The title compound (C
25H
39NO
6), a polycyclic diterpenoid alkaloid, has been isolated from
Delphinium roylei Munz. Two
cis-fused ring junctions are observed between cyclohexane
A and piperidine
E rings and between cyclohexane
B and cyclopentane
C rings. Two
trans-fused ring junctions involve cyclohexane
A and cyclopentane
B rings and also piperidine
E and cyclopentane
F rings. Cyclopentane ring
F is in a twist conformation, while the other cyclopentane ring,
C, forms an envelope conformation. Piperidine ring
E is in a chair conformation, the two cyclohexane rings
A and
B adopt twist–boat conformations and cyclohexane ring
D is in a screw-boat conformation. Of the five substituents, only one is α-oriented. The molecules are packed along the
c axis in layers parallel to the
ab plane and stabilized by weak inter- and intramolecular O—H
O and O—H
N hydrogen bonds.
Supporting information
CCDC reference: 604945
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.085
- Data-to-parameter ratio = 7.2
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_4_C Flack test results are meaningless.
From the CIF: _refine_ls_abs_structure_Flack 0.000
From the CIF: _refine_ls_abs_structure_Flack_su 10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.25
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.53 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.17 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C25 H39 N O6
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
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 25.00
From the CIF: _reflns_number_total 2152
Count of symmetry unique reflns 2161
Completeness (_total/calc) 99.58%
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
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
6 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).
14-Acetyl-20-ethyl-1,8-dihydroxy-16–18-dimethoxylycoctonine
top
Crystal data top
C25H39NO6 | F(000) = 488 |
Mr = 449.57 | Dx = 1.279 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9484 (12) Å | Cell parameters from 3947 reflections |
b = 13.2080 (17) Å | θ = 2.1–25.0° |
c = 9.8945 (13) Å | µ = 0.09 mm−1 |
β = 93.553 (2)° | T = 293 K |
V = 1167.2 (3) Å3 | Block, colorless |
Z = 2 | 0.45 × 0.20 × 0.19 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2152 independent reflections |
Radiation source: fine-focus sealed tube | 2103 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→15 |
Tmin = 0.961, Tmax = 0.983 | l = −11→5 |
