) | 0.0299 (15) | 0.0000 (12) | 0.0069 (12) | −0.0038 (12) |
C9 | 0.0207 (13) | 0.0258 (15) | 0.0329 (15) | −0.0002 (12) | 0.0076 (12) | −0.0055 (12) |
C10 | 0.0266 (14) | 0.0286 (16) | 0.0287 (15) | −0.0050 (12) | 0.0082 (12) | −0.0030 (12) |
C11 | 0.0331 (16) | 0.0324 (17) | 0.0314 (15) | −0.0076 (14) | 0.0054 (12) | 0.0000 (13) |
C12 | 0.0290 (15) | 0.0323 (17) | 0.0261 (15) | −0.0021 (13) | 0.0027 (12) | −0.0017 (13) |
C13 | 0.0247 (14) | 0.0269 (16) | 0.0319 (15) | 0.0019 (12) | 0.0071 (12) | 0.0032 (13) |
C14 | 0.0253 (14) | 0.0216 (15) | 0.0361 (16) | 0.0032 (12) | 0.0064 (12) | 0.0023 (12) |
C15 | 0.0385 (18) | 0.045 (2) | 0.0362 (17) | −0.0130 (16) | 0.0036 (14) | 0.0015 (15) |
C16 | 0.0427 (19) | 0.063 (3) | 0.053 (2) | −0.0276 (19) | 0.0086 (17) | 0.0049 (19) |
C17 | 0.050 (2) | 0.037 (2) | 0.051 (2) | −0.0089 (16) | 0.0103 (16) | 0.0133 (16) |
C18 | 0.0279 (15) | 0.0275 (16) | 0.0362 (16) | 0.0060 (12) | 0.0123 (13) | 0.0030 (13) |
C19 | 0.0433 (18) | 0.0399 (19) | 0.0364 (17) | 0.0078 (15) | 0.0160 (14) | 0.0072 (15) |
C20 | 0.0414 (18) | 0.053 (2) | 0.0400 (18) | 0.0120 (17) | 0.0157 (15) | 0.0134 (17) |
C21 | 0.097 (3) | 0.066 (3) | 0.057 (2) | −0.020 (3) | 0.012 (2) | 0.026 (2) |
C22 | 0.075 (3) | 0.095 (4) | 0.059 (3) | −0.041 (3) | 0.012 (2) | 0.024 (3) |
C23 | 0.049 (2) | 0.047 (2) | 0.0296 (16) | −0.0062 (16) | 0.0080 (15) | −0.0012 (15) |
C24 | 0.060 (2) | 0.058 (2) | 0.0317 (17) | 0.0014 (19) | 0.0220 (16) | −0.0057 (17) |
C25 | 0.0464 (19) | 0.0293 (17) | 0.0406 (18) | 0.0078 (15) | 0.0129 (15) | −0.0033 (14) |
C26 | 0.0341 (17) | 0.044 (2) | 0.0373 (17) | −0.0018 (15) | 0.0103 (14) | 0.0008 (15) |
C27 | 0.0400 (18) | 0.0312 (17) | 0.0361 (17) | 0.0085 (14) | 0.0114 (14) | 0.0068 (14) |
C28 | 0.105 (4) | 0.029 (2) | 0.091 (3) | −0.007 (2) | −0.001 (3) | 0.003 (2) |
C29 | 0.055 (3) | 0.134 (5) | 0.062 (3) | 0.022 (3) | 0.012 (2) | 0.042 (3) |
C30 | 0.123 (4) | 0.083 (4) | 0.038 (2) | 0.033 (3) | 0.031 (2) | 0.019 (2) |
C31 | 0.0453 (18) | 0.0307 (17) | 0.0279 (16) | −0.0103 (14) | 0.0121 (14) | −0.0101 (14) |
