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In order to obtain complexes held together by hydrogen as well as halogen bonds, 6-chlorouracil [6-chloropyrimidin-2,4(1H,3H)-dione; 6CU] and its 3-methyl derivative [6-chloro-3-methylpyrimidin-2,4(1H,3H)-dione; M6CU] were cocrystallized with 2,4,6-triaminopyrimidine and the three triazine derivatives 2,4,6-triamino-1,3,5-triazine (melamine), 2,4-diamino-6-methyl-1,3,5-triazine and 2-chloro-4,6-diamino-1,3,5-triazine, which all offer complementary hydrogen-bonding sites. Three of these compounds form cocrystals with 6CU; however, melamine yielded only a new pseudopolymorph with 6CU, but formed a cocrystal with M6CU. All six cocrystals contain solvent molecules (N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidin-2-one), whose intermolecular interactions contribute significantly to the stabilization of the crystal packing. Each of these structures comprises chains, which are primarily formed by strong hydrogen bonds with a basic framework built by R22(8) hydrogen bonds of either pure N—H...N or mixed patterns. Solvent molecules are aligned to the border of these chains via N—H...O hydrogen bonds. Two of the reported crystal structures containing 6CU show additional Cl...O halogen bonds, which connect the chains to two-dimensional layers, while one weak and one strong Cl...Cl interaction are observed in the two structures in which molecules of M6CU are present.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615003790/ao5001sup1.cif
Contains datablocks I, II, III, IV, Va, Vb, VI, VII

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CCDC references: 1043316; 1043317; 1043318; 1043319; 1043320; 1043321; 1043322; 1043323

Introduction top

During the last years we have studied a number of cocrystals in which the components are held together by two or three hydrogen bonds (Tutughamiarso et al., 2012; Tutughamiarso & Egert, 2012; Ton & Egert, 2015a; Ton & Egert, 2015b; Hützler & Egert, 2015). The resulting patterns, of which some resemble the Watson-Crick base pairs adenine/thymine (or uracil) and guanine/cytosine, are simple models of molecular recognition, e.g. between a biologically active molecule and its receptor. We wondered if halogen-substituted coformers would give rise to extend patterns where, in addition to hydrogen bonds (HB), halogen bonds (XB) contribute significally to their stabilization.

XB, which are caused by the anisotropic distribution of electron density, have experienced a rising inter­est in various fields (metrangolo & Resnati, 2012; Metrangolo &Resnati, 2014), such as supra­molecular chemistry (Aakeröy et al., 2013; Sarwar et al., 2013), crystal engineering (Desiraju, 2013; Mukherjee et al., 2014), medicine (Heshmati et al., 2009), pharmaceutical chemistry (Baldrighi et al., 2013) and material sciences (Shin et al., 2014). Similar to HB, XB are non-covalent and highly directional inter­actions (Shields et al., 2010), wherein a covalently bonded halogen atom X inter­acts with a Lewis base or a second halogen atom (Troff et al., 2013; Desiraju et al., 2013). Their strength depends on the halogen-bond donor as well as on the type of halogen and ranges from 5 up to 180 kJ/mol (Metrangolo et al., 2007).

X···O contacts are of special inter­est in biological inter­actions (Auffinger et al., 2004; Parisini et al., 2011); for example, they have been shown to influence the binding selectivity and affinity in protein-ligand complexes (Hardegger et al., 2011). In crystal engineering, the combination of HB and XB is of increasing importance (Corradi et al., 2000; Saha et al., 2005) since they both obtain special geometrical properties and synthons, which are partially orthoghonal (Politzer et al., 2007; Aakeröy et al., 2011). However, the supra­molecular inter­actions based on HB and XB, especially single-point and multi-point inter­actions, are difficult to predict, therefore the development of new synthons is still a major task in crystal engineering (Aakeröy et al., 2011).

Due to their relevance as nucleobases and their role in important biological processes uracil derivatives are continually exposed to scientific investigations. For example, halogen-substituted uracil derivatives were examined as new inhibitors of the angiogenic actions of thymidine phospho­rylase and show significant better inhibitory characteristics compared with the corresponding methyl-substituted compounds (Klein et al., 2001). On the basis of these and related results, we have studied cocrystals of 6-chloro­uracil (6CU) and its derivative 6-chloro-3-methyl­uracil (M6CU) with several coformers. Since both uracil derivatives exhibit an ADA (A = acceptor and D = donor) hydrogen-bonding site with the the N—H group at position 1 as donor and the O and Cl atoms at positions 2 and 6 as acceptors (strong and weak, respectively), we chose coformers with complementary DAD sites and were successful with 2,4,6-tri­amino­pyrimidine (TAP) and three triazine derivatives [2,4,6-tri­amino-1,3,5-triazine (melamine, TAT), 2,4-di­amino-6-methyl-1,3,5-triazine (DMT) and 2-chloro-4,6-di­amino-1,3,5-triazine (CDT)] (Scheme 1).

Experimental top

Crystallization top

All experiments were performed with commercially available substances in various hydrous solvents and at various temperatures. Isothermal solvent evaporation experiments of 6CU with TAP in N-methyl­pyrrolidin-2-one (NMP) yielded cocrystal (I), which also contains NMP and H2O, while experiments with TAT in NMP only led to a new pseudopolymorph of TAT with NMP and H2O (II). Similar experiments with DMT in N,N- di­methyl­acetamide (DMAC) or N,N-di­methyl­formamide (DMF) yielded the cocrystal solvates (III) and (IV). Further experiments of 6CU with CDT in DMF led to the two DMF-containing cocrystals (Va) and (Vb). When M6CU was cocrystallized with iso­butyl 3,5-di­amino-4-chloro­benzoate in DMAC, a solvent-free crystal of M6CU (VI) was obtained, whereas cocrystallization experiments with TAT in DMAC under acidic conditions provided cocrystal (VII), which contains M6CU, TAT, DMAC, (CH3)2NH, and HCl. A detailled summary of the solvent evaporation experiments performed is presented in Table 10.

Crystal Structure Analysis top

Crystal data, data collection and structure refinement details are summarized in Table 1. 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) = 1.5 Ueq(C) for methyl H atoms or 1.2 Ueq(C) for the other H atoms, whereby ordered methyl groups were allowed to rotate about their local threefold axis. H atoms bonded to N atoms were refined isotropically with Uiso(H) = 1.2 Ueq(N), and with N—H distance restraints in (I), (Va), (Vb) and (VII). 1,2 and 1,3 distance restraints were applied for the H2O molecules, as well as for the NMP solvent molecules in (I) and for the DMAC molecule in (VII).

In (I), one NMP molecule (X) is disordered across a pseudo-mirror plane, which passes approximately through atoms O2X and C5X with a site occupation factor of 0.816 (6) for the major occupied site, while this value amounts to 0.625 (19) for the disordered DMAC molecule in (VII). For the two positions of the disordered solvent molecule in (I), the 1,2 and 1,3 distances were restrained to be the same; also the dispacement parameters were constrained to the same values. In (VII), only the TAT molecule and one chloride ion occupy general positions, whereas the remaining atoms are located on a mirror plane or, in the case of the second chloride ion (Cl1D), on a twofold axis.

Results top

The crystal structures obtained from the various cocrystallization experiments exhibit repeatedly certain inter­action patterns which can be regarded as supra­molecular synthons (Desiraju, 1995). Especially important is the formation of two or three hydrogen bonds between the donor and acceptor groups of two molecules. If two HB are formed leading to an R22(8) pattern according to Bernstein et al. (1995), we will call this synthon 2 and distinguish if the pair of HB is formed between identical (2i) or different functional groups (2d). In order to clarify the participating donor/acceptor groups involved in synthon 2, they can be added in paranthesis [2iD.A and 2dD.A;D'A', respectively]. If three HB are formed there will either be a symmetric ADA-DAD (synthon 3s) or an unsymmetric AAD-DDA (synthon 3u) pattern (Fig. 1). The use of these synthons abbreviates the following discussion considerably.

Co-crystallization experiments with 6-chloro­uracil top

Cocrystallization attempts of 6CU with TAP in NMP yielded cocrystal (I) as a disolvate-monohydrate. The asymmetric unit of the triclinic crystal comprises one molecule of 6CU (A) deprotonated at N1A, one molecule of TAP (B) which is protonated at N3B, one H2O molecule (W) and two planar NMP molecules (X, Y) (r.m.s. deviations for non-H atoms of X and Y = 0.044 and 0.021 Å, respectively), of which X is disordered (Fig. 2). 6CU and TAP are connected via synthon 2dN.N;N.O (r.m.s. deviation for non-H atoms of 6CU and TAP = 0.040 Å). Furthermore, X is directly N—H···O hydrogen bonded to TAP, whereas Y is bridged to TAP via the H2O molecule. In the crystal packing molecules of 6CU and TAP are connected to their respective inversion-symmetric equivalent via synthon 2iN.O between 6CU and 2iN.N inter­actions between TAP molecules (Fig. 3 and Table 2). Almost flat chains of alternating 6CU and TAP molecules, running parallel to (130), result in additional R32(8) and R32(10) HB inter­actions. In the first case two molecules of TAP are connected to one molecule of 6CU via one N—H···N and two N—H···O hydrogen bonds, and in the latter one two molecules of 6CU are linked with one molecule of TAP via three N—H···O hydrogen bonds. Additional O—H···O inter­actions from the water molecules connect chains which are situated on top of each other to a multi-storied two-dimensional network (Fig. 4).

The cocrystallization experiments of 6CU with TAT in DMAC yielded one cocrystal monosolvate of only minor quality (Gerhardt, 2014), wherein a proton transfer from 6CU to TAT, similar to that in (I), is observed. In the crystal, TAT molecules are connected to 6CU via synthon 2dN.N;N.O hydrogen bonds forming chains. Attempts to cocrystallize 6CU with TAT in hydrous NMP we obtained the TAT-pseudopolymorph (II). (II) crystallizes in P21/n with one TAT molecule, two NMP (X, Y) molecules (r.m.s. deviations for non-H atoms of X and Y = 0.042 and 0.087 Å, respectively) and one H2O (W) molecule in the asymmetric unit. The TAT molecule is bridged to the solvent molecule X via the H2O molecule by one N—H···O and one O—H···O hydrogen bond, whereas the second NMP molecule (Y) is connected directly to TAT (Fig. 2). Synthon 2iN.N patterns of TAT form almost planar chains (r.m.s. deviation for non-H atoms of TAT plus O1W = 0.041 Å) parallel to (101). These are strengthened by R32(8) inter­actions of TAT with the solvent molecule Y as well as with the water molecue, with two further N—H···O hydrogen bonds in each case (Fig. 5 and Table 3). Similar to (I), R42(8) O—H···O inter­actions of W with X connect the chains to two-dimensional layers (see supplementary material).

The cocrystallization of 6CU and DMT yielded two cocrystals, (III) and (IV). From DMAC we obtained the DMAC monosolvate of 6CU-DMT (III), which crystallizes in the triclinic space group P1 with one molecule of 6CU (A), DMT (B) and DMAC (X) within the asymmetric unit. Again a proton transfer from the 6CU to the DMT is observed. The resulting ions are connected by the planar synthon 3s (r.m.s. deviation for non-H atoms = 0.078 Å). One further N—H···O hydrogen bond links the solvent molecule with the DMT molecule, whereby X is oriented at an angle of 65.95 (5)° with respect to synthon 3s (Fig. 9). A one-dimensional framework of chains is built by alternating patterns of synthon 2dN.N;N.O with synthon 3s parallel to (403); between these chains there are only van der Waals inter­actions (Fig. 6 and Table 4).

The second cocrystal, (IV), which is also triclinic, was obtained from DMF. The asymmetric unit of (IV) consists of one molecule of 6CU (A), DMT (B), DMF (X) and H2O (W) each (Fig. 11). Similar to (I) and (III), a proton transfer from 6CU to DMT has taken place. As in (III), the planar synthon 3s (r.m.s. deviation for non-H atoms = 0.035 Å) is formed. The water molecule and the solvent molecule, which is located at an angle of 78.40 (14)° with respect to synthon 3s, are connected to 6CU and DMT, respectively, by one O—H···O and one N—H···O hydrogen bond. The crystal packing of (IV) shows chains parallel to (403) consisting of synthon 3s connected by 2dN.N;N.O patterns. Additional R43(9) patterns including a very weak Cl···O inter­action between 6CU and water [d= 3.455 (4) Å] and three different (N,O)—H···(N,O) hydrogen bonds stabilize the chains further (Fig. 7 and Table 5). Two parallel chains, which are arranged one above the other, are connected by an additional O—H···O hydrogen bond from the water to the solvent molecule resulting in a two-dimensional network of tubes (Fig. 8).

During the cocrystallization experiments of 6CU with CDT in DMF at different temperatures two cocrystals, (Va) and (Vb), were formed as DMF monosolvates. At 277 K, compound (Va) crystallized in P1 with three coplanar molecules in the asymmetric unit, namely one 6CU (A), one CDT (B) and one DMF (X) molecule (r.m.s. deviation for all non-H atoms = 0.077 Å). Again synthon 3s is present, but unlike in (I), (III) and (IV) no proton transfer is observed. The solvent molecule is connected to 6CU by an R22(7) pattern with a strong N—H···O hydrogen bond and a weak C—H···O inter­action (Fig. 2). Chains parallel to (211) are built through two symmetry-independent synthon 2iN.N patterns between CDT molecules solely. 6CU molecules are adjusted via synthon 3s in sort of a zig-zag arrangement to these chains, and the solvent molecules are oriented in an anti­parallel fashion. Due to this arrangement an R42(10) inter­action is formed by two inversion-symmetric Cl···O halogen bonds [d = 3.081 (2) Å] which fulfil the criteria of a halogen bond (Desiraju et al.,2013), extending the chains to two-dimensional layers (Fig. 9, and Table 6).

At 323 K, a second DMF monosolvate of 6CU-CDT, (Vb), was obtained. Compound (Vb) is also triclinic (P1), but comprises two molecules of 6CU (A and C), CDT (B and D) and DMF (X and Y), respectively, in the asymmetric unit (Fig. 2). Similar to (Va) the planar synthon 3s is formed between pairs of 6CU and CDT molecules (r.m.s. deviation for non-H atoms of A/B = 0.078 Å and C/D = 0.074 Å]. Also, R22(7) patterns with a strong N—H···O hydrogen bond and a weak C—H···O inter­action connect the solvent molecules to 6CU. The two 3s synthons are linked by a 2iN.N pattern between the two independent CDT molecules, yielding chains parallel to (011) (Fig. 10 and Table 7). As in (Va), the 3s synthons within these chains are arranged in a zig-zag fashion, whereby the heterodimers (A/B and C/D) are related by a pseudo-21 screw axis parallel to the crystallograpic a axis. The parallel chains allow for Cl···O halogen bonds between Cl6A and O1Y [d = 3.031 (3) Å], thus forming relatively flat two-dimensional layers (r.m.s. deviation for all non-H atoms = 0.103 Å). In contrast to (Va), all solvent molecules within one layer are oriented in the same direction, but they are oriented oppositely in neighbouring layers, due to inversion centers located between them.

Cocrystallization experiments with 6-chloro-3-methyl­uracil top

During the cocrystallization experiments with 6CU we did not obtain cocrystals between 6CU and TAT with a good quality. After replacing 6CU with its 3-methyl derivative M6CU, we also used various coformers in various solvents at various temperatures. First we got a solvent-free structure of M6CU, (VI), but finally also the desired cocrystal with TAT, (VII).

The solvent-free structure crystallizes in the monoclinic space group P21/c with one planar molecule of M6CU (r.m.s. deviation for non-H atoms = 0.015 Å) in the asymmetric unit (Fig. 2). The crystal packing of (VI) is characterized by R22(8) patterns, with an N—H···O hydrogen bond supported by a weak C—H···O inter­action (synthon 2dN.O;C.O), the translation of which leads to chains parallel to (102). These chains are further stabilized by Cl···Cl inter­actions [d = 3.353 (1) Å] between two inversion-symmetric chlorine atoms thus forming layers (Fig. 11, and Table 8).

The asymmetric unit of cocrystal (VII), which crystallizes in space group C2/m, contains five different entities: besides one molecule of M6CU (A), TAT (B) and DMAC (X), which had be expected, one molecule of (CH3)2NH (E), which had obviously been formed upon hydrolysis of DMAC, and two chloride ions (C and D) from HCl molecules, which have protonated the molecules of TAT and (CH3)2NH (Fig. 2). There are no synthon 3s heterodimers formed between the M6CU and TAT molecules, but the protonated TAT molecules are linked by synthon 2iN.N to chains parallel to (001). These chains are further connected to two-dimensional layers via N—H···Cl hydrogen bonds (Fig. 12 and Table 9). An additional N—H···Cl hydrogen bond from the di­methyl­ammonium ion to the chloride ion Cl1C inter­links adjacent layers to a three-dimensional arrangement. The latter contains voids that are occupied by M6CU molecules, which are N—H···O hydrogen bonded to the DMAC molecules and form dimers via Cl···Cl inter­actions [d = 3.070 (4) Å] (Fig. 13).

Discussion top

In a Cambridge Structural Database (CSD, version 5.36 of November 2014, plus one update; Groom & Allen, 2014) search for melamine, which was restricted to organic compounds with known 3D coordinates and the exclusion of ions, 31 unique structures were found. One of the primary motifs within these structures is synthon 2i; it is present in 13 structures that form chains or dimers, either solely by melamine or with participation of the corresponding coformers, which are related to those observed in (II). Only four crystals contain synthon 2d connecting the melamine molecules with their coformer. Synthon 3s is also found in 15 structures but no predominant packing arrangement is observed therein. Inter­estingly, only the melamine-adipidic acid hydrate (CSD refcode: NUSHIT; Zhao et al., 2010) shows a 2i chain arrangement of melamine molecules and a three-dimensional network formed between the water molecules and the coformer, in a similar way to the inter­actions observed in (II).

A further CSD search for uracil (U), 6-methyl­uracil (6MU) and 6-chloro­uracil (6CU) yielded altogether seven structures, viz. one solvent-free structure of U (CSD refcode URACIL; Stewart & Jensen, 1967), one cocrystal of U with TAT (VIFKUR; Thomas & Kulkarni, 2007), two solvent-free structures of 6MU [(CEWVOP01 (Reck et al., 1988) and CEWVOP02 (Leonidow et al., 1993)], one structure of C5-substituted 6CU (NIYGIN; Al-Omary et al., 2014), one trihydrate cocrystal of 6CU with 4-(di­methyl­amino)­pyridine (QECNOB; Schmidt et al., 1999), and a structure of N1-substituted 6CU (VEXYUS, Ishikawa et al., 1990). URACIL crystallizes in space group P21/a; the packing shows two-dimensional layers, which are built by 2iN.O and 2dN.O;C.O patterns. Synthon 3s is observed in VIFKUR where each synthon is connected with its neighbour via 2iN.N hydrogen bonds between two TAT molecules and via 2dN.N;N.O hydrogen bonds between TAT and U, resulting in a three-dimensional network. Both solvent-free 6MU crystals contain 2i(N.O) HB providing a two-dimensional network of dimers in CEWVOP01 and chains in CEWVOP02. Similar to (I), (III) and (IV), a proton transfer from 6CU to its counterpart 4-(2-meth­oxy­phenyl)­piperazine (MOP) is observed in NIYGIN. In this structure, chains are built by alternating 2iN.O hydrogen bonds between 6CU molecules and R44(8) N—H···O inter­actions between 6CU and MOP. In QECNOB, again, 2iN.O inter­actions connect deprotonated 6CU molecules; single N—H···O hydrogen bonds link 6CU molecules with their protonated counterpart 4-(di­methyl­amino)­pyridine to form tetra­mers. In VEXYUS, dimers are formed by 2iN.O hydrogen bonds and, related to (Va) and (Vb), a Cl···O halogen bond expands those dimers to chains.

The structures (I)–(VII) are essentially dominated by hydrogen bonds, either by both synthon 2 types or synthon 3s patterns. In (VI) the packing is mainly stabilized by weak C—H···O inter­actions within the chains together with Cl···Cl inter­actions, which help to form two-dimensional layers, whereas only one N—H···O hydrogen bond is formed. In (I), (III), (IV) and (VI) synthon 2d is observed, as well as in the 6CU-TAT cocrystal monosolvate (Gerhardt, 2014). In contrast, synthon 2i is predominant in (II), (Va) and (Vb) and is also found in CEWVOP01, CEWVOP02, NIYGIN, QECNOB and VEXYUS. Only in URACIL both synthon 2 types are present for the main compounds. Five structures contain synthon 3s, viz. (III), (IV), (Va), (Vb) and VIFKUR. A proton transfer, which has taken place in the compounds (I), (III) and (IV) and the 6CU-TAT cocrystal monosolvate, is also present in NIYGIN.

In the crystal structures reported, chains are prevalent, either with alternating components, as in (I), (III) and (IV), or consisting of only one component, as in (Va) and (Vb); in (Va) an anti­parallel and in (Vb) a parallel arrangement of the solvent DMF molecules is displayed, which leads to different types of linkage in the packing. Surprisingly, a three-dimensional network is observed only in VIFKUR. In the structures CEWVOP02, NIYGIN, QECNOB and VEXYUS, there is a tendency of one-dimensional packing motifs, while only URACIL and CEWVOP01 show two-dimensional networks. In contrast to this trend, six of the structures reported by us show two-dimensional motifs, mainly in the form of layers [(II), (Va), (Vb) and (VI)], but tubes [(IV)] and stair-like [(I)] arrangements are also present.

