The crystal structures of three ester derivatives of glycyrrhetinic acid (GE) are reported. X-ray crystallography revealed that despite differences in the size of the ester substituents (ethyl, isopropyl and 2-morpholinoethyl) the scheme of molecular self-assembly is similar in all three cases but differs significantly from that observed in other known GE esters. According to our analysis, the two basic patterns of self-assembly of GE esters observed in their unsolvated crystals correspond to two distinct orientations of the ester groups relative to the triterpene backbone. Moreover, comparison of the self-assembly modes of GE esters in their unsolvated forms with the supramolecular organization of GE and carbenoxolone in their solvated crystals revealed that ester substituents replace solvent molecules hydrogen bonded to the COOH group at the triterpene skeleton, resulting in similar packing arrangements of these compounds.
Supporting information
CCDC references: 1480870; 1480871; 1480872
For all compounds, data collection: CrysAlis PRO (Agilent Technologies, 2014); cell refinement: CrysAlis PRO (Agilent Technologies, 2014); data reduction: CrysAlis PRO (Agilent Technologies, 2014); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2014) for (4), (5); SHELXL2014/7 (Sheldrick, 2014) for (6).
(4) ethyl-3/b-hydroxy-11-oxoolean-12-en-30-oate
top
Crystal data top
C32H50O4 | Dx = 1.196 Mg m−3 |
Mr = 498.72 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3007 reflections |
a = 12.9577 (5) Å | θ = 3.5–28.7° |
b = 13.0369 (4) Å | µ = 0.08 mm−1 |
c = 16.3908 (5) Å | T = 130 K |
V = 2768.87 (16) Å3 | Plate, colorless |
Z = 4 | 0.60 × 0.20 × 0.15 mm |
F(000) = 1096 | |
Data collection top
Xcalibur, Eos diffractometer | 4597 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3513 reflections with I > 2σ(I) |
Detector resolution: 16.1544 pixels mm-1 | Rint = 0.038 |
ω scans | θmax = 25.3°, θmin = 2.9° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, 2014
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −15→15 |
Tmin = 0.885, Tmax = 1.000 | k = −15→15 |
9373 measured reflections | l = −19→19 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0213P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 0.92 | Δρmax = 0.17 e Å−3 |
4597 reflections | Δρmin = −0.20 e Å−3 |
334 parameters | Absolute structure: Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.8 (9) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.62524 (15) | −0.27111 (16) | 0.75263 (16) | 0.0324 (6) | |
H3 | 0.5615 | −0.2827 | 0.7522 | 0.049* | |
O11 | 0.60802 (15) | 0.23850 (15) | 0.72977 (13) | 0.0252 (6) | |
O30 | 0.60960 (14) | 0.59512 (15) | 0.47474 (13) | 0.0234 (5) | |
O31 | 0.72376 (16) | 0.70751 (17) | 0.42517 (15) | 0.0416 (7) | |
C1 | 0.6060 (2) | 0.0141 (2) | 0.71619 (18) | 0.0183 (7) | |
H1A | 0.5652 | 0.0677 | 0.7444 | 0.022* | |
H1B | 0.5821 | 0.0109 | 0.6589 | 0.022* | |
C2 | 0.5860 (2) | −0.0887 (2) | 0.75694 (19) | 0.0198 (8) | |
H2A | 0.6069 | −0.0850 | 0.8150 | 0.024* | |
H2B | 0.5112 | −0.1042 | 0.7549 | 0.024* | |
C3 | 0.6453 (2) | −0.1736 (2) | 0.71516 (19) | 0.0212 (8) | |
H3A | 0.6205 | −0.1774 | 0.6574 | 0.025* | |
C4 | 0.7627 (2) | −0.1560 (2) | 0.71300 (18) | 0.0177 (7) | |
C5 | 0.7833 (2) | −0.0462 (2) | 0.67933 (18) | 0.0151 (7) | |
H5 | 0.7601 | −0.0489 | 0.6212 | 0.018* | |
C6 | 0.8983 (2) | −0.0186 (2) | 0.67482 (18) | 0.0170 (7) | |
H6A | 0.9237 | −0.0010 | 0.7300 | 0.020* | |
H6B | 0.9379 | −0.0787 | 0.6552 | 0.020* | |
C7 | 0.9162 (2) | 0.0719 (2) | 0.61751 (18) | 0.0182 (7) | |
H7A | 0.9002 | 0.0500 | 0.5611 | 0.022* | |
H7B | 0.9902 | 0.0907 | 0.6193 | 0.022* | |
C8 | 0.8516 (2) | 0.1676 (2) | 0.63759 (18) | 0.0150 (7) | |
C9 | 0.7376 (2) | 0.1374 (2) | 0.65859 (17) | 0.0135 (7) | |
H9 | 0.7077 | 0.1140 | 0.6055 | 0.016* | |
C10 | 0.7214 (2) | 0.0448 (2) | 0.71752 (17) | 0.0142 (7) | |
C11 | 0.6783 (2) | 0.2348 (2) | 0.67915 (18) | 0.0165 (7) | |
C12 | 0.7044 (2) | 0.3275 (2) | 0.63302 (17) | 0.0169 (7) | |
H12 | 0.6633 | 0.3868 | 0.6420 | 0.020* | |
C13 | 0.7819 (2) | 0.3352 (2) | 0.57915 (17) | 0.0144 (7) | |
C14 | 0.8494 (2) | 0.2418 (2) | 0.56074 (18) | 0.0148 (7) | |
C15 | 0.9613 (2) | 0.2731 (2) | 0.53688 (18) | 0.0174 (7) | |
H15A | 1.0018 | 0.2838 | 0.5874 | 0.021* | |
H15B | 0.9935 | 0.2158 | 0.5065 | 0.021* | |
C16 | 0.9679 (2) | 0.3706 (2) | 0.48463 (18) | 0.0179 (7) | |
H16A | 1.0414 | 0.3890 | 0.4771 | 0.021* | |
H16B | 0.9383 | 0.3562 | 0.4301 | 0.021* | |
C17 | 0.9111 (2) | 0.4619 (2) | 0.52201 (19) | 0.0170 (7) | |
C18 | 0.7959 (2) | 0.4342 (2) | 0.53182 (17) | 0.0161 (7) | |
H18 | 0.7634 | 0.4900 | 0.5648 | 0.019* | |
C19 | 0.7381 (2) | 0.4303 (2) | 0.44961 (17) | 0.0173 (7) | |
H19A | 0.7639 | 0.3709 | 0.4179 | 0.021* | |
H19B | 0.6639 | 0.4188 | 0.4604 | 0.021* | |
C20 | 0.7496 (2) | 0.5273 (2) | 0.39749 (18) | 0.0183 (7) | |
C21 | 0.8643 (2) | 0.5508 (2) | 0.38608 (18) | 0.0206 (8) | |
H21A | 0.8962 | 0.4962 | 0.3525 | 0.025* | |
H21B | 0.8719 | 0.6165 | 0.3565 | 0.025* | |
C22 | 0.9206 (2) | 0.5577 (2) | 0.46731 (18) | 0.0208 (8) | |
H22A | 0.8936 | 0.6176 | 0.4977 | 0.025* | |
H22B | 0.9947 | 0.5704 | 0.4564 | 0.025* | |
C23 | 0.8081 (2) | −0.2357 (2) | 0.6535 (2) | 0.0274 (8) | |
H23A | 0.8836 | −0.2345 | 0.6570 | 0.041* | |
H23B | 0.7867 | −0.2191 | 0.5977 | 0.041* | |
H23C | 0.7829 | −0.3042 | 0.6680 | 0.041* | |
C24 | 0.8118 (2) | −0.1736 (2) | 0.79646 (18) | 0.0221 (8) | |
H24A | 0.8859 | −0.1593 | 0.7933 | 0.033* | |
H24B | 0.8011 | −0.2450 | 0.8131 | 0.033* | |
H24C | 0.7798 | −0.1277 | 0.8365 | 0.033* | |
C25 | 0.7511 (2) | 0.0710 (2) | 0.80644 (17) | 0.0178 (7) | |
H25A | 0.7158 | 0.0239 | 0.8437 | 0.027* | |
H25B | 0.7303 | 0.1417 | 0.8187 | 0.027* | |
H25C | 0.8259 | 0.0642 | 0.8133 | 0.027* | |
C26 | 0.9017 (2) | 0.2208 (2) | 0.71192 (17) | 0.0200 (7) | |
H26A | 0.8564 | 0.2757 | 0.7314 | 0.030* | |
H26B | 0.9684 | 0.2499 | 0.6959 | 0.030* | |
H26C | 0.9121 | 0.1704 | 0.7556 | 0.030* | |
C27 | 0.8009 (2) | 0.1895 (2) | 0.48505 (17) | 0.0195 (7) | |
H27A | 0.7255 | 0.1927 | 0.4890 | 0.029* | |
H27B | 0.8229 | 0.1176 | 0.4827 | 0.029* | |
H27C | 0.8236 | 0.2251 | 0.4355 | 0.029* | |
C28 | 0.9576 (2) | 0.4890 (2) | 0.60528 (18) | 0.0241 (8) | |
H28A | 1.0318 | 0.5015 | 0.5992 | 0.036* | |
H28B | 0.9465 | 0.4319 | 0.6432 | 0.036* | |
H28C | 0.9241 | 0.5508 | 0.6266 | 0.036* | |
C29 | 0.7001 (2) | 0.5087 (2) | 0.31360 (18) | 0.0249 (8) | |
H29A | 0.6264 | 0.4940 | 0.3206 | 0.037* | |
H29B | 0.7337 | 0.4503 | 0.2871 | 0.037* | |
H29C | 0.7084 | 0.5701 | 0.2797 | 0.037* | |
C30 | 0.6958 (2) | 0.6199 (2) | 0.43409 (19) | 0.0214 (7) | |
C31 | 0.5513 (2) | 0.6803 (3) | 0.5081 (2) | 0.0291 (9) | |
H31A | 0.5204 | 0.7210 | 0.4633 | 0.035* | |
H31B | 0.5974 | 0.7257 | 0.5400 | 0.035* | |
C32 | 0.4683 (3) | 0.6383 (3) | 0.5617 (2) | 0.0540 (12) | |
H32A | 0.4198 | 0.5982 | 0.5288 | 0.081* | |
H32B | 0.4315 | 0.6950 | 0.5880 | 0.081* | |
H32C | 0.4992 | 0.5942 | 0.6035 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0236 (12) | 0.0177 (13) | 0.0559 (17) | −0.0061 (11) | 0.0038 (13) | 0.0086 (12) |
O11 | 0.0213 (11) | 0.0229 (13) | 0.0312 (14) | 0.0047 (10) | 0.0128 (11) | 0.0062 (11) |
O30 | 0.0198 (11) | 0.0216 (13) | 0.0288 (13) | 0.0013 (10) | 0.0069 (11) | −0.0030 (10) |
O31 | 0.0389 (14) | 0.0196 (14) | 0.0662 (19) | 0.0011 (12) | 0.0214 (14) | 0.0078 (13) |
C1 | 0.0140 (16) | 0.0179 (18) | 0.0230 (19) | 0.0024 (14) | 0.0006 (15) | 0.0033 (15) |
C2 | 0.0131 (15) | 0.0206 (19) | 0.0258 (19) | −0.0038 (14) | −0.0001 (15) | 0.0040 (15) |
C3 | 0.0218 (16) | 0.0164 (17) | 0.0253 (19) | −0.0052 (15) | −0.0001 (15) | 0.0030 (16) |
C4 | 0.0161 (15) | 0.0149 (16) | 0.0221 (18) | 0.0012 (14) | 0.0045 (15) | 0.0018 (15) |
C5 | 0.0154 (16) | 0.0157 (17) | 0.0141 (17) | 0.0001 (14) | −0.0014 (14) | 0.0010 (14) |
C6 | 0.0118 (15) | 0.0180 (18) | 0.0211 (18) | 0.0047 (14) | 0.0020 (15) | 0.0034 (14) |
C7 | 0.0145 (15) | 0.0180 (18) | 0.0222 (18) | 0.0026 (14) | 0.0030 (15) | 0.0048 (15) |
C8 | 0.0114 (15) | 0.0154 (17) | 0.0181 (18) | 0.0006 (14) | −0.0016 (14) | 0.0020 (15) |
C9 | 0.0136 (15) | 0.0145 (16) | 0.0124 (17) | 0.0013 (14) | −0.0014 (13) | −0.0010 (13) |
C10 | 0.0110 (15) | 0.0149 (16) | 0.0166 (17) | 0.0017 (13) | 0.0016 (14) | 0.0015 (14) |
C11 | 0.0132 (15) | 0.0176 (18) | 0.0186 (18) | 0.0014 (14) | −0.0011 (14) | 0.0004 (15) |
C12 | 0.0153 (15) | 0.0145 (17) | 0.0208 (18) | 0.0064 (14) | −0.0005 (15) | 0.0019 (15) |
C13 | 0.0113 (14) | 0.0163 (16) | 0.0158 (17) | −0.0028 (13) | −0.0033 (14) | 0.0015 (14) |
C14 | 0.0142 (15) | 0.0164 (17) | 0.0138 (17) | −0.0006 (13) | 0.0002 (13) | 0.0022 (14) |
C15 | 0.0140 (15) | 0.0189 (18) | 0.0193 (19) | 0.0025 (14) | 0.0033 (14) | 0.0022 (15) |
C16 | 0.0127 (15) | 0.0195 (18) | 0.0216 (18) | −0.0015 (14) | 0.0016 (14) | 0.0032 (15) |
C17 | 0.0107 (15) | 0.0172 (17) | 0.0231 (18) | −0.0025 (14) | −0.0016 (15) | 0.0040 (15) |
C18 | 0.0148 (15) | 0.0155 (16) | 0.0181 (18) | 0.0025 (14) | 0.0019 (14) | −0.0009 (14) |
C19 | 0.0131 (15) | 0.0174 (17) | 0.0215 (18) | 0.0016 (14) | −0.0001 (14) | 0.0024 (14) |
C20 | 0.0162 (15) | 0.0199 (17) | 0.0189 (18) | 0.0017 (15) | 0.0021 (14) | 0.0045 (14) |
C21 | 0.0176 (16) | 0.0192 (18) | 0.025 (2) | −0.0001 (14) | 0.0047 (15) | 0.0075 (15) |
C22 | 0.0185 (16) | 0.0173 (18) | 0.027 (2) | −0.0030 (14) | 0.0031 (16) | 0.0029 (15) |
C23 | 0.0296 (18) | 0.0188 (19) | 0.034 (2) | −0.0005 (16) | 0.0071 (17) | −0.0011 (16) |
C24 | 0.0195 (16) | 0.0177 (18) | 0.029 (2) | 0.0025 (15) | 0.0045 (16) | 0.0090 (15) |
C25 | 0.0178 (15) | 0.0169 (17) | 0.0185 (18) | 0.0002 (15) | 0.0016 (15) | 0.0002 (14) |
C26 | 0.0165 (15) | 0.0217 (18) | 0.0219 (19) | −0.0019 (15) | −0.0028 (15) | 0.0040 (15) |
C27 | 0.0224 (16) | 0.0164 (17) | 0.0196 (18) | 0.0009 (15) | 0.0024 (15) | 0.0009 (14) |
C28 | 0.0238 (17) | 0.021 (2) | 0.027 (2) | −0.0012 (15) | −0.0011 (16) | 0.0005 (16) |
C29 | 0.0238 (16) | 0.028 (2) | 0.0228 (19) | 0.0019 (16) | 0.0007 (17) | 0.0068 (16) |
C30 | 0.0155 (16) | 0.026 (2) | 0.0231 (19) | −0.0010 (16) | −0.0010 (16) | 0.0073 (16) |
C31 | 0.0269 (19) | 0.027 (2) | 0.034 (2) | 0.0069 (16) | 0.0010 (17) | −0.0089 (17) |
C32 | 0.052 (2) | 0.043 (3) | 0.067 (3) | 0.002 (2) | 0.037 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
O3—C3 | 1.435 (4) | C16—H16A | 0.9900 |
O3—H3 | 0.8400 | C16—H16B | 0.9900 |
O11—C11 | 1.233 (3) | C17—C28 | 1.533 (4) |
O30—C30 | 1.340 (3) | C17—C22 | 1.542 (4) |
O30—C31 | 1.450 (3) | C17—C18 | 1.545 (4) |
O31—C30 | 1.208 (3) | C18—C19 | 1.542 (4) |
C1—C2 | 1.520 (4) | C18—H18 | 1.0000 |
C1—C10 | 1.549 (4) | C19—C20 | 1.532 (4) |
C1—H1A | 0.9900 | C19—H19A | 0.9900 |
C1—H1B | 0.9900 | C19—H19B | 0.9900 |
C2—C3 | 1.511 (4) | C20—C30 | 1.518 (4) |
C2—H2A | 0.9900 | C20—C21 | 1.529 (4) |
C2—H2B | 0.9900 | C20—C29 | 1.537 (4) |
C3—C4 | 1.539 (4) | C21—C22 | 1.521 (4) |
C3—H3A | 1.0000 | C21—H21A | 0.9900 |
C4—C24 | 1.526 (4) | C21—H21B | 0.9900 |
C4—C23 | 1.541 (4) | C22—H22A | 0.9900 |
C4—C5 | 1.557 (4) | C22—H22B | 0.9900 |
C5—C6 | 1.535 (4) | C23—H23A | 0.9800 |
C5—C10 | 1.563 (4) | C23—H23B | 0.9800 |
C5—H5 | 1.0000 | C23—H23C | 0.9800 |
C6—C7 | 1.526 (4) | C24—H24A | 0.9800 |
C6—H6A | 0.9900 | C24—H24B | 0.9800 |
C6—H6B | 0.9900 | C24—H24C | 0.9800 |
C7—C8 | 1.539 (4) | C25—H25A | 0.9800 |
C7—H7A | 0.9900 | C25—H25B | 0.9800 |
C7—H7B | 0.9900 | C25—H25C | 0.9800 |
C8—C26 | 1.544 (4) | C26—H26A | 0.9800 |
C8—C9 | 1.567 (4) | C26—H26B | 0.9800 |
C8—C14 | 1.588 (4) | C26—H26C | 0.9800 |
C9—C11 | 1.522 (4) | C27—H27A | 0.9800 |
C9—C10 | 1.560 (4) | C27—H27B | 0.9800 |
C9—H9 | 1.0000 | C27—H27C | 0.9800 |
C10—C25 | 1.546 (4) | C28—H28A | 0.9800 |
C11—C12 | 1.466 (4) | C28—H28B | 0.9800 |
C12—C13 | 1.341 (4) | C28—H28C | 0.9800 |
C12—H12 | 0.9500 | C29—H29A | 0.9800 |
C13—C18 | 1.517 (4) | C29—H29B | 0.9800 |
C13—C14 | 1.530 (4) | C29—H29C | 0.9800 |
C14—C27 | 1.549 (4) | C31—C32 | 1.493 (4) |
C14—C15 | 1.555 (4) | C31—H31A | 0.9900 |
C15—C16 | 1.535 (4) | C31—H31B | 0.9900 |
C15—H15A | 0.9900 | C32—H32A | 0.9800 |
C15—H15B | 0.9900 | C32—H32B | 0.9800 |
C16—C17 | 1.527 (4) | C32—H32C | 0.9800 |
| | | |
C3—O3—H3 | 109.5 | C28—C17—C22 | 107.5 (2) |
C30—O30—C31 | 115.9 (2) | C16—C17—C18 | 108.9 (2) |
C2—C1—C10 | 112.7 (2) | C28—C17—C18 | 109.9 (2) |
C2—C1—H1A | 109.0 | C22—C17—C18 | 109.1 (2) |
C10—C1—H1A | 109.0 | C13—C18—C19 | 111.2 (2) |
C2—C1—H1B | 109.0 | C13—C18—C17 | 111.6 (2) |
C10—C1—H1B | 109.0 | C19—C18—C17 | 112.7 (2) |
H1A—C1—H1B | 107.8 | C13—C18—H18 | 107.0 |
C3—C2—C1 | 111.1 (3) | C19—C18—H18 | 107.0 |
C3—C2—H2A | 109.4 | C17—C18—H18 | 107.0 |
C1—C2—H2A | 109.4 | C20—C19—C18 | 114.4 (2) |
C3—C2—H2B | 109.4 | C20—C19—H19A | 108.7 |
C1—C2—H2B | 109.4 | C18—C19—H19A | 108.7 |
H2A—C2—H2B | 108.0 | C20—C19—H19B | 108.7 |
O3—C3—C2 | 111.3 (3) | C18—C19—H19B | 108.7 |
O3—C3—C4 | 108.7 (2) | H19A—C19—H19B | 107.6 |
C2—C3—C4 | 113.8 (2) | C30—C20—C21 | 109.6 (2) |
O3—C3—H3A | 107.6 | C30—C20—C19 | 113.0 (3) |
C2—C3—H3A | 107.6 | C21—C20—C19 | 109.1 (2) |
C4—C3—H3A | 107.6 | C30—C20—C29 | 106.7 (2) |
C24—C4—C3 | 111.7 (2) | C21—C20—C29 | 109.2 (2) |
C24—C4—C23 | 107.9 (2) | C19—C20—C29 | 109.2 (2) |
C3—C4—C23 | 106.9 (2) | C22—C21—C20 | 111.8 (2) |
C24—C4—C5 | 112.6 (2) | C22—C21—H21A | 109.3 |
C3—C4—C5 | 108.3 (2) | C20—C21—H21A | 109.3 |
C23—C4—C5 | 109.3 (2) | C22—C21—H21B | 109.3 |
C6—C5—C4 | 113.5 (2) | C20—C21—H21B | 109.3 |
C6—C5—C10 | 109.8 (2) | H21A—C21—H21B | 107.9 |
C4—C5—C10 | 117.9 (2) | C21—C22—C17 | 115.0 (3) |
C6—C5—H5 | 104.7 | C21—C22—H22A | 108.5 |
C4—C5—H5 | 104.7 | C17—C22—H22A | 108.5 |
C10—C5—H5 | 104.7 | C21—C22—H22B | 108.5 |
C7—C6—C5 | 111.0 (2) | C17—C22—H22B | 108.5 |
C7—C6—H6A | 109.4 | H22A—C22—H22B | 107.5 |
C5—C6—H6A | 109.4 | C4—C23—H23A | 109.5 |
C7—C6—H6B | 109.4 | C4—C23—H23B | 109.5 |
C5—C6—H6B | 109.4 | H23A—C23—H23B | 109.5 |
H6A—C6—H6B | 108.0 | C4—C23—H23C | 109.5 |
C6—C7—C8 | 114.4 (2) | H23A—C23—H23C | 109.5 |
C6—C7—H7A | 108.7 | H23B—C23—H23C | 109.5 |
C8—C7—H7A | 108.7 | C4—C24—H24A | 109.5 |
C6—C7—H7B | 108.7 | C4—C24—H24B | 109.5 |
C8—C7—H7B | 108.7 | H24A—C24—H24B | 109.5 |
H7A—C7—H7B | 107.6 | C4—C24—H24C | 109.5 |
C7—C8—C26 | 107.7 (2) | H24A—C24—H24C | 109.5 |
C7—C8—C9 | 110.9 (2) | H24B—C24—H24C | 109.5 |
C26—C8—C9 | 109.6 (2) | C10—C25—H25A | 109.5 |
C7—C8—C14 | 109.5 (2) | C10—C25—H25B | 109.5 |
C26—C8—C14 | 111.1 (2) | H25A—C25—H25B | 109.5 |
C9—C8—C14 | 108.1 (2) | C10—C25—H25C | 109.5 |
C11—C9—C10 | 116.1 (2) | H25A—C25—H25C | 109.5 |
C11—C9—C8 | 108.4 (2) | H25B—C25—H25C | 109.5 |
C10—C9—C8 | 117.2 (2) | C8—C26—H26A | 109.5 |
C11—C9—H9 | 104.5 | C8—C26—H26B | 109.5 |
C10—C9—H9 | 104.5 | H26A—C26—H26B | 109.5 |
C8—C9—H9 | 104.5 | C8—C26—H26C | 109.5 |
C25—C10—C1 | 108.1 (2) | H26A—C26—H26C | 109.5 |
C25—C10—C9 | 112.3 (2) | H26B—C26—H26C | 109.5 |