C32 | 0.0437 (18) | 0.0347 (18) | 0.0312 (16) | −0.0097 (15) | 0.0117 (14) | −0.0004 (14) |
C33 | 0.0415 (18) | 0.0403 (19) | 0.0352 (17) | −0.0094 (15) | 0.0175 (15) | −0.0054 (15) |
C34 | 0.0431 (18) | 0.0328 (17) | 0.0299 (16) | −0.0011 (14) | 0.0114 (13) | −0.0074 (14) |
C35 | 0.046 (2) | 0.050 (2) | 0.0435 (19) | −0.0004 (16) | 0.0213 (16) | −0.0013 (17) |
C36 | 0.0413 (18) | 0.069 (3) | 0.041 (2) | 0.0067 (18) | 0.0097 (16) | 0.0016 (18) |
C37 | 0.053 (2) | 0.049 (2) | 0.0284 (16) | 0.0073 (17) | 0.0108 (15) | −0.0029 (15) |
C38 | 0.0500 (19) | 0.0383 (19) | 0.0300 (16) | 0.0016 (15) | 0.0135 (14) | −0.0017 (14) |
C39 | 0.0393 (17) | 0.0345 (18) | 0.0382 (18) | −0.0029 (14) | 0.0105 (14) | −0.0046 (14) |
C40 | 0.057 (2) | 0.070 (3) | 0.055 (2) | 0.005 (2) | 0.0318 (19) | 0.018 (2) |
Cl1 | 0.1454 (16) | 0.1149 (14) | 0.1460 (16) | 0.0114 (13) | −0.0015 (13) | 0.0218 (13) |
Cl2A | 0.21 (2) | 0.41 (4) | 0.115 (10) | −0.25 (3) | −0.104 (13) | 0.148 (17) |
Cl2B | 0.133 (5) | 0.251 (8) | 0.101 (3) | −0.057 (5) | 0.042 (3) | −0.057 (4) |
Cl2C | 0.075 (6) | 0.39 (3) | 0.101 (8) | −0.099 (11) | 0.001 (7) | −0.028 (12) |
C41 | 0.125 (6) | 0.128 (7) | 0.221 (10) | −0.037 (5) | 0.061 (7) | −0.065 (7) |
Geometric parameters (Å, º) top
O1—C31 | 1.349 (4) | C20—C21 | 1.535 (6) |
O1—C3 | 1.457 (4) | C21—C22 | 1.527 (6) |
O2—C31 | 1.211 (4) | C21—H21A | 0.97 |
O3—C38 | 1.369 (4) | C21—H21B | 0.97 |
O3—C40 | 1.410 (4) | C22—H22A | 0.97 |
O4—C37 | 1.357 (4) | C22—H22B | 0.97 |
O4—H4 | 0.82 | C23—H23A | 0.96 |
C1—C2 | 1.523 (4) | C23—H23B | 0.96 |
C1—C10 | 1.546 (4) | C23—H23C | 0.96 |
C1—H1A | 0.97 | C24—H24A | 0.96 |
C1—H1B | 0.97 | C24—H24B | 0.96 |
C2—C3 | 1.518 (4) | C24—H24C | 0.96 |
C2—H2A | 0.97 | C25—H25A | 0.96 |
C2—H2B | 0.97 | C25—H25B | 0.96 |
C3—C4 | 1.542 (5) | C25—H25C | 0.96 |
C3—H3 | 0.98 | C26—H26A | 0.96 |
C4—C23 | 1.531 (4) | C26—H26B | 0.96 |
C4—C24 | 1.543 (4) | C26—H26C | 0.96 |
C4—C5 | 1.563 (4) | C27—H27A | 0.96 |
C5—C6 | 1.530 (4) | C27—H27B | 0.96 |
C5—C10 | 1.558 (4) | C27—H27C | 0.96 |
C5—H5 | 0.98 | C28—H28A | 0.96 |
