3α-Hy-droxy-tirucalla-8,24-dien-21-oic acid.

The title compound, C(30)H(48)O(3), a triterpene isolated from the resin of canarium schweinfurthiiand, is an isomer of the previously reported triterpene 3α-hy-droxy-tirucalla-7,24-dien-21-oic acid [Mora et al. (2001 ▶). Acta Cryst. C57, 638-640], which crystallizes in the same trigonal space group. The title mol-ecule consists of four fused rings having chair, half-chair, half-chair and envelope conformations for rings A, B, C and D, respectively (steroid labelling). An intra-molecular C-H⋯O hydrogen bond generates an S(7) ring. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O inter-actions, forming (001) sheets.

Related literature

For the crystal structure of 3α-hy­droxy­tirucalla-7,24-diene-21-oic acid, see: Mora et al. (2001 ▶). For the biological activity of canarium schweinfurthiiand, see: Atawodi (2010 ▶); Dongmo et al. (2010 ▶) and for its botany, see: Tchiégang et al. (2001 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C30H48O3

M = 456.68

Trigonal,

a = 11.2794 (2) Å

c = 36.6986 (6) Å

V = 4043.45 (12) Å3

Z = 6

Cu Kα radiation

μ = 0.54 mm−1

T = 100 K

0.29 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.859, T max = 0.935

29022 measured reflections

5154 independent reflections

5062 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 0.97

5154 reflections

305 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 2099 Friedel pairs

Flack parameter: −0.35 (19)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008956/hb5815sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008956/hb5815Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H48O3	Dx = 1.125 Mg m−3
Mr = 456.68	Cu Kα radiation, λ = 1.54178 Å
Trigonal, P3121	Cell parameters from 16991 reflections
a = 11.2794 (2) Å	θ = 3.6–71.8°
c = 36.6986 (6) Å	µ = 0.54 mm−1
V = 4043.45 (12) Å3	T = 100 K
Z = 6	Block, colorless
F(000) = 1512	0.29 × 0.24 × 0.13 mm

Bruker SMART APEXII DUO CCD diffractometer	5154 independent reflections
Radiation source: fine-focus sealed tube	5062 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 71.8°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→10
Tmin = 0.859, Tmax = 0.935	k = −13→13
29022 measured reflections	l = −45→43

