Download citation
Download citation
link to html
Two structures presenting an uncomplexed 2,6-diamino­purine (dap) group are reported, namely 2,6-diamino-9H-purine monohydrate, C5H6N6·H2O, (I), and bis­(2,6-diamino-9H-purin-1-ium) 2-(2-carboxyl­atophenyl)acetate hepta­hydrate, 2C5H7N6+·C9H6O42−·7H2O, (II). Both structures are rather featureless from a mol­ecular point of view, but present instead an outstanding hydrogen-bonding scheme. In compound (I), this is achieved through a rather simple independent unit content (one neutral dap and one water mol­ecule) and takes the form of two-dimensional layers tightly connected by strong hydrogen bonds, and inter­linked by much weaker hydrogen bonds and π–π inter­actions. In compound (II), the fundamental building blocks are more complex, consisting of two independent 2,6-diamino-9H-purin-1-ium (Hdap+) cat­ions, one homophthalate [2-(2-carboxyl­atophenyl)acetate] dianion and seven solvent water mol­ecules. The large number of hydrogen-bond donors and acceptors produces 26 independent inter­actions, leading to an extended and complicated network of hydrogen bonds in a packing organization characterized by the stacking of inter­leaved anionic and cationic planar arrays. These structural characteristics are compared with those of similar compounds in the literature.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110035985/dn3149sup1.cif
Contains datablocks I, II, gobal

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110035985/dn3149Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110035985/dn3149IIsup3.hkl
Contains datablock II

CCDC references: 804129; 804130

Comment top

Purines constitute a family of heterocyclic compounds characterized by a fused pair of pyrimidine and imidazole rings. The simplest representative is purine itself, mostly found in nature as methyl-, hydroxyl- and amino-substituted derivatives. These are esential compounds for biological systems, to the extent that many of the building blocks of DNA and RNA are purines of this kind. The relevance of these small molecules resides mainly in their highly interactive hydrogen-bonding capabilities resulting from the many active sites (both donors and acceptors) available in their structures. This conditon is, of course, not restricted to life processes, and renders these compounds extremely appealing from a synthetic point of view when searching for suitable building blocks for complicated supramolecular structures. Accordingly, much structural work has been devoted to some of these purines (adenine and guanine, among others) but many have not been adequately surveyed from a structural point of view. In this latter category, 2,6-diaminopurine (C5H6N6, hereinafter dap) occupies a noted position: only two appearances of compounds containing the molecule could be found in the Cambridge Structural Database (CSD, Version?; Allen, 2002). We shall return to this point in the discussion below.

Since it seemed this was a gap worth filling, we decided to explore the synthesis and crystallographic study of transition metal complexes, surveying dap as the main ligand, through a project which is beginning to provide interesting results (in preparation). As an introductory paper to this intended series of structural reports, we report here two different structures which feature the dap molecule as an uncomplexed group. One of them, dap monohydrate, (I), presents the molecule as a neutral free base, while in the other, bis(2,6-diamino-9H-purin-1-ium) homophthalate heptahydrate or 2Hdap+.hpt2-.7H2O, (II) [where H2hpt is homophthalic acid, 2-(2-carboxylatophenyl)acetic acid], it fulfils the role of a cation. In spite of the obvious differences displayed by these two structures, viz. the protonation state of the dap group, the number of solvent water molecules etc., the molecule provides a similarly complex hydrogen-bonding network, which will be discussed below.

From the molecular point of view both structures are quite simple, since the individual components do not deviate from the expected geometries, with bond distances and angles lying within reported values for these species (CSD; Allen 2002).

Fig. 1 presents an ellipsoid plot of the asymmetric unit contents in structure (I), consisting of a neutral dap molecule and one solvent water molecule. As expected, the dap unit is planar [maximum deviation from the mean plane is 0.015 (1) Å for atom C1], and the mean plane defined by the molecule deviates by just 0.15 Å from the crystallographic centre of symmetry at (0, 0, 1/2), so that a `thin' planar arrangement builds up via this 1 symmetry operation, with an overall deviation from the mean plane of 0.15 (1) Å and a maximum deviation of 0.42 (1) Å for atom N6. In the resulting two-dimensional structure parallel to (121), molecules of dap are interlinked by most of the existing hydrogen-bonding interactions (six out of a total of seven; Fig. 2 and Table 1) which define a number of closed structures, in particular a couple of centrosymmetric loops with graph-set descriptors R22(8) [The general form of a graph-set descriptor is Gda(n), with possible codings for G being S (intramolecular, or self, hydrogen bonds), D (dimeric system), R (cyclic system) or C (chain). The sub- and superscripts d and a define the number of donors and acceptors in the motif, while n stands for number of atoms involved. For more details on graph-set notation as applied to hydrogen-bonding, see Bernstein et al. (1995).] (labelled A1 and A2 in Fig. 2) involving only dap molecules with no intervention of the solvent water molecule (first two entries in Table 1), and which define a zigzag chain along [101]. These parallel chains are in turn connected along [111] by a number of loops where the water molecule plays an active role, being involved in four different hydrogen bonds in the plane, three of them as an acceptor (entries 3–5 in Table 1) and one as a donor (entry 6). The result is the formation of a centrosymmetric R42(8) ring (B1 in Fig. 2), around which another three different loops build up in pairs, with graph-set descriptors R32(8) (B2), R22(7) (B3) and a rather large R66(20) (B4). The planar structures stack parallel to each other at a distance of ca 3.5 Å (Fig. 3), and are weakly linked by a mixture of hydrogen bonds [through an N···H—O—H···N chain involving both water H atoms (entries 6 and 7 in Table 1), which define a centrosymmetric R44(14) loop around the inversion centre at (1/2, 1/2, 1/2)] (labelled C in Fig. 3) and some ππ interactions, presumably involving the whole two-dimensional structure in a generalized fashion. Individual short contacts between parallel rings fulfilling the ππ bonding criteria are presented in Table 2.

Fig. 4 shows a molecular view of (II). The asymmetric unit, noticeably more complex than that in structure (I), consists of two Hdap+ cations (atoms identified by trailing labels 1 and 2, respectively) counterbalanced by one homophthalate hpt2- anion (trailing label 3) and completed by seven solvent water molecules. It is worth mentioning, for future reference, that both independent Hdap+ cations of (II) are identical, with protonation at N taking place at the same sites, viz. N11 and N31, and N12 and N32.