C1—C10—C9 | 108.7 (2) | C14—C27—H27A | 109.5 |
C25—C10—C5 | 114.7 (2) | C14—C27—H27B | 109.5 |
C1—C10—C5 | 107.1 (2) | H27A—C27—H27B | 109.5 |
C9—C10—C5 | 105.7 (2) | C14—C27—H27C | 109.5 |
O11—C11—C12 | 119.0 (3) | H27A—C27—H27C | 109.5 |
O11—C11—C9 | 123.7 (3) | H27B—C27—H27C | 109.5 |
C12—C11—C9 | 117.2 (2) | C17—C28—H28A | 109.5 |
C13—C12—C11 | 125.0 (3) | C17—C28—H28B | 109.5 |
C13—C12—H12 | 117.5 | H28A—C28—H28B | 109.5 |
C11—C12—H12 | 117.5 | C17—C28—H28C | 109.5 |
C12—C13—C18 | 119.3 (3) | H28A—C28—H28C | 109.5 |
C12—C13—C14 | 119.9 (3) | H28B—C28—H28C | 109.5 |
C18—C13—C14 | 120.5 (2) | C20—C29—H29A | 109.5 |
C13—C14—C27 | 106.0 (2) | C20—C29—H29B | 109.5 |
C13—C14—C15 | 111.9 (2) | H29A—C29—H29B | 109.5 |
C27—C14—C15 | 107.0 (2) | C20—C29—H29C | 109.5 |
C13—C14—C8 | 109.8 (2) | H29A—C29—H29C | 109.5 |
C27—C14—C8 | 112.0 (2) | H29B—C29—H29C | 109.5 |
C15—C14—C8 | 110.1 (2) | O31—C30—O30 | 122.5 (3) |
C16—C15—C14 | 114.2 (2) | O31—C30—C20 | 124.5 (3) |
C16—C15—H15A | 108.7 | O30—C30—C20 | 112.8 (3) |
C14—C15—H15A | 108.7 | O30—C31—C32 | 108.4 (3) |
C16—C15—H15B | 108.7 | O30—C31—H31A | 110.0 |
C14—C15—H15B | 108.7 | C32—C31—H31A | 110.0 |
H15A—C15—H15B | 107.6 | O30—C31—H31B | 110.0 |
C17—C16—C15 | 113.3 (2) | C32—C31—H31B | 110.0 |
C17—C16—H16A | 108.9 | H31A—C31—H31B | 108.4 |
C15—C16—H16A | 108.9 | C31—C32—H32A | 109.5 |
C17—C16—H16B | 108.9 | C31—C32—H32B | 109.5 |
C15—C16—H16B | 108.9 | H32A—C32—H32B | 109.5 |
H16A—C16—H16B | 107.7 | C31—C32—H32C | 109.5 |
C16—C17—C28 | 110.3 (2) | H32A—C32—H32C | 109.5 |
C16—C17—C22 | 111.1 (3) | H32B—C32—H32C | 109.5 |
| | | |
C10—C1—C2—C3 | −59.7 (3) | C12—C13—C14—C15 | −150.0 (3) |
C1—C2—C3—O3 | −179.0 (2) | C18—C13—C14—C15 | 35.1 (4) |
C1—C2—C3—C4 | 57.8 (3) | C12—C13—C14—C8 | −27.5 (3) |
O3—C3—C4—C24 | −50.6 (3) | C18—C13—C14—C8 | 157.6 (2) |
C2—C3—C4—C24 | 74.0 (3) | C7—C8—C14—C13 | 177.8 (2) |
O3—C3—C4—C23 | 67.2 (3) | C26—C8—C14—C13 | −63.3 (3) |
C2—C3—C4—C23 | −168.2 (3) | C9—C8—C14—C13 | 57.0 (3) |
O3—C3—C4—C5 | −175.1 (2) | C7—C8—C14—C27 | 60.4 (3) |
C2—C3—C4—C5 | −50.5 (3) | C26—C8—C14—C27 | 179.2 (2) |
C24—C4—C5—C6 | 55.5 (3) | C9—C8—C14—C27 | −60.5 (3) |
C3—C4—C5—C6 | 179.5 (2) | C7—C8—C14—C15 | −58.6 (3) |
C23—C4—C5—C6 | −64.4 (3) | C26—C8—C14—C15 | 60.3 (3) |
C24—C4—C5—C10 | −75.0 (3) | C9—C8—C14—C15 | −179.4 (2) |
C3—C4—C5—C10 | 49.0 (3) | C13—C14—C15—C16 | −37.6 (3) |
C23—C4—C5—C10 | 165.1 (2) | C27—C14—C15—C16 | 78.1 (3) |
C4—C5—C6—C7 | 161.6 (2) | C8—C14—C15—C16 | −160.0 (2) |
C10—C5—C6—C7 | −64.1 (3) | C14—C15—C16—C17 | 52.8 (3) |
C5—C6—C7—C8 | 54.3 (3) | C15—C16—C17—C28 | 60.7 (3) |
C6—C7—C8—C26 | 76.6 (3) | C15—C16—C17—C22 | 179.8 (2) |
C6—C7—C8—C9 | −43.3 (3) | C15—C16—C17—C18 | −60.0 (3) |
C6—C7—C8—C14 | −162.4 (2) | C12—C13—C18—C19 | −92.3 (3) |
C7—C8—C9—C11 | 179.1 (2) | C14—C13—C18—C19 | 82.6 (3) |
C26—C8—C9—C11 | 60.4 (3) | C12—C13—C18—C17 | 141.0 (3) |
C14—C8—C9—C11 | −60.9 (3) | C14—C13—C18—C17 | −44.2 (3) |
C7—C8—C9—C10 | 45.3 (3) | C16—C17—C18—C13 | 53.7 (3) |
C26—C8—C9—C10 | −73.5 (3) | C28—C17—C18—C13 | −67.2 (3) |
C14—C8—C9—C10 | 165.3 (2) | C22—C17—C18—C13 | 175.1 (2) |
C2—C1—C10—C25 | −70.2 (3) | C16—C17—C18—C19 | −72.2 (3) |
C2—C1—C10—C9 | 167.7 (2) | C28—C17—C18—C19 | 166.9 (2) |
C2—C1—C10—C5 | 53.9 (3) | C22—C17—C18—C19 | 49.2 (3) |
C11—C9—C10—C25 | −58.4 (3) | C13—C18—C19—C20 | −179.3 (2) |
C8—C9—C10—C25 | 71.9 (3) | C17—C18—C19—C20 | −53.1 (3) |
C11—C9—C10—C1 | 61.1 (3) | C18—C19—C20—C30 | −68.3 (3) |
C8—C9—C10—C1 | −168.6 (2) | C18—C19—C20—C21 | 53.9 (3) |
C11—C9—C10—C5 | 175.8 (2) | C18—C19—C20—C29 | 173.2 (2) |
C8—C9—C10—C5 | −53.9 (3) | C30—C20—C21—C22 | 70.1 (3) |
C6—C5—C10—C25 | −62.9 (3) | C19—C20—C21—C22 | −54.1 (3) |
C4—C5—C10—C25 | 69.3 (3) | C29—C20—C21—C22 | −173.4 (2) |
C6—C5—C10—C1 | 177.2 (2) | C20—C21—C22—C17 | 56.2 (3) |
C4—C5—C10—C1 | −50.6 (3) | C16—C17—C22—C21 | 67.9 (3) |
C6—C5—C10—C9 | 61.4 (3) | C28—C17—C22—C21 | −171.3 (2) |
C4—C5—C10—C9 | −166.4 (2) | C18—C17—C22—C21 | −52.2 (3) |
C10—C9—C11—O11 | −12.2 (4) | C31—O30—C30—O31 | −0.2 (4) |
C8—C9—C11—O11 | −146.6 (3) | C31—O30—C30—C20 | −177.1 (2) |
C10—C9—C11—C12 | 170.4 (2) | C21—C20—C30—O31 | 27.8 (4) |
C8—C9—C11—C12 | 36.0 (3) | C19—C20—C30—O31 | 149.8 (3) |
O11—C11—C12—C13 | 176.7 (3) | C29—C20—C30—O31 | −90.2 (4) |
C9—C11—C12—C13 | −5.8 (4) | C21—C20—C30—O30 | −155.4 (2) |
C11—C12—C13—C18 | 176.2 (3) | C19—C20—C30—O30 | −33.4 (3) |
C11—C12—C13—C14 | 1.3 (4) | C29—C20—C30—O30 | 86.6 (3) |
C12—C13—C14—C27 | 93.6 (3) | C30—O30—C31—C32 | −171.2 (3) |
C18—C13—C14—C27 | −81.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O11i | 0.84 | 2.23 | 3.039 (3) | 161 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
(5) isopropyl-3/b-hydroxy-11-oxoolean-12-en-30-oate
top
Crystal data top
C33H52O4 | Dx = 1.177 Mg m−3 |
Mr = 512.74 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 8245 reflections |
a = 11.7789 (2) Å | θ = 4.0–76.1° |
b = 13.0812 (3) Å | µ = 0.58 mm−1 |
c = 18.7845 (4) Å | T = 130 K |
V = 2894.36 (10) Å3 | Parallelepiped, colorless |
Z = 4 | 0.20 × 0.20 × 0.10 mm |
F(000) = 1128 | |
Data collection top
SuperNova, Dual, Cu at zero, Atlas diffractometer | 5719 independent reflections |
Radiation source: sealed X-ray tube | 5231 reflections with I > 2σ(I) |
Detector resolution: 5.1996 pixels mm-1 | Rint = 0.037 |
ω scans | θmax = 74.5°, θmin = 6.8° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, 2014
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −14→9 |
Tmin = 0.544, Tmax = 1.000 | k = −16→16 |
15070 measured reflections | l = −17→23 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.091P)2 + 0.4078P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.144 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.33 e Å−3 |
5719 reflections | Δρmin = −0.21 e Å−3 |
344 parameters | Absolute structure: Flack x determined using 2089 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: 0.08 (14) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.66526 (19) | −0.29625 (16) | 0.73372 (12) | 0.0418 (5) | |
H3 | 0.6220 | −0.2973 | 0.7692 | 0.063* | |
O11 | 0.48456 (16) | 0.17424 (16) | 0.65081 (11) | 0.0384 (4) | |
O30 | 0.52455 (18) | 0.56389 (16) | 0.47100 (10) | 0.0378 (4) | |
O31 | 0.6292 (2) | 0.68540 (18) | 0.41794 (14) | 0.0545 (6) | |
C1 | 0.5689 (2) | −0.0337 (2) | 0.67458 (14) | 0.0339 (5) | |
H1A | 0.4950 | 0.0017 | 0.6794 | 0.041* | |
H1B | 0.5827 | −0.0452 | 0.6232 | 0.041* | |
C2 | 0.5619 (2) | −0.1374 (2) | 0.71225 (15) | 0.0350 (6) | |
H2A | 0.5423 | −0.1266 | 0.7629 | 0.042* | |
H2B | 0.5008 | −0.1787 | 0.6903 | 0.042* | |
C3 | 0.6732 (2) | −0.1951 (2) | 0.70738 (14) | 0.0343 (5) | |
H3A | 0.6908 | −0.2014 | 0.6555 | 0.041* | |
C4 | 0.7729 (2) | −0.1350 (2) | 0.74056 (14) | 0.0324 (5) | |
C5 | 0.7762 (2) | −0.0272 (2) | 0.70494 (13) | 0.0309 (5) | |
H5 | 0.7914 | −0.0417 | 0.6535 | 0.037* | |
C6 | 0.8761 (2) | 0.0393 (2) | 0.72829 (15) | 0.0352 (6) | |
H6A | 0.9451 | −0.0034 | 0.7332 | 0.042* | |
H6B | 0.8595 | 0.0703 | 0.7752 | 0.042* | |
C7 | 0.8973 (2) | 0.1237 (2) | 0.67347 (15) | 0.0333 (5) | |
H7A | 0.9196 | 0.0919 | 0.6278 | 0.040* | |
H7B | 0.9614 | 0.1666 | 0.6898 | 0.040* | |
C8 | 0.7933 (2) | 0.1925 (2) | 0.66084 (13) | 0.0294 (5) | |
C9 | 0.6842 (2) | 0.1262 (2) | 0.65021 (13) | 0.0294 (5) | |
H9 | 0.6965 | 0.0912 | 0.6035 | 0.035* | |
C10 | 0.6636 (2) | 0.0359 (2) | 0.70442 (13) | 0.0296 (5) | |