5883 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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1886P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.002 |
2152 reflections | Δρmax = 0.16 e Å−3 |
297 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (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 | |
N1 | −0.3639 (2) | 0.48219 (15) | 0.27905 (19) | 0.0341 (4) | |
O1 | −0.2970 (3) | 0.81512 (16) | 0.4893 (2) | 0.0576 (5) | |
O2 | 0.1244 (3) | 0.6113 (3) | −0.3640 (2) | 0.0817 (8) | |
O3 | −0.0185 (2) | 0.38135 (16) | −0.22029 (18) | 0.0524 (5) | |
O4 | −0.55491 (17) | 0.55829 (14) | 0.08037 (18) | 0.0439 (5) | |
H1O4 | −0.5287 | 0.5244 | 0.1463 | 0.058 (10)* | |
O5 | 0.15078 (18) | 0.53292 (16) | 0.16063 (18) | 0.0459 (5) | |
H1O5 | 0.2106 | 0.5458 | 0.1105 | 0.039 (8)* | |
O6 | 0.14475 (18) | 0.58007 (14) | −0.14183 (16) | 0.0419 (4) | |
C1 | −0.4650 (3) | 0.64769 (19) | 0.0919 (2) | 0.0364 (5) | |
H1 | −0.4679 | 0.6785 | 0.0017 | 0.044* | |
C2 | −0.5291 (3) | 0.7251 (2) | 0.1858 (3) | 0.0466 (6) | |
H2A | −0.4785 | 0.7894 | 0.1759 | 0.056* | |
H2B | −0.6346 | 0.7351 | 0.1604 | 0.056* | |
C3 | −0.5113 (3) | 0.6916 (2) | 0.3326 (3) | 0.0463 (6) | |
H3A | −0.5801 | 0.6363 | 0.3463 | 0.056* | |
H3B | −0.5386 | 0.7473 | 0.3900 | 0.056* | |
C4 | −0.3496 (3) | 0.65655 (19) | 0.3770 (2) | 0.0370 (5) | |
C5 | −0.2377 (3) | 0.67786 (18) | 0.2659 (2) | 0.0321 (5) | |
H5 | −0.2240 | 0.7507 | 0.2524 | 0.039* | |
C6 | −0.0863 (2) | 0.62416 (19) | 0.3004 (2) | 0.0353 (5) | |
H6A | −0.0037 | 0.6651 | 0.2724 | 0.042* | |
H6B | −0.0722 | 0.6116 | 0.3970 | 0.042* | |
C7 | −0.0959 (2) | 0.52348 (18) | 0.2210 (2) | 0.0321 (5) | |
H7 | −0.0655 | 0.4666 | 0.2800 | 0.038* | |
C8 | 0.0021 (2) | 0.52910 (19) | 0.0995 (2) | 0.0326 (5) | |
C9 | −0.0354 (2) | 0.62819 (19) | 0.0211 (2) | 0.0331 (5) | |
H9 | 0.0210 | 0.6850 | 0.0626 | 0.040* | |
C10 | −0.2052 (2) | 0.65248 (17) | 0.0109 (2) | 0.0311 (5) | |
H10 | −0.2158 | 0.7255 | −0.0040 | 0.037* | |
C11 | −0.2965 (2) | 0.62503 (17) | 0.1333 (2) | 0.0294 (5) | |
C12 | −0.2649 (3) | 0.59827 (19) | −0.1223 (2) | 0.0353 (5) | |
H12A | −0.3390 | 0.5476 | −0.1028 | 0.042* | |
H12B | −0.3105 | 0.6469 | −0.1857 | 0.042* | |
C13 | −0.1286 (2) | 0.54858 (18) | −0.1813 (2) | 0.0332 (5) | |
H13 | −0.1382 | 0.5498 | −0.2804 | 0.040* | |
C14 | −0.0044 (3) | 0.61904 (19) | −0.1284 (2) | 0.0369 (5) | |
H14 | −0.0152 | 0.6852 | −0.1726 | 0.044* | |
C15 | −0.0121 (3) | 0.4334 (2) | 0.0075 (3) | 0.0388 (5) | |
H15A | 0.0884 | 0.4117 | −0.0099 | 0.055 (9)* | |
H15B | −0.0563 | 0.3801 | 0.0595 | 0.040 (7)* | |
C16 | −0.1019 (3) | 0.44004 (19) | −0.1295 (2) | 0.0372 (5) | |