The two independent Hdap+ cations also show very small individual deviations from planarity: 0.029 (1) Å for atom N51 and 0.033 (1) Å for atom C22, respectively. In addition, they lie almost on the same plane, parallel to (101), with a slightly larger deviation from the mean plane (0.069 Å for atom N51) when both cations are considered in bulk. A peculiar result of this disposition is that these molecules and their (x + 1, y, z - 1) and (x - 1, y, z + 1) translation images determine almost perfect and extremely `thin' infinite `strips' running along [101] [overall deviation from the mean plane for the whole assembly 0.02 (1) Å, with a maximum of 0.09 (1) Å for atom N51]. This structure (to be discussed below) somehow resembles the planar disposition of the dap molecules in (I).

The hpt2- anion of (II), in turn, presents a planar inner phenyl core [maximum deviation from the least-squares plane 0.017 (1) Å for atom C63], the deviations from planarity residing instead in the lateral arms due to rotations in both the carboxylate and the ethyl groups. Fig. 4 gives a qualitative view of this out-of-plane geometry, while Table 3 presents a few torsion angles, quantitatively describing the situation.

In contrast with the deceptive simplicity of the structure when only the molecular aspects are considered, the assembly of the elemental units into a three-dimensional supramolecular organization proves to be extremely complex and possesses a great richness of detail, mainly due to the very large number of hydrogen-bonding donors and acceptors present both in anions, cations and solvates.

A detailed analysis of the hydrogen-bonding scheme of (II) reveals that there are 26 potentially active H atoms (14 Hwater and 12 HHdap), all of which are involved, and 15 potential acceptors (seven Owater, four Ohpt and four NHdap), all of them active. This leads to a large ratio of 1.73 hydrogen bonds per acceptor.

As a result of the abundance of hydrogen-bonding interactions (Table 4) and ππ contacts (Table 5), the structure naturally segregates into two well differentiated substructures, one of them cationic, made up of Hdap+ cations only, and the remaining one anionic and composed of hpt2- anions and water molecules. Both substructures present neat well differentiated characteristics, which we shall describe below.

In the cationic substructure, the basic component is the pair of coplanar Hdap+ cations strongly interlinked into a dimeric hydrogen-bonded structure through head-to-tail interactions, forming R22(8) loops (A in Fig. 5) involving atoms H61A and H62A (Table 4, entries 1 and 2). These hydrogen-bonded dimers, in turn, link to their (x + 1, y, z - 1) and (x - 1, y, z + 1) translation images, forming R22(10) loops (B in Fig. 5) involving atoms H51B and H52B (entries 3 and 4 in Table 4), thus defining planar strips running along [101], as shown in Fig. 5. When the c-glide operates on these strips, it generates a parallel image separated from the former, original, ones by a distance of roughly one-quarter of a [101] translation (Fig. 6a), to build up broad two-dimensional structures parallel to (010) at y ~ 1/4, 3/4 (Figs. 6a and 6b). Even if there are in principle particular aromatic rings fulfilling the expected geometric conditions for ππ contacts (Table 5, first and second entries), the interaction between strips should probably be considered as a collective one, with an interplanar distance equal to d(202) = 3.358 (1) Å.

The anionic substructure is of a completely different nature. It is built up of hpt2- anions and water molecules, generating hollow structures parallel to [010] at y ~0, 1/2 and limited by two parallel `walls' completely made out of hydrophilic entities (water molecules and carboxylate groups), linked into a planar hydrogen-bonding network involving 13 out of the 14 available water H atoms (Table 4, entries 5 to 17, and Fig. 7a). These interactions give rise to a variety of ring motifs (Fig. 7a): R66(18) (C), R55(16) (D), R64(12) (E), R43(10) (F) and R54(10) (G). Adjacent walls join together along b through a centrosymmetric R44(8) loop (H in Fig. 7b) including the water H atom not involved in the planar structure described earlier (Table 4, entry 18). The hydrophilic [hydrophobic?] constituents, in turn, represented by the phenyl rings, lean inwards into the space defined by the limiting walls, and interact with one another in pairs via ππ interactions (Table 5, third entry).

Finally, these anionic and cationic substructures are interleaved, defining a compact three-dimensional structure. Fig. 8 shows the way in which this is achieved. Being ionic in nature, the alternating substructures are obviously held together by Coulombian forces, but in addition their interlinkage is reinforced by a number of hydrogen bonds having H atoms from the anionic side as donors and O atoms from the cationic side as acceptors (Table 4, entries 19 to 26, and Fig. 8)

The structures herein reported are singular in a number of aspects. In spite of pertaining to the most populated nitrogenated group in nature, the dap molecule, in either its neutral or any of its ionic forms, has rarely been reported in structural studies: compound (I) constitutes only the second reported case of an isolated neutral dap molecule, the first one being in the form of a cocrystal with a Ln(crotonate) complex (Atria et al., 2009). Similarly, structure (II) is only the second one to be reported with an ionic dap as a constituent, and the first one with an Hdap+ cationic group; there has been an anionic case already reported (Badura & Vahrenkamp, 2002), corresponding to a deprotonated dap- unit in a pyrazolylborate–zinc(II) complex. Finally, to our knowledge no reported appearance of an hpt2- group as an isolated counterion has been reported: the group has always been found coordinating to a metal atom.

The most attractive aspect of both structures resides in their extensive hydrogen-bonding scheme. In order to assess their real complexity compared with similar structures, we searched the CSD for compounds containing any kind of uncomplexed aminopurines (with allowance for substituents of any sort and eventually any number of carboxylate groups), with the restriction that they should not be bonded to any metal centre. To our surprise, this search provided only five entries, the packing schemes of which we analysed. An initial conclusion was that when the compound is ionic, the packing disposition in well differentiated ionic zones, as found in (II), seems to be typical. However, the particular geometries adopted in any particular case (planar, columnar etc.) can be flexible and ligand-dependent. This comparison with related structures also confirmed the, perhaps obvious, observation that the complexity of the hydrogen-bonding scheme sustaining a structure is strongly related to the hydration state of the compound. In this respect (II), with its seven solvent water molecules, giving rise to 26 independent hydrogen bonds, produces a scheme not only far more complex than that in (I), but also than those in related structures found in the literature, for example those structures which, complying with the restrictions of our search, appeared to have the largest number of such interactions, viz. ethyl 2,6-diaminopurine-9-acetate hemihydrate (Sood et al., 1997), with nine independent hydrogen bonds, or 3,4-dihydroxy-2,4-dimethyl-1,2,3,4-tetrahydropyrimido[2,1-f]- 9H-purine-2-carboxylate dihydrate (Routaboul et al., 2002), with seven independent hydrogen bonds.

