(-)-Argemonine hemihydrate

(-)-Argemonine hemihydrate [systematic name: (6S,12S)-2,3,8,9-tetra­methoxy-13-methyl-13-aza­dibenzo­[b,f]­bi­cyclo[3.3.1]­nona-2,6-diene hemi­hy­drate], C₂₁H₂₅NO₄·0.5H₂O, is a tertiary pavinane alkaloid. Both partially saturated nitro­gen heterocycles adopt twisted half-chair conformations. The angle between the two aromatic rings is 86.90 (5)°.

S1. Comment

(–)-Argemonine hemihydrate, (I), is a member of a relatively small group of pavinane alkaloids occurring in some plant species of the genera Argemone (Papaveraceae), Thalictrum (Ranunculaceae), and Berberis and some Leontice (Berberidaceae) (Gözler et al., 1983). In the Leontice species, argemonine occurs as the dextrorotatory enantiomer (Gözler et al., 1983). (–)-Argemonine has been isolated for the first time from Argemone hispida Gray (Soine & Gisvold, 1944; Schermerhorn & Soine, 1951) and later found in some other Argemone species which occur naturally in the southern regions of North America. The structure of argemonine was determined by Martell et al. (1963) and Stermitz et al. (1963), and the identity with N-methylpavine, a semisynthetic derivative of papaverine, was proved (Schöpf, 1949; Battersby & Binks, 1955). The absolute configuration was established as 6S,12S (Červinka et al., 1966) and confirmed by the X-ray study of (–)-argemonine methiodide (Kaneda et al., 1976). \scheme

Argemonine possesses an azabicyclo[3.3.1]nonadiene system fused with two benzene rings each of them bearing two methoxyl groups (Fig. 1). All bond lengths and angles are within normal range. The bond lengths involving trivalent nitrogen N1—C6, N1—C12 and N1—C17 are 1.4610 (18), 1.4648 (18) and 1.4582 (18) Å, respectively. They are shorter than the corresponding distances involving tetravalent nitrogen in argemonine methiodide (Kaneda et al., 1976). The bond angles C12—N1—C17 [113.24 (12)°] and C6—N1—C17 [113.32 (12)°] are somewhat enlarged probably due to sterical repulsion of the N-methyl group within a rigid azabicyclononadiene. The bond angles around the O atoms O18, O19 and O21 are enlarged [average value 116.2 (5)°] compared with the C8—O20—C15 angle [112.41 (12)°]. Similar findings were made in (–)-argemonine methiodide (Kaneda et al., 1976). The three methoxyl groups (C2—OMe, C3—OMe and C9—OMe) essentially lie in the planes of the adjacent aromatic rings [cis-torsion angles -0.9 (2), -0.8 (2) and 5.6 (2)°, respectively]. The remaining methoxyl (O20—C15, attached to C8 atom) is almost perpendicular to the aromatic plane [torsion angle C15—O20—C8—C7 - 75.56 (18)°]. The angle between the two aromatic rings is 86.90 (5)° (Fig. 2). Both partially saturated nitrogen heterocycles adopt twisted half-chair conformations, with atoms N1, C6 and C12 deviating significantly from the planes of the aromatic rings. Both the last mentioned methoxy and the N-methyl group deviate most from molecular twofold symmetry. As they rotate freely, their position can be most easily affected by packing interactions, including hydrogen bonding interactions. The conformation is nearly identical to the structure of argemonine methiodide, with the r.m.s. deviation of the superimposition being only 0.08 Å.

The water O atom of this hemihydrate lies on a twofold axis and takes part in O—H···O hydrogen bonding to symmetry-related argemonine molecules (Table 1). Their mutual orientation can be described as two crossed L letters (Fig. 2). This finding is in contrast with the previously published structure of (–)-argemonine methiodide (Kaneda et al., 1976) where the crystal packing revealed molecules aligned in a sandwich-like arrangement.

