Propargylaminyl 3α-hy-droxy-11-oxo-18β-olean-12-en-29-oate.

The title compound, C(33)H(49)NO(3), is the propargyl-amide of 18β-glycyrrhetinic acid, a penta-cyclic triterpenoid of inter-est as a therapeutic agent. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring C in a half-chair conformation. In the crystal, the terminal N-propargylcarboxamide group has remarkable structural effects on weak hydrogen-bond-like inter-actions. Particularly noteworthy are an inter-molecular O-H⋯π inter-action accepted side-on by the terminal alkyne group [O⋯C = 3.097 (2) and 3.356 (2) Å] and a short inter-molecular C-H⋯O inter-action [C⋯O = 3.115 (2) Å] donated by the alkyne C-H group. An N-H⋯O [N⋯O = 3.251 (2) Å] and a C(alkyl)-H⋯O [C⋯O = 3.254 (2) Å] interaction complement the crystal structure.

Related literature

For general information on the therapeutic aspects of the parent compounds glycyrrhizin and 18β-glycyrrhetinic acid, see: Baran et al. (1974 ▶); Kitagawa (2002 ▶); Asl & Hosseinzadeh (2008 ▶). For the synthesis of derivatives of 18β-glycyrrhetinic acid with a therapeutic background, see: Su et al. (2004 ▶); Beseda et al. (2010 ▶). For the crystal structures of 18β-glycyrrhetinic acid and derivatives, see: Campsteyn et al. (1977 ▶); Alvarez-Larena et al. (2007 ▶); Beseda et al. (2010 ▶); Amer et al. (2010 ▶). For the crystal structure data of several N-propargylcarboxamides, see: Hashmi et al. (2004 ▶); Frey et al. (2008 ▶). For weak hydrogen bonds involving C C—H moieties, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C33H49NO3

M = 507.73

Orthorhombic,

a = 6.7534 (8) Å

b = 13.4879 (16) Å

c = 31.132 (4) Å

V = 2835.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.56 × 0.43 × 0.38 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.87, T max = 0.97

41876 measured reflections

4658 independent reflections

4531 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.08

4658 reflections

349 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT, SADABS and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043534/jj2102sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043534/jj2102Isup2.hkl

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

C33H49NO3	F(000) = 1112
Mr = 507.73	Dx = 1.189 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9975 reflections
a = 6.7534 (8) Å	θ = 2.5–31.0°
b = 13.4879 (16) Å	µ = 0.07 mm−1
c = 31.132 (4) Å	T = 100 K
V = 2835.8 (6) Å3	Block, colourless
Z = 4	0.56 × 0.43 × 0.38 mm

Bruker Kappa APEXII CCD diffractometer	4658 independent reflections
Radiation source: fine-focus sealed tube	4531 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.87, Tmax = 0.97	k = −18→18
41876 measured reflections	l = −43→43

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.405P] where P = (Fo2 + 2Fc2)/3
4658 reflections	(Δ/σ)max < 0.001
349 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s 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.