C11 | 0.5831 (2) | 0.1968 (2) | 0.63689 (13) | 0.0312 (5) | |
C12 | 0.6062 (2) | 0.2968 (2) | 0.60305 (14) | 0.0330 (5) | |
H12 | 0.5435 | 0.3411 | 0.5954 | 0.040* | |
C13 | 0.7081 (2) | 0.3294 (2) | 0.58241 (13) | 0.0311 (5) | |
C14 | 0.8114 (2) | 0.2597 (2) | 0.59117 (14) | 0.0302 (5) | |
C15 | 0.9250 (2) | 0.3199 (2) | 0.59561 (15) | 0.0356 (6) | |
H15A | 0.9365 | 0.3429 | 0.6453 | 0.043* | |
H15B | 0.9882 | 0.2733 | 0.5833 | 0.043* | |
C16 | 0.9296 (2) | 0.4127 (2) | 0.54657 (16) | 0.0371 (6) | |
H16A | 0.9274 | 0.3893 | 0.4965 | 0.045* | |
H16B | 1.0024 | 0.4491 | 0.5541 | 0.045* | |
C17 | 0.8311 (3) | 0.4871 (2) | 0.55960 (15) | 0.0364 (6) | |
C18 | 0.7172 (2) | 0.4320 (2) | 0.54481 (14) | 0.0331 (5) | |
H18 | 0.6558 | 0.4765 | 0.5646 | 0.040* | |
C19 | 0.6910 (2) | 0.4172 (2) | 0.46445 (14) | 0.0325 (5) | |
H19A | 0.7424 | 0.3641 | 0.4452 | 0.039* | |
H19B | 0.6123 | 0.3916 | 0.4595 | 0.039* | |
C20 | 0.7036 (3) | 0.5142 (2) | 0.41937 (14) | 0.0357 (6) | |
C21 | 0.8220 (3) | 0.5582 (2) | 0.43184 (16) | 0.0410 (6) | |
H21A | 0.8306 | 0.6219 | 0.4039 | 0.049* | |
H21B | 0.8795 | 0.5088 | 0.4148 | 0.049* | |
C22 | 0.8429 (3) | 0.5811 (2) | 0.51047 (17) | 0.0418 (6) | |
H22A | 0.7884 | 0.6341 | 0.5262 | 0.050* | |
H22B | 0.9203 | 0.6096 | 0.5159 | 0.050* | |
C23 | 0.7643 (3) | −0.1331 (2) | 0.82253 (15) | 0.0403 (6) | |
H23A | 0.6890 | −0.1083 | 0.8366 | 0.060* | |
H23B | 0.8226 | −0.0874 | 0.8418 | 0.060* | |
H23C | 0.7757 | −0.2022 | 0.8412 | 0.060* | |
C24 | 0.8820 (2) | −0.1934 (2) | 0.72134 (16) | 0.0385 (6) | |
H24A | 0.8745 | −0.2650 | 0.7358 | 0.058* | |
H24B | 0.9467 | −0.1624 | 0.7461 | 0.058* | |
H24C | 0.8945 | −0.1898 | 0.6698 | 0.058* | |
C25 | 0.6254 (2) | 0.0750 (2) | 0.77802 (14) | 0.0353 (6) | |
H25A | 0.5750 | 0.1340 | 0.7719 | 0.053* | |
H25B | 0.6921 | 0.0955 | 0.8058 | 0.053* | |
H25C | 0.5848 | 0.0205 | 0.8032 | 0.053* | |
C26 | 0.7800 (2) | 0.2624 (2) | 0.72715 (14) | 0.0345 (5) | |
H26A | 0.7837 | 0.2207 | 0.7704 | 0.052* | |
H26B | 0.7066 | 0.2975 | 0.7251 | 0.052* | |
H26C | 0.8413 | 0.3131 | 0.7278 | 0.052* | |
C27 | 0.8187 (2) | 0.1932 (2) | 0.52232 (14) | 0.0337 (5) | |
H27A | 0.7431 | 0.1670 | 0.5104 | 0.050* | |
H27B | 0.8705 | 0.1357 | 0.5304 | 0.050* | |
H27C | 0.8471 | 0.2350 | 0.4829 | 0.050* | |
C28 | 0.8325 (3) | 0.5255 (2) | 0.63692 (17) | 0.0453 (7) | |
H28A | 0.8143 | 0.4688 | 0.6691 | 0.068* | |
H28B | 0.7759 | 0.5799 | 0.6426 | 0.068* | |
H28C | 0.9080 | 0.5523 | 0.6483 | 0.068* | |
C29 | 0.6901 (3) | 0.4873 (2) | 0.33985 (15) | 0.0412 (6) | |
H29A | 0.6128 | 0.4625 | 0.3311 | 0.062* | |
H29B | 0.7448 | 0.4340 | 0.3270 | 0.062* | |
H29C | 0.7039 | 0.5484 | 0.3110 | 0.062* | |
C30 | 0.6169 (3) | 0.5976 (2) | 0.43563 (15) | 0.0383 (6) | |
C31 | 0.4469 (3) | 0.6428 (2) | 0.49698 (16) | 0.0435 (7) | |
H31 | 0.4336 | 0.6945 | 0.4587 | 0.052* | |
C32 | 0.4998 (4) | 0.6941 (3) | 0.56098 (19) | 0.0551 (9) | |
H32A | 0.5217 | 0.6421 | 0.5960 | 0.083* | |
H32B | 0.4448 | 0.7411 | 0.5824 | 0.083* | |
H32C | 0.5673 | 0.7323 | 0.5460 | 0.083* | |
C33 | 0.3365 (3) | 0.5894 (3) | 0.51460 (18) | 0.0504 (8) | |
H33A | 0.3059 | 0.5573 | 0.4715 | 0.076* | |
H33B | 0.2819 | 0.6394 | 0.5329 | 0.076* | |
H33C | 0.3503 | 0.5369 | 0.5508 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0473 (11) | 0.0342 (10) | 0.0440 (11) | 0.0000 (9) | 0.0067 (9) | 0.0044 (8) |
O11 | 0.0329 (9) | 0.0421 (11) | 0.0401 (10) | 0.0034 (8) | 0.0030 (8) | 0.0036 (8) |
O30 | 0.0487 (11) | 0.0347 (10) | 0.0299 (9) | 0.0067 (9) | 0.0037 (8) | 0.0021 (8) |
O31 | 0.0659 (15) | 0.0405 (12) | 0.0570 (14) | 0.0023 (11) | 0.0045 (12) | 0.0143 (10) |
C1 | 0.0351 (12) | 0.0364 (13) | 0.0303 (12) | 0.0001 (11) | −0.0020 (10) | 0.0028 (11) |
C2 | 0.0366 (13) | 0.0358 (13) | 0.0328 (13) | −0.0040 (11) | −0.0001 (11) | 0.0024 (11) |
C3 | 0.0408 (13) | 0.0339 (13) | 0.0282 (12) | −0.0009 (12) | 0.0023 (10) | 0.0017 (10) |
C4 | 0.0385 (13) | 0.0336 (12) | 0.0251 (12) | 0.0012 (11) | 0.0000 (10) | 0.0023 (10) |
C5 | 0.0338 (12) | 0.0335 (12) | 0.0255 (11) | 0.0013 (10) | −0.0009 (10) | 0.0012 (10) |
C6 | 0.0358 (12) | 0.0396 (13) | 0.0303 (12) | 0.0032 (11) | −0.0049 (10) | 0.0011 (11) |
C7 | 0.0309 (12) | 0.0350 (13) | 0.0342 (13) | −0.0011 (10) | −0.0027 (10) | 0.0013 (11) |
C8 | 0.0313 (11) | 0.0308 (12) | 0.0261 (11) | −0.0009 (10) | −0.0012 (9) | −0.0004 (10) |
C9 | 0.0320 (11) | 0.0327 (12) | 0.0236 (11) | 0.0026 (10) | −0.0001 (9) | 0.0004 (9) |
C10 | 0.0336 (12) | 0.0318 (12) | 0.0233 (11) | 0.0017 (10) | 0.0004 (9) | 0.0007 (9) |
C11 | 0.0341 (12) | 0.0346 (12) | 0.0251 (11) | 0.0032 (11) | −0.0012 (9) | −0.0030 (10) |
C12 | 0.0344 (12) | 0.0357 (13) | 0.0289 (12) | 0.0037 (11) | −0.0005 (10) | 0.0004 (10) |
C13 | 0.0379 (12) | 0.0319 (12) | 0.0234 (10) | 0.0023 (11) | −0.0023 (10) | −0.0033 (9) |
C14 | 0.0318 (12) | 0.0304 (11) | 0.0285 (12) | −0.0011 (10) | 0.0000 (9) | 0.0006 (9) |
C15 | 0.0346 (13) | 0.0357 (14) | 0.0366 (14) | −0.0020 (11) | −0.0010 (11) | 0.0009 (11) |
C16 | 0.0383 (13) | 0.0351 (13) | 0.0381 (14) | −0.0061 (11) | −0.0006 (11) | 0.0023 (11) |
C17 | 0.0451 (14) | 0.0321 (12) | 0.0319 (13) | −0.0030 (12) | −0.0027 (11) | −0.0008 (10) |
C18 | 0.0404 (13) | 0.0310 (12) | 0.0279 (12) | 0.0035 (11) | 0.0011 (10) | 0.0005 (10) |
C19 | 0.0375 (12) | 0.0317 (12) | 0.0282 (12) | −0.0002 (11) | 0.0003 (10) | 0.0016 (10) |
C20 | 0.0427 (14) | 0.0361 (13) | 0.0285 (12) | −0.0024 (11) | 0.0017 (11) | 0.0020 (10) |
C21 | 0.0463 (15) | 0.0404 (14) | 0.0364 (14) | −0.0073 (13) | 0.0014 (12) | 0.0079 (11) |
C22 | 0.0480 (15) | 0.0356 (14) | 0.0419 (15) | −0.0063 (13) | −0.0048 (12) | 0.0026 (12) |
C23 | 0.0511 (16) | 0.0437 (15) | 0.0260 (12) | 0.0032 (13) | −0.0012 (11) | 0.0062 (11) |
C24 | 0.0382 (13) | 0.0376 (14) | 0.0396 (14) | 0.0043 (12) | 0.0004 (11) | 0.0043 (11) |
C25 | 0.0412 (13) | 0.0402 (13) | 0.0245 (11) | 0.0034 (12) | 0.0023 (10) | 0.0000 (10) |
C26 | 0.0420 (13) | 0.0345 (13) | 0.0270 (12) | −0.0019 (11) | −0.0041 (10) | −0.0024 (10) |
C27 | 0.0389 (13) | 0.0349 (12) | 0.0272 (12) | 0.0015 (11) | 0.0035 (10) | −0.0009 (10) |
C28 | 0.0599 (18) | 0.0386 (14) | 0.0375 (15) | −0.0021 (14) | −0.0066 (13) | −0.0052 (12) |
C29 | 0.0516 (16) | 0.0450 (15) | 0.0269 (13) | −0.0038 (13) | 0.0013 (12) | 0.0031 (11) |
C30 | 0.0493 (15) | 0.0363 (14) | 0.0294 (12) | 0.0000 (12) | −0.0016 (11) | 0.0019 (11) |
C31 | 0.0604 (18) | 0.0403 (15) | 0.0298 (13) | 0.0146 (14) | −0.0009 (13) | 0.0008 (11) |
C32 | 0.076 (2) | 0.0502 (18) | 0.0387 (15) | 0.0175 (18) | −0.0052 (16) | −0.0087 (14) |
C33 | 0.0563 (18) | 0.0575 (19) | 0.0373 (15) | 0.0146 (16) | 0.0045 (13) | −0.0054 (14) |
Geometric parameters (Å, º) top
O3—C3 | 1.415 (3) | C17—C28 | 1.537 (4) |
O3—H3 | 0.8400 | C17—C22 | 1.543 (4) |
O11—C11 | 1.227 (3) | C17—C18 | 1.548 (4) |
O30—C30 | 1.349 (4) | C18—C19 | 1.553 (4) |
O30—C31 | 1.462 (4) | C18—H18 | 1.0000 |
O31—C30 | 1.204 (4) | C19—C20 | 1.532 (4) |
C1—C2 | 1.531 (4) | C19—H19A | 0.9900 |
C1—C10 | 1.546 (4) | C19—H19B | 0.9900 |
C1—H1A | 0.9900 | C20—C30 | 1.525 (4) |
C1—H1B | 0.9900 | C20—C21 | 1.526 (4) |
C2—C3 | 1.516 (4) | C20—C29 | 1.543 (4) |
C2—H2A | 0.9900 | C21—C22 | 1.527 (4) |
C2—H2B | 0.9900 | C21—H21A | 0.9900 |
C3—C4 | 1.544 (4) | C21—H21B | 0.9900 |
C3—H3A | 1.0000 | C22—H22A | 0.9900 |
C4—C24 | 1.538 (4) | C22—H22B | 0.9900 |
C4—C23 | 1.543 (4) | C23—H23A | 0.9800 |
C4—C5 | 1.562 (4) | C23—H23B | 0.9800 |
