Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053913/hg2320sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053913/hg2320Isup2.hkl |
CCDC reference: 673090
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.006 Å
- R factor = 0.075
- wR factor = 0.176
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 9.76 Ratio
Author Response: It has not been possible to improve the result of the refinements in spite of the different approaches that we have carried out : measuring of different crystals, low temperature, study of models of disorder, etc. We think that there are two factors that could explain this fact, on one hand the low quality of the available crystals, on the other hand the hight thermal motion of the long lateral chain of the perhydrocyclopentanophenantrene moiety, particularly, the isopropyl terminal group. In this sense the behavior of the present compound it is not very different from those mentioned in the related bibliography and that were published in this journal. |
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 10.00 Ratio
Author Response: Same as above |
Alert level C PLAT213_ALERT_2_C Atom C7" has ADP max/min Ratio ............. 3.10 prola PLAT230_ALERT_2_C Hirshfeld Test Diff for C5" - C7" .. 6.86 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C5" - C6" ... 1.43 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C5" - C7" ... 1.43 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 22
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 3625 Count of symmetry unique reflns 3659 Completeness (_total/calc) 99.07% 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 C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1' = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1" = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4B = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11B = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11C = . R
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Auhmani et al. (2005); Mazoir et al. (2006); Mazoir, Giorgi & Auhmani (2005); Mazoir, Giorgi & Benharrei (2005).
The oxidation of the natural triterpene 4α,14α-dimethyl-5α-cholest-8-en-3β-ol, during 1 h with 3 equivalents of chromic anhydride (CrO3) in acetone at 273 K followed by heating under reflux with 1 equivalent of phenylhydrazine in the presence of acetic acid afforded, after chromatographic purification on silica gel column, the title compound, with an overall 92% yield. Crystals were obtained by evaporation from methanol solution at 277 K. Spectroscopic analysis: 1H NMR (500 MHz, CDCl3, δ (p.p.m.): 7.60 (H8,d,J=7.7 Hz),7.33 (H9,t, J1=15.1 Hz; J2=7.6 Hz),7.18 (H10,t, J1=14.8; J2=7.4 Hz, 7.43 (H11,d, J=7.4 Hz), 0.85 (H6'', d, J =2.3 Hz), 0.86 (H7'',J=2.3 Hz), 0.87 (H8'', d, J=6.3 Hz), 0.72 (H9'', s), 1.31 (H10'', s), 1.33 (H11'', s), 0.75 (H12'', s);13C NMR (125 MHz, CDCl3, δ (p.p.m.): 49.3 (C1), 44.3 (C2),25.7 (C3), 27.9 (C4),135.2 (C4a), 36.3 (C4b), 39.4 (C5), 40.8 (C6), 192.2 (C6a),154.5 (C7a), 127.9 (C8), 123.4 (C9), 120.7 (C10), 124.8 (C11), 147.9 (C11a),57.6 (C11b), 50.4 (C11c), 21.6 (C12), 20.1 (C13), 133.2 (C13a), 51.4 (C1'),25.6 (C2'), 23.9 (C3'), 35.3 (C1''), 30.7 (C2''), 30.8 (C3''),34.6 (C4''),28.0 (C5''), 22.4 (C6''), 22.7 (C7''), 19.0 (C8''),15.6 (C9''), 18.6 (C10''),24.1 (C11''), 16.2 (C12'').
The lack of suitable anomalous scatters did not allow us to reliably determine the absolute structure according to the Flack parameters and, therefore, 2641 Friedels pairs were merged before the final refinement. However, the absolute configuration of the title compound could be assigned by comparation with the known stereochemistry of the starting compound. H-atoms were positioned geometrically and refined using a riding model with C—H =0.95–0.99 Å and with Uiso (H) = 1.2 (1.5 for methyl groups) times Ueq (C).
Data collection: COLLECT (Nonius 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia,1999).