In five structures [(IV), (Va), (Vb), (VI) and (VII)] the Cl atoms are involved in noticable inter­molecular inter­actions. In (IV) a very weak Cl···O contact between 6CU and the water molecule is observed, however, this inter­action seems only to support the packing, which is dominated by hydrogen bonds. In (VI) and (VII), on the other hand, Cl···Cl inter­actions are explicitly involved in the formation of layers [in (VI)] or dimers [in (VII)]. Similar characteristics to those observed in (VI) and (VII), but with Cl···O halogen bonds that act as linkers to form more complex packing motifs are found in (Va), (Vb) and VEXYUS.

In conclusion, our investigation showed that, for 6-chloro­uracil and 6-chloro-3-methyl­uracil in combination with several triazine and pyrimidine derivatives, distinct synthons are formed. Inter­molecular inter­actions of the Cl atoms are able to expand one-dimensional hydrogen-bonded networks to more complex packing motifs. These findings might help to design new two- and possibly three-dimensional networks of more complex molecules by using such synthons as building blocks.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Version 3.1, Macrae et al., 2008) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Synthons used for supramolecular patterns with two or three hydrogen bonds. In synthon 2 the D—H and D'—H bonds can be oriented either antiparallel (as shown above) or parallel.
[Figure 2] Fig. 2. The asymmetric units and atom numbering schemes of (I)-(VII). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. In (I) and (VII), only the major occupied site of the disordered solvent molecule X is shown.
[Figure 3] Fig. 3. A partial packing diagram for (I). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. The minor occupied sites of the solvent molecule X are omitted. [symmetry codes: (i) -x + 1, -y, -z+2; (ii) -x + 1, -y, -z+1; (iii) x, y, z-1]
[Figure 4] Fig. 4. A partial packing diagram for (I), showing the two-dimensional networks parallel to (130). Dashed lines indicate hydrogen bonds.
[Figure 5] Fig. 5. A partial packing diagram for (II). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [symmetry codes: (i) x + 1/2, -y + 1/2, z+1/2; (ii) x - 1/2, -y + 1/2, z-1/2]
[Figure 6] Fig. 6. A partial packing diagram for (III). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [symmetry code: (i) x, y - 1, z]
[Figure 7] Fig. 7. A partial packing diagram for (IV). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds and solid lines represent halogen bonds. [symmetry codes: (i) x, y+1, z; (ii) -x + 1, -y + 1, -z+1; (iii) x, y - 1, z]
[Figure 8] Fig. 8. A partial packing diagram for (IV), showing the two-dimensional arrangement of tubes.
[Figure 9] Fig. 9. A partial packing diagram for (Va). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds and solid lines represent halogen bonds. [symmetry codes: (i) -x + 1, -y + 2, -z + 1; (ii) -x + 1, -y + 1, -z+2; (iii) -x, -y, -z + 1]
[Figure 10] Fig. 10. A partial packing diagram for (Vb). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds and solid lines represent halogen bonds. [symmetry codes: (i) x + 1, y, z; (ii) x - 1, y, z; (iii) x + 1, y + 1, z - 1]
[Figure 11] Fig. 11. A partial packing diagram for (VI). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds and solid lines represent halogen bonds. [symmetry codes: (i) x - 1, -y + 1/2, z - 1/2; (ii) x + 1, -y + 1/2, z + 1/2; (iii) -x, -y + 1, -z + 1]
[Figure 12] Fig. 12. A partial packing diagram for (VII) showing the layer built by melamine molecules and chloride ions. Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [symmetry codes: (i) -x + 1/2, -y + 1/2, -z + 2; (ii) -x + 1/2, -y + 1/2, -z + 1; (iii) -x + 1, y, -z + 2]
[Figure 13] Fig. 13. A partial packing diagram for (VII) showing the M6CU homodimers and the dimethylammonium cations in between the melamine / chloride layers (see Fig. 12). Only hydrogen atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. Halogen bonds are emphasized by solid lines. [symmetry code: (iv) -x + 1, -y, -z]
(I) top
Crystal data top
C4H3ClN2O2·C4H7N5·2(C5H9NO)·H2OZ = 2
Mr = 487.96F(000) = 516
Triclinic, P1Dx = 1.381 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4450 (6) ÅCell parameters from 26327 reflections
b = 10.3974 (7) Åθ = 4.2–25.9°
c = 13.3661 (8) ŵ = 0.21 mm1
α = 77.188 (5)°T = 173 K
β = 89.846 (5)°Block, colourless
γ = 67.043 (5)°0.63 × 0.18 × 0.13 mm
V = 1173.40 (13) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
4521 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source3965 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.050
ω scansθmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1111
Tmin = 0.879, Tmax = 0.972k = 1212
23834 measured reflectionsl = 1614
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)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0843P)2 + 4.5246P]
where P = (Fo2 + 2Fc2)/3
4521 reflections(Δ/σ)max < 0.001
350 parametersΔρmax = 1.27 e Å3
102 restraintsΔρmin = 0.53 e Å3
Crystal data top
C4H3ClN2O2·C4H7N5·2(C5H9NO)·H2Oγ = 67.043 (5)°
Mr = 487.96V = 1173.40 (13) Å3
Triclinic, P1Z = 2
a = 9.4450 (6) ÅMo Kα radiation
b = 10.3974 (7) ŵ = 0.21 mm1
c = 13.3661 (8) ÅT = 173 K
α = 77.188 (5)°0.63 × 0.18 × 0.13 mm
β = 89.846 (5)°
Data collection top
STOE IPDS II two-circle
diffractometer
4521 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
3965 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.972Rint = 0.050
23834 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.084102 restraints
wR(F2) = 0.244H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 1.27 e Å3
4521 reflectionsΔρmin = 0.53 e Å3
350 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)
N1A0.1098 (4)0.1306 (4)0.9239 (3)0.0263 (7)
C2A0.2646 (5)0.0755 (4)0.9510 (3)0.0259 (8)
O2A0.3610 (3)0.0410 (3)0.8867 (2)0.0308 (7)
N3A0.3144 (4)0.0601 (4)1.0506 (2)0.0249 (7)
H3A0.413 (3)0.028 (5)1.069 (4)0.030*
C4A0.2210 (5)0.0921 (5)1.1284 (3)0.0295 (9)
O4A0.2817 (3)0.0728 (4)1.2150 (2)0.0391 (8)
C5A0.0601 (5)0.1465 (5)1.0990 (3)0.0296 (9)
H5A0.01480.17131.14670.036*
C6A0.0200 (4)0.1612 (4)0.9977 (3)0.0259 (8)
Cl6A0.17873 (11)0.23212 (12)0.95603 (8)0.0334 (3)
N1B0.2802 (4)0.0736 (4)0.5073 (2)0.0253 (7)
C2B0.3235 (4)0.0573 (4)0.6055 (3)0.0240 (8)
N2B0.4720 (4)0.0062 (5)0.6369 (3)0.0333 (8)
H21B0.507 (6)0.004 (6)0.701 (2)0.040*
H22B0.540 (5)0.017 (5)0.592 (3)0.040*
N3B0.2197 (4)0.0894 (4)0.6766 (3)0.0257 (7)
H3B0.258 (6)0.073 (5)0.734 (4)0.031*
C4B0.0647 (4)0.1359 (4)0.6500 (3)0.0267 (8)
N4B0.0281 (4)0.1631 (5)0.7249 (3)0.0386 (9)
H41B0.002 (5)0.154 (6)0.7884 (19)0.046*
H42B0.127 (2)0.194 (6)0.713 (3)0.046*
C5B0.0162 (5)0.1534 (5)0.5497 (3)0.0287 (9)
H5B0.09050.18660.52820.034*
C6B0.1272 (4)0.1212 (4)0.4794 (3)0.0244 (8)
N6B0.0859 (4)0.1381 (4)0.3798 (3)0.0320 (8)
H61B0.158 (4)0.117 (5)0.338 (3)0.038*
H62B0.003 (3)0.173 (5)0.347 (3)0.038*
O1W0.3421 (4)0.2228 (5)0.6820 (4)0.0656 (12)
H2W0.352 (8)0.149 (4)0.716 (6)0.098*
H1W0.414 (6)0.300 (4)0.685 (6)0.098*
O2X0.2254 (5)0.2456 (8)0.2848 (4)0.0427 (13)0.816 (6)
N1X0.4882 (5)0.3345 (5)0.2501 (4)0.0387 (11)0.816 (6)
C1X0.4877 (9)0.3138 (9)0.1477 (5)0.0521 (17)0.816 (6)
H1X10.59430.35130.11670.078*0.408 (3)
H1X20.43690.21090.15000.078*0.408 (3)
H1X30.43160.36500.10610.078*0.408 (3)
H1X40.38090.26680.13190.078*0.408 (3)
H1X50.53830.40730.09850.078*0.408 (3)
H1X60.54360.25310.14250.078*0.408 (3)
C2X0.3594 (6)0.2952 (7)0.3125 (4)0.0364 (13)0.816 (6)
C3X0.4070 (8)0.3216 (8)0.4163 (5)0.0459 (14)0.816 (6)
H3X10.36100.38330.43750.055*0.816 (6)
H3X20.37290.22950.46920.055*0.816 (6)
C4X0.5823 (8)0.3964 (9)0.4036 (6)0.0597 (17)0.816 (6)
H4X10.62800.34790.45830.072*0.816 (6)
H4X20.61630.49830.40640.072*0.816 (6)
C5X0.6292 (7)0.3851 (14)0.2982 (6)0.0491 (16)0.816 (6)
H5X10.67970.31650.30520.059*0.816 (6)
H5X20.70160.48010.25710.059*0.816 (6)
O2X'0.2292 (19)0.231 (5)0.3165 (19)0.0427 (13)0.184 (6)
N1X'0.4899 (18)0.331 (2)0.3294 (12)0.0387 (11)0.184 (6)
C1X'0.484 (3)0.330 (4)0.4367 (15)0.0521 (17)0.184 (6)
H1X70.58860.36380.45810.078*0.092 (3)
H1X80.43440.39330.44820.078*0.092 (3)
H1X90.42340.23160.47710.078*0.092 (3)
H1XX0.37570.29540.46420.078*0.092 (3)
H1XY0.52990.26590.47400.078*0.092 (3)
H1XZ0.54090.42750.44520.078*0.092 (3)
C2X'0.3661 (17)0.285 (4)0.2766 (15)0.0364 (13)0.184 (6)
C3X'0.422 (3)0.292 (4)0.1689 (15)0.0459 (14)0.184 (6)
H3X30.37990.19520.15510.055*0.184 (6)
H3X40.38780.35610.11730.055*0.184 (6)
C4X'0.597 (3)0.352 (4)0.1645 (17)0.0597 (17)0.184 (6)
H4X30.64390.44010.10840.072*0.184 (6)
H4X40.63560.27990.15280.072*0.184 (6)
C5X'0.6353 (18)0.385 (7)0.269 (2)0.0491 (16)0.184 (6)
H5X30.68980.49000.26110.059*0.184 (6)
H5X40.70190.33720.30130.059*0.184 (6)
N1Y0.8861 (7)0.4619 (6)0.7251 (5)0.0778 (17)
C1Y0.9714 (10)0.4862 (9)0.6341 (6)0.088 (2)
H1Y11.08170.52900.64330.132*
H1Y20.94690.39490.61470.132*
H1Y30.94630.55220.57970.132*
C2Y0.7319 (6)0.4054 (6)0.7362 (6)0.072 (2)
O2Y0.6521 (6)0.3656 (6)0.6661 (5)0.0887 (16)
C3Y0.6762 (10)0.3906 (7)0.8402 (6)0.083 (2)
H3Y10.60600.44070.84010.100*
H3Y20.61920.28780.87490.100*
C4Y0.8173 (7)0.4579 (7)0.8956 (7)0.080 (2)
H4Y10.81690.54430.91490.096*
H4Y20.82040.38840.95870.096*
C5Y0.9592 (7)0.4993 (7)0.8154 (5)0.0645 (17)
H5Y11.02190.44330.84000.077*
H5Y21.02590.60320.80150.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0200 (16)0.0351 (18)0.0223 (16)0.0084 (14)0.0010 (13)0.0085 (14)
C2A0.030 (2)0.030 (2)0.0195 (18)0.0132 (17)0.0015 (15)0.0074 (15)
O2A0.0227 (14)0.0488 (18)0.0223 (14)0.0128 (13)0.0056 (11)0.0144 (13)
N3A0.0156 (15)0.0358 (18)0.0216 (16)0.0072 (14)0.0010 (12)0.0091 (14)
C4A0.027 (2)0.039 (2)0.022 (2)0.0113 (18)0.0032 (16)0.0092 (17)
O4A0.0283 (16)0.066 (2)0.0202 (15)0.0129 (15)0.0046 (12)0.0159 (14)
C5A0.025 (2)0.037 (2)0.025 (2)0.0090 (17)0.0064 (16)0.0107 (17)
C6A0.0186 (18)0.031 (2)0.028 (2)0.0095 (16)0.0009 (15)0.0061 (16)
Cl6A0.0200 (5)0.0469 (6)0.0285 (5)0.0079 (4)0.0005 (4)0.0098 (4)
N1B0.0229 (16)0.0352 (18)0.0181 (16)0.0108 (14)0.0011 (12)0.0082 (13)
C2B0.0211 (19)0.0273 (19)0.0232 (19)0.0097 (15)0.0024 (15)0.0054 (15)
N2B0.0191 (17)0.057 (2)0.0207 (17)0.0098 (16)0.0009 (13)0.0126 (16)
N3B0.0254 (17)0.0366 (19)0.0167 (16)0.0131 (15)0.0002 (13)0.0079 (14)
C4B0.0225 (19)0.033 (2)0.025 (2)0.0106 (16)0.0037 (15)0.0075 (16)
N4B0.0244 (18)0.071 (3)0.0219 (18)0.0183 (19)0.0038 (14)0.0162 (18)
C5B0.0210 (19)0.043 (2)0.0216 (19)0.0111 (17)0.0016 (15)0.0095 (17)
C6B0.0222 (19)0.030 (2)0.0198 (18)0.0092 (16)0.0010 (14)0.0053 (15)
N6B0.0255 (18)0.048 (2)0.0189 (17)0.0110 (16)0.0002 (13)0.0092 (15)
O1W0.032 (2)0.076 (3)0.079 (3)0.019 (2)0.0037 (19)0.003 (3)
O2X0.0283 (18)0.051 (3)0.040 (3)0.0108 (16)0.0014 (19)0.005 (3)
N1X0.026 (2)0.047 (3)0.042 (2)0.0135 (19)0.0006 (19)0.010 (2)
C1X0.044 (4)0.068 (4)0.046 (4)0.021 (4)0.003 (3)0.021 (3)
C2X0.036 (3)0.037 (3)0.035 (3)0.015 (2)0.004 (2)0.004 (3)
C3X0.044 (3)0.053 (3)0.041 (3)0.019 (3)0.001 (3)0.012 (3)
C4X0.049 (4)0.070 (4)0.053 (4)0.016 (3)0.009 (3)0.017 (3)
C5X0.032 (2)0.055 (3)0.056 (4)0.013 (2)0.005 (3)0.012 (4)
O2X'0.0283 (18)0.051 (3)0.040 (3)0.0108 (16)0.0014 (19)0.005 (3)
N1X'0.026 (2)0.047 (3)0.042 (2)0.0135 (19)0.0006 (19)0.010 (2)
C1X'0.044 (4)0.068 (4)0.046 (4)0.021 (4)0.003 (3)0.021 (3)
C2X'0.036 (3)0.037 (3)0.035 (3)0.015 (2)0.004 (2)0.004 (3)
C3X'0.044 (3)0.053 (3)0.041 (3)0.019 (3)0.001 (3)0.012 (3)
C4X'0.049 (4)0.070 (4)0.053 (4)0.016 (3)0.009 (3)0.017 (3)
C5X'0.032 (2)0.055 (3)0.056 (4)0.013 (2)0.005 (3)0.012 (4)
N1Y0.084 (4)0.062 (3)0.099 (5)0.037 (3)0.014 (4)0.026 (3)
C1Y0.081 (5)0.081 (5)0.101 (6)0.024 (4)0.003 (5)0.032 (5)
C2Y0.040 (3)0.041 (3)0.122 (6)0.006 (3)0.038 (4)0.012 (4)
O2Y0.063 (3)0.093 (4)0.099 (4)0.018 (3)0.007 (3)0.024 (3)
C3Y0.118 (7)0.044 (4)0.097 (6)0.044 (4)0.004 (5)0.015 (4)
C4Y0.054 (4)0.048 (3)0.139 (7)0.021 (3)0.010 (4)0.024 (4)
C5Y0.058 (4)0.048 (3)0.080 (5)0.018 (3)0.017 (3)0.007 (3)
Geometric parameters (Å, º) top
N1A—C6A1.310 (5)C3X—H3X10.9900
N1A—C2A1.362 (5)C3X—H3X20.9900
C2A—O2A1.255 (5)C4X—C5X1.520 (9)
C2A—N3A1.367 (5)C4X—H4X10.9900
N3A—C4A1.375 (5)C4X—H4X20.9900
N3A—H3A0.869 (19)C5X—H5X10.9900
C4A—O4A1.233 (5)C5X—H5X20.9900
C4A—C5A1.420 (6)O2X'—C2X'1.256 (10)
C5A—C6A1.366 (6)N1X'—C2X'1.341 (10)
C5A—H5A0.9500N1X'—C1X'1.433 (11)
C6A—Cl6A1.766 (4)N1X'—C5X'1.437 (11)
N1B—C2B1.331 (5)C1X'—H1X70.9800
N1B—C6B1.355 (5)C1X'—H1X80.9800
C2B—N2B1.322 (5)C1X'—H1X90.9800
C2B—N3B1.362 (5)C1X'—H1XX0.9800
N2B—H21B0.88 (2)C1X'—H1XY0.9800
N2B—H22B0.88 (2)C1X'—H1XZ0.9800
N3B—C4B1.371 (5)C2X'—C3X'1.510 (12)
N3B—H3B0.80 (5)C3X'—C4X'1.523 (13)
C4B—N4B1.333 (5)C3X'—H3X30.9900
C4B—C5B1.368 (6)C3X'—H3X40.9900
N4B—H41B0.860 (19)C4X'—C5X'1.516 (14)
N4B—H42B0.865 (19)C4X'—H4X30.9900
C5B—C6B1.398 (6)C4X'—H4X40.9900
C5B—H5B0.9500C5X'—H5X30.9900
C6B—N6B1.342 (5)C5X'—H5X40.9900
N6B—H61B0.870 (19)N1Y—C2Y1.335 (7)
N6B—H62B0.853 (19)N1Y—C1Y1.379 (7)
O1W—H2W0.838 (10)N1Y—C5Y1.442 (7)
O1W—H1W0.837 (10)C1Y—H1Y10.9800
O2X—C2X1.256 (6)C1Y—H1Y20.9800
N1X—C2X1.345 (6)C1Y—H1Y30.9800
N1X—C1X1.432 (8)C2Y—O2Y1.242 (8)
N1X—C5X1.436 (7)C2Y—C3Y1.442 (10)
C1X—H1X10.9800C3Y—C4Y1.520 (10)
C1X—H1X20.9800C3Y—H3Y10.9900
C1X—H1X30.9800C3Y—H3Y20.9900
C1X—H1X40.9800C4Y—C5Y1.577 (9)
C1X—H1X50.9800C4Y—H4Y10.9900
C1X—H1X60.9800C4Y—H4Y20.9900
C2X—C3X1.508 (8)C5Y—H5Y10.9900