H16 | −0.1993 | 0.4075 | −0.1209 | 0.045* | |
C17 | −0.2625 (2) | 0.51501 (17) | 0.1739 (2) | 0.0290 (5) | |
H17 | −0.2748 | 0.4708 | 0.0945 | 0.035* | |
C18 | −0.2986 (3) | 0.7095 (2) | 0.5092 (3) | 0.0441 (6) | |
H18A | −0.3661 | 0.6928 | 0.5788 | 0.053* | |
H18B | −0.1991 | 0.6864 | 0.5391 | 0.053* | |
C19 | −0.3468 (3) | 0.5422 (2) | 0.4042 (2) | 0.0386 (6) | |
H19A | −0.2527 | 0.5245 | 0.4525 | 0.046* | |
H19B | −0.4270 | 0.5251 | 0.4618 | 0.046* | |
C20 | −0.3509 (3) | 0.3739 (2) | 0.3107 (3) | 0.0445 (6) | |
H20A | −0.4098 | 0.3590 | 0.3874 | 0.053* | |
H20B | −0.2472 | 0.3584 | 0.3370 | 0.053* | |
C21 | −0.4027 (4) | 0.3064 (2) | 0.1936 (3) | 0.0612 (8) | |
H21A | −0.4158 | 0.2386 | 0.2257 | 0.092* | |
H21B | −0.3291 | 0.3066 | 0.1270 | 0.092* | |
H21C | −0.4962 | 0.3311 | 0.1536 | 0.092* | |
C22 | −0.2325 (4) | 0.8685 (3) | 0.6025 (3) | 0.0688 (9) | |
H22A | −0.2309 | 0.9395 | 0.5824 | 0.103* | |
H22B | −0.1320 | 0.8450 | 0.6226 | 0.103* | |
H22C | −0.2907 | 0.8571 | 0.6793 | 0.103* | |
C23 | 0.1917 (3) | 0.5753 (3) | −0.2680 (3) | 0.0520 (7) | |
C24 | 0.3351 (3) | 0.5177 (3) | −0.2694 (3) | 0.0674 (9) | |
H24A | 0.3961 | 0.5461 | −0.3363 | 0.101* | |
H24B | 0.3141 | 0.4481 | −0.2908 | 0.101* | |
H24C | 0.3873 | 0.5220 | −0.1818 | 0.101* | |
C25 | −0.0966 (5) | 0.3594 (3) | −0.3456 (3) | 0.0738 (10) | |
H25A | −0.0436 | 0.3081 | −0.3921 | 0.111* | |
H25B | −0.1037 | 0.4196 | −0.4000 | 0.111* | |
H25C | −0.1953 | 0.3356 | −0.3298 | 0.111* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0343 (10) | 0.0366 (10) | 0.0317 (10) | −0.0065 (8) | 0.0047 (8) | 0.0033 (8) |
O1 | 0.0828 (15) | 0.0459 (11) | 0.0428 (11) | −0.0013 (10) | −0.0073 (9) | −0.0110 (9) |
O2 | 0.0679 (14) | 0.136 (2) | 0.0426 (11) | 0.0125 (16) | 0.0150 (10) | 0.0190 (15) |
O3 | 0.0632 (12) | 0.0532 (11) | 0.0403 (10) | 0.0214 (10) | −0.0004 (8) | −0.0054 (9) |
O4 | 0.0284 (8) | 0.0597 (12) | 0.0430 (10) | −0.0003 (8) | −0.0039 (7) | −0.0021 (9) |
O5 | 0.0234 (8) | 0.0722 (13) | 0.0416 (9) | 0.0000 (8) | −0.0009 (7) | 0.0104 (9) |
O6 | 0.0314 (8) | 0.0577 (11) | 0.0374 (9) | −0.0013 (8) | 0.0079 (7) | 0.0025 (8) |
C1 | 0.0319 (12) | 0.0465 (14) | 0.0305 (11) | 0.0079 (10) | −0.0010 (9) | 0.0027 (10) |
C2 | 0.0406 (13) | 0.0551 (16) | 0.0438 (14) | 0.0182 (12) | 0.0009 (11) | −0.0030 (12) |
C3 | 0.0410 (14) | 0.0583 (17) | 0.0403 (13) | 0.0077 (12) | 0.0063 (10) | −0.0106 (12) |
C4 | 0.0382 (13) | 0.0426 (13) | 0.0304 (12) | 0.0011 (10) | 0.0038 (10) | −0.0030 (10) |
C5 | 0.0353 (12) | 0.0318 (11) | 0.0290 (11) | −0.0024 (9) | 0.0000 (9) | 0.0006 (9) |
