The title compound, C23H29NO2, has two independent molecules in the asymmetric unit, differing in the conformation of the propylene side chain. Hydrogen bonding of the oxime moiety joins the independent molecules into a dimer, with graph-set R22[6].
Supporting information
CCDC reference: 204675
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.007 Å
- R factor = 0.057
- wR factor = 0.156
- Data-to-parameter ratio = 8.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.42
From the CIF: _reflns_number_total 3787
Count of symmetry unique reflns 3825
Completeness (_total/calc) 99.01%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
Crystals were obtained from hexane/ether. Details of the synthesis and crystallization are described by Drach et al. (2003).
Due to the absence of significant anomalous scatterers, the absolute configuration could not be determined ab initio. The chirality was chosen in agreement with the well known stereochemistry of atom C3. Of 3152 of the 3787 unique reflections reported above, the intensities of the Friedel-related reflections were measured. Friedel opposites were merged before refinement. H atoms bonded to C atoms were introduced on calculated positions, and were riding on their carrier atoms during refinement. The oxime H atom could be located on a difference Fourier map. To improve the data/parameter ratio, the oxime H was not refined but included in the model in riding mode on the oxime O atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: PLATON.
Crystal data top
C23H29NO2 | F(000) = 760 |
Mr = 351.47 | Quoted _cell_measurement_* data items refer to the initial cell
determination. The cell parameters as reported in _cell_* are based
on the complete data set. |
Monoclinic, P21 | Dx = 1.219 Mg m−3 |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 8.137 (2) Å | Cell parameters from 212 reflections |
b = 7.519 (2) Å | θ = 2.0–25.0° |
c = 31.439 (8) Å | µ = 0.08 mm−1 |
β = 95.535 (8)° | T = 150 K |
V = 1914.5 (8) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.18 × 0.02 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2770 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.096 |
Graphite monochromator | θmax = 25.4°, θmin = 1.3° |
Detector resolution: 18.4 pixels mm-1 | h = −9→9 |
ϕ scans and ω scans with κ offset | k = −9→9 |
37857 measured reflections | l = −37→37 |
3787 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0776P)2 + 0.92P] where P = (Fo2 + 2Fc2)/3 |
3787 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 0.24 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
Crystal data top
C23H29NO2 | V = 1914.5 (8) Å3 |
Mr = 351.47 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.137 (2) Å | µ = 0.08 mm−1 |
b = 7.519 (2) Å | T = 150 K |
c = 31.439 (8) Å | 0.30 × 0.18 × 0.02 mm |
β = 95.535 (8)° | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2770 reflections with I > 2σ(I) |
37857 measured reflections | Rint = 0.096 |
3787 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.057 | 1 restraint |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.24 e Å−3 |
3787 reflections | Δρmin = −0.24 e Å−3 |
469 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | |
O14 | 0.7483 (4) | 0.7763 (5) | 0.24098 (10) | 0.0392 (11) | |
O18 | 0.6712 (5) | 0.5124 (5) | 0.62014 (10) | 0.0402 (12) | |
N13 | 0.6859 (5) | 0.7490 (5) | 0.28110 (12) | 0.0334 (12) | |
C1 | 0.7887 (6) | 0.6681 (6) | 0.30820 (14) | 0.0299 (17) | |
C2 | 0.9552 (6) | 0.6077 (7) | 0.29795 (15) | 0.0349 (17) | |
C3 | 1.0086 (6) | 0.4306 (7) | 0.31799 (14) | 0.0324 (17) | |
C4 | 0.9908 (6) | 0.4377 (7) | 0.36576 (14) | 0.0329 (17) | |
C4A | 0.8103 (6) | 0.4701 (6) | 0.37458 (14) | 0.0298 (17) | |
C4B | 0.7931 (6) | 0.4661 (6) | 0.42211 (15) | 0.0295 (17) | |
C5 | 0.8117 (6) | 0.2845 (6) | 0.44305 (14) | 0.0326 (16) | |
C6 | 0.8782 (6) | 0.2979 (7) | 0.48936 (14) | 0.0365 (17) | |
C6A | 0.7876 (6) | 0.4347 (6) | 0.51302 (15) | 0.0295 (17) | |
C7 | 0.7638 (6) | 0.4145 (7) | 0.55601 (15) | 0.0336 (17) | |
C8 | 0.6885 (6) | 0.5467 (7) | 0.57792 (14) | 0.0307 (17) | |
C9 | 0.6378 (6) | 0.7043 (6) | 0.55692 (15) | 0.0318 (17) | |
C10 | 0.6584 (6) | 0.7222 (7) | 0.51374 (15) | 0.0326 (17) | |
C10A | 0.7341 (6) | 0.5903 (6) | 0.49088 (14) | 0.0276 (16) | |
C10B | 0.7580 (6) | 0.6087 (6) | 0.44536 (14) | 0.0279 (17) | |
C11 | 0.7386 (7) | 0.7913 (6) | 0.42538 (14) | 0.0350 (17) | |
C12 | 0.7942 (6) | 0.8008 (6) | 0.38061 (14) | 0.0312 (16) | |
C12A | 0.7323 (6) | 0.6410 (6) | 0.35292 (14) | 0.0297 (16) | |
C15 | 0.9217 (6) | 0.2699 (7) | 0.29666 (15) | 0.0338 (17) | |
C16 | 1.0128 (7) | 0.0967 (7) | 0.30335 (17) | 0.0459 (19) | |
C17 | 0.7780 (7) | 0.2762 (8) | 0.27380 (15) | 0.0463 (19) | |
