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The structures of cocrystals of 2,6-di­chloro­phenol with 2,4-di­amino-6-methyl-1,3,5-triazine, C6H4Cl2O·C4H7N5, (III), and 2,6-di­chloro­aniline with 2,6-diaminopyrimidin-4(3H)-one and N,N-di­methyl­acetamide, C6H5Cl2N·C4H6N4O·C4H9NO, (V), plus three new pseudopolymorphs of their coformers, namely 2,4-di­amino-6-methyl-1,3,5-triazine–N,N-di­methyl­acetamide (1/1), C4H7N5·C4H9NO, (I), 2,4-di­amino-6-methyl-1,3,5-triazine–N-methyl­pyrrolidin-2-one (1/1), C4H7N5·C5H9NO, (II), and 6-amino­isocytosine–N-methyl­pyrrolidin-2-one (1/1), C4H6N4O·C5H9NO, (IV), are reported. Both 2,6-di­chloro­phenol and 2,6-di­chloro­aniline are capable of forming definite synthon motifs, which usually lead to either two- or three-dimensional crystal-packing arrangements. Thus, the two isomorphous pseudopolymorphs of 2,4-di­amino-6-methyl-1,3,5-triazine, i.e. (I) and (II), form a three-dimensional network, while the N-methyl­pyrrolidin-2-one solvate of 6-amino­isocytosine, i.e. (IV), displays two-dimensional layers. On the basis of these results, attempts to cocrystallize 2,6-di­chloro­phenol with 2,4-di­amino-6-methyl-1,3,5-triazine, (III), and 2,6-di­chloro­aniline with 6-amino­isocytosine, (V), yielded two-dimensional networks, whereby in cocrystal (III) the overall structure is a consequence of the inter­action between the two compounds. By comparison, cocrystal–solvate (V) is mainly built by 6-amino­isocytosine forming layers, with 2,6-di­chloro­aniline and the solvent mol­ecules arranged between the layers.

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CCDC references: 1418579; 1418578; 1418577; 1418576; 1418575

Introduction top

As part of our ongoing research, we are inter­ested in the crystal structures of 2,6-di­chloro­aniline (DCA) and 2,6-di­chloro­phenol (DCP), and in the inter­actions of these two compounds in their respective crystal structures. Both compounds contain, aside from their hydrogen -ond donor (–OH and –NH2,respectively), two Cl atoms which can either inter­act as hydrogen/halogen-bond acceptors, or as halogen-bond donors. Di­chloro­phenol and its derivatives are widely known as pollutants and their cytotoxic nature towards freshwater, marine algae and animal cells and tissues has been examined previously (Wang et al., 2010). Regardless of this, di­chloro­phenol derivatives are used as building blocks that can be found in pharmaceuticals and formerly deployed herbicides i.e. Triclosan (McMurry et al., 1998) and Chlometoxyfen (Hikawa, 1984) and also in chemical synthesis (Bourguignon et al., 1993). 2,6-Di­chloro­phenol, especially, had been used for the characterization of Mitsunobu-type inter­mediates (Kumara Swamy et al., 2006). In comparison with the di­chloro­phenol derivatives, chloro­phenols are widely used as fungicides, herbicides and insecticides (Zhang et al., 2010). 2,6-Di­chloro­aniline, however, which is also identified to be toxic to fish, crustaceans and mammals, shows the least toxic properties in comparison with its structural isomers (Valentovic et al., 1995). Similar to their di­chloro derivatives, chloro­aniline and chloro­phenol derivatives can be found as structural components in herbicides and pharmaceuticals, i.e. Linuron (Katsumata et al., 2005), Buturon (Lin et al., 2003), Metosulam (Laganà et al., 2002) and Vancomycin (Loll, 2001). For our research, we decided to cocrystallize the 2,6-di­chloro derivatives of aniline and phenol with 2,4-di­amino-6-methyl-1,3,5-triazine (DMT) and 6-amino­isocytosine (AIC). Both coformers display strong abilities to form hydrogen bonds (Gerhardt et al., 2011). Moreover, they have a tendency to form certain synthons, precisely synthon 2 and 3s for DMT and both types of synthon 3 for AIC (Gerhardt & Egert, 2015) (Fig. 1). In contrast to their coformers, DCP and DCA are capable to form synthon 2, solely. Thus, they usually form only one- or two-dimensional networks.

Integrating DCP or DCA into the synthon-based networks of DMT or AIC might stabilize, or even expand, the usual packing motifs of DCP and DCA to two- or three-dimensional arrangements. However, the latter probably suggests that the Cl atoms participate in the packing and also implies a noncoplanar arrangement of the di­chloro derivatives with their coformers. In order to investigate this issue, cocrystallization attempts of DCP with DMT, and DCA with AIC have been performed.

Unfortunately, only two cocrystals of DCP and DCA were obtained. Three of the obtained crystals contain only DMT or ACI. Nevertheless, it is inter­esting to investigate the inter­molecular inter­actions and the packing motifs of these structures. The structures studied are 2,4-di­amino-6-methyl-1,3,5-triazine–N,N-di­methyl­acetamide (DMT–DMAC) (1/1), (I), 2,4-di­amino-6-methyl-1,3,5-triazine–N-methyl­pyrrolidin-2-one (DMT–NMP) (1/1), (II), 2,4-di­amino-6-methyl-1,3,5-triazine–2,6-di­chloro­phenol (DMT–DCP) (1/1), (III), 6-amino­isocytosine–N-methyl­pyrrolidin-2-one (AIC–NMP) (1/1), (IV), and 6-amino­isocytosine–2,6-di­chloro­aniline–N,N-di­methyl­acetamide (AIC–DCA–DMAC) (1/1/1), (V).

Experimental top

Synthesis and crystallization top

All experiments have been performed with commercially available substances in various hydrous solvents and at different temperatures. Isothermal solvent evaporation experiments of 3-methyl-6-chloro­uracil (M6CU), C5H5ClN2O2, with 2,4-di­amino-6-methyl-1,3,5-triazine (DMT), C4H7N5, in N,N-di­methyl­acetamide, C4H9NO, (DMAC), and N-methyl­pyrrolidin-2-one C5H9NO, (NMP), each at 50 °C, yielded the two DMT and solvent containing crystals (I) and (II). (III) was obtained during crystallization attempts of DMT with 2,6-di­chloro­phenole (DCP), C6H4Cl2O, in a mixture of methanol and DMSO (di­methyl sulfoxide) at room temperature. The NMP solvate of 6-amino­isocytosine, (IV), C4H6N4O, (AIC), had been crystallized via isothermal solvent evaporation experiments at room temperature with 2-amino-4-chloro-6-methyl­pyrimidine. The cocrystal-mono-solvate of AIC with 2,6-di­chloro­aniline, (V), was also crystallized at room temperature. A detailed summary of the performed isothermal solvent evaporation experiments is presented in Table 1.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were initially located by difference Fourier synthesis. Subsequently, H atoms bonded to C atoms were refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å, and Uiso(H) = 1.5Ueq (C) for methyl H atoms or 1.2Ueq (C) for secondary and aromatic H atoms. H atoms bonded to N and O atoms were refined isotropically, with Uiso(H) = 1.2Ueq(N) for (I), (III) and (V), and 1.5Ueq (O) in (III). For the methyl groups in (II) and (III), free rotation about their local threefold axis was allowed. Distance restraints for the solvent molecules were applied to the 1,2 and 1,3 distances in (IV) and (V). Furthermore, in (IV) and (V), the solvent molecules X are disordered across a pseudo-mirror plane, which passes through atoms O2X and C5X with major site-occupation factors of 0.591 (10) in (IV) and 0.635 (9) in (V). Additionally, in (IV), an isotropic extinction parameter has been refined.

Due to the absence of anomalous scatterers in (I) and in (II), 959 Friedel pairs for (I) and 968 Friedel pairs for (II) were merged before refinement and the absolute structure was not determined.

For the CSD, searches only organic structures with determined three-dimensional coordinates have been analyzed and doubled entries, as well as disordered structures of DCA and DCP derivatives, have been omitted.

Results and discussion top

The DMAC solvate of DMT, (I), crystallizes in the orthorhombic space group Fdd2 with one planar molecule of DMT and one planar DMAC molecule (r.m.s. deviations for non-H atoms = 0.031 Å for DMT and 0.026 Å for DMAC) within the asymmetric unit (Fig. 2). Both molecules are linked by an N—H···O hydrogen bond, and a dihedral angle of 39.95 (12)° is observed between the planes of the DMT and DMAC molecules. In the packing, synthon 2iN·N connects DMT molecules into chains parallel to [101] and to [101] (Fig. 3 and Table 3). The chains are oriented with an angle of about 35° with respect to each other, resulting in a three-dimensional network (Fig. 4). Furthermore, the NMP molecules fill the empty spaces between the DMT molecules to which they are connected via an N—H···O hydrogen bond (Fig. 3 and Table 3).

An NMP solvate of DMT, (II), shows similar cell parameters and similar hydrogen-bonding patterns as (I). It also crystallizes in the Fdd2 space group and has one planar molecule each of DMT and NMP (r.m.s. deviations for non-H atoms = 0.009 Å for DMT and 0.050 Å for DMAC), which are linked via one N—H···O hydrogen bond (Fig. 5). Synthon 2iN·N chains parallel to [101] and to [101] are arranged at an angle of about 35° with respect to each other (Fig. 6 and Table 4). The NMP solvent molecules make a dihedral angle of 42.15 (7) ° with the DMT molecules to which they are hydrogen bonded. As in (I), a three-dimensional network is observed (Fig. 7).

Solvent evaporation experiments of DMT with DCP in a methanol/di­methyl sulfoxide (DMSO) mixture yielded the solvent-free cocrystal, denoted (III). The asymmetric unit of the triclinic cell contains one planar DMT molecule (r.m.s. deviation for non-H atoms = 0.028 Å) and one planar DCP molecule (r.m.s. deviation for non-H atoms = 0.008 Å), which enclose a dihedral angle of 88.76 (3)° with respect to each other (Fig. 8). As in (I) and (II), DMT molecules form synthon 2iN·N chains running parallel to [110]. The plane of the DMT molecules is parallel to (112), whereas the plane of the DCP molecules is parallel to (243), with a dihedral angle of about 85° between these planes. One DCP molecule connects two adjacent chains via N—H···O and O—H···N hydrogen bonds, resulting in two-dimensional sheets parallel to (001) (Fig. 9 and Table 5).

Cocrystal (IV) features one molecule of 6-amino­isocytosine (AIC) and one disordered NMP molecule within the asymmetric unit (Fig. 10). Both molecules are connected via one N—H···O hydrogen bond and are almost planar, whereby the molecular planes are inclined by an angle of 13.19 (16) ° with respect to each other (r.m.s. deviation for non-H atoms = 0.013 Å for AIC and 0.055 Å for NMP). In the packing, AIC molecules are connected according to synthon 3u via two N—H···N inter­actions and one N—H···O inter­action, forming undulated layers parallel to (001) (Fig. 11 and Table 6). The solvent molecules are located above and below these layers and are connected to the AIC molecules via N—H···O hydrogen bonds (Fig. 12).

Crystallization attempts of DCA with AIC yielded a cocrystal of these two compounds as a DMAC solvate, denoted (V). The asymmetric unit contains one molecule of 2,6-di­chloro­aniline, A, one disordered DMAC molecule, X, and one molecule of AIC, B (Fig. 13). Each molecule is planar. The AIC molecules are oriented at an angle of 39.13 (5) ° with respect to the DCA molecules (r.m.s. deviation for non-H atoms = 0.018 Å for A, 0.014 Å for B and 0.019 Å for X). N—H···O inter­actions connect molecules A with B, and B with X, which is inclined by 23.58 (5) ° in relation to B. Similar to (IV), molecules of AIC form synthon 3u-based undulated layers which run parallel to (001) (Fig. 14 and Table 7). An R34(12) hydrogen-bonding pattern (Bernstein et al., 1995), consisting of three N—H···O and one N—H···N inter­action by two molecules of B with one molecule each of A and DMAC stabilizes the two-dimensional arrangement in the packing (Fig. 15). The DMAC and DCA molecules are located above and below these layers and are connected to the AIC molecules by N—H···O hydrogen bonds.

