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Acta Cryst. (2009). E65, o1547    [ doi:10.1107/S1600536809020996 ]

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

J. Hu, L. Yu, R. Wang and Y. Ju

Abstract top

The title compound [systematic name: 11-oxo-2,3-(oxydinitrilo)olean-12-en-29-oic acid], C30H42N2O4, contains a linear array of five six-membered rings and a five-membered heterocyclic ring. The C ring, containing an [alpha],[beta]-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 enantiomer 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, intermolecular O-H...O hydrogen bonds link the molecules.

Comment top

Glycyrrhetinic acid is the aglycone of glycyrrhizin, a triterpenoid saponin found in the roots of licorice(glycyrrhiza glabra)(Yoshida et al., 2001). It is well known as a potent sweet saponin and a number of triterpenoids. Glycyrrhetinic acid and its derivatives have several pharmacological activities, such as anti-inflammatory(Finney et al., 1960), anti-viral(Yu et al., 2006) and anti-tumor(Su et al. 2004). Recently, our group has designed and synthesized a novel series of glycyrrhetinic acid derivatives by chemical modification, and [2,3-c][1,2,5]oxadiazol-glycyrrhetinic acid showed primarily considerable bioactivity of inhibiting growth of HepG-2 tumour cell.

The title compound was obtained as colourless plate in the orthorhombic space group P2(1)2(1)2(1). A view of the molecular structure with the numbering scheme is shown in Fig. 1 and selected dimensions are given in Table 1. The molecule is composed of five fused six-membered rings and a five-membered heterocyclic ring, viz. A(C1–C5/C10), B(C5–C10), C(C8/C9/C11–C14), D(C13–C18), E(C17–C22) and F(C2—N2—O2—N1—C3). Ring B, D and E adopt chair conformations, while ring A and C adopt a slightly distorted half-chair conformation as a result of the double bonds being in or out of rings. The lengths of single bonds N1–C2 and N2–C3 are nearly equal, though there is a gem-dimethyl on C4.

Related literature top

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 top

2,3-dihydroxyimino-glycyrrhetinic acid (500 mg, 0.98 mmol), 18-Crown-6 (35 mg, 0.13 mmol) and t-BuOK (220 mg, 1.96 mmol) were dissolved in 15 mL THF and 15 mL DCM. The mixture was stirred for 10 min at 50°C. The product was treated with hydrochloric acid, then washed with H2O and extracted with EtOAc. The combined organic phase was washed with brine, dried and evaporated. Purification by flash chromatography(DCM:Methanol=20:1) gave title compound(439 mg, 91%). Crystals suitable for X-ray structure analysis were obtained via slow evaporation of a solution(chloroform: acetone = 1:7) at room temperature.

Refinement top

All non-hydrogen atoms were subjected to anisotropic refinement. All hydrogen atoms were generated geometrically with O—H bond distance of 0.82 Å and C—H bonds of 0.93–0.98 Å according to criteria described in the SHELXTL manual (Sheldrick, 2008). They were included in the refinement with Uiso(H) = 1.2Ueq or 1.5Ueq (for methyl C). Final difference Fourier maps showed the highestand lowest electron densities of -0.182 and 0.157 e Å-3, respectively. Friedel pairs were averaged in the final refinement.

