Crystal structure and Hirshfeld surface analysis of 3-oxours-12-ene-27a,28-dioic acid (quafrinoic acid)

The title compound, known as quafrinoic acid, is a penta­cyclic triterpene isolated from Nauclea Pobeguinii. The compound is composed of five fused six-membered rings and the mol­ecular conformation is stabilized by intra­molecular C—H...O inter­action, forming S6 and S8 rings.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.115
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.26 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.70 eA-3
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        6.7 Ratio
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H15A   ..  H20C    ..       1.89 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H21C   ..  H22B    ..       1.88 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT791_ALERT_4_G The Model has Chirality at C5      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C8      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C9      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C10     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C17     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C18     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C25     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C26     (Chiral SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-Oxours-12-ene-27a,28-dioic acid

Crystal data

C30H44O5	F(000) = 528
Mr = 484.65	Dx = 1.221 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 8.3465 (2) Å	Cell parameters from 9925 reflections
b = 10.9783 (3) Å	θ = 5.1–72.1°
c = 14.6583 (4) Å	µ = 0.64 mm^−1
β = 101.056 (1)°	T = 100 K
V = 1318.22 (6) Å^3	Block, colourless
Z = 2	0.45 × 0.23 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5116 independent reflections
Radiation source: fine-focus sealed tube	5023 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 72.2°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.760, Tmax = 0.927	k = −12→13
28696 measured reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 0.4209P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.70 e Å^−3
5116 reflections	Δρmin = −0.31 e Å^−3
325 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0047 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack, 1983
