Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616008180/fx5001sup1.cif
Contains datablocks 4, 5, 6, block_global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616008180/fx50014sup2.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616008180/fx50015sup3.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616008180/fx50016sup4.hkl
Contains datablock 6

CCDC references: 1480870; 1480871; 1480872

Computing details top

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
C32H50O4Dx = 1.196 Mg m3
Mr = 498.72Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3007 reflections
a = 12.9577 (5) Åθ = 3.5–28.7°
b = 13.0369 (4) ŵ = 0.08 mm1
c = 16.3908 (5) ÅT = 130 K
V = 2768.87 (16) Å3Plate, colorless
Z = 40.60 × 0.20 × 0.15 mm
F(000) = 1096
Data collection top
Xcalibur, Eos
diffractometer
4597 independent reflections
Radiation source: Enhance (Mo) X-ray Source3513 reflections with I > 2σ(I)
Detector resolution: 16.1544 pixels mm-1Rint = 0.038
ω scansθmax = 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 = 1515
Tmin = 0.885, Tmax = 1.000k = 1515
9373 measured reflectionsl = 1919
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 0.92Δρmax = 0.17 e Å3
4597 reflectionsΔρmin = 0.20 e Å3
334 parametersAbsolute structure: Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O30.62524 (15)0.27111 (16)0.75263 (16)0.0324 (6)
H30.56150.28270.75220.049*
O110.60802 (15)0.23850 (15)0.72977 (13)0.0252 (6)
O300.60960 (14)0.59512 (15)0.47474 (13)0.0234 (5)
O310.72376 (16)0.70751 (17)0.42517 (15)0.0416 (7)
C10.6060 (2)0.0141 (2)0.71619 (18)0.0183 (7)
H1A0.56520.06770.74440.022*
H1B0.58210.01090.65890.022*
C20.5860 (2)0.0887 (2)0.75694 (19)0.0198 (8)
H2A0.60690.08500.81500.024*
H2B0.51120.10420.75490.024*
C30.6453 (2)0.1736 (2)0.71516 (19)0.0212 (8)
H3A0.62050.17740.65740.025*
C40.7627 (2)0.1560 (2)0.71300 (18)0.0177 (7)
C50.7833 (2)0.0462 (2)0.67933 (18)0.0151 (7)
H50.76010.04890.62120.018*
C60.8983 (2)0.0186 (2)0.67482 (18)0.0170 (7)
H6A0.92370.00100.73000.020*
H6B0.93790.07870.65520.020*
C70.9162 (2)0.0719 (2)0.61751 (18)0.0182 (7)
H7A0.90020.05000.56110.022*
H7B0.99020.09070.61930.022*
C80.8516 (2)0.1676 (2)0.63759 (18)0.0150 (7)
C90.7376 (2)0.1374 (2)0.65859 (17)0.0135 (7)
H90.70770.11400.60550.016*
C100.7214 (2)0.0448 (2)0.71752 (17)0.0142 (7)
C110.6783 (2)0.2348 (2)0.67915 (18)0.0165 (7)
C120.7044 (2)0.3275 (2)0.63302 (17)0.0169 (7)
H120.66330.38680.64200.020*
C130.7819 (2)0.3352 (2)0.57915 (17)0.0144 (7)
C140.8494 (2)0.2418 (2)0.56074 (18)0.0148 (7)
C150.9613 (2)0.2731 (2)0.53688 (18)0.0174 (7)
H15A1.00180.28380.58740.021*
H15B0.99350.21580.50650.021*
C160.9679 (2)0.3706 (2)0.48463 (18)0.0179 (7)
H16A1.04140.38900.47710.021*
H16B0.93830.35620.43010.021*
C170.9111 (2)0.4619 (2)0.52201 (19)0.0170 (7)
C180.7959 (2)0.4342 (2)0.53182 (17)0.0161 (7)
H180.76340.49000.56480.019*
C190.7381 (2)0.4303 (2)0.44961 (17)0.0173 (7)
H19A0.76390.37090.41790.021*
H19B0.66390.41880.46040.021*
C200.7496 (2)0.5273 (2)0.39749 (18)0.0183 (7)
C210.8643 (2)0.5508 (2)0.38608 (18)0.0206 (8)
H21A0.89620.49620.35250.025*
H21B0.87190.61650.35650.025*
C220.9206 (2)0.5577 (2)0.46731 (18)0.0208 (8)
H22A0.89360.61760.49770.025*
H22B0.99470.57040.45640.025*
C230.8081 (2)0.2357 (2)0.6535 (2)0.0274 (8)
H23A0.88360.23450.65700.041*
H23B0.78670.21910.59770.041*
H23C0.78290.30420.66800.041*
C240.8118 (2)0.1736 (2)0.79646 (18)0.0221 (8)
H24A0.88590.15930.79330.033*
H24B0.80110.24500.81310.033*
H24C0.77980.12770.83650.033*
C250.7511 (2)0.0710 (2)0.80644 (17)0.0178 (7)
H25A0.71580.02390.84370.027*
H25B0.73030.14170.81870.027*
H25C0.82590.06420.81330.027*
C260.9017 (2)0.2208 (2)0.71192 (17)0.0200 (7)
H26A0.85640.27570.73140.030*
H26B0.96840.24990.69590.030*
H26C0.91210.17040.75560.030*
C270.8009 (2)0.1895 (2)0.48505 (17)0.0195 (7)
H27A0.72550.19270.48900.029*
H27B0.82290.11760.48270.029*
H27C0.82360.22510.43550.029*
C280.9576 (2)0.4890 (2)0.60528 (18)0.0241 (8)
H28A1.03180.50150.59920.036*
H28B0.94650.43190.64320.036*
H28C0.92410.55080.62660.036*
C290.7001 (2)0.5087 (2)0.31360 (18)0.0249 (8)
H29A0.62640.49400.32060.037*
H29B0.73370.45030.28710.037*
H29C0.70840.57010.27970.037*
C300.6958 (2)0.6199 (2)0.43409 (19)0.0214 (7)
C310.5513 (2)0.6803 (3)0.5081 (2)0.0291 (9)
H31A0.52040.72100.46330.035*
H31B0.59740.72570.54000.035*
C320.4683 (3)0.6383 (3)0.5617 (2)0.0540 (12)
H32A0.41980.59820.52880.081*
H32B0.43150.69500.58800.081*
H32C0.49920.59420.60350.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0236 (12)0.0177 (13)0.0559 (17)0.0061 (11)0.0038 (13)0.0086 (12)
O110.0213 (11)0.0229 (13)0.0312 (14)0.0047 (10)0.0128 (11)0.0062 (11)
O300.0198 (11)0.0216 (13)0.0288 (13)0.0013 (10)0.0069 (11)0.0030 (10)
O310.0389 (14)0.0196 (14)0.0662 (19)0.0011 (12)0.0214 (14)0.0078 (13)
C10.0140 (16)0.0179 (18)0.0230 (19)0.0024 (14)0.0006 (15)0.0033 (15)
C20.0131 (15)0.0206 (19)0.0258 (19)0.0038 (14)0.0001 (15)0.0040 (15)
C30.0218 (16)0.0164 (17)0.0253 (19)0.0052 (15)0.0001 (15)0.0030 (16)
C40.0161 (15)0.0149 (16)0.0221 (18)0.0012 (14)0.0045 (15)0.0018 (15)
C50.0154 (16)0.0157 (17)0.0141 (17)0.0001 (14)0.0014 (14)0.0010 (14)
C60.0118 (15)0.0180 (18)0.0211 (18)0.0047 (14)0.0020 (15)0.0034 (14)
C70.0145 (15)0.0180 (18)0.0222 (18)0.0026 (14)0.0030 (15)0.0048 (15)
C80.0114 (15)0.0154 (17)0.0181 (18)0.0006 (14)0.0016 (14)0.0020 (15)
C90.0136 (15)0.0145 (16)0.0124 (17)0.0013 (14)0.0014 (13)0.0010 (13)
C100.0110 (15)0.0149 (16)0.0166 (17)0.0017 (13)0.0016 (14)0.0015 (14)
C110.0132 (15)0.0176 (18)0.0186 (18)0.0014 (14)0.0011 (14)0.0004 (15)
C120.0153 (15)0.0145 (17)0.0208 (18)0.0064 (14)0.0005 (15)0.0019 (15)