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	0.33309 (16)	0.31149 (7)	−0.07972 (3)	0.02015 (19)
H1O	0.442 (4)	0.2913 (16)	−0.0864 (7)	0.037 (6)*
O2	0.69829 (15)	0.41262 (7)	0.11669 (3)	0.02086 (19)
O3	0.54563 (16)	0.58041 (7)	0.29778 (3)	0.0230 (2)
N1	0.44107 (17)	0.70328 (9)	0.34128 (3)	0.0200 (2)
H1N	0.359 (4)	0.7444 (15)	0.3467 (6)	0.036 (5)*
C1	0.48914 (18)	0.36216 (8)	0.03539 (3)	0.0145 (2)
H1A	0.5902	0.3298	0.0537	0.017*
H1B	0.3582	0.3510	0.0489	0.017*
C2	0.49087 (19)	0.31341 (8)	−0.00911 (4)	0.0151 (2)
H2A	0.6258	0.3179	−0.0214	0.018*
H2B	0.4570	0.2423	−0.0062	0.018*
C3	0.34512 (18)	0.36236 (8)	−0.03949 (4)	0.0145 (2)
H3	0.2116	0.3569	−0.0258	0.017*
C4	0.38603 (19)	0.47405 (8)	−0.04565 (4)	0.0146 (2)
C5	0.38760 (18)	0.52135 (8)	0.00015 (3)	0.0134 (2)
H5	0.2524	0.5076	0.0118	0.016*
C6	0.4025 (2)	0.63474 (9)	−0.00030 (4)	0.0185 (2)
H6A	0.5416	0.6548	−0.0053	0.022*
H6B	0.3206	0.6617	−0.0239	0.022*
C7	0.3310 (2)	0.67657 (9)	0.04257 (4)	0.0189 (2)
H7A	0.1891	0.6601	0.0463	0.023*
H7B	0.3428	0.7497	0.0419	0.023*
C8	0.44738 (18)	0.63652 (8)	0.08139 (3)	0.0136 (2)
C9	0.47071 (17)	0.52100 (8)	0.07863 (3)	0.01207 (19)
H9	0.3343	0.4950	0.0840	0.014*
C10	0.53109 (17)	0.47525 (8)	0.03395 (3)	0.01207 (19)
C11	0.59034 (18)	0.48589 (8)	0.11744 (3)	0.0141 (2)
C12	0.57055 (18)	0.54248 (8)	0.15768 (4)	0.0150 (2)
H12	0.6418	0.5195	0.1820	0.018*
C13	0.45862 (17)	0.62445 (8)	0.16244 (3)	0.0131 (2)
C14	0.33519 (18)	0.66155 (8)	0.12473 (4)	0.0138 (2)
C15	0.2914 (2)	0.77451 (9)	0.12719 (4)	0.0201 (2)
H15A	0.4054	0.8110	0.1150	0.024*
H15B	0.1743	0.7892	0.1091	0.024*
C16	0.2526 (2)	0.81288 (9)	0.17273 (4)	0.0206 (2)
H16A	0.1269	0.7843	0.1834	0.025*
H16B	0.2370	0.8858	0.1718	0.025*
C17	0.4198 (2)	0.78659 (9)	0.20414 (4)	0.0167 (2)
C18	0.44227 (18)	0.67238 (8)	0.20660 (3)	0.0139 (2)
H18	0.5696	0.6588	0.2219	0.017*
C19	0.27685 (19)	0.62085 (9)	0.23255 (4)	0.0164 (2)
H19A	0.1517	0.6249	0.2161	0.020*
H19B	0.3107	0.5498	0.2357	0.020*
C20	0.24291 (18)	0.66535 (9)	0.27734 (4)	0.0163 (2)
C21	0.2018 (2)	0.77698 (10)	0.27197 (4)	0.0203 (2)
H21A	0.0784	0.7862	0.2553	0.024*