C6—C7 | 1.531 (4) | C28—H28B | 0.96 |
C6—H6A | 0.97 | C28—H28C | 0.96 |
C6—H6B | 0.97 | C29—H29A | 0.96 |
C7—C8 | 1.541 (4) | C29—H29B | 0.96 |
C7—H7A | 0.97 | C29—H29C | 0.96 |
C7—H7B | 0.97 | C30—H30A | 0.96 |
C8—C14 | 1.536 (4) | C30—H30B | 0.96 |
C8—C25 | 1.555 (4) | C30—H30C | 0.96 |
C8—C9 | 1.556 (4) | C31—C32 | 1.470 (4) |
C9—C11 | 1.552 (4) | C32—C33 | 1.324 (5) |
C9—C10 | 1.570 (4) | C32—H32 | 0.93 |
C9—H9 | 0.98 | C33—C34 | 1.472 (5) |
C10—C26 | 1.549 (4) | C33—H33 | 0.93 |
C11—C12 | 1.532 (4) | C34—C35 | 1.386 (5) |
C11—H11A | 0.97 | C34—C39 | 1.407 (4) |
C11—H11B | 0.97 | C35—C36 | 1.373 (5) |
C12—C13 | 1.535 (4) | C35—H35 | 0.93 |
C12—H12A | 0.97 | C36—C37 | 1.373 (5) |
C12—H12B | 0.97 | C36—H36 | 0.93 |
C13—C14 | 1.525 (4) | C37—C38 | 1.403 (5) |
C13—C27 | 1.552 (4) | C38—C39 | 1.377 (5) |
C13—C18 | 1.577 (4) | C39—H39 | 0.93 |
C14—C15 | 1.328 (4) | C40—H40A | 0.96 |
C15—C16 | 1.491 (5) | C40—H40B | 0.96 |
C15—H15 | 0.93 | C40—H40C | 0.96 |
C16—C17 | 1.545 (5) | Cl1—C41 | 1.617 (9) |
C16—H16A | 0.97 | Cl2A—C41 | 1.780 (12) |
C16—H16B | 0.97 | Cl2A—H41C | 1.7526 |
C17—C28 | 1.530 (6) | Cl2B—C41 | 1.785 (10) |
C17—C22 | 1.541 (5) | Cl2B—H41F | 1.4974 |
C17—C18 | 1.568 (4) | Cl2C—C41 | 1.777 (11) |
C18—C19 | 1.531 (4) | Cl2C—H41C | 1.5866 |
C18—H18 | 0.98 | C41—H41A | 0.97 |
C19—C20 | 1.535 (5) | C41—H41B | 0.97 |
C19—H19A | 0.97 | C41—H41C | 0.96 |
C19—H19B | 0.97 | C41—H41D | 0.96 |
C20—C29 | 1.515 (5) | C41—H41E | 0.96 |
C20—C30 | 1.524 (5) | C41—H41F | 0.96 |
| | | |
C31—O1—C3 | 117.6 (2) | C29—C20—C19 | 110.7 (3) |
C38—O3—C40 | 118.6 (3) | C30—C20—C19 | 108.7 (3) |
C37—O4—H4 | 109.5 | C21—C20—C19 | 109.5 (3) |
C2—C1—C10 | 112.6 (3) | C22—C21—C20 | 112.5 (3) |
C2—C1—H1A | 109.1 | C22—C21—H21A | 109.1 |
C10—C1—H1A | 109.1 | C20—C21—H21A | 109.1 |
C2—C1—H1B | 109.1 | C22—C21—H21B | 109.1 |
C10—C1—H1B | 109.1 | C20—C21—H21B | 109.1 |
H1A—C1—H1B | 107.8 | H21A—C21—H21B | 107.8 |
C3—C2—C1 | 113.1 (3) | C21—C22—C17 | 112.3 (3) |
C3—C2—H2A | 109.0 | C21—C22—H22A | 109.1 |
C1—C2—H2A | 109.0 | C17—C22—H22A | 109.1 |