C130.0113 (14)0.0163 (16)0.0158 (17)0.0028 (13)0.0033 (14)0.0015 (14)
C140.0142 (15)0.0164 (17)0.0138 (17)0.0006 (13)0.0002 (13)0.0022 (14)
C150.0140 (15)0.0189 (18)0.0193 (19)0.0025 (14)0.0033 (14)0.0022 (15)
C160.0127 (15)0.0195 (18)0.0216 (18)0.0015 (14)0.0016 (14)0.0032 (15)
C170.0107 (15)0.0172 (17)0.0231 (18)0.0025 (14)0.0016 (15)0.0040 (15)
C180.0148 (15)0.0155 (16)0.0181 (18)0.0025 (14)0.0019 (14)0.0009 (14)
C190.0131 (15)0.0174 (17)0.0215 (18)0.0016 (14)0.0001 (14)0.0024 (14)
C200.0162 (15)0.0199 (17)0.0189 (18)0.0017 (15)0.0021 (14)0.0045 (14)
C210.0176 (16)0.0192 (18)0.025 (2)0.0001 (14)0.0047 (15)0.0075 (15)
C220.0185 (16)0.0173 (18)0.027 (2)0.0030 (14)0.0031 (16)0.0029 (15)
C230.0296 (18)0.0188 (19)0.034 (2)0.0005 (16)0.0071 (17)0.0011 (16)
C240.0195 (16)0.0177 (18)0.029 (2)0.0025 (15)0.0045 (16)0.0090 (15)
C250.0178 (15)0.0169 (17)0.0185 (18)0.0002 (15)0.0016 (15)0.0002 (14)
C260.0165 (15)0.0217 (18)0.0219 (19)0.0019 (15)0.0028 (15)0.0040 (15)
C270.0224 (16)0.0164 (17)0.0196 (18)0.0009 (15)0.0024 (15)0.0009 (14)
C280.0238 (17)0.021 (2)0.027 (2)0.0012 (15)0.0011 (16)0.0005 (16)
C290.0238 (16)0.028 (2)0.0228 (19)0.0019 (16)0.0007 (17)0.0068 (16)
C300.0155 (16)0.026 (2)0.0231 (19)0.0010 (16)0.0010 (16)0.0073 (16)
C310.0269 (19)0.027 (2)0.034 (2)0.0069 (16)0.0010 (17)0.0089 (17)
C320.052 (2)0.043 (3)0.067 (3)0.002 (2)0.037 (2)0.009 (2)
Geometric parameters (Å, º) top
O3—C31.435 (4)C16—H16A0.9900
O3—H30.8400C16—H16B0.9900
O11—C111.233 (3)C17—C281.533 (4)
O30—C301.340 (3)C17—C221.542 (4)
O30—C311.450 (3)C17—C181.545 (4)
O31—C301.208 (3)C18—C191.542 (4)
C1—C21.520 (4)C18—H181.0000
C1—C101.549 (4)C19—C201.532 (4)
C1—H1A0.9900C19—H19A0.9900
C1—H1B0.9900C19—H19B0.9900
C2—C31.511 (4)C20—C301.518 (4)
C2—H2A0.9900C20—C211.529 (4)
C2—H2B0.9900C20—C291.537 (4)
C3—C41.539 (4)C21—C221.521 (4)
C3—H3A1.0000C21—H21A0.9900
C4—C241.526 (4)C21—H21B0.9900
C4—C231.541 (4)C22—H22A0.9900
C4—C51.557 (4)C22—H22B0.9900
C5—C61.535 (4)C23—H23A0.9800
C5—C101.563 (4)C23—H23B0.9800
C5—H51.0000C23—H23C0.9800
C6—C71.526 (4)C24—H24A0.9800
C6—H6A0.9900C24—H24B0.9800
C6—H6B0.9900C24—H24C0.9800
C7—C81.539 (4)C25—H25A0.9800
C7—H7A0.9900C25—H25B0.9800
C7—H7B0.9900C25—H25C0.9800
C8—C261.544 (4)C26—H26A0.9800
C8—C91.567 (4)C26—H26B0.9800
C8—C141.588 (4)C26—H26C0.9800
C9—C111.522 (4)C27—H27A0.9800
C9—C101.560 (4)C27—H27B0.9800
C9—H91.0000C27—H27C0.9800
C10—C251.546 (4)C28—H28A0.9800
C11—C121.466 (4)C28—H28B0.9800
C12—C131.341 (4)C28—H28C0.9800
C12—H120.9500C29—H29A0.9800
C13—C181.517 (4)C29—H29B0.9800
C13—C141.530 (4)C29—H29C0.9800
C14—C271.549 (4)C31—C321.493 (4)
C14—C151.555 (4)C31—H31A0.9900
C15—C161.535 (4)C31—H31B0.9900
C15—H15A0.9900C32—H32A0.9800
C15—H15B0.9900C32—H32B0.9800
C16—C171.527 (4)C32—H32C0.9800
C3—O3—H3109.5C28—C17—C22107.5 (2)
C30—O30—C31115.9 (2)C16—C17—C18108.9 (2)
C2—C1—C10112.7 (2)C28—C17—C18109.9 (2)
C2—C1—H1A109.0C22—C17—C18109.1 (2)
C10—C1—H1A109.0C13—C18—C19111.2 (2)
C2—C1—H1B109.0C13—C18—C17111.6 (2)
C10—C1—H1B109.0C19—C18—C17112.7 (2)
H1A—C1—H1B107.8C13—C18—H18107.0
C3—C2—C1111.1 (3)C19—C18—H18107.0
C3—C2—H2A109.4C17—C18—H18107.0
C1—C2—H2A109.4C20—C19—C18114.4 (2)
C3—C2—H2B109.4C20—C19—H19A108.7
C1—C2—H2B109.4C18—C19—H19A108.7
H2A—C2—H2B108.0C20—C19—H19B108.7
O3—C3—C2111.3 (3)C18—C19—H19B108.7
O3—C3—C4108.7 (2)H19A—C19—H19B107.6
C2—C3—C4113.8 (2)C30—C20—C21109.6 (2)
O3—C3—H3A107.6C30—C20—C19113.0 (3)
C2—C3—H3A107.6C21—C20—C19109.1 (2)
C4—C3—H3A107.6C30—C20—C29106.7 (2)
C24—C4—C3111.7 (2)C21—C20—C29109.2 (2)
C24—C4—C23107.9 (2)C19—C20—C29109.2 (2)
C3—C4—C23106.9 (2)C22—C21—C20111.8 (2)
C24—C4—C5112.6 (2)C22—C21—H21A109.3
C3—C4—C5108.3 (2)C20—C21—H21A109.3
C23—C4—C5109.3 (2)C22—C21—H21B109.3
C6—C5—C4113.5 (2)C20—C21—H21B109.3
C6—C5—C10109.8 (2)H21A—C21—H21B107.9
C4—C5—C10117.9 (2)C21—C22—C17115.0 (3)
C6—C5—H5104.7C21—C22—H22A108.5
C4—C5—H5104.7C17—C22—H22A108.5
C10—C5—H5104.7C21—C22—H22B108.5
C7—C6—C5111.0 (2)C17—C22—H22B108.5
C7—C6—H6A109.4H22A—C22—H22B107.5
C5—C6—H6A109.4C4—C23—H23A109.5
C7—C6—H6B109.4C4—C23—H23B109.5
C5—C6—H6B109.4H23A—C23—H23B109.5
H6A—C6—H6B108.0C4—C23—H23C109.5
C6—C7—C8114.4 (2)H23A—C23—H23C109.5
C6—C7—H7A108.7H23B—C23—H23C109.5
C8—C7—H7A108.7C4—C24—H24A109.5
C6—C7—H7B108.7C4—C24—H24B109.5
C8—C7—H7B108.7H24A—C24—H24B109.5
H7A—C7—H7B107.6C4—C24—H24C109.5
C7—C8—C26107.7 (2)H24A—C24—H24C109.5
C7—C8—C9110.9 (2)H24B—C24—H24C109.5
C26—C8—C9109.6 (2)C10—C25—H25A109.5
C7—C8—C14109.5 (2)C10—C25—H25B109.5
C26—C8—C14111.1 (2)H25A—C25—H25B109.5
C9—C8—C14108.1 (2)C10—C25—H25C109.5
C11—C9—C10116.1 (2)H25A—C25—H25C109.5
C11—C9—C8108.4 (2)H25B—C25—H25C109.5
C10—C9—C8117.2 (2)C8—C26—H26A109.5
C11—C9—H9104.5C8—C26—H26B109.5
C10—C9—H9104.5H26A—C26—H26B109.5
C8—C9—H9104.5C8—C26—H26C109.5
C25—C10—C1108.1 (2)H26A—C26—H26C109.5
C25—C10—C9112.3 (2)H26B—C26—H26C109.5
C1—C10—C9108.7 (2)C14—C27—H27A109.5
C25—C10—C5114.7 (2)C14—C27—H27B109.5
C1—C10—C5107.1 (2)H27A—C27—H27B109.5
C9—C10—C5105.7 (2)C14—C27—H27C109.5
O11—C11—C12119.0 (3)H27A—C27—H27C109.5
O11—C11—C9123.7 (3)H27B—C27—H27C109.5
C12—C11—C9117.2 (2)C17—C28—H28A109.5
C13—C12—C11125.0 (3)C17—C28—H28B109.5
C13—C12—H12117.5H28A—C28—H28B109.5
C11—C12—H12117.5C17—C28—H28C109.5
C12—C13—C18119.3 (3)H28A—C28—H28C109.5
C12—C13—C14119.9 (3)H28B—C28—H28C109.5
C18—C13—C14120.5 (2)C20—C29—H29A109.5
C13—C14—C27106.0 (2)C20—C29—H29B109.5
C13—C14—C15111.9 (2)H29A—C29—H29B109.5
C27—C14—C15107.0 (2)C20—C29—H29C109.5
C13—C14—C8109.8 (2)H29A—C29—H29C109.5
C27—C14—C8112.0 (2)H29B—C29—H29C109.5
C15—C14—C8110.1 (2)O31—C30—O30122.5 (3)
C16—C15—C14114.2 (2)O31—C30—C20124.5 (3)
C16—C15—H15A108.7O30—C30—C20112.8 (3)
C14—C15—H15A108.7O30—C31—C32108.4 (3)