H21B	0.1822	0.8074	0.3006	0.024*
C22	0.3723 (2)	0.82909 (9)	0.24901 (4)	0.0198 (2)
H22A	0.4924	0.8242	0.2671	0.024*
H22B	0.3393	0.9003	0.2460	0.024*
C23	0.2125 (2)	0.51640 (10)	−0.07188 (4)	0.0226 (3)
H23A	0.1912	0.4754	−0.0974	0.034*
H23B	0.2435	0.5844	−0.0807	0.034*
H23C	0.0923	0.5164	−0.0542	0.034*
C24	0.5763 (2)	0.49108 (10)	−0.07175 (4)	0.0205 (2)
H24A	0.5542	0.4710	−0.1016	0.031*
H24B	0.6841	0.4516	−0.0595	0.031*
H24C	0.6117	0.5615	−0.0708	0.031*
C25	0.75367 (19)	0.49072 (9)	0.02375 (4)	0.0169 (2)
H25A	0.8296	0.4909	0.0506	0.025*
H25B	0.7716	0.5542	0.0090	0.025*
H25C	0.8005	0.4368	0.0053	0.025*
C26	0.6530 (2)	0.68636 (9)	0.08061 (4)	0.0188 (2)
H26A	0.7187	0.6717	0.0533	0.028*
H26B	0.7334	0.6608	0.1044	0.028*
H26C	0.6375	0.7582	0.0837	0.028*
C27	0.13253 (18)	0.60715 (10)	0.12792 (4)	0.0190 (2)
H27A	0.0469	0.6422	0.1483	0.028*
H27B	0.1538	0.5391	0.1379	0.028*
H27C	0.0693	0.6060	0.0996	0.028*
C28	0.6161 (2)	0.83234 (10)	0.18927 (4)	0.0232 (3)
H28A	0.6539	0.8038	0.1615	0.035*
H28B	0.7194	0.8182	0.2105	0.035*
H28C	0.6005	0.9042	0.1863	0.035*
C29	0.42524 (18)	0.64604 (9)	0.30565 (4)	0.0158 (2)
C30	0.0673 (2)	0.61229 (11)	0.29881 (4)	0.0229 (3)
H30A	−0.0528	0.6233	0.2818	0.034*
H30B	0.0480	0.6388	0.3278	0.034*
H30C	0.0948	0.5411	0.3005	0.034*
C31	0.5958 (2)	0.68737 (9)	0.37267 (4)	0.0198 (2)
H31A	0.6567	0.6216	0.3676	0.024*
H31B	0.5365	0.6868	0.4017	0.024*
C32	0.7511 (2)	0.76365 (9)	0.37105 (4)	0.0189 (2)
C33	0.8791 (2)	0.82502 (10)	0.37026 (4)	0.0225 (2)
H33	0.9807	0.8737	0.3696	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0240 (5)	0.0186 (4)	0.0179 (4)	0.0004 (4)	−0.0040 (3)	−0.0042 (3)
O2	0.0255 (5)	0.0196 (4)	0.0175 (4)	0.0108 (4)	−0.0036 (4)	−0.0009 (3)
O3	0.0276 (5)	0.0207 (4)	0.0207 (4)	0.0077 (4)	−0.0027 (4)	−0.0045 (3)
N1	0.0178 (5)	0.0238 (5)	0.0186 (4)	0.0035 (4)	−0.0015 (4)	−0.0069 (4)
C1	0.0187 (5)	0.0115 (4)	0.0132 (4)	0.0004 (4)	0.0004 (4)	0.0013 (4)
C2	0.0184 (5)	0.0123 (4)	0.0147 (5)	0.0009 (4)	−0.0007 (4)	0.0011 (4)
C3	0.0163 (5)	0.0132 (4)	0.0139 (4)	−0.0009 (4)	−0.0012 (4)	−0.0006 (4)
C4	0.0186 (5)	0.0127 (4)	0.0125 (4)	−0.0004 (4)	−0.0012 (4)	0.0009 (4)
