1,2,5-Oxadiazolo[3,4-b]glycyrrhetinic acid.

THE TITLE COMPOUND [SYSTEMATIC NAME: 11-oxo-2,3-(oxy-dinitrilo)olean-12-en-29-oic acid], C(30)H(42)N(2)O(4), contains a linear array of five six-membered rings and a five-membered heterocyclic ring. The C ring, containing an α,β-unsaturated ketone, has a slightly distorted half-chair conformation, as does the A ring, with N-C-C angles 125.3 (5), 111.2 (4), 124.9 (5) and 109.2 (5)°, while the other three six-membered rings adopt chair conformations. The enanti-omer has been assigned by reference to unchanging chiral centres in the synthetic procedure. An intramolecular C-H⋯O interaction is present. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules.

Related literature

Glycyrrhetinic acid is the aglycone of glycyrrhizin, a triterpenoid saponin found in the roots of liquorice, see: Yoshida et al. (2001 ▶). For the pharmacological activities of glycyrrhetinic acid and its derivatives, see: Finney & Tarknoy (1960 ▶); Yu et al. (2006 ▶); Su et al. (2004 ▶).

Experimental

Crystal data

C30H42N2O4

M = 494.66

Orthorhombic,

a = 8.5489 (11) Å

b = 10.9019 (18) Å

c = 28.898 (3) Å

V = 2693.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.5 × 0.4 × 0.3 mm

Data collection

Bruker P4 diffractometer

Absorption correction: none

3717 measured reflections

2855 independent reflections

2178 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.109

S = 1.02

2855 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: XSCANS (Bruker, 1997 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020996/at2805sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020996/at2805Isup2.hkl

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

C30H42N2O4	F(000) = 1072
Mr = 494.66	Dx = 1.220 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 52 reflections
a = 8.5489 (11) Å	θ = 3.7–19.0°
b = 10.9019 (18) Å	µ = 0.08 mm−1
c = 28.898 (3) Å	T = 295 K
V = 2693.2 (6) Å3	Prism, colorless
Z = 4	0.5 × 0.4 × 0.3 mm

Bruker P4 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.0°
graphite	h = −1→10
ω scans	k = −13→1
3717 measured reflections	l = −1→35
2855 independent reflections	3 standard reflections every 97 reflections
2178 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.001P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3
2855 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. absolute configuration has not been established by anomalous dispersion effects in diffraction measurements on the crystal. The enantiomer has been assigned by reference to unchanging chiral centres in the synthetic procedure.

