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The asymmetric unit of the title compound, C24H36O4, contains three mol­ecules, all differing in their side-chain conformations and all linked by hydrogen bonding confined entirely within a three-mol­ecule block. One connection is of the acid-to-ketone type [O...O = 2.7055 (19) Å and O-H...O = 180°] and the other involves carboxyl pairing [O...O = 2.6485 (18) and 2.6598 (18) Å, and O-H...O = 168 and 174°]. Numerous inter­molecular C-H...O close contacts connect neighbouring mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010601136X/sk3014sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010601136X/sk3014Isup2.hkl
Contains datablock I

CCDC reference: 616138

Comment top

For our study of H-bonding modes in crystalline keto acids, steroid examples are of special value as molecularly rigid single enantiomers with the potential for multiple ketone receptors. The title compound (I) supplements our previous reports on steroidal diketo acids related to the bile acids (Thompson et al., 2001; Newman et al., 2002; Lalancette & Thompson, 2003). The natural bile acids all have cis AB ring junctures, a carboxyl in the C17 side-chain and oxygenation at the 3-position; most are oxygenated at the 6-, 7- and/or 12-positions as well. Various combinations of these acids are present in substantial quantities in vertebrate bile, where they function as surfactants, and are isolatable directly from gall bladders. Although the ring-oxygenation typically involves hydroxyl groups, a few natural bile acids contain ketone functions as well (Fieser & Fieser, 1959). Compound (I) is not known to occur naturally, but was produced by oxidation of a known natural source (Experimental).

Fig. 1 shows the asymmetric unit for (I), consisting of three molecules, designated (IA), (IB) & (IC), which have significant conformational differences only at the extremity of the 5-carbon acid-chain attached at C17. Superimposition of truncated molecules lacking the carboxyl (C24) and stripped of all H atoms shows negligible differences, with r.m.s. deviations averaging less than 0.1 Å.

All three molecules have an anti conformational arrangement about the C20—C22 bond, but only (IC) also has an anti conformation about C22—C23, whose torsion angle (C20—C22—C23—C24) is −174.27 (16)°. The two remaining molecules have similar gauche arrangements about C22—C23, with the above torsion angle being 80.2 (2)° for (IA) and 67.2 (2)° for (IB). However, these two molecules differ in the conformation of their carboxyl groups; the torsion angle O3—C24—C23—C22 is 129.8 (2)° for (IA) and −0.3 (3)° for (IB).

Values typical of C—O bond lengths and C—C—O angles in highly ordered dimeric carboxyls are 1.21 & 1.31 Å and 123 & 112°, respectively (Borthwick, 1980). Full or partial averaging of these lengths and angles by disorder is common in dimeric acids, but is invariably absent in other H-bonding modes, which cannot support the underlying averaging mechanisms. All the carboxyl groups in (I) show negligible disordering (see Table 1).

Fig. 1 also illustrates the entire H-bonding scheme, which consists of (IA), (IB) & (IC), with no H bonding beyond the three molecules shown. This leaves the two C3 ketone functions at the remote ends of this block without H-bonding partners, as is the case for all the B-ring ketones at C7.

Fig. 2 shows the packing of the cell with the chosen asymmetric unit and includes extra molecules to illustrate its isolation from other H bonding. Within the 2.7 Å range we standardly survey for non-bonded H···O packing interactions (Steiner, 1997), a dozen intermolecular C—H···O close contacts exist (see Table 2).

We characterize the geometry of H bonding to carbonyls using a combination of H···O=C angle and H···O=C—C torsion angle. These describe the approach of the acid H atom to the receptor O in terms of its deviation from, respectively, C=O axiality (ideal = 120°) and planarity with the carbonyl (ideal = 0°). In the acid-to-ketone connection in (I), these two angles are 124.3° and 40.2°.

The solid-state (KBr) infrared spectrum of (I) has broad C=O absorption centered at 1703 cm−1, which is shifted to 1711 cm−1 in CHCl3 solution. In addition, the KBr spectrum contains a much smaller peak at 1653 cm−1, absent in CHCl3 and probably due to the single ketone (of the six in the asymmetric unit) whose position is shifted by H bonding.

Experimental top

3α-Hydroxy-7-oxo-5β-cholanic acid (7-ketolithocholic acid, isolatable from the bile of guinea pig and nutria), purchased from TCI America, Portland, Oregon, USA (Quantity?), was dissolved in acetone (Volume?) and subjected to Jones oxidation (Is a reference needed here?), yielding 92% of (I). Refrigerating an acetonitrile solution produced the crystal used (m.p. 433 K). Compound (I) may also be obtained by oxidation of either `ursodeoxycholic' or `chenodeoxycholic' acids, the latter being one of the two principal steroidal acids in human bile. The sign of rotation for (I) is well established (Kagan & Jacques, 1957) and the absolute stereochemistry of (I), consistent with our experimental Flack parameter (Flack, 1983), corresponds to that of other steroids and bile acids (Fieser & Fieser, 1959; Klyne & Buckingham, 1978).

Refinement top

All H atoms of (I) were found in electron-density difference maps but were placed in calculated positions and allowed to refine as riding on their respective C or O atoms. The O—H distances were fixed at 0.84 Å. For methyl, methylene and methine H atoms, C—H distances were fixed at 0.98, 0.99 and 1.00 Å, respectively. Uiso(H) = 1.5Ueq(parent) for H atoms on O and methyl C atoms, and 1.2Ueq(parent) for all others. [Please check added text and correct as necessary]

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1]
[Figure 2]
Fig. 1. The asymmetric unit of (I); the three identically numbered molecules differ significantly only in their side-chain conformations. Molecules (IB) and (IC) are identified by numbering at O1. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.

Fig. 2. The hydrogen-bonded block consisting of molecules (IB), (IC) and (IA) (left to right, respectively), shown in their linear isolated hydrogen-bonded arrangement. The hydrogen-bonding mode connecting molecules (IA) and (IC) differs from that between (IB) and (IC). Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Fig. 3. A partial packing diagram for (I), with extra molecules included to illustrate the three-molecule hydrogen-bonded block and its isolation from other hydrogen bonding. For clarity, all C-bound H atoms have been omitted. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
(-)-3,7-Dioxo-5β-cholanic acid top
Crystal data top
C24H36O4Dx = 1.226 Mg m3
Mr = 388.53Melting point: 433 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab'Cell parameters from 27061 reflections
a = 7.6177 (1) Åθ = 2.2–69.6°
b = 27.6911 (4) ŵ = 0.65 mm1
c = 29.9256 (4) ÅT = 100 K
V = 6312.58 (15) Å3Block, colourless
Z = 120.22 × 0.13 × 0.12 mm
F(000) = 2544
Data collection top
Bruker SMART CCD APEX II area-detector
diffractometer
10459 independent reflections
Radiation source: fine-focus sealed tube9648 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 69.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Blessing, 1995)
h = 79
Tmin = 0.871, Tmax = 0.927k = 2733
27061 measured reflectionsl = 3523
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0471P)2 + 1.0308P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max = 0.01
S = 1.07Δρmax = 0.21 e Å3
10459 reflectionsΔρmin = 0.16 e Å3
758 parametersExtinction correction: SHELXL97 (Sheldrick,1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00006 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.14 (13)
Crystal data top
C24H36O4V = 6312.58 (15) Å3
Mr = 388.53Z = 12
Orthorhombic, P212121Cu Kα radiation
a = 7.6177 (1) ŵ = 0.65 mm1
b = 27.6911 (4) ÅT = 100 K
c = 29.9256 (4) Å0.22 × 0.13 × 0.12 mm
Data collection top
Bruker SMART CCD APEX II area-detector
diffractometer
10459 independent reflections
Absorption correction: multi-scan
(SADABS; Blessing, 1995)
9648 reflections with I > 2σ(I)
Tmin = 0.871, Tmax = 0.927Rint = 0.022
27061 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.091Δρmax = 0.21 e Å3
S = 1.07Δρmin = 0.16 e Å3
10459 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
758 parametersAbsolute structure parameter: 0.14 (13)
0 restraints
Special details top

Experimental. crystal mounted on cryoloop using Paratone-N

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1B0.0703 (3)0.08970 (7)0.10454 (7)0.0242 (4)
H1BA0.03920.10740.09750.029*
H1BB0.04240.06560.12790.029*
O1C0.2229 (3)1.05006 (6)0.23980 (6)0.0541 (5)
C1C0.3510 (3)0.95205 (7)0.30150 (6)0.0221 (4)
H1CA0.34380.97720.32500.026*
H1CB0.45620.93220.30770.026*
O1B0.3251 (2)0.00527 (5)0.06408 (5)0.0315 (3)
O2C0.20804 (18)0.87207 (5)0.22685 (4)0.0261 (3)
O2B0.67573 (17)0.17489 (5)0.08846 (5)0.0303 (3)
C2B0.1317 (3)0.06287 (7)0.06220 (7)0.0256 (4)
H2BA0.04160.03910.05300.031*
H2BB0.14780.08620.03750.031*
C2C0.3751 (3)0.97685 (7)0.25622 (7)0.0279 (4)
H2CA0.48110.99750.25670.033*
H2CB0.38950.95240.23240.033*
O3B0.26444 (19)0.46326 (5)0.09675 (4)0.0270 (3)
O3C0.1446 (2)0.56650 (5)0.14071 (5)0.0334 (4)
C3B0.3013 (3)0.03752 (7)0.07151 (6)0.0234 (4)
C3C0.2153 (3)1.00698 (7)0.24737 (7)0.0328 (5)
O4C0.33746 (18)0.51493 (5)0.16933 (4)0.0253 (3)
H4CC0.31250.49930.14620.038*
O4B0.1241 (2)0.52327 (5)0.06194 (5)0.0348 (4)
H4BC0.13190.53640.08720.052*
C4C0.0440 (3)0.98022 (8)0.25057 (7)0.0301 (5)
H4CA0.03370.95810.22470.036*
H4CB0.05361.00380.24870.036*
C4B0.4423 (2)0.06828 (7)0.09164 (6)0.0218 (4)
H4BA0.48740.09070.06860.026*
H4BB0.54080.04730.10110.026*
C5B0.3792 (3)0.09785 (7)0.13217 (6)0.0208 (4)
H5BA0.35690.07470.15720.025*
C5C0.0247 (3)0.95082 (7)0.29388 (6)0.0232 (4)
H5CA0.00960.97440.31890.028*
C6B0.5301 (3)0.13179 (7)0.14703 (6)0.0245 (4)
H6BA0.50320.14580.17670.029*
H6BB0.64110.11340.14940.029*
C6C0.1459 (3)0.92032 (7)0.29117 (7)0.0258 (4)
H6CA0.17810.90880.32140.031*
H6CB0.24310.94070.27980.031*
C7C0.1204 (2)0.87750 (7)0.26052 (6)0.0215 (4)
C7B0.5491 (3)0.17147 (7)0.11283 (6)0.0218 (4)
C8C0.0299 (2)0.84461 (6)0.27338 (6)0.0176 (4)
H8CA0.01180.83390.30500.021*
C8B0.3872 (2)0.20283 (6)0.10814 (6)0.0178 (4)
H8BA0.35280.21460.13850.021*
C9C0.1994 (2)0.87638 (6)0.27151 (6)0.0182 (4)
H9CA0.20270.89080.24090.022*
C9B0.2394 (2)0.16826 (6)0.09051 (6)0.0171 (4)
H9BA0.28540.15360.06230.021*
C10B0.2056 (3)0.12557 (6)0.12331 (6)0.0201 (4)
C10C0.1875 (2)0.91968 (6)0.30481 (6)0.0193 (4)
C11C0.3682 (2)0.84661 (6)0.27623 (7)0.0214 (4)
H11A0.38330.83770.30800.026*
H11B0.46920.86710.26760.026*
C11B0.0724 (2)0.19599 (6)0.07756 (6)0.0198 (4)
H11C0.00900.20500.10520.024*
H11D0.00480.17410.06030.024*
C12B0.1042 (2)0.24190 (6)0.04995 (6)0.0196 (4)
H12A0.14810.23280.02000.024*
H12B0.00830.25930.04600.024*
C12C0.3715 (2)0.80036 (7)0.24790 (6)0.0219 (4)
H12C0.37550.80910.21580.026*
H12D0.47880.78170.25490.026*
C13C0.2096 (2)0.76890 (6)0.25675 (6)0.0181 (4)
C13B0.2372 (2)0.27552 (6)0.07246 (6)0.0169 (4)
C14C0.0479 (2)0.79995 (6)0.24422 (6)0.0171 (4)
H14A0.06600.81140.21290.021*
C14B0.4087 (2)0.24625 (6)0.07752 (6)0.0177 (4)
H14B0.43960.23360.04720.021*
C15B0.5460 (3)0.28426 (7)0.08952 (7)0.0247 (4)
H15A0.66470.27370.08020.030*
H15B0.54660.29060.12210.030*
C15C0.1060 (2)0.76445 (6)0.24341 (6)0.0202 (4)
H15C0.19870.77550.22260.024*
H15D0.15730.76050.27360.024*
C16C0.0219 (2)0.71675 (6)0.22697 (6)0.0187 (4)
H16A0.06670.70830.19690.022*
H16B0.05060.69000.24770.022*
C16B0.4886 (2)0.32975 (7)0.06333 (6)0.0227 (4)
H16C0.57120.33620.03850.027*
H16D0.48690.35820.08330.027*
C17B0.3007 (2)0.31960 (6)0.04470 (6)0.0184 (4)
H17A0.31360.30880.01300.022*
C17C0.1806 (2)0.72495 (6)0.22534 (6)0.0175 (4)
H17B0.21080.73560.19430.021*
C18B0.1676 (3)0.29308 (7)0.11795 (6)0.0212 (4)
H18A0.12750.26530.13550.032*
H18B0.06930.31530.11320.032*
H18C0.26150.30980.13410.032*
C18C0.2049 (3)0.75198 (6)0.30556 (6)0.0201 (4)
H18D0.22320.77970.32540.030*
H18E0.29800.72810.31050.030*
H18F0.09060.73730.31200.030*
C19C0.1761 (3)0.90257 (7)0.35363 (6)0.0239 (4)
H19A0.16870.93070.37340.036*
H19B0.28100.88370.36110.036*
H19C0.07140.88240.35750.036*
C19B0.1309 (3)0.14349 (7)0.16807 (6)0.0275 (4)
H19D0.11120.11590.18790.041*
H19E0.01940.16020.16280.041*
H19F0.21450.16580.18200.041*
C20B0.1860 (3)0.36548 (6)0.04463 (6)0.0190 (4)
H20A0.17650.37720.07610.023*
C20C0.2825 (2)0.67792 (6)0.23457 (6)0.0188 (4)
H20B0.25140.66640.26520.023*
C21C0.4830 (3)0.68510 (7)0.23239 (6)0.0236 (4)
H21A0.54190.65430.23840.035*
H21B0.51880.70900.25480.035*
H21C0.51590.69660.20260.035*
C21B0.0008 (3)0.35638 (7)0.02719 (7)0.0257 (4)
H21D0.06760.38660.02790.039*
H21E0.05890.33230.04610.039*
H21F0.00500.34440.00360.039*
C22C0.2232 (3)0.63960 (6)0.20082 (6)0.0204 (4)
H22A0.09410.63630.20300.024*
H22B0.25060.65150.17040.024*
C22B0.2757 (3)0.40527 (6)0.01701 (6)0.0221 (4)
H22C0.39830.40860.02750.027*
H22D0.28000.39470.01460.027*
C23C0.3050 (3)0.58969 (7)0.20637 (6)0.0248 (4)
H23A0.43440.59280.20690.030*
H23B0.26720.57570.23530.030*
C23B0.1885 (3)0.45498 (6)0.01880 (6)0.0242 (4)
H23C0.24530.47600.00370.029*
H23D0.06380.45140.01010.029*
C24C0.2525 (2)0.55633 (6)0.16906 (6)0.0209 (4)
C24B0.1960 (3)0.47999 (6)0.06339 (6)0.0219 (4)
O1A0.2803 (2)0.49928 (6)0.16173 (5)0.0421 (4)
C1A0.1323 (3)0.42128 (7)0.08165 (7)0.0253 (4)
H1AA0.14220.45170.06450.030*
H1AB0.02400.40470.07170.030*
O2A0.68691 (18)0.31652 (5)0.13052 (4)0.0274 (3)
C2A0.1143 (3)0.43359 (7)0.13136 (7)0.0280 (4)
H2AA0.01140.45480.13620.034*
H2AB0.09760.40370.14900.034*
O3A0.2354 (3)0.02130 (5)0.03940 (5)0.0450 (4)
C3A0.2787 (3)0.45881 (7)0.14572 (6)0.0302 (5)
O4A0.2099 (2)0.05186 (5)0.00978 (4)0.0386 (4)
H4AC0.24570.03730.01310.058*
C4A0.4453 (3)0.43121 (8)0.13653 (7)0.0275 (4)
H4AA0.44990.40260.15630.033*
H4AB0.54730.45190.14370.033*
C5A0.4590 (3)0.41457 (7)0.08738 (6)0.0252 (4)
H5AA0.47600.44410.06870.030*
C6A0.6249 (3)0.38302 (7)0.08185 (7)0.0250 (4)
H6AA0.65510.38060.04970.030*
H6AB0.72470.39850.09750.030*
C7A0.5960 (3)0.33292 (7)0.10072 (6)0.0226 (4)
C8A0.4400 (2)0.30677 (7)0.08124 (6)0.0211 (4)
H8AA0.45450.30590.04800.025*
C9A0.2756 (2)0.33799 (7)0.09198 (6)0.0218 (4)
H9AA0.27600.34310.12510.026*
C10A0.2911 (3)0.38904 (7)0.07038 (6)0.0227 (4)
C11A0.1020 (3)0.31243 (7)0.08093 (7)0.0276 (4)
H11E0.08320.31370.04820.033*
H11F0.00460.33030.09530.033*
C12A0.0946 (2)0.25925 (7)0.09619 (7)0.0253 (4)
H12E0.09290.25800.12930.030*
H12F0.01530.24440.08520.030*
C13A0.2506 (2)0.23040 (7)0.07902 (6)0.0210 (4)
C14A0.4173 (2)0.25511 (7)0.09763 (6)0.0201 (4)
H14C0.40300.25680.13080.024*
C15A0.5659 (3)0.21942 (7)0.08849 (6)0.0239 (4)
H15E0.65910.22220.11140.029*
H15F0.61800.22510.05860.029*
C16A0.4765 (2)0.16919 (7)0.09070 (7)0.0241 (4)
H16E0.52460.15020.11590.029*
H16F0.49700.15110.06260.029*
C17A0.2769 (2)0.17831 (7)0.09754 (6)0.0207 (4)
H17C0.25610.17980.13050.025*
C18A0.2509 (3)0.22842 (7)0.02745 (6)0.0260 (4)
H18G0.23440.26100.01550.039*
H18H0.15520.20760.01720.039*
H18I0.36330.21540.01700.039*
C19A0.2986 (3)0.38614 (7)0.01886 (6)0.0286 (4)
H19G0.30820.41880.00640.043*
H19H0.19150.37080.00770.043*
H19I0.40090.36710.00980.043*
C20A0.1627 (3)0.13683 (7)0.07929 (6)0.0226 (4)
H20C0.18610.13360.04650.027*
C21A0.0329 (3)0.14693 (8)0.08574 (7)0.0295 (4)
H21G0.10140.11990.07380.044*
H21H0.06470.17660.06990.044*
H21I0.05800.15070.11770.044*
C22A0.2149 (3)0.08917 (7)0.10212 (6)0.0278 (4)
H22E0.34330.08500.09870.033*
H22F0.19080.09240.13450.033*
C23A0.1247 (3)0.04276 (7)0.08543 (7)0.0303 (5)
H23E0.13200.01820.10940.036*
H23F0.00120.05000.08060.036*
C24A0.1961 (3)0.02083 (7)0.04335 (7)0.0262 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1B0.0199 (9)0.0179 (9)0.0349 (10)0.0017 (8)0.0034 (8)0.0045 (8)
O1C0.0667 (12)0.0287 (8)0.0670 (11)0.0068 (9)0.0081 (10)0.0215 (8)
C1C0.0235 (10)0.0184 (9)0.0244 (9)0.0038 (8)0.0004 (8)0.0016 (8)
O1B0.0382 (8)0.0198 (7)0.0367 (7)0.0064 (6)0.0096 (7)0.0073 (6)
O2C0.0215 (7)0.0257 (7)0.0311 (7)0.0006 (6)0.0046 (6)0.0006 (6)
O2B0.0161 (7)0.0273 (7)0.0474 (8)0.0000 (6)0.0003 (7)0.0038 (7)
C2B0.0221 (10)0.0203 (9)0.0344 (10)0.0013 (8)0.0070 (9)0.0023 (9)
C2C0.0309 (11)0.0241 (10)0.0285 (10)0.0092 (9)0.0028 (9)0.0003 (9)
O3B0.0353 (8)0.0194 (6)0.0263 (7)0.0012 (6)0.0041 (6)0.0023 (6)
O3C0.0380 (9)0.0246 (7)0.0377 (8)0.0120 (7)0.0165 (7)0.0090 (6)
C3B0.0284 (10)0.0199 (9)0.0218 (9)0.0010 (8)0.0007 (8)0.0002 (7)
C3C0.0468 (13)0.0258 (10)0.0258 (9)0.0050 (10)0.0051 (10)0.0064 (9)
O4C0.0318 (8)0.0192 (6)0.0249 (6)0.0061 (6)0.0038 (6)0.0018 (5)
O4B0.0476 (9)0.0215 (7)0.0353 (8)0.0088 (7)0.0133 (7)0.0082 (6)
C4C0.0354 (12)0.0249 (10)0.0300 (10)0.0052 (9)0.0092 (10)0.0022 (9)
C4B0.0206 (9)0.0191 (9)0.0258 (9)0.0037 (7)0.0002 (8)0.0022 (8)
C5B0.0253 (10)0.0175 (9)0.0197 (8)0.0026 (8)0.0005 (8)0.0009 (7)
C5C0.0237 (10)0.0196 (9)0.0264 (9)0.0021 (8)0.0008 (8)0.0038 (8)
C6B0.0258 (10)0.0223 (10)0.0256 (9)0.0041 (8)0.0077 (8)0.0018 (8)
C6C0.0199 (10)0.0236 (10)0.0340 (10)0.0033 (8)0.0001 (8)0.0052 (8)
C7C0.0150 (9)0.0221 (9)0.0274 (10)0.0027 (8)0.0025 (8)0.0006 (8)
C7B0.0192 (9)0.0200 (9)0.0262 (9)0.0016 (8)0.0072 (8)0.0040 (8)
C8C0.0164 (8)0.0186 (9)0.0177 (8)0.0019 (7)0.0011 (7)0.0011 (7)
C8B0.0189 (9)0.0170 (9)0.0176 (8)0.0013 (8)0.0021 (7)0.0024 (7)
C9C0.0187 (9)0.0166 (8)0.0195 (8)0.0017 (8)0.0002 (8)0.0004 (7)
C9B0.0176 (9)0.0159 (8)0.0179 (8)0.0015 (7)0.0023 (7)0.0016 (7)
C10B0.0215 (9)0.0174 (8)0.0215 (9)0.0016 (8)0.0045 (8)0.0009 (7)
C10C0.0200 (9)0.0176 (8)0.0202 (9)0.0030 (8)0.0011 (8)0.0007 (7)
C11C0.0155 (9)0.0185 (9)0.0302 (10)0.0025 (7)0.0010 (8)0.0018 (8)
C11B0.0160 (9)0.0162 (8)0.0270 (9)0.0013 (7)0.0009 (8)0.0013 (8)
C12B0.0184 (9)0.0177 (9)0.0227 (9)0.0016 (7)0.0013 (8)0.0005 (7)
C12C0.0168 (9)0.0216 (9)0.0273 (9)0.0005 (8)0.0027 (8)0.0025 (8)
C13C0.0183 (9)0.0171 (8)0.0189 (8)0.0003 (8)0.0005 (7)0.0007 (7)
C13B0.0170 (9)0.0165 (8)0.0172 (8)0.0005 (7)0.0004 (7)0.0019 (7)
C14C0.0153 (9)0.0177 (9)0.0184 (8)0.0023 (7)0.0010 (7)0.0004 (7)
C14B0.0156 (8)0.0188 (9)0.0187 (8)0.0000 (7)0.0001 (7)0.0022 (7)
C15B0.0200 (9)0.0230 (9)0.0312 (10)0.0009 (8)0.0057 (8)0.0007 (9)
C15C0.0181 (9)0.0200 (9)0.0224 (9)0.0011 (8)0.0009 (8)0.0023 (8)
C16C0.0203 (9)0.0176 (9)0.0183 (8)0.0023 (7)0.0009 (8)0.0007 (7)
C16B0.0195 (9)0.0197 (9)0.0290 (9)0.0035 (8)0.0024 (8)0.0006 (8)
C17B0.0199 (9)0.0181 (8)0.0171 (8)0.0016 (8)0.0015 (8)0.0031 (7)
C17C0.0199 (9)0.0183 (9)0.0144 (8)0.0020 (8)0.0016 (7)0.0007 (7)
C18B0.0240 (10)0.0198 (9)0.0199 (9)0.0011 (8)0.0029 (8)0.0004 (7)
C18C0.0212 (9)0.0197 (8)0.0194 (8)0.0002 (8)0.0016 (8)0.0021 (7)
C19C0.0285 (10)0.0226 (9)0.0206 (9)0.0036 (8)0.0015 (8)0.0001 (8)
C19B0.0334 (11)0.0242 (10)0.0250 (9)0.0048 (9)0.0107 (9)0.0031 (8)
C20B0.0226 (9)0.0165 (8)0.0179 (8)0.0001 (8)0.0005 (8)0.0013 (7)
C20C0.0203 (9)0.0192 (9)0.0169 (8)0.0001 (8)0.0011 (7)0.0002 (7)
C21C0.0230 (10)0.0200 (9)0.0277 (9)0.0002 (8)0.0007 (8)0.0017 (8)
C21B0.0260 (10)0.0193 (9)0.0318 (10)0.0005 (8)0.0037 (9)0.0031 (8)
C22C0.0221 (9)0.0196 (9)0.0194 (8)0.0021 (8)0.0003 (8)0.0019 (7)
C22B0.0279 (10)0.0184 (9)0.0200 (8)0.0017 (8)0.0009 (8)0.0005 (7)
C23C0.0291 (10)0.0199 (9)0.0254 (9)0.0021 (9)0.0033 (9)0.0012 (8)
C23B0.0322 (10)0.0174 (9)0.0230 (9)0.0032 (8)0.0016 (9)0.0015 (7)
C24C0.0198 (9)0.0175 (9)0.0255 (9)0.0005 (7)0.0024 (8)0.0031 (8)
C24B0.0205 (9)0.0165 (8)0.0287 (10)0.0042 (8)0.0005 (8)0.0014 (8)
O1A0.0505 (10)0.0324 (8)0.0435 (8)0.0075 (8)0.0081 (8)0.0085 (7)
C1A0.0223 (10)0.0242 (10)0.0295 (10)0.0021 (8)0.0018 (8)0.0025 (8)
O2A0.0206 (7)0.0343 (8)0.0274 (7)0.0006 (6)0.0040 (6)0.0056 (6)
C2A0.0253 (10)0.0257 (10)0.0331 (10)0.0075 (9)0.0044 (9)0.0013 (9)
O3A0.0637 (12)0.0236 (8)0.0477 (9)0.0042 (8)0.0092 (9)0.0024 (7)
C3A0.0399 (12)0.0268 (11)0.0237 (9)0.0033 (10)0.0001 (9)0.0032 (8)
O4A0.0666 (11)0.0245 (7)0.0246 (7)0.0136 (8)0.0056 (8)0.0006 (6)
C4A0.0255 (10)0.0301 (11)0.0270 (10)0.0029 (9)0.0016 (8)0.0020 (9)
C5A0.0256 (10)0.0250 (10)0.0251 (9)0.0002 (8)0.0021 (8)0.0046 (9)
C6A0.0191 (9)0.0289 (10)0.0271 (10)0.0015 (8)0.0014 (8)0.0051 (8)
C7A0.0180 (9)0.0290 (10)0.0208 (9)0.0039 (8)0.0051 (8)0.0010 (8)
C8A0.0185 (9)0.0263 (10)0.0183 (8)0.0038 (8)0.0017 (7)0.0023 (8)
C9A0.0194 (9)0.0242 (9)0.0219 (8)0.0037 (8)0.0010 (8)0.0005 (8)
C10A0.0222 (9)0.0239 (9)0.0220 (9)0.0035 (8)0.0013 (8)0.0032 (8)
C11A0.0178 (9)0.0262 (10)0.0388 (11)0.0048 (8)0.0000 (9)0.0006 (9)
C12A0.0157 (9)0.0241 (10)0.0361 (11)0.0003 (8)0.0011 (8)0.0029 (9)
C13A0.0175 (9)0.0258 (9)0.0197 (9)0.0023 (8)0.0008 (7)0.0005 (8)
C14A0.0178 (9)0.0252 (10)0.0172 (8)0.0009 (8)0.0003 (7)0.0026 (8)
C15A0.0206 (9)0.0272 (10)0.0238 (9)0.0038 (8)0.0011 (8)0.0039 (8)
C16A0.0207 (9)0.0265 (10)0.0250 (9)0.0033 (8)0.0023 (8)0.0023 (9)
C17A0.0215 (9)0.0251 (9)0.0156 (8)0.0032 (8)0.0005 (7)0.0008 (7)
C18A0.0272 (10)0.0285 (10)0.0222 (9)0.0005 (8)0.0060 (8)0.0019 (8)
C19A0.0304 (11)0.0327 (11)0.0226 (9)0.0024 (9)0.0035 (9)0.0035 (8)
C20A0.0247 (10)0.0246 (9)0.0186 (8)0.0023 (8)0.0005 (8)0.0026 (8)
C21A0.0265 (10)0.0309 (11)0.0312 (10)0.0024 (9)0.0005 (9)0.0051 (9)
C22A0.0332 (11)0.0288 (10)0.0215 (9)0.0001 (9)0.0025 (9)0.0008 (8)
C23A0.0360 (11)0.0249 (10)0.0300 (10)0.0024 (9)0.0001 (10)0.0038 (9)
C24A0.0254 (10)0.0216 (9)0.0318 (10)0.0017 (9)0.0031 (9)0.0014 (8)
Geometric parameters (Å, º) top
C1B—C10B1.538 (3)C18C—H18D0.9800
C1B—C2B1.542 (3)C18C—H18E0.9800
C1B—H1BA0.9900C18C—H18F0.9800
C1B—H1BB0.9900C19C—H19A0.9800
O1C—C3C1.216 (2)C19C—H19B0.9800
C1C—C2C1.530 (3)C19C—H19C0.9800
C1C—C10C1.537 (2)C19B—H19D0.9800
C1C—H1CA0.9900C19B—H19E0.9800
C1C—H1CB0.9900C19B—H19F0.9800
O1B—C3B1.219 (2)C20B—C21B1.536 (3)
O2C—C7C1.218 (2)C20B—C22B1.538 (2)
O2B—C7B1.213 (2)C20B—H20A1.0000
C2B—C3B1.496 (3)C20C—C22C1.533 (2)
C2B—H2BA0.9900C20C—C21C1.542 (3)
C2B—H2BB0.9900C20C—H20B1.0000
C2C—C3C1.499 (3)C21C—H21A0.9800
C2C—H2CA0.9900C21C—H21B0.9800
C2C—H2CB0.9900C21C—H21C0.9800
O3B—C24B1.218 (2)C21B—H21D0.9800
O3C—C24C1.214 (2)C21B—H21E0.9800
C3B—C4B1.498 (3)C21B—H21F0.9800
C3C—C4C1.504 (3)C22C—C23C1.525 (2)
O4C—C24C1.317 (2)C22C—H22A0.9900
O4C—H4CC0.8400C22C—H22B0.9900
O4B—C24B1.318 (2)C22B—C23B1.529 (2)
O4B—H4BC0.8400C22B—H22C0.9900
C4C—C5C1.537 (3)C22B—H22D0.9900
C4C—H4CA0.9900C23C—C24C1.503 (3)
C4C—H4CB0.9900C23C—H23A0.9900
C4B—C5B1.540 (3)C23C—H23B0.9900
C4B—H4BA0.9900C23B—C24B1.504 (3)
C4B—H4BB0.9900C23B—H23C0.9900
C5B—C6B1.550 (3)C23B—H23D0.9900
C5B—C10B1.552 (2)O1A—C3A1.219 (2)
C5B—H5BA1.0000C1A—C2A1.532 (3)
C5C—C10C1.546 (3)C1A—C10A1.541 (3)
C5C—C6C1.552 (3)C1A—H1AA0.9900
C5C—H5CA1.0000C1A—H1AB0.9900
C6B—C7B1.508 (3)O2A—C7A1.217 (2)
C6B—H6BA0.9900C2A—C3A1.497 (3)
C6B—H6BB0.9900C2A—H2AA0.9900
C6C—C7C1.512 (3)C2A—H2AB0.9900
C6C—H6CA0.9900O3A—C24A1.210 (2)
C6C—H6CB0.9900C3A—C4A1.507 (3)
C7C—C8C1.513 (2)O4A—C24A1.326 (2)
C7B—C8B1.515 (2)O4A—H4AC0.8400
C8C—C14C1.520 (2)C4A—C5A1.545 (3)
C8C—C9C1.563 (2)C4A—H4AA0.9900
C8C—H8CA1.0000C4A—H4AB0.9900
C8B—C14B1.520 (2)C5A—C6A1.545 (3)
C8B—C9B1.569 (2)C5A—C10A1.547 (3)
C8B—H8BA1.0000C5A—H5AA1.0000
C9C—C11C1.534 (2)C6A—C7A1.514 (3)
C9C—C10C1.562 (2)C6A—H6AA0.9900
C9C—H9CA1.0000C6A—H6AB0.9900
C9B—C11B1.536 (2)C7A—C8A1.509 (3)
C9B—C10B1.558 (2)C8A—C14A1.522 (3)
C9B—H9BA1.0000C8A—C9A1.555 (2)
C10B—C19B1.538 (2)C8A—H8AA1.0000
C10C—C19C1.538 (2)C9A—C11A1.535 (3)
C11C—C12C1.536 (2)C9A—C10A1.559 (2)
C11C—H11A0.9900C9A—H9AA1.0000
C11C—H11B0.9900C10A—C19A1.545 (2)
C11B—C12B1.536 (2)C11A—C12A1.543 (3)
C11B—H11C0.9900C11A—H11E0.9900
C11B—H11D0.9900C11A—H11F0.9900
C12B—C13B1.532 (2)C12A—C13A1.522 (3)
C12B—H12A0.9900C12A—H12E0.9900
C12B—H12B0.9900C12A—H12F0.9900
C12C—C13C1.533 (2)C13A—C18A1.544 (2)
C12C—H12C0.9900C13A—C14A1.546 (2)
C12C—H12D0.9900C13A—C17A1.558 (2)
C13C—C18C1.534 (2)C14A—C15A1.527 (2)
C13C—C14C1.548 (2)C14A—H14C1.0000
C13C—C17C1.553 (2)C15A—C16A1.550 (3)
C13B—C18B1.540 (2)C15A—H15E0.9900
C13B—C14B1.545 (2)C15A—H15F0.9900
C13B—C17B1.553 (2)C16A—C17A1.555 (3)
C14C—C15C1.530 (2)C16A—H16E0.9900
C14C—H14A1.0000C16A—H16F0.9900
C14B—C15B1.527 (2)C17A—C20A1.541 (3)
C14B—H14B1.0000C17A—H17C1.0000
C15B—C16B1.547 (3)C18A—H18G0.9800
C15B—H15A0.9900C18A—H18H0.9800
C15B—H15B0.9900C18A—H18I0.9800
C15C—C16C1.548 (2)C19A—H19G0.9800
C15C—H15C0.9900C19A—H19H0.9800
C15C—H15D0.9900C19A—H19I0.9800
C16C—C17C1.560 (2)C20A—C21A1.528 (3)
C16C—H16A0.9900C20A—C22A1.538 (3)
C16C—H16B0.9900C20A—H20C1.0000
C16B—C17B1.562 (2)C21A—H21G0.9800
C16B—H16C0.9900C21A—H21H0.9800
C16B—H16D0.9900C21A—H21I0.9800
C17B—C20B1.542 (2)C22A—C23A1.541 (3)
C17B—H17A1.0000C22A—H22E0.9900
C17C—C20C1.541 (2)C22A—H22F0.9900
C17C—H17B1.0000C23A—C24A1.500 (3)
C18B—H18A0.9800C23A—H23E0.9900
C18B—H18B0.9800C23A—H23F0.9900
C18B—H18C0.9800
C10B—C1B—C2B114.08 (16)H18D—C18C—H18F109.5
C10B—C1B—H1BA108.7H18E—C18C—H18F109.5
C2B—C1B—H1BA108.7C10C—C19C—H19A109.5
C10B—C1B—H1BB108.7C10C—C19C—H19B109.5
C2B—C1B—H1BB108.7H19A—C19C—H19B109.5
H1BA—C1B—H1BB107.6C10C—C19C—H19C109.5
C2C—C1C—C10C114.59 (16)H19A—C19C—H19C109.5
C2C—C1C—H1CA108.6H19B—C19C—H19C109.5
C10C—C1C—H1CA108.6C10B—C19B—H19D109.5
C2C—C1C—H1CB108.6C10B—C19B—H19E109.5
C10C—C1C—H1CB108.6H19D—C19B—H19E109.5
H1CA—C1C—H1CB107.6C10B—C19B—H19F109.5
C3B—C2B—C1B109.58 (16)H19D—C19B—H19F109.5
C3B—C2B—H2BA109.8H19E—C19B—H19F109.5
C1B—C2B—H2BA109.8C21B—C20B—C22B110.29 (15)
C3B—C2B—H2BB109.8C21B—C20B—C17B112.96 (15)
C1B—C2B—H2BB109.8C22B—C20B—C17B109.82 (15)
H2BA—C2B—H2BB108.2C21B—C20B—H20A107.9
C3C—C2C—C1C107.99 (17)C22B—C20B—H20A107.9
C3C—C2C—H2CA110.1C17B—C20B—H20A107.9
C1C—C2C—H2CA110.1C22C—C20C—C17C108.57 (14)
C3C—C2C—H2CB110.1C22C—C20C—C21C110.68 (15)
C1C—C2C—H2CB110.1C17C—C20C—C21C112.47 (15)
H2CA—C2C—H2CB108.4C22C—C20C—H20B108.3
O1B—C3B—C2B123.42 (19)C17C—C20C—H20B108.3
O1B—C3B—C4B121.26 (19)C21C—C20C—H20B108.3
C2B—C3B—C4B115.32 (16)C20C—C21C—H21A109.5
O1C—C3C—C2C122.7 (2)C20C—C21C—H21B109.5
O1C—C3C—C4C122.5 (2)H21A—C21C—H21B109.5
C2C—C3C—C4C114.78 (16)C20C—C21C—H21C109.5
C24C—O4C—H4CC109.5H21A—C21C—H21C109.5
C24B—O4B—H4BC109.5H21B—C21C—H21C109.5
C3C—C4C—C5C113.44 (17)C20B—C21B—H21D109.5
C3C—C4C—H4CA108.9C20B—C21B—H21E109.5
C5C—C4C—H4CA108.9H21D—C21B—H21E109.5
C3C—C4C—H4CB108.9C20B—C21B—H21F109.5
C5C—C4C—H4CB108.9H21D—C21B—H21F109.5
H4CA—C4C—H4CB107.7H21E—C21B—H21F109.5
C3B—C4B—C5B113.26 (16)C23C—C22C—C20C115.80 (15)
C3B—C4B—H4BA108.9C23C—C22C—H22A108.3
C5B—C4B—H4BA108.9C20C—C22C—H22A108.3
C3B—C4B—H4BB108.9C23C—C22C—H22B108.3
C5B—C4B—H4BB108.9C20C—C22C—H22B108.3
H4BA—C4B—H4BB107.7H22A—C22C—H22B107.4
C4B—C5B—C6B108.46 (15)C23B—C22B—C20B115.66 (16)
C4B—C5B—C10B113.23 (15)C23B—C22B—H22C108.4
C6B—C5B—C10B112.40 (15)C20B—C22B—H22C108.4
C4B—C5B—H5BA107.5C23B—C22B—H22D108.4
C6B—C5B—H5BA107.5C20B—C22B—H22D108.4
C10B—C5B—H5BA107.5H22C—C22B—H22D107.4
C4C—C5C—C10C113.39 (16)C24C—C23C—C22C111.56 (15)
C4C—C5C—C6C108.93 (16)C24C—C23C—H23A109.3
C10C—C5C—C6C112.31 (15)C22C—C23C—H23A109.3
C4C—C5C—H5CA107.3C24C—C23C—H23B109.3
C10C—C5C—H5CA107.3C22C—C23C—H23B109.3
C6C—C5C—H5CA107.3H23A—C23C—H23B108.0
C7B—C6B—C5B108.55 (15)C24B—C23B—C22B115.41 (16)
C7B—C6B—H6BA110.0C24B—C23B—H23C108.4
C5B—C6B—H6BA110.0C22B—C23B—H23C108.4
C7B—C6B—H6BB110.0C24B—C23B—H23D108.4
C5B—C6B—H6BB110.0C22B—C23B—H23D108.4
H6BA—C6B—H6BB108.4H23C—C23B—H23D107.5
C7C—C6C—C5C110.51 (15)O3C—C24C—O4C122.61 (17)
C7C—C6C—H6CA109.5O3C—C24C—C23C123.81 (17)
C5C—C6C—H6CA109.5O4C—C24C—C23C113.56 (16)
C7C—C6C—H6CB109.5O3B—C24B—O4B123.41 (17)
C5C—C6C—H6CB109.5O3B—C24B—C23B124.62 (17)
H6CA—C6C—H6CB108.1O4B—C24B—C23B111.93 (16)
O2C—C7C—C8C123.44 (17)C2A—C1A—C10A114.32 (16)
O2C—C7C—C6C121.87 (17)C2A—C1A—H1AA108.7
C8C—C7C—C6C114.55 (16)C10A—C1A—H1AA108.7
O2B—C7B—C6B122.75 (18)C2A—C1A—H1AB108.7
O2B—C7B—C8B123.16 (17)C10A—C1A—H1AB108.7
C6B—C7B—C8B113.73 (16)H1AA—C1A—H1AB107.6
C7C—C8C—C14C114.34 (15)C3A—C2A—C1A107.91 (17)
C7C—C8C—C9C106.09 (14)C3A—C2A—H2AA110.1
C14C—C8C—C9C111.29 (14)C1A—C2A—H2AA110.1
C7C—C8C—H8CA108.3C3A—C2A—H2AB110.1
C14C—C8C—H8CA108.3C1A—C2A—H2AB110.1
C9C—C8C—H8CA108.3H2AA—C2A—H2AB108.4
C7B—C8B—C14B114.92 (15)O1A—C3A—C2A123.4 (2)
C7B—C8B—C9B105.39 (14)O1A—C3A—C4A122.0 (2)
C14B—C8B—C9B110.93 (14)C2A—C3A—C4A114.55 (16)
C7B—C8B—H8BA108.5C24A—O4A—H4AC109.5
C14B—C8B—H8BA108.5C3A—C4A—C5A112.47 (17)
C9B—C8B—H8BA108.5C3A—C4A—H4AA109.1
C11C—C9C—C10C113.73 (15)C5A—C4A—H4AA109.1
C11C—C9C—C8C112.73 (13)C3A—C4A—H4AB109.1
C10C—C9C—C8C111.19 (14)C5A—C4A—H4AB109.1
C11C—C9C—H9CA106.2H4AA—C4A—H4AB107.8
C10C—C9C—H9CA106.2C6A—C5A—C4A109.03 (16)
C8C—C9C—H9CA106.2C6A—C5A—C10A112.50 (16)
C11B—C9B—C10B113.68 (15)C4A—C5A—C10A113.16 (16)
C11B—C9B—C8B111.97 (14)C6A—C5A—H5AA107.3
C10B—C9B—C8B111.69 (14)C4A—C5A—H5AA107.3
C11B—C9B—H9BA106.3C10A—C5A—H5AA107.3
C10B—C9B—H9BA106.3C7A—C6A—C5A111.04 (15)
C8B—C9B—H9BA106.3C7A—C6A—H6AA109.4
C1B—C10B—C19B106.17 (16)C5A—C6A—H6AA109.4
C1B—C10B—C5B108.32 (15)C7A—C6A—H6AB109.4
C19B—C10B—C5B109.03 (15)C5A—C6A—H6AB109.4
C1B—C10B—C9B111.76 (15)H6AA—C6A—H6AB108.0
C19B—C10B—C9B111.42 (15)O2A—C7A—C8A123.52 (18)
C5B—C10B—C9B110.01 (15)O2A—C7A—C6A122.16 (18)
C1C—C10C—C19C106.67 (15)C8A—C7A—C6A114.23 (16)
C1C—C10C—C5C108.12 (14)C7A—C8A—C14A114.57 (15)
C19C—C10C—C5C109.11 (15)C7A—C8A—C9A106.72 (15)
C1C—C10C—C9C111.08 (15)C14A—C8A—C9A111.38 (15)
C19C—C10C—C9C111.88 (14)C7A—C8A—H8AA108.0
C5C—C10C—C9C109.85 (14)C14A—C8A—H8AA108.0
C9C—C11C—C12C114.28 (15)C9A—C8A—H8AA108.0
C9C—C11C—H11A108.7C11A—C9A—C8A113.11 (15)
C12C—C11C—H11A108.7C11A—C9A—C10A113.21 (16)
C9C—C11C—H11B108.7C8A—C9A—C10A110.92 (15)
C12C—C11C—H11B108.7C11A—C9A—H9AA106.3
H11A—C11C—H11B107.6C8A—C9A—H9AA106.3
C9B—C11B—C12B114.77 (15)C10A—C9A—H9AA106.3
C9B—C11B—H11C108.6C1A—C10A—C19A106.12 (16)
C12B—C11B—H11C108.6C1A—C10A—C5A108.21 (15)
C9B—C11B—H11D108.6C19A—C10A—C5A108.75 (16)
C12B—C11B—H11D108.6C1A—C10A—C9A112.01 (15)
H11C—C11B—H11D107.5C19A—C10A—C9A111.68 (15)
C13B—C12B—C11B111.78 (15)C5A—C10A—C9A109.92 (15)
C13B—C12B—H12A109.3C9A—C11A—C12A114.06 (16)
C11B—C12B—H12A109.3C9A—C11A—H11E108.7
C13B—C12B—H12B109.3C12A—C11A—H11E108.7
C11B—C12B—H12B109.3C9A—C11A—H11F108.7
H12A—C12B—H12B107.9C12A—C11A—H11F108.7
C13C—C12C—C11C111.42 (15)H11E—C11A—H11F107.6
C13C—C12C—H12C109.3C13A—C12A—C11A111.88 (16)
C11C—C12C—H12C109.3C13A—C12A—H12E109.2
C13C—C12C—H12D109.3C11A—C12A—H12E109.2
C11C—C12C—H12D109.3C13A—C12A—H12F109.2
H12C—C12C—H12D108.0C11A—C12A—H12F109.2
C18C—C13C—C12C110.89 (15)H12E—C12A—H12F107.9
C18C—C13C—C14C112.43 (15)C12A—C13A—C18A110.93 (16)
C12C—C13C—C14C106.41 (14)C12A—C13A—C14A106.70 (15)
C18C—C13C—C17C109.50 (14)C18A—C13A—C14A111.99 (15)
C12C—C13C—C17C117.06 (15)C12A—C13A—C17A117.80 (16)
C14C—C13C—C17C100.12 (14)C18A—C13A—C17A108.82 (15)
C12B—C13B—C18B110.64 (15)C14A—C13A—C17A100.13 (14)
C12B—C13B—C14B106.47 (14)C8A—C14A—C15A117.81 (15)
C18B—C13B—C14B111.74 (14)C8A—C14A—C13A113.13 (15)
C12B—C13B—C17B116.62 (14)C15A—C14A—C13A104.93 (15)
C18B—C13B—C17B109.38 (14)C8A—C14A—H14C106.8
C14B—C13B—C17B101.64 (14)C15A—C14A—H14C106.8
C8C—C14C—C15C117.57 (15)C13A—C14A—H14C106.8
C8C—C14C—C13C112.62 (14)C14A—C15A—C16A104.34 (15)
C15C—C14C—C13C104.87 (14)C14A—C15A—H15E110.9
C8C—C14C—H14A107.1C16A—C15A—H15E110.9
C15C—C14C—H14A107.1C14A—C15A—H15F110.9
C13C—C14C—H14A107.1C16A—C15A—H15F110.9
C8B—C14B—C15B118.51 (15)H15E—C15A—H15F108.9
C8B—C14B—C13B112.51 (14)C15A—C16A—C17A106.82 (15)
C15B—C14B—C13B103.92 (14)C15A—C16A—H16E110.4
C8B—C14B—H14B107.1C17A—C16A—H16E110.4
C15B—C14B—H14B107.1C15A—C16A—H16F110.4
C13B—C14B—H14B107.1C17A—C16A—H16F110.4
C14B—C15B—C16B104.39 (14)H16E—C16A—H16F108.6
C14B—C15B—H15A110.9C20A—C17A—C16A112.60 (15)
C16B—C15B—H15A110.9C20A—C17A—C13A119.43 (15)
C14B—C15B—H15B110.9C16A—C17A—C13A103.25 (15)
C16B—C15B—H15B110.9C20A—C17A—H17C107.0
H15A—C15B—H15B108.9C16A—C17A—H17C107.0
C14C—C15C—C16C103.66 (14)C13A—C17A—H17C107.0
C14C—C15C—H15C111.0C13A—C18A—H18G109.5
C16C—C15C—H15C111.0C13A—C18A—H18H109.5
C14C—C15C—H15D111.0H18G—C18A—H18H109.5
C16C—C15C—H15D111.0C13A—C18A—H18I109.5
H15C—C15C—H15D109.0H18G—C18A—H18I109.5
C15C—C16C—C17C107.15 (14)H18H—C18A—H18I109.5
C15C—C16C—H16A110.3C10A—C19A—H19G109.5
C17C—C16C—H16A110.3C10A—C19A—H19H109.5
C15C—C16C—H16B110.3H19G—C19A—H19H109.5
C17C—C16C—H16B110.3C10A—C19A—H19I109.5
H16A—C16C—H16B108.5H19G—C19A—H19I109.5
C15B—C16B—C17B107.07 (15)H19H—C19A—H19I109.5
C15B—C16B—H16C110.3C21A—C20A—C22A110.66 (17)
C17B—C16B—H16C110.3C21A—C20A—C17A111.67 (16)
C15B—C16B—H16D110.3C22A—C20A—C17A109.64 (15)
C17B—C16B—H16D110.3C21A—C20A—H20C108.3
H16C—C16B—H16D108.6C22A—C20A—H20C108.3
C20B—C17B—C13B118.16 (15)C17A—C20A—H20C108.3
C20B—C17B—C16B111.81 (14)C20A—C21A—H21G109.5
C13B—C17B—C16B103.63 (14)C20A—C21A—H21H109.5
C20B—C17B—H17A107.6H21G—C21A—H21H109.5
C13B—C17B—H17A107.6C20A—C21A—H21I109.5
C16B—C17B—H17A107.6H21G—C21A—H21I109.5
C20C—C17C—C13C118.82 (14)H21H—C21A—H21I109.5
C20C—C17C—C16C111.66 (14)C23A—C22A—C20A117.15 (16)
C13C—C17C—C16C103.62 (14)C23A—C22A—H22E108.0
C20C—C17C—H17B107.4C20A—C22A—H22E108.0
C13C—C17C—H17B107.4C23A—C22A—H22F108.0
C16C—C17C—H17B107.4C20A—C22A—H22F108.0
C13B—C18B—H18A109.5H22E—C22A—H22F107.3
C13B—C18B—H18B109.5C24A—C23A—C22A116.59 (18)
H18A—C18B—H18B109.5C24A—C23A—H23E108.1
C13B—C18B—H18C109.5C22A—C23A—H23E108.1
H18A—C18B—H18C109.5C24A—C23A—H23F108.1
H18B—C18B—H18C109.5C22A—C23A—H23F108.1
C13C—C18C—H18D109.5H23E—C23A—H23F107.3
C13C—C18C—H18E109.5O3A—C24A—O4A122.06 (19)
H18D—C18C—H18E109.5O3A—C24A—C23A124.19 (19)
C13C—C18C—H18F109.5O4A—C24A—C23A113.73 (17)
C10B—C1B—C2B—C3B56.0 (2)C14B—C15B—C16B—C17B10.99 (19)
C10C—C1C—C2C—C3C58.6 (2)C12B—C13B—C17B—C20B83.72 (19)
C1B—C2B—C3B—O1B127.5 (2)C18B—C13B—C17B—C20B42.7 (2)
C1B—C2B—C3B—C4B51.5 (2)C14B—C13B—C17B—C20B160.99 (14)
C1C—C2C—C3C—O1C123.7 (2)C12B—C13B—C17B—C16B151.99 (15)
C1C—C2C—C3C—C4C53.7 (2)C18B—C13B—C17B—C16B81.55 (17)
O1C—C3C—C4C—C5C127.2 (2)C14B—C13B—C17B—C16B36.70 (16)
C2C—C3C—C4C—C5C50.3 (2)C15B—C16B—C17B—C20B144.54 (15)
O1B—C3B—C4B—C5B129.71 (19)C15B—C16B—C17B—C13B16.23 (18)
C2B—C3B—C4B—C5B49.3 (2)C18C—C13C—C17C—C20C45.6 (2)
C3B—C4B—C5B—C6B174.40 (15)C12C—C13C—C17C—C20C81.7 (2)
C3B—C4B—C5B—C10B48.9 (2)C14C—C13C—C17C—C20C163.91 (15)
C3C—C4C—C5C—C10C47.8 (2)C18C—C13C—C17C—C16C78.94 (17)
C3C—C4C—C5C—C6C173.61 (17)C12C—C13C—C17C—C16C153.80 (15)
C4B—C5B—C6B—C7B72.01 (19)C14C—C13C—C17C—C16C39.38 (16)
C10B—C5B—C6B—C7B54.0 (2)C15C—C16C—C17C—C20C149.29 (14)
C4C—C5C—C6C—C7C75.5 (2)C15C—C16C—C17C—C13C20.25 (18)
C10C—C5C—C6C—C7C51.0 (2)C13B—C17B—C20B—C21B58.9 (2)
C5C—C6C—C7C—O2C118.9 (2)C16B—C17B—C20B—C21B179.04 (15)
C5C—C6C—C7C—C8C56.9 (2)C13B—C17B—C20B—C22B177.52 (15)
C5B—C6B—C7B—O2B111.5 (2)C16B—C17B—C20B—C22B57.39 (19)
C5B—C6B—C7B—C8B61.76 (19)C13C—C17C—C20C—C22C176.80 (15)
O2C—C7C—C8C—C14C7.9 (3)C16C—C17C—C20C—C22C56.29 (19)
C6C—C7C—C8C—C14C176.32 (15)C13C—C17C—C20C—C21C60.4 (2)
O2C—C7C—C8C—C9C115.09 (19)C16C—C17C—C20C—C21C179.12 (14)
C6C—C7C—C8C—C9C60.65 (19)C17C—C20C—C22C—C23C177.34 (15)
O2B—C7B—C8B—C14B12.8 (3)C21C—C20C—C22C—C23C58.8 (2)
C6B—C7B—C8B—C14B173.92 (15)C21B—C20B—C22B—C23B62.3 (2)
O2B—C7B—C8B—C9B109.62 (19)C17B—C20B—C22B—C23B172.55 (15)
C6B—C7B—C8B—C9B63.64 (18)C20C—C22C—C23C—C24C174.27 (16)
C7C—C8C—C9C—C11C170.62 (15)C20B—C22B—C23B—C24B67.2 (2)
C14C—C8C—C9C—C11C45.69 (19)C22C—C23C—C24C—O3C6.9 (3)
C7C—C8C—C9C—C10C60.30 (18)C22C—C23C—C24C—O4C171.78 (16)
C14C—C8C—C9C—C10C174.77 (14)C22B—C23B—C24B—O3B0.3 (3)
C7B—C8B—C9B—C11B171.88 (14)C22B—C23B—C24B—O4B177.66 (17)
C14B—C8B—C9B—C11B46.91 (19)C10A—C1A—C2A—C3A58.7 (2)
C7B—C8B—C9B—C10B59.32 (18)C1A—C2A—C3A—O1A121.6 (2)
C14B—C8B—C9B—C10B175.71 (14)C1A—C2A—C3A—C4A55.3 (2)
C2B—C1B—C10B—C19B172.97 (16)O1A—C3A—C4A—C5A124.6 (2)
C2B—C1B—C10B—C5B56.0 (2)C2A—C3A—C4A—C5A52.2 (2)
C2B—C1B—C10B—C9B65.4 (2)C3A—C4A—C5A—C6A175.23 (16)
C4B—C5B—C10B—C1B51.3 (2)C3A—C4A—C5A—C10A49.2 (2)
C6B—C5B—C10B—C1B174.63 (15)C4A—C5A—C6A—C7A76.3 (2)
C4B—C5B—C10B—C19B166.41 (16)C10A—C5A—C6A—C7A50.1 (2)
C6B—C5B—C10B—C19B70.25 (19)C5A—C6A—C7A—O2A121.0 (2)
C4B—C5B—C10B—C9B71.13 (19)C5A—C6A—C7A—C8A55.8 (2)
C6B—C5B—C10B—C9B52.21 (19)O2A—C7A—C8A—C14A7.3 (3)
C11B—C9B—C10B—C1B56.18 (19)C6A—C7A—C8A—C14A175.96 (15)
C8B—C9B—C10B—C1B175.94 (14)O2A—C7A—C8A—C9A116.4 (2)
C11B—C9B—C10B—C19B62.4 (2)C6A—C7A—C8A—C9A60.27 (19)
C8B—C9B—C10B—C19B65.5 (2)C7A—C8A—C9A—C11A170.83 (16)
C11B—C9B—C10B—C5B176.54 (14)C14A—C8A—C9A—C11A45.1 (2)
C8B—C9B—C10B—C5B55.58 (18)C7A—C8A—C9A—C10A60.71 (18)
C2C—C1C—C10C—C19C174.22 (16)C14A—C8A—C9A—C10A173.57 (15)
C2C—C1C—C10C—C5C57.0 (2)C2A—C1A—C10A—C19A173.26 (17)
C2C—C1C—C10C—C9C63.6 (2)C2A—C1A—C10A—C5A56.7 (2)
C4C—C5C—C10C—C1C49.7 (2)C2A—C1A—C10A—C9A64.6 (2)
C6C—C5C—C10C—C1C173.72 (15)C6A—C5A—C10A—C1A174.47 (16)
C4C—C5C—C10C—C19C165.35 (16)C4A—C5A—C10A—C1A50.3 (2)
C6C—C5C—C10C—C19C70.63 (19)C6A—C5A—C10A—C19A70.7 (2)
C4C—C5C—C10C—C9C71.66 (19)C4A—C5A—C10A—C19A165.20 (17)
C6C—C5C—C10C—C9C52.36 (19)C6A—C5A—C10A—C9A51.9 (2)
C11C—C9C—C10C—C1C53.83 (19)C4A—C5A—C10A—C9A72.3 (2)
C8C—C9C—C10C—C1C177.62 (14)C11A—C9A—C10A—C1A53.3 (2)
C11C—C9C—C10C—C19C65.3 (2)C8A—C9A—C10A—C1A178.32 (15)
C8C—C9C—C10C—C19C63.3 (2)C11A—C9A—C10A—C19A65.6 (2)
C11C—C9C—C10C—C5C173.40 (15)C8A—C9A—C10A—C19A62.8 (2)
C8C—C9C—C10C—C5C58.05 (18)C11A—C9A—C10A—C5A173.61 (16)
C10C—C9C—C11C—C12C172.74 (15)C8A—C9A—C10A—C5A57.99 (19)
C8C—C9C—C11C—C12C45.0 (2)C8A—C9A—C11A—C12A44.4 (2)
C10B—C9B—C11B—C12B172.84 (15)C10A—C9A—C11A—C12A171.68 (16)
C8B—C9B—C11B—C12B45.1 (2)C9A—C11A—C12A—C13A53.0 (2)
C9B—C11B—C12B—C13B52.7 (2)C11A—C12A—C13A—C18A62.9 (2)
C9C—C11C—C12C—C13C53.6 (2)C11A—C12A—C13A—C14A59.4 (2)
C11C—C12C—C13C—C18C62.5 (2)C11A—C12A—C13A—C17A170.83 (16)
C11C—C12C—C13C—C14C60.06 (18)C7A—C8A—C14A—C15A60.4 (2)
C11C—C12C—C13C—C17C170.91 (15)C9A—C8A—C14A—C15A178.40 (15)
C11B—C12B—C13B—C18B62.64 (19)C7A—C8A—C14A—C13A176.82 (15)
C11B—C12B—C13B—C14B58.97 (18)C9A—C8A—C14A—C13A55.58 (19)
C11B—C12B—C13B—C17B171.53 (15)C12A—C13A—C14A—C8A62.32 (19)
C7C—C8C—C14C—C15C61.3 (2)C18A—C13A—C14A—C8A59.2 (2)
C9C—C8C—C14C—C15C178.53 (15)C17A—C13A—C14A—C8A174.43 (14)
C7C—C8C—C14C—C13C176.62 (15)C12A—C13A—C14A—C15A167.96 (15)
C9C—C8C—C14C—C13C56.45 (18)C18A—C13A—C14A—C15A70.48 (19)
C18C—C13C—C14C—C8C58.39 (19)C17A—C13A—C14A—C15A44.71 (16)
C12C—C13C—C14C—C8C63.19 (18)C8A—C14A—C15A—C16A157.44 (16)
C17C—C13C—C14C—C8C174.52 (14)C13A—C14A—C15A—C16A30.55 (18)
C18C—C13C—C14C—C15C70.61 (18)C14A—C15A—C16A—C17A4.13 (19)
C12C—C13C—C14C—C15C167.81 (14)C15A—C16A—C17A—C20A153.45 (15)
C17C—C13C—C14C—C15C45.52 (16)C15A—C16A—C17A—C13A23.30 (18)
C7B—C8B—C14B—C15B61.1 (2)C12A—C13A—C17A—C20A78.1 (2)
C9B—C8B—C14B—C15B179.51 (15)C18A—C13A—C17A—C20A49.2 (2)
C7B—C8B—C14B—C13B177.49 (14)C14A—C13A—C17A—C20A166.79 (15)
C9B—C8B—C14B—C13B58.08 (18)C12A—C13A—C17A—C16A156.02 (16)
C12B—C13B—C14B—C8B63.49 (18)C18A—C13A—C17A—C16A76.66 (18)
C18B—C13B—C14B—C8B57.42 (19)C14A—C13A—C17A—C16A40.91 (16)
C17B—C13B—C14B—C8B173.96 (14)C16A—C17A—C20A—C21A179.13 (16)
C12B—C13B—C14B—C15B167.10 (14)C13A—C17A—C20A—C21A57.8 (2)
C18B—C13B—C14B—C15B72.00 (17)C16A—C17A—C20A—C22A57.8 (2)
C17B—C13B—C14B—C15B44.55 (16)C13A—C17A—C20A—C22A179.17 (16)
C8B—C14B—C15B—C16B160.06 (16)C21A—C20A—C22A—C23A61.1 (2)
C13B—C14B—C15B—C16B34.37 (18)C17A—C20A—C22A—C23A175.30 (17)
C8C—C14C—C15C—C16C159.10 (15)C20A—C22A—C23A—C24A80.2 (2)
C13C—C14C—C15C—C16C33.11 (17)C22A—C23A—C24A—O3A129.8 (2)
C14C—C15C—C16C—C17C7.62 (18)C22A—C23A—C24A—O4A51.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1AA···O1Bi0.992.693.145 (2)108
C4A—H4AA···O2Cii0.992.573.369 (2)137
C6A—H6AA···O4Aiii0.992.623.345 (2)130
C11A—H11F···O2Aiv0.992.673.495 (2)141
C16A—H16E···O3Cii0.992.603.459 (2)145
C22A—H22E···O3Cii0.992.673.527 (3)145
C1C—H1CA···O4Cv0.992.653.070 (2)106
C2C—H2CA···O4Cv0.992.653.297 (2)123
C11B—H11D···O2Biv0.992.583.095 (2)113
C19B—H19D···O1Cvi0.982.543.434 (2)152
C6C—H6CB···O4Cvii0.992.663.223 (2)117
C14C—H14A···O2Aviii1.002.643.593 (2)161
O4A—H4AC···O1B0.841.872.7055 (19)180
O4B—H4BC···O3C0.841.812.6485 (19)178
O4C—H4CC···O3B0.841.822.6598 (18)178
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z; (iv) x1, y, z; (v) x+1, y+1/2, z+1/2; (vi) x, y1, z; (vii) x, y+1/2, z+1/2; (viii) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC24H36O4
Mr388.53
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)7.6177 (1), 27.6911 (4), 29.9256 (4)
V3)6312.58 (15)
Z12
Radiation typeCu Kα
µ (mm1)0.65
Crystal size (mm)0.22 × 0.13 × 0.12
Data collection
DiffractometerBruker SMART CCD APEX II area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Blessing, 1995)
Tmin, Tmax0.871, 0.927
No. of measured, independent and
observed [I > 2σ(I)] reflections
27061, 10459, 9648
Rint0.022
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.091, 1.07
No. of reflections10459
No. of parameters758
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.16
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.14 (13)

