3β-Hy-droxy-lup-20(29)-en-28-yl 1H-imidazole-1-carboxyl-ate.

The title triterpene, C(34)H(52)N(2)O(3), is a C-28 carbamate derivative of betulin prepared in a one-step reaction from the commercially available 1,1'-carbonyl-diimidazole (CDI). All rings are fused trans. The X-ray study shows the retention of the configuration of C-28 with respect to the known chiral centres of the molecule. In the crystal, the mol-ecules are O-H⋯O hydrogen bonded via the hy-droxy group and the carbonyl group of the carbamate function into chains running along the c axis. A quantum-mechanical ab initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond-lengths and valency angles close to the experimental values. The calculations also reproduce the mol-ecular conformation well, with calculated puckering parameters that agree well with the observed values.

Related literature

For the synthesis of the title compound, see: Santos et al. (2009 ▶). For the biological activity of betulin and betulinic acid, see: Dzubak et al. (2006 ▶); Tolstikova et al. (2006 ▶); Petronelli et al. (2009 ▶). For plant triterpenes as potential anti-cancer drugs, see: Kinghorn et al. (2004 ▶); Setzer & Setzer (2003 ▶). For products afforded by the reaction of CDI with alcohols and phenols, see: Tang et al. (2004 ▶); Totleben et al. (1997 ▶); Herbez & Fischer (2005 ▶); Moreira et al. (2008 ▶); Ramos Silva et al. (2007 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Duax & Norton (1975 ▶). The quantum chemical calculations were performed with the computer program GAMESS (Schmidt et al., 1993 ▶).

Experimental

Crystal data

C34H52N2O3

M = 536.78

Orthorhombic,

a = 8.2575 (2) Å

b = 12.3909 (4) Å

c = 29.0992 (8) Å

V = 2977.37 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.898, T max = 1.0

54547 measured reflections

3117 independent reflections

2106 reflections with I > 2σ(I)

R int = 0.111

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.119

S = 1.02

3117 reflections

360 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002489X/ez2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002489X/ez2217Isup2.hkl

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

C34H52N2O3	Dx = 1.197 Mg m−3
Mr = 536.78	Melting point: 476 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3394 reflections
a = 8.2575 (2) Å	θ = 2.6–19.6°
b = 12.3909 (4) Å	µ = 0.08 mm−1
c = 29.0992 (8) Å	T = 293 K
V = 2977.37 (15) Å3	Block, colourless
Z = 4	0.25 × 0.22 × 0.18 mm
F(000) = 1176

Bruker APEXII CCD area-detector diffractometer	3117 independent reflections
Radiation source: fine-focus sealed tube	2106 reflections with I > 2σ(I)
graphite	Rint = 0.111
φ and ω scans	θmax = 25.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→9
Tmin = 0.898, Tmax = 1.0	k = −14→14
54547 measured reflections	l = −35→35

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.259P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3117 reflections	Δρmax = 0.17 e Å−3
360 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (6)

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
O3A	1.2324 (3)	0.9802 (3)	−0.21004 (8)	0.0692 (9)
H3A	1.1856	0.9476	−0.2307	0.104*
O28A	0.3667 (3)	1.0883 (2)	0.12637 (8)	0.0487 (7)
O28B	0.3861 (3)	1.1078 (3)	0.20317 (9)	0.0608 (8)
N28A	0.1558 (3)	1.1559 (2)	0.16449 (11)	0.0456 (8)
N28B	−0.0758 (4)	1.2165 (3)	0.13709 (15)	0.0720 (11)
C1	1.1881 (4)	0.9825 (3)	−0.08289 (11)	0.0431 (10)
H1A	1.2619	1.0103	−0.0598	0.052*
H1B	1.1784	0.9052	−0.0782	0.052*
C2	1.2598 (4)	1.0030 (4)	−0.13052 (11)	0.0472 (10)
H2A	1.2766	1.0799	−0.1346	0.057*
H2B	1.3643	0.9676	−0.1328	0.057*
C3	1.1511 (4)	0.9619 (3)	−0.16763 (11)	0.0447 (9)
H3	1.1410	0.8837	−0.1636	0.054*
C4	0.9786 (4)	1.0102 (3)	−0.16640 (12)	0.0403 (9)
C5	0.9112 (4)	0.9973 (3)	−0.11667 (11)	0.0351 (8)
H5	0.9023	0.9191	−0.1124	0.042*
C6	0.7385 (4)	1.0385 (3)	−0.11032 (11)	0.0449 (10)
H6A	0.7396	1.1166	−0.1081	0.054*
H6B	0.6739	1.0187	−0.1369	0.054*
C7	0.6626 (4)	0.9911 (3)	−0.06708 (11)	0.0452 (10)
H7A	0.6511	0.9138	−0.0711	0.054*
H7B	0.5549	1.0211	−0.0634	0.054*
C8	0.7600 (4)	1.0123 (3)	−0.02291 (11)	0.0354 (8)
C9	0.9435 (4)	0.9876 (3)	−0.03140 (11)	0.0342 (8)
H9	0.9479	0.9092	−0.0358	0.041*
C10	1.0205 (4)	1.0351 (3)	−0.07616 (11)	0.0350 (8)
C11	1.0414 (4)	1.0077 (3)	0.01245 (11)	0.0421 (9)
H11A	1.1537	0.9890	0.0069	0.051*
H11B	1.0369	1.0839	0.0200	0.051*
C12	0.9792 (4)	0.9427 (3)	0.05311 (11)	0.0390 (9)
H12A	1.0394	0.9628	0.0804	0.047*
H12B	0.9980	0.8666	0.0474	0.047*
C13	0.7987 (4)	0.9610 (3)	0.06169 (10)	0.0334 (8)
H13	0.7858	1.0383	0.0678	0.040*
C14	0.6979 (4)	0.9367 (3)	0.01754 (11)	0.0346 (8)
C15	0.5141 (4)	0.9542 (3)	0.02663 (12)	0.0455 (10)
H15A	0.4933	1.0311	0.0280	0.055*
H15B	0.4539	0.9255	0.0007	0.055*
C16	0.4497 (4)	0.9020 (3)	0.07071 (12)	0.0470 (10)
H16A	0.3380	0.9237	0.0754	0.056*
H16B	0.4520	0.8241	0.0674	0.056*
C17	0.5496 (4)	0.9344 (3)	0.11233 (12)	0.0376 (9)
C18	0.7289 (4)	0.9020 (3)	0.10367 (11)	0.0365 (9)
H18	0.7282	0.8250	0.0959	0.044*
C19	0.8096 (4)	0.9114 (3)	0.15107 (11)	0.0403 (9)
H19	0.8379	0.9874	0.1560	0.048*
C20	0.9578 (5)	0.8441 (3)	0.16120 (13)	0.0477 (10)
C21	0.6699 (5)	0.8817 (4)	0.18491 (13)	0.0552 (11)
H21A	0.6939	0.8144	0.2005	0.066*
H21B	0.6571	0.9379	0.2079	0.066*
C22	0.5159 (4)	0.8707 (3)	0.15669 (13)	0.0466 (10)
H22A	0.4240	0.9008	0.1730	0.056*
H22B	0.4938	0.7955	0.1499	0.056*
C23	0.9800 (6)	1.1274 (3)	−0.18353 (14)	0.0609 (12)
H23A	1.0188	1.1295	−0.2146	0.091*
H23B	1.0499	1.1699	−0.1643	0.091*
H23C	0.8722	1.1563	−0.1824	0.091*
C24	0.8719 (5)	0.9437 (4)	−0.19920 (12)	0.0549 (11)
H24A	0.7664	0.9760	−0.2012	0.082*
H24B	0.8620	0.8714	−0.1877	0.082*
H24C	0.9206	0.9422	−0.2291	0.082*
C25	1.0456 (5)	1.1586 (3)	−0.07340 (13)	0.0534 (11)
H25A	1.0781	1.1780	−0.0428	0.080*
H25B	0.9461	1.1946	−0.0809	0.080*
H25C	1.1282	1.1799	−0.0948	0.080*
C26	0.7317 (5)	1.1319 (3)	−0.01023 (12)	0.0494 (10)
H26A	0.7605	1.1768	−0.0358	0.074*
H26B	0.7974	1.1505	0.0158	0.074*
H26C	0.6196	1.1427	−0.0028	0.074*
C27	0.7156 (5)	0.8154 (3)	0.00488 (12)	0.0455 (10)
H27A	0.6582	0.7723	0.0269	0.068*
H27B	0.8281	0.7959	0.0051	0.068*
H27C	0.6715	0.8031	−0.0252	0.068*
C28	0.5360 (4)	1.0553 (3)	0.12224 (13)	0.0461 (10)
H28A	0.5927	1.0719	0.1506	0.055*
H28B	0.5870	1.0956	0.0976	0.055*
C28A	0.3144 (4)	1.1153 (3)	0.16739 (14)	0.0452 (9)
C28B	0.0639 (5)	1.1753 (3)	0.12673 (15)	0.0536 (11)
H28C	0.0974	1.1608	0.0968	0.064*
C28C	−0.0750 (6)	1.2231 (4)	0.18384 (19)	0.0810 (16)
H28D	−0.1615	1.2487	0.2012	0.097*
C28D	0.0650 (5)	1.1884 (4)	0.20191 (16)	0.0702 (14)
H28E	0.0945	1.1867	0.2327	0.084*
C29	0.9945 (6)	0.7521 (4)	0.13855 (17)	0.0801 (15)
H29A	1.0819	0.7103	0.1480	0.096*
H29B	0.9324	0.7306	0.1135	0.096*
C30	1.0532 (6)	0.8776 (4)	0.19981 (16)	0.0818 (16)
H30A	1.1456	0.8311	0.2028	0.123*
H30B	0.9890	0.8735	0.2273	0.123*
H30C	1.0889	0.9506	0.1953	0.123*

	U11	U22	U33	U12	U13	U23
O3A	0.0532 (18)	0.118 (3)	0.0366 (15)	−0.0123 (18)	0.0124 (13)	−0.0020 (16)
O28A	0.0432 (15)	0.0619 (18)	0.0411 (15)	0.0164 (13)	0.0093 (12)	−0.0033 (14)
O28B	0.0542 (17)	0.083 (2)	0.0449 (17)	0.0161 (16)	−0.0023 (14)	0.0079 (16)
N28A	0.0382 (16)	0.0482 (19)	0.0505 (19)	0.0132 (15)	0.0066 (16)	0.0009 (17)
N28B	0.054 (2)	0.071 (3)	0.091 (3)	0.020 (2)	−0.016 (2)	−0.009 (2)
C1	0.0292 (18)	0.063 (3)	0.038 (2)	−0.0043 (19)	−0.0011 (15)	0.0032 (19)
C2	0.034 (2)	0.070 (3)	0.038 (2)	−0.005 (2)	0.0047 (16)	0.001 (2)
C3	0.041 (2)	0.060 (3)	0.034 (2)	−0.0035 (18)	0.0061 (18)	0.0000 (19)
C4	0.043 (2)	0.048 (2)	0.0300 (19)	−0.0036 (18)	−0.0006 (17)	0.0017 (18)
C5	0.0328 (18)	0.040 (2)	0.0322 (19)	−0.0014 (17)	−0.0038 (15)	0.0012 (17)
C6	0.038 (2)	0.058 (3)	0.039 (2)	0.0024 (19)	−0.0030 (17)	0.0054 (19)
C7	0.0283 (17)	0.065 (3)	0.042 (2)	0.0008 (19)	−0.0018 (16)	−0.001 (2)
C8	0.0311 (18)	0.039 (2)	0.0362 (19)	0.0052 (16)	−0.0016 (15)	−0.0024 (17)
C9	0.0282 (17)	0.043 (2)	0.0319 (19)	−0.0013 (16)	−0.0053 (15)	−0.0007 (16)
C10	0.0297 (19)	0.040 (2)	0.035 (2)	−0.0021 (16)	0.0007 (16)	−0.0016 (16)
C11	0.0297 (18)	0.065 (3)	0.0313 (19)	−0.0065 (19)	−0.0005 (15)	−0.0022 (19)
C12	0.0309 (18)	0.052 (2)	0.034 (2)	0.0016 (18)	−0.0033 (16)	−0.0058 (17)
C13	0.0308 (18)	0.038 (2)	0.0311 (18)	−0.0021 (15)	0.0020 (15)	−0.0038 (16)
C14	0.0269 (17)	0.042 (2)	0.0349 (19)	−0.0031 (16)	0.0042 (15)	−0.0044 (16)
C15	0.0309 (19)	0.062 (3)	0.043 (2)	0.0027 (18)	−0.0013 (17)	−0.0008 (19)
C16	0.0302 (18)	0.060 (3)	0.050 (2)	0.0003 (19)	0.0032 (18)	−0.002 (2)
C17	0.036 (2)	0.036 (2)	0.041 (2)	0.0021 (17)	0.0088 (17)	−0.0011 (17)
C18	0.0317 (18)	0.040 (2)	0.038 (2)	0.0027 (16)	0.0008 (16)	−0.0015 (17)
C19	0.042 (2)	0.040 (2)	0.039 (2)	−0.0010 (17)	−0.0004 (17)	−0.0028 (18)
C20	0.044 (2)	0.056 (3)	0.043 (2)	−0.002 (2)	0.004 (2)	0.016 (2)
C21	0.060 (3)	0.062 (3)	0.045 (2)	0.002 (2)	0.007 (2)	0.005 (2)
C22	0.043 (2)	0.045 (2)	0.051 (2)	0.0038 (18)	0.0128 (19)	0.0057 (19)
C23	0.070 (3)	0.060 (3)	0.053 (3)	0.003 (2)	−0.002 (2)	0.021 (2)
C24	0.049 (2)	0.076 (3)	0.040 (2)	−0.008 (2)	−0.0032 (19)	0.000 (2)
C25	0.063 (3)	0.048 (3)	0.049 (2)	−0.015 (2)	0.003 (2)	−0.006 (2)
C26	0.050 (2)	0.049 (3)	0.050 (2)	0.006 (2)	0.0109 (19)	0.0034 (19)
C27	0.045 (2)	0.045 (2)	0.046 (2)	−0.0104 (19)	−0.0012 (19)	−0.0084 (18)
C28	0.038 (2)	0.052 (3)	0.047 (2)	0.0067 (19)	0.0117 (18)	0.0009 (19)
C28A	0.042 (2)	0.044 (2)	0.050 (3)	0.0037 (19)	0.005 (2)	0.005 (2)
C28B	0.057 (3)	0.050 (3)	0.054 (3)	0.002 (2)	−0.010 (2)	−0.004 (2)
C28C	0.057 (3)	0.098 (4)	0.088 (4)	0.033 (3)	0.009 (3)	−0.011 (3)
C28D	0.061 (3)	0.095 (4)	0.054 (3)	0.024 (3)	0.008 (2)	−0.009 (3)
C29	0.076 (3)	0.069 (3)	0.095 (4)	0.028 (3)	−0.025 (3)	−0.018 (3)
C30	0.064 (3)	0.110 (4)	0.072 (3)	0.004 (3)	−0.010 (3)	−0.004 (3)

O3A—C3	1.423 (4)	C14—C15	1.555 (4)
O3A—H3A	0.8200	C15—C16	1.532 (5)
O28A—C28A	1.312 (4)	C15—H15A	0.9700
O28A—C28	1.462 (4)	C15—H15B	0.9700
O28B—C28A	1.201 (4)	C16—C17	1.520 (5)
N28A—C28B	1.357 (5)	C16—H16A	0.9700
N28A—C28D	1.382 (5)	C16—H16B	0.9700
N28A—C28A	1.406 (5)	C17—C28	1.529 (5)
N28B—C28B	1.297 (5)	C17—C22	1.539 (5)
N28B—C28C	1.363 (6)	C17—C18	1.555 (5)
C1—C2	1.528 (4)	C18—C19	1.536 (4)
C1—C10	1.543 (5)	C18—H18	0.9800
C1—H1A	0.9700	C19—C20	1.510 (5)
C1—H1B	0.9700	C19—C21	1.561 (5)
C2—C3	1.494 (5)	C19—H19	0.9800
C2—H2A	0.9700	C20—C29	1.352 (6)
C2—H2B	0.9700	C20—C30	1.433 (6)
C3—C4	1.546 (5)	C21—C22	1.520 (5)
C3—H3	0.9800	C21—H21A	0.9700
C4—C23	1.535 (5)	C21—H21B	0.9700
C4—C24	1.539 (5)	C22—H22A	0.9700
C4—C5	1.559 (5)	C22—H22B	0.9700
C5—C6	1.526 (5)	C23—H23A	0.9600
C5—C10	1.557 (5)	C23—H23B	0.9600
C5—H5	0.9800	C23—H23C	0.9600
C6—C7	1.524 (4)	C24—H24A	0.9600
C6—H6A	0.9700	C24—H24B	0.9600
C6—H6B	0.9700	C24—H24C	0.9600
C7—C8	1.539 (5)	C25—H25A	0.9600
C7—H7A	0.9700	C25—H25B	0.9600
C7—H7B	0.9700	C25—H25C	0.9600
C8—C26	1.545 (5)	C26—H26A	0.9600
C8—C9	1.566 (4)	C26—H26B	0.9600
C8—C14	1.590 (5)	C26—H26C	0.9600
C9—C11	1.531 (4)	C27—H27A	0.9600
C9—C10	1.565 (4)	C27—H27B	0.9600
C9—H9	0.9800	C27—H27C	0.9600
C10—C25	1.547 (5)	C28—H28A	0.9700
C11—C12	1.520 (4)	C28—H28B	0.9700
C11—H11A	0.9700	C28B—H28C	0.9300
C11—H11B	0.9700	C28C—C28D	1.341 (6)
C12—C13	1.528 (4)	C28C—H28D	0.9300
C12—H12A	0.9700	C28D—H28E	0.9300
C12—H12B	0.9700	C29—H29A	0.9300
C13—C18	1.536 (4)	C29—H29B	0.9300
C13—C14	1.560 (4)	C30—H30A	0.9600
C13—H13	0.9800	C30—H30B	0.9600
C14—C27	1.554 (5)	C30—H30C	0.9600
C3—O3A—H3A	109.5	C17—C16—C15	111.5 (3)
C28A—O28A—C28	117.4 (3)	C17—C16—H16A	109.3
C28B—N28A—C28D	106.5 (3)	C15—C16—H16A	109.3
C28B—N28A—C28A	129.3 (4)	C17—C16—H16B	109.3
C28D—N28A—C28A	124.2 (4)	C15—C16—H16B	109.3
C28B—N28B—C28C	104.6 (4)	H16A—C16—H16B	108.0
C2—C1—C10	113.1 (3)	C16—C17—C28	111.7 (3)
C2—C1—H1A	109.0	C16—C17—C22	115.8 (3)
C10—C1—H1A	109.0	C28—C17—C22	109.3 (3)
C2—C1—H1B	109.0	C16—C17—C18	108.6 (3)
C10—C1—H1B	109.0	C28—C17—C18	110.7 (3)
H1A—C1—H1B	107.8	C22—C17—C18	100.1 (3)
C3—C2—C1	111.5 (3)	C13—C18—C19	121.0 (3)
C3—C2—H2A	109.3	C13—C18—C17	111.3 (3)
C1—C2—H2A	109.3	C19—C18—C17	104.4 (3)
C3—C2—H2B	109.3	C13—C18—H18	106.4
C1—C2—H2B	109.3	C19—C18—H18	106.4
H2A—C2—H2B	108.0	C17—C18—H18	106.4
O3A—C3—C2	106.8 (3)	C20—C19—C18	119.0 (3)
O3A—C3—C4	113.1 (3)	C20—C19—C21	110.2 (3)
C2—C3—C4	113.9 (3)	C18—C19—C21	103.2 (3)
O3A—C3—H3	107.6	C20—C19—H19	108.0
C2—C3—H3	107.6	C18—C19—H19	108.0
C4—C3—H3	107.6	C21—C19—H19	108.0
C23—C4—C24	108.0 (3)	C29—C20—C30	120.2 (4)
C23—C4—C3	110.6 (3)	C29—C20—C19	123.5 (4)
C24—C4—C3	107.8 (3)	C30—C20—C19	116.0 (4)
C23—C4—C5	113.7 (3)	C22—C21—C19	107.4 (3)
C24—C4—C5	108.4 (3)	C22—C21—H21A	110.2
C3—C4—C5	108.1 (3)	C19—C21—H21A	110.2
C6—C5—C10	110.4 (3)	C22—C21—H21B	110.2
C6—C5—C4	114.3 (3)	C19—C21—H21B	110.2
C10—C5—C4	117.7 (3)	H21A—C21—H21B	108.5
C6—C5—H5	104.2	C21—C22—C17	104.8 (3)
C10—C5—H5	104.2	C21—C22—H22A	110.8
C4—C5—H5	104.2	C17—C22—H22A	110.8
C7—C6—C5	110.8 (3)	C21—C22—H22B	110.8
C7—C6—H6A	109.5	C17—C22—H22B	110.8
C5—C6—H6A	109.5	H22A—C22—H22B	108.9
C7—C6—H6B	109.5	C4—C23—H23A	109.5
C5—C6—H6B	109.5	C4—C23—H23B	109.5
H6A—C6—H6B	108.1	H23A—C23—H23B	109.5
C6—C7—C8	114.1 (3)	C4—C23—H23C	109.5
C6—C7—H7A	108.7	H23A—C23—H23C	109.5
C8—C7—H7A	108.7	H23B—C23—H23C	109.5
C6—C7—H7B	108.7	C4—C24—H24A	109.5
C8—C7—H7B	108.7	C4—C24—H24B	109.5
H7A—C7—H7B	107.6	H24A—C24—H24B	109.5
C7—C8—C26	106.5 (3)	C4—C24—H24C	109.5
C7—C8—C9	109.9 (3)	H24A—C24—H24C	109.5
C26—C8—C9	111.8 (3)	H24B—C24—H24C	109.5
C7—C8—C14	110.4 (3)	C10—C25—H25A	109.5
C26—C8—C14	109.9 (3)	C10—C25—H25B	109.5
C9—C8—C14	108.3 (3)	H25A—C25—H25B	109.5
C11—C9—C10	114.7 (3)	C10—C25—H25C	109.5
C11—C9—C8	110.3 (3)	H25A—C25—H25C	109.5
C10—C9—C8	116.8 (3)	H25B—C25—H25C	109.5
C11—C9—H9	104.5	C8—C26—H26A	109.5
C10—C9—H9	104.5	C8—C26—H26B	109.5
C8—C9—H9	104.5	H26A—C26—H26B	109.5
C1—C10—C25	107.8 (3)	C8—C26—H26C	109.5
C1—C10—C5	107.2 (3)	H26A—C26—H26C	109.5
C25—C10—C5	114.5 (3)	H26B—C26—H26C	109.5
C1—C10—C9	108.1 (3)	C14—C27—H27A	109.5
C25—C10—C9	112.6 (3)	C14—C27—H27B	109.5
C5—C10—C9	106.3 (3)	H27A—C27—H27B	109.5
C12—C11—C9	112.6 (3)	C14—C27—H27C	109.5
C12—C11—H11A	109.1	H27A—C27—H27C	109.5
C9—C11—H11A	109.1	H27B—C27—H27C	109.5
C12—C11—H11B	109.1	O28A—C28—C17	111.1 (3)
C9—C11—H11B	109.1	O28A—C28—H28A	109.4
H11A—C11—H11B	107.8	C17—C28—H28A	109.4
C11—C12—C13	112.2 (3)	O28A—C28—H28B	109.4
C11—C12—H12A	109.2	C17—C28—H28B	109.4
C13—C12—H12A	109.2	H28A—C28—H28B	108.0
C11—C12—H12B	109.2	O28B—C28A—O28A	127.3 (3)
C13—C12—H12B	109.2	O28B—C28A—N28A	122.6 (4)
H12A—C12—H12B	107.9	O28A—C28A—N28A	110.1 (3)
C12—C13—C18	115.1 (3)	N28B—C28B—N28A	112.2 (4)
C12—C13—C14	110.9 (3)	N28B—C28B—H28C	123.9
C18—C13—C14	111.3 (3)	N28A—C28B—H28C	123.9
C12—C13—H13	106.3	C28D—C28C—N28B	112.1 (4)
C18—C13—H13	106.3	C28D—C28C—H28D	124.0
C14—C13—H13	106.3	N28B—C28C—H28D	124.0
C27—C14—C15	105.5 (3)	C28C—C28D—N28A	104.6 (4)
C27—C14—C13	109.4 (3)	C28C—C28D—H28E	127.7
C15—C14—C13	110.7 (3)	N28A—C28D—H28E	127.7
C27—C14—C8	111.4 (3)	C20—C29—H29A	120.0
C15—C14—C8	111.0 (3)	C20—C29—H29B	120.0
C13—C14—C8	108.9 (3)	H29A—C29—H29B	120.0
C16—C15—C14	115.0 (3)	C20—C30—H30A	109.5
C16—C15—H15A	108.5	C20—C30—H30B	109.5
C14—C15—H15A	108.5	H30A—C30—H30B	109.5
C16—C15—H15B	108.5	C20—C30—H30C	109.5
C14—C15—H15B	108.5	H30A—C30—H30C	109.5
H15A—C15—H15B	107.5	H30B—C30—H30C	109.5
C10—C1—C2—C3	−58.5 (4)	C9—C8—C14—C27	−60.7 (3)
C1—C2—C3—O3A	−177.2 (3)	C7—C8—C14—C15	−57.6 (4)
C1—C2—C3—C4	57.1 (4)	C26—C8—C14—C15	59.6 (4)
O3A—C3—C4—C23	−48.1 (4)	C9—C8—C14—C15	−178.0 (3)
C2—C3—C4—C23	74.1 (4)	C7—C8—C14—C13	−179.7 (3)
O3A—C3—C4—C24	69.8 (4)	C26—C8—C14—C13	−62.5 (3)
C2—C3—C4—C24	−168.0 (3)	C9—C8—C14—C13	59.9 (3)
O3A—C3—C4—C5	−173.2 (3)	C27—C14—C15—C16	70.6 (4)
C2—C3—C4—C5	−51.0 (4)	C13—C14—C15—C16	−47.6 (4)
C23—C4—C5—C6	58.6 (4)	C8—C14—C15—C16	−168.6 (3)
C24—C4—C5—C6	−61.6 (4)	C14—C15—C16—C17	52.6 (4)
C3—C4—C5—C6	−178.2 (3)	C15—C16—C17—C28	65.0 (4)
C23—C4—C5—C10	−73.5 (4)	C15—C16—C17—C22	−169.0 (3)
C24—C4—C5—C10	166.3 (3)	C15—C16—C17—C18	−57.4 (4)
C3—C4—C5—C10	49.7 (4)	C12—C13—C18—C19	51.4 (4)
C10—C5—C6—C7	−63.2 (4)	C14—C13—C18—C19	178.7 (3)
C4—C5—C6—C7	161.3 (3)	C12—C13—C18—C17	174.4 (3)
C5—C6—C7—C8	56.1 (4)	C14—C13—C18—C17	−58.3 (4)
C6—C7—C8—C26	75.0 (4)	C16—C17—C18—C13	61.6 (4)
C6—C7—C8—C9	−46.3 (4)	C28—C17—C18—C13	−61.4 (4)
C6—C7—C8—C14	−165.7 (3)	C22—C17—C18—C13	−176.7 (3)
C7—C8—C9—C11	−179.6 (3)	C16—C17—C18—C19	−166.3 (3)
C26—C8—C9—C11	62.3 (4)	C28—C17—C18—C19	70.7 (4)
C14—C8—C9—C11	−58.9 (4)	C22—C17—C18—C19	−44.6 (3)
C7—C8—C9—C10	47.0 (4)	C13—C18—C19—C20	−79.6 (4)
C26—C8—C9—C10	−71.1 (4)	C17—C18—C19—C20	154.2 (3)
C14—C8—C9—C10	167.7 (3)	C13—C18—C19—C21	158.0 (3)
C2—C1—C10—C25	−70.7 (4)	C17—C18—C19—C21	31.8 (4)
C2—C1—C10—C5	53.0 (4)	C18—C19—C20—C29	−22.7 (5)
C2—C1—C10—C9	167.4 (3)	C21—C19—C20—C29	96.1 (5)
C6—C5—C10—C1	175.3 (3)	C18—C19—C20—C30	163.0 (4)
C4—C5—C10—C1	−51.0 (4)	C21—C19—C20—C30	−78.2 (4)
C6—C5—C10—C25	−65.2 (4)	C20—C19—C21—C22	−134.8 (3)
C4—C5—C10—C25	68.5 (4)	C18—C19—C21—C22	−6.7 (4)
C6—C5—C10—C9	59.8 (4)	C19—C21—C22—C17	−21.2 (4)
C4—C5—C10—C9	−166.5 (3)	C16—C17—C22—C21	156.3 (3)
C11—C9—C10—C1	60.2 (4)	C28—C17—C22—C21	−76.5 (4)
C8—C9—C10—C1	−168.4 (3)	C18—C17—C22—C21	39.8 (4)
C11—C9—C10—C25	−58.7 (4)	C28A—O28A—C28—C17	109.7 (4)
C8—C9—C10—C25	72.7 (4)	C16—C17—C28—O28A	53.7 (4)
C11—C9—C10—C5	175.1 (3)	C22—C17—C28—O28A	−75.7 (4)
C8—C9—C10—C5	−53.5 (4)	C18—C17—C28—O28A	174.9 (3)
C10—C9—C11—C12	−169.2 (3)	C28—O28A—C28A—O28B	−6.5 (6)
C8—C9—C11—C12	56.4 (4)	C28—O28A—C28A—N28A	173.6 (3)
C9—C11—C12—C13	−54.2 (4)	C28B—N28A—C28A—O28B	175.4 (4)
C11—C12—C13—C18	−177.3 (3)	C28D—N28A—C28A—O28B	−1.8 (6)
C11—C12—C13—C14	55.2 (4)	C28B—N28A—C28A—O28A	−4.7 (5)
C12—C13—C14—C27	63.5 (4)	C28D—N28A—C28A—O28A	178.1 (4)
C18—C13—C14—C27	−66.0 (3)	C28C—N28B—C28B—N28A	−0.6 (5)
C12—C13—C14—C15	179.4 (3)	C28D—N28A—C28B—N28B	−0.3 (5)
C18—C13—C14—C15	49.8 (4)	C28A—N28A—C28B—N28B	−177.9 (4)
C12—C13—C14—C8	−58.4 (4)	C28B—N28B—C28C—C28D	1.3 (7)
C18—C13—C14—C8	172.1 (3)	N28B—C28C—C28D—N28A	−1.4 (6)
C7—C8—C14—C27	59.6 (4)	C28B—N28A—C28D—C28C	1.0 (5)
C26—C8—C14—C27	176.9 (3)	C28A—N28A—C28D—C28C	178.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H3A···O28Bi	0.82	2.13	2.920 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3A—H3A⋯O28Bi	0.82	2.13	2.920 (4)	162

Symmetry code: (i) .