Experimental top

A methanolic solution (20 ml) of the ligand 2,6-diaminopurine (0.5 mmol) was mixed with an aqueous solution containing homophthalic acid (0.5 mmol) and NaOH (1.0 mmol), and the resulting mixture was heated to reflux with stirring for 2 h. When trying to obtain suitable crystals for X-ray analysis by slow evaporation at room temperature, two well differentiated species appeared: thin colourless plates [Prisms given in CIF tables - please clarify] of (I), as a minor component, and well developed brownish prisms of (II) as the major one.

Refinement top

All H atoms were found in a difference Fourier map; they were, however, treated differently. H atoms attached to C atoms were positioned at their expected locations and allowed to ride, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C). H atoms attached to N and O atoms were initially refined with restrained distances to their hosts [N—H = O—H = 0.85 (1) Å and H···H = 1.35 (1) Å] and restricted to ride after convergence, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O).

Computing details top

For both compounds, data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2002); data reduction: SAINT-NT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme used. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing view of (I), showing a single plane and the rings which the hydrogen bonds (dashed lines) generate. Note the definitions of the ring centroids.
[Figure 3] Fig. 3. A packing view of (I), at right angles to that in Fig. 2, showing the way in which the planes interact. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]
[Figure 4] Fig. 4. The molecular structure of (II), showing the atom-labelling scheme used. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 5] Fig. 5. A partial packing view of (II), showing a single strip in the cationic structure. The reference dimeric pair of Hdpa+ ions is shown in bold and the symmetry related ones in simple lines. Labels 1 and 2 characterize the Hdpa+ ions, and A and B denote the rings produced by the hydrogen bonds (dashed lines). [Symmetry codes: (i) x - 1, y, z + 1; (ii) x + 1, y, z - 1.]
[Figure 6] Fig. 6. A partial packing view of (II), showing the relative positioning of the cationic strips shown in Fig 5, viewed (a) along [010], showing the way strips stack, and (b) at right angle to the previous view, projected along the strip direction, [101]."
[Figure 7] Fig. 7. A partial packing view of the anionic bilayered substructure of (II). (a) Projection down [010], displaying a single wall of the bilayer and showing the formation of the four hydrogen-bonded rings (C to F) [five, C to G?]. (b) A view at right angles to the previous one, projected along [001] and showing the complete bilayer sideways, as well as the R8(4,2) loop (G) [H?] linking both limiting walls. [Symmetry codes: (i) x + 1, y, z; (ii) -x + 1, -y + 1, -z + 1; (iii) x, y, z - 1; (iv) -x + 1, -y + 1, -z + 1; (v) -x + 2, -y + 1, -z + 2; (vi) -x + 1, -y + 1, -z + 2.]
[Figure 8] Fig. 8. A full packing view of the structure of (II), projected along [001], showing how the substructures interleave. Anionic substructures are drawn with simple lines, labelled (I), and cationic ones with heavy lines and labelled (II).
(I) 2,6-Diamino-9H-purine monohydrate top
Crystal data top
C5H6N6·H2OZ = 2
Mr = 168.17F(000) = 176
Triclinic, P1Dx = 1.574 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9331 (15) ÅCell parameters from 1887 reflections
b = 7.1079 (16) Åθ = 3.1–25.7°
c = 7.5564 (17) ŵ = 0.12 mm1
α = 99.089 (4)°T = 298 K
β = 98.029 (3)°Plate, colourless
γ = 101.331 (4)°0.28 × 0.25 × 0.08 mm
V = 354.89 (14) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1521 independent reflections
Radiation source: fine-focus sealed tube1280 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
ϕ and ω scansθmax = 27.9°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS in SAINT-NT; Bruker, 2002)
h = 98
Tmin = 0.96, Tmax = 0.99k = 99
2992 measured reflectionsl = 99
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1765P]
where P = (Fo2 + 2Fc2)/3
1521 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C5H6N6·H2Oγ = 101.331 (4)°
Mr = 168.17V = 354.89 (14) Å3
Triclinic, P1Z = 2
a = 6.9331 (15) ÅMo Kα radiation
b = 7.1079 (16) ŵ = 0.12 mm1
c = 7.5564 (17) ÅT = 298 K
α = 99.089 (4)°0.28 × 0.25 × 0.08 mm