C16—C15—H15B108.7O30—C31—H31A110.0
C14—C15—H15B108.7C32—C31—H31A110.0
H15A—C15—H15B107.6O30—C31—H31B110.0
C17—C16—C15113.3 (2)C32—C31—H31B110.0
C17—C16—H16A108.9H31A—C31—H31B108.4
C15—C16—H16A108.9C31—C32—H32A109.5
C17—C16—H16B108.9C31—C32—H32B109.5
C15—C16—H16B108.9H32A—C32—H32B109.5
H16A—C16—H16B107.7C31—C32—H32C109.5
C16—C17—C28110.3 (2)H32A—C32—H32C109.5
C16—C17—C22111.1 (3)H32B—C32—H32C109.5
C10—C1—C2—C359.7 (3)C12—C13—C14—C15150.0 (3)
C1—C2—C3—O3179.0 (2)C18—C13—C14—C1535.1 (4)
C1—C2—C3—C457.8 (3)C12—C13—C14—C827.5 (3)
O3—C3—C4—C2450.6 (3)C18—C13—C14—C8157.6 (2)
C2—C3—C4—C2474.0 (3)C7—C8—C14—C13177.8 (2)
O3—C3—C4—C2367.2 (3)C26—C8—C14—C1363.3 (3)
C2—C3—C4—C23168.2 (3)C9—C8—C14—C1357.0 (3)
O3—C3—C4—C5175.1 (2)C7—C8—C14—C2760.4 (3)
C2—C3—C4—C550.5 (3)C26—C8—C14—C27179.2 (2)
C24—C4—C5—C655.5 (3)C9—C8—C14—C2760.5 (3)
C3—C4—C5—C6179.5 (2)C7—C8—C14—C1558.6 (3)
C23—C4—C5—C664.4 (3)C26—C8—C14—C1560.3 (3)
C24—C4—C5—C1075.0 (3)C9—C8—C14—C15179.4 (2)
C3—C4—C5—C1049.0 (3)C13—C14—C15—C1637.6 (3)
C23—C4—C5—C10165.1 (2)C27—C14—C15—C1678.1 (3)
C4—C5—C6—C7161.6 (2)C8—C14—C15—C16160.0 (2)
C10—C5—C6—C764.1 (3)C14—C15—C16—C1752.8 (3)
C5—C6—C7—C854.3 (3)C15—C16—C17—C2860.7 (3)
C6—C7—C8—C2676.6 (3)C15—C16—C17—C22179.8 (2)
C6—C7—C8—C943.3 (3)C15—C16—C17—C1860.0 (3)
C6—C7—C8—C14162.4 (2)C12—C13—C18—C1992.3 (3)
C7—C8—C9—C11179.1 (2)C14—C13—C18—C1982.6 (3)
C26—C8—C9—C1160.4 (3)C12—C13—C18—C17141.0 (3)
C14—C8—C9—C1160.9 (3)C14—C13—C18—C1744.2 (3)
C7—C8—C9—C1045.3 (3)C16—C17—C18—C1353.7 (3)
C26—C8—C9—C1073.5 (3)C28—C17—C18—C1367.2 (3)
C14—C8—C9—C10165.3 (2)C22—C17—C18—C13175.1 (2)
C2—C1—C10—C2570.2 (3)C16—C17—C18—C1972.2 (3)
C2—C1—C10—C9167.7 (2)C28—C17—C18—C19166.9 (2)
C2—C1—C10—C553.9 (3)C22—C17—C18—C1949.2 (3)
C11—C9—C10—C2558.4 (3)C13—C18—C19—C20179.3 (2)
C8—C9—C10—C2571.9 (3)C17—C18—C19—C2053.1 (3)
C11—C9—C10—C161.1 (3)C18—C19—C20—C3068.3 (3)
C8—C9—C10—C1168.6 (2)C18—C19—C20—C2153.9 (3)
C11—C9—C10—C5175.8 (2)C18—C19—C20—C29173.2 (2)
C8—C9—C10—C553.9 (3)C30—C20—C21—C2270.1 (3)
C6—C5—C10—C2562.9 (3)C19—C20—C21—C2254.1 (3)
C4—C5—C10—C2569.3 (3)C29—C20—C21—C22173.4 (2)
C6—C5—C10—C1177.2 (2)C20—C21—C22—C1756.2 (3)
C4—C5—C10—C150.6 (3)C16—C17—C22—C2167.9 (3)
C6—C5—C10—C961.4 (3)C28—C17—C22—C21171.3 (2)
C4—C5—C10—C9166.4 (2)C18—C17—C22—C2152.2 (3)
C10—C9—C11—O1112.2 (4)C31—O30—C30—O310.2 (4)
C8—C9—C11—O11146.6 (3)C31—O30—C30—C20177.1 (2)
C10—C9—C11—C12170.4 (2)C21—C20—C30—O3127.8 (4)
C8—C9—C11—C1236.0 (3)C19—C20—C30—O31149.8 (3)
O11—C11—C12—C13176.7 (3)C29—C20—C30—O3190.2 (4)
C9—C11—C12—C135.8 (4)C21—C20—C30—O30155.4 (2)
C11—C12—C13—C18176.2 (3)C19—C20—C30—O3033.4 (3)
C11—C12—C13—C141.3 (4)C29—C20—C30—O3086.6 (3)
C12—C13—C14—C2793.6 (3)C30—O30—C31—C32171.2 (3)
C18—C13—C14—C2781.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O11i0.842.233.039 (3)161
Symmetry code: (i) x+1, y1/2, z+3/2.
(5) isopropyl-3/b-hydroxy-11-oxoolean-12-en-30-oate top
Crystal data top
C33H52O4Dx = 1.177 Mg m3
Mr = 512.74Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 8245 reflections
a = 11.7789 (2) Åθ = 4.0–76.1°
b = 13.0812 (3) ŵ = 0.58 mm1
c = 18.7845 (4) ÅT = 130 K
V = 2894.36 (10) Å3Parallelepiped, colorless
Z = 40.20 × 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 tube5231 reflections with I > 2σ(I)
Detector resolution: 5.1996 pixels mm-1Rint = 0.037
ω scansθmax = 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 = 149
Tmin = 0.544, Tmax = 1.000k = 1616
15070 measured reflectionsl = 1723
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.08Δρmax = 0.33 e Å3
5719 reflectionsΔρmin = 0.21 e Å3
344 parametersAbsolute structure: Flack x determined using 2089 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O30.66526 (19)0.29625 (16)0.73372 (12)0.0418 (5)
H30.62200.29730.76920.063*
O110.48456 (16)0.17424 (16)0.65081 (11)0.0384 (4)
O300.52455 (18)0.56389 (16)0.47100 (10)0.0378 (4)
O310.6292 (2)0.68540 (18)0.41794 (14)0.0545 (6)
C10.5689 (2)0.0337 (2)0.67458 (14)0.0339 (5)
H1A0.49500.00170.67940.041*
H1B0.58270.04520.62320.041*
C20.5619 (2)0.1374 (2)0.71225 (15)0.0350 (6)
H2A0.54230.12660.76290.042*
H2B0.50080.17870.69030.042*
C30.6732 (2)0.1951 (2)0.70738 (14)0.0343 (5)
H3A0.69080.20140.65550.041*
C40.7729 (2)0.1350 (2)0.74056 (14)0.0324 (5)
C50.7762 (2)0.0272 (2)0.70494 (13)0.0309 (5)
H50.79140.04170.65350.037*
C60.8761 (2)0.0393 (2)0.72829 (15)0.0352 (6)
H6A0.94510.00340.73320.042*
H6B0.85950.07030.77520.042*
C70.8973 (2)0.1237 (2)0.67347 (15)0.0333 (5)
H7A0.91960.09190.62780.040*
H7B0.96140.16660.68980.040*
C80.7933 (2)0.1925 (2)0.66084 (13)0.0294 (5)
C90.6842 (2)0.1262 (2)0.65021 (13)0.0294 (5)
H90.69650.09120.60350.035*
C100.6636 (2)0.0359 (2)0.70442 (13)0.0296 (5)
C110.5831 (2)0.1968 (2)0.63689 (13)0.0312 (5)
C120.6062 (2)0.2968 (2)0.60305 (14)0.0330 (5)
H120.54350.34110.59540.040*
C130.7081 (2)0.3294 (2)0.58241 (13)0.0311 (5)
C140.8114 (2)0.2597 (2)0.59117 (14)0.0302 (5)
C150.9250 (2)0.3199 (2)0.59561 (15)0.0356 (6)
H15A0.93650.34290.64530.043*
H15B0.98820.27330.58330.043*
C160.9296 (2)0.4127 (2)0.54657 (16)0.0371 (6)
H16A0.92740.38930.49650.045*
H16B1.00240.44910.55410.045*
C170.8311 (3)0.4871 (2)0.55960 (15)0.0364 (6)
C180.7172 (2)0.4320 (2)0.54481 (14)0.0331 (5)
H180.65580.47650.56460.040*
C190.6910 (2)0.4172 (2)0.46445 (14)0.0325 (5)
H19A0.74240.36410.44520.039*
H19B0.61230.39160.45950.039*
C200.7036 (3)0.5142 (2)0.41937 (14)0.0357 (6)
C210.8220 (3)0.5582 (2)0.43184 (16)0.0410 (6)
H21A0.83060.62190.40390.049*
H21B0.87950.50880.41480.049*
C220.8429 (3)0.5811 (2)0.51047 (17)0.0418 (6)
H22A0.78840.63410.52620.050*
H22B0.92030.60960.51590.050*
