organic papers
Acta Cryst.(2006). E62, o3269–o3270 doi:10.1107/S1600536806025657 Wuet al. C
20H26O5
o3269
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
8
a
,9
a
-Epoxy-7-oxoroyleanon
Li Wu,aYang Lu,a* Qi-Tai Zheng,aXiao-Li Liband Qin-Shi Zhaob
aInstitute of Materia Medica, Chinese Academy
of Medical Sciences and Peking Union Medical College, 1 Xiannong Tan street, Beijing 100050, People’s Republic of China, andbState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 296 K
Mean(C–C) = 0.006 A˚
Rfactor = 0.060
wRfactor = 0.152 Data-to-parameter ratio = 9.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 20 June 2006 Accepted 3 July 2006
#2006 International Union of Crystallography
All rights reserved
The title compound, C20H26O5, is a naturally occurring
diterpenoid epoxyquinone. Its geometrical parameters are normal. The hydroxy group forms an intermolecular O— H O hydrogen bond which links the molecules into infinite chains extended along thebaxis.
Comment
The title compound, (I), was isolated from an Abyssinian Plectranthus species (Ru¨edi, 1984). Recently, we have obtained this compound fromLycopodium japonicumThunb. Here we report its crystal structure.
Compound (I) crystallizes in the monoclinic space group
P21 with one molecule in the asymmetric unit (Fig. 1). The
geometrical parameters for (I) fall within their expected ranges (Allenet al., 1987). The six-membered ringAadopts the usual chair conformation, while ringBadopts a twist-boat conformation. Ring C is essentially planar with an r.m.s. deviation of 0.042 (2) A˚ . The dihedral angle between the ring
Cand the three-membered ring C8/C9/O22 is 81.2 (3).
In the crystal structure, the hydroxy group forms an inter-molecular O—H O hydrogen bond (Table 21), which links the molecules into infinite chains extended along the b axis (Fig. 2).
Experimental
Crystal data
C20H26O5 Mr= 346.41
Monoclinic,P21
a= 10.336 (2) A˚
b= 7.4770 (15) A˚
c= 11.760 (2) A˚
= 101.61 (3)
V= 890.2 (3) A˚3
Z= 2
Dx= 1.292 Mg m 3
MoKradiation
= 0.09 mm 1 T= 296 (2) K Block, yellow 0.300.200.10 mm
Data collection
MAC DIP 2030K diffractometer
!scans
Absorption correction: none 5289 measured reflections
2066 independent reflections 1845 reflections withI> 2(I)
Rint= 0.038 max= 27.1
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.060 wR(F2) = 0.152 S= 1.09 2066 reflections 227 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.071P)2
+ 0.3757P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.25 e A˚ 3
min= 0.18 e A˚ 3
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O24—H24A O25i
0.82 2.20 2.820 (4) 132
Symmetry code: (i)x;y 1;z.
In the absence of significant anomalous scatterers, Friedel pairs were merged. All H atoms were constrained to an ideal geometry,
with C—H = 0.98 A˚ andUiso(H) = 1.2Ueq(C) for CH, C—H = 0.97 A˚
and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 A˚ and Uiso(H) =
1.5Ueq(C) for CH3, and O—H = 0.82 A˚ andUiso(H) = 1.5Ueq(O).
Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure:
SHELXS97(Sheldrick, 1997); program(s) used to refine structure:
SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII
(Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication:SHELXL97
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Ru¨edi, P. (1984).Helv. Chim. Acta,67, 1116–1120.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
[image:2.610.312.565.68.353.2]Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
Figure 1
View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary size.
