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It is well known that pyrimidin-4-one derivatives are able to adopt either the 1H- or the 3H-tautomeric form in (co)crystals, depending on the coformer. As part of ongoing research to investigate the preferred hydrogen-bonding patterns of active pharmaceutical ingredients and their model systems, 2-amino-6-chloro­pyrimidin-4-one and 2-amino-5-bromo-6-methylpyrimidin-4-one have been cocrystallized with several coformers and with each other. Since Cl and Br atoms both have versatile possibilities to inter­act with the coformers, such as via hydrogen or halogen bonds, their behaviour within the crystal packing was also of inter­est. The experiments yielded five crystal structures, namely 2-amino­pyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide-2-amino-6-chloro­pyrimidin-4(3H)-one (1/3), C5H7N2+·C4H3ClN3O-·3C4H4ClN3O, (Ia), 2-amino­pyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide-2-amino-6-chloro­pyrimidin-4(3H)-one-2-amino­pyridine (2/10/1), 2C5H7N2+·2C4H3ClN3O-·10C4H4ClN3O·C5H6N2, (Ib), the solvent-free cocrystal 2-amino-5-bromo-6-methyl­pyrimidin-4(3H)-one-2-amino-5-bromo-6-methyl­pyrimidin-4(1H)-one (1/1), C5H6BrN3O·C5H6BrN3O, (II), the solvate 2-amino-5-bromo-6-methyl­pyrimidin-4(3H)-one-2-amino-5-bromo-6-methyl­pyrimidin-4(1H)-one-N-methyl­pyrrolidin-2-one (1/1/1), C5H6BrN3O·C5H6BrN3O·C5H9NO, (III), and the partial cocrystal 2-amino-5-bromo-6-methyl­pyrimidin-4(3H)-one-2-amino-5-bromo-6-methyl­pyrimidin-4(1H)-one-2-amino-6-chloropyrimidin-4(3H)-one (0.635/1/0.365), C5H6BrN3O·C5H6BrN3O·C4H4ClN3O, (IV). All five structures show R22(8) hydrogen-bond-based patterns, either by synthon 2 or by synthon 3, which are related to the Watson-Crick base pairs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615024080/uk3121sup1.cif
Contains datablocks Ia, Ib, II, III, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121Iasup2.hkl
Contains datablock Ia

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121Ibsup3.hkl
Contains datablock Ib

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IIsup4.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IIIsup5.hkl
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615024080/uk3121IVsup6.hkl
Contains datablock IV

CCDC references: 1442480; 1442479; 1442478; 1442477; 1442476

Introduction top

Research into active pharmaceutical ingredients (API's), especially their polymorphism, salts and preferred solvate formation, is one of the key steps within drug development (Aitipamula et al., 2012). This particularly includes the physicochemical properties of the API, viz. solubility, dissolution rate, physicochemical stability, melting point and manufacturability, but most of all the bioavailability (Vangala et al., 2012). Due to their frequent low solubility and therefore diminished bioavailability, API's are generally applied as salts because of their hundred- to thousand-fold higher solubility in the ionic form compared with the pure API (Rajput et al., 2013). Another approach to enhance solubility (and bioavailability) is the formation of pharmaceutical cocrystals of the API and a GRAS (generally regarded as safe) coformer, such as caffeine, theophylline or urea (Sanphui et al., 2012), resulting in a solubility 40–160 times higher (Rajput et al., 2013). With regard to combining the API with its coformer, it is essential to determine the favoured tautomeric forms of both components, as they usually contain different hydrogen-bonding sites. The formation of a cocrystal requires complementary binding sites of the API and its coformer. These are often described in model systems, such as two hydrogen bonds with a DAAD (D denotes a donor and A an acceptor) or DDAA pattern, or three hydrogen bonds with DDAAAD or DADADA arrangements.

In an earlier study of the pyrimidin-4-one derivatives 2,6-di­amino­pyrimidin-4-one (AIC) and 2-amino-6-methyl­pyrimidin-4-one (MIC), we showed that for AIC the 3H-tautomer is strongly preferred, while for MIC both tautomeric forms are possible (Gerhardt et al., 2011). Therefore, we are inter­ested in seeing if the exchange of the methyl and amino groups, respectively, with a Cl atom in 2-amino-6-chloro­pyrimidin-4-one (6-chloro­isocytosine, CIC) would lead to similar characteristics to either AIC or MIC. Additionally, we are inter­ested in whether the substitution of the H atom with a Br atom at position 5 in 2-amino-5-bromo-6-methyl­pyrimidin-4-one (BMIC) affects the tautomerism and the packing motifs within the crystal structures.

Both components, CIC and BMIC, are able to form three hydrogen bonds, with an AAD binding site as the 1H-tautomer or with a DDA binding site as the 3H-tautomer, respectively. In addition, they are able to form two hydrogen bonds with an AD or DD site, depending on their tautomeric form and assuming that the halogen atoms do not participate in the crystal packings. It is also possible that the Cl and Br atoms are involved in weak inter­actions, such as hydrogen-bond or halogen inter­actions. In order to determine their preferred inter­action patterns, as well as their tautomeric forms, we crystallized CIC and BMIC with several coformers and with each other, yielding five crystal structures, namely two cocrystals of CIC with 2-amino­pyridine (AHP) with differing compositions in (Ia) and (Ib), one solvent-free structure, (II), and one N-methyl­pyrrolidine-4-one solvate of BMIC, (III), both showing a 1:1 mixture of the 1H- and 3H-tautomers. Attempts to cocrystallize CIC with BMIC yielded one cocrystal, (IV), wherein the 3H-tautomeric form of BMIC is partially substituted by CIC molecules (Scheme 1).

Experimental top

Synthesis and crystallization top

All experiments were performed with commercially available substances in various hydrous solvents and at different temperatures. Solubility tests of 2-amino-6-chloro­pyrimidin-4-one (6-chloro­isocytosine), C4H4ClN3O, did not lead to well diffracting crystals. Thus, isothermal solvent evaporation experiments of CIC with 2-amino­pyridine, C5H6N2, at 323 K in N,N-di­methyl­formamide (DMF) and N,N-di­methyl­acetamide (DMAC) were performed, yielding two cocrystals, (Ia) and (Ib). Both cocrystals differ within their chemical compositions as a result of proton transfer from molecules of CIC to AHP. In (Ia) a total molecular ratio of (3/1/1) (CIC/CIC-/AHP+) is observed, while in (Ib) the proton transfer yields a total molecular ratio of 10/2/2/1 (CIC/CIC-/AHP+/AHP).

Cocrystallization experiments of 2-amino-5-bromo-6-methyl­pyrimidin-4-one, C5H6BrN3O, with 2-amino-4-chloro-6-methyl­pyrimidine, C5H6N3Cl, in di­methyl­sulfoxide, C2H6SO (DMSO), at 323 K, yielded the solvent-free crystal, (II), while solubility tests of BMIC in NMP at 277 K provided the pseudopolymorph, (III). Attempts to cocrystallize BMIC with CIC were successful in DMAC at room temperature, forming the partial cocrystal (IV). A detailed summary of the solvent evaporation experiments performed is presented in Table 1.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were initially located by difference Fourier synthesis. Subsequently, C-bound H 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 with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) for aromatic H atoms. For the H atoms of the methyl groups in (II) and (III), free rotation about their local threefold axis was allowed.

N- and O-bound H atoms were refined isotropically, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O) for all structures. Also, 1,2 distance restraints for N—H bonds were applied to all structures and additional 1,3 distance restraints were used for the amino groups in (Ib), molecule B in (II), atom H1P in (Ib) and atom H1A in (IV).

In (Ib) and (IV) the main molecules are disordered. In (Ib) the non-protonated AHP molecule is disordered across a pseudo-mirror plane, which passes through atom N1R, while in (IV) one molecule of BMIC (B) is partially substituted with one molecule of CIC. The site-occupancy factors for the major occupied sites amount to 0.522 (2) for (Ib) and 0.635 (5) for (IV). The model for the disorder in (IV) was derived from the two electron density peaks at C6B.

In (Ib) a similar-ADP restraint (SIMU command in SHELXL97; Sheldrick, 2008), a rigid-bond restraint (DELU command in SHELXL97) and a planarity restraint (FLAT command in SHELXL97) were applied to the disordered AHP molecule.

Since (Ib) is a non-merohedral twin defined by the matrix (0 1 0 / 1 0 0 / 0.3 0.3 1), the reflection data file was prepared using PLATON (Spek, 2009). As a result, a file including 3597 reflections was generated. Thus, the domain ratio could be defined to 0.443 (3):0.557 (3) via the HKLF5 command (SHELXL97) and an additional variable (BASF command in SHELXL97).

Results and discussion top

The hydrogen-bond patterns which occur repeatedly within our research are usually built up by either one or two R22(8) hydrogen bonds (Bernstein et al.,1995). These are defined as synthon 2 [one R22(8) hydrogen-bond pattern] and synthon 3 [two connected R22(8) hydrogen-bond motifs], respectively (Fig. 1), and will be used in the following discussion. The two synthons can be specified further. The D or A groups which are involved in synthon 2 will be added as subscripts, e.g. 2iD'·A' and 2dD'·A';D''·A'' [What does the i signify? Also the d used below]. For synthon 3, either a symmetric ADADAD (synthon 3s) or an unsymmetric AADDDA (synthon 3u) pattern can be observed (Gerhardt & Egert, 2015).