β = 98.029 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1521 independent reflections
Absorption correction: multi-scan
(SADABS in SAINT-NT; Bruker, 2002)
1280 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.99Rint = 0.011
2992 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å3
1521 reflectionsΔρmin = 0.36 e Å3
109 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3620 (3)0.2931 (3)0.7865 (2)0.0361 (4)
H1A0.35000.33140.90720.038 (5)*
C20.4791 (2)0.2560 (2)0.5406 (2)0.0286 (4)
C30.5899 (2)0.2490 (2)0.3984 (2)0.0296 (4)
C40.3081 (2)0.0475 (2)0.2101 (2)0.0295 (4)
C50.2831 (2)0.1508 (2)0.4993 (2)0.0279 (4)
N10.2095 (2)0.1767 (2)0.65794 (19)0.0332 (4)
H10.09570.11770.67320.040*
N20.5270 (2)0.3460 (2)0.7230 (2)0.0338 (4)
N30.5019 (2)0.1444 (2)0.23351 (19)0.0308 (4)
N40.1883 (2)0.0441 (2)0.33584 (19)0.0306 (4)
N50.7835 (2)0.3421 (2)0.4228 (2)0.0422 (4)
H5B0.84140.34470.33100.051*
H5A0.83840.40380.52940.051*
N60.2269 (2)0.0500 (2)0.0386 (2)0.0382 (4)
H6B0.11890.13490.02860.046*
H6A0.30720.07410.03280.046*
O1W0.9117 (2)0.5693 (3)0.8411 (2)0.0673 (5)
H1WA0.79870.49510.83840.101*
H1WB0.88730.66920.80140.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (9)0.0412 (10)0.0304 (9)0.0028 (8)0.0109 (7)0.0021 (7)
C20.0259 (8)0.0291 (8)0.0294 (9)0.0027 (6)0.0073 (7)0.0036 (7)
C30.0256 (8)0.0300 (8)0.0327 (9)0.0018 (6)0.0091 (7)0.0062 (7)
C40.0260 (8)0.0323 (8)0.0302 (9)0.0045 (7)0.0076 (7)0.0059 (7)
C50.0251 (8)0.0299 (8)0.0290 (8)0.0043 (6)0.0082 (6)0.0056 (7)
N10.0268 (7)0.0397 (8)0.0304 (8)0.0004 (6)0.0105 (6)0.0030 (6)
N20.0304 (8)0.0362 (8)0.0309 (8)0.0005 (6)0.0068 (6)0.0021 (6)
N30.0252 (7)0.0350 (8)0.0305 (8)0.0012 (6)0.0097 (6)0.0036 (6)
N40.0234 (7)0.0374 (8)0.0287 (7)0.0012 (6)0.0071 (6)0.0038 (6)
N50.0284 (8)0.0534 (10)0.0361 (9)0.0083 (7)0.0120 (6)0.0010 (7)
N60.0273 (7)0.0508 (9)0.0292 (8)0.0030 (6)0.0069 (6)0.0008 (7)
O1W0.0523 (10)0.0695 (11)0.0622 (11)0.0199 (8)0.0148 (8)0.0020 (8)
Geometric parameters (Å, º) top
C1—N21.312 (2)C4—N31.357 (2)
C1—N11.364 (2)C5—N41.347 (2)
C1—H1A0.9300C5—N11.367 (2)
C2—C51.383 (2)N1—H10.8500
C2—N21.389 (2)N5—H5B0.8500
C2—C31.406 (2)N5—H5A0.8500
C3—N31.339 (2)N6—H6B0.8500
C3—N51.348 (2)N6—H6A0.8500
C4—N41.347 (2)O1W—H1WA0.8500
C4—N61.354 (2)O1W—H1WB0.8500
N2—C1—N1113.42 (16)N1—C5—C2105.68 (15)
N2—C1—H1A123.3C1—N1—C5106.50 (14)
N1—C1—H1A123.3C1—N1—H1128.0
C5—C2—N2110.39 (14)C5—N1—H1125.0
C5—C2—C3116.63 (15)C1—N2—C2104.00 (14)
N2—C2—C3132.96 (15)C3—N3—C4118.54 (14)
N3—C3—N5118.62 (15)C5—N4—C4112.11 (14)
N3—C3—C2119.24 (15)C3—N5—H5B119.1
N5—C3—C2122.13 (16)C3—N5—H5A117.4
N4—C4—N6117.38 (15)H5B—N5—H5A123.2
N4—C4—N3127.25 (16)C4—N6—H6B115.5
N6—C4—N3115.33 (15)C4—N6—H6A117.2
N4—C5—N1128.08 (15)H6B—N6—H6A117.6
N4—C5—C2126.23 (15)H1WA—O1W—H1WB106.1
C5—C2—C3—N30.5 (2)N1—C1—N2—C20.6 (2)
N2—C2—C3—N3178.60 (16)C5—C2—N2—C10.27 (19)
C5—C2—C3—N5178.57 (16)C3—C2—N2—C1177.92 (19)
N2—C2—C3—N50.5 (3)N5—C3—N3—C4178.68 (16)
N2—C2—C5—N4179.17 (15)C2—C3—N3—C40.4 (2)
C3—C2—C5—N40.7 (3)N4—C4—N3—C30.5 (3)
N2—C2—C5—N10.15 (19)N6—C4—N3—C3177.96 (15)
C3—C2—C5—N1178.67 (15)N1—C5—N4—C4178.51 (16)
N2—C1—N1—C50.7 (2)C2—C5—N4—C40.7 (2)
N4—C5—N1—C1178.81 (17)N6—C4—N4—C5177.99 (14)
C2—C5—N1—C10.49 (19)N3—C4—N4—C50.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.852.062.903 (2)170
N6—H6A···N3ii0.852.213.059 (2)176
N6—H6B···O1Wiii0.852.413.133 (2)144
N5—H5A···O1W0.852.403.229 (2)166
N5—H5B···O1Wiv0.852.343.145 (2)159
O1W—H1WA···N20.851.972.767 (2)155
O1W—H1WB···N4v0.852.543.387 (2)177
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x1, y1, z1; (iv) x+2, y+1, z+1; (v) x+1, y+1, z+1.
(II) bis(2,6-diamino-9H-purin-1-ium) 2-(2-carboxylatophenyl)acetate heptahydrate top
Crystal data top
2C5H7N6+·C9H6O42·7H2OF(000) = 1280
Mr = 606.58Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9999 reflections
a = 8.928 (2) Åθ = 2.9–26.5°
b = 31.393 (8) ŵ = 0.12 mm1
c = 10.091 (3) ÅT = 298 K
β = 90.833 (5)°Prism, brown
V = 2828.2 (12) Å30.22 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6234 independent reflections
Radiation source: fine-focus sealed tube3511 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ϕ and ω scansθmax = 27.8°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS in SAINT-NT; Bruker, 2002)
h = 1111
Tmin = 0.962, Tmax = 0.986k = 4040
23079 measured reflectionsl = 1213
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.5016P]
where P = (Fo2 + 2Fc2)/3
6234 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
2C5H7N6+·C9H6O42·7H2OV = 2828.2 (12) Å3
Mr = 606.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.928 (2) ŵ = 0.12 mm1
b = 31.393 (8) ÅT = 298 K
c = 10.091 (3) Å0.22 × 0.16 × 0.12 mm
β = 90.833 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6234 independent reflections
Absorption correction: multi-scan
(SADABS in SAINT-NT; Bruker, 2002)
3511 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.986Rint = 0.058
23079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.12Δρmax = 0.17 e Å3
6234 reflectionsΔρmin = 0.18 e Å3
379 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1W0.8540 (3)0.55442 (9)0.9469 (2)0.1140 (8)
H1WA0.88630.56480.87500.171*
H1WB0.83060.52860.93160.171*
O2W0.3226 (3)0.58889 (9)0.9746 (3)0.1327 (10)
H2WA0.30090.59290.89320.199*
H2WB0.26130.57061.00440.199*
O3W0.2003 (2)0.61023 (5)0.73207 (18)0.0666 (5)
H3WA0.23440.60620.65480.100*
H3WB0.10740.60470.72510.100*
O4W0.6160 (3)0.60760 (8)0.9989 (3)0.1248 (10)
H4WA0.68650.59060.97960.187*
H4WB0.54680.60170.94320.187*
O5W0.8768 (3)0.46547 (9)0.9075 (2)0.1202 (9)
H5WA0.95840.46140.95010.180*
H5WB0.88440.45630.82860.180*
O6W0.9002 (2)0.44366 (9)0.6532 (2)0.1193 (9)
H6WA0.84510.42220.63590.179*
H6WB0.95550.44710.58620.179*
O7W0.7748 (2)0.62405 (7)0.2604 (2)0.0909 (7)
H7WA0.76470.60600.19810.136*
H7WB0.79610.61130.33250.136*
O130.3162 (2)0.59642 (6)0.48500 (19)0.0709 (5)
O230.5334 (2)0.61856 (6)0.57094 (19)0.0681 (5)
O330.8917 (2)0.60391 (6)0.50298 (19)0.0691 (5)
O430.8829 (2)0.60191 (6)0.7208 (2)0.0701 (5)
C130.5388 (3)0.55952 (7)0.4231 (2)0.0484 (6)
C230.6702 (3)0.54000 (7)0.4707 (2)0.0499 (6)
C330.7405 (3)0.51037 (8)0.3883 (3)0.0640 (7)
H330.82730.49690.41860.077*
C430.6861 (4)0.50080 (9)0.2663 (3)0.0761 (9)
H430.73660.48150.21330.091*
C530.5539 (4)0.51983 (9)0.2195 (3)0.0716 (8)
H530.51580.51350.13550.086*
C630.4829 (3)0.54769 (8)0.2993 (3)0.0599 (7)
H630.39270.55940.27000.072*
C730.4580 (3)0.59389 (8)0.4988 (3)0.0550 (6)
C830.7400 (3)0.54957 (8)0.6034 (3)0.0563 (7)
H83A0.79550.52470.63280.068*
H83B0.66040.55430.66620.068*
C930.8453 (3)0.58796 (8)0.6079 (3)0.0556 (6)
N110.9412 (2)0.68531 (6)0.13969 (18)0.0496 (5)
H110.89580.66700.18660.060*
N211.0877 (2)0.71704 (6)0.01009 (18)0.0481 (5)
N310.9239 (2)0.81043 (6)0.15483 (17)0.0458 (5)
H310.92260.83740.16040.055*
N410.8328 (2)0.74640 (6)0.24859 (18)0.0451 (5)
N511.0880 (2)0.81605 (6)0.02174 (19)0.0551 (5)
H51A1.07280.84280.02170.066*
H51B1.14710.80510.07750.066*
N610.7529 (2)0.81180 (7)0.3237 (2)0.0578 (6)
H61A0.70260.79840.38120.069*
H61B0.75710.83870.31600.069*
C111.0417 (3)0.68113 (8)0.0394 (2)0.0522 (6)
H11A1.07450.65480.00920.063*
C211.0139 (2)0.74728 (7)0.0674 (2)0.0427 (5)
C311.0123 (2)0.79190 (7)0.0624 (2)0.0421 (5)
C410.8363 (2)0.78891 (7)0.2419 (2)0.0426 (5)
C510.9219 (2)0.72808 (7)0.1583 (2)0.0423 (5)
N120.4558 (2)0.82560 (6)0.62823 (19)0.0571 (6)
H120.49140.84660.58580.069*
N220.3081 (2)0.79386 (6)0.77641 (18)0.0496 (5)
N320.46583 (19)0.70019 (6)0.60898 (17)0.0427 (4)
H320.46910.67320.60310.051*
N420.5618 (2)0.76468 (6)0.51689 (18)0.0477 (5)
N520.2953 (2)0.69577 (6)0.77972 (18)0.0494 (5)
H52A0.29710.66880.77260.059*
H52B0.23940.70690.83770.059*
N620.6405 (2)0.69896 (7)0.44262 (19)0.0552 (5)
H62A0.69250.71180.38520.066*
H62B0.63300.67210.44960.066*
C120.3553 (3)0.83013 (8)0.7284 (2)0.0573 (7)
H12A0.32340.85650.75930.069*
C220.3853 (2)0.76376 (7)0.7010 (2)0.0395 (5)
C320.3786 (2)0.71928 (7)0.7006 (2)0.0395 (5)
C420.5553 (2)0.72234 (8)0.5223 (2)0.0455 (6)
C520.4737 (2)0.78323 (7)0.6093 (2)0.0434 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.117 (2)0.122 (2)0.1034 (18)0.0091 (16)0.0037 (15)0.0128 (15)
O2W0.150 (3)0.138 (2)0.110 (2)0.029 (2)0.0255 (18)0.0001 (17)
O3W0.0585 (11)0.0649 (11)0.0766 (12)0.0065 (9)0.0069 (9)0.0041 (9)
O4W0.127 (2)0.0894 (18)0.160 (2)0.0049 (15)0.0441 (19)0.0362 (16)
O5W0.113 (2)0.150 (2)0.0964 (17)0.0032 (18)0.0261 (15)0.0047 (16)
O6W0.0665 (15)0.169 (3)0.122 (2)0.0102 (15)0.0007 (14)0.0434 (18)
O7W0.0908 (16)0.0836 (15)0.0986 (15)0.0213 (12)0.0072 (12)0.0309 (12)
O130.0502 (12)0.0781 (13)0.0845 (13)0.0065 (9)0.0101 (10)0.0059 (10)
O230.0616 (12)0.0559 (11)0.0871 (13)0.0017 (9)0.0066 (10)0.0177 (10)
O330.0664 (12)0.0597 (11)0.0815 (13)0.0164 (9)0.0169 (10)0.0029 (10)
O430.0657 (12)0.0679 (12)0.0768 (13)0.0083 (10)0.0031 (10)0.0128 (10)