C6 | 0.0324 (11) | 0.0445 (13) | 0.0284 (11) | −0.0041 (10) | −0.0020 (9) | 0.0013 (10) |
C7 | 0.0296 (11) | 0.0368 (12) | 0.0292 (11) | 0.0001 (10) | −0.0026 (9) | 0.0072 (10) |
C8 | 0.0224 (10) | 0.0425 (12) | 0.0326 (11) | 0.0014 (9) | −0.0011 (8) | 0.0048 (11) |
C9 | 0.0287 (11) | 0.0390 (13) | 0.0317 (11) | −0.0033 (10) | 0.0037 (9) | 0.0026 (10) |
C10 | 0.0318 (11) | 0.0306 (11) | 0.0309 (11) | 0.0025 (9) | 0.0015 (9) | 0.0054 (9) |
C11 | 0.0270 (11) | 0.0341 (11) | 0.0270 (10) | 0.0013 (9) | 0.0021 (8) | 0.0007 (9) |
C12 | 0.0347 (11) | 0.0413 (13) | 0.0295 (11) | 0.0071 (10) | −0.0009 (9) | 0.0054 (10) |
C13 | 0.0353 (12) | 0.0378 (13) | 0.0264 (11) | 0.0041 (10) | 0.0015 (9) | 0.0032 (9) |
C14 | 0.0363 (12) | 0.0397 (13) | 0.0352 (12) | 0.0015 (10) | 0.0060 (10) | 0.0089 (10) |
C15 | 0.0384 (12) | 0.0405 (13) | 0.0377 (13) | 0.0101 (11) | 0.0044 (10) | 0.0070 (11) |
C16 | 0.0354 (12) | 0.0375 (12) | 0.0389 (13) | 0.0050 (10) | 0.0040 (10) | 0.0007 (10) |
C17 | 0.0271 (10) | 0.0336 (12) | 0.0263 (10) | 0.0009 (9) | 0.0003 (8) | 0.0024 (9) |
C18 | 0.0521 (15) | 0.0485 (16) | 0.0319 (13) | 0.0013 (12) | 0.0036 (11) | −0.0016 (11) |
C19 | 0.0428 (13) | 0.0449 (14) | 0.0288 (11) | −0.0045 (11) | 0.0071 (9) | 0.0020 (11) |
C20 | 0.0495 (14) | 0.0417 (14) | 0.0424 (14) | −0.0085 (12) | 0.0056 (11) | 0.0068 (12) |
C21 | 0.082 (2) | 0.0407 (15) | 0.0615 (19) | −0.0156 (15) | 0.0057 (15) | −0.0028 (14) |
C22 | 0.081 (2) | 0.067 (2) | 0.0578 (18) | −0.0142 (18) | −0.0002 (16) | −0.0212 (17) |
C23 | 0.0418 (14) | 0.0720 (19) | 0.0433 (15) | −0.0085 (14) | 0.0130 (12) | −0.0039 (14) |
C24 | 0.0497 (16) | 0.088 (3) | 0.067 (2) | −0.0017 (17) | 0.0184 (15) | −0.0215 (19) |
C25 | 0.111 (3) | 0.059 (2) | 0.0485 (17) | 0.0249 (19) | −0.0163 (17) | −0.0134 (15) |
Geometric parameters (Å, º) top
N1—C20 | 1.468 (3) | C9—C10 | 1.550 (3) |
N1—C19 | 1.470 (3) | C9—H9 | 0.9800 |
N1—C17 | 1.487 (3) | C10—C11 | 1.545 (3) |
O1—C18 | 1.408 (4) | C10—C12 | 1.564 (3) |
O1—C22 | 1.416 (4) | C10—H10 | 0.9800 |
O2—C23 | 1.191 (4) | C11—C17 | 1.533 (3) |
O3—C25 | 1.415 (4) | C12—C13 | 1.532 (3) |
O3—C16 | 1.432 (3) | C12—H12A | 0.9700 |
O4—C1 | 1.429 (3) | C12—H12B | 0.9700 |
O4—H1O4 | 0.8140 | C13—C14 | 1.518 (3) |
O5—C8 | 1.428 (3) | C13—C16 | 1.536 (3) |
O5—H1O5 | 0.7709 | C13—H13 | 0.9800 |
O6—C23 | 1.344 (3) | C14—H14 | 0.9800 |
O6—C14 | 1.444 (3) | C15—C16 | 1.535 (3) |
C1—C2 | 1.518 (4) | C15—H15A | 0.9700 |
C1—C11 | 1.567 (3) | C15—H15B | 0.9700 |
C1—H1 | 0.9800 | C16—H16 | 0.9800 |