C19 | 0.5862 (7) | 0.6390 (8) | 0.64338 (16) | 0.0427 (17) | |
C20 | 0.5434 (6) | 0.6264 (7) | 0.35064 (15) | 0.0340 (17) | |
O64 | 0.3779 (4) | 0.8831 (5) | 0.25212 (10) | 0.0373 (11) | |
O68 | 0.2486 (5) | 0.5978 (5) | −0.13131 (10) | 0.0453 (11) | |
N63 | 0.4225 (5) | 0.8398 (5) | 0.21051 (11) | 0.0331 (14) | |
C51 | 0.3045 (6) | 0.7814 (6) | 0.18518 (14) | 0.0271 (16) | |
C52 | 0.1331 (6) | 0.7497 (6) | 0.19804 (15) | 0.0314 (17) | |
C53 | 0.0712 (6) | 0.5633 (6) | 0.18347 (14) | 0.0310 (17) | |
C54 | 0.0703 (6) | 0.5585 (6) | 0.13484 (14) | 0.0305 (16) | |
C54A | 0.2481 (6) | 0.5755 (6) | 0.12083 (14) | 0.0263 (14) | |
C54B | 0.2434 (5) | 0.5646 (6) | 0.07254 (14) | 0.0270 (16) | |
C55 | 0.2106 (6) | 0.3827 (6) | 0.05312 (15) | 0.0315 (17) | |
C56 | 0.1220 (6) | 0.3935 (7) | 0.00895 (15) | 0.0378 (17) | |
C56A | 0.1991 (6) | 0.5262 (6) | −0.01896 (14) | 0.0286 (17) | |
C57 | 0.1949 (6) | 0.5047 (7) | −0.06281 (15) | 0.0358 (17) | |
C58 | 0.2590 (6) | 0.6332 (7) | −0.08831 (15) | 0.0340 (17) | |
C59 | 0.3296 (6) | 0.7852 (7) | −0.06958 (15) | 0.0338 (17) | |
C60 | 0.3357 (6) | 0.8070 (7) | −0.02545 (15) | 0.0331 (17) | |
C60A | 0.2706 (6) | 0.6807 (6) | 0.00078 (15) | 0.0277 (17) | |
C60B | 0.2712 (6) | 0.7040 (6) | 0.04736 (15) | 0.0285 (17) | |
C61 | 0.3087 (6) | 0.8871 (6) | 0.06533 (14) | 0.0330 (17) | |
C62 | 0.2767 (6) | 0.9065 (6) | 0.11184 (14) | 0.0299 (16) | |
C62A | 0.3401 (6) | 0.7454 (6) | 0.13922 (14) | 0.0269 (16) | |
C65 | 0.1680 (6) | 0.4106 (7) | 0.20571 (15) | 0.0312 (16) | |
C66 | 0.1133 (8) | 0.2269 (7) | 0.19125 (17) | 0.0440 (19) | |
C67 | 0.2898 (7) | 0.4321 (7) | 0.23617 (16) | 0.0423 (19) | |
C69 | 0.3301 (8) | 0.7163 (8) | −0.15762 (16) | 0.051 (2) | |
C70 | 0.5262 (6) | 0.7182 (7) | 0.13644 (15) | 0.0323 (17) | |
H2A | 1.03760 | 0.69930 | 0.30780 | 0.0420* | |
H2B | 0.95460 | 0.59780 | 0.26650 | 0.0420* | |
H3 | 1.12900 | 0.41700 | 0.31470 | 0.0390* | |
H4A | 0.74510 | 0.36720 | 0.36180 | 0.0360* | |
H4B | 1.06100 | 0.53440 | 0.37890 | 0.0400* | |
H4C | 1.02970 | 0.32420 | 0.37910 | 0.0400* | |
H5A | 0.70280 | 0.22460 | 0.44100 | 0.0390* | |
H5B | 0.88730 | 0.21090 | 0.42760 | 0.0390* | |
H6A | 0.86870 | 0.18060 | 0.50320 | 0.0440* | |
H6B | 0.99680 | 0.32970 | 0.49120 | 0.0440* | |
H7 | 0.79970 | 0.30860 | 0.57050 | 0.0400* | |
H9 | 0.59010 | 0.79770 | 0.57190 | 0.0380* | |
H10 | 0.61980 | 0.82720 | 0.49920 | 0.0390* | |
H11A | 0.80360 | 0.87770 | 0.44390 | 0.0420* | |
H11B | 0.62120 | 0.82700 | 0.42410 | 0.0420* | |
H12A | 0.91630 | 0.80430 | 0.38260 | 0.0380* | |
H12B | 0.75220 | 0.91200 | 0.36670 | 0.0380* | |
H14 | 0.65620 | 0.79750 | 0.22040 | 0.0590* | |
H16A | 0.94190 | −0.00100 | 0.29200 | 0.0680* | |
H16B | 1.04280 | 0.07820 | 0.33400 | 0.0680* | |
H16C | 1.11310 | 0.10000 | 0.28840 | 0.0680* | |
H17A | 0.73070 | 0.17060 | 0.26130 | 0.0560* | |
H17B | 0.72130 | 0.38620 | 0.26970 | 0.0560* | |
H19A | 0.64400 | 0.75340 | 0.64350 | 0.0640* | |
H19B | 0.58270 | 0.59760 | 0.67280 | 0.0640* | |
H19C | 0.47340 | 0.65340 | 0.62990 | 0.0640* | |
H20A | 0.49380 | 0.74120 | 0.34200 | 0.0510* | |
H20B | 0.51070 | 0.59340 | 0.37880 | 0.0510* | |
H20C | 0.50510 | 0.53530 | 0.32970 | 0.0510* | |
H52A | 0.05700 | 0.84140 | 0.18490 | 0.0370* | |
H52B | 0.13430 | 0.75950 | 0.22950 | 0.0370* | |
H53 | −0.04590 | 0.55240 | 0.19030 | 0.0370* | |
H54A | 0.00140 | 0.65720 | 0.12220 | 0.0360* | |
H54B | 0.02070 | 0.44520 | 0.12390 | 0.0360* | |
H54C | 0.31220 | 0.47040 | 0.13280 | 0.0320* | |
H55A | 0.31690 | 0.31980 | 0.05180 | 0.0380* | |
H55B | 0.14320 | 0.31280 | 0.07170 | 0.0380* | |
H56A | 0.00550 | 0.42710 | 0.01110 | 0.0450* | |
H56B | 0.12270 | 0.27470 | −0.00460 | 0.0450* | |
H57 | 0.14720 | 0.40010 | −0.07570 | 0.0430* | |
H59 | 0.37360 | 0.87410 | −0.08670 | 0.0400* | |
H60 | 0.38580 | 0.91090 | −0.01280 | 0.0400* | |
H61A | 0.24040 | 0.97510 | 0.04810 | 0.0390* | |
H61B | 0.42600 | 0.91510 | 0.06250 | 0.0390* | |
H62A | 0.15650 | 0.92010 | 0.11360 | 0.0360* | |
H62B | 0.33160 | 1.01580 | 0.12360 | 0.0360* | |
H64 | 0.45170 | 0.85300 | 0.27150 | 0.0560* | |
H66A | 0.18750 | 0.13820 | 0.20560 | 0.0660* | |
H66B | 0.11630 | 0.21710 | 0.16030 | 0.0660* | |
H66C | 0.00040 | 0.20590 | 0.19850 | 0.0660* | |
H67A | 0.34390 | 0.33120 | 0.24920 | 0.0510* | |
H67B | 0.32330 | 0.54840 | 0.24500 | 0.0510* | |
H69A | 0.27710 | 0.83330 | −0.15770 | 0.0770* | |
H69B | 0.32320 | 0.66960 | −0.18680 | 0.0770* | |
H69C | 0.44630 | 0.72750 | −0.14640 | 0.0770* | |
H70A | 0.58570 | 0.82730 | 0.14540 | 0.0480* | |
H70B | 0.54580 | 0.68980 | 0.10690 | 0.0480* | |
H70C | 0.56570 | 0.62000 | 0.15520 | 0.0480* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O14 | 0.043 (2) | 0.046 (2) | 0.0284 (18) | 0.0004 (19) | 0.0022 (15) | 0.0083 (17) |