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.14 (17)

Special details

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.

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.27554 (19)	0.9227 (2)	0.81577 (14)	0.0587 (6)
O2	0.63334 (15)	0.29733 (12)	0.81088 (9)	0.0213 (3)
O3	0.56617 (14)	0.43709 (13)	0.70046 (8)	0.0232 (3)
O4	1.26493 (17)	0.36149 (16)	0.66220 (11)	0.0376 (4)
O5	1.31424 (15)	0.25278 (16)	0.79245 (10)	0.0328 (3)
C1	0.6083 (2)	0.84362 (18)	0.72071 (13)	0.0250 (4)
H1A	0.6715	0.8743	0.6748	0.030*
H1B	0.5291	0.7829	0.6889	0.030*
C2	0.5145 (2)	0.9494 (2)	0.75258 (15)	0.0315 (4)
H2A	0.5919	1.0146	0.7786	0.038*
H2B	0.4378	0.9833	0.6986	0.038*
C3	0.4206 (2)	0.90781 (18)	0.82544 (14)	0.0295 (4)
C4	0.5182 (2)	0.84228 (17)	0.91042 (13)	0.0235 (4)
C5	0.62587 (19)	0.74263 (16)	0.87525 (12)	0.0190 (3)
H5A	0.5453	0.6818	0.8430	0.023*
C6	0.7330 (2)	0.66974 (17)	0.95315 (12)	0.0217 (4)
H6A	0.8352	0.7148	0.9770	0.026*
H6B	0.6745	0.6572	1.0051	0.026*
C7	0.7722 (2)	0.54683 (17)	0.91361 (11)	0.0206 (3)
H7A	0.6692	0.5010	0.8938	0.025*
H7B	0.8419	0.4994	0.9634	0.025*
C8	0.85976 (19)	0.55753 (17)	0.83033 (11)	0.0186 (3)
C9	0.7771 (2)	0.65618 (17)	0.75961 (11)	0.0192 (3)
H9A	0.6722	0.6185	0.7277	0.023*
C10	0.7266 (2)	0.77963 (16)	0.80027 (12)	0.0204 (4)
C11	0.8786 (2)	0.67108 (18)	0.68322 (14)	0.0281 (4)
H11A	0.8169	0.7212	0.6321	0.034*
H11B	0.9813	0.7144	0.7090	0.034*
C12	0.9178 (2)	0.55000 (19)	0.64540 (13)	0.0262 (4)
H12A	0.9584	0.5508	0.5891	0.031*
C13	0.90136 (19)	0.44199 (17)	0.68303 (11)	0.0195 (3)
C14	0.84932 (18)	0.42886 (17)	0.77766 (11)	0.0175 (3)
C15	0.96004 (19)	0.33334 (16)	0.83675 (11)	0.0171 (3)
H15A	1.0692	0.3697	0.8584	0.021*
H15B	0.9137	0.3141	0.8924	0.021*
C16	0.98026 (19)	0.21453 (16)	0.78546 (12)	0.0185 (3)
H16A	0.8734	0.1728	0.7695	0.022*
H16B	1.0563	0.1601	0.8269	0.022*
C17	1.0464 (2)	0.23782 (16)	0.69610 (12)	0.0194 (4)
C18	0.9318 (2)	0.32589 (17)	0.63186 (12)	0.0211 (4)
H18A	0.9905	0.3507	0.5814	0.025*
C19	0.6708 (2)	0.38454 (17)	0.76152 (11)	0.0174 (3)
C20	1.0395 (2)	0.59073 (18)	0.86730 (14)	0.0258 (4)
H20A	1.0453	0.6693	0.8996	0.039*
H20B	1.0973	0.5964	0.8152	0.039*
H20C	1.0904	0.5277	0.9107	0.039*
C21	0.8701 (2)	0.86653 (17)	0.83604 (14)	0.0254 (4)
H21A	0.9272	0.8856	0.7853	0.038*
H21B	0.9460	0.8273	0.8869	0.038*
H21C	0.8283	0.9419	0.8587	0.038*