C130.0461 (15)0.0401 (13)0.0594 (15)0.0097 (11)0.0114 (12)0.0002 (11)
C230.0481 (15)0.0374 (13)0.0644 (16)0.0082 (11)0.0094 (12)0.0013 (11)
C330.0614 (17)0.0479 (15)0.083 (2)0.0042 (13)0.0073 (15)0.0048 (14)
C430.092 (2)0.0568 (18)0.080 (2)0.0012 (17)0.0207 (19)0.0171 (15)
C530.085 (2)0.0637 (18)0.0659 (18)0.0026 (17)0.0031 (17)0.0106 (15)
C630.0593 (17)0.0535 (16)0.0671 (17)0.0067 (13)0.0083 (14)0.0016 (13)
C730.0521 (17)0.0495 (15)0.0637 (16)0.0024 (12)0.0085 (13)0.0036 (13)
C830.0526 (16)0.0451 (14)0.0715 (17)0.0014 (12)0.0081 (13)0.0063 (12)
C930.0484 (15)0.0470 (15)0.0716 (18)0.0005 (12)0.0079 (14)0.0045 (14)
N110.0495 (12)0.0491 (12)0.0505 (11)0.0081 (9)0.0144 (10)0.0027 (9)
N210.0497 (12)0.0461 (11)0.0488 (11)0.0009 (9)0.0118 (10)0.0011 (9)
N310.0420 (11)0.0481 (11)0.0475 (11)0.0043 (9)0.0101 (9)0.0043 (9)
N410.0376 (11)0.0510 (12)0.0469 (11)0.0029 (9)0.0084 (9)0.0031 (9)
N510.0650 (14)0.0442 (11)0.0566 (12)0.0044 (10)0.0205 (11)0.0012 (9)
N610.0535 (13)0.0561 (13)0.0644 (13)0.0025 (10)0.0208 (11)0.0062 (10)
C110.0563 (16)0.0461 (14)0.0544 (15)0.0009 (12)0.0125 (13)0.0028 (11)
C210.0385 (13)0.0476 (14)0.0423 (13)0.0001 (10)0.0068 (10)0.0012 (10)
C310.0380 (13)0.0479 (14)0.0406 (12)0.0010 (10)0.0022 (10)0.0003 (10)
C410.0307 (12)0.0563 (15)0.0407 (13)0.0003 (10)0.0022 (10)0.0030 (11)
C510.0376 (12)0.0471 (14)0.0423 (12)0.0036 (10)0.0029 (11)0.0018 (10)
N120.0650 (14)0.0471 (12)0.0598 (13)0.0095 (10)0.0193 (11)0.0016 (10)
N220.0500 (12)0.0495 (12)0.0498 (11)0.0037 (9)0.0145 (9)0.0085 (9)
N320.0409 (11)0.0416 (10)0.0459 (11)0.0004 (8)0.0078 (9)0.0025 (8)
N420.0448 (11)0.0502 (12)0.0484 (11)0.0008 (9)0.0094 (9)0.0015 (9)
N520.0555 (12)0.0418 (11)0.0514 (11)0.0047 (9)0.0184 (10)0.0009 (9)
N620.0466 (12)0.0582 (13)0.0612 (13)0.0027 (10)0.0175 (10)0.0034 (10)
C120.0634 (17)0.0469 (15)0.0619 (16)0.0066 (12)0.0172 (14)0.0097 (12)
C220.0342 (12)0.0445 (13)0.0399 (12)0.0015 (10)0.0050 (10)0.0028 (10)
C320.0338 (12)0.0444 (13)0.0403 (12)0.0005 (10)0.0002 (10)0.0030 (10)
C420.0364 (13)0.0555 (15)0.0448 (13)0.0003 (11)0.0061 (11)0.0026 (11)
C520.0397 (13)0.0462 (14)0.0446 (13)0.0030 (10)0.0042 (11)0.0026 (10)
Geometric parameters (Å, º) top
O1W—H1WA0.8500N21—C111.302 (3)
O1W—H1WB0.8501N21—C211.401 (3)
O2W—H2WA0.8500N31—C311.361 (3)
O2W—H2WB0.8499N31—C411.364 (3)
O3W—H3WA0.8501N31—H310.8500
O3W—H3WB0.8501N41—C411.336 (3)
O4W—H4WA0.8500N41—C511.347 (3)
O4W—H4WB0.8500N51—C311.330 (3)
O5W—H5WA0.8500N51—H51A0.8500
O5W—H5WB0.8500N51—H51B0.8500
O6W—H6WA0.8499N61—C411.330 (3)
O6W—H6WB0.8500N61—H61A0.8500
O7W—H7WA0.8499N61—H61B0.8500
O7W—H7WB0.8500C11—H11A0.9300
O13—C731.274 (3)C21—C511.379 (3)
O23—C731.252 (3)C21—C311.402 (3)
O33—C931.247 (3)N12—C521.354 (3)
O43—C931.262 (3)N12—C121.369 (3)
C13—C631.389 (3)N12—H120.8500
C13—C231.403 (3)N22—C121.310 (3)
C13—C731.511 (3)N22—C221.401 (3)
C23—C331.402 (3)N32—C321.357 (3)
C23—C831.499 (4)N32—C421.381 (3)
C33—C431.351 (4)N32—H320.8500
C33—H330.9300N42—C421.332 (3)
C43—C531.399 (4)N42—C521.360 (3)
C43—H430.9300N52—C321.324 (3)
C53—C631.353 (4)N52—H52A0.8500
C53—H530.9300N52—H52B0.8500
C63—H630.9300N62—C421.335 (3)
C83—C931.529 (3)N62—H62A0.8500
C83—H83A0.9700N62—H62B0.8500
C83—H83B0.9700C12—H12A0.9300
N11—C511.367 (3)C22—C521.369 (3)
N11—C111.369 (3)C22—C321.398 (3)
N11—H110.8500
H1WA—O1W—H1WB107.3C41—N61—H61A117.6
H2WA—O2W—H2WB107.6C41—N61—H61B117.1
H3WA—O3W—H3WB104.8H61A—N61—H61B125.3
H4WA—O4W—H4WB104.1N21—C11—N11114.5 (2)
H5WA—O5W—H5WB110.1N21—C11—H11A122.8
H6WA—O6W—H6WB106.2N11—C11—H11A122.8
H7WA—O7W—H7WB109.9C51—C21—N21111.4 (2)
C63—C13—C23118.6 (2)C51—C21—C31117.1 (2)
C63—C13—C73118.6 (2)N21—C21—C31131.4 (2)
C23—C13—C73122.8 (2)N51—C31—N31119.9 (2)
C33—C23—C13117.8 (2)N51—C31—C21126.0 (2)
C33—C23—C83118.6 (2)N31—C31—C21114.07 (19)
C13—C23—C83123.6 (2)N61—C41—N41119.6 (2)
C43—C33—C23122.0 (3)N61—C41—N31117.6 (2)
C43—C33—H33119.0N41—C41—N31122.77 (19)
C23—C33—H33119.0N41—C51—N11126.1 (2)
C33—C43—C53120.3 (3)N41—C51—C21128.8 (2)
C33—C43—H43119.9N11—C51—C21105.10 (19)
C53—C43—H43119.9C52—N12—C12106.61 (19)
C63—C53—C43118.3 (3)C52—N12—H12130.2
C63—C53—H53120.8C12—N12—H12123.1
C43—C53—H53120.8C12—N22—C22102.83 (18)
C53—C63—C13122.9 (3)C32—N32—C42123.53 (19)
C53—C63—H63118.5C32—N32—H32120.5
C13—C63—H63118.5C42—N32—H32115.9
O23—C73—O13123.4 (2)C42—N42—C52111.91 (19)
O23—C73—C13118.6 (2)C32—N52—H52A119.5
O13—C73—C13118.0 (2)C32—N52—H52B121.8
C23—C83—C93115.6 (2)H52A—N52—H52B118.7
C23—C83—H83A108.4C42—N62—H62A118.1
C93—C83—H83A108.4C42—N62—H62B116.7
C23—C83—H83B108.4H62A—N62—H62B125.0
C93—C83—H83B108.4N22—C12—N12113.7 (2)
H83A—C83—H83B107.4N22—C12—H12A123.2
O33—C93—O43122.7 (2)N12—C12—H12A123.2
O33—C93—C83120.2 (3)C52—C22—C32117.98 (19)
O43—C93—C83117.1 (2)C52—C22—N22111.03 (19)
C51—N11—C11106.32 (18)C32—C22—N22130.87 (19)
C51—N11—H11121.6N52—C32—N32119.9 (2)
C11—N11—H11132.0N52—C32—C22125.43 (19)
C11—N21—C21102.64 (18)N32—C32—C22114.72 (19)
C31—N31—C41125.0 (2)N42—C42—N62119.9 (2)
C31—N31—H31118.7N42—C42—N32123.7 (2)
C41—N31—H31116.3N62—C42—N32116.4 (2)
C41—N41—C51112.18 (18)N12—C52—N42126.0 (2)
C31—N51—H51A118.7N12—C52—C22105.86 (19)
C31—N51—H51B121.2N42—C52—C22128.1 (2)
H51A—N51—H51B120.0
C63—C13—C23—C331.8 (3)C31—N31—C41—N412.6 (3)
C73—C13—C23—C33176.2 (2)C41—N41—C51—N11179.4 (2)
C63—C13—C23—C83179.0 (2)C41—N41—C51—C211.8 (3)
C73—C13—C23—C833.0 (3)C11—N11—C51—N41179.4 (2)
C13—C23—C33—C430.6 (4)C11—N11—C51—C210.4 (2)
C83—C23—C33—C43178.6 (2)N21—C21—C51—N41179.5 (2)
C23—C33—C43—C531.5 (4)C31—C21—C51—N412.9 (4)
C33—C43—C53—C630.2 (4)N21—C21—C51—N111.5 (3)
C43—C53—C63—C132.8 (4)C31—C21—C51—N11178.1 (2)
C23—C13—C63—C533.6 (4)C22—N22—C12—N120.2 (3)
C73—C13—C63—C53174.4 (2)C52—N12—C12—N220.7 (3)
C63—C13—C73—O23146.4 (2)C12—N22—C22—C521.0 (3)
C23—C13—C73—O2331.6 (3)C12—N22—C22—C32176.9 (2)
C63—C13—C73—O1333.1 (3)C42—N32—C32—N52179.6 (2)
C23—C13—C73—O13148.9 (2)C42—N32—C32—C220.2 (3)
C33—C23—C83—C9393.9 (3)C52—C22—C32—N52177.8 (2)
C13—C23—C83—C9385.3 (3)N22—C22—C32—N522.2 (4)
C23—C83—C93—O3314.1 (3)C52—C22—C32—N321.6 (3)
C23—C83—C93—O43166.6 (2)N22—C22—C32—N32177.2 (2)
C21—N21—C11—N111.8 (3)C52—N42—C42—N62176.8 (2)
C51—N11—C11—N211.0 (3)C52—N42—C42—N321.9 (3)
C11—N21—C21—C512.0 (3)C32—N32—C42—N422.1 (3)
C11—N21—C21—C31178.0 (3)C32—N32—C42—N62176.6 (2)
C41—N31—C31—N51176.9 (2)C12—N12—C52—N42178.5 (2)
C41—N31—C31—C213.4 (3)C12—N12—C52—C221.2 (3)
C51—C21—C31—N51177.0 (2)C42—N42—C52—N12179.6 (2)
N21—C21—C31—N511.2 (4)C42—N42—C52—C220.1 (3)
C51—C21—C31—N313.3 (3)C32—C22—C52—N12177.9 (2)
N21—C21—C31—N31179.1 (2)N22—C22—C52—N121.4 (3)
C51—N41—C41—N61179.2 (2)C32—C22—C52—N421.8 (4)
C51—N41—C41—N311.5 (3)N22—C22—C52—N42178.3 (2)
C31—N31—C41—N61178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N61—H61A···N420.852.153.000 (3)176
N62—H62A···N410.852.173.016 (3)177
N51—H51B···N22i0.852.102.934 (3)166
N52—H52B···N21ii0.852.092.914 (3)165
O7W—H7WB···O330.851.922.722 (3)156
O7W—H7WA···O4Wiii0.852.393.022 (4)131
O6W—H6WA···O13iv0.851.962.680 (3)141
O6W—H6WB···O33v0.852.302.872 (3)125
O5W—H5WB···O6W0.851.822.667 (4)173
O5W—H5WA···O1Wvi0.852.022.867 (4)174
O4W—H4WB···O2W0.852.072.693 (4)130
O4W—H4WA···O1W0.851.912.758 (4)176
O3W—H3WA···O130.851.902.748 (3)178
O3W—H3WB···O43vii0.852.012.847 (3)170
O2W—H2WA···O3W0.851.932.748 (3)163
O2W—H2WB···O5Wviii0.851.902.749 (4)172
O1W—H1WA···O430.851.942.741 (3)156
O1W—H1WB···O5W0.852.042.829 (4)154
N62—H62B···O230.852.273.000 (3)144
N52—H52A···O3W0.852.072.855 (3)153
N32—H32···O230.851.842.662 (3)162
N12—H12···O4Wix0.852.032.864 (3)169
N61—H61B···O43ix0.852.383.130 (3)147
N51—H51A···O33ix0.852.343.076 (3)145
N31—H31···O43ix0.852.032.856 (3)163
N11—H11···O7W0.851.892.728 (3)169
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1; (iii) x, y, z1; (iv) x+1, y+1, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+1, z+2; (vii) x1, y, z; (viii) x+1, y+1, z+2; (ix) x, y+3/2, z1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC5H6N6·H2O2C5H7N6+·C9H6O42·7H2O
Mr168.17606.58
Crystal system, space groupTriclinic, P1Monoclinic, P21/c
Temperature (K)298298
a, b, c (Å)6.9331 (15), 7.1079 (16), 7.5564 (17)8.928 (2), 31.393 (8), 10.091 (3)
α, β, γ (°)99.089 (4), 98.029 (3), 101.331 (4)90, 90.833 (5), 90
V3)354.89 (14)2828.2 (12)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.120.12
Crystal size (mm)0.28 × 0.25 × 0.080.22 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS in SAINT-NT; Bruker, 2002)
Multi-scan
(SADABS in SAINT-NT; Bruker, 2002)
Tmin, Tmax0.96, 0.990.962, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
2992, 1521, 1280 23079, 6234, 3511
Rint0.0110.058
(sin θ/λ)max1)0.6580.656
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.03 0.059, 0.140, 1.12
No. of reflections15216234
No. of parameters109379
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.360.17, 0.18

