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Hydantoin-5-acetic acid [2-(2,5-dioxoimidazolidin-4-yl)acetic acid] and orotic acid (2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidine-4-carb­oxy­lic acid) each contain one rigid acceptor-donor-acceptor hydrogen-bonding site and a flexible side chain, which can adopt different conformations. Since both com­pounds may be used as coformers for supra­molecular com­plexes, they have been crystallized in order to examine their conformational preferences, giving solvent-free hydantoin-5-acetic acid, C5H6N2O4, (I), and three crystals containing orotic acid, namely, orotic acid dimethyl sulfoxide monosolvate, C5H4N2O4·C2H6OS, (IIa), dimethyl­ammonium oro­tate-orotic acid (1/1), C2H8N+·C5H3N2O4-·C5H4N2O4, (IIb), and dimethyl­ammonium orotate-orotic acid (3/1), 3C2H8N+·3C5H3N2O4-·C5H4N2O4, (IIc). The crystal structure of (I) shows a three-dimensional network, with the acid function located perpendicular to the ring. Inter­estingly, the hy­droxy O atom acts as an acceptor, even though the carbonyl O atom is not involved in any hydrogen bonds. However, in (IIa), (IIb) and (IIc), the acid functions are only slightly twisted out of the ring planes. All H atoms of the acidic functions are directed away from the rings and, with respect to the carbonyl O atoms, they show an anti­periplanar conformation in (I) and synperiplanar conformations in (IIa), (IIb) and (IIc). Furthermore, in (IIa), (IIb) and (IIc), different con­formations of the acid O=C-C-N torsion angle are observed, leading to different hydrogen-bonding arrangements depending on their conformation and composition.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112001151/sk3419sup1.cif
Contains datablocks I, IIa, IIb, IIc, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112001151/sk3419Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112001151/sk3419IIasup3.hkl
Contains datablock IIa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112001151/sk3419IIbsup4.hkl
Contains datablock IIb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112001151/sk3419IIcsup5.hkl
Contains datablock IIc

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112001151/sk3419Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112001151/sk3419IIasup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112001151/sk3419IIbsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270112001151/sk3419IIcsup9.cml
Supplementary material

CCDC references: 867030; 867031; 867032; 867033

Comment top

Active pharmaceutical ingredients (APIs) usually contain functional groups that are involved in recognition processes. Their polymorphic nature often leads to new opportunities in drug development. APIs are mostly administered as salts or together with a pharmaceutically inactive carrier compound, which possibly changes the desired pharmaceutical effects (Almarsson & Zaworotko, 2004). The design of cocrystals with an API presents an alternative route to obtain new dosage forms without affecting the pharmaceutical activity (Ghosh et al., 2011; Vishweshwar et al., 2005). The most promising approach for the design of cocrystals deals with supramolecular synthons (Blagden et al., 2008). The most-studied synthon is that formed between an amide and a carboxylic acid (Rodríguez-Cuamatzi et al., 2007). Since carboxylic acids form robust and directed hydrogen bonds (Blagden et al., 2007) they are ideal candidates as coformers for APIs (Almarsson & Zaworotko, 2004). Although carboxylic acids are able to improve the stability of API-containing complexes (Seaton & Parkin, 2011), they show conformational polymorphism. Therefore, the possible conformations of carboxylic acids must be examined prior to their use as coformers for APIs. For this reason, we crystallized hydantoin-5-acetic acid, (I), and orotic acid, (II), under several different sets of conditions.

Compounds (I) and (II) contain heterocyclic ring structures, rigid ADA (A = acceptor, D = donor) hydrogen-bonding sites and rotatable acid functionalities. Various crystallization attempts with hydantoin-5-acetic acid yielded only the solvent-free structure, (I), while crystallization experiments with (II) resulted in three structures, namely a dimethyl sulfoxide monosolvate, (IIa), and two dimethylammonium orotate–orotic acid compounds with varying compositions, (IIb) and (IIc). Both (IIb) and (IIc) crystallized from dimethylformamide but at different temperatures [(IIb) at room temperature and (IIc) at 277 K].

Compound (I) crystallizes in the orthorhombic space group P212121 with one molecule in the asymmetric unit. The molecule contains a centre of chirality at C5, the absolute configuration of which was not determined due to the absence of significant anomalous scatterers (Fig. 1). The planar side chain (r.m.s. deviation for all non-H atoms = 0.006 Å) is perpendicular [dihedral angle = 89.28 (6)°] to the planar hydantoin ring (r.m.s deviation = 0.026 Å for all non-H atoms). Hydroxyl atom H54 points away from the hydantoin ring and the O—H bond is trans to the CO bond [O53—C52—O54—H54 = 180 (2)°].

The crystal packing of (I) shows sheets of hydantoin-5-acetic acid molecules, which are parallel to the (012) plane (Fig. 2). The sheets are characterized by R33(15) interactions (Bernstein et al., 1995) with one O—H···O and two N—H···O hydrogen bonds (Table 1). Adjacent sheets are connected via R44(20) patterns which consist of two N—H···O and two O—H···O bonds, building a three-dimensional network in the form of a zigzag pattern (Fig. 3). Interestingly, the N—H···O interactions of the R44(20) patterns are connected via atom O54 of the carboxyl group and not via carbonyl atom O53.

The orotic acid dimethyl sulfoxide (DMSO) monosolvate (IIa) crystallizes in the monoclinic space group P21/c, with one planar orotic acid molecule (r.m.s deviation = 0.038 Å for all non-H atoms) and one DMSO molecule in the asymmetric unit (Fig. 4). The carbonyl O atom of the acid functionality is located in an antiperiplanar arrangement with respect to atom N5 [torsion angle N5—C4—C41—O42 = 176.17 (18)°] and is synperiplanar to atom H43. In the asymmetric unit, the DMSO and orotic acid molecules are connected via an O—H···O hydrogen bond.

In the packing of (IIa), two orotic acid molecules are connected to form a centrosymmetric dimer. These dimers are further connected via DMSO molecules by N—H···O and O—H···O hydrogen bonds (Table 2) to form chains running in the [120] and [120] directions, respectively (Fig. 5).

Compound (IIb) crystallizes from dimethylformamide (DMF) in the triclinic space group P1. Since we did not use a water-free solvent, acidic hydrolysis of DMF, followed by an acid–base reaction with orotic acid, has taken place, resulting in the formation of a dimethylammonium cation (DMC) and an orotate anion. The asymmetric unit of (IIb) contains an orotic acid molecule (A) and an orotate anion (B), both of which are planar (r.m.s deviation for all non-H atoms of molecule A = 0.054 Å; r.m.s deviation of all non-H atoms of anion B = 0.081 Å), and one DMC cation [angle C1X—N2X—C3X = 113.4 (2)°] (Fig. 6). In the asymmetric unit, the molecule A and anion B are connected through a short O—H···O acid bridge [D···A = 2.482 (3) Å; Table 3], while the DMC forms an N—H···O hydrogen bond with anion B. Both molecule A and anion B show slightly twisted acid functionalities, with dihedral angles between the COO groups and the ring planes [r.m.s deviations for all non-H atoms of the ring = 0.018 Å (molecule A) and 0.009 Å (anion B)] of 6.5 (5)° in molecule A and 10.7 (4)° in anion B. Moreover, molecule A and anion B are oriented at an angle of 9.25 (5)° (for all non-H atoms of A and B) with respect to each other. Both molecule A and cation B contain bond lengths of their COO groups which are indicative of double [C41A—O42A = 1.226 (3) Å and C41B—O42B = 1.222 (3) Å] and single bonds [C41A—O43A = 1.281 (3) Å and C41B—O43B = 1.293 (3) Å]. The torsion angle N5A—C4A—C41A—O42A is -3.9 (3)°, while the corresponding angle in anion B is N5B—C4B—C41B—O42B = 9.0 (3)°. In contrast with (IIa), anion B prefers a synperiplanar conformation between atoms N5 and O42 in (IIb).

The crystal packing of (IIb) shows slightly rippled chains (r.m.s deviation of all non-H atoms of the rings = 0.087 Å) of molecules A and anions B, in turn characterized by an R22(8) pattern of two N—H···O bonds and, alternately, one O—H···O interaction. Adjacent chains are connected via R22(8) patterns of two N—H···O hydrogen bonds, resulting in honeycomb-shaped layers parallel to (111). In addition, the DMC connects molecule A and anion B via two N—H···O interactions. Furthermore, `double layers' are formed between adjacent layers by N—H···O interactions between the DMCs and molecules A and anions B, respectively (Fig. 7).

The second dimethylammonium orotate–orotic acid (3/1), (IIc), crystallizes in the monoclinic space group P21. As in (IIb), acid hydrolysis of DMF followed by an acid–base reaction with orotic acid have taken place, yielding three DMCs [angles 112.1 (6) (cation X), 113.7 (8) (cation Y) and 113.8 (7)° (cation Z)], two orotate anions (A and C) and, interestingly, two partially deprotonated orotic acid molecules (B and D), sharing one H atom of the acidic function, within the asymmetric unit (Fig. 8). All orotate anions and orotic acid molecules are essentially planar [r.m.s. deviations of all non-H atoms = 0.103 (anion A), 0.070 (molecule B), 0.027 (anion C) and 0.063 Å (molecule D)] and contain slightly twisted acid functionalities, with dihedral angles between the COO groups and the ring planes [r.m.s. deviations of all non-H atoms of the ring = 0.021 (anion A), 0.014 (molecule B), 0.020 (anion C) and 0.017 Å (molecule D)] of 13.4 (6)° in A, 9.2 (6)° in B, 2.9 (7)° in C and 7.9 (6)° in D. In A and C, similar bond lengths of both carboxy O atoms indicate delocalized charges [C41A—O42A = 1.240 (9) Å and C41A—O43A = 1.258 (9) Å, and C41C—O42C = 1.248 (9) Å and C41C—O43C = 1.282 (9) Å], while in B and D the bond lengths of atoms O42 and O43 are indicative of single [C41B—O43B = 1.297 (8) Å and C41D—O43D = 1.294 (8) Å] and double [C41B—O42B = 1.207 (9) Å and C41D—O42D = 1.232 (9) Å] bonds. In accordance with (IIb) and in contrast with (IIa), molecules B and D in (IIc) prefer a synperiplanar conformation between atoms N5 and O42 [N5B—C4B—C41B—O42B = 7.9 (11)° and N5D—C4D—C41D—O42D = 7.6 (11)°]. In the asymmetric unit, A is connected to C via two bridging DMCs (Y and Z), providing an R44(18) pattern with four N—H···O hydrogen bonds, while the third DMC, X, interacts with molecule D through one N—H···O hydrogen bond. Molecules B and D are connected via a short O—H···O acid bridge formed between atoms O43B and O43D [O···O = 2.433 (6) Å; Table 4].