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	0.6409 (6)	−0.3844 (3)	0.25922 (12)	0.0902 (11)
O2	0.4151 (4)	−0.0311 (2)	0.41200 (9)	0.0636 (9)
O3	0.0227 (4)	0.4128 (3)	0.47645 (11)	0.0733 (9)
O4	0.0196 (5)	0.6051 (3)	0.50103 (11)	0.0802 (10)
H4A	−0.0380	0.5758	0.5208	0.096*
N1	0.5282 (6)	−0.3188 (3)	0.28470 (14)	0.0767 (12)
N2	0.7751 (6)	−0.3138 (4)	0.25298 (14)	0.0826 (14)
C1	0.5253 (6)	−0.1096 (4)	0.31919 (14)	0.0592 (12)
H1A	0.4552	−0.1415	0.3427	0.071*
H1B	0.4653	−0.0574	0.2986	0.071*
C2	0.5954 (6)	−0.2133 (4)	0.29242 (14)	0.0587 (12)
C3	0.7457 (6)	−0.2096 (4)	0.27309 (14)	0.0621 (13)
C4	0.8579 (6)	−0.1039 (4)	0.27610 (14)	0.0586 (12)
C5	0.7758 (5)	0.0033 (4)	0.30352 (13)	0.0535 (11)
H5A	0.7143	0.0485	0.2805	0.064*
C6	0.8964 (5)	0.0951 (4)	0.32221 (14)	0.0585 (11)
H6A	0.9502	0.0594	0.3485	0.070*
H6B	0.9734	0.1123	0.2985	0.070*
C7	0.8171 (5)	0.2144 (4)	0.33693 (14)	0.0573 (11)
H7A	0.7717	0.2530	0.3098	0.069*
H7B	0.8959	0.2696	0.3492	0.069*
C8	0.6882 (5)	0.1969 (4)	0.37362 (13)	0.0462 (10)
C9	0.5807 (5)	0.0872 (3)	0.36035 (13)	0.0466 (10)
H9A	0.5194	0.1173	0.3340	0.056*
C10	0.6578 (5)	−0.0339 (3)	0.34242 (13)	0.0483 (10)
C11	0.4616 (5)	0.0705 (4)	0.39885 (14)	0.0526 (11)
C12	0.3977 (6)	0.1813 (4)	0.41969 (14)	0.0535 (11)
H12A	0.3130	0.1726	0.4396	0.064*
C13	0.4519 (5)	0.2939 (3)	0.41227 (13)	0.0450 (10)
C14	0.5843 (5)	0.3161 (3)	0.37735 (13)	0.0463 (10)
C15	0.6873 (5)	0.4283 (4)	0.39076 (15)	0.0553 (11)
H15A	0.7681	0.4011	0.4119	0.066*
H15B	0.7386	0.4587	0.3631	0.066*
C16	0.5968 (5)	0.5356 (3)	0.41356 (14)	0.0576 (11)
H16A	0.6712	0.5968	0.4240	0.069*
H16B	0.5302	0.5737	0.3905	0.069*
C17	0.4960 (5)	0.4953 (4)	0.45462 (14)	0.0521 (10)
C18	0.3760 (5)	0.4008 (3)	0.43689 (13)	0.0487 (10)
H18A	0.3251	0.3666	0.4644	0.058*
C19	0.2459 (5)	0.4588 (4)	0.40792 (14)	0.0541 (11)
H19A	0.2902	0.4872	0.3789	0.065*
H19B	0.1690	0.3963	0.4007	0.065*
C20	0.1633 (5)	0.5660 (4)	0.43147 (15)	0.0554 (11)
C21	0.2844 (6)	0.6604 (4)	0.44773 (17)	0.0653 (13)
H21A	0.3316	0.6990	0.4209	0.078*
H21B	0.2319	0.7237	0.4655	0.078*
C22	0.4116 (6)	0.6038 (4)	0.47708 (16)	0.0644 (12)
H22A	0.3659	0.5766	0.5060	0.077*
H22B	0.4882	0.6666	0.4843	0.077*
C23	1.0152 (6)	−0.1466 (5)	0.29607 (17)	0.0815 (16)
H23A	0.9998	−0.1769	0.3269	0.122*
H23B	1.0868	−0.0788	0.2967	0.122*
H23C	1.0573	−0.2107	0.2770	0.122*
C24	0.8894 (7)	−0.0563 (4)	0.22619 (13)	0.0768 (15)
H24A	0.7932	−0.0282	0.2128	0.115*
H24B	0.9316	−0.1216	0.2077	0.115*
H24C	0.9629	0.0102	0.2273	0.115*
C25	0.7345 (5)	−0.1141 (4)	0.38010 (14)	0.0589 (12)
H25A	0.7778	−0.1865	0.3662	0.088*
H25B	0.6572	−0.1373	0.4026	0.088*
H25C	0.8162	−0.0685	0.3950	0.088*
C26	0.7706 (5)	0.1700 (4)	0.42047 (13)	0.0566 (11)
H26A	0.8343	0.0980	0.4175	0.085*
H26B	0.6932	0.1570	0.4440	0.085*
H26C	0.8351	0.2386	0.4288	0.085*
C27	0.5036 (6)	0.3478 (4)	0.33047 (13)	0.0582 (12)
H27A	0.4405	0.4199	0.3342	0.087*
H27B	0.4387	0.2804	0.3210	0.087*
H27C	0.5820	0.3625	0.3073	0.087*
C28	0.5997 (6)	0.4369 (4)	0.49226 (14)	0.0668 (12)
H28A	0.5356	0.4117	0.5178	0.100*
H28B	0.6753	0.4958	0.5027	0.100*
H28C	0.6528	0.3668	0.4797	0.100*
C29	0.0481 (6)	0.6278 (5)	0.39767 (16)	0.0791 (15)
H29A	−0.0275	0.5687	0.3873	0.119*
H29B	0.1045	0.6592	0.3715	0.119*
H29C	−0.0046	0.6940	0.4131	0.119*
C30	0.0645 (5)	0.5169 (4)	0.47178 (15)	0.0557 (11)