C22	0.6152 (2)	0.93770 (19)	0.97522 (14)	0.0301 (4)
H22A	0.5396	0.9967	0.9940	0.045*
H22B	0.6908	0.9801	0.9425	0.045*
H22C	0.6770	0.8972	1.0305	0.045*
C23	0.3981 (2)	0.78061 (19)	0.96218 (14)	0.0283 (4)
H23A	0.3303	0.8426	0.9844	0.042*
H23B	0.4587	0.7351	1.0153	0.042*
H23C	0.3284	0.7246	0.9201	0.042*
C24	1.2189 (2)	0.29000 (17)	0.71987 (12)	0.0206 (3)
C25	0.7705 (2)	0.26347 (19)	0.58354 (13)	0.0248 (4)
H25A	0.7031	0.2461	0.6316	0.030*
C26	0.8008 (3)	0.1421 (2)	0.53560 (14)	0.0326 (5)
H26A	0.8574	0.1613	0.4831	0.039*
C27	0.9097 (2)	0.0580 (2)	0.60201 (14)	0.0307 (4)
H27A	0.9316	−0.0164	0.5682	0.037*
H27B	0.8519	0.0331	0.6520	0.037*
C28	1.0706 (2)	0.11713 (18)	0.64521 (14)	0.0266 (4)
H28A	1.1338	0.1340	0.5959	0.032*
H28B	1.1348	0.0598	0.6900	0.032*
C29	0.6414 (3)	0.0764 (3)	0.49574 (18)	0.0475 (6)
H29A	0.6656	0.0004	0.4659	0.071*
H29B	0.5734	0.1287	0.4497	0.071*
H29C	0.5830	0.0578	0.5460	0.071*
C30	0.6761 (3)	0.3486 (2)	0.51214 (15)	0.0378 (5)
H30A	0.6568	0.4257	0.5420	0.057*
H30B	0.5712	0.3114	0.4847	0.057*
H30C	0.7389	0.3642	0.4633	0.057*
H19A	0.539 (5)	0.281 (4)	0.796 (3)	0.082 (12)*
H4A	1.367 (3)	0.391 (5)	0.680 (4)	0.14 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0238 (8)	0.0760 (14)	0.0769 (12)	0.0147 (8)	0.0113 (8)	0.0335 (11)
O2	0.0138 (5)	0.0251 (7)	0.0263 (6)	−0.0035 (5)	0.0067 (4)	0.0021 (5)
O3	0.0123 (5)	0.0291 (7)	0.0266 (6)	−0.0014 (5)	−0.0003 (4)	0.0041 (5)
O4	0.0185 (6)	0.0464 (10)	0.0495 (9)	−0.0092 (6)	0.0106 (6)	0.0124 (7)
O5	0.0139 (6)	0.0527 (9)	0.0318 (7)	−0.0003 (6)	0.0041 (5)	0.0018 (6)
C1	0.0204 (8)	0.0245 (9)	0.0283 (9)	−0.0002 (7)	0.0004 (7)	0.0056 (7)
C2	0.0255 (9)	0.0282 (11)	0.0386 (10)	0.0046 (8)	0.0002 (8)	0.0076 (8)
C3	0.0225 (9)	0.0230 (10)	0.0414 (10)	0.0048 (7)	0.0024 (8)	0.0016 (8)
C4	0.0178 (8)	0.0217 (9)	0.0303 (9)	0.0001 (7)	0.0030 (7)	−0.0035 (7)
C5	0.0146 (7)	0.0187 (8)	0.0229 (8)	−0.0023 (6)	0.0019 (6)	−0.0014 (6)
C6	0.0226 (8)	0.0214 (9)	0.0206 (8)	−0.0003 (7)	0.0029 (7)	−0.0018 (7)
C7	0.0209 (8)	0.0211 (9)	0.0191 (7)	−0.0016 (7)	0.0026 (6)	0.0017 (7)
C8	0.0143 (7)	0.0198 (8)	0.0212 (8)	−0.0002 (6)	0.0020 (6)	0.0025 (7)
C9	0.0162 (7)	0.0204 (9)	0.0210 (8)	−0.0015 (6)	0.0034 (6)	0.0041 (7)
C10	0.0163 (7)	0.0171 (9)	0.0273 (8)	−0.0006 (6)	0.0026 (6)	0.0029 (7)
C11	0.0308 (9)	0.0240 (10)	0.0328 (10)	0.0003 (8)	0.0141 (8)	0.0095 (7)