S2. Experimental

(–)-Argemonine was isolated from Argemone platyceras Link et Otto (Slavík & Slavíková, 1963), crystallized from ether and recrystallized from aqueous methanol (m.p. 427–428 K), [α]_D²¹ = -208° (0.5 M in CHCl₃).

S3. Refinement

The absolute structure could not be established from the present data (Flack, 1983) because of the weak anomalous scattering signal. Friedel reflections were merged for the final refinement. The absolute configuration shown, the 6S,12S isomer, is based on the absolute stereochemistry established previously (Červinka et al., 1966; Kaneda et al., 1976). All argemonine H atoms were treated as riding, with C—H = 0.93–0.98 Å. The H atom (H30A) of the water molecule was postioned from a difference map and allowed to refine isotropically.

Computing details

Data collection: KM-4 Software (Kuma, 1992); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996).

Figures

	Fig. 1. A perspective view of the (–)-argemonine molecule with the atom-numbering scheme. Ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of two molecules of (–)-argemonine linked by O—H···O hydrogen bonds with the water molecule on a twofold axis.

(6S,12S)-2,3,8,9-tetramethoxy-13-methyl-13- azadibenzo[b,f]bicyclo[3.3.1]nona-2,6-diene hemihydrate

Crystal data

C21H25NO4·0.5H2O	F(000) = 780
Mr = 364.43	Dx = 1.337 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 18.169 (4) Å	Cell parameters from 50 reflections
b = 9.801 (2) Å	θ = 11.0–20.8°
c = 12.726 (3) Å	µ = 0.09 mm^−1
β = 126.96 (3)°	T = 130 K
V = 1810.8 (7) Å^3	Trigonal bipyramid, colourless
Z = 4	0.70 × 0.50 × 0.50 mm

Data collection

Kuma KM-4 CCD diffractometer	2201 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.5°, θmin = 4.0°
ω scans	h = −23→23
6415 measured reflections	k = −12→13
2254 independent reflections	l = −16→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.4286P] where P = (Fo^2 + 2Fc^2)/3
2254 reflections	(Δ/σ)max < 0.001
249 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O18	0.20462 (7)	−0.02808 (11)	0.71574 (10)	0.0185 (2)
O19	0.11674 (7)	0.16177 (13)	0.54123 (11)	0.0231 (2)
O20	0.59998 (8)	0.67489 (12)	0.89583 (11)	0.0222 (2)
O21	0.64642 (8)	0.55233 (12)	1.11413 (11)	0.0241 (2)
N1	0.50822 (8)	0.09674 (14)	0.66303 (12)	0.0167 (2)
C1	0.34395 (9)	0.00897 (14)	0.73301 (13)	0.0147 (3)
H1	0.3760	−0.0616	0.7963	0.018*
C2	0.25372 (9)	0.03771 (15)	0.68216 (13)	0.0153 (3)
C3	0.20607 (9)	0.14204 (15)	0.58740 (13)	0.0170 (3)
C4	0.25100 (9)	0.21543 (16)	0.54884 (13)	0.0172 (3)
H4	0.2192	0.2864	0.4859	0.021*
C4A	0.34288 (10)	0.18693 (14)	0.60110 (13)	0.0159 (3)
C5	0.38981 (10)	0.26917 (16)	0.55722 (13)	0.0179 (3)
H5A	0.3774	0.3674	0.5580	0.021*
H5B	0.3645	0.2437	0.4660	0.021*
C6	0.49433 (10)	0.24432 (14)	0.64784 (13)	0.0157 (3)
H6	0.5207	0.2798	0.6032	0.019*
C6A	0.53892 (9)	0.32075 (15)	0.77685 (13)	0.0151 (3)
C7	0.55162 (10)	0.46154 (15)	0.77932 (14)	0.0168 (3)
H7	0.5348	0.5069	0.7018	0.020*
C8	0.58810 (10)	0.53527 (15)	0.89255 (15)	0.0177 (3)
C9	0.61269 (9)	0.46963 (16)	1.00783 (14)	0.0176 (3)
C10	0.60070 (9)	0.33018 (15)	1.00613 (14)	0.0165 (3)
H10	0.6173	0.2850	1.0836	0.020*
C10A	0.56435 (9)	0.25494 (14)	0.89111 (13)	0.0142 (3)
C11	0.55449 (9)	0.10271 (15)	0.89139 (13)	0.0152 (3)
H11A	0.5317	0.0791	0.9428	0.018*
H11B	0.6156	0.0594	0.9345	0.018*
C12	0.48756 (9)	0.04657 (15)	0.75113 (13)	0.0148 (3)
H12	0.4931	−0.0551	0.7553	0.018*
C12A	0.38865 (9)	0.08291 (14)	0.69218 (12)	0.0144 (3)
C13	0.25171 (10)	−0.13501 (17)	0.80910 (15)	0.0209 (3)
H13A	0.2687	−0.2061	0.7731	0.031*
H13B	0.2114	−0.1741	0.8285	0.031*
H13C	0.3075	−0.0987	0.8901	0.031*
C14	0.06546 (10)	0.25843 (18)	0.43721 (15)	0.0254 (3)
H14A	0.0920	0.3495	0.4696	0.038*
H14B	0.0012	0.2586	0.4058	0.038*
H14C	0.0680	0.2335	0.3648	0.038*
C15	0.67676 (11)	0.71114 (17)	0.89810 (16)	0.0238 (3)
H15A	0.7327	0.6694	0.9748	0.036*
H15B	0.6837	0.8106	0.9034	0.036*
H15C	0.6668	0.6784	0.8176	0.036*
C16	0.66980 (13)	0.4889 (2)	1.23151 (16)	0.0303 (4)
H16A	0.6149	0.4459	1.2145	0.045*
H16B	0.6934	0.5579	1.3006	0.045*
H16C	0.7172	0.4195	1.2601	0.045*
C17	0.59854 (10)	0.05447 (16)	0.70245 (16)	0.0212 (3)
H17A	0.6058	0.0826	0.6352	0.032*
H17B	0.6040	−0.0450	0.7121	0.032*
H17C	0.6466	0.0974	0.7865	0.032*
O30	0.5000	0.8061 (2)	1.0000	0.0331 (4)
H30A	0.533 (2)	0.757 (4)	0.983 (3)	0.084 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O18	0.0174 (4)	0.0170 (5)	0.0222 (5)	0.0010 (4)	0.0125 (4)	0.0032 (4)
O19	0.0159 (5)	0.0238 (6)	0.0248 (5)	0.0053 (4)	0.0097 (4)	0.0063 (5)
O20	0.0298 (5)	0.0109 (5)	0.0297 (5)	−0.0011 (4)	0.0199 (5)	−0.0013 (4)
O21	0.0338 (6)	0.0171 (5)	0.0199 (5)	−0.0059 (5)	0.0154 (5)	−0.0045 (4)
N1	0.0209 (5)	0.0130 (5)	0.0202 (5)	0.0004 (5)	0.0144 (5)	0.0003 (4)
C1	0.0157 (6)	0.0127 (6)	0.0135 (5)	0.0007 (5)	0.0075 (5)	0.0005 (5)
C2	0.0171 (6)	0.0134 (6)	0.0153 (6)	−0.0020 (5)	0.0096 (5)	−0.0021 (5)
C3	0.0154 (6)	0.0156 (6)	0.0158 (6)	0.0016 (5)	0.0073 (5)	−0.0009 (5)
C4	0.0183 (6)	0.0143 (6)	0.0144 (6)	0.0022 (5)	0.0074 (5)	0.0014 (5)
C4A	0.0186 (6)	0.0140 (6)	0.0136 (5)	−0.0004 (5)	0.0089 (5)	−0.0001 (5)
C5	0.0225 (6)	0.0155 (6)	0.0159 (6)	0.0012 (5)	0.0117 (5)	0.0026 (5)
C6	0.0219 (6)	0.0124 (6)	0.0169 (6)	−0.0010 (5)	0.0138 (5)	0.0004 (5)
C6A	0.0167 (6)	0.0131 (6)	0.0179 (6)	0.0000 (5)	0.0116 (5)	0.0001 (5)
C7	0.0207 (6)	0.0137 (6)	0.0192 (6)	0.0005 (5)	0.0136 (6)	0.0019 (5)
C8	0.0204 (6)	0.0121 (6)	0.0227 (7)	−0.0007 (5)	0.0141 (6)	−0.0002 (5)
C9	0.0177 (6)	0.0163 (7)	0.0182 (6)	−0.0021 (5)	0.0105 (5)	−0.0023 (5)
C10	0.0167 (6)	0.0164 (7)	0.0158 (6)	−0.0007 (5)	0.0094 (5)	0.0011 (5)
C10A	0.0143 (5)	0.0111 (6)	0.0174 (6)	−0.0006 (5)	0.0096 (5)	0.0000 (5)
C11	0.0159 (6)	0.0127 (6)	0.0159 (6)	0.0003 (5)	0.0090 (5)	0.0028 (5)
C12	0.0174 (6)	0.0111 (6)	0.0175 (6)	0.0005 (5)	0.0114 (5)	0.0013 (5)
C12A	0.0167 (6)	0.0123 (6)	0.0132 (6)	−0.0012 (5)	0.0084 (5)	−0.0010 (5)
C13	0.0184 (6)	0.0191 (7)	0.0228 (7)	−0.0020 (6)	0.0111 (6)	0.0052 (6)
C14	0.0199 (6)	0.0223 (7)	0.0243 (7)	0.0065 (6)	0.0080 (6)	0.0046 (6)
C15	0.0276 (7)	0.0150 (6)	0.0293 (7)	−0.0045 (6)	0.0173 (6)	−0.0005 (6)
C16	0.0430 (9)	0.0274 (8)	0.0202 (7)	−0.0090 (8)	0.0188 (7)	−0.0056 (7)
C17	0.0237 (7)	0.0185 (7)	0.0289 (7)	0.0007 (6)	0.0198 (6)	0.0012 (6)
O30	0.0294 (9)	0.0193 (8)	0.0492 (11)	0.000	0.0228 (9)	0.000

Geometric parameters (Å, º)

O18—C2	1.3611 (16)	C7—H7	0.9500
O18—C13	1.4211 (18)	C8—C9	1.406 (2)
O19—C3	1.3675 (17)	C9—C10	1.382 (2)
O19—C14	1.4264 (19)	C10—C10A	1.4000 (19)
O20—C8	1.3820 (18)	C10—H10	0.9500
O20—C15	1.4230 (19)	C10A—C11	1.5029 (19)
O21—C9	1.3659 (18)	C11—C12	1.535 (2)
O21—C16	1.426 (2)	C11—H11A	0.9900
N1—C6	1.4610 (18)	C11—H11B	0.9900
N1—C12	1.4648 (17)	C12—C12A	1.5159 (18)
N1—C17	1.4582 (18)	C12—H12	1.0000
C1—C2	1.3821 (19)	C13—H13A	0.9800
C1—C12A	1.4008 (19)	C13—H13B	0.9800
C1—H1	0.9500	C13—H13C	0.9800
C2—C3	1.4120 (19)	C14—H14A	0.9800
C3—C4	1.381 (2)	C14—H14B	0.9800
C4—C4A	1.404 (2)	C14—H14C	0.9800
C4—H4	0.9500	C15—H15A	0.9800
C4A—C12A	1.3839 (19)	C15—H15B	0.9800
C4A—C5	1.5037 (19)	C15—H15C	0.9800
C5—C6	1.537 (2)	C16—H16A	0.9800
C5—H5A	0.9900	C16—H16B	0.9800
C5—H5B	0.9900	C16—H16C	0.9800
C6—C6A	1.5209 (19)	C17—H17A	0.9800
C6—H6	1.0000	C17—H17B	0.9800
C6A—C10A	1.3914 (19)	C17—H17C	0.9800
C6A—C7	1.3963 (19)	O30—H30A	0.90 (4)
C7—C8	1.375 (2)
C2—O18—C13	115.67 (11)	C6A—C10A—C10	119.99 (13)
C3—O19—C14	115.91 (12)	C6A—C10A—C11	119.83 (13)
C8—O20—C15	112.41 (12)	C10—C10A—C11	120.17 (12)
C9—O21—C16	116.90 (13)	C10A—C11—C12	111.42 (11)
C17—N1—C6	113.32 (12)	C10A—C11—H11A	109.3
C17—N1—C12	113.24 (12)	C12—C11—H11A	109.3
C6—N1—C12	109.29 (11)	C10A—C11—H11B	109.3
C2—C1—C12A	120.66 (12)	C12—C11—H11B	109.3
C2—C1—H1	119.7	H11A—C11—H11B	108.0
C12A—C1—H1	119.7	N1—C12—C12A	108.39 (11)
O18—C2—C1	124.98 (12)	N1—C12—C11	112.41 (11)
O18—C2—C3	115.47 (12)	C12A—C12—C11	111.45 (11)
C1—C2—C3	119.54 (12)	N1—C12—H12	108.2
O19—C3—C4	125.18 (13)	C12A—C12—H12	108.2
O19—C3—C2	115.42 (13)	C11—C12—H12	108.2
C4—C3—C2	119.40 (13)	C4A—C12A—C1	120.09 (12)
C3—C4—C4A	121.10 (13)	C4A—C12A—C12	121.61 (12)
C3—C4—H4	119.5	C1—C12A—C12	118.30 (12)
C4A—C4—H4	119.5	O18—C13—H13A	109.5
C12A—C4A—C4	119.20 (13)	O18—C13—H13B	109.5
C12A—C4A—C5	121.10 (12)	H13A—C13—H13B	109.5
C4—C4A—C5	119.70 (13)	O18—C13—H13C	109.5
C4A—C5—C6	110.93 (11)	H13A—C13—H13C	109.5
C4A—C5—H5A	109.5	H13B—C13—H13C	109.5
C6—C5—H5A	109.5	O19—C14—H14A	109.5
C4A—C5—H5B	109.5	O19—C14—H14B	109.5
C6—C5—H5B	109.5	H14A—C14—H14B	109.5
H5A—C5—H5B	108.0	O19—C14—H14C	109.5
N1—C6—C6A	114.03 (12)	H14A—C14—H14C	109.5
N1—C6—C5	107.05 (11)	H14B—C14—H14C	109.5
C6A—C6—C5	110.35 (12)	O20—C15—H15A	109.5
N1—C6—H6	108.4	O20—C15—H15B	109.5
C6A—C6—H6	108.4	H15A—C15—H15B	109.5
C5—C6—H6	108.4	O20—C15—H15C	109.5
C10A—C6A—C7	119.21 (13)	H15A—C15—H15C	109.5
C10A—C6A—C6	121.77 (13)	H15B—C15—H15C	109.5
C7—C6A—C6	118.98 (12)	O21—C16—H16A	109.5
C8—C7—C6A	120.81 (13)	O21—C16—H16B	109.5
C8—C7—H7	119.6	H16A—C16—H16B	109.5
C6A—C7—H7	119.6	O21—C16—H16C	109.5
C7—C8—O20	121.35 (13)	H16A—C16—H16C	109.5
C7—C8—C9	120.24 (14)	H16B—C16—H16C	109.5
O20—C8—C9	118.40 (13)	N1—C17—H17A	109.5
O21—C9—C10	125.10 (13)	N1—C17—H17B	109.5
O21—C9—C8	115.70 (13)	H17A—C17—H17B	109.5
C10—C9—C8	119.20 (14)	N1—C17—H17C	109.5
C9—C10—C10A	120.54 (13)	H17A—C17—H17C	109.5
C9—C10—H10	119.7	H17B—C17—H17C	109.5
C10A—C10—H10	119.7	H30A—O30—H30A^i	115 (4)
C13—O18—C2—C1	−0.9 (2)	C16—O21—C9—C10	−0.8 (2)
C13—O18—C2—C3	178.77 (12)	C16—O21—C9—C8	178.50 (14)
C12A—C1—C2—O18	−179.88 (13)	C7—C8—C9—O21	−178.61 (12)
C12A—C1—C2—C3	0.5 (2)	O20—C8—C9—O21	0.2 (2)
C14—O19—C3—C4	5.6 (2)	C7—C8—C9—C10	0.7 (2)
C14—O19—C3—C2	−174.66 (13)	O20—C8—C9—C10	179.56 (13)
O18—C2—C3—O19	−0.67 (18)	O21—C9—C10—C10A	179.15 (13)
C1—C2—C3—O19	179.02 (12)	C8—C9—C10—C10A	−0.1 (2)
O18—C2—C3—C4	179.12 (12)	C7—C6A—C10A—C10	1.1 (2)
C1—C2—C3—C4	−1.2 (2)	C6—C6A—C10A—C10	−176.60 (12)
O19—C3—C4—C4A	−179.45 (13)	C7—C6A—C10A—C11	−177.65 (13)
C2—C3—C4—C4A	0.8 (2)	C6—C6A—C10A—C11	4.7 (2)
C3—C4—C4A—C12A	0.4 (2)	C9—C10—C10A—C6A	−0.8 (2)
C3—C4—C4A—C5	−179.81 (13)	C9—C10—C10A—C11	177.96 (13)
C12A—C4A—C5—C6	−13.16 (18)	C6A—C10A—C11—C12	−18.97 (17)
C4—C4A—C5—C6	167.03 (12)	C10—C10A—C11—C12	162.29 (12)
C17—N1—C6—C6A	−79.59 (15)	C17—N1—C12—C12A	−173.65 (12)
C12—N1—C6—C6A	47.71 (15)	C6—N1—C12—C12A	59.01 (14)
C17—N1—C6—C5	158.06 (11)	C17—N1—C12—C11	62.72 (16)
C12—N1—C6—C5	−74.64 (14)	C6—N1—C12—C11	−64.63 (15)
C4A—C5—C6—N1	48.37 (15)	C10A—C11—C12—N1	49.41 (15)
C4A—C5—C6—C6A	−76.25 (15)	C10A—C11—C12—C12A	−72.50 (14)
N1—C6—C6A—C10A	−19.05 (19)	C4—C4A—C12A—C1	−1.11 (19)
C5—C6—C6A—C10A	101.48 (15)	C5—C4A—C12A—C1	179.07 (12)
N1—C6—C6A—C7	163.25 (12)	C4—C4A—C12A—C12	179.45 (12)
C5—C6—C6A—C7	−76.23 (16)	C5—C4A—C12A—C12	−0.4 (2)
C10A—C6A—C7—C8	−0.5 (2)	C2—C1—C12A—C4A	0.7 (2)
C6—C6A—C7—C8	177.27 (12)	C2—C1—C12A—C12	−179.85 (12)
C6A—C7—C8—O20	−179.21 (13)	N1—C12—C12A—C4A	−21.45 (18)
C6A—C7—C8—C9	−0.4 (2)	C11—C12—C12A—C4A	102.76 (14)
C15—O20—C8—C7	−75.56 (18)	N1—C12—C12A—C1	159.10 (12)
C15—O20—C8—C9	105.63 (15)	C11—C12—C12A—C1	−76.69 (16)

Symmetry code: (i) −x+1, y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O30—H30A···O20	0.90 (4)	2.23 (3)	3.0997 (15)	164 (3)