	U11	U22	U33	U12	U13	U23
O1	0.123 (3)	0.0579 (19)	0.090 (2)	0.001 (3)	0.019 (3)	−0.0219 (19)
O2	0.081 (2)	0.0426 (15)	0.0673 (18)	−0.0104 (17)	0.0202 (19)	0.0001 (14)
O3	0.084 (2)	0.0523 (18)	0.084 (2)	−0.007 (2)	0.012 (2)	−0.0047 (16)
O4	0.109 (3)	0.0517 (17)	0.080 (2)	0.006 (2)	0.023 (2)	−0.0056 (17)
N1	0.102 (3)	0.053 (2)	0.075 (2)	0.001 (3)	0.008 (3)	−0.011 (2)
N2	0.107 (4)	0.061 (3)	0.079 (3)	0.012 (3)	0.020 (3)	−0.013 (2)
C1	0.069 (3)	0.048 (2)	0.061 (2)	0.002 (3)	0.000 (3)	−0.003 (2)
C2	0.082 (3)	0.044 (2)	0.050 (2)	0.001 (3)	−0.003 (3)	−0.003 (2)
C3	0.086 (4)	0.053 (3)	0.047 (2)	0.009 (3)	0.005 (3)	−0.002 (2)
C4	0.066 (3)	0.058 (3)	0.052 (2)	0.010 (3)	0.006 (2)	−0.002 (2)
C5	0.059 (3)	0.053 (2)	0.048 (2)	0.006 (2)	0.004 (2)	0.0004 (19)
C6	0.054 (3)	0.062 (3)	0.059 (2)	−0.004 (3)	0.009 (2)	0.002 (2)
C7	0.058 (3)	0.054 (2)	0.060 (3)	−0.007 (2)	0.012 (2)	0.000 (2)
C8	0.048 (2)	0.043 (2)	0.047 (2)	−0.003 (2)	0.003 (2)	0.0021 (18)
C9	0.052 (2)	0.041 (2)	0.048 (2)	−0.003 (2)	0.000 (2)	0.0028 (17)
C10	0.053 (2)	0.042 (2)	0.049 (2)	0.006 (2)	0.003 (2)	0.0019 (19)
C11	0.057 (3)	0.044 (2)	0.056 (2)	−0.005 (2)	0.006 (2)	−0.0002 (19)
C12	0.059 (3)	0.045 (2)	0.057 (2)	−0.008 (2)	0.013 (2)	0.000 (2)
C13	0.045 (2)	0.045 (2)	0.045 (2)	−0.002 (2)	0.000 (2)	0.0007 (18)
C14	0.051 (2)	0.040 (2)	0.048 (2)	−0.003 (2)	−0.003 (2)	−0.0002 (18)
C15	0.055 (3)	0.049 (2)	0.062 (3)	−0.013 (2)	0.002 (2)	0.002 (2)
C16	0.060 (3)	0.043 (2)	0.070 (3)	−0.009 (2)	−0.004 (3)	−0.001 (2)
C17	0.050 (2)	0.048 (2)	0.058 (2)	−0.007 (2)	−0.001 (2)	−0.007 (2)
C18	0.051 (2)	0.043 (2)	0.053 (2)	0.002 (2)	−0.003 (2)	−0.0029 (18)
C19	0.054 (3)	0.051 (2)	0.058 (2)	0.002 (2)	−0.004 (2)	0.001 (2)
C20	0.054 (3)	0.048 (2)	0.064 (3)	0.007 (2)	−0.004 (2)	0.002 (2)
C21	0.065 (3)	0.047 (2)	0.084 (3)	−0.001 (2)	0.003 (3)	−0.003 (2)
C22	0.061 (3)	0.050 (2)	0.082 (3)	−0.002 (3)	−0.007 (3)	−0.016 (2)
C23	0.079 (4)	0.083 (4)	0.082 (3)	0.025 (3)	0.007 (3)	−0.004 (3)
C24	0.098 (4)	0.080 (3)	0.052 (2)	0.002 (4)	0.017 (3)	−0.008 (2)
C25	0.075 (3)	0.052 (2)	0.050 (2)	0.008 (3)	0.000 (2)	0.005 (2)
C26	0.061 (3)	0.058 (3)	0.051 (2)	0.005 (2)	−0.005 (2)	0.003 (2)
C27	0.071 (3)	0.053 (2)	0.051 (2)	0.001 (3)	−0.003 (2)	0.0071 (19)
C28	0.066 (3)	0.075 (3)	0.059 (3)	0.005 (3)	−0.009 (3)	−0.009 (2)
C29	0.078 (4)	0.078 (3)	0.082 (3)	0.016 (3)	−0.001 (3)	0.024 (3)
C30	0.053 (3)	0.048 (2)	0.066 (3)	0.008 (2)	−0.012 (2)	−0.001 (2)