C12	0.0259 (9)	0.0295 (10)	0.0265 (9)	0.0002 (8)	0.0137 (7)	0.0041 (8)
C13	0.0124 (7)	0.0265 (9)	0.0199 (8)	−0.0019 (7)	0.0042 (6)	0.0025 (7)
C14	0.0103 (7)	0.0217 (8)	0.0202 (7)	−0.0022 (6)	0.0021 (5)	0.0028 (7)
C15	0.0118 (7)	0.0209 (8)	0.0186 (7)	−0.0014 (6)	0.0028 (6)	0.0021 (6)
C16	0.0134 (7)	0.0200 (9)	0.0226 (8)	−0.0007 (6)	0.0043 (6)	0.0025 (7)
C17	0.0136 (7)	0.0224 (9)	0.0231 (8)	−0.0024 (6)	0.0057 (6)	−0.0021 (7)
C18	0.0157 (7)	0.0294 (10)	0.0192 (8)	−0.0032 (7)	0.0058 (6)	0.0013 (7)
C19	0.0123 (7)	0.0225 (9)	0.0186 (7)	−0.0009 (6)	0.0059 (6)	0.0000 (6)
C20	0.0160 (8)	0.0222 (9)	0.0369 (10)	−0.0025 (6)	−0.0006 (7)	−0.0020 (7)
C21	0.0189 (8)	0.0196 (9)	0.0371 (10)	−0.0039 (7)	0.0040 (7)	0.0023 (7)
C22	0.0266 (9)	0.0245 (10)	0.0382 (10)	−0.0022 (8)	0.0036 (8)	−0.0081 (8)
C23	0.0249 (9)	0.0262 (10)	0.0355 (10)	−0.0009 (8)	0.0101 (7)	−0.0057 (8)
C24	0.0156 (7)	0.0243 (9)	0.0237 (8)	−0.0002 (7)	0.0082 (6)	−0.0025 (7)
C25	0.0173 (8)	0.0331 (10)	0.0228 (8)	−0.0050 (7)	0.0010 (6)	−0.0005 (7)
C26	0.0323 (10)	0.0416 (12)	0.0255 (9)	−0.0099 (9)	0.0094 (8)	−0.0086 (9)
C27	0.0333 (10)	0.0301 (11)	0.0316 (10)	−0.0093 (9)	0.0137 (8)	−0.0097 (8)
C28	0.0243 (9)	0.0261 (10)	0.0317 (10)	−0.0007 (7)	0.0109 (7)	−0.0041 (8)
C29	0.0463 (13)	0.0494 (15)	0.0411 (12)	−0.0124 (12)	−0.0062 (10)	−0.0105 (11)
C30	0.0314 (10)	0.0439 (13)	0.0355 (11)	0.0079 (9)	0.0003 (8)	−0.0029 (9)

Geometric parameters (Å, º)

O1—C3	1.203 (3)	C14—C15	1.548 (2)
O2—C19	1.275 (2)	C15—C16	1.531 (2)
O2—H19A	0.79 (4)	C15—H15A	0.9900
O3—C19	1.264 (2)	C15—H15B	0.9900
O4—C24	1.266 (2)	C16—C17	1.537 (2)
O4—H4A	0.906 (10)	C16—H16A	0.9900
O5—C24	1.268 (2)	C16—H16B	0.9900
C1—C2	1.523 (3)	C17—C24	1.526 (2)
C1—C10	1.545 (2)	C17—C18	1.546 (2)
C1—H1A	0.9900	C17—C28	1.553 (3)
C1—H1B	0.9900	C18—C25	1.555 (2)
C2—C3	1.511 (3)	C18—H18A	1.0000
C2—H2A	0.9900	C20—H20A	0.9800
C2—H2B	0.9900	C20—H20B	0.9800
C3—C4	1.531 (3)	C20—H20C	0.9800
C4—C23	1.526 (3)	C21—H21A	0.9800
C4—C22	1.536 (3)	C21—H21B	0.9800
C4—C5	1.565 (2)	C21—H21C	0.9800
C5—C6	1.534 (2)	C22—H22A	0.9800
C5—C10	1.560 (2)	C22—H22B	0.9800
C5—H5A	1.0000	C22—H22C	0.9800
C6—C7	1.529 (2)	C23—H23A	0.9800
C6—H6A	0.9900	C23—H23B	0.9800
C6—H6B	0.9900	C23—H23C	0.9800
C7—C8	1.543 (2)	C25—C30	1.508 (3)
C7—H7A	0.9900	C25—C26	1.550 (3)
C7—H7B	0.9900	C25—H25A	1.0000