Cocrystallization of 6-chloro­isocytosine and 5-bromo-6-methyl­isocytosine top

Cocrystallization attempts of 6-chloro­isocytosine with 2-amino­pyridine at 323 K in DMF and DMAC led to the cocrystals (Ia) and (Ib), respectively. In (Ia) the asymmetric unit consists of four planar molecules of CIC (r.m.s. deviations for non-H atoms = 0.0165, 0.0222, 0.0165 and 0.0092 Å for molecules A, B, C and D, respectively) and one planar molecule of AHP (r.m.s. deviation for non-H atoms of AHP = 0.0209 Å), which is located at an angle of 69.14 (6)° with respect to the essentially coplanar molecules AD. A proton transfer from molecule A of CIC to AHP has taken place and enables the formation of synthon 3u between molecules A and B. Apart from this proton transfer, only the 3H-tautomer of CIC is present. Furthermore, synthon 2iN.N connects molecule A with molecule C and molecule B with molecule D (Fig. 2; Table 3). As a consequence of this arrangement, the packing shows chains parallel to [202] in the synthon order 3u–2iN·N–2iN·O–2iN·N (Fig. 3). Molecules A and B in parallel chains are linked by N—H···O hydrogen bonds via one AHP molecule (Fig. 4). Despite the fact that the amino groups in molecules C and D are involved in only one of two possible hydrogen bonds, only one Cl atom participates in the packing, viz. atom Cl6D shows a halogen bond to the pyramidal amino group (N2E) of the AHP molecule, with a distance of 3.108 (3) Å.

Compound (Ib) crystallizes with 12(!) essentially planar molecules of CIC (labelled AM) and three planar molecules of AHP (O, P and R/S) in the asymmetric unit (see Table 4 for r.m.s. deviation values). Similar to (Ia), a proton transfer occurs from molecule B to molecule P and from molecule G to molecule O and, with the exception of these two deprotonated CIC molecules, again only the 3H-tautomer is observed for the CIC molecules. The third AHP molecule, R/S, in contrast to molecules O and P, is not protonated. Also, related to the inter­actions in (Ia), (Ib) shows chains within the asymmetric unit which are built by molecules AF and GM, both with synthon order 3u–2iN·N–2iN·O–2iN·N–2iN·O–2iN·N (Fig. 5, Table 5). Both chains are connected via N—H···O hydrogen bonds from molecule P to molecules B and H. In addition, molecules R and O are hydrogen-bonded to molecules E and F, and to L and M, with an R32(8) pattern that includes the amino group of R and O inter­acting as a donor as well as an acceptor. In the packing, the chains consisting of molecules AF are arranged parallel to [211], while the chains built by molecules GM are oriented parallel to [120]. `Double-layers', similar to those in (Ia), are built either by molecules A–F through N—H···O hydrogen bonds to molecule R or by molecules GM through N—H···O hydrogen bonds with the protonated AHP molecule O (Fig. 6). These `double-layers' are further connected via molecule P and via molecules O and R, which are linked through one N—H···N hydrogen bond, resulting in a three-dimensional network (Fig. 7). Again, similar to (Ia), not all hydrogen-bond donors fully participate within the packing, viz. the amino groups N2C, N2D, N2E, N2I, N2K and N2M only act as donors of just one hydrogen bond each. Two halogen inter­actions can be observed within the packing that involve atoms Cl6A [N···Cl = 3.257 (9) Å] and Cl6L [N···Cl = 3.245 (9) Å] to the pyridine atom N1R.

Experiments to cocrystallize BMIC with 2-amino-4-chloro-6-methyl­pyrimidine yielded the solvent-free crystal (II), which crystallizes with two molecules in the asymmetric unit (Fig. 8). Both molecules are essentially planar [r.m.s. deviations for non-H atoms of molecule A = 0.0112 Å and B = 0.0233 Å] and, due to their differing tautomeric forms, they provide a dimer, which is built by synthon 3u (Fig. 9; Table 6). In the packing the dimers are arranged parallel to (222) and to (222), and they are linked by two N—H···O hydrogen bonds from molecule A to atoms O4B and O4A. Finally, a weak hydrogen bond between atoms N2B and Br5A supports the two-dimensional arrangement within the packing (Fig. 10).

The NMP monosolvate (III) crystallizes in the monoclinic space group P21/n, again with both tautomeric forms of BMIC within the asymmetric unit (Fig. 11). As in (II), the planar synthon 3u can be observed (r.m.s. deviation for all non-H atoms of molecule A = 0.0200 Å and B = 0.0096 Å) and the solvent molecule X is R21(6) N—H···O hydrogen-bonded to molecule A (Table 7). In the packing the dimers form tetra­mers parallel to (301) through an R42(8) N—H···O hydrogen-bond pattern from molecules B to molecules A. Unlike (II), the packing of monosolvate (III) only shows that different tetra­mers are not further connected by hydrogen bonds and that the Br atoms do not participate in any hydrogen bonds (Fig. 12).

Attempts to cocrystallize CIC with BMIC led to the partial cocrystal (IV). Similar to (II) and (III), the asymmetric unit comprises the planar 1H-tautomer of BMIC, A, and the planar 3H-tautomeric form of BMIC, B, but with CIC disordered (r.m.s. deviation for all non-H atoms of molecule A = 0.0263 Å, BBMIC = 0.0509 Å and BCIC = 0.0117 Å) (Fig. 13). Nevertheless, synthon 3u is observed again. In the packing, a tetra­meric arrangement in the sequence of molecules ABBA is formed by synthon 2iN·N between two molecules of B (Fig. 14). The tetra­mers are linked to their neighbours through two additional N—H···O hydrogen bonds, enclosing an angle of approximately 68.3 (3)° to each other, and they assemble into a three-dimensional network (Table 8; Fig. 15). As in (III), no halogen inter­action is observed.

A previous substructure search of the Cambridge Structural Database (CSD, Version?; Groom & Allen, 2014) for pyrimidine-4-one revealed the favoured 3H-tautomeric form with 39 structures, while 15 structures showed the 1H-tautomeric form (Gerhardt et al., 2011). The 1H- and 3H-tautomers were found in five crystal structures. Considering these results, a higher tendency for the formation of the 3H-tautomer can be expected. On this basis, three CSD (Version for these searches?) searches for CIC, BMIC and 6-methyl­isocytosine (MIC), which were restricted to organic compounds with determined three-dimensional coordinates and including either the 1H- or 3H-tautomeric form, were performed and yielded 12 unique structures only of MIC. These results can be divided into three salts [XOWKOK (Oueslati et al., 2009), YOCZUN (Wang et al., 2014) and EXIPOR (Kaabi et al., 2011)], two entries that contain solely the 1H-tautomer [FETSEC (Lowe et al., 1987) and MECXUP (Tutughamiarso & Egert, 2012)], four entries with only the 3H-tautomer [MECXID (Tutughamiarso & Egert, 2012), MECXOJ (Tutughamiarso & Egert, 2012), ZUKXAE (Liao et al., 1996) and ZUKXEI (Liao et al., 1996)], two crystal structures containing both the 1H- and the 3H-tautomeric forms of MIC [OQURAU (Gerhardt et al., 2011) and OQUREY (Gerhardt et al., 2011)] and one undefined entry, which is disordered over the 1H- and 3H-positions [MINVIP01 (Portalone & Irrera, 2011)]. Inter­estingly, the formation of the 3H-tautomeric form of MIC is not strongly preferred in comparison with the 1H/3H-mixture or the 1H-tautomer. All four 3H entries are cocrystals or a cocrystal monohydrate and show two-dimensional packing motifs, while the 1H/3H-mixtures are mono- or disolvates with a one-dimensional packing arrangement. Due to the lack of hydrogen-bonding donors and acceptors of the coformer in ZUKXAE and ZUKXEI, only synthon 2dN·O;O·N is formed with molecules of MIC. Nevertheless, in ZUKXAE synthon 2iN·O forms between two molecules of MIC, which can also be found in MECXID but between MIC and its coformer 5-fluoro­cytosine. However, the prevailing synthon within the CSD search of MIC is 3u, as it occurs within all three 1H/3H-mixtures and two of the four 3H-tautomer-containing crystal structures. FETSEC, which contains only the 1H-tautomeric form of MIC, provides the second prevailing synthon 2iN·N, which is also included in the three solvates.

A comparison of the crystal structures of MIC with BMIC reveals similar behaviour regarding the formation of 1H/3H-mixtures in solvates. Thus, the addition of Br to the system does not affect the tautomerism therein. Inter­estingly, in the solvent-free structure, (II), the Br atom of the 1H-tautomer participates in the packing, and only the 3H-tautomer is partially disordered with CIC in (IV).

Conclusion top

All five structures are essentially built by synthon 3u hydrogen bonds. In (Ia) and (Ib) synthon 3u results in a proton transfer from CIC to its coformer AHP and is part of a synthon sequence, which also includes synthon 2iN·O and synthon 2iN·N. While (Ia) provides a two-dimensional network, (Ib) shows a three-dimensional arrangement. In both cases the packing is supported by Cl···N halogen inter­actions. Comparing these two cocrystals with ZUKXAE and ZUKXEI, the tendency to form synthon 2iN·O and 2dN·O;O·N, rather than solely 2iN·N, is indicated.

In (II), dimers are present, while in (III) and (IV) tetra­mers are the main packing motif. In (IV), the additional synthon 2iN·N inter­actions are responsible for extension of the tetra­mers to a three-dimensional hydrogen-bonding network in the packing. Nevertheless, the formation of dimers and tetra­mers with BMIC via synthon 3u hydrogen bonds is a direct consequence of the occurence of both tautomeric forms within the same crystal. Thus, and in compliance with our earlier studies, BMIC shows related behaviour patterns to its non-halogenated derivate 6-methyl­isocytosine, while, on the other hand, CIC only provides the 3H-tautomer in its cocrystals, which is in agreement with some of the cocrystals of MIC and the results of our previous investigations of 2,6-di­amino­pyrimidin-4(3H)-one.