A Cambridge Structural Database (CSD, Version 5.36 of November 2014, plus two updates; Groom & Allen, 2014) search was performed for DCP and DCA. The independent hits (16 for DCP and 15 for DCA) are one solvent-free structure for each of DCP and DCA [DCP: CSD refcode DCLPHL (Bavoux & Michel, 1974); DCA: WEMDEX (Dou et al., 1993)], one chlorine salt of I [DCP?] (XEGTOT; Swarmy et al., 2006), a cocrystal of II [DCA?] (NEPXEN; Venter et al., 2013), and 14 (for DCP) or 13 (for DCA) C4-substituted derivatives.

For DCP, ten structures are neutral, of which three crystals display a three-dimensional network [CAKYOE (Varughese et al., 2010), GAKVAP (McKinney & Singh, 1988) and SILGOK (González Martínez & Bernès, 2007)]. In CAKYOE, a C—H···Cl hydrogen bond supports the three-dimensional network, while O—H···Cl and weak Cl···Cl inter­actions are present in SILGOK. In GAKVAP, a weak Cl···Cl inter­action connects two-dimensional chains into a three-dimensional network. Two-dimensional networks are observed in ITEKOH (Kai et al., 2002) and TIJVEN (Eriksson & Eriksson, 2001), wherein no halogen inter­actions are present in the former case, while weak C—H···Cl hydrogen bonds are found in the latter case. One-dimensional chains and ribbons in five structures [LADTUF (Yang et al., 1993), WOMGUB (Desiraju & Bhatt, 2008), and XAZVUQ, XAZWAX and XAZWEB (Britton, 2006)] are mainly built by O—H···O and O—H···N inter­actions, but are also stabilized by weak Cl···O and Cl···π inter­actions. Three of the four ionic crystals are three-dimensional [OBEHOS (Habata et al., 1999), SAQJOJ (Szafran et al., 1997) and XOSGET (Szafran et al., 2015)], whereas the fourth ionic crystal (XAMTOV; Dega-Szafran et al., 2005) shows a one-dimensional arrangement of chains within the packing.

Similar to DCP, ten structures retrieved from the CSD for DCA are neutral. In contrast, no one-dimensional network is observed, while six three-dimensional and four two-dimensional packing arrangements are present. Except for one (ZOBCOI; Simonov et al., 1995), all the three-dimensional crystal structures reveal an involvement of Cl atoms in N—H···Cl hydrogen bonds [FIWGOI (Arun Prasad et al., 2005), TCANIL02 (Gowda et al., 2007) and VABFAH (Qin et al., 2010)], weak C—H···Cl inter­actions (JEQPAX; Soural et al., 2006) or weak Cl···O inter­actions (ZOBCIC; Simonov et al., 1992). Opposite to this trend, the two-dimensional networks contain no chlorine inter­actions [EVICES (Liu et al., 2011), KOGSEE (Dvorkin et al., 1991) and KOGSEF (Simonov et al., 1992)], except for UNUQOK (Wang, 2011), wherein a weak C—H···Cl hydrogen bond is found. Three ionic crystals have been examined. Each includes ionic chlorine, which participates in either a three-dimensional (ACBUET; Carpy et al., 1980) or a two-dimensional network within the packing [SAZRUH (Roschenthaler et al., 2005) and SAZSAO (Roschenthaler et al., 2005)].

Taking a closer look at the two solvent-free crystals, as well as at the cocrystal of DCA and the salt of DCP, one two-dimensional and one three-dimensional arrangement is present in the crystals of DCA. In NEPXEN, chains running along the c maxis are connected via weak C—H···O hydrogen bonds and weak Cl···Cl inter­actions, forming a two-dimensional pattern, while in WEMDEX, a three-dimensional network is built by a mixture of weak Cl···Cl , C—H···Cl and N—H···N inter­actions. The solvent-free structure of DCP (DCLPHL) also shows a three-dimensional network, that is mainly built by weak Cl···Cl halogen contacts and O—H···O hydogen bonds. In contrast to the chloride salt of DCA, a three-dimensional pattern is observed for the salt of DCP (XEGTOT), showing O—H···Cl and N—H···Cl hydrogen bonds with the chloride ions.

Comparing the results of the crystallization experiments and the CSD search, no obvious trend including both, i.e. DCP and DCA, can be determined. Both molecules prefer noncoplanar arrangements in cocrystals regarding their coformers and usually show strong hydrogen bonds. Nevertheless, it can be assumed that for neutral cocrystals, two-dimensional networks might be slightly preferred as well as for the CSD search of DCA. In contrast to the solvent-free structures of DCP and DCA, three-dimensional arrangements are slightly favoured and only for DCP derivatives are one-dimensional arrangements present. Both types of molecules differ within their preferred one- or two-dimensional patterns. For DCP, only one H atom inter­acts as a strong hydrogen-bond donor and, as a consequence of this limitation, one-dimensional networks are predominantly formed. Inter­estingly, the crystal packing of (III) is mainly a result of strong inter­actions of almost orthogonal molecules of DCP with respect to DMT, resulting in the two-dimensional arrangement. Otherwise, in (V), the packing is built only by AIC molecules, and DCA molecules are adjusted [attached] to both sides of the layers.

In summary, noncoplanar arrangements of DCP and DCA with respect to their coformers are favoured, which is in agreement with the frequent occurance of structural analogues in pharmacology and biology. Additionally, the integration of DCP and DCA into synthon-based networks enhances their ability to form two-dimensional networks, either strongly involved or just as stabilizing compounds.

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL (Sheldrick, 2008) for (I); SHELXL97 (Sheldrick, 2008) for (II), (III), (IV), (V). For all compounds, molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Synthons used for two and three hydrogen bonds according to Bernstein et al. (1995) and Gerhardt & Egert (2015).
[Figure 2] Fig. 2. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
[Figure 3] Fig. 3. A partial packing diagram for (I). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) x-1/4, -y+3/4, z+1/4; (ii) -x+1, -y+1, z; (iii) x+1/4, -y+3/4, z-1/4.]
[Figure 4] Fig. 4. A partial packing diagram for (I), showing the three-dimensional arrangement of chains. Solvent molecules have been omitted. Hydrogen bonds are represented by dashed lines.
[Figure 5] Fig. 5. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
[Figure 6] Fig. 6. A partial packing diagram for (II). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x+1, -y+1, z; (ii) x-1/4, -y+3/4, z+1/4; (iii) x+1/4, -y+3/4, z-1/4.]
[Figure 7] Fig. 7. A partial packing diagram for (II), showing the three-dimensional arrangement of chains. Solvent molecules have been omitted. Hydrogen bonds are represented by dashed lines.
[Figure 8] Fig. 8. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
[Figure 9] Fig. 9. A partial packing diagram for (III). Only hydrogen atoms which participate in hydrogen bonds are shown and hydrogen bonds are indicated by dashed lines. [Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y, -z+1.]
[Figure 10] Fig. 10. A perspective view of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. The solvent molecule, X, is disordered and only the major occupied site is shown.
[Figure 11] Fig. 11. A partial packing diagram for (IV), showing the two-dimensional layers, according to synthon 3u, parallel to (001). For reasons of clarity, the solvent molecules have been omitted. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x+1, y-1/2, -z+3/2; (ii) -x+1, y+1/2, -z+3/2; (iii) -x, y-1/2, -z+3/2.]
[Figure 12] Fig. 12. A partial packing diagram of (IV), showing the arrangement of solvent molecules with respect to the two-dimensional network. Hydrogen bonds are shown as dashed lines.
[Figure 13] Fig. 13. A perspective view of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. The solvent molecule, X, is disordered and only the major occupied site is shown.
[Figure 14] Fig. 14. A partial packing diagram for (V), showing the two-dimensional layers built by synthon 3u, parallel to (001). Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x+1, y+1/2, -z+1; (ii) -x+1, y-1/2, -z+1.]
[Figure 15] Fig. 15. A partial packing diagram of (V), showing the two-dimensional network. Hydrogen bonds are shown as dashed lines.
(I) 2,4-Diamino-6-methyl-1,3,5-triazine–N,N-dimethylacetamide (1/1) top
Crystal data top
C4H7N5·C4H9NOF(000) = 1824
Mr = 212.27Dx = 1.267 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 8606 reflections
a = 23.198 (3) Åθ = 3.5–25.8°
b = 26.327 (3) ŵ = 0.09 mm1
c = 7.288 (1) ÅT = 173 K
V = 4451.0 (10) Å3Needle, colourless
Z = 160.14 × 0.12 × 0.08 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1139 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source996 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.109
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 2828
Tmin = 0.884, Tmax = 0.922k = 3131
17579 measured reflectionsl = 88
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)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159 w = 1/[σ2(Fo2) + (0.0846P)2 + 6.4135P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
1139 reflectionsΔρmax = 0.24 e Å3
148 parametersΔρmin = 0.28 e Å3
5 restraintsAbsolute structure: -
Primary atom site location: structure-invariant direct methods
Crystal data top
C4H7N5·C4H9NOV = 4451.0 (10) Å3
Mr = 212.27Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 23.198 (3) ŵ = 0.09 mm1
b = 26.327 (3) ÅT = 173 K
c = 7.288 (1) Å0.14 × 0.12 × 0.08 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1139 independent reflections
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
996 reflections with I > 2σ(I)
Tmin = 0.884, Tmax = 0.922Rint = 0.109
17579 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0665 restraints
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.24 e Å3
1139 reflectionsΔρmin = 0.28 e Å3
148 parametersAbsolute structure: -
Special details top

Experimental. ;