C8—C20	1.538 (2)	C26—C27	1.512 (3)
C8—C9	1.565 (2)	C26—C29	1.528 (3)
C8—C14	1.604 (2)	C26—H26A	1.0000
C9—C11	1.537 (2)	C27—C28	1.517 (3)
C9—C10	1.571 (2)	C27—H27A	0.9900
C9—H9A	1.0000	C27—H27B	0.9900
C10—C21	1.543 (2)	C28—H28A	0.9900
C11—C12	1.501 (3)	C28—H28B	0.9900
C11—H11A	0.9900	C29—H29A	0.9800
C11—H11B	0.9900	C29—H29B	0.9800
C12—C13	1.326 (3)	C29—H29C	0.9800
C12—H12A	0.9500	C30—H30A	0.9800
C13—C18	1.525 (3)	C30—H30B	0.9800
C13—C14	1.538 (2)	C30—H30C	0.9800
C14—C19	1.542 (2)
C19—O2—H19A	111 (3)	C15—C16—H16A	109.3
C24—O4—H4A	115 (3)	C17—C16—H16A	109.3
C2—C1—C10	113.99 (16)	C15—C16—H16B	109.3
C2—C1—H1A	108.8	C17—C16—H16B	109.3
C10—C1—H1A	108.8	H16A—C16—H16B	108.0
C2—C1—H1B	108.8	C24—C17—C16	110.18 (13)
C10—C1—H1B	108.8	C24—C17—C18	110.52 (14)
H1A—C1—H1B	107.6	C16—C17—C18	109.97 (13)
C3—C2—C1	110.69 (17)	C24—C17—C28	103.06 (13)
C3—C2—H2A	109.5	C16—C17—C28	111.63 (15)
C1—C2—H2A	109.5	C18—C17—C28	111.31 (14)
C3—C2—H2B	109.5	C13—C18—C17	111.42 (13)
C1—C2—H2B	109.5	C13—C18—C25	112.39 (14)
H2A—C2—H2B	108.1	C17—C18—C25	112.48 (15)
O1—C3—C2	121.49 (18)	C13—C18—H18A	106.7
O1—C3—C4	121.75 (19)	C17—C18—H18A	106.7
C2—C3—C4	116.73 (16)	C25—C18—H18A	106.7
C23—C4—C3	108.39 (15)	O3—C19—O2	122.26 (15)
C23—C4—C22	108.26 (15)	O3—C19—C14	118.73 (15)
C3—C4—C22	108.53 (16)	O2—C19—C14	119.00 (15)
C23—C4—C5	109.09 (15)	C8—C20—H20A	109.5
C3—C4—C5	108.06 (15)	C8—C20—H20B	109.5
C22—C4—C5	114.37 (14)	H20A—C20—H20B	109.5
C6—C5—C10	110.16 (13)	C8—C20—H20C	109.5
C6—C5—C4	114.15 (14)	H20A—C20—H20C	109.5
C10—C5—C4	118.11 (14)	H20B—C20—H20C	109.5
C6—C5—H5A	104.2	C10—C21—H21A	109.5
C10—C5—H5A	104.2	C10—C21—H21B	109.5
C4—C5—H5A	104.2	H21A—C21—H21B	109.5
C7—C6—C5	108.36 (13)	C10—C21—H21C	109.5
C7—C6—H6A	110.0	H21A—C21—H21C	109.5
C5—C6—H6A	110.0	H21B—C21—H21C	109.5
C7—C6—H6B	110.0	C4—C22—H22A	109.5
C5—C6—H6B	110.0	C4—C22—H22B	109.5
H6A—C6—H6B	108.4	H22A—C22—H22B	109.5
C6—C7—C8	113.65 (15)	C4—C22—H22C	109.5
C6—C7—H7A	108.8	H22A—C22—H22C	109.5
C8—C7—H7A	108.8	H22B—C22—H22C	109.5
C6—C7—H7B	108.8	C4—C23—H23A	109.5
C8—C7—H7B	108.8	C4—C23—H23B	109.5
H7A—C7—H7B	107.7	H23A—C23—H23B	109.5
C20—C8—C7	108.50 (14)	C4—C23—H23C	109.5
C20—C8—C9	110.22 (14)	H23A—C23—H23C	109.5
C7—C8—C9	111.18 (13)	H23B—C23—H23C	109.5
C20—C8—C14	109.73 (14)	O4—C24—O5	122.53 (16)
C7—C8—C14	108.88 (14)	O4—C24—C17	118.30 (15)
C9—C8—C14	108.31 (12)	O5—C24—C17	118.91 (15)