C3X—C4X1.521 (9)C5Y—H5Y20.9900
C6A—N1A—C2A116.3 (3)N1X—C5X—C4X105.5 (5)
O2A—C2A—N1A121.6 (4)N1X—C5X—H5X1110.6
O2A—C2A—N3A119.9 (4)C4X—C5X—H5X1110.6
N1A—C2A—N3A118.5 (3)N1X—C5X—H5X2110.6
C2A—N3A—C4A125.5 (3)C4X—C5X—H5X2110.6
C2A—N3A—H3A120 (3)H5X1—C5X—H5X2108.8
C4A—N3A—H3A115 (3)C2X'—N1X'—C1X'124.8 (13)
O4A—C4A—N3A118.6 (4)C2X'—N1X'—C5X'114.2 (10)
O4A—C4A—C5A126.3 (4)C1X'—N1X'—C5X'121.0 (13)
N3A—C4A—C5A115.1 (3)N1X'—C1X'—H1X7109.5
C6A—C5A—C4A115.7 (4)N1X'—C1X'—H1X8109.5
C6A—C5A—H5A122.1H1X7—C1X'—H1X8109.5
C4A—C5A—H5A122.1N1X'—C1X'—H1X9109.5
N1A—C6A—C5A128.8 (4)H1X7—C1X'—H1X9109.5
N1A—C6A—Cl6A113.4 (3)H1X8—C1X'—H1X9109.5
C5A—C6A—Cl6A117.8 (3)N1X'—C1X'—H1XX109.5
C2B—N1B—C6B117.7 (3)H1X7—C1X'—H1XX141.1
N2B—C2B—N1B119.7 (4)H1X8—C1X'—H1XX56.3
N2B—C2B—N3B118.1 (4)H1X9—C1X'—H1XX56.3
N1B—C2B—N3B122.2 (3)N1X'—C1X'—H1XY109.5
C2B—N2B—H21B123 (3)H1X7—C1X'—H1XY56.3
C2B—N2B—H22B119 (4)H1X8—C1X'—H1XY141.1
H21B—N2B—H22B118 (5)H1X9—C1X'—H1XY56.3
C2B—N3B—C4B120.8 (3)H1XX—C1X'—H1XY109.5
C2B—N3B—H3B114 (4)N1X'—C1X'—H1XZ109.5
C4B—N3B—H3B125 (4)H1X7—C1X'—H1XZ56.3
N4B—C4B—C5B124.9 (4)H1X8—C1X'—H1XZ56.3
N4B—C4B—N3B116.6 (4)H1X9—C1X'—H1XZ141.1
C5B—C4B—N3B118.4 (4)H1XX—C1X'—H1XZ109.5
C4B—N4B—H41B127 (3)H1XY—C1X'—H1XZ109.5
C4B—N4B—H42B121 (3)O2X'—C2X'—N1X'123.9 (14)
H41B—N4B—H42B112 (3)O2X'—C2X'—C3X'127.3 (15)
C4B—C5B—C6B118.5 (4)N1X'—C2X'—C3X'108.3 (9)
C4B—C5B—H5B120.8C2X'—C3X'—C4X'106.0 (9)
C6B—C5B—H5B120.8C2X'—C3X'—H3X3110.5
N6B—C6B—N1B116.7 (4)C4X'—C3X'—H3X3110.5
N6B—C6B—C5B121.0 (4)C2X'—C3X'—H3X4110.5
N1B—C6B—C5B122.3 (3)C4X'—C3X'—H3X4110.5
C6B—N6B—H61B119 (3)H3X3—C3X'—H3X4108.7
C6B—N6B—H62B130 (3)C5X'—C4X'—C3X'105.0 (10)
H61B—N6B—H62B111 (3)C5X'—C4X'—H4X3110.7
H2W—O1W—H1W115 (3)C3X'—C4X'—H4X3110.7
C2X—N1X—C1X123.8 (5)C5X'—C4X'—H4X4110.7
C2X—N1X—C5X114.4 (5)C3X'—C4X'—H4X4110.7
C1X—N1X—C5X121.4 (5)H4X3—C4X'—H4X4108.8
N1X—C1X—H1X1109.5N1X'—C5X'—C4X'105.9 (10)
N1X—C1X—H1X2109.5N1X'—C5X'—H5X3110.6
H1X1—C1X—H1X2109.5C4X'—C5X'—H5X3110.6
N1X—C1X—H1X3109.5N1X'—C5X'—H5X4110.6
H1X1—C1X—H1X3109.5C4X'—C5X'—H5X4110.6
H1X2—C1X—H1X3109.5H5X3—C5X'—H5X4108.7
N1X—C1X—H1X4109.5C2Y—N1Y—C1Y123.4 (7)
H1X1—C1X—H1X4141.1C2Y—N1Y—C5Y115.1 (6)
H1X2—C1X—H1X456.3C1Y—N1Y—C5Y121.5 (6)
H1X3—C1X—H1X456.3N1Y—C1Y—H1Y1109.5
N1X—C1X—H1X5109.5N1Y—C1Y—H1Y2109.5
H1X1—C1X—H1X556.3H1Y1—C1Y—H1Y2109.5
H1X2—C1X—H1X5141.1N1Y—C1Y—H1Y3109.5
H1X3—C1X—H1X556.3H1Y1—C1Y—H1Y3109.5
H1X4—C1X—H1X5109.5H1Y2—C1Y—H1Y3109.5
N1X—C1X—H1X6109.5O2Y—C2Y—N1Y122.8 (8)
H1X1—C1X—H1X656.3O2Y—C2Y—C3Y126.6 (6)
H1X2—C1X—H1X656.3N1Y—C2Y—C3Y110.5 (6)
H1X3—C1X—H1X6141.1C2Y—C3Y—C4Y106.7 (7)
H1X4—C1X—H1X6109.5C2Y—C3Y—H3Y1110.4
H1X5—C1X—H1X6109.5C4Y—C3Y—H3Y1110.4
O2X—C2X—N1X123.6 (6)C2Y—C3Y—H3Y2110.4
O2X—C2X—C3X128.3 (5)C4Y—C3Y—H3Y2110.4
N1X—C2X—C3X108.0 (5)H3Y1—C3Y—H3Y2108.6
C2X—C3X—C4X106.0 (5)C3Y—C4Y—C5Y104.7 (6)
C2X—C3X—H3X1110.5C3Y—C4Y—H4Y1110.8
C4X—C3X—H3X1110.5C5Y—C4Y—H4Y1110.8
C2X—C3X—H3X2110.5C3Y—C4Y—H4Y2110.8
C4X—C3X—H3X2110.5C5Y—C4Y—H4Y2110.8
H3X1—C3X—H3X2108.7H4Y1—C4Y—H4Y2108.9
C5X—C4X—C3X104.8 (5)N1Y—C5Y—C4Y102.7 (5)
C5X—C4X—H4X1110.8N1Y—C5Y—H5Y1111.2
C3X—C4X—H4X1110.8C4Y—C5Y—H5Y1111.2
C5X—C4X—H4X2110.8N1Y—C5Y—H5Y2111.2
C3X—C4X—H4X2110.8C4Y—C5Y—H5Y2111.2
H4X1—C4X—H4X2108.9H5Y1—C5Y—H5Y2109.1
C6A—N1A—C2A—O2A179.2 (4)C5X—N1X—C2X—C3X1.4 (9)
C6A—N1A—C2A—N3A1.8 (6)O2X—C2X—C3X—C4X174.3 (8)
O2A—C2A—N3A—C4A179.1 (4)N1X—C2X—C3X—C4X5.7 (8)
N1A—C2A—N3A—C4A1.9 (6)C2X—C3X—C4X—C5X10.0 (9)
C2A—N3A—C4A—O4A180.0 (4)C2X—N1X—C5X—C4X7.9 (11)
C2A—N3A—C4A—C5A0.6 (6)C1X—N1X—C5X—C4X178.6 (7)
O4A—C4A—C5A—C6A178.7 (5)C3X—C4X—C5X—N1X10.7 (11)
N3A—C4A—C5A—C6A0.6 (6)C1X'—N1X'—C2X'—O2X'3 (6)
C2A—N1A—C6A—C5A0.6 (7)C5X'—N1X'—C2X'—O2X'178 (5)
C2A—N1A—C6A—Cl6A180.0 (3)C1X'—N1X'—C2X'—C3X'175 (3)
C4A—C5A—C6A—N1A0.7 (7)C5X'—N1X'—C2X'—C3X'6 (5)
C4A—C5A—C6A—Cl6A178.7 (3)O2X'—C2X'—C3X'—C4X'173 (4)
C6B—N1B—C2B—N2B177.6 (4)N1X'—C2X'—C3X'—C4X'1 (4)
C6B—N1B—C2B—N3B1.3 (6)C2X'—C3X'—C4X'—C5X'3 (5)
N2B—C2B—N3B—C4B176.7 (4)C2X'—N1X'—C5X'—C4X'8 (6)
N1B—C2B—N3B—C4B2.2 (6)C1X'—N1X'—C5X'—C4X'173 (3)
C2B—N3B—C4B—N4B179.2 (4)C3X'—C4X'—C5X'—N1X'6 (5)
C2B—N3B—C4B—C5B1.9 (6)C1Y—N1Y—C2Y—O2Y2.5 (11)
N4B—C4B—C5B—C6B179.6 (4)C5Y—N1Y—C2Y—O2Y178.8 (6)
N3B—C4B—C5B—C6B0.9 (6)C1Y—N1Y—C2Y—C3Y178.9 (7)
C2B—N1B—C6B—N6B179.4 (4)C5Y—N1Y—C2Y—C3Y2.3 (8)
C2B—N1B—C6B—C5B0.2 (6)O2Y—C2Y—C3Y—C4Y179.0 (7)
C4B—C5B—C6B—N6B179.2 (4)N1Y—C2Y—C3Y—C4Y4.7 (7)
C4B—C5B—C6B—N1B0.0 (6)C2Y—C3Y—C4Y—C5Y5.1 (7)
C1X—N1X—C2X—O2X5.2 (11)C2Y—N1Y—C5Y—C4Y1.0 (7)
C5X—N1X—C2X—O2X178.6 (9)C1Y—N1Y—C5Y—C4Y177.7 (6)
C1X—N1X—C2X—C3X174.8 (6)C3Y—C4Y—C5Y—N1Y3.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O2Ai0.87 (2)2.02 (2)2.884 (4)178 (5)
N2B—H21B···O4Ai0.88 (2)2.08 (4)2.796 (5)138 (5)
N2B—H22B···N1Bii0.88 (2)2.13 (2)3.008 (5)175 (5)
N3B—H3B···O2A0.80 (5)2.17 (5)2.964 (4)177 (5)
N4B—H41B···N1A0.86 (2)2.01 (2)2.857 (5)166 (4)
N4B—H42B···O1W0.87 (2)1.96 (2)2.815 (5)168 (5)
N6B—H61B···O4Aiii0.87 (2)2.05 (2)2.898 (5)165 (4)
N6B—H62B···O2X0.85 (2)2.04 (2)2.887 (6)173 (4)
O1W—H1W···O2Y0.84 (1)2.08 (6)2.701 (6)131 (7)
O1W—H2W···O4Aiv0.84 (1)2.12 (3)2.903 (6)156 (6)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x, y, z1; (iv) x, y, z+2.
(II) ; top
Crystal data top
C3H6N6·2(C5H9NO)·H2OF(000) = 736
Mr = 342.42Dx = 1.309 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 42744 reflections
a = 7.6291 (4) Åθ = 2.9–26.4°
b = 21.0118 (8) ŵ = 0.10 mm1
c = 10.9690 (6) ÅT = 173 K
β = 98.950 (4)°Plate, colourless
V = 1736.93 (15) Å30.32 × 0.20 × 0.07 mm
Z = 4
Data collection top
STOE IPDS II two-circle
diffractometer
3394 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2914 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.058
ω scansθmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 99
Tmin = 0.970, Tmax = 0.993k = 2525
50506 measured reflectionsl = 1313
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.8452P]
where P = (Fo2 + 2Fc2)/3
3394 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.18 e Å3
Crystal data top
C3H6N6·2(C5H9NO)·H2OV = 1736.93 (15) Å3
Mr = 342.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.6291 (4) ŵ = 0.10 mm1
b = 21.0118 (8) ÅT = 173 K
c = 10.9690 (6) Å0.32 × 0.20 × 0.07 mm
β = 98.950 (4)°
Data collection top
STOE IPDS II two-circle
diffractometer
3394 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2914 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.993Rint = 0.058
50506 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0443 restraints
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.18 e Å3
3394 reflectionsΔρmin = 0.18 e Å3
243 parameters
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
N10.57216 (18)0.23511 (6)0.32536 (12)0.0253 (3)
C20.5679 (2)0.29920 (7)0.31483 (15)0.0242 (3)
N20.6625 (2)0.33208 (7)0.40692 (14)0.0302 (3)
H210.723 (3)0.3118 (10)0.471 (2)0.036*
H220.663 (3)0.3720 (11)0.4023 (19)0.036*
N30.47915 (18)0.33242 (6)0.22077 (12)0.0264 (3)
C40.3856 (2)0.29598 (7)0.13273 (15)0.0245 (3)
N40.2952 (2)0.32570 (7)0.03575 (14)0.0338 (4)
H410.237 (3)0.3030 (10)0.027 (2)0.041*
H420.299 (3)0.3676 (11)0.0322 (19)0.041*
N50.37670 (18)0.23186 (6)0.13293 (12)0.0252 (3)
C60.4748 (2)0.20421 (7)0.23057 (14)0.0234 (3)
N60.4749 (2)0.14032 (7)0.23526 (14)0.0303 (3)
H610.420 (3)0.1182 (10)0.168 (2)0.036*
H620.549 (3)0.1209 (10)0.292 (2)0.036*
O1W0.82290 (19)0.44772 (6)0.52417 (13)0.0388 (3)
H1W10.817 (3)0.4877 (5)0.534 (2)0.058*
H1W20.916 (2)0.4418 (10)0.492 (2)0.058*
N1X0.7549 (2)0.67951 (7)0.49912 (14)0.0335 (3)
C1X0.8635 (3)0.71339 (9)0.59756 (19)0.0403 (4)
H1X10.93300.68290.65290.060*
H1X20.78740.73820.64390.060*
H1X30.94400.74210.56270.060*
C2X0.7504 (2)0.61649 (8)0.48894 (17)0.0321 (4)
O2X0.84431 (18)0.57929 (6)0.55929 (13)0.0415 (3)
C3X0.6158 (3)0.59790 (9)0.38030 (19)0.0405 (4)
H3X10.51460.57550.40770.049*
H3X20.66960.56960.32410.049*
C4X0.5551 (3)0.66021 (10)0.3161 (2)0.0452 (5)
H4X10.42400.66310.30200.054*
H4X20.59800.66350.23570.054*
C5X0.6357 (3)0.71267 (9)0.40343 (19)0.0392 (4)
H5X10.70170.74360.35970.047*
H5X20.54230.73560.43910.047*
N1Y0.7454 (2)0.03784 (7)0.51588 (15)0.0377 (4)
C1Y0.8290 (3)0.01487 (12)0.6341 (2)0.0579 (6)
H1Y10.95460.02690.64730.087*
H1Y20.77070.03360.69910.087*
H1Y30.81860.03160.63650.087*
C2Y0.6946 (2)0.00107 (8)0.41834 (17)0.0330 (4)
O2Y0.7016 (2)0.05755 (6)0.41793 (12)0.0452 (4)
C3Y0.6352 (3)0.04271 (9)0.3087 (2)0.0472 (5)
H3Y10.72400.04270.25180.057*
H3Y20.52000.02790.26330.057*
C4Y0.6175 (3)0.10836 (9)0.3620 (2)0.0506 (6)
H4Y10.49250.11750.37000.061*
H4Y20.66040.14140.30940.061*
C5Y0.7321 (3)0.10592 (9)0.4871 (2)0.0503 (6)
H5Y10.67590.12920.54930.060*
H5Y20.85060.12440.48390.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0294 (7)0.0224 (7)0.0224 (7)0.0005 (5)0.0013 (6)0.0003 (5)
C20.0249 (8)0.0236 (8)0.0239 (8)0.0017 (6)0.0031 (6)0.0009 (6)
N20.0377 (8)0.0213 (7)0.0281 (8)0.0037 (6)0.0062 (6)0.0003 (6)
N30.0307 (7)0.0217 (6)0.0251 (7)0.0011 (5)0.0009 (6)0.0006 (5)
C40.0257 (8)0.0220 (7)0.0250 (8)0.0006 (6)0.0014 (6)0.0003 (6)
N40.0458 (9)0.0205 (7)0.0299 (8)0.0001 (6)0.0104 (7)0.0015 (6)
N50.0281 (7)0.0224 (7)0.0235 (7)0.0002 (5)0.0013 (6)0.0005 (5)
C60.0252 (8)0.0227 (7)0.0221 (8)0.0001 (6)0.0029 (6)0.0001 (6)
N60.0403 (8)0.0199 (7)0.0267 (8)0.0005 (6)0.0075 (6)0.0010 (6)
O1W0.0442 (7)0.0233 (6)0.0469 (8)0.0033 (5)0.0010 (6)0.0007 (6)
N1X0.0349 (8)0.0250 (7)0.0405 (9)0.0021 (6)0.0057 (7)0.0022 (6)
C1X0.0424 (10)0.0321 (9)0.0473 (11)0.0045 (8)0.0096 (9)0.0110 (8)
C2X0.0331 (9)0.0265 (8)0.0365 (10)0.0032 (7)0.0054 (7)0.0025 (7)
O2X0.0461 (8)0.0277 (6)0.0470 (8)0.0076 (6)0.0040 (6)0.0010 (6)
C3X0.0409 (10)0.0352 (10)0.0433 (11)0.0001 (8)0.0001 (9)0.0065 (8)
C4X0.0402 (11)0.0506 (12)0.0427 (11)0.0084 (9)0.0001 (9)0.0021 (9)
C5X0.0413 (10)0.0309 (9)0.0478 (11)0.0082 (8)0.0147 (9)0.0099 (8)
N1Y0.0446 (9)0.0275 (8)0.0399 (9)0.0053 (6)0.0033 (7)0.0085 (6)
C1Y0.0668 (15)0.0599 (14)0.0417 (12)0.0007 (11)0.0085 (11)0.0145 (10)
C2Y0.0367 (9)0.0267 (9)0.0336 (9)0.0014 (7)0.0012 (7)0.0003 (7)
O2Y0.0697 (10)0.0193 (6)0.0392 (8)0.0004 (6)0.0145 (7)0.0009 (5)
C3Y0.0655 (14)0.0315 (10)0.0429 (12)0.0085 (9)0.0032 (10)0.0083 (8)
C4Y0.0602 (13)0.0262 (9)0.0709 (15)0.0085 (9)0.0277 (12)0.0108 (9)
C5Y0.0674 (14)0.0244 (9)0.0654 (14)0.0097 (9)0.0296 (12)0.0107 (9)
Geometric parameters (Å, º) top
N1—C61.347 (2)C3X—C4X1.524 (3)
N1—C21.352 (2)C3X—H3X10.9900
C2—N21.338 (2)C3X—H3X20.9900
C2—N31.339 (2)C4X—C5X1.525 (3)
N2—H210.89 (2)C4X—H4X10.9900
N2—H220.84 (2)C4X—H4X20.9900
N3—C41.347 (2)C5X—H5X10.9900
C4—N41.330 (2)C5X—H5X20.9900
C4—N51.349 (2)N1Y—C2Y1.328 (2)
N4—H410.89 (2)N1Y—C1Y1.436 (3)
N4—H420.88 (2)N1Y—C5Y1.465 (2)
N5—C61.340 (2)C1Y—H1Y10.9800
C6—N61.343 (2)C1Y—H1Y20.9800
N6—H610.91 (2)C1Y—H1Y30.9800
N6—H620.87 (2)C2Y—O2Y1.233 (2)
O1W—H1W10.850 (9)C2Y—C3Y1.499 (3)
O1W—H1W20.852 (9)C3Y—C4Y1.513 (3)
N1X—C2X1.329 (2)C3Y—H3Y10.9900
N1X—C1X1.443 (2)C3Y—H3Y20.9900
N1X—C5X1.455 (2)C4Y—C5Y1.508 (4)
C1X—H1X10.9800C4Y—H4Y10.9900
C1X—H1X20.9800C4Y—H4Y20.9900
C1X—H1X30.9800C5Y—H5Y10.9900
C2X—O2X1.244 (2)C5Y—H5Y20.9900
C2X—C3X1.499 (3)
C6—N1—C2114.29 (13)C3X—C4X—H4X1110.6
N2—C2—N3117.46 (14)C5X—C4X—H4X1110.6
N2—C2—N1116.54 (14)C3X—C4X—H4X2110.6
N3—C2—N1126.00 (14)C5X—C4X—H4X2110.6
C2—N2—H21120.1 (13)H4X1—C4X—H4X2108.8
C2—N2—H22118.5 (14)N1X—C5X—C4X104.62 (15)
H21—N2—H22121.5 (19)N1X—C5X—H5X1110.8
C2—N3—C4113.85 (13)C4X—C5X—H5X1110.8
N4—C4—N3117.23 (14)N1X—C5X—H5X2110.8
N4—C4—N5116.77 (14)C4X—C5X—H5X2110.8
N3—C4—N5125.99 (14)H5X1—C5X—H5X2108.9
C4—N4—H41119.7 (14)C2Y—N1Y—C1Y124.38 (17)
C4—N4—H42119.2 (14)C2Y—N1Y—C5Y113.13 (17)
H41—N4—H42121 (2)C1Y—N1Y—C5Y121.93 (17)
C6—N5—C4114.37 (13)N1Y—C1Y—H1Y1109.5
N5—C6—N6117.46 (14)N1Y—C1Y—H1Y2109.5
N5—C6—N1125.47 (14)H1Y1—C1Y—H1Y2109.5
N6—C6—N1117.07 (14)N1Y—C1Y—H1Y3109.5
C6—N6—H61118.7 (13)H1Y1—C1Y—H1Y3109.5
C6—N6—H62119.4 (13)H1Y2—C1Y—H1Y3109.5
H61—N6—H62120.0 (18)O2Y—C2Y—N1Y125.24 (17)
H1W1—O1W—H1W2105.1 (17)O2Y—C2Y—C3Y126.01 (17)
C2X—N1X—C1X123.98 (16)N1Y—C2Y—C3Y108.70 (16)
C2X—N1X—C5X114.30 (15)C2Y—C3Y—C4Y104.84 (17)
C1X—N1X—C5X121.69 (15)C2Y—C3Y—H3Y1110.8
N1X—C1X—H1X1109.5C4Y—C3Y—H3Y1110.8
N1X—C1X—H1X2109.5C2Y—C3Y—H3Y2110.8
H1X1—C1X—H1X2109.5C4Y—C3Y—H3Y2110.8
N1X—C1X—H1X3109.5H3Y1—C3Y—H3Y2108.9
H1X1—C1X—H1X3109.5C5Y—C4Y—C3Y104.28 (16)
H1X2—C1X—H1X3109.5C5Y—C4Y—H4Y1110.9
O2X—C2X—N1X124.68 (17)C3Y—C4Y—H4Y1110.9
O2X—C2X—C3X125.93 (16)C5Y—C4Y—H4Y2110.9
N1X—C2X—C3X109.39 (15)C3Y—C4Y—H4Y2110.9
C2X—C3X—C4X105.36 (15)H4Y1—C4Y—H4Y2108.9
C2X—C3X—H3X1110.7N1Y—C5Y—C4Y103.90 (16)
C4X—C3X—H3X1110.7N1Y—C5Y—H5Y1111.0
C2X—C3X—H3X2110.7C4Y—C5Y—H5Y1111.0
C4X—C3X—H3X2110.7N1Y—C5Y—H5Y2111.0
H3X1—C3X—H3X2108.8C4Y—C5Y—H5Y2111.0
C3X—C4X—C5X105.48 (16)H5Y1—C5Y—H5Y2109.0
C6—N1—C2—N2179.89 (14)O2X—C2X—C3X—C4X173.06 (18)
C6—N1—C2—N30.6 (2)N1X—C2X—C3X—C4X6.8 (2)
N2—C2—N3—C4179.18 (14)C2X—C3X—C4X—C5X9.1 (2)
N1—C2—N3—C41.3 (2)C2X—N1X—C5X—C4X4.4 (2)
C2—N3—C4—N4179.40 (15)C1X—N1X—C5X—C4X177.27 (16)
C2—N3—C4—N50.3 (2)C3X—C4X—C5X—N1X8.2 (2)
N4—C4—N5—C6177.86 (15)C1Y—N1Y—C2Y—O2Y4.9 (3)
N3—C4—N5—C61.2 (2)C5Y—N1Y—C2Y—O2Y176.41 (19)
C4—N5—C6—N6178.64 (15)C1Y—N1Y—C2Y—C3Y172.7 (2)
C4—N5—C6—N12.1 (2)C5Y—N1Y—C2Y—C3Y1.2 (2)
C2—N1—C6—N51.3 (2)O2Y—C2Y—C3Y—C4Y169.4 (2)
C2—N1—C6—N6179.46 (14)N1Y—C2Y—C3Y—C4Y13.0 (2)
C1X—N1X—C2X—O2X3.4 (3)C2Y—C3Y—C4Y—C5Y21.3 (2)
C5X—N1X—C2X—O2X178.34 (17)C2Y—N1Y—C5Y—C4Y14.9 (2)
C1X—N1X—C2X—C3X176.74 (17)C1Y—N1Y—C5Y—C4Y173.32 (19)
C5X—N1X—C2X—C3X1.6 (2)C3Y—C4Y—C5Y—N1Y21.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N5i0.89 (2)2.18 (2)3.060 (2)176.1 (18)
N2—H22···O1W0.84 (2)2.30 (2)2.9268 (19)131.4 (18)
N4—H41···N1ii0.89 (2)2.06 (2)2.938 (2)169.6 (19)
N4—H42···O2Yii0.88 (2)2.08 (2)2.8126 (19)140.6 (19)
N6—H61···O1Wii0.91 (2)2.15 (2)3.048 (2)169.3 (18)
N6—H62···O2Y0.87 (2)2.13 (2)2.992 (2)168.9 (19)
O1W—H1W1···O2X0.85 (1)1.95 (1)2.7926 (17)171 (2)
O1W—H1W2···O2Xiii0.85 (1)2.04 (1)2.886 (2)171 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+2, y+1, z+1.
(III) ; top
Crystal data top
C4H3ClN2O2·C4H7N5·C4H9NOZ = 2
Mr = 358.80F(000) = 376
Triclinic, P1Dx = 1.483 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9970 (5) ÅCell parameters from 33416 reflections
b = 8.6140 (5) Åθ = 3.3–26.3°
c = 13.8513 (9) ŵ = 0.27 mm1
α = 85.725 (5)°T = 173 K
β = 84.516 (5)°Plate, colourless
γ = 75.572 (5)°0.44 × 0.31 × 0.05 mm
V = 803.70 (9) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
3103 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2815 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.045
ω scansθmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 88
Tmin = 0.890, Tmax = 0.986k = 1010
27171 measured reflectionsl = 1616
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.042P)2 + 0.5034P]
where P = (Fo2 + 2Fc2)/3
3103 reflections(Δ/σ)max < 0.001
239 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C4H3ClN2O2·C4H7N5·C4H9NOγ = 75.572 (5)°
Mr = 358.80V = 803.70 (9) Å3
Triclinic, P1Z = 2
a = 6.9970 (5) ÅMo Kα radiation
b = 8.6140 (5) ŵ = 0.27 mm1
c = 13.8513 (9) ÅT = 173 K
α = 85.725 (5)°0.44 × 0.31 × 0.05 mm
β = 84.516 (5)°
Data collection top
STOE IPDS II two-circle
diffractometer
3103 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2815 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.986Rint = 0.045
27171 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.28 e Å3
3103 reflectionsΔρmin = 0.24 e Å3
239 parameters
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
N1A0.3519 (2)0.82955 (17)0.35115 (11)0.0232 (3)
C2A0.3130 (3)0.7147 (2)0.41647 (13)0.0205 (3)
O2A0.2482 (2)0.74520 (14)0.50291 (9)0.0262 (3)
N3A0.3438 (2)0.56102 (17)0.38803 (11)0.0217 (3)
H3A0.314 (3)0.490 (3)0.4316 (16)0.026*
C4A0.4099 (3)0.5120 (2)0.29560 (13)0.0227 (4)
O4A0.4297 (2)0.37024 (15)0.27664 (10)0.0313 (3)
C5A0.4491 (3)0.6352 (2)0.22779 (13)0.0250 (4)
H5A0.49640.61400.16230.030*
C6A0.4156 (3)0.7840 (2)0.26146 (13)0.0225 (4)
Cl6A0.45510 (8)0.94166 (5)0.18076 (3)0.03276 (15)
N1B0.2060 (2)0.05636 (18)0.55784 (11)0.0228 (3)
H1B0.224 (3)0.042 (3)0.5365 (16)0.027*
C2B0.2423 (3)0.1777 (2)0.49481 (13)0.0218 (4)
N2B0.3016 (3)0.1458 (2)0.40461 (12)0.0300 (4)
H2B10.338 (3)0.220 (3)0.3674 (18)0.036*
H2B20.320 (3)0.047 (3)0.3850 (17)0.036*
N3B0.2183 (2)0.32494 (17)0.52511 (11)0.0217 (3)
C4B0.1553 (2)0.3465 (2)0.61899 (13)0.0206 (3)
N4B0.1285 (2)0.49194 (18)0.65006 (12)0.0247 (3)
H4B10.100 (3)0.509 (3)0.7112 (18)0.030*
H4B20.153 (3)0.569 (3)0.6094 (17)0.030*
N5B0.1172 (2)0.22898 (18)0.68548 (11)0.0233 (3)
C6B0.1460 (3)0.0866 (2)0.65163 (13)0.0221 (4)
C61B0.1165 (3)0.0530 (2)0.71617 (14)0.0283 (4)
H61A0.07290.01800.78210.043*
H61B0.24160.13540.71720.043*
H61C0.01580.09760.69160.043*
C1X0.2197 (3)0.6746 (3)0.93637 (17)0.0389 (5)
H1X10.27380.64050.88100.058*
H1X20.29010.78520.94990.058*
H1X30.23650.60370.99360.058*
C2X0.0028 (3)0.6659 (2)0.91266 (14)0.0282 (4)
O2X0.0892 (2)0.5991 (2)0.84235 (11)0.0412 (4)
N3X0.0863 (2)0.7354 (2)0.97338 (12)0.0307 (4)
C4X0.0034 (4)0.7936 (3)1.06727 (17)0.0443 (6)
H4X10.14650.80431.07050.067*
H4X20.02240.89841.07540.067*
H4X30.05380.71731.11910.067*
C5X0.2953 (3)0.7296 (3)0.95317 (16)0.0351 (5)
H5X10.37260.64610.99560.053*
H5X20.31890.83380.96500.053*
H5X30.33560.70500.88520.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0308 (8)0.0162 (7)0.0230 (8)0.0073 (6)0.0009 (6)0.0010 (6)
C2A0.0242 (8)0.0174 (8)0.0212 (9)0.0066 (6)0.0024 (7)0.0029 (6)
O2A0.0400 (7)0.0186 (6)0.0209 (7)0.0098 (5)0.0027 (5)0.0045 (5)
N3A0.0307 (8)0.0147 (7)0.0203 (8)0.0077 (6)0.0004 (6)0.0005 (6)
C4A0.0279 (9)0.0187 (8)0.0219 (9)0.0064 (7)0.0006 (7)0.0034 (7)
O4A0.0500 (8)0.0188 (6)0.0261 (7)0.0126 (6)0.0067 (6)0.0064 (5)
C5A0.0327 (10)0.0216 (9)0.0206 (9)0.0073 (7)0.0007 (7)0.0019 (7)
C6A0.0259 (9)0.0186 (8)0.0234 (9)0.0071 (7)0.0029 (7)0.0029 (7)
Cl6A0.0481 (3)0.0222 (2)0.0278 (3)0.0121 (2)0.0019 (2)0.00586 (17)
N1B0.0315 (8)0.0150 (7)0.0225 (8)0.0070 (6)0.0014 (6)0.0015 (6)
C2B0.0265 (9)0.0173 (8)0.0224 (9)0.0069 (7)0.0022 (7)0.0018 (7)
N2B0.0536 (11)0.0164 (7)0.0217 (8)0.0142 (7)0.0064 (7)0.0037 (6)
N3B0.0297 (8)0.0156 (7)0.0208 (7)0.0075 (6)0.0016 (6)0.0022 (5)
C4B0.0221 (8)0.0187 (8)0.0218 (8)0.0051 (6)0.0041 (6)0.0018 (6)
N4B0.0370 (9)0.0189 (7)0.0191 (8)0.0081 (6)0.0010 (6)0.0042 (6)
N5B0.0290 (8)0.0201 (7)0.0216 (7)0.0071 (6)0.0020 (6)0.0022 (6)
C6B0.0240 (8)0.0199 (8)0.0227 (9)0.0058 (7)0.0037 (7)0.0002 (7)
C61B0.0402 (11)0.0216 (9)0.0234 (9)0.0098 (8)0.0003 (8)0.0011 (7)
C1X0.0322 (11)0.0403 (12)0.0455 (13)0.0122 (9)0.0087 (9)0.0083 (10)
C2X0.0345 (10)0.0252 (9)0.0248 (10)0.0079 (8)0.0036 (8)0.0025 (7)
O2X0.0472 (9)0.0481 (9)0.0321 (8)0.0173 (7)0.0028 (7)0.0151 (7)
N3X0.0302 (8)0.0343 (9)0.0274 (9)0.0071 (7)0.0004 (7)0.0072 (7)
C4X0.0471 (13)0.0539 (14)0.0329 (12)0.0128 (11)0.0059 (10)0.0183 (10)
C5X0.0305 (10)0.0387 (11)0.0379 (11)0.0119 (9)0.0019 (8)0.0029 (9)
Geometric parameters (Å, º) top
N1A—C6A1.333 (2)N4B—H4B10.87 (2)
N1A—C2A1.351 (2)N4B—H4B20.88 (2)
C2A—O2A1.262 (2)N5B—C6B1.307 (2)
C2A—N3A1.369 (2)C6B—C61B1.489 (2)
N3A—C4A1.379 (2)C61B—H61A0.9800
N3A—H3A0.88 (2)C61B—H61B0.9800
C4A—O4A1.239 (2)C61B—H61C0.9800
C4A—C5A1.425 (2)C1X—C2X1.506 (3)
C5A—C6A1.355 (2)C1X—H1X10.9800
C5A—H5A0.9500C1X—H1X20.9800
C6A—Cl6A1.7524 (17)C1X—H1X30.9800
N1B—C6B1.350 (2)C2X—O2X1.214 (2)
N1B—C2B1.369 (2)C2X—N3X1.347 (3)
N1B—H1B0.89 (2)N3X—C5X1.452 (3)
C2B—N2B1.305 (2)N3X—C4X1.456 (3)
C2B—N3B1.331 (2)C4X—H4X10.9800
N2B—H2B10.87 (3)C4X—H4X20.9800
N2B—H2B20.89 (3)C4X—H4X30.9800
N3B—C4B1.344 (2)C5X—H5X10.9800
C4B—N4B1.318 (2)C5X—H5X20.9800
C4B—N5B1.376 (2)C5X—H5X30.9800
C6A—N1A—C2A116.56 (15)N5B—C6B—N1B122.80 (16)
O2A—C2A—N1A121.86 (15)N5B—C6B—C61B121.05 (16)
O2A—C2A—N3A119.02 (15)N1B—C6B—C61B116.15 (15)
N1A—C2A—N3A119.12 (15)C6B—C61B—H61A109.5
C2A—N3A—C4A125.01 (15)C6B—C61B—H61B109.5
C2A—N3A—H3A117.0 (14)H61A—C61B—H61B109.5
C4A—N3A—H3A117.9 (14)C6B—C61B—H61C109.5
O4A—C4A—N3A120.09 (16)H61A—C61B—H61C109.5
O4A—C4A—C5A124.99 (16)H61B—C61B—H61C109.5
N3A—C4A—C5A114.92 (15)C2X—C1X—H1X1109.5
C6A—C5A—C4A116.60 (16)C2X—C1X—H1X2109.5
C6A—C5A—H5A121.7H1X1—C1X—H1X2109.5
C4A—C5A—H5A121.7C2X—C1X—H1X3109.5
N1A—C6A—C5A127.78 (16)H1X1—C1X—H1X3109.5
N1A—C6A—Cl6A113.47 (13)H1X2—C1X—H1X3109.5
C5A—C6A—Cl6A118.74 (14)O2X—C2X—N3X120.98 (19)
C6B—N1B—C2B119.49 (15)O2X—C2X—C1X121.97 (19)
C6B—N1B—H1B121.0 (14)N3X—C2X—C1X117.05 (18)
C2B—N1B—H1B119.5 (14)C2X—N3X—C5X118.77 (17)
N2B—C2B—N3B120.81 (16)C2X—N3X—C4X124.24 (18)
N2B—C2B—N1B118.59 (16)C5X—N3X—C4X116.18 (17)
N3B—C2B—N1B120.60 (16)N3X—C4X—H4X1109.5
C2B—N2B—H2B1117.5 (16)N3X—C4X—H4X2109.5
C2B—N2B—H2B2120.5 (16)H4X1—C4X—H4X2109.5
H2B1—N2B—H2B2121 (2)N3X—C4X—H4X3109.5
C2B—N3B—C4B116.52 (15)H4X1—C4X—H4X3109.5
N4B—C4B—N3B117.38 (16)H4X2—C4X—H4X3109.5
N4B—C4B—N5B117.31 (16)N3X—C5X—H5X1109.5
N3B—C4B—N5B125.31 (15)N3X—C5X—H5X2109.5
C4B—N4B—H4B1120.1 (15)H5X1—C5X—H5X2109.5
C4B—N4B—H4B2119.4 (15)N3X—C5X—H5X3109.5
H4B1—N4B—H4B2120 (2)H5X1—C5X—H5X3109.5
C6B—N5B—C4B115.26 (15)H5X2—C5X—H5X3109.5
C6A—N1A—C2A—O2A178.58 (16)N2B—C2B—N3B—C4B179.48 (17)
C6A—N1A—C2A—N3A1.1 (2)N1B—C2B—N3B—C4B0.8 (2)
O2A—C2A—N3A—C4A178.55 (16)C2B—N3B—C4B—N4B179.25 (16)
N1A—C2A—N3A—C4A1.1 (3)C2B—N3B—C4B—N5B1.1 (3)
C2A—N3A—C4A—O4A178.68 (17)N4B—C4B—N5B—C6B179.88 (16)
C2A—N3A—C4A—C5A0.8 (3)N3B—C4B—N5B—C6B0.2 (3)
O4A—C4A—C5A—C6A178.91 (18)C4B—N5B—C6B—N1B1.0 (3)
N3A—C4A—C5A—C6A0.6 (3)C4B—N5B—C6B—C61B178.14 (16)
C2A—N1A—C6A—C5A1.0 (3)C2B—N1B—C6B—N5B1.2 (3)
C2A—N1A—C6A—Cl6A178.17 (13)C2B—N1B—C6B—C61B177.92 (16)
C4A—C5A—C6A—N1A0.8 (3)O2X—C2X—N3X—C5X0.2 (3)
C4A—C5A—C6A—Cl6A178.38 (13)C1X—C2X—N3X—C5X179.92 (17)
C6B—N1B—C2B—N2B179.47 (17)O2X—C2X—N3X—C4X169.1 (2)
C6B—N1B—C2B—N3B0.3 (3)C1X—C2X—N3X—C4X10.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···N3B0.88 (2)2.04 (2)2.917 (2)174 (2)
N1B—H1B···O2Ai0.89 (2)1.89 (2)2.7779 (19)174 (2)
N2B—H2B1···O4A0.87 (3)1.92 (3)2.780 (2)175 (2)
N2B—H2B2···N1Ai0.89 (3)1.92 (3)2.805 (2)176 (2)
N4B—H4B1···O2X0.87 (2)2.02 (3)2.850 (2)161 (2)
N4B—H4B2···O2A0.88 (2)2.21 (2)3.088 (2)173 (2)
Symmetry code: (i) x, y1, z.
(IV) ; top
Crystal data top
C4H3ClN2O2·C4H7N5·C3H7NO·H2OZ = 2
Mr = 362.79F(000) = 380
Triclinic, P1Dx = 1.472 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1719 (11) ÅCell parameters from 12063 reflections
b = 8.6197 (11) Åθ = 3.3–26.2°
c = 13.5029 (19) ŵ = 0.27 mm1
α = 94.574 (11)°T = 173 K
β = 92.707 (12)°Block, colourless
γ = 99.840 (11)°0.16 × 0.14 × 0.11 mm
V = 818.3 (2) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
3149 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2270 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.117
ω scansθmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 88
Tmin = 0.958, Tmax = 0.972k = 1010
13964 measured reflectionsl = 1616
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0926P)2 + 0.0699P]
where P = (Fo2 + 2Fc2)/3
3149 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.32 e Å3
3 restraintsΔρmin = 0.42 e Å3
Crystal data top
C4H3ClN2O2·C4H7N5·C3H7NO·H2Oγ = 99.840 (11)°
Mr = 362.79V = 818.3 (2) Å3
Triclinic, P1Z = 2
a = 7.1719 (11) ÅMo Kα radiation
b = 8.6197 (11) ŵ = 0.27 mm1
c = 13.5029 (19) ÅT = 173 K
α = 94.574 (11)°0.16 × 0.14 × 0.11 mm
β = 92.707 (12)°
Data collection top
STOE IPDS II two-circle
diffractometer
3149 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2270 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.972Rint = 0.117
13964 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0623 restraints
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.32 e Å3
3149 reflectionsΔρmin = 0.42 e Å3
244 parameters
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
N1A0.3252 (4)0.1427 (3)0.37736 (17)0.0314 (6)
C2A0.2869 (4)0.2611 (4)0.4408 (2)0.0306 (6)
O2A0.2276 (3)0.2352 (3)0.52532 (14)0.0348 (5)
N3A0.3137 (4)0.4116 (3)0.41226 (17)0.0308 (6)
H3A0.281 (5)0.486 (5)0.451 (3)0.037*
C4A0.3711 (4)0.4551 (4)0.3213 (2)0.0317 (7)
O4A0.3851 (3)0.5947 (3)0.30202 (16)0.0407 (6)
C5A0.4091 (4)0.3284 (4)0.2552 (2)0.0324 (7)
H5A0.45090.34540.19060.039*
C6A0.3829 (4)0.1837 (4)0.2885 (2)0.0313 (6)
Cl6A0.42203 (12)0.02266 (9)0.20984 (5)0.0398 (3)
N1B0.1959 (4)0.9265 (3)0.58219 (17)0.0313 (6)
H1B0.211 (5)1.021 (5)0.564 (3)0.038*
C2B0.2342 (4)0.8050 (4)0.5196 (2)0.0330 (7)
N2B0.2951 (5)0.8361 (4)0.4329 (2)0.0398 (7)
H21B0.309 (5)0.925 (5)0.414 (3)0.048*
H22B0.323 (5)0.768 (5)0.398 (3)0.048*
N3B0.2124 (4)0.6585 (3)0.54793 (17)0.0316 (6)
C4B0.1470 (4)0.6369 (4)0.6383 (2)0.0302 (6)
N4B0.1223 (4)0.4930 (3)0.6668 (2)0.0360 (6)
H41B0.090 (5)0.471 (5)0.722 (3)0.043*
H42B0.153 (5)0.421 (5)0.628 (3)0.043*
N5B0.1044 (4)0.7548 (3)0.70368 (17)0.0338 (6)
C6B0.1321 (4)0.8961 (4)0.6727 (2)0.0317 (7)
C61B0.0943 (5)1.0341 (4)0.7371 (2)0.0390 (7)
H61A0.03560.99740.79700.059*
H61B0.00851.08950.70050.059*
H61C0.21391.10630.75610.059*
O1W0.5689 (4)0.6740 (5)0.1317 (2)0.0703 (9)
H1W0.530 (6)0.654 (7)0.189 (2)0.105*
H2W0.679 (4)0.651 (7)0.126 (4)0.105*
C1X0.0839 (5)0.3389 (4)0.9020 (2)0.0434 (8)
H1X0.20270.34700.87050.052*
O1X0.0606 (4)0.3911 (3)0.86028 (17)0.0486 (6)
N2X0.0855 (4)0.2729 (4)0.98674 (19)0.0460 (7)
C3X0.2618 (6)0.2178 (6)1.0324 (3)0.0595 (11)
H3X10.36770.24870.99470.089*
H3X20.25470.26521.10120.089*
H3X30.28180.10241.03200.089*
C4X0.0891 (6)0.2543 (6)1.0402 (3)0.0616 (11)
H4X10.10700.14411.02980.092*
H4X20.08140.28271.11140.092*
H4X30.19640.32351.01540.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0405 (14)0.0257 (13)0.0287 (12)0.0091 (11)0.0022 (10)0.0011 (10)
C2A0.0359 (16)0.0307 (16)0.0264 (14)0.0094 (13)0.0001 (11)0.0030 (11)
O2A0.0485 (13)0.0313 (12)0.0262 (10)0.0096 (9)0.0067 (9)0.0040 (8)
N3A0.0420 (15)0.0265 (14)0.0248 (12)0.0096 (11)0.0045 (10)0.0002 (10)
C4A0.0340 (16)0.0298 (17)0.0311 (14)0.0054 (13)0.0028 (12)0.0010 (12)
O4A0.0586 (15)0.0286 (12)0.0371 (12)0.0103 (10)0.0139 (10)0.0046 (9)
C5A0.0364 (17)0.0328 (17)0.0277 (13)0.0051 (13)0.0050 (12)0.0009 (12)
C6A0.0345 (16)0.0291 (16)0.0294 (14)0.0058 (12)0.0008 (12)0.0024 (12)
Cl6A0.0503 (5)0.0328 (4)0.0358 (4)0.0084 (3)0.0089 (3)0.0064 (3)
N1B0.0430 (15)0.0228 (13)0.0293 (12)0.0097 (11)0.0034 (10)0.0006 (10)
C2B0.0411 (17)0.0328 (17)0.0260 (14)0.0108 (13)0.0006 (12)0.0011 (12)
N2B0.0652 (19)0.0268 (15)0.0300 (13)0.0122 (14)0.0136 (13)0.0036 (11)
N3B0.0426 (14)0.0281 (14)0.0250 (11)0.0081 (11)0.0046 (10)0.0028 (10)
C4B0.0352 (16)0.0301 (16)0.0257 (13)0.0083 (12)0.0003 (11)0.0016 (11)
N4B0.0497 (17)0.0335 (16)0.0255 (12)0.0079 (12)0.0069 (11)0.0040 (11)
N5B0.0416 (15)0.0350 (15)0.0248 (11)0.0085 (12)0.0015 (10)0.0010 (10)
C6B0.0364 (16)0.0321 (17)0.0264 (13)0.0082 (13)0.0016 (12)0.0014 (12)
C61B0.054 (2)0.0332 (17)0.0312 (15)0.0135 (15)0.0068 (14)0.0033 (12)
O1W0.0632 (19)0.103 (3)0.0505 (16)0.0207 (18)0.0112 (14)0.0241 (16)
C1X0.050 (2)0.051 (2)0.0298 (15)0.0111 (16)0.0046 (14)0.0007 (14)
O1X0.0525 (15)0.0624 (17)0.0344 (12)0.0153 (12)0.0090 (10)0.0122 (11)
N2X0.0500 (18)0.0576 (19)0.0305 (13)0.0080 (14)0.0074 (12)0.0052 (13)
C3X0.058 (2)0.079 (3)0.0396 (19)0.002 (2)0.0097 (17)0.0121 (19)
C4X0.058 (2)0.089 (3)0.0418 (19)0.018 (2)0.0038 (17)0.022 (2)
Geometric parameters (Å, º) top
N1A—C6A1.342 (4)N4B—H41B0.82 (4)
N1A—C2A1.352 (4)N4B—H42B0.84 (4)
C2A—O2A1.259 (3)N5B—C6B1.306 (4)
C2A—N3A1.368 (4)C6B—C61B1.487 (4)
N3A—C4A1.374 (4)C61B—H61A0.9800
N3A—H3A0.87 (4)C61B—H61B0.9800
C4A—O4A1.240 (4)C61B—H61C0.9800
C4A—C5A1.426 (4)O1W—H1W0.852 (10)
C5A—C6A1.346 (4)O1W—H2W0.855 (10)
C5A—H5A0.9500C1X—O1X1.237 (4)
C6A—Cl6A1.749 (3)C1X—N2X1.318 (4)
N1B—C6B1.354 (4)C1X—H1X0.9500
N1B—C2B1.366 (4)N2X—C4X1.455 (5)
N1B—H1B0.86 (4)N2X—C3X1.456 (5)
C2B—N2B1.301 (4)C3X—H3X10.9800
C2B—N3B1.335 (4)C3X—H3X20.9800
N2B—H21B0.81 (4)C3X—H3X30.9800
N2B—H22B0.78 (4)C4X—H4X10.9800
N3B—C4B1.343 (4)C4X—H4X20.9800
C4B—N4B1.314 (4)C4X—H4X30.9800
C4B—N5B1.376 (4)
C6A—N1A—C2A116.1 (3)H41B—N4B—H42B118 (4)
O2A—C2A—N1A121.3 (3)C6B—N5B—C4B115.4 (2)
O2A—C2A—N3A119.7 (3)N5B—C6B—N1B123.1 (3)
N1A—C2A—N3A119.0 (3)N5B—C6B—C61B120.6 (3)
C2A—N3A—C4A125.6 (3)N1B—C6B—C61B116.3 (3)
C2A—N3A—H3A119 (2)C6B—C61B—H61A109.5
C4A—N3A—H3A115 (2)C6B—C61B—H61B109.5
O4A—C4A—N3A120.2 (3)H61A—C61B—H61B109.5
O4A—C4A—C5A125.3 (3)C6B—C61B—H61C109.5
N3A—C4A—C5A114.5 (3)H61A—C61B—H61C109.5
C6A—C5A—C4A117.0 (3)H61B—C61B—H61C109.5
C6A—C5A—H5A121.5H1W—O1W—H2W110 (3)
C4A—C5A—H5A121.5O1X—C1X—N2X125.0 (3)
N1A—C6A—C5A127.9 (3)O1X—C1X—H1X117.5
N1A—C6A—Cl6A113.0 (2)N2X—C1X—H1X117.5
C5A—C6A—Cl6A119.1 (2)C1X—N2X—C4X121.6 (3)
C6B—N1B—C2B119.2 (3)C1X—N2X—C3X121.6 (3)
C6B—N1B—H1B121 (2)C4X—N2X—C3X116.8 (3)
C2B—N1B—H1B120 (2)N2X—C3X—H3X1109.5
N2B—C2B—N3B121.1 (3)N2X—C3X—H3X2109.5
N2B—C2B—N1B118.5 (3)H3X1—C3X—H3X2109.5
N3B—C2B—N1B120.5 (3)N2X—C3X—H3X3109.5
C2B—N2B—H21B123 (3)H3X1—C3X—H3X3109.5
C2B—N2B—H22B119 (3)H3X2—C3X—H3X3109.5
H21B—N2B—H22B118 (4)N2X—C4X—H4X1109.5
C2B—N3B—C4B117.0 (3)N2X—C4X—H4X2109.5
N4B—C4B—N3B117.8 (3)H4X1—C4X—H4X2109.5
N4B—C4B—N5B117.4 (3)N2X—C4X—H4X3109.5
N3B—C4B—N5B124.8 (3)H4X1—C4X—H4X3109.5
C4B—N4B—H41B124 (3)H4X2—C4X—H4X3109.5
C4B—N4B—H42B118 (3)
C6A—N1A—C2A—O2A178.3 (3)C6B—N1B—C2B—N3B1.2 (4)
C6A—N1A—C2A—N3A1.8 (4)N2B—C2B—N3B—C4B179.4 (3)
O2A—C2A—N3A—C4A177.6 (3)N1B—C2B—N3B—C4B1.8 (4)
N1A—C2A—N3A—C4A2.6 (4)C2B—N3B—C4B—N4B179.1 (3)
C2A—N3A—C4A—O4A177.7 (3)C2B—N3B—C4B—N5B1.1 (4)
C2A—N3A—C4A—C5A1.9 (4)N4B—C4B—N5B—C6B179.6 (3)
O4A—C4A—C5A—C6A178.9 (3)N3B—C4B—N5B—C6B0.2 (4)
N3A—C4A—C5A—C6A0.7 (4)C4B—N5B—C6B—N1B0.8 (4)
C2A—N1A—C6A—C5A0.7 (5)C4B—N5B—C6B—C61B179.0 (3)
C2A—N1A—C6A—Cl6A178.1 (2)C2B—N1B—C6B—N5B0.2 (5)
C4A—C5A—C6A—N1A0.2 (5)C2B—N1B—C6B—C61B179.7 (3)
C4A—C5A—C6A—Cl6A178.6 (2)O1X—C1X—N2X—C4X0.4 (6)
C6B—N1B—C2B—N2B179.9 (3)O1X—C1X—N2X—C3X178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···N3B0.87 (4)2.04 (4)2.906 (4)177 (3)
N1B—H1B···O2Ai0.86 (4)1.94 (4)2.803 (3)176 (3)
N2B—H21B···N1Ai0.81 (4)1.97 (4)2.781 (4)175 (4)
N2B—H22B···O4A0.78 (4)2.02 (4)2.802 (4)177 (4)
N4B—H41B···O1X0.82 (4)2.05 (4)2.852 (4)167 (4)
N4B—H42B···O2A0.84 (4)2.19 (4)3.031 (4)179 (3)
O1W—H1W···O4A0.85 (1)1.94 (2)2.779 (4)167 (5)
O1W—H2W···O1Xii0.86 (1)1.96 (2)2.807 (4)169 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1.
(Va) ; top
Crystal data top
C4H3ClN2O2·C3H4ClN5·C3H7NOZ = 2
Mr = 365.19F(000) = 376
Triclinic, P1Dx = 1.543 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4573 (10) ÅCell parameters from 11913 reflections
b = 9.3488 (10) Åθ = 3.4–26.3°
c = 10.8269 (11) ŵ = 0.44 mm1
α = 72.144 (8)°T = 173 K
β = 77.879 (9)°Plate, colourless
γ = 77.444 (9)°0.38 × 0.10 × 0.04 mm
V = 785.79 (15) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
3027 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2270 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.065
ω scansθmax = 25.9°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1010
Tmin = 0.849, Tmax = 0.983k = 1110
17138 measured reflectionsl = 1313
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0418P)2]
where P = (Fo2 + 2Fc2)/3
3027 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.45 e Å3
6 restraintsΔρmin = 0.18 e Å3
Crystal data top
C4H3ClN2O2·C3H4ClN5·C3H7NOγ = 77.444 (9)°
Mr = 365.19V = 785.79 (15) Å3
Triclinic, P1Z = 2
a = 8.4573 (10) ÅMo Kα radiation
b = 9.3488 (10) ŵ = 0.44 mm1
c = 10.8269 (11) ÅT = 173 K
α = 72.144 (8)°0.38 × 0.10 × 0.04 mm
β = 77.879 (9)°
Data collection top
STOE IPDS II two-circle
diffractometer
3027 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2270 reflections with I > 2σ(I)
Tmin = 0.849, Tmax = 0.983Rint = 0.065
17138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0386 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.45 e Å3
3027 reflectionsΔρmin = 0.18 e Å3
228 parameters
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
N3A0.2679 (2)0.4575 (2)0.56294 (16)0.0262 (4)
H3A0.312 (3)0.509 (3)0.597 (2)0.031*
C2A0.2306 (3)0.3210 (3)0.6430 (2)0.0279 (5)
O2A0.2557 (2)0.27378 (19)0.75712 (14)0.0359 (4)
N1A0.1619 (2)0.2407 (2)0.58756 (16)0.0281 (4)
H1A0.139 (3)0.150 (2)0.636 (2)0.034*
C6A0.1313 (2)0.2963 (3)0.46136 (19)0.0265 (5)
Cl6A0.04350 (7)0.18198 (7)0.40860 (5)0.03486 (16)
C5A0.1659 (3)0.4313 (3)0.3832 (2)0.0274 (5)
H5A0.14240.46610.29580.033*
C4A0.2394 (3)0.5228 (3)0.43389 (19)0.0262 (5)
O4A0.2749 (2)0.64760 (18)0.37309 (13)0.0332 (4)
N1B0.5019 (2)0.6631 (2)0.85823 (15)0.0255 (4)
C2B0.5252 (2)0.7981 (3)0.78126 (19)0.0258 (5)
Cl2B0.60189 (8)0.90762 (7)0.85200 (5)0.03968 (17)
N3B0.4988 (2)0.8646 (2)0.66009 (16)0.0243 (4)
C4B0.4341 (2)0.7766 (2)0.60976 (18)0.0234 (4)
N4B0.4060 (2)0.8327 (2)0.48765 (17)0.0287 (4)
H4B10.430 (3)0.920 (2)0.440 (2)0.034*
H4B20.365 (3)0.781 (3)0.452 (2)0.034*
N5B0.3993 (2)0.6372 (2)0.67718 (15)0.0239 (4)
C6B0.4350 (2)0.5850 (2)0.79993 (19)0.0235 (4)
N6B0.4042 (2)0.4484 (2)0.87209 (17)0.0297 (4)
H6B10.366 (3)0.391 (3)0.838 (2)0.036*
H6B20.431 (3)0.414 (3)0.9517 (18)0.036*
C1X0.1418 (3)0.0607 (3)0.8601 (2)0.0331 (5)
H1X0.20440.00670.87030.040*
O1X0.0903 (2)0.02903 (19)0.75371 (14)0.0365 (4)
N2X0.1159 (2)0.1815 (2)0.96019 (17)0.0331 (4)
C3X0.1854 (3)0.2139 (3)1.0795 (2)0.0468 (7)
H3X10.24300.13121.07370.070*
H3X20.26270.31001.09030.070*
H3X30.09730.22241.15510.070*
C4X0.0232 (3)0.2910 (3)0.9521 (2)0.0453 (6)
H4X10.01850.25570.86810.068*
H4X20.06900.30131.02450.068*
H4X30.09450.38990.95830.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N3A0.0361 (10)0.0259 (10)0.0216 (8)0.0125 (8)0.0097 (7)0.0050 (7)
C2A0.0324 (11)0.0288 (12)0.0247 (10)0.0129 (9)0.0055 (8)0.0043 (9)
O2A0.0538 (10)0.0385 (10)0.0204 (7)0.0228 (8)0.0120 (7)0.0004 (7)
N1A0.0385 (11)0.0265 (11)0.0218 (8)0.0157 (9)0.0069 (7)0.0017 (7)
C6A0.0288 (11)0.0328 (13)0.0223 (10)0.0079 (9)0.0062 (8)0.0104 (9)
Cl6A0.0477 (3)0.0345 (3)0.0314 (3)0.0186 (3)0.0119 (2)0.0099 (2)
C5A0.0364 (11)0.0271 (13)0.0219 (10)0.0069 (9)0.0092 (8)0.0068 (9)
C4A0.0315 (11)0.0284 (12)0.0200 (9)0.0072 (9)0.0067 (8)0.0051 (8)
O4A0.0521 (10)0.0256 (9)0.0246 (7)0.0154 (7)0.0133 (7)0.0003 (6)
N1B0.0343 (10)0.0270 (10)0.0180 (8)0.0114 (8)0.0082 (7)0.0028 (7)
C2B0.0296 (11)0.0279 (12)0.0243 (10)0.0086 (9)0.0062 (8)0.0095 (9)
Cl2B0.0608 (4)0.0371 (4)0.0317 (3)0.0213 (3)0.0181 (3)0.0082 (2)
N3B0.0322 (9)0.0219 (10)0.0207 (8)0.0081 (7)0.0081 (7)0.0033 (7)
C4B0.0256 (11)0.0243 (11)0.0213 (9)0.0052 (9)0.0066 (8)0.0051 (8)
N4B0.0457 (11)0.0234 (10)0.0207 (8)0.0163 (8)0.0146 (8)0.0023 (7)
N5B0.0305 (9)0.0234 (10)0.0187 (8)0.0080 (7)0.0076 (7)0.0020 (7)
C6B0.0244 (10)0.0252 (12)0.0205 (9)0.0057 (9)0.0043 (8)0.0040 (8)
N6B0.0452 (11)0.0270 (11)0.0204 (8)0.0150 (9)0.0127 (7)0.0001 (8)
C1X0.0370 (13)0.0312 (13)0.0331 (12)0.0092 (10)0.0072 (9)0.0078 (10)
O1X0.0470 (10)0.0343 (10)0.0293 (8)0.0144 (8)0.0112 (7)0.0016 (7)
N2X0.0380 (11)0.0320 (11)0.0281 (9)0.0076 (9)0.0073 (8)0.0036 (8)
C3X0.0499 (15)0.0548 (18)0.0300 (12)0.0027 (13)0.0137 (11)0.0026 (11)
C4X0.0560 (16)0.0398 (16)0.0391 (13)0.0190 (13)0.0046 (11)0.0033 (11)
Geometric parameters (Å, º) top
N3A—C2A1.364 (3)C4B—N5B1.346 (3)
N3A—C4A1.392 (3)N4B—H4B10.868 (17)
N3A—H3A0.869 (16)N4B—H4B20.865 (17)
C2A—O2A1.225 (3)N5B—C6B1.342 (3)
C2A—N1A1.369 (3)C6B—N6B1.326 (3)
N1A—C6A1.363 (3)N6B—H6B10.885 (17)
N1A—H1A0.892 (17)N6B—H6B20.883 (16)
C6A—C5A1.340 (3)C1X—O1X1.245 (3)
C6A—Cl6A1.708 (2)C1X—N2X1.325 (3)
C5A—C4A1.443 (3)C1X—H1X0.9500
C5A—H5A0.9500N2X—C4X1.450 (3)
C4A—O4A1.218 (3)N2X—C3X1.452 (3)
N1B—C2B1.311 (3)C3X—H3X10.9800
N1B—C6B1.365 (3)C3X—H3X20.9800
C2B—N3B1.311 (3)C3X—H3X30.9800
C2B—Cl2B1.742 (2)C4X—H4X10.9800
N3B—C4B1.367 (3)C4X—H4X20.9800
C4B—N4B1.316 (3)C4X—H4X30.9800
C2A—N3A—C4A126.62 (18)C4B—N4B—H4B2120.1 (17)
C2A—N3A—H3A116.3 (16)H4B1—N4B—H4B2118 (2)
C4A—N3A—H3A117.0 (16)C6B—N5B—C4B115.78 (18)
O2A—C2A—N3A122.4 (2)N6B—C6B—N5B119.10 (19)
O2A—C2A—N1A122.2 (2)N6B—C6B—N1B116.20 (17)
N3A—C2A—N1A115.43 (18)N5B—C6B—N1B124.69 (19)
C6A—N1A—C2A121.52 (19)C6B—N6B—H6B1120.0 (17)
C6A—N1A—H1A120.5 (16)C6B—N6B—H6B2118.1 (17)
C2A—N1A—H1A118.0 (16)H6B1—N6B—H6B2122 (2)
C5A—C6A—N1A123.08 (19)O1X—C1X—N2X124.9 (2)
C5A—C6A—Cl6A121.64 (16)O1X—C1X—H1X117.6
N1A—C6A—Cl6A115.28 (17)N2X—C1X—H1X117.6
C6A—C5A—C4A118.94 (19)C1X—N2X—C4X121.0 (2)
C6A—C5A—H5A120.5C1X—N2X—C3X121.7 (2)
C4A—C5A—H5A120.5C4X—N2X—C3X117.2 (2)
O4A—C4A—N3A120.54 (19)N2X—C3X—H3X1109.5
O4A—C4A—C5A125.06 (18)N2X—C3X—H3X2109.5
N3A—C4A—C5A114.40 (19)H3X1—C3X—H3X2109.5
C2B—N1B—C6B112.24 (16)N2X—C3X—H3X3109.5
N3B—C2B—N1B130.55 (19)H3X1—C3X—H3X3109.5
N3B—C2B—Cl2B114.70 (16)H3X2—C3X—H3X3109.5
N1B—C2B—Cl2B114.74 (14)N2X—C4X—H4X1109.5
C2B—N3B—C4B112.79 (17)N2X—C4X—H4X2109.5
N4B—C4B—N5B118.78 (18)H4X1—C4X—H4X2109.5
N4B—C4B—N3B117.29 (19)N2X—C4X—H4X3109.5
N5B—C4B—N3B123.92 (17)H4X1—C4X—H4X3109.5
C4B—N4B—H4B1121.8 (16)H4X2—C4X—H4X3109.5
C4A—N3A—C2A—O2A177.8 (2)C6B—N1B—C2B—Cl2B177.26 (15)
C4A—N3A—C2A—N1A1.6 (3)N1B—C2B—N3B—C4B1.2 (3)
O2A—C2A—N1A—C6A178.5 (2)Cl2B—C2B—N3B—C4B178.15 (15)
N3A—C2A—N1A—C6A0.9 (3)C2B—N3B—C4B—N4B178.85 (19)
C2A—N1A—C6A—C5A0.1 (3)C2B—N3B—C4B—N5B0.6 (3)
C2A—N1A—C6A—Cl6A179.43 (16)N4B—C4B—N5B—C6B178.27 (19)
N1A—C6A—C5A—C4A0.2 (3)N3B—C4B—N5B—C6B1.2 (3)
Cl6A—C6A—C5A—C4A179.70 (17)C4B—N5B—C6B—N6B179.89 (18)
C2A—N3A—C4A—O4A178.3 (2)C4B—N5B—C6B—N1B0.2 (3)
C2A—N3A—C4A—C5A1.4 (3)C2B—N1B—C6B—N6B178.67 (19)
C6A—C5A—C4A—O4A179.3 (2)C2B—N1B—C6B—N5B1.3 (3)
C6A—C5A—C4A—N3A0.4 (3)O1X—C1X—N2X—C4X0.7 (4)
C6B—N1B—C2B—N3B2.1 (3)O1X—C1X—N2X—C3X177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1X0.89 (2)1.83 (2)2.718 (2)173 (2)
N3A—H3A···N5B0.87 (2)2.01 (2)2.873 (2)176 (2)
N4B—H4B1···N3Bi0.87 (2)2.12 (2)2.981 (3)174 (2)
N4B—H4B2···O4A0.87 (2)2.05 (2)2.914 (2)177 (2)
N6B—H6B1···O2A0.89 (2)2.05 (2)2.930 (3)174 (2)
N6B—H6B2···N1Bii0.88 (2)2.12 (2)2.998 (2)179 (2)
C1X—H1X···O2A0.952.513.267 (3)137
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+2.
(Vb) ; top
Crystal data top
C4H3ClN2O2·C3H4ClN5·C3H7NOZ = 4
Mr = 365.19F(000) = 752
Triclinic, P1Dx = 1.556 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.9691 (7) ÅCell parameters from 49386 reflections
b = 12.3455 (7) Åθ = 3.3–26.2°
c = 12.4618 (7) ŵ = 0.45 mm1
α = 109.385 (4)°T = 173 K
β = 96.199 (5)°Block, colourless
γ = 111.598 (4)°0.33 × 0.23 × 0.12 mm
V = 1558.46 (15) Å3
Data collection top
STOE IPDS II two-circle
diffractometer
6006 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source5104 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.113
ω scansθmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1414
Tmin = 0.867, Tmax = 0.949k = 1515
43838 measured reflectionsl = 1515
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0884P)2 + 0.2231P]
where P = (Fo2 + 2Fc2)/3
6006 reflections(Δ/σ)max = 0.001
455 parametersΔρmax = 0.53 e Å3
12 restraintsΔρmin = 0.55 e Å3
Crystal data top
C4H3ClN2O2·C3H4ClN5·C3H7NOγ = 111.598 (4)°
Mr = 365.19V = 1558.46 (15) Å3
Triclinic, P1Z = 4
a = 11.9691 (7) ÅMo Kα radiation
b = 12.3455 (7) ŵ = 0.45 mm1
c = 12.4618 (7) ÅT = 173 K
α = 109.385 (4)°0.33 × 0.23 × 0.12 mm
β = 96.199 (5)°
Data collection top
STOE IPDS II two-circle
diffractometer
6006 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
5104 reflections with I > 2σ(I)
Tmin = 0.867, Tmax = 0.949Rint = 0.113
43838 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05012 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.53 e Å3
6006 reflectionsΔρmin = 0.55 e Å3
455 parameters
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
N1A1.10387 (17)0.71445 (18)0.01328 (16)0.0332 (4)
H1A1.0418 (17)0.731 (2)0.006 (2)0.040*
C2A1.0893 (2)0.6518 (2)0.08711 (18)0.0322 (5)
O2A0.99504 (14)0.62269 (17)0.12223 (14)0.0393 (4)
N3A1.18501 (16)0.62431 (18)0.11771 (16)0.0319 (4)
H3A1.178 (2)0.588 (2)0.167 (2)0.038*
C4A1.2915 (2)0.6491 (2)0.07770 (19)0.0337 (5)
O4A1.37070 (15)0.61858 (18)0.11124 (15)0.0434 (4)
C5A1.2991 (2)0.7135 (2)0.00107 (19)0.0340 (5)
H5A1.36890.73440.03280.041*
C6A1.2065 (2)0.7431 (2)0.02845 (18)0.0321 (4)
Cl6A1.20924 (5)0.82486 (6)0.11633 (5)0.03922 (16)
N1B1.03171 (16)0.39213 (18)0.37766 (15)0.0311 (4)
C2B1.12287 (19)0.3634 (2)0.40395 (17)0.0288 (4)
Cl2B1.09762 (5)0.27155 (5)0.48701 (5)0.03683 (16)
N3B1.23014 (16)0.39184 (18)0.37696 (15)0.0306 (4)
C4B1.24436 (18)0.4624 (2)0.31082 (17)0.0284 (4)
N4B1.35034 (17)0.4953 (2)0.27861 (16)0.0336 (4)
H41B1.405 (2)0.469 (2)0.300 (2)0.040*
H42B1.359 (2)0.540 (2)0.236 (2)0.040*
N5B1.16003 (16)0.50033 (17)0.27749 (15)0.0298 (4)
C6B1.05566 (18)0.4642 (2)0.31321 (17)0.0287 (4)
N6B0.96892 (17)0.4990 (2)0.28446 (17)0.0346 (4)
H61B0.9022 (16)0.469 (2)0.308 (2)0.042*
H62B0.977 (2)0.544 (2)0.243 (2)0.042*
N1C0.44441 (18)0.06150 (19)0.70656 (17)0.0367 (4)
H1C0.3725 (18)0.040 (3)0.724 (2)0.044*
C2C0.4598 (2)0.1297 (2)0.6364 (2)0.0366 (5)
O2C0.38156 (15)0.16306 (19)0.60756 (16)0.0466 (4)
N3C0.56785 (17)0.15543 (19)0.60167 (16)0.0351 (4)
H3C0.576 (2)0.198 (2)0.557 (2)0.042*
C4C0.6608 (2)0.1208 (2)0.62992 (19)0.0345 (5)
O4C0.75319 (16)0.14906 (18)0.59262 (16)0.0450 (4)
C5C0.6387 (2)0.0516 (2)0.7046 (2)0.0362 (5)
H5C0.69770.02410.72870.043*
C6C0.5335 (2)0.0269 (2)0.73910 (19)0.0344 (5)
Cl6C0.50222 (6)0.05056 (6)0.83176 (5)0.04304 (17)
N1D0.52898 (16)0.39743 (18)0.34964 (15)0.0316 (4)
C2D0.63648 (19)0.4272 (2)0.32350 (17)0.0300 (4)
Cl2D0.66167 (5)0.52286 (6)0.24403 (5)0.04027 (17)
N3D0.72737 (16)0.39691 (17)0.34702 (15)0.0309 (4)
C4D0.70355 (18)0.3238 (2)0.41140 (17)0.0283 (4)
N4D0.78999 (17)0.28810 (19)0.43875 (16)0.0329 (4)
H41D0.8587 (15)0.318 (2)0.418 (2)0.039*
H42D0.780 (2)0.246 (2)0.4840 (19)0.039*
N5D0.59895 (15)0.28691 (17)0.44660 (15)0.0293 (4)
C6D0.51435 (19)0.3249 (2)0.41448 (18)0.0298 (4)
N6D0.40816 (17)0.2905 (2)0.44504 (18)0.0376 (4)
H61D0.357 (2)0.322 (2)0.429 (2)0.045*
H62D0.400 (2)0.252 (2)0.4942 (19)0.045*
C1X0.8254 (2)0.7195 (2)0.0061 (2)0.0375 (5)
H1X0.83050.66270.02830.045*
O1X0.91428 (14)0.76902 (17)0.04360 (15)0.0429 (4)
N2X0.72423 (18)0.73971 (19)0.01031 (17)0.0384 (4)
C3X0.7081 (3)0.8212 (3)0.0654 (2)0.0500 (6)
H3X10.78410.86130.08730.075*
H3X20.69110.88720.00990.075*
H3X30.63800.77030.13610.075*
C4X0.6234 (2)0.6752 (3)0.0321 (3)0.0519 (6)
H4X10.64250.61650.05920.078*
H4X20.54640.62750.03170.078*
H4X30.61270.73800.09780.078*
C1Y0.1566 (2)0.0425 (2)0.7171 (2)0.0438 (6)
H1Y0.18920.08540.66890.053*
O1Y0.22262 (16)0.00372 (18)0.76253 (15)0.0458 (4)
N2Y0.04442 (19)0.0293 (2)0.72996 (18)0.0418 (5)
C3Y0.0267 (3)0.0768 (3)0.6730 (3)0.0629 (8)
H3Y10.02370.12380.63230.094*
H3Y20.04990.13370.73230.094*
H3Y30.10210.00530.61570.094*
C4Y0.0136 (3)0.0392 (3)0.7995 (2)0.0498 (6)
H4Y10.03600.08110.81950.075*
H4Y20.09790.10340.75350.075*
H4Y30.01760.02080.87200.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0338 (9)0.0421 (10)0.0362 (9)0.0193 (8)0.0134 (8)0.0259 (8)
C2A0.0361 (11)0.0364 (12)0.0302 (10)0.0167 (9)0.0111 (8)0.0186 (9)
O2A0.0362 (8)0.0571 (10)0.0445 (9)0.0244 (7)0.0190 (7)0.0360 (8)
N3A0.0332 (9)0.0417 (10)0.0324 (9)0.0179 (8)0.0123 (7)0.0254 (8)
C4A0.0353 (11)0.0381 (12)0.0332 (11)0.0164 (9)0.0121 (9)0.0190 (9)
O4A0.0399 (9)0.0640 (11)0.0522 (10)0.0312 (8)0.0227 (7)0.0402 (9)
C5A0.0336 (10)0.0423 (12)0.0345 (11)0.0178 (9)0.0153 (9)0.0218 (10)
C6A0.0381 (11)0.0343 (11)0.0278 (10)0.0140 (9)0.0106 (8)0.0184 (9)
Cl6A0.0444 (3)0.0474 (3)0.0395 (3)0.0207 (2)0.0164 (2)0.0307 (3)
N1B0.0314 (9)0.0392 (10)0.0304 (9)0.0166 (8)0.0103 (7)0.0207 (8)
C2B0.0337 (10)0.0324 (11)0.0245 (9)0.0145 (8)0.0082 (8)0.0158 (8)
Cl2B0.0426 (3)0.0442 (3)0.0360 (3)0.0202 (2)0.0137 (2)0.0279 (2)
N3B0.0321 (9)0.0383 (10)0.0281 (8)0.0177 (8)0.0093 (7)0.0180 (8)
C4B0.0295 (10)0.0339 (11)0.0250 (9)0.0153 (8)0.0081 (8)0.0134 (8)
N4B0.0326 (9)0.0495 (11)0.0353 (9)0.0231 (8)0.0154 (7)0.0280 (9)
N5B0.0308 (8)0.0379 (10)0.0294 (9)0.0176 (7)0.0114 (7)0.0195 (8)
C6B0.0296 (9)0.0349 (11)0.0261 (9)0.0148 (8)0.0090 (8)0.0158 (8)
N6B0.0319 (9)0.0490 (11)0.0405 (10)0.0220 (8)0.0163 (8)0.0313 (9)
N1C0.0362 (10)0.0455 (11)0.0400 (10)0.0187 (9)0.0149 (8)0.0281 (9)
C2C0.0372 (11)0.0415 (13)0.0397 (12)0.0176 (10)0.0140 (9)0.0243 (10)
O2C0.0428 (9)0.0658 (12)0.0600 (11)0.0311 (9)0.0246 (8)0.0468 (10)
N3C0.0379 (10)0.0446 (11)0.0377 (10)0.0213 (8)0.0158 (8)0.0280 (9)
C4C0.0365 (11)0.0404 (12)0.0344 (11)0.0189 (9)0.0120 (9)0.0208 (10)
O4C0.0440 (9)0.0638 (11)0.0544 (10)0.0313 (8)0.0255 (8)0.0422 (9)
C5C0.0377 (11)0.0427 (13)0.0372 (11)0.0191 (10)0.0110 (9)0.0243 (10)
C6C0.0409 (11)0.0345 (11)0.0295 (10)0.0140 (9)0.0065 (9)0.0184 (9)
Cl6C0.0489 (3)0.0493 (4)0.0402 (3)0.0179 (3)0.0136 (2)0.0317 (3)
N1D0.0323 (9)0.0396 (10)0.0325 (9)0.0185 (8)0.0107 (7)0.0214 (8)
C2D0.0342 (10)0.0361 (11)0.0251 (9)0.0156 (9)0.0083 (8)0.0178 (9)
Cl2D0.0419 (3)0.0536 (4)0.0414 (3)0.0223 (3)0.0139 (2)0.0349 (3)
N3D0.0336 (9)0.0383 (10)0.0281 (9)0.0168 (8)0.0113 (7)0.0195 (8)
C4D0.0312 (10)0.0316 (10)0.0250 (9)0.0137 (8)0.0081 (8)0.0144 (8)
N4D0.0307 (9)0.0449 (11)0.0382 (10)0.0204 (8)0.0161 (7)0.0276 (9)
N5D0.0297 (8)0.0368 (10)0.0290 (8)0.0162 (7)0.0101 (7)0.0190 (8)
C6D0.0311 (10)0.0348 (11)0.0282 (10)0.0146 (8)0.0091 (8)0.0171 (9)
N6D0.0337 (9)0.0522 (12)0.0482 (11)0.0252 (9)0.0183 (8)0.0351 (10)
C1X0.0407 (12)0.0425 (13)0.0346 (11)0.0199 (10)0.0094 (9)0.0195 (10)
O1X0.0386 (9)0.0548 (11)0.0475 (9)0.0247 (8)0.0153 (7)0.0284 (8)
N2X0.0379 (10)0.0442 (11)0.0371 (10)0.0188 (8)0.0090 (8)0.0202 (9)
C3X0.0495 (14)0.0599 (17)0.0538 (15)0.0308 (13)0.0114 (12)0.0307 (13)
C4X0.0409 (13)0.0606 (17)0.0547 (15)0.0184 (12)0.0147 (11)0.0271 (14)
C1Y0.0470 (13)0.0489 (14)0.0438 (13)0.0206 (11)0.0170 (10)0.0267 (11)
O1Y0.0440 (9)0.0601 (11)0.0495 (10)0.0256 (8)0.0191 (8)0.0351 (9)
N2Y0.0455 (11)0.0456 (11)0.0432 (11)0.0219 (9)0.0148 (9)0.0249 (9)
C3Y0.0655 (18)0.075 (2)0.074 (2)0.0434 (16)0.0224 (15)0.0444 (17)
C4Y0.0507 (14)0.0561 (16)0.0471 (14)0.0202 (12)0.0227 (12)0.0263 (13)
Geometric parameters (Å, º) top
N1A—C6A1.358 (3)C6C—Cl6C1.718 (2)
N1A—C2A1.372 (3)N1D—C2D1.311 (3)
N1A—H1A0.872 (10)N1D—C6D1.372 (3)
C2A—O2A1.227 (3)C2D—N3D1.309 (3)
C2A—N3A1.361 (3)C2D—Cl2D1.745 (2)
N3A—C4A1.385 (3)N3D—C4D1.371 (3)
N3A—H3A0.869 (17)C4D—N4D1.319 (3)
C4A—O4A1.224 (3)C4D—N5D1.341 (3)
C4A—C5A1.445 (3)N4D—H41D0.873 (10)
C5A—C6A1.333 (3)N4D—H42D0.877 (10)
C5A—H5A0.9500N5D—C6D1.338 (3)
C6A—Cl6A1.714 (2)C6D—N6D1.325 (3)
N1B—C2B1.307 (3)N6D—H61D0.874 (10)
N1B—C6B1.362 (3)N6D—H62D0.885 (10)
C2B—N3B1.313 (3)C1X—O1X1.242 (3)
C2B—Cl2B1.745 (2)C1X—N2X1.323 (3)
N3B—C4B1.365 (3)C1X—H1X0.9500
C4B—N4B1.332 (3)N2X—C4X1.442 (3)
C4B—N5B1.341 (3)N2X—C3X1.447 (3)
N4B—H41B0.879 (10)C3X—H3X10.9800
N4B—H42B0.878 (10)C3X—H3X20.9800
N5B—C6B1.341 (3)C3X—H3X30.9800
C6B—N6B1.319 (3)C4X—H4X10.9800
N6B—H61B0.878 (10)C4X—H4X20.9800
N6B—H62B0.872 (10)C4X—H4X30.9800
N1C—C6C1.357 (3)C1Y—O1Y1.240 (3)
N1C—C2C1.384 (3)C1Y—N2Y1.326 (3)
N1C—H1C0.876 (17)C1Y—H1Y0.9500
C2C—O2C1.219 (3)N2Y—C3Y1.445 (3)
C2C—N3C1.367 (3)N2Y—C4Y1.460 (3)
N3C—C4C1.383 (3)C3Y—H3Y10.9800
N3C—H3C0.883 (17)C3Y—H3Y20.9800
C4C—O4C1.223 (3)C3Y—H3Y30.9800
C4C—C5C1.442 (3)C4Y—H4Y10.9800
C5C—C6C1.336 (3)C4Y—H4Y20.9800
C5C—H5C0.9500C4Y—H4Y30.9800
C6A—N1A—C2A121.27 (18)C2D—N1D—C6D112.34 (17)
C6A—N1A—H1A123.6 (18)N3D—C2D—N1D130.68 (19)
C2A—N1A—H1A115.1 (18)N3D—C2D—Cl2D115.04 (15)
O2A—C2A—N3A122.84 (19)N1D—C2D—Cl2D114.29 (15)
O2A—C2A—N1A121.37 (19)C2D—N3D—C4D112.50 (18)
N3A—C2A—N1A115.79 (18)N4D—C4D—N5D119.15 (18)
C2A—N3A—C4A126.10 (18)N4D—C4D—N3D116.75 (18)
C2A—N3A—H3A116.2 (17)N5D—C4D—N3D124.10 (18)
C4A—N3A—H3A117.7 (17)C4D—N4D—H41D116.7 (17)
O4A—C4A—N3A119.82 (19)C4D—N4D—H42D118.9 (17)
O4A—C4A—C5A125.4 (2)H41D—N4D—H42D124 (2)
N3A—C4A—C5A114.73 (18)C6D—N5D—C4D116.11 (18)
C6A—C5A—C4A118.93 (19)N6D—C6D—N5D119.33 (19)
C6A—C5A—H5A120.5N6D—C6D—N1D116.42 (18)
C4A—C5A—H5A120.5N5D—C6D—N1D124.25 (18)
C5A—C6A—N1A123.13 (19)C6D—N6D—H61D118.2 (19)
C5A—C6A—Cl6A122.60 (17)C6D—N6D—H62D118.2 (18)
N1A—C6A—Cl6A114.24 (16)H61D—N6D—H62D122 (3)
C2B—N1B—C6B112.89 (17)O1X—C1X—N2X124.9 (2)
N1B—C2B—N3B130.28 (19)O1X—C1X—H1X117.5
N1B—C2B—Cl2B114.93 (15)N2X—C1X—H1X117.5
N3B—C2B—Cl2B114.79 (15)C1X—N2X—C4X121.5 (2)
C2B—N3B—C4B112.33 (17)C1X—N2X—C3X120.5 (2)
N4B—C4B—N5B118.77 (18)C4X—N2X—C3X117.9 (2)
N4B—C4B—N3B116.66 (18)N2X—C3X—H3X1109.5
N5B—C4B—N3B124.57 (18)N2X—C3X—H3X2109.5
C4B—N4B—H41B118.4 (18)H3X1—C3X—H3X2109.5
C4B—N4B—H42B116.7 (17)N2X—C3X—H3X3109.5
H41B—N4B—H42B125 (2)H3X1—C3X—H3X3109.5
C4B—N5B—C6B115.66 (17)H3X2—C3X—H3X3109.5
N6B—C6B—N5B119.02 (19)N2X—C4X—H4X1109.5
N6B—C6B—N1B116.73 (18)N2X—C4X—H4X2109.5
N5B—C6B—N1B124.26 (18)H4X1—C4X—H4X2109.5
C6B—N6B—H61B113.4 (18)N2X—C4X—H4X3109.5
C6B—N6B—H62B122.1 (18)H4X1—C4X—H4X3109.5
H61B—N6B—H62B124 (3)H4X2—C4X—H4X3109.5
C6C—N1C—C2C120.84 (19)O1Y—C1Y—N2Y125.6 (2)
C6C—N1C—H1C124.4 (18)O1Y—C1Y—H1Y117.2
C2C—N1C—H1C114.7 (18)N2Y—C1Y—H1Y117.2
O2C—C2C—N3C123.0 (2)C1Y—N2Y—C3Y122.0 (2)
O2C—C2C—N1C121.8 (2)C1Y—N2Y—C4Y120.4 (2)
N3C—C2C—N1C115.21 (19)C3Y—N2Y—C4Y117.6 (2)
C2C—N3C—C4C126.65 (19)N2Y—C3Y—H3Y1109.5
C2C—N3C—H3C114.0 (17)N2Y—C3Y—H3Y2109.5
C4C—N3C—H3C119.3 (17)H3Y1—C3Y—H3Y2109.5
O4C—C4C—N3C120.4 (2)N2Y—C3Y—H3Y3109.5
O4C—C4C—C5C124.8 (2)H3Y1—C3Y—H3Y3109.5
N3C—C4C—C5C114.83 (19)H3Y2—C3Y—H3Y3109.5
C6C—C5C—C4C118.6 (2)N2Y—C4Y—H4Y1109.5
C6C—C5C—H5C120.7N2Y—C4Y—H4Y2109.5
C4C—C5C—H5C120.7H4Y1—C4Y—H4Y2109.5
C5C—C6C—N1C123.8 (2)N2Y—C4Y—H4Y3109.5
C5C—C6C—Cl6C121.58 (17)H4Y1—C4Y—H4Y3109.5
N1C—C6C—Cl6C114.57 (16)H4Y2—C4Y—H4Y3109.5
C6A—N1A—C2A—O2A177.9 (2)O2C—C2C—N3C—C4C179.7 (2)
C6A—N1A—C2A—N3A1.8 (3)N1C—C2C—N3C—C4C0.3 (3)
O2A—C2A—N3A—C4A177.0 (2)C2C—N3C—C4C—O4C179.6 (2)
N1A—C2A—N3A—C4A2.7 (3)C2C—N3C—C4C—C5C0.6 (3)
C2A—N3A—C4A—O4A179.4 (2)O4C—C4C—C5C—C6C180.0 (2)
C2A—N3A—C4A—C5A1.8 (3)N3C—C4C—C5C—C6C0.2 (3)
O4A—C4A—C5A—C6A178.8 (2)C4C—C5C—C6C—N1C1.1 (4)
N3A—C4A—C5A—C6A0.0 (3)C4C—C5C—C6C—Cl6C177.92 (17)
C4A—C5A—C6A—N1A0.7 (3)C2C—N1C—C6C—C5C2.0 (4)
C4A—C5A—C6A—Cl6A177.37 (17)C2C—N1C—C6C—Cl6C177.05 (17)
C2A—N1A—C6A—C5A0.2 (3)C6D—N1D—C2D—N3D1.6 (3)
C2A—N1A—C6A—Cl6A178.45 (16)C6D—N1D—C2D—Cl2D178.51 (15)
C6B—N1B—C2B—N3B0.9 (3)N1D—C2D—N3D—C4D1.2 (3)
C6B—N1B—C2B—Cl2B179.78 (14)Cl2D—C2D—N3D—C4D178.84 (14)
N1B—C2B—N3B—C4B0.1 (3)C2D—N3D—C4D—N4D179.65 (18)
Cl2B—C2B—N3B—C4B179.25 (14)C2D—N3D—C4D—N5D0.1 (3)
C2B—N3B—C4B—N4B179.67 (19)N4D—C4D—N5D—C6D179.07 (19)
C2B—N3B—C4B—N5B0.7 (3)N3D—C4D—N5D—C6D0.5 (3)
N4B—C4B—N5B—C6B179.81 (19)C4D—N5D—C6D—N6D179.19 (19)
N3B—C4B—N5B—C6B0.2 (3)C4D—N5D—C6D—N1D0.1 (3)
C4B—N5B—C6B—N6B179.48 (19)C2D—N1D—C6D—N6D179.90 (19)
C4B—N5B—C6B—N1B1.0 (3)C2D—N1D—C6D—N5D0.8 (3)
C2B—N1B—C6B—N6B179.02 (19)O1X—C1X—N2X—C4X178.1 (2)
C2B—N1B—C6B—N5B1.4 (3)O1X—C1X—N2X—C3X2.3 (4)
C6C—N1C—C2C—O2C179.0 (2)O1Y—C1Y—N2Y—C3Y179.6 (3)
C6C—N1C—C2C—N3C1.5 (3)O1Y—C1Y—N2Y—C4Y2.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1X0.87 (1)1.81 (1)2.683 (2)179 (3)
N3A—H3A···N5B0.87 (2)2.00 (2)2.866 (2)179 (2)
N4B—H41B···N1Di0.88 (1)2.13 (1)3.003 (3)177 (2)
N4B—H42B···O4A0.88 (1)2.07 (1)2.944 (2)171 (2)
N6B—H61B···N3D0.88 (1)2.13 (1)3.002 (3)172 (2)
N6B—H62B···O2A0.87 (1)2.03 (1)2.890 (2)170 (2)
N1C—H1C···O1Y0.88 (2)1.84 (2)2.716 (3)177 (3)
N3C—H3C···N5D0.88 (2)2.00 (2)2.881 (3)176 (2)
N6D—H61D···N3Bii0.87 (1)2.14 (1)3.017 (3)176 (3)
N6D—H62D···O2C0.89 (1)2.04 (1)2.927 (2)180 (3)
N4D—H41D···N1B0.87 (1)2.13 (1)2.998 (3)177 (2)
N4D—H42D···O4C0.88 (1)2.06 (1)2.937 (2)178 (2)
C1X—H1X···O2A0.952.473.234 (3)138
C1Y—H1Y···O2C0.952.463.244 (3)140
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(VI) ; top
Crystal data top
C5H5ClN2O2F(000) = 328
Mr = 160.56Dx = 1.690 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5122 reflections
a = 4.4135 (6) Åθ = 3.4–25.9°
b = 15.780 (3) ŵ = 0.53 mm1
c = 9.0645 (14) ÅT = 173 K
β = 92.025 (12)°Plate, colourless
V = 630.91 (17) Å30.11 × 0.09 × 0.08 mm
Z = 4
Data collection top
STOE IPDS II two-circle
diffractometer
1179 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source970 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.044
ω scansθmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 55
Tmin = 0.943, Tmax = 0.959k = 1919
4810 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.1541P]
where P = (Fo2 + 2Fc2)/3
1179 reflections(Δ/σ)max < 0.001
96 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C5H5ClN2O2V = 630.91 (17) Å3
Mr = 160.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.4135 (6) ŵ = 0.53 mm1
b = 15.780 (3) ÅT = 173 K
c = 9.0645 (14) Å0.11 × 0.09 × 0.08 mm
β = 92.025 (12)°
Data collection top
STOE IPDS II two-circle
diffractometer
1179 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
970 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.959Rint = 0.044
4810 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.19 e Å3
1179 reflectionsΔρmin = 0.20 e Å3
96 parameters
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
N10.0809 (3)0.26316 (10)0.53362 (17)0.0228 (3)
H10.050 (6)0.2800 (17)0.467 (3)0.039 (6)*
C20.1005 (4)0.17687 (11)0.54497 (19)0.0214 (4)
O20.0581 (3)0.13002 (9)0.46897 (15)0.0295 (3)
N30.3132 (3)0.14704 (9)0.64970 (16)0.0211 (3)
C30.3435 (5)0.05577 (12)0.6677 (2)0.0291 (4)
H3A0.54760.03830.64130.044*
H3B0.19310.02700.60330.044*
H3C0.31030.04050.77070.044*
C40.4967 (4)0.19943 (12)0.7379 (2)0.0209 (4)
O40.6823 (3)0.16599 (9)0.82585 (15)0.0286 (3)
C50.4570 (4)0.28859 (12)0.72132 (18)0.0224 (4)
H50.57330.32730.78030.027*
C60.2515 (4)0.31643 (11)0.62035 (19)0.0223 (4)
Cl60.18286 (12)0.42189 (3)0.59132 (5)0.03316 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0215 (8)0.0250 (8)0.0214 (7)0.0002 (6)0.0074 (6)0.0007 (6)
C20.0199 (9)0.0255 (10)0.0186 (9)0.0014 (7)0.0022 (7)0.0003 (7)
O20.0312 (7)0.0280 (7)0.0283 (7)0.0068 (6)0.0128 (6)0.0000 (6)
N30.0207 (8)0.0212 (8)0.0210 (8)0.0002 (6)0.0044 (6)0.0011 (6)
C30.0365 (11)0.0198 (9)0.0304 (10)0.0011 (8)0.0084 (8)0.0001 (7)
C40.0186 (8)0.0265 (9)0.0173 (8)0.0003 (7)0.0015 (6)0.0017 (7)
O40.0280 (7)0.0298 (7)0.0270 (7)0.0033 (6)0.0129 (6)0.0012 (6)
C50.0213 (9)0.0251 (9)0.0204 (9)0.0007 (7)0.0036 (7)0.0036 (7)
C60.0229 (10)0.0222 (9)0.0217 (9)0.0004 (7)0.0000 (7)0.0003 (7)
Cl60.0425 (3)0.0208 (2)0.0352 (3)0.0037 (2)0.0119 (2)0.00035 (19)
Geometric parameters (Å, º) top
N1—C61.360 (2)C3—H3B0.9800
N1—C21.368 (2)C3—H3C0.9800
N1—H10.86 (3)C4—O41.241 (2)
C2—O21.215 (2)C4—C51.425 (3)
C2—N31.393 (2)C5—C61.340 (2)
N3—C41.390 (2)C5—H50.9500
N3—C31.455 (2)C6—Cl61.7103 (19)
C3—H3A0.9800
C6—N1—C2122.65 (16)N3—C3—H3C109.5
C6—N1—H1123.9 (18)H3A—C3—H3C109.5
C2—N1—H1113.4 (18)H3B—C3—H3C109.5
O2—C2—N1121.96 (17)O4—C4—N3118.33 (17)
O2—C2—N3122.77 (17)O4—C4—C5124.30 (17)
N1—C2—N3115.27 (15)N3—C4—C5117.37 (16)
C4—N3—C2123.75 (16)C6—C5—C4118.26 (16)
C4—N3—C3118.34 (15)C6—C5—H5120.9
C2—N3—C3117.91 (15)C4—C5—H5120.9
N3—C3—H3A109.5C5—C6—N1122.67 (17)
N3—C3—H3B109.5C5—C6—Cl6122.42 (14)
H3A—C3—H3B109.5N1—C6—Cl6114.91 (13)
C6—N1—C2—O2178.34 (18)C2—N3—C4—C51.5 (3)
C6—N1—C2—N31.4 (3)C3—N3—C4—C5178.26 (16)
O2—C2—N3—C4179.92 (18)O4—C4—C5—C6178.94 (19)
N1—C2—N3—C40.2 (3)N3—C4—C5—C61.4 (3)
O2—C2—N3—C30.1 (3)C4—C5—C6—N10.1 (3)
N1—C2—N3—C3179.62 (16)C4—C5—C6—Cl6179.65 (14)
C2—N3—C4—O4178.75 (16)C2—N1—C6—C51.6 (3)
C3—N3—C4—O41.5 (3)C2—N1—C6—Cl6178.18 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.86 (3)1.91 (3)2.767 (2)171 (3)
C5—H5···O2ii0.952.413.306 (2)156
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2.
(VII) top
Crystal data top
C5H5ClN2O2·2(C3H6N6)·C4H9NO·C2H7N·3(HCl)F(000) = 1368
Mr = 654.42Dx = 1.480 Mg m3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yCell parameters from 29644 reflections
a = 18.6341 (15) Åθ = 3.4–26.3°
b = 13.0507 (10) ŵ = 0.46 mm1
c = 12.3166 (10) ÅT = 173 K
β = 101.365 (7)°Plate, colourless
V = 2936.5 (4) Å30.15 × 0.14 × 0.07 mm
Z = 4
Data collection top
STOE IPDS II two-circle-
diffractometer
2960 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source2332 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromatorRint = 0.056
ω scansθmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 2222
Tmin = 0.935, Tmax = 0.969k = 1515
25210 measured reflectionsl = 1515
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0738P)2 + 7.4826P]
where P = (Fo2 + 2Fc2)/3
2960 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.34 e Å3
25 restraintsΔρmin = 0.62 e Å3
Crystal data top
C5H5ClN2O2·2(C3H6N6)·C4H9NO·C2H7N·3(HCl)V = 2936.5 (4) Å3
Mr = 654.42Z = 4
Monoclinic, C2/mMo Kα radiation
a = 18.6341 (15) ŵ = 0.46 mm1
b = 13.0507 (10) ÅT = 173 K
c = 12.3166 (10) Å0.15 × 0.14 × 0.07 mm
β = 101.365 (7)°
Data collection top
STOE IPDS II two-circle-
diffractometer
2960 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2332 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.969Rint = 0.056
25210 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06725 restraints
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.34 e Å3
2960 reflectionsΔρmin = 0.62 e Å3
250 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)
N1A0.2794 (3)0.00000.0591 (4)0.0497 (13)
H1A0.291 (4)0.00000.126 (3)0.060*
C2A0.2082 (3)0.00000.0565 (5)0.0428 (14)
O2A0.1602 (2)0.00000.1410 (4)0.0648 (14)
N3A0.1896 (3)0.00000.0481 (4)0.0435 (12)
C3A0.1114 (3)0.00000.0516 (5)0.0484 (15)
H3A10.08400.03450.01440.073*0.50
H3A20.09420.07080.05360.073*0.50
H3A30.10380.03630.11810.073*0.50
C4A0.2410 (3)0.00000.1459 (5)0.0455 (15)
O4A0.2202 (2)0.00000.2347 (3)0.0565 (12)
C5A0.3166 (3)0.00000.1360 (5)0.0535 (17)
H5A0.35460.00000.20000.064*
C6A0.3322 (4)0.00000.0361 (6)0.0594 (19)
Cl6A0.42010 (10)0.00000.0147 (2)0.0930 (8)
N1B0.23525 (18)0.2494 (3)0.8426 (3)0.0448 (9)
C2B0.2018 (2)0.2539 (3)0.7342 (3)0.0407 (10)
N2B0.12996 (19)0.2587 (3)0.7133 (3)0.0488 (10)
H2B10.103 (2)0.250 (4)0.763 (3)0.059*
H2B20.106 (2)0.259 (4)0.645 (2)0.059*
N3B0.23541 (17)0.2543 (3)0.6472 (3)0.0360 (7)
C4B0.3076 (2)0.2531 (3)0.6710 (3)0.0353 (9)
N4B0.34571 (19)0.2542 (3)0.5913 (3)0.0401 (8)
H4B10.3940 (11)0.251 (4)0.604 (4)0.048*
H4B20.320 (2)0.253 (3)0.524 (2)0.048*
N5B0.34509 (18)0.2511 (3)0.7776 (3)0.0394 (8)
H5B0.3927 (11)0.257 (3)0.790 (4)0.047*
C6B0.3076 (2)0.2488 (3)0.8611 (3)0.0422 (10)
N6B0.3454 (2)0.2465 (3)0.9644 (3)0.0513 (11)
H6B10.3914 (13)0.252 (4)0.965 (4)0.062*
H6B20.323 (3)0.251 (4)1.021 (3)0.062*
Cl1C0.49320 (5)0.29003 (8)1.15072 (7)0.0399 (3)
Cl1D0.00000.24959 (11)0.50000.0393 (4)
C1E0.4320 (4)0.50001.3603 (5)0.0516 (16)
H1E10.38150.50001.31850.077*
H1E20.44040.56131.40700.077*0.50
H1E30.44040.43871.40700.077*0.50
N2E0.4833 (3)0.50001.2819 (4)0.0443 (12)
H2E10.474 (2)0.448 (3)1.236 (3)0.053*
C3E0.5599 (3)0.50001.3414 (5)0.0479 (15)
H3E10.59250.50001.28780.072*
H3E20.56920.43871.38800.072*0.50
H3E30.56920.56131.38800.072*0.50
C2X0.3534 (7)0.00000.3328 (8)0.046 (4)0.626 (19)
N3X0.3273 (5)0.00000.4391 (7)0.040 (3)0.626 (19)
C2X'0.3129 (7)0.00000.3732 (11)0.034 (5)0.374 (19)
N3X'0.3783 (7)0.00000.4019 (9)0.039 (5)0.374 (19)
C1X0.4389 (5)0.00000.3022 (8)0.084 (3)
H1X10.45870.00000.37020.126*0.626 (19)
H1X20.45570.06130.25870.126*0.313 (9)
H1X30.45570.06130.25870.126*0.313 (9)
H4XA0.48610.00000.32580.126*0.374 (19)
H4XB0.43510.06130.25780.126*0.187 (9)
H4XC0.43510.06130.25780.126*0.187 (9)
O2X0.3105 (3)0.00000.2688 (4)0.0646 (14)
C4X0.2471 (3)0.00000.4732 (5)0.0476 (15)
H4X10.23360.00000.55420.071*0.626 (19)
H4X20.22710.06130.44400.071*0.313 (9)
H4X30.22710.06130.44400.071*0.313 (9)
H1XA0.26540.00000.54250.071*0.374 (19)
H1XB0.21720.06130.47000.071*0.187 (9)
H1XC0.21720.06130.47000.071*0.187 (9)
C5X0.3786 (4)0.00000.5218 (5)0.0601 (19)
H5X10.34960.00000.59740.090*0.626 (19)
H5X20.40950.06130.51050.090*0.313 (9)
H5X30.40950.06130.51050.090*0.313 (9)
H5XA0.42920.00000.53300.090*0.374 (19)
H5XB0.35330.06130.55600.090*0.187 (9)
H5XC0.35330.06130.55600.090*0.187 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.045 (3)0.067 (4)0.036 (3)0.0000.006 (2)0.000
C2A0.040 (3)0.047 (4)0.038 (3)0.0000.002 (2)0.000
O2A0.046 (3)0.097 (4)0.048 (3)0.0000.000 (2)0.000
N3A0.041 (3)0.049 (3)0.040 (3)0.0000.008 (2)0.000
C3A0.039 (3)0.062 (4)0.045 (3)0.0000.010 (3)0.000
C4A0.051 (4)0.048 (4)0.037 (3)0.0000.008 (3)0.000
O4A0.056 (3)0.080 (4)0.034 (2)0.0000.009 (2)0.000
C5A0.040 (3)0.078 (5)0.039 (3)0.0000.001 (3)0.000
C6A0.037 (3)0.079 (5)0.059 (4)0.0000.001 (3)0.000
Cl6A0.0386 (10)0.156 (3)0.0842 (15)0.0000.0117 (9)0.000
N1B0.0450 (19)0.053 (2)0.0284 (16)0.0272 (17)0.0117 (14)0.0168 (15)
C2B0.045 (2)0.039 (2)0.032 (2)0.0195 (18)0.0103 (16)0.0122 (16)
N2B0.0408 (19)0.074 (3)0.0258 (16)0.0241 (18)0.0080 (14)0.0149 (17)
N3B0.0380 (17)0.0332 (18)0.0310 (16)0.0099 (14)0.0074 (13)0.0070 (13)
C4B0.044 (2)0.0216 (18)0.0339 (19)0.0089 (16)0.0083 (16)0.0074 (15)
N4B0.0368 (17)0.0364 (19)0.0409 (19)0.0012 (15)0.0072 (15)0.0019 (15)
N5B0.0360 (17)0.0343 (19)0.0399 (18)0.0118 (15)0.0124 (14)0.0074 (14)
C6B0.047 (2)0.035 (2)0.037 (2)0.0242 (18)0.0124 (18)0.0155 (17)
N6B0.049 (2)0.059 (2)0.0354 (18)0.0272 (19)0.0166 (16)0.0186 (18)
Cl1C0.0323 (5)0.0509 (6)0.0321 (5)0.0078 (4)0.0042 (3)0.0039 (4)
Cl1D0.0380 (7)0.0437 (8)0.0295 (6)0.0000.0093 (5)0.000
C1E0.050 (4)0.059 (4)0.045 (3)0.0000.009 (3)0.000
N2E0.050 (3)0.045 (3)0.033 (3)0.0000.003 (2)0.000
C3E0.040 (3)0.060 (4)0.041 (3)0.0000.002 (3)0.000
C2X0.073 (9)0.026 (6)0.035 (6)0.0000.002 (6)0.000
N3X0.062 (7)0.029 (4)0.029 (5)0.0000.007 (4)0.000
C2X'0.057 (11)0.019 (8)0.024 (11)0.0000.004 (8)0.000
N3X'0.040 (9)0.030 (8)0.042 (10)0.0000.008 (7)0.000
C1X0.073 (5)0.064 (6)0.096 (6)0.0000.027 (5)0.000
O2X0.091 (4)0.069 (4)0.038 (2)0.0000.022 (3)0.000
C4X0.057 (4)0.042 (4)0.043 (3)0.0000.008 (3)0.000
C5X0.092 (6)0.047 (4)0.048 (4)0.0000.030 (4)0.000
Geometric parameters (Å, º) top
N1A—C2A1.332 (8)C1E—H1E30.9800
N1A—C6A1.375 (8)N2E—C3E1.471 (8)
N1A—H1A0.89 (2)N2E—H2E10.877 (19)
C2A—O2A1.231 (7)C3E—H3E10.9800
C2A—N3A1.399 (7)C3E—H3E20.9800
N3A—C4A1.384 (8)C3E—H3E30.9800
N3A—C3A1.466 (7)C2X—O2X1.227 (11)
C3A—H3A10.9800C2X—N3X1.304 (12)
C3A—H3A20.9800C2X—C1X1.563 (15)
C3A—H3A30.9800N3X—C4X1.470 (10)
C4A—O4A1.230 (7)N3X—C5X1.528 (10)
C4A—C5A1.438 (9)C2X'—O2X1.295 (13)
C5A—C6A1.319 (9)C2X'—N3X'1.334 (16)
C5A—H5A0.9500C2X'—C4X1.558 (13)
C6A—Cl6A1.709 (7)N3X'—C5X1.478 (12)
N1B—C6B1.322 (5)N3X'—C1X1.495 (12)
N1B—C2B1.359 (5)C1X—H1X10.9800
C2B—N2B1.314 (6)C1X—H1X20.9800
C2B—N3B1.344 (5)C1X—H1X30.9800
N2B—H2B10.882 (19)C1X—H4XA0.9800
N2B—H2B20.87 (2)C1X—H4XB0.9800
N3B—C4B1.320 (5)C1X—H4XC0.9800
C4B—N4B1.319 (5)C4X—H4X10.9800
C4B—N5B1.361 (5)C4X—H4X20.9800
N4B—H4B10.884 (19)C4X—H4X30.9800
N4B—H4B20.874 (19)C4X—H1XA0.9800
N5B—C6B1.352 (6)C4X—H1XB0.9800
N5B—H5B0.874 (19)C4X—H1XC0.9800
C6B—N6B1.327 (5)C5X—H5X10.9800
N6B—H6B10.86 (2)C5X—H5X20.9800
N6B—H6B20.879 (19)C5X—H5X30.9800
C1E—N2E1.486 (8)C5X—H5XA0.9800
C1E—H1E10.9800C5X—H5XB0.9800
C1E—H1E20.9800C5X—H5XC0.9800
C2A—N1A—C6A121.9 (5)C2X—C1X—H1X1109.5
C2A—N1A—H1A116 (5)N3X'—C1X—H1X2123.9
C6A—N1A—H1A122 (5)C2X—C1X—H1X2109.5
O2A—C2A—N1A122.7 (6)H1X1—C1X—H1X2109.5
O2A—C2A—N3A120.5 (5)N3X'—C1X—H1X3123.9
N1A—C2A—N3A116.8 (5)C2X—C1X—H1X3109.5
C4A—N3A—C2A123.2 (5)H1X1—C1X—H1X3109.5
C4A—N3A—C3A119.7 (5)H1X2—C1X—H1X3109.5
C2A—N3A—C3A117.1 (5)N3X'—C1X—H4XA109.5
N3A—C3A—H3A1109.5C2X—C1X—H4XA149.5
N3A—C3A—H3A2109.5H1X2—C1X—H4XA87.3
H3A1—C3A—H3A2109.5H1X3—C1X—H4XA87.3
N3A—C3A—H3A3109.5N3X'—C1X—H4XB109.5
H3A1—C3A—H3A3109.5C2X—C1X—H4XB87.3
H3A2—C3A—H3A3109.5H1X1—C1X—H4XB123.9
O4A—C4A—N3A119.2 (6)H1X3—C1X—H4XB114.3
O4A—C4A—C5A124.2 (6)H4XA—C1X—H4XB109.5
N3A—C4A—C5A116.6 (5)N3X'—C1X—H4XC109.5
C6A—C5A—C4A118.6 (6)C2X—C1X—H4XC87.3
C6A—C5A—H5A120.7H1X1—C1X—H4XC123.9
C4A—C5A—H5A120.7H1X2—C1X—H4XC114.3
C5A—C6A—N1A122.9 (6)H4XA—C1X—H4XC109.5
C5A—C6A—Cl6A122.5 (5)H4XB—C1X—H4XC109.5
N1A—C6A—Cl6A114.6 (5)N3X—C4X—H4X1109.5
C6B—N1B—C2B115.1 (4)C2X'—C4X—H4X1144.0
N2B—C2B—N3B117.4 (3)N3X—C4X—H4X2109.5
N2B—C2B—N1B116.6 (4)C2X'—C4X—H4X290.4
N3B—C2B—N1B126.0 (4)H4X1—C4X—H4X2109.5
C2B—N2B—H2B1124 (3)N3X—C4X—H4X3109.5
C2B—N2B—H2B2120 (3)C2X'—C4X—H4X390.4
H2B1—N2B—H2B2115 (5)H4X1—C4X—H4X3109.5
C4B—N3B—C2B116.0 (3)H4X2—C4X—H4X3109.5
N4B—C4B—N3B120.6 (3)N3X—C4X—H1XA74.9
N4B—C4B—N5B118.0 (4)C2X'—C4X—H1XA109.5
N3B—C4B—N5B121.4 (4)H4X2—C4X—H1XA122.8
C4B—N4B—H4B1123 (3)H4X3—C4X—H1XA122.8
C4B—N4B—H4B2115 (3)N3X—C4X—H1XB122.8
H4B1—N4B—H4B2122 (4)C2X'—C4X—H1XB109.5
C6B—N5B—C4B119.4 (3)H4X1—C4X—H1XB90.4
C6B—N5B—H5B122 (3)H4X3—C4X—H1XB113.1
C4B—N5B—H5B118 (3)H1XA—C4X—H1XB109.5
N1B—C6B—N6B119.7 (4)N3X—C4X—H1XC122.8
N1B—C6B—N5B122.1 (3)C2X'—C4X—H1XC109.5
N6B—C6B—N5B118.2 (4)H4X1—C4X—H1XC90.4
C6B—N6B—H6B1111 (4)H4X2—C4X—H1XC113.1
C6B—N6B—H6B2121 (4)H1XA—C4X—H1XC109.5
H6B1—N6B—H6B2128 (5)H1XB—C4X—H1XC109.5
N2E—C1E—H1E1109.5N3X'—C5X—H5X1147.1
N2E—C1E—H1E2109.5N3X—C5X—H5X1109.5
H1E1—C1E—H1E2109.5N3X'—C5X—H5X288.6
N2E—C1E—H1E3109.5N3X—C5X—H5X2109.5
H1E1—C1E—H1E3109.5H5X1—C5X—H5X2109.5
H1E2—C1E—H1E3109.5N3X'—C5X—H5X388.6
C3E—N2E—C1E111.2 (5)N3X—C5X—H5X3109.5
C3E—N2E—H2E1111 (3)H5X1—C5X—H5X3109.5
C1E—N2E—H2E1111 (3)H5X2—C5X—H5X3109.5
N2E—C3E—H3E1109.5N3X'—C5X—H5XA109.5
N2E—C3E—H3E2109.5N3X—C5X—H5XA147.1
H3E1—C3E—H3E2109.5H5X1—C5X—H5XA103.4
N2E—C3E—H3E3109.5H5X2—C5X—H5XA57.6
H3E1—C3E—H3E3109.5H5X3—C5X—H5XA57.6
H3E2—C3E—H3E3109.5N3X'—C5X—H5XB109.5
O2X—C2X—N3X118.9 (11)N3X—C5X—H5XB88.6
O2X—C2X—C1X127.4 (9)H5X1—C5X—H5XB57.6
N3X—C2X—C1X113.7 (9)H5X2—C5X—H5XB161.2
C2X—N3X—C4X116.3 (9)H5X3—C5X—H5XB67.2
C2X—N3X—C5X120.7 (9)H5XA—C5X—H5XB109.5
C4X—N3X—C5X122.9 (7)N3X'—C5X—H5XC109.5
O2X—C2X'—N3X'118.4 (12)N3X—C5X—H5XC88.6
O2X—C2X'—C4X127.5 (10)H5X1—C5X—H5XC57.6
N3X'—C2X'—C4X114.1 (11)H5X2—C5X—H5XC67.2
C2X'—N3X'—C5X116.6 (11)H5X3—C5X—H5XC161.2
C2X'—N3X'—C1X111.3 (11)H5XA—C5X—H5XC109.5
C5X—N3X'—C1X132.1 (10)H5XB—C5X—H5XC109.5
N3X'—C1X—H1X169.5
C6A—N1A—C2A—O2A180.0C4B—N5B—C6B—N1B0.6 (6)
C6A—N1A—C2A—N3A0.0C4B—N5B—C6B—N6B179.7 (4)
O2A—C2A—N3A—C4A180.0O2X—C2X—N3X—C4X0.000 (1)
N1A—C2A—N3A—C4A0.0C1X—C2X—N3X—C4X180.0
O2A—C2A—N3A—C3A0.0O2X—C2X—N3X—C5X180.000 (1)
N1A—C2A—N3A—C3A180.0C1X—C2X—N3X—C5X0.000 (1)
C2A—N3A—C4A—O4A180.0O2X—C2X'—N3X'—C5X180.000 (1)
C3A—N3A—C4A—O4A0.0C4X—C2X'—N3X'—C5X0.000 (2)
C2A—N3A—C4A—C5A0.0O2X—C2X'—N3X'—C1X0.000 (2)
C3A—N3A—C4A—C5A180.0C4X—C2X'—N3X'—C1X180.000 (2)
O4A—C4A—C5A—C6A180.0C2X'—N3X'—C1X—C2X0.000 (2)
N3A—C4A—C5A—C6A0.0C5X—N3X'—C1X—C2X180.000 (2)
C4A—C5A—C6A—N1A0.0O2X—C2X—C1X—N3X'180.000 (2)
C4A—C5A—C6A—Cl6A180.0N3X—C2X—C1X—N3X'0.000 (2)
C2A—N1A—C6A—C5A0.0N3X—C2X—O2X—C2X'0.000 (3)
C2A—N1A—C6A—Cl6A180.0C1X—C2X—O2X—C2X'180.000 (2)
C6B—N1B—C2B—N2B177.4 (4)N3X'—C2X'—O2X—C2X0.000 (3)
C6B—N1B—C2B—N3B2.3 (6)C4X—C2X'—O2X—C2X180.000 (2)
N2B—C2B—N3B—C4B177.6 (4)C2X—N3X—C4X—C2X'0.000 (2)
N1B—C2B—N3B—C4B2.0 (6)C5X—N3X—C4X—C2X'180.000 (2)
C2B—N3B—C4B—N4B179.4 (4)O2X—C2X'—C4X—N3X180.000 (2)
C2B—N3B—C4B—N5B0.3 (6)N3X'—C2X'—C4X—N3X0.000 (2)
N4B—C4B—N5B—C6B179.3 (4)C2X'—N3X'—C5X—N3X0.000 (2)
N3B—C4B—N5B—C6B0.9 (6)C1X—N3X'—C5X—N3X180.000 (2)
C2B—N1B—C6B—N6B178.8 (4)C2X—N3X—C5X—N3X'0.000 (2)
C2B—N1B—C6B—N5B0.9 (6)C4X—N3X—C5X—N3X'180.000 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2X0.89 (2)1.87 (2)2.757 (7)178 (7)
N2B—H2B1···Cl1Ci0.88 (2)2.31 (2)3.161 (4)163 (5)
N2B—H2B2···Cl1D0.87 (2)2.39 (3)3.205 (3)156 (4)
N4B—H4B1···Cl1Dii0.88 (2)2.56 (3)3.288 (4)140 (4)
N4B—H4B2···N3Bii0.87 (2)2.16 (2)3.029 (5)175 (4)
N5B—H5B···Cl1Ciii0.87 (2)2.15 (2)3.012 (3)168 (4)
N6B—H6B1···Cl1C0.86 (2)2.71 (5)3.269 (3)124 (4)
N6B—H6B1···Cl1Ciii0.86 (2)2.85 (3)3.614 (4)149 (5)
N6B—H6B2···N1Bi0.88 (2)2.18 (2)3.053 (6)175 (5)
N2E—H2E1···Cl1C0.88 (2)2.37 (3)3.205 (3)158 (4)
Symmetry codes: (i) x+1/2, y+1/2, z+2; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y, z+2.