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
N10.50038 (16)0.36665 (13)0.5231 (5)0.0230 (9)
C20.50245 (19)0.41755 (16)0.5102 (6)0.0204 (9)
N20.45481 (15)0.44296 (14)0.5518 (6)0.0247 (9)
H210.4229 (15)0.4268 (17)0.584 (7)0.030*
H220.451 (2)0.4764 (10)0.539 (7)0.030*
N30.54958 (16)0.44451 (13)0.4587 (6)0.0229 (8)
C40.59571 (18)0.41644 (16)0.4191 (6)0.0204 (10)
N40.64339 (16)0.44023 (15)0.3637 (6)0.0285 (10)
H410.6757 (15)0.4232 (18)0.346 (8)0.034*
H420.642 (2)0.4728 (11)0.332 (8)0.034*
N50.59932 (17)0.36526 (14)0.4306 (6)0.0258 (9)
C60.5497 (2)0.34317 (15)0.4814 (7)0.0230 (9)
C610.5499 (2)0.28668 (17)0.4904 (10)0.0388 (13)
H61A0.58820.27400.45710.058*
H61B0.52120.27310.40470.058*
H61C0.54040.27580.61540.058*
C1X0.5649 (3)0.5457 (3)0.0886 (10)0.0545 (17)
H1X10.54000.57310.04400.082*
H1X20.54520.52720.18700.082*
H1X30.57350.52230.01240.082*
C2X0.6213 (3)0.5683 (2)0.1627 (8)0.0471 (15)
O2X0.65926 (18)0.54120 (14)0.2260 (7)0.0509 (11)
N3X0.6268 (3)0.6178 (2)0.1502 (8)0.0600 (16)
C4X0.6817 (4)0.6403 (3)0.2137 (11)0.075 (2)
H4X10.68050.67720.19730.112*
H4X20.71370.62620.14210.112*
H4X30.68740.63230.34390.112*
C5X0.5813 (4)0.6515 (3)0.0847 (14)0.092 (3)
H5X10.59510.68670.08720.138*
H5X20.54740.64820.16400.138*
H5X30.57090.64220.04130.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0193 (17)0.0193 (17)0.031 (2)0.0009 (15)0.0003 (16)0.0028 (17)
C20.019 (2)0.021 (2)0.021 (2)0.0024 (18)0.0004 (18)0.0011 (19)
N20.0166 (19)0.0161 (17)0.042 (2)0.0027 (16)0.0080 (18)0.0042 (18)
N30.0185 (16)0.0186 (17)0.032 (2)0.0002 (16)0.0032 (15)0.0046 (18)
C40.015 (2)0.018 (2)0.028 (2)0.0005 (17)0.0015 (19)0.0011 (19)
N40.0182 (19)0.0193 (18)0.048 (3)0.0029 (16)0.0025 (19)0.0050 (18)
N50.0217 (19)0.0187 (19)0.037 (2)0.0019 (15)0.0018 (18)0.0018 (18)
C60.022 (2)0.023 (2)0.024 (2)0.0007 (19)0.0029 (18)0.007 (2)
C610.026 (2)0.021 (2)0.070 (4)0.003 (2)0.010 (3)0.002 (3)
C1X0.062 (4)0.045 (3)0.056 (4)0.000 (3)0.002 (3)0.004 (3)
C2X0.068 (4)0.038 (3)0.035 (3)0.003 (3)0.017 (3)0.006 (3)
O2X0.056 (3)0.036 (2)0.061 (3)0.0007 (19)0.001 (2)0.018 (2)
N3X0.092 (4)0.038 (3)0.050 (4)0.006 (3)0.015 (3)0.013 (3)
C4X0.121 (7)0.050 (4)0.053 (4)0.032 (4)0.018 (5)0.007 (4)
C5X0.129 (8)0.062 (5)0.086 (6)0.046 (5)0.036 (6)0.038 (5)
Geometric parameters (Å, º) top
N1—C61.335 (6)C61—H61C0.9800
N1—C21.344 (6)C1X—C2X1.536 (9)
C2—N21.327 (6)C1X—H1X10.9800
C2—N31.356 (6)C1X—H1X20.9800
N2—H210.89 (2)C1X—H1X30.9800
N2—H220.89 (2)C2X—O2X1.224 (7)
N3—C41.332 (5)C2X—N3X1.311 (8)
C4—N41.334 (6)N3X—C5X1.459 (9)
C4—N51.352 (6)N3X—C4X1.479 (9)
N4—H410.88 (2)C4X—H4X10.9800
N4—H420.89 (2)C4X—H4X20.9800
N5—C61.342 (6)C4X—H4X30.9800
C6—C611.489 (6)C5X—H5X10.9800
C61—H61A0.9800C5X—H5X20.9800
C61—H61B0.9800C5X—H5X30.9800
C6—N1—C2114.5 (4)C2X—C1X—H1X1109.5
N2—C2—N1117.2 (4)C2X—C1X—H1X2109.5
N2—C2—N3118.1 (4)H1X1—C1X—H1X2109.5
N1—C2—N3124.7 (4)C2X—C1X—H1X3109.5
C2—N2—H21121 (3)H1X1—C1X—H1X3109.5
C2—N2—H22124 (3)H1X2—C1X—H1X3109.5
H21—N2—H22115 (5)O2X—C2X—N3X122.4 (6)
C4—N3—C2114.6 (3)O2X—C2X—C1X121.3 (5)
N3—C4—N4118.1 (4)N3X—C2X—C1X116.3 (6)
N3—C4—N5126.1 (4)C2X—N3X—C5X123.8 (7)
N4—C4—N5115.8 (4)C2X—N3X—C4X117.4 (6)
C4—N4—H41121 (4)C5X—N3X—C4X118.8 (7)
C4—N4—H42120 (3)N3X—C4X—H4X1109.5
H41—N4—H42119 (5)N3X—C4X—H4X2109.5
C6—N5—C4113.3 (4)H4X1—C4X—H4X2109.5
N1—C6—N5126.7 (4)N3X—C4X—H4X3109.5
N1—C6—C61117.1 (4)H4X1—C4X—H4X3109.5
N5—C6—C61116.3 (4)H4X2—C4X—H4X3109.5
C6—C61—H61A109.5N3X—C5X—H5X1109.5
C6—C61—H61B109.5N3X—C5X—H5X2109.5
H61A—C61—H61B109.5H5X1—C5X—H5X2109.5
C6—C61—H61C109.5N3X—C5X—H5X3109.5
H61A—C61—H61C109.5H5X1—C5X—H5X3109.5
H61B—C61—H61C109.5H5X2—C5X—H5X3109.5
C6—N1—C2—N2179.4 (4)C2—N1—C6—N50.4 (7)
C6—N1—C2—N30.4 (7)C2—N1—C6—C61179.1 (5)
N2—C2—N3—C4180.0 (4)C4—N5—C6—N11.7 (7)
N1—C2—N3—C40.3 (7)C4—N5—C6—C61177.9 (5)
C2—N3—C4—N4178.6 (4)O2X—C2X—N3X—C5X176.6 (7)
C2—N3—C4—N51.8 (7)C1X—C2X—N3X—C5X4.9 (9)
N3—C4—N5—C62.4 (7)O2X—C2X—N3X—C4X0.9 (9)
N4—C4—N5—C6178.0 (4)C1X—C2X—N3X—C4X177.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N5i0.89 (2)2.15 (3)3.037 (5)175 (5)
N2—H22···N3ii0.89 (2)2.16 (3)3.041 (5)169 (5)
N4—H41···N1iii0.88 (2)2.10 (3)2.973 (5)174 (6)
N4—H42···O2X0.89 (2)2.00 (3)2.865 (5)163 (5)
Symmetry codes: (i) x1/4, y+3/4, z+1/4; (ii) x+1, y+1, z; (iii) x+1/4, y+3/4, z1/4.
(II) 2,4-Diamino-6-methyl-1,3,5-triazine–N-methylpyrrolidin-2-one (1/1) top
Crystal data top
C4H7N5·C5H9NOF(000) = 1920
Mr = 224.28Dx = 1.330 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 15487 reflections
a = 23.178 (2) Åθ = 3.5–26.0°
b = 26.3327 (17) ŵ = 0.09 mm1
c = 7.3428 (5) ÅT = 173 K
V = 4481.7 (6) Å3Block, colourless
Z = 160.19 × 0.14 × 0.10 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1147 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source1050 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.104
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 2828
Tmin = 0.623, Tmax = 0.776k = 3231
27934 measured reflectionsl = 88
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)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0505P)2 + 1.9967P]
where P = (Fo2 + 2Fc2)/3
S = 1.22(Δ/σ)max < 0.001
1147 reflectionsΔρmax = 0.16 e Å3
159 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: -
Primary atom site location: structure-invariant direct methods
Crystal data top
C4H7N5·C5H9NOV = 4481.7 (6) Å3
Mr = 224.28Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 23.178 (2) ŵ = 0.09 mm1
b = 26.3327 (17) ÅT = 173 K
c = 7.3428 (5) Å0.19 × 0.14 × 0.10 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
1147 independent reflections
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
1050 reflections with I > 2σ(I)
Tmin = 0.623, Tmax = 0.776Rint = 0.104
27934 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.22Δρmax = 0.16 e Å3
1147 reflectionsΔρmin = 0.20 e Å3
159 parametersAbsolute structure: -
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
N10.49594 (12)0.36682 (10)0.5730 (4)0.0228 (7)
C20.49845 (14)0.41812 (12)0.5642 (5)0.0200 (7)
N20.45130 (13)0.44390 (12)0.6090 (5)0.0249 (7)
H210.4501 (17)0.4796 (17)0.595 (5)0.030*
H220.4216 (18)0.4258 (16)0.627 (6)0.030*
N30.54562 (12)0.44473 (10)0.5151 (5)0.0209 (6)
C40.59207 (14)0.41692 (12)0.4753 (5)0.0199 (8)
N40.63988 (13)0.44089 (12)0.4230 (5)0.0233 (7)
H410.6692 (19)0.4242 (16)0.388 (6)0.028*
H420.6392 (16)0.4738 (16)0.406 (6)0.028*
N50.59445 (12)0.36540 (10)0.4812 (4)0.0224 (7)
C60.54485 (15)0.34311 (12)0.5305 (6)0.0227 (8)
C610.54503 (18)0.28666 (13)0.5392 (7)0.0377 (11)
H61A0.55230.27580.66470.056*
H61B0.57540.27340.45950.056*
H61C0.50750.27370.49910.056*
N1X0.58914 (12)0.58571 (12)0.1681 (5)0.0305 (8)
C1X0.55352 (18)0.54228 (16)0.1290 (7)0.0385 (10)
H1X10.57420.51120.16230.058*
H1X20.54440.54160.00130.058*
H1X30.51770.54450.19940.058*
C2X0.64175 (16)0.58309 (15)0.2446 (6)0.0308 (9)
O2X0.66470 (12)0.54405 (11)0.2990 (5)0.0427 (8)
C3X0.66724 (16)0.63528 (14)0.2470 (6)0.0316 (9)
H3X10.70030.63740.16210.038*
H3X20.68080.64410.37100.038*
C4X0.61915 (17)0.67100 (14)0.1875 (6)0.0333 (9)
H4X10.63300.69460.09210.040*
H4X20.60490.69110.29210.040*
C5X0.57135 (16)0.63644 (14)0.1128 (6)0.0314 (9)
H5X10.53350.64530.16630.038*
H5X20.56880.63900.02150.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0182 (14)0.0193 (14)0.0308 (18)0.0020 (12)0.0057 (12)0.0016 (14)
C20.0174 (15)0.0232 (17)0.0195 (17)0.0006 (14)0.0017 (13)0.0004 (16)
N20.0183 (15)0.0167 (15)0.0396 (19)0.0023 (13)0.0052 (15)0.0013 (14)
N30.0154 (12)0.0186 (13)0.0288 (15)0.0002 (12)0.0012 (12)0.0015 (14)
C40.0150 (15)0.0229 (18)0.0218 (19)0.0003 (14)0.0006 (14)0.0010 (16)
N40.0149 (14)0.0161 (14)0.0389 (19)0.0021 (13)0.0058 (14)0.0008 (13)
N50.0195 (15)0.0159 (15)0.0319 (18)0.0021 (11)0.0021 (13)0.0009 (14)
C60.0202 (15)0.0219 (16)0.0260 (19)0.0002 (15)0.0025 (14)0.0000 (16)
C610.0282 (18)0.0218 (18)0.063 (3)0.0013 (17)0.012 (2)0.004 (2)
N1X0.0261 (16)0.0292 (17)0.0362 (19)0.0025 (13)0.0013 (16)0.0057 (15)
C1X0.033 (2)0.035 (2)0.047 (3)0.0059 (18)0.002 (2)0.002 (2)