C5	0.0166 (5)	0.0116 (4)	0.0120 (4)	0.0009 (4)	−0.0014 (4)	0.0013 (4)
C6	0.0302 (6)	0.0117 (4)	0.0137 (4)	0.0015 (5)	−0.0027 (5)	0.0021 (4)
C7	0.0284 (6)	0.0135 (5)	0.0148 (5)	0.0057 (5)	−0.0044 (5)	0.0005 (4)
C8	0.0173 (5)	0.0105 (4)	0.0131 (4)	0.0012 (4)	−0.0013 (4)	0.0010 (4)
C9	0.0130 (4)	0.0118 (4)	0.0114 (4)	0.0018 (4)	−0.0004 (4)	0.0004 (4)
C10	0.0122 (4)	0.0118 (4)	0.0122 (4)	0.0009 (4)	0.0001 (4)	0.0008 (4)
C11	0.0158 (5)	0.0135 (4)	0.0132 (4)	0.0015 (4)	−0.0008 (4)	0.0009 (4)
C12	0.0170 (5)	0.0155 (5)	0.0126 (4)	0.0037 (4)	−0.0016 (4)	0.0005 (4)
C13	0.0130 (5)	0.0128 (4)	0.0133 (4)	−0.0001 (4)	−0.0003 (4)	0.0005 (4)
C14	0.0148 (5)	0.0125 (4)	0.0142 (4)	0.0024 (4)	−0.0018 (4)	−0.0007 (4)
C15	0.0289 (6)	0.0142 (5)	0.0172 (5)	0.0071 (5)	−0.0030 (5)	−0.0007 (4)
C16	0.0280 (6)	0.0150 (5)	0.0188 (5)	0.0068 (5)	−0.0025 (5)	−0.0022 (4)
C17	0.0207 (5)	0.0133 (5)	0.0162 (5)	0.0005 (4)	−0.0008 (4)	−0.0023 (4)
C18	0.0154 (5)	0.0126 (4)	0.0135 (4)	0.0004 (4)	−0.0005 (4)	−0.0013 (4)
C19	0.0169 (5)	0.0178 (5)	0.0147 (4)	−0.0019 (4)	0.0013 (4)	−0.0036 (4)
C20	0.0148 (5)	0.0189 (5)	0.0153 (4)	−0.0005 (4)	0.0012 (4)	−0.0038 (4)
C21	0.0213 (6)	0.0209 (6)	0.0186 (5)	0.0059 (5)	0.0008 (5)	−0.0053 (4)
C22	0.0273 (6)	0.0148 (5)	0.0174 (5)	0.0007 (5)	−0.0004 (5)	−0.0036 (4)
C23	0.0303 (7)	0.0190 (5)	0.0183 (5)	0.0053 (5)	−0.0091 (5)	0.0003 (4)
C24	0.0279 (6)	0.0184 (5)	0.0152 (5)	−0.0057 (5)	0.0041 (5)	0.0009 (4)
C25	0.0135 (5)	0.0195 (5)	0.0177 (5)	−0.0019 (4)	0.0014 (4)	−0.0015 (4)
C26	0.0223 (6)	0.0161 (5)	0.0179 (5)	−0.0051 (5)	0.0020 (4)	0.0000 (4)
C27	0.0132 (5)	0.0236 (5)	0.0200 (5)	0.0022 (4)	−0.0012 (4)	−0.0044 (4)
C28	0.0292 (7)	0.0172 (5)	0.0231 (6)	−0.0062 (5)	0.0022 (5)	−0.0015 (5)
C29	0.0166 (5)	0.0157 (5)	0.0150 (5)	−0.0029 (4)	0.0024 (4)	−0.0007 (4)
C30	0.0176 (5)	0.0302 (6)	0.0210 (5)	−0.0046 (5)	0.0048 (4)	−0.0044 (5)
C31	0.0201 (6)	0.0225 (6)	0.0168 (5)	−0.0013 (5)	−0.0017 (5)	−0.0021 (4)
C32	0.0186 (5)	0.0210 (5)	0.0171 (5)	0.0027 (5)	0.0013 (4)	−0.0032 (4)
C33	0.0189 (6)	0.0220 (5)	0.0266 (6)	0.0021 (5)	0.0025 (5)	−0.0028 (5)