C230.7643 (3)0.1331 (2)0.82253 (15)0.0403 (6)
H23A0.68900.10830.83660.060*
H23B0.82260.08740.84180.060*
H23C0.77570.20220.84120.060*
C240.8820 (2)0.1934 (2)0.72134 (16)0.0385 (6)
H24A0.87450.26500.73580.058*
H24B0.94670.16240.74610.058*
H24C0.89450.18980.66980.058*
C250.6254 (2)0.0750 (2)0.77802 (14)0.0353 (6)
H25A0.57500.13400.77190.053*
H25B0.69210.09550.80580.053*
H25C0.58480.02050.80320.053*
C260.7800 (2)0.2624 (2)0.72715 (14)0.0345 (5)
H26A0.78370.22070.77040.052*
H26B0.70660.29750.72510.052*
H26C0.84130.31310.72780.052*
C270.8187 (2)0.1932 (2)0.52232 (14)0.0337 (5)
H27A0.74310.16700.51040.050*
H27B0.87050.13570.53040.050*
H27C0.84710.23500.48290.050*
C280.8325 (3)0.5255 (2)0.63692 (17)0.0453 (7)
H28A0.81430.46880.66910.068*
H28B0.77590.57990.64260.068*
H28C0.90800.55230.64830.068*
C290.6901 (3)0.4873 (2)0.33985 (15)0.0412 (6)
H29A0.61280.46250.33110.062*
H29B0.74480.43400.32700.062*
H29C0.70390.54840.31100.062*
C300.6169 (3)0.5976 (2)0.43563 (15)0.0383 (6)
C310.4469 (3)0.6428 (2)0.49698 (16)0.0435 (7)
H310.43360.69450.45870.052*
C320.4998 (4)0.6941 (3)0.56098 (19)0.0551 (9)
H32A0.52170.64210.59600.083*
H32B0.44480.74110.58240.083*
H32C0.56730.73230.54600.083*
C330.3365 (3)0.5894 (3)0.51460 (18)0.0504 (8)
H33A0.30590.55730.47150.076*
H33B0.28190.63940.53290.076*
H33C0.35030.53690.55080.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0473 (11)0.0342 (10)0.0440 (11)0.0000 (9)0.0067 (9)0.0044 (8)
O110.0329 (9)0.0421 (11)0.0401 (10)0.0034 (8)0.0030 (8)0.0036 (8)
O300.0487 (11)0.0347 (10)0.0299 (9)0.0067 (9)0.0037 (8)0.0021 (8)
O310.0659 (15)0.0405 (12)0.0570 (14)0.0023 (11)0.0045 (12)0.0143 (10)
C10.0351 (12)0.0364 (13)0.0303 (12)0.0001 (11)0.0020 (10)0.0028 (11)
C20.0366 (13)0.0358 (13)0.0328 (13)0.0040 (11)0.0001 (11)0.0024 (11)
C30.0408 (13)0.0339 (13)0.0282 (12)0.0009 (12)0.0023 (10)0.0017 (10)
C40.0385 (13)0.0336 (12)0.0251 (12)0.0012 (11)0.0000 (10)0.0023 (10)
C50.0338 (12)0.0335 (12)0.0255 (11)0.0013 (10)0.0009 (10)0.0012 (10)
C60.0358 (12)0.0396 (13)0.0303 (12)0.0032 (11)0.0049 (10)0.0011 (11)
C70.0309 (12)0.0350 (13)0.0342 (13)0.0011 (10)0.0027 (10)0.0013 (11)
C80.0313 (11)0.0308 (12)0.0261 (11)0.0009 (10)0.0012 (9)0.0004 (10)
C90.0320 (11)0.0327 (12)0.0236 (11)0.0026 (10)0.0001 (9)0.0004 (9)
C100.0336 (12)0.0318 (12)0.0233 (11)0.0017 (10)0.0004 (9)0.0007 (9)
C110.0341 (12)0.0346 (12)0.0251 (11)0.0032 (11)0.0012 (9)0.0030 (10)
C120.0344 (12)0.0357 (13)0.0289 (12)0.0037 (11)0.0005 (10)0.0004 (10)
C130.0379 (12)0.0319 (12)0.0234 (10)0.0023 (11)0.0023 (10)0.0033 (9)
C140.0318 (12)0.0304 (11)0.0285 (12)0.0011 (10)0.0000 (9)0.0006 (9)
C150.0346 (13)0.0357 (14)0.0366 (14)0.0020 (11)0.0010 (11)0.0009 (11)
C160.0383 (13)0.0351 (13)0.0381 (14)0.0061 (11)0.0006 (11)0.0023 (11)
C170.0451 (14)0.0321 (12)0.0319 (13)0.0030 (12)0.0027 (11)0.0008 (10)
C180.0404 (13)0.0310 (12)0.0279 (12)0.0035 (11)0.0011 (10)0.0005 (10)
C190.0375 (12)0.0317 (12)0.0282 (12)0.0002 (11)0.0003 (10)0.0016 (10)
C200.0427 (14)0.0361 (13)0.0285 (12)0.0024 (11)0.0017 (11)0.0020 (10)
C210.0463 (15)0.0404 (14)0.0364 (14)0.0073 (13)0.0014 (12)0.0079 (11)
C220.0480 (15)0.0356 (14)0.0419 (15)0.0063 (13)0.0048 (12)0.0026 (12)
C230.0511 (16)0.0437 (15)0.0260 (12)0.0032 (13)0.0012 (11)0.0062 (11)
C240.0382 (13)0.0376 (14)0.0396 (14)0.0043 (12)0.0004 (11)0.0043 (11)
C250.0412 (13)0.0402 (13)0.0245 (11)0.0034 (12)0.0023 (10)0.0000 (10)
C260.0420 (13)0.0345 (13)0.0270 (12)0.0019 (11)0.0041 (10)0.0024 (10)
C270.0389 (13)0.0349 (12)0.0272 (12)0.0015 (11)0.0035 (10)0.0009 (10)
C280.0599 (18)0.0386 (14)0.0375 (15)0.0021 (14)0.0066 (13)0.0052 (12)
C290.0516 (16)0.0450 (15)0.0269 (13)0.0038 (13)0.0013 (12)0.0031 (11)
C300.0493 (15)0.0363 (14)0.0294 (12)0.0000 (12)0.0016 (11)0.0019 (11)
C310.0604 (18)0.0403 (15)0.0298 (13)0.0146 (14)0.0009 (13)0.0008 (11)
C320.076 (2)0.0502 (18)0.0387 (15)0.0175 (18)0.0052 (16)0.0087 (14)
C330.0563 (18)0.0575 (19)0.0373 (15)0.0146 (16)0.0045 (13)0.0054 (14)
Geometric parameters (Å, º) top
O3—C31.415 (3)C17—C281.537 (4)
O3—H30.8400C17—C221.543 (4)
O11—C111.227 (3)C17—C181.548 (4)
O30—C301.349 (4)C18—C191.553 (4)
O30—C311.462 (4)C18—H181.0000
O31—C301.204 (4)C19—C201.532 (4)
C1—C21.531 (4)C19—H19A0.9900
C1—C101.546 (4)C19—H19B0.9900
C1—H1A0.9900C20—C301.525 (4)
C1—H1B0.9900C20—C211.526 (4)
C2—C31.516 (4)C20—C291.543 (4)
C2—H2A0.9900C21—C221.527 (4)
C2—H2B0.9900C21—H21A0.9900
C3—C41.544 (4)C21—H21B0.9900
C3—H3A1.0000C22—H22A0.9900
C4—C241.538 (4)C22—H22B0.9900
C4—C231.543 (4)C23—H23A0.9800
C4—C51.562 (4)C23—H23B0.9800
C5—C61.528 (4)C23—H23C0.9800
C5—C101.562 (4)C24—H24A0.9800
C5—H51.0000C24—H24B0.9800
C6—C71.530 (4)C24—H24C0.9800
C6—H6A0.9900C25—H25A0.9800
C6—H6B0.9900C25—H25B0.9800
C7—C81.538 (3)C25—H25C0.9800
C7—H7A0.9900C26—H26A0.9800
C7—H7B0.9900C26—H26B0.9800
C8—C261.553 (3)C26—H26C0.9800
C8—C91.564 (3)C27—H27A0.9800
C8—C141.591 (3)C27—H27B0.9800
C9—C111.528 (3)C27—H27C0.9800
C9—C101.578 (3)C28—H28A0.9800
C9—H91.0000C28—H28B0.9800
C10—C251.541 (3)C28—H28C0.9800
C11—C121.479 (4)C29—H29A0.9800
C12—C131.331 (4)C29—H29B0.9800
C12—H120.9500C29—H29C0.9800
C13—C181.521 (4)C31—C321.512 (5)
C13—C141.529 (4)C31—C331.512 (5)
C14—C151.555 (4)C31—H311.0000
C14—C271.561 (4)C32—H32A0.9800
C15—C161.525 (4)C32—H32B0.9800
C15—H15A0.9900C32—H32C0.9800
C15—H15B0.9900C33—H33A0.9800
C16—C171.534 (4)C33—H33B0.9800
C16—H16A0.9900C33—H33C0.9800
C16—H16B0.9900
C3—O3—H3109.5C22—C17—C18109.9 (2)
C30—O30—C31116.0 (2)C13—C18—C17112.9 (2)
C2—C1—C10113.1 (2)C13—C18—C19109.1 (2)
C2—C1—H1A108.9C17—C18—C19113.9 (2)
C10—C1—H1A108.9C13—C18—H18106.8
C2—C1—H1B108.9C17—C18—H18106.8
C10—C1—H1B108.9C19—C18—H18106.8
