(6aR)-1-Hydr­oxy-2,2,6a,6b,9,9,12a-hepta­methyl-10-(methyl­carbon­yloxy)perhydro-4-picenylmethyl acetate

Flekhter, O.B.; Medvedeva, N.I.; Suponitsky, K.Y.

doi:10.1107/S1600536807015231

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(6aR)-1-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-(methylcarbonyloxy)perhydro-4-picenylmethyl acetate

O. B. Flekhter, N. I. Medvedeva and K. Y. Suponitsky

The title compound, C₃₄H₅₆O₅, an oleanane triterpene, is a key intermediate in the synthetic route from betulin to 18(19)-oleanene triterpenoids. In the molecule, all bond lengths and angles are normal. The hydroxy groups are involved in intermolecular O—H

O hydrogen bonds, which link the molecules into zigzag chains running along the a axis. The crystal packing is further stabilized by weak intermolecular C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015231/cv2220sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015231/cv2220Isup2.hkl Contains datablock I

CCDC reference: 634043

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R factor = 0.044
wR factor = 0.071
Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H9A    ..  H27B    ..       1.84 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H18A   ..  H27A    ..       1.87 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _reflns_number_total               4154
           Count of symmetry unique reflns         4162
           Completeness (_total/calc)             99.81%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
  11 ALERT level G = General alerts; check

  10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(6aR)-1-Hydroxy-2,2,6a,6 b,9,9,12a-heptamethyl-10-(methylcarbonyloxy)perhydro- 4-picenylmethyl acetate top

Crystal data top

C₃₄H₅₆O₅	F(000) = 1200
M_r = 544.79	D_x = 1.185 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2486 reflections
a = 8.4190 (6) Å	θ = 2.5–19.7°
b = 11.4960 (8) Å	µ = 0.08 mm⁻¹
c = 31.541 (2) Å	T = 120 K
V = 3052.7 (4) Å³	Prism, colourless
Z = 4	0.20 × 0.20 × 0.15 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2421 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.080
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
φ and ω scans	h = −11→11
25843 measured reflections	k = −15→15
4154 independent reflections	l = −37→41

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.071	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.016P)²] where P = (F_o² + 2F_c²)/3
4154 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.6290 (2)	0.48924 (15)	0.39470 (5)	0.0270 (5)
O2	0.7732 (2)	0.64760 (17)	0.37850 (6)	0.0449 (6)
O3	−0.2176 (2)	0.33947 (16)	0.07776 (6)	0.0331 (5)
O4	−0.1612 (2)	0.19333 (16)	0.03295 (6)	0.0344 (5)
O5	0.2654 (2)	0.40876 (14)	0.05285 (5)	0.0296 (5)
H5A	0.3051	0.4049	0.0281	0.035*
C1	0.5961 (3)	0.4450 (2)	0.27607 (8)	0.0262 (7)
H1A	0.6692	0.4068	0.2558	0.031*
H1B	0.5867	0.5277	0.2677	0.031*
C2	0.6688 (3)	0.4387 (2)	0.32037 (8)	0.0273 (7)
H2A	0.6896	0.3565	0.3279	0.033*
H2B	0.7714	0.4809	0.3207	0.033*
C3	0.5573 (3)	0.4922 (2)	0.35262 (8)	0.0258 (7)
H3A	0.5401	0.5755	0.3447	0.031*
C4	0.3938 (3)	0.4324 (2)	0.35487 (8)	0.0231 (6)
C5	0.3255 (3)	0.4347 (2)	0.30893 (8)	0.0216 (6)
H5B	0.3135	0.5194	0.3024	0.026*
C6	0.1567 (3)	0.3860 (2)	0.30503 (8)	0.0282 (7)
H6A	0.1608	0.2999	0.3047	0.034*
H6B	0.0931	0.4104	0.3299	0.034*
C7	0.0781 (3)	0.4293 (2)	0.26473 (8)	0.0266 (7)
H7A	0.0647	0.5147	0.2668	0.032*
H7B	−0.0291	0.3943	0.2626	0.032*
C8	0.1708 (3)	0.4011 (2)	0.22388 (8)	0.0203 (6)
C9	0.3515 (3)	0.4293 (2)	0.23020 (8)	0.0196 (6)
H9A	0.3550	0.5161	0.2321	0.024*
C10	0.4315 (3)	0.3874 (2)	0.27255 (8)	0.0212 (6)
C11	0.4453 (3)	0.4014 (2)	0.19001 (8)	0.0265 (7)
H11A	0.4361	0.3174	0.1837	0.032*
H11B	0.5589	0.4194	0.1947	0.032*
C12	0.3841 (3)	0.4717 (2)	0.15212 (8)	0.0247 (7)
H12A	0.4045	0.5554	0.1572	0.030*
H12B	0.4434	0.4485	0.1264	0.030*
C13	0.2065 (3)	0.4534 (2)	0.14458 (8)	0.0200 (6)
H13A	0.1915	0.3692	0.1377	0.024*
C14	0.1080 (3)	0.4783 (2)	0.18537 (8)	0.0213 (6)
C15	−0.0679 (3)	0.4510 (2)	0.17528 (8)	0.0279 (7)
H15A	−0.0794	0.3662	0.1707	0.033*
H15B	−0.1337	0.4723	0.2001	0.033*
C16	−0.1306 (3)	0.5147 (2)	0.13654 (8)	0.0279 (7)
H16A	−0.1313	0.5992	0.1425	0.034*
H16B	−0.2417	0.4902	0.1314	0.034*
C17	−0.0333 (3)	0.4926 (2)	0.09616 (8)	0.0248 (7)
C18	0.1429 (3)	0.5234 (2)	0.10635 (8)	0.0234 (6)
H18A	0.1396	0.6058	0.1165	0.028*
C19	0.2504 (4)	0.5262 (2)	0.06726 (8)	0.0310 (7)
H19A	0.3578	0.5533	0.0765	0.037*
C20	0.1900 (3)	0.6107 (2)	0.03309 (9)	0.0317 (7)
C21	0.0181 (3)	0.5770 (3)	0.02203 (9)	0.0344 (8)
H21A	−0.0244	0.6338	0.0013	0.041*
H21B	0.0185	0.4996	0.0082	0.041*
C22	−0.0923 (3)	0.5729 (2)	0.06040 (8)	0.0308 (7)
H22A	−0.1984	0.5460	0.0510	0.037*
H22B	−0.1045	0.6526	0.0718	0.037*
C23	0.2883 (3)	0.5065 (2)	0.38379 (8)	0.0324 (7)
H23A	0.2744	0.5838	0.3713	0.049*
H23B	0.3386	0.5141	0.4117	0.049*
H23C	0.1845	0.4690	0.3870	0.049*
C24	0.4058 (3)	0.3106 (2)	0.37437 (8)	0.0346 (8)
H24A	0.4844	0.2648	0.3587	0.052*
H24B	0.3021	0.2721	0.3728	0.052*
H24C	0.4385	0.3170	0.4041	0.052*
C25	0.4585 (3)	0.2548 (2)	0.27392 (8)	0.0303 (7)
H25A	0.4942	0.2278	0.2460	0.045*
H25B	0.3589	0.2158	0.2814	0.045*
H25C	0.5397	0.2366	0.2952	0.045*
C26	0.1451 (3)	0.2702 (2)	0.21435 (8)	0.0307 (7)
H26A	0.1899	0.2236	0.2375	0.046*
H26B	0.1980	0.2500	0.1877	0.046*
H26C	0.0311	0.2543	0.2119	0.046*
C27	0.1167 (3)	0.6097 (2)	0.19726 (8)	0.0289 (7)
H27A	0.1016	0.6570	0.1717	0.043*
H27B	0.2208	0.6269	0.2097	0.043*
H27C	0.0332	0.6279	0.2179	0.043*
C28	−0.0487 (3)	0.3652 (2)	0.08179 (9)	0.0287 (7)
H28A	0.0054	0.3538	0.0542	0.034*
H28B	0.0008	0.3128	0.1029	0.034*
C29	0.2973 (4)	0.6020 (2)	−0.00615 (8)	0.0388 (8)
H29A	0.2872	0.5243	−0.0187	0.058*
H29B	0.4080	0.6153	0.0022	0.058*
H29C	0.2653	0.6607	−0.0270	0.058*
C30	0.2014 (4)	0.7363 (2)	0.04932 (9)	0.0380 (8)
H30A	0.3104	0.7521	0.0586	0.057*
H30B	0.1286	0.7467	0.0733	0.057*
H30C	0.1725	0.7901	0.0265	0.057*
C31	−0.2573 (4)	0.2516 (2)	0.05218 (8)	0.0271 (7)
C32	−0.4332 (3)	0.2367 (2)	0.04917 (9)	0.0383 (8)
H32A	−0.4586	0.1538	0.0463	0.057*
H32B	−0.4731	0.2789	0.0244	0.057*
H32C	−0.4834	0.2674	0.0749	0.057*
C33	0.7367 (3)	0.5730 (2)	0.40336 (8)	0.0282 (7)
C34	0.8028 (3)	0.5626 (2)	0.44701 (8)	0.0356 (8)
H34A	0.7955	0.6380	0.4614	0.053*
H34B	0.9143	0.5386	0.4454	0.053*
H34C	0.7421	0.5045	0.4629	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0279 (11)	0.0307 (11)	0.0225 (11)	−0.0064 (10)	−0.0040 (10)	0.0006 (9)
O2	0.0596 (16)	0.0428 (13)	0.0323 (13)	−0.0212 (12)	−0.0087 (12)	0.0108 (10)
O3	0.0261 (12)	0.0380 (12)	0.0353 (12)	0.0022 (10)	−0.0046 (10)	−0.0076 (10)
O4	0.0315 (12)	0.0387 (12)	0.0331 (12)	−0.0021 (11)	0.0047 (10)	−0.0063 (10)
O5	0.0366 (12)	0.0310 (11)	0.0210 (10)	0.0065 (10)	0.0042 (10)	−0.0024 (9)
C1	0.0201 (16)	0.0361 (17)	0.0225 (16)	0.0037 (14)	0.0013 (14)	−0.0030 (13)
C2	0.0269 (17)	0.0297 (17)	0.0251 (17)	−0.0002 (14)	−0.0018 (14)	0.0015 (13)
C3	0.0287 (17)	0.0318 (17)	0.0169 (16)	−0.0016 (14)	−0.0049 (14)	0.0016 (13)
C4	0.0237 (16)	0.0301 (16)	0.0155 (15)	−0.0024 (13)	−0.0015 (13)	−0.0016 (12)
C5	0.0197 (16)	0.0256 (15)	0.0195 (15)	−0.0016 (13)	0.0001 (13)	0.0005 (12)
C6	0.0260 (17)	0.0382 (17)	0.0203 (16)	−0.0040 (14)	0.0052 (14)	−0.0024 (13)
C7	0.0170 (15)	0.0416 (18)	0.0212 (17)	−0.0042 (14)	0.0016 (13)	0.0007 (14)
C8	0.0183 (15)	0.0263 (15)	0.0163 (15)	−0.0014 (12)	0.0029 (12)	−0.0032 (12)
C9	0.0193 (15)	0.0221 (14)	0.0174 (15)	0.0007 (12)	−0.0009 (13)	0.0015 (12)
C10	0.0230 (16)	0.0215 (14)	0.0192 (15)	−0.0006 (13)	0.0017 (13)	−0.0003 (13)
C11	0.0184 (15)	0.0360 (17)	0.0250 (17)	−0.0006 (14)	−0.0021 (14)	−0.0034 (14)
C12	0.0246 (16)	0.0316 (16)	0.0178 (16)	0.0017 (14)	0.0031 (13)	−0.0003 (13)
C13	0.0204 (15)	0.0225 (15)	0.0170 (15)	0.0027 (12)	−0.0035 (12)	−0.0004 (12)
C14	0.0171 (15)	0.0285 (16)	0.0183 (15)	0.0023 (13)	−0.0025 (13)	−0.0035 (12)
C15	0.0231 (17)	0.0341 (18)	0.0264 (18)	−0.0012 (14)	0.0006 (14)	−0.0009 (13)
C16	0.0232 (16)	0.0307 (16)	0.0299 (17)	0.0016 (14)	−0.0035 (14)	−0.0050 (14)
C17	0.0245 (16)	0.0284 (16)	0.0215 (16)	0.0024 (13)	−0.0025 (14)	−0.0049 (13)
C18	0.0262 (16)	0.0247 (15)	0.0192 (15)	0.0057 (13)	−0.0014 (14)	−0.0029 (12)
C19	0.0372 (19)	0.0346 (17)	0.0213 (16)	0.0069 (15)	−0.0012 (15)	−0.0040 (13)
C20	0.0370 (19)	0.0313 (17)	0.0268 (17)	0.0028 (15)	0.0012 (15)	0.0026 (14)
C21	0.0341 (19)	0.0419 (19)	0.0270 (18)	0.0023 (15)	−0.0032 (15)	−0.0033 (15)
C22	0.0296 (18)	0.0343 (17)	0.0284 (18)	0.0067 (15)	−0.0040 (14)	−0.0020 (14)
C23	0.0281 (17)	0.0461 (19)	0.0232 (17)	−0.0052 (15)	0.0020 (14)	−0.0049 (14)
C24	0.0363 (19)	0.0405 (18)	0.0268 (17)	−0.0097 (16)	−0.0037 (15)	0.0051 (14)
C25	0.0363 (19)	0.0307 (17)	0.0239 (16)	0.0036 (14)	−0.0040 (15)	−0.0043 (14)
C26	0.0333 (19)	0.0296 (16)	0.0292 (17)	−0.0046 (14)	0.0016 (15)	0.0019 (13)
C27	0.0264 (17)	0.0319 (16)	0.0285 (17)	0.0021 (14)	−0.0005 (14)	−0.0050 (13)
C28	0.0215 (16)	0.0360 (18)	0.0287 (18)	0.0028 (14)	−0.0053 (14)	−0.0086 (14)
C29	0.050 (2)	0.0406 (18)	0.0259 (17)	−0.0045 (17)	0.0024 (16)	0.0007 (14)
C30	0.046 (2)	0.0318 (18)	0.0356 (19)	−0.0038 (16)	−0.0008 (17)	0.0021 (15)
C31	0.0334 (19)	0.0272 (16)	0.0208 (16)	−0.0034 (15)	−0.0057 (15)	0.0044 (14)
C32	0.0311 (19)	0.0358 (18)	0.048 (2)	−0.0037 (15)	−0.0062 (16)	0.0018 (16)
C33	0.0288 (17)	0.0293 (17)	0.0266 (17)	−0.0021 (14)	−0.0047 (15)	−0.0019 (14)
C34	0.0350 (19)	0.0441 (19)	0.0278 (17)	−0.0118 (16)	−0.0065 (16)	0.0023 (14)

Geometric parameters (Å, º) top

O1—C33	1.351 (3)	C16—C17	1.535 (3)
O1—C3	1.459 (3)	C16—H16A	0.9900
O2—C33	1.202 (3)	C16—H16B	0.9900
O3—C31	1.335 (3)	C17—C28	1.539 (3)
O3—C28	1.458 (3)	C17—C22	1.539 (3)
O4—C31	1.213 (3)	C17—C18	1.559 (3)
O5—C19	1.430 (3)	C18—C19	1.529 (3)
O5—H5A	0.8502	C18—H18A	1.0000
C1—C2	1.527 (3)	C19—C20	1.538 (3)
C1—C10	1.540 (3)	C19—H19A	1.0000
C1—H1A	0.9900	C20—C30	1.534 (3)
C1—H1B	0.9900	C20—C29	1.536 (4)
C2—C3	1.515 (3)	C20—C21	1.538 (4)
C2—H2A	0.9900	C21—C22	1.527 (3)
C2—H2B	0.9900	C21—H21A	0.9900
C3—C4	1.540 (4)	C21—H21B	0.9900
C3—H3A	1.0000	C22—H22A	0.9900
C4—C23	1.531 (3)	C22—H22B	0.9900
C4—C24	1.533 (3)	C23—H23A	0.9800
C4—C5	1.560 (3)	C23—H23B	0.9800
C5—C6	1.532 (3)	C23—H23C	0.9800
C5—C10	1.553 (3)	C24—H24A	0.9800
C5—H5B	1.0000	C24—H24B	0.9800
C6—C7	1.517 (3)	C24—H24C	0.9800
C6—H6A	0.9900	C25—H25A	0.9800
C6—H6B	0.9900	C25—H25B	0.9800
C7—C8	1.541 (3)	C25—H25C	0.9800
C7—H7A	0.9900	C26—H26A	0.9800
C7—H7B	0.9900	C26—H26B	0.9800
C8—C26	1.549 (3)	C26—H26C	0.9800
C8—C9	1.568 (3)	C27—H27A	0.9800
C8—C14	1.595 (3)	C27—H27B	0.9800
C9—C11	1.527 (3)	C27—H27C	0.9800
C9—C10	1.572 (3)	C28—H28A	0.9900
C9—H9A	1.0000	C28—H28B	0.9900
C10—C25	1.541 (3)	C29—H29A	0.9800
C11—C12	1.532 (3)	C29—H29B	0.9800
C11—H11A	0.9900	C29—H29C	0.9800
C11—H11B	0.9900	C30—H30A	0.9800
C12—C13	1.529 (3)	C30—H30B	0.9800
C12—H12A	0.9900	C30—H30C	0.9800
C12—H12B	0.9900	C31—C32	1.494 (4)
C13—C18	1.545 (3)	C32—H32A	0.9800
C13—C14	1.557 (3)	C32—H32B	0.9800
C13—H13A	1.0000	C32—H32C	0.9800
C14—C15	1.547 (3)	C33—C34	1.490 (3)
C14—C27	1.559 (3)	C34—H34A	0.9800
C15—C16	1.519 (3)	C34—H34B	0.9800
C15—H15A	0.9900	C34—H34C	0.9800
C15—H15B	0.9900

C33—O1—C3	116.4 (2)	C28—C17—C22	109.1 (2)
C31—O3—C28	116.8 (2)	C16—C17—C18	107.4 (2)
C19—O5—H5A	112.1	C28—C17—C18	110.9 (2)
C2—C1—C10	114.0 (2)	C22—C17—C18	108.8 (2)
C2—C1—H1A	108.8	C19—C18—C13	115.8 (2)
C10—C1—H1A	108.8	C19—C18—C17	113.7 (2)
C2—C1—H1B	108.8	C13—C18—C17	111.9 (2)
C10—C1—H1B	108.8	C19—C18—H18A	104.7
H1A—C1—H1B	107.7	C13—C18—H18A	104.7
C3—C2—C1	110.3 (2)	C17—C18—H18A	104.7
C3—C2—H2A	109.6	O5—C19—C18	106.7 (2)
C1—C2—H2A	109.6	O5—C19—C20	113.8 (2)
C3—C2—H2B	109.6	C18—C19—C20	112.5 (2)
C1—C2—H2B	109.6	O5—C19—H19A	107.9
H2A—C2—H2B	108.1	C18—C19—H19A	107.9
O1—C3—C2	110.2 (2)	C20—C19—H19A	107.9
O1—C3—C4	108.5 (2)	C30—C20—C29	107.1 (2)
C2—C3—C4	113.8 (2)	C30—C20—C19	109.9 (2)
O1—C3—H3A	108.1	C29—C20—C19	109.2 (2)
C2—C3—H3A	108.1	C30—C20—C21	111.8 (2)
C4—C3—H3A	108.1	C29—C20—C21	110.8 (2)
C23—C4—C24	107.9 (2)	C19—C20—C21	108.1 (2)
C23—C4—C3	107.3 (2)	C22—C21—C20	113.6 (2)
C24—C4—C3	111.6 (2)	C22—C21—H21A	108.8
C23—C4—C5	109.3 (2)	C20—C21—H21A	108.8
C24—C4—C5	114.4 (2)	C22—C21—H21B	108.8
C3—C4—C5	106.2 (2)	C20—C21—H21B	108.8
C6—C5—C10	110.2 (2)	H21A—C21—H21B	107.7
C6—C5—C4	114.2 (2)	C21—C22—C17	113.8 (2)
C10—C5—C4	117.9 (2)	C21—C22—H22A	108.8
C6—C5—H5B	104.2	C17—C22—H22A	108.8
C10—C5—H5B	104.2	C21—C22—H22B	108.8
C4—C5—H5B	104.2	C17—C22—H22B	108.8
C7—C6—C5	110.6 (2)	H22A—C22—H22B	107.7
C7—C6—H6A	109.5	C4—C23—H23A	109.5
C5—C6—H6A	109.5	C4—C23—H23B	109.5
C7—C6—H6B	109.5	H23A—C23—H23B	109.5
C5—C6—H6B	109.5	C4—C23—H23C	109.5
H6A—C6—H6B	108.1	H23A—C23—H23C	109.5
C6—C7—C8	114.2 (2)	H23B—C23—H23C	109.5
C6—C7—H7A	108.7	C4—C24—H24A	109.5
C8—C7—H7A	108.7	C4—C24—H24B	109.5
C6—C7—H7B	108.7	H24A—C24—H24B	109.5
C8—C7—H7B	108.7	C4—C24—H24C	109.5
H7A—C7—H7B	107.6	H24A—C24—H24C	109.5
C7—C8—C26	107.2 (2)	H24B—C24—H24C	109.5
C7—C8—C9	110.0 (2)	C10—C25—H25A	109.5
C26—C8—C9	111.2 (2)	C10—C25—H25B	109.5
C7—C8—C14	110.6 (2)	H25A—C25—H25B	109.5
C26—C8—C14	110.3 (2)	C10—C25—H25C	109.5
C9—C8—C14	107.6 (2)	H25A—C25—H25C	109.5
C11—C9—C8	110.6 (2)	H25B—C25—H25C	109.5
C11—C9—C10	114.8 (2)	C8—C26—H26A	109.5
C8—C9—C10	117.4 (2)	C8—C26—H26B	109.5
C11—C9—H9A	104.1	H26A—C26—H26B	109.5
C8—C9—H9A	104.1	C8—C26—H26C	109.5
C10—C9—H9A	104.1	H26A—C26—H26C	109.5
C1—C10—C25	106.9 (2)	H26B—C26—H26C	109.5
C1—C10—C5	108.3 (2)	C14—C27—H27A	109.5
C25—C10—C5	114.3 (2)	C14—C27—H27B	109.5
C1—C10—C9	108.4 (2)	H27A—C27—H27B	109.5
C25—C10—C9	113.0 (2)	C14—C27—H27C	109.5
C5—C10—C9	105.9 (2)	H27A—C27—H27C	109.5
C9—C11—C12	111.3 (2)	H27B—C27—H27C	109.5
C9—C11—H11A	109.4	O3—C28—C17	107.5 (2)
C12—C11—H11A	109.4	O3—C28—H28A	110.2
C9—C11—H11B	109.4	C17—C28—H28A	110.2
C12—C11—H11B	109.4	O3—C28—H28B	110.2
H11A—C11—H11B	108.0	C17—C28—H28B	110.2
C13—C12—C11	112.2 (2)	H28A—C28—H28B	108.5
C13—C12—H12A	109.2	C20—C29—H29A	109.5
C11—C12—H12A	109.2	C20—C29—H29B	109.5
C13—C12—H12B	109.2	H29A—C29—H29B	109.5
C11—C12—H12B	109.2	C20—C29—H29C	109.5
H12A—C12—H12B	107.9	H29A—C29—H29C	109.5
C12—C13—C18	112.8 (2)	H29B—C29—H29C	109.5
C12—C13—C14	111.5 (2)	C20—C30—H30A	109.5
C18—C13—C14	111.4 (2)	C20—C30—H30B	109.5
C12—C13—H13A	106.9	H30A—C30—H30B	109.5
C18—C13—H13A	106.9	C20—C30—H30C	109.5
C14—C13—H13A	106.9	H30A—C30—H30C	109.5
C15—C14—C13	107.6 (2)	H30B—C30—H30C	109.5
C15—C14—C27	106.9 (2)	O4—C31—O3	123.6 (3)
C13—C14—C27	110.6 (2)	O4—C31—C32	124.5 (3)
C15—C14—C8	111.2 (2)	O3—C31—C32	111.9 (3)
C13—C14—C8	110.55 (19)	C31—C32—H32A	109.5
C27—C14—C8	109.9 (2)	C31—C32—H32B	109.5
C16—C15—C14	113.6 (2)	H32A—C32—H32B	109.5
C16—C15—H15A	108.8	C31—C32—H32C	109.5
C14—C15—H15A	108.8	H32A—C32—H32C	109.5
C16—C15—H15B	108.8	H32B—C32—H32C	109.5
C14—C15—H15B	108.8	O2—C33—O1	123.3 (3)
H15A—C15—H15B	107.7	O2—C33—C34	124.4 (3)
C15—C16—C17	113.7 (2)	O1—C33—C34	112.4 (2)
C15—C16—H16A	108.8	C33—C34—H34A	109.5
C17—C16—H16A	108.8	C33—C34—H34B	109.5
C15—C16—H16B	108.8	H34A—C34—H34B	109.5
C17—C16—H16B	108.8	C33—C34—H34C	109.5
H16A—C16—H16B	107.7	H34A—C34—H34C	109.5
C16—C17—C28	110.9 (2)	H34B—C34—H34C	109.5
C16—C17—C22	109.7 (2)

C10—C1—C2—C3	−56.3 (3)	C12—C13—C14—C8	−55.4 (3)
C33—O1—C3—C2	80.1 (3)	C18—C13—C14—C8	177.5 (2)
C33—O1—C3—C4	−154.7 (2)	C7—C8—C14—C15	−62.9 (3)
C1—C2—C3—O1	−178.3 (2)	C26—C8—C14—C15	55.5 (3)
C1—C2—C3—C4	59.5 (3)	C9—C8—C14—C15	176.9 (2)
O1—C3—C4—C23	65.0 (3)	C7—C8—C14—C13	177.6 (2)
C2—C3—C4—C23	−172.0 (2)	C26—C8—C14—C13	−64.0 (3)
O1—C3—C4—C24	−53.0 (3)	C9—C8—C14—C13	57.5 (2)
C2—C3—C4—C24	70.0 (3)	C7—C8—C14—C27	55.3 (3)
O1—C3—C4—C5	−178.3 (2)	C26—C8—C14—C27	173.7 (2)
C2—C3—C4—C5	−55.2 (3)	C9—C8—C14—C27	−64.9 (3)
C23—C4—C5—C6	−60.6 (3)	C13—C14—C15—C16	−54.1 (3)
C24—C4—C5—C6	60.4 (3)	C27—C14—C15—C16	64.8 (3)
C3—C4—C5—C6	−176.1 (2)	C8—C14—C15—C16	−175.3 (2)
C23—C4—C5—C10	167.5 (2)	C14—C15—C16—C17	56.1 (3)
C24—C4—C5—C10	−71.5 (3)	C15—C16—C17—C28	66.9 (3)
C3—C4—C5—C10	52.0 (3)	C15—C16—C17—C22	−172.5 (2)
C10—C5—C6—C7	−64.8 (3)	C15—C16—C17—C18	−54.4 (3)
C4—C5—C6—C7	159.7 (2)	C12—C13—C18—C19	41.1 (3)
C5—C6—C7—C8	56.6 (3)	C14—C13—C18—C19	167.5 (2)
C6—C7—C8—C26	75.6 (3)	C12—C13—C18—C17	173.5 (2)
C6—C7—C8—C9	−45.4 (3)	C14—C13—C18—C17	−60.1 (3)
C6—C7—C8—C14	−164.1 (2)	C16—C17—C18—C19	−170.0 (2)
C7—C8—C9—C11	179.8 (2)	C28—C17—C18—C19	68.7 (3)
C26—C8—C9—C11	61.2 (3)	C22—C17—C18—C19	−51.3 (3)
C14—C8—C9—C11	−59.7 (2)	C16—C17—C18—C13	56.5 (3)
C7—C8—C9—C10	45.4 (3)	C28—C17—C18—C13	−64.8 (3)
C26—C8—C9—C10	−73.2 (3)	C22—C17—C18—C13	175.2 (2)
C14—C8—C9—C10	166.0 (2)	C13—C18—C19—O5	62.4 (3)
C2—C1—C10—C25	−73.4 (3)	C17—C18—C19—O5	−69.2 (3)
C2—C1—C10—C5	50.1 (3)	C13—C18—C19—C20	−172.1 (2)
C2—C1—C10—C9	164.5 (2)	C17—C18—C19—C20	56.3 (3)
C6—C5—C10—C1	176.3 (2)	O5—C19—C20—C30	−171.6 (2)
C4—C5—C10—C1	−50.0 (3)	C18—C19—C20—C30	66.8 (3)
C6—C5—C10—C25	−64.8 (3)	O5—C19—C20—C29	−54.5 (3)
C4—C5—C10—C25	68.9 (3)	C18—C19—C20—C29	−176.0 (2)
C6—C5—C10—C9	60.2 (2)	O5—C19—C20—C21	66.1 (3)
C4—C5—C10—C9	−166.1 (2)	C18—C19—C20—C21	−55.5 (3)
C11—C9—C10—C1	58.8 (3)	C30—C20—C21—C22	−66.0 (3)
C8—C9—C10—C1	−168.7 (2)	C29—C20—C21—C22	174.7 (2)
C11—C9—C10—C25	−59.5 (3)	C19—C20—C21—C22	55.1 (3)
C8—C9—C10—C25	73.1 (3)	C20—C21—C22—C17	−55.1 (3)
C11—C9—C10—C5	174.7 (2)	C16—C17—C22—C21	167.6 (2)
C8—C9—C10—C5	−52.7 (3)	C28—C17—C22—C21	−70.8 (3)
C8—C9—C11—C12	59.4 (3)	C18—C17—C22—C21	50.3 (3)
C10—C9—C11—C12	−164.9 (2)	C31—O3—C28—C17	157.0 (2)
C9—C11—C12—C13	−55.8 (3)	C16—C17—C28—O3	54.2 (3)
C11—C12—C13—C18	−179.8 (2)	C22—C17—C28—O3	−66.8 (3)
C11—C12—C13—C14	53.9 (3)	C18—C17—C28—O3	173.4 (2)
C12—C13—C14—C15	−177.0 (2)	C28—O3—C31—O4	0.6 (4)
C18—C13—C14—C15	55.9 (3)	C28—O3—C31—C32	−177.6 (2)
C12—C13—C14—C27	66.6 (3)	C3—O1—C33—O2	0.4 (4)
C18—C13—C14—C27	−60.5 (3)	C3—O1—C33—C34	179.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱ	0.85	2.25	3.014 (2)	149
C26—H26B···O2ⁱⁱ	0.98	2.41	3.322 (3)	155
C32—H32B···O4ⁱⁱⁱ	0.98	2.43	3.323 (3)	152

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1/2, −y+1/2, −z.

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