In the crystal packing of (IIc), two different alternating layer structures parallel to (100), built by entities A, C, Y and Z in one case and entities B, D and X in the other, can be observed. The former layer structure contains chains running along [001] of alternating A and C entities, characterized by N—H···O-bonded R22(8) patterns. In addition, adjacent chains of A and C entities are connected to form rippled layers [r.m.s deviation of all non-H atoms of the rings of A and C = 0.487 Å] through DMCs Y and Z, providing N—H···O-bonded R44(18) patterns and R86(24) interactions of eight N—H···O bonds in turn (Fig. 9). In the second case, distorted honeycomb-shaped and slightly rippled layers [r.m.s deviation of all non-H atoms of the rings of entities B and D = 0.283 Å], which are related to those in (IIb), are observed (Fig. 10). Molecules B and D are arranged alternately and form hydrogen-bonded chains, characterized by R22(8) N—H···O interactions, running in the direction of the c axis. In contrast with (IIb), adjacent chains are linked to form layers by O—H···O interactions of the short acid bridge. Furthermore, the DMCs X in (IIc) connect both layer structures via two N—H···O interactions to form a three-dimensional network, while in (IIb) double layers are formed.

In order to study the preferred conformation of the CH—CH2O torsion angle in (I) and the N—C—CO torsion angle in (II), a Cambridge Structural Database (CSD, Version 5.32 of November 2010 plus five updates; Allen, 2002) substructure search for hydantoin derivatives [(I)] and for orotic acid [(II)] was undertaken. The search for (I) did not yield comparable structures, while for (II), excluding metal-coordinated orotic acid molecules, four entries containing orotate [CSD refcodes AMOROT (Solbakk, 1971), HOXHEI (Nichol & Clegg, 2009), KEDZEZ (Nichol & Clegg, 2006) and TUWCOE (Portalone, 2010)] and two entries with orotic acid molecules [OROTAC (Takusagawa & Shimada, 1973) and OROTAC01 (Portalone, 2008)] were found. In addition, a cocrystal of orotate [Neutral orotic acid?] with pyrimethamine has been reported recently by our group (Tutughamiarso & Bolte, 2011). All CSD entries confirm the synperiplanar conformation between the N atom and the carbonyl O atom, as shown in (IIb) and (IIc). This result is in agreement with a DFT calculation (Bekiroglu & Kristiansson, 2002). In contrast, only the antiperiplanar conformation could be observed in (IIa).

Related literature top

For related literature, see: Allen (2002); Almarsson & Zaworotko (2004); Bekiroglu & Kristiansson (2002); Bernstein et al. (1995); Blagden et al. (2007, 2008); Ghosh et al. (2011); Nichol & Clegg (2006, 2009); Portalone (2008, 2010); Rodríguez-Cuamatzi, Arillo-Flores, Bernal-Uruchurtu & Höpfl (2007); Seaton & Parkin (2011); Solbakk (1971); Takusagawa & Shimada (1973); Tutughamiarso & Bolte (2011); Vishweshwar et al. (2005).

Experimental top

Solvent evaporation experiments with a racemic mixture of commercially available hydantoin-5-acetic acid (5.2 mg, 0.033 mmol) in H2O (250 µl) at room temperature yielded one crystal, (I). Three single crystals of (II) were obtained during crystallization attempts with commercially available orotic acid [(IIa): 2.1 mg, 0.014 mmol in DMSO (50 µl) at room temperature; (IIb): 1.7 mg, 0.011 mmol in DMF (150 µl) at room temperature; (IIc): 4.5 mg, 0.029 mmol in DMF (450 µl) at 277 K].

Refinement top

The H atoms of (I), (IIa) and (IIb) were initially located in difference Fourier syntheses, while in (IIc) the H atom of the carboxylic acid group between molecules B and D, and two of the six DMC H atoms, could not be observed. Since both molecules B and D show bond lengths indicative of single and double bonds, the H atom of the carboxylic acid group was placed in the middle of the two O atoms, with Uiso(H) = 1.5Ueq(O43B).

H atoms bonded to C atoms in all structures were refined using a riding model, with methyl C—H = 0.98, secondary C—H = 0.99 and aromatic C—H = 0.95 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H or 1.2Ueq(C) for secondary and aromatic H. In (I), (IIa) and (IIb), H atoms bonded to N and O atoms were refined isotropically, while in (IIc) they were refined using a riding model, with amide N—H = 0.88 Å and protonated N—H = 0.92 Å, and with Uiso(H) = 1.2Ueq(N).

Due to the weak anomalous signals in the racemic mixture of (I) and in (IIc), 452 Friedel pairs for (I) and 2966 Friedel pairs for (IIc) were merged before refinement. The absolute structures of (I) and (IIc) were not determined.