C3—C2—H2B | 109.0 | C21—C22—H22B | 109.1 |
C1—C2—H2B | 109.0 | C17—C22—H22B | 109.1 |
H2A—C2—H2B | 107.8 | H22A—C22—H22B | 107.9 |
O1—C3—C2 | 106.8 (2) | C4—C23—H23A | 109.5 |
O1—C3—C4 | 108.5 (2) | C4—C23—H23B | 109.5 |
C2—C3—C4 | 114.1 (3) | H23A—C23—H23B | 109.5 |
O1—C3—H3 | 109.1 | C4—C23—H23C | 109.5 |
C2—C3—H3 | 109.1 | H23A—C23—H23C | 109.5 |
C4—C3—H3 | 109.1 | H23B—C23—H23C | 109.5 |
C23—C4—C3 | 108.4 (3) | C4—C24—H24A | 109.5 |
C23—C4—C24 | 106.5 (3) | C4—C24—H24B | 109.5 |
C3—C4—C24 | 108.0 (3) | H24A—C24—H24B | 109.5 |
C23—C4—C5 | 109.9 (2) | C4—C24—H24C | 109.5 |
C3—C4—C5 | 110.0 (2) | H24A—C24—H24C | 109.5 |
C24—C4—C5 | 113.8 (3) | H24B—C24—H24C | 109.5 |
C6—C5—C10 | 110.4 (2) | C8—C25—H25A | 109.5 |
C6—C5—C4 | 114.0 (2) | C8—C25—H25B | 109.5 |
C10—C5—C4 | 117.2 (2) | H25A—C25—H25B | 109.5 |
C6—C5—H5 | 104.6 | C8—C25—H25C | 109.5 |
C10—C5—H5 | 104.6 | H25A—C25—H25C | 109.5 |
C4—C5—H5 | 104.6 | H25B—C25—H25C | 109.5 |
C5—C6—C7 | 110.8 (2) | C10—C26—H26A | 109.5 |
C5—C6—H6A | 109.5 | C10—C26—H26B | 109.5 |
C7—C6—H6A | 109.5 | H26A—C26—H26B | 109.5 |
C5—C6—H6B | 109.5 | C10—C26—H26C | 109.5 |
C7—C6—H6B | 109.5 | H26A—C26—H26C | 109.5 |
H6A—C6—H6B | 108.1 | H26B—C26—H26C | 109.5 |
C6—C7—C8 | 114.4 (2) | C13—C27—H27A | 109.5 |
C6—C7—H7A | 108.7 | C13—C27—H27B | 109.5 |
C8—C7—H7A | 108.7 | H27A—C27—H27B | 109.5 |
C6—C7—H7B | 108.7 | C13—C27—H27C | 109.5 |
C8—C7—H7B | 108.7 | H27A—C27—H27C | 109.5 |
H7A—C7—H7B | 107.6 | H27B—C27—H27C | 109.5 |
C14—C8—C7 | 109.7 (2) | C17—C28—H28A | 109.5 |
C14—C8—C25 | 108.0 (2) | C17—C28—H28B | 109.5 |
C7—C8—C25 | 108.0 (2) | H28A—C28—H28B | 109.5 |
C14—C8—C9 | 108.5 (2) | C17—C28—H28C | 109.5 |
C7—C8—C9 | 108.3 (2) | H28A—C28—H28C | 109.5 |
C25—C8—C9 | 114.2 (2) | H28B—C28—H28C | 109.5 |
C11—C9—C8 | 112.3 (2) | C20—C29—H29A | 109.5 |
C11—C9—C10 | 113.3 (2) | C20—C29—H29B | 109.5 |
C8—C9—C10 | 116.3 (2) | H29A—C29—H29B | 109.5 |
C11—C9—H9 | 104.5 | C20—C29—H29C | 109.5 |
C8—C9—H9 | 104.5 | H29A—C29—H29C | 109.5 |
C10—C9—H9 | 104.5 | H29B—C29—H29C | 109.5 |
C1—C10—C26 | 108.3 (2) | C20—C30—H30A | 109.5 |