O18 | 0.054 (2) | 0.035 (2) | 0.032 (2) | 0.0060 (18) | 0.0068 (17) | −0.0021 (16) |
N13 | 0.039 (2) | 0.031 (2) | 0.030 (2) | 0.003 (2) | 0.0028 (18) | 0.0044 (19) |
C1 | 0.034 (3) | 0.026 (3) | 0.029 (3) | −0.006 (2) | 0.000 (2) | 0.002 (2) |
C2 | 0.035 (3) | 0.032 (3) | 0.038 (3) | 0.000 (2) | 0.005 (2) | 0.002 (2) |
C3 | 0.033 (3) | 0.032 (3) | 0.032 (3) | 0.005 (2) | 0.002 (2) | 0.001 (2) |
C4 | 0.035 (3) | 0.026 (3) | 0.037 (3) | 0.002 (2) | 0.000 (2) | 0.000 (2) |
C4A | 0.035 (3) | 0.023 (3) | 0.031 (3) | −0.002 (2) | 0.001 (2) | −0.001 (2) |
C4B | 0.034 (3) | 0.024 (3) | 0.030 (3) | 0.000 (2) | 0.001 (2) | 0.004 (2) |
C5 | 0.043 (3) | 0.022 (2) | 0.033 (3) | 0.008 (2) | 0.004 (2) | 0.000 (2) |
C6 | 0.041 (3) | 0.029 (3) | 0.039 (3) | 0.008 (2) | 0.001 (2) | 0.005 (2) |
C6A | 0.029 (3) | 0.025 (3) | 0.034 (3) | 0.001 (2) | 0.000 (2) | 0.000 (2) |
C7 | 0.035 (3) | 0.026 (3) | 0.039 (3) | 0.006 (2) | −0.001 (2) | 0.003 (2) |
C8 | 0.033 (3) | 0.029 (3) | 0.030 (3) | −0.005 (2) | 0.002 (2) | 0.000 (2) |
C9 | 0.032 (3) | 0.026 (3) | 0.038 (3) | 0.000 (2) | 0.007 (2) | −0.005 (2) |
C10 | 0.037 (3) | 0.025 (3) | 0.036 (3) | 0.005 (2) | 0.004 (2) | 0.005 (2) |
C10A | 0.028 (3) | 0.021 (2) | 0.033 (3) | 0.001 (2) | −0.001 (2) | 0.003 (2) |
C10B | 0.028 (3) | 0.020 (3) | 0.035 (3) | 0.002 (2) | 0.000 (2) | −0.002 (2) |
C11 | 0.052 (3) | 0.022 (3) | 0.031 (3) | −0.001 (2) | 0.004 (2) | 0.003 (2) |
C12 | 0.037 (3) | 0.020 (2) | 0.036 (3) | 0.004 (2) | 0.001 (2) | 0.003 (2) |
C12A | 0.033 (3) | 0.024 (2) | 0.032 (3) | 0.002 (2) | 0.002 (2) | 0.004 (2) |
C15 | 0.037 (3) | 0.035 (3) | 0.030 (3) | 0.000 (3) | 0.006 (2) | −0.001 (2) |
C16 | 0.053 (4) | 0.029 (3) | 0.055 (3) | 0.001 (3) | 0.002 (3) | 0.002 (3) |
C17 | 0.053 (4) | 0.039 (3) | 0.045 (3) | 0.002 (3) | −0.005 (3) | −0.009 (3) |
C19 | 0.047 (3) | 0.043 (3) | 0.039 (3) | 0.003 (3) | 0.009 (2) | 0.001 (3) |
C20 | 0.032 (3) | 0.033 (3) | 0.037 (3) | 0.000 (2) | 0.003 (2) | 0.006 (2) |
O64 | 0.043 (2) | 0.038 (2) | 0.0300 (19) | 0.0031 (17) | −0.0016 (15) | −0.0029 (16) |
O68 | 0.062 (2) | 0.041 (2) | 0.0323 (19) | 0.006 (2) | 0.0015 (17) | −0.0005 (18) |
N63 | 0.044 (3) | 0.029 (2) | 0.026 (2) | 0.0026 (19) | 0.0026 (19) | −0.0001 (18) |
C51 | 0.031 (3) | 0.015 (2) | 0.034 (3) | 0.000 (2) | −0.003 (2) | 0.001 (2) |
C52 | 0.035 (3) | 0.025 (3) | 0.034 (3) | −0.001 (2) | 0.003 (2) | −0.003 (2) |
C53 | 0.032 (3) | 0.024 (3) | 0.038 (3) | 0.001 (2) | 0.009 (2) | 0.001 (2) |
C54 | 0.031 (3) | 0.021 (2) | 0.039 (3) | 0.000 (2) | 0.001 (2) | 0.000 (2) |
C54A | 0.023 (2) | 0.020 (2) | 0.036 (3) | 0.001 (2) | 0.003 (2) | 0.000 (2) |
C54B | 0.021 (2) | 0.021 (3) | 0.039 (3) | −0.002 (2) | 0.003 (2) | −0.003 (2) |
C55 | 0.033 (3) | 0.024 (3) | 0.038 (3) | 0.003 (2) | 0.006 (2) | −0.002 (2) |
C56 | 0.040 (3) | 0.030 (3) | 0.043 (3) | −0.006 (3) | 0.002 (2) | −0.004 (2) |
C56A | 0.022 (3) | 0.029 (3) | 0.034 (3) | 0.001 (2) | −0.002 (2) | 0.000 (2) |
C57 | 0.033 (3) | 0.032 (3) | 0.041 (3) | 0.005 (2) | −0.003 (2) | −0.002 (2) |
C58 | 0.036 (3) | 0.036 (3) | 0.029 (3) | 0.010 (2) | −0.002 (2) | −0.002 (2) |
C59 | 0.032 (3) | 0.033 (3) | 0.037 (3) | −0.002 (2) | 0.006 (2) | 0.008 (2) |
C60 | 0.036 (3) | 0.026 (3) | 0.037 (3) | −0.005 (2) | 0.002 (2) | −0.001 (2) |
C60A | 0.024 (3) | 0.023 (3) | 0.036 (3) | 0.002 (2) | 0.002 (2) | −0.001 (2) |
C60B | 0.025 (3) | 0.027 (3) | 0.034 (3) | −0.004 (2) | 0.005 (2) | 0.000 (2) |
C61 | 0.044 (3) | 0.022 (3) | 0.032 (3) | −0.007 (2) | −0.001 (2) | 0.002 (2) |
C62 | 0.033 (3) | 0.022 (2) | 0.034 (3) | −0.006 (2) | −0.001 (2) | 0.000 (2) |
C62A | 0.027 (3) | 0.021 (2) | 0.032 (3) | −0.003 (2) | −0.0002 (19) | 0.001 (2) |
C65 | 0.041 (3) | 0.023 (2) | 0.031 (3) | 0.000 (2) | 0.011 (2) | 0.001 (2) |
C66 | 0.061 (4) | 0.023 (3) | 0.048 (3) | −0.002 (3) | 0.006 (3) | 0.001 (2) |
C67 | 0.053 (4) | 0.029 (3) | 0.044 (3) | 0.004 (3) | 0.000 (3) | 0.006 (2) |
C69 | 0.071 (4) | 0.049 (4) | 0.034 (3) | −0.006 (3) | 0.005 (3) | 0.006 (3) |
C70 | 0.031 (3) | 0.030 (3) | 0.036 (3) | −0.001 (2) | 0.004 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
O14—N13 | 1.419 (5) | C19—H19B | 0.9789 |
N13—C1 | 1.288 (6) | C19—H19C | 0.9792 |
O18—C8 | 1.373 (5) | C19—H19A | 0.9802 |
O18—C19 | 1.420 (7) | C20—H20C | 0.9799 |
C4B—C10B | 1.344 (6) | C20—H20A | 0.9801 |
O64—N63 | 1.428 (5) | C20—H20B | 0.9806 |
N63—C51 | 1.265 (6) | C51—C62A | 1.525 (6) |
O68—C58 | 1.372 (6) | C51—C52 | 1.508 (7) |
O68—C69 | 1.423 (7) | C52—C53 | 1.544 (6) |
C54B—C60B | 1.346 (6) | C53—C65 | 1.524 (7) |
O64—H64 | 0.8441 | C53—C54 | 1.529 (6) |
O14—H14 | 0.9551 | C54—C54A | 1.558 (7) |