C5—C6 | 1.528 (4) | C23—H23C | 0.9800 |
C5—C10 | 1.562 (4) | C24—H24A | 0.9800 |
C5—H5 | 1.0000 | C24—H24B | 0.9800 |
C6—C7 | 1.530 (4) | C24—H24C | 0.9800 |
C6—H6A | 0.9900 | C25—H25A | 0.9800 |
C6—H6B | 0.9900 | C25—H25B | 0.9800 |
C7—C8 | 1.538 (3) | C25—H25C | 0.9800 |
C7—H7A | 0.9900 | C26—H26A | 0.9800 |
C7—H7B | 0.9900 | C26—H26B | 0.9800 |
C8—C26 | 1.553 (3) | C26—H26C | 0.9800 |
C8—C9 | 1.564 (3) | C27—H27A | 0.9800 |
C8—C14 | 1.591 (3) | C27—H27B | 0.9800 |
C9—C11 | 1.528 (3) | C27—H27C | 0.9800 |
C9—C10 | 1.578 (3) | C28—H28A | 0.9800 |
C9—H9 | 1.0000 | C28—H28B | 0.9800 |
C10—C25 | 1.541 (3) | C28—H28C | 0.9800 |
C11—C12 | 1.479 (4) | C29—H29A | 0.9800 |
C12—C13 | 1.331 (4) | C29—H29B | 0.9800 |
C12—H12 | 0.9500 | C29—H29C | 0.9800 |
C13—C18 | 1.521 (4) | C31—C32 | 1.512 (5) |
C13—C14 | 1.529 (4) | C31—C33 | 1.512 (5) |
C14—C15 | 1.555 (4) | C31—H31 | 1.0000 |
C14—C27 | 1.561 (4) | C32—H32A | 0.9800 |
C15—C16 | 1.525 (4) | C32—H32B | 0.9800 |
C15—H15A | 0.9900 | C32—H32C | 0.9800 |
C15—H15B | 0.9900 | C33—H33A | 0.9800 |
C16—C17 | 1.534 (4) | C33—H33B | 0.9800 |
C16—H16A | 0.9900 | C33—H33C | 0.9800 |
C16—H16B | 0.9900 | | |
| | | |
C3—O3—H3 | 109.5 | C22—C17—C18 | 109.9 (2) |
C30—O30—C31 | 116.0 (2) | C13—C18—C17 | 112.9 (2) |
C2—C1—C10 | 113.1 (2) | C13—C18—C19 | 109.1 (2) |
C2—C1—H1A | 108.9 | C17—C18—C19 | 113.9 (2) |
C10—C1—H1A | 108.9 | C13—C18—H18 | 106.8 |
C2—C1—H1B | 108.9 | C17—C18—H18 | 106.8 |
C10—C1—H1B | 108.9 | C19—C18—H18 | 106.8 |
H1A—C1—H1B | 107.8 | C20—C19—C18 | 114.5 (2) |
C3—C2—C1 | 111.5 (2) | C20—C19—H19A | 108.6 |
C3—C2—H2A | 109.3 | C18—C19—H19A | 108.6 |
C1—C2—H2A | 109.3 | C20—C19—H19B | 108.6 |
C3—C2—H2B | 109.3 | C18—C19—H19B | 108.6 |
C1—C2—H2B | 109.3 | H19A—C19—H19B | 107.6 |
H2A—C2—H2B | 108.0 | C30—C20—C21 | 108.1 (2) |
O3—C3—C2 | 112.8 (2) | C30—C20—C19 | 114.6 (2) |
O3—C3—C4 | 112.7 (2) | C21—C20—C19 | 108.4 (2) |
C2—C3—C4 | 112.3 (2) | C30—C20—C29 | 106.7 (2) |
O3—C3—H3A | 106.2 | C21—C20—C29 | 109.2 (2) |
C2—C3—H3A | 106.2 | C19—C20—C29 | 109.7 (2) |
C4—C3—H3A | 106.2 | C20—C21—C22 | 111.7 (2) |
C24—C4—C23 | 107.3 (2) | C20—C21—H21A | 109.3 |
C24—C4—C3 | 106.7 (2) | C22—C21—H21A | 109.3 |
C23—C4—C3 | 111.2 (2) | C20—C21—H21B | 109.3 |
C24—C4—C5 | 109.1 (2) | C22—C21—H21B | 109.3 |
C23—C4—C5 | 114.5 (2) | H21A—C21—H21B | 107.9 |
C3—C4—C5 | 107.8 (2) | C21—C22—C17 | 114.0 (2) |
C6—C5—C4 | 114.2 (2) | C21—C22—H22A | 108.7 |
C6—C5—C10 | 110.8 (2) | C17—C22—H22A | 108.7 |
C4—C5—C10 | 117.3 (2) | C21—C22—H22B | 108.7 |
C6—C5—H5 | 104.3 | C17—C22—H22B | 108.7 |
C4—C5—H5 | 104.3 | H22A—C22—H22B | 107.6 |
C10—C5—H5 | 104.3 | C4—C23—H23A | 109.5 |
C5—C6—C7 | 110.1 (2) | C4—C23—H23B | 109.5 |
C5—C6—H6A | 109.6 | H23A—C23—H23B | 109.5 |
C7—C6—H6A | 109.6 | C4—C23—H23C | 109.5 |
C5—C6—H6B | 109.6 | H23A—C23—H23C | 109.5 |
C7—C6—H6B | 109.6 | H23B—C23—H23C | 109.5 |
H6A—C6—H6B | 108.2 | C4—C24—H24A | 109.5 |
C6—C7—C8 | 113.4 (2) | C4—C24—H24B | 109.5 |
C6—C7—H7A | 108.9 | H24A—C24—H24B | 109.5 |
C8—C7—H7A | 108.9 | C4—C24—H24C | 109.5 |
C6—C7—H7B | 108.9 | H24A—C24—H24C | 109.5 |
C8—C7—H7B | 108.9 | H24B—C24—H24C | 109.5 |
H7A—C7—H7B | 107.7 | C10—C25—H25A | 109.5 |
C7—C8—C26 | 107.5 (2) | C10—C25—H25B | 109.5 |
C7—C8—C9 | 110.4 (2) | H25A—C25—H25B | 109.5 |
C26—C8—C9 | 110.2 (2) | C10—C25—H25C | 109.5 |
C7—C8—C14 | 110.1 (2) | H25A—C25—H25C | 109.5 |
C26—C8—C14 | 110.4 (2) | H25B—C25—H25C | 109.5 |
C9—C8—C14 | 108.16 (19) | C8—C26—H26A | 109.5 |
C11—C9—C8 | 109.0 (2) | C8—C26—H26B | 109.5 |
C11—C9—C10 | 116.0 (2) | H26A—C26—H26B | 109.5 |
C8—C9—C10 | 117.3 (2) | C8—C26—H26C | 109.5 |
C11—C9—H9 | 104.3 | H26A—C26—H26C | 109.5 |
C8—C9—H9 | 104.3 | H26B—C26—H26C | 109.5 |
C10—C9—H9 | 104.3 | C14—C27—H27A | 109.5 |
C25—C10—C1 | 108.1 (2) | C14—C27—H27B | 109.5 |
C25—C10—C5 | 114.7 (2) | H27A—C27—H27B | 109.5 |
C1—C10—C5 | 107.6 (2) | C14—C27—H27C | 109.5 |
C25—C10—C9 | 112.1 (2) | H27A—C27—H27C | 109.5 |
C1—C10—C9 | 108.5 (2) | H27B—C27—H27C | 109.5 |
C5—C10—C9 | 105.6 (2) | C17—C28—H28A | 109.5 |
O11—C11—C12 | 118.6 (2) | C17—C28—H28B | 109.5 |
O11—C11—C9 | 123.8 (3) | H28A—C28—H28B | 109.5 |
C12—C11—C9 | 117.5 (2) | C17—C28—H28C | 109.5 |
C13—C12—C11 | 125.0 (2) | H28A—C28—H28C | 109.5 |
C13—C12—H12 | 117.5 | H28B—C28—H28C | 109.5 |
C11—C12—H12 | 117.5 | C20—C29—H29A | 109.5 |
C12—C13—C18 | 118.8 (2) | C20—C29—H29B | 109.5 |
C12—C13—C14 | 119.7 (2) | H29A—C29—H29B | 109.5 |
C18—C13—C14 | 121.3 (2) | C20—C29—H29C | 109.5 |
C13—C14—C15 | 112.9 (2) | H29A—C29—H29C | 109.5 |
C13—C14—C27 | 106.7 (2) | H29B—C29—H29C | 109.5 |
C15—C14—C27 | 106.2 (2) | O31—C30—O30 | 123.0 (3) |
C13—C14—C8 | 108.1 (2) | O31—C30—C20 | 123.1 (3) |
C15—C14—C8 | 110.5 (2) | O30—C30—C20 | 113.9 (2) |
C27—C14—C8 | 112.4 (2) | O30—C31—C32 | 108.7 (3) |
C16—C15—C14 | 113.7 (2) | O30—C31—C33 | 106.6 (3) |
C16—C15—H15A | 108.8 | C32—C31—C33 | 112.7 (3) |
C14—C15—H15A | 108.8 | O30—C31—H31 | 109.6 |
C16—C15—H15B | 108.8 | C32—C31—H31 | 109.6 |
C14—C15—H15B | 108.8 | C33—C31—H31 | 109.6 |
H15A—C15—H15B | 107.7 | C31—C32—H32A | 109.5 |
C15—C16—C17 | 112.4 (2) | C31—C32—H32B | 109.5 |
C15—C16—H16A | 109.1 | H32A—C32—H32B | 109.5 |
C17—C16—H16A | 109.1 | C31—C32—H32C | 109.5 |
C15—C16—H16B | 109.1 | H32A—C32—H32C | 109.5 |
C17—C16—H16B | 109.1 | H32B—C32—H32C | 109.5 |
H16A—C16—H16B | 107.9 | C31—C33—H33A | 109.5 |
C16—C17—C28 | 110.5 (3) | C31—C33—H33B | 109.5 |
C16—C17—C22 | 110.0 (2) | H33A—C33—H33B | 109.5 |
C28—C17—C22 | 107.7 (2) | C31—C33—H33C | 109.5 |
C16—C17—C18 | 109.4 (2) | H33A—C33—H33C | 109.5 |
C28—C17—C18 | 109.3 (2) | H33B—C33—H33C | 109.5 |
| | | |
C10—C1—C2—C3 | −58.1 (3) | C12—C13—C14—C27 | 88.0 (3) |
C1—C2—C3—O3 | −172.5 (2) | C18—C13—C14—C27 | −86.8 (3) |
C1—C2—C3—C4 | 58.9 (3) | C12—C13—C14—C8 | −33.1 (3) |
O3—C3—C4—C24 | 60.4 (3) | C18—C13—C14—C8 | 152.1 (2) |
C2—C3—C4—C24 | −171.0 (2) | C7—C8—C14—C13 | −178.0 (2) |
O3—C3—C4—C23 | −56.4 (3) | C26—C8—C14—C13 | −59.4 (3) |
C2—C3—C4—C23 | 72.3 (3) | C9—C8—C14—C13 | 61.3 (2) |
O3—C3—C4—C5 | 177.4 (2) | C7—C8—C14—C15 | −53.9 (3) |
C2—C3—C4—C5 | −53.9 (3) | C26—C8—C14—C15 | 64.6 (3) |
C24—C4—C5—C6 | −60.2 (3) | C9—C8—C14—C15 | −174.7 (2) |
C23—C4—C5—C6 | 60.0 (3) | C7—C8—C14—C27 | 64.5 (3) |
C3—C4—C5—C6 | −175.8 (2) | C26—C8—C14—C27 | −176.9 (2) |
C24—C4—C5—C10 | 167.7 (2) | C9—C8—C14—C27 | −56.2 (3) |
C23—C4—C5—C10 | −72.1 (3) | C13—C14—C15—C16 | −37.8 (3) |
C3—C4—C5—C10 | 52.2 (3) | C27—C14—C15—C16 | 78.8 (3) |
C4—C5—C6—C7 | 159.7 (2) | C8—C14—C15—C16 | −159.0 (2) |
C10—C5—C6—C7 | −65.2 (3) | C14—C15—C16—C17 | 55.9 (3) |
C5—C6—C7—C8 | 57.8 (3) | C15—C16—C17—C28 | 59.2 (3) |
C6—C7—C8—C26 | 73.3 (3) | C15—C16—C17—C22 | 177.9 (2) |
C6—C7—C8—C9 | −47.0 (3) | C15—C16—C17—C18 | −61.2 (3) |
C6—C7—C8—C14 | −166.4 (2) | C12—C13—C18—C17 | 148.8 (2) |
C7—C8—C9—C11 | −179.3 (2) | C14—C13—C18—C17 | −36.4 (3) |
C26—C8—C9—C11 | 62.0 (3) | C12—C13—C18—C19 | −83.5 (3) |
C14—C8—C9—C11 | −58.7 (2) | C14—C13—C18—C19 | 91.3 (3) |
C7—C8—C9—C10 | 46.3 (3) | C16—C17—C18—C13 | 49.8 (3) |
C26—C8—C9—C10 | −72.4 (3) | C28—C17—C18—C13 | −71.3 (3) |
C14—C8—C9—C10 | 166.8 (2) | C22—C17—C18—C13 | 170.6 (2) |
C2—C1—C10—C25 | −72.8 (3) | C16—C17—C18—C19 | −75.4 (3) |
C2—C1—C10—C5 | 51.6 (3) | C28—C17—C18—C19 | 163.5 (2) |
C2—C1—C10—C9 | 165.4 (2) | C22—C17—C18—C19 | 45.5 (3) |
C6—C5—C10—C25 | −64.2 (3) | C13—C18—C19—C20 | −176.8 (2) |
C4—C5—C10—C25 | 69.4 (3) | C17—C18—C19—C20 | −49.7 (3) |