H1A—C1—H1B107.8C20—C19—C18114.5 (2)
C3—C2—C1111.5 (2)C20—C19—H19A108.6
C3—C2—H2A109.3C18—C19—H19A108.6
C1—C2—H2A109.3C20—C19—H19B108.6
C3—C2—H2B109.3C18—C19—H19B108.6
C1—C2—H2B109.3H19A—C19—H19B107.6
H2A—C2—H2B108.0C30—C20—C21108.1 (2)
O3—C3—C2112.8 (2)C30—C20—C19114.6 (2)
O3—C3—C4112.7 (2)C21—C20—C19108.4 (2)
C2—C3—C4112.3 (2)C30—C20—C29106.7 (2)
O3—C3—H3A106.2C21—C20—C29109.2 (2)
C2—C3—H3A106.2C19—C20—C29109.7 (2)
C4—C3—H3A106.2C20—C21—C22111.7 (2)
C24—C4—C23107.3 (2)C20—C21—H21A109.3
C24—C4—C3106.7 (2)C22—C21—H21A109.3
C23—C4—C3111.2 (2)C20—C21—H21B109.3
C24—C4—C5109.1 (2)C22—C21—H21B109.3
C23—C4—C5114.5 (2)H21A—C21—H21B107.9
C3—C4—C5107.8 (2)C21—C22—C17114.0 (2)
C6—C5—C4114.2 (2)C21—C22—H22A108.7
C6—C5—C10110.8 (2)C17—C22—H22A108.7
C4—C5—C10117.3 (2)C21—C22—H22B108.7
C6—C5—H5104.3C17—C22—H22B108.7
C4—C5—H5104.3H22A—C22—H22B107.6
C10—C5—H5104.3C4—C23—H23A109.5
C5—C6—C7110.1 (2)C4—C23—H23B109.5
C5—C6—H6A109.6H23A—C23—H23B109.5
C7—C6—H6A109.6C4—C23—H23C109.5
C5—C6—H6B109.6H23A—C23—H23C109.5
C7—C6—H6B109.6H23B—C23—H23C109.5
H6A—C6—H6B108.2C4—C24—H24A109.5
C6—C7—C8113.4 (2)C4—C24—H24B109.5
C6—C7—H7A108.9H24A—C24—H24B109.5
C8—C7—H7A108.9C4—C24—H24C109.5
C6—C7—H7B108.9H24A—C24—H24C109.5
C8—C7—H7B108.9H24B—C24—H24C109.5
H7A—C7—H7B107.7C10—C25—H25A109.5
C7—C8—C26107.5 (2)C10—C25—H25B109.5
C7—C8—C9110.4 (2)H25A—C25—H25B109.5
C26—C8—C9110.2 (2)C10—C25—H25C109.5
C7—C8—C14110.1 (2)H25A—C25—H25C109.5
C26—C8—C14110.4 (2)H25B—C25—H25C109.5
C9—C8—C14108.16 (19)C8—C26—H26A109.5
C11—C9—C8109.0 (2)C8—C26—H26B109.5
C11—C9—C10116.0 (2)H26A—C26—H26B109.5
C8—C9—C10117.3 (2)C8—C26—H26C109.5
C11—C9—H9104.3H26A—C26—H26C109.5
C8—C9—H9104.3H26B—C26—H26C109.5
C10—C9—H9104.3C14—C27—H27A109.5
C25—C10—C1108.1 (2)C14—C27—H27B109.5
C25—C10—C5114.7 (2)H27A—C27—H27B109.5
C1—C10—C5107.6 (2)C14—C27—H27C109.5
C25—C10—C9112.1 (2)H27A—C27—H27C109.5
C1—C10—C9108.5 (2)H27B—C27—H27C109.5
C5—C10—C9105.6 (2)C17—C28—H28A109.5
O11—C11—C12118.6 (2)C17—C28—H28B109.5
O11—C11—C9123.8 (3)H28A—C28—H28B109.5
C12—C11—C9117.5 (2)C17—C28—H28C109.5
C13—C12—C11125.0 (2)H28A—C28—H28C109.5
C13—C12—H12117.5H28B—C28—H28C109.5
C11—C12—H12117.5C20—C29—H29A109.5
C12—C13—C18118.8 (2)C20—C29—H29B109.5
C12—C13—C14119.7 (2)H29A—C29—H29B109.5
C18—C13—C14121.3 (2)C20—C29—H29C109.5
C13—C14—C15112.9 (2)H29A—C29—H29C109.5
C13—C14—C27106.7 (2)H29B—C29—H29C109.5
C15—C14—C27106.2 (2)O31—C30—O30123.0 (3)
C13—C14—C8108.1 (2)O31—C30—C20123.1 (3)
C15—C14—C8110.5 (2)O30—C30—C20113.9 (2)
C27—C14—C8112.4 (2)O30—C31—C32108.7 (3)
C16—C15—C14113.7 (2)O30—C31—C33106.6 (3)
C16—C15—H15A108.8C32—C31—C33112.7 (3)
C14—C15—H15A108.8O30—C31—H31109.6
C16—C15—H15B108.8C32—C31—H31109.6
C14—C15—H15B108.8C33—C31—H31109.6
H15A—C15—H15B107.7C31—C32—H32A109.5
C15—C16—C17112.4 (2)C31—C32—H32B109.5
C15—C16—H16A109.1H32A—C32—H32B109.5
C17—C16—H16A109.1C31—C32—H32C109.5
C15—C16—H16B109.1H32A—C32—H32C109.5
C17—C16—H16B109.1H32B—C32—H32C109.5
H16A—C16—H16B107.9C31—C33—H33A109.5
C16—C17—C28110.5 (3)C31—C33—H33B109.5
C16—C17—C22110.0 (2)H33A—C33—H33B109.5
C28—C17—C22107.7 (2)C31—C33—H33C109.5
C16—C17—C18109.4 (2)H33A—C33—H33C109.5
C28—C17—C18109.3 (2)H33B—C33—H33C109.5
C10—C1—C2—C358.1 (3)C12—C13—C14—C2788.0 (3)
C1—C2—C3—O3172.5 (2)C18—C13—C14—C2786.8 (3)
C1—C2—C3—C458.9 (3)C12—C13—C14—C833.1 (3)
O3—C3—C4—C2460.4 (3)C18—C13—C14—C8152.1 (2)
C2—C3—C4—C24171.0 (2)C7—C8—C14—C13178.0 (2)
O3—C3—C4—C2356.4 (3)C26—C8—C14—C1359.4 (3)
C2—C3—C4—C2372.3 (3)C9—C8—C14—C1361.3 (2)
O3—C3—C4—C5177.4 (2)C7—C8—C14—C1553.9 (3)
C2—C3—C4—C553.9 (3)C26—C8—C14—C1564.6 (3)
C24—C4—C5—C660.2 (3)C9—C8—C14—C15174.7 (2)
C23—C4—C5—C660.0 (3)C7—C8—C14—C2764.5 (3)
C3—C4—C5—C6175.8 (2)C26—C8—C14—C27176.9 (2)
C24—C4—C5—C10167.7 (2)C9—C8—C14—C2756.2 (3)
C23—C4—C5—C1072.1 (3)C13—C14—C15—C1637.8 (3)
C3—C4—C5—C1052.2 (3)C27—C14—C15—C1678.8 (3)
C4—C5—C6—C7159.7 (2)C8—C14—C15—C16159.0 (2)
C10—C5—C6—C765.2 (3)C14—C15—C16—C1755.9 (3)
C5—C6—C7—C857.8 (3)C15—C16—C17—C2859.2 (3)
C6—C7—C8—C2673.3 (3)C15—C16—C17—C22177.9 (2)
C6—C7—C8—C947.0 (3)C15—C16—C17—C1861.2 (3)
C6—C7—C8—C14166.4 (2)C12—C13—C18—C17148.8 (2)
C7—C8—C9—C11179.3 (2)C14—C13—C18—C1736.4 (3)
C26—C8—C9—C1162.0 (3)C12—C13—C18—C1983.5 (3)
C14—C8—C9—C1158.7 (2)C14—C13—C18—C1991.3 (3)
C7—C8—C9—C1046.3 (3)C16—C17—C18—C1349.8 (3)
C26—C8—C9—C1072.4 (3)C28—C17—C18—C1371.3 (3)
C14—C8—C9—C10166.8 (2)C22—C17—C18—C13170.6 (2)
C2—C1—C10—C2572.8 (3)C16—C17—C18—C1975.4 (3)
C2—C1—C10—C551.6 (3)C28—C17—C18—C19163.5 (2)
C2—C1—C10—C9165.4 (2)C22—C17—C18—C1945.5 (3)
C6—C5—C10—C2564.2 (3)C13—C18—C19—C20176.8 (2)
C4—C5—C10—C2569.4 (3)C17—C18—C19—C2049.7 (3)
C6—C5—C10—C1175.5 (2)C18—C19—C20—C3067.0 (3)
C4—C5—C10—C150.9 (3)C18—C19—C20—C2153.9 (3)
C6—C5—C10—C959.7 (3)C18—C19—C20—C29173.0 (2)
C4—C5—C10—C9166.7 (2)C30—C20—C21—C2267.3 (3)
C11—C9—C10—C2557.6 (3)C19—C20—C21—C2257.5 (3)
C8—C9—C10—C2573.7 (3)C29—C20—C21—C22177.0 (2)
C11—C9—C10—C161.7 (3)C20—C21—C22—C1758.7 (4)
C8—C9—C10—C1167.0 (2)C16—C17—C22—C2169.8 (3)
C11—C9—C10—C5176.9 (2)C28—C17—C22—C21169.7 (3)
C8—C9—C10—C551.8 (3)C18—C17—C22—C2150.7 (3)
C8—C9—C11—O11153.6 (2)C31—O30—C30—O319.3 (4)
C10—C9—C11—O1118.5 (4)C31—O30—C30—C20171.4 (2)
C8—C9—C11—C1228.5 (3)C21—C20—C30—O3141.4 (4)
C10—C9—C11—C12163.6 (2)C19—C20—C30—O31162.5 (3)
O11—C11—C12—C13177.1 (3)C29—C20—C30—O3176.0 (4)
C9—C11—C12—C130.9 (4)C21—C20—C30—O30139.3 (3)
C11—C12—C13—C18176.9 (2)C19—C20—C30—O3018.2 (3)
C11—C12—C13—C142.0 (4)C29—C20—C30—O30103.4 (3)
C12—C13—C14—C15155.8 (2)C30—O30—C31—C3274.6 (3)
C18—C13—C14—C1529.5 (3)C30—O30—C31—C33163.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O11i0.841.992.823 (3)170
Symmetry code: (i) x+1, y1/2, z+3/2.