C1—C2 | 1.493 (7) | C54A—C54B | 1.517 (6) |
C1—C12A | 1.534 (6) | C54A—C62A | 1.563 (6) |
C2—C3 | 1.519 (7) | C54B—C55 | 1.511 (6) |
C3—C4 | 1.524 (6) | C55—C56 | 1.504 (7) |
C3—C15 | 1.523 (7) | C56—C56A | 1.505 (7) |
C4—C4A | 1.540 (7) | C56A—C60A | 1.415 (6) |
C4A—C12A | 1.560 (6) | C56A—C57 | 1.385 (6) |
C4A—C4B | 1.515 (6) | C57—C58 | 1.389 (7) |
C4B—C5 | 1.517 (6) | C58—C59 | 1.385 (7) |
C5—C6 | 1.507 (6) | C59—C60 | 1.393 (7) |
C6—C6A | 1.504 (7) | C60—C60A | 1.395 (7) |
C6A—C10A | 1.409 (6) | C60A—C60B | 1.474 (7) |
C6A—C7 | 1.392 (7) | C60B—C61 | 1.508 (6) |
C7—C8 | 1.385 (7) | C61—C62 | 1.517 (6) |
C8—C9 | 1.399 (7) | C62—C62A | 1.546 (6) |
C9—C10 | 1.390 (7) | C62A—C70 | 1.539 (7) |
C10—C10A | 1.402 (7) | C65—C66 | 1.508 (7) |
C10A—C10B | 1.469 (6) | C65—C67 | 1.320 (7) |
C10B—C11 | 1.512 (6) | C52—H52A | 0.9900 |
C11—C12 | 1.521 (6) | C52—H52B | 0.9909 |
C12—C12A | 1.540 (6) | C53—H53 | 1.0001 |
C12A—C20 | 1.536 (7) | C54—H54A | 0.9900 |
C15—C16 | 1.503 (7) | C54—H54B | 0.9900 |
C15—C17 | 1.313 (7) | C54A—H54C | 1.0001 |
C2—H2A | 0.9898 | C55—H55A | 0.9902 |
C2—H2B | 0.9911 | C55—H55B | 0.9900 |
C3—H3 | 1.0003 | C56—H56A | 0.9896 |
C4—H4C | 0.9893 | C56—H56B | 0.9899 |
C4—H4B | 0.9900 | C57—H57 | 0.9503 |
C4A—H4A | 1.0002 | C59—H59 | 0.9497 |
C5—H5A | 0.9906 | C60—H60 | 0.9505 |
C5—H5B | 0.9891 | C61—H61A | 0.9910 |
C6—H6A | 0.9898 | C61—H61B | 0.9898 |
C6—H6B | 0.9905 | C62—H62A | 0.9902 |
C7—H7 | 0.9493 | C62—H62B | 0.9898 |
C9—H9 | 0.9492 | C66—H66A | 0.9800 |
C10—H10 | 0.9504 | C66—H66B | 0.9785 |
C11—H11A | 0.9906 | C66—H66C | 0.9804 |
C11—H11B | 0.9894 | C67—H67A | 0.9499 |
C12—H12B | 0.9891 | C67—H67B | 0.9494 |
C12—H12A | 0.9898 | C69—H69A | 0.9796 |
C16—H16B | 0.9809 | C69—H69B | 0.9788 |
C16—H16C | 0.9806 | C69—H69C | 0.9804 |
C16—H16A | 0.9798 | C70—H70A | 0.9800 |
C17—H17B | 0.9498 | C70—H70B | 0.9809 |
C17—H17A | 0.9507 | C70—H70C | 0.9797 |
| | | |
O14···O64 | 3.171 (5) | H7···H6A | 2.4387 |
O14···N63 | 2.772 (5) | H9···C19 | 2.5473 |
O18···C16i | 3.407 (7) | H9···H19A | 2.2760 |
O64···O14 | 3.171 (5) | H9···H5Av | 2.4414 |
O64···N13 | 2.773 (5) | H9···H19C | 2.3954 |
O68···C70ii | 3.404 (7) | H10···H11A | 2.4301 |
O14···H2B | 2.2368 | H10···C11 | 2.6127 |
O14···H16Aiii | 2.7150 | H10···H11B | 2.3622 |
O14···H64 | 2.7431 | H11A···H10 | 2.4301 |
O18···H20Aiv | 2.7723 | H11A···H6Bi | 2.5084 |
O18···H16Bi | 2.6631 | H11A···C5iii | 3.0596 |
O64···H67B | 2.5616 | H11A···C10 | 2.8433 |
O64···H52B | 2.2420 | H11B···C20 | 2.7798 |
O64···H66Aiii | 2.7895 | H11B···C10 | 2.9138 |
O64···H19Bv | 2.8513 | H11B···H20B | 2.3822 |
O64···H14 | 2.6405 | H11B···C8v | 3.0087 |
O68···H66Cvi | 2.8987 | H11B···H10 | 2.3622 |
O68···H70Aii | 2.5032 | H12A···C4B | 3.0421 |
N13···O64 | 2.773 (5) | H12A···H4B | 2.3547 |
N13···N63 | 3.011 (5) | H12A···C2 | 3.0871 |
N63···O14 | 2.772 (5) | H12A···C4 | 2.8823 |
N63···N13 | 3.011 (5) | H12B···H20A | 2.5216 |
N63···C67 | 3.374 (7) | H12B···H19Cv | 2.5911 |
N13···H17B | 2.7700 | H14···H70A | 2.3829 |
N13···H20A | 2.5865 | H14···C70 | 2.8113 |
N13···H16Aiii | 2.8022 | H14···H64 | 2.4576 |
N13···H20C | 2.7412 | H14···O64 | 2.6405 |
N13···H64 | 2.0551 | H14···N63 | 1.9235 |
N63···H67B | 2.6071 | H14···C51 | 2.9697 |
N63···H14 | 1.9235 | H14···H70C | 2.4968 |
N63···H66Aiii | 2.9424 | H16A···H2Aix | 2.4200 |
N63···H70C | 2.7393 | H16A···H17A | 2.2869 |
N63···H70A | 2.5469 | H16A···O14ix | 2.7149 |
C1···C17 | 3.137 (7) | H16A···N13ix | 2.8022 |
C4A···C17 | 3.475 (7) | H16A···C1ix | 2.8506 |
C6···C10Avii | 3.521 (7) | H16A···C2ix | 2.9494 |
C10A···C6i | 3.521 (7) | H16B···C19vii | 3.0682 |
C10B···C20 | 3.306 (7) | H16B···C4 | 2.9265 |
C16···O18vii | 3.407 (7) | H16B···H4C | 2.3393 |
C16···C19vii | 3.535 (8) | H16B···O18vii | 2.6631 |
C17···C4A | 3.475 (7) | H16C···H3 | 2.5221 |
C17···C1 | 3.137 (7) | H17A···H16A | 2.2869 |
C19···C16i | 3.535 (8) | H17A···H69Bii | 2.3410 |
C20···C10B | 3.306 (7) | H17B···C1 | 2.4760 |
C51···C67 | 3.085 (7) | H17B···N13 | 2.7700 |
C52···C66iii | 3.597 (7) | H17B···H2B | 2.4864 |
C56···C60Aviii | 3.560 (7) | H17B···C2 | 2.6189 |
C60A···C56vi | 3.560 (7) | H19A···C9 | 2.7425 |
C60B···C70 | 3.323 (7) | H19A···H3i | 2.4867 |
C66···C52ix | 3.597 (7) | H19A···H9 | 2.2760 |
C67···C51 | 3.085 (7) | H19B···H64iv | 2.5733 |
C67···N63 | 3.374 (7) | H19B···O64iv | 2.8513 |
C70···O68x | 3.404 (7) | H19C···H12Biv | 2.5911 |
C70···C60B | 3.323 (7) | H19C···H9 | 2.3954 |
C1···H17B | 2.4760 | H19C···H4Av | 2.4296 |
C1···H16Aiii | 2.8506 | H19C···C9 | 2.7915 |
C2···H16Aiii | 2.9494 | H19C···H5Av | 2.5873 |
C2···H17B | 2.6189 | H20A···H12B | 2.5216 |
C2···H52Bxi | 2.9432 | H20A···H64 | 2.3644 |
C2···H12A | 3.0871 | H20A···N13 | 2.5865 |