O1—C3	1.4303 (14)	C16—C17	1.5354 (18)
O1—H1O	0.81 (2)	C16—H16A	0.9900
O2—C11	1.2284 (14)	C16—H16B	0.9900
O3—C29	1.2266 (15)	C17—C28	1.5339 (19)
N1—C29	1.3557 (15)	C17—C22	1.5438 (16)
N1—C31	1.4468 (17)	C17—C18	1.5498 (16)
N1—H1N	0.80 (2)	C18—C19	1.5439 (17)
C1—C2	1.5335 (15)	C18—H18	1.0000
C1—C10	1.5521 (15)	C19—C20	1.5352 (16)
C1—H1A	0.9900	C19—H19A	0.9900
C1—H1B	0.9900	C19—H19B	0.9900
C2—C3	1.5165 (16)	C20—C29	1.5366 (17)
C2—H2A	0.9900	C20—C30	1.5381 (18)
C2—H2B	0.9900	C20—C21	1.5403 (18)
C3—C4	1.5434 (15)	C21—C22	1.5269 (19)
C3—H3	1.0000	C21—H21A	0.9900
C4—C24	1.5373 (17)	C21—H21B	0.9900
C4—C23	1.5383 (18)	C22—H22A	0.9900
C4—C5	1.5622 (15)	C22—H22B	0.9900
C5—C6	1.5328 (15)	C23—H23A	0.9800
C5—C10	1.5597 (15)	C23—H23B	0.9800
C5—H5	1.0000	C23—H23C	0.9800
C6—C7	1.5276 (16)	C24—H24A	0.9800
C6—H6A	0.9900	C24—H24B	0.9800
C6—H6B	0.9900	C24—H24C	0.9800
C7—C8	1.5397 (16)	C25—H25A	0.9800
C7—H7A	0.9900	C25—H25B	0.9800
C7—H7B	0.9900	C25—H25C	0.9800
C8—C26	1.5429 (17)	C26—H26A	0.9800
C8—C9	1.5685 (15)	C26—H26B	0.9800
C8—C14	1.5837 (16)	C26—H26C	0.9800
C9—C11	1.5286 (15)	C27—H27A	0.9800
C9—C10	1.5754 (15)	C27—H27B	0.9800
C9—H9	1.0000	C27—H27C	0.9800
C10—C25	1.5505 (17)	C28—H28A	0.9800
C11—C12	1.4731 (15)	C28—H28B	0.9800
C12—C13	1.3475 (15)	C28—H28C	0.9800
C12—H12	0.9500	C30—H30A	0.9800
C13—C18	1.5232 (15)	C30—H30B	0.9800
C13—C14	1.5243 (15)	C30—H30C	0.9800
C14—C15	1.5539 (16)	C31—C32	1.4697 (18)
C14—C27	1.5561 (17)	C31—H31A	0.9900
C15—C16	1.5318 (17)	C31—H31B	0.9900
C15—H15A	0.9900	C32—C33	1.1973 (19)
C15—H15B	0.9900	C33—H33	0.9500
C3—O1—H1O	109.5 (15)	H16A—C16—H16B	107.8
C29—N1—C31	121.67 (11)	C28—C17—C16	110.53 (10)
C29—N1—H1N	120.6 (15)	C28—C17—C22	107.66 (10)
C31—N1—H1N	117.5 (15)	C16—C17—C22	109.74 (10)
C2—C1—C10	113.20 (9)	C28—C17—C18	109.28 (11)
C2—C1—H1A	108.9	C16—C17—C18	109.45 (10)
C10—C1—H1A	108.9	C22—C17—C18	110.16 (9)
C2—C1—H1B	108.9	C13—C18—C19	109.49 (9)
C10—C1—H1B	108.9	C13—C18—C17	112.60 (9)
H1A—C1—H1B	107.8	C19—C18—C17	113.74 (10)
C3—C2—C1	111.83 (10)	C13—C18—H18	106.9
C3—C2—H2A	109.3	C19—C18—H18	106.9
C1—C2—H2A	109.3	C17—C18—H18	106.9
C3—C2—H2B	109.3	C20—C19—C18	114.03 (9)
C1—C2—H2B	109.3	C20—C19—H19A	108.7
H2A—C2—H2B	107.9	C18—C19—H19A	108.7
O1—C3—C2	111.97 (9)	C20—C19—H19B	108.7
O1—C3—C4	111.69 (9)	C18—C19—H19B	108.7
C2—C3—C4	112.72 (10)	H19A—C19—H19B	107.6
O1—C3—H3	106.7	C19—C20—C29	109.58 (10)
C2—C3—H3	106.7	C19—C20—C30	109.15 (10)
C4—C3—H3	106.7	C29—C20—C30	106.84 (10)
C24—C4—C23	107.49 (10)	C19—C20—C21	108.10 (10)
C24—C4—C3	111.17 (10)	C29—C20—C21	111.87 (10)
C23—C4—C3	106.98 (10)	C30—C20—C21	111.27 (11)
C24—C4—C5	114.57 (10)	C22—C21—C20	111.39 (10)
C23—C4—C5	109.76 (10)	C22—C21—H21A	109.4
C3—C4—C5	106.64 (9)	C20—C21—H21A	109.4
C6—C5—C10	111.30 (10)	C22—C21—H21B	109.4
C6—C5—C4	113.55 (9)	C20—C21—H21B	109.4
C10—C5—C4	117.20 (9)	H21A—C21—H21B	108.0
C6—C5—H5	104.4	C21—C22—C17	114.17 (10)
C10—C5—H5	104.4	C21—C22—H22A	108.7
C4—C5—H5	104.4	C17—C22—H22A	108.7
C7—C6—C5	109.85 (10)	C21—C22—H22B	108.7
C7—C6—H6A	109.7	C17—C22—H22B	108.7
C5—C6—H6A	109.7	H22A—C22—H22B	107.6
C7—C6—H6B	109.7	C4—C23—H23A	109.5
C5—C6—H6B	109.7	C4—C23—H23B	109.5
H6A—C6—H6B	108.2	H23A—C23—H23B	109.5
C6—C7—C8	113.25 (10)	C4—C23—H23C	109.5
C6—C7—H7A	108.9	H23A—C23—H23C	109.5
C8—C7—H7A	108.9	H23B—C23—H23C	109.5
C6—C7—H7B	108.9	C4—C24—H24A	109.5
C8—C7—H7B	108.9	C4—C24—H24B	109.5
H7A—C7—H7B	107.7	H24A—C24—H24B	109.5
C7—C8—C26	107.12 (9)	C4—C24—H24C	109.5
C7—C8—C9	110.90 (9)	H24A—C24—H24C	109.5
C26—C8—C9	109.97 (10)	H24B—C24—H24C	109.5
C7—C8—C14	110.46 (9)	C10—C25—H25A	109.5
C26—C8—C14	110.56 (9)	C10—C25—H25B	109.5
C9—C8—C14	107.85 (9)	H25A—C25—H25B	109.5
C11—C9—C8	108.51 (9)	C10—C25—H25C	109.5
C11—C9—C10	116.09 (9)	H25A—C25—H25C	109.5
C8—C9—C10	117.61 (9)	H25B—C25—H25C	109.5
C11—C9—H9	104.3	C8—C26—H26A	109.5
C8—C9—H9	104.3	C8—C26—H26B	109.5
C10—C9—H9	104.3	H26A—C26—H26B	109.5
C25—C10—C1	108.37 (9)	C8—C26—H26C	109.5
C25—C10—C5	114.24 (9)	H26A—C26—H26C	109.5
C1—C10—C5	107.33 (9)	H26B—C26—H26C	109.5
C25—C10—C9	112.28 (9)	C14—C27—H27A	109.5
C1—C10—C9	108.19 (9)	C14—C27—H27B	109.5
C5—C10—C9	106.18 (9)	H27A—C27—H27B	109.5
O2—C11—C12	119.14 (10)	C14—C27—H27C	109.5
O2—C11—C9	123.22 (10)	H27A—C27—H27C	109.5
C12—C11—C9	117.63 (10)	H27B—C27—H27C	109.5
C13—C12—C11	124.71 (10)	C17—C28—H28A	109.5
C13—C12—H12	117.6	C17—C28—H28B	109.5