(6) 2-(morpholin-4-yl)ethyl-3/b-hydroxy-11-oxoolean-12-en-30-oate top
Crystal data top
C36H57NO5Dx = 1.185 Mg m3
Mr = 583.82Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 7311 reflections
a = 12.8700 (1) Åθ = 3.2–76.3°
b = 13.6972 (2) ŵ = 0.61 mm1
c = 18.5682 (3) ÅT = 130 K
V = 3273.26 (8) Å3Needle, colorless
Z = 40.40 × 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 tube5438 reflections with I > 2σ(I)
Detector resolution: 10.5357 pixels mm-1Rint = 0.022
ω scansθmax = 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 = 1512
Tmin = 0.682, Tmax = 1.000k = 1616
10943 measured reflectionsl = 2220
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.22 e Å3
5691 reflectionsΔρmin = 0.14 e Å3
387 parametersAbsolute structure: Flack x determined using 2127 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
0 restraintsAbsolute 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
xyzUiso*/Ueq
O10.7055 (3)0.8239 (2)0.59632 (14)0.0759 (8)
O30.65653 (14)0.16649 (15)0.82861 (11)0.0482 (5)
H30.59420.18460.82960.072*
O110.54649 (13)0.26264 (14)0.67741 (11)0.0443 (5)
O300.56396 (13)0.51804 (13)0.41113 (11)0.0436 (4)
O310.67502 (17)0.62859 (14)0.36686 (11)0.0479 (5)
N10.59212 (19)0.67066 (18)0.52715 (13)0.0454 (5)
C10.59145 (16)0.06262 (18)0.72404 (14)0.0323 (5)
H1A0.53250.10870.72820.039*
H1B0.58850.03280.67550.039*
C20.57917 (18)0.01746 (19)0.78058 (14)0.0360 (5)
H2A0.57630.01250.82910.043*
H2B0.51300.05260.77240.043*
C30.66826 (18)0.08905 (19)0.77751 (14)0.0353 (5)
H3A0.66830.11900.72840.042*
C40.77514 (19)0.0410 (2)0.78898 (13)0.0374 (6)
C50.78438 (16)0.04375 (18)0.73321 (12)0.0304 (5)
H50.78110.01090.68520.037*
C60.89021 (18)0.0948 (2)0.73423 (15)0.0400 (6)
H6A0.89360.14020.77570.048*
H6B0.94600.04560.74000.048*
C70.90666 (17)0.15134 (19)0.66429 (14)0.0365 (6)
H7A0.90980.10440.62380.044*
H7B0.97450.18530.66670.044*
C80.82130 (16)0.22695 (17)0.64859 (12)0.0269 (4)
C90.71170 (15)0.18159 (16)0.66134 (11)0.0254 (4)
H90.70320.13350.62130.030*
C100.69436 (17)0.11999 (17)0.73160 (12)0.0287 (5)
C110.63024 (17)0.25991 (18)0.64599 (14)0.0319 (5)
C120.65425 (17)0.33248 (17)0.59067 (14)0.0329 (5)
H120.60220.37940.57960.039*
C130.74432 (16)0.33788 (16)0.55426 (12)0.0274 (5)
C140.82829 (16)0.26092 (16)0.56725 (12)0.0273 (4)
C150.93950 (17)0.29838 (18)0.54945 (13)0.0336 (5)
H15A0.96760.33230.59230.040*
H15B0.98470.24140.53970.040*
C160.94485 (18)0.36783 (19)0.48508 (14)0.0356 (5)
H16A0.92680.33150.44070.043*
H16B1.01690.39210.47990.043*
C170.87087 (17)0.45539 (18)0.49318 (13)0.0331 (5)
C180.75794 (17)0.41645 (17)0.49728 (13)0.0304 (5)
H180.71290.47260.51170.036*
C190.71744 (17)0.37979 (18)0.42417 (13)0.0327 (5)
H19A0.75830.32200.40930.039*
H19B0.64410.35920.42950.039*
C200.72453 (18)0.45806 (19)0.36519 (13)0.0346 (5)
C210.83798 (19)0.4914 (2)0.35856 (14)0.0398 (6)
H21A0.88070.43630.34090.048*
H21B0.84250.54470.32270.048*
C220.88161 (19)0.52706 (19)0.43020 (15)0.0401 (6)
H22A0.84600.58860.44330.048*
H22B0.95620.54230.42360.048*
C240.7892 (2)0.0093 (3)0.86776 (15)0.0526 (8)
H24A0.72910.02950.88290.079*
H24B0.85240.03010.87220.079*
H24C0.79500.06730.89840.079*
C230.8578 (2)0.1188 (2)0.7717 (2)0.0545 (8)
H23A0.92680.09360.78380.082*
H23B0.85520.13470.72020.082*
H23C0.84390.17780.80000.082*
C250.6878 (2)0.1845 (2)0.79958 (13)0.0409 (6)
H25A0.65120.24520.78800.061*
H25B0.75810.19970.81650.061*
H25C0.65000.14950.83740.061*
C260.8385 (2)0.3136 (2)0.70017 (13)0.0378 (5)
H26A0.84780.28910.74930.057*
H26B0.77790.35690.69860.057*
H26C0.90060.34980.68540.057*
C270.8048 (2)0.17678 (18)0.51343 (13)0.0354 (5)
H27A0.73000.16350.51300.053*
H27B0.84230.11790.52830.053*
H27C0.82740.19590.46500.053*
C280.8964 (2)0.5116 (2)0.56228 (16)0.0442 (6)
H28A0.88240.47010.60420.066*
H28B0.85330.57050.56490.066*
H28C0.97000.53020.56200.066*
C290.6894 (2)0.4154 (2)0.29241 (14)0.0406 (6)
H29A0.61760.39210.29650.061*
H29B0.73490.36090.27920.061*
H29C0.69330.46620.25530.061*
C300.6546 (2)0.54522 (19)0.38143 (13)0.0364 (5)
C310.4901 (2)0.5939 (2)0.42854 (19)0.0516 (7)
H31A0.41900.57100.41720.062*
H31B0.50450.65230.39870.062*
C320.4964 (2)0.6209 (2)0.5071 (2)0.0550 (8)
H32A0.43680.66370.51910.066*
H32B0.48980.56080.53640.066*
C330.6019 (3)0.6775 (3)0.60549 (18)0.0643 (9)
H33A0.60150.61110.62650.077*
H33B0.54170.71370.62520.077*
C340.6992 (4)0.7281 (3)0.6259 (2)0.0784 (13)
H34A0.70340.73220.67900.094*
H34B0.75920.68930.60880.094*
C350.6954 (4)0.8181 (3)0.5207 (2)0.0730 (11)
H35A0.75530.78160.50090.088*
H35B0.69720.88480.50030.088*
C360.5966 (3)0.7687 (2)0.49781 (18)0.0533 (7)
H36A0.53620.80680.51500.064*
H36B0.59340.76580.44460.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.102 (2)0.0663 (15)0.0596 (14)0.0007 (15)0.0148 (14)0.0175 (13)
O30.0340 (9)0.0529 (11)0.0577 (11)0.0136 (8)0.0102 (8)0.0256 (10)
O110.0283 (8)0.0441 (10)0.0605 (12)0.0082 (7)0.0156 (8)0.0080 (9)
O300.0321 (9)0.0384 (9)0.0604 (12)0.0019 (7)0.0014 (9)0.0001 (9)
O310.0588 (12)0.0384 (10)0.0464 (10)0.0005 (9)0.0061 (9)0.0099 (8)
N10.0477 (12)0.0450 (12)0.0435 (12)0.0066 (11)0.0076 (10)0.0035 (11)
C10.0203 (9)0.0370 (12)0.0394 (12)0.0036 (9)0.0017 (9)0.0021 (11)
C20.0265 (10)0.0426 (13)0.0389 (13)0.0089 (10)0.0005 (9)0.0016 (11)
C30.0308 (11)0.0380 (12)0.0370 (12)0.0076 (10)0.0063 (10)0.0080 (11)