The displacement ellipsoids of (IIc) (Fig. 8) are significantly enlarged, although the data for this compound were definitely collected at 173 K. The only explanation we have for this is that the molecules in the crystals are not perfectly ordered but adopt slightly different positions in different unit cells.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001) for (I), (IIa), (IIc); SMART (Siemens, 1994) for (IIb). Cell refinement: X-AREA (Stoe & Cie, 2001) for (I), (IIa), (IIc); SAINT (Siemens, 1994) for (IIb). Data reduction: X-AREA (Stoe & Cie, 2001) for (I), (IIa), (IIc); SAINT (Siemens, 1994) for (IIb). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram for (I). Only H atoms which participate in hydrogen bonds are shown. Hydrogen bonds are drawn as dashed lines. [Symmetry codes: (i) -x + 1, y - 1/2, -z + 1/2; (ii) x + 1/2, -y + 3/2, -z + 1; (iii) x - 1, y, z.]
[Figure 3] Fig. 3. A partial packing diagram for (I), viewed along the a axis (red in the electronic version of the paper, pointing to the far side); the b axis (in green) points from left to right and the c axis (in blue) points downwards. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds.
[Figure 4] Fig. 4. A perspective view of (IIa), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The hydrogen bond is shown as a dashed line.
[Figure 5] Fig. 5. A partial packing diagram for (IIa). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x + 2, -y - 1, -z + 1; (ii) -x + 1, -y + 1, -z + 1.]
[Figure 6] Fig. 6. A perspective view of (IIb), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 7] Fig. 7. A partial packing diagram for (IIb). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) x - 1, y, z + 1; (iii) x + 1, y, z - 1; (iv) x, y - 1, z - 1.]
[Figure 8] Fig. 8. A perspective view of (IIc), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 9] Fig. 9. A partial packing diagram for (IIc), showing the layer built of entities A, C, Y and Z. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x + 1, y - 1/2, -z + 2; (ii) -x + 1, y - 1/2, -z + 1; (v) -x + 1, y + 1/2, -z + 1; (vi) -x + 1, y + 1/2, -z + 2.]
[Figure 10] Fig. 10. A partial packing diagram for (IIc), showing the layer built of entities B, D and X. Only H atoms which participate in hydrogen bonds are shown. Hydrogen bonds are drawn as dashed lines. [Symmetry codes: (iv) -x + 2, y + 1/2, -z + 1; (vii) -x + 2, y - 1/2, -z + 1.]
(I) 2-(2,5-dioxoimidazolidin-4-yl)acetic acid top
Crystal data top
C5H6N2O4F(000) = 328
Mr = 158.12Dx = 1.725 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7026 reflections
a = 7.6148 (5) Åθ = 3.2–26.0°
b = 8.5592 (6) ŵ = 0.15 mm1
c = 9.3406 (6) ÅT = 173 K
V = 608.79 (7) Å3Block, colourless
Z = 40.50 × 0.10 × 0.10 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
607 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.107
Graphite monochromatorθmax = 25.7°, θmin = 3.2°
ω scansh = 99
10371 measured reflectionsk = 1010
692 independent reflectionsl = 1111
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)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.0331P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
692 reflectionsΔρmax = 0.14 e Å3
113 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.074 (8)
Crystal data top
C5H6N2O4V = 608.79 (7) Å3
Mr = 158.12Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.6148 (5) ŵ = 0.15 mm1
b = 8.5592 (6) ÅT = 173 K
c = 9.3406 (6) Å0.50 × 0.10 × 0.10 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
607 reflections with I > 2σ(I)
10371 measured reflectionsRint = 0.107
692 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.055H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.14 e Å3
692 reflectionsΔρmin = 0.15 e Å3
113 parameters
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*/Ueq
N10.7709 (2)0.3562 (2)0.39865 (18)0.0166 (4)
H10.754 (3)0.262 (3)0.371 (3)0.028 (7)*
C20.9253 (3)0.4268 (2)0.3742 (2)0.0169 (5)
O211.05432 (19)0.37022 (17)0.31350 (16)0.0237 (4)
N30.9153 (2)0.57583 (19)0.43026 (18)0.0169 (4)
H31.005 (3)0.646 (3)0.425 (3)0.027 (7)*
C40.7561 (3)0.6037 (2)0.4920 (2)0.0159 (4)
O410.71109 (19)0.72508 (17)0.54961 (16)0.0219 (4)
C50.6520 (3)0.4518 (2)0.4832 (2)0.0148 (4)
H50.64330.40600.58140.018*
C510.4675 (3)0.4669 (2)0.4217 (2)0.0153 (5)
H51A0.41590.36130.41220.018*
H51B0.39400.52640.49010.018*
C520.4614 (3)0.5467 (2)0.2786 (2)0.0148 (4)
O530.58083 (19)0.62326 (17)0.22980 (16)0.0230 (4)
O540.31095 (19)0.53338 (18)0.20578 (15)0.0195 (4)
H540.224 (4)0.466 (4)0.261 (4)0.066 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0142 (9)0.0115 (9)0.0240 (9)0.0006 (7)0.0015 (7)0.0023 (8)
C20.0158 (11)0.0159 (10)0.0191 (10)0.0013 (9)0.0040 (9)0.0003 (8)
O210.0129 (7)0.0236 (8)0.0345 (8)0.0015 (7)0.0029 (7)0.0079 (7)
N30.0129 (8)0.0144 (9)0.0233 (9)0.0007 (7)0.0012 (7)0.0015 (7)
C40.0143 (10)0.0155 (10)0.0180 (9)0.0009 (8)0.0032 (8)0.0011 (8)
O410.0172 (7)0.0188 (7)0.0297 (8)0.0020 (6)0.0006 (7)0.0071 (7)
C50.0141 (10)0.0144 (10)0.0159 (10)0.0003 (8)0.0005 (8)0.0020 (9)
C510.0128 (9)0.0167 (10)0.0164 (10)0.0013 (8)0.0001 (8)0.0022 (9)
C520.0135 (9)0.0145 (10)0.0165 (10)0.0025 (8)0.0013 (8)0.0011 (9)
O530.0192 (8)0.0266 (8)0.0233 (8)0.0028 (7)0.0018 (6)0.0070 (7)
O540.0174 (7)0.0223 (8)0.0187 (7)0.0001 (6)0.0048 (6)0.0011 (7)
Geometric parameters (Å, º) top
N1—C21.341 (3)C5—C511.523 (3)
N1—C51.454 (3)C5—H51.0000
N1—H10.86 (3)C51—C521.502 (3)
C2—O211.233 (3)C51—H51A0.9900
C2—N31.381 (3)C51—H51B0.9900
N3—C41.363 (3)C52—O531.210 (2)
N3—H30.91 (3)C52—O541.337 (3)
C4—O411.219 (3)O54—H541.02 (4)
C4—C51.525 (3)
C2—N1—C5112.65 (17)C51—C5—C4115.33 (17)
C2—N1—H1120.3 (16)N1—C5—H5108.6
C5—N1—H1126.9 (16)C51—C5—H5108.6
O21—C2—N1126.87 (19)C4—C5—H5108.6
O21—C2—N3125.50 (19)C52—C51—C5113.74 (17)
N1—C2—N3107.63 (18)C52—C51—H51A108.8
C4—N3—C2111.78 (17)C5—C51—H51A108.8
C4—N3—H3125.1 (16)C52—C51—H51B108.8
C2—N3—H3123.1 (16)C5—C51—H51B108.8
O41—C4—N3125.84 (18)H51A—C51—H51B107.7
O41—C4—C5127.18 (19)O53—C52—O54119.92 (18)
N3—C4—C5106.88 (16)O53—C52—C51123.91 (19)
N1—C5—C51114.69 (16)O54—C52—C51116.14 (18)
N1—C5—C4100.69 (16)C52—O54—H54110 (2)
C5—N1—C2—O21175.3 (2)O41—C4—C5—N1178.0 (2)
C5—N1—C2—N34.4 (2)N3—C4—C5—N15.6 (2)
O21—C2—N3—C4179.3 (2)O41—C4—C5—C5153.9 (3)
N1—C2—N3—C40.3 (2)N3—C4—C5—C51129.59 (17)
C2—N3—C4—O41180.0 (2)N1—C5—C51—C5263.1 (2)
C2—N3—C4—C53.5 (2)C4—C5—C51—C5253.2 (2)
C2—N1—C5—C51130.58 (18)C5—C51—C52—O5316.0 (3)
C2—N1—C5—C46.1 (2)C5—C51—C52—O54166.01 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O54i0.86 (3)2.14 (3)2.996 (2)175 (2)
N3—H3···O41ii0.91 (3)1.93 (3)2.831 (2)168 (2)
O54—H54···O21iii1.02 (4)1.61 (4)2.604 (2)165 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) x1, y, z.
(IIa) 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid dimethyl sulfoxide monosolvate top
Crystal data top
C5H4N2O4·C2H6OSF(000) = 488
Mr = 234.23Dx = 1.570 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9844 reflections
a = 9.3710 (6) Åθ = 3.4–26.0°
b = 5.9752 (3) ŵ = 0.33 mm1
c = 17.8433 (13) ÅT = 173 K
β = 97.447 (6)°Block, colourless
V = 990.68 (11) Å30.35 × 0.25 × 0.20 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
1865 independent reflections
Radiation source: fine-focus sealed tube1383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
ω scansθmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan
(MULABS; Blessing, 1995; Spek, 2009)
h = 1111
Tmin = 0.893, Tmax = 0.937k = 77
18676 measured reflectionsl = 2121
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0406P)2]
where P = (Fo2 + 2Fc2)/3
1865 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C5H4N2O4·C2H6OSV = 990.68 (11) Å3
Mr = 234.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3710 (6) ŵ = 0.33 mm1
b = 5.9752 (3) ÅT = 173 K
c = 17.8433 (13) Å0.35 × 0.25 × 0.20 mm
β = 97.447 (6)°
Data collection top
Stoe IPDS II two-circle
diffractometer
1865 independent reflections
Absorption correction: multi-scan
(MULABS; Blessing, 1995; Spek, 2009)
1383 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.937Rint = 0.076
18676 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.17 e Å3
1865 reflectionsΔρmin = 0.32 e Å3
150 parameters
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*/Ueq
N10.89572 (19)0.2416 (3)0.51608 (8)0.0217 (4)
H10.960 (3)0.319 (4)0.5367 (13)0.038 (7)*
C20.8290 (2)0.3166 (3)0.44711 (10)0.0226 (4)
O210.86777 (16)0.4924 (2)0.41954 (7)0.0319 (4)
C30.7156 (2)0.1743 (3)0.41215 (10)0.0233 (4)
H30.66580.21190.36400.028*
C40.68033 (19)0.0119 (3)0.44777 (9)0.0195 (4)
C410.5632 (2)0.1634 (3)0.41131 (10)0.0211 (4)
O420.50315 (17)0.1265 (3)0.34854 (8)0.0407 (4)
O430.53739 (16)0.3326 (2)0.45316 (7)0.0321 (4)
H430.465 (3)0.428 (5)0.4243 (15)0.062 (8)*
N50.74985 (17)0.0713 (3)0.51739 (8)0.0212 (3)
H50.720 (3)0.201 (4)0.5416 (13)0.043 (7)*
C60.86277 (19)0.0504 (3)0.55333 (9)0.0199 (4)
O610.92976 (15)0.0044 (2)0.61383 (7)0.0271 (3)
C1X0.1119 (3)0.4769 (4)0.29052 (12)0.0419 (6)
H1X10.10140.32750.31170.063*
H1X20.07110.47760.23710.063*
H1X30.06100.58640.31820.063*
S2X0.29746 (6)0.54840 (9)0.29868 (3)0.03026 (15)
O21X0.34198 (15)0.5853 (2)0.38341 (7)0.0321 (4)
C3X0.2768 (2)0.8194 (4)0.25787 (11)0.0320 (5)
H3X10.21980.91280.28790.048*
H3X20.22760.80750.20610.048*
H3X30.37180.88730.25700.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0236 (9)0.0208 (8)0.0195 (8)0.0085 (7)0.0023 (7)0.0004 (6)
C20.0247 (10)0.0212 (10)0.0212 (9)0.0041 (8)0.0002 (8)0.0013 (8)
O210.0368 (8)0.0266 (8)0.0293 (7)0.0146 (6)0.0073 (6)0.0092 (6)
C30.0244 (10)0.0240 (11)0.0201 (9)0.0031 (8)0.0030 (7)0.0015 (7)
C40.0187 (9)0.0202 (11)0.0195 (8)0.0016 (7)0.0021 (7)0.0019 (7)
C410.0196 (10)0.0210 (10)0.0223 (9)0.0023 (8)0.0010 (7)0.0014 (7)
O420.0487 (10)0.0369 (9)0.0304 (8)0.0162 (7)0.0183 (7)0.0087 (7)
O430.0352 (9)0.0357 (9)0.0227 (7)0.0210 (7)0.0069 (6)0.0067 (6)
N50.0224 (9)0.0208 (9)0.0195 (7)0.0057 (7)0.0007 (6)0.0006 (7)
C60.0219 (10)0.0191 (9)0.0187 (9)0.0041 (8)0.0021 (7)0.0024 (8)
O610.0317 (8)0.0263 (8)0.0208 (6)0.0051 (6)0.0058 (5)0.0038 (5)
C1X0.0525 (15)0.0376 (14)0.0309 (11)0.0141 (11)0.0122 (10)0.0080 (10)
S2X0.0388 (3)0.0310 (3)0.0189 (2)0.0155 (2)0.00447 (19)0.0020 (2)
O21X0.0366 (9)0.0380 (9)0.0186 (7)0.0187 (7)0.0083 (6)0.0033 (6)
C3X0.0335 (12)0.0346 (12)0.0264 (10)0.0003 (10)0.0012 (9)0.0037 (9)
Geometric parameters (Å, º) top
N1—C61.377 (2)N5—C61.372 (2)
N1—C21.381 (2)N5—H50.95 (3)
N1—H10.81 (3)C6—O611.221 (2)
C2—O211.235 (2)C1X—S2X1.778 (2)
C2—C31.438 (3)C1X—H1X10.9800
C3—C41.344 (3)C1X—H1X20.9800
C3—H30.9500C1X—H1X30.9800
C4—N51.373 (2)S2X—O21X1.5313 (12)
C4—C411.504 (2)S2X—C3X1.775 (2)
C41—O421.207 (2)C3X—H3X10.9800
C41—O431.298 (2)C3X—H3X20.9800
O43—H430.98 (3)C3X—H3X30.9800
C6—N1—C2126.55 (16)O61—C6—N5123.24 (17)
C6—N1—H1116.9 (17)O61—C6—N1121.83 (17)
C2—N1—H1116.5 (17)N5—C6—N1114.93 (15)
O21—C2—N1120.57 (17)S2X—C1X—H1X1109.5
O21—C2—C3124.69 (16)S2X—C1X—H1X2109.5
N1—C2—C3114.74 (16)H1X1—C1X—H1X2109.5
C4—C3—C2119.84 (16)S2X—C1X—H1X3109.5
C4—C3—H3120.1H1X1—C1X—H1X3109.5
C2—C3—H3120.1H1X2—C1X—H1X3109.5
C3—C4—N5121.67 (16)O21X—S2X—C3X105.96 (9)
C3—C4—C41120.30 (16)O21X—S2X—C1X104.71 (9)
N5—C4—C41118.03 (15)C3X—S2X—C1X97.59 (10)
O42—C41—O43125.26 (17)S2X—C3X—H3X1109.5
O42—C41—C4121.16 (16)S2X—C3X—H3X2109.5
O43—C41—C4113.57 (15)H3X1—C3X—H3X2109.5
C41—O43—H43108.7 (16)S2X—C3X—H3X3109.5
C4—N5—C6122.19 (16)H3X1—C3X—H3X3109.5
C4—N5—H5119.2 (14)H3X2—C3X—H3X3109.5
C6—N5—H5118.6 (14)
C6—N1—C2—O21179.51 (18)C3—C4—C41—O43177.81 (17)
C6—N1—C2—C30.9 (3)N5—C4—C41—O432.9 (2)
O21—C2—C3—C4178.84 (19)C3—C4—N5—C62.6 (3)
N1—C2—C3—C41.6 (3)C41—C4—N5—C6176.69 (16)
C2—C3—C4—N50.1 (3)C4—N5—C6—O61176.99 (17)
C2—C3—C4—C41179.23 (17)C4—N5—C6—N13.2 (3)
C3—C4—C41—O423.2 (3)C2—N1—C6—O61178.73 (18)
N5—C4—C41—O42176.17 (18)C2—N1—C6—N51.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O21i0.81 (3)2.04 (3)2.846 (2)175 (2)
N5—H5···O21Xii0.95 (3)1.99 (3)2.912 (2)164 (2)
O43—H43···O21X0.98 (3)1.59 (3)2.5675 (18)176 (2)
Symmetry codes: (i) x+2, y1, z+1; (ii) x+1, y+1, z+1.
(IIb) dimethylammonium 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid top
Crystal data top
C2H8N+·C5H3N2O4·C5H4N2O4Z = 2
Mr = 357.29F(000) = 372
Triclinic, P1Dx = 1.615 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.111 (1) ÅCell parameters from 1108 reflections
b = 8.9503 (11) Åθ = 3.0–25.0°
c = 11.6804 (15) ŵ = 0.14 mm1
α = 112.366 (3)°T = 173 K
β = 97.263 (2)°Block, colourless
γ = 104.621 (2)°0.20 × 0.20 × 0.10 mm
V = 734.94 (16) Å3
Data collection top
Siemens SMART three-circle
diffractometer
1341 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
ω scansh = 99
4208 measured reflectionsk = 109
2555 independent reflectionsl = 013
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 0.86 w = 1/[σ2(Fo2) + (0.0314P)2]
where P = (Fo2 + 2Fc2)/3
2555 reflections(Δ/σ)max = 0.001
254 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C2H8N+·C5H3N2O4·C5H4N2O4γ = 104.621 (2)°
Mr = 357.29V = 734.94 (16) Å3
Triclinic, P1Z = 2
a = 8.111 (1) ÅMo Kα radiation
b = 8.9503 (11) ŵ = 0.14 mm1
c = 11.6804 (15) ÅT = 173 K
α = 112.366 (3)°0.20 × 0.20 × 0.10 mm
β = 97.263 (2)°
Data collection top
Siemens SMART three-circle
diffractometer
1341 reflections with I > 2σ(I)
4208 measured reflectionsRint = 0.072
2555 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 0.86Δρmax = 0.25 e Å3
2555 reflectionsΔρmin = 0.30 e Å3
254 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.3067 (3)0.5065 (3)0.9463 (2)0.0156 (5)
H1A0.246 (5)0.516 (4)1.011 (3)0.051 (12)*
C2A0.2633 (3)0.3452 (3)0.8476 (2)0.0157 (5)
O21A0.1483 (3)0.2228 (2)0.84705 (18)0.0226 (5)
C3A0.3581 (4)0.3324 (4)0.7507 (3)0.0173 (5)
H3A0.33890.22470.68200.021*
C4A0.4745 (4)0.4744 (3)0.7582 (3)0.0183 (6)
C41A0.5780 (4)0.4822 (3)0.6587 (2)0.0187 (6)
O42A0.6688 (3)0.6239 (2)0.6744 (2)0.0270 (5)
O43A0.5591 (2)0.3367 (2)0.56875 (19)0.0216 (4)
N5A0.5078 (3)0.6319 (3)0.8588 (2)0.0167 (5)
H5A0.585 (4)0.716 (4)0.859 (3)0.022 (8)*
C6A0.4281 (3)0.6537 (3)0.9579 (2)0.0151 (5)
O61A0.4608 (2)0.7915 (2)1.04936 (17)0.0218 (5)
N1B0.9550 (3)0.2335 (3)0.0314 (2)0.0189 (5)
H1B1.003 (4)0.230 (4)0.033 (3)0.034 (10)*
C2B1.0178 (3)0.3844 (3)0.1408 (2)0.0172 (6)
O21B1.1311 (2)0.5086 (2)0.14177 (16)0.0216 (4)
C3B0.9408 (4)0.3862 (3)0.2447 (2)0.0192 (6)
H3B0.97670.48670.32280.023*
C4B0.8181 (3)0.2451 (3)0.2306 (2)0.0161 (5)
C41B0.7279 (3)0.2328 (3)0.3331 (3)0.0193 (6)
O42B0.6337 (3)0.0945 (3)0.3206 (2)0.0401 (6)
O43B0.7568 (3)0.3775 (2)0.4296 (2)0.0317 (5)
H430.654 (6)0.361 (5)0.485 (4)0.075 (14)*
N5B0.7646 (3)0.0966 (3)0.1194 (2)0.0200 (5)
H5B0.684 (5)0.010 (4)0.109 (3)0.041 (10)*
C6B0.8285 (3)0.0856 (3)0.0153 (2)0.0164 (6)
O61B0.7798 (2)0.0441 (2)0.08620 (17)0.0226 (4)
C1X0.7368 (4)0.0946 (4)0.3393 (3)0.0408 (9)
H1X10.63900.11870.30270.061*
H1X20.72050.09470.42380.061*
H1X30.84780.18260.28320.061*
N2X0.7416 (3)0.0753 (3)0.3516 (3)0.0283 (6)
H2X10.749 (6)0.073 (6)0.260 (5)0.105 (18)*
H2X20.633 (5)0.152 (4)0.402 (3)0.041 (10)*
C3X0.8856 (4)0.1228 (4)0.4060 (3)0.0344 (7)
H3X10.88230.23540.41110.052*
H3X20.99880.03770.35110.052*
H3X30.87140.12670.49180.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0139 (12)0.0143 (12)0.0151 (13)0.0001 (9)0.0087 (10)0.0040 (11)
C2A0.0110 (12)0.0172 (12)0.0199 (13)0.0045 (8)0.0087 (10)0.0075 (11)
O21A0.0230 (11)0.0191 (9)0.0241 (11)0.0024 (7)0.0153 (9)0.0074 (8)
C3A0.0213 (12)0.0164 (11)0.0178 (13)0.0039 (8)0.0130 (10)0.0102 (11)
C4A0.0203 (14)0.0201 (12)0.0108 (12)0.0073 (10)0.0025 (10)0.0029 (9)
C41A0.0147 (11)0.0252 (13)0.0146 (14)0.0055 (8)0.0021 (10)0.0082 (11)
O42A0.0303 (12)0.0188 (9)0.0290 (11)0.0009 (8)0.0166 (9)0.0090 (9)
O43A0.0231 (10)0.0197 (8)0.0177 (11)0.0043 (6)0.0127 (8)0.0029 (8)
N5A0.0145 (11)0.0151 (11)0.0178 (12)0.0009 (8)0.0089 (9)0.0062 (9)
C6A0.0120 (13)0.0184 (12)0.0148 (13)0.0035 (9)0.0027 (10)0.0080 (10)
O61A0.0243 (10)0.0161 (10)0.0197 (10)0.0030 (7)0.0104 (8)0.0029 (8)
N1B0.0222 (13)0.0189 (11)0.0136 (12)0.0053 (9)0.0102 (11)0.0041 (9)
C2B0.0192 (14)0.0171 (12)0.0149 (12)0.0073 (11)0.0049 (11)0.0054 (9)
O21B0.0242 (11)0.0185 (9)0.0166 (10)0.0009 (7)0.0084 (8)0.0058 (9)
C3B0.0220 (14)0.0188 (14)0.0098 (14)0.0063 (10)0.0052 (11)0.0013 (12)
C4B0.0178 (12)0.0161 (11)0.0105 (13)0.0057 (9)0.0034 (9)0.0019 (9)
C41B0.0149 (14)0.0245 (12)0.0175 (15)0.0056 (9)0.0108 (11)0.0064 (12)
O42B0.0513 (16)0.0246 (11)0.0344 (13)0.0036 (9)0.0303 (11)0.0066 (9)
O43B0.0286 (11)0.0259 (11)0.0273 (12)0.0045 (8)0.0187 (9)0.0026 (9)
N5B0.0199 (14)0.0160 (10)0.0197 (13)0.0009 (9)0.0090 (11)0.0062 (9)
C6B0.0188 (15)0.0150 (11)0.0192 (15)0.0045 (10)0.0125 (13)0.0094 (11)
O61B0.0252 (11)0.0147 (9)0.0178 (11)0.0009 (7)0.0116 (8)0.0008 (9)
C1X0.0339 (17)0.0243 (14)0.066 (3)0.0073 (11)0.0125 (18)0.0230 (17)
N2X0.0256 (14)0.0259 (11)0.0305 (16)0.0010 (9)0.0079 (12)0.0137 (11)
C3X0.0266 (18)0.0341 (15)0.039 (2)0.0054 (11)0.0147 (15)0.0129 (15)
Geometric parameters (Å, º) top
N1A—C6A1.378 (3)C3B—H3B0.9500
N1A—C2A1.383 (3)C4B—N5B1.376 (3)
N1A—H1A0.95 (4)C4B—C41B1.504 (4)
C2A—O21A1.244 (3)C41B—O42B1.222 (3)
C2A—C3A1.432 (4)C41B—O43B1.293 (3)
C3A—C4A1.343 (3)O43B—H431.13 (4)
C3A—H3A0.9500N5B—C6B1.360 (4)
C4A—N5A1.381 (3)N5B—H5B0.83 (3)
C4A—C41A1.529 (4)C6B—O61B1.230 (3)
C41A—O42A1.226 (3)C1X—N2X1.482 (3)
C41A—O43A1.281 (3)C1X—H1X10.9800
N5A—C6A1.370 (4)C1X—H1X20.9800
N5A—H5A0.84 (3)C1X—H1X30.9800
C6A—O61A1.222 (3)N2X—C3X1.478 (4)
N1B—C2B1.375 (3)N2X—H2X11.06 (5)
N1B—C6B1.384 (3)N2X—H2X20.92 (3)
N1B—H1B0.88 (3)C3X—H3X10.9800
C2B—O21B1.246 (3)C3X—H3X20.9800
C2B—C3B1.430 (4)C3X—H3X30.9800
C3B—C4B1.334 (3)
C6A—N1A—C2A126.2 (2)C3B—C4B—N5B122.0 (2)
C6A—N1A—H1A117 (2)C3B—C4B—C41B123.7 (2)
C2A—N1A—H1A116 (2)N5B—C4B—C41B114.3 (2)
O21A—C2A—N1A120.0 (2)O42B—C41B—O43B125.1 (3)
O21A—C2A—C3A124.3 (3)O42B—C41B—C4B120.4 (2)
N1A—C2A—C3A115.7 (2)O43B—C41B—C4B114.5 (2)
C4A—C3A—C2A119.3 (3)C41B—O43B—H43109 (2)
C4A—C3A—H3A120.4C6B—N5B—C4B122.4 (2)
C2A—C3A—H3A120.4C6B—N5B—H5B115 (2)
C3A—C4A—N5A121.4 (3)C4B—N5B—H5B122 (3)
C3A—C4A—C41A125.2 (2)O61B—C6B—N5B123.7 (2)
N5A—C4A—C41A113.4 (2)O61B—C6B—N1B121.5 (2)
O42A—C41A—O43A128.0 (3)N5B—C6B—N1B114.8 (2)
O42A—C41A—C4A117.2 (2)N2X—C1X—H1X1109.5
O43A—C41A—C4A114.8 (2)N2X—C1X—H1X2109.5
C41A—O43A—H43109.2 (16)H1X1—C1X—H1X2109.5
C6A—N5A—C4A122.8 (2)N2X—C1X—H1X3109.5
C6A—N5A—H5A120 (2)H1X1—C1X—H1X3109.5
C4A—N5A—H5A117 (2)H1X2—C1X—H1X3109.5
O61A—C6A—N5A123.3 (2)C1X—N2X—C3X113.4 (2)
O61A—C6A—N1A122.2 (3)C1X—N2X—H2X1107 (2)
N5A—C6A—N1A114.4 (2)C3X—N2X—H2X1112 (3)
C2B—N1B—C6B125.8 (2)C1X—N2X—H2X2105.6 (19)
C2B—N1B—H1B117 (2)C3X—N2X—H2X2111 (2)
C6B—N1B—H1B117 (2)H2X1—N2X—H2X2107 (3)
O21B—C2B—N1B119.1 (2)N2X—C3X—H3X1109.5
O21B—C2B—C3B125.1 (2)N2X—C3X—H3X2109.5
N1B—C2B—C3B115.8 (2)H3X1—C3X—H3X2109.5
C4B—C3B—C2B119.2 (2)N2X—C3X—H3X3109.5
C4B—C3B—H3B120.4H3X1—C3X—H3X3109.5
C2B—C3B—H3B120.4H3X2—C3X—H3X3109.5
C6A—N1A—C2A—O21A178.5 (2)C6B—N1B—C2B—O21B179.4 (2)
C6A—N1A—C2A—C3A1.6 (4)C6B—N1B—C2B—C3B1.3 (3)
O21A—C2A—C3A—C4A177.3 (2)O21B—C2B—C3B—C4B178.8 (2)
N1A—C2A—C3A—C4A2.8 (4)N1B—C2B—C3B—C4B0.9 (3)
C2A—C3A—C4A—N5A1.5 (4)C2B—C3B—C4B—N5B0.8 (4)
C2A—C3A—C4A—C41A176.6 (2)C2B—C3B—C4B—C41B179.68 (19)
C3A—C4A—C41A—O42A174.4 (3)C3B—C4B—C41B—O42B170.5 (3)
N5A—C4A—C41A—O42A3.9 (3)N5B—C4B—C41B—O42B9.0 (3)
C3A—C4A—C41A—O43A6.3 (4)C3B—C4B—C41B—O43B10.7 (3)
N5A—C4A—C41A—O43A175.5 (2)N5B—C4B—C41B—O43B169.8 (2)
C3A—C4A—N5A—C6A1.2 (3)C3B—C4B—N5B—C6B2.3 (4)
C41A—C4A—N5A—C6A179.6 (2)C41B—C4B—N5B—C6B178.1 (2)
C4A—N5A—C6A—O61A177.6 (2)C4B—N5B—C6B—O61B178.2 (2)
C4A—N5A—C6A—N1A2.4 (3)C4B—N5B—C6B—N1B1.8 (4)
C2A—N1A—C6A—O61A179.0 (2)C2B—N1B—C6B—O61B180.0 (2)
C2A—N1A—C6A—N5A1.0 (3)C2B—N1B—C6B—N5B0.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O21Bi0.95 (4)1.90 (4)2.836 (3)172 (3)
N5A—H5A···O61Bii0.84 (3)2.12 (3)2.947 (3)165 (3)
N1B—H1B···O21Aiii0.88 (3)1.94 (3)2.807 (3)169 (3)
O43B—H43···O43A1.13 (4)1.37 (4)2.482 (3)167 (4)
N5B—H5B···O61Aiv0.83 (3)2.11 (3)2.931 (3)169 (3)
N2X—H2X1···O61B1.06 (5)1.92 (5)2.973 (3)174 (4)
N2X—H2X2···O43Av0.92 (3)2.11 (3)2.982 (3)159 (3)
Symmetry codes: (i) x1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z1; (iv) x, y1, z1; (v) x+1, y, z.
(IIc) tris(dimethylammonium) tris(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate) 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid top
Crystal data top
3C2H8N+·3C5H3N2O4·C5H4N2O4F(000) = 796
Mr = 759.67Dx = 1.551 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7480 reflections
a = 7.0176 (14) Åθ = 3.4–25.9°
b = 18.026 (4) ŵ = 0.13 mm1
c = 12.906 (3) ÅT = 173 K
β = 94.94 (3)°Plate, colourless
V = 1626.5 (6) Å30.18 × 0.16 × 0.06 mm
Z = 2
Data collection top
Stoe IPDS II two-circle
diffractometer
2207 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.091
Genix 3D multilayer optics monochromatorθmax = 25.0°, θmin = 3.4°
ω scansh = 88
15886 measured reflectionsk = 2121
2968 independent reflectionsl = 1515
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)] = 0.065H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0963P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2968 reflectionsΔρmax = 0.30 e Å3
479 parametersΔρmin = 0.31 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (4)
Crystal data top
3C2H8N+·3C5H3N2O4·C5H4N2O4V = 1626.5 (6) Å3
Mr = 759.67Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.0176 (14) ŵ = 0.13 mm1
b = 18.026 (4) ÅT = 173 K
c = 12.906 (3) Å0.18 × 0.16 × 0.06 mm
β = 94.94 (3)°
Data collection top
Stoe IPDS II two-circle
diffractometer
2207 reflections with I > 2σ(I)
15886 measured reflectionsRint = 0.091
2968 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0651 restraint
wR(F2) = 0.169H-atom parameters constrained
S = 1.02Δρmax = 0.30 e Å3
2968 reflectionsΔρmin = 0.31 e Å3
479 parameters
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*/Ueq
N1A0.5478 (9)0.1209 (3)0.8501 (5)0.0726 (14)
H1A0.56890.08770.89980.087*
C2A0.4817 (11)0.1885 (4)0.8787 (5)0.0698 (15)
O21A0.4495 (9)0.1988 (3)0.9713 (4)0.0786 (13)
C3A0.4514 (11)0.2422 (4)0.7965 (5)0.0706 (15)
H3A0.40780.29070.81060.085*
C4A0.4857 (11)0.2226 (4)0.6998 (6)0.0707 (15)
C41A0.4582 (11)0.2755 (4)0.6077 (6)0.0728 (16)
O42A0.4646 (10)0.2489 (3)0.5195 (4)0.0869 (15)
O43A0.4359 (9)0.3425 (3)0.6311 (4)0.0804 (13)
N5A0.5457 (9)0.1528 (3)0.6766 (5)0.0709 (13)
H5A0.55980.14170.61130.085*
C6A0.5849 (12)0.0994 (4)0.7515 (6)0.0744 (17)
O61A0.6483 (9)0.0386 (3)0.7327 (4)0.0813 (13)
N1B0.9926 (10)0.6659 (3)0.0180 (5)0.0709 (13)
H1B1.01600.69910.06520.085*
C2B0.9659 (11)0.5947 (4)0.0513 (6)0.0721 (16)
O21B0.9672 (8)0.5786 (3)0.1452 (4)0.0777 (12)
C3B0.9387 (11)0.5408 (4)0.0285 (5)0.0710 (16)
H3B0.92400.48980.01140.085*
C4B0.9344 (11)0.5636 (3)0.1280 (5)0.0683 (15)
C41B0.8977 (11)0.5112 (4)0.2152 (6)0.0711 (16)
O42B0.8692 (9)0.5348 (3)0.3000 (4)0.0810 (13)
O43B0.8973 (8)0.4426 (3)0.1851 (4)0.0745 (12)
H43B0.89150.39140.24570.112*
N5B0.9566 (9)0.6366 (3)0.1554 (5)0.0711 (14)
H5B0.95180.64950.22090.085*
C6B0.9865 (12)0.6908 (4)0.0821 (6)0.0750 (17)
O61B1.0074 (10)0.7572 (3)0.1050 (4)0.0865 (15)
N1C0.4892 (9)0.6574 (3)0.6523 (5)0.0708 (13)
H1C0.51590.69010.60500.085*
C2C0.4150 (10)0.5909 (4)0.6170 (6)0.0704 (15)
O21C0.3860 (8)0.5797 (3)0.5216 (4)0.0784 (13)
C3C0.3769 (11)0.5376 (4)0.6964 (5)0.0714 (16)
H3C0.32980.48970.67760.086*
C4C0.4087 (10)0.5566 (4)0.7966 (6)0.0686 (15)
C41C0.3723 (10)0.5057 (4)0.8854 (6)0.0695 (15)
O42C0.4194 (9)0.5276 (3)0.9757 (4)0.0809 (14)
O43C0.2976 (8)0.4428 (3)0.8593 (4)0.0749 (12)
N5C0.4787 (9)0.6252 (3)0.8262 (5)0.0692 (13)
H5C0.49400.63600.89290.083*
C6C0.5261 (12)0.6778 (4)0.7553 (6)0.0725 (16)
O61C0.5984 (9)0.7377 (3)0.7812 (4)0.0838 (14)
N1D1.0712 (9)0.1202 (3)0.5173 (5)0.0725 (14)
H1D1.11010.08800.56590.087*
C2D1.0083 (11)0.1883 (4)0.5484 (6)0.0760 (17)
O21D1.0007 (10)0.2003 (3)0.6430 (4)0.0858 (15)
C3D0.9573 (12)0.2411 (4)0.4673 (6)0.0748 (17)
H3D0.91850.28980.48400.090*
C4D0.9649 (10)0.2209 (4)0.3675 (6)0.0678 (15)
C41D0.9167 (11)0.2723 (4)0.2781 (5)0.0694 (15)
O42D0.9107 (8)0.2489 (3)0.1882 (4)0.0787 (13)
O43D0.8839 (8)0.3396 (3)0.3062 (4)0.0768 (13)
N5D1.0226 (9)0.1513 (3)0.3408 (5)0.0701 (13)
H5D1.02490.13970.27470.084*
C6D1.0772 (11)0.0991 (4)0.4157 (6)0.0720 (16)
O61D1.1343 (9)0.0365 (3)0.3941 (4)0.0819 (14)
C1X1.2307 (11)0.0877 (4)0.1829 (6)0.0783 (18)
H1X11.24920.04660.13510.117*
H1X21.20430.13340.14300.117*
H1X31.34670.09430.23000.117*
N2X1.0695 (9)0.0711 (3)0.2435 (5)0.0734 (14)
H2X10.96160.06370.19890.088*
H2X21.09410.02790.28020.088*
C3X1.0335 (14)0.1311 (4)0.3163 (7)0.086 (2)
H3X10.92410.11790.35490.129*
H3X21.14690.13820.36510.129*
H3X31.00540.17700.27740.129*
C1Y0.5844 (15)0.4151 (6)0.4069 (9)0.101 (3)
H1Y10.69840.43260.44910.152*
H1Y20.57390.44090.33990.152*
H1Y30.59490.36160.39530.152*
N2Y0.4141 (9)0.4303 (3)0.4615 (5)0.0730 (13)
H2Y10.42640.40670.52490.088*
H2Y20.40740.48050.47380.088*
C3Y0.2354 (14)0.4064 (6)0.4043 (8)0.098 (3)
H3Y10.12750.41870.44460.147*
H3Y20.23900.35270.39320.147*
H3Y30.22010.43180.33700.147*
C1Z0.5618 (12)0.3634 (6)1.0729 (8)0.091 (2)
H1Z10.65480.34591.02590.136*
H1Z20.58390.33801.14000.136*
H1Z30.57670.41701.08320.136*
N2Z0.3659 (9)0.3472 (3)1.0269 (5)0.0734 (14)
H2Z10.34740.37050.96340.088*
H2Z20.35470.29691.01550.088*
C3Z0.2167 (12)0.3706 (4)1.0912 (7)0.0815 (19)
H3Z10.09120.35851.05600.122*
H3Z20.22560.42431.10260.122*
H3Z30.23260.34491.15830.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.087 (4)0.069 (3)0.063 (3)0.012 (3)0.008 (3)0.001 (2)
C2A0.078 (4)0.065 (3)0.066 (4)0.003 (3)0.004 (3)0.003 (3)
O21A0.095 (4)0.076 (3)0.065 (3)0.006 (2)0.009 (2)0.003 (2)
C3A0.081 (4)0.067 (3)0.063 (3)0.006 (3)0.000 (3)0.005 (3)
C4A0.075 (4)0.063 (3)0.073 (4)0.002 (3)0.002 (3)0.001 (3)
C41A0.078 (4)0.071 (3)0.070 (4)0.005 (3)0.005 (3)0.007 (3)
O42A0.117 (5)0.078 (3)0.065 (3)0.009 (3)0.010 (3)0.002 (2)
O43A0.095 (4)0.074 (3)0.072 (3)0.000 (2)0.004 (3)0.002 (2)
N5A0.078 (4)0.067 (3)0.067 (3)0.010 (3)0.003 (3)0.001 (2)
C6A0.082 (5)0.074 (4)0.067 (4)0.007 (3)0.005 (3)0.001 (3)
O61A0.097 (4)0.074 (3)0.073 (3)0.011 (3)0.003 (3)0.001 (2)
N1B0.082 (4)0.065 (3)0.066 (3)0.002 (2)0.006 (3)0.006 (2)
C2B0.079 (4)0.069 (3)0.068 (4)0.000 (3)0.006 (3)0.003 (3)
O21B0.089 (3)0.076 (3)0.068 (3)0.003 (2)0.009 (2)0.000 (2)
C3B0.081 (4)0.067 (3)0.066 (4)0.004 (3)0.008 (3)0.002 (3)
C4B0.079 (4)0.063 (3)0.063 (3)0.003 (3)0.004 (3)0.005 (2)
C41B0.075 (4)0.065 (3)0.073 (4)0.004 (3)0.005 (3)0.000 (3)
O42B0.096 (4)0.078 (3)0.071 (3)0.009 (3)0.014 (3)0.000 (2)
O43B0.093 (3)0.063 (2)0.066 (3)0.001 (2)0.006 (2)0.001 (2)
N5B0.082 (4)0.057 (3)0.074 (3)0.003 (2)0.008 (3)0.001 (2)
C6B0.085 (5)0.074 (4)0.067 (4)0.000 (3)0.009 (3)0.006 (3)
O61B0.121 (5)0.064 (2)0.075 (3)0.009 (3)0.011 (3)0.002 (2)
N1C0.071 (3)0.074 (3)0.067 (3)0.006 (2)0.002 (2)0.000 (2)
C2C0.066 (4)0.071 (3)0.073 (4)0.006 (3)0.001 (3)0.002 (3)
O21C0.093 (4)0.080 (3)0.062 (3)0.004 (2)0.001 (2)0.002 (2)
C3C0.079 (4)0.065 (3)0.068 (4)0.005 (3)0.002 (3)0.002 (3)
C4C0.067 (4)0.066 (3)0.072 (4)0.005 (3)0.002 (3)0.001 (3)
C41C0.066 (4)0.071 (3)0.070 (4)0.001 (3)0.002 (3)0.005 (3)
O42C0.098 (4)0.077 (3)0.066 (3)0.004 (3)0.003 (2)0.004 (2)
O43C0.077 (3)0.070 (2)0.077 (3)0.007 (2)0.001 (2)0.002 (2)
N5C0.073 (3)0.072 (3)0.062 (3)0.006 (3)0.002 (2)0.003 (2)
C6C0.082 (5)0.068 (3)0.068 (4)0.005 (3)0.006 (3)0.004 (3)
O61C0.100 (4)0.071 (3)0.080 (3)0.015 (2)0.005 (3)0.004 (2)
N1D0.079 (4)0.071 (3)0.068 (3)0.006 (3)0.005 (3)0.001 (2)
C2D0.079 (5)0.076 (4)0.071 (4)0.005 (3)0.003 (3)0.000 (3)
O21D0.118 (5)0.073 (3)0.067 (3)0.006 (3)0.006 (3)0.001 (2)
C3D0.089 (5)0.069 (4)0.066 (4)0.006 (3)0.006 (3)0.003 (3)
C4D0.066 (4)0.065 (3)0.072 (4)0.000 (3)0.006 (3)0.003 (3)
C41D0.079 (4)0.068 (3)0.060 (3)0.005 (3)0.003 (3)0.003 (3)
O42D0.091 (4)0.072 (3)0.071 (3)0.011 (2)0.001 (2)0.001 (2)
O43D0.095 (4)0.062 (2)0.073 (3)0.001 (2)0.009 (3)0.002 (2)
N5D0.073 (4)0.069 (3)0.067 (3)0.006 (2)0.002 (3)0.006 (2)
C6D0.076 (4)0.073 (4)0.064 (3)0.001 (3)0.008 (3)0.005 (3)
O61D0.102 (4)0.067 (2)0.075 (3)0.015 (3)0.001 (3)0.002 (2)
C1X0.076 (5)0.082 (4)0.078 (4)0.005 (3)0.009 (3)0.005 (3)
N2X0.075 (4)0.075 (3)0.070 (3)0.001 (3)0.007 (3)0.005 (3)
C3X0.096 (6)0.075 (4)0.087 (5)0.008 (4)0.007 (4)0.008 (3)
C1Y0.091 (6)0.103 (6)0.113 (7)0.015 (5)0.023 (5)0.022 (5)
N2Y0.079 (4)0.070 (3)0.069 (3)0.003 (3)0.001 (3)0.001 (2)
C3Y0.090 (6)0.100 (6)0.101 (6)0.012 (4)0.010 (5)0.020 (5)
C1Z0.073 (5)0.096 (5)0.101 (6)0.007 (4)0.010 (4)0.019 (4)
N2Z0.072 (4)0.075 (3)0.073 (3)0.002 (3)0.006 (3)0.003 (3)
C3Z0.081 (5)0.083 (4)0.081 (4)0.012 (3)0.012 (4)0.007 (3)
Geometric parameters (Å, º) top
N1A—C2A1.367 (9)N1D—C2D1.377 (9)
N1A—C6A1.376 (9)N1D—H1D0.8800
N1A—H1A0.8800C2D—O21D1.245 (9)
C2A—O21A1.249 (8)C2D—C3D1.437 (10)
C2A—C3A1.438 (9)C3D—C4D1.343 (10)
C3A—C4A1.339 (10)C3D—H3D0.9500
C3A—H3A0.9500C4D—N5D1.371 (9)
C4A—N5A1.368 (9)C4D—C41D1.496 (9)
C4A—C41A1.523 (10)C41D—O42D1.232 (9)
C41A—O42A1.240 (9)C41D—O43D1.294 (8)
C41A—O43A1.258 (9)O43D—H43B1.2216
N5A—C6A1.374 (9)N5D—C6D1.379 (9)
N5A—H5A0.8800N5D—H5D0.8800
C6A—O61A1.215 (9)C6D—O61D1.238 (9)
N1B—C2B1.361 (9)C1X—N2X1.461 (9)
N1B—C6B1.371 (9)C1X—H1X10.9800
N1B—H1B0.8800C1X—H1X20.9800
C2B—O21B1.247 (9)C1X—H1X30.9800
C2B—C3B1.441 (9)N2X—C3X1.468 (9)
C3B—C4B1.351 (10)N2X—H2X10.9200
C3B—H3B0.9500N2X—H2X20.9200
C4B—N5B1.367 (8)C3X—H3X10.9800
C4B—C41B1.507 (9)C3X—H3X20.9800
C41B—O42B1.207 (9)C3X—H3X30.9800
C41B—O43B1.297 (8)C1Y—N2Y1.465 (11)
O43B—H43B1.2118C1Y—H1Y10.9800
N5B—C6B1.389 (9)C1Y—H1Y20.9800
N5B—H5B0.8800C1Y—H1Y30.9800
C6B—O61B1.239 (9)N2Y—C3Y1.464 (12)
N1C—C2C1.369 (9)N2Y—H2Y10.9200
N1C—C6C1.382 (9)N2Y—H2Y20.9200
N1C—H1C0.8800C3Y—H3Y10.9800
C2C—O21C1.247 (9)C3Y—H3Y20.9800
C2C—C3C1.446 (9)C3Y—H3Y30.9800
C3C—C4C1.338 (10)C1Z—N2Z1.479 (11)
C3C—H3C0.9500C1Z—H1Z10.9800
C4C—N5C1.373 (8)C1Z—H1Z20.9800
C4C—C41C1.506 (9)C1Z—H1Z30.9800
C41C—O42C1.248 (9)N2Z—C3Z1.454 (9)
C41C—O43C1.282 (9)N2Z—H2Z10.9200
N5C—C6C1.378 (9)N2Z—H2Z20.9200
N5C—H5C0.8800C3Z—H3Z10.9800
C6C—O61C1.226 (9)C3Z—H3Z20.9800
N1D—C6D1.368 (10)C3Z—H3Z30.9800
C2A—N1A—C6A126.6 (6)C4D—C3D—C2D119.4 (7)
C2A—N1A—H1A116.7C4D—C3D—H3D120.3
C6A—N1A—H1A116.7C2D—C3D—H3D120.3
O21A—C2A—N1A119.0 (6)C3D—C4D—N5D121.8 (7)
O21A—C2A—C3A125.3 (6)C3D—C4D—C41D123.1 (6)
N1A—C2A—C3A115.6 (6)N5D—C4D—C41D115.1 (6)
C4A—C3A—C2A119.0 (6)O42D—C41D—O43D126.3 (6)
C4A—C3A—H3A120.5O42D—C41D—C4D120.2 (6)
C2A—C3A—H3A120.5O43D—C41D—C4D113.5 (6)
C3A—C4A—N5A122.0 (7)C41D—O43D—H43B121.2
C3A—C4A—C41A122.8 (6)C4D—N5D—C6D121.2 (6)
N5A—C4A—C41A115.2 (6)C4D—N5D—H5D119.4
O42A—C41A—O43A127.4 (7)C6D—N5D—H5D119.4
O42A—C41A—C4A117.5 (6)O61D—C6D—N1D120.4 (7)
O43A—C41A—C4A115.1 (7)O61D—C6D—N5D122.7 (7)
C4A—N5A—C6A122.5 (6)N1D—C6D—N5D116.9 (6)
C4A—N5A—H5A118.8N2X—C1X—H1X1109.5
C6A—N5A—H5A118.8N2X—C1X—H1X2109.5
O61A—C6A—N5A123.1 (7)H1X1—C1X—H1X2109.5
O61A—C6A—N1A122.6 (7)N2X—C1X—H1X3109.5
N5A—C6A—N1A114.3 (6)H1X1—C1X—H1X3109.5
C2B—N1B—C6B126.3 (6)H1X2—C1X—H1X3109.5
C2B—N1B—H1B116.9C1X—N2X—C3X112.1 (6)
C6B—N1B—H1B116.9C1X—N2X—H2X1109.2
O21B—C2B—N1B121.0 (6)C3X—N2X—H2X1109.2
O21B—C2B—C3B123.3 (6)C1X—N2X—H2X2109.2
N1B—C2B—C3B115.6 (6)C3X—N2X—H2X2109.2
C4B—C3B—C2B119.3 (6)H2X1—N2X—H2X2107.9
C4B—C3B—H3B120.3N2X—C3X—H3X1109.5
C2B—C3B—H3B120.3N2X—C3X—H3X2109.5
C3B—C4B—N5B121.8 (6)H3X1—C3X—H3X2109.5
C3B—C4B—C41B122.5 (6)N2X—C3X—H3X3109.5
N5B—C4B—C41B115.7 (6)H3X1—C3X—H3X3109.5
O42B—C41B—O43B127.7 (7)H3X2—C3X—H3X3109.5
O42B—C41B—C4B120.5 (6)N2Y—C1Y—H1Y1109.5
O43B—C41B—C4B111.8 (6)N2Y—C1Y—H1Y2109.5
C41B—O43B—H43B122.2H1Y1—C1Y—H1Y2109.5
C4B—N5B—C6B121.5 (6)N2Y—C1Y—H1Y3109.5
C4B—N5B—H5B119.3H1Y1—C1Y—H1Y3109.5
C6B—N5B—H5B119.3H1Y2—C1Y—H1Y3109.5
O61B—C6B—N1B121.9 (7)C3Y—N2Y—C1Y113.7 (8)
O61B—C6B—N5B122.7 (7)C3Y—N2Y—H2Y1108.8
N1B—C6B—N5B115.5 (6)C1Y—N2Y—H2Y1108.8
C2C—N1C—C6C126.0 (6)C3Y—N2Y—H2Y2108.8
C2C—N1C—H1C117.0C1Y—N2Y—H2Y2108.8
C6C—N1C—H1C117.0H2Y1—N2Y—H2Y2107.7
O21C—C2C—N1C119.7 (6)N2Y—C3Y—H3Y1109.5
O21C—C2C—C3C124.6 (6)N2Y—C3Y—H3Y2109.5
N1C—C2C—C3C115.7 (6)H3Y1—C3Y—H3Y2109.5
C4C—C3C—C2C119.3 (6)N2Y—C3Y—H3Y3109.5
C4C—C3C—H3C120.3H3Y1—C3Y—H3Y3109.5
C2C—C3C—H3C120.3H3Y2—C3Y—H3Y3109.5
C3C—C4C—N5C121.6 (6)N2Z—C1Z—H1Z1109.5
C3C—C4C—C41C123.7 (6)N2Z—C1Z—H1Z2109.5
N5C—C4C—C41C114.7 (6)H1Z1—C1Z—H1Z2109.5
O42C—C41C—O43C126.5 (7)N2Z—C1Z—H1Z3109.5
O42C—C41C—C4C117.9 (6)H1Z1—C1Z—H1Z3109.5
O43C—C41C—C4C115.5 (6)H1Z2—C1Z—H1Z3109.5
C4C—N5C—C6C122.5 (6)C3Z—N2Z—C1Z113.8 (7)
C4C—N5C—H5C118.8C3Z—N2Z—H2Z1108.8
C6C—N5C—H5C118.8C1Z—N2Z—H2Z1108.8
O61C—C6C—N5C122.8 (7)C3Z—N2Z—H2Z2108.8
O61C—C6C—N1C122.4 (7)C1Z—N2Z—H2Z2108.8
N5C—C6C—N1C114.7 (6)H2Z1—N2Z—H2Z2107.7
C6D—N1D—C2D124.3 (7)N2Z—C3Z—H3Z1109.5
C6D—N1D—H1D117.8N2Z—C3Z—H3Z2109.5
C2D—N1D—H1D117.8H3Z1—C3Z—H3Z2109.5
O21D—C2D—N1D118.9 (7)N2Z—C3Z—H3Z3109.5
O21D—C2D—C3D124.8 (7)H3Z1—C3Z—H3Z3109.5
N1D—C2D—C3D116.3 (7)H3Z2—C3Z—H3Z3109.5
C6A—N1A—C2A—O21A177.8 (7)C6C—N1C—C2C—O21C179.0 (7)
C6A—N1A—C2A—C3A1.0 (12)C6C—N1C—C2C—C3C1.4 (11)
O21A—C2A—C3A—C4A177.6 (8)O21C—C2C—C3C—C4C178.2 (8)
N1A—C2A—C3A—C4A1.1 (11)N1C—C2C—C3C—C4C2.3 (10)
C2A—C3A—C4A—N5A1.0 (12)C2C—C3C—C4C—N5C0.7 (11)
C2A—C3A—C4A—C41A179.9 (7)C2C—C3C—C4C—C41C179.4 (7)
C3A—C4A—C41A—O42A168.9 (8)C3C—C4C—C41C—O42C175.3 (7)
N5A—C4A—C41A—O42A10.2 (11)N5C—C4C—C41C—O42C4.6 (10)
C3A—C4A—C41A—O43A12.7 (12)C3C—C4C—C41C—O43C3.6 (11)
N5A—C4A—C41A—O43A168.1 (7)N5C—C4C—C41C—O43C176.5 (6)
C3A—C4A—N5A—C6A3.6 (12)C3C—C4C—N5C—C6C2.1 (11)
C41A—C4A—N5A—C6A177.2 (7)C41C—C4C—N5C—C6C177.8 (7)
C4A—N5A—C6A—O61A175.8 (8)C4C—N5C—C6C—O61C175.9 (7)
C4A—N5A—C6A—N1A3.6 (11)C4C—N5C—C6C—N1C2.9 (10)
C2A—N1A—C6A—O61A178.1 (8)C2C—N1C—C6C—O61C177.7 (8)
C2A—N1A—C6A—N5A1.3 (12)C2C—N1C—C6C—N5C1.1 (11)
C6B—N1B—C2B—O21B177.2 (8)C6D—N1D—C2D—O21D176.7 (7)
C6B—N1B—C2B—C3B3.4 (12)C6D—N1D—C2D—C3D3.8 (11)
O21B—C2B—C3B—C4B178.3 (8)O21D—C2D—C3D—C4D177.6 (8)
N1B—C2B—C3B—C4B2.3 (11)N1D—C2D—C3D—C4D2.9 (11)
C2B—C3B—C4B—N5B0.5 (12)C2D—C3D—C4D—N5D0.9 (12)
C2B—C3B—C4B—C41B177.2 (7)C2D—C3D—C4D—C41D179.3 (7)
C3B—C4B—C41B—O42B169.9 (8)C3D—C4D—C41D—O42D173.9 (8)
N5B—C4B—C41B—O42B7.9 (11)N5D—C4D—C41D—O42D7.6 (11)
C3B—C4B—C41B—O43B8.6 (11)C3D—C4D—C41D—O43D5.9 (11)
N5B—C4B—C41B—O43B173.6 (7)N5D—C4D—C41D—O43D172.6 (7)
C3B—C4B—N5B—C6B0.6 (12)C3D—C4D—N5D—C6D0.6 (11)
C41B—C4B—N5B—C6B178.4 (7)C41D—C4D—N5D—C6D177.9 (7)
C2B—N1B—C6B—O61B178.0 (8)C2D—N1D—C6D—O61D179.4 (7)
C2B—N1B—C6B—N5B2.4 (12)C2D—N1D—C6D—N5D2.5 (11)
C4B—N5B—C6B—O61B179.8 (8)C4D—N5D—C6D—O61D178.2 (7)
C4B—N5B—C6B—N1B0.2 (11)C4D—N5D—C6D—N1D0.1 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O42Ci0.881.932.801 (8)168
N5A—H5A···O21Cii0.882.112.953 (8)161
N1B—H1B···O42Diii0.881.932.790 (8)165
N5B—H5B···O21Div0.881.982.837 (8)163
O43B—H43B···O43D1.211.222.433 (6)179
N1C—H1C···O42Av0.881.942.805 (8)167
N5C—H5C···O21Avi0.882.102.936 (8)159
N1D—H1D···O42Bvii0.881.972.817 (8)160
N5D—H5D···O21Bviii0.882.012.852 (8)160
N2X—H2X1···O43Cii0.921.912.805 (9)164
N2X—H2X2···O61D0.921.882.755 (8)159
N2Y—H2Y1···O43A0.921.792.695 (8)167
N2Y—H2Y2···O21C0.921.902.813 (8)171
N2Z—H2Z1···O43C0.921.882.776 (8)163
N2Z—H2Z2···O21A0.921.992.843 (8)154
Symmetry codes: (i) x+1, y1/2, z+2; (ii) x+1, y1/2, z+1; (iii) x+2, y+1/2, z; (iv) x+2, y+1/2, z+1; (v) x+1, y+1/2, z+1; (vi) x+1, y+1/2, z+2; (vii) x+2, y1/2, z+1; (viii) x+2, y1/2, z.

Experimental details

(I)(IIa)(IIb)(IIc)
Crystal data
Chemical formulaC5H6N2O4C5H4N2O4·C2H6OSC2H8N+·C5H3N2O4·C5H4N2O43C2H8N+·3C5H3N2O4·C5H4N2O4
Mr158.12234.23357.29759.67
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/cTriclinic, P1Monoclinic, P21
Temperature (K)173173173173
a, b, c (Å)7.6148 (5), 8.5592 (6), 9.3406 (6)9.3710 (6), 5.9752 (3), 17.8433 (13)8.111 (1), 8.9503 (11), 11.6804 (15)7.0176 (14), 18.026 (4), 12.906 (3)
α, β, γ (°)90, 90, 9090, 97.447 (6), 90112.366 (3), 97.263 (2), 104.621 (2)90, 94.94 (3), 90
V3)608.79 (7)990.68 (11)734.94 (16)1626.5 (6)
Z4422
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.150.330.140.13
Crystal size (mm)0.50 × 0.10 × 0.100.35 × 0.25 × 0.200.20 × 0.20 × 0.100.18 × 0.16 × 0.06
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Stoe IPDS II two-circle
diffractometer
Siemens SMART three-circle
diffractometer
Stoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Blessing, 1995; Spek, 2009)
Tmin, Tmax0.893, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections
10371, 692, 607 18676, 1865, 1383 4208, 2555, 1341 15886, 2968, 2207
Rint0.1070.0760.0720.091
(sin θ/λ)max1)0.6100.6090.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.055, 0.99 0.032, 0.072, 0.91 0.061, 0.104, 0.86 0.065, 0.169, 1.02
No. of reflections692186525552968
No. of parameters113150254479
No. of restraints0001
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.150.17, 0.320.25, 0.300.30, 0.31

Computer programs: X-AREA (Stoe & Cie, 2001), SMART (Siemens, 1994), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O54i0.86 (3)2.14 (3)2.996 (2)175 (2)
N3—H3···O41ii0.91 (3)1.93 (3)2.831 (2)168 (2)
O54—H54···O21iii1.02 (4)1.61 (4)2.604 (2)165 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (IIa) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O21i0.81 (3)2.04 (3)2.846 (2)175 (2)
N5—H5···O21Xii0.95 (3)1.99 (3)2.912 (2)164 (2)
O43—H43···O21X0.98 (3)1.59 (3)2.5675 (18)176 (2)
Symmetry codes: (i) x+2, y1, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (IIb) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O21Bi0.95 (4)1.90 (4)2.836 (3)172 (3)
N5A—H5A···O61Bii0.84 (3)2.12 (3)2.947 (3)165 (3)
N1B—H1B···O21Aiii0.88 (3)1.94 (3)2.807 (3)169 (3)
O43B—H43···O43A1.13 (4)1.37 (4)2.482 (3)167 (4)
N5B—H5B···O61Aiv0.83 (3)2.11 (3)2.931 (3)169 (3)
N2X—H2X1···O61B1.06 (5)1.92 (5)2.973 (3)174 (4)
N2X—H2X2···O43Av0.92 (3)2.11 (3)2.982 (3)159 (3)
Symmetry codes: (i) x1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z1; (iv) x, y1, z1; (v) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (IIc) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O42Ci0.881.932.801 (8)168
N5A—H5A···O21Cii0.882.112.953 (8)161
N1B—H1B···O42Diii0.881.932.790 (8)165
N5B—H5B···O21Div0.881.982.837 (8)163
O43B—H43B···O43D1.211.222.433 (6)179
N1C—H1C···O42Av0.881.942.805 (8)167
N5C—H5C···O21Avi0.882.102.936 (8)159
N1D—H1D···O42Bvii0.881.972.817 (8)160
N5D—H5D···O21Bviii0.882.012.852 (8)160
N2X—H2X1···O43Cii0.921.912.805 (9)164
N2X—H2X2···O61D0.921.882.755 (8)159
N2Y—H2Y1···O43A0.921.792.695 (8)167
N2Y—H2Y2···O21C0.921.902.813 (8)171
N2Z—H2Z1···O43C0.921.882.776 (8)163
N2Z—H2Z2···O21A0.921.992.843 (8)154
Symmetry codes: (i) x+1, y1/2, z+2; (ii) x+1, y1/2, z+1; (iii) x+2, y+1/2, z; (iv) x+2, y+1/2, z+1; (v) x+1, y+1/2, z+1; (vi) x+1, y+1/2, z+2; (vii) x+2, y1/2, z+1; (viii) x+2, y1/2, z.
 

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