C4···H5B | 2.7772 | H20A···O18v | 2.7723 |
C4···H12A | 2.8823 | H20B···C4B | 2.7289 |
C4···H16B | 2.9265 | H20B···C10B | 2.7621 |
C4B···H12A | 3.0421 | H20B···H11B | 2.3822 |
C4B···H20B | 2.7289 | H20B···C11 | 2.6970 |
C5···H4C | 2.8224 | H20C···H4A | 2.4596 |
C5···H11Aix | 3.0596 | H20C···N13 | 2.7412 |
C8···H11Biv | 3.0087 | H52A···C62 | 3.0828 |
C9···H19A | 2.7425 | H52A···C66iii | 2.9383 |
C9···H5Av | 2.7827 | H52A···H54A | 2.4159 |
C9···H19C | 2.7915 | H52A···H62A | 2.5260 |
C10···H11B | 2.9138 | H52A···H66Aiii | 2.5294 |
C10···H6Bi | 2.9382 | H52B···O64 | 2.2420 |
C10···H11A | 2.8433 | H52B···C2xii | 2.9432 |
C10A···H6Bi | 2.8486 | H52B···C67 | 2.7666 |
C10B···H20B | 2.7621 | H52B···H2Bxii | 2.3016 |
C11···H10 | 2.6127 | H52B···H67B | 2.2310 |
C11···H20B | 2.6970 | H53···H2Bxii | 2.4195 |
C12···H4B | 2.9582 | H54A···C62 | 2.9629 |
C15···H4A | 2.7133 | H54A···H52A | 2.4159 |
C16···H4C | 2.9246 | H54A···H62A | 2.3747 |
C16···H2Aix | 2.9972 | H54A···H57vi | 2.5679 |
C17···H69Bii | 2.8926 | H54B···C55 | 2.8677 |
C17···H4A | 2.8874 | H54B···C66 | 2.7272 |
C17···H2B | 2.8335 | H54B···H55B | 2.2346 |
C19···H9 | 2.5473 | H54B···H66B | 2.1644 |
C19···H16Bi | 3.0682 | H54C···C65 | 2.7115 |
C20···H64 | 3.0483 | H54C···H55B | 2.5447 |
C20···H11B | 2.7798 | H54C···H70C | 2.3950 |
C51···H14 | 2.9697 | H55A···C59ii | 2.8886 |
C51···H67B | 2.5640 | H55A···C60ii | 3.0229 |
C51···H66Aiii | 2.9383 | H55B···C54 | 2.8165 |
C52···H67B | 2.5348 | H55B···H54B | 2.2346 |
C52···H2Bxii | 2.9410 | H55B···H54C | 2.5447 |
C52···H62A | 2.9703 | H56A···C60viii | 2.9948 |
C52···H66Aiii | 2.9606 | H56A···C60Aviii | 2.9082 |
C53···H2Bxii | 2.8739 | H56B···H57 | 2.4518 |
C54···H66B | 2.7041 | H57···H56B | 2.4518 |
C54···H62A | 2.9018 | H57···H54Aviii | 2.5679 |
C54···H55B | 2.8165 | H59···C69 | 2.5204 |
C54B···H62A | 3.0802 | H59···H69A | 2.3141 |
C54B···H70B | 2.7559 | H59···H69C | 2.3026 |
C55···H54B | 2.8677 | H59···H70Bx | 2.5590 |
C55···H61Aix | 3.0796 | H60···C61 | 2.5993 |
C58···H61Bii | 3.0848 | H60···H61A | 2.3949 |
C59···H69C | 2.7139 | H60···H61B | 2.3586 |
C59···H69A | 2.7857 | H61A···C55iii | 3.0796 |
C59···H55Ax | 2.8886 | H61A···C60 | 2.8092 |
C60···H56Avi | 2.9948 | H61A···H60 | 2.3949 |
C60···H61B | 2.9076 | H61B···C60 | 2.9076 |
C60···H55Ax | 3.0229 | H61B···C70 | 2.8098 |
C60···H61A | 2.8092 | H61B···H60 | 2.3586 |
C60A···H56Avi | 2.9082 | H61B···H70B | 2.3465 |
C60B···H70B | 2.7751 | H61B···C58x | 3.0848 |
C61···H60 | 2.5993 | H62A···C52 | 2.9703 |
C61···H70B | 2.6729 | H62A···C54 | 2.9018 |
C62···H54A | 2.9629 | H62A···C54B | 3.0802 |
C62···H52A | 3.0828 | H62A···H52A | 2.5260 |
C65···H2Bxii | 3.0478 | H62A···H54A | 2.3747 |
C65···H54C | 2.7115 | H62B···H70A | 2.5456 |
C66···H54B | 2.7272 | H62B···H69Cx | 2.4625 |
C66···H52Aix | 2.9383 | H64···O14 | 2.7431 |
C67···H3xii | 2.9058 | H64···N13 | 2.0551 |
C67···H52B | 2.7666 | H64···C20 | 3.0483 |
C69···H66Cvi | 2.8676 | H64···H14 | 2.4576 |
C69···H59 | 2.5204 | H64···H20A | 2.3644 |
C69···H70Aii | 3.0201 | H64···H19Bv | 2.5733 |
C70···H61B | 2.8098 | H66A···O64ix | 2.7895 |
C70···H14 | 2.8113 | H66A···N63ix | 2.9424 |
H2A···C16iii | 2.9972 | H66A···C51ix | 2.9383 |
H2A···H4B | 2.5472 | H66A···C52ix | 2.9606 |
H2A···H16Aiii | 2.4200 | H66A···H52Aix | 2.5294 |
H2B···C65xi | 3.0478 | H66A···H67A | 2.2952 |
H2B···C52xi | 2.9410 | H66B···C54 | 2.7041 |
H2B···C53xi | 2.8739 | H66B···H54B | 2.1644 |
H2B···O14 | 2.2368 | H66C···O68viii | 2.8987 |
H2B···C17 | 2.8335 | H66C···C69viii | 2.8676 |
H2B···H53xi | 2.4195 | H67A···H66A | 2.2952 |
H2B···H17B | 2.4864 | H67B···O64 | 2.5616 |
H2B···H52Bxi | 2.3016 | H67B···N63 | 2.6071 |
H3···H19Avii | 2.4867 | H67B···C51 | 2.5640 |
H3···H16C | 2.5221 | H67B···C52 | 2.5348 |
H3···C67xi | 2.9058 | H67B···H52B | 2.2310 |
H4A···C17 | 2.8874 | H69A···C59 | 2.7857 |
H4A···H5B | 2.5569 | H69A···H59 | 2.3141 |
H4A···C15 | 2.7133 | H69A···H70Cx | 2.5040 |
H4A···H20C | 2.4596 | H69B···C17x | 2.8926 |
H4A···H19Civ | 2.4296 | H69B···H17Ax | 2.3410 |
H4B···C12 | 2.9582 | H69C···C59 | 2.7139 |
H4B···H12A | 2.3547 | H69C···H59 | 2.3026 |
H4B···H2A | 2.5472 | H69C···H62Bii | 2.4625 |
H4C···C5 | 2.8224 | H70A···N63 | 2.5469 |
H4C···C16 | 2.9246 | H70A···H14 | 2.3829 |
H4C···H5B | 2.1758 | H70A···H62B | 2.5456 |
H4C···H16B | 2.3393 | H70A···O68x | 2.5032 |
H5A···H19Civ | 2.5873 | H70A···C69x | 3.0201 |
H5A···C9iv | 2.7827 | H70B···C54B | 2.7559 |
H5A···H9iv | 2.4414 | H70B···C60B | 2.7751 |
H5B···H4A | 2.5569 | H70B···C61 | 2.6729 |
H5B···H4C | 2.1758 | H70B···H61B | 2.3465 |
H5B···C4 | 2.7772 | H70B···H59ii | 2.5590 |
H6A···H7 | 2.4387 | H70C···N63 | 2.7393 |
H6B···C10vii | 2.9382 | H70C···H14 | 2.4968 |
H6B···C10Avii | 2.8486 | H70C···H54C | 2.3950 |