Structure description top

Research into active pharmaceutical ingredients (API's), especially their polymorphism, salts and preferred solvate formation, is one of the key steps within drug development (Aitipamula et al., 2012). This particularly includes the physicochemical properties of the API, viz. solubility, dissolution rate, physicochemical stability, melting point and manufacturability, but most of all the bioavailability (Vangala et al., 2012). Due to their frequent low solubility and therefore diminished bioavailability, API's are generally applied as salts because of their hundred- to thousand-fold higher solubility in the ionic form compared with the pure API (Rajput et al., 2013). Another approach to enhance solubility (and bioavailability) is the formation of pharmaceutical cocrystals of the API and a GRAS (generally regarded as safe) coformer, such as caffeine, theophylline or urea (Sanphui et al., 2012), resulting in a solubility 40–160 times higher (Rajput et al., 2013). With regard to combining the API with its coformer, it is essential to determine the favoured tautomeric forms of both components, as they usually contain different hydrogen-bonding sites. The formation of a cocrystal requires complementary binding sites of the API and its coformer. These are often described in model systems, such as two hydrogen bonds with a DAAD (D denotes a donor and A an acceptor) or DDAA pattern, or three hydrogen bonds with DDAAAD or DADADA arrangements.

In an earlier study of the pyrimidin-4-one derivatives 2,6-di­amino­pyrimidin-4-one (AIC) and 2-amino-6-methyl­pyrimidin-4-one (MIC), we showed that for AIC the 3H-tautomer is strongly preferred, while for MIC both tautomeric forms are possible (Gerhardt et al., 2011). Therefore, we are inter­ested in seeing if the exchange of the methyl and amino groups, respectively, with a Cl atom in 2-amino-6-chloro­pyrimidin-4-one (6-chloro­isocytosine, CIC) would lead to similar characteristics to either AIC or MIC. Additionally, we are inter­ested in whether the substitution of the H atom with a Br atom at position 5 in 2-amino-5-bromo-6-methyl­pyrimidin-4-one (BMIC) affects the tautomerism and the packing motifs within the crystal structures.

Both components, CIC and BMIC, are able to form three hydrogen bonds, with an AAD binding site as the 1H-tautomer or with a DDA binding site as the 3H-tautomer, respectively. In addition, they are able to form two hydrogen bonds with an AD or DD site, depending on their tautomeric form and assuming that the halogen atoms do not participate in the crystal packings. It is also possible that the Cl and Br atoms are involved in weak inter­actions, such as hydrogen-bond or halogen inter­actions. In order to determine their preferred inter­action patterns, as well as their tautomeric forms, we crystallized CIC and BMIC with several coformers and with each other, yielding five crystal structures, namely two cocrystals of CIC with 2-amino­pyridine (AHP) with differing compositions in (Ia) and (Ib), one solvent-free structure, (II), and one N-methyl­pyrrolidine-4-one solvate of BMIC, (III), both showing a 1:1 mixture of the 1H- and 3H-tautomers. Attempts to cocrystallize CIC with BMIC yielded one cocrystal, (IV), wherein the 3H-tautomeric form of BMIC is partially substituted by CIC molecules (Scheme 1).

The hydrogen-bond patterns which occur repeatedly within our research are usually built up by either one or two R22(8) hydrogen bonds (Bernstein et al.,1995). These are defined as synthon 2 [one R22(8) hydrogen-bond pattern] and synthon 3 [two connected R22(8) hydrogen-bond motifs], respectively (Fig. 1), and will be used in the following discussion. The two synthons can be specified further. The D or A groups which are involved in synthon 2 will be added as subscripts, e.g. 2iD'·A' and 2dD'·A';D''·A'' [What does the i signify? Also the d used below]. For synthon 3, either a symmetric ADADAD (synthon 3s) or an unsymmetric AADDDA (synthon 3u) pattern can be observed (Gerhardt & Egert, 2015).

Cocrystallization attempts of 6-chloro­isocytosine with 2-amino­pyridine at 323 K in DMF and DMAC led to the cocrystals (Ia) and (Ib), respectively. In (Ia) the asymmetric unit consists of four planar molecules of CIC (r.m.s. deviations for non-H atoms = 0.0165, 0.0222, 0.0165 and 0.0092 Å for molecules A, B, C and D, respectively) and one planar molecule of AHP (r.m.s. deviation for non-H atoms of AHP = 0.0209 Å), which is located at an angle of 69.14 (6)° with respect to the essentially coplanar molecules AD. A proton transfer from molecule A of CIC to AHP has taken place and enables the formation of synthon 3u between molecules A and B. Apart from this proton transfer, only the 3H-tautomer of CIC is present. Furthermore, synthon 2iN.N connects molecule A with molecule C and molecule B with molecule D (Fig. 2; Table 3). As a consequence of this arrangement, the packing shows chains parallel to [202] in the synthon order 3u–2iN·N–2iN·O–2iN·N (Fig. 3). Molecules A and B in parallel chains are linked by N—H···O hydrogen bonds via one AHP molecule (Fig. 4). Despite the fact that the amino groups in molecules C and D are involved in only one of two possible hydrogen bonds, only one Cl atom participates in the packing, viz. atom Cl6D shows a halogen bond to the pyramidal amino group (N2E) of the AHP molecule, with a distance of 3.108 (3) Å.

Compound (Ib) crystallizes with 12(!) essentially planar molecules of CIC (labelled AM) and three planar molecules of AHP (O, P and R/S) in the asymmetric unit (see Table 4 for r.m.s. deviation values). Similar to (Ia), a proton transfer occurs from molecule B to molecule P and from molecule G to molecule O and, with the exception of these two deprotonated CIC molecules, again only the 3H-tautomer is observed for the CIC molecules. The third AHP molecule, R/S, in contrast to molecules O and P, is not protonated. Also, related to the inter­actions in (Ia), (Ib) shows chains within the asymmetric unit which are built by molecules AF and GM, both with synthon order 3u–2iN·N–2iN·O–2iN·N–2iN·O–2iN·N (Fig. 5, Table 5). Both chains are connected via N—H···O hydrogen bonds from molecule P to molecules B and H. In addition, molecules R and O are hydrogen-bonded to molecules E and F, and to L and M, with an R32(8) pattern that includes the amino group of R and O inter­acting as a donor as well as an acceptor. In the packing, the chains consisting of molecules AF are arranged parallel to [211], while the chains built by molecules GM are oriented parallel to [120]. `Double-layers', similar to those in (Ia), are built either by molecules A–F through N—H···O hydrogen bonds to molecule R or by molecules GM through N—H···O hydrogen bonds with the protonated AHP molecule O (Fig. 6). These `double-layers' are further connected via molecule P and via molecules O and R, which are linked through one N—H···N hydrogen bond, resulting in a three-dimensional network (Fig. 7). Again, similar to (Ia), not all hydrogen-bond donors fully participate within the packing, viz. the amino groups N2C, N2D, N2E, N2I, N2K and N2M only act as donors of just one hydrogen bond each. Two halogen inter­actions can be observed within the packing that involve atoms Cl6A [N···Cl = 3.257 (9) Å] and Cl6L [N···Cl = 3.245 (9) Å] to the pyridine atom N1R.

Experiments to cocrystallize BMIC with 2-amino-4-chloro-6-methyl­pyrimidine yielded the solvent-free crystal (II), which crystallizes with two molecules in the asymmetric unit (Fig. 8). Both molecules are essentially planar [r.m.s. deviations for non-H atoms of molecule A = 0.0112 Å and B = 0.0233 Å] and, due to their differing tautomeric forms, they provide a dimer, which is built by synthon 3u (Fig. 9; Table 6). In the packing the dimers are arranged parallel to (222) and to (222), and they are linked by two N—H···O hydrogen bonds from molecule A to atoms O4B and O4A. Finally, a weak hydrogen bond between atoms N2B and Br5A supports the two-dimensional arrangement within the packing (Fig. 10).

The NMP monosolvate (III) crystallizes in the monoclinic space group P21/n, again with both tautomeric forms of BMIC within the asymmetric unit (Fig. 11). As in (II), the planar synthon 3u can be observed (r.m.s. deviation for all non-H atoms of molecule A = 0.0200 Å and B = 0.0096 Å) and the solvent molecule X is R21(6) N—H···O hydrogen-bonded to molecule A (Table 7). In the packing the dimers form tetra­mers parallel to (301) through an R42(8) N—H···O hydrogen-bond pattern from molecules B to molecules A. Unlike (II), the packing of monosolvate (III) only shows that different tetra­mers are not further connected by hydrogen bonds and that the Br atoms do not participate in any hydrogen bonds (Fig. 12).

Attempts to cocrystallize CIC with BMIC led to the partial cocrystal (IV). Similar to (II) and (III), the asymmetric unit comprises the planar 1H-tautomer of BMIC, A, and the planar 3H-tautomeric form of BMIC, B, but with CIC disordered (r.m.s. deviation for all non-H atoms of molecule A = 0.0263 Å, BBMIC = 0.0509 Å and BCIC = 0.0117 Å) (Fig. 13). Nevertheless, synthon 3u is observed again. In the packing, a tetra­meric arrangement in the sequence of molecules ABBA is formed by synthon 2iN·N between two molecules of B (Fig. 14). The tetra­mers are linked to their neighbours through two additional N—H···O hydrogen bonds, enclosing an angle of approximately 68.3 (3)° to each other, and they assemble into a three-dimensional network (Table 8; Fig. 15). As in (III), no halogen inter­action is observed.

A previous substructure search of the Cambridge Structural Database (CSD, Version?; Groom & Allen, 2014) for pyrimidine-4-one revealed the favoured 3H-tautomeric form with 39 structures, while 15 structures showed the 1H-tautomeric form (Gerhardt et al., 2011). The 1H- and 3H-tautomers were found in five crystal structures. Considering these results, a higher tendency for the formation of the 3H-tautomer can be expected. On this basis, three CSD (Version for these searches?) searches for CIC, BMIC and 6-methyl­isocytosine (MIC), which were restricted to organic compounds with determined three-dimensional coordinates and including either the 1H- or 3H-tautomeric form, were performed and yielded 12 unique structures only of MIC. These results can be divided into three salts [XOWKOK (Oueslati et al., 2009), YOCZUN (Wang et al., 2014) and EXIPOR (Kaabi et al., 2011)], two entries that contain solely the 1H-tautomer [FETSEC (Lowe et al., 1987) and MECXUP (Tutughamiarso & Egert, 2012)], four entries with only the 3H-tautomer [MECXID (Tutughamiarso & Egert, 2012), MECXOJ (Tutughamiarso & Egert, 2012), ZUKXAE (Liao et al., 1996) and ZUKXEI (Liao et al., 1996)], two crystal structures containing both the 1H- and the 3H-tautomeric forms of MIC [OQURAU (Gerhardt et al., 2011) and OQUREY (Gerhardt et al., 2011)] and one undefined entry, which is disordered over the 1H- and 3H-positions [MINVIP01 (Portalone & Irrera, 2011)]. Inter­estingly, the formation of the 3H-tautomeric form of MIC is not strongly preferred in comparison with the 1H/3H-mixture or the 1H-tautomer. All four 3H entries are cocrystals or a cocrystal monohydrate and show two-dimensional packing motifs, while the 1H/3H-mixtures are mono- or disolvates with a one-dimensional packing arrangement. Due to the lack of hydrogen-bonding donors and acceptors of the coformer in ZUKXAE and ZUKXEI, only synthon 2dN·O;O·N is formed with molecules of MIC. Nevertheless, in ZUKXAE synthon 2iN·O forms between two molecules of MIC, which can also be found in MECXID but between MIC and its coformer 5-fluoro­cytosine. However, the prevailing synthon within the CSD search of MIC is 3u, as it occurs within all three 1H/3H-mixtures and two of the four 3H-tautomer-containing crystal structures. FETSEC, which contains only the 1H-tautomeric form of MIC, provides the second prevailing synthon 2iN·N, which is also included in the three solvates.

A comparison of the crystal structures of MIC with BMIC reveals similar behaviour regarding the formation of 1H/3H-mixtures in solvates. Thus, the addition of Br to the system does not affect the tautomerism therein. Inter­estingly, in the solvent-free structure, (II), the Br atom of the 1H-tautomer participates in the packing, and only the 3H-tautomer is partially disordered with CIC in (IV).

All five structures are essentially built by synthon 3u hydrogen bonds. In (Ia) and (Ib) synthon 3u results in a proton transfer from CIC to its coformer AHP and is part of a synthon sequence, which also includes synthon 2iN·O and synthon 2iN·N. While (Ia) provides a two-dimensional network, (Ib) shows a three-dimensional arrangement. In both cases the packing is supported by Cl···N halogen inter­actions. Comparing these two cocrystals with ZUKXAE and ZUKXEI, the tendency to form synthon 2iN·O and 2dN·O;O·N, rather than solely 2iN·N, is indicated.

In (II), dimers are present, while in (III) and (IV) tetra­mers are the main packing motif. In (IV), the additional synthon 2iN·N inter­actions are responsible for extension of the tetra­mers to a three-dimensional hydrogen-bonding network in the packing. Nevertheless, the formation of dimers and tetra­mers with BMIC via synthon 3u hydrogen bonds is a direct consequence of the occurence of both tautomeric forms within the same crystal. Thus, and in compliance with our earlier studies, BMIC shows related behaviour patterns to its non-halogenated derivate 6-methyl­isocytosine, while, on the other hand, CIC only provides the 3H-tautomer in its cocrystals, which is in agreement with some of the cocrystals of MIC and the results of our previous investigations of 2,6-di­amino­pyrimidin-4(3H)-one.

Synthesis and crystallization top

All experiments were performed with commercially available substances in various hydrous solvents and at different temperatures. Solubility tests of 2-amino-6-chloro­pyrimidin-4-one (6-chloro­isocytosine), C4H4ClN3O, did not lead to well diffracting crystals. Thus, isothermal solvent evaporation experiments of CIC with 2-amino­pyridine, C5H6N2, at 323 K in N,N-di­methyl­formamide (DMF) and N,N-di­methyl­acetamide (DMAC) were performed, yielding two cocrystals, (Ia) and (Ib). Both cocrystals differ within their chemical compositions as a result of proton transfer from molecules of CIC to AHP. In (Ia) a total molecular ratio of (3/1/1) (CIC/CIC-/AHP+) is observed, while in (Ib) the proton transfer yields a total molecular ratio of 10/2/2/1 (CIC/CIC-/AHP+/AHP).

Cocrystallization experiments of 2-amino-5-bromo-6-methyl­pyrimidin-4-one, C5H6BrN3O, with 2-amino-4-chloro-6-methyl­pyrimidine, C5H6N3Cl, in di­methyl­sulfoxide, C2H6SO (DMSO), at 323 K, yielded the solvent-free crystal, (II), while solubility tests of BMIC in NMP at 277 K provided the pseudopolymorph, (III). Attempts to cocrystallize BMIC with CIC were successful in DMAC at room temperature, forming the partial cocrystal (IV). A detailed summary of the solvent evaporation experiments performed is presented in Table 1.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were initially located by difference Fourier synthesis. Subsequently, C-bound H 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 with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) for aromatic H atoms. For the H atoms of the methyl groups in (II) and (III), free rotation about their local threefold axis was allowed.

N- and O-bound H atoms were refined isotropically, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O) for all structures. Also, 1,2 distance restraints for N—H bonds were applied to all structures and additional 1,3 distance restraints were used for the amino groups in (Ib), molecule B in (II), atom H1P in (Ib) and atom H1A in (IV).

In (Ib) and (IV) the main molecules are disordered. In (Ib) the non-protonated AHP molecule is disordered across a pseudo-mirror plane, which passes through atom N1R, while in (IV) one molecule of BMIC (B) is partially substituted with one molecule of CIC. The site-occupancy factors for the major occupied sites amount to 0.522 (2) for (Ib) and 0.635 (5) for (IV). The model for the disorder in (IV) was derived from the two electron density peaks at C6B.

In (Ib) a similar-ADP restraint (SIMU command in SHELXL97; Sheldrick, 2008), a rigid-bond restraint (DELU command in SHELXL97) and a planarity restraint (FLAT command in SHELXL97) were applied to the disordered AHP molecule.

Since (Ib) is a non-merohedral twin defined by the matrix (0 1 0 / 1 0 0 / 0.3 0.3 1), the reflection data file was prepared using PLATON (Spek, 2009). As a result, a file including 3597 reflections was generated. Thus, the domain ratio could be defined to 0.443 (3):0.557 (3) via the HKLF5 command (SHELXL97) and an additional variable (BASF command in SHELXL97).

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 (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Synthons used for two and three hydrogen bonds according to Bernstein et al. (1995) and Gerhardt & Egert (2015).
[Figure 2] Fig. 2. A perspective view of (Ia), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are indicated as dashed lines.
[Figure 3] Fig. 3. A partial packing diagram for (Ia), representing the synthon sequence 3u–2iN·N–2iN·O–2iN·N. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry code: (ii) x - 1, y, z - 1.]
[Figure 4] Fig. 4. A partial packing diagram for (Ia). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds.
[Figure 5] Fig. 5. A perspective view of (Ib), showing the atom-numbering scheme. Part (a) contains the 6-chloroisocytosine molecules A to F, the 2-aminopyridine P and the disordered AHP molecule R/S, and part (b) contains the molecules G to M and the 2-aminopyridine molecule O. In both parts, displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are displayed as dashed lines.
[Figure 6] Fig. 6. A partial packing diagram for (Ib), representing the synthon sequence 3u–2iN·N–2iN·O–2iN·N–2iN·O–2iN·N. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry code: (vii) x - 2, y + 1, z.]
[Figure 7] Fig. 7. A partial packing diagram for (Ib). Only H atoms which participate in hydrogen bonds are shown. For a better presentation of the packing, all molecules are colour coded: molecules A to F are yellow, G to M light green, O purple, P orange and R/S blue.
[Figure 8] Fig. 8. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are indicated by dashed lines.
[Figure 9] Fig. 9. A partial packing diagram for (II). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) -x + 1/2, y + 1/2, -z + 1/2; (ii) x - 1/2, -y + 3/2, z - 1/2; (iii) -x + 3/2, y - 1/2, -z + 3/2.]
[Figure 10] Fig. 10. A partial packing diagram for (II), showing the two-dimensional arrangement in the crystal structure. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds.
[Figure 11] Fig. 11. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are displayed as dashed lines.
[Figure 12] Fig. 12. A partial packing diagram for (III). Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds. [Symmetry code: (i) -x + 1, -y + 1, -z.]
[Figure 13] Fig. 13. A perspective view of (IV), showing the atom-numbering scheme. Part (a) contains the two tautomeric forms of BMIC, while part (b) shows the 6-chloroisocytosine molecule, which is substituted with the 3H tautomeric form of BMIC. In both parts, displacement ellipsoids are drawn at the 50% probability level and hydrogen bonds are indicated as dashed lines.
[Figure 14] Fig. 14. A partial packing diagram for (IV), representing the synthon sequence 3u–2iN·N–3u of the tetrameric arrangement. Only H 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; (iii) -x + 2, -y + 1, -z + 1.]
[Figure 15] Fig. 15. A partial packing diagram for (IV), showing the three-dimensional arrangement in the crystal structure. Only H atoms which participate in hydrogen bonds are shown. Dashed lines indicate hydrogen bonds.
(Ia) (2-aminopyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide)–[2-amino-6-chloropyrimidin-4(3H)-one] (1/3) top
Crystal data top
C5H7N2+·C4H3ClN3O·3C4H4ClN3OZ = 2
Mr = 676.32F(000) = 692
Triclinic, P1Dx = 1.651 Mg m3
a = 10.8229 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7395 (14) ÅCell parameters from 11802 reflections
c = 12.7637 (13) Åθ = 3.3–26.3°
α = 62.633 (8)°µ = 0.50 mm1
β = 70.877 (8)°T = 173 K
γ = 81.182 (9)°Plate, colourless
V = 1360.7 (3) Å30.26 × 0.09 × 0.07 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
3077 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.125
ω scansθmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1313
Tmin = 0.880, Tmax = 0.960k = 1414
22097 measured reflectionsl = 1515
5228 independent reflections
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)] = 0.058Hydrogen site location: mixed
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
5228 reflections(Δ/σ)max < 0.001
430 parametersΔρmax = 0.42 e Å3
14 restraintsΔρmin = 0.43 e Å3
Crystal data top
C5H7N2+·C4H3ClN3O·3C4H4ClN3Oγ = 81.182 (9)°
Mr = 676.32V = 1360.7 (3) Å3
Triclinic, P1Z = 2
a = 10.8229 (11) ÅMo Kα radiation
b = 11.7395 (14) ŵ = 0.50 mm1
c = 12.7637 (13) ÅT = 173 K
α = 62.633 (8)°0.26 × 0.09 × 0.07 mm
β = 70.877 (8)°
Data collection top
Stoe IPDSII two-circle
diffractometer
5228 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
3077 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.960Rint = 0.125
22097 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05814 restraints
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.42 e Å3
5228 reflectionsΔρmin = 0.43 e Å3
430 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.5541 (3)0.3919 (3)0.8172 (3)0.0302 (7)
C2A0.4893 (3)0.4800 (4)0.7403 (4)0.0305 (8)
N2A0.4876 (3)0.5997 (3)0.7272 (4)0.0384 (8)
H21A0.456 (4)0.667 (3)0.674 (3)0.046*
H22A0.532 (4)0.605 (4)0.771 (4)0.046*
N3A0.4248 (3)0.4576 (3)0.6771 (3)0.0278 (7)
C4A0.4232 (3)0.3365 (4)0.6933 (4)0.0287 (8)
O4A0.3569 (3)0.3127 (3)0.6368 (3)0.0362 (7)
C5A0.4907 (3)0.2389 (4)0.7693 (4)0.0306 (8)
H5A0.49310.15310.77980.037*
C6A0.5522 (3)0.2743 (4)0.8267 (3)0.0284 (8)
Cl6A0.63910 (9)0.16052 (10)0.92239 (10)0.0375 (3)
N1B0.1553 (3)0.7179 (3)0.3900 (3)0.0295 (7)
C2B0.2268 (3)0.6322 (4)0.4590 (4)0.0277 (8)
N2B0.2281 (3)0.5110 (3)0.4790 (3)0.0318 (7)
H21B0.187 (3)0.499 (4)0.436 (4)0.038*
H22B0.270 (4)0.450 (3)0.529 (3)0.038*
N3B0.2981 (3)0.6644 (3)0.5124 (3)0.0275 (7)
H3B0.347 (3)0.603 (3)0.552 (3)0.033*
C4B0.3078 (3)0.7883 (4)0.4928 (4)0.0295 (8)
O4B0.3812 (2)0.8121 (2)0.5385 (3)0.0327 (6)
C5B0.2298 (3)0.8801 (4)0.4224 (4)0.0333 (9)
H5B0.22600.96700.40890.040*