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0607P)2 + 1.1875P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
5154 reflections	Δρmax = 0.34 e Å−3
305 parameters	Δρmin = −0.14 e Å−3
0 restraints	Absolute structure: Flack (1983), 2099 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.35 (19)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.12186 (11)	0.02017 (12)	0.12824 (3)	0.0298 (2)
H1O1	0.1165	0.0104	0.1543	0.045*
O2	−0.10300 (11)	−0.06580 (12)	0.13280 (3)	0.0294 (2)
O3	0.65407 (12)	0.90621 (15)	0.10227 (3)	0.0431 (3)
H1O3	0.7207	0.9089	0.1129	0.065*
C1	0.41649 (17)	0.72932 (17)	0.14749 (4)	0.0300 (3)
H1A	0.3776	0.6804	0.1707	0.036*
H1B	0.4653	0.6870	0.1357	0.036*
C2	0.51897 (18)	0.87967 (18)	0.15572 (4)	0.0330 (3)
H2A	0.4719	0.9207	0.1691	0.040*
H2B	0.5926	0.8852	0.1716	0.040*
C3	0.58166 (15)	0.96055 (17)	0.12096 (4)	0.0300 (3)
H3A	0.6466	1.0583	0.1274	0.036*
C4	0.47387 (16)	0.95453 (17)	0.09408 (4)	0.0314 (3)
C5	0.36344 (15)	0.80196 (16)	0.08805 (4)	0.0276 (3)
H5A	0.4118	0.7604	0.0751	0.033*
C6	0.24806 (18)	0.78286 (18)	0.06230 (5)	0.0368 (4)
H6A	0.1839	0.8038	0.0753	0.044*
H6B	0.2869	0.8465	0.0414	0.044*
C7	0.17160 (16)	0.63491 (17)	0.04855 (4)	0.0305 (3)
H7A	0.0803	0.6141	0.0396	0.037*
H7B	0.2224	0.6269	0.0276	0.037*
C8	0.15280 (15)	0.52984 (16)	0.07647 (4)	0.0273 (3)
C9	0.21172 (16)	0.56210 (16)	0.10983 (4)	0.0293 (3)
C10	0.29897 (15)	0.71123 (16)	0.12250 (4)	0.0266 (3)
C11	0.18977 (18)	0.45252 (16)	0.13711 (4)	0.0305 (3)
H11A	0.1557	0.4717	0.1600	0.037*
H11B	0.2801	0.4622	0.1426	0.037*
C12	0.09172 (17)	0.30243 (16)	0.12677 (4)	0.0289 (3)
H12A	0.1200	0.2428	0.1393	0.035*
H12B	−0.0022	0.2755	0.1348	0.035*
C13	0.09242 (15)	0.28248 (15)	0.08549 (4)	0.0248 (3)
C14	0.05170 (15)	0.38169 (16)	0.06713 (4)	0.0261 (3)
C15	0.03784 (19)	0.33660 (18)	0.02702 (4)	0.0343 (4)
H15A	0.1284	0.3796	0.0149	0.041*
H15B	−0.0227	0.3613	0.0135	0.041*
C16	−0.02608 (18)	0.17853 (17)	0.02912 (4)	0.0328 (3)
H16A	0.0254	0.1486	0.0134	0.039*
H16B	−0.1226	0.1322	0.0209	0.039*
C17	−0.01783 (15)	0.14260 (16)	0.06977 (4)	0.0256 (3)
H17A	−0.1070	0.1187	0.0815	0.031*
C18	0.23593 (16)	0.31412 (18)	0.07350 (4)	0.0328 (3)
H18A	0.2655	0.2621	0.0886	0.049*
H18B	0.3005	0.4123	0.0763	0.049*
H18C	0.2332	0.2882	0.0479	0.049*
C19	0.20263 (18)	0.7441 (2)	0.14522 (5)	0.0401 (4)
H19A	0.1593	0.6757	0.1646	0.060*
H19B	0.1319	0.7422	0.1293	0.060*
H19C	0.2560	0.8353	0.1561	0.060*
C20	0.00323 (16)	0.01791 (16)	0.07414 (4)	0.0263 (3)
H20A	0.0943	0.0414	0.0637	0.032*
C21	0.00184 (15)	−0.01382 (16)	0.11427 (4)	0.0253 (3)
C22	−0.10897 (16)	−0.10907 (16)	0.05432 (4)	0.0273 (3)
H22A	−0.1985	−0.1361	0.0657	0.033*
H22B	−0.1133	−0.0848	0.0286	0.033*
C23	−0.08548 (18)	−0.23138 (18)	0.05517 (5)	0.0339 (3)
H23A	0.0057	−0.2034	0.0447	0.041*
H23B	−0.0852	−0.2583	0.0808	0.041*
C24	−0.19244 (19)	−0.35336 (18)	0.03441 (4)	0.0331 (3)
H24A	−0.1793	−0.3524	0.0088	0.040*
C25	−0.30231 (19)	−0.46146 (18)	0.04752 (4)	0.0353 (4)
C26	−0.3398 (2)	−0.4808 (3)	0.08726 (5)	0.0611 (6)
H26A	−0.2694	−0.4035	0.1012	0.092*
H26B	−0.3461	−0.5660	0.0959	0.092*
H26C	−0.4283	−0.4856	0.0906	0.092*
C27	−0.4008 (2)	−0.5768 (2)	0.02355 (6)	0.0502 (5)
H27A	−0.3706	−0.5563	−0.0019	0.075*
H27B	−0.4923	−0.5877	0.0259	0.075*
H27C	−0.4039	−0.6618	0.0310	0.075*
C28	0.54466 (19)	1.0165 (2)	0.05767 (5)	0.0461 (5)
H28A	0.6284	1.1039	0.0621	0.069*
H28B	0.4828	1.0316	0.0421	0.069*
H28C	0.5680	0.9534	0.0455	0.069*
C29	0.4192 (2)	1.04643 (19)	0.10886 (6)	0.0443 (4)
H29A	0.4931	1.1421	0.1088	0.066*
H29B	0.3858	1.0187	0.1338	0.066*
H29C	0.3441	1.0367	0.0933	0.066*
C30	−0.08957 (17)	0.35873 (17)	0.07938 (5)	0.0346 (4)
H30A	−0.1093	0.4232	0.0666	0.052*
H30B	−0.0884	0.3737	0.1057	0.052*
H30C	−0.1605	0.2648	0.0736	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (5)	0.0419 (6)	0.0230 (5)	0.0203 (5)	−0.0021 (4)	−0.0007 (4)
O2	0.0250 (5)	0.0409 (6)	0.0199 (4)	0.0146 (5)	−0.0005 (4)	0.0017 (4)
O3	0.0251 (6)	0.0665 (9)	0.0380 (6)	0.0232 (6)	−0.0050 (5)	−0.0111 (6)
C1	0.0328 (8)	0.0353 (8)	0.0182 (6)	0.0144 (7)	−0.0059 (6)	−0.0014 (6)
C2	0.0327 (8)	0.0378 (9)	0.0218 (7)	0.0127 (7)	−0.0062 (6)	−0.0057 (6)