H6B···H11Avii | 2.5084 | H70C···H69Aii | 2.5040 |
| | | |
C8—O18—C19 | 118.2 (4) | H20A—C20—H20B | 109.43 |
N13—O14—H14 | 107.55 | C12A—C20—H20A | 109.48 |
C58—O68—C69 | 117.6 (4) | H20A—C20—H20C | 109.49 |
N63—O64—H64 | 111.96 | N63—C51—C52 | 123.5 (4) |
O14—N13—C1 | 113.0 (4) | C52—C51—C62A | 119.4 (4) |
O64—N63—C51 | 114.3 (4) | N63—C51—C62A | 117.1 (4) |
N13—C1—C2 | 123.1 (4) | C51—C52—C53 | 110.3 (4) |
C2—C1—C12A | 121.0 (4) | C52—C53—C65 | 114.1 (4) |
N13—C1—C12A | 115.9 (4) | C54—C53—C65 | 113.2 (4) |
C1—C2—C3 | 114.0 (4) | C52—C53—C54 | 106.7 (4) |
C4—C3—C15 | 112.2 (4) | C53—C54—C54A | 111.5 (4) |
C2—C3—C15 | 114.3 (4) | C54—C54A—C62A | 112.8 (4) |
C2—C3—C4 | 109.1 (4) | C54B—C54A—C62A | 112.3 (4) |
C3—C4—C4A | 111.5 (4) | C54—C54A—C54B | 110.1 (4) |
C4—C4A—C12A | 114.0 (4) | C54A—C54B—C60B | 123.9 (4) |
C4B—C4A—C12A | 112.0 (4) | C55—C54B—C60B | 120.0 (4) |
C4—C4A—C4B | 110.8 (4) | C54A—C54B—C55 | 116.1 (4) |
C5—C4B—C10B | 120.0 (4) | C54B—C55—C56 | 112.0 (4) |
C4A—C4B—C10B | 124.4 (4) | C55—C56—C56A | 112.6 (4) |
C4A—C4B—C5 | 115.5 (4) | C56—C56A—C57 | 122.1 (4) |
C4B—C5—C6 | 111.8 (4) | C57—C56A—C60A | 120.1 (4) |
C5—C6—C6A | 112.1 (4) | C56—C56A—C60A | 117.7 (4) |
C6—C6A—C10A | 117.8 (4) | C56A—C57—C58 | 121.2 (5) |
C7—C6A—C10A | 120.3 (4) | O68—C58—C59 | 124.2 (4) |
C6—C6A—C7 | 121.8 (4) | C57—C58—C59 | 119.5 (4) |
C6A—C7—C8 | 120.9 (5) | O68—C58—C57 | 116.3 (4) |
O18—C8—C7 | 115.9 (4) | C58—C59—C60 | 119.6 (5) |
O18—C8—C9 | 124.2 (4) | C59—C60—C60A | 122.0 (5) |
C7—C8—C9 | 119.8 (4) | C56A—C60A—C60 | 117.6 (4) |
C8—C9—C10 | 119.0 (4) | C56A—C60A—C60B | 119.7 (4) |
C9—C10—C10A | 122.2 (5) | C60—C60A—C60B | 122.8 (4) |
C6A—C10A—C10B | 119.7 (4) | C54B—C60B—C61 | 122.0 (4) |
C6A—C10A—C10 | 117.7 (4) | C60A—C60B—C61 | 117.5 (4) |
C10—C10A—C10B | 122.6 (4) | C54B—C60B—C60A | 120.5 (4) |
C10A—C10B—C11 | 118.2 (4) | C60B—C61—C62 | 113.7 (4) |
C4B—C10B—C10A | 120.6 (4) | C61—C62—C62A | 112.5 (4) |
C4B—C10B—C11 | 121.2 (4) | C51—C62A—C54A | 111.6 (4) |
C10B—C11—C12 | 113.5 (4) | C51—C62A—C62 | 107.8 (4) |
C11—C12—C12A | 112.1 (4) | C54A—C62A—C62 | 108.2 (4) |
C1—C12A—C4A | 111.4 (4) | C54A—C62A—C70 | 108.0 (4) |
C12—C12A—C20 | 110.7 (4) | C62—C62A—C70 | 110.5 (4) |
C1—C12A—C20 | 110.7 (4) | C51—C62A—C70 | 110.8 (4) |
C4A—C12A—C12 | 107.4 (4) | C53—C65—C67 | 124.0 (5) |
C1—C12A—C12 | 107.7 (4) | C66—C65—C67 | 120.7 (5) |
C4A—C12A—C20 | 108.9 (4) | C53—C65—C66 | 115.3 (4) |
C3—C15—C16 | 115.1 (4) | C51—C52—H52A | 109.60 |
C3—C15—C17 | 124.3 (5) | C51—C52—H52B | 109.60 |
C16—C15—C17 | 120.6 (5) | C53—C52—H52A | 109.60 |
C3—C2—H2A | 108.80 | C53—C52—H52B | 109.58 |
H2A—C2—H2B | 107.60 | H52A—C52—H52B | 108.07 |
C1—C2—H2B | 108.72 | C52—C53—H53 | 107.52 |
C3—C2—H2B | 108.77 | C54—C53—H53 | 107.46 |
C1—C2—H2A | 108.79 | C65—C53—H53 | 107.51 |
C2—C3—H3 | 106.90 | C53—C54—H54A | 109.37 |
C15—C3—H3 | 106.93 | C53—C54—H54B | 109.28 |
C4—C3—H3 | 107.02 | C54A—C54—H54A | 109.30 |
C3—C4—H4C | 109.31 | C54A—C54—H54B | 109.33 |
C3—C4—H4B | 109.34 | H54A—C54—H54B | 108.03 |
H4B—C4—H4C | 107.97 | C54—C54A—H54C | 107.08 |
C4A—C4—H4B | 109.30 | C54B—C54A—H54C | 107.20 |
C4A—C4—H4C | 109.38 | C62A—C54A—H54C | 107.03 |
C4—C4A—H4A | 106.46 | C54B—C55—H55A | 109.17 |
C4B—C4A—H4A | 106.56 | C54B—C55—H55B | 109.17 |
C12A—C4A—H4A | 106.50 | C56—C55—H55A | 109.27 |
C4B—C5—H5A | 109.26 | C56—C55—H55B | 109.27 |
H5A—C5—H5B | 107.97 | H55A—C55—H55B | 107.88 |
C6—C5—H5B | 109.24 | C55—C56—H56A | 109.13 |
C6—C5—H5A | 109.20 | C55—C56—H56B | 109.06 |
C4B—C5—H5B | 109.34 | C56A—C56—H56A | 109.05 |
C5—C6—H6A | 109.22 | C56A—C56—H56B | 109.11 |
C6A—C6—H6B | 109.11 | H56A—C56—H56B | 107.76 |
C6A—C6—H6A | 109.23 | C56A—C57—H57 | 119.40 |
C5—C6—H6B | 109.25 | C58—C57—H57 | 119.36 |
H6A—C6—H6B | 107.84 | C58—C59—H59 | 120.23 |
C8—C7—H7 | 119.58 | C60—C59—H59 | 120.16 |
C6A—C7—H7 | 119.49 | C59—C60—H60 | 119.08 |
C8—C9—H9 | 120.57 | C60A—C60—H60 | 118.95 |
C10—C9—H9 | 120.43 | C60B—C61—H61A | 108.80 |
C10A—C10—H10 | 118.84 | C60B—C61—H61B | 108.82 |
C9—C10—H10 | 118.99 | C62—C61—H61A | 108.87 |
C12—C11—H11B | 108.77 | C62—C61—H61B | 108.84 |
H11A—C11—H11B | 107.74 | H61A—C61—H61B | 107.68 |
C12—C11—H11A | 108.87 | C61—C62—H62A | 109.03 |
C10B—C11—H11A | 108.84 | C61—C62—H62B | 109.07 |
C10B—C11—H11B | 108.97 | C62A—C62—H62A | 109.16 |
C12A—C12—H12B | 109.24 | C62A—C62—H62B | 109.17 |
C11—C12—H12B | 109.14 | H62A—C62—H62B | 107.82 |
C12A—C12—H12A | 109.15 | C65—C66—H66A | 109.50 |
C11—C12—H12A | 109.21 | C65—C66—H66B | 109.50 |
H12A—C12—H12B | 107.90 | C65—C66—H66C | 109.48 |
C15—C16—H16B | 109.45 | H66A—C66—H66B | 109.46 |
H16A—C16—H16C | 109.42 | H66A—C66—H66C | 109.44 |
H16B—C16—H16C | 109.55 | H66B—C66—H66C | 109.44 |
H16A—C16—H16B | 109.48 | C65—C67—H67A | 119.96 |
C15—C16—H16A | 109.48 | C65—C67—H67B | 119.95 |
C15—C16—H16C | 109.45 | H67A—C67—H67B | 120.10 |
H17A—C17—H17B | 119.95 | O68—C69—H69A | 109.52 |
C15—C17—H17A | 119.99 | O68—C69—H69B | 109.42 |
C15—C17—H17B | 120.07 | O68—C69—H69C | 109.40 |
O18—C19—H19B | 109.45 | H69A—C69—H69B | 109.53 |
H19A—C19—H19C | 109.51 | H69A—C69—H69C | 109.44 |
O18—C19—H19C | 109.53 | H69B—C69—H69C | 109.52 |
O18—C19—H19A | 109.45 | C62A—C70—H70A | 109.51 |
H19A—C19—H19B | 109.46 | C62A—C70—H70B | 109.48 |
H19B—C19—H19C | 109.43 | C62A—C70—H70C | 109.48 |
C12A—C20—H20C | 109.47 | H70A—C70—H70B | 109.48 |
C12A—C20—H20B | 109.48 | H70A—C70—H70C | 109.48 |
H20B—C20—H20C | 109.47 | H70B—C70—H70C | 109.39 |
| | | |
C19—O18—C8—C7 | −176.4 (5) | C10B—C11—C12—C12A | 44.3 (6) |
C19—O18—C8—C9 | 4.6 (7) | C11—C12—C12A—C20 | 56.5 (5) |
C69—O68—C58—C57 | −172.8 (5) | C11—C12—C12A—C4A | −62.4 (5) |
C69—O68—C58—C59 | 6.5 (7) | C11—C12—C12A—C1 | 177.6 (4) |
O14—N13—C1—C2 | −0.8 (6) | N63—C51—C62A—C62 | −98.9 (5) |
O14—N13—C1—C12A | 177.5 (4) | N63—C51—C62A—C54A | 142.4 (4) |
O64—N63—C51—C52 | −3.3 (6) | C52—C51—C62A—C62 | 80.0 (5) |
O64—N63—C51—C62A | 175.6 (4) | N63—C51—C62A—C70 | 22.0 (6) |
C12A—C1—C2—C3 | 39.2 (6) | C52—C51—C62A—C54A | −38.6 (6) |
N13—C1—C2—C3 | −142.6 (5) | C62A—C51—C52—C53 | 49.9 (5) |
N13—C1—C12A—C4A | 150.6 (4) | N63—C51—C52—C53 | −131.3 (5) |
N13—C1—C12A—C12 | −91.9 (5) | C52—C51—C62A—C70 | −159.0 (4) |
C2—C1—C12A—C4A | −31.1 (6) | C51—C52—C53—C54 | −60.0 (5) |
N13—C1—C12A—C20 | 29.2 (6) | C51—C52—C53—C65 | 65.8 (5) |
C2—C1—C12A—C12 | 86.4 (5) | C65—C53—C54—C54A | −61.7 (5) |
C2—C1—C12A—C20 | −152.5 (4) | C52—C53—C65—C66 | −178.4 (4) |
C1—C2—C3—C15 | 74.5 (5) | C52—C53—C65—C67 | 2.8 (7) |
C1—C2—C3—C4 | −52.0 (5) | C52—C53—C54—C54A | 64.7 (5) |
C2—C3—C15—C16 | 157.2 (4) | C54—C53—C65—C66 | −56.0 (6) |
C2—C3—C4—C4A | 61.2 (5) | C54—C53—C65—C67 | 125.2 (5) |
C15—C3—C4—C4A | −66.5 (5) | C53—C54—C54A—C62A | −55.4 (5) |
C4—C3—C15—C17 | 102.2 (6) | C53—C54—C54A—C54B | 178.3 (4) |
C2—C3—C15—C17 | −22.7 (7) | C54—C54A—C54B—C60B | 108.9 (5) |
C4—C3—C15—C16 | −77.9 (5) | C62A—C54A—C54B—C55 | 160.2 (4) |
C3—C4—C4A—C12A | −55.9 (5) | C62A—C54A—C54B—C60B | −17.7 (6) |
C3—C4—C4A—C4B | 176.7 (4) | C54—C54A—C54B—C55 | −73.2 (5) |
C4B—C4A—C12A—C12 | 47.5 (5) | C54B—C54A—C62A—C62 | 46.2 (5) |
C12A—C4A—C4B—C5 | 160.5 (4) | C54B—C54A—C62A—C70 | −73.4 (5) |
C4B—C4A—C12A—C1 | 165.2 (4) | C54—C54A—C62A—C70 | 161.5 (4) |
C4B—C4A—C12A—C20 | −72.5 (5) | C54—C54A—C62A—C51 | 39.4 (5) |
C4—C4A—C12A—C20 | 160.8 (4) | C54—C54A—C62A—C62 | −78.9 (4) |
C4—C4A—C12A—C12 | −79.3 (5) | C54B—C54A—C62A—C51 | 164.6 (4) |
C4—C4A—C4B—C5 | −71.0 (5) | C54A—C54B—C55—C56 | 149.8 (4) |
C4—C4A—C4B—C10B | 111.3 (5) | C55—C54B—C60B—C61 | −178.4 (4) |
C12A—C4A—C4B—C10B | −17.2 (7) | C55—C54B—C60B—C60A | −0.2 (7) |
C4—C4A—C12A—C1 | 38.4 (5) | C60B—C54B—C55—C56 | −32.1 (6) |
C4A—C4B—C10B—C11 | −2.4 (8) | C54A—C54B—C60B—C60A | 177.6 (4) |
C4A—C4B—C5—C6 | 151.1 (4) | C54A—C54B—C60B—C61 | −0.6 (7) |
C4A—C4B—C10B—C10A | 176.4 (4) | C54B—C55—C56—C56A | 47.7 (5) |
C5—C4B—C10B—C11 | −180.0 (4) | C55—C56—C56A—C60A | −33.7 (6) |
C5—C4B—C10B—C10A | −1.2 (7) | C55—C56—C56A—C57 | 149.2 (5) |
C10B—C4B—C5—C6 | −31.1 (6) | C56—C56A—C57—C58 | 176.5 (5) |
C4B—C5—C6—C6A | 48.2 (5) | C57—C56A—C60A—C60B | 178.7 (5) |
C5—C6—C6A—C10A | −36.1 (6) | C56—C56A—C60A—C60 | −177.3 (4) |
C5—C6—C6A—C7 | 147.2 (5) | C56—C56A—C60A—C60B | 1.6 (7) |
C7—C6A—C10A—C10B | −179.2 (4) | C60A—C56A—C57—C58 | −0.4 (7) |
C10A—C6A—C7—C8 | −0.5 (7) | C57—C56A—C60A—C60 | −0.2 (7) |
C7—C6A—C10A—C10 | 0.5 (7) | C56A—C57—C58—O68 | 179.8 (4) |
C6—C6A—C7—C8 | 176.2 (5) | C56A—C57—C58—C59 | 0.5 (8) |
C6—C6A—C10A—C10 | −176.3 (4) | O68—C58—C59—C60 | −179.2 (5) |
C6—C6A—C10A—C10B | 4.0 (7) | C57—C58—C59—C60 | 0.1 (7) |
C6A—C7—C8—C9 | −1.1 (7) | C58—C59—C60—C60A | −0.8 (8) |
C6A—C7—C8—O18 | 179.9 (4) | C59—C60—C60A—C60B | −178.0 (5) |
C7—C8—C9—C10 | 2.5 (7) | C59—C60—C60A—C56A | 0.9 (7) |
O18—C8—C9—C10 | −178.5 (5) | C56A—C60A—C60B—C61 | −165.1 (4) |
C8—C9—C10—C10A | −2.5 (7) | C60—C60A—C60B—C54B | −164.5 (5) |
C9—C10—C10A—C10B | −179.4 (5) | C56A—C60A—C60B—C54B | 16.7 (7) |
C9—C10—C10A—C6A | 1.0 (7) | C60—C60A—C60B—C61 | 13.8 (7) |
C10—C10A—C10B—C4B | −163.7 (5) | C54B—C60B—C61—C62 | −12.1 (7) |
C6A—C10A—C10B—C4B | 15.9 (7) | C60A—C60B—C61—C62 | 169.6 (4) |
C10—C10A—C10B—C11 | 15.1 (7) | C60B—C61—C62—C62A | 43.3 (6) |
C6A—C10A—C10B—C11 | −165.3 (5) | C61—C62—C62A—C54A | −60.4 (5) |
C10A—C10B—C11—C12 | 170.2 (4) | C61—C62—C62A—C70 | 57.7 (5) |