C2—C3 | 1.517 (4) | C17—H17 | 0.9800 |
C2—H2A | 0.9700 | C18—H18A | 0.9700 |
C2—H2B | 0.9700 | C18—H18B | 0.9700 |
C3—C4 | 1.556 (3) | C19—H19A | 0.9700 |
C3—H3A | 0.9700 | C19—H19B | 0.9700 |
C3—H3B | 0.9700 | C20—C21 | 1.512 (4) |
C4—C18 | 1.528 (3) | C20—H20A | 0.9700 |
C4—C19 | 1.534 (4) | C20—H20B | 0.9700 |
C4—C5 | 1.557 (3) | C21—H21A | 0.9600 |
C5—C6 | 1.548 (3) | C21—H21B | 0.9600 |
C5—C11 | 1.549 (3) | C21—H21C | 0.9600 |
C5—H5 | 0.9800 | C22—H22A | 0.9600 |
C6—C7 | 1.544 (3) | C22—H22B | 0.9600 |
C6—H6A | 0.9700 | C22—H22C | 0.9600 |
C6—H6B | 0.9700 | C23—C24 | 1.492 (4) |
C7—C8 | 1.534 (3) | C24—H24A | 0.9600 |
C7—C17 | 1.539 (3) | C24—H24B | 0.9600 |
C7—H7 | 0.9800 | C24—H24C | 0.9600 |
C8—C9 | 1.547 (3) | C25—H25A | 0.9600 |
C8—C15 | 1.558 (4) | C25—H25B | 0.9600 |
C9—C14 | 1.527 (3) | C25—H25C | 0.9600 |
| | | |
C20—N1—C19 | 110.04 (19) | C10—C12—H12B | 110.5 |
C20—N1—C17 | 113.0 (2) | H12A—C12—H12B | 108.7 |
C19—N1—C17 | 113.34 (18) | C14—C13—C12 | 100.91 (19) |
C18—O1—C22 | 112.9 (2) | C14—C13—C16 | 111.22 (18) |
C25—O3—C16 | 114.4 (2) | C12—C13—C16 | 112.55 (19) |
C1—O4—H1O4 | 104.9 | C14—C13—H13 | 110.6 |
C8—O5—H1O5 | 113.6 | C12—C13—H13 | 110.6 |
C23—O6—C14 | 116.5 (2) | C16—C13—H13 | 110.6 |
O4—C1—C2 | 111.9 (2) | O6—C14—C13 | 114.3 (2) |
O4—C1—C11 | 113.00 (19) | O6—C14—C9 | 110.02 (18) |
C2—C1—C11 | 111.27 (19) | C13—C14—C9 | 102.07 (18) |
O4—C1—H1 | 106.7 | O6—C14—H14 | 110.1 |
C2—C1—H1 | 106.7 | C13—C14—H14 | 110.1 |
C11—C1—H1 | 106.7 | C9—C14—H14 | 110.1 |
C3—C2—C1 | 111.6 (2) | C16—C15—C8 | 119.2 (2) |
C3—C2—H2A | 109.3 | C16—C15—H15A | 107.5 |
C1—C2—H2A | 109.3 | C8—C15—H15A | 107.5 |
C3—C2—H2B | 109.3 | C16—C15—H15B | 107.5 |
C1—C2—H2B | 109.3 | C8—C15—H15B | 107.5 |
H2A—C2—H2B | 108.0 | H15A—C15—H15B | 107.0 |
C2—C3—C4 | 113.4 (2) | O3—C16—C15 | 104.98 (19) |
C2—C3—H3A | 108.9 | O3—C16—C13 | 111.8 (2) |
C4—C3—H3A | 108.9 | C15—C16—C13 | 114.2 (2) |
C2—C3—H3B | 108.9 | O3—C16—H16 | 108.5 |
C4—C3—H3B | 108.9 | C15—C16—H16 | 108.5 |
H3A—C3—H3B | 107.7 | C13—C16—H16 | 108.5 |
C18—C4—C19 | 107.4 (2) | N1—C17—C11 | 109.88 (18) |
C18—C4—C3 | 109.2 (2) | N1—C17—C7 | 115.51 (17) |
C19—C4—C3 | 110.3 (2) | C11—C17—C7 | 100.56 (17) |
C18—C4—C5 | 110.5 (2) | N1—C17—H17 | 110.2 |
C19—C4—C5 | 107.32 (19) | C11—C17—H17 | 110.2 |
C3—C4—C5 | 112.0 (2) | C7—C17—H17 | 110.2 |
C6—C5—C11 | 103.12 (18) | O1—C18—C4 | 109.8 (2) |
C6—C5—C4 | 110.72 (18) | O1—C18—H18A | 109.7 |
C11—C5—C4 | 108.46 (18) | C4—C18—H18A | 109.7 |
C6—C5—H5 | 111.4 | O1—C18—H18B | 109.7 |
C11—C5—H5 | 111.4 | C4—C18—H18B | 109.7 |