C2X0.0286 (19)0.033 (2)0.031 (2)0.0023 (17)0.0052 (18)0.0052 (18)
O2X0.0350 (15)0.0310 (15)0.062 (2)0.0070 (12)0.0020 (14)0.0141 (15)
C3X0.030 (2)0.033 (2)0.031 (2)0.0018 (17)0.0016 (18)0.0044 (18)
C4X0.041 (2)0.0260 (19)0.033 (2)0.0008 (18)0.0035 (18)0.0027 (17)
C5X0.0297 (19)0.032 (2)0.033 (2)0.0076 (17)0.0028 (18)0.0079 (18)
Geometric parameters (Å, º) top
N1—C61.331 (4)N1X—C2X1.344 (5)
N1—C21.354 (4)N1X—C1X1.439 (5)
C2—N21.328 (5)N1X—C5X1.456 (5)
C2—N31.348 (4)C1X—H1X10.9800
N2—H210.95 (4)C1X—H1X20.9800
N2—H220.85 (4)C1X—H1X30.9800
N3—C41.334 (4)C2X—O2X1.224 (5)
C4—N41.332 (4)C2X—C3X1.496 (5)
C4—N51.358 (4)C3X—C4X1.522 (5)
N4—H410.85 (5)C3X—H3X10.9900
N4—H420.88 (4)C3X—H3X20.9900
N5—C61.341 (4)C4X—C5X1.535 (6)
C6—C611.488 (5)C4X—H4X10.9900
C61—H61A0.9800C4X—H4X20.9900
C61—H61B0.9800C5X—H5X10.9900
C61—H61C0.9800C5X—H5X20.9900
C6—N1—C2114.8 (3)N1X—C1X—H1X1109.5
N2—C2—N3117.9 (3)N1X—C1X—H1X2109.5
N2—C2—N1117.6 (3)H1X1—C1X—H1X2109.5
N3—C2—N1124.5 (3)N1X—C1X—H1X3109.5
C2—N2—H21120 (2)H1X1—C1X—H1X3109.5
C2—N2—H22115 (3)H1X2—C1X—H1X3109.5
H21—N2—H22124 (4)O2X—C2X—N1X125.0 (4)
C4—N3—C2115.3 (3)O2X—C2X—C3X126.6 (4)
N4—C4—N3118.3 (3)N1X—C2X—C3X108.4 (3)
N4—C4—N5116.7 (3)C2X—C3X—C4X106.0 (3)
N3—C4—N5125.0 (3)C2X—C3X—H3X1110.5
C4—N4—H41121 (3)C4X—C3X—H3X1110.5
C4—N4—H42120 (3)C2X—C3X—H3X2110.5
H41—N4—H42119 (4)C4X—C3X—H3X2110.5
C6—N5—C4114.2 (3)H3X1—C3X—H3X2108.7
N1—C6—N5126.0 (3)C3X—C4X—C5X105.4 (3)
N1—C6—C61117.4 (3)C3X—C4X—H4X1110.7
N5—C6—C61116.5 (3)C5X—C4X—H4X1110.7
C6—C61—H61A109.5C3X—C4X—H4X2110.7
C6—C61—H61B109.5C5X—C4X—H4X2110.7
H61A—C61—H61B109.5H4X1—C4X—H4X2108.8
C6—C61—H61C109.5N1X—C5X—C4X103.9 (3)
H61A—C61—H61C109.5N1X—C5X—H5X1111.0
H61B—C61—H61C109.5C4X—C5X—H5X1111.0
C2X—N1X—C1X124.3 (3)N1X—C5X—H5X2111.0
C2X—N1X—C5X114.9 (3)C4X—C5X—H5X2111.0
C1X—N1X—C5X120.7 (3)H5X1—C5X—H5X2109.0
C6—N1—C2—N2178.6 (4)C4—N5—C6—C61180.0 (4)
C6—N1—C2—N30.7 (6)C1X—N1X—C2X—O2X4.0 (6)
N2—C2—N3—C4178.6 (3)C5X—N1X—C2X—O2X179.5 (4)
N1—C2—N3—C40.6 (6)C1X—N1X—C2X—C3X174.7 (4)
C2—N3—C4—N4179.0 (3)C5X—N1X—C2X—C3X0.8 (5)
C2—N3—C4—N50.0 (6)O2X—C2X—C3X—C4X173.0 (4)
N4—C4—N5—C6178.5 (3)N1X—C2X—C3X—C4X8.3 (4)
N3—C4—N5—C60.4 (5)C2X—C3X—C4X—C5X12.1 (4)
C2—N1—C6—N50.1 (6)C2X—N1X—C5X—C4X6.9 (5)
C2—N1—C6—C61179.5 (4)C1X—N1X—C5X—C4X177.4 (4)
C4—N5—C6—N10.4 (6)C3X—C4X—C5X—N1X11.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N3i0.95 (4)2.08 (4)3.013 (4)169 (4)
N2—H22···N5ii0.85 (4)2.23 (5)3.062 (4)168 (4)
N4—H41···N1iii0.85 (5)2.14 (5)2.982 (4)175 (4)
N4—H42···O2X0.88 (4)2.09 (4)2.922 (4)157 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x1/4, y+3/4, z+1/4; (iii) x+1/4, y+3/4, z1/4.
(III) 2,4-Diamino-6-methyl-1,3,5-triazine–2,6-dichlorophenol (1/1) top
Crystal data top
C6H4Cl2O·C4H7N5Z = 2
Mr = 288.14F(000) = 296
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0318 (7) ÅCell parameters from 2942 reflections
b = 8.5779 (11) Åθ = 3.5–26.0°
c = 15.008 (2) ŵ = 0.51 mm1
α = 93.929 (11)°T = 173 K
β = 96.214 (11)°Needle, colourless
γ = 100.121 (11)°0.19 × 0.12 × 0.06 mm
V = 631.41 (15) Å3
Data collection top
Stoe IPDS II two-circle
diffractometer
2354 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source1864 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.033
ω scansθmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 65
Tmin = 0.719, Tmax = 0.872k = 1010
5126 measured reflectionsl = 1816
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0448P)2]
where P = (Fo2 + 2Fc2)/3
2354 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C6H4Cl2O·C4H7N5γ = 100.121 (11)°
Mr = 288.14V = 631.41 (15) Å3
Triclinic, P1Z = 2
a = 5.0318 (7) ÅMo Kα radiation
b = 8.5779 (11) ŵ = 0.51 mm1
c = 15.008 (2) ÅT = 173 K
α = 93.929 (11)°0.19 × 0.12 × 0.06 mm
β = 96.214 (11)°
Data collection top
Stoe IPDS II two-circle
diffractometer
2354 independent reflections
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
1864 reflections with I > 2σ(I)
Tmin = 0.719, Tmax = 0.872Rint = 0.033
5126 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.19 e Å3
2354 reflectionsΔρmin = 0.21 e Å3
180 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*/UeqOcc. (<1)
N1B0.9771 (3)0.16148 (16)0.42259 (10)0.0264 (3)
C2B0.8271 (4)0.21542 (19)0.48369 (12)0.0246 (4)
N2B0.7876 (4)0.1316 (2)0.55389 (12)0.0329 (4)
H2B10.706 (5)0.168 (3)0.5937 (16)0.040*
H2B20.853 (5)0.048 (3)0.5601 (16)0.040*
N3B0.7150 (3)0.34583 (16)0.47818 (10)0.0248 (3)
C4B0.7728 (4)0.42905 (19)0.40828 (11)0.0227 (4)
N4B0.6633 (4)0.55767 (19)0.39815 (12)0.0294 (4)
H4B10.679 (5)0.603 (3)0.3510 (16)0.035*
H4B20.545 (5)0.579 (3)0.4332 (16)0.035*
N5B0.9340 (3)0.39039 (16)0.34689 (10)0.0256 (3)
C6B1.0255 (4)0.2552 (2)0.35688 (12)0.0246 (4)
C61B1.1942 (4)0.2055 (2)0.28837 (14)0.0332 (5)
H6B11.32210.14340.31580.050*0.71 (2)
H6B21.29560.30000.26590.050*0.71 (2)
H6B31.07580.14040.23830.050*0.71 (2)
H6BA1.38560.25320.30690.050*0.29 (2)
H6BB1.13420.24120.23020.050*0.29 (2)
H6BC1.17380.08940.28290.050*0.29 (2)
C1A0.1526 (4)0.6818 (2)0.19030 (12)0.0261 (4)
O1A0.1896 (3)0.62854 (16)0.27128 (9)0.0325 (3)
H1A0.083 (6)0.545 (3)0.2841 (17)0.049*
C2A0.0606 (4)0.6224 (2)0.12390 (13)0.0326 (4)
Cl2A0.30587 (12)0.46466 (7)0.14567 (4)0.04572 (17)
C3A0.0874 (5)0.6851 (3)0.04147 (15)0.0466 (6)
H3A0.23530.64090.00300.056*
C4A0.1029 (6)0.8121 (3)0.02492 (16)0.0551 (7)
H4A0.08580.85630.03130.066*
C5A0.3175 (6)0.8757 (3)0.08890 (16)0.0473 (6)
H5A0.44820.96380.07730.057*
C6A0.3417 (4)0.8105 (2)0.17021 (13)0.0315 (4)
Cl6A0.61299 (11)0.88885 (6)0.25170 (4)0.04033 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1B0.0305 (9)0.0197 (7)0.0300 (8)0.0056 (6)0.0067 (7)0.0020 (6)
C2B0.0262 (10)0.0188 (8)0.0280 (9)0.0020 (7)0.0032 (8)0.0016 (7)
N2B0.0466 (12)0.0248 (8)0.0336 (9)0.0150 (8)0.0145 (8)0.0093 (7)
N3B0.0244 (8)0.0221 (7)0.0283 (8)0.0048 (6)0.0038 (6)0.0039 (6)
C4B0.0192 (9)0.0215 (8)0.0257 (9)0.0016 (7)0.0013 (7)0.0026 (7)
N4B0.0314 (10)0.0301 (8)0.0319 (9)0.0131 (7)0.0091 (7)0.0126 (7)
N5B0.0246 (8)0.0243 (8)0.0282 (8)0.0038 (6)0.0049 (6)0.0036 (6)
C6B0.0236 (10)0.0201 (8)0.0284 (9)0.0015 (7)0.0014 (7)0.0004 (7)
C61B0.0354 (12)0.0279 (9)0.0386 (11)0.0066 (8)0.0140 (9)0.0027 (8)
C1A0.0271 (10)0.0267 (9)0.0275 (9)0.0099 (7)0.0065 (8)0.0046 (7)
O1A0.0320 (8)0.0326 (7)0.0295 (7)0.0032 (6)0.0015 (6)0.0107 (6)
C2A0.0330 (11)0.0364 (10)0.0298 (10)0.0095 (8)0.0055 (8)0.0035 (8)
Cl2A0.0367 (3)0.0533 (3)0.0395 (3)0.0067 (2)0.0046 (2)0.0029 (2)
C3A0.0510 (15)0.0591 (14)0.0296 (11)0.0143 (11)0.0035 (10)0.0059 (10)
C4A0.0724 (19)0.0630 (15)0.0335 (12)0.0149 (14)0.0078 (12)0.0223 (11)
C5A0.0588 (16)0.0437 (12)0.0433 (13)0.0072 (11)0.0191 (12)0.0179 (10)
C6A0.0316 (11)0.0303 (10)0.0349 (11)0.0080 (8)0.0091 (9)0.0049 (8)
Cl6A0.0348 (3)0.0338 (3)0.0491 (3)0.0038 (2)0.0066 (2)0.0050 (2)
Geometric parameters (Å, º) top
N1B—C6B1.330 (2)C61B—H6BA0.9800
N1B—C2B1.356 (2)C61B—H6BB0.9800
C2B—N2B1.329 (2)C61B—H6BC0.9800
C2B—N3B1.342 (2)C1A—O1A1.333 (2)
N2B—H2B10.84 (2)C1A—C2A1.382 (3)
N2B—H2B20.85 (3)C1A—C6A1.397 (3)
N3B—C4B1.338 (2)O1A—H1A0.86 (3)
C4B—N4B1.328 (2)C2A—C3A1.385 (3)
C4B—N5B1.354 (2)C2A—Cl2A1.738 (2)
N4B—H4B10.83 (2)C3A—C4A1.374 (4)
N4B—H4B20.87 (3)C3A—H3A0.9500
N5B—C6B1.332 (2)C4A—C5A1.372 (4)
C6B—C61B1.488 (3)C4A—H4A0.9500
C61B—H6B10.9800C5A—C6A1.379 (3)
C61B—H6B20.9800C5A—H5A0.9500
C61B—H6B30.9800C6A—Cl6A1.736 (2)
C6B—N1B—C2B114.68 (15)H6BA—C61B—H6BB109.5
N2B—C2B—N3B117.89 (17)C6B—C61B—H6BC109.5
N2B—C2B—N1B117.13 (16)H6BA—C61B—H6BC109.5
N3B—C2B—N1B124.98 (15)H6BB—C61B—H6BC109.5
C2B—N2B—H2B1117.3 (15)O1A—C1A—C2A125.68 (17)
C2B—N2B—H2B2121.3 (16)O1A—C1A—C6A117.98 (18)
H2B1—N2B—H2B2121 (2)C2A—C1A—C6A116.34 (17)
C4B—N3B—C2B114.98 (15)C1A—O1A—H1A120.0 (17)
N4B—C4B—N3B117.81 (17)C1A—C2A—C3A122.5 (2)
N4B—C4B—N5B117.79 (16)C1A—C2A—Cl2A118.49 (14)
N3B—C4B—N5B124.40 (16)C3A—C2A—Cl2A119.03 (18)
C4B—N4B—H4B1118.5 (15)C4A—C3A—C2A119.1 (2)
C4B—N4B—H4B2119.1 (14)C4A—C3A—H3A120.4
H4B1—N4B—H4B2121 (2)C2A—C3A—H3A120.4