C40.0283 (11)0.0477 (14)0.0363 (12)0.0081 (10)0.0063 (10)0.0142 (11)
C50.0219 (10)0.0400 (12)0.0294 (10)0.0029 (9)0.0030 (8)0.0057 (10)
C60.0225 (10)0.0534 (15)0.0442 (14)0.0067 (10)0.0061 (10)0.0170 (13)
C70.0194 (10)0.0467 (14)0.0435 (13)0.0017 (10)0.0002 (9)0.0138 (12)
C80.0201 (9)0.0336 (11)0.0271 (10)0.0016 (8)0.0002 (8)0.0004 (9)
C90.0200 (9)0.0293 (10)0.0269 (10)0.0003 (8)0.0006 (8)0.0037 (9)
C100.0231 (10)0.0344 (11)0.0286 (10)0.0062 (9)0.0016 (8)0.0023 (9)
C110.0224 (10)0.0335 (11)0.0399 (12)0.0013 (9)0.0031 (9)0.0039 (10)
C120.0231 (10)0.0313 (11)0.0442 (13)0.0049 (9)0.0024 (9)0.0018 (10)
C130.0236 (9)0.0270 (10)0.0316 (11)0.0002 (8)0.0016 (8)0.0028 (9)
C140.0219 (9)0.0313 (11)0.0287 (10)0.0028 (9)0.0022 (8)0.0011 (9)
C150.0216 (10)0.0411 (13)0.0380 (13)0.0026 (9)0.0046 (9)0.0064 (11)
C160.0229 (10)0.0424 (13)0.0415 (13)0.0015 (9)0.0034 (10)0.0061 (11)
C170.0266 (10)0.0334 (11)0.0394 (12)0.0038 (9)0.0006 (9)0.0030 (11)
C180.0257 (10)0.0283 (10)0.0373 (12)0.0010 (9)0.0002 (9)0.0014 (10)
C190.0271 (10)0.0333 (11)0.0376 (12)0.0011 (9)0.0017 (9)0.0040 (10)
C200.0302 (11)0.0376 (12)0.0361 (12)0.0012 (10)0.0002 (10)0.0061 (10)
C210.0309 (12)0.0458 (14)0.0427 (13)0.0029 (11)0.0032 (11)0.0119 (12)
C220.0300 (11)0.0400 (13)0.0504 (15)0.0068 (10)0.0016 (11)0.0084 (12)
C240.0466 (15)0.073 (2)0.0382 (14)0.0285 (15)0.0164 (12)0.0202 (14)
C230.0318 (12)0.0584 (17)0.073 (2)0.0058 (12)0.0005 (13)0.0321 (16)
C250.0462 (13)0.0456 (14)0.0309 (11)0.0136 (12)0.0097 (11)0.0071 (11)
C260.0380 (12)0.0442 (13)0.0312 (11)0.0136 (11)0.0003 (10)0.0033 (11)
C270.0438 (13)0.0323 (11)0.0301 (11)0.0051 (10)0.0041 (10)0.0007 (10)
C280.0410 (13)0.0403 (14)0.0513 (15)0.0068 (11)0.0053 (12)0.0023 (13)
C290.0407 (12)0.0442 (14)0.0368 (13)0.0007 (11)0.0023 (11)0.0037 (11)
C300.0400 (12)0.0380 (13)0.0313 (11)0.0021 (11)0.0049 (10)0.0062 (10)
C310.0343 (13)0.0474 (15)0.073 (2)0.0043 (12)0.0062 (13)0.0056 (15)
C320.0418 (14)0.0516 (16)0.072 (2)0.0044 (13)0.0165 (15)0.0002 (16)
C330.098 (3)0.0476 (16)0.0469 (17)0.0147 (18)0.0105 (17)0.0026 (14)
C340.116 (3)0.059 (2)0.060 (2)0.031 (2)0.031 (2)0.0194 (17)
C350.092 (3)0.070 (2)0.0564 (19)0.027 (2)0.0067 (19)0.0109 (18)
C360.0649 (18)0.0475 (16)0.0474 (16)0.0018 (14)0.0003 (14)0.0025 (14)
Geometric parameters (Å, º) top
O1—C351.412 (4)C17—C281.532 (4)
O1—C341.425 (5)C17—C221.533 (3)
O3—C31.431 (3)C17—C181.550 (3)
O3—H30.8400C18—C191.539 (3)
O11—C111.226 (3)C18—H181.0000
O30—C301.343 (3)C19—C201.535 (3)
O30—C311.445 (3)C19—H19A0.9900
O31—C301.203 (3)C19—H19B0.9900
N1—C361.450 (4)C20—C301.525 (4)
N1—C321.456 (4)C20—C211.535 (3)
N1—C331.463 (4)C20—C291.540 (4)
C1—C21.527 (3)C21—C221.524 (4)
C1—C101.547 (3)C21—H21A0.9900
C1—H1A0.9900C21—H21B0.9900
C1—H1B0.9900C22—H22A0.9900
C2—C31.510 (4)C22—H22B0.9900
C2—H2A0.9900C24—H24A0.9800
C2—H2B0.9900C24—H24B0.9800
C3—C41.540 (3)C24—H24C0.9800
C3—H3A1.0000C23—H23A0.9800
C4—C241.536 (4)C23—H23B0.9800
C4—C231.540 (4)C23—H23C0.9800
C4—C51.560 (3)C25—H25A0.9800
C5—C61.531 (3)C25—H25B0.9800
C5—C101.560 (3)C25—H25C0.9800
C5—H51.0000C26—H26A0.9800
C6—C71.527 (3)C26—H26B0.9800
C6—H6A0.9900C26—H26C0.9800
C6—H6B0.9900C27—H27A0.9800
C7—C81.538 (3)C27—H27B0.9800
C7—H7A0.9900C27—H27C0.9800
C7—H7B0.9900C28—H28A0.9800
C8—C261.541 (3)C28—H28B0.9800
C8—C91.559 (3)C28—H28C0.9800
C8—C141.583 (3)C29—H29A0.9800
C9—C111.527 (3)C29—H29B0.9800
C9—C101.570 (3)C29—H29C0.9800
C9—H91.0000C31—C321.508 (5)
C10—C251.543 (3)C31—H31A0.9900
C11—C121.462 (3)C31—H31B0.9900
C12—C131.344 (3)C32—H32A0.9900
C12—H120.9500C32—H32B0.9900
C13—C181.519 (3)C33—C341.480 (6)
C13—C141.529 (3)C33—H33A0.9900
C14—C271.555 (3)C33—H33B0.9900
C14—C151.556 (3)C34—H34A0.9900
C15—C161.529 (3)C34—H34B0.9900
C15—H15A0.9900C35—C361.502 (5)
C15—H15B0.9900C35—H35A0.9900
C16—C171.539 (3)C35—H35B0.9900
C16—H16A0.9900C36—H36A0.9900
C16—H16B0.9900C36—H36B0.9900
C35—O1—C34109.0 (3)C20—C19—C18112.42 (19)
C3—O3—H3109.5C20—C19—H19A109.1
C30—O30—C31117.6 (2)C18—C19—H19A109.1
C36—N1—C32111.8 (3)C20—C19—H19B109.1
C36—N1—C33108.1 (3)C18—C19—H19B109.1
C32—N1—C33110.9 (3)H19A—C19—H19B107.9
C2—C1—C10113.04 (19)C30—C20—C21110.1 (2)
C2—C1—H1A109.0C30—C20—C19111.8 (2)
C10—C1—H1A109.0C21—C20—C19108.74 (19)
C2—C1—H1B109.0C30—C20—C29107.3 (2)
C10—C1—H1B109.0C21—C20—C29108.8 (2)
H1A—C1—H1B107.8C19—C20—C29110.1 (2)
C3—C2—C1111.2 (2)C22—C21—C20112.1 (2)
C3—C2—H2A109.4C22—C21—H21A109.2
C1—C2—H2A109.4C20—C21—H21A109.2
C3—C2—H2B109.4C22—C21—H21B109.2
C1—C2—H2B109.4C20—C21—H21B109.2
H2A—C2—H2B108.0H21A—C21—H21B107.9
O3—C3—C2112.1 (2)C21—C22—C17115.3 (2)
O3—C3—C4108.63 (18)C21—C22—H22A108.5
C2—C3—C4113.3 (2)C17—C22—H22A108.5
O3—C3—H3A107.5C21—C22—H22B108.5
C2—C3—H3A107.5C17—C22—H22B108.5
C4—C3—H3A107.5H22A—C22—H22B107.5
C24—C4—C3110.9 (2)C4—C24—H24A109.5
C24—C4—C23108.2 (2)C4—C24—H24B109.5
C3—C4—C23107.0 (2)H24A—C24—H24B109.5
C24—C4—C5114.4 (2)C4—C24—H24C109.5
C3—C4—C5107.12 (18)H24A—C24—H24C109.5
C23—C4—C5108.9 (2)H24B—C24—H24C109.5
C6—C5—C4113.53 (19)C4—C23—H23A109.5
C6—C5—C10110.8 (2)C4—C23—H23B109.5
C4—C5—C10117.01 (19)H23A—C23—H23B109.5
C6—C5—H5104.7C4—C23—H23C109.5
C4—C5—H5104.7H23A—C23—H23C109.5
C10—C5—H5104.7H23B—C23—H23C109.5
C7—C6—C5110.14 (19)C10—C25—H25A109.5
C7—C6—H6A109.6C10—C25—H25B109.5
C5—C6—H6A109.6H25A—C25—H25B109.5