Figure 2
[image:2.610.46.300.71.258.2]supporting information
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Acta Cryst. (2006). E62, o3269–o3270
supporting information
Acta Cryst. (2006). E62, o3269–o3270 [https://doi.org/10.1107/S1600536806025657]
8
α
,9
α
-Epoxy-7-oxoroyleanon
Li Wu, Yang Lu, Qi-Tai Zheng, Xiao-Li Li and Qin-Shi Zhao
8α,9α-Epoxy-7-oxoroyleanon
Crystal data
C20H26O5 Mr = 346.41
Monoclinic, P21 Hall symbol: P 2yb a = 10.336 (2) Å b = 7.4770 (15) Å c = 11.760 (2) Å β = 101.61 (3)° V = 890.2 (3) Å3 Z = 2
F(000) = 372 Dx = 1.292 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5289 reflections θ = 2.4–27.1°
µ = 0.09 mm−1 T = 296 K Block, yellow
0.30 × 0.20 × 0.10 mm
Data collection
MAC DIP 2030K diffractometer
Radiation source: rotating anode Graphite monochromator ω scans
5289 measured reflections 2066 independent reflections
1845 reflections with I > 2σ(I) Rint = 0.038
θmax = 27.1°, θmin = 2.4° h = −13→13
k = −9→9 l = −15→14
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.060 wR(F2) = 0.152 S = 1.09 2066 reflections 227 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.071P)2 + 0.3757P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001 Δρmax = 0.25 e Å−3 Δρmin = −0.18 e Å−3
Special details
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)
x y z Uiso*/Ueq
C1 0.5603 (4) 0.5027 (6) −0.1434 (3) 0.0601 (10)
H1A 0.5932 0.3828 −0.1237 0.072*
H1B 0.5013 0.5338 −0.0919 0.072*
C2 0.4829 (5) 0.5047 (7) −0.2694 (4) 0.0724 (13)
H2A 0.5398 0.4633 −0.3203 0.087*
H2B 0.4089 0.4229 −0.2769 0.087*
C3 0.4323 (4) 0.6895 (8) −0.3067 (4) 0.0660 (12)
H3A 0.3693 0.7257 −0.2602 0.079*
H3B 0.3861 0.6848 −0.3871 0.079*
C4 0.5423 (4) 0.8313 (6) −0.2948 (3) 0.0548 (9)
C5 0.6237 (3) 0.8211 (5) −0.1668 (3) 0.0456 (8)
H5A 0.5595 0.8498 −0.1184 0.055*
C6 0.7271 (5) 0.9698 (7) −0.1404 (3) 0.0694 (13)
H6A 0.7746 0.9755 −0.2035 0.083*
H6B 0.6817 1.0830 −0.1385 0.083*
C7 0.8254 (4) 0.9487 (6) −0.0286 (3) 0.0536 (9)
C8 0.7966 (3) 0.8170 (5) 0.0587 (3) 0.0412 (7)
C9 0.7334 (3) 0.6482 (5) 0.0077 (3) 0.0406 (7)
C10 0.6777 (3) 0.6346 (5) −0.1240 (3) 0.0417 (8)
C11 0.7819 (4) 0.4836 (6) 0.0789 (3) 0.0474 (8)
C12 0.8710 (4) 0.5051 (5) 0.1954 (3) 0.0461 (8)
C13 0.9102 (4) 0.6617 (6) 0.2471 (3) 0.0467 (8)
C14 0.8759 (3) 0.8261 (6) 0.1823 (3) 0.0442 (8)
C15 0.9810 (4) 0.6684 (7) 0.3734 (3) 0.0607 (10)
H15A 0.9994 0.5434 0.3961 0.073*
C16 0.8894 (5) 0.7348 (9) 0.4491 (4) 0.0799 (17)
H16A 0.9356 0.7379 0.5285 0.120*
H16B 0.8149 0.6558 0.4419 0.120*
H16C 0.8593 0.8529 0.4250 0.120*
C17 1.1124 (4) 0.7584 (9) 0.3949 (4) 0.0761 (14)