C11—C9—C8	108.79 (14)	C30—C25—C26	109.11 (16)
C11—C9—C10	114.23 (15)	C30—C25—C18	109.54 (17)
C8—C9—C10	117.53 (13)	C26—C25—C18	112.50 (15)
C11—C9—H9A	105.0	C30—C25—H25A	108.5
C8—C9—H9A	105.0	C26—C25—H25A	108.5
C10—C9—H9A	105.0	C18—C25—H25A	108.5
C21—C10—C1	108.51 (14)	C27—C26—C29	109.2 (2)
C21—C10—C5	114.20 (14)	C27—C26—C25	111.32 (15)
C1—C10—C5	107.32 (13)	C29—C26—C25	111.93 (19)
C21—C10—C9	114.51 (14)	C27—C26—H26A	108.1
C1—C10—C9	106.57 (14)	C29—C26—H26A	108.1
C5—C10—C9	105.25 (13)	C25—C26—H26A	108.1
C12—C11—C9	111.40 (15)	C26—C27—C28	112.44 (17)
C12—C11—H11A	109.3	C26—C27—H27A	109.1
C9—C11—H11A	109.3	C28—C27—H27A	109.1
C12—C11—H11B	109.3	C26—C27—H27B	109.1
C9—C11—H11B	109.3	C28—C27—H27B	109.1
H11A—C11—H11B	108.0	H27A—C27—H27B	107.8
C13—C12—C11	126.23 (15)	C27—C28—C17	112.29 (15)
C13—C12—H12A	116.9	C27—C28—H28A	109.1
C11—C12—H12A	116.9	C17—C28—H28A	109.1
C12—C13—C18	120.17 (15)	C27—C28—H28B	109.1
C12—C13—C14	121.93 (17)	C17—C28—H28B	109.1
C18—C13—C14	117.89 (15)	H28A—C28—H28B	107.9
C13—C14—C19	108.85 (13)	C26—C29—H29A	109.5
C13—C14—C15	109.06 (13)	C26—C29—H29B	109.5
C19—C14—C15	109.13 (14)	H29A—C29—H29B	109.5
C13—C14—C8	110.66 (14)	C26—C29—H29C	109.5
C19—C14—C8	108.26 (13)	H29A—C29—H29C	109.5
C15—C14—C8	110.83 (12)	H29B—C29—H29C	109.5
C16—C15—C14	114.36 (13)	C25—C30—H30A	109.5
C16—C15—H15A	108.7	C25—C30—H30B	109.5
C14—C15—H15A	108.7	H30A—C30—H30B	109.5
C16—C15—H15B	108.7	C25—C30—H30C	109.5
C14—C15—H15B	108.7	H30A—C30—H30C	109.5
H15A—C15—H15B	107.6	H30B—C30—H30C	109.5
C15—C16—C17	111.60 (14)
C10—C1—C2—C3	−56.5 (2)	C20—C8—C14—C13	−73.60 (17)
C1—C2—C3—O1	−124.2 (2)	C7—C8—C14—C13	167.79 (13)
C1—C2—C3—C4	53.9 (2)	C9—C8—C14—C13	46.77 (16)
O1—C3—C4—C23	12.1 (3)	C20—C8—C14—C19	167.19 (14)
C2—C3—C4—C23	−165.95 (17)	C7—C8—C14—C19	48.58 (16)
O1—C3—C4—C22	−105.2 (2)	C9—C8—C14—C19	−72.45 (15)
C2—C3—C4—C22	76.7 (2)	C20—C8—C14—C15	47.54 (17)
O1—C3—C4—C5	130.2 (2)	C7—C8—C14—C15	−71.08 (15)
C2—C3—C4—C5	−47.9 (2)	C9—C8—C14—C15	167.90 (12)
C23—C4—C5—C6	−63.04 (19)	C13—C14—C15—C16	−48.13 (18)
C3—C4—C5—C6	179.32 (15)	C19—C14—C15—C16	70.66 (16)
C22—C4—C5—C6	58.3 (2)	C8—C14—C15—C16	−170.20 (12)
C23—C4—C5—C10	165.07 (15)	C14—C15—C16—C17	56.47 (17)
C3—C4—C5—C10	47.43 (19)	C15—C16—C17—C24	64.84 (18)
C22—C4—C5—C10	−73.5 (2)	C15—C16—C17—C18	−57.23 (17)
C10—C5—C6—C7	−68.31 (17)	C15—C16—C17—C28	178.72 (14)