C11—C12—H12	117.6	H28A—C28—H28B	109.5
C12—C13—C18	119.21 (10)	C17—C28—H28C	109.5
C12—C13—C14	119.44 (10)	H28A—C28—H28C	109.5
C18—C13—C14	121.08 (9)	H28B—C28—H28C	109.5
C13—C14—C15	112.83 (9)	O3—C29—N1	121.48 (12)
C13—C14—C27	106.08 (9)	O3—C29—C20	122.60 (11)
C15—C14—C27	106.96 (10)	N1—C29—C20	115.86 (11)
C13—C14—C8	108.94 (9)	C20—C30—H30A	109.5
C15—C14—C8	110.00 (9)	C20—C30—H30B	109.5
C27—C14—C8	112.00 (9)	H30A—C30—H30B	109.5
C16—C15—C14	114.17 (10)	C20—C30—H30C	109.5
C16—C15—H15A	108.7	H30A—C30—H30C	109.5
C14—C15—H15A	108.7	H30B—C30—H30C	109.5
C16—C15—H15B	108.7	N1—C31—C32	112.85 (11)
C14—C15—H15B	108.7	N1—C31—H31A	109.0
H15A—C15—H15B	107.6	C32—C31—H31A	109.0
C15—C16—C17	112.68 (11)	N1—C31—H31B	109.0
C15—C16—H16A	109.1	C32—C31—H31B	109.0
C17—C16—H16A	109.1	H31A—C31—H31B	107.8
C15—C16—H16B	109.1	C33—C32—C31	178.94 (15)
C17—C16—H16B	109.1	C32—C33—H33	180.0
C10—C1—C2—C3	−56.26 (13)	C12—C13—C14—C27	88.45 (13)
C1—C2—C3—O1	−174.64 (9)	C18—C13—C14—C27	−85.52 (12)
C1—C2—C3—C4	58.41 (13)	C12—C13—C14—C8	−32.28 (14)
O1—C3—C4—C24	−56.59 (13)	C18—C13—C14—C8	153.74 (10)
C2—C3—C4—C24	70.50 (12)	C7—C8—C14—C13	−177.79 (9)
O1—C3—C4—C23	60.48 (13)	C26—C8—C14—C13	−59.40 (11)
C2—C3—C4—C23	−172.42 (10)	C9—C8—C14—C13	60.87 (12)
O1—C3—C4—C5	177.88 (10)	C7—C8—C14—C15	−53.63 (13)
C2—C3—C4—C5	−55.02 (12)	C26—C8—C14—C15	64.75 (12)
C24—C4—C5—C6	63.27 (14)	C9—C8—C14—C15	−174.98 (10)
C23—C4—C5—C6	−57.75 (14)	C7—C8—C14—C27	65.18 (12)
C3—C4—C5—C6	−173.29 (11)	C26—C8—C14—C27	−176.43 (9)
C24—C4—C5—C10	−68.75 (13)	C9—C8—C14—C27	−56.16 (12)
C23—C4—C5—C10	170.23 (10)	C13—C14—C15—C16	−37.49 (16)
C3—C4—C5—C10	54.69 (13)	C27—C14—C15—C16	78.78 (13)
C10—C5—C6—C7	−65.10 (14)	C8—C14—C15—C16	−159.35 (11)
C4—C5—C6—C7	160.06 (10)	C14—C15—C16—C17	54.15 (15)
C5—C6—C7—C8	58.01 (14)	C15—C16—C17—C28	60.43 (13)
C6—C7—C8—C26	73.20 (12)	C15—C16—C17—C22	179.01 (10)
C6—C7—C8—C9	−46.81 (14)	C15—C16—C17—C18	−59.98 (14)
C6—C7—C8—C14	−166.33 (10)	C12—C13—C18—C19	−85.20 (13)
C7—C8—C9—C11	178.96 (10)	C14—C13—C18—C19	88.79 (12)
C26—C8—C9—C11	60.67 (12)	C12—C13—C18—C17	147.22 (12)
C14—C8—C9—C11	−59.97 (12)	C14—C13—C18—C17	−38.79 (15)
C7—C8—C9—C10	44.66 (14)	C28—C17—C18—C13	−70.48 (12)
C26—C8—C9—C10	−73.64 (12)	C16—C17—C18—C13	50.69 (13)
C14—C8—C9—C10	165.72 (9)	C22—C17—C18—C13	171.44 (10)
C2—C1—C10—C25	−72.74 (12)	C28—C17—C18—C19	164.22 (10)
C2—C1—C10—C5	51.10 (12)	C16—C17—C18—C19	−74.61 (12)
C2—C1—C10—C9	165.29 (10)	C22—C17—C18—C19	46.14 (14)
C6—C5—C10—C25	−65.74 (13)	C13—C18—C19—C20	−178.29 (9)
C4—C5—C10—C25	67.29 (13)	C17—C18—C19—C20	−51.35 (14)
C6—C5—C10—C1	174.08 (10)	C18—C19—C20—C29	−66.74 (13)
C4—C5—C10—C1	−52.88 (12)	C18—C19—C20—C30	176.58 (10)
C6—C5—C10—C9	58.55 (12)	C18—C19—C20—C21	55.41 (13)
C4—C5—C10—C9	−168.41 (9)	C19—C20—C21—C22	−57.84 (13)
C11—C9—C10—C25	−55.10 (13)	C29—C20—C21—C22	62.90 (13)
C8—C9—C10—C25	75.83 (12)	C30—C20—C21—C22	−177.68 (10)
C11—C9—C10—C1	64.45 (12)	C20—C21—C22—C17	57.88 (14)
C8—C9—C10—C1	−164.63 (10)	C28—C17—C22—C21	−169.30 (10)
C11—C9—C10—C5	179.40 (9)	C16—C17—C22—C21	70.36 (13)
C8—C9—C10—C5	−49.68 (13)	C18—C17—C22—C21	−50.22 (14)
C8—C9—C11—O2	−149.86 (12)	C31—N1—C29—O3	−2.50 (19)
C10—C9—C11—O2	−14.78 (17)	C31—N1—C29—C20	174.64 (11)
C8—C9—C11—C12	31.32 (14)	C19—C20—C29—O3	−20.57 (16)
C10—C9—C11—C12	166.40 (10)	C30—C20—C29—O3	97.56 (14)
O2—C11—C12—C13	179.31 (12)	C21—C20—C29—O3	−140.44 (12)
C9—C11—C12—C13	−1.82 (18)	C19—C20—C29—N1	162.32 (10)
C11—C12—C13—C18	176.53 (11)	C30—C20—C29—N1	−79.55 (13)
C11—C12—C13—C14	2.44 (18)	C21—C20—C29—N1	42.45 (14)
C12—C13—C14—C15	−154.75 (11)	C29—N1—C31—C32	106.52 (14)
C18—C13—C14—C15	31.27 (15)

Please add C—H···π interaction to table

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···C32i	0.81 (2)	2.57 (2)	3.3559 (17)	164 (2)
O1—H1O···C33i	0.81 (2)	2.40 (2)	3.0973 (17)	145 (2)
N1—H1N···O2ii	0.80 (2)	2.57 (2)	3.2511 (15)	144 (2)
C31—H31B···O1iii	0.99	2.56	3.2541 (17)	127.
C33—H33···O2iv	0.95	2.27	3.1154 (17)	148.

Table 1

Hydrogen-bond and O—H⋯π geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯C32i	0.81 (2)	2.57 (2)	3.3559 (17)	164 (2)
O1—H1O⋯C33i	0.81 (2)	2.40 (2)	3.0973 (17)	145 (2)
N1—H1N⋯O2ii	0.80 (2)	2.57 (2)	3.2511 (15)	144 (2)
C31—H31B⋯O1iii	0.99	2.56	3.2541 (17)	127
C33—H33⋯O2iv	0.95	2.27	3.1154 (17)	148

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