Experimental details

(I)(II)(III)(IV)(Va)
Crystal data
Chemical formulaC4H3ClN2O2·C4H7N5·2(C5H9NO)·H2OC3H6N6·2(C5H9NO)·H2OC4H3ClN2O2·C4H7N5·C4H9NOC4H3ClN2O2·C4H7N5·C3H7NO·H2OC4H3ClN2O2·C3H4ClN5·C3H7NO
Mr487.96342.42358.80362.79365.19
Crystal system, space groupTriclinic, P1Monoclinic, P21/nTriclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)173173173173173
a, b, c (Å)9.4450 (6), 10.3974 (7), 13.3661 (8)7.6291 (4), 21.0118 (8), 10.9690 (6)6.9970 (5), 8.6140 (5), 13.8513 (9)7.1719 (11), 8.6197 (11), 13.5029 (19)8.4573 (10), 9.3488 (10), 10.8269 (11)
α, β, γ (°)77.188 (5), 89.846 (5), 67.043 (5)90, 98.950 (4), 9085.725 (5), 84.516 (5), 75.572 (5)94.574 (11), 92.707 (12), 99.840 (11)72.144 (8), 77.879 (9), 77.444 (9)
V3)1173.40 (13)1736.93 (15)803.70 (9)818.3 (2)785.79 (15)
Z24222
Radiation typeMo KαMo KαMo KαMo KαMo Kα
µ (mm1)0.210.100.270.270.44
Crystal size (mm)0.63 × 0.18 × 0.130.32 × 0.20 × 0.070.44 × 0.31 × 0.050.16 × 0.14 × 0.110.38 × 0.10 × 0.04
Data collection
DiffractometerSTOE IPDS II two-circle
diffractometer
STOE IPDS II two-circle
diffractometer
STOE 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)
Multi-scan
X-AREA (Stoe & Cie, 2001)
Multi-scan
X-AREA (Stoe & Cie, 2001)
Tmin, Tmax0.879, 0.9720.970, 0.9930.890, 0.9860.958, 0.9720.849, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
23834, 4521, 3965 50506, 3394, 2914 27171, 3103, 2815 13964, 3149, 2270 17138, 3027, 2270
Rint0.0500.0580.0450.1170.065
(sin θ/λ)max1)0.6140.6160.6140.6140.615
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.084, 0.244, 1.13 0.044, 0.118, 1.10 0.038, 0.104, 1.16 0.062, 0.169, 1.05 0.038, 0.083, 0.98
No. of reflections45213394310331493027
No. of parameters350243239244228
No. of restraints1023036
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.27, 0.530.18, 0.180.28, 0.240.32, 0.420.45, 0.18


(Vb)(VI)(VII)
Crystal data
Chemical formulaC4H3ClN2O2·C3H4ClN5·C3H7NOC5H5ClN2O2C5H5ClN2O2·2(C3H6N6)·C4H9NO·C2H7N·3(HCl)
Mr365.19160.56654.42
Crystal system, space groupTriclinic, P1Monoclinic, P21/cMonoclinic, C2/m
Temperature (K)173173173
a, b, c (Å)11.9691 (7), 12.3455 (7), 12.4618 (7)4.4135 (6), 15.780 (3), 9.0645 (14)18.6341 (15), 13.0507 (10), 12.3166 (10)
α, β, γ (°)109.385 (4), 96.199 (5), 111.598 (4)90, 92.025 (12), 9090, 101.365 (7), 90
V3)1558.46 (15)630.91 (17)2936.5 (4)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.450.530.46
Crystal size (mm)0.33 × 0.23 × 0.120.11 × 0.09 × 0.080.15 × 0.14 × 0.07
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, Tmax0.867, 0.9490.943, 0.9590.935, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
43838, 6006, 5104 4810, 1179, 970 25210, 2960, 2332
Rint0.1130.0440.056
(sin θ/λ)max1)0.6140.6070.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.139, 1.06 0.032, 0.072, 1.03 0.067, 0.174, 1.17
No. of reflections600611792960
No. of parameters45596250
No. of restraints12025
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)0.53, 0.550.19, 0.200.34, 0.62

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Version 3.1, Macrae et al., 2008) and XP (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O2Ai0.869 (19)2.02 (2)2.884 (4)178 (5)
N2B—H21B···O4Ai0.88 (2)2.08 (4)2.796 (5)138 (5)
N2B—H22B···N1Bii0.88 (2)2.13 (2)3.008 (5)175 (5)
N3B—H3B···O2A0.80 (5)2.17 (5)2.964 (4)177 (5)
N4B—H41B···N1A0.860 (19)2.01 (2)2.857 (5)166 (4)
N4B—H42B···O1W0.865 (19)1.96 (2)2.815 (5)168 (5)
N6B—H61B···O4Aiii0.870 (19)2.05 (2)2.898 (5)165 (4)
N6B—H62B···O2X0.853 (19)2.038 (19)2.887 (6)173 (4)
O1W—H1W···O2Y0.837 (10)2.08 (6)2.701 (6)131 (7)
O1W—H2W···O4Aiv0.838 (10)2.12 (3)2.903 (6)156 (6)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x, y, z1; (iv) x, y, z+2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H21···N5i0.89 (2)2.18 (2)3.060 (2)176.1 (18)
N2—H22···O1W0.84 (2)2.30 (2)2.9268 (19)131.4 (18)
N4—H41···N1ii0.89 (2)2.06 (2)2.938 (2)169.6 (19)
N4—H42···O2Yii0.88 (2)2.08 (2)2.8126 (19)140.6 (19)
N6—H61···O1Wii0.91 (2)2.15 (2)3.048 (2)169.3 (18)
N6—H62···O2Y0.87 (2)2.13 (2)2.992 (2)168.9 (19)
O1W—H1W1···O2X0.850 (9)1.951 (11)2.7926 (17)171 (2)
O1W—H1W2···O2Xiii0.852 (9)2.041 (10)2.886 (2)171 (2)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···N3B0.88 (2)2.04 (2)2.917 (2)174 (2)
N1B—H1B···O2Ai0.89 (2)1.89 (2)2.7779 (19)174 (2)
N2B—H2B1···O4A0.87 (3)1.92 (3)2.780 (2)175 (2)
N2B—H2B2···N1Ai0.89 (3)1.92 (3)2.805 (2)176 (2)
N4B—H4B1···O2X0.87 (2)2.02 (3)2.850 (2)161 (2)
N4B—H4B2···O2A0.88 (2)2.21 (2)3.088 (2)173 (2)
Symmetry code: (i) x, y1, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···N3B0.87 (4)2.04 (4)2.906 (4)177 (3)
N1B—H1B···O2Ai0.86 (4)1.94 (4)2.803 (3)176 (3)
N2B—H21B···N1Ai0.81 (4)1.97 (4)2.781 (4)175 (4)
N2B—H22B···O4A0.78 (4)2.02 (4)2.802 (4)177 (4)
N4B—H41B···O1X0.82 (4)2.05 (4)2.852 (4)167 (4)
N4B—H42B···O2A0.84 (4)2.19 (4)3.031 (4)179 (3)
O1W—H1W···O4A0.852 (10)1.943 (15)2.779 (4)167 (5)
O1W—H2W···O1Xii0.855 (10)1.963 (15)2.807 (4)169 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (Va) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1X0.892 (17)1.831 (17)2.718 (2)173 (2)
N3A—H3A···N5B0.869 (16)2.005 (17)2.873 (2)176 (2)
N4B—H4B1···N3Bi0.868 (17)2.117 (17)2.981 (3)174 (2)
N4B—H4B2···O4A0.865 (17)2.049 (17)2.914 (2)177 (2)
N6B—H6B1···O2A0.885 (17)2.048 (17)2.930 (3)174 (2)
N6B—H6B2···N1Bii0.883 (16)2.115 (17)2.998 (2)179 (2)
C1X—H1X···O2A0.952.513.267 (3)136.8
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) for (Vb) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1X0.872 (10)1.811 (10)2.683 (2)179 (3)
N3A—H3A···N5B0.869 (17)1.997 (17)2.866 (2)179 (2)
N4B—H41B···N1Di0.879 (10)2.125 (10)3.003 (3)177 (2)
N4B—H42B···O4A0.878 (10)2.074 (11)2.944 (2)171 (2)
N6B—H61B···N3D0.878 (10)2.129 (11)3.002 (3)172 (2)
N6B—H62B···O2A0.872 (10)2.027 (11)2.890 (2)170 (2)
N1C—H1C···O1Y0.876 (17)1.841 (17)2.716 (3)177 (3)
N3C—H3C···N5D0.883 (17)1.999 (18)2.881 (3)176 (2)
N6D—H61D···N3Bii0.874 (10)2.144 (11)3.017 (3)176 (3)
N6D—H62D···O2C0.885 (10)2.042 (10)2.927 (2)180 (3)
N4D—H41D···N1B0.873 (10)2.126 (10)2.998 (3)177 (2)
N4D—H42D···O4C0.877 (10)2.061 (10)2.937 (2)178 (2)
C1X—H1X···O2A0.952.473.234 (3)137.5
C1Y—H1Y···O2C0.952.463.244 (3)139.8
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (VI) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.86 (3)1.91 (3)2.767 (2)171 (3)
C5—H5···O2ii0.952.413.306 (2)156.2
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (VII) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2X0.89 (2)1.87 (2)2.757 (7)178 (7)
N2B—H2B1···Cl1Ci0.882 (19)2.31 (2)3.161 (4)163 (5)
N2B—H2B2···Cl1D0.87 (2)2.39 (3)3.205 (3)156 (4)
N4B—H4B1···Cl1Dii0.884 (19)2.56 (3)3.288 (4)140 (4)
N4B—H4B2···N3Bii0.874 (19)2.16 (2)3.029 (5)175 (4)
N5B—H5B···Cl1Ciii0.874 (19)2.15 (2)3.012 (3)168 (4)
N6B—H6B1···Cl1C0.86 (2)2.71 (5)3.269 (3)124 (4)
N6B—H6B1···Cl1Ciii0.86 (2)2.85 (3)3.614 (4)149 (5)
N6B—H6B2···N1Bi0.879 (19)2.18 (2)3.053 (6)175 (5)
N2E—H2E1···Cl1C0.877 (19)2.37 (3)3.205 (3)158 (4)
Symmetry codes: (i) x+1/2, y+1/2, z+2; (ii) x+1/2, y+1/2, z+1; (iii) x+1, y, z+2.
Isothermal solvent evaporation experiments of 6-chlorouracil and 6-chloro-3-methyluracil top
crystal no.compound 1 [mg; mmol]compound 2 [mg; mmol]solvent [µL]temperature [°C; K]
I6CU [1.0; 0.007]TAP [1.0; 0.008]NMP [80]23; 296
II6CU [1.0; 0.007]TAT [1.2; 0.010]NMP [80]4; 277
III6CU [1.6; 0.011]DMT [1.4; 0.011]DMAC [160] *4; 277
IV6CU [1.1; 0.008]DMT [1.0; 0.008]DMF [160] *4; 277
Va6CU [0.9; 0.006]CDT [1.0; 0.007]DMF [160]4; 277
Vb6CU [3.4; 0.023]CDT [3.4; 0.023]DMF [500]50; 323
VIM6CU [2.2; 0.014]** [2.2; 0.009]DMAC [50]23; 296
VIIM6CU [5.9; 0.037]TAT [4.6; 0.036]DMAC [80] ***50; 323
* plus 50 µL dimethylsulfoxide (DMSO) ** isobutyl 3,5-diamino-4-chlorobenzoate *** plus 20 µL HCl (1M)
Geometries of halogen bonds (see Fig. 1 for the definition of geometrical parameters) top
crystal no.D [Å]d [Å]θ1 [°]θ2 [°]
IV5.133 (5)3.455 (4)160.0 (1)/
Va4.755 (3)3.081 (2)165.8 (1)/
Vb4.732 (4)3.031 (3)171.3 (1)/
VI4.914 (2)3.352 (1)150.6 (1)150.6 (1)
VII4.777 (7)3.070 (4)178.0 (3)178.0 (3)

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