C4B—C10B—C11—C12 | −11.0 (7) | C61—C62—C62A—C51 | 178.9 (4) |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z; (iii) x, y+1, z; (iv) −x+1, y−1/2, −z+1; (v) −x+1, y+1/2, −z+1; (vi) −x, y+1/2, −z; (vii) −x+2, y−1/2, −z+1; (viii) −x, y−1/2, −z; (ix) x, y−1, z; (x) −x+1, y+1/2, −z; (xi) x+1, y, z; (xii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N63 | 0.96 | 1.92 | 2.772 (5) | 147 |
O64—H64···N13 | 0.84 | 2.06 | 2.773 (5) | 142 |
C2—H2B···O14 | 0.99 | 2.24 | 2.659 (6) | 104 |
C52—H52B···O64 | 0.99 | 2.24 | 2.685 (6) | 106 |
C67—H67B···O64 | 0.95 | 2.56 | 3.492 (7) | 167 |
C67—H67B···N63 | 0.95 | 2.61 | 3.374 (7) | 138 |
C70—H70A···O68x | 0.98 | 2.50 | 3.404 (7) | 153 |
Symmetry code: (x) −x+1, y+1/2, −z. |
Experimental details
Crystal data |
Chemical formula | C23H29NO2 |
Mr | 351.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 150 |
a, b, c (Å) | 8.137 (2), 7.519 (2), 31.439 (8) |
β (°) | 95.535 (8) |
V (Å3) | 1914.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.18 × 0.02 |
|
Data collection |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37857, 3787, 2770 |
Rint | 0.096 |
(sin θ/λ)max (Å−1) | 0.604 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.156, 1.07 |
No. of reflections | 3787 |
No. of parameters | 469 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.24 |
Selected geometric parameters (Å, º) topO14—N13 | 1.419 (5) | O64—N63 | 1.428 (5) |
N13—C1 | 1.288 (6) | N63—C51 | 1.265 (6) |
O18—C8 | 1.373 (5) | O68—C58 | 1.372 (6) |
O18—C19 | 1.420 (7) | O68—C69 | 1.423 (7) |
C4B—C10B | 1.344 (6) | C54B—C60B | 1.346 (6) |
| | | |
O14—N13—C1 | 113.0 (4) | O64—N63—C51 | 114.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N63 | 0.96 | 1.92 | 2.772 (5) | 147 |
O64—H64···N13 | 0.84 | 2.06 | 2.773 (5) | 142 |
The crystal structure of the title compound, (I), was determined to confirm beyond any doubt the stereochemistry around ring junction C4a—C12a of this (unnatural) D-homosteroid skeleton (Drach et al., 2003). The configuration of atom C3 was known to be R. In both independent molecules (see below), the configurations of atoms C4a and C12a were found to be S and R, respectively.
The title compound crystallizes with two independent molecules in the asymmetric unit. An atomic displacement ellipsoid plot is given in Fig. 1, together with the adopted labelling scheme for atoms and rings. The molecule labelled C1–C20 will be referred to as molecule 1. The labels of molecule 2 are obtained by adding 50 to the numerical part of the label of the corresponding atom in molecule 1. The independent molecules differ only slightly in conformation. Fig. 2 shows a plot of the superposition of the two molecules using the quaternion transformation method (Mackay, 1984). The independent molecules are related by a 172° rotation along the vector [−0.02, 1.00, 0.00], see Fig. 3. The most obvious difference is the orientation of the isopropenyl moiety, as can be expressed by the torsion angles C2—C3—C15—C17 and C52—C53—C65—C67, which amount to −22.7 (7) and 2.8 (7)°, respectively. There is also a small difference in the orientation of the oxime H atom, as is indicated by the torsion angles C1—N13—O14—H14 (160°) and C51—N63—O64—H64 (140°).
The conformation of the steroid skeleton in both independent molecules is the same. Ring B has adopted a screw-boat conformation with the local twofold rotation axes running through the midpoint of the bond C10A—C10B [relevant asymmetry parameters (Duax & Norton, 1975) are ΔC2[C10A—C10B] = 5.1 (7)° for molecule 1 and ΔC2[C60A—C60B] = 1.7 (7)° for molecule 2; Cremer & Pople puckering parameters θ and ϕ (Cremer & Pople, 1975) are 65.4 (7) and 94.6 (8)° for molecule 1, and 66.4 (7) and 91.6 (7)° for molecule 2, ideal values are 67.5 and 90°, respectively]. Ring C is in a half-chair conformation, with the local twofold axis running through the midpoint of the bond C4B—C10B [relevant asymmetry parameters are ΔC2[C4B—C10B] = 4.9 (7)° for molecule 1 and ΔC2[C60A—C60B] = 4.5 (6)° for molecule 2; Cremer & Pople puckering parameters θ and ϕ are 51.8 (6) and 276.9 (7)° for molecule 1, and 50.5 (6) and 276.7 (7)° for molecule 2, ideal values are 50.8 and 270°, respectively]. Ring D has taken a somewhat distorted chair conformation (all relevant asymmetry parameters are in the range 2.8 (5)–23.4 (6)° for molecule 1 and 4.2 (4)–23.4 (5)° for molecule 2, respectively; the Cremer & Pople parameter θ amounts to 157.1 (6)° for molecule 1 and 160.5 (5)° for molecule 2, the ideal value is 180°.
The methoxy C—O bond makes an angle of 3.5 (3)° with ring A in molecule 1 and and angle of 6.2 (3)° in molecule 2.
The oxime moieties of the independent molecules donate a hydrogen bond to each other, forming a hydrogen bonded dimer (see Fig. 3). The graph set (Bernstein et al., 1995) of the dimer is R22[6].