C1—C10—C5 | 107.4 (2) | C20—C30—H30B | 109.5 |
C26—C10—C5 | 114.2 (2) | H30A—C30—H30B | 109.5 |
C1—C10—C9 | 108.4 (2) | C20—C30—H30C | 109.5 |
C26—C10—C9 | 112.0 (2) | H30A—C30—H30C | 109.5 |
C5—C10—C9 | 106.3 (2) | H30B—C30—H30C | 109.5 |
C12—C11—C9 | 114.8 (2) | O2—C31—O1 | 124.2 (3) |
C12—C11—H11A | 108.6 | O2—C31—C32 | 126.7 (3) |
C9—C11—H11A | 108.6 | O1—C31—C32 | 109.1 (3) |
C12—C11—H11B | 108.6 | C33—C32—C31 | 130.0 (3) |
C9—C11—H11B | 108.6 | C33—C32—H32 | 115.0 |
H11A—C11—H11B | 107.5 | C31—C32—H32 | 115.0 |
C11—C12—C13 | 114.6 (2) | C32—C33—C34 | 136.1 (3) |
C11—C12—H12A | 108.6 | C32—C33—H33 | 111.9 |
C13—C12—H12A | 108.6 | C34—C33—H33 | 111.9 |
C11—C12—H12B | 108.6 | C35—C34—C39 | 117.8 (3) |
C13—C12—H12B | 108.6 | C35—C34—C33 | 117.4 (3) |
H12A—C12—H12B | 107.6 | C39—C34—C33 | 124.8 (3) |
C14—C13—C12 | 110.4 (2) | C36—C35—C34 | 122.0 (3) |
C14—C13—C27 | 107.1 (2) | C36—C35—H35 | 119.0 |
C12—C13—C27 | 107.3 (2) | C34—C35—H35 | 119.0 |
C14—C13—C18 | 111.6 (2) | C37—C36—C35 | 120.2 (3) |
C12—C13—C18 | 108.4 (2) | C37—C36—H36 | 119.9 |
C27—C13—C18 | 112.0 (2) | C35—C36—H36 | 119.9 |
C15—C14—C13 | 117.5 (3) | O4—C37—C36 | 120.2 (3) |
C15—C14—C8 | 123.0 (3) | O4—C37—C38 | 120.6 (3) |
C13—C14—C8 | 119.5 (2) | C36—C37—C38 | 119.2 (3) |
C14—C15—C16 | 121.4 (3) | O3—C38—C39 | 125.7 (3) |
C14—C15—H15 | 119.3 | O3—C38—C37 | 114.0 (3) |
C16—C15—H15 | 119.3 | C39—C38—C37 | 120.4 (3) |
C15—C16—C17 | 109.6 (3) | C38—C39—C34 | 120.4 (3) |
C15—C16—H16A | 109.7 | C38—C39—H39 | 119.8 |
C17—C16—H16A | 109.7 | C34—C39—H39 | 119.8 |
C15—C16—H16B | 109.7 | O3—C40—H40A | 109.5 |
C17—C16—H16B | 109.7 | O3—C40—H40B | 109.5 |
H16A—C16—H16B | 108.2 | H40A—C40—H40B | 109.5 |
C28—C17—C22 | 110.3 (4) | O3—C40—H40C | 109.5 |
C28—C17—C16 | 108.2 (3) | H40A—C40—H40C | 109.5 |
C22—C17—C16 | 108.3 (3) | H40B—C40—H40C | 109.5 |
C28—C17—C18 | 109.3 (3) | Cl1—C41—Cl2A | 125.8 (7) |
C22—C17—C18 | 110.0 (3) | Cl1—C41—Cl2B | 116.3 (5) |
C16—C17—C18 | 110.6 (3) | Cl1—C41—Cl2C | 113.3 (6) |
C19—C18—C17 | 111.1 (3) | Cl1—C41—H41A | 105.9 |
C19—C18—C13 | 112.9 (3) | Cl1—C41—H41B | 105.9 |