O1—N2	1.393 (5)	C15—H15B	0.9700
O1—N1	1.408 (5)	C16—C17	1.531 (5)
O2—C11	1.237 (4)	C16—H16A	0.9700
O3—C30	1.197 (5)	C16—H16B	0.9700
O4—C30	1.336 (5)	C17—C22	1.530 (5)
O4—H4A	0.8200	C17—C18	1.541 (5)
N1—C2	1.304 (5)	C17—C28	1.541 (5)
N2—C3	1.301 (5)	C18—C19	1.528 (5)
C1—C2	1.495 (6)	C18—H18A	0.9800
C1—C10	1.554 (6)	C19—C20	1.526 (5)
C1—H1A	0.9700	C19—H19A	0.9700
C1—H1B	0.9700	C19—H19B	0.9700
C2—C3	1.401 (7)	C20—C21	1.534 (6)
C3—C4	1.501 (6)	C20—C30	1.535 (6)
C4—C23	1.535 (6)	C20—C29	1.542 (6)
C4—C24	1.556 (5)	C21—C22	1.511 (6)
C4—C5	1.578 (6)	C21—H21A	0.9700
C5—C6	1.534 (6)	C21—H21B	0.9700
C5—C10	1.564 (6)	C22—H22A	0.9700
C5—H5A	0.9800	C22—H22B	0.9700
C6—C7	1.527 (6)	C23—H23A	0.9600
C6—H6A	0.9700	C23—H23B	0.9600
C6—H6B	0.9700	C23—H23C	0.9600
C7—C8	1.541 (5)	C24—H24A	0.9600
C7—H7A	0.9700	C24—H24B	0.9600
C7—H7B	0.9700	C24—H24C	0.9600
C8—C9	1.556 (5)	C25—H25A	0.9600
C8—C26	1.554 (5)	C25—H25B	0.9600
C8—C14	1.578 (5)	C25—H25C	0.9600
C9—C11	1.519 (5)	C26—H26A	0.9600
C9—C10	1.565 (5)	C26—H26B	0.9600
C9—H9A	0.9800	C26—H26C	0.9600
C10—C25	1.543 (5)	C27—H27A	0.9600
C11—C12	1.456 (5)	C27—H27B	0.9600
C12—C13	1.330 (5)	C27—H27C	0.9600
C12—H12A	0.9300	C28—H28A	0.9600
C13—C18	1.512 (5)	C28—H28B	0.9600
C13—C14	1.536 (5)	C28—H28C	0.9600
C14—C15	1.556 (5)	C29—H29A	0.9600
C14—C27	1.559 (5)	C29—H29B	0.9600
C15—C16	1.549 (5)	C29—H29C	0.9600
C15—H15A	0.9700
N2—O1—N1	110.5 (3)	C15—C16—H16B	108.9
C30—O4—H4A	109.5	H16A—C16—H16B	107.8
C2—N1—O1	103.6 (4)	C22—C17—C16	111.8 (3)
C3—N2—O1	105.4 (4)	C22—C17—C18	110.1 (3)
C2—C1—C10	109.4 (4)	C16—C17—C18	108.0 (3)
C2—C1—H1A	109.8	C22—C17—C28	106.9 (3)
C10—C1—H1A	109.8	C16—C17—C28	110.0 (4)
C2—C1—H1B	109.8	C18—C17—C28	110.0 (3)
C10—C1—H1B	109.8	C13—C18—C19	111.9 (3)
H1A—C1—H1B	108.2	C13—C18—C17	112.7 (3)
N1—C2—C3	111.2 (4)	C19—C18—C17	113.0 (3)
N1—C2—C1	125.3 (5)	C13—C18—H18A	106.2
C3—C2—C1	123.5 (4)	C19—C18—H18A	106.2
N2—C3—C2	109.2 (5)	C17—C18—H18A	106.2
N2—C3—C4	124.9 (5)	C20—C19—C18	114.2 (3)
C2—C3—C4	125.8 (4)	C20—C19—H19A	108.7
C3—C4—C23	110.4 (4)	C18—C19—H19A	108.7
C3—C4—C24	108.2 (4)	C20—C19—H19B	108.7
C23—C4—C24	107.3 (4)	C18—C19—H19B	108.7
C3—C4—C5	108.3 (4)	H19A—C19—H19B	107.6
C23—C4—C5	115.2 (4)	C19—C20—C21	109.8 (4)
C24—C4—C5	107.2 (3)	C19—C20—C30	109.0 (3)
C6—C5—C10	110.5 (3)	C21—C20—C30	111.9 (4)
C6—C5—C4	111.2 (4)	C19—C20—C29	110.4 (4)
C10—C5—C4	117.1 (3)	C21—C20—C29	109.4 (4)
C6—C5—H5A	105.7	C30—C20—C29	106.3 (4)
C10—C5—H5A	105.7	C22—C21—C20	112.6 (3)
C4—C5—H5A	105.7	C22—C21—H21A	109.1
C7—C6—C5	110.8 (4)	C20—C21—H21A	109.1
C7—C6—H6A	109.5	C22—C21—H21B	109.1
C5—C6—H6A	109.5	C20—C21—H21B	109.1
C7—C6—H6B	109.5	H21A—C21—H21B	107.8
C5—C6—H6B	109.5	C21—C22—C17	114.6 (4)
H6A—C6—H6B	108.1	C21—C22—H22A	108.6
C6—C7—C8	113.8 (3)	C17—C22—H22A	108.6
C6—C7—H7A	108.8	C21—C22—H22B	108.6
C8—C7—H7A	108.8	C17—C22—H22B	108.6
C6—C7—H7B	108.8	H22A—C22—H22B	107.6
C8—C7—H7B	108.8	C4—C23—H23A	109.5
H7A—C7—H7B	107.7	C4—C23—H23B	109.5
C7—C8—C9	110.4 (3)	H23A—C23—H23B	109.5
C7—C8—C26	107.4 (3)	C4—C23—H23C	109.5
C9—C8—C26	109.8 (3)	H23A—C23—H23C	109.5
C7—C8—C14	110.3 (3)	H23B—C23—H23C	109.5
C9—C8—C14	108.5 (3)	C4—C24—H24A	109.5
C26—C8—C14	110.5 (3)	C4—C24—H24B	109.5
C11—C9—C8	107.9 (3)	H24A—C24—H24B	109.5
C11—C9—C10	115.1 (3)	C4—C24—H24C	109.5
C8—C9—C10	118.8 (3)	H24A—C24—H24C	109.5
C11—C9—H9A	104.5	H24B—C24—H24C	109.5
C8—C9—H9A	104.5	C10—C25—H25A	109.5
C10—C9—H9A	104.5	C10—C25—H25B	109.5
C25—C10—C1	108.3 (3)	H25A—C25—H25B	109.5
C25—C10—C9	115.1 (3)	C10—C25—H25C	109.5
C1—C10—C9	106.5 (3)	H25A—C25—H25C	109.5
C25—C10—C5	112.3 (4)	H25B—C25—H25C	109.5
C1—C10—C5	107.3 (3)	C8—C26—H26A	109.5
C9—C10—C5	106.9 (3)	C8—C26—H26B	109.5
O2—C11—C12	119.7 (4)	H26A—C26—H26B	109.5
O2—C11—C9	123.2 (4)	C8—C26—H26C	109.5
C12—C11—C9	117.0 (3)	H26A—C26—H26C	109.5
C13—C12—C11	124.7 (4)	H26B—C26—H26C	109.5
C13—C12—H12A	117.7	C14—C27—H27A	109.5
C11—C12—H12A	117.7	C14—C27—H27B	109.5
C12—C13—C18	119.1 (4)	H27A—C27—H27B	109.5
C12—C13—C14	120.5 (4)	C14—C27—H27C	109.5
C18—C13—C14	120.3 (3)	H27A—C27—H27C	109.5
C13—C14—C15	112.1 (3)	H27B—C27—H27C	109.5
C13—C14—C27	106.2 (3)	C17—C28—H28A	109.5
C15—C14—C27	107.0 (3)	C17—C28—H28B	109.5
C13—C14—C8	109.3 (3)	H28A—C28—H28B	109.5
C15—C14—C8	110.3 (3)	C17—C28—H28C	109.5
C27—C14—C8	111.9 (3)	H28A—C28—H28C	109.5
C16—C15—C14	114.7 (3)	H28B—C28—H28C	109.5
C16—C15—H15A	108.6	C20—C29—H29A	109.5
C14—C15—H15A	108.6	C20—C29—H29B	109.5
C16—C15—H15B	108.6	H29A—C29—H29B	109.5
C14—C15—H15B	108.6	C20—C29—H29C	109.5
H15A—C15—H15B	107.6	H29A—C29—H29C	109.5
C17—C16—C15	113.2 (3)	H29B—C29—H29C	109.5
C17—C16—H16A	108.9	O3—C30—O4	121.7 (4)
C15—C16—H16A	108.9	O3—C30—C20	125.5 (4)
C17—C16—H16B	108.9	O4—C30—C20	112.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2i	0.82	2.04	2.787 (4)	151
C1—H1A···O2	0.97	2.36	2.969 (5)	120
C25—H25B···O2	0.96	2.39	3.021 (5)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2i	0.82	2.04	2.787 (4)	151
C1—H1A⋯O2	0.97	2.36	2.969 (5)	120
C25—H25B⋯O2	0.96	2.39	3.021 (5)	123

Symmetry code: (i) .