C6B—N5B—C4B115.45 (14)C5A—C4A—C3A120.5 (2)
N1B—C6B—N5B125.32 (17)C5A—C4A—H4A119.7
N1B—C6B—C61B117.75 (16)C3A—C4A—H4A119.7
N5B—C6B—C61B116.93 (15)C4A—C5A—C6A119.4 (2)
C6B—C61B—H6B1109.5C4A—C5A—H5A120.3
C6B—C61B—H6B2109.5C6A—C5A—H5A120.3
C6B—C61B—H6B3109.5C5A—C6A—C1A122.1 (2)
C6B—C61B—H6BA109.5C5A—C6A—Cl6A119.97 (17)
C6B—C61B—H6BB109.5C1A—C6A—Cl6A117.89 (14)
C6B—N1B—C2B—N2B175.78 (18)C6A—C1A—C2A—C3A0.3 (3)
C6B—N1B—C2B—N3B4.6 (3)O1A—C1A—C2A—Cl2A0.1 (3)
N2B—C2B—N3B—C4B177.00 (17)C6A—C1A—C2A—Cl2A178.86 (14)
N1B—C2B—N3B—C4B3.4 (3)C1A—C2A—C3A—C4A0.6 (3)
C2B—N3B—C4B—N4B178.67 (16)Cl2A—C2A—C3A—C4A178.52 (19)
C2B—N3B—C4B—N5B0.9 (3)C2A—C3A—C4A—C5A0.3 (4)
N4B—C4B—N5B—C6B176.09 (17)C3A—C4A—C5A—C6A0.3 (4)
N3B—C4B—N5B—C6B3.5 (3)C4A—C5A—C6A—C1A0.6 (3)
C2B—N1B—C6B—N5B1.7 (3)C4A—C5A—C6A—Cl6A179.68 (19)
C2B—N1B—C6B—C61B178.69 (17)O1A—C1A—C6A—C5A178.74 (19)
C4B—N5B—C6B—N1B2.1 (3)C2A—C1A—C6A—C5A0.3 (3)
C4B—N5B—C6B—C61B177.56 (16)O1A—C1A—C6A—Cl6A1.0 (2)
O1A—C1A—C2A—C3A179.3 (2)C2A—C1A—C6A—Cl6A179.97 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4B—H4B1···O1A0.83 (2)2.68 (2)3.060 (2)110 (2)
N4B—H4B1···Cl6A0.83 (2)3.01 (2)3.7354 (17)147 (2)
N2B—H2B1···O1Ai0.84 (2)2.53 (2)3.200 (2)139 (2)
N2B—H2B2···N1Bii0.85 (3)2.14 (3)2.987 (2)179 (2)
N4B—H4B2···N3Bi0.87 (3)2.11 (3)2.977 (2)174 (2)
O1A—H1A···N5Biii0.86 (3)1.78 (3)2.6123 (19)160 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z+1; (iii) x1, y, z.
(IV) 2,6-Diaminopyrimidin-4(3H)-one–N-methylpyrrolidin-2-one (1/1) top
Crystal data top
C4H6N4O·C5H9NOF(000) = 480
Mr = 225.26Dx = 1.338 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25481 reflections
a = 8.1456 (5) Åθ = 3.3–26.0°
b = 9.2289 (6) ŵ = 0.10 mm1
c = 14.9731 (9) ÅT = 173 K
β = 96.463 (5)°Block, colourless
V = 1118.45 (12) Å30.50 × 0.45 × 0.30 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
2098 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source1912 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.073
ω scansθmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 99
Tmin = 0.869, Tmax = 0.914k = 1111
28235 measured reflectionsl = 1718
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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.179 w = 1/[σ2(Fo2) + (0.0893P)2 + 0.8169P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2098 reflectionsΔρmax = 0.61 e Å3
212 parametersΔρmin = 0.41 e Å3
32 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (7)
Crystal data top
C4H6N4O·C5H9NOV = 1118.45 (12) Å3
Mr = 225.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1456 (5) ŵ = 0.10 mm1
b = 9.2289 (6) ÅT = 173 K
c = 14.9731 (9) Å0.50 × 0.45 × 0.30 mm
β = 96.463 (5)°
Data collection top
Stoe IPDS II two-circle
diffractometer
2098 independent reflections
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
1912 reflections with I > 2σ(I)
Tmin = 0.869, Tmax = 0.914Rint = 0.073
28235 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06532 restraints
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.61 e Å3
2098 reflectionsΔρmin = 0.41 e Å3
212 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*/UeqOcc. (<1)
N10.3959 (2)0.33450 (19)0.70055 (13)0.0351 (5)
C20.4815 (3)0.4517 (2)0.72640 (15)0.0352 (5)
N20.6421 (2)0.4574 (2)0.71351 (16)0.0426 (6)
H210.689 (4)0.371 (3)0.7025 (19)0.048 (7)*
H220.704 (4)0.530 (3)0.745 (2)0.051 (8)*
N30.4148 (2)0.5680 (2)0.76271 (14)0.0360 (5)
H30.479 (4)0.646 (4)0.7774 (19)0.052 (8)*
C40.2487 (3)0.5746 (2)0.77620 (15)0.0347 (5)
O40.19854 (19)0.68802 (17)0.81076 (12)0.0420 (5)
C50.1561 (3)0.4521 (2)0.74841 (16)0.0365 (6)
H50.04160.44820.75530.044*
C60.2316 (3)0.3366 (2)0.71089 (15)0.0337 (5)
N60.1494 (3)0.2150 (2)0.68309 (16)0.0409 (5)
H610.191 (4)0.162 (3)0.644 (2)0.049 (8)*
H620.038 (5)0.214 (3)0.686 (2)0.060 (9)*
O2X0.2800 (4)0.0024 (3)0.5758 (2)0.1088 (12)
C5X0.2443 (8)0.3733 (4)0.5204 (3)0.1028 (17)
H5X10.28620.45440.55980.123*0.591 (9)
H5X20.25100.39830.45660.123*0.591 (9)
H5XA0.18780.39780.46020.123*0.409 (9)
H5XB0.23110.45470.56200.123*0.409 (9)
N1X0.3228 (8)0.2372 (5)0.5459 (3)0.0684 (18)0.591 (9)
C1X0.4979 (10)0.2377 (10)0.5403 (8)0.085 (3)0.591 (9)
H1X10.53500.33730.53170.127*0.591 (9)
H1X20.55560.19840.59600.127*0.591 (9)
H1X30.52240.17790.48940.127*0.591 (9)
C2X0.2360 (11)0.1221 (7)0.5557 (9)0.063 (3)0.591 (9)
C3X0.0540 (8)0.1597 (11)0.5493 (6)0.095 (3)0.591 (9)
H3X10.00500.13310.60460.114*0.591 (9)
H3X20.00970.11380.49660.114*0.591 (9)
C4X0.0661 (13)0.3216 (12)0.5385 (10)0.142 (6)0.591 (9)
H4X10.01480.35290.48780.171*0.591 (9)
H4X20.03630.36920.59370.171*0.591 (9)
N1X'0.1840 (11)0.2455 (8)0.5520 (5)0.080 (3)0.409 (9)
C1X'0.0141 (14)0.2659 (16)0.5624 (11)0.082 (4)0.409 (9)
H1XA0.01770.36610.54720.123*0.409 (9)
H1XB0.05310.19950.52240.123*0.409 (9)
H1XC0.00410.24610.62490.123*0.409 (9)
C2X'0.2852 (17)0.1335 (11)0.5626 (19)0.093 (6)0.409 (9)
C3X'0.4550 (19)0.1781 (14)0.5369 (13)0.122 (7)0.409 (9)
H3XA0.48280.12420.48340.147*0.409 (9)
H3XB0.54280.16190.58720.147*0.409 (9)
C4X'0.4317 (13)0.3364 (12)0.5169 (8)0.104 (5)0.409 (9)
H4XA0.50140.39480.56190.125*0.409 (9)
H4XB0.46400.35870.45660.125*0.409 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0279 (9)0.0272 (9)0.0509 (11)0.0002 (7)0.0078 (8)0.0002 (8)
C20.0307 (11)0.0282 (11)0.0472 (13)0.0005 (8)0.0070 (9)0.0022 (9)
N20.0281 (10)0.0306 (10)0.0707 (15)0.0024 (8)0.0124 (9)0.0074 (10)
N30.0288 (10)0.0265 (10)0.0534 (12)0.0012 (7)0.0077 (8)0.0021 (8)
C40.0303 (11)0.0284 (11)0.0462 (12)0.0021 (8)0.0070 (9)0.0019 (9)
O40.0321 (8)0.0289 (8)0.0665 (11)0.0015 (6)0.0122 (7)0.0068 (7)
C50.0275 (11)0.0303 (11)0.0526 (13)0.0007 (8)0.0077 (9)0.0010 (9)
C60.0296 (11)0.0280 (10)0.0436 (12)0.0006 (8)0.0049 (9)0.0041 (9)
N60.0304 (10)0.0309 (10)0.0622 (13)0.0025 (8)0.0089 (9)0.0064 (9)
O2X0.135 (3)0.0803 (19)0.104 (2)0.0409 (19)0.0184 (19)0.0484 (17)
C5X0.185 (6)0.062 (2)0.061 (2)0.016 (3)0.016 (3)0.0039 (18)
N1X0.106 (5)0.047 (3)0.052 (3)0.004 (3)0.013 (3)0.002 (2)
C1X0.101 (6)0.074 (6)0.085 (5)0.030 (5)0.032 (4)0.003 (5)
C2X0.078 (5)0.066 (5)0.043 (4)0.001 (4)0.003 (5)0.014 (3)
C3X0.072 (4)0.140 (8)0.071 (4)0.008 (5)0.000 (3)0.031 (5)
C4X0.163 (15)0.128 (11)0.122 (12)0.027 (10)0.046 (10)0.060 (9)
N1X'0.106 (8)0.083 (7)0.050 (4)0.005 (6)0.011 (4)0.003 (4)
C1X'0.086 (7)0.092 (11)0.071 (6)0.015 (7)0.021 (5)0.031 (7)
C2X'0.119 (13)0.084 (11)0.066 (8)0.026 (8)0.031 (9)0.025 (7)
C3X'0.162 (18)0.122 (14)0.088 (9)0.056 (12)0.031 (10)0.027 (10)
C4X'0.166 (14)0.073 (8)0.078 (7)0.050 (8)0.034 (7)0.001 (6)
Geometric parameters (Å, º) top
N1—C21.321 (3)C5X—H5XB0.9901
N1—C61.365 (3)N1X—C2X1.293 (8)
C2—N21.345 (3)N1X—C1X1.438 (8)
C2—N31.345 (3)C1X—H1X10.9800
N2—H210.91 (3)C1X—H1X20.9800
N2—H220.94 (3)C1X—H1X30.9800
N3—C41.391 (3)C2X—C3X1.515 (8)
N3—H30.91 (3)C3X—C4X1.507 (9)
C4—O41.256 (3)C3X—H3X10.9900
C4—C51.397 (3)C3X—H3X20.9900
C5—C61.381 (3)C4X—H4X10.9900
C5—H50.9500C4X—H4X20.9900
C6—N61.348 (3)N1X'—C2X'1.321 (9)
N6—H610.87 (3)N1X'—C1X'1.423 (9)
N6—H620.92 (4)C1X'—H1XA0.9800
O2X—C2X1.189 (7)C1X'—H1XB0.9800
O2X—C2X'1.228 (9)C1X'—H1XC0.9800
C5X—N1X'1.381 (7)C2X'—C3X'1.534 (10)
C5X—N1X1.441 (6)C3X'—C4X'1.499 (10)
C5X—C4X'1.571 (9)C3X'—H3XA0.9900
C5X—C4X1.580 (9)C3X'—H3XB0.9900
C5X—H5X10.9900C4X'—H4XA0.9900
C5X—H5X20.9900C4X'—H4XB0.9900
C5X—H5XA0.9900
C2—N1—C6116.57 (18)C2X—N1X—C1X124.6 (7)
N1—C2—N2118.7 (2)C2X—N1X—C5X121.0 (6)
N1—C2—N3123.2 (2)C1X—N1X—C5X113.3 (6)
N2—C2—N3118.1 (2)N1X—C1X—H1X1109.5
C2—N2—H21115.3 (18)N1X—C1X—H1X2109.5
C2—N2—H22115.4 (18)H1X1—C1X—H1X2109.5
H21—N2—H22121 (3)N1X—C1X—H1X3109.5
C2—N3—C4122.52 (19)H1X1—C1X—H1X3109.5
C2—N3—H3119.2 (19)H1X2—C1X—H1X3109.5
C4—N3—H3118.3 (19)O2X—C2X—N1X129.7 (8)
O4—C4—N3117.61 (19)O2X—C2X—C3X119.6 (7)
O4—C4—C5127.4 (2)N1X—C2X—C3X110.3 (6)
N3—C4—C5114.99 (19)C4X—C3X—C2X99.1 (7)
C6—C5—C4119.7 (2)C4X—C3X—H3X1111.9
C6—C5—H5120.1C2X—C3X—H3X1111.9
C4—C5—H5120.1C4X—C3X—H3X2111.9
N6—C6—N1114.36 (19)C2X—C3X—H3X2111.9
N6—C6—C5122.6 (2)H3X1—C3X—H3X2109.6
N1—C6—C5122.99 (19)C3X—C4X—C5X113.0 (7)
C6—N6—H61117 (2)C3X—C4X—H4X1109.0
C6—N6—H62117 (2)C5X—C4X—H4X1109.0
H61—N6—H62120 (3)C3X—C4X—H4X2109.0
N1X'—C5X—N1X47.9 (4)C5X—C4X—H4X2109.0
N1X'—C5X—C4X'102.2 (6)H4X1—C4X—H4X2107.8
N1X—C5X—C4X'54.3 (5)C2X'—N1X'—C5X117.9 (8)
N1X'—C5X—C4X46.7 (6)C2X'—N1X'—C1X'133.8 (10)
N1X—C5X—C4X94.6 (6)C5X—N1X'—C1X'108.2 (8)
C4X'—C5X—C4X148.8 (6)N1X'—C1X'—H1XA109.5
N1X'—C5X—H5X1123.6N1X'—C1X'—H1XB109.5
N1X—C5X—H5X1112.8H1XA—C1X'—H1XB109.5
C4X'—C5X—H5X185.0N1X'—C1X'—H1XC109.5
C4X—C5X—H5X1112.8H1XA—C1X'—H1XC109.5
N1X'—C5X—H5X2126.2H1XB—C1X'—H1XC109.5
N1X—C5X—H5X2112.8O2X—C2X'—N1X'139.4 (12)
C4X'—C5X—H5X281.9O2X—C2X'—C3X'110.7 (9)
C4X—C5X—H5X2112.8N1X'—C2X'—C3X'109.2 (9)
H5X1—C5X—H5X2110.3C4X'—C3X'—C2X'102.4 (9)
N1X'—C5X—H5XA111.1C4X'—C3X'—H3XA111.3
N1X—C5X—H5XA125.9C2X'—C3X'—H3XA111.3
C4X'—C5X—H5XA111.9C4X'—C3X'—H3XB111.3
C4X—C5X—H5XA83.3C2X'—C3X'—H3XB111.3
H5X1—C5X—H5XA117.6H3XA—C3X'—H3XB109.2
N1X'—C5X—H5XB111.4C3X'—C4X'—C5X107.8 (8)
N1X—C5X—H5XB124.8C3X'—C4X'—H4XA110.1
C4X'—C5X—H5XB111.1C5X—C4X'—H4XA110.1
C4X—C5X—H5XB87.4C3X'—C4X'—H4XB110.1
H5X2—C5X—H5XB116.9C5X—C4X'—H4XB110.1
H5XA—C5X—H5XB109.1H4XA—C4X'—H4XB108.5
C6—N1—C2—N2176.8 (2)O2X—C2X—C3X—C4X170.9 (12)
C6—N1—C2—N31.1 (3)N1X—C2X—C3X—C4X2.6 (13)
N1—C2—N3—C40.0 (4)C2X—C3X—C4X—C5X10.8 (12)
N2—C2—N3—C4178.0 (2)N1X'—C5X—C4X—C3X15.6 (7)
C2—N3—C4—O4179.9 (2)N1X—C5X—C4X—C3X13.8 (10)
C2—N3—C4—C50.6 (3)C4X'—C5X—C4X—C3X10 (2)
O4—C4—C5—C6179.5 (2)N1X—C5X—N1X'—C2X'5.6 (15)
N3—C4—C5—C60.0 (3)C4X'—C5X—N1X'—C2X'5.2 (16)
C2—N1—C6—N6179.6 (2)C4X—C5X—N1X'—C2X'172.0 (18)
C2—N1—C6—C51.7 (3)N1X—C5X—N1X'—C1X'177.0 (10)
C4—C5—C6—N6179.7 (2)C4X'—C5X—N1X'—C1X'177.4 (9)
C4—C5—C6—N11.1 (3)C4X—C5X—N1X'—C1X'5.4 (13)
N1X'—C5X—N1X—C2X14.8 (9)C2X—O2X—C2X'—N1X'18 (2)
C4X'—C5X—N1X—C2X164.6 (10)C2X—O2X—C2X'—C3X'150 (7)
C4X—C5X—N1X—C2X13.1 (10)C5X—N1X'—C2X'—O2X167 (3)
N1X'—C5X—N1X—C1X177.3 (8)C1X'—N1X'—C2X'—O2X9 (5)
C4X'—C5X—N1X—C1X3.3 (7)C5X—N1X'—C2X'—C3X'1 (2)
C4X—C5X—N1X—C1X179.0 (7)C1X'—N1X'—C2X'—C3X'177.6 (14)
C2X'—O2X—C2X—N1X10 (4)O2X—C2X'—C3X'—C4X'175.7 (18)
C2X'—O2X—C2X—C3X162 (6)N1X'—C2X'—C3X'—C4X'4 (2)
C1X—N1X—C2X—O2X13 (2)C2X'—C3X'—C4X'—C5X6.7 (18)
C5X—N1X—C2X—O2X179.6 (10)N1X'—C5X—C4X'—C3X'7.3 (12)
C1X—N1X—C2X—C3X174.2 (8)N1X—C5X—C4X'—C3X'7.7 (10)
C5X—N1X—C2X—C3X7.7 (13)C4X—C5X—C4X'—C3X'3.2 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O4i0.91 (3)1.94 (3)2.846 (3)175 (3)
N2—H22···N6ii0.94 (3)2.28 (3)3.216 (3)177 (3)
N3—H3···N1ii0.91 (3)2.02 (3)2.922 (3)173 (3)
N6—H61···O2X0.87 (3)2.01 (3)2.850 (3)165 (3)
N6—H62···O4iii0.92 (4)1.94 (4)2.857 (3)173 (3)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2; (iii) x, y1/2, z+3/2.
(V) 2,6-Diaminopyrimidin-4(3H)-one–2,6-dichloroaniline–\ N,N-dimethylacetamide (1/1/1) top
Crystal data top
C6H5Cl2N·C4H6N4O·C4H9NOF(000) = 392
Mr = 375.26Dx = 1.388 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 23474 reflections
a = 8.1060 (5) Åθ = 3.3–26.4°
b = 9.0448 (5) ŵ = 0.38 mm1
c = 12.5656 (8) ÅT = 173 K
β = 102.859 (5)°Block, colourless
V = 898.17 (9) Å30.20 × 0.14 × 0.12 mm
Z = 2
Data collection top
Stoe IPDS II two-circle
diffractometer
3534 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source3330 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.046
ω scansθmax = 26.1°, θmin = 3.3°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 1010
Tmin = 0.794, Tmax = 0.916k = 1111
21925 measured 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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1437P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3534 reflectionsΔρmax = 0.26 e Å3
257 parametersΔρmin = 0.18 e Å3
17 restraintsAbsolute structure: Flack (1983), Number of Bijvoet pairs: 1646
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (5)
Crystal data top
C6H5Cl2N·C4H6N4O·C4H9NOV = 898.17 (9) Å3
Mr = 375.26Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.1060 (5) ŵ = 0.38 mm1
b = 9.0448 (5) ÅT = 173 K
c = 12.5656 (8) Å0.20 × 0.14 × 0.12 mm
β = 102.859 (5)°
Data collection top
Stoe IPDS II two-circle
diffractometer
3534 independent reflections
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
3330 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.916Rint = 0.046
21925 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080Δρmax = 0.26 e Å3
S = 1.10Δρmin = 0.18 e Å3
3534 reflectionsAbsolute structure: Flack (1983), Number of Bijvoet pairs: 1646
257 parametersAbsolute structure parameter: 0.04 (5)
17 restraints
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7878 (3)0.9517 (2)0.87440 (16)0.0252 (4)
N1A0.7379 (3)0.8483 (2)0.79611 (17)0.0352 (5)
H1A10.789 (4)0.853 (3)0.750 (2)0.042*
H1A20.642 (4)0.814 (3)0.791 (2)0.042*
C2A0.9313 (3)1.0404 (3)0.87964 (17)0.0306 (4)
Cl2A1.04435 (8)1.01771 (7)0.77792 (5)0.04277 (16)
C3A0.9862 (3)1.1433 (3)0.9603 (2)0.0407 (6)
H3A1.08551.19940.96100.049*
C4A0.8958 (4)1.1648 (3)1.0406 (2)0.0441 (6)
H4A0.93261.23541.09680.053*
C5A0.7518 (3)1.0823 (3)1.03762 (19)0.0369 (5)
H5A0.68761.09741.09140.044*
C6A0.7011 (3)0.9790 (3)0.95776 (17)0.0298 (5)
Cl6A0.51908 (8)0.87668 (7)0.95601 (5)0.04686 (18)
N1B0.56730 (19)0.42237 (18)0.43752 (13)0.0186 (3)
C2B0.5014 (2)0.5401 (2)0.47486 (14)0.0184 (4)
N2B0.3341 (2)0.5485 (2)0.46373 (15)0.0250 (4)
H21B0.269 (3)0.468 (3)0.439 (2)0.030*
H22B0.292 (3)0.620 (3)0.496 (2)0.030*
N3B0.5969 (2)0.6551 (2)0.52280 (13)0.0205 (3)
H3B0.548 (3)0.729 (3)0.5441 (19)0.025*
C4B0.7719 (2)0.6587 (2)0.53695 (15)0.0192 (4)
O4B0.84738 (16)0.76997 (15)0.58309 (12)0.0232 (3)
C5B0.8424 (2)0.5367 (2)0.49467 (15)0.0204 (4)
H5B0.96090.53220.49930.024*
C6B0.7383 (2)0.4227 (2)0.44609 (15)0.0183 (4)
N6B0.7971 (2)0.30113 (19)0.40550 (15)0.0226 (3)
H61B0.902 (3)0.299 (3)0.4059 (19)0.027*
H62B0.728 (3)0.252 (3)0.361 (2)0.027*
C1X0.3033 (3)0.0586 (4)0.2158 (3)0.0550 (8)
H11X0.29270.16610.20770.082*0.635 (9)
H12X0.24970.01080.14680.082*0.635 (9)
H13X0.24750.02580.27330.082*0.635 (9)
H4AX0.21860.13770.20290.082*0.365 (9)
H4BX0.28390.00560.27470.082*0.365 (9)
H4CX0.29390.00030.14900.082*0.365 (9)
O2X0.5497 (2)0.11334 (17)0.26385 (14)0.0350 (4)
C4X0.5361 (5)0.2831 (3)0.2364 (2)0.0531 (8)
H41X0.63200.35170.25140.080*0.635 (9)
H42X0.47760.29080.15940.080*0.635 (9)
H43X0.45740.30790.28270.080*0.635 (9)
H1AX0.43780.34910.22260.080*0.365 (9)
H1BX0.59250.28860.17510.080*0.365 (9)
H1CX0.61530.31330.30370.080*0.365 (9)
C5X0.7811 (3)0.0953 (3)0.2912 (2)0.0437 (6)
H51X0.84610.18750.29900.066*0.635 (9)
H52X0.80580.04160.36070.066*0.635 (9)
H53X0.81250.03400.23450.066*0.635 (9)
H5AX0.77060.20320.28690.066*0.365 (9)
H5BX0.84250.06040.23710.066*0.365 (9)
H5CX0.84310.06680.36450.066*0.365 (9)
C2X0.4921 (6)0.0160 (5)0.2469 (3)0.0257 (11)0.635 (9)
N3X0.5987 (5)0.1294 (4)0.2602 (2)0.0316 (12)0.635 (9)
N3X'0.4761 (9)0.1240 (8)0.2466 (4)0.038 (2)0.365 (9)
C2X'0.5992 (10)0.0249 (8)0.2677 (5)0.027 (2)0.365 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0255 (9)0.0256 (10)0.0236 (9)0.0033 (8)0.0035 (7)0.0048 (8)
N1A0.0349 (11)0.0404 (12)0.0321 (10)0.0137 (9)0.0111 (8)0.0073 (9)
C2A0.0300 (11)0.0316 (12)0.0317 (10)0.0013 (9)0.0098 (8)0.0011 (10)
Cl2A0.0397 (3)0.0499 (4)0.0446 (3)0.0146 (3)0.0218 (2)0.0087 (3)
C3A0.0399 (13)0.0388 (14)0.0439 (13)0.0114 (11)0.0101 (11)0.0060 (11)
C4A0.0530 (16)0.0383 (14)0.0398 (13)0.0056 (12)0.0082 (11)0.0134 (11)
C5A0.0432 (14)0.0371 (13)0.0321 (12)0.0070 (10)0.0117 (10)0.0005 (9)
C6A0.0270 (10)0.0335 (12)0.0295 (10)0.0020 (9)0.0076 (8)0.0076 (9)
Cl6A0.0415 (3)0.0562 (4)0.0489 (3)0.0133 (3)0.0229 (3)0.0016 (3)
N1B0.0139 (7)0.0158 (8)0.0268 (8)0.0011 (6)0.0064 (6)0.0005 (6)
C2B0.0158 (8)0.0162 (9)0.0239 (8)0.0006 (7)0.0057 (7)0.0008 (7)
N2B0.0137 (8)0.0217 (9)0.0414 (9)0.0011 (7)0.0096 (7)0.0077 (8)
N3B0.0154 (7)0.0173 (8)0.0306 (8)0.0014 (6)0.0091 (6)0.0022 (7)
C4B0.0161 (8)0.0170 (9)0.0253 (9)0.0006 (7)0.0061 (7)0.0032 (8)
O4B0.0148 (6)0.0213 (7)0.0337 (7)0.0030 (5)0.0059 (5)0.0043 (6)
C5B0.0134 (8)0.0196 (9)0.0296 (9)0.0007 (7)0.0076 (7)0.0011 (8)
C6B0.0156 (8)0.0191 (9)0.0218 (8)0.0013 (7)0.0075 (7)0.0039 (7)
N6B0.0139 (8)0.0195 (8)0.0359 (10)0.0001 (7)0.0084 (7)0.0029 (7)
C1X0.0344 (14)0.067 (2)0.0603 (17)0.0076 (13)0.0047 (12)0.0119 (15)
O2X0.0407 (9)0.0252 (8)0.0394 (9)0.0010 (7)0.0097 (7)0.0058 (7)
C4X0.085 (2)0.0273 (13)0.0431 (15)0.0061 (13)0.0062 (14)0.0027 (11)
C5X0.0337 (12)0.0548 (17)0.0414 (12)0.0070 (12)0.0057 (10)0.0003 (12)
C2X0.029 (2)0.025 (3)0.0222 (16)0.0050 (17)0.0049 (15)0.0063 (13)
N3X0.040 (3)0.021 (2)0.0329 (16)0.0042 (15)0.0063 (14)0.0066 (13)
N3X'0.042 (5)0.038 (5)0.034 (3)0.013 (3)0.007 (2)0.007 (3)
C2X'0.034 (5)0.028 (5)0.017 (3)0.004 (3)0.001 (3)0.001 (2)
Geometric parameters (Å, º) top
C1A—N1A1.353 (3)C1X—N3X'1.490 (8)
C1A—C2A1.402 (3)C1X—C2X1.542 (5)
C1A—C6A1.407 (3)C1X—H11X0.9800
N1A—H1A10.79 (3)C1X—H12X0.9800
N1A—H1A20.83 (3)C1X—H13X0.9800
C2A—C3A1.375 (3)C1X—H4AX0.9800
C2A—Cl2A1.743 (2)C1X—H4BX0.9799
C3A—C4A1.386 (4)C1X—H4CX0.9802
C3A—H3A0.9500O2X—C2X1.260 (5)
C4A—C5A1.378 (4)O2X—C2X'1.311 (8)
C4A—H4A0.9500C4X—N3X1.487 (5)
C5A—C6A1.366 (3)C4X—N3X'1.533 (8)
C5A—H5A0.9500C4X—H41X0.9800
C6A—Cl6A1.738 (2)C4X—H42X0.9800
N1B—C2B1.323 (2)C4X—H43X0.9800
N1B—C6B1.366 (2)C4X—H1AX0.9800
C2B—N2B1.334 (2)C4X—H1BX0.9801
C2B—N3B1.355 (3)C4X—H1CX0.9799
N2B—H21B0.91 (3)C5X—N3X1.475 (5)
N2B—H22B0.87 (3)C5X—C2X'1.573 (8)
N3B—C4B1.390 (2)C5X—H51X0.9800
N3B—H3B0.85 (3)C5X—H52X0.9800
C4B—O4B1.252 (2)C5X—H53X0.9800
C4B—C5B1.400 (3)C5X—H5AX0.9800
C5B—C6B1.385 (3)C5X—H5BX0.9800
C5B—H5B0.9500C5X—H5CX0.9800
C6B—N6B1.344 (3)C2X—N3X1.327 (6)
N6B—H61B0.85 (3)N3X'—C2X'1.324 (11)
N6B—H62B0.83 (3)
N1A—C1A—C2A122.7 (2)H4BX—C1X—H4CX109.5
N1A—C1A—C6A123.0 (2)N3X—C4X—H41X109.5
C2A—C1A—C6A114.28 (19)N3X'—C4X—H41X146.3
C1A—N1A—H1A1112 (2)N3X—C4X—H42X109.5
C1A—N1A—H1A2117 (2)N3X'—C4X—H42X93.2
H1A1—N1A—H1A2127 (3)H41X—C4X—H42X109.5
C3A—C2A—C1A123.4 (2)N3X—C4X—H43X109.5
C3A—C2A—Cl2A118.92 (18)N3X'—C4X—H43X84.6
C1A—C2A—Cl2A117.64 (16)H41X—C4X—H43X109.5
C2A—C3A—C4A119.6 (2)H42X—C4X—H43X109.5
C2A—C3A—H3A120.2N3X—C4X—H1AX146.4
C4A—C3A—H3A120.2N3X'—C4X—H1AX109.0
C5A—C4A—C3A119.1 (2)H41X—C4X—H1AX103.1
C5A—C4A—H4A120.5H42X—C4X—H1AX65.6
C3A—C4A—H4A120.5H43X—C4X—H1AX49.8
C6A—C5A—C4A120.3 (2)N3X—C4X—H1BX90.4
C6A—C5A—H5A119.9N3X'—C4X—H1BX109.0
C4A—C5A—H5A119.9H41X—C4X—H1BX68.3
C5A—C6A—C1A123.2 (2)H42X—C4X—H1BX55.2
C5A—C6A—Cl6A119.31 (18)H43X—C4X—H1BX158.9
C1A—C6A—Cl6A117.44 (17)H1AX—C4X—H1BX109.5
C2B—N1B—C6B116.92 (16)N3X—C4X—H1CX87.6
N1B—C2B—N2B119.33 (17)N3X'—C4X—H1CX110.4
N1B—C2B—N3B122.67 (16)H41X—C4X—H1CX47.0
N2B—C2B—N3B117.99 (18)H42X—C4X—H1CX155.7
C2B—N2B—H21B119.3 (15)H43X—C4X—H1CX79.2
C2B—N2B—H22B119.1 (17)H1AX—C4X—H1CX109.5
H21B—N2B—H22B119 (2)H1BX—C4X—H1CX109.5
C2B—N3B—C4B122.70 (17)N3X—C5X—H51X109.5
C2B—N3B—H3B119.0 (16)C2X'—C5X—H51X145.5
C4B—N3B—H3B118.3 (16)N3X—C5X—H52X109.5
O4B—C4B—N3B117.26 (17)C2X'—C5X—H52X88.0
O4B—C4B—C5B127.63 (17)H51X—C5X—H52X109.5
N3B—C4B—C5B115.10 (17)N3X—C5X—H53X109.5
C6B—C5B—C4B119.56 (16)C2X'—C5X—H53X91.1
C6B—C5B—H5B120.2H51X—C5X—H53X109.5
C4B—C5B—H5B120.2H52X—C5X—H53X109.5
N6B—C6B—N1B114.07 (17)N3X—C5X—H5AX73.0
N6B—C6B—C5B122.93 (16)C2X'—C5X—H5AX109.1
N1B—C6B—C5B122.98 (17)H52X—C5X—H5AX122.7
C6B—N6B—H61B117.0 (17)H53X—C5X—H5AX123.8
C6B—N6B—H62B116.5 (17)N3X—C5X—H5BX121.2
H61B—N6B—H62B122 (2)C2X'—C5X—H5BX109.9
N3X'—C1X—H11X71.9H51X—C5X—H5BX89.9
C2X—C1X—H11X109.5H52X—C5X—H5BX115.1
N3X'—C1X—H12X127.6H5AX—C5X—H5BX109.5
C2X—C1X—H12X109.5N3X—C5X—H5CX125.3
H11X—C1X—H12X109.5C2X'—C5X—H5CX109.5
N3X'—C1X—H13X119.4H51X—C5X—H5CX88.7
C2X—C1X—H13X109.5H53X—C5X—H5CX111.9
H11X—C1X—H13X109.5H5AX—C5X—H5CX109.5
H12X—C1X—H13X109.5H5BX—C5X—H5CX109.5
N3X'—C1X—H4AX109.6O2X—C2X—N3X119.3 (5)
C2X—C1X—H4AX147.5O2X—C2X—C1X125.7 (4)
H12X—C1X—H4AX91.1N3X—C2X—C1X114.9 (4)
H13X—C1X—H4AX85.5C2X—N3X—C5X117.3 (4)
N3X'—C1X—H4BX109.8C2X—N3X—C4X120.9 (4)
C2X—C1X—H4BX88.7C5X—N3X—C4X121.7 (3)
H11X—C1X—H4BX129.9C2X—N3X—H5AX155.5
H12X—C1X—H4BX107.1C4X—N3X—H5AX83.6
H4AX—C1X—H4BX109.5C2X'—N3X'—C1X114.0 (7)
N3X'—C1X—H4CX109.0C2X'—N3X'—C4X114.4 (7)
C2X—C1X—H4CX88.1C1X—N3X'—C4X130.4 (5)
H11X—C1X—H4CX117.1O2X—C2X'—N3X'115.3 (8)
H13X—C1X—H4CX120.6O2X—C2X'—C5X131.3 (6)
H4AX—C1X—H4CX109.5N3X'—C2X'—C5X113.4 (6)
N1A—C1A—C2A—C3A178.2 (2)C4B—C5B—C6B—N1B0.4 (3)
C6A—C1A—C2A—C3A1.4 (3)C2X'—O2X—C2X—N3X1.8 (4)
N1A—C1A—C2A—Cl2A1.8 (3)C2X'—O2X—C2X—C1X175.3 (6)
C6A—C1A—C2A—Cl2A178.56 (15)N3X'—C1X—C2X—O2X172.9 (6)
C1A—C2A—C3A—C4A1.2 (4)N3X'—C1X—C2X—N3X4.4 (4)
Cl2A—C2A—C3A—C4A178.7 (2)O2X—C2X—N3X—C5X1.9 (4)
C2A—C3A—C4A—C5A0.1 (4)C1X—C2X—N3X—C5X179.3 (3)
C3A—C4A—C5A—C6A1.2 (4)O2X—C2X—N3X—C4X177.4 (3)
C4A—C5A—C6A—C1A1.0 (4)C1X—C2X—N3X—C4X5.2 (4)
C4A—C5A—C6A—Cl6A180.0 (2)C2X'—C5X—N3X—C2X2.8 (4)
N1A—C1A—C6A—C5A179.4 (2)C2X'—C5X—N3X—C4X178.3 (5)
C2A—C1A—C6A—C5A0.3 (3)N3X'—C4X—N3X—C2X8.3 (4)
N1A—C1A—C6A—Cl6A1.7 (3)N3X'—C4X—N3X—C5X176.4 (5)
C2A—C1A—C6A—Cl6A178.68 (16)C2X—C1X—N3X'—C2X'1.5 (4)
C6B—N1B—C2B—N2B176.80 (17)C2X—C1X—N3X'—C4X165.0 (8)
C6B—N1B—C2B—N3B2.0 (3)N3X—C4X—N3X'—C2X'2.2 (4)
N1B—C2B—N3B—C4B0.2 (3)N3X—C4X—N3X'—C1X168.7 (8)
N2B—C2B—N3B—C4B179.01 (17)C2X—O2X—C2X'—N3X'4.5 (4)
C2B—N3B—C4B—O4B179.43 (17)C2X—O2X—C2X'—C5X174.2 (9)
C2B—N3B—C4B—C5B2.1 (3)C1X—N3X'—C2X'—O2X3.4 (7)
O4B—C4B—C5B—C6B179.93 (18)C4X—N3X'—C2X'—O2X172.2 (4)
N3B—C4B—C5B—C6B1.8 (3)C1X—N3X'—C2X'—C5X175.5 (4)
C2B—N1B—C6B—N6B179.18 (16)C4X—N3X'—C2X'—C5X6.8 (6)
C2B—N1B—C6B—C5B2.3 (3)N3X—C5X—C2X'—O2X175.7 (8)
C4B—C5B—C6B—N6B178.78 (18)N3X—C5X—C2X'—N3X'3.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A1···O4B0.79 (3)2.37 (3)3.084 (3)151 (3)
N1A—H1A1···Cl2A0.79 (3)2.51 (3)2.971 (2)119 (3)
N1A—H1A2···O2Xi0.83 (3)2.39 (3)3.120 (3)149 (3)
N1A—H1A2···Cl6A0.83 (3)2.56 (3)2.972 (2)112 (2)
N2B—H21B···O4Bii0.91 (3)2.02 (3)2.911 (2)167 (2)
N2B—H22B···N6Bi0.87 (3)2.27 (3)3.135 (3)174 (2)
N3B—H3B···N1Bi0.85 (3)2.02 (3)2.857 (2)168 (2)
N6B—H61B···O4Biii0.85 (3)2.02 (3)2.867 (2)173 (2)
N6B—H62B···O2X0.83 (3)2.09 (3)2.913 (2)173 (2)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x+2, y1/2, z+1.
Isothermal solvent evaporation experiments of DMT, DCP, AIC and DCA.
M6CU is 3-methyl-6-chlorouracil, DMT is 2,4-diamino-6-methyl-1,3,5-triazine, DCP is 2,6-dichlorophenol, ACM is ???? AIC is 6-aminoisocytosine and DCA is 2,6-dichloroaniline.
top
CocrystalExperiment 1 (mg; mmol)Experiment 2 (mg; mmol)Solvent (µl)Temperature (°C; K)
(I)M6CU: 5; 0.03DMT: 1; 0.0126050; 323
(II)M6CU: 5; 0.03DMT: 2; 0.0219550; 323
(III)DCP: 52; 0.32DMT: 22; 0.1750*23; 296
(IV)ACM: 2; 0.01AIC: 4; 0.0315023; 296
(V)DCA: 169; 1.04AIC: 26; 0.220023; 296
Notes: (*) plus 30 µl DMSO (dimethyl sulfoxide); ACM = 2-amino-4-chloro-6-methylpyrimidine.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC4H7N5·C4H9NOC4H7N5·C5H9NOC6H4Cl2O·C4H7N5
Mr212.27224.28288.14
Crystal system, space groupOrthorhombic, Fdd2Orthorhombic, Fdd2Triclinic, P1
Temperature (K)173173173
a, b, c (Å)23.198 (3), 26.327 (3), 7.288 (1)23.178 (2), 26.3327 (17), 7.3428 (5)5.0318 (7), 8.5779 (11), 15.008 (2)
α, β, γ (°)90, 90, 9090, 90, 9093.929 (11), 96.214 (11), 100.121 (11)
V3)4451.0 (10)4481.7 (6)631.41 (15)
Z16162
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.090.51
Crystal size (mm)0.14 × 0.12 × 0.080.19 × 0.14 × 0.100.19 × 0.12 × 0.06
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Stoe IPDS II two-circle
diffractometer
Stoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(X-AREA; Stoe & Cie, 2001)
Multi-scan
(X-AREA; Stoe & Cie, 2001)
Multi-scan
(X-AREA; Stoe & Cie, 2001)
Tmin, Tmax0.884, 0.9220.623, 0.7760.719, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
17579, 1139, 996 27934, 1147, 1050 5126, 2354, 1864
Rint0.1090.1040.033
(sin θ/λ)max1)0.6090.6090.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.159, 1.14 0.052, 0.103, 1.22 0.033, 0.081, 1.03
No. of reflections113911472354
No. of parameters148159180
No. of restraints510
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 refinement
Δρmax, Δρmin (e Å3)0.24, 0.280.16, 0.200.19, 0.21
Absolute structure--?
Absolute structure parameter???


(IV)(V)
Crystal data
Chemical formulaC4H6N4O·C5H9NOC6H5Cl2N·C4H6N4O·C4H9NO
Mr225.26375.26
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21
Temperature (K)173173
a, b, c (Å)8.1456 (5), 9.2289 (6), 14.9731 (9)8.1060 (5), 9.0448 (5), 12.5656 (8)
α, β, γ (°)90, 96.463 (5), 9090, 102.859 (5), 90
V3)1118.45 (12)898.17 (9)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.100.38
Crystal size (mm)0.50 × 0.45 × 0.300.20 × 0.14 × 0.12
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Stoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(X-AREA; Stoe & Cie, 2001)
Multi-scan
(X-AREA; Stoe & Cie, 2001)
Tmin, Tmax0.869, 0.9140.794, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
28235, 2098, 1912 21925, 3534, 3330
Rint0.0730.046
(sin θ/λ)max1)0.6110.619
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.179, 1.07 0.031, 0.080, 1.10
No. of reflections20983534
No. of parameters212257
No. of restraints3217
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.61, 0.410.26, 0.18
Absolute structure?Flack (1983), Number of Bijvoet pairs: 1646
Absolute structure parameter?0.04 (5)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N5i0.89 (2)2.15 (3)3.037 (5)175 (5)
N2—H22···N3ii0.89 (2)2.16 (3)3.041 (5)169 (5)
N4—H41···N1iii0.88 (2)2.10 (3)2.973 (5)174 (6)
N4—H42···O2X0.89 (2)2.00 (3)2.865 (5)163 (5)
Symmetry codes: (i) x1/4, y+3/4, z+1/4; (ii) x+1, y+1, z; (iii) x+1/4, y+3/4, z1/4.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N3i0.95 (4)2.08 (4)3.013 (4)169 (4)
N2—H22···N5ii0.85 (4)2.23 (5)3.062 (4)168 (4)
N4—H41···N1iii0.85 (5)2.14 (5)2.982 (4)175 (4)
N4—H42···O2X0.88 (4)2.09 (4)2.922 (4)157 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x1/4, y+3/4, z+1/4; (iii) x+1/4, y+3/4, z1/4.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N4B—H4B1···O1A0.83 (2)2.68 (2)3.060 (2)110 (2)
N4B—H4B1···Cl6A0.83 (2)3.01 (2)3.7354 (17)147 (2)
N2B—H2B1···O1Ai0.84 (2)2.53 (2)3.200 (2)139 (2)
N2B—H2B2···N1Bii0.85 (3)2.14 (3)2.987 (2)179 (2)
N4B—H4B2···N3Bi0.87 (3)2.11 (3)2.977 (2)174 (2)
O1A—H1A···N5Biii0.86 (3)1.78 (3)2.6123 (19)160 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z+1; (iii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O4i0.91 (3)1.94 (3)2.846 (3)175 (3)
N2—H22···N6ii0.94 (3)2.28 (3)3.216 (3)177 (3)
N3—H3···N1ii0.91 (3)2.02 (3)2.922 (3)173 (3)
N6—H61···O2X0.87 (3)2.01 (3)2.850 (3)165 (3)
N6—H62···O4iii0.92 (4)1.94 (4)2.857 (3)173 (3)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1/2, z+3/2; (iii) x, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A1···O4B0.79 (3)2.37 (3)3.084 (3)151 (3)
N1A—H1A1···Cl2A0.79 (3)2.51 (3)2.971 (2)119 (3)
N1A—H1A2···O2Xi0.83 (3)2.39 (3)3.120 (3)149 (3)
N1A—H1A2···Cl6A0.83 (3)2.56 (3)2.972 (2)112 (2)
N2B—H21B···O4Bii0.91 (3)2.02 (3)2.911 (2)167 (2)
N2B—H22B···N6Bi0.87 (3)2.27 (3)3.135 (3)174 (2)
N3B—H3B···N1Bi0.85 (3)2.02 (3)2.857 (2)168 (2)
N6B—H61B···O4Biii0.85 (3)2.02 (3)2.867 (2)173 (2)
N6B—H62B···O2X0.83 (3)2.09 (3)2.913 (2)173 (2)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x+2, y1/2, z+1.
 

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