Computer programs: SMART-NT (Bruker, 2001), SAINT-NT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.852.062.903 (2)170.4
N6—H6A···N3ii0.852.213.059 (2)176.1
N6—H6B···O1Wiii0.852.413.133 (2)143.7
N5—H5A···O1W0.852.403.229 (2)166.2
N5—H5B···O1Wiv0.852.343.145 (2)159.2
O1W—H1WA···N20.851.972.767 (2)154.7
O1W—H1WB···N4v0.852.543.387 (2)176.6
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x1, y1, z1; (iv) x+2, y+1, z+1; (v) x+1, y+1, z+1.
ππ contacts (Å, °) for (I) top
Group 1/group 2CCD (Å)IPD (Å)SA (°)
Cg1···Cg2i3.501 (2)3.30 (2)19.5 (6)
Cg2···Cg2ii3.514 (1)3.307 (1)19.72 (1)
Symmetry codes: (i) -x + 1, -y, -z + 1; (ii) -x + 1, -y + 1, -z + 1. Notes: Cg1 is the centroid of the N1/C1/N2/C2/C5 ring and Cg2 is the centroid of the N3/C3/C2/C5/N4/C4 ring. CCD id the centre-to-centre distance (distance between ring centroids), IPD is the mean interplanar distance (distance from one plane to the neighbouring centroid) and SA is the mean slippage angle (angle subtended by the intercentroid vector to the plane normal). For details, see Janiak (2000).
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N61—H61A···N420.852.153.000 (3)175.9
N62—H62A···N410.852.173.016 (3)176.5
N51—H51B···N22i0.852.102.934 (3)165.7
N52—H52B···N21ii0.852.092.914 (3)164.5
O7W—H7WB···O330.851.922.722 (3)156.1
O7W—H7WA···O4Wiii0.852.393.022 (4)131.2
O6W—H6WA···O13iv0.851.962.680 (3)141.3
O6W—H6WB···O33v0.852.302.872 (3)125.3
O5W—H5WB···O6W0.851.822.667 (4)172.9
O5W—H5WA···O1Wvi0.852.022.867 (4)174.4
O4W—H4WB···O2W0.852.072.693 (4)129.5
O4W—H4WA···O1W0.851.912.758 (4)175.5
O3W—H3WA···O130.851.902.748 (3)178.1
O3W—H3WB···O43vii0.852.012.847 (3)169.9
O2W—H2WA···O3W0.851.932.748 (3)162.6
O2W—H2WB···O5Wviii0.851.902.749 (4)172.0
O1W—H1WA···O430.851.942.741 (3)155.8
O1W—H1WB···O5W0.852.042.829 (4)153.8
N62—H62B···O230.852.273.000 (3)144.4
N52—H52A···O3W0.852.072.855 (3)153.3
N32—H32···O230.851.842.662 (3)162.4
N12—H12···O4Wix0.852.032.864 (3)168.6
N61—H61B···O43ix0.852.383.130 (3)146.7
N51—H51A···O33ix0.852.343.076 (3)144.6
N31—H31···O43ix0.852.032.856 (3)163.2
N11—H11···O7W0.851.892.728 (3)169.0
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1; (iii) x, y, z1; (iv) x+1, y+1, z+1; (v) x+2, y+1, z+1; (vi) x+2, y+1, z+2; (vii) x1, y, z; (viii) x+1, y+1, z+2; (ix) x, y+3/2, z1/2.
ππ contacts (Å, °) for (II) top
Group 1/group 2CCD (Å)IPD (Å)SA (°)
Cg1···Cg2i3.693 (2)3.35 (1)24.7 (1)
Cg3···Cg4ii4.083 (2)3.34 (1)35.1 (3)
Cg5···Cg5iii4.184 (2)3.74 (1)26.52 (1)
Symmetry codes: (i) x + 1, -y + 3/2, z - 1/2; (ii) x, -y + 3/2, z - 1/2; (iii) -x + 1, -y + 1, -z + 1. Notes: Cg1 is the centroid of the N11/C11/N21/C21/C51 ring, Cg2 of the N12/C12/N22/C22/C52 ring, Cg3 of the N31/C31/C21/C51/N41/C41 ring, Cg4 of the N32/C32/C22/C52/N42/C42 ring and Cg5 of the C13/C23/C33/C43/C53/C63 ring. CCD is the centre-to-centre distance (distance between ring centroids), IPD is the mean interplanar distance (distance from one plane to the neighbouring centroid) and SA is the mean slippage angle (angle subtended by the intercentroid vector to the plane normal). For details, see Janiak (2000)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds