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The crystal structures of triethyl­ammonium adenosine cyclic 2′,3′-phosphate {systematic name: triethyl­ammonium 4-(6-amino­purin-9-yl)-6-hydroxy­methyl-2-oxido-2-oxoperhydro­furano[3,4-c][1,3,2]dioxaphosphole}, Et3NH(2′,3′-cAMP) or C6H16N+·C10H11N5O6P, (I), and guanosine cyclic 2′,3′-phosphate monohydrate {systematic name: triethyl­ammonium 6-hydroxy­methyl-2-oxido-2-oxo-4-(6-oxo-1,6-dihydro­purin-9-yl)perhydro­furano[3,4-c][1,3,2]dioxaphosphole monohydrate}, [Et3NH(2′,3′-cGMP)]·H2O or C6H16N+·C10H11N5O7P·H2O, (II), reveal different nucleobase orientations, viz. anti in (I) and syn in (II). These are stabilized by different inter- and intra­molecular hydrogen bonds. The structures also exhibit different ribose ring puckering [4E in (I) and 3T2 in (II)] and slightly different 1,3,2-dioxaphospho­lane ring conformations, viz. envelope in (I) and puckered in (II). Infinite ribbons of 2′,3′-cAMP and helical chains of 2′,3′-cGMP ions, both formed by O—H...O, N—H...X and C—H...X (X = O or N) hydrogen-bond contacts, characterize (I) and (II), respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106017811/fg3019sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106017811/fg3019Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106017811/fg3019IIsup3.hkl
Contains datablock II

CCDC references: 269300; 269301

Comment top

The title compounds, ribonucleoside 2',3'-O,O-cyclic phosphates, are the intermediates of RNA degradation (Raines, 1998; Kuimelis & McLaughlin, 1998; Oivanen et al., 1998). The mechanisms of the two steps of this ribonuclease-catalyzed process, viz. (1) transphosphorylation giving the respective nucleoside 2',3'-O,O-cyclic phosphate and (2) its hydrolysis (by the same enzyme) towards the nucleoside 3'-phosphate, are well recognized. However, accumulation of the respective nucleoside 2',3'-O,O-cyclic phosphates has been observed during degradation of the RNA chain, which makes the reasons for the different kinetics of the above steps intriguing (Cuchillo et al., 1993). The fact that nucleoside 2',3'-O,O-cyclic phosphates are chemically less stable than linear dinucleoside phosphates (Thompson et al., 1994) has to be another cause of the kinetic advantage of enzymatic transphosphorylation of RNA over hydrolysis of the produced nucleoside 2',3'-O,O-cyclic phosphates. Since enzyme-catalyzed reactions are discussed it might be acceptable to postulate that linear (3'-5') dinucleoside phosphates have different conformations compared with their 2',3'-O,O-cyclic analogues. In consequence, the latter form might give a less productive complex with the enzyme. If this is the case, the crystal structure of nucleoside 2',3'-O,O-cyclic phosphates becomes of high importance in verification of the above postulates.

Nucleoside 2',3'-O,O-cyclic phosphates have been poorly explored as regards their solid-state structure. The only X-ray data available so far for two pyrimidine nucleotides [2',3'-cCMP (Reddy & Saenger, 1978) and Na(2',3'-cCMP) (Coulter, 1973] and one uridine phosphorothioate analogue [Et3NH(2',3'-cUMPS) (Saenger & Eckstein, 1970)] do not reveal any correlations between the nucleobase type or the chemical environment and the molecular structure observed in the crystal. In particular, no such influence on nucloeobase orientation, ribose puckering or 1,3,2-dioxaphospholane ring conformation has been observed. The purine 2',3'-O,O-cyclic phosphates have never been crystallized and structurally characterized by X-ray crystallography.

We report here the results of our single-crystal X-ray study of two 2',3'-O,O-cyclic phosphates of purine ribonucleosides in the form of their triethylammonium salts, (I) and (II), and compare the results with those previously described and deposited with the Cambridge Structural Database (CSD; Allen, 2002) for three analogous pyrimidine compounds, viz. 2',3'-cCMP (Reddy & Saenger, 1978; CSD refcode CYCYPH10), Na(2',3'-cCMP) (Coulter, 1973; CSD refcode CYTCYP20) and Et3NH(2',3'-cUMPS) (Saenger & Eckstein, 1970; CSD refcode URIDPS10).

The compounds presented here crystallize with one 2',3'-cyclic nucleotide anion (Fig. 1), one Et3NH+ cation [disordered in both (I) and (II); Fig. 2] and one water molecule [for (II)] in the asymmetric unit. 2',3'-cAMP in (I) and 2',3'-cGMP in (II) reveal different orientation of the nucleobase with respect to the ribose ring. This is reflected in the conformation about the glycosidic (C1'—N9) bond, which is anti in (I) and syn in (II), and gives rise to different values of the χCN angle (O1'—C1'—N9—C8; see Tables 1 and 3). Most nucleosides and nucleotides show a preference for the anti conformation about the glycosidic bond in the crystalline state; however, some of the cyclic nucleotides, e.g. 2',3'-cCMP in its sodium salt, 3',5'-cAMP and 3',5'-cGMP, exist in the syn conformation (Coulter, 1973; Sundaralingam, 1969; Allen, 2002). Surprisingly, 2',3'-cCMP in the form of free acid and its sodium salt crystallize with a different conformation about the χCN bond, viz. anti and syn, respectively (Reddy & Saenger, 1978; Coulter, 1973).

The different orientation of the nucleobase with respect to the ribose ring observed in 2',3'-cAMP and 2',3'-cGMP anions is accompanied by a different ribose ring puckering. Although the conformation of the sugar moiety of the 2',3'-cyclic phosphates may be described by the use of the classical conformational descriptors for envelope and twist puckering, the presence of another cyclic system (O/P/O/C/C) results in significant deformation, mainly flattening of the furanose ring. Therefore, the sugar conformations observed in (I) and (II) are distorted C4'-exo envelope (4E) and C3'-endo, C2'-exo twist (3T2), respectively. The q2 and Φ2 (Cremer & Pople, 1975) puckering parameters are 0.354 (3) Å and 319.4 (5)° for (I), and 0.165 (2) Å and 273.5 (5)° for (II). The puckered atom C4' in the anion in (I) is displaced by about 0.54 Å out of the four-atom plane of the sugar ring. The angle between the O1'/C4'/C3' and O1'/C1'/C2'/C3' is 36.0 (2)°. The distances of the puckered C3' and C2' atoms from the three-atom plane in 3T2 ribose ring in (II) are only about 0.16 and 0.11 Å, respectively. The conformations of the ribose rings observed in (I) and (II) differ from those previously observed in the related compounds described so far, viz. Na(2',3'-cCMP) (Coulter, 1973) and Et3NH(2',3'-cUMPS) (Saenger & Eckstein, 1970), which show the ribose ring in an envelope conformation with O1'-endo or O1'-exo puckering, and also differ from the 2T3 conformation observed in 2',3'-cCMP (Reddy & Saenger, 1978).

The orientation of the ribose hydroxymethyl O5' atom with relation to the sugar ring is also different in the 2',3'-cyclic phosphates of purine ribonucleotides presented here. The differences are reflected in the conformation about the C4'—C5' bond, which is gauchetrans for (I) and transgauche for (II) (see the O1'—C4'—C5'—O5' and C3'—C4'—C5'—O5' torsion angles in Tables 1 and 3). The previously reported data reveal the gauchetrans conformation for one of two crystallographically independent anions in Na[2',3'-cCMP] and transgauche for Et3NH(2',3'-cUMPS). However, the conformation about the C4'—C5' bond observed in the second anion in Na[2',3'-cCMP] and in the acid, 2',3'-cCMP is gauchegauche, which is also the commonly observed C4'—C5' conformation in nucleotides, their phosphate monoesters and polinucleotides in the solid state (Sundaralingam, 1969; Allen, 2002).

The 1,3,2-dioxaphospholane ring (O/P/O/C/C) in both (I) and (II) exists in an envelope conformation, with atom C2' and C3', respectively, displaced from the four-atom plane by about 0.41 and 0.31 Å, respectively. The mutual orientation of the two cyclic systems – ribose and dioxaphospholane rings – might be described by the angle between the planes built up from three or four atoms of each ring. Thus, the angle between the O1'/C1'/C2'/C3' and O2'/P1/O3'/C3' planes in (I) is 47.4 (2)°, and that between the C4'/O1'/C1' and C2'/O2'/P1/O3' planes in (II) is 108.4 (2)°.

Significant deviation from the ideal tetrahedral geometry around the P atom is observed in both 2',3'-cAMP and 2',3'-cGMP anions. This is mainly reflected in the values of the exocyclic O1—P1—O2 and the endocyclic O2'—P1—O3' angles, which differ one from another by about 21°.

The crystal and molecular structures of (I) and (II) are stabilized by a network of O—H···X and N—H···X hydrogen bonds, and C—H···X close contacts (where X = O and N). Some of these bonds also stabilize the different orientation of the nucleobase with respect to the ribose ring observed in the 2',3'-cAMP and 2',3'-cGMP anions.

Adjacent symmetry-related anions in (I) are linked by O5'—H5'···O2i, N6—H61···N3ii and C8—H8···O2ii interactions, in which hydroxymethyl, phosphate and nucleobase groups are involved (the geometry and symmetry codes are listed in Table 2). Such a combination of direct a axis translation [generating R22(15) ring motifs] and [100] screw rotation [resulting in R23(18) rings] gives rise to infinite ribbons of anions parallel to the a axis, shown in Fig. 3. It is noted that the ribbon–stabilizing, intermolecular N—H···O and C—H···O contacts, in which the nucleobase acts as the donor, may also stabilize the anti orientation of the adenine moiety to the ribose ring. In the crystal structure of (I), every ribbon is connected to four adjacent ribbons by N—H···O and N—H···N hydrogen bonds. In the channels formed in this way, the Et3NH cations are located and linked with the anions by N20—H20···O1 interactions. As a result, a three–dimensional hydrogen-bond network is formed in the crystal structure of (I).

The crystal of (II) is built up from 2',3'-cGMP anions, Et3NH cations and water molecules. Adjacent 21-related anions are linked each other by O—H···O, N—H···O and C—H···O interactions to form infinite helical chains along the b axis. As shown in Fig. 4 and Table 4, sugar atoms O5' and C3' as well as guanine atom N2 of one anion act as the donors in these three intermolecular contacts, while only one phosphate O atom (O1) from the adjacent anion is an acceptor. Hence, the four–centered bonds stabilize the structure of the chains formed in the crystal of (II). It is possible that a rather weak intramolecular C5'—H52'···N3 interaction, accompanied by the moderately strong N2—H22···O1v (see Table 4) interaction, may increase the stability of the syn conformation of the base with relation to the ribose ring of the 2',3'-cGMP anion.

Adjacent chains in the crystal structure of (II) are linked each other by a three–centered hydrogen bond formed by N1—H1···O6vii and N2—H21···O6vii contacts (both having the common acceptor O6vii; Table 4) and by the C8—H8···O1'viii interaction. Additionally the water molecules act as bridges between pairs of adjacent chains. The voids formed in this way between the chains, partly filled with the water molecules, are additionally occupied by Et3NH cations linked with the phosphate O atoms by N—H···O hydrogen bonds similar to those found in (I). This results in the extensive three-dimensional hydrogen-bond network in the crystal structure of (II).

In conclusion, the crystal and molecular structure of two purine 2',3'-cyclic ribonucleotides (synthesized and crystallized in the form of their triethylammonium salts) have been described. The conformations observed in the presented 2',3'-cAMP and 2',3'-cGMP anions reveal significant differences, the most impressive being the different nucleobase orientation.

Experimental top

Compounds (I) and (II) were synthesized according to previously described procedures (Jankowska et al., 2000). Crystals were obtained by slow evaporation of 2-propanol/water or water/ethanol/methanol solutions of (I) and (II), respectively, at 280 K. The data for (II) were collected at 200 (2) K owing to weak reflections at 1/3c* and 2/3c* observed at lower temperature.

Refinement top

The Et3NH+ cations are disordered over two positions in (I) [with site occupancy factors equal to 0.830 (5) for N20 and 0.170 (5) for N30] and into three positions in (II) [with site occuancy factors of 0.698 (3), 0.192 (5) and 0.111 (5) for N20, N30 and N40]. Only the high-occupancy positions of Et3NH+ [N20 in (I) and (II)] are discussed. In the refinement procedure of (I) and (II), some geometrical parameters of the positions of the disordered cations (equivalent bond distances and angles but not torsion angles) were restrained to be equal. The positions of pairs of atoms in (II) (N30 and N40, C31 and C41, C32 and C42, C33 and C43, and C34 and C44), were refined with the same x, y, z and anisotropic displacement parameters. All the non-H atoms were refined anisotropically, except for the low-occupied positions of disordered atoms of Et3NH+ cations in both (I) and (II). The H atoms of the anions in (I) and (II) and of water molecule in (II) were found in difference Fourier maps and were refined isotropically, except for atoms H1', H2' and H2W in (II), which were refined with Uiso(H) = Ueq(C1',C2') or Uiso(H) = 1.2Ueq(OW) [please check; values in CIF seem to contradict this]. All H atoms of disordered cations in (I) and (II) were included from geometry and treated as riding atoms, with N—H distances of 0.93 Å and C—H distances of 0.98 or 0.99 Å (for methyl and methylene groups), and with Uiso(H) values of 1.2Ueq(N,C) or 1.5Ueq(C).

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of the 2',3'-cAMP and 2',3'-cGMP anions in (I) and (II), respectively, showing the atom–numbering scheme and the intramolecular C—H···N hydrogen bond in (II) (marked with a dashed line). Displacement ellipsoids are drawn at the 20% probability level for the non-H atoms.
[Figure 2] Fig. 2. The molecular structure of the disordered triethylammonium cations in (I) [site occupancy factors: 0.830 (5), solid; 0.170 (5), double-dashed line] and (II) (site occupancy factors: 0.698 (3), solid; 0.192 (5), open; 0.111 (5), double-dashed line]. Atoms are shown as circles of arbitrary radii.
[Figure 3] Fig. 3. The arrangement of the 2',3'-cAMP anions in (I) within the ribbon formed by the adjacent anions related by 21 and direct a axis translation, linked by O—H···O and N—H···N (dashed lines) and by C—H···O (dotted lines) interactions. The H atoms not involved in these contacts are not shown. Symmetry codes are given in Table 2.
[Figure 4] Fig. 4. The arrangement of the 2',3'-cGMP anions in (II) within the helical chain formed by the adjacent, 21-related anions joined each other by the O—H···O, N—H···O (dashed lines) and C—H···N (dotted lines) interactions. H atoms not involved in these contacts are not shown. Symmetry codes are given in Table 4.
(I) Triethylammonium 4-(6-aminopurin-7-yl)-6-hydroxymethyl-2-oxido-2- oxoperhydrofurano[3,4-c][1,3,2]dioxaphosphole top
Crystal data top
C6H16N+·C10H11N5O6PF(000) = 912
Mr = 430.41Dx = 1.424 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 11796 reflections
a = 6.704 (2) Åθ = 4.5–75.8°
b = 10.493 (3) ŵ = 1.63 mm1
c = 28.536 (7) ÅT = 100 K
V = 2007.4 (10) Å3Needle, colourless
Z = 40.29 × 0.09 × 0.03 mm
Data collection top
Xcalibur PX κ-geometry
diffractometer with Onyx CCD camera
3911 independent reflections
Radiation source: fine-focus sealed tube3559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω and ϕ scansθmax = 75.8°, θmin = 4.5°
Absorption correction: analytical
CrysAlis RED (Oxford Diffraction, 2003)
h = 78
Tmin = 0.742, Tmax = 0.954k = 139
14174 measured reflectionsl = 3525
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0714P)2 + 0.7467P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.29 e Å3
3911 reflectionsΔρmin = 0.43 e Å3
336 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
12 restraintsExtinction coefficient: 0.0018 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 1481 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (3)
Crystal data top
C6H16N+·C10H11N5O6PV = 2007.4 (10) Å3
Mr = 430.41Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 6.704 (2) ŵ = 1.63 mm1
b = 10.493 (3) ÅT = 100 K
c = 28.536 (7) Å0.29 × 0.09 × 0.03 mm
Data collection top
Xcalibur PX κ-geometry
diffractometer with Onyx CCD camera
3911 independent reflections
Absorption correction: analytical
CrysAlis RED (Oxford Diffraction, 2003)
3559 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 0.954Rint = 0.063
14174 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 0.29 e Å3
S = 1.09Δρmin = 0.43 e Å3
3911 reflectionsAbsolute structure: (Flack, 1983), 1481 Friedel pairs
336 parametersAbsolute structure parameter: 0.02 (3)
12 restraints
Special details top

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*/UeqOcc. (<1)
P10.44603 (11)0.53283 (7)0.58565 (2)0.02082 (18)
O10.4791 (3)0.6720 (2)0.59020 (8)0.0318 (5)
O20.2404 (3)0.4871 (2)0.57621 (7)0.0251 (4)
O1'0.7434 (3)0.18430 (18)0.60525 (6)0.0228 (4)
O2'0.5349 (3)0.45957 (19)0.63120 (7)0.0217 (4)
O3'0.6018 (3)0.4743 (2)0.54838 (7)0.0257 (5)
O5'0.6294 (4)0.0615 (2)0.51564 (8)0.0330 (5)
H5'0.680 (8)0.041 (6)0.4816 (19)0.073 (16)*
C1'0.7422 (5)0.2724 (3)0.64361 (9)0.0188 (5)
H1'0.632 (5)0.256 (3)0.6656 (12)0.019 (8)*
C2'0.7296 (4)0.4065 (3)0.62207 (9)0.0200 (6)
H2'0.832 (6)0.468 (4)0.6354 (13)0.035 (10)*
C3'0.7325 (4)0.3830 (3)0.56946 (9)0.0193 (5)
H3'0.862 (6)0.399 (4)0.5568 (15)0.037 (11)*
C4'0.6586 (4)0.2461 (3)0.56471 (9)0.0203 (6)
H4'0.506 (6)0.240 (4)0.5671 (12)0.027 (9)*
C5'0.7283 (5)0.1803 (3)0.52112 (10)0.0259 (6)
H51'0.697 (6)0.236 (4)0.4933 (14)0.035 (10)*
H52'0.886 (6)0.168 (4)0.5252 (13)0.033 (10)*
N11.0554 (4)0.0560 (3)0.78775 (9)0.0284 (6)
C20.8651 (5)0.0658 (3)0.77331 (11)0.0258 (6)
H20.770 (6)0.023 (4)0.7916 (13)0.034 (10)*
N30.7926 (4)0.1278 (2)0.73607 (8)0.0220 (5)
C40.9396 (4)0.1836 (3)0.71136 (9)0.0185 (5)
C51.1412 (4)0.1809 (3)0.72162 (9)0.0190 (5)
C61.1987 (4)0.1150 (3)0.76241 (10)0.0235 (6)
N61.3886 (4)0.1079 (3)0.77699 (10)0.0307 (6)
H611.481 (6)0.137 (4)0.7593 (15)0.035 (11)*
H621.418 (7)0.040 (5)0.8027 (17)0.059 (13)*
N71.2516 (4)0.2462 (2)0.68797 (8)0.0213 (5)
C81.1160 (4)0.2860 (3)0.65823 (10)0.0212 (6)
H81.146 (5)0.340 (3)0.6291 (12)0.021 (8)*
N90.9228 (4)0.2511 (2)0.67048 (8)0.0191 (5)
N200.1931 (5)0.8461 (3)0.59896 (10)0.0297 (10)0.830 (5)
H200.28980.78570.59170.036*0.830 (5)
C210.0926 (5)0.8807 (3)0.55352 (10)0.0320 (9)0.830 (5)
H21A0.19380.91080.53080.038*0.830 (5)
H21B0.00320.95100.55900.038*0.830 (5)
C220.0206 (18)0.7626 (11)0.5326 (3)0.054 (3)0.830 (5)
H22A0.06410.68680.53510.082*0.830 (5)
H22B0.05190.77860.49960.082*0.830 (5)
H22C0.14450.74880.55010.082*0.830 (5)
C230.0542 (8)0.7842 (4)0.63362 (15)0.0400 (11)0.830 (5)
H23A0.13220.75720.66140.048*0.830 (5)
H23B0.00340.70670.61920.048*0.830 (5)
C240.1143 (9)0.8700 (6)0.6496 (2)0.0634 (18)0.830 (5)
H24A0.05890.94520.66530.095*0.830 (5)
H24B0.20000.82330.67160.095*0.830 (5)
H24C0.19300.89680.62240.095*0.830 (5)
C250.3009 (8)0.9590 (4)0.61777 (17)0.0422 (11)0.830 (5)
H25A0.20491.02980.62210.051*0.830 (5)
H25B0.40190.98680.59460.051*0.830 (5)
C260.4026 (12)0.9324 (5)0.6637 (2)0.0617 (18)0.830 (5)
H26A0.30190.91890.68810.093*0.830 (5)
H26B0.48691.00510.67220.093*0.830 (5)
H26C0.48540.85590.66070.093*0.830 (5)
N300.144 (3)0.8318 (19)0.6046 (6)0.023 (5)*0.170 (5)
H300.21430.75550.60470.028*0.170 (5)
C310.267 (3)0.9189 (19)0.5737 (7)0.045 (6)*0.170 (5)
H31A0.27080.88440.54140.054*0.170 (5)
H31B0.40570.92270.58560.054*0.170 (5)
C320.177 (4)1.053 (2)0.5731 (10)0.061 (8)*0.170 (5)
H32A0.25681.10850.55270.092*0.170 (5)
H32B0.17671.08810.60500.092*0.170 (5)
H32C0.03991.04930.56130.092*0.170 (5)
C330.136 (3)0.869 (3)0.6556 (7)0.053 (7)*0.170 (5)
H33A0.06850.80080.67350.063*0.170 (5)
H33B0.05430.94760.65880.063*0.170 (5)
C340.340 (3)0.893 (3)0.6769 (8)0.035 (5)*0.170 (5)
H34A0.32440.91990.70960.052*0.170 (5)
H34B0.40800.96020.65920.052*0.170 (5)
H34C0.41860.81450.67560.052*0.170 (5)
C350.052 (4)0.797 (4)0.5845 (9)0.086 (11)*0.170 (5)
H35A0.15010.86470.59190.103*0.170 (5)
H35B0.09900.71680.59890.103*0.170 (5)
C360.040 (7)0.781 (4)0.5320 (10)0.025 (8)*0.170 (5)
H36A0.17190.75950.51970.037*0.170 (5)
H36B0.05380.71170.52460.037*0.170 (5)
H36C0.00730.86010.51770.037*0.170 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0226 (4)0.0203 (3)0.0195 (3)0.0025 (3)0.0015 (3)0.0008 (3)
O10.0363 (13)0.0213 (10)0.0377 (12)0.0021 (9)0.0064 (10)0.0038 (10)
O20.0236 (10)0.0304 (10)0.0214 (9)0.0006 (8)0.0019 (8)0.0010 (8)
O1'0.0332 (12)0.0211 (9)0.0141 (8)0.0023 (9)0.0062 (8)0.0018 (8)
O2'0.0212 (10)0.0260 (9)0.0179 (8)0.0063 (8)0.0014 (8)0.0005 (8)
O3'0.0278 (11)0.0283 (11)0.0211 (9)0.0077 (9)0.0013 (8)0.0073 (9)
O5'0.0421 (13)0.0304 (11)0.0267 (11)0.0016 (9)0.0026 (10)0.0091 (9)
C1'0.0197 (14)0.0206 (13)0.0163 (11)0.0036 (11)0.0035 (11)0.0007 (10)
C2'0.0204 (14)0.0202 (12)0.0192 (12)0.0024 (10)0.0021 (11)0.0023 (11)
C3'0.0219 (14)0.0220 (12)0.0140 (11)0.0036 (11)0.0008 (10)0.0036 (10)
C4'0.0245 (15)0.0232 (13)0.0132 (12)0.0044 (11)0.0043 (11)0.0014 (11)
C5'0.0311 (17)0.0274 (14)0.0193 (13)0.0014 (13)0.0012 (12)0.0034 (12)
N10.0185 (12)0.0395 (14)0.0272 (12)0.0021 (11)0.0009 (11)0.0139 (11)
C20.0181 (14)0.0363 (17)0.0230 (14)0.0018 (12)0.0012 (11)0.0101 (12)
N30.0175 (12)0.0284 (12)0.0201 (11)0.0001 (9)0.0006 (9)0.0063 (10)
C40.0183 (13)0.0215 (12)0.0157 (12)0.0020 (11)0.0015 (11)0.0038 (10)
C50.0157 (13)0.0234 (13)0.0178 (12)0.0014 (10)0.0015 (10)0.0038 (11)
C60.0158 (14)0.0354 (15)0.0193 (13)0.0022 (11)0.0014 (11)0.0052 (12)
N60.0176 (14)0.0478 (17)0.0268 (13)0.0003 (11)0.0008 (10)0.0160 (13)
N70.0199 (12)0.0271 (12)0.0170 (10)0.0013 (10)0.0017 (9)0.0017 (9)
C80.0207 (15)0.0221 (13)0.0209 (13)0.0018 (10)0.0030 (11)0.0016 (11)
N90.0167 (11)0.0262 (11)0.0144 (10)0.0012 (10)0.0017 (9)0.0031 (9)
N200.038 (3)0.0238 (18)0.0274 (19)0.0066 (17)0.0029 (17)0.0013 (14)
C210.038 (2)0.0300 (18)0.0282 (18)0.0049 (16)0.0004 (16)0.0092 (15)
C220.053 (5)0.060 (6)0.051 (4)0.019 (4)0.016 (3)0.000 (3)
C230.057 (3)0.0293 (19)0.034 (2)0.0087 (19)0.017 (2)0.0074 (17)
C240.074 (4)0.052 (3)0.064 (3)0.018 (3)0.043 (3)0.011 (3)
C250.058 (3)0.0203 (17)0.049 (3)0.0004 (18)0.007 (2)0.0055 (18)
C260.090 (5)0.034 (3)0.061 (4)0.002 (3)0.026 (4)0.010 (3)
Geometric parameters (Å, º) top
P1—O11.483 (2)C21—C221.571 (12)
P1—O21.484 (2)C21—H21A0.9900
P1—O2'1.623 (2)C21—H21B0.9900
P1—O3'1.612 (2)C22—H22A0.9800
O1'—C1'1.433 (3)C22—H22B0.9800
O1'—C4'1.443 (3)C22—H22C0.9800
O2'—C2'1.443 (3)C23—C241.515 (6)
O3'—C3'1.431 (3)C23—H23A0.9900
O5'—C5'1.420 (4)C23—H23B0.9900
C1'—N91.450 (4)C24—H24A0.9800
O5'—H5'1.05 (5)C24—H24B0.9800
C1'—C2'1.538 (4)C24—H24C0.9800
C1'—H1'0.99 (4)C25—C261.503 (7)
C2'—C3'1.522 (4)C25—H25A0.9900
C2'—H2'1.02 (4)C25—H25B0.9900
C3'—C4'1.525 (4)C26—H26A0.9800
C3'—H3'0.96 (4)C26—H26B0.9800
C4'—C5'1.498 (4)C26—H26C0.9800
C4'—H4'1.03 (4)N30—C351.477 (18)
C5'—H51'1.01 (4)N30—C331.507 (17)
C5'—H52'1.07 (4)N30—C311.517 (16)
N1—C21.345 (4)N30—H300.9300
N1—C61.352 (4)C31—C321.54 (2)
C2—N31.338 (4)C31—H31A0.9900
C2—H20.94 (4)C31—H31B0.9900
N3—C41.346 (4)C32—H32A0.9800
C4—N91.370 (3)C32—H32B0.9800
C4—C51.383 (4)C32—H32C0.9800
C5—N71.392 (4)C33—C341.517 (18)
C5—C61.408 (4)C33—H33A0.9900
C6—N61.341 (4)C33—H33B0.9900
N6—H610.86 (4)C34—H34A0.9800
N6—H621.04 (5)C34—H34B0.9800
N7—C81.312 (4)C34—H34C0.9800
C8—N91.391 (4)C35—C361.51 (2)
C8—H81.03 (3)C35—H35A0.9900
N20—C251.488 (5)C35—H35B0.9900
N20—C231.505 (5)C36—H36A0.9800
N20—C211.5057C36—H36B0.9800
N20—H200.9300C36—H36C0.9800
O1—P1—O2118.2 (2)C25—N20—C21109.6 (2)
O1—P1—O2'110.0 (2)C23—N20—C21113.2 (2)
O1—P1—O3'109.7 (2)C25—N20—H20106.5
O2—P1—O2'109.5 (2)C23—N20—H20106.5
O2—P1—O3'111.0 (2)C21—N20—H20106.5
O2'—P1—O3'96.3 (1)N20—C21—C22110.6 (4)
C1'—O1'—C4'108.7 (2)N20—C21—H21A109.5
C2'—O2'—P1111.7 (2)C22—C21—H21A109.5
C3'—O3'—P1112.0 (2)N20—C21—H21B109.5
O1'—C1'—N9107.5 (2)C22—C21—H21B109.5
O1'—C1'—C2'106.6 (2)H21A—C21—H21B108.1
C5'—O5'—H5'98 (3)N20—C23—C24113.8 (4)
N9—C1'—C2'113.5 (2)N20—C23—H23A108.8
O1'—C1'—H1'112 (2)C24—C23—H23A108.8
N9—C1'—H1'105 (2)N20—C23—H23B108.8
C2'—C1'—H1'112 (2)C24—C23—H23B108.8
O2'—C2'—C3'104.6 (2)H23A—C23—H23B107.7
O2'—C2'—C1'109.3 (2)N20—C25—C26112.8 (4)
C3'—C2'—C1'104.2 (2)N20—C25—H25A109.0
O2'—C2'—H2'107 (2)C26—C25—H25A109.0
C3'—C2'—H2'118 (2)N20—C25—H25B109.0
C1'—C2'—H2'113 (2)C26—C25—H25B109.0
O3'—C3'—C2'107.4 (2)H25A—C25—H25B107.8
O3'—C3'—C4'113.2 (2)C35—N30—C33114.1 (17)
C2'—C3'—C4'103.7 (2)C35—N30—C31113.9 (17)
O3'—C3'—H3'106 (3)C33—N30—C31115.1 (16)
C2'—C3'—H3'111 (3)C35—N30—H30104.0
C4'—C3'—H3'116 (3)C33—N30—H30104.0
O1'—C4'—C5'109.6 (2)C31—N30—H30104.0
O1'—C4'—C3'103.0 (2)N30—C31—C32110.1 (17)
C5'—C4'—C3'114.0 (2)N30—C31—H31A109.6
O1'—C4'—H4'108 (2)C32—C31—H31A109.6
C5'—C4'—H4'110 (2)N30—C31—H31B109.6
C3'—C4'—H4'112 (2)C32—C31—H31B109.6
O5'—C5'—C4'110.5 (3)H31A—C31—H31B108.1
O5'—C5'—H51'109 (2)C31—C32—H32A109.5
C4'—C5'—H51'109 (2)C31—C32—H32B109.5
O5'—C5'—H52'112 (2)H32A—C32—H32B109.5
C4'—C5'—H52'106 (2)C31—C32—H32C109.5
H51'—C5'—H52'111 (3)H32A—C32—H32C109.5
C2—N1—C6118.4 (3)H32B—C32—H32C109.5
N3—C2—N1128.7 (3)N30—C33—C34113.4 (17)
N3—C2—H2115 (2)N30—C33—H33A108.9
N1—C2—H2116 (2)C34—C33—H33A108.9
C2—N3—C4111.2 (2)N30—C33—H33B108.9
N3—C4—N9127.7 (3)C34—C33—H33B108.9
N3—C4—C5126.6 (2)H33A—C33—H33B107.7
N9—C4—C5105.7 (2)C33—C34—H34A109.5
C4—C5—N7111.3 (2)C33—C34—H34B109.5
C4—C5—C6116.9 (3)H34A—C34—H34B109.5
N7—C5—C6131.8 (3)C33—C34—H34C109.5
N6—C6—N1118.9 (3)H34A—C34—H34C109.5
N6—C6—C5122.9 (3)H34B—C34—H34C109.5
N1—C6—C5118.2 (3)N30—C35—C36111 (2)
C6—N6—H61119 (3)N30—C35—H35A109.3
C6—N6—H62116 (3)C36—C35—H35A109.3
H61—N6—H62121 (4)N30—C35—H35B109.3
C8—N7—C5103.6 (2)C36—C35—H35B109.3
N7—C8—N9113.5 (2)H35A—C35—H35B108.0
N7—C8—H8124 (2)C35—C36—H36A109.5
N9—C8—H8122 (2)C35—C36—H36B109.5
C4—N9—C8105.9 (2)H36A—C36—H36B109.5
C4—N9—C1'126.8 (2)C35—C36—H36C109.5
C8—N9—C1'127.2 (2)H36A—C36—H36C109.5
C25—N20—C23114.0 (3)H36B—C36—H36C109.5
O1—P1—O2'—C2'98.9 (2)C2—N3—C4—N9177.6 (3)
O2—P1—O2'—C2'129.7 (2)C2—N3—C4—C50.3 (4)
O3'—P1—O2'—C2'14.7 (2)N3—C4—C5—N7178.6 (3)
O1—P1—O3'—C3'117.7 (2)N9—C4—C5—N70.3 (3)
O2—P1—O3'—C3'109.9 (2)N3—C4—C5—C61.1 (5)
O2'—P1—O3'—C3'3.8 (2)N9—C4—C5—C6179.4 (3)
P1—O2'—C2'—C1'138.0 (2)C2—N1—C6—N6178.7 (3)
P1—O2'—C2'—C3'26.9 (3)C2—N1—C6—C51.5 (5)
P1—O3'—C3'—C2'19.8 (3)C4—C5—C6—N6178.2 (3)
P1—O3'—C3'—C4'94.0 (2)N7—C5—C6—N62.2 (5)
C4'—O1'—C1'—N9143.4 (2)C4—C5—C6—N12.0 (4)
C4'—O1'—C1'—C2'21.5 (3)N7—C5—C6—N1177.6 (3)
C1'—O1'—C4'—C3'36.2 (3)C4—C5—N7—C80.3 (3)
C1'—O1'—C4'—C5'157.8 (2)C6—C5—N7—C8179.3 (3)
O1'—C1'—C2'—O2'109.2 (2)C5—N7—C8—N90.2 (3)
N9—C1'—C2'—O2'132.7 (2)N3—C4—N9—C8178.4 (3)
O1'—C1'—C2'—C3'2.2 (3)C5—C4—N9—C80.1 (3)
N9—C1'—C2'—C3'115.9 (3)N3—C4—N9—C1'3.0 (5)
O2'—C2'—C3'—O3'28.5 (3)C5—C4—N9—C1'175.2 (3)
C1'—C2'—C3'—O3'143.2 (2)N7—C8—N9—C40.1 (3)
O2'—C2'—C3'—C4'91.6 (2)N7—C8—N9—C1'175.4 (3)
C1'—C2'—C3'—C4'23.2 (3)C25—N20—C21—C22179.4 (6)
O3'—C3'—C4'—O1'152.0 (2)C23—N20—C21—C2252.1 (5)
C2'—C3'—C4'—O1'36.0 (3)C25—N20—C23—C2462.7 (6)
O3'—C3'—C4'—C5'89.3 (3)C21—N20—C23—C2463.5 (5)
C2'—C3'—C4'—C5'154.7 (2)C23—N20—C25—C2651.0 (6)
O1'—C4'—C5'—O5'74.2 (3)C21—N20—C25—C26179.1 (4)
C3'—C4'—C5'—O5'171.0 (2)C35—N30—C31—C3272 (3)
O1'—C1'—N9—C4100.3 (3)C33—N30—C31—C3263 (3)
C2'—C1'—N9—C4142.1 (3)C35—N30—C33—C34175 (3)
O1'—C1'—N9—C874.1 (3)C31—N30—C33—C3451 (3)
C2'—C1'—N9—C843.5 (4)C33—N30—C35—C36171 (3)
C6—N1—C2—N30.1 (5)C31—N30—C35—C3636 (4)
N1—C2—N3—C41.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i1.05 (5)1.72 (5)2.772 (3)174 (5)
N6—H61···N3ii0.86 (4)2.19 (4)2.957 (4)149 (4)
N6—H62···O2iii1.04 (5)2.09 (5)3.090 (3)160 (4)
N20—H20···O10.931.742.660 (4)168
C2—H2···N1iv1.02 (4)2.49 (4)3.341 (4)140 (3)
C8—H8···O2ii1.03 (3)2.25 (3)3.260 (4)168 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y, z; (iii) x+2, y1/2, z+3/2; (iv) x+2, y+1/2, z+3/2.
(II) triethylammonium 4-(6-oxo-1,6-dihydropurin-7-yl)-6-hydroxymethyl-2-oxido-2- oxoperhydrofurano[3,4-c][1,3,2]dioxaphosphole monohydrate top
Crystal data top
C6H16N+·C10H11N5O7P·H2OF(000) = 492
Mr = 464.42Dx = 1.467 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9219 reflections
a = 10.611 (3) Åθ = 3.0–36.6°
b = 7.931 (3) ŵ = 0.19 mm1
c = 12.585 (3) ÅT = 200 K
β = 96.89 (3)°Plate, colourless
V = 1051.5 (6) Å30.60 × 0.40 × 0.15 mm
Z = 2
Data collection top
KUMA KM4 κ-geometry
diffractometer with Saphire CCD camera
5239 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 35.0°, θmin = 3.0°
ω scansh = 1617
21121 measured reflectionsk = 1012
6943 independent reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.033P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6943 reflectionsΔρmax = 0.42 e Å3
369 parametersΔρmin = 0.29 e Å3
65 restraintsAbsolute structure: (Flack, 1983), 2054 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.08 (6)
Crystal data top
C6H16N+·C10H11N5O7P·H2OV = 1051.5 (6) Å3
Mr = 464.42Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.611 (3) ŵ = 0.19 mm1
b = 7.931 (3) ÅT = 200 K
c = 12.585 (3) Å0.60 × 0.40 × 0.15 mm
β = 96.89 (3)°
Data collection top
KUMA KM4 κ-geometry
diffractometer with Saphire CCD camera
5239 reflections with I > 2σ(I)
21121 measured reflectionsRint = 0.042
6943 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077Δρmax = 0.42 e Å3
S = 1.03Δρmin = 0.29 e Å3
6943 reflectionsAbsolute structure: (Flack, 1983), 2054 Friedel pairs
369 parametersAbsolute structure parameter: 0.08 (6)
65 restraints
Special details top

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*/UeqOcc. (<1)
P10.48060 (3)0.73953 (5)0.65759 (3)0.02015 (8)
O10.61892 (10)0.70706 (15)0.66807 (9)0.0281 (3)
O20.42019 (11)0.74566 (18)0.75822 (9)0.0328 (3)
N10.10953 (13)0.83062 (18)0.08786 (11)0.0238 (3)
H10.0897 (18)0.890 (3)0.0264 (16)0.033 (5)*
N20.25135 (16)1.0403 (2)0.14829 (14)0.0383 (4)
H210.227 (2)1.088 (3)0.095 (2)0.053 (7)*
H220.298 (2)1.095 (3)0.2071 (17)0.041 (6)*
N30.21589 (12)0.82551 (17)0.26454 (10)0.0215 (3)
N70.00367 (13)0.47057 (17)0.23847 (10)0.0241 (3)
N90.14462 (12)0.59064 (15)0.36346 (10)0.0193 (3)
C20.19297 (14)0.8970 (2)0.16951 (12)0.0227 (3)
C40.14657 (14)0.68541 (19)0.27264 (11)0.0183 (3)
C50.06052 (15)0.60979 (19)0.19621 (12)0.0196 (3)
C60.03649 (14)0.6861 (2)0.09378 (12)0.0209 (3)
C80.05654 (15)0.4644 (2)0.33762 (13)0.0225 (3)
H80.0338 (17)0.382 (2)0.3881 (14)0.028 (5)*
C1'0.19991 (14)0.63613 (19)0.47166 (11)0.0176 (3)
H1'0.1867 (16)0.541 (2)0.5154 (13)0.018*
C2'0.34147 (14)0.67968 (19)0.48199 (12)0.0185 (3)
H2'0.3847 (16)0.644 (2)0.4198 (13)0.018*
C3'0.34801 (14)0.87225 (19)0.49963 (12)0.0188 (3)
H3'0.3666 (16)0.941 (3)0.4381 (14)0.023 (4)*
C4'0.21827 (13)0.92064 (19)0.53194 (12)0.0191 (3)
H4'0.2246 (15)0.937 (2)0.6087 (14)0.018 (4)*
C5'0.16112 (16)1.0754 (2)0.47422 (15)0.0257 (3)
H51'0.073 (2)1.102 (3)0.4927 (19)0.059 (7)*
H52'0.1536 (16)1.056 (2)0.3997 (15)0.023 (5)*
O1'0.13472 (10)0.77832 (13)0.50631 (9)0.0238 (2)
O2'0.40304 (11)0.60522 (13)0.57810 (9)0.0258 (3)
O3'0.44854 (10)0.90318 (14)0.58443 (9)0.0246 (2)
O5'0.23862 (12)1.21920 (15)0.50298 (11)0.0320 (3)
H5'0.284 (2)1.228 (4)0.453 (2)0.065 (8)*
O60.03906 (11)0.64293 (16)0.01639 (9)0.0307 (3)
OW0.25914 (17)0.9334 (2)0.87921 (12)0.0464 (4)
H1W0.300 (3)0.890 (3)0.836 (2)0.054 (8)*
H2W0.181 (3)0.944 (4)0.838 (2)0.065*
N200.3156 (3)0.4803 (5)0.8421 (2)0.0263 (6)0.698 (3)
H200.34300.56590.79990.032*0.698 (3)
C210.1797 (2)0.5209 (4)0.8561 (2)0.0312 (6)0.698 (3)
H21A0.14330.42500.89250.037*0.698 (3)
H21B0.17850.62070.90320.037*0.698 (3)
C220.0979 (4)0.5555 (5)0.7542 (3)0.0395 (8)0.698 (3)
H22A0.01130.57970.76930.047*0.698 (3)
H22B0.09710.45670.70740.047*0.698 (3)
H22C0.13130.65290.71870.047*0.698 (3)
C230.3234 (3)0.3194 (4)0.7796 (3)0.0416 (7)0.698 (3)
H23A0.28730.22640.81890.050*0.698 (3)
H23B0.27040.33150.70970.050*0.698 (3)
C240.4559 (6)0.2723 (9)0.7601 (5)0.0541 (16)0.698 (3)
H24A0.45280.17360.71300.065*0.698 (3)
H24B0.50640.24560.82840.065*0.698 (3)
H24C0.49500.36690.72610.065*0.698 (3)
C250.3963 (3)0.4920 (4)0.9480 (2)0.0428 (7)0.698 (3)
H25A0.38810.60670.97740.051*0.698 (3)
H25B0.48620.47550.93680.051*0.698 (3)
C260.3624 (4)0.3654 (6)1.0289 (3)0.0613 (11)0.698 (3)
H26A0.41170.38831.09830.074*0.698 (3)
H26B0.38170.25151.00520.074*0.698 (3)
H26C0.27160.37381.03590.074*0.698 (3)
N300.3233 (8)0.4357 (10)0.8466 (6)0.034 (3)*0.191 (5)
H300.35570.53530.82190.041*0.191 (5)
C310.2147 (8)0.3775 (12)0.7690 (7)0.064 (2)*0.191 (5)
H31A0.17600.27800.79990.077*0.191 (5)
H31B0.24840.34010.70290.077*0.191 (5)
C320.1108 (10)0.5075 (14)0.7388 (9)0.048 (3)*0.191 (5)
H32A0.04280.45630.68970.057*0.191 (5)
H32B0.14640.60380.70370.057*0.191 (5)
H32C0.07640.54600.80340.057*0.191 (5)
C330.4279 (6)0.3051 (9)0.8626 (5)0.0433 (17)*0.191 (5)
H33A0.49910.35200.91180.052*0.191 (5)
H33B0.39540.20520.89790.052*0.191 (5)
C340.4772 (16)0.250 (2)0.7638 (11)0.052 (4)*0.191 (5)
H34A0.53510.15430.77980.062*0.191 (5)
H34B0.52300.34290.73460.062*0.191 (5)
H34C0.40640.21490.71110.062*0.191 (5)
C350.2627 (10)0.4714 (16)0.9476 (7)0.046 (3)*0.191 (5)
H35A0.20030.56400.93440.055*0.191 (5)
H35B0.21770.36970.96880.055*0.191 (5)
C360.3654 (10)0.5204 (15)1.0358 (8)0.039 (3)*0.191 (5)
H36A0.32710.54471.10120.047*0.191 (5)
H36B0.40960.62101.01420.047*0.191 (5)
H36C0.42600.42751.04910.047*0.191 (5)
N400.3233 (8)0.4357 (10)0.8466 (6)0.034 (3)*0.111 (5)
H400.36020.51400.80480.041*0.111 (5)
C410.2147 (8)0.3775 (12)0.7690 (7)0.064 (2)*0.111 (5)
H41A0.17600.27800.79990.077*0.111 (5)
H41B0.24840.34010.70290.077*0.111 (5)
C420.1108 (10)0.5075 (14)0.7388 (9)0.048 (3)*0.111 (5)
H42A0.04270.45620.68980.057*0.111 (5)
H42B0.14640.60370.70360.057*0.111 (5)
H42C0.07650.54610.80350.057*0.111 (5)
C430.4279 (6)0.3051 (9)0.8626 (5)0.0433 (17)*0.111 (5)
H43A0.49910.35200.91180.052*0.111 (5)
H43B0.39540.20520.89790.052*0.111 (5)
C440.4772 (16)0.250 (2)0.7638 (11)0.052 (4)*0.111 (5)
H44A0.53480.15390.77980.062*0.111 (5)
H44B0.52340.34280.73480.062*0.111 (5)
H44C0.40640.21550.71100.062*0.111 (5)
C450.3260 (19)0.5355 (19)0.9529 (9)0.035 (5)*0.111 (5)
H45A0.40900.59350.96600.042*0.111 (5)
H45B0.26000.62420.94200.042*0.111 (5)
C460.3062 (18)0.441 (2)1.0531 (11)0.031 (4)*0.111 (5)
H46A0.35620.33641.05690.037*0.111 (5)
H46B0.21600.41291.05200.037*0.111 (5)
H46C0.33350.51071.11580.037*0.111 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01731 (18)0.02209 (18)0.01993 (17)0.00351 (16)0.00235 (12)0.00053 (16)
O10.0177 (5)0.0332 (7)0.0317 (6)0.0075 (4)0.0035 (4)0.0016 (5)
O20.0324 (6)0.0386 (7)0.0282 (6)0.0001 (6)0.0078 (4)0.0032 (6)
N10.0270 (7)0.0243 (6)0.0179 (6)0.0057 (5)0.0066 (5)0.0043 (5)
N20.0451 (9)0.0362 (9)0.0282 (8)0.0208 (7)0.0174 (7)0.0155 (7)
N30.0203 (6)0.0222 (6)0.0205 (6)0.0054 (5)0.0037 (5)0.0040 (5)
N70.0251 (7)0.0218 (6)0.0244 (7)0.0063 (5)0.0015 (5)0.0002 (5)
N90.0206 (6)0.0181 (6)0.0183 (6)0.0038 (5)0.0011 (4)0.0026 (5)
C20.0228 (8)0.0234 (8)0.0203 (7)0.0049 (6)0.0042 (5)0.0034 (6)
C40.0180 (7)0.0196 (7)0.0168 (7)0.0001 (5)0.0007 (5)0.0012 (5)
C50.0196 (7)0.0189 (7)0.0195 (7)0.0022 (5)0.0005 (5)0.0017 (5)
C60.0208 (7)0.0222 (7)0.0190 (7)0.0004 (6)0.0006 (5)0.0023 (5)
C80.0234 (8)0.0184 (7)0.0253 (8)0.0043 (6)0.0015 (6)0.0024 (6)
C1'0.0209 (7)0.0165 (7)0.0149 (7)0.0011 (5)0.0003 (5)0.0009 (5)
C2'0.0190 (7)0.0188 (7)0.0166 (7)0.0034 (5)0.0020 (5)0.0012 (5)
C3'0.0149 (7)0.0183 (7)0.0222 (7)0.0008 (5)0.0018 (5)0.0021 (6)
C4'0.0176 (7)0.0187 (7)0.0209 (7)0.0006 (5)0.0021 (5)0.0007 (6)
C5'0.0205 (8)0.0200 (8)0.0364 (10)0.0031 (6)0.0023 (6)0.0024 (7)
O1'0.0183 (5)0.0206 (6)0.0331 (6)0.0026 (4)0.0060 (4)0.0047 (4)
O2'0.0303 (6)0.0182 (5)0.0254 (6)0.0029 (4)0.0114 (4)0.0013 (4)
O3'0.0203 (6)0.0203 (5)0.0303 (6)0.0005 (4)0.0087 (4)0.0025 (5)
O5'0.0346 (7)0.0195 (6)0.0431 (7)0.0001 (5)0.0096 (5)0.0004 (5)
O60.0347 (7)0.0326 (6)0.0220 (6)0.0090 (5)0.0079 (5)0.0017 (5)
OW0.0481 (9)0.0525 (9)0.0391 (8)0.0120 (8)0.0075 (7)0.0057 (7)
N200.0314 (14)0.0248 (16)0.0240 (13)0.0035 (11)0.0082 (8)0.0029 (10)
C210.0245 (12)0.0383 (14)0.0309 (13)0.0030 (11)0.0041 (9)0.0066 (11)
C220.0402 (19)0.0311 (19)0.048 (2)0.0015 (15)0.0059 (14)0.0014 (16)
C230.0437 (17)0.0272 (13)0.0550 (18)0.0020 (12)0.0102 (13)0.0016 (13)
C240.051 (3)0.036 (2)0.080 (3)0.011 (2)0.023 (2)0.0026 (18)
C250.0354 (17)0.0541 (19)0.0370 (16)0.0089 (14)0.0027 (11)0.0086 (13)
C260.056 (2)0.081 (3)0.0448 (19)0.001 (2)0.0013 (16)0.0310 (19)
Geometric parameters (Å, º) top
P1—O11.4803 (12)C21—H21B0.9900
P1—O21.4872 (12)C22—H22A0.9800
P1—O2'1.6172 (12)C22—H22B0.9800
P1—O3'1.6040 (12)C22—H22C0.9800
O1'—C1'1.419 (2)C23—C241.504 (6)
O1'—C4'1.448 (2)C23—H23A0.9900
O2'—C2'1.432 (2)C23—H23B0.9900
O3'—C3'1.437 (2)C24—H24A0.9800
O5'—C5'1.427 (2)C24—H24B0.9800
C1'—N91.462 (2)C24—H24C0.9800
N1—C21.378 (2)C25—C261.504 (4)
N1—C61.391 (2)C25—H25A0.9900
N1—H10.91 (2)C25—H25B0.9900
N2—C21.337 (2)C26—H26A0.9800
N2—H210.79 (3)C26—H26B0.9800
N2—H220.94 (2)C26—H26C0.9800
N3—C21.320 (2)N30—C311.491 (8)
N3—C41.343 (2)N30—C331.514 (8)
N7—C81.306 (2)N30—C351.518 (10)
N7—C51.394 (2)N30—H300.9300
N9—C41.370 (2)C31—C321.524 (11)
N9—C81.381 (2)C31—H31A0.9900
C4—C51.381 (2)C31—H31B0.9900
C5—C61.419 (2)C32—H32A0.9800
C6—O61.233 (2)C32—H32B0.9800
C8—H80.96 (2)C32—H32C0.9800
C1'—C2'1.531 (2)C33—C341.473 (12)
C1'—H1'0.95 (2)C33—H33A0.9900
C2'—C3'1.544 (2)C33—H33B0.9900
C2'—H2'0.99 (2)C34—H34A0.9800
C3'—C4'1.530 (2)C34—H34B0.9800
C3'—H3'0.99 (2)C34—H34C0.9800
C4'—C5'1.516 (2)C35—C361.510 (12)
C4'—H4'0.97 (2)C35—H35A0.9900
C5'—H51'1.02 (3)C35—H35B0.9900
C5'—H52'0.94 (2)C36—H36A0.9800
O5'—H5'0.84 (3)C36—H36B0.9800
OW—H1W0.81 (3)C36—H36C0.9800
OW—H2W0.93 (3)C45—C461.506 (14)
N20—C251.498 (4)C45—H45A0.9900
N20—C231.507 (5)C45—H45B0.9900
N20—C211.508 (4)C46—H46A0.9800
N20—H200.9300C46—H46B0.9800
C21—C221.485 (4)C46—H46C0.9800
C21—H21A0.9900
O1—P1—O2116.99 (7)N20—C21—H21B108.7
O1—P1—O3'109.37 (7)H21A—C21—H21B107.6
O1—P1—O2'111.47 (7)C21—C22—H22A109.5
O2—P1—O2'107.99 (7)C21—C22—H22B109.5
O2—P1—O3'112.27 (7)H22A—C22—H22B109.5
O2'—P1—O3'96.94 (6)C21—C22—H22C109.5
C1'—O1'—C4'112.34 (11)H22A—C22—H22C109.5
C2'—O2'—P1113.44 (10)H22B—C22—H22C109.5
C3'—O3'—P1112.07 (10)C24—C23—N20114.0 (3)
O1'—C1'—N9109.06 (12)C24—C23—H23A108.7
O1'—C1'—C2'107.70 (12)N20—C23—H23A108.7
C2—N1—C6125.96 (13)C24—C23—H23B108.7
C2—N1—H1120.1 (13)N20—C23—H23B108.7
C6—N1—H1113.4 (12)H23A—C23—H23B107.6
C2—N2—H21117.9 (18)C23—C24—H24A109.5
C2—N2—H22116.5 (13)C23—C24—H24B109.5
H21—N2—H22122 (2)H24A—C24—H24B109.5
C2—N3—C4112.40 (12)C23—C24—H24C109.5
C8—N7—C5103.77 (13)H24A—C24—H24C109.5
C4—N9—C8106.17 (12)H24B—C24—H24C109.5
C4—N9—C1'126.66 (12)N20—C25—C26113.8 (3)
C8—N9—C1'125.64 (13)N20—C25—H25A108.8
N3—C2—N2120.46 (14)C26—C25—H25A108.8
N3—C2—N1122.96 (14)N20—C25—H25B108.8
N2—C2—N1116.59 (14)C26—C25—H25B108.8
N3—C4—N9125.47 (12)H25A—C25—H25B107.7
N3—C4—C5128.95 (13)C25—C26—H26A109.5
N9—C4—C5105.54 (13)C25—C26—H26B109.5
C4—C5—N7111.00 (13)H26A—C26—H26B109.5
C4—C5—C6118.63 (14)C25—C26—H26C109.5
N7—C5—C6130.21 (13)H26A—C26—H26C109.5
O6—C6—N1120.01 (14)H26B—C26—H26C109.5
O6—C6—C5128.89 (15)C31—N30—C33111.8 (6)
N1—C6—C5111.08 (13)C31—N30—C35103.5 (7)
N7—C8—N9113.51 (14)C33—N30—C35113.2 (7)
N7—C8—H8122.8 (11)C31—N30—H30109.4
N9—C8—H8123.6 (11)C33—N30—H30109.4
N9—C1'—C2'114.49 (12)C35—N30—H30109.4
O1'—C1'—H1'109.9 (10)N30—C31—C32115.7 (8)
N9—C1'—H1'105.8 (10)N30—C31—H31A108.4
C2'—C1'—H1'109.9 (10)C32—C31—H31A108.4
O2'—C2'—C1'108.80 (12)N30—C31—H31B108.4
O2'—C2'—C3'106.17 (12)C32—C31—H31B108.4
C1'—C2'—C3'105.19 (12)H31A—C31—H31B107.4
O2'—C2'—H2'110.0 (10)C31—C32—H32A109.5
C1'—C2'—H2'114.2 (10)C31—C32—H32B109.5
C3'—C2'—H2'112.1 (11)H32A—C32—H32B109.5
O3'—C3'—C4'111.79 (13)C31—C32—H32C109.5
O3'—C3'—C2'107.00 (12)H32A—C32—H32C109.5
C4'—C3'—C2'105.07 (13)H32B—C32—H32C109.5
O3'—C3'—H3'106.8 (10)C34—C33—N30114.9 (8)
C4'—C3'—H3'109.9 (10)C34—C33—H33A108.5
C2'—C3'—H3'116.4 (11)N30—C33—H33A108.5
O1'—C4'—C5'109.01 (12)C34—C33—H33B108.5
O1'—C4'—C3'106.96 (12)N30—C33—H33B108.5
C5'—C4'—C3'113.38 (13)H33A—C33—H33B107.5
O1'—C4'—H4'107.2 (11)C33—C34—H34A109.5
C5'—C4'—H4'110.0 (11)C33—C34—H34B109.5
C3'—C4'—H4'110.0 (10)H34A—C34—H34B109.5
O5'—C5'—C4'109.90 (13)C33—C34—H34C109.5
O5'—C5'—H51'107.3 (15)H34A—C34—H34C109.5
C4'—C5'—H51'112.7 (15)H34B—C34—H34C109.5
O5'—C5'—H52'111.2 (11)C36—C35—N30108.8 (8)
C4'—C5'—H52'108.9 (12)C36—C35—H35A109.9
H51'—C5'—H52'106.9 (17)N30—C35—H35A109.9
C5'—O5'—H5'104 (2)C36—C35—H35B109.9
H1W—OW—H2W100 (2)N30—C35—H35B109.9
C25—N20—C23117.1 (3)H35A—C35—H35B108.3
C25—N20—C21109.6 (3)C35—C36—H36A109.5
C23—N20—C21110.8 (2)C35—C36—H36B109.5
C25—N20—H20106.2H36A—C36—H36B109.5
C23—N20—H20106.2C35—C36—H36C109.5
C21—N20—H20106.2H36A—C36—H36C109.5
C22—C21—N20114.0 (3)H36B—C36—H36C109.5
C22—C21—H21A108.7C46—C45—H45A107.7
N20—C21—H21A108.7C46—C45—H45B107.7
C22—C21—H21B108.7H45A—C45—H45B107.1
O1—P1—O2'—C2'114.1 (1)C6—N1—C2—N2178.03 (16)
O2—P1—O2'—C2'116.1 (1)C2—N3—C4—N9175.90 (15)
O3'—P1—O2'—C2'0.1 (1)C2—N3—C4—C51.4 (2)
O1—P1—O3'—C3'129.1 (1)C8—N9—C4—N3177.04 (15)
O2—P1—O3'—C3'99.3 (1)C1'—N9—C4—N310.6 (2)
O2'—P1—O3'—C3'13.4 (1)C8—N9—C4—C50.77 (16)
P1—O2'—C2'—C1'124.7 (1)C1'—N9—C4—C5167.26 (14)
P1—O2'—C2'—C3'11.9 (2)N3—C4—C5—N7176.89 (15)
P1—O3'—C3'—C2'21.4 (2)N9—C4—C5—N70.81 (18)
P1—O3'—C3'—C4'93.1 (2)N3—C4—C5—C61.1 (2)
C4'—O1'—C1'—N9120.4 (2)N9—C4—C5—C6176.64 (13)
C4'—O1'—C1'—C2'4.4 (2)C8—N7—C5—C40.50 (18)
C1'—O1'—C4'—C3'6.4 (2)C8—N7—C5—C6175.71 (16)
C1'—O1'—C4'—C5'129.4 (2)C2—N1—C6—O6176.93 (16)
O1'—C1'—C2'—O2'100.2 (2)C2—N1—C6—C51.4 (2)
N9—C1'—C2'—O2'138.3 (2)C4—C5—C6—O6177.23 (17)
O1'—C1'—C2'—C3'13.2 (2)N7—C5—C6—O62.3 (3)
N9—C1'—C2'—C3'108.3 (2)C4—C5—C6—N10.9 (2)
O2'—C2'—C3'—O3'20.3 (2)N7—C5—C6—N1175.79 (16)
C1'—C2'—C3'—O3'135.5 (2)C5—N7—C8—N90.01 (18)
O2'—C2'—C3'—C4'98.7 (2)C4—N9—C8—N70.51 (18)
C1'—C2'—C3'—C4'16.5 (2)C1'—N9—C8—N7167.18 (14)
O3'—C3'—C4'—O1'130.0 (2)C25—N20—C21—C22165.4 (3)
C2'—C3'—C4'—O1'14.3 (2)C23—N20—C21—C2263.9 (4)
O3'—C3'—C4'—C5'109.8 (2)C25—N20—C23—C2454.6 (5)
C2'—C3'—C4'—C5'134.5 (2)C21—N20—C23—C24178.7 (4)
O1'—C4'—C5'—O5'176.9 (2)C23—N20—C25—C2663.6 (4)
C3'—C4'—C5'—O5'64.1 (2)C21—N20—C25—C2663.7 (4)
O1'—C1'—N9—C465.2 (2)C33—N30—C31—C32173.9 (8)
C2'—C1'—N9—C455.5 (2)C35—N30—C31—C3264.0 (11)
O1'—C1'—N9—C898.8 (2)C31—N30—C33—C3455.5 (12)
C2'—C1'—N9—C8140.5 (2)C35—N30—C33—C34172.0 (11)
C4—N3—C2—N2178.27 (16)C31—N30—C35—C36176.1 (9)
C4—N3—C2—N11.7 (2)C33—N30—C35—C3654.8 (11)
C6—N1—C2—N32.0 (3)

Experimental details

(I)(II)
Crystal data
Chemical formulaC6H16N+·C10H11N5O6PC6H16N+·C10H11N5O7P·H2O
Mr430.41464.42
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)100200
a, b, c (Å)6.704 (2), 10.493 (3), 28.536 (7)10.611 (3), 7.931 (3), 12.585 (3)
α, β, γ (°)90, 90, 9090, 96.89 (3), 90
V3)2007.4 (10)1051.5 (6)
Z42
Radiation typeCu KαMo Kα
µ (mm1)1.630.19
Crystal size (mm)0.29 × 0.09 × 0.030.60 × 0.40 × 0.15
Data collection
DiffractometerXcalibur PX κ-geometry
diffractometer with Onyx CCD camera
KUMA KM4 κ-geometry
diffractometer with Saphire CCD camera
Absorption correctionAnalytical
CrysAlis RED (Oxford Diffraction, 2003)
Tmin, Tmax0.742, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
14174, 3911, 3559 21121, 6943, 5239
Rint0.0630.042
(sin θ/λ)max1)0.6290.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.126, 1.09 0.042, 0.077, 1.03
No. of reflections39116943
No. of parameters336369
No. of restraints1265
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.430.42, 0.29
Absolute structure(Flack, 1983), 1481 Friedel pairs(Flack, 1983), 2054 Friedel pairs
Absolute structure parameter0.02 (3)0.08 (6)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
P1—O11.483 (2)P1—O2'1.623 (2)
P1—O21.484 (2)P1—O3'1.612 (2)
O1—P1—O2118.2 (2)O2—P1—O3'111.0 (2)
O1—P1—O2'110.0 (2)O2'—P1—O3'96.3 (1)
O1—P1—O3'109.7 (2)C2'—O2'—P1111.7 (2)
O2—P1—O2'109.5 (2)C3'—O3'—P1112.0 (2)
O1—P1—O2'—C2'98.9 (2)O1'—C1'—C2'—O2'109.2 (2)
O2—P1—O2'—C2'129.7 (2)O1'—C1'—C2'—C3'2.2 (3)
O3'—P1—O2'—C2'14.7 (2)O2'—C2'—C3'—O3'28.5 (3)
O1—P1—O3'—C3'117.7 (2)C1'—C2'—C3'—O3'143.2 (2)
O2—P1—O3'—C3'109.9 (2)O2'—C2'—C3'—C4'91.6 (2)
O2'—P1—O3'—C3'3.8 (2)C1'—C2'—C3'—C4'23.2 (3)
P1—O2'—C2'—C1'138.0 (2)O3'—C3'—C4'—O1'152.0 (2)
P1—O2'—C2'—C3'26.9 (3)C2'—C3'—C4'—O1'36.0 (3)
P1—O3'—C3'—C2'19.8 (3)O1'—C4'—C5'—O5'74.2 (3)
P1—O3'—C3'—C4'94.0 (2)C3'—C4'—C5'—O5'171.0 (2)
C4'—O1'—C1'—C2'21.5 (3)O1'—C1'—N9—C874.1 (3)
C1'—O1'—C4'—C3'36.2 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O5'—H5'···O2i1.05 (5)1.72 (5)2.772 (3)174 (5)
N6—H61···N3ii0.86 (4)2.19 (4)2.957 (4)149 (4)
N6—H62···O2'iii1.04 (5)2.09 (5)3.090 (3)160 (4)
N20—H20···O10.931.742.660 (4)168
C2'—H2'···N1iv1.02 (4)2.49 (4)3.341 (4)140 (3)
C8—H8···O2ii1.03 (3)2.25 (3)3.260 (4)168 (3)
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x+1, y, z; (iii) x+2, y1/2, z+3/2; (iv) x+2, y+1/2, z+3/2.
Selected geometric parameters (Å, º) for (II) top
P1—O11.4803 (12)P1—O2'1.6172 (12)
P1—O21.4872 (12)P1—O3'1.6040 (12)
O1—P1—O2116.99 (7)O2—P1—O3'112.27 (7)
O1—P1—O3'109.37 (7)O2'—P1—O3'96.94 (6)
O1—P1—O2'111.47 (7)C2'—O2'—P1113.44 (10)
O2—P1—O2'107.99 (7)C3'—O3'—P1112.07 (10)
O1—P1—O2'—C2'114.1 (1)O1'—C1'—C2'—O2'100.2 (2)
O2—P1—O2'—C2'116.1 (1)O1'—C1'—C2'—C3'13.2 (2)
O3'—P1—O2'—C2'0.1 (1)O2'—C2'—C3'—O3'20.3 (2)
O1—P1—O3'—C3'129.1 (1)C1'—C2'—C3'—O3'135.5 (2)
O2—P1—O3'—C3'99.3 (1)O2'—C2'—C3'—C4'98.7 (2)
O2'—P1—O3'—C3'13.4 (1)C1'—C2'—C3'—C4'16.5 (2)
P1—O2'—C2'—C1'124.7 (1)O3'—C3'—C4'—O1'130.0 (2)
P1—O2'—C2'—C3'11.9 (2)C2'—C3'—C4'—O1'14.3 (2)
P1—O3'—C3'—C2'21.4 (2)O1'—C4'—C5'—O5'176.9 (2)
P1—O3'—C3'—C4'93.1 (2)C3'—C4'—C5'—O5'64.1 (2)
C4'—O1'—C1'—C2'4.4 (2)O1'—C1'—N9—C898.8 (2)
C1'—O1'—C4'—C3'6.4 (2)
Hydrogen-bonding geometry (Å, °) for 2 top
D—H···AD—HH···AD···AD—H···A
O5'—H5'···O1v0.84 (3)1.95 (3)2.777 (2)170 (3)
OW—H1W···O20.81 (3)2.05 (3)2.843 (2)166 (3)
OW—H2W···N7vi0.93 (3)2.09 (3)3.011 (2)174 (2)
N1—H1···O6vii0.91 (2)2.13 (2)2.860 (2)137 (2)
N2—H21···O6vii0.79 (3)2.33 (3)2.985 (2)141 (2)
N2—H22···O1v0.94 (2)1.93 (2)2.867 (2)176 (2)
N20—H20···O20.931.762.656 (4)162
C3'—H3'···O1v0.99 (2)2.51 (2)3.436 (2)156 (2)
C5'—H52'···N30.94 (2)2.63 (2)3.406 (2)139 (2)
C8—H8···O1'viii0.96 (2)2.49 (2)3.333 (2)146 (2)
Symmetry codes: (v) 1 − x, 1/2 + y, 1 − z; (vi) −x, 1/2 + y, 1 − z; (vii) −x, 1/2 + y, −z; (viii) −x, y − 1/2, 1 − z.
 

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