C3	0.0222 (7)	0.0365 (8)	0.0251 (7)	0.0099 (6)	−0.0041 (6)	−0.0042 (6)
C4	0.0229 (7)	0.0325 (8)	0.0305 (7)	0.0076 (7)	−0.0057 (6)	0.0028 (6)
C5	0.0218 (7)	0.0295 (8)	0.0242 (6)	0.0072 (6)	−0.0042 (5)	0.0037 (6)
C6	0.0283 (8)	0.0328 (9)	0.0374 (8)	0.0064 (7)	−0.0098 (7)	0.0096 (7)
C7	0.0249 (7)	0.0347 (8)	0.0230 (6)	0.0084 (6)	−0.0053 (6)	0.0061 (6)
C8	0.0209 (7)	0.0302 (8)	0.0254 (7)	0.0087 (6)	−0.0014 (5)	0.0055 (6)
C9	0.0287 (8)	0.0312 (8)	0.0220 (6)	0.0105 (6)	−0.0021 (6)	0.0042 (6)
C10	0.0225 (7)	0.0302 (8)	0.0239 (6)	0.0109 (6)	−0.0013 (6)	0.0032 (6)
C11	0.0377 (9)	0.0310 (8)	0.0190 (6)	0.0143 (7)	−0.0015 (6)	0.0013 (6)
C12	0.0347 (8)	0.0301 (8)	0.0183 (7)	0.0134 (7)	−0.0020 (6)	0.0029 (5)
C13	0.0220 (7)	0.0303 (7)	0.0195 (6)	0.0111 (6)	0.0004 (5)	0.0038 (5)
C14	0.0235 (7)	0.0306 (8)	0.0192 (6)	0.0099 (6)	−0.0025 (5)	0.0038 (6)
C15	0.0419 (9)	0.0345 (9)	0.0199 (7)	0.0141 (7)	−0.0068 (6)	0.0016 (6)
C16	0.0407 (9)	0.0358 (9)	0.0194 (7)	0.0172 (7)	−0.0057 (6)	−0.0002 (6)
C17	0.0243 (7)	0.0324 (8)	0.0184 (6)	0.0129 (6)	−0.0006 (5)	0.0004 (5)
C18	0.0236 (7)	0.0394 (9)	0.0321 (8)	0.0133 (7)	0.0016 (6)	0.0028 (7)
C19	0.0320 (8)	0.0386 (9)	0.0454 (9)	0.0143 (7)	0.0094 (7)	0.0034 (8)
C20	0.0256 (7)	0.0335 (8)	0.0195 (6)	0.0145 (6)	0.0005 (5)	0.0003 (6)
C21	0.0256 (7)	0.0292 (8)	0.0224 (6)	0.0148 (6)	−0.0021 (5)	−0.0018 (6)
C22	0.0313 (8)	0.0343 (8)	0.0179 (6)	0.0177 (7)	−0.0018 (5)	−0.0019 (6)
C23	0.0355 (8)	0.0376 (9)	0.0331 (8)	0.0216 (7)	−0.0006 (7)	0.0003 (7)
C24	0.0449 (9)	0.0356 (8)	0.0255 (7)	0.0251 (8)	0.0015 (7)	−0.0013 (6)
C25	0.0400 (9)	0.0388 (9)	0.0309 (8)	0.0224 (8)	−0.0010 (7)	0.0012 (7)
C26	0.0495 (12)	0.0782 (16)	0.0365 (10)	0.0176 (12)	0.0085 (9)	0.0057 (10)
C27	0.0547 (12)	0.0410 (10)	0.0492 (10)	0.0196 (10)	−0.0079 (9)	−0.0037 (8)
C28	0.0343 (9)	0.0401 (10)	0.0347 (8)	−0.0033 (8)	−0.0102 (7)	0.0079 (7)
C29	0.0350 (9)	0.0337 (9)	0.0607 (11)	0.0145 (7)	−0.0089 (8)	−0.0001 (8)
C30	0.0245 (7)	0.0285 (8)	0.0465 (9)	0.0101 (6)	−0.0018 (7)	0.0053 (7)

O1—C21	1.3128 (18)	C15—C16	1.555 (2)
O1—H1O1	0.9626	C15—H15A	0.9900
O2—C21	1.2293 (18)	C15—H15B	0.9900
O3—C3	1.419 (2)	C16—C17	1.5606 (19)
O3—H1O3	0.8340	C16—H16A	0.9900
C1—C2	1.531 (2)	C16—H16B	0.9900
C1—C10	1.539 (2)	C17—C20	1.547 (2)
C1—H1A	0.9900	C17—H17A	1.0000
C1—H1B	0.9900	C18—H18A	0.9800
C2—C3	1.521 (2)	C18—H18B	0.9800
C2—H2A	0.9900	C18—H18C	0.9800
C2—H2B	0.9900	C19—H19A	0.9800
C3—C4	1.541 (2)	C19—H19B	0.9800
C3—H3A	1.0000	C19—H19C	0.9800
C4—C28	1.534 (2)	C20—C21	1.5139 (18)
C4—C29	1.545 (3)	C20—C22	1.539 (2)
C4—C5	1.555 (2)	C20—H20A	1.0000
C5—C6	1.534 (2)	C22—C23	1.530 (2)
C5—C10	1.5591 (19)	C22—H22A	0.9900
C5—H5A	1.0000	C22—H22B	0.9900
C6—C7	1.531 (2)	C23—C24	1.506 (2)
C6—H6A	0.9900	C23—H23A	0.9900
C6—H6B	0.9900	C23—H23B	0.9900
C7—C8	1.499 (2)	C24—C25	1.320 (3)
C7—H7A	0.9900	C24—H24A	0.9500
C7—H7B	0.9900	C25—C27	1.502 (3)
C8—C9	1.353 (2)	C25—C26	1.504 (2)
C8—C14	1.518 (2)	C26—H26A	0.9800
C9—C11	1.512 (2)	C26—H26B	0.9800
C9—C10	1.536 (2)	C26—H26C	0.9800
C10—C19	1.555 (2)	C27—H27A	0.9800
C11—C12	1.537 (2)	C27—H27B	0.9800
C11—H11A	0.9900	C27—H27C	0.9800
C11—H11B	0.9900	C28—H28A	0.9800
C12—C13	1.5319 (18)	C28—H28B	0.9800
C12—H12A	0.9900	C28—H28C	0.9800
C12—H12B	0.9900	C29—H29A	0.9800
C13—C18	1.537 (2)	C29—H29B	0.9800
C13—C17	1.551 (2)	C29—H29C	0.9800
C13—C14	1.559 (2)	C30—H30A	0.9800
C14—C15	1.539 (2)	C30—H30B	0.9800
C14—C30	1.548 (2)	C30—H30C	0.9800
C21—O1—H1O1	111.0	C16—C15—H15B	110.9
C3—O3—H1O3	117.4	H15A—C15—H15B	109.0
C2—C1—C10	112.80 (14)	C15—C16—C17	106.94 (12)
C2—C1—H1A	109.0	C15—C16—H16A	110.3
C10—C1—H1A	109.0	C17—C16—H16A	110.3
C2—C1—H1B	109.0	C15—C16—H16B	110.3
C10—C1—H1B	109.0	C17—C16—H16B	110.3
H1A—C1—H1B	107.8	H16A—C16—H16B	108.6
C3—C2—C1	111.47 (12)	C20—C17—C13	118.46 (12)
C3—C2—H2A	109.3	C20—C17—C16	113.03 (12)
C1—C2—H2A	109.3	C13—C17—C16	102.30 (12)
C3—C2—H2B	109.3	C20—C17—H17A	107.5
C1—C2—H2B	109.3	C13—C17—H17A	107.5
H2A—C2—H2B	108.0	C16—C17—H17A	107.5
O3—C3—C2	109.98 (14)	C13—C18—H18A	109.5
O3—C3—C4	106.45 (12)	C13—C18—H18B	109.5
C2—C3—C4	112.99 (13)	H18A—C18—H18B	109.5
O3—C3—H3A	109.1	C13—C18—H18C	109.5
C2—C3—H3A	109.1	H18A—C18—H18C	109.5
C4—C3—H3A	109.1	H18B—C18—H18C	109.5
C28—C4—C3	108.55 (13)	C10—C19—H19A	109.5
C28—C4—C29	106.96 (16)	C10—C19—H19B	109.5
C3—C4—C29	108.45 (14)	H19A—C19—H19B	109.5
C28—C4—C5	109.05 (13)	C10—C19—H19C	109.5
C3—C4—C5	108.52 (13)	H19A—C19—H19C	109.5
C29—C4—C5	115.14 (14)	H19B—C19—H19C	109.5
C6—C5—C4	113.39 (13)	C21—C20—C22	109.46 (12)
C6—C5—C10	108.84 (12)	C21—C20—C17	109.12 (12)
C4—C5—C10	117.61 (12)	C22—C20—C17	111.61 (12)
C6—C5—H5A	105.3	C21—C20—H20A	108.9
C4—C5—H5A	105.3	C22—C20—H20A	108.9
C10—C5—H5A	105.3	C17—C20—H20A	108.9
C7—C6—C5	109.39 (14)	O2—C21—O1	121.94 (12)
C7—C6—H6A	109.8	O2—C21—C20	122.99 (13)
C5—C6—H6A	109.8	O1—C21—C20	115.06 (12)
C7—C6—H6B	109.8	C23—C22—C20	113.39 (13)
C5—C6—H6B	109.8	C23—C22—H22A	108.9
H6A—C6—H6B	108.2	C20—C22—H22A	108.9
C8—C7—C6	114.61 (13)	C23—C22—H22B	108.9
C8—C7—H7A	108.6	C20—C22—H22B	108.9
C6—C7—H7A	108.6	H22A—C22—H22B	107.7
C8—C7—H7B	108.6	C24—C23—C22	113.12 (14)
C6—C7—H7B	108.6	C24—C23—H23A	109.0
H7A—C7—H7B	107.6	C22—C23—H23A	109.0
C9—C8—C7	123.32 (14)	C24—C23—H23B	109.0
C9—C8—C14	119.87 (13)	C22—C23—H23B	109.0
C7—C8—C14	116.57 (12)	H23A—C23—H23B	107.8
C8—C9—C11	121.45 (14)	C25—C24—C23	127.76 (14)
C8—C9—C10	121.88 (13)	C25—C24—H24A	116.1
C11—C9—C10	116.62 (12)	C23—C24—H24A	116.1
C9—C10—C1	111.30 (13)	C24—C25—C27	122.20 (16)
C9—C10—C19	106.40 (13)	C24—C25—C26	123.61 (17)
C1—C10—C19	107.89 (13)	C27—C25—C26	114.19 (17)
C9—C10—C5	107.84 (12)	C25—C26—H26A	109.5
C1—C10—C5	107.95 (12)	C25—C26—H26B	109.5
C19—C10—C5	115.50 (13)	H26A—C26—H26B	109.5
C9—C11—C12	118.07 (12)	C25—C26—H26C	109.5
C9—C11—H11A	107.8	H26A—C26—H26C	109.5
C12—C11—H11A	107.8	H26B—C26—H26C	109.5
C9—C11—H11B	107.8	C25—C27—H27A	109.5
C12—C11—H11B	107.8	C25—C27—H27B	109.5
H11A—C11—H11B	107.1	H27A—C27—H27B	109.5
C13—C12—C11	110.63 (12)	C25—C27—H27C	109.5
C13—C12—H12A	109.5	H27A—C27—H27C	109.5
C11—C12—H12A	109.5	H27B—C27—H27C	109.5
C13—C12—H12B	109.5	C4—C28—H28A	109.5
C11—C12—H12B	109.5	C4—C28—H28B	109.5
H12A—C12—H12B	108.1	H28A—C28—H28B	109.5
C12—C13—C18	109.33 (12)	C4—C28—H28C	109.5
C12—C13—C17	117.18 (11)	H28A—C28—H28C	109.5
C18—C13—C17	110.19 (13)	H28B—C28—H28C	109.5
C12—C13—C14	107.28 (12)	C4—C29—H29A	109.5
C18—C13—C14	111.32 (12)	C4—C29—H29B	109.5
C17—C13—C14	101.25 (11)	H29A—C29—H29B	109.5
C8—C14—C15	118.41 (13)	C4—C29—H29C	109.5
C8—C14—C30	105.21 (13)	H29A—C29—H29C	109.5
C15—C14—C30	107.25 (13)	H29B—C29—H29C	109.5
C8—C14—C13	111.32 (12)	C14—C30—H30A	109.5
C15—C14—C13	101.18 (12)	C14—C30—H30B	109.5
C30—C14—C13	113.73 (12)	H30A—C30—H30B	109.5
C14—C15—C16	104.10 (12)	C14—C30—H30C	109.5
C14—C15—H15A	110.9	H30A—C30—H30C	109.5
C16—C15—H15A	110.9	H30B—C30—H30C	109.5
C14—C15—H15B	110.9
C10—C1—C2—C3	−58.31 (18)	C11—C12—C13—C17	−170.39 (13)
C1—C2—C3—O3	−61.29 (17)	C11—C12—C13—C14	−57.48 (16)
C1—C2—C3—C4	57.51 (19)	C9—C8—C14—C15	−151.76 (16)
O3—C3—C4—C28	−49.08 (18)	C7—C8—C14—C15	33.7 (2)
C2—C3—C4—C28	−169.90 (15)	C9—C8—C14—C30	88.46 (17)
O3—C3—C4—C29	−164.95 (14)	C7—C8—C14—C30	−86.04 (16)
C2—C3—C4—C29	74.23 (17)	C9—C8—C14—C13	−35.2 (2)
O3—C3—C4—C5	69.31 (16)	C7—C8—C14—C13	150.34 (13)
C2—C3—C4—C5	−51.51 (18)	C12—C13—C14—C8	60.59 (15)
C28—C4—C5—C6	−63.26 (19)	C18—C13—C14—C8	−58.98 (16)
C3—C4—C5—C6	178.67 (14)	C17—C13—C14—C8	−176.07 (11)
C29—C4—C5—C6	56.93 (19)	C12—C13—C14—C15	−172.69 (12)
C28—C4—C5—C10	168.18 (15)	C18—C13—C14—C15	67.73 (15)
C3—C4—C5—C10	50.10 (18)	C17—C13—C14—C15	−49.35 (14)
C29—C4—C5—C10	−71.63 (18)	C12—C13—C14—C30	−58.04 (16)
C4—C5—C6—C7	162.20 (13)	C18—C13—C14—C30	−177.61 (13)
C10—C5—C6—C7	−64.86 (17)	C17—C13—C14—C30	65.30 (15)
C5—C6—C7—C8	38.2 (2)	C8—C14—C15—C16	159.15 (14)
C6—C7—C8—C9	−7.5 (2)	C30—C14—C15—C16	−82.13 (15)
C6—C7—C8—C14	166.80 (14)	C13—C14—C15—C16	37.27 (15)
C7—C8—C9—C11	179.99 (15)	C14—C15—C16—C17	−11.73 (17)
C14—C8—C9—C11	5.9 (2)	C12—C13—C17—C20	−77.28 (17)
C7—C8—C9—C10	2.6 (2)	C18—C13—C17—C20	48.55 (16)
C14—C8—C9—C10	−171.46 (14)	C14—C13—C17—C20	166.46 (12)
C8—C9—C10—C1	−146.20 (15)	C12—C13—C17—C16	157.72 (13)
C11—C9—C10—C1	36.34 (18)	C18—C13—C17—C16	−76.45 (14)
C8—C9—C10—C19	96.51 (18)	C14—C13—C17—C16	41.45 (14)
C11—C9—C10—C19	−80.96 (17)	C15—C16—C17—C20	−147.10 (14)
C8—C9—C10—C5	−28.0 (2)	C15—C16—C17—C13	−18.60 (16)
C11—C9—C10—C5	154.56 (14)	C13—C17—C20—C21	63.61 (16)
C2—C1—C10—C9	170.77 (12)	C16—C17—C20—C21	−176.81 (13)
C2—C1—C10—C19	−72.85 (16)	C13—C17—C20—C22	−175.29 (11)
C2—C1—C10—C5	52.61 (17)	C16—C17—C20—C22	−55.71 (17)
C6—C5—C10—C9	58.30 (17)	C22—C20—C21—O2	−49.73 (19)
C4—C5—C10—C9	−171.02 (13)	C17—C20—C21—O2	72.68 (18)
C6—C5—C10—C1	178.66 (14)	C22—C20—C21—O1	131.25 (14)
C4—C5—C10—C1	−50.65 (18)	C17—C20—C21—O1	−106.34 (15)
C6—C5—C10—C19	−60.53 (18)	C21—C20—C22—C23	−64.01 (16)
C4—C5—C10—C19	70.16 (18)	C17—C20—C22—C23	175.09 (13)
C8—C9—C11—C12	−3.3 (2)	C20—C22—C23—C24	−177.61 (12)
C10—C9—C11—C12	174.14 (14)	C22—C23—C24—C25	−97.4 (2)
C9—C11—C12—C13	30.5 (2)	C23—C24—C25—C27	−179.74 (18)
C11—C12—C13—C18	63.36 (17)	C23—C24—C25—C26	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.96	1.74	2.6762 (14)	162
O3—H1O3···O2ii	0.83	2.00	2.828 (2)	172
C12—H12A···O1	0.99	2.55	3.367 (2)	139
C22—H22A···O3iii	0.99	2.36	3.276 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.96	1.74	2.6762 (14)	162
O3—H1O3⋯O2ii	0.83	2.00	2.828 (2)	172
C12—H12A⋯O1	0.99	2.55	3.367 (2)	139
C22—H22A⋯O3iii	0.99	2.36	3.276 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) .