C4—C5—H5 | 111.4 | H18A—C18—H18B | 108.2 |
C7—C6—C5 | 105.19 (17) | N1—C19—C4 | 112.51 (19) |
C7—C6—H6A | 110.7 | N1—C19—H19A | 109.1 |
C5—C6—H6A | 110.7 | C4—C19—H19A | 109.1 |
C7—C6—H6B | 110.7 | N1—C19—H19B | 109.1 |
C5—C6—H6B | 110.7 | C4—C19—H19B | 109.1 |
H6A—C6—H6B | 108.8 | H19A—C19—H19B | 107.8 |
C8—C7—C17 | 110.87 (17) | N1—C20—C21 | 113.2 (2) |
C8—C7—C6 | 109.92 (19) | N1—C20—H20A | 108.9 |
C17—C7—C6 | 103.83 (18) | C21—C20—H20A | 108.9 |
C8—C7—H7 | 110.7 | N1—C20—H20B | 108.9 |
C17—C7—H7 | 110.7 | C21—C20—H20B | 108.9 |
C6—C7—H7 | 110.7 | H20A—C20—H20B | 107.7 |
O5—C8—C7 | 103.43 (17) | C20—C21—H21A | 109.5 |
O5—C8—C9 | 110.49 (19) | C20—C21—H21B | 109.5 |
C7—C8—C9 | 108.49 (18) | H21A—C21—H21B | 109.5 |
O5—C8—C15 | 108.44 (19) | C20—C21—H21C | 109.5 |
C7—C8—C15 | 112.87 (19) | H21A—C21—H21C | 109.5 |
C9—C8—C15 | 112.73 (18) | H21B—C21—H21C | 109.5 |
C14—C9—C8 | 111.82 (19) | O1—C22—H22A | 109.5 |
C14—C9—C10 | 100.95 (18) | O1—C22—H22B | 109.5 |
C8—C9—C10 | 112.90 (18) | H22A—C22—H22B | 109.5 |
C14—C9—H9 | 110.3 | O1—C22—H22C | 109.5 |
C8—C9—H9 | 110.3 | H22A—C22—H22C | 109.5 |
C10—C9—H9 | 110.3 | H22B—C22—H22C | 109.5 |
C11—C10—C9 | 117.66 (17) | O2—C23—O6 | 123.4 (3) |
C11—C10—C12 | 112.54 (18) | O2—C23—C24 | 126.1 (3) |
C9—C10—C12 | 104.01 (18) | O6—C23—C24 | 110.5 (3) |
C11—C10—H10 | 107.4 | C23—C24—H24A | 109.5 |
C9—C10—H10 | 107.4 | C23—C24—H24B | 109.5 |
C12—C10—H10 | 107.4 | H24A—C24—H24B | 109.5 |
C17—C11—C10 | 108.77 (18) | C23—C24—H24C | 109.5 |
C17—C11—C5 | 98.84 (16) | H24A—C24—H24C | 109.5 |
C10—C11—C5 | 112.93 (18) | H24B—C24—H24C | 109.5 |
C17—C11—C1 | 114.93 (18) | O3—C25—H25A | 109.5 |
C10—C11—C1 | 107.30 (17) | O3—C25—H25B | 109.5 |
C5—C11—C1 | 113.97 (18) | H25A—C25—H25B | 109.5 |
C13—C12—C10 | 106.19 (18) | O3—C25—H25C | 109.5 |
C13—C12—H12A | 110.5 | H25A—C25—H25C | 109.5 |
C10—C12—H12A | 110.5 | H25B—C25—H25C | 109.5 |
C13—C12—H12B | 110.5 | | |
| | | |
O4—C1—C2—C3 | 71.3 (3) | C9—C10—C12—C13 | −1.0 (2) |
C11—C1—C2—C3 | −56.2 (3) | C10—C12—C13—C14 | −28.6 (2) |
C1—C2—C3—C4 | 49.5 (3) | C10—C12—C13—C16 | 90.1 (2) |
C2—C3—C4—C18 | 130.5 (2) | C23—O6—C14—C13 | 70.8 (3) |
C2—C3—C4—C19 | −111.6 (3) | C23—O6—C14—C9 | −175.1 (2) |
C2—C3—C4—C5 | 7.8 (3) | C12—C13—C14—O6 | 166.94 (18) |
C18—C4—C5—C6 | 69.0 (3) | C16—C13—C14—O6 | 47.3 (2) |
C19—C4—C5—C6 | −47.8 (2) | C12—C13—C14—C9 | 48.2 (2) |
C3—C4—C5—C6 | −169.0 (2) | C16—C13—C14—C9 | −71.4 (2) |
C18—C4—C5—C11 | −178.5 (2) | C8—C9—C14—O6 | −50.4 (3) |
C19—C4—C5—C11 | 64.6 (2) | C10—C9—C14—O6 | −170.73 (19) |
