Cocrystals of 2,6-di­chloro­aniline and 2,6-di­chloro­phenol plus three new pseudopolymorphs of their coformers

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.

S1. Introduction

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).

S2. Experimental

S2.1. Synthesis and crystallization

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.

S2.2. Refinement

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 U_iso(H) = 1.5U_eq (C) for methyl H atoms or 1.2U_eq (C) for secondary and aromatic H atoms. H atoms bonded to N and O atoms were refined isotropically, with U_iso(H) = 1.2U_eq(N) for (I), (III) and (V), and 1.5U_eq (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.

S3. Results and discussion

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 2i_N·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 2i_N·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 2i_N·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

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

	Fig. 1. Synthons used for two and three hydrogen bonds according to Bernstein et al. (1995) and Gerhardt & Egert (2015).
	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.
	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.]
	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.
	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.
	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.]
	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.
	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.
	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.]
	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.
	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.]
	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.
	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.
	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.]
	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)

Crystal data

C4H7N5·C4H9NO	F(000) = 1824
Mr = 212.27	Dx = 1.267 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 8606 reflections
a = 23.198 (3) Å	θ = 3.5–25.8°
b = 26.327 (3) Å	µ = 0.09 mm^−1
c = 7.288 (1) Å	T = 173 K
V = 4451.0 (10) Å^3	Needle, colourless
Z = 16	0.14 × 0.12 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer	1139 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	996 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.109
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −28→28
Tmin = 0.884, Tmax = 0.922	k = −31→31
17579 measured reflections	l = −8→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0846P)^2 + 6.4135P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
1139 reflections	Δρmax = 0.24 e Å^−3
148 parameters	Δρmin = −0.28 e Å^−3
5 restraints	Absolute structure: -
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.50038 (16)	0.36665 (13)	0.5231 (5)	0.0230 (9)
C2	0.50245 (19)	0.41755 (16)	0.5102 (6)	0.0204 (9)
N2	0.45481 (15)	0.44296 (14)	0.5518 (6)	0.0247 (9)
H21	0.4229 (15)	0.4268 (17)	0.584 (7)	0.030*
H22	0.451 (2)	0.4764 (10)	0.539 (7)	0.030*
N3	0.54958 (16)	0.44451 (13)	0.4587 (6)	0.0229 (8)
C4	0.59571 (18)	0.41644 (16)	0.4191 (6)	0.0204 (10)
N4	0.64339 (16)	0.44023 (15)	0.3637 (6)	0.0285 (10)
H41	0.6757 (15)	0.4232 (18)	0.346 (8)	0.034*
H42	0.642 (2)	0.4728 (11)	0.332 (8)	0.034*
N5	0.59932 (17)	0.36526 (14)	0.4306 (6)	0.0258 (9)
C6	0.5497 (2)	0.34317 (15)	0.4814 (7)	0.0230 (9)
C61	0.5499 (2)	0.28668 (17)	0.4904 (10)	0.0388 (13)
H61A	0.5882	0.2740	0.4571	0.058*
H61B	0.5212	0.2731	0.4047	0.058*
H61C	0.5404	0.2758	0.6154	0.058*
C1X	0.5649 (3)	0.5457 (3)	0.0886 (10)	0.0545 (17)
H1X1	0.5400	0.5731	0.0440	0.082*
H1X2	0.5452	0.5272	0.1870	0.082*
H1X3	0.5735	0.5223	−0.0124	0.082*
C2X	0.6213 (3)	0.5683 (2)	0.1627 (8)	0.0471 (15)
O2X	0.65926 (18)	0.54120 (14)	0.2260 (7)	0.0509 (11)
N3X	0.6268 (3)	0.6178 (2)	0.1502 (8)	0.0600 (16)
C4X	0.6817 (4)	0.6403 (3)	0.2137 (11)	0.075 (2)
H4X1	0.6805	0.6772	0.1973	0.112*
H4X2	0.7137	0.6262	0.1421	0.112*
H4X3	0.6874	0.6323	0.3439	0.112*
C5X	0.5813 (4)	0.6515 (3)	0.0847 (14)	0.092 (3)
H5X1	0.5951	0.6867	0.0872	0.138*
H5X2	0.5474	0.6482	0.1640	0.138*
H5X3	0.5709	0.6422	−0.0413	0.138*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0193 (17)	0.0193 (17)	0.031 (2)	−0.0009 (15)	0.0003 (16)	0.0028 (17)
C2	0.019 (2)	0.021 (2)	0.021 (2)	−0.0024 (18)	−0.0004 (18)	0.0011 (19)
N2	0.0166 (19)	0.0161 (17)	0.042 (2)	0.0027 (16)	0.0080 (18)	0.0042 (18)
N3	0.0185 (16)	0.0186 (17)	0.032 (2)	−0.0002 (16)	0.0032 (15)	0.0046 (18)
C4	0.015 (2)	0.018 (2)	0.028 (2)	−0.0005 (17)	−0.0015 (19)	−0.0011 (19)
N4	0.0182 (19)	0.0193 (18)	0.048 (3)	0.0029 (16)	0.0025 (19)	0.0050 (18)
N5	0.0217 (19)	0.0187 (19)	0.037 (2)	0.0019 (15)	0.0018 (18)	0.0018 (18)
C6	0.022 (2)	0.023 (2)	0.024 (2)	0.0007 (19)	−0.0029 (18)	0.007 (2)
C61	0.026 (2)	0.021 (2)	0.070 (4)	−0.003 (2)	0.010 (3)	−0.002 (3)
C1X	0.062 (4)	0.045 (3)	0.056 (4)	0.000 (3)	−0.002 (3)	0.004 (3)
C2X	0.068 (4)	0.038 (3)	0.035 (3)	0.003 (3)	0.017 (3)	0.006 (3)
O2X	0.056 (3)	0.036 (2)	0.061 (3)	0.0007 (19)	0.001 (2)	0.018 (2)
N3X	0.092 (4)	0.038 (3)	0.050 (4)	0.006 (3)	0.015 (3)	0.013 (3)
C4X	0.121 (7)	0.050 (4)	0.053 (4)	−0.032 (4)	0.018 (5)	−0.007 (4)
C5X	0.129 (8)	0.062 (5)	0.086 (6)	0.046 (5)	0.036 (6)	0.038 (5)

Geometric parameters (Å, º)

N1—C6	1.335 (6)	C61—H61C	0.9800
N1—C2	1.344 (6)	C1X—C2X	1.536 (9)
C2—N2	1.327 (6)	C1X—H1X1	0.9800
C2—N3	1.356 (6)	C1X—H1X2	0.9800
N2—H21	0.89 (2)	C1X—H1X3	0.9800
N2—H22	0.89 (2)	C2X—O2X	1.224 (7)
N3—C4	1.332 (5)	C2X—N3X	1.311 (8)
C4—N4	1.334 (6)	N3X—C5X	1.459 (9)
C4—N5	1.352 (6)	N3X—C4X	1.479 (9)
N4—H41	0.88 (2)	C4X—H4X1	0.9800
N4—H42	0.89 (2)	C4X—H4X2	0.9800
N5—C6	1.342 (6)	C4X—H4X3	0.9800
C6—C61	1.489 (6)	C5X—H5X1	0.9800
C61—H61A	0.9800	C5X—H5X2	0.9800
C61—H61B	0.9800	C5X—H5X3	0.9800
C6—N1—C2	114.5 (4)	C2X—C1X—H1X1	109.5
N2—C2—N1	117.2 (4)	C2X—C1X—H1X2	109.5
N2—C2—N3	118.1 (4)	H1X1—C1X—H1X2	109.5
N1—C2—N3	124.7 (4)	C2X—C1X—H1X3	109.5
C2—N2—H21	121 (3)	H1X1—C1X—H1X3	109.5
C2—N2—H22	124 (3)	H1X2—C1X—H1X3	109.5
H21—N2—H22	115 (5)	O2X—C2X—N3X	122.4 (6)
C4—N3—C2	114.6 (3)	O2X—C2X—C1X	121.3 (5)
N3—C4—N4	118.1 (4)	N3X—C2X—C1X	116.3 (6)
N3—C4—N5	126.1 (4)	C2X—N3X—C5X	123.8 (7)
N4—C4—N5	115.8 (4)	C2X—N3X—C4X	117.4 (6)
C4—N4—H41	121 (4)	C5X—N3X—C4X	118.8 (7)
C4—N4—H42	120 (3)	N3X—C4X—H4X1	109.5
H41—N4—H42	119 (5)	N3X—C4X—H4X2	109.5
C6—N5—C4	113.3 (4)	H4X1—C4X—H4X2	109.5
N1—C6—N5	126.7 (4)	N3X—C4X—H4X3	109.5
N1—C6—C61	117.1 (4)	H4X1—C4X—H4X3	109.5
N5—C6—C61	116.3 (4)	H4X2—C4X—H4X3	109.5
C6—C61—H61A	109.5	N3X—C5X—H5X1	109.5
C6—C61—H61B	109.5	N3X—C5X—H5X2	109.5
H61A—C61—H61B	109.5	H5X1—C5X—H5X2	109.5
C6—C61—H61C	109.5	N3X—C5X—H5X3	109.5
H61A—C61—H61C	109.5	H5X1—C5X—H5X3	109.5
H61B—C61—H61C	109.5	H5X2—C5X—H5X3	109.5
C6—N1—C2—N2	−179.4 (4)	C2—N1—C6—N5	0.4 (7)
C6—N1—C2—N3	0.4 (7)	C2—N1—C6—C61	−179.1 (5)
N2—C2—N3—C4	−180.0 (4)	C4—N5—C6—N1	−1.7 (7)
N1—C2—N3—C4	0.3 (7)	C4—N5—C6—C61	177.9 (5)
C2—N3—C4—N4	178.6 (4)	O2X—C2X—N3X—C5X	−176.6 (7)
C2—N3—C4—N5	−1.8 (7)	C1X—C2X—N3X—C5X	4.9 (9)
N3—C4—N5—C6	2.4 (7)	O2X—C2X—N3X—C4X	0.9 (9)
N4—C4—N5—C6	−178.0 (4)	C1X—C2X—N3X—C4X	−177.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N5^i	0.89 (2)	2.15 (3)	3.037 (5)	175 (5)
N2—H22···N3^ii	0.89 (2)	2.16 (3)	3.041 (5)	169 (5)
N4—H41···N1^iii	0.88 (2)	2.10 (3)	2.973 (5)	174 (6)
N4—H42···O2X	0.89 (2)	2.00 (3)	2.865 (5)	163 (5)

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.

(II) 2,4-Diamino-6-methyl-1,3,5-triazine–N-methylpyrrolidin-2-one (1/1)

Crystal data

C4H7N5·C5H9NO	F(000) = 1920
Mr = 224.28	Dx = 1.330 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 15487 reflections
a = 23.178 (2) Å	θ = 3.5–26.0°
b = 26.3327 (17) Å	µ = 0.09 mm^−1
c = 7.3428 (5) Å	T = 173 K
V = 4481.7 (6) Å^3	Block, colourless
Z = 16	0.19 × 0.14 × 0.10 mm

Data collection

Stoe IPDS II two-circle diffractometer	1147 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1050 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.104
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −28→28
Tmin = 0.623, Tmax = 0.776	k = −32→31
27934 measured reflections	l = −8→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 1.9967P] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max < 0.001
1147 reflections	Δρmax = 0.16 e Å^−3
159 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Absolute structure: -
Primary atom site location: structure-invariant direct methods

Special details

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.49594 (12)	0.36682 (10)	0.5730 (4)	0.0228 (7)
C2	0.49845 (14)	0.41812 (12)	0.5642 (5)	0.0200 (7)
N2	0.45130 (13)	0.44390 (12)	0.6090 (5)	0.0249 (7)
H21	0.4501 (17)	0.4796 (17)	0.595 (5)	0.030*
H22	0.4216 (18)	0.4258 (16)	0.627 (6)	0.030*
N3	0.54562 (12)	0.44473 (10)	0.5151 (5)	0.0209 (6)
C4	0.59207 (14)	0.41692 (12)	0.4753 (5)	0.0199 (8)
N4	0.63988 (13)	0.44089 (12)	0.4230 (5)	0.0233 (7)
H41	0.6692 (19)	0.4242 (16)	0.388 (6)	0.028*
H42	0.6392 (16)	0.4738 (16)	0.406 (6)	0.028*
N5	0.59445 (12)	0.36540 (10)	0.4812 (4)	0.0224 (7)
C6	0.54485 (15)	0.34311 (12)	0.5305 (6)	0.0227 (8)
C61	0.54503 (18)	0.28666 (13)	0.5392 (7)	0.0377 (11)
H61A	0.5523	0.2758	0.6647	0.056*
H61B	0.5754	0.2734	0.4595	0.056*
H61C	0.5075	0.2737	0.4991	0.056*
N1X	0.58914 (12)	0.58571 (12)	0.1681 (5)	0.0305 (8)
C1X	0.55352 (18)	0.54228 (16)	0.1290 (7)	0.0385 (10)
H1X1	0.5742	0.5112	0.1623	0.058*
H1X2	0.5444	0.5416	−0.0013	0.058*
H1X3	0.5177	0.5445	0.1994	0.058*
C2X	0.64175 (16)	0.58309 (15)	0.2446 (6)	0.0308 (9)
O2X	0.66470 (12)	0.54405 (11)	0.2990 (5)	0.0427 (8)
C3X	0.66724 (16)	0.63528 (14)	0.2470 (6)	0.0316 (9)
H3X1	0.7003	0.6374	0.1621	0.038*
H3X2	0.6808	0.6441	0.3710	0.038*
C4X	0.61915 (17)	0.67100 (14)	0.1875 (6)	0.0333 (9)
H4X1	0.6330	0.6946	0.0921	0.040*
H4X2	0.6049	0.6911	0.2921	0.040*
C5X	0.57135 (16)	0.63644 (14)	0.1128 (6)	0.0314 (9)
H5X1	0.5335	0.6453	0.1663	0.038*
H5X2	0.5688	0.6390	−0.0215	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0182 (14)	0.0193 (14)	0.0308 (18)	0.0020 (12)	0.0057 (12)	0.0016 (14)
C2	0.0174 (15)	0.0232 (17)	0.0195 (17)	0.0006 (14)	−0.0017 (13)	−0.0004 (16)
N2	0.0183 (15)	0.0167 (15)	0.0396 (19)	−0.0023 (13)	0.0052 (15)	0.0013 (14)
N3	0.0154 (12)	0.0186 (13)	0.0288 (15)	−0.0002 (12)	0.0012 (12)	0.0015 (14)
C4	0.0150 (15)	0.0229 (18)	0.0218 (19)	−0.0003 (14)	−0.0006 (14)	−0.0010 (16)
N4	0.0149 (14)	0.0161 (14)	0.0389 (19)	0.0021 (13)	0.0058 (14)	0.0008 (13)
N5	0.0195 (15)	0.0159 (15)	0.0319 (18)	0.0021 (11)	0.0021 (13)	0.0009 (14)
C6	0.0202 (15)	0.0219 (16)	0.0260 (19)	−0.0002 (15)	−0.0025 (14)	0.0000 (16)
C61	0.0282 (18)	0.0218 (18)	0.063 (3)	0.0013 (17)	0.012 (2)	−0.004 (2)
N1X	0.0261 (16)	0.0292 (17)	0.0362 (19)	−0.0025 (13)	0.0013 (16)	0.0057 (15)
C1X	0.033 (2)	0.035 (2)	0.047 (3)	−0.0059 (18)	0.002 (2)	−0.002 (2)
C2X	0.0286 (19)	0.033 (2)	0.031 (2)	0.0023 (17)	0.0052 (18)	0.0052 (18)
O2X	0.0350 (15)	0.0310 (15)	0.062 (2)	0.0070 (12)	−0.0020 (14)	0.0141 (15)
C3X	0.030 (2)	0.033 (2)	0.031 (2)	−0.0018 (17)	0.0016 (18)	0.0044 (18)
C4X	0.041 (2)	0.0260 (19)	0.033 (2)	0.0008 (18)	0.0035 (18)	0.0027 (17)
C5X	0.0297 (19)	0.032 (2)	0.033 (2)	0.0076 (17)	0.0028 (18)	0.0079 (18)

Geometric parameters (Å, º)

N1—C6	1.331 (4)	N1X—C2X	1.344 (5)
N1—C2	1.354 (4)	N1X—C1X	1.439 (5)
C2—N2	1.328 (5)	N1X—C5X	1.456 (5)
C2—N3	1.348 (4)	C1X—H1X1	0.9800
N2—H21	0.95 (4)	C1X—H1X2	0.9800
N2—H22	0.85 (4)	C1X—H1X3	0.9800
N3—C4	1.334 (4)	C2X—O2X	1.224 (5)
C4—N4	1.332 (4)	C2X—C3X	1.496 (5)
C4—N5	1.358 (4)	C3X—C4X	1.522 (5)
N4—H41	0.85 (5)	C3X—H3X1	0.9900
N4—H42	0.88 (4)	C3X—H3X2	0.9900
N5—C6	1.341 (4)	C4X—C5X	1.535 (6)
C6—C61	1.488 (5)	C4X—H4X1	0.9900
C61—H61A	0.9800	C4X—H4X2	0.9900
C61—H61B	0.9800	C5X—H5X1	0.9900
C61—H61C	0.9800	C5X—H5X2	0.9900
C6—N1—C2	114.8 (3)	N1X—C1X—H1X1	109.5
N2—C2—N3	117.9 (3)	N1X—C1X—H1X2	109.5
N2—C2—N1	117.6 (3)	H1X1—C1X—H1X2	109.5
N3—C2—N1	124.5 (3)	N1X—C1X—H1X3	109.5
C2—N2—H21	120 (2)	H1X1—C1X—H1X3	109.5
C2—N2—H22	115 (3)	H1X2—C1X—H1X3	109.5
H21—N2—H22	124 (4)	O2X—C2X—N1X	125.0 (4)
C4—N3—C2	115.3 (3)	O2X—C2X—C3X	126.6 (4)
N4—C4—N3	118.3 (3)	N1X—C2X—C3X	108.4 (3)
N4—C4—N5	116.7 (3)	C2X—C3X—C4X	106.0 (3)
N3—C4—N5	125.0 (3)	C2X—C3X—H3X1	110.5
C4—N4—H41	121 (3)	C4X—C3X—H3X1	110.5
C4—N4—H42	120 (3)	C2X—C3X—H3X2	110.5
H41—N4—H42	119 (4)	C4X—C3X—H3X2	110.5
C6—N5—C4	114.2 (3)	H3X1—C3X—H3X2	108.7
N1—C6—N5	126.0 (3)	C3X—C4X—C5X	105.4 (3)
N1—C6—C61	117.4 (3)	C3X—C4X—H4X1	110.7
N5—C6—C61	116.5 (3)	C5X—C4X—H4X1	110.7
C6—C61—H61A	109.5	C3X—C4X—H4X2	110.7
C6—C61—H61B	109.5	C5X—C4X—H4X2	110.7
H61A—C61—H61B	109.5	H4X1—C4X—H4X2	108.8
C6—C61—H61C	109.5	N1X—C5X—C4X	103.9 (3)
H61A—C61—H61C	109.5	N1X—C5X—H5X1	111.0
H61B—C61—H61C	109.5	C4X—C5X—H5X1	111.0
C2X—N1X—C1X	124.3 (3)	N1X—C5X—H5X2	111.0
C2X—N1X—C5X	114.9 (3)	C4X—C5X—H5X2	111.0
C1X—N1X—C5X	120.7 (3)	H5X1—C5X—H5X2	109.0
C6—N1—C2—N2	−178.6 (4)	C4—N5—C6—C61	180.0 (4)
C6—N1—C2—N3	0.7 (6)	C1X—N1X—C2X—O2X	−4.0 (6)
N2—C2—N3—C4	178.6 (3)	C5X—N1X—C2X—O2X	−179.5 (4)
N1—C2—N3—C4	−0.6 (6)	C1X—N1X—C2X—C3X	174.7 (4)
C2—N3—C4—N4	179.0 (3)	C5X—N1X—C2X—C3X	−0.8 (5)
C2—N3—C4—N5	0.0 (6)	O2X—C2X—C3X—C4X	−173.0 (4)
N4—C4—N5—C6	−178.5 (3)	N1X—C2X—C3X—C4X	8.3 (4)
N3—C4—N5—C6	0.4 (5)	C2X—C3X—C4X—C5X	−12.1 (4)
C2—N1—C6—N5	−0.1 (6)	C2X—N1X—C5X—C4X	−6.9 (5)
C2—N1—C6—C61	179.5 (4)	C1X—N1X—C5X—C4X	177.4 (4)
C4—N5—C6—N1	−0.4 (6)	C3X—C4X—C5X—N1X	11.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N3^i	0.95 (4)	2.08 (4)	3.013 (4)	169 (4)
N2—H22···N5^ii	0.85 (4)	2.23 (5)	3.062 (4)	168 (4)
N4—H41···N1^iii	0.85 (5)	2.14 (5)	2.982 (4)	175 (4)
N4—H42···O2X	0.88 (4)	2.09 (4)	2.922 (4)	157 (4)

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.

(III) 2,4-Diamino-6-methyl-1,3,5-triazine–2,6-dichlorophenol (1/1)

Crystal data

C6H4Cl2O·C4H7N5	Z = 2
Mr = 288.14	F(000) = 296
Triclinic, P1	Dx = 1.516 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0318 (7) Å	Cell parameters from 2942 reflections
b = 8.5779 (11) Å	θ = 3.5–26.0°
c = 15.008 (2) Å	µ = 0.51 mm^−1
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) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	2354 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1864 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.033
ω scans	θmax = 25.6°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −6→5
Tmin = 0.719, Tmax = 0.872	k = −10→10
5126 measured reflections	l = −18→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0448P)^2] where P = (Fo^2 + 2Fc^2)/3
2354 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1B	0.9771 (3)	0.16148 (16)	0.42259 (10)	0.0264 (3)
C2B	0.8271 (4)	0.21542 (19)	0.48369 (12)	0.0246 (4)
N2B	0.7876 (4)	0.1316 (2)	0.55389 (12)	0.0329 (4)
H2B1	0.706 (5)	0.168 (3)	0.5937 (16)	0.040*
H2B2	0.853 (5)	0.048 (3)	0.5601 (16)	0.040*
N3B	0.7150 (3)	0.34583 (16)	0.47818 (10)	0.0248 (3)
C4B	0.7728 (4)	0.42905 (19)	0.40828 (11)	0.0227 (4)
N4B	0.6633 (4)	0.55767 (19)	0.39815 (12)	0.0294 (4)
H4B1	0.679 (5)	0.603 (3)	0.3510 (16)	0.035*
H4B2	0.545 (5)	0.579 (3)	0.4332 (16)	0.035*
N5B	0.9340 (3)	0.39039 (16)	0.34689 (10)	0.0256 (3)
C6B	1.0255 (4)	0.2552 (2)	0.35688 (12)	0.0246 (4)
C61B	1.1942 (4)	0.2055 (2)	0.28837 (14)	0.0332 (5)
H6B1	1.3221	0.1434	0.3158	0.050*	0.71 (2)
H6B2	1.2956	0.3000	0.2659	0.050*	0.71 (2)
H6B3	1.0758	0.1404	0.2383	0.050*	0.71 (2)
H6BA	1.3856	0.2532	0.3069	0.050*	0.29 (2)
H6BB	1.1342	0.2412	0.2302	0.050*	0.29 (2)
H6BC	1.1738	0.0894	0.2829	0.050*	0.29 (2)
C1A	0.1526 (4)	0.6818 (2)	0.19030 (12)	0.0261 (4)
O1A	0.1896 (3)	0.62854 (16)	0.27128 (9)	0.0325 (3)
H1A	0.083 (6)	0.545 (3)	0.2841 (17)	0.049*
C2A	−0.0606 (4)	0.6224 (2)	0.12390 (13)	0.0326 (4)
Cl2A	−0.30587 (12)	0.46466 (7)	0.14567 (4)	0.04572 (17)
C3A	−0.0874 (5)	0.6851 (3)	0.04147 (15)	0.0466 (6)
H3A	−0.2353	0.6409	−0.0030	0.056*
C4A	0.1029 (6)	0.8121 (3)	0.02492 (16)	0.0551 (7)
H4A	0.0858	0.8563	−0.0313	0.066*
C5A	0.3175 (6)	0.8757 (3)	0.08890 (16)	0.0473 (6)
H5A	0.4482	0.9638	0.0773	0.057*
C6A	0.3417 (4)	0.8105 (2)	0.17021 (13)	0.0315 (4)
Cl6A	0.61299 (11)	0.88885 (6)	0.25170 (4)	0.04033 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1B	0.0305 (9)	0.0197 (7)	0.0300 (8)	0.0056 (6)	0.0067 (7)	0.0020 (6)
C2B	0.0262 (10)	0.0188 (8)	0.0280 (9)	0.0020 (7)	0.0032 (8)	0.0016 (7)
N2B	0.0466 (12)	0.0248 (8)	0.0336 (9)	0.0150 (8)	0.0145 (8)	0.0093 (7)
N3B	0.0244 (8)	0.0221 (7)	0.0283 (8)	0.0048 (6)	0.0038 (6)	0.0039 (6)
C4B	0.0192 (9)	0.0215 (8)	0.0257 (9)	0.0016 (7)	−0.0013 (7)	0.0026 (7)
N4B	0.0314 (10)	0.0301 (8)	0.0319 (9)	0.0131 (7)	0.0091 (7)	0.0126 (7)
N5B	0.0246 (8)	0.0243 (8)	0.0282 (8)	0.0038 (6)	0.0049 (6)	0.0036 (6)
C6B	0.0236 (10)	0.0201 (8)	0.0284 (9)	0.0015 (7)	0.0014 (7)	0.0004 (7)
C61B	0.0354 (12)	0.0279 (9)	0.0386 (11)	0.0066 (8)	0.0140 (9)	0.0027 (8)
C1A	0.0271 (10)	0.0267 (9)	0.0275 (9)	0.0099 (7)	0.0065 (8)	0.0046 (7)
O1A	0.0320 (8)	0.0326 (7)	0.0295 (7)	−0.0032 (6)	−0.0015 (6)	0.0107 (6)
C2A	0.0330 (11)	0.0364 (10)	0.0298 (10)	0.0095 (8)	0.0055 (8)	0.0035 (8)
Cl2A	0.0367 (3)	0.0533 (3)	0.0395 (3)	−0.0067 (2)	−0.0046 (2)	0.0029 (2)
C3A	0.0510 (15)	0.0591 (14)	0.0296 (11)	0.0143 (11)	−0.0035 (10)	0.0059 (10)
C4A	0.0724 (19)	0.0630 (15)	0.0335 (12)	0.0149 (14)	0.0078 (12)	0.0223 (11)
C5A	0.0588 (16)	0.0437 (12)	0.0433 (13)	0.0072 (11)	0.0191 (12)	0.0179 (10)
C6A	0.0316 (11)	0.0303 (10)	0.0349 (11)	0.0080 (8)	0.0091 (9)	0.0049 (8)
Cl6A	0.0348 (3)	0.0338 (3)	0.0491 (3)	−0.0038 (2)	0.0066 (2)	0.0050 (2)

Geometric parameters (Å, º)

N1B—C6B	1.330 (2)	C61B—H6BA	0.9800
N1B—C2B	1.356 (2)	C61B—H6BB	0.9800
C2B—N2B	1.329 (2)	C61B—H6BC	0.9800
C2B—N3B	1.342 (2)	C1A—O1A	1.333 (2)
N2B—H2B1	0.84 (2)	C1A—C2A	1.382 (3)
N2B—H2B2	0.85 (3)	C1A—C6A	1.397 (3)
N3B—C4B	1.338 (2)	O1A—H1A	0.86 (3)
C4B—N4B	1.328 (2)	C2A—C3A	1.385 (3)
C4B—N5B	1.354 (2)	C2A—Cl2A	1.738 (2)
N4B—H4B1	0.83 (2)	C3A—C4A	1.374 (4)
N4B—H4B2	0.87 (3)	C3A—H3A	0.9500
N5B—C6B	1.332 (2)	C4A—C5A	1.372 (4)
C6B—C61B	1.488 (3)	C4A—H4A	0.9500
C61B—H6B1	0.9800	C5A—C6A	1.379 (3)
C61B—H6B2	0.9800	C5A—H5A	0.9500
C61B—H6B3	0.9800	C6A—Cl6A	1.736 (2)
C6B—N1B—C2B	114.68 (15)	H6BA—C61B—H6BB	109.5
N2B—C2B—N3B	117.89 (17)	C6B—C61B—H6BC	109.5
N2B—C2B—N1B	117.13 (16)	H6BA—C61B—H6BC	109.5
N3B—C2B—N1B	124.98 (15)	H6BB—C61B—H6BC	109.5
C2B—N2B—H2B1	117.3 (15)	O1A—C1A—C2A	125.68 (17)
C2B—N2B—H2B2	121.3 (16)	O1A—C1A—C6A	117.98 (18)
H2B1—N2B—H2B2	121 (2)	C2A—C1A—C6A	116.34 (17)
C4B—N3B—C2B	114.98 (15)	C1A—O1A—H1A	120.0 (17)
N4B—C4B—N3B	117.81 (17)	C1A—C2A—C3A	122.5 (2)
N4B—C4B—N5B	117.79 (16)	C1A—C2A—Cl2A	118.49 (14)
N3B—C4B—N5B	124.40 (16)	C3A—C2A—Cl2A	119.03 (18)
C4B—N4B—H4B1	118.5 (15)	C4A—C3A—C2A	119.1 (2)
C4B—N4B—H4B2	119.1 (14)	C4A—C3A—H3A	120.4
H4B1—N4B—H4B2	121 (2)	C2A—C3A—H3A	120.4
C6B—N5B—C4B	115.45 (14)	C5A—C4A—C3A	120.5 (2)
N1B—C6B—N5B	125.32 (17)	C5A—C4A—H4A	119.7
N1B—C6B—C61B	117.75 (16)	C3A—C4A—H4A	119.7
N5B—C6B—C61B	116.93 (15)	C4A—C5A—C6A	119.4 (2)
C6B—C61B—H6B1	109.5	C4A—C5A—H5A	120.3
C6B—C61B—H6B2	109.5	C6A—C5A—H5A	120.3
C6B—C61B—H6B3	109.5	C5A—C6A—C1A	122.1 (2)
C6B—C61B—H6BA	109.5	C5A—C6A—Cl6A	119.97 (17)
C6B—C61B—H6BB	109.5	C1A—C6A—Cl6A	117.89 (14)
C6B—N1B—C2B—N2B	−175.78 (18)	C6A—C1A—C2A—C3A	0.3 (3)
C6B—N1B—C2B—N3B	4.6 (3)	O1A—C1A—C2A—Cl2A	0.1 (3)
N2B—C2B—N3B—C4B	177.00 (17)	C6A—C1A—C2A—Cl2A	−178.86 (14)
N1B—C2B—N3B—C4B	−3.4 (3)	C1A—C2A—C3A—C4A	−0.6 (3)
C2B—N3B—C4B—N4B	178.67 (16)	Cl2A—C2A—C3A—C4A	178.52 (19)
C2B—N3B—C4B—N5B	−0.9 (3)	C2A—C3A—C4A—C5A	0.3 (4)
N4B—C4B—N5B—C6B	−176.09 (17)	C3A—C4A—C5A—C6A	0.3 (4)
N3B—C4B—N5B—C6B	3.5 (3)	C4A—C5A—C6A—C1A	−0.6 (3)
C2B—N1B—C6B—N5B	−1.7 (3)	C4A—C5A—C6A—Cl6A	179.68 (19)
C2B—N1B—C6B—C61B	178.69 (17)	O1A—C1A—C6A—C5A	−178.74 (19)
C4B—N5B—C6B—N1B	−2.1 (3)	C2A—C1A—C6A—C5A	0.3 (3)
C4B—N5B—C6B—C61B	177.56 (16)	O1A—C1A—C6A—Cl6A	1.0 (2)
O1A—C1A—C2A—C3A	179.3 (2)	C2A—C1A—C6A—Cl6A	−179.97 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4B—H4B1···O1A	0.83 (2)	2.68 (2)	3.060 (2)	110 (2)
N4B—H4B1···Cl6A	0.83 (2)	3.01 (2)	3.7354 (17)	147 (2)
N2B—H2B1···O1A^i	0.84 (2)	2.53 (2)	3.200 (2)	139 (2)
N2B—H2B2···N1B^ii	0.85 (3)	2.14 (3)	2.987 (2)	179 (2)
N4B—H4B2···N3B^i	0.87 (3)	2.11 (3)	2.977 (2)	174 (2)
O1A—H1A···N5B^iii	0.86 (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) x−1, y, z.

(IV) 2,6-Diaminopyrimidin-4(3H)-one–N-methylpyrrolidin-2-one (1/1)

Crystal data

C4H6N4O·C5H9NO	F(000) = 480
Mr = 225.26	Dx = 1.338 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25481 reflections
a = 8.1456 (5) Å	θ = 3.3–26.0°
b = 9.2289 (6) Å	µ = 0.10 mm^−1
c = 14.9731 (9) Å	T = 173 K
β = 96.463 (5)°	Block, colourless
V = 1118.45 (12) Å^3	0.50 × 0.45 × 0.30 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	2098 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1912 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.073
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.869, Tmax = 0.914	k = −11→11
28235 measured reflections	l = −17→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0893P)^2 + 0.8169P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2098 reflections	Δρmax = 0.61 e Å^−3
212 parameters	Δρmin = −0.41 e Å^−3
32 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (7)

Special details

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.3959 (2)	0.33450 (19)	0.70055 (13)	0.0351 (5)
C2	0.4815 (3)	0.4517 (2)	0.72640 (15)	0.0352 (5)
N2	0.6421 (2)	0.4574 (2)	0.71351 (16)	0.0426 (6)
H21	0.689 (4)	0.371 (3)	0.7025 (19)	0.048 (7)*
H22	0.704 (4)	0.530 (3)	0.745 (2)	0.051 (8)*
N3	0.4148 (2)	0.5680 (2)	0.76271 (14)	0.0360 (5)
H3	0.479 (4)	0.646 (4)	0.7774 (19)	0.052 (8)*
C4	0.2487 (3)	0.5746 (2)	0.77620 (15)	0.0347 (5)
O4	0.19854 (19)	0.68802 (17)	0.81076 (12)	0.0420 (5)
C5	0.1561 (3)	0.4521 (2)	0.74841 (16)	0.0365 (6)
H5	0.0416	0.4482	0.7553	0.044*
C6	0.2316 (3)	0.3366 (2)	0.71089 (15)	0.0337 (5)
N6	0.1494 (3)	0.2150 (2)	0.68309 (16)	0.0409 (5)
H61	0.191 (4)	0.162 (3)	0.644 (2)	0.049 (8)*
H62	0.038 (5)	0.214 (3)	0.686 (2)	0.060 (9)*
O2X	0.2800 (4)	−0.0024 (3)	0.5758 (2)	0.1088 (12)
C5X	0.2443 (8)	−0.3733 (4)	0.5204 (3)	0.1028 (17)
H5X1	0.2862	−0.4544	0.5598	0.123*	0.591 (9)
H5X2	0.2510	−0.3983	0.4566	0.123*	0.591 (9)
H5XA	0.1878	−0.3978	0.4602	0.123*	0.409 (9)
H5XB	0.2311	−0.4547	0.5620	0.123*	0.409 (9)
N1X	0.3228 (8)	−0.2372 (5)	0.5459 (3)	0.0684 (18)	0.591 (9)
C1X	0.4979 (10)	−0.2377 (10)	0.5403 (8)	0.085 (3)	0.591 (9)
H1X1	0.5350	−0.3373	0.5317	0.127*	0.591 (9)
H1X2	0.5556	−0.1984	0.5960	0.127*	0.591 (9)
H1X3	0.5224	−0.1779	0.4894	0.127*	0.591 (9)
C2X	0.2360 (11)	−0.1221 (7)	0.5557 (9)	0.063 (3)	0.591 (9)
C3X	0.0540 (8)	−0.1597 (11)	0.5493 (6)	0.095 (3)	0.591 (9)
H3X1	0.0050	−0.1331	0.6046	0.114*	0.591 (9)
H3X2	−0.0097	−0.1138	0.4966	0.114*	0.591 (9)
C4X	0.0661 (13)	−0.3216 (12)	0.5385 (10)	0.142 (6)	0.591 (9)
H4X1	−0.0148	−0.3529	0.4878	0.171*	0.591 (9)
H4X2	0.0363	−0.3692	0.5937	0.171*	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)
H1XA	−0.0177	−0.3661	0.5472	0.123*	0.409 (9)
H1XB	−0.0531	−0.1995	0.5224	0.123*	0.409 (9)
H1XC	−0.0041	−0.2461	0.6249	0.123*	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)
H3XA	0.4828	−0.1242	0.4834	0.147*	0.409 (9)
H3XB	0.5428	−0.1619	0.5872	0.147*	0.409 (9)
C4X'	0.4317 (13)	−0.3364 (12)	0.5169 (8)	0.104 (5)	0.409 (9)
H4XA	0.5014	−0.3948	0.5619	0.125*	0.409 (9)
H4XB	0.4640	−0.3587	0.4566	0.125*	0.409 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0279 (9)	0.0272 (9)	0.0509 (11)	0.0002 (7)	0.0078 (8)	−0.0002 (8)
C2	0.0307 (11)	0.0282 (11)	0.0472 (13)	0.0005 (8)	0.0070 (9)	0.0022 (9)
N2	0.0281 (10)	0.0306 (10)	0.0707 (15)	−0.0024 (8)	0.0124 (9)	−0.0074 (10)
N3	0.0288 (10)	0.0265 (10)	0.0534 (12)	−0.0012 (7)	0.0077 (8)	−0.0021 (8)
C4	0.0303 (11)	0.0284 (11)	0.0462 (12)	0.0021 (8)	0.0070 (9)	0.0019 (9)
O4	0.0321 (8)	0.0289 (8)	0.0665 (11)	0.0015 (6)	0.0122 (7)	−0.0068 (7)
C5	0.0275 (11)	0.0303 (11)	0.0526 (13)	0.0007 (8)	0.0077 (9)	0.0010 (9)
C6	0.0296 (11)	0.0280 (10)	0.0436 (12)	−0.0006 (8)	0.0049 (9)	0.0041 (9)
N6	0.0304 (10)	0.0309 (10)	0.0622 (13)	−0.0025 (8)	0.0089 (9)	−0.0064 (9)
O2X	0.135 (3)	0.0803 (19)	0.104 (2)	0.0409 (19)	−0.0184 (19)	−0.0484 (17)
C5X	0.185 (6)	0.062 (2)	0.061 (2)	−0.016 (3)	0.016 (3)	0.0039 (18)
N1X	0.106 (5)	0.047 (3)	0.052 (3)	0.004 (3)	0.013 (3)	−0.002 (2)
C1X	0.101 (6)	0.074 (6)	0.085 (5)	0.030 (5)	0.032 (4)	−0.003 (5)
C2X	0.078 (5)	0.066 (5)	0.043 (4)	−0.001 (4)	0.003 (5)	−0.014 (3)
C3X	0.072 (4)	0.140 (8)	0.071 (4)	−0.008 (5)	0.000 (3)	−0.031 (5)
C4X	0.163 (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)

N1—C2	1.321 (3)	C5X—H5XB	0.9901
N1—C6	1.365 (3)	N1X—C2X	1.293 (8)
C2—N2	1.345 (3)	N1X—C1X	1.438 (8)
C2—N3	1.345 (3)	C1X—H1X1	0.9800
N2—H21	0.91 (3)	C1X—H1X2	0.9800
N2—H22	0.94 (3)	C1X—H1X3	0.9800
N3—C4	1.391 (3)	C2X—C3X	1.515 (8)
N3—H3	0.91 (3)	C3X—C4X	1.507 (9)
C4—O4	1.256 (3)	C3X—H3X1	0.9900
C4—C5	1.397 (3)	C3X—H3X2	0.9900
C5—C6	1.381 (3)	C4X—H4X1	0.9900
C5—H5	0.9500	C4X—H4X2	0.9900
C6—N6	1.348 (3)	N1X'—C2X'	1.321 (9)
N6—H61	0.87 (3)	N1X'—C1X'	1.423 (9)
N6—H62	0.92 (4)	C1X'—H1XA	0.9800
O2X—C2X	1.189 (7)	C1X'—H1XB	0.9800
O2X—C2X'	1.228 (9)	C1X'—H1XC	0.9800
C5X—N1X'	1.381 (7)	C2X'—C3X'	1.534 (10)
C5X—N1X	1.441 (6)	C3X'—C4X'	1.499 (10)
C5X—C4X'	1.571 (9)	C3X'—H3XA	0.9900
C5X—C4X	1.580 (9)	C3X'—H3XB	0.9900
C5X—H5X1	0.9900	C4X'—H4XA	0.9900
C5X—H5X2	0.9900	C4X'—H4XB	0.9900
C5X—H5XA	0.9900
C2—N1—C6	116.57 (18)	C2X—N1X—C1X	124.6 (7)
N1—C2—N2	118.7 (2)	C2X—N1X—C5X	121.0 (6)
N1—C2—N3	123.2 (2)	C1X—N1X—C5X	113.3 (6)
N2—C2—N3	118.1 (2)	N1X—C1X—H1X1	109.5
C2—N2—H21	115.3 (18)	N1X—C1X—H1X2	109.5
C2—N2—H22	115.4 (18)	H1X1—C1X—H1X2	109.5
H21—N2—H22	121 (3)	N1X—C1X—H1X3	109.5
C2—N3—C4	122.52 (19)	H1X1—C1X—H1X3	109.5
C2—N3—H3	119.2 (19)	H1X2—C1X—H1X3	109.5
C4—N3—H3	118.3 (19)	O2X—C2X—N1X	129.7 (8)
O4—C4—N3	117.61 (19)	O2X—C2X—C3X	119.6 (7)
O4—C4—C5	127.4 (2)	N1X—C2X—C3X	110.3 (6)
N3—C4—C5	114.99 (19)	C4X—C3X—C2X	99.1 (7)
C6—C5—C4	119.7 (2)	C4X—C3X—H3X1	111.9
C6—C5—H5	120.1	C2X—C3X—H3X1	111.9
C4—C5—H5	120.1	C4X—C3X—H3X2	111.9
N6—C6—N1	114.36 (19)	C2X—C3X—H3X2	111.9
N6—C6—C5	122.6 (2)	H3X1—C3X—H3X2	109.6
N1—C6—C5	122.99 (19)	C3X—C4X—C5X	113.0 (7)
C6—N6—H61	117 (2)	C3X—C4X—H4X1	109.0
C6—N6—H62	117 (2)	C5X—C4X—H4X1	109.0
H61—N6—H62	120 (3)	C3X—C4X—H4X2	109.0
N1X'—C5X—N1X	47.9 (4)	C5X—C4X—H4X2	109.0
N1X'—C5X—C4X'	102.2 (6)	H4X1—C4X—H4X2	107.8
N1X—C5X—C4X'	54.3 (5)	C2X'—N1X'—C5X	117.9 (8)
N1X'—C5X—C4X	46.7 (6)	C2X'—N1X'—C1X'	133.8 (10)
N1X—C5X—C4X	94.6 (6)	C5X—N1X'—C1X'	108.2 (8)
C4X'—C5X—C4X	148.8 (6)	N1X'—C1X'—H1XA	109.5
N1X'—C5X—H5X1	123.6	N1X'—C1X'—H1XB	109.5
N1X—C5X—H5X1	112.8	H1XA—C1X'—H1XB	109.5
C4X'—C5X—H5X1	85.0	N1X'—C1X'—H1XC	109.5
C4X—C5X—H5X1	112.8	H1XA—C1X'—H1XC	109.5
N1X'—C5X—H5X2	126.2	H1XB—C1X'—H1XC	109.5
N1X—C5X—H5X2	112.8	O2X—C2X'—N1X'	139.4 (12)
C4X'—C5X—H5X2	81.9	O2X—C2X'—C3X'	110.7 (9)
C4X—C5X—H5X2	112.8	N1X'—C2X'—C3X'	109.2 (9)
H5X1—C5X—H5X2	110.3	C4X'—C3X'—C2X'	102.4 (9)
N1X'—C5X—H5XA	111.1	C4X'—C3X'—H3XA	111.3
N1X—C5X—H5XA	125.9	C2X'—C3X'—H3XA	111.3
C4X'—C5X—H5XA	111.9	C4X'—C3X'—H3XB	111.3
C4X—C5X—H5XA	83.3	C2X'—C3X'—H3XB	111.3
H5X1—C5X—H5XA	117.6	H3XA—C3X'—H3XB	109.2
N1X'—C5X—H5XB	111.4	C3X'—C4X'—C5X	107.8 (8)
N1X—C5X—H5XB	124.8	C3X'—C4X'—H4XA	110.1
C4X'—C5X—H5XB	111.1	C5X—C4X'—H4XA	110.1
C4X—C5X—H5XB	87.4	C3X'—C4X'—H4XB	110.1
H5X2—C5X—H5XB	116.9	C5X—C4X'—H4XB	110.1
H5XA—C5X—H5XB	109.1	H4XA—C4X'—H4XB	108.5
C6—N1—C2—N2	−176.8 (2)	O2X—C2X—C3X—C4X	−170.9 (12)
C6—N1—C2—N3	1.1 (3)	N1X—C2X—C3X—C4X	2.6 (13)
N1—C2—N3—C4	0.0 (4)	C2X—C3X—C4X—C5X	−10.8 (12)
N2—C2—N3—C4	178.0 (2)	N1X'—C5X—C4X—C3X	15.6 (7)
C2—N3—C4—O4	179.9 (2)	N1X—C5X—C4X—C3X	13.8 (10)
C2—N3—C4—C5	−0.6 (3)	C4X'—C5X—C4X—C3X	10 (2)
O4—C4—C5—C6	179.5 (2)	N1X—C5X—N1X'—C2X'	5.6 (15)
N3—C4—C5—C6	0.0 (3)	C4X'—C5X—N1X'—C2X'	5.2 (16)
C2—N1—C6—N6	179.6 (2)	C4X—C5X—N1X'—C2X'	−172.0 (18)
C2—N1—C6—C5	−1.7 (3)	N1X—C5X—N1X'—C1X'	−177.0 (10)
C4—C5—C6—N6	179.7 (2)	C4X'—C5X—N1X'—C1X'	−177.4 (9)
C4—C5—C6—N1	1.1 (3)	C4X—C5X—N1X'—C1X'	5.4 (13)
N1X'—C5X—N1X—C2X	−14.8 (9)	C2X—O2X—C2X'—N1X'	−18 (2)
C4X'—C5X—N1X—C2X	164.6 (10)	C2X—O2X—C2X'—C3X'	150 (7)
C4X—C5X—N1X—C2X	−13.1 (10)	C5X—N1X'—C2X'—O2X	167 (3)
N1X'—C5X—N1X—C1X	177.3 (8)	C1X'—N1X'—C2X'—O2X	−9 (5)
C4X'—C5X—N1X—C1X	−3.3 (7)	C5X—N1X'—C2X'—C3X'	−1 (2)
C4X—C5X—N1X—C1X	179.0 (7)	C1X'—N1X'—C2X'—C3X'	−177.6 (14)
C2X'—O2X—C2X—N1X	−10 (4)	O2X—C2X'—C3X'—C4X'	−175.7 (18)
C2X'—O2X—C2X—C3X	162 (6)	N1X'—C2X'—C3X'—C4X'	−4 (2)
C1X—N1X—C2X—O2X	−13 (2)	C2X'—C3X'—C4X'—C5X	6.7 (18)
C5X—N1X—C2X—O2X	−179.6 (10)	N1X'—C5X—C4X'—C3X'	−7.3 (12)
C1X—N1X—C2X—C3X	174.2 (8)	N1X—C5X—C4X'—C3X'	−7.7 (10)
C5X—N1X—C2X—C3X	7.7 (13)	C4X—C5X—C4X'—C3X'	−3.2 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O4^i	0.91 (3)	1.94 (3)	2.846 (3)	175 (3)
N2—H22···N6^ii	0.94 (3)	2.28 (3)	3.216 (3)	177 (3)
N3—H3···N1^ii	0.91 (3)	2.02 (3)	2.922 (3)	173 (3)
N6—H61···O2X	0.87 (3)	2.01 (3)	2.850 (3)	165 (3)
N6—H62···O4^iii	0.92 (4)	1.94 (4)	2.857 (3)	173 (3)

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.

(V) 2,6-Diaminopyrimidin-4(3H)-one–2,6-dichloroaniline–\ N,N-dimethylacetamide (1/1/1)

Crystal data

C6H5Cl2N·C4H6N4O·C4H9NO	F(000) = 392
Mr = 375.26	Dx = 1.388 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 23474 reflections
a = 8.1060 (5) Å	θ = 3.3–26.4°
b = 9.0448 (5) Å	µ = 0.38 mm^−1
c = 12.5656 (8) Å	T = 173 K
β = 102.859 (5)°	Block, colourless
V = 898.17 (9) Å^3	0.20 × 0.14 × 0.12 mm
Z = 2

Data collection

Stoe IPDS II two-circle diffractometer	3534 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	3330 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.046
ω scans	θmax = 26.1°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
Tmin = 0.794, Tmax = 0.916	k = −11→11
21925 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.1437P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3534 reflections	Δρmax = 0.26 e Å^−3
257 parameters	Δρmin = −0.18 e Å^−3
17 restraints	Absolute structure: Flack (1983), Number of Bijvoet pairs: 1646
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Special details

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.7878 (3)	0.9517 (2)	0.87440 (16)	0.0252 (4)
N1A	0.7379 (3)	0.8483 (2)	0.79611 (17)	0.0352 (5)
H1A1	0.789 (4)	0.853 (3)	0.750 (2)	0.042*
H1A2	0.642 (4)	0.814 (3)	0.791 (2)	0.042*
C2A	0.9313 (3)	1.0404 (3)	0.87964 (17)	0.0306 (4)
Cl2A	1.04435 (8)	1.01771 (7)	0.77792 (5)	0.04277 (16)
C3A	0.9862 (3)	1.1433 (3)	0.9603 (2)	0.0407 (6)
H3A	1.0855	1.1994	0.9610	0.049*
C4A	0.8958 (4)	1.1648 (3)	1.0406 (2)	0.0441 (6)
H4A	0.9326	1.2354	1.0968	0.053*
C5A	0.7518 (3)	1.0823 (3)	1.03762 (19)	0.0369 (5)
H5A	0.6876	1.0974	1.0914	0.044*
C6A	0.7011 (3)	0.9790 (3)	0.95776 (17)	0.0298 (5)
Cl6A	0.51908 (8)	0.87668 (7)	0.95601 (5)	0.04686 (18)
N1B	0.56730 (19)	0.42237 (18)	0.43752 (13)	0.0186 (3)
C2B	0.5014 (2)	0.5401 (2)	0.47486 (14)	0.0184 (4)
N2B	0.3341 (2)	0.5485 (2)	0.46373 (15)	0.0250 (4)
H21B	0.269 (3)	0.468 (3)	0.439 (2)	0.030*
H22B	0.292 (3)	0.620 (3)	0.496 (2)	0.030*
N3B	0.5969 (2)	0.6551 (2)	0.52280 (13)	0.0205 (3)
H3B	0.548 (3)	0.729 (3)	0.5441 (19)	0.025*
C4B	0.7719 (2)	0.6587 (2)	0.53695 (15)	0.0192 (4)
O4B	0.84738 (16)	0.76997 (15)	0.58309 (12)	0.0232 (3)
C5B	0.8424 (2)	0.5367 (2)	0.49467 (15)	0.0204 (4)
H5B	0.9609	0.5322	0.4993	0.024*
C6B	0.7383 (2)	0.4227 (2)	0.44609 (15)	0.0183 (4)
N6B	0.7971 (2)	0.30113 (19)	0.40550 (15)	0.0226 (3)
H61B	0.902 (3)	0.299 (3)	0.4059 (19)	0.027*
H62B	0.728 (3)	0.252 (3)	0.361 (2)	0.027*
C1X	0.3033 (3)	−0.0586 (4)	0.2158 (3)	0.0550 (8)
H11X	0.2927	−0.1661	0.2077	0.082*	0.635 (9)
H12X	0.2497	−0.0108	0.1468	0.082*	0.635 (9)
H13X	0.2475	−0.0258	0.2733	0.082*	0.635 (9)
H4AX	0.2186	−0.1377	0.2029	0.082*	0.365 (9)
H4BX	0.2839	0.0056	0.2747	0.082*	0.365 (9)
H4CX	0.2939	−0.0003	0.1490	0.082*	0.365 (9)
O2X	0.5497 (2)	0.11334 (17)	0.26385 (14)	0.0350 (4)
C4X	0.5361 (5)	−0.2831 (3)	0.2364 (2)	0.0531 (8)
H41X	0.6320	−0.3517	0.2514	0.080*	0.635 (9)
H42X	0.4776	−0.2908	0.1594	0.080*	0.635 (9)
H43X	0.4574	−0.3079	0.2827	0.080*	0.635 (9)
H1AX	0.4378	−0.3491	0.2226	0.080*	0.365 (9)
H1BX	0.5925	−0.2886	0.1751	0.080*	0.365 (9)
H1CX	0.6153	−0.3133	0.3037	0.080*	0.365 (9)
C5X	0.7811 (3)	−0.0953 (3)	0.2912 (2)	0.0437 (6)
H51X	0.8461	−0.1875	0.2990	0.066*	0.635 (9)
H52X	0.8058	−0.0416	0.3607	0.066*	0.635 (9)
H53X	0.8125	−0.0340	0.2345	0.066*	0.635 (9)
H5AX	0.7706	−0.2032	0.2869	0.066*	0.365 (9)
H5BX	0.8425	−0.0604	0.2371	0.066*	0.365 (9)
H5CX	0.8431	−0.0668	0.3645	0.066*	0.365 (9)
C2X	0.4921 (6)	−0.0160 (5)	0.2469 (3)	0.0257 (11)	0.635 (9)
N3X	0.5987 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0255 (9)	0.0256 (10)	0.0236 (9)	0.0033 (8)	0.0035 (7)	0.0048 (8)
N1A	0.0349 (11)	0.0404 (12)	0.0321 (10)	−0.0137 (9)	0.0111 (8)	−0.0073 (9)
C2A	0.0300 (11)	0.0316 (12)	0.0317 (10)	−0.0013 (9)	0.0098 (8)	0.0011 (10)
Cl2A	0.0397 (3)	0.0499 (4)	0.0446 (3)	−0.0146 (3)	0.0218 (2)	−0.0087 (3)
C3A	0.0399 (13)	0.0388 (14)	0.0439 (13)	−0.0114 (11)	0.0101 (11)	−0.0060 (11)
C4A	0.0530 (16)	0.0383 (14)	0.0398 (13)	−0.0056 (12)	0.0082 (11)	−0.0134 (11)
C5A	0.0432 (14)	0.0371 (13)	0.0321 (12)	0.0070 (10)	0.0117 (10)	−0.0005 (9)
C6A	0.0270 (10)	0.0335 (12)	0.0295 (10)	0.0020 (9)	0.0076 (8)	0.0076 (9)
Cl6A	0.0415 (3)	0.0562 (4)	0.0489 (3)	−0.0133 (3)	0.0229 (3)	−0.0016 (3)
N1B	0.0139 (7)	0.0158 (8)	0.0268 (8)	−0.0011 (6)	0.0064 (6)	−0.0005 (6)
C2B	0.0158 (8)	0.0162 (9)	0.0239 (8)	0.0006 (7)	0.0057 (7)	0.0008 (7)
N2B	0.0137 (8)	0.0217 (9)	0.0414 (9)	−0.0011 (7)	0.0096 (7)	−0.0077 (8)
N3B	0.0154 (7)	0.0173 (8)	0.0306 (8)	0.0014 (6)	0.0091 (6)	−0.0022 (7)
C4B	0.0161 (8)	0.0170 (9)	0.0253 (9)	−0.0006 (7)	0.0061 (7)	0.0032 (8)
O4B	0.0148 (6)	0.0213 (7)	0.0337 (7)	−0.0030 (5)	0.0059 (5)	−0.0043 (6)
C5B	0.0134 (8)	0.0196 (9)	0.0296 (9)	0.0007 (7)	0.0076 (7)	0.0011 (8)
C6B	0.0156 (8)	0.0191 (9)	0.0218 (8)	0.0013 (7)	0.0075 (7)	0.0039 (7)
N6B	0.0139 (8)	0.0195 (8)	0.0359 (10)	0.0001 (7)	0.0084 (7)	−0.0029 (7)
C1X	0.0344 (14)	0.067 (2)	0.0603 (17)	−0.0076 (13)	0.0047 (12)	−0.0119 (15)
O2X	0.0407 (9)	0.0252 (8)	0.0394 (9)	−0.0010 (7)	0.0097 (7)	−0.0058 (7)
C4X	0.085 (2)	0.0273 (13)	0.0431 (15)	−0.0061 (13)	0.0062 (14)	−0.0027 (11)
C5X	0.0337 (12)	0.0548 (17)	0.0414 (12)	0.0070 (12)	0.0057 (10)	0.0003 (12)
C2X	0.029 (2)	0.025 (3)	0.0222 (16)	−0.0050 (17)	0.0049 (15)	−0.0063 (13)
N3X	0.040 (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)

C1A—N1A	1.353 (3)	C1X—N3X'	1.490 (8)
C1A—C2A	1.402 (3)	C1X—C2X	1.542 (5)
C1A—C6A	1.407 (3)	C1X—H11X	0.9800
N1A—H1A1	0.79 (3)	C1X—H12X	0.9800
N1A—H1A2	0.83 (3)	C1X—H13X	0.9800
C2A—C3A	1.375 (3)	C1X—H4AX	0.9800
C2A—Cl2A	1.743 (2)	C1X—H4BX	0.9799
C3A—C4A	1.386 (4)	C1X—H4CX	0.9802
C3A—H3A	0.9500	O2X—C2X	1.260 (5)
C4A—C5A	1.378 (4)	O2X—C2X'	1.311 (8)
C4A—H4A	0.9500	C4X—N3X	1.487 (5)
C5A—C6A	1.366 (3)	C4X—N3X'	1.533 (8)
C5A—H5A	0.9500	C4X—H41X	0.9800
C6A—Cl6A	1.738 (2)	C4X—H42X	0.9800
N1B—C2B	1.323 (2)	C4X—H43X	0.9800
N1B—C6B	1.366 (2)	C4X—H1AX	0.9800
C2B—N2B	1.334 (2)	C4X—H1BX	0.9801
C2B—N3B	1.355 (3)	C4X—H1CX	0.9799
N2B—H21B	0.91 (3)	C5X—N3X	1.475 (5)
N2B—H22B	0.87 (3)	C5X—C2X'	1.573 (8)
N3B—C4B	1.390 (2)	C5X—H51X	0.9800
N3B—H3B	0.85 (3)	C5X—H52X	0.9800
C4B—O4B	1.252 (2)	C5X—H53X	0.9800
C4B—C5B	1.400 (3)	C5X—H5AX	0.9800
C5B—C6B	1.385 (3)	C5X—H5BX	0.9800
C5B—H5B	0.9500	C5X—H5CX	0.9800
C6B—N6B	1.344 (3)	C2X—N3X	1.327 (6)
N6B—H61B	0.85 (3)	N3X'—C2X'	1.324 (11)
N6B—H62B	0.83 (3)
N1A—C1A—C2A	122.7 (2)	H4BX—C1X—H4CX	109.5
N1A—C1A—C6A	123.0 (2)	N3X—C4X—H41X	109.5
C2A—C1A—C6A	114.28 (19)	N3X'—C4X—H41X	146.3
C1A—N1A—H1A1	112 (2)	N3X—C4X—H42X	109.5
C1A—N1A—H1A2	117 (2)	N3X'—C4X—H42X	93.2
H1A1—N1A—H1A2	127 (3)	H41X—C4X—H42X	109.5
C3A—C2A—C1A	123.4 (2)	N3X—C4X—H43X	109.5
C3A—C2A—Cl2A	118.92 (18)	N3X'—C4X—H43X	84.6
C1A—C2A—Cl2A	117.64 (16)	H41X—C4X—H43X	109.5
C2A—C3A—C4A	119.6 (2)	H42X—C4X—H43X	109.5
C2A—C3A—H3A	120.2	N3X—C4X—H1AX	146.4
C4A—C3A—H3A	120.2	N3X'—C4X—H1AX	109.0
C5A—C4A—C3A	119.1 (2)	H41X—C4X—H1AX	103.1
C5A—C4A—H4A	120.5	H42X—C4X—H1AX	65.6
C3A—C4A—H4A	120.5	H43X—C4X—H1AX	49.8
C6A—C5A—C4A	120.3 (2)	N3X—C4X—H1BX	90.4
C6A—C5A—H5A	119.9	N3X'—C4X—H1BX	109.0
C4A—C5A—H5A	119.9	H41X—C4X—H1BX	68.3
C5A—C6A—C1A	123.2 (2)	H42X—C4X—H1BX	55.2
C5A—C6A—Cl6A	119.31 (18)	H43X—C4X—H1BX	158.9
C1A—C6A—Cl6A	117.44 (17)	H1AX—C4X—H1BX	109.5
C2B—N1B—C6B	116.92 (16)	N3X—C4X—H1CX	87.6
N1B—C2B—N2B	119.33 (17)	N3X'—C4X—H1CX	110.4
N1B—C2B—N3B	122.67 (16)	H41X—C4X—H1CX	47.0
N2B—C2B—N3B	117.99 (18)	H42X—C4X—H1CX	155.7
C2B—N2B—H21B	119.3 (15)	H43X—C4X—H1CX	79.2
C2B—N2B—H22B	119.1 (17)	H1AX—C4X—H1CX	109.5
H21B—N2B—H22B	119 (2)	H1BX—C4X—H1CX	109.5
C2B—N3B—C4B	122.70 (17)	N3X—C5X—H51X	109.5
C2B—N3B—H3B	119.0 (16)	C2X'—C5X—H51X	145.5
C4B—N3B—H3B	118.3 (16)	N3X—C5X—H52X	109.5
O4B—C4B—N3B	117.26 (17)	C2X'—C5X—H52X	88.0
O4B—C4B—C5B	127.63 (17)	H51X—C5X—H52X	109.5
N3B—C4B—C5B	115.10 (17)	N3X—C5X—H53X	109.5
C6B—C5B—C4B	119.56 (16)	C2X'—C5X—H53X	91.1
C6B—C5B—H5B	120.2	H51X—C5X—H53X	109.5
C4B—C5B—H5B	120.2	H52X—C5X—H53X	109.5
N6B—C6B—N1B	114.07 (17)	N3X—C5X—H5AX	73.0
N6B—C6B—C5B	122.93 (16)	C2X'—C5X—H5AX	109.1
N1B—C6B—C5B	122.98 (17)	H52X—C5X—H5AX	122.7
C6B—N6B—H61B	117.0 (17)	H53X—C5X—H5AX	123.8
C6B—N6B—H62B	116.5 (17)	N3X—C5X—H5BX	121.2
H61B—N6B—H62B	122 (2)	C2X'—C5X—H5BX	109.9
N3X'—C1X—H11X	71.9	H51X—C5X—H5BX	89.9
C2X—C1X—H11X	109.5	H52X—C5X—H5BX	115.1
N3X'—C1X—H12X	127.6	H5AX—C5X—H5BX	109.5
C2X—C1X—H12X	109.5	N3X—C5X—H5CX	125.3
H11X—C1X—H12X	109.5	C2X'—C5X—H5CX	109.5
N3X'—C1X—H13X	119.4	H51X—C5X—H5CX	88.7
C2X—C1X—H13X	109.5	H53X—C5X—H5CX	111.9
H11X—C1X—H13X	109.5	H5AX—C5X—H5CX	109.5
H12X—C1X—H13X	109.5	H5BX—C5X—H5CX	109.5
N3X'—C1X—H4AX	109.6	O2X—C2X—N3X	119.3 (5)
C2X—C1X—H4AX	147.5	O2X—C2X—C1X	125.7 (4)
H12X—C1X—H4AX	91.1	N3X—C2X—C1X	114.9 (4)
H13X—C1X—H4AX	85.5	C2X—N3X—C5X	117.3 (4)
N3X'—C1X—H4BX	109.8	C2X—N3X—C4X	120.9 (4)
C2X—C1X—H4BX	88.7	C5X—N3X—C4X	121.7 (3)
H11X—C1X—H4BX	129.9	C2X—N3X—H5AX	155.5
H12X—C1X—H4BX	107.1	C4X—N3X—H5AX	83.6
H4AX—C1X—H4BX	109.5	C2X'—N3X'—C1X	114.0 (7)
N3X'—C1X—H4CX	109.0	C2X'—N3X'—C4X	114.4 (7)
C2X—C1X—H4CX	88.1	C1X—N3X'—C4X	130.4 (5)
H11X—C1X—H4CX	117.1	O2X—C2X'—N3X'	115.3 (8)
H13X—C1X—H4CX	120.6	O2X—C2X'—C5X	131.3 (6)
H4AX—C1X—H4CX	109.5	N3X'—C2X'—C5X	113.4 (6)
N1A—C1A—C2A—C3A	−178.2 (2)	C4B—C5B—C6B—N1B	−0.4 (3)
C6A—C1A—C2A—C3A	1.4 (3)	C2X'—O2X—C2X—N3X	−1.8 (4)
N1A—C1A—C2A—Cl2A	1.8 (3)	C2X'—O2X—C2X—C1X	175.3 (6)
C6A—C1A—C2A—Cl2A	−178.56 (15)	N3X'—C1X—C2X—O2X	−172.9 (6)
C1A—C2A—C3A—C4A	−1.2 (4)	N3X'—C1X—C2X—N3X	4.4 (4)
Cl2A—C2A—C3A—C4A	178.7 (2)	O2X—C2X—N3X—C5X	−1.9 (4)
C2A—C3A—C4A—C5A	−0.1 (4)	C1X—C2X—N3X—C5X	−179.3 (3)
C3A—C4A—C5A—C6A	1.2 (4)	O2X—C2X—N3X—C4X	−177.4 (3)
C4A—C5A—C6A—C1A	−1.0 (4)	C1X—C2X—N3X—C4X	5.2 (4)
C4A—C5A—C6A—Cl6A	−180.0 (2)	C2X'—C5X—N3X—C2X	2.8 (4)
N1A—C1A—C6A—C5A	179.4 (2)	C2X'—C5X—N3X—C4X	178.3 (5)
C2A—C1A—C6A—C5A	−0.3 (3)	N3X'—C4X—N3X—C2X	−8.3 (4)
N1A—C1A—C6A—Cl6A	−1.7 (3)	N3X'—C4X—N3X—C5X	176.4 (5)
C2A—C1A—C6A—Cl6A	178.68 (16)	C2X—C1X—N3X'—C2X'	1.5 (4)
C6B—N1B—C2B—N2B	176.80 (17)	C2X—C1X—N3X'—C4X	−165.0 (8)
C6B—N1B—C2B—N3B	−2.0 (3)	N3X—C4X—N3X'—C2X'	2.2 (4)
N1B—C2B—N3B—C4B	−0.2 (3)	N3X—C4X—N3X'—C1X	168.7 (8)
N2B—C2B—N3B—C4B	−179.01 (17)	C2X—O2X—C2X'—N3X'	−4.5 (4)
C2B—N3B—C4B—O4B	−179.43 (17)	C2X—O2X—C2X'—C5X	174.2 (9)
C2B—N3B—C4B—C5B	2.1 (3)	C1X—N3X'—C2X'—O2X	3.4 (7)
O4B—C4B—C5B—C6B	179.93 (18)	C4X—N3X'—C2X'—O2X	172.2 (4)
N3B—C4B—C5B—C6B	−1.8 (3)	C1X—N3X'—C2X'—C5X	−175.5 (4)
C2B—N1B—C6B—N6B	−179.18 (16)	C4X—N3X'—C2X'—C5X	−6.8 (6)
C2B—N1B—C6B—C5B	2.3 (3)	N3X—C5X—C2X'—O2X	−175.7 (8)
C4B—C5B—C6B—N6B	−178.78 (18)	N3X—C5X—C2X'—N3X'	3.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A1···O4B	0.79 (3)	2.37 (3)	3.084 (3)	151 (3)
N1A—H1A1···Cl2A	0.79 (3)	2.51 (3)	2.971 (2)	119 (3)
N1A—H1A2···O2X^i	0.83 (3)	2.39 (3)	3.120 (3)	149 (3)
N1A—H1A2···Cl6A	0.83 (3)	2.56 (3)	2.972 (2)	112 (2)
N2B—H21B···O4B^ii	0.91 (3)	2.02 (3)	2.911 (2)	167 (2)
N2B—H22B···N6B^i	0.87 (3)	2.27 (3)	3.135 (3)	174 (2)
N3B—H3B···N1B^i	0.85 (3)	2.02 (3)	2.857 (2)	168 (2)
N6B—H61B···O4B^iii	0.85 (3)	2.02 (3)	2.867 (2)	173 (2)
N6B—H62B···O2X	0.83 (3)	2.09 (3)	2.913 (2)	173 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y−1/2, −z+1.