C35H51N | F(000) = 1072 |
Mr = 485.77 | Dx = 1.101 Mg m−3 Dm = not performed Mg m−3 Dm measured by not measured |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2013 reflections |
a = 6.563 (2) Å | θ = 3.4–27.0° |
b = 18.668 (4) Å | µ = 0.06 mm−1 |
c = 23.930 (7) Å | T = 170 K |
V = 2931.9 (14) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Enraf-Nonius KappaCCD diffractometer | 3234 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 27.0°, θmin = 3.4° |
Detector resolution: 9 pixels mm-1 | h = 0→8 |
ϕ and ω scans | k = 0→23 |
16251 measured reflections | l = 0→30 |
3625 independent 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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0624P)2 + 2.356P] where P = (Fo2 + 2Fc2)/3 |
3625 reflections | (Δ/σ)max < 0.001 |
330 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C35H51N | V = 2931.9 (14) Å3 |
Mr = 485.77 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.563 (2) Å | µ = 0.06 mm−1 |
b = 18.668 (4) Å | T = 170 K |
c = 23.930 (7) Å | 0.20 × 0.15 × 0.10 mm |
Enraf-Nonius KappaCCD diffractometer | 3234 reflections with I > 2σ(I) |
16251 measured reflections | Rint = 0.071 |
3625 independent reflections |
R[F2 > 2σ(F2)] = 0.075 | 0 restraints |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.37 e Å−3 |
3625 reflections | Δρmin = −0.26 e Å−3 |
330 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7821 (5) | 0.11990 (16) | 0.13819 (14) | 0.0218 (7) | |
C1' | 0.7970 (6) | 0.05385 (18) | 0.05148 (14) | 0.0265 (8) | |
H1' | 0.6820 | 0.0226 | 0.0608 | 0.032* | |
C1" | 0.8396 (7) | 0.0449 (2) | −0.01160 (15) | 0.0355 (9) | |
H1" | 0.9563 | 0.0753 | −0.0213 | 0.043* | |
C2 | 0.7460 (5) | 0.12964 (18) | 0.07411 (14) | 0.0235 (7) | |
C2' | 0.9805 (6) | 0.0304 (2) | 0.08873 (16) | 0.0345 (9) | |
H2'1 | 0.9611 | −0.0183 | 0.1018 | 0.041* | |
H2'2 | 1.1063 | 0.0324 | 0.0675 | 0.041* | |
C2" | 0.8968 (8) | −0.0333 (2) | −0.02462 (17) | 0.0458 (11) | |
H2"1 | 0.9809 | −0.0515 | 0.0056 | 0.055* | |
H2"2 | 0.7731 | −0.0617 | −0.0255 | 0.055* | |
C3 | 0.5296 (6) | 0.15825 (19) | 0.06657 (15) | 0.0276 (8) | |
H3A | 0.4328 | 0.1220 | 0.0783 | 0.033* | |
H3B | 0.5058 | 0.1682 | 0.0273 | 0.033* | |
C3' | 0.9900 (6) | 0.08280 (19) | 0.13891 (16) | 0.0298 (8) | |
H3'1 | 1.0106 | 0.0571 | 0.1737 | 0.036* | |
H3'2 | 1.0992 | 0.1173 | 0.1342 | 0.036* | |
C3" | 1.0112 (11) | −0.0440 (3) | −0.08002 (19) | 0.0670 (16) | |
H3"1 | 0.9258 | −0.0268 | −0.1103 | 0.080* | |
H3"2 | 1.1334 | −0.0147 | −0.0795 | 0.080* | |
C4 | 0.4946 (6) | 0.22715 (19) | 0.10081 (15) | 0.0295 (8) | |
H4A | 0.5169 | 0.2677 | 0.0762 | 0.035* | |
H4B | 0.3525 | 0.2283 | 0.1119 | 0.035* | |
C4" | 1.0700 (14) | −0.1188 (4) | −0.0919 (3) | 0.114 (3) | |
H4"1 | 0.9463 | −0.1463 | −0.0978 | 0.136* | |
H4"2 | 1.1358 | −0.1380 | −0.0588 | 0.136* | |
C4A | 0.6224 (5) | 0.23830 (17) | 0.15256 (14) | 0.0211 (7) | |