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS (Bruker, 1997); data reduction: XSCANS (Bruker, 1997); 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).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of title compound with 35% probability ellipsoids, showing the atomic numbering scheme.
[Figure 2] Fig. 2. A packing view along the a direction.
(I) top
Crystal data top
C30H42N2O4F(000) = 1072
Mr = 494.66Dx = 1.220 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 52 reflections
a = 8.5489 (11) Åθ = 3.7–19.0°
b = 10.9019 (18) ŵ = 0.08 mm−1
c = 28.898 (3) ÅT = 295 K
V = 2693.2 (6) Å3Prism, colorless
Z = 40.5 × 0.4 × 0.3 mm
Data collection top
Bruker P4
diffractometer		Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 2.0°
graphiteh = −1→10
ω scansk = −13→1
3717 measured reflectionsl = −1→35
2855 independent reflections3 standard reflections every 97 reflections
2178 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-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 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
Crystal data top
C30H42N2O4V = 2693.2 (6) Å3
Mr = 494.66Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.5489 (11) ŵ = 0.08 mm−1
b = 10.9019 (18) ÅT = 295 K
c = 28.898 (3) Å0.5 × 0.4 × 0.3 mm
Data collection top
Bruker P4
diffractometer		Rint = 0.031
3717 measured reflectionsθmax = 25.5°
2855 independent reflections3 standard reflections every 97 reflections
2178 reflections with I > 2σ(I) intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.16 e Å−3
S = 1.02Δρmin = −0.18 e Å−3
2855 reflectionsAbsolute structure: ?
326 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6409 (6)−0.3844 (3)0.25922 (12)0.0902 (11)
O20.4151 (4)−0.0311 (2)0.41200 (9)0.0636 (9)
O30.0227 (4)0.4128 (3)0.47645 (11)0.0733 (9)
O40.0196 (5)0.6051 (3)0.50103 (11)0.0802 (10)
H4A−0.03800.57580.52080.096*
N10.5282 (6)−0.3188 (3)0.28470 (14)0.0767 (12)
N20.7751 (6)−0.3138 (4)0.25298 (14)0.0826 (14)
C10.5253 (6)−0.1096 (4)0.31919 (14)0.0592 (12)
H1A0.4552−0.14150.34270.071*
H1B0.4653−0.05740.29860.071*
C20.5954 (6)−0.2133 (4)0.29242 (14)0.0587 (12)
C30.7457 (6)−0.2096 (4)0.27309 (14)0.0621 (13)
C40.8579 (6)−0.1039 (4)0.27610 (14)0.0586 (12)
C50.7758 (5)0.0033 (4)0.30352 (13)0.0535 (11)
H5A0.71430.04850.28050.064*
C60.8964 (5)0.0951 (4)0.32221 (14)0.0585 (11)
H6A0.95020.05940.34850.070*
H6B0.97340.11230.29850.070*
C70.8171 (5)0.2144 (4)0.33693 (14)0.0573 (11)
H7A0.77170.25300.30980.069*
H7B0.89590.26960.34920.069*
C80.6882 (5)0.1969 (4)0.37362 (13)0.0462 (10)
C90.5807 (5)0.0872 (3)0.36035 (13)0.0466 (10)
H9A0.51940.11730.33400.056*
C100.6578 (5)−0.0339 (3)0.34242 (13)0.0483 (10)
C110.4616 (5)0.0705 (4)0.39885 (14)0.0526 (11)
C120.3977 (6)0.1813 (4)0.41969 (14)0.0535 (11)
H12A0.31300.17260.43960.064*
C130.4519 (5)0.2939 (3)0.41227 (13)0.0450 (10)
C140.5843 (5)0.3161 (3)0.37735 (13)0.0463 (10)
C150.6873 (5)0.4283 (4)0.39076 (15)0.0553 (11)
H15A0.76810.40110.41190.066*
H15B0.73860.45870.36310.066*
C160.5968 (5)0.5356 (3)0.41356 (14)0.0576 (11)
H16A0.67120.59680.42400.069*
H16B0.53020.57370.39050.069*
C170.4960 (5)0.4953 (4)0.45462 (14)0.0521 (10)
C180.3760 (5)0.4008 (3)0.43689 (13)0.0487 (10)
H18A0.32510.36660.46440.058*
C190.2459 (5)0.4588 (4)0.40792 (14)0.0541 (11)
H19A0.29020.48720.37890.065*
H19B0.16900.39630.40070.065*
C200.1633 (5)0.5660 (4)0.43147 (15)0.0554 (11)
C210.2844 (6)0.6604 (4)0.44773 (17)0.0653 (13)
H21A0.33160.69900.42090.078*
H21B0.23190.72370.46550.078*
C220.4116 (6)0.6038 (4)0.47708 (16)0.0644 (12)
H22A0.36590.57660.50600.077*
H22B0.48820.66660.48430.077*
C231.0152 (6)−0.1466 (5)0.29607 (17)0.0815 (16)
H23A0.9998−0.17690.32690.122*
H23B1.0868−0.07880.29670.122*
H23C1.0573−0.21070.27700.122*
C240.8894 (7)−0.0563 (4)0.22619 (13)0.0768 (15)
H24A0.7932−0.02820.21280.115*
H24B0.9316−0.12160.20770.115*
H24C0.96290.01020.22730.115*
C250.7345 (5)−0.1141 (4)0.38010 (14)0.0589 (12)
H25A0.7778−0.18650.36620.088*
H25B0.6572−0.13730.40260.088*
H25C0.8162−0.06850.39500.088*
C260.7706 (5)0.1700 (4)0.42047 (13)0.0566 (11)
H26A0.83430.09800.41750.085*
H26B0.69320.15700.44400.085*
H26C0.83510.23860.42880.085*
C270.5036 (6)0.3478 (4)0.33047 (13)0.0582 (12)
H27A0.44050.41990.33420.087*
H27B0.43870.28040.32100.087*
H27C0.58200.36250.30730.087*
C280.5997 (6)0.4369 (4)0.49226 (14)0.0668 (12)
H28A0.53560.41170.51780.100*
H28B0.67530.49580.50270.100*
H28C0.65280.36680.47970.100*
C290.0481 (6)0.6278 (5)0.39767 (16)0.0791 (15)
H29A−0.02750.56870.38730.119*
H29B0.10450.65920.37150.119*
H29C−0.00460.69400.41310.119*
C300.0645 (5)0.5169 (4)0.47178 (15)0.0557 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.123 (3)0.0579 (19)0.090 (2)0.001 (3)0.019 (3)−0.0219 (19)
O20.081 (2)0.0426 (15)0.0673 (18)−0.0104 (17)0.0202 (19)0.0001 (14)
O30.084 (2)0.0523 (18)0.084 (2)−0.007 (2)0.012 (2)−0.0047 (16)
O40.109 (3)0.0517 (17)0.080 (2)0.006 (2)0.023 (2)−0.0056 (17)
N10.102 (3)0.053 (2)0.075 (2)0.001 (3)0.008 (3)−0.011 (2)
N20.107 (4)0.061 (3)0.079 (3)0.012 (3)0.020 (3)−0.013 (2)
C10.069 (3)0.048 (2)0.061 (2)0.002 (3)0.000 (3)−0.003 (2)
C20.082 (3)0.044 (2)0.050 (2)0.001 (3)−0.003 (3)−0.003 (2)
C30.086 (4)0.053 (3)0.047 (2)0.009 (3)0.005 (3)−0.002 (2)
C40.066 (3)0.058 (3)0.052 (2)0.010 (3)0.006 (2)−0.002 (2)
C50.059 (3)0.053 (2)0.048 (2)0.006 (2)0.004 (2)0.0004 (19)
C60.054 (3)0.062 (3)0.059 (2)−0.004 (3)0.009 (2)0.002 (2)
C70.058 (3)0.054 (2)0.060 (3)−0.007 (2)0.012 (2)0.000 (2)
C80.048 (2)0.043 (2)0.047 (2)−0.003 (2)0.003 (2)0.0021 (18)
C90.052 (2)0.041 (2)0.048 (2)−0.003 (2)0.000 (2)0.0028 (17)
C100.053 (2)0.042 (2)0.049 (2)0.006 (2)0.003 (2)0.0019 (19)
C110.057 (3)0.044 (2)0.056 (2)−0.005 (2)0.006 (2)−0.0002 (19)
C120.059 (3)0.045 (2)0.057 (2)−0.008 (2)0.013 (2)0.000 (2)
C130.045 (2)0.045 (2)0.045 (2)−0.002 (2)0.000 (2)0.0007 (18)