C17—C18—C13 | 115.1 (2) | Cl1—C41—H41C | 109.2 |
C19—C18—H18 | 105.6 | Cl1—C41—H41D | 107.9 |
C17—C18—H18 | 105.6 | Cl1—C41—H41E | 108.3 |
C13—C18—H18 | 105.6 | Cl1—C41—H41F | 108.6 |
C18—C19—C20 | 115.6 (3) | Cl2A—C41—H41A | 105.9 |
C18—C19—H19A | 108.4 | Cl2A—C41—H41B | 105.9 |
C20—C19—H19A | 108.4 | H41A—C41—H41B | 106.2 |
C18—C19—H19B | 108.4 | Cl2B—C41—H41C | 105.4 |
C20—C19—H19B | 108.4 | Cl2B—C41—H41D | 110.1 |
H19A—C19—H19B | 107.4 | H41C—C41—H41D | 107.7 |
C29—C20—C30 | 108.7 (4) | Cl2C—C41—H41E | 116.1 |
C29—C20—C21 | 110.2 (4) | Cl2C—C41—H41F | 102.3 |
C30—C20—C21 | 109.0 (3) | H41E—C41—H41F | 107.8 |
| | | |
C10—C1—C2—C3 | −57.4 (4) | C25—C8—C14—C15 | 93.3 (3) |
C31—O1—C3—C2 | −121.4 (3) | C9—C8—C14—C15 | −142.4 (3) |
C31—O1—C3—C4 | 115.2 (3) | C7—C8—C14—C13 | 157.2 (2) |
C1—C2—C3—O1 | −67.4 (3) | C25—C8—C14—C13 | −85.3 (3) |
C1—C2—C3—C4 | 52.5 (4) | C9—C8—C14—C13 | 39.1 (3) |
O1—C3—C4—C23 | −47.4 (3) | C13—C14—C15—C16 | 6.7 (5) |
C2—C3—C4—C23 | −166.3 (2) | C8—C14—C15—C16 | −171.9 (3) |
O1—C3—C4—C24 | −162.4 (2) | C14—C15—C16—C17 | 44.5 (5) |
C2—C3—C4—C24 | 78.7 (3) | C15—C16—C17—C28 | 65.8 (4) |
O1—C3—C4—C5 | 72.8 (3) | C15—C16—C17—C22 | −174.6 (4) |
C2—C3—C4—C5 | −46.1 (3) | C15—C16—C17—C18 | −54.0 (4) |
C23—C4—C5—C6 | −61.4 (3) | C28—C17—C18—C19 | 129.1 (3) |
C3—C4—C5—C6 | 179.4 (2) | C22—C17—C18—C19 | 7.8 (4) |
C24—C4—C5—C6 | 58.0 (3) | C16—C17—C18—C19 | −111.8 (3) |
C23—C4—C5—C10 | 167.6 (3) | C28—C17—C18—C13 | −101.0 (3) |
C3—C4—C5—C10 | 48.3 (3) | C22—C17—C18—C13 | 137.7 (3) |
C24—C4—C5—C10 | −73.1 (3) | C16—C17—C18—C13 | 18.1 (4) |
C10—C5—C6—C7 | −61.2 (3) | C14—C13—C18—C19 | 158.0 (2) |
C4—C5—C6—C7 | 164.4 (2) | C12—C13—C18—C19 | −80.3 (3) |
C5—C6—C7—C8 | 56.6 (3) | C27—C13—C18—C19 | 37.9 (3) |
C6—C7—C8—C14 | −167.6 (3) | C14—C13—C18—C17 | 29.0 (3) |
C6—C7—C8—C25 | 74.9 (3) | C12—C13—C18—C17 | 150.7 (3) |
C6—C7—C8—C9 | −49.3 (3) | C27—C13—C18—C17 | −91.1 (3) |
C14—C8—C9—C11 | −57.1 (3) | C17—C18—C19—C20 | −57.0 (4) |
C7—C8—C9—C11 | −176.1 (2) | C13—C18—C19—C20 | 172.0 (3) |