C6—C5—C10—C1 | 175.5 (2) | C18—C19—C20—C30 | −67.0 (3) |
C4—C5—C10—C1 | −50.9 (3) | C18—C19—C20—C21 | 53.9 (3) |
C6—C5—C10—C9 | 59.7 (3) | C18—C19—C20—C29 | 173.0 (2) |
C4—C5—C10—C9 | −166.7 (2) | C30—C20—C21—C22 | 67.3 (3) |
C11—C9—C10—C25 | −57.6 (3) | C19—C20—C21—C22 | −57.5 (3) |
C8—C9—C10—C25 | 73.7 (3) | C29—C20—C21—C22 | −177.0 (2) |
C11—C9—C10—C1 | 61.7 (3) | C20—C21—C22—C17 | 58.7 (4) |
C8—C9—C10—C1 | −167.0 (2) | C16—C17—C22—C21 | 69.8 (3) |
C11—C9—C10—C5 | 176.9 (2) | C28—C17—C22—C21 | −169.7 (3) |
C8—C9—C10—C5 | −51.8 (3) | C18—C17—C22—C21 | −50.7 (3) |
C8—C9—C11—O11 | −153.6 (2) | C31—O30—C30—O31 | −9.3 (4) |
C10—C9—C11—O11 | −18.5 (4) | C31—O30—C30—C20 | 171.4 (2) |
C8—C9—C11—C12 | 28.5 (3) | C21—C20—C30—O31 | 41.4 (4) |
C10—C9—C11—C12 | 163.6 (2) | C19—C20—C30—O31 | 162.5 (3) |
O11—C11—C12—C13 | −177.1 (3) | C29—C20—C30—O31 | −76.0 (4) |
C9—C11—C12—C13 | 0.9 (4) | C21—C20—C30—O30 | −139.3 (3) |
C11—C12—C13—C18 | 176.9 (2) | C19—C20—C30—O30 | −18.2 (3) |
C11—C12—C13—C14 | 2.0 (4) | C29—C20—C30—O30 | 103.4 (3) |
C12—C13—C14—C15 | −155.8 (2) | C30—O30—C31—C32 | −74.6 (3) |
C18—C13—C14—C15 | 29.5 (3) | C30—O30—C31—C33 | 163.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O11i | 0.84 | 1.99 | 2.823 (3) | 170 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |
(6) 2-(morpholin-4-yl)ethyl-3/b-hydroxy-11-oxoolean-12-en-30-oate
top
Crystal data top
C36H57NO5 | Dx = 1.185 Mg m−3 |
Mr = 583.82 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 7311 reflections |
a = 12.8700 (1) Å | θ = 3.2–76.3° |
b = 13.6972 (2) Å | µ = 0.61 mm−1 |
c = 18.5682 (3) Å | T = 130 K |
V = 3273.26 (8) Å3 | Needle, colorless |
Z = 4 | 0.40 × 0.15 × 0.05 mm |
F(000) = 1280 | |
Data collection top
SuperNova, Single source at offset, Atlas diffractometer | 5691 independent reflections |
Radiation source: sealed X-ray tube | 5438 reflections with I > 2σ(I) |
Detector resolution: 10.5357 pixels mm-1 | Rint = 0.022 |
ω scans | θmax = 68.2°, θmin = 6.5° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, 2014
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −15→12 |
Tmin = 0.682, Tmax = 1.000 | k = −16→16 |
10943 measured reflections | l = −22→20 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0635P)2 + 0.446P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.22 e Å−3 |
5691 reflections | Δρmin = −0.14 e Å−3 |
387 parameters | Absolute structure: Flack x determined using 2127 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: −0.17 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.7055 (3) | 0.8239 (2) | 0.59632 (14) | 0.0759 (8) | |
O3 | 0.65653 (14) | −0.16649 (15) | 0.82861 (11) | 0.0482 (5) | |
H3 | 0.5942 | −0.1846 | 0.8296 | 0.072* | |
O11 | 0.54649 (13) | 0.26264 (14) | 0.67741 (11) | 0.0443 (5) | |
O30 | 0.56396 (13) | 0.51804 (13) | 0.41113 (11) | 0.0436 (4) | |
O31 | 0.67502 (17) | 0.62859 (14) | 0.36686 (11) | 0.0479 (5) | |
N1 | 0.59212 (19) | 0.67066 (18) | 0.52715 (13) | 0.0454 (5) | |
C1 | 0.59145 (16) | 0.06262 (18) | 0.72404 (14) | 0.0323 (5) | |
H1A | 0.5325 | 0.1087 | 0.7282 | 0.039* | |
H1B | 0.5885 | 0.0328 | 0.6755 | 0.039* | |
C2 | 0.57917 (18) | −0.01746 (19) | 0.78058 (14) | 0.0360 (5) | |
H2A | 0.5763 | 0.0125 | 0.8291 | 0.043* | |
H2B | 0.5130 | −0.0526 | 0.7724 | 0.043* | |
C3 | 0.66826 (18) | −0.08905 (19) | 0.77751 (14) | 0.0353 (5) | |
H3A | 0.6683 | −0.1190 | 0.7284 | 0.042* | |
C4 | 0.77514 (19) | −0.0410 (2) | 0.78898 (13) | 0.0374 (6) | |
C5 | 0.78438 (16) | 0.04375 (18) | 0.73321 (12) | 0.0304 (5) | |
H5 | 0.7811 | 0.0109 | 0.6852 | 0.037* | |
C6 | 0.89021 (18) | 0.0948 (2) | 0.73423 (15) | 0.0400 (6) | |
H6A | 0.8936 | 0.1402 | 0.7757 | 0.048* | |
H6B | 0.9460 | 0.0456 | 0.7400 | 0.048* | |
C7 | 0.90666 (17) | 0.15134 (19) | 0.66429 (14) | 0.0365 (6) | |
H7A | 0.9098 | 0.1044 | 0.6238 | 0.044* | |
H7B | 0.9745 | 0.1853 | 0.6667 | 0.044* | |
C8 | 0.82130 (16) | 0.22695 (17) | 0.64859 (12) | 0.0269 (4) | |
C9 | 0.71170 (15) | 0.18159 (16) | 0.66134 (11) | 0.0254 (4) | |
H9 | 0.7032 | 0.1335 | 0.6213 | 0.030* | |
C10 | 0.69436 (17) | 0.11999 (17) | 0.73160 (12) | 0.0287 (5) | |
C11 | 0.63024 (17) | 0.25991 (18) | 0.64599 (14) | 0.0319 (5) | |
C12 | 0.65425 (17) | 0.33248 (17) | 0.59067 (14) | 0.0329 (5) | |
H12 | 0.6022 | 0.3794 | 0.5796 | 0.039* | |
C13 | 0.74432 (16) | 0.33788 (16) | 0.55426 (12) | 0.0274 (5) | |
C14 | 0.82829 (16) | 0.26092 (16) | 0.56725 (12) | 0.0273 (4) | |
C15 | 0.93950 (17) | 0.29838 (18) | 0.54945 (13) | 0.0336 (5) | |
H15A | 0.9676 | 0.3323 | 0.5923 | 0.040* | |
H15B | 0.9847 | 0.2414 | 0.5397 | 0.040* | |
C16 | 0.94485 (18) | 0.36783 (19) | 0.48508 (14) | 0.0356 (5) | |
H16A | 0.9268 | 0.3315 | 0.4407 | 0.043* | |
H16B | 1.0169 | 0.3921 | 0.4799 | 0.043* | |
C17 | 0.87087 (17) | 0.45539 (18) | 0.49318 (13) | 0.0331 (5) | |
C18 | 0.75794 (17) | 0.41645 (17) | 0.49728 (13) | 0.0304 (5) | |
H18 | 0.7129 | 0.4726 | 0.5117 | 0.036* | |
C19 | 0.71744 (17) | 0.37979 (18) | 0.42417 (13) | 0.0327 (5) | |
H19A | 0.7583 | 0.3220 | 0.4093 | 0.039* | |
H19B | 0.6441 | 0.3592 | 0.4295 | 0.039* | |
C20 | 0.72453 (18) | 0.45806 (19) | 0.36519 (13) | 0.0346 (5) | |
C21 | 0.83798 (19) | 0.4914 (2) | 0.35856 (14) | 0.0398 (6) | |
H21A | 0.8807 | 0.4363 | 0.3409 | 0.048* | |
H21B | 0.8425 | 0.5447 | 0.3227 | 0.048* | |
C22 | 0.88161 (19) | 0.52706 (19) | 0.43020 (15) | 0.0401 (6) | |
H22A | 0.8460 | 0.5886 | 0.4433 | 0.048* | |
H22B | 0.9562 | 0.5423 | 0.4236 | 0.048* | |
C24 | 0.7892 (2) | −0.0093 (3) | 0.86776 (15) | 0.0526 (8) | |
H24A | 0.7291 | 0.0295 | 0.8829 | 0.079* | |
H24B | 0.8524 | 0.0301 | 0.8722 | 0.079* | |
H24C | 0.7950 | −0.0673 | 0.8984 | 0.079* | |
C23 | 0.8578 (2) | −0.1188 (2) | 0.7717 (2) | 0.0545 (8) | |
H23A | 0.9268 | −0.0936 | 0.7838 | 0.082* | |
H23B | 0.8552 | −0.1347 | 0.7202 | 0.082* | |
H23C | 0.8439 | −0.1778 | 0.8000 | 0.082* | |
C25 | 0.6878 (2) | 0.1845 (2) | 0.79958 (13) | 0.0409 (6) | |
H25A | 0.6512 | 0.2452 | 0.7880 | 0.061* | |
H25B | 0.7581 | 0.1997 | 0.8165 | 0.061* | |
H25C | 0.6500 | 0.1495 | 0.8374 | 0.061* | |
C26 | 0.8385 (2) | 0.3136 (2) | 0.70017 (13) | 0.0378 (5) | |
H26A | 0.8478 | 0.2891 | 0.7493 | 0.057* | |
H26B | 0.7779 | 0.3569 | 0.6986 | 0.057* | |
H26C | 0.9006 | 0.3498 | 0.6854 | 0.057* | |
C27 | 0.8048 (2) | 0.17678 (18) | 0.51343 (13) | 0.0354 (5) | |
H27A | 0.7300 | 0.1635 | 0.5130 | 0.053* | |
H27B | 0.8423 | 0.1179 | 0.5283 | 0.053* | |
H27C | 0.8274 | 0.1959 | 0.4650 | 0.053* | |
C28 | 0.8964 (2) | 0.5116 (2) | 0.56228 (16) | 0.0442 (6) | |
H28A | 0.8824 | 0.4701 | 0.6042 | 0.066* | |
H28B | 0.8533 | 0.5705 | 0.5649 | 0.066* | |
H28C | 0.9700 | 0.5302 | 0.5620 | 0.066* | |
C29 | 0.6894 (2) | 0.4154 (2) | 0.29241 (14) | 0.0406 (6) | |
H29A | 0.6176 | 0.3921 | 0.2965 | 0.061* | |
H29B | 0.7349 | 0.3609 | 0.2792 | 0.061* | |
H29C | 0.6933 | 0.4662 | 0.2553 | 0.061* | |
C30 | 0.6546 (2) | 0.54522 (19) | 0.38143 (13) | 0.0364 (5) | |
C31 | 0.4901 (2) | 0.5939 (2) | 0.42854 (19) | 0.0516 (7) | |
H31A | 0.4190 | 0.5710 | 0.4172 | 0.062* | |
H31B | 0.5045 | 0.6523 | 0.3987 | 0.062* | |
C32 | 0.4964 (2) | 0.6209 (2) | 0.5071 (2) | 0.0550 (8) | |
H32A | 0.4368 | 0.6637 | 0.5191 | 0.066* | |
H32B | 0.4898 | 0.5608 | 0.5364 | 0.066* | |
C33 | 0.6019 (3) | 0.6775 (3) | 0.60549 (18) | 0.0643 (9) | |
H33A | 0.6015 | 0.6111 | 0.6265 | 0.077* | |
H33B | 0.5417 | 0.7137 | 0.6252 | 0.077* | |
C34 | 0.6992 (4) | 0.7281 (3) | 0.6259 (2) | 0.0784 (13) | |