Computer programs: SMART (Bruker, 2000), SMART, SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top
O3B—C24B1.218 (2)O4B—C24B1.318 (2)
O3C—C24C1.214 (2)O3A—C24A1.210 (2)
O4C—C24C1.317 (2)O4A—C24A1.326 (2)
O3C—C24C—C23C123.81 (17)O4B—C24B—C23B111.93 (16)
O4C—C24C—C23C113.56 (16)O3A—C24A—C23A124.19 (19)
O3B—C24B—C23B124.62 (17)O4A—C24A—C23A113.73 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1AA···O1Bi0.992.693.145 (2)108
C4A—H4AA···O2Cii0.992.573.369 (2)137
C6A—H6AA···O4Aiii0.992.623.345 (2)130
C11A—H11F···O2Aiv0.992.673.495 (2)141
C16A—H16E···O3Cii0.992.603.459 (2)145
C22A—H22E···O3Cii0.992.673.527 (3)145
C1C—H1CA···O4Cv0.992.653.070 (2)106
C2C—H2CA···O4Cv0.992.653.297 (2)123
C11B—H11D···O2Biv0.992.583.095 (2)113
C19B—H19D···O1Cvi0.982.543.434 (2)152
C6C—H6CB···O4Cvii0.992.663.223 (2)117
C14C—H14A···O2Aviii1.002.643.593 (2)161
O4A—H4AC···O1B0.841.872.7055 (19)180
O4B—H4BC···O3C0.841.812.6485 (19)178
O4C—H4CC···O3B0.841.822.6598 (18)178
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z; (iv) x1, y, z; (v) x+1, y+1/2, z+1/2; (vi) x, y1, z; (vii) x, y+1/2, z+1/2; (viii) x1/2, y+1/2, z.
 

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