C25—C8—C9—C11 | 63.5 (3) | C18—C19—C20—C29 | −77.1 (4) |
C14—C8—C9—C10 | 170.0 (2) | C18—C19—C20—C30 | 163.5 (3) |
C7—C8—C9—C10 | 51.0 (3) | C18—C19—C20—C21 | 44.6 (4) |
C25—C8—C9—C10 | −69.4 (3) | C29—C20—C21—C22 | 136.0 (4) |
C2—C1—C10—C26 | −69.0 (3) | C30—C20—C21—C22 | −104.8 (4) |
C2—C1—C10—C5 | 54.8 (3) | C19—C20—C21—C22 | 14.0 (5) |
C2—C1—C10—C9 | 169.3 (2) | C20—C21—C22—C17 | −62.6 (6) |
C6—C5—C10—C1 | 175.0 (2) | C28—C17—C22—C21 | −71.7 (5) |
C4—C5—C10—C1 | −52.3 (3) | C16—C17—C22—C21 | 170.0 (4) |
C6—C5—C10—C26 | −64.8 (3) | C18—C17—C22—C21 | 49.0 (5) |
C4—C5—C10—C26 | 67.9 (3) | C3—O1—C31—O2 | 7.3 (4) |
C6—C5—C10—C9 | 59.1 (3) | C3—O1—C31—C32 | −172.8 (2) |
C4—C5—C10—C9 | −168.1 (2) | O2—C31—C32—C33 | −16.1 (6) |
C11—C9—C10—C1 | 56.1 (3) | O1—C31—C32—C33 | 164.0 (3) |
C8—C9—C10—C1 | −171.5 (2) | C31—C32—C33—C34 | 3.2 (7) |
C11—C9—C10—C26 | −63.4 (3) | C32—C33—C34—C35 | −161.1 (4) |
C8—C9—C10—C26 | 69.0 (3) | C32—C33—C34—C39 | 21.8 (6) |
C11—C9—C10—C5 | 171.3 (2) | C39—C34—C35—C36 | −1.4 (5) |
C8—C9—C10—C5 | −56.3 (3) | C33—C34—C35—C36 | −178.7 (3) |
C8—C9—C11—C12 | 22.0 (3) | C34—C35—C36—C37 | 2.6 (6) |
C10—C9—C11—C12 | 156.3 (2) | C35—C36—C37—O4 | 178.1 (4) |
C9—C11—C12—C13 | 33.8 (4) | C35—C36—C37—C38 | −2.4 (6) |
C11—C12—C13—C14 | −52.0 (3) | C40—O3—C38—C39 | −10.8 (5) |
C11—C12—C13—C27 | 64.5 (3) | C40—O3—C38—C37 | 171.3 (3) |
C11—C12—C13—C18 | −174.4 (2) | O4—C37—C38—O3 | −1.3 (5) |
C12—C13—C14—C15 | −164.7 (3) | C36—C37—C38—O3 | 179.2 (3) |
C27—C13—C14—C15 | 78.7 (3) | O4—C37—C38—C39 | −179.4 (3) |
C18—C13—C14—C15 | −44.2 (4) | C36—C37—C38—C39 | 1.2 (5) |
C12—C13—C14—C8 | 13.9 (4) | O3—C38—C39—C34 | −177.9 (3) |
C27—C13—C14—C8 | −102.6 (3) | C37—C38—C39—C34 | 0.0 (5) |
C18—C13—C14—C8 | 134.5 (3) | C35—C34—C39—C38 | 0.1 (5) |
C7—C8—C14—C15 | −24.2 (4) | C33—C34—C39—C38 | 177.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3 | 0.82 | 2.19 | 2.651 (4) | 115 |
O4—H4···O2i | 0.82 | 2.04 | 2.768 (4) | 147 |
C3—H3···O2 | 0.98 | 2.27 | 2.724 (4) | 107 |
C39—H39···O2 | 0.93 | 2.18 | 2.932 (4) | 137 |
Symmetry code: (i) −x+1, y−1/2, −z+1. |