H34A | 0.7034 | 0.7322 | 0.6790 | 0.094* | |
H34B | 0.7592 | 0.6893 | 0.6088 | 0.094* | |
C35 | 0.6954 (4) | 0.8181 (3) | 0.5207 (2) | 0.0730 (11) | |
H35A | 0.7553 | 0.7816 | 0.5009 | 0.088* | |
H35B | 0.6972 | 0.8848 | 0.5003 | 0.088* | |
C36 | 0.5966 (3) | 0.7687 (2) | 0.49781 (18) | 0.0533 (7) | |
H36A | 0.5362 | 0.8068 | 0.5150 | 0.064* | |
H36B | 0.5934 | 0.7658 | 0.4446 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.102 (2) | 0.0663 (15) | 0.0596 (14) | 0.0007 (15) | −0.0148 (14) | −0.0175 (13) |
O3 | 0.0340 (9) | 0.0529 (11) | 0.0577 (11) | −0.0136 (8) | −0.0102 (8) | 0.0256 (10) |
O11 | 0.0283 (8) | 0.0441 (10) | 0.0605 (12) | 0.0082 (7) | 0.0156 (8) | 0.0080 (9) |
O30 | 0.0321 (9) | 0.0384 (9) | 0.0604 (12) | 0.0019 (7) | −0.0014 (9) | −0.0001 (9) |
O31 | 0.0588 (12) | 0.0384 (10) | 0.0464 (10) | 0.0005 (9) | 0.0061 (9) | 0.0099 (8) |
N1 | 0.0477 (12) | 0.0450 (12) | 0.0435 (12) | 0.0066 (11) | 0.0076 (10) | 0.0035 (11) |
C1 | 0.0203 (9) | 0.0370 (12) | 0.0394 (12) | −0.0036 (9) | −0.0017 (9) | 0.0021 (11) |
C2 | 0.0265 (10) | 0.0426 (13) | 0.0389 (13) | −0.0089 (10) | −0.0005 (9) | 0.0016 (11) |
C3 | 0.0308 (11) | 0.0380 (12) | 0.0370 (12) | −0.0076 (10) | −0.0063 (10) | 0.0080 (11) |
C4 | 0.0283 (11) | 0.0477 (14) | 0.0363 (12) | −0.0081 (10) | −0.0063 (10) | 0.0142 (11) |
C5 | 0.0219 (10) | 0.0400 (12) | 0.0294 (10) | −0.0029 (9) | −0.0030 (8) | 0.0057 (10) |
C6 | 0.0225 (10) | 0.0534 (15) | 0.0442 (14) | −0.0067 (10) | −0.0061 (10) | 0.0170 (13) |
C7 | 0.0194 (10) | 0.0467 (14) | 0.0435 (13) | 0.0017 (10) | 0.0002 (9) | 0.0138 (12) |
C8 | 0.0201 (9) | 0.0336 (11) | 0.0271 (10) | −0.0016 (8) | 0.0002 (8) | 0.0004 (9) |
C9 | 0.0200 (9) | 0.0293 (10) | 0.0269 (10) | 0.0003 (8) | 0.0006 (8) | −0.0037 (9) |
C10 | 0.0231 (10) | 0.0344 (11) | 0.0286 (10) | −0.0062 (9) | 0.0016 (8) | −0.0023 (9) |
C11 | 0.0224 (10) | 0.0335 (11) | 0.0399 (12) | 0.0013 (9) | 0.0031 (9) | −0.0039 (10) |
C12 | 0.0231 (10) | 0.0313 (11) | 0.0442 (13) | 0.0049 (9) | 0.0024 (9) | 0.0018 (10) |
C13 | 0.0236 (9) | 0.0270 (10) | 0.0316 (11) | −0.0002 (8) | −0.0016 (8) | −0.0028 (9) |
C14 | 0.0219 (9) | 0.0313 (11) | 0.0287 (10) | 0.0028 (9) | 0.0022 (8) | −0.0011 (9) |
C15 | 0.0216 (10) | 0.0411 (13) | 0.0380 (13) | 0.0026 (9) | 0.0046 (9) | 0.0064 (11) |
C16 | 0.0229 (10) | 0.0424 (13) | 0.0415 (13) | 0.0015 (9) | 0.0034 (10) | 0.0061 (11) |
C17 | 0.0266 (10) | 0.0334 (11) | 0.0394 (12) | −0.0038 (9) | 0.0006 (9) | 0.0030 (11) |
C18 | 0.0257 (10) | 0.0283 (10) | 0.0373 (12) | 0.0010 (9) | −0.0002 (9) | 0.0014 (10) |
C19 | 0.0271 (10) | 0.0333 (11) | 0.0376 (12) | −0.0011 (9) | −0.0017 (9) | 0.0040 (10) |
C20 | 0.0302 (11) | 0.0376 (12) | 0.0361 (12) | −0.0012 (10) | −0.0002 (10) | 0.0061 (10) |
C21 | 0.0309 (12) | 0.0458 (14) | 0.0427 (13) | −0.0029 (11) | 0.0032 (11) | 0.0119 (12) |
C22 | 0.0300 (11) | 0.0400 (13) | 0.0504 (15) | −0.0068 (10) | −0.0016 (11) | 0.0084 (12) |
C24 | 0.0466 (15) | 0.073 (2) | 0.0382 (14) | −0.0285 (15) | −0.0164 (12) | 0.0202 (14) |
C23 | 0.0318 (12) | 0.0584 (17) | 0.073 (2) | 0.0058 (12) | −0.0005 (13) | 0.0321 (16) |
C25 | 0.0462 (13) | 0.0456 (14) | 0.0309 (11) | −0.0136 (12) | 0.0097 (11) | −0.0071 (11) |
C26 | 0.0380 (12) | 0.0442 (13) | 0.0312 (11) | −0.0136 (11) | −0.0003 (10) | −0.0033 (11) |
C27 | 0.0438 (13) | 0.0323 (11) | 0.0301 (11) | 0.0051 (10) | 0.0041 (10) | −0.0007 (10) |
C28 | 0.0410 (13) | 0.0403 (14) | 0.0513 (15) | −0.0068 (11) | −0.0053 (12) | −0.0023 (13) |
C29 | 0.0407 (12) | 0.0442 (14) | 0.0368 (13) | −0.0007 (11) | 0.0023 (11) | 0.0037 (11) |
C30 | 0.0400 (12) | 0.0380 (13) | 0.0313 (11) | −0.0021 (11) | −0.0049 (10) | 0.0062 (10) |
C31 | 0.0343 (13) | 0.0474 (15) | 0.073 (2) | 0.0043 (12) | −0.0062 (13) | −0.0056 (15) |
C32 | 0.0418 (14) | 0.0516 (16) | 0.072 (2) | 0.0044 (13) | 0.0165 (15) | −0.0002 (16) |
C33 | 0.098 (3) | 0.0476 (16) | 0.0469 (17) | 0.0147 (18) | 0.0105 (17) | 0.0026 (14) |
C34 | 0.116 (3) | 0.059 (2) | 0.060 (2) | 0.031 (2) | −0.031 (2) | −0.0194 (17) |
C35 | 0.092 (3) | 0.070 (2) | 0.0564 (19) | −0.027 (2) | 0.0067 (19) | −0.0109 (18) |
C36 | 0.0649 (18) | 0.0475 (16) | 0.0474 (16) | 0.0018 (14) | −0.0003 (14) | 0.0025 (14) |
Geometric parameters (Å, º) top
O1—C35 | 1.412 (4) | C17—C28 | 1.532 (4) |
O1—C34 | 1.425 (5) | C17—C22 | 1.533 (3) |
O3—C3 | 1.431 (3) | C17—C18 | 1.550 (3) |
O3—H3 | 0.8400 | C18—C19 | 1.539 (3) |
O11—C11 | 1.226 (3) | C18—H18 | 1.0000 |
O30—C30 | 1.343 (3) | C19—C20 | 1.535 (3) |
O30—C31 | 1.445 (3) | C19—H19A | 0.9900 |
O31—C30 | 1.203 (3) | C19—H19B | 0.9900 |
N1—C36 | 1.450 (4) | C20—C30 | 1.525 (4) |
N1—C32 | 1.456 (4) | C20—C21 | 1.535 (3) |
N1—C33 | 1.463 (4) | C20—C29 | 1.540 (4) |
C1—C2 | 1.527 (3) | C21—C22 | 1.524 (4) |
C1—C10 | 1.547 (3) | C21—H21A | 0.9900 |
C1—H1A | 0.9900 | C21—H21B | 0.9900 |
C1—H1B | 0.9900 | C22—H22A | 0.9900 |
C2—C3 | 1.510 (4) | C22—H22B | 0.9900 |
C2—H2A | 0.9900 | C24—H24A | 0.9800 |
C2—H2B | 0.9900 | C24—H24B | 0.9800 |
C3—C4 | 1.540 (3) | C24—H24C | 0.9800 |
C3—H3A | 1.0000 | C23—H23A | 0.9800 |
C4—C24 | 1.536 (4) | C23—H23B | 0.9800 |
C4—C23 | 1.540 (4) | C23—H23C | 0.9800 |
C4—C5 | 1.560 (3) | C25—H25A | 0.9800 |
C5—C6 | 1.531 (3) | C25—H25B | 0.9800 |
C5—C10 | 1.560 (3) | C25—H25C | 0.9800 |
C5—H5 | 1.0000 | C26—H26A | 0.9800 |
C6—C7 | 1.527 (3) | C26—H26B | 0.9800 |
C6—H6A | 0.9900 | C26—H26C | 0.9800 |
C6—H6B | 0.9900 | C27—H27A | 0.9800 |
C7—C8 | 1.538 (3) | C27—H27B | 0.9800 |
C7—H7A | 0.9900 | C27—H27C | 0.9800 |
C7—H7B | 0.9900 | C28—H28A | 0.9800 |
C8—C26 | 1.541 (3) | C28—H28B | 0.9800 |
C8—C9 | 1.559 (3) | C28—H28C | 0.9800 |
C8—C14 | 1.583 (3) | C29—H29A | 0.9800 |
C9—C11 | 1.527 (3) | C29—H29B | 0.9800 |
C9—C10 | 1.570 (3) | C29—H29C | 0.9800 |
C9—H9 | 1.0000 | C31—C32 | 1.508 (5) |
C10—C25 | 1.543 (3) | C31—H31A | 0.9900 |
C11—C12 | 1.462 (3) | C31—H31B | 0.9900 |
C12—C13 | 1.344 (3) | C32—H32A | 0.9900 |
C12—H12 | 0.9500 | C32—H32B | 0.9900 |
C13—C18 | 1.519 (3) | C33—C34 | 1.480 (6) |
C13—C14 | 1.529 (3) | C33—H33A | 0.9900 |
C14—C27 | 1.555 (3) | C33—H33B | 0.9900 |
C14—C15 | 1.556 (3) | C34—H34A | 0.9900 |
C15—C16 | 1.529 (3) | C34—H34B | 0.9900 |
C15—H15A | 0.9900 | C35—C36 | 1.502 (5) |
C15—H15B | 0.9900 | C35—H35A | 0.9900 |
C16—C17 | 1.539 (3) | C35—H35B | 0.9900 |
C16—H16A | 0.9900 | C36—H36A | 0.9900 |
C16—H16B | 0.9900 | C36—H36B | 0.9900 |
| | | |
C35—O1—C34 | 109.0 (3) | C20—C19—C18 | 112.42 (19) |
C3—O3—H3 | 109.5 | C20—C19—H19A | 109.1 |
C30—O30—C31 | 117.6 (2) | C18—C19—H19A | 109.1 |
C36—N1—C32 | 111.8 (3) | C20—C19—H19B | 109.1 |
C36—N1—C33 | 108.1 (3) | C18—C19—H19B | 109.1 |
C32—N1—C33 | 110.9 (3) | H19A—C19—H19B | 107.9 |
C2—C1—C10 | 113.04 (19) | C30—C20—C21 | 110.1 (2) |
C2—C1—H1A | 109.0 | C30—C20—C19 | 111.8 (2) |
C10—C1—H1A | 109.0 | C21—C20—C19 | 108.74 (19) |
C2—C1—H1B | 109.0 | C30—C20—C29 | 107.3 (2) |
C10—C1—H1B | 109.0 | C21—C20—C29 | 108.8 (2) |
H1A—C1—H1B | 107.8 | C19—C20—C29 | 110.1 (2) |
C3—C2—C1 | 111.2 (2) | C22—C21—C20 | 112.1 (2) |
C3—C2—H2A | 109.4 | C22—C21—H21A | 109.2 |
C1—C2—H2A | 109.4 | C20—C21—H21A | 109.2 |
C3—C2—H2B | 109.4 | C22—C21—H21B | 109.2 |
C1—C2—H2B | 109.4 | C20—C21—H21B | 109.2 |
H2A—C2—H2B | 108.0 | H21A—C21—H21B | 107.9 |
O3—C3—C2 | 112.1 (2) | C21—C22—C17 | 115.3 (2) |
O3—C3—C4 | 108.63 (18) | C21—C22—H22A | 108.5 |
C2—C3—C4 | 113.3 (2) | C17—C22—H22A | 108.5 |
O3—C3—H3A | 107.5 | C21—C22—H22B | 108.5 |