C7—C6—H6B109.6C10—C25—H25C109.5
C5—C6—H6B109.6H25A—C25—H25C109.5
H6A—C6—H6B108.1H25B—C25—H25C109.5
C6—C7—C8113.8 (2)C8—C26—H26A109.5
C6—C7—H7A108.8C8—C26—H26B109.5
C8—C7—H7A108.8H26A—C26—H26B109.5
C6—C7—H7B108.8C8—C26—H26C109.5
C8—C7—H7B108.8H26A—C26—H26C109.5
H7A—C7—H7B107.7H26B—C26—H26C109.5
C7—C8—C26107.37 (19)C14—C27—H27A109.5
C7—C8—C9110.44 (18)C14—C27—H27B109.5
C26—C8—C9110.02 (18)H27A—C27—H27B109.5
C7—C8—C14109.77 (18)C14—C27—H27C109.5
C26—C8—C14111.00 (19)H27A—C27—H27C109.5
C9—C8—C14108.26 (16)H27B—C27—H27C109.5
C11—C9—C8108.24 (18)C17—C28—H28A109.5
C11—C9—C10115.80 (18)C17—C28—H28B109.5
C8—C9—C10117.96 (17)H28A—C28—H28B109.5
C11—C9—H9104.4C17—C28—H28C109.5
C8—C9—H9104.4H28A—C28—H28C109.5
C10—C9—H9104.4H28B—C28—H28C109.5
C25—C10—C1108.58 (18)C20—C29—H29A109.5
C25—C10—C5114.1 (2)C20—C29—H29B109.5
C1—C10—C5107.31 (18)H29A—C29—H29B109.5
C25—C10—C9112.34 (18)C20—C29—H29C109.5
C1—C10—C9108.63 (18)H29A—C29—H29C109.5
C5—C10—C9105.68 (17)H29B—C29—H29C109.5
O11—C11—C12119.9 (2)O31—C30—O30123.0 (2)
O11—C11—C9122.4 (2)O31—C30—C20124.8 (2)
C12—C11—C9117.62 (18)O30—C30—C20112.1 (2)
C13—C12—C11125.0 (2)O30—C31—C32111.0 (2)
C13—C12—H12117.5O30—C31—H31A109.4
C11—C12—H12117.5C32—C31—H31A109.4
C12—C13—C18119.3 (2)O30—C31—H31B109.4
C12—C13—C14119.5 (2)C32—C31—H31B109.4
C18—C13—C14121.12 (18)H31A—C31—H31B108.0
C13—C14—C27105.79 (18)N1—C32—C31114.0 (2)
C13—C14—C15112.91 (18)N1—C32—H32A108.7
C27—C14—C15106.65 (18)C31—C32—H32A108.7
C13—C14—C8108.25 (17)N1—C32—H32B108.7
C27—C14—C8112.60 (18)C31—C32—H32B108.7
C15—C14—C8110.60 (17)H32A—C32—H32B107.6
C16—C15—C14114.37 (18)N1—C33—C34110.9 (3)
C16—C15—H15A108.7N1—C33—H33A109.5
C14—C15—H15A108.7C34—C33—H33A109.5
C16—C15—H15B108.7N1—C33—H33B109.5
C14—C15—H15B108.7C34—C33—H33B109.5
H15A—C15—H15B107.6H33A—C33—H33B108.0
C15—C16—C17112.4 (2)O1—C34—C33112.4 (3)
C15—C16—H16A109.1O1—C34—H34A109.1
C17—C16—H16A109.1C33—C34—H34A109.1
C15—C16—H16B109.1O1—C34—H34B109.1
C17—C16—H16B109.1C33—C34—H34B109.1
H16A—C16—H16B107.9H34A—C34—H34B107.9
C28—C17—C22107.3 (2)O1—C35—C36112.6 (3)
C28—C17—C16109.9 (2)O1—C35—H35A109.1
C22—C17—C16111.6 (2)C36—C35—H35A109.1
C28—C17—C18109.5 (2)O1—C35—H35B109.1
C22—C17—C18110.02 (19)C36—C35—H35B109.1
C16—C17—C18108.47 (19)H35A—C35—H35B107.8
C13—C18—C19110.13 (18)N1—C36—C35110.1 (3)
C13—C18—C17112.72 (18)N1—C36—H36A109.6
C19—C18—C17112.74 (19)C35—C36—H36A109.6
C13—C18—H18107.0N1—C36—H36B109.6
C19—C18—H18107.0C35—C36—H36B109.6
C17—C18—H18107.0H36A—C36—H36B108.1
C10—C1—C2—C357.7 (3)C26—C8—C14—C1360.0 (2)
C1—C2—C3—O3178.2 (2)C9—C8—C14—C1360.9 (2)
C1—C2—C3—C458.5 (3)C7—C8—C14—C2764.9 (2)
O3—C3—C4—C2453.7 (3)C26—C8—C14—C27176.56 (18)
C2—C3—C4—C2471.6 (3)C9—C8—C14—C2755.7 (2)
O3—C3—C4—C2364.1 (3)C7—C8—C14—C1554.3 (2)
C2—C3—C4—C23170.6 (2)C26—C8—C14—C1564.2 (2)
O3—C3—C4—C5179.2 (2)C9—C8—C14—C15174.93 (18)
C2—C3—C4—C553.9 (3)C13—C14—C15—C1635.7 (3)
C24—C4—C5—C660.6 (3)C27—C14—C15—C1680.0 (2)
C3—C4—C5—C6176.0 (2)C8—C14—C15—C16157.2 (2)
C23—C4—C5—C660.7 (3)C14—C15—C16—C1754.4 (3)
C24—C4—C5—C1070.5 (3)C15—C16—C17—C2857.9 (3)
C3—C4—C5—C1052.9 (3)C15—C16—C17—C22176.9 (2)
C23—C4—C5—C10168.3 (2)C15—C16—C17—C1861.7 (3)
C4—C5—C6—C7161.3 (2)C12—C13—C18—C1987.6 (3)
C10—C5—C6—C764.7 (3)C14—C13—C18—C1988.3 (2)
C5—C6—C7—C856.9 (3)C12—C13—C18—C17145.6 (2)
C6—C7—C8—C2674.2 (3)C14—C13—C18—C1738.6 (3)
C6—C7—C8—C945.8 (3)C28—C17—C18—C1367.6 (3)
C6—C7—C8—C14165.1 (2)C22—C17—C18—C13174.7 (2)
C7—C8—C9—C11179.27 (19)C16—C17—C18—C1352.3 (3)
C26—C8—C9—C1160.9 (2)C28—C17—C18—C19166.9 (2)
C14—C8—C9—C1160.5 (2)C22—C17—C18—C1949.2 (3)
C7—C8—C9—C1045.3 (3)C16—C17—C18—C1973.2 (2)
C26—C8—C9—C1073.0 (2)C13—C18—C19—C20177.30 (18)
C14—C8—C9—C10165.54 (18)C17—C18—C19—C2055.9 (3)
C2—C1—C10—C2571.2 (3)C18—C19—C20—C3064.4 (3)
C2—C1—C10—C552.6 (3)C18—C19—C20—C2157.4 (3)
C2—C1—C10—C9166.40 (19)C18—C19—C20—C29176.5 (2)
C6—C5—C10—C2564.5 (2)C30—C20—C21—C2267.3 (3)
C4—C5—C10—C2567.9 (3)C19—C20—C21—C2255.5 (3)
C6—C5—C10—C1175.23 (19)C29—C20—C21—C22175.4 (2)
C4—C5—C10—C152.5 (3)C20—C21—C22—C1753.6 (3)
C6—C5—C10—C959.4 (2)C28—C17—C22—C21167.9 (2)
C4—C5—C10—C9168.25 (19)C16—C17—C22—C2171.6 (3)
C11—C9—C10—C2557.1 (3)C18—C17—C22—C2148.9 (3)
C8—C9—C10—C2573.4 (2)C31—O30—C30—O312.4 (4)
C11—C9—C10—C163.0 (2)C31—O30—C30—C20179.4 (2)
C8—C9—C10—C1166.43 (18)C21—C20—C30—O3124.0 (4)
C11—C9—C10—C5177.90 (18)C19—C20—C30—O31145.0 (2)
C8—C9—C10—C551.5 (2)C29—C20—C30—O3194.2 (3)
C8—C9—C11—O11149.0 (2)C21—C20—C30—O30159.0 (2)
C10—C9—C11—O1114.0 (3)C19—C20—C30—O3038.0 (3)
C8—C9—C11—C1232.0 (3)C29—C20—C30—O3082.7 (2)
C10—C9—C11—C12167.1 (2)C30—O30—C31—C3298.1 (3)
O11—C11—C12—C13178.2 (2)C36—N1—C32—C3170.4 (3)
C9—C11—C12—C132.8 (4)C33—N1—C32—C31169.0 (3)
C11—C12—C13—C18179.1 (2)O30—C31—C32—N168.8 (3)
C11—C12—C13—C143.2 (4)C36—N1—C33—C3457.2 (4)
C12—C13—C14—C2788.7 (2)C32—N1—C33—C34180.0 (3)
C18—C13—C14—C2787.2 (2)C35—O1—C34—C3356.6 (5)
C12—C13—C14—C15155.0 (2)N1—C33—C34—O158.3 (4)
C18—C13—C14—C1529.1 (3)C34—O1—C35—C3656.7 (5)
C12—C13—C14—C832.2 (3)C32—N1—C36—C35179.0 (3)
C18—C13—C14—C8151.92 (19)C33—N1—C36—C3556.7 (4)
C7—C8—C14—C13178.50 (18)O1—C35—C36—N158.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O11i0.841.952.790 (2)173
Symmetry code: (i) x+1, y1/2, z+3/2.
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds