(+)-14bα-3-Oxoglycyrrhetinic acid: catemeric hydrogen bonding in a non-racemic triterpenoid diketo acid

Thompson, H.W.; Lalancette, R.A.; Kikolski, E.M.

doi:10.1107/S1600536806045788

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(+)-14bα-3-Oxoglycyrrhetinic acid: catemeric hydrogen bonding in a non-racemic triterpenoid diketo acid

H. W. Thompson, R. A. Lalancette and E. M. Kikolski

The title compound, (+)-10,13-dioxo-2α,4aβ,6aα,6bβ,9,9,12aβ-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8aα,9,10,11,12,12a,12bα,13,14bα-eicosahydropicene-2β-carboxylic acid, C₃₀H₄₄O₄, aggregates as carboxyl-to-ketone hydrogen-bonding catemers. Hydrogen bonds progress from the carboxyl group of one molecule to the remote-ring ketone group of a translationally related neighbor in an adjoining cell connected by a common a cell-edge [O

O = 2.766 (3) Å and O—H

O = 163°], yielding chains that extend in the [011] direction. In the crystal structure, there are also four C—H

O close contacts.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045788/lh2223sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045788/lh2223Isup2.hkl Contains datablock I

CCDC reference: 630050

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.046
wR factor = 0.113
Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Author Response: _diffrn_measured_fraction_theta_full Low .......0.91. (Alert level A). Even though we collected data out to 0.83 \%A, the crystal diffracted poorly beyond 0.88 \%A resolution, where more than 40% of the missing data lie. Larger crystals were not obtainable, and since the crystals of this compound are no longer available, we can only rely on the current data set.


Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2     -   C16     ..       7.94 su

Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       0.30
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6A    -   C18     ..       5.35 su
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H7A    ..  H18B    ..       1.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  O2      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17C   ..  O3      ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B   ..  O4      ..       2.69 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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           67.71
           From the CIF: _reflns_number_total               3702
           Count of symmetry unique reflns         2259
           Completeness (_total/calc)            163.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1443
           Fraction of Friedel pairs measured     0.639
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4A    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6B    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8A    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A   = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14B   = .          S

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

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

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.

(+)-10,13-dioxo-2α,4aβ,6aα,6 bβ,9,9,12aβ-heptamethyl- 1,2,3,4,4a,5,6,6a,6 b,7,8,8aα,9,10,11,12,12a,12bα,13,14bα- eicosahydropicene-2β-carboxylic acid top

Crystal data top

C₃₀H₄₄O₄	Z = 1
M_r = 468.65	F(000) = 256
Triclinic, P1	D_x = 1.238 Mg m⁻³
Hall symbol: P 1	Melting point: 598 K
a = 6.6054 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.2228 (2) Å	Cell parameters from 8622 reflections
c = 14.5495 (3) Å	θ = 3.1–67.7°
α = 90.085 (2)°	µ = 0.63 mm⁻¹
β = 96.287 (2)°	T = 100 K
γ = 114.225 (2)°	Parallelepiped, colourless
V = 628.39 (3) Å³	0.28 × 0.14 × 0.09 mm

Data collection top

Bruker SMART CCD APEX-II area-detector diffractometer	3702 independent reflections
Radiation source: fine-focus sealed tube	3345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 67.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→7
T_min = 0.843, T_max = 0.945	k = −8→8
8622 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0454P)² + 0.3681P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3702 reflections	Δρ_max = 0.29 e Å⁻³
315 parameters	Δρ_min = −0.20 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1651 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (3)

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

	x	y	z	U_iso*/U_eq
C1	1.0963 (6)	0.3181 (5)	0.8084 (2)	0.0384 (8)
H1A	0.9926	0.3822	0.7892	0.046*
H1B	1.2383	0.3957	0.7827	0.046*
O1	1.2654 (4)	−0.0900 (3)	0.13736 (15)	0.0420 (6)
C2	1.1424 (5)	0.3330 (5)	0.9151 (2)	0.0362 (8)
O2	1.0843 (4)	0.4036 (3)	0.47008 (14)	0.0369 (5)
C3	0.9278 (6)	0.1925 (5)	0.9563 (2)	0.0447 (9)
H3A	0.9648	0.1871	1.0238	0.054*
H3B	0.8165	0.2519	0.9472	0.054*
O3	1.1774 (4)	0.6796 (4)	0.90149 (16)	0.0544 (7)
C4	0.8252 (6)	−0.0202 (5)	0.9135 (2)	0.0485 (10)
H4A	0.6841	−0.0981	0.9398	0.058*
H4B	0.9279	−0.0863	0.9305	0.058*
C4A	0.7751 (5)	−0.0307 (5)	0.8073 (2)	0.0396 (8)
O4	1.2512 (4)	0.5752 (4)	1.03971 (15)	0.0505 (7)
H4	1.2475	0.6838	1.0582	0.076*
C5	0.7100 (6)	−0.2479 (5)	0.7720 (2)	0.0445 (9)
H5A	0.5730	−0.3384	0.7980	0.053*
H5B	0.8309	−0.2902	0.7943	0.053*
C6	0.6679 (6)	−0.2742 (5)	0.6663 (2)	0.0414 (9)
H6A	0.5336	−0.2503	0.6448	0.050*
H6B	0.6358	−0.4164	0.6478	0.050*
C6A	0.8666 (5)	−0.1293 (4)	0.61690 (19)	0.0277 (6)
C6B	0.7869 (5)	−0.1274 (4)	0.51001 (19)	0.0274 (6)
C7	0.7242 (5)	−0.3363 (4)	0.46163 (19)	0.0289 (7)
H7A	0.8391	−0.3863	0.4836	0.035*
H7B	0.5800	−0.4330	0.4803	0.035*
C8	0.7034 (5)	−0.3363 (4)	0.3564 (2)	0.0313 (7)
H8A	0.5794	−0.2989	0.3331	0.038*
H8B	0.6683	−0.4745	0.3306	0.038*
C8A	0.9209 (5)	−0.1856 (4)	0.32446 (19)	0.0287 (7)
H8A1	1.0413	−0.2154	0.3603	0.034*
C9	0.9426 (5)	−0.2203 (4)	0.21993 (19)	0.0323 (7)
C10	1.1550 (5)	−0.0550 (4)	0.19087 (18)	0.0315 (7)
C11	1.2240 (5)	0.1602 (4)	0.2279 (2)	0.0318 (7)
H11A	1.1304	0.2196	0.1925	0.038*
H11B	1.3814	0.2419	0.2180	0.038*
C12	1.2017 (5)	0.1746 (4)	0.33116 (18)	0.0286 (7)
H12A	1.2337	0.3170	0.3492	0.034*
H12B	1.3152	0.1387	0.3673	0.034*
C12A	0.9688 (5)	0.0350 (4)	0.35646 (19)	0.0268 (7)
C12B	0.9836 (5)	0.0391 (4)	0.46472 (18)	0.0249 (6)
H12C	1.1173	0.0110	0.4854	0.030*
C13	1.0356 (5)	0.2455 (4)	0.51112 (19)	0.0291 (7)
C14	1.0400 (5)	0.2501 (4)	0.61213 (19)	0.0308 (7)
H14	1.1003	0.3796	0.6442	0.037*
C14A	0.9656 (5)	0.0860 (4)	0.66254 (19)	0.0297 (7)
C14B	0.9965 (5)	0.1019 (5)	0.7674 (2)	0.0344 (7)
H14B	1.1057	0.0426	0.7880	0.041*
C15	1.1923 (5)	0.5472 (5)	0.9484 (2)	0.0373 (8)
C16	1.3405 (6)	0.2824 (5)	0.9505 (2)	0.0421 (8)
H16A	1.4762	0.3787	0.9270	0.063*
H16B	1.3098	0.1439	0.9288	0.063*
H16C	1.3620	0.2924	1.0184	0.063*
C17	0.5905 (6)	0.0420 (6)	0.7776 (2)	0.0468 (9)
H17A	0.5717	0.0469	0.7100	0.070*
H17B	0.6323	0.1780	0.8058	0.070*
H17C	0.4496	−0.0525	0.7980	0.070*
C18	1.0542 (6)	−0.2055 (5)	0.6326 (2)	0.0417 (8)
H18A	1.1874	−0.1104	0.6070	0.062*
H18B	1.0033	−0.3402	0.6016	0.062*
H18C	1.0908	−0.2141	0.6991	0.062*
C19	0.5797 (5)	−0.0779 (5)	0.4975 (2)	0.0322 (7)
H19A	0.5491	−0.0520	0.4325	0.048*
H19B	0.6081	0.0430	0.5365	0.048*
H19C	0.4502	−0.1933	0.5156	0.048*
C20	0.9524 (7)	−0.4273 (5)	0.2079 (2)	0.0520 (10)
H20A	0.9722	−0.4493	0.1436	0.078*
H20B	0.8129	−0.5350	0.2231	0.078*
H20C	1.0785	−0.4299	0.2494	0.078*
C21	0.7467 (6)	−0.2230 (5)	0.1517 (2)	0.0408 (8)
H21A	0.7460	−0.0876	0.1521	0.061*
H21B	0.6056	−0.3220	0.1701	0.061*
H21C	0.7634	−0.2611	0.0892	0.061*
C22	0.7943 (5)	0.1076 (5)	0.3114 (2)	0.0315 (7)
H22A	0.6464	−0.0064	0.3038	0.047*
H22B	0.8338	0.1591	0.2506	0.047*
H22C	0.7914	0.2163	0.3509	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0376 (19)	0.0403 (18)	0.0318 (17)	0.0094 (15)	0.0095 (14)	−0.0001 (13)
O1	0.0504 (14)	0.0424 (12)	0.0333 (12)	0.0170 (11)	0.0138 (10)	−0.0023 (9)
C2	0.0300 (17)	0.0441 (18)	0.0280 (16)	0.0089 (14)	0.0041 (13)	−0.0020 (13)
O2	0.0513 (14)	0.0302 (11)	0.0290 (10)	0.0151 (10)	0.0101 (10)	0.0041 (8)
C3	0.0382 (19)	0.058 (2)	0.0262 (15)	0.0077 (16)	0.0061 (14)	−0.0012 (14)
O3	0.0674 (19)	0.0524 (15)	0.0367 (13)	0.0191 (13)	0.0018 (12)	0.0014 (11)
C4	0.040 (2)	0.056 (2)	0.0310 (17)	−0.0005 (16)	0.0103 (15)	0.0067 (15)
C4A	0.0261 (17)	0.055 (2)	0.0250 (15)	0.0031 (15)	0.0072 (13)	0.0039 (13)
O4	0.0661 (18)	0.0614 (16)	0.0320 (12)	0.0359 (14)	−0.0007 (11)	−0.0104 (10)
C5	0.039 (2)	0.049 (2)	0.0306 (17)	0.0018 (16)	0.0064 (15)	0.0132 (14)
C6	0.046 (2)	0.0367 (17)	0.0288 (16)	0.0035 (15)	0.0063 (15)	0.0054 (12)
C6A	0.0239 (15)	0.0341 (15)	0.0259 (14)	0.0130 (13)	0.0014 (12)	0.0038 (11)
C6B	0.0245 (16)	0.0340 (14)	0.0232 (13)	0.0107 (12)	0.0062 (12)	0.0031 (11)
C7	0.0259 (16)	0.0282 (15)	0.0303 (15)	0.0082 (12)	0.0059 (12)	0.0060 (11)
C8	0.0312 (17)	0.0282 (14)	0.0306 (15)	0.0088 (13)	0.0025 (12)	−0.0003 (11)
C8A	0.0311 (17)	0.0271 (14)	0.0259 (14)	0.0102 (12)	0.0030 (12)	0.0023 (11)
C9	0.043 (2)	0.0281 (15)	0.0258 (15)	0.0134 (13)	0.0070 (13)	−0.0006 (11)
C10	0.0399 (19)	0.0363 (16)	0.0198 (14)	0.0173 (14)	0.0030 (13)	0.0032 (11)
C11	0.0366 (18)	0.0293 (14)	0.0265 (14)	0.0090 (13)	0.0100 (13)	0.0045 (11)
C12	0.0346 (17)	0.0274 (14)	0.0233 (14)	0.0121 (13)	0.0049 (13)	0.0031 (11)
C12A	0.0275 (17)	0.0296 (15)	0.0257 (14)	0.0136 (13)	0.0057 (12)	0.0017 (11)
C12B	0.0215 (16)	0.0277 (14)	0.0224 (13)	0.0075 (12)	0.0003 (11)	0.0036 (11)
C13	0.0261 (17)	0.0306 (15)	0.0294 (15)	0.0099 (13)	0.0056 (12)	0.0023 (12)
C14	0.0263 (17)	0.0338 (15)	0.0288 (15)	0.0085 (13)	0.0050 (12)	−0.0030 (11)
C14A	0.0207 (16)	0.0407 (16)	0.0242 (14)	0.0088 (13)	0.0043 (12)	0.0027 (12)
C14B	0.0287 (17)	0.0423 (17)	0.0264 (15)	0.0087 (14)	0.0046 (12)	0.0035 (12)
C15	0.0293 (18)	0.0515 (19)	0.0287 (16)	0.0138 (15)	0.0047 (13)	−0.0014 (14)
C16	0.057 (2)	0.0363 (17)	0.0324 (16)	0.0162 (16)	0.0149 (15)	−0.0006 (13)
C17	0.0316 (18)	0.065 (2)	0.0332 (17)	0.0074 (16)	0.0126 (14)	−0.0052 (15)
C18	0.054 (2)	0.0477 (19)	0.0301 (16)	0.0304 (17)	−0.0035 (15)	0.0009 (13)
C19	0.0274 (16)	0.0432 (17)	0.0258 (14)	0.0139 (14)	0.0047 (12)	0.0046 (12)
C20	0.077 (3)	0.0356 (18)	0.045 (2)	0.0201 (18)	0.0277 (19)	0.0044 (15)
C21	0.0410 (19)	0.0430 (18)	0.0253 (15)	0.0045 (15)	0.0026 (13)	0.0007 (12)
C22	0.0371 (17)	0.0339 (15)	0.0262 (14)	0.0173 (13)	0.0040 (12)	0.0052 (11)

Geometric parameters (Å, º) top

C1—C14B	1.515 (4)	C8A—H8A1	1.0000
C1—C2	1.544 (4)	C9—C10	1.527 (4)
C1—H1A	0.9900	C9—C20	1.534 (4)
C1—H1B	0.9900	C9—C21	1.536 (5)
O1—C10	1.215 (3)	C10—C11	1.508 (4)
C2—C15	1.510 (4)	C11—C12	1.533 (4)
C2—C16	1.535 (5)	C11—H11A	0.9900
C2—C3	1.551 (4)	C11—H11B	0.9900
O2—C13	1.227 (3)	C12—C12A	1.540 (4)
C3—C4	1.502 (5)	C12—H12A	0.9900
C3—H3A	0.9900	C12—H12B	0.9900
C3—H3B	0.9900	C12A—C22	1.538 (4)
O3—C15	1.206 (4)	C12A—C12B	1.567 (4)
C4—C4A	1.540 (4)	C12B—C13	1.524 (4)
C4—H4A	0.9900	C12B—H12C	1.0000
C4—H4B	0.9900	C13—C14	1.467 (4)
C4A—C5	1.519 (5)	C14—C14A	1.337 (4)
C4A—C17	1.536 (5)	C14—H14	0.9500
C4A—C14B	1.558 (4)	C14A—C14B	1.515 (4)
O4—C15	1.334 (4)	C14B—H14B	1.0000
O4—H4	0.8400	C16—H16A	0.9800
C5—C6	1.529 (4)	C16—H16B	0.9800
C5—H5A	0.9900	C16—H16C	0.9800
C5—H5B	0.9900	C17—H17A	0.9800
C6—C6A	1.555 (4)	C17—H17B	0.9800
C6—H6A	0.9900	C17—H17C	0.9800
C6—H6B	0.9900	C18—H18A	0.9800
C6A—C14A	1.534 (4)	C18—H18B	0.9800
C6A—C18	1.545 (5)	C18—H18C	0.9800
C6A—C6B	1.588 (4)	C19—H19A	0.9800
C6B—C7	1.538 (4)	C19—H19B	0.9800
C6B—C19	1.543 (5)	C19—H19C	0.9800
C6B—C12B	1.574 (3)	C20—H20A	0.9800
C7—C8	1.522 (4)	C20—H20B	0.9800
C7—H7A	0.9900	C20—H20C	0.9800
C7—H7B	0.9900	C21—H21A	0.9800
C8—C8A	1.526 (4)	C21—H21B	0.9800
C8—H8A	0.9900	C21—H21C	0.9800
C8—H8B	0.9900	C22—H22A	0.9800
C8A—C12A	1.552 (4)	C22—H22B	0.9800
C8A—C9	1.572 (4)	C22—H22C	0.9800

C14B—C1—C2	113.5 (3)	C10—C11—H11A	108.9
C14B—C1—H1A	108.9	C12—C11—H11A	108.9
C2—C1—H1A	108.9	C10—C11—H11B	108.9
C14B—C1—H1B	108.9	C12—C11—H11B	108.9
C2—C1—H1B	108.9	H11A—C11—H11B	107.8
H1A—C1—H1B	107.7	C11—C12—C12A	113.5 (2)
C15—C2—C16	109.0 (3)	C11—C12—H12A	108.9
C15—C2—C1	108.3 (3)	C12A—C12—H12A	108.9
C16—C2—C1	112.5 (3)	C11—C12—H12B	108.9
C15—C2—C3	106.3 (3)	C12A—C12—H12B	108.9
C16—C2—C3	110.9 (3)	H12A—C12—H12B	107.7
C1—C2—C3	109.6 (3)	C22—C12A—C12	109.5 (2)
C4—C3—C2	113.2 (3)	C22—C12A—C8A	113.0 (2)
C4—C3—H3A	108.9	C12—C12A—C8A	107.5 (2)
C2—C3—H3A	108.9	C22—C12A—C12B	112.8 (2)
C4—C3—H3B	108.9	C12—C12A—C12B	107.4 (2)
C2—C3—H3B	108.9	C8A—C12A—C12B	106.2 (2)
H3A—C3—H3B	107.7	C13—C12B—C12A	114.9 (2)
C3—C4—C4A	113.8 (3)	C13—C12B—C6B	108.4 (2)
C3—C4—H4A	108.8	C12A—C12B—C6B	118.0 (2)
C4A—C4—H4A	108.8	C13—C12B—H12C	104.6
C3—C4—H4B	108.8	C12A—C12B—H12C	104.6
C4A—C4—H4B	108.8	C6B—C12B—H12C	104.6
H4A—C4—H4B	107.7	O2—C13—C14	120.0 (3)
C5—C4A—C17	111.6 (3)	O2—C13—C12B	124.2 (2)
C5—C4A—C4	108.3 (3)	C14—C13—C12B	115.7 (2)
C17—C4A—C4	110.9 (3)	C14A—C14—C13	125.0 (3)
C5—C4A—C14B	106.4 (3)	C14A—C14—H14	117.5
C17—C4A—C14B	111.4 (3)	C13—C14—H14	117.5
C4—C4A—C14B	108.1 (2)	C14—C14A—C14B	122.0 (3)
C15—O4—H4	109.5	C14—C14A—C6A	121.2 (2)
C4A—C5—C6	112.9 (3)	C14B—C14A—C6A	116.5 (2)
C4A—C5—H5A	109.0	C1—C14B—C14A	114.0 (2)
C6—C5—H5A	109.0	C1—C14B—C4A	111.5 (3)
C4A—C5—H5B	109.0	C14A—C14B—C4A	111.3 (2)
C6—C5—H5B	109.0	C1—C14B—H14B	106.5
H5A—C5—H5B	107.8	C14A—C14B—H14B	106.5
C5—C6—C6A	113.9 (3)	C4A—C14B—H14B	106.5
C5—C6—H6A	108.8	O3—C15—O4	122.1 (3)
C6A—C6—H6A	108.8	O3—C15—C2	126.4 (3)
C5—C6—H6B	108.8	O4—C15—C2	111.5 (3)
C6A—C6—H6B	108.8	C2—C16—H16A	109.5
H6A—C6—H6B	107.7	C2—C16—H16B	109.5
C14A—C6A—C18	105.8 (2)	H16A—C16—H16B	109.5
C14A—C6A—C6	110.8 (2)	C2—C16—H16C	109.5
C18—C6A—C6	107.3 (3)	H16A—C16—H16C	109.5
C14A—C6A—C6B	110.9 (2)	H16B—C16—H16C	109.5
C18—C6A—C6B	112.0 (2)	C4A—C17—H17A	109.5
C6—C6A—C6B	110.0 (2)	C4A—C17—H17B	109.5
C7—C6B—C19	108.3 (2)	H17A—C17—H17B	109.5
C7—C6B—C12B	109.6 (2)	C4A—C17—H17C	109.5
C19—C6B—C12B	109.6 (2)	H17A—C17—H17C	109.5
C7—C6B—C6A	110.5 (2)	H17B—C17—H17C	109.5
C19—C6B—C6A	110.3 (2)	C6A—C18—H18A	109.5
C12B—C6B—C6A	108.6 (2)	C6A—C18—H18B	109.5
C8—C7—C6B	114.4 (2)	H18A—C18—H18B	109.5
C8—C7—H7A	108.7	C6A—C18—H18C	109.5
C6B—C7—H7A	108.7	H18A—C18—H18C	109.5
C8—C7—H7B	108.7	H18B—C18—H18C	109.5
C6B—C7—H7B	108.7	C6B—C19—H19A	109.5
H7A—C7—H7B	107.6	C6B—C19—H19B	109.5
C7—C8—C8A	110.5 (2)	H19A—C19—H19B	109.5
C7—C8—H8A	109.6	C6B—C19—H19C	109.5
C8A—C8—H8A	109.6	H19A—C19—H19C	109.5
C7—C8—H8B	109.6	H19B—C19—H19C	109.5
C8A—C8—H8B	109.6	C9—C20—H20A	109.5
H8A—C8—H8B	108.1	C9—C20—H20B	109.5
C8—C8A—C12A	110.7 (2)	H20A—C20—H20B	109.5
C8—C8A—C9	113.9 (2)	C9—C20—H20C	109.5
C12A—C8A—C9	116.1 (2)	H20A—C20—H20C	109.5
C8—C8A—H8A1	105.0	H20B—C20—H20C	109.5
C12A—C8A—H8A1	105.0	C9—C21—H21A	109.5
C9—C8A—H8A1	105.0	C9—C21—H21B	109.5
C10—C9—C20	109.0 (3)	H21A—C21—H21B	109.5
C10—C9—C21	106.8 (2)	C9—C21—H21C	109.5
C20—C9—C21	107.2 (3)	H21A—C21—H21C	109.5
C10—C9—C8A	111.0 (2)	H21B—C21—H21C	109.5
C20—C9—C8A	108.2 (2)	C12A—C22—H22A	109.5
C21—C9—C8A	114.4 (3)	C12A—C22—H22B	109.5
O1—C10—C11	119.4 (3)	H22A—C22—H22B	109.5
O1—C10—C9	122.4 (3)	C12A—C22—H22C	109.5
C11—C10—C9	118.2 (2)	H22A—C22—H22C	109.5
C10—C11—C12	113.1 (2)	H22B—C22—H22C	109.5