C2—C3—H3A | 107.5 | C17—C22—H22B | 108.5 |
C4—C3—H3A | 107.5 | H22A—C22—H22B | 107.5 |
C24—C4—C3 | 110.9 (2) | C4—C24—H24A | 109.5 |
C24—C4—C23 | 108.2 (2) | C4—C24—H24B | 109.5 |
C3—C4—C23 | 107.0 (2) | H24A—C24—H24B | 109.5 |
C24—C4—C5 | 114.4 (2) | C4—C24—H24C | 109.5 |
C3—C4—C5 | 107.12 (18) | H24A—C24—H24C | 109.5 |
C23—C4—C5 | 108.9 (2) | H24B—C24—H24C | 109.5 |
C6—C5—C4 | 113.53 (19) | C4—C23—H23A | 109.5 |
C6—C5—C10 | 110.8 (2) | C4—C23—H23B | 109.5 |
C4—C5—C10 | 117.01 (19) | H23A—C23—H23B | 109.5 |
C6—C5—H5 | 104.7 | C4—C23—H23C | 109.5 |
C4—C5—H5 | 104.7 | H23A—C23—H23C | 109.5 |
C10—C5—H5 | 104.7 | H23B—C23—H23C | 109.5 |
C7—C6—C5 | 110.14 (19) | C10—C25—H25A | 109.5 |
C7—C6—H6A | 109.6 | C10—C25—H25B | 109.5 |
C5—C6—H6A | 109.6 | H25A—C25—H25B | 109.5 |
C7—C6—H6B | 109.6 | C10—C25—H25C | 109.5 |
C5—C6—H6B | 109.6 | H25A—C25—H25C | 109.5 |
H6A—C6—H6B | 108.1 | H25B—C25—H25C | 109.5 |
C6—C7—C8 | 113.8 (2) | C8—C26—H26A | 109.5 |
C6—C7—H7A | 108.8 | C8—C26—H26B | 109.5 |
C8—C7—H7A | 108.8 | H26A—C26—H26B | 109.5 |
C6—C7—H7B | 108.8 | C8—C26—H26C | 109.5 |
C8—C7—H7B | 108.8 | H26A—C26—H26C | 109.5 |
H7A—C7—H7B | 107.7 | H26B—C26—H26C | 109.5 |
C7—C8—C26 | 107.37 (19) | C14—C27—H27A | 109.5 |
C7—C8—C9 | 110.44 (18) | C14—C27—H27B | 109.5 |
C26—C8—C9 | 110.02 (18) | H27A—C27—H27B | 109.5 |
C7—C8—C14 | 109.77 (18) | C14—C27—H27C | 109.5 |
C26—C8—C14 | 111.00 (19) | H27A—C27—H27C | 109.5 |
C9—C8—C14 | 108.26 (16) | H27B—C27—H27C | 109.5 |
C11—C9—C8 | 108.24 (18) | C17—C28—H28A | 109.5 |
C11—C9—C10 | 115.80 (18) | C17—C28—H28B | 109.5 |
C8—C9—C10 | 117.96 (17) | H28A—C28—H28B | 109.5 |
C11—C9—H9 | 104.4 | C17—C28—H28C | 109.5 |
C8—C9—H9 | 104.4 | H28A—C28—H28C | 109.5 |
C10—C9—H9 | 104.4 | H28B—C28—H28C | 109.5 |
C25—C10—C1 | 108.58 (18) | C20—C29—H29A | 109.5 |
C25—C10—C5 | 114.1 (2) | C20—C29—H29B | 109.5 |
C1—C10—C5 | 107.31 (18) | H29A—C29—H29B | 109.5 |
C25—C10—C9 | 112.34 (18) | C20—C29—H29C | 109.5 |
C1—C10—C9 | 108.63 (18) | H29A—C29—H29C | 109.5 |
C5—C10—C9 | 105.68 (17) | H29B—C29—H29C | 109.5 |
O11—C11—C12 | 119.9 (2) | O31—C30—O30 | 123.0 (2) |
O11—C11—C9 | 122.4 (2) | O31—C30—C20 | 124.8 (2) |
C12—C11—C9 | 117.62 (18) | O30—C30—C20 | 112.1 (2) |
C13—C12—C11 | 125.0 (2) | O30—C31—C32 | 111.0 (2) |
C13—C12—H12 | 117.5 | O30—C31—H31A | 109.4 |
C11—C12—H12 | 117.5 | C32—C31—H31A | 109.4 |
C12—C13—C18 | 119.3 (2) | O30—C31—H31B | 109.4 |
C12—C13—C14 | 119.5 (2) | C32—C31—H31B | 109.4 |
C18—C13—C14 | 121.12 (18) | H31A—C31—H31B | 108.0 |
C13—C14—C27 | 105.79 (18) | N1—C32—C31 | 114.0 (2) |
C13—C14—C15 | 112.91 (18) | N1—C32—H32A | 108.7 |
C27—C14—C15 | 106.65 (18) | C31—C32—H32A | 108.7 |
C13—C14—C8 | 108.25 (17) | N1—C32—H32B | 108.7 |
C27—C14—C8 | 112.60 (18) | C31—C32—H32B | 108.7 |
C15—C14—C8 | 110.60 (17) | H32A—C32—H32B | 107.6 |
C16—C15—C14 | 114.37 (18) | N1—C33—C34 | 110.9 (3) |
C16—C15—H15A | 108.7 | N1—C33—H33A | 109.5 |
C14—C15—H15A | 108.7 | C34—C33—H33A | 109.5 |
C16—C15—H15B | 108.7 | N1—C33—H33B | 109.5 |
C14—C15—H15B | 108.7 | C34—C33—H33B | 109.5 |
H15A—C15—H15B | 107.6 | H33A—C33—H33B | 108.0 |
C15—C16—C17 | 112.4 (2) | O1—C34—C33 | 112.4 (3) |
C15—C16—H16A | 109.1 | O1—C34—H34A | 109.1 |
C17—C16—H16A | 109.1 | C33—C34—H34A | 109.1 |
C15—C16—H16B | 109.1 | O1—C34—H34B | 109.1 |
C17—C16—H16B | 109.1 | C33—C34—H34B | 109.1 |
H16A—C16—H16B | 107.9 | H34A—C34—H34B | 107.9 |
C28—C17—C22 | 107.3 (2) | O1—C35—C36 | 112.6 (3) |
C28—C17—C16 | 109.9 (2) | O1—C35—H35A | 109.1 |
C22—C17—C16 | 111.6 (2) | C36—C35—H35A | 109.1 |
C28—C17—C18 | 109.5 (2) | O1—C35—H35B | 109.1 |
C22—C17—C18 | 110.02 (19) | C36—C35—H35B | 109.1 |
C16—C17—C18 | 108.47 (19) | H35A—C35—H35B | 107.8 |
C13—C18—C19 | 110.13 (18) | N1—C36—C35 | 110.1 (3) |
C13—C18—C17 | 112.72 (18) | N1—C36—H36A | 109.6 |
C19—C18—C17 | 112.74 (19) | C35—C36—H36A | 109.6 |
C13—C18—H18 | 107.0 | N1—C36—H36B | 109.6 |
C19—C18—H18 | 107.0 | C35—C36—H36B | 109.6 |
C17—C18—H18 | 107.0 | H36A—C36—H36B | 108.1 |
| | | |
C10—C1—C2—C3 | −57.7 (3) | C26—C8—C14—C13 | −60.0 (2) |
C1—C2—C3—O3 | −178.2 (2) | C9—C8—C14—C13 | 60.9 (2) |
C1—C2—C3—C4 | 58.5 (3) | C7—C8—C14—C27 | 64.9 (2) |
O3—C3—C4—C24 | −53.7 (3) | C26—C8—C14—C27 | −176.56 (18) |
C2—C3—C4—C24 | 71.6 (3) | C9—C8—C14—C27 | −55.7 (2) |
O3—C3—C4—C23 | 64.1 (3) | C7—C8—C14—C15 | −54.3 (2) |
C2—C3—C4—C23 | −170.6 (2) | C26—C8—C14—C15 | 64.2 (2) |
O3—C3—C4—C5 | −179.2 (2) | C9—C8—C14—C15 | −174.93 (18) |
C2—C3—C4—C5 | −53.9 (3) | C13—C14—C15—C16 | −35.7 (3) |
C24—C4—C5—C6 | 60.6 (3) | C27—C14—C15—C16 | 80.0 (2) |
C3—C4—C5—C6 | −176.0 (2) | C8—C14—C15—C16 | −157.2 (2) |
C23—C4—C5—C6 | −60.7 (3) | C14—C15—C16—C17 | 54.4 (3) |
C24—C4—C5—C10 | −70.5 (3) | C15—C16—C17—C28 | 57.9 (3) |
C3—C4—C5—C10 | 52.9 (3) | C15—C16—C17—C22 | 176.9 (2) |
C23—C4—C5—C10 | 168.3 (2) | C15—C16—C17—C18 | −61.7 (3) |
C4—C5—C6—C7 | 161.3 (2) | C12—C13—C18—C19 | −87.6 (3) |
C10—C5—C6—C7 | −64.7 (3) | C14—C13—C18—C19 | 88.3 (2) |
C5—C6—C7—C8 | 56.9 (3) | C12—C13—C18—C17 | 145.6 (2) |
C6—C7—C8—C26 | 74.2 (3) | C14—C13—C18—C17 | −38.6 (3) |
C6—C7—C8—C9 | −45.8 (3) | C28—C17—C18—C13 | −67.6 (3) |
C6—C7—C8—C14 | −165.1 (2) | C22—C17—C18—C13 | 174.7 (2) |
C7—C8—C9—C11 | 179.27 (19) | C16—C17—C18—C13 | 52.3 (3) |
C26—C8—C9—C11 | 60.9 (2) | C28—C17—C18—C19 | 166.9 (2) |
C14—C8—C9—C11 | −60.5 (2) | C22—C17—C18—C19 | 49.2 (3) |
C7—C8—C9—C10 | 45.3 (3) | C16—C17—C18—C19 | −73.2 (2) |
C26—C8—C9—C10 | −73.0 (2) | C13—C18—C19—C20 | 177.30 (18) |
C14—C8—C9—C10 | 165.54 (18) | C17—C18—C19—C20 | −55.9 (3) |
C2—C1—C10—C25 | −71.2 (3) | C18—C19—C20—C30 | −64.4 (3) |
C2—C1—C10—C5 | 52.6 (3) | C18—C19—C20—C21 | 57.4 (3) |
C2—C1—C10—C9 | 166.40 (19) | C18—C19—C20—C29 | 176.5 (2) |
C6—C5—C10—C25 | −64.5 (2) | C30—C20—C21—C22 | 67.3 (3) |
C4—C5—C10—C25 | 67.9 (3) | C19—C20—C21—C22 | −55.5 (3) |
C6—C5—C10—C1 | 175.23 (19) | C29—C20—C21—C22 | −175.4 (2) |
C4—C5—C10—C1 | −52.5 (3) | C20—C21—C22—C17 | 53.6 (3) |
C6—C5—C10—C9 | 59.4 (2) | C28—C17—C22—C21 | −167.9 (2) |
C4—C5—C10—C9 | −168.25 (19) | C16—C17—C22—C21 | 71.6 (3) |
C11—C9—C10—C25 | −57.1 (3) | C18—C17—C22—C21 | −48.9 (3) |
C8—C9—C10—C25 | 73.4 (2) | C31—O30—C30—O31 | −2.4 (4) |
C11—C9—C10—C1 | 63.0 (2) | C31—O30—C30—C20 | −179.4 (2) |
C8—C9—C10—C1 | −166.43 (18) | C21—C20—C30—O31 | 24.0 (4) |
C11—C9—C10—C5 | 177.90 (18) | C19—C20—C30—O31 | 145.0 (2) |
C8—C9—C10—C5 | −51.5 (2) | C29—C20—C30—O31 | −94.2 (3) |
C8—C9—C11—O11 | −149.0 (2) | C21—C20—C30—O30 | −159.0 (2) |
C10—C9—C11—O11 | −14.0 (3) | C19—C20—C30—O30 | −38.0 (3) |
C8—C9—C11—C12 | 32.0 (3) | C29—C20—C30—O30 | 82.7 (2) |
C10—C9—C11—C12 | 167.1 (2) | C30—O30—C31—C32 | −98.1 (3) |
O11—C11—C12—C13 | 178.2 (2) | C36—N1—C32—C31 | 70.4 (3) |
C9—C11—C12—C13 | −2.8 (4) | C33—N1—C32—C31 | −169.0 (3) |
C11—C12—C13—C18 | 179.1 (2) | O30—C31—C32—N1 | 68.8 (3) |
C11—C12—C13—C14 | 3.2 (4) | C36—N1—C33—C34 | −57.2 (4) |
C12—C13—C14—C27 | 88.7 (2) | C32—N1—C33—C34 | 180.0 (3) |
C18—C13—C14—C27 | −87.2 (2) | C35—O1—C34—C33 | −56.6 (5) |
C12—C13—C14—C15 | −155.0 (2) | N1—C33—C34—O1 | 58.3 (4) |
C18—C13—C14—C15 | 29.1 (3) | C34—O1—C35—C36 | 56.7 (5) |
C12—C13—C14—C8 | −32.2 (3) | C32—N1—C36—C35 | 179.0 (3) |
C18—C13—C14—C8 | 151.92 (19) | C33—N1—C36—C35 | 56.7 (4) |
C7—C8—C14—C13 | −178.50 (18) | O1—C35—C36—N1 | −58.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O11i | 0.84 | 1.95 | 2.790 (2) | 173 |
Symmetry code: (i) −x+1, y−1/2, −z+3/2. |