H17A 1.1497 0.7570 0.4766 0.114*
H17B 1.1020 0.8799 0.3682 0.114*
H17C 1.1701 0.6963 0.3538 0.114*
C18 0.4767 (6) 1.0156 (8) −0.3122 (5) 0.0850 (17)
H18A 0.4262 1.0248 −0.3900 0.127*
H18B 0.5434 1.1068 −0.2995 0.127*
H18C 0.4193 1.0308 −0.2581 0.127*
C19 0.6226 (5) 0.8076 (9) −0.3901 (3) 0.0745 (14)
H19A 0.5648 0.8153 −0.4648 0.112*
supporting information
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Acta Cryst. (2006). E62, o3269–o3270
H19C 0.6883 0.9000 −0.3832 0.112*
C20 0.7906 (4) 0.5657 (8) −0.1790 (3) 0.0662 (13)
H20A 0.7606 0.5558 −0.2615 0.099*
H20B 0.8185 0.4504 −0.1473 0.099*
H20C 0.8634 0.6477 −0.1626 0.099*
O21 0.9324 (3) 1.0220 (6) −0.0125 (3) 0.0772 (10)
O22 0.6612 (2) 0.7711 (4) 0.0659 (2) 0.0488 (6)
O23 0.7526 (3) 0.3336 (4) 0.0465 (3) 0.0703 (9)
O24 0.9033 (3) 0.3505 (4) 0.2517 (2) 0.0622 (8)
H24A 0.8703 0.2670 0.2107 0.093*
O25 0.8999 (3) 0.9757 (4) 0.2247 (2) 0.0606 (8)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.063 (2) 0.055 (2) 0.053 (2) −0.016 (2) −0.0118 (17) 0.0048 (19) C2 0.067 (3) 0.066 (3) 0.069 (3) −0.016 (2) −0.023 (2) 0.005 (2) C3 0.0452 (19) 0.083 (3) 0.060 (2) −0.002 (2) −0.0131 (16) 0.008 (2) C4 0.060 (2) 0.055 (2) 0.0413 (17) 0.007 (2) −0.0084 (14) 0.0052 (18) C5 0.0489 (17) 0.048 (2) 0.0361 (15) 0.0046 (17) −0.0003 (12) 0.0018 (15) C6 0.092 (3) 0.058 (3) 0.047 (2) −0.021 (2) −0.013 (2) 0.010 (2) C7 0.065 (2) 0.050 (2) 0.0436 (18) −0.0144 (19) 0.0050 (16) 0.0002 (17) C8 0.0428 (16) 0.0426 (19) 0.0354 (15) −0.0028 (15) 0.0010 (12) 0.0004 (14) C9 0.0410 (15) 0.0418 (18) 0.0366 (16) 0.0028 (15) 0.0019 (12) −0.0002 (14) C10 0.0417 (16) 0.046 (2) 0.0340 (15) 0.0028 (14) −0.0012 (12) −0.0024 (14) C11 0.0509 (19) 0.046 (2) 0.0425 (17) −0.0007 (17) 0.0029 (14) −0.0019 (16) C12 0.0477 (17) 0.047 (2) 0.0401 (17) 0.0042 (17) 0.0006 (14) 0.0037 (16) C13 0.0485 (18) 0.052 (2) 0.0368 (17) −0.0017 (18) 0.0028 (14) 0.0007 (16) C14 0.0455 (16) 0.048 (2) 0.0377 (16) −0.0012 (17) 0.0053 (13) −0.0040 (15) C15 0.077 (3) 0.058 (2) 0.0399 (18) −0.002 (2) −0.0067 (17) 0.0035 (19) C16 0.080 (3) 0.116 (5) 0.045 (2) −0.032 (3) 0.0162 (19) −0.020 (3) C17 0.056 (2) 0.102 (4) 0.064 (2) −0.001 (3) −0.0056 (18) −0.007 (3) C18 0.100 (4) 0.074 (3) 0.067 (3) 0.030 (3) −0.016 (3) 0.012 (3) C19 0.080 (3) 0.099 (4) 0.0387 (18) 0.001 (3) −0.0018 (17) 0.008 (2) C20 0.056 (2) 0.097 (4) 0.0423 (18) 0.025 (2) 0.0020 (16) −0.010 (2) O21 0.0695 (18) 0.094 (3) 0.0645 (17) −0.0275 (19) 0.0041 (14) 0.0131 (18) O22 0.0502 (13) 0.0533 (15) 0.0429 (12) 0.0029 (12) 0.0092 (10) −0.0047 (12) O23 0.098 (2) 0.0409 (15) 0.0573 (17) −0.0057 (17) −0.0207 (15) −0.0002 (13) O24 0.083 (2) 0.0443 (14) 0.0480 (15) 0.0025 (15) −0.0127 (13) 0.0021 (13) O25 0.082 (2) 0.0460 (16) 0.0466 (14) −0.0063 (15) −0.0051 (13) −0.0062 (13)
Geometric parameters (Å, º)
C1—C2 1.536 (5) C10—C20 1.533 (5)
C1—C10 1.544 (5) C11—O23 1.204 (5)
C1—H1A 0.9700 C11—C12 1.498 (5)
C1—H1B 0.9700 C12—O24 1.341 (5)
C2—H2A 0.9700 C13—C14 1.452 (6)
C2—H2B 0.9700 C13—C15 1.519 (5)
C3—C4 1.540 (7) C14—O25 1.229 (5)
C3—H3A 0.9700 C15—C17 1.491 (6)
C3—H3B 0.9700 C15—C16 1.508 (7)
C4—C18 1.532 (7) C15—H15A 0.9800
C4—C19 1.534 (6) C16—H16A 0.9600
C4—C5 1.572 (4) C16—H16B 0.9600
C5—C6 1.530 (6) C16—H16C 0.9600
C5—C10 1.547 (5) C17—H17A 0.9600
C5—H5A 0.9800 C17—H17B 0.9600
C6—C7 1.499 (5) C17—H17C 0.9600
C6—H6A 0.9700 C18—H18A 0.9600
C6—H6B 0.9700 C18—H18B 0.9600
C7—O21 1.215 (5) C18—H18C 0.9600
C7—C8 1.495 (5) C19—H19A 0.9600
C8—O22 1.460 (4) C19—H19B 0.9600
C8—C9 1.491 (5) C19—H19C 0.9600
C8—C14 1.520 (4) C20—H20A 0.9600
C9—O22 1.441 (4) C20—H20B 0.9600
C9—C11 1.517 (5) C20—H20C 0.9600
C9—C10 1.543 (4) O24—H24A 0.8200
C2—C1—C10 112.1 (3) C20—C10—C5 114.9 (3)
C2—C1—H1A 109.2 C9—C10—C5 107.7 (3)
C10—C1—H1A 109.2 C1—C10—C5 107.9 (3)
C2—C1—H1B 109.2 O23—C11—C12 117.4 (4)
C10—C1—H1B 109.2 O23—C11—C9 123.1 (3)
H1A—C1—H1B 107.9 C12—C11—C9 119.5 (3)
C3—C2—C1 111.8 (4) O24—C12—C13 120.4 (3)
C3—C2—H2A 109.3 O24—C12—C11 113.9 (3)
C1—C2—H2A 109.3 C13—C12—C11 125.5 (3)
C3—C2—H2B 109.3 C12—C13—C14 118.8 (3)
C1—C2—H2B 109.3 C12—C13—C15 120.8 (4)
H2A—C2—H2B 107.9 C14—C13—C15 120.3 (4)
C2—C3—C4 113.4 (3) O25—C14—C13 123.3 (3)
C2—C3—H3A 108.9 O25—C14—C8 117.0 (3)
C4—C3—H3A 108.9 C13—C14—C8 119.4 (3)
C2—C3—H3B 108.9 C17—C15—C16 114.2 (4)
C4—C3—H3B 108.9 C17—C15—C13 115.1 (4)
H3A—C3—H3B 107.7 C16—C15—C13 110.6 (4)
C18—C4—C19 107.2 (4) C17—C15—H15A 105.3
C18—C4—C3 108.0 (4) C16—C15—H15A 105.3
C19—C4—C3 110.6 (4) C13—C15—H15A 105.3
C18—C4—C5 108.0 (4) C15—C16—H16A 109.5
C19—C4—C5 115.5 (3) C15—C16—H16B 109.5
C3—C4—C5 107.3 (3) H16A—C16—H16B 109.5
supporting information
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Acta Cryst. (2006). E62, o3269–o3270
C6—C5—C4 112.1 (3) H16A—C16—H16C 109.5
C10—C5—C4 116.3 (3) H16B—C16—H16C 109.5
C6—C5—H5A 104.5 C15—C17—H17A 109.5
C10—C5—H5A 104.5 C15—C17—H17B 109.5
C4—C5—H5A 104.5 H17A—C17—H17B 109.5
C7—C6—C5 115.1 (3) C15—C17—H17C 109.5
C7—C6—H6A 108.5 H17A—C17—H17C 109.5
C5—C6—H6A 108.5 H17B—C17—H17C 109.5
C7—C6—H6B 108.5 C4—C18—H18A 109.5
C5—C6—H6B 108.5 C4—C18—H18B 109.5
H6A—C6—H6B 107.5 H18A—C18—H18B 109.5
O21—C7—C8 119.4 (3) C4—C18—H18C 109.5
O21—C7—C6 121.7 (4) H18A—C18—H18C 109.5
C8—C7—C6 118.5 (3) H18B—C18—H18C 109.5
O22—C8—C9 58.5 (2) C4—C19—H19A 109.5
O22—C8—C7 121.4 (3) C4—C19—H19B 109.5
C9—C8—C7 114.4 (3) H19A—C19—H19B 109.5
O22—C8—C14 107.1 (2) C4—C19—H19C 109.5
C9—C8—C14 122.1 (3) H19A—C19—H19C 109.5
C7—C8—C14 118.9 (3) H19B—C19—H19C 109.5
O22—C9—C8 59.7 (2) C10—C20—H20A 109.5
O22—C9—C11 113.6 (3) C10—C20—H20B 109.5
C8—C9—C11 113.3 (3) H20A—C20—H20B 109.5
O22—C9—C10 113.2 (3) C10—C20—H20C 109.5
C8—C9—C10 120.3 (3) H20A—C20—H20C 109.5
C11—C9—C10 121.1 (3) H20B—C20—H20C 109.5
C20—C10—C9 106.4 (3) C9—O22—C8 61.8 (2)
C20—C10—C1 111.4 (4) C12—O24—H24A 109.5
C9—C10—C1 108.3 (3)
C10—C1—C2—C3 −57.2 (5) C2—C1—C10—C5 53.7 (5)
C1—C2—C3—C4 57.3 (6) C6—C5—C10—C20 −61.5 (4)
C2—C3—C4—C18 −169.2 (4) C4—C5—C10—C20 70.8 (4)
C2—C3—C4—C19 73.8 (5) C6—C5—C10—C9 57.0 (4)
C2—C3—C4—C5 −53.0 (5) C4—C5—C10—C9 −170.8 (3)
C18—C4—C5—C6 −57.7 (5) C6—C5—C10—C1 173.6 (3)
C19—C4—C5—C6 62.3 (5) C4—C5—C10—C1 −54.2 (4)
C3—C4—C5—C6 −173.9 (4) O22—C9—C11—O23 121.8 (4)
C18—C4—C5—C10 169.5 (4) C8—C9—C11—O23 −172.5 (4)
C19—C4—C5—C10 −70.5 (5) C10—C9—C11—O23 −18.1 (6)
C3—C4—C5—C10 53.3 (4) O22—C9—C11—C12 −58.4 (4)
C10—C5—C6—C7 −34.5 (5) C8—C9—C11—C12 7.3 (5)
C4—C5—C6—C7 −168.8 (4) C10—C9—C11—C12 161.6 (3)
C5—C6—C7—O21 157.9 (5) O23—C11—C12—O24 −2.4 (6)
C5—C6—C7—C8 −14.8 (6) C9—C11—C12—O24 177.8 (3)
O21—C7—C8—O22 159.1 (4) O23—C11—C12—C13 −177.6 (4)
C6—C7—C8—O22 −28.1 (6) C9—C11—C12—C13 2.6 (6)
C6—C7—C8—C9 38.6 (5) C11—C12—C13—C14 −6.6 (6)
O21—C7—C8—C14 22.1 (6) O24—C12—C13—C15 −5.6 (6)
C6—C7—C8—C14 −165.0 (4) C11—C12—C13—C15 169.3 (4)
C7—C8—C9—O22 −113.1 (3) C12—C13—C14—O25 175.1 (4)
C14—C8—C9—O22 91.3 (3) C15—C13—C14—O25 −0.8 (5)
O22—C8—C9—C11 −104.7 (3) C12—C13—C14—C8 0.3 (5)
C7—C8—C9—C11 142.2 (3) C15—C13—C14—C8 −175.7 (3)
C14—C8—C9—C11 −13.3 (4) O22—C8—C14—O25 −101.8 (4)
O22—C8—C9—C10 100.8 (3) C9—C8—C14—O25 −164.9 (3)
C7—C8—C9—C10 −12.3 (4) C7—C8—C14—O25 40.6 (5)
C14—C8—C9—C10 −167.9 (3) O22—C8—C14—C13 73.3 (4)
O22—C9—C10—C20 157.5 (4) C9—C8—C14—C13 10.3 (5)
C8—C9—C10—C20 90.2 (4) C7—C8—C14—C13 −144.2 (4)
C11—C9—C10—C20 −62.4 (5) C12—C13—C15—C17 124.0 (5)
O22—C9—C10—C1 −82.6 (4) C14—C13—C15—C17 −60.2 (6)
C8—C9—C10—C1 −149.9 (3) C12—C13—C15—C16 −104.8 (5)
C11—C9—C10—C1 57.5 (4) C14—C13—C15—C16 71.1 (5)
O22—C9—C10—C5 33.8 (4) C11—C9—O22—C8 104.2 (3)
C8—C9—C10—C5 −33.5 (4) C10—C9—O22—C8 −112.7 (3)
C11—C9—C10—C5 173.9 (3) C7—C8—O22—C9 101.1 (4)
C2—C1—C10—C20 −73.3 (5) C14—C8—O22—C9 −117.6 (3)
C2—C1—C10—C9 170.0 (4)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O24—H24A···O25i 0.82 2.20 2.820 (4) 132