C14B—C1—C2—C15	−167.8 (3)	C8—C8A—C12A—C22	−65.1 (3)
C14B—C1—C2—C16	71.6 (3)	C9—C8A—C12A—C22	66.8 (3)
C14B—C1—C2—C3	−52.2 (4)	C8—C8A—C12A—C12	173.9 (2)
C15—C2—C3—C4	167.1 (3)	C9—C8A—C12A—C12	−54.2 (3)
C16—C2—C3—C4	−74.5 (4)	C8—C8A—C12A—C12B	59.1 (3)
C1—C2—C3—C4	50.3 (4)	C9—C8A—C12A—C12B	−169.0 (2)
C2—C3—C4—C4A	−54.6 (4)	C22—C12A—C12B—C13	−57.0 (3)
C3—C4—C4A—C5	170.5 (3)	C12—C12A—C12B—C13	63.8 (3)
C3—C4—C4A—C17	−66.7 (4)	C8A—C12A—C12B—C13	178.7 (3)
C3—C4—C4A—C14B	55.7 (4)	C22—C12A—C12B—C6B	73.0 (3)
C17—C4A—C5—C6	60.6 (3)	C12—C12A—C12B—C6B	−166.2 (2)
C4—C4A—C5—C6	−177.1 (3)	C8A—C12A—C12B—C6B	−51.3 (3)
C14B—C4A—C5—C6	−61.1 (4)	C7—C6B—C12B—C13	177.6 (2)
C4A—C5—C6—C6A	55.0 (4)	C19—C6B—C12B—C13	58.9 (3)
C5—C6—C6A—C14A	−42.7 (4)	C6A—C6B—C12B—C13	−61.7 (3)
C5—C6—C6A—C18	72.3 (3)	C7—C6B—C12B—C12A	44.7 (3)
C5—C6—C6A—C6B	−165.7 (3)	C19—C6B—C12B—C12A	−74.0 (3)
C14A—C6A—C6B—C7	170.7 (3)	C6A—C6B—C12B—C12A	165.4 (2)
C18—C6A—C6B—C7	52.8 (3)	C12A—C12B—C13—O2	−6.8 (4)
C6—C6A—C6B—C7	−66.3 (3)	C6B—C12B—C13—O2	−141.4 (3)
C14A—C6A—C6B—C19	−69.6 (3)	C12A—C12B—C13—C14	177.3 (2)
C18—C6A—C6B—C19	172.5 (3)	C6B—C12B—C13—C14	42.8 (3)
C6—C6A—C6B—C19	53.4 (3)	O2—C13—C14—C14A	171.8 (3)
C14A—C6A—C6B—C12B	50.6 (3)	C12B—C13—C14—C14A	−12.2 (4)
C18—C6A—C6B—C12B	−67.3 (3)	C13—C14—C14A—C14B	173.8 (3)
C6—C6A—C6B—C12B	173.5 (3)	C13—C14—C14A—C6A	0.3 (5)
C19—C6B—C7—C8	74.0 (3)	C18—C6A—C14A—C14	101.0 (3)
C12B—C6B—C7—C8	−45.5 (3)	C6—C6A—C14A—C14	−143.0 (3)
C6A—C6B—C7—C8	−165.1 (2)	C6B—C6A—C14A—C14	−20.6 (4)
C6B—C7—C8—C8A	57.2 (3)	C18—C6A—C14A—C14B	−72.7 (3)
C7—C8—C8A—C12A	−64.4 (3)	C6—C6A—C14A—C14B	43.2 (4)
C7—C8—C8A—C9	162.6 (2)	C6B—C6A—C14A—C14B	165.7 (2)
C8—C8A—C9—C10	175.7 (3)	C2—C1—C14B—C14A	−175.9 (3)
C12A—C8A—C9—C10	45.4 (4)	C2—C1—C14B—C4A	57.0 (4)
C8—C8A—C9—C20	−64.7 (4)	C14—C14A—C14B—C1	5.9 (4)
C12A—C8A—C9—C20	165.0 (3)	C6A—C14A—C14B—C1	179.6 (3)
C8—C8A—C9—C21	54.7 (3)	C14—C14A—C14B—C4A	133.0 (3)
C12A—C8A—C9—C21	−75.7 (3)	C6A—C14A—C14B—C4A	−53.3 (4)
C20—C9—C10—O1	24.1 (4)	C5—C4A—C14B—C1	−172.1 (3)
C21—C9—C10—O1	−91.3 (3)	C17—C4A—C14B—C1	66.0 (3)
C8A—C9—C10—O1	143.3 (3)	C4—C4A—C14B—C1	−56.0 (4)
C20—C9—C10—C11	−158.0 (3)	C5—C4A—C14B—C14A	59.3 (4)
C21—C9—C10—C11	86.5 (3)	C17—C4A—C14B—C14A	−62.5 (3)
C8A—C9—C10—C11	−38.9 (4)	C4—C4A—C14B—C14A	175.4 (3)
O1—C10—C11—C12	−138.8 (3)	C16—C2—C15—O3	129.6 (4)
C9—C10—C11—C12	43.3 (4)	C1—C2—C15—O3	6.8 (5)
C10—C11—C12—C12A	−52.6 (4)	C3—C2—C15—O3	−110.8 (4)
C11—C12—C12A—C22	−66.4 (3)	C16—C2—C15—O4	−52.3 (3)
C11—C12—C12A—C8A	56.8 (3)	C1—C2—C15—O4	−175.0 (3)
C11—C12—C12A—C12B	170.8 (2)	C3—C2—C15—O4	67.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.84	1.95	2.766 (3)	163
C7—H7A···O2ⁱⁱ	0.99	2.66	3.579 (4)	155
C17—H17C···O3ⁱⁱⁱ	0.98	2.64	3.575 (4)	159
C20—H20A···O4^iv	0.98	2.46	3.304 (4)	144
C21—H21B···O4^v	0.98	2.69	3.225 (4)	115

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

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