C4—C5—C6—C7	156.07 (14)	C12—C13—C18—C17	130.96 (17)
C5—C6—C7—C8	58.19 (18)	C14—C13—C18—C17	−49.90 (18)
C6—C7—C8—C20	76.36 (18)	C12—C13—C18—C25	−101.75 (19)
C6—C7—C8—C9	−45.00 (19)	C14—C13—C18—C25	77.39 (18)
C6—C7—C8—C14	−164.25 (13)	C24—C17—C18—C13	−68.80 (17)
C20—C8—C9—C11	54.48 (19)	C16—C17—C18—C13	53.07 (18)
C7—C8—C9—C11	174.83 (15)	C28—C17—C18—C13	177.31 (13)
C14—C8—C9—C11	−65.58 (17)	C24—C17—C18—C25	163.96 (13)
C20—C8—C9—C10	−77.29 (18)	C16—C17—C18—C25	−74.17 (17)
C7—C8—C9—C10	43.06 (19)	C28—C17—C18—C25	50.07 (18)
C14—C8—C9—C10	162.65 (13)	C13—C14—C19—O3	−47.5 (2)
C2—C1—C10—C21	−70.20 (19)	C15—C14—C19—O3	−166.42 (15)
C2—C1—C10—C5	53.7 (2)	C8—C14—C19—O3	72.86 (18)
C2—C1—C10—C9	166.01 (15)	C13—C14—C19—O2	133.37 (16)
C6—C5—C10—C21	−63.99 (19)	C15—C14—C19—O2	14.4 (2)
C4—C5—C10—C21	69.65 (19)	C8—C14—C19—O2	−106.28 (17)
C6—C5—C10—C1	175.69 (14)	C16—C17—C24—O4	−149.64 (17)
C4—C5—C10—C1	−50.67 (19)	C18—C17—C24—O4	−27.9 (2)
C6—C5—C10—C9	62.44 (16)	C28—C17—C24—O4	91.1 (2)
C4—C5—C10—C9	−163.91 (14)	C16—C17—C24—O5	36.0 (2)
C11—C9—C10—C21	−53.9 (2)	C18—C17—C24—O5	157.70 (16)
C8—C9—C10—C21	75.37 (18)	C28—C17—C24—O5	−83.28 (19)
C11—C9—C10—C1	66.10 (18)	C13—C18—C25—C30	61.30 (19)
C8—C9—C10—C1	−164.65 (14)	C17—C18—C25—C30	−171.98 (15)
C11—C9—C10—C5	179.87 (14)	C13—C18—C25—C26	−177.17 (14)
C8—C9—C10—C5	−50.88 (17)	C17—C18—C25—C26	−50.45 (19)
C8—C9—C11—C12	48.4 (2)	C30—C25—C26—C27	174.28 (17)
C10—C9—C11—C12	−178.13 (15)	C18—C25—C26—C27	52.5 (2)
C9—C11—C12—C13	−13.7 (3)	C30—C25—C26—C29	−63.2 (2)
C11—C12—C13—C18	174.45 (18)	C18—C25—C26—C29	175.04 (18)
C11—C12—C13—C14	−4.7 (3)	C29—C26—C27—C28	−179.62 (17)
C12—C13—C14—C19	106.02 (19)	C25—C26—C27—C28	−55.5 (2)
C18—C13—C14—C19	−73.11 (18)	C26—C27—C28—C17	56.3 (2)
C12—C13—C14—C15	−135.01 (17)	C24—C17—C28—C27	−171.43 (15)
C18—C13—C14—C15	45.86 (18)	C16—C17—C28—C27	70.3 (2)
C12—C13—C14—C8	−12.8 (2)	C18—C17—C28—C27	−53.0 (2)
C18—C13—C14—C8	168.04 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3^i	0.91 (1)	1.70 (1)	2.6046 (18)	172 (5)
O2—H19A···O5^ii	0.80 (4)	1.89 (4)	2.6702 (18)	165 (4)
C7—H7A···O2	0.99	2.54	3.232 (2)	127
C9—H9A···O3	1.00	2.18	3.009 (2)	139
C28—H28B···O1^iii	0.99	2.49	3.477 (3)	173
C29—H29A···O4^iv	0.98	2.57	3.497 (3)	158
C30—H30A···O3	0.98	2.58	3.221 (3)	123

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