C140.051 (2)0.040 (2)0.048 (2)−0.003 (2)−0.003 (2)−0.0002 (18)
C150.055 (3)0.049 (2)0.062 (3)−0.013 (2)0.002 (2)0.002 (2)
C160.060 (3)0.043 (2)0.070 (3)−0.009 (2)−0.004 (3)−0.001 (2)
C170.050 (2)0.048 (2)0.058 (2)−0.007 (2)−0.001 (2)−0.007 (2)
C180.051 (2)0.043 (2)0.053 (2)0.002 (2)−0.003 (2)−0.0029 (18)
C190.054 (3)0.051 (2)0.058 (2)0.002 (2)−0.004 (2)0.001 (2)
C200.054 (3)0.048 (2)0.064 (3)0.007 (2)−0.004 (2)0.002 (2)
C210.065 (3)0.047 (2)0.084 (3)−0.001 (2)0.003 (3)−0.003 (2)
C220.061 (3)0.050 (2)0.082 (3)−0.002 (3)−0.007 (3)−0.016 (2)
C230.079 (4)0.083 (4)0.082 (3)0.025 (3)0.007 (3)−0.004 (3)
C240.098 (4)0.080 (3)0.052 (2)0.002 (4)0.017 (3)−0.008 (2)
C250.075 (3)0.052 (2)0.050 (2)0.008 (3)0.000 (2)0.005 (2)
C260.061 (3)0.058 (3)0.051 (2)0.005 (2)−0.005 (2)0.003 (2)
C270.071 (3)0.053 (2)0.051 (2)0.001 (3)−0.003 (2)0.0071 (19)
C280.066 (3)0.075 (3)0.059 (3)0.005 (3)−0.009 (3)−0.009 (2)
C290.078 (4)0.078 (3)0.082 (3)0.016 (3)−0.001 (3)0.024 (3)
C300.053 (3)0.048 (2)0.066 (3)0.008 (2)−0.012 (2)−0.001 (2)
Geometric parameters (Å, °) top
O1—N21.393 (5)C15—H15B0.9700
O1—N11.408 (5)C16—C171.531 (5)
O2—C111.237 (4)C16—H16A0.9700
O3—C301.197 (5)C16—H16B0.9700
O4—C301.336 (5)C17—C221.530 (5)
O4—H4A0.8200C17—C181.541 (5)
N1—C21.304 (5)C17—C281.541 (5)
N2—C31.301 (5)C18—C191.528 (5)
C1—C21.495 (6)C18—H18A0.9800
C1—C101.554 (6)C19—C201.526 (5)
C1—H1A0.9700C19—H19A0.9700
C1—H1B0.9700C19—H19B0.9700
C2—C31.401 (7)C20—C211.534 (6)
C3—C41.501 (6)C20—C301.535 (6)
C4—C231.535 (6)C20—C291.542 (6)
C4—C241.556 (5)C21—C221.511 (6)
C4—C51.578 (6)C21—H21A0.9700
C5—C61.534 (6)C21—H21B0.9700
C5—C101.564 (6)C22—H22A0.9700
C5—H5A0.9800C22—H22B0.9700
C6—C71.527 (6)C23—H23A0.9600
C6—H6A0.9700C23—H23B0.9600
C6—H6B0.9700C23—H23C0.9600
C7—C81.541 (5)C24—H24A0.9600
C7—H7A0.9700C24—H24B0.9600
C7—H7B0.9700C24—H24C0.9600
C8—C91.556 (5)C25—H25A0.9600
C8—C261.554 (5)C25—H25B0.9600
C8—C141.578 (5)C25—H25C0.9600
C9—C111.519 (5)C26—H26A0.9600
C9—C101.565 (5)C26—H26B0.9600
C9—H9A0.9800C26—H26C0.9600
C10—C251.543 (5)C27—H27A0.9600
C11—C121.456 (5)C27—H27B0.9600
C12—C131.330 (5)C27—H27C0.9600
C12—H12A0.9300C28—H28A0.9600
C13—C181.512 (5)C28—H28B0.9600
C13—C141.536 (5)C28—H28C0.9600
C14—C151.556 (5)C29—H29A0.9600
C14—C271.559 (5)C29—H29B0.9600
C15—C161.549 (5)C29—H29C0.9600
C15—H15A0.9700
N2—O1—N1110.5 (3)C15—C16—H16B108.9
C30—O4—H4A109.5H16A—C16—H16B107.8
C2—N1—O1103.6 (4)C22—C17—C16111.8 (3)
C3—N2—O1105.4 (4)C22—C17—C18110.1 (3)
C2—C1—C10109.4 (4)C16—C17—C18108.0 (3)
C2—C1—H1A109.8C22—C17—C28106.9 (3)
C10—C1—H1A109.8C16—C17—C28110.0 (4)
C2—C1—H1B109.8C18—C17—C28110.0 (3)
C10—C1—H1B109.8C13—C18—C19111.9 (3)
H1A—C1—H1B108.2C13—C18—C17112.7 (3)
N1—C2—C3111.2 (4)C19—C18—C17113.0 (3)
N1—C2—C1125.3 (5)C13—C18—H18A106.2
C3—C2—C1123.5 (4)C19—C18—H18A106.2
N2—C3—C2109.2 (5)C17—C18—H18A106.2
N2—C3—C4124.9 (5)C20—C19—C18114.2 (3)
C2—C3—C4125.8 (4)C20—C19—H19A108.7
C3—C4—C23110.4 (4)C18—C19—H19A108.7
C3—C4—C24108.2 (4)C20—C19—H19B108.7
C23—C4—C24107.3 (4)C18—C19—H19B108.7
C3—C4—C5108.3 (4)H19A—C19—H19B107.6
C23—C4—C5115.2 (4)C19—C20—C21109.8 (4)
C24—C4—C5107.2 (3)C19—C20—C30109.0 (3)
C6—C5—C10110.5 (3)C21—C20—C30111.9 (4)
C6—C5—C4111.2 (4)C19—C20—C29110.4 (4)
C10—C5—C4117.1 (3)C21—C20—C29109.4 (4)
C6—C5—H5A105.7C30—C20—C29106.3 (4)
C10—C5—H5A105.7C22—C21—C20112.6 (3)
C4—C5—H5A105.7C22—C21—H21A109.1
C7—C6—C5110.8 (4)C20—C21—H21A109.1
C7—C6—H6A109.5C22—C21—H21B109.1
C5—C6—H6A109.5C20—C21—H21B109.1
C7—C6—H6B109.5H21A—C21—H21B107.8
C5—C6—H6B109.5C21—C22—C17114.6 (4)
H6A—C6—H6B108.1C21—C22—H22A108.6
C6—C7—C8113.8 (3)C17—C22—H22A108.6
C6—C7—H7A108.8C21—C22—H22B108.6
C8—C7—H7A108.8C17—C22—H22B108.6
C6—C7—H7B108.8H22A—C22—H22B107.6
C8—C7—H7B108.8C4—C23—H23A109.5
H7A—C7—H7B107.7C4—C23—H23B109.5
C7—C8—C9110.4 (3)H23A—C23—H23B109.5
C7—C8—C26107.4 (3)C4—C23—H23C109.5
C9—C8—C26109.8 (3)H23A—C23—H23C109.5
C7—C8—C14110.3 (3)H23B—C23—H23C109.5
C9—C8—C14108.5 (3)C4—C24—H24A109.5
C26—C8—C14110.5 (3)C4—C24—H24B109.5
C11—C9—C8107.9 (3)H24A—C24—H24B109.5
C11—C9—C10115.1 (3)C4—C24—H24C109.5
C8—C9—C10118.8 (3)H24A—C24—H24C109.5
C11—C9—H9A104.5H24B—C24—H24C109.5
C8—C9—H9A104.5C10—C25—H25A109.5
C10—C9—H9A104.5C10—C25—H25B109.5
C25—C10—C1108.3 (3)H25A—C25—H25B109.5
C25—C10—C9115.1 (3)C10—C25—H25C109.5
C1—C10—C9106.5 (3)H25A—C25—H25C109.5
C25—C10—C5112.3 (4)H25B—C25—H25C109.5
C1—C10—C5107.3 (3)C8—C26—H26A109.5
C9—C10—C5106.9 (3)C8—C26—H26B109.5
O2—C11—C12119.7 (4)H26A—C26—H26B109.5
O2—C11—C9123.2 (4)C8—C26—H26C109.5
C12—C11—C9117.0 (3)H26A—C26—H26C109.5
C13—C12—C11124.7 (4)H26B—C26—H26C109.5
C13—C12—H12A117.7C14—C27—H27A109.5
C11—C12—H12A117.7C14—C27—H27B109.5
C12—C13—C18119.1 (4)H27A—C27—H27B109.5
C12—C13—C14120.5 (4)C14—C27—H27C109.5
C18—C13—C14120.3 (3)H27A—C27—H27C109.5
C13—C14—C15112.1 (3)H27B—C27—H27C109.5
C13—C14—C27106.2 (3)C17—C28—H28A109.5
C15—C14—C27107.0 (3)C17—C28—H28B109.5
C13—C14—C8109.3 (3)H28A—C28—H28B109.5
C15—C14—C8110.3 (3)C17—C28—H28C109.5
C27—C14—C8111.9 (3)H28A—C28—H28C109.5
C16—C15—C14114.7 (3)H28B—C28—H28C109.5
C16—C15—H15A108.6C20—C29—H29A109.5
C14—C15—H15A108.6C20—C29—H29B109.5
C16—C15—H15B108.6H29A—C29—H29B109.5
C14—C15—H15B108.6C20—C29—H29C109.5
H15A—C15—H15B107.6H29A—C29—H29C109.5
C17—C16—C15113.2 (3)H29B—C29—H29C109.5
C17—C16—H16A108.9O3—C30—O4121.7 (4)
C15—C16—H16A108.9O3—C30—C20125.5 (4)
C17—C16—H16B108.9O4—C30—C20112.8 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O2i0.822.042.787 (4)151
C1—H1A···O20.972.362.969 (5)120
C25—H25B···O20.962.393.021 (5)123
Symmetry codes: (i) x−1/2, −y+1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4A···O2i0.822.042.787 (4)151
C1—H1A···O20.972.362.969 (5)120
C25—H25B···O20.962.393.021 (5)123
Symmetry codes: (i) x−1/2, −y+1/2, −z+1.
Acknowledgements top

The authors acknowledge financial support from the NSFC (No. 20772071)

references
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