C3—C4—C5—C11 | −56.6 (3) | C8—C9—C14—C13 | 71.2 (2) |
C11—C5—C6—C7 | −19.9 (2) | C10—C9—C14—C13 | −49.1 (2) |
C4—C5—C6—C7 | 95.9 (2) | O5—C8—C15—C16 | −140.7 (2) |
C5—C6—C7—C8 | 106.04 (19) | C7—C8—C15—C16 | 105.3 (2) |
C5—C6—C7—C17 | −12.6 (2) | C9—C8—C15—C16 | −18.1 (3) |
C17—C7—C8—O5 | −178.02 (19) | C25—O3—C16—C15 | 167.4 (3) |
C6—C7—C8—O5 | 67.8 (2) | C25—O3—C16—C13 | −68.3 (3) |
C17—C7—C8—C9 | 64.6 (2) | C8—C15—C16—O3 | 140.8 (2) |
C6—C7—C8—C9 | −49.6 (2) | C8—C15—C16—C13 | 17.9 (3) |
C17—C7—C8—C15 | −61.0 (2) | C14—C13—C16—O3 | −91.0 (2) |
C6—C7—C8—C15 | −175.27 (18) | C12—C13—C16—O3 | 156.64 (19) |
O5—C8—C9—C14 | 94.1 (2) | C14—C13—C16—C15 | 28.1 (3) |
C7—C8—C9—C14 | −153.14 (18) | C12—C13—C16—C15 | −84.3 (2) |
C15—C8—C9—C14 | −27.4 (3) | C20—N1—C17—C11 | 172.81 (18) |
O5—C8—C9—C10 | −152.85 (19) | C19—N1—C17—C11 | −61.2 (2) |
C7—C8—C9—C10 | −40.1 (2) | C20—N1—C17—C7 | −74.3 (3) |
C15—C8—C9—C10 | 85.6 (2) | C19—N1—C17—C7 | 51.7 (3) |
C14—C9—C10—C11 | 155.2 (2) | C10—C11—C17—N1 | −172.40 (17) |
C8—C9—C10—C11 | 35.7 (3) | C5—C11—C17—N1 | 69.61 (19) |
C14—C9—C10—C12 | 30.0 (2) | C1—C11—C17—N1 | −52.1 (2) |
C8—C9—C10—C12 | −89.6 (2) | C10—C11—C17—C7 | 65.37 (19) |
C9—C10—C11—C17 | −49.9 (2) | C5—C11—C17—C7 | −52.63 (19) |
C12—C10—C11—C17 | 71.0 (2) | C1—C11—C17—C7 | −174.34 (17) |
C9—C10—C11—C5 | 58.8 (3) | C8—C7—C17—N1 | 164.58 (19) |
C12—C10—C11—C5 | 179.66 (18) | C6—C7—C17—N1 | −77.4 (2) |
C9—C10—C11—C1 | −174.79 (19) | C8—C7—C17—C11 | −77.2 (2) |
C12—C10—C11—C1 | −53.9 (2) | C6—C7—C17—C11 | 40.8 (2) |
C6—C5—C11—C17 | 44.8 (2) | C22—O1—C18—C4 | −172.3 (2) |
C4—C5—C11—C17 | −72.7 (2) | C19—C4—C18—O1 | 179.2 (2) |
C6—C5—C11—C10 | −70.0 (2) | C3—C4—C18—O1 | −61.2 (3) |
C4—C5—C11—C10 | 172.52 (18) | C5—C4—C18—O1 | 62.4 (3) |
C6—C5—C11—C1 | 167.17 (19) | C20—N1—C19—C4 | 176.4 (2) |
C4—C5—C11—C1 | 49.7 (2) | C17—N1—C19—C4 | 48.9 (3) |
O4—C1—C11—C17 | −8.5 (3) | C18—C4—C19—N1 | −168.33 (19) |
C2—C1—C11—C17 | 118.4 (2) | C3—C4—C19—N1 | 72.8 (3) |
O4—C1—C11—C10 | 112.6 (2) | C5—C4—C19—N1 | −49.5 (3) |
C2—C1—C11—C10 | −120.5 (2) | C19—N1—C20—C21 | 166.5 (2) |
O4—C1—C11—C5 | −121.6 (2) | C17—N1—C20—C21 | −65.8 (3) |
C2—C1—C11—C5 | 5.3 (3) | C14—O6—C23—O2 | 8.6 (4) |
C11—C10—C12—C13 | −129.41 (19) | C14—O6—C23—C24 | −170.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H1O4···N1 | 0.81 | 1.99 | 2.7166 (19) | 148 |
O5—H1O5···O4i | 0.77 | 2.15 | 2.8184 (17) | 146 |
O5—H1O5···O6 | 0.77 | 2.57 | 3.0546 (18) | 123 |
C3—H3B···O1 | 0.97 | 2.49 | 2.895 (3) | 105 |
C6—H6A···O5 | 0.97 | 2.52 | 2.868 (2) | 101 |
Symmetry code: (i) x+1, y, z. |