C4B | 0.5965 (5) | 0.31121 (17) | 0.18229 (15) | 0.0226 (7) | |
C5 | 0.3720 (5) | 0.33502 (19) | 0.18046 (16) | 0.0270 (8) | |
H5A | 0.2867 | 0.2956 | 0.1928 | 0.032* | |
H5B | 0.3354 | 0.3460 | 0.1421 | 0.032* | |
C5" | 1.2102 (14) | −0.1319 (6) | −0.1415 (3) | 0.138 (4) | |
H5" | 1.2279 | −0.1840 | −0.1418 | 0.165* | |
C6 | 0.3279 (5) | 0.40146 (18) | 0.21742 (16) | 0.0286 (8) | |
H6A | 0.4003 | 0.4428 | 0.2030 | 0.034* | |
H6B | 0.1832 | 0.4120 | 0.2172 | 0.034* | |
C6" | 1.1121 (13) | −0.1172 (4) | −0.1936 (3) | 0.100 (2) | |
H6"1 | 0.9720 | −0.1318 | −0.1916 | 0.150* | |
H6"2 | 1.1793 | −0.1432 | −0.2229 | 0.150* | |
H6"3 | 1.1192 | −0.0668 | −0.2012 | 0.150* | |
C6A | 0.3964 (5) | 0.38538 (17) | 0.27494 (16) | 0.0263 (8) | |
N7 | 0.2790 (5) | 0.37794 (17) | 0.31774 (14) | 0.0311 (7) | |
C7" | 1.4140 (13) | −0.1051 (8) | −0.1367 (4) | 0.207 (7) | |
H7"1 | 1.4693 | −0.1185 | −0.1010 | 0.310* | |
H7"2 | 1.4126 | −0.0538 | −0.1398 | 0.310* | |
H7"3 | 1.4966 | −0.1249 | −0.1659 | 0.310* | |
C7A | 0.4075 (6) | 0.3549 (2) | 0.36270 (17) | 0.0335 (9) | |
C8 | 0.3491 (7) | 0.3450 (3) | 0.41768 (19) | 0.0468 (11) | |
H8 | 0.2149 | 0.3517 | 0.4290 | 0.056* | |
C8" | 0.6588 (8) | 0.0684 (2) | −0.04728 (17) | 0.0475 (11) | |
H8"1 | 0.6824 | 0.0551 | −0.0855 | 0.071* | |
H8"2 | 0.6430 | 0.1194 | −0.0448 | 0.071* | |
H8"3 | 0.5372 | 0.0454 | −0.0340 | 0.071* | |
C9 | 0.4993 (9) | 0.3248 (3) | 0.4551 (2) | 0.0585 (14) | |
H9 | 0.4650 | 0.3174 | 0.4924 | 0.070* | |
C9" | 0.8963 (6) | 0.18492 (19) | 0.04933 (16) | 0.0328 (9) | |
H9"1 | 0.8606 | 0.1945 | 0.0111 | 0.049* | |
H9"2 | 1.0323 | 0.1661 | 0.0509 | 0.049* | |
H9"3 | 0.8894 | 0.2285 | 0.0705 | 0.049* | |
C10 | 0.6972 (9) | 0.3154 (3) | 0.4385 (2) | 0.0584 (14) | |
H10 | 0.7943 | 0.3017 | 0.4648 | 0.070* | |
C10" | 0.7275 (6) | 0.36513 (18) | 0.14958 (17) | 0.0324 (9) | |
H10A | 0.8691 | 0.3552 | 0.1559 | 0.049* | |
H10B | 0.6969 | 0.4128 | 0.1620 | 0.049* | |
H10C | 0.6982 | 0.3610 | 0.1104 | 0.049* | |
C11 | 0.7561 (7) | 0.3259 (2) | 0.38344 (18) | 0.0472 (11) | |
H11 | 0.8911 | 0.3202 | 0.3725 | 0.057* | |
C11" | 0.7645 (6) | 0.4297 (2) | 0.27791 (18) | 0.0353 (9) | |
H11A | 0.7225 | 0.4673 | 0.3027 | 0.053* | |
H11B | 0.7605 | 0.4467 | 0.2401 | 0.053* | |
H11C | 0.9009 | 0.4152 | 0.2870 | 0.053* | |
C11A | 0.6074 (6) | 0.3450 (2) | 0.34519 (16) | 0.0319 (9) | |
C11B | 0.6194 (5) | 0.36520 (18) | 0.28420 (16) | 0.0265 (8) | |
C11C | 0.6612 (5) | 0.30024 (17) | 0.24441 (15) | 0.0215 (7) | |
H11D | 0.5745 | 0.2614 | 0.2584 | 0.026* | |
C12 | 0.8779 (5) | 0.2720 (2) | 0.24856 (17) | 0.0301 (8) | |
H12A | 0.9156 | 0.2670 | 0.2876 | 0.036* | |
H12B | 0.9709 | 0.3059 | 0.2314 | 0.036* | |
C12" | 0.6261 (6) | 0.06843 (19) | 0.16539 (15) | 0.0312 (8) | |
H12C | 0.6580 | 0.0626 | 0.2043 | 0.047* | |
H12D | 0.6320 | 0.0227 | 0.1471 | 0.047* | |
H12E | 0.4915 | 0.0880 | 0.1617 | 0.047* | |
C13 | 0.8958 (6) | 0.19978 (18) | 0.21951 (16) | 0.0291 (8) | |
H13A | 1.0366 | 0.1927 | 0.2085 | 0.035* | |
H13B | 0.8617 | 0.1625 | 0.2462 | 0.035* | |
C13A | 0.7632 (5) | 0.19075 (17) | 0.16878 (14) | 0.0219 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0261 (17) | 0.0158 (15) | 0.0235 (18) | 0.0017 (13) | −0.0030 (15) | 0.0042 (13) |
C1' | 0.0300 (18) | 0.0262 (17) | 0.0232 (18) | −0.0008 (15) | 0.0027 (15) | 0.0029 (15) |
C1" | 0.049 (2) | 0.035 (2) | 0.0226 (19) | −0.0009 (18) | 0.0076 (18) | 0.0043 (16) |
C2 | 0.0292 (18) | 0.0235 (17) | 0.0177 (17) | 0.0007 (15) | 0.0008 (15) | 0.0046 (13) |
C2' | 0.040 (2) | 0.0307 (19) | 0.033 (2) | 0.0076 (17) | 0.0022 (19) | −0.0001 (17) |
C2" | 0.069 (3) | 0.042 (2) | 0.027 (2) | 0.007 (2) | 0.007 (2) | −0.0063 (18) |
C3 | 0.0302 (19) | 0.0292 (19) | 0.0235 (18) | 0.0036 (16) | −0.0053 (16) | −0.0018 (15) |
C3' | 0.0344 (19) | 0.0257 (19) | 0.0293 (19) | 0.0106 (16) | −0.0040 (17) | −0.0010 (15) |
C3" | 0.100 (4) | 0.069 (3) | 0.032 (2) | 0.004 (3) | 0.015 (3) | 0.001 (2) |
C4 | 0.0250 (17) | 0.034 (2) | 0.030 (2) | 0.0078 (16) | −0.0034 (17) | 0.0008 (16) |
C4" | 0.146 (7) | 0.141 (7) | 0.054 (4) | 0.076 (6) | 0.011 (4) | −0.029 (4) |
C4A | 0.0159 (15) | 0.0235 (16) | 0.0238 (17) | −0.0012 (13) | 0.0024 (14) | 0.0057 (14) |
C4B | 0.0190 (15) | 0.0188 (16) | 0.0299 (19) | 0.0026 (14) | 0.0021 (15) | 0.0042 (14) |
C5 | 0.0238 (17) | 0.0271 (18) | 0.0302 (19) | 0.0035 (15) | 0.0000 (16) | 0.0010 (15) |
C5" | 0.120 (7) | 0.247 (11) | 0.047 (4) | 0.095 (8) | 0.023 (4) | 0.004 (5) |
C6 | 0.0212 (17) | 0.0212 (16) | 0.043 (2) | 0.0043 (14) | 0.0004 (16) | −0.0004 (16) |
C6" | 0.110 (6) | 0.131 (6) | 0.060 (4) | 0.014 (5) | 0.008 (4) | −0.020 (4) |
C6A | 0.0221 (16) | 0.0161 (15) | 0.041 (2) | 0.0011 (14) | −0.0001 (17) | −0.0086 (15) |
N7 | 0.0189 (14) | 0.0336 (17) | 0.0410 (19) | 0.0001 (13) | 0.0028 (14) | −0.0116 (15) |
C7" | 0.063 (5) | 0.42 (2) | 0.136 (8) | 0.021 (9) | −0.006 (5) | −0.174 (11) |
C7A | 0.036 (2) | 0.0294 (19) | 0.035 (2) | −0.0015 (17) | 0.0002 (18) | −0.0100 (17) |
C8 | 0.044 (2) | 0.058 (3) | 0.039 (2) | −0.001 (2) | 0.005 (2) | −0.014 (2) |
C8" | 0.069 (3) | 0.051 (3) | 0.023 (2) | 0.006 (2) | −0.001 (2) | 0.0003 (19) |
C9 | 0.078 (4) | 0.066 (3) | 0.032 (2) | −0.001 (3) | 0.001 (3) | −0.010 (2) |
C9" | 0.039 (2) | 0.0298 (19) | 0.029 (2) | −0.0013 (18) | 0.0099 (18) | 0.0056 (16) |
C10 | 0.065 (3) | 0.072 (3) | 0.038 (3) | 0.016 (3) | −0.018 (2) | −0.010 (2) |
C10" | 0.0327 (19) | 0.0241 (18) | 0.040 (2) | 0.0006 (16) | 0.0047 (18) | 0.0024 (16) |
C11 | 0.043 (2) | 0.060 (3) | 0.039 (2) | 0.014 (2) | −0.010 (2) | −0.014 (2) |
C11" | 0.0231 (18) | 0.0301 (19) | 0.053 (2) | −0.0044 (16) | −0.0004 (18) | −0.0173 (19) |
C11A | 0.0335 (19) | 0.0299 (19) | 0.032 (2) | −0.0002 (16) | −0.0063 (17) | −0.0128 (16) |
C11B | 0.0189 (16) | 0.0249 (17) | 0.036 (2) | 0.0045 (14) | −0.0020 (16) | −0.0053 (16) |
C11C | 0.0180 (15) | 0.0169 (15) | 0.0296 (19) | 0.0001 (13) | −0.0028 (14) | −0.0013 (14) |
C12 | 0.0211 (17) | 0.034 (2) | 0.036 (2) | 0.0048 (16) | −0.0061 (17) | −0.0050 (17) |
C12" | 0.046 (2) | 0.0252 (18) | 0.0226 (18) | −0.0024 (17) | 0.0074 (18) | 0.0029 (15) |
C13 | 0.0267 (17) | 0.0274 (18) | 0.033 (2) | 0.0084 (15) | −0.0051 (17) | 0.0008 (16) |
C13A | 0.0175 (15) | 0.0237 (16) | 0.0244 (18) | −0.0019 (14) | 0.0012 (14) | 0.0029 (14) |
C1—C13A | 1.517 (5) | C6—H6B | 0.9700 |
C1—C3' | 1.530 (5) | C6"—H6"1 | 0.9600 |
C1—C12" | 1.548 (5) | C6"—H6"2 | 0.9600 |
C1—C2 | 1.562 (5) | C6"—H6"3 | 0.9600 |
C1'—C1" | 1.544 (5) | C6A—N7 | 1.289 (5) |
C1'—C2 | 1.552 (5) | C6A—C11B | 1.527 (5) |
C1'—C2' | 1.561 (5) | N7—C7A | 1.433 (5) |
C1'—H1' | 0.9800 | C7"—H7"1 | 0.9600 |
C1"—C8" | 1.526 (6) | C7"—H7"2 | 0.9600 |
C1"—C2" | 1.540 (6) | C7"—H7"3 | 0.9600 |
C1"—H1" | 0.9800 | C7A—C8 | 1.383 (6) |
C2—C3 | 1.528 (5) | C7A—C11A | 1.389 (6) |
C2—C9" | 1.546 (5) | C8—C9 | 1.385 (7) |
C2'—C3' | 1.550 (5) | C8—H8 | 0.9300 |
C2'—H2'1 | 0.9700 | C8"—H8"1 | 0.9600 |
C2'—H2'2 | 0.9700 | C8"—H8"2 | 0.9600 |
C2"—C3" | 1.537 (6) | C8"—H8"3 | 0.9600 |
C2"—H2"1 | 0.9700 | C9—C10 | 1.370 (8) |
C2"—H2"2 | 0.9700 | C9—H9 | 0.9300 |
C3—C4 | 1.542 (5) | C9"—H9"1 | 0.9600 |
C3—H3A | 0.9700 | C9"—H9"2 | 0.9600 |
C3—H3B | 0.9700 | C9"—H9"3 | 0.9600 |
C3'—H3'1 | 0.9700 | C10—C11 | 1.388 (7) |
C3'—H3'2 | 0.9700 | C10—H10 | 0.9300 |
C3"—C4" | 1.478 (8) | C10"—H10A | 0.9600 |
C3"—H3"1 | 0.9700 | C10"—H10B | 0.9600 |
C3"—H3"2 | 0.9700 | C10"—H10C | 0.9600 |
C4—C4A | 1.510 (5) | C11—C11A | 1.385 (6) |
C4—H4A | 0.9700 | C11—H11 | 0.9300 |
C4—H4B | 0.9700 | C11"—C11B | 1.543 (5) |
C4"—C5" | 1.522 (9) | C11"—H11A | 0.9600 |
C4"—H4"1 | 0.9700 | C11"—H11B | 0.9600 |
C4"—H4"2 | 0.9700 | C11"—H11C | 0.9600 |
C4A—C13A | 1.339 (4) | C11A—C11B | 1.509 (5) |
C4A—C4B | 1.545 (5) | C11B—C11C | 1.566 (5) |
C4B—C10" | 1.538 (5) | C11C—C12 | 1.520 (5) |
C4B—C5 | 1.540 (5) | C11C—H11D | 0.9800 |
C4B—C11C | 1.559 (5) | C12—C13 | 1.522 (5) |
C5—C6 | 1.550 (5) | C12—H12A | 0.9700 |
C5—H5A | 0.9700 | C12—H12B | 0.9700 |
C5—H5B | 0.9700 | C12"—H12C | 0.9600 |
C5"—C6" | 1.429 (10) | C12"—H12D | 0.9600 |
C5"—C7" | 1.433 (13) | C12"—H12E | 0.9600 |
C5"—H5" | 0.9800 | C13—C13A | 1.503 (5) |
C6—C6A | 1.479 (5) | C13—H13A | 0.9700 |
C6—H6A | 0.9700 | C13—H13B | 0.9700 |
C13A—C1—C3' | 117.5 (3) | H6A—C6—H6B | 108.4 |
C13A—C1—C12" | 106.5 (3) | C5"—C6"—H6"1 | 109.5 |
C3'—C1—C12" | 107.7 (3) | C5"—C6"—H6"2 | 109.5 |
C13A—C1—C2 | 111.1 (3) | H6"1—C6"—H6"2 | 109.5 |
C3'—C1—C2 | 101.5 (3) | C5"—C6"—H6"3 | 109.5 |
C12"—C1—C2 | 112.6 (3) | H6"1—C6"—H6"3 | 109.5 |
C1"—C1'—C2 | 118.6 (3) | H6"2—C6"—H6"3 | 109.5 |
C1"—C1'—C2' | 112.8 (3) | N7—C6A—C6 | 125.4 (3) |
C2—C1'—C2' | 102.9 (3) | N7—C6A—C11B | 115.5 (3) |
C1"—C1'—H1' | 107.3 | C6—C6A—C11B | 118.5 (3) |
C2—C1'—H1' | 107.3 | C6A—N7—C7A | 106.1 (3) |
C2'—C1'—H1' | 107.3 | C5"—C7"—H7"1 | 109.5 |
C8"—C1"—C2" | 110.4 (4) | C5"—C7"—H7"2 | 109.5 |
C8"—C1"—C1' | 112.0 (3) | H7"1—C7"—H7"2 | 109.5 |
C2"—C1"—C1' | 110.1 (3) | C5"—C7"—H7"3 | 109.5 |
C8"—C1"—H1" | 108.1 | H7"1—C7"—H7"3 | 109.5 |
C2"—C1"—H1" | 108.1 | H7"2—C7"—H7"3 | 109.5 |
C1'—C1"—H1" | 108.1 | C8—C7A—C11A | 122.1 (4) |
C3—C2—C9" | 108.3 (3) | C8—C7A—N7 | 126.2 (4) |
C3—C2—C1' | 118.6 (3) | C11A—C7A—N7 | 111.6 (3) |
C9"—C2—C1' | 109.7 (3) | C7A—C8—C9 | 117.1 (4) |
C3—C2—C1 | 107.3 (3) | C7A—C8—H8 | 121.5 |
C9"—C2—C1 | 110.9 (3) | C9—C8—H8 | 121.5 |
C1'—C2—C1 | 101.7 (3) | C1"—C8"—H8"1 | 109.5 |
C3'—C2'—C1' | 107.2 (3) | C1"—C8"—H8"2 | 109.5 |
C3'—C2'—H2'1 | 110.3 | H8"1—C8"—H8"2 | 109.5 |
C1'—C2'—H2'1 | 110.3 | C1"—C8"—H8"3 | 109.5 |
C3'—C2'—H2'2 | 110.3 | H8"1—C8"—H8"3 | 109.5 |
C1'—C2'—H2'2 | 110.3 | H8"2—C8"—H8"3 | 109.5 |
H2'1—C2'—H2'2 | 108.5 | C10—C9—C8 | 121.5 (5) |
C3"—C2"—C1" | 114.6 (4) | C10—C9—H9 | 119.3 |
C3"—C2"—H2"1 | 108.6 | C8—C9—H9 | 119.3 |
C1"—C2"—H2"1 | 108.6 | C2—C9"—H9"1 | 109.5 |
C3"—C2"—H2"2 | 108.6 | C2—C9"—H9"2 | 109.5 |
C1"—C2"—H2"2 | 108.6 | H9"1—C9"—H9"2 | 109.5 |
H2"1—C2"—H2"2 | 107.6 | C2—C9"—H9"3 | 109.5 |
C2—C3—C4 | 111.5 (3) | H9"1—C9"—H9"3 | 109.5 |
C2—C3—H3A | 109.3 | H9"2—C9"—H9"3 | 109.5 |
C4—C3—H3A | 109.3 | C9—C10—C11 | 121.4 (5) |
C2—C3—H3B | 109.3 | C9—C10—H10 | 119.3 |
C4—C3—H3B | 109.3 | C11—C10—H10 | 119.3 |
H3A—C3—H3B | 108.0 | C4B—C10"—H10A | 109.5 |
C1—C3'—C2' | 104.0 (3) | C4B—C10"—H10B | 109.5 |
C1—C3'—H3'1 | 111.0 | H10A—C10"—H10B | 109.5 |
C2'—C3'—H3'1 | 111.0 | C4B—C10"—H10C | 109.5 |
C1—C3'—H3'2 | 111.0 | H10A—C10"—H10C | 109.5 |
C2'—C3'—H3'2 | 111.0 | H10B—C10"—H10C | 109.5 |
H3'1—C3'—H3'2 | 109.0 | C11A—C11—C10 | 117.9 (4) |
C4"—C3"—C2" | 114.5 (5) | C11A—C11—H11 | 121.0 |
C4"—C3"—H3"1 | 108.6 | C10—C11—H11 | 121.0 |
C2"—C3"—H3"1 | 108.6 | C11B—C11"—H11A | 109.5 |
C4"—C3"—H3"2 | 108.6 | C11B—C11"—H11B | 109.5 |
C2"—C3"—H3"2 | 108.6 | H11A—C11"—H11B | 109.5 |
H3"1—C3"—H3"2 | 107.6 | C11B—C11"—H11C | 109.5 |
C4A—C4—C3 | 117.9 (3) | H11A—C11"—H11C | 109.5 |
C4A—C4—H4A | 107.8 | H11B—C11"—H11C | 109.5 |
C3—C4—H4A | 107.8 | C11—C11A—C7A | 120.0 (4) |
C4A—C4—H4B | 107.8 | C11—C11A—C11B | 131.8 (4) |
C3—C4—H4B | 107.8 | C7A—C11A—C11B | 107.9 (3) |
H4A—C4—H4B | 107.2 | C11A—C11B—C6A | 98.7 (3) |
C3"—C4"—C5" | 117.3 (7) | C11A—C11B—C11" | 108.7 (3) |
C3"—C4"—H4"1 | 108.0 | C6A—C11B—C11" | 112.6 (3) |
C5"—C4"—H4"1 | 108.0 | C11A—C11B—C11C | 113.8 (3) |
C3"—C4"—H4"2 | 108.0 | C6A—C11B—C11C | 105.7 (3) |
C5"—C4"—H4"2 | 108.0 | C11"—C11B—C11C | 115.9 (3) |
H4"1—C4"—H4"2 | 107.2 | C12—C11C—C4B | 111.2 (3) |
C13A—C4A—C4 | 122.0 (3) | C12—C11C—C11B | 113.1 (3) |
C13A—C4A—C4B | 121.8 (3) | C4B—C11C—C11B | 115.5 (3) |
C4—C4A—C4B | 116.0 (3) | C12—C11C—H11D | 105.3 |
C10"—C4B—C5 | 109.4 (3) | C4B—C11C—H11D | 105.3 |
C10"—C4B—C4A | 106.3 (3) | C11B—C11C—H11D | 105.3 |
C5—C4B—C4A | 110.3 (3) | C11C—C12—C13 | 110.4 (3) |
C10"—C4B—C11C | 114.8 (3) | C11C—C12—H12A | 109.6 |
C5—C4B—C11C | 109.0 (3) | C13—C12—H12A | 109.6 |
C4A—C4B—C11C | 107.1 (3) | C11C—C12—H12B | 109.6 |
C4B—C5—C6 | 113.2 (3) | C13—C12—H12B | 109.6 |
C4B—C5—H5A | 108.9 | H12A—C12—H12B | 108.1 |
C6—C5—H5A | 108.9 | C1—C12"—H12C | 109.5 |
C4B—C5—H5B | 108.9 | C1—C12"—H12D | 109.5 |
C6—C5—H5B | 108.9 | H12C—C12"—H12D | 109.5 |
H5A—C5—H5B | 107.8 | C1—C12"—H12E | 109.5 |
C6"—C5"—C7" | 115.1 (9) | H12C—C12"—H12E | 109.5 |
C6"—C5"—C4" | 112.2 (7) | H12D—C12"—H12E | 109.5 |
C7"—C5"—C4" | 116.4 (8) | C13A—C13—C12 | 115.1 (3) |
C6"—C5"—H5" | 103.7 | C13A—C13—H13A | 108.5 |
C7"—C5"—H5" | 103.7 | C12—C13—H13A | 108.5 |
C4"—C5"—H5" | 103.7 | C13A—C13—H13B | 108.5 |
C6A—C6—C5 | 108.2 (3) | C12—C13—H13B | 108.5 |
C6A—C6—H6A | 110.1 | H13A—C13—H13B | 107.5 |
C5—C6—H6A | 110.1 | C4A—C13A—C13 | 124.0 (3) |
C6A—C6—H6B | 110.1 | C4A—C13A—C1 | 119.7 (3) |
C5—C6—H6B | 110.1 | C13—C13A—C1 | 116.1 (3) |
C2—C1'—C1"—C8" | −59.5 (5) | C6A—N7—C7A—C11A | −2.9 (4) |
C2'—C1'—C1"—C8" | −179.8 (3) | C11A—C7A—C8—C9 | 0.1 (6) |
C2—C1'—C1"—C2" | 177.3 (4) | N7—C7A—C8—C9 | −177.8 (4) |
C2'—C1'—C1"—C2" | 56.9 (5) | C7A—C8—C9—C10 | 0.4 (8) |
C1"—C1'—C2—C3 | 79.7 (4) | C8—C9—C10—C11 | 0.1 (8) |
C2'—C1'—C2—C3 | −155.0 (3) | C9—C10—C11—C11A | −1.1 (8) |
C1"—C1'—C2—C9" | −45.5 (4) | C10—C11—C11A—C7A | 1.5 (6) |
C2'—C1'—C2—C9" | 79.9 (3) | C10—C11—C11A—C11B | 175.2 (4) |
C1"—C1'—C2—C1 | −163.0 (3) | C8—C7A—C11A—C11 | −1.1 (6) |
C2'—C1'—C2—C1 | −37.6 (3) | N7—C7A—C11A—C11 | 177.1 (3) |
C13A—C1—C2—C3 | −61.1 (3) | C8—C7A—C11A—C11B | −176.1 (4) |
C3'—C1—C2—C3 | 173.2 (3) | N7—C7A—C11A—C11B | 2.1 (4) |
C12"—C1—C2—C3 | 58.3 (4) | C11—C11A—C11B—C6A | −174.7 (4) |
C13A—C1—C2—C9" | 57.1 (4) | C7A—C11A—C11B—C6A | −0.5 (4) |
C3'—C1—C2—C9" | −68.6 (3) | C11—C11A—C11B—C11" | −57.1 (5) |
C12"—C1—C2—C9" | 176.5 (3) | C7A—C11A—C11B—C11" | 117.1 (3) |
C13A—C1—C2—C1' | 173.7 (3) | C11—C11A—C11B—C11C | 73.8 (5) |
C3'—C1—C2—C1' | 48.0 (3) | C7A—C11A—C11B—C11C | −112.0 (3) |
C12"—C1—C2—C1' | −66.9 (3) | N7—C6A—C11B—C11A | −1.4 (4) |
C1"—C1'—C2'—C3' | 143.0 (3) | C6—C6A—C11B—C11A | −173.0 (3) |
C2—C1'—C2'—C3' | 14.0 (4) | N7—C6A—C11B—C11" | −116.0 (4) |
C8"—C1"—C2"—C3" | 75.7 (5) | C6—C6A—C11B—C11" | 72.4 (4) |
C1'—C1"—C2"—C3" | −160.1 (4) | N7—C6A—C11B—C11C | 116.5 (3) |
C9"—C2—C3—C4 | −65.0 (4) | C6—C6A—C11B—C11C | −55.1 (4) |
C1'—C2—C3—C4 | 169.2 (3) | C10"—C4B—C11C—C12 | −60.6 (4) |
C1—C2—C3—C4 | 54.9 (4) | C5—C4B—C11C—C12 | 176.3 (3) |
C13A—C1—C3'—C2' | −160.1 (3) | C4A—C4B—C11C—C12 | 57.1 (3) |
C12"—C1—C3'—C2' | 79.7 (4) | C10"—C4B—C11C—C11B | 70.0 (4) |
C2—C1—C3'—C2' | −38.8 (3) | C5—C4B—C11C—C11B | −53.0 (4) |
C1'—C2'—C3'—C1 | 15.6 (4) | C4A—C4B—C11C—C11B | −172.3 (3) |
C1"—C2"—C3"—C4" | 178.7 (6) | C11A—C11B—C11C—C12 | −72.1 (4) |
C2—C3—C4—C4A | −26.4 (4) | C6A—C11B—C11C—C12 | −179.3 (3) |
C2"—C3"—C4"—C5" | −171.2 (6) | C11"—C11B—C11C—C12 | 55.2 (4) |
C3—C4—C4A—C13A | 0.4 (5) | C11A—C11B—C11C—C4B | 158.2 (3) |
C3—C4—C4A—C4B | 174.4 (3) | C6A—C11B—C11C—C4B | 50.9 (4) |
C13A—C4A—C4B—C10" | 93.4 (4) | C11"—C11B—C11C—C4B | −74.6 (4) |
C4—C4A—C4B—C10" | −80.7 (4) | C4B—C11C—C12—C13 | −60.9 (4) |
C13A—C4A—C4B—C5 | −148.2 (3) | C11B—C11C—C12—C13 | 167.2 (3) |
C4—C4A—C4B—C5 | 37.8 (4) | C11C—C12—C13—C13A | 34.0 (4) |
C13A—C4A—C4B—C11C | −29.7 (4) | C4—C4A—C13A—C13 | 179.3 (3) |
C4—C4A—C4B—C11C | 156.2 (3) | C4B—C4A—C13A—C13 | 5.6 (5) |
C10"—C4B—C5—C6 | −72.6 (4) | C4—C4A—C13A—C1 | −6.4 (5) |
C4A—C4B—C5—C6 | 170.9 (3) | C4B—C4A—C13A—C1 | 179.9 (3) |
C11C—C4B—C5—C6 | 53.6 (4) | C12—C13—C13A—C4A | −6.9 (5) |
C3"—C4"—C5"—C6" | −68.2 (12) | C12—C13—C13A—C1 | 178.5 (3) |
C3"—C4"—C5"—C7" | 67.3 (12) | C3'—C1—C13A—C4A | 153.6 (3) |
C4B—C5—C6—C6A | −55.2 (4) | C12"—C1—C13A—C4A | −85.6 (4) |
C5—C6—C6A—N7 | −112.6 (4) | C2—C1—C13A—C4A | 37.4 (4) |
C5—C6—C6A—C11B | 58.1 (4) | C3'—C1—C13A—C13 | −31.6 (4) |
C6—C6A—N7—C7A | 173.5 (3) | C12"—C1—C13A—C13 | 89.2 (4) |
C11B—C6A—N7—C7A | 2.6 (4) | C2—C1—C13A—C13 | −147.8 (3) |
C6A—N7—C7A—C8 | 175.1 (4) |
Experimental details
Crystal data | |
Chemical formula | C35H51N |
Mr | 485.77 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 170 |
a, b, c (Å) | 6.563 (2), 18.668 (4), 23.930 (7) |
V (Å3) | 2931.9 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.20 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Enraf-Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16251, 3625, 3234 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.176, 1.14 |
No. of reflections | 3625 |
No. of parameters | 330 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.26 |
Computer programs: COLLECT (Nonius 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), WinGX (Farrugia,1999).
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The title compound (II) (Scheme 1) was obtained by transformation of the natural triterpene: 4α,14α-dimethyl-5α-cholest-8-en-3β-ol(I) (Scheme1). In the course of the reaction the α stereochemistry at C4 in (I) changes to β at the C11b in (II), because the new C11a—C11b bond is preferably developed through the less crowdy α face of (I). However, that of the remaining stereocenters remains unchanged. The above-mentioned, together with the known absolute stereochemistry of (I) allows us to assign the absolute configuration of (II) as 1(R),1'(R),1"(R),2(R),4 b(S),C11b(R), C11c(R). For structural details of related hemisynthesized derivatives from moroccan natural products, see:Auhmani et al. (2005); Mazoir, Giorgi & Benharrei (2005); Mazoir, Giorgi & Auhmani (2005); Mazoir et al. (2006).