C6B0.1607 (3)0.8381 (4)0.3750 (4)0.0310 (9)
Cl6B0.06668 (9)0.94686 (9)0.28506 (10)0.0400 (3)
N1C0.6284 (3)0.6441 (3)0.8735 (3)0.0295 (7)
C2C0.6923 (3)0.5555 (4)0.9476 (3)0.0262 (8)
N2C0.6971 (3)0.4350 (3)0.9613 (3)0.0344 (8)
H21C0.650 (3)0.425 (4)0.921 (4)0.041*
H22C0.717 (4)0.373 (3)1.026 (3)0.041*
N3C0.7574 (3)0.5832 (3)1.0080 (3)0.0287 (7)
H3C0.804 (4)0.521 (3)1.050 (3)0.034*
C4C0.7642 (3)0.7063 (4)0.9953 (3)0.0263 (8)
O4C0.8291 (2)0.7227 (2)1.0520 (3)0.0325 (6)
C5C0.6956 (3)0.8006 (4)0.9168 (4)0.0314 (9)
H5C0.69420.88770.90210.038*
C6C0.6321 (3)0.7622 (4)0.8633 (3)0.0286 (8)
Cl6C0.54311 (9)0.87294 (10)0.76902 (10)0.0377 (3)
N1D0.0838 (3)0.4633 (3)0.3370 (3)0.0300 (7)
C2D0.0142 (3)0.5503 (4)0.2695 (4)0.0296 (8)
N2D0.0095 (3)0.6703 (3)0.2564 (4)0.0385 (8)
H21D0.046 (4)0.681 (4)0.304 (4)0.046*
H22D0.039 (4)0.729 (3)0.215 (4)0.046*
N3D0.0505 (3)0.5239 (3)0.2085 (3)0.0310 (7)
H3D0.092 (4)0.592 (3)0.164 (3)0.037*
C4D0.0500 (3)0.4055 (4)0.2115 (4)0.0307 (8)
O4D0.1115 (3)0.3893 (3)0.1522 (3)0.0406 (7)
C5D0.0224 (3)0.3107 (4)0.2854 (4)0.0324 (9)
H5D0.02740.22510.29510.039*
C6D0.0846 (3)0.3467 (4)0.3418 (4)0.0303 (9)
Cl6D0.17609 (9)0.23424 (10)0.43204 (10)0.0375 (3)
N1E0.2719 (3)0.0830 (3)0.7469 (3)0.0299 (7)
H1E0.315 (3)0.156 (2)0.697 (3)0.036*
C2E0.2825 (3)0.0046 (4)0.6931 (4)0.0292 (8)
N2E0.3585 (3)0.0405 (3)0.5774 (3)0.0336 (8)
H21E0.372 (4)0.014 (3)0.548 (4)0.040*
H22E0.416 (3)0.103 (3)0.543 (4)0.040*
C3E0.2128 (3)0.1108 (3)0.7621 (4)0.0294 (8)
H3E0.21680.16670.72590.035*
C4E0.1394 (3)0.1429 (4)0.8807 (4)0.0348 (9)
H4E0.09010.22000.92680.042*
C5E0.1366 (3)0.0623 (4)0.9353 (4)0.0345 (9)
H5E0.08970.08581.01950.041*
C6E0.2023 (4)0.0501 (4)0.8647 (4)0.0347 (9)
H6E0.19890.10700.89970.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0285 (15)0.0341 (18)0.034 (2)0.0005 (13)0.0137 (14)0.0166 (16)
C2A0.0228 (17)0.039 (2)0.032 (2)0.0021 (16)0.0078 (16)0.0171 (19)
N2A0.049 (2)0.0333 (19)0.048 (2)0.0001 (16)0.0306 (17)0.0193 (18)
N3A0.0276 (14)0.0322 (17)0.0307 (19)0.0014 (13)0.0136 (13)0.0157 (15)
C4A0.0266 (17)0.036 (2)0.026 (2)0.0046 (15)0.0069 (15)0.0142 (18)
O4A0.0442 (15)0.0332 (15)0.0453 (19)0.0002 (12)0.0267 (14)0.0198 (14)
C5A0.0276 (17)0.035 (2)0.037 (2)0.0003 (16)0.0119 (16)0.0210 (19)
C6A0.0217 (16)0.035 (2)0.028 (2)0.0019 (15)0.0067 (15)0.0141 (18)
Cl6A0.0345 (5)0.0423 (6)0.0405 (6)0.0073 (4)0.0197 (4)0.0184 (5)
N1B0.0252 (14)0.0353 (18)0.032 (2)0.0018 (13)0.0106 (13)0.0158 (16)
C2B0.0222 (16)0.036 (2)0.028 (2)0.0026 (15)0.0059 (15)0.0162 (18)
N2B0.0348 (17)0.0319 (18)0.038 (2)0.0013 (14)0.0193 (15)0.0168 (17)
N3B0.0251 (14)0.0294 (17)0.0320 (19)0.0001 (12)0.0103 (13)0.0155 (15)
C4B0.0283 (18)0.031 (2)0.030 (2)0.0025 (15)0.0040 (16)0.0162 (18)
O4B0.0342 (13)0.0349 (15)0.0374 (17)0.0035 (11)0.0151 (12)0.0187 (13)
C5B0.0295 (18)0.034 (2)0.044 (3)0.0025 (16)0.0145 (17)0.021 (2)
C6B0.0212 (16)0.034 (2)0.034 (2)0.0001 (15)0.0032 (15)0.0148 (19)
Cl6B0.0338 (5)0.0362 (5)0.0501 (7)0.0031 (4)0.0208 (5)0.0143 (5)
N1C0.0240 (14)0.0344 (18)0.032 (2)0.0016 (13)0.0095 (13)0.0148 (15)
C2C0.0217 (16)0.033 (2)0.026 (2)0.0029 (15)0.0066 (15)0.0139 (17)
N2C0.0408 (18)0.0323 (19)0.039 (2)0.0010 (15)0.0211 (16)0.0165 (17)
N3C0.0257 (15)0.0307 (17)0.033 (2)0.0006 (13)0.0118 (13)0.0150 (16)
C4C0.0227 (16)0.032 (2)0.027 (2)0.0036 (14)0.0069 (15)0.0139 (17)
O4C0.0339 (13)0.0342 (15)0.0409 (17)0.0000 (11)0.0177 (12)0.0213 (14)
C5C0.0265 (17)0.032 (2)0.037 (2)0.0009 (16)0.0100 (16)0.0160 (19)
C6C0.0221 (16)0.036 (2)0.025 (2)0.0014 (15)0.0056 (15)0.0125 (18)
Cl6C0.0346 (5)0.0406 (6)0.0413 (6)0.0052 (4)0.0198 (4)0.0165 (5)
N1D0.0259 (15)0.0314 (17)0.034 (2)0.0008 (13)0.0144 (14)0.0123 (15)
C2D0.0254 (17)0.034 (2)0.029 (2)0.0028 (15)0.0081 (16)0.0133 (18)
N2D0.048 (2)0.0325 (19)0.048 (2)0.0016 (15)0.0288 (17)0.0183 (18)
N3D0.0332 (16)0.0292 (17)0.037 (2)0.0023 (14)0.0196 (15)0.0147 (16)
C4D0.0267 (17)0.035 (2)0.031 (2)0.0052 (15)0.0074 (16)0.0144 (18)
O4D0.0445 (15)0.0409 (16)0.055 (2)0.0024 (13)0.0313 (14)0.0259 (16)
C5D0.0273 (18)0.035 (2)0.037 (2)0.0014 (16)0.0118 (17)0.0172 (19)
C6D0.0239 (17)0.035 (2)0.028 (2)0.0005 (15)0.0039 (15)0.0127 (18)
Cl6D0.0341 (5)0.0398 (6)0.0406 (6)0.0069 (4)0.0173 (4)0.0170 (5)
N1E0.0273 (15)0.0307 (17)0.039 (2)0.0002 (13)0.0146 (15)0.0180 (16)
C2E0.0204 (16)0.034 (2)0.041 (2)0.0047 (15)0.0158 (16)0.0199 (19)
N2E0.0276 (16)0.039 (2)0.040 (2)0.0042 (14)0.0070 (15)0.0236 (18)
C3E0.0242 (16)0.0275 (19)0.043 (3)0.0010 (14)0.0113 (16)0.0206 (18)
C4E0.0248 (17)0.034 (2)0.048 (3)0.0004 (16)0.0125 (17)0.019 (2)
C5E0.0295 (18)0.039 (2)0.034 (2)0.0063 (17)0.0116 (17)0.016 (2)
C6E0.0329 (19)0.042 (2)0.040 (3)0.0065 (17)0.0160 (18)0.025 (2)
Geometric parameters (Å, º) top
N1A—C6A1.332 (4)C4C—O4C1.247 (4)
N1A—C2A1.349 (5)C4C—C5C1.413 (5)
C2A—N2A1.334 (5)C5C—C6C1.351 (5)
C2A—N3A1.352 (4)C5C—H5C0.9500
N2A—H21A0.885 (19)C6C—Cl6C1.733 (4)
N2A—H22A0.880 (19)N1D—C2D1.317 (5)
N3A—C4A1.341 (5)N1D—C6D1.340 (5)
C4A—O4A1.303 (4)C2D—N2D1.335 (5)
C4A—C5A1.405 (5)C2D—N3D1.356 (5)
C5A—C6A1.356 (5)N2D—H21D0.888 (19)
C5A—H5A0.9500N2D—H22D0.870 (19)
C6A—Cl6A1.740 (4)N3D—C4D1.372 (5)
N1B—C2B1.334 (5)N3D—H3D0.891 (19)
N1B—C6B1.342 (5)C4D—O4D1.246 (4)
C2B—N2B1.323 (5)C4D—C5D1.412 (5)
C2B—N3B1.369 (5)C5D—C6D1.355 (5)
N2B—H21B0.873 (19)C5D—H5D0.9500
N2B—H22B0.897 (19)C6D—Cl6D1.731 (4)
N3B—C4B1.373 (5)N1E—C6E1.338 (5)
N3B—H3B0.875 (19)N1E—C2E1.353 (4)
C4B—O4B1.254 (4)N1E—H1E0.890 (19)
C4B—C5B1.417 (5)C2E—N2E1.331 (5)
C5B—C6B1.361 (5)C2E—C3E1.400 (5)
C5B—H5B0.9500N2E—H21E0.862 (19)
C6B—Cl6B1.733 (4)N2E—H22E0.889 (19)
N1C—C2C1.326 (5)C3E—C4E1.358 (6)
N1C—C6C1.338 (5)C3E—H3E0.9500
C2C—N2C1.338 (5)C4E—C5E1.402 (5)
C2C—N3C1.362 (4)C4E—H4E0.9500
N2C—H21C0.880 (19)C5E—C6E1.354 (6)
N2C—H22C0.884 (19)C5E—H5E0.9500
N3C—C4C1.389 (5)C6E—H6E0.9500
N3C—H3C0.884 (19)
C6A—N1A—C2A113.9 (3)N3C—C4C—C5C114.7 (3)
N2A—C2A—N1A116.6 (3)C6C—C5C—C4C117.5 (3)
N2A—C2A—N3A117.4 (3)C6C—C5C—H5C121.2
N1A—C2A—N3A126.0 (3)C4C—C5C—H5C121.2
C2A—N2A—H21A125 (3)N1C—C6C—C5C127.5 (3)
C2A—N2A—H22A111 (3)N1C—C6C—Cl6C112.9 (3)
H21A—N2A—H22A123 (4)C5C—C6C—Cl6C119.6 (3)
C4A—N3A—C2A117.3 (3)C2D—N1D—C6D115.0 (3)
O4A—C4A—N3A117.9 (3)N1D—C2D—N2D119.7 (3)
O4A—C4A—C5A121.4 (3)N1D—C2D—N3D122.3 (3)
N3A—C4A—C5A120.7 (3)N2D—C2D—N3D117.9 (3)
C6A—C5A—C4A116.1 (3)C2D—N2D—H21D115 (3)
C6A—C5A—H5A122.0C2D—N2D—H22D122 (3)
C4A—C5A—H5A122.0H21D—N2D—H22D122 (4)
N1A—C6A—C5A126.0 (3)C2D—N3D—C4D123.5 (3)
N1A—C6A—Cl6A114.4 (3)C2D—N3D—H3D113 (3)
C5A—C6A—Cl6A119.6 (3)C4D—N3D—H3D123 (3)
C2B—N1B—C6B115.0 (3)O4D—C4D—N3D119.6 (3)
N2B—C2B—N1B119.6 (3)O4D—C4D—C5D125.7 (3)
N2B—C2B—N3B118.1 (3)N3D—C4D—C5D114.7 (3)
N1B—C2B—N3B122.3 (3)C6D—C5D—C4D117.4 (3)
C2B—N2B—H21B113 (3)C6D—C5D—H5D121.3
C2B—N2B—H22B122 (3)C4D—C5D—H5D121.3
H21B—N2B—H22B125 (4)N1D—C6D—C5D127.1 (3)
C2B—N3B—C4B122.5 (3)N1D—C6D—Cl6D113.8 (3)
C2B—N3B—H3B116 (3)C5D—C6D—Cl6D119.1 (3)
C4B—N3B—H3B121 (3)C6E—N1E—C2E121.7 (4)
O4B—C4B—N3B119.1 (3)C6E—N1E—H1E125 (3)
O4B—C4B—C5B125.0 (3)C2E—N1E—H1E114 (3)
N3B—C4B—C5B115.8 (3)N2E—C2E—N1E118.6 (4)
C6B—C5B—C4B117.0 (3)N2E—C2E—C3E123.2 (3)
C6B—C5B—H5B121.5N1E—C2E—C3E118.3 (4)
C4B—C5B—H5B121.5C2E—N2E—H21E117 (3)
N1B—C6B—C5B127.2 (3)C2E—N2E—H22E121 (3)
N1B—C6B—Cl6B113.8 (3)H21E—N2E—H22E118 (4)
C5B—C6B—Cl6B119.0 (3)C4E—C3E—C2E120.0 (3)
C2C—N1C—C6C115.0 (3)C4E—C3E—H3E120.0
N1C—C2C—N2C119.5 (3)C2E—C3E—H3E120.0
N1C—C2C—N3C122.3 (3)C3E—C4E—C5E120.0 (4)
N2C—C2C—N3C118.2 (3)C3E—C4E—H4E120.0
C2C—N2C—H21C112 (3)C5E—C4E—H4E120.0
C2C—N2C—H22C118 (3)C6E—C5E—C4E118.3 (4)
H21C—N2C—H22C125 (4)C6E—C5E—H5E120.9
C2C—N3C—C4C122.9 (3)C4E—C5E—H5E120.9
C2C—N3C—H3C117 (3)N1E—C6E—C5E121.6 (3)
C4C—N3C—H3C120 (3)N1E—C6E—H6E119.2
O4C—C4C—N3C118.1 (3)C5E—C6E—H6E119.2
O4C—C4C—C5C127.1 (3)
C6A—N1A—C2A—N2A179.9 (3)C2C—N3C—C4C—O4C178.1 (3)
C6A—N1A—C2A—N3A0.9 (5)C2C—N3C—C4C—C5C1.4 (5)
N2A—C2A—N3A—C4A178.0 (3)O4C—C4C—C5C—C6C179.4 (4)
N1A—C2A—N3A—C4A1.0 (5)N3C—C4C—C5C—C6C0.1 (5)
C2A—N3A—C4A—O4A177.2 (3)C2C—N1C—C6C—C5C1.8 (5)
C2A—N3A—C4A—C5A2.5 (5)C2C—N1C—C6C—Cl6C178.2 (3)
O4A—C4A—C5A—C6A177.7 (3)C4C—C5C—C6C—N1C1.6 (6)
N3A—C4A—C5A—C6A2.1 (5)C4C—C5C—C6C—Cl6C178.5 (3)
C2A—N1A—C6A—C5A1.4 (5)C6D—N1D—C2D—N2D178.5 (3)
C2A—N1A—C6A—Cl6A178.4 (3)C6D—N1D—C2D—N3D0.7 (5)
C4A—C5A—C6A—N1A0.0 (6)N1D—C2D—N3D—C4D0.2 (6)
C4A—C5A—C6A—Cl6A179.7 (3)N2D—C2D—N3D—C4D178.1 (3)
C6B—N1B—C2B—N2B179.9 (3)C2D—N3D—C4D—O4D179.6 (4)
C6B—N1B—C2B—N3B1.2 (5)C2D—N3D—C4D—C5D0.8 (5)
N2B—C2B—N3B—C4B177.0 (3)O4D—C4D—C5D—C6D179.1 (4)
N1B—C2B—N3B—C4B4.1 (5)N3D—C4D—C5D—C6D1.4 (5)
C2B—N3B—C4B—O4B175.6 (3)C2D—N1D—C6D—C5D0.1 (6)
C2B—N3B—C4B—C5B5.4 (5)C2D—N1D—C6D—Cl6D179.6 (3)
O4B—C4B—C5B—C6B177.0 (4)C4D—C5D—C6D—N1D1.0 (6)
N3B—C4B—C5B—C6B4.2 (5)C4D—C5D—C6D—Cl6D179.3 (3)
C2B—N1B—C6B—C5B0.2 (5)C6E—N1E—C2E—N2E176.7 (3)
C2B—N1B—C6B—Cl6B180.0 (3)C6E—N1E—C2E—C3E3.2 (5)
C4B—C5B—C6B—N1B1.8 (6)N2E—C2E—C3E—C4E178.4 (3)
C4B—C5B—C6B—Cl6B178.5 (3)N1E—C2E—C3E—C4E1.5 (5)
C6C—N1C—C2C—N2C178.3 (3)C2E—C3E—C4E—C5E1.8 (5)
C6C—N1C—C2C—N3C0.3 (5)C3E—C4E—C5E—C6E3.6 (5)
N1C—C2C—N3C—C4C1.3 (5)C2E—N1E—C6E—C5E1.4 (5)
N2C—C2C—N3C—C4C176.7 (3)C4E—C5E—C6E—N1E2.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H21A···O4B0.89 (2)2.08 (2)2.960 (4)173 (4)
N2A—H22A···N1C0.88 (2)2.14 (2)3.014 (4)172 (4)
N2B—H21B···N1D0.87 (2)2.14 (2)3.016 (4)178 (4)
N2B—H22B···O4A0.90 (2)1.92 (2)2.820 (4)177 (4)
N3B—H3B···N3A0.88 (2)2.03 (2)2.893 (4)167 (4)
N2C—H21C···N1A0.88 (2)2.12 (2)2.999 (4)174 (4)
N3C—H3C···O4Di0.88 (2)1.85 (2)2.730 (4)174 (4)
N2D—H21D···N1B0.89 (2)2.06 (2)2.936 (4)171 (4)
N3D—H3D···O4Cii0.89 (2)1.88 (2)2.760 (4)170 (4)
N1E—H1E···O4A0.89 (2)1.70 (2)2.554 (4)160 (4)
N2E—H21E···O4Biii0.86 (2)2.08 (2)2.905 (4)161 (4)
N2E—H22E···O4Biv0.89 (2)2.26 (2)3.086 (4)155 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z1; (iii) x, y1, z; (iv) x+1, y+1, z+1.
(Ib) bis-(2-aminopyridin-1-ium 2-amino-6-chloro-4-oxo-4H-pyrimidin-3-ide)–[2-amino-6-chloropyrimidin-4(3H)-one]–2-aminopyridine (2/10/1) top
Crystal data top
2C5H7N2+·2C4H3ClN3O·10C4H4ClN3O·C5H6N2Z = 2
Mr = 2028.97F(000) = 2076
Triclinic, P1Dx = 1.628 Mg m3
a = 14.0097 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.0185 (7) ÅCell parameters from 38798 reflections
c = 21.4229 (11) Åθ = 1.7–27.0°
α = 83.774 (4)°µ = 0.49 mm1
β = 84.000 (4)°T = 173 K
γ = 83.554 (4)°Needle, colourless
V = 4137.9 (4) Å30.24 × 0.10 × 0.04 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
10620 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.026
ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1717
Tmin = 0.890, Tmax = 0.980k = 1717
20468 measured reflectionsl = 2626
16871 independent reflections
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)] = 0.136Hydrogen site location: mixed
wR(F2) = 0.379H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1287P)2 + 31.8979P]
where P = (Fo2 + 2Fc2)/3
16871 reflections(Δ/σ)max < 0.001
1350 parametersΔρmax = 1.51 e Å3
313 restraintsΔρmin = 1.23 e Å3
Crystal data top
2C5H7N2+·2C4H3ClN3O·10C4H4ClN3O·C5H6N2γ = 83.554 (4)°
Mr = 2028.97V = 4137.9 (4) Å3
Triclinic, P1Z = 2
a = 14.0097 (7) ÅMo Kα radiation
b = 14.0185 (7) ŵ = 0.49 mm1
c = 21.4229 (11) ÅT = 173 K
α = 83.774 (4)°0.24 × 0.10 × 0.04 mm
β = 84.000 (4)°
Data collection top
Stoe IPDSII two-circle
diffractometer
16871 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
10620 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.980Rint = 0.026
20468 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.136313 restraints
wR(F2) = 0.379H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1287P)2 + 31.8979P]
where P = (Fo2 + 2Fc2)/3
16871 reflectionsΔρmax = 1.51 e Å3
1350 parametersΔρmin = 1.23 e Å3
Special details top

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

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.8070 (6)0.1876 (6)0.0539 (4)0.0378 (19)
C2A0.8272 (7)0.1132 (7)0.0103 (4)0.032 (2)
N2A0.7919 (7)0.1203 (6)0.0490 (4)0.0377 (19)
H2A10.754 (6)0.171 (4)0.0612 (15)0.045*
H2A20.799 (7)0.073 (3)0.0790 (13)0.045*
N3A0.8834 (6)0.0318 (6)0.0253 (4)0.0340 (18)
H3A0.895 (8)0.015 (5)0.005 (3)0.041*
C4A0.9241 (7)0.0194 (6)0.0857 (5)0.033 (2)
O4A0.9772 (5)0.0576 (5)0.0950 (3)0.0390 (16)
C5A0.9006 (7)0.0955 (7)0.1325 (5)0.035 (2)
H5A0.92380.09220.17560.042*
C6A0.8433 (7)0.1735 (7)0.1128 (5)0.037 (2)
Cl6A0.8109 (2)0.26860 (18)0.16844 (12)0.0454 (6)
N1B0.9707 (6)0.2975 (6)0.0972 (4)0.0352 (18)
C2B0.9517 (7)0.2214 (6)0.0536 (4)0.0305 (19)
N2B0.9856 (7)0.2339 (6)0.0054 (4)0.039 (2)
H2B10.986 (8)0.187 (2)0.0359 (13)0.047*
H2B21.025 (6)0.284 (4)0.0158 (13)0.047*
N3B0.9001 (6)0.1365 (5)0.0659 (4)0.0316 (17)
C4B0.8655 (7)0.1254 (6)0.1247 (4)0.031 (2)
O4B0.8160 (6)0.0443 (5)0.1369 (3)0.0437 (18)
C5B0.8805 (7)0.2019 (7)0.1738 (5)0.037 (2)
H5B0.85520.19630.21630.045*
C6B0.9335 (8)0.2827 (7)0.1554 (5)0.037 (2)
Cl6B0.9569 (2)0.37946 (19)0.21292 (13)0.0484 (7)
N1C1.1026 (6)0.4340 (6)0.0268 (4)0.0387 (19)
C2C1.1197 (7)0.5009 (7)0.0211 (5)0.034 (2)
N2C1.0881 (7)0.4815 (6)0.0799 (4)0.042 (2)
H2C11.066 (8)0.4228 (19)0.0889 (15)0.050*
H2C21.097 (8)0.524 (3)0.1125 (9)0.050*
N3C1.1694 (6)0.5882 (6)0.0130 (4)0.0350 (18)
H3C1.176 (8)0.631 (6)0.046 (3)0.042*
C4C1.2057 (7)0.6156 (7)0.0468 (5)0.034 (2)
O4C1.2535 (5)0.6961 (5)0.0494 (3)0.0412 (17)
C5C1.1903 (8)0.5447 (7)0.0969 (5)0.040 (2)
H5C1.21580.55490.13880.048*
C6C1.1381 (7)0.4614 (7)0.0837 (5)0.037 (2)
Cl6C1.1113 (2)0.3749 (2)0.14599 (13)0.0496 (7)
N1D1.3220 (6)0.9898 (6)0.0840 (4)0.0349 (18)
C2D1.3019 (7)0.9198 (7)0.0384 (4)0.031 (2)
N2D1.3341 (7)0.9340 (6)0.0210 (4)0.039 (2)
H2D11.374 (6)0.985 (4)0.0304 (12)0.047*
H2D21.329 (8)0.888 (3)0.0521 (11)0.047*
N3D1.2528 (6)0.8345 (6)0.0508 (4)0.0343 (18)
H3D1.248 (8)0.794 (6)0.016 (3)0.041*
C4D1.2202 (7)0.8120 (7)0.1101 (5)0.033 (2)
O4D1.1777 (5)0.7284 (5)0.1189 (3)0.0394 (16)
C5D1.2398 (7)0.8858 (7)0.1605 (5)0.035 (2)
H5D1.21980.87660.20330.042*
C6D1.2881 (7)0.9685 (7)0.1433 (5)0.034 (2)
Cl6D1.3141 (2)1.06311 (19)0.20076 (12)0.0438 (6)
N1E1.4527 (6)1.1232 (6)0.0341 (4)0.0350 (18)
C2E1.4684 (7)1.1920 (6)0.0122 (5)0.033 (2)
N2E1.4337 (7)1.1762 (6)0.0710 (4)0.040 (2)
H2E11.401 (7)1.121 (3)0.0802 (14)0.048*
H2E21.444 (7)1.219 (4)0.1033 (10)0.048*
N3E1.5202 (6)1.2778 (6)0.0022 (4)0.0351 (18)
H3E1.535 (8)1.322 (6)0.033 (3)0.042*
C4E1.5597 (8)1.3009 (8)0.0572 (5)0.041 (2)
O4E1.6042 (6)1.3822 (5)0.0611 (3)0.0418 (17)
C5E1.5442 (7)1.2283 (7)0.1069 (5)0.035 (2)
H5E1.56951.23730.14900.041*
C6E1.4910 (7)1.1439 (7)0.0922 (5)0.035 (2)
Cl6E1.4673 (2)1.05247 (18)0.15099 (12)0.0427 (6)
N1F1.6781 (6)1.6819 (5)0.0737 (4)0.0342 (18)
C2F1.6636 (7)1.6118 (7)0.0267 (4)0.032 (2)
N2F1.6951 (7)1.6277 (6)0.0318 (4)0.039 (2)
H2F11.732 (7)1.680 (4)0.0420 (13)0.047*
H2F21.691 (8)1.584 (3)0.0642 (10)0.047*
N3F1.6143 (6)1.5252 (5)0.0380 (4)0.0341 (18)
H3F1.600 (8)1.479 (5)0.008 (3)0.041*
C4F1.5750 (8)1.5011 (7)0.0963 (5)0.037 (2)
O4F1.5300 (6)1.4199 (5)0.1026 (3)0.0426 (17)
C5F1.5915 (8)1.5741 (7)0.1467 (5)0.038 (2)
H5F1.56761.56430.18890.046*
C6F1.6431 (7)1.6594 (7)0.1320 (5)0.034 (2)
Cl6F1.6654 (2)1.74992 (19)0.19134 (13)0.0469 (7)
N1G0.8200 (6)0.0350 (5)0.5557 (4)0.0309 (17)
C2G0.7576 (7)0.0008 (7)0.5119 (5)0.034 (2)
N2G0.7896 (6)0.0102 (7)0.4517 (4)0.039 (2)
H2G10.7494 (18)0.007 (8)0.4224 (12)0.047*
H2G20.841 (5)0.050 (6)0.4418 (12)0.047*
N3G0.6706 (6)0.0473 (5)0.5244 (4)0.0331 (17)
C4G0.6411 (7)0.0639 (7)0.5845 (5)0.035 (2)
O4G0.5587 (5)0.1121 (5)0.5965 (3)0.0362 (15)
C5G0.6991 (7)0.0262 (7)0.6329 (5)0.033 (2)
H5G0.67920.03440.67600.040*
C6G0.7854 (7)0.0226 (7)0.6148 (4)0.031 (2)
Cl6G0.86379 (18)0.07143 (19)0.67053 (12)0.0410 (6)
N1H0.3919 (6)0.1808 (6)0.4014 (4)0.0342 (18)
C2H0.4505 (7)0.1451 (7)0.4446 (5)0.034 (2)
N2H0.4239 (6)0.1598 (6)0.5048 (4)0.0356 (18)
H2H10.366 (3)0.188 (7)0.5168 (14)0.043*
H2H20.465 (3)0.149 (8)0.5339 (13)0.043*
N3H0.5380 (6)0.0979 (6)0.4298 (4)0.0318 (17)
H3H0.572 (6)0.078 (7)0.462 (3)0.038*
C4H0.5718 (6)0.0785 (6)0.3694 (4)0.0283 (19)
O4H0.6520 (5)0.0335 (5)0.3583 (3)0.0388 (16)
C5H0.5104 (7)0.1178 (7)0.3216 (4)0.035 (2)
H5H0.52880.11140.27820.042*
C6H0.4243 (7)0.1648 (7)0.3416 (5)0.033 (2)
Cl6H0.34671 (19)0.2150 (2)0.28590 (12)0.0427 (6)
N1I0.2221 (6)0.2633 (6)0.5268 (4)0.0343 (18)
C2I0.1672 (7)0.2957 (7)0.4789 (5)0.035 (2)
N2I0.2013 (7)0.2836 (7)0.4204 (4)0.045 (2)
H2I10.261 (2)0.261 (8)0.4093 (14)0.054*
H2I20.169 (4)0.302 (8)0.3873 (9)0.054*
N3I0.0780 (6)0.3425 (6)0.4907 (4)0.0334 (18)
H3I0.040 (6)0.359 (8)0.461 (3)0.040*
C4I0.0360 (7)0.3598 (7)0.5500 (5)0.036 (2)
O4I0.0476 (5)0.4035 (5)0.5554 (3)0.0427 (17)
C5I0.0929 (7)0.3276 (7)0.6002 (5)0.035 (2)
H5I0.07100.33790.64260.042*
C6I0.1812 (7)0.2810 (7)0.5841 (5)0.036 (2)
Cl6I0.2543 (2)0.2356 (2)0.64367 (13)0.0458 (6)
N1K0.3005 (6)0.5248 (5)0.4172 (4)0.0321 (17)
C2K0.2457 (7)0.4941 (7)0.4638 (5)0.035 (2)
N2K0.2809 (6)0.5090 (6)0.5233 (4)0.0383 (19)
H2K10.342 (2)0.529 (8)0.5321 (15)0.046*
H2K20.245 (3)0.493 (8)0.5549 (10)0.046*
N3K0.1567 (6)0.4474 (6)0.4541 (4)0.0320 (17)
H3K0.121 (6)0.436 (8)0.486 (3)0.038*
C4K0.1135 (7)0.4307 (7)0.3947 (5)0.035 (2)
O4K0.0316 (5)0.3869 (5)0.3894 (3)0.0421 (17)
C5K0.1707 (8)0.4642 (7)0.3446 (5)0.037 (2)
H5K0.14770.45590.30210.044*
C6K0.2584 (8)0.5082 (7)0.3598 (5)0.037 (2)
Cl6K0.3318 (2)0.5513 (2)0.29917 (13)0.0462 (6)
N1L0.4776 (6)0.6115 (6)0.5423 (4)0.0345 (18)
C2L0.5317 (7)0.6457 (6)0.4955 (5)0.033 (2)
N2L0.4968 (6)0.6328 (7)0.4369 (4)0.041 (2)
H2L10.445 (5)0.593 (6)0.4272 (12)0.049*
H2L20.532 (2)0.641 (8)0.4049 (11)0.049*
N3L0.6201 (6)0.6923 (6)0.5061 (4)0.0335 (18)
H3L0.656 (8)0.710 (8)0.482 (5)0.040*
C4L0.6646 (7)0.7103 (6)0.5665 (4)0.0281 (19)
O4L0.7475 (5)0.7521 (5)0.5710 (3)0.0386 (16)
C5L0.6064 (7)0.6761 (7)0.6159 (5)0.034 (2)
H5L0.62860.68640.65830.040*
C6L0.5184 (7)0.6286 (7)0.6018 (5)0.032 (2)
Cl6L0.4470 (2)0.5796 (2)0.66006 (13)0.0448 (6)
N1M1.0047 (6)0.8800 (6)0.4321 (4)0.0354 (18)
C2M0.9486 (7)0.8539 (6)0.4784 (5)0.031 (2)
N2M0.9815 (6)0.8748 (7)0.5375 (4)0.040 (2)
H2M11.040 (3)0.904 (7)0.5450 (15)0.048*
H2M20.946 (4)0.857 (7)0.5689 (11)0.048*
N3M0.8590 (6)0.8073 (6)0.4699 (4)0.0318 (17)
H3M0.822 (8)0.785 (8)0.505 (5)0.038*
C4M0.8184 (7)0.7827 (7)0.4117 (4)0.031 (2)
O4M0.7358 (5)0.7379 (5)0.4070 (3)0.0389 (16)
C5M0.8756 (7)0.8111 (8)0.3600 (5)0.038 (2)
H5M0.85330.79920.31790.046*
C6M0.9635 (7)0.8559 (7)0.3756 (5)0.035 (2)
Cl6M1.0380 (2)0.8939 (2)0.31489 (12)0.0435 (6)
N1O0.4965 (6)0.8227 (6)0.2960 (4)0.0344 (18)
H1O0.528 (8)0.850 (8)0.334 (5)0.041*
C3O0.4774 (8)0.7158 (7)0.2161 (5)0.037 (2)
H3O0.49720.66230.19890.045*
C6O0.4212 (7)0.8666 (7)0.2681 (5)0.038 (2)
H6O0.40080.91850.28670.045*
C2O0.5275 (7)0.7503 (7)0.2715 (4)0.031 (2)
N2O0.6046 (7)0.7081 (7)0.3007 (5)0.048 (2)
H2O10.636 (5)0.730 (6)0.335 (3)0.058*
H2O20.608 (5)0.646 (2)0.299 (5)0.058*
C4O0.4012 (7)0.7601 (7)0.1882 (5)0.038 (2)
H4O0.36710.73730.15110.045*
C5O0.3720 (7)0.8377 (8)0.2124 (5)0.041 (2)
H5O0.31990.87050.19190.049*
N1P0.9210 (6)0.1114 (5)0.2057 (3)0.0333 (18)
H1P0.931 (4)0.079 (5)0.172 (2)0.040*
C2P0.8464 (7)0.0993 (6)0.2538 (4)0.031 (2)
N2P0.7876 (7)0.0364 (7)0.2480 (4)0.040 (2)
H2P10.794 (4)0.004 (5)0.219 (3)0.048*
H2P20.730 (3)0.032 (5)0.269 (4)0.048*
C6P0.9861 (8)0.1762 (8)0.2108 (5)0.045 (3)
H6P1.03700.18250.17810.054*
C5P0.9827 (9)0.2299 (9)0.2579 (6)0.050 (3)
H5P1.02910.27370.25980.060*
C4P0.9059 (8)0.2184 (7)0.3052 (5)0.038 (2)
H4P0.90000.25720.33940.045*
C3P0.8420 (7)0.1566 (7)0.3043 (4)0.033 (2)
H3P0.79250.15060.33800.040*
N1R1.7088 (7)1.5563 (6)0.2592 (4)0.0416 (18)
C2R1.7214 (16)1.4963 (15)0.2174 (11)0.041 (5)0.522 (16)
N2R1.6537 (14)1.5003 (11)0.1663 (9)0.046 (4)0.522 (16)
H2R11.618 (9)1.549 (7)0.161 (5)0.055*0.522 (16)
H2R21.639 (11)1.449 (5)0.146 (6)0.055*0.522 (16)
C3R1.788 (2)1.431 (2)0.2198 (17)0.042 (5)0.522 (16)
H3R1.78661.38630.18920.050*0.522 (16)
C4R1.857 (2)1.435 (2)0.2704 (14)0.045 (5)0.522 (16)
H4R1.90661.39340.27530.054*0.522 (16)
C5R1.8550 (15)1.5039 (14)0.3160 (10)0.038 (4)0.522 (16)
H5R1.90211.51030.35090.045*0.522 (16)
C6R1.7826 (18)1.5560 (19)0.3048 (12)0.038 (4)0.522 (16)
H6R1.78161.60200.33420.046*0.522 (16)
C2S1.783 (2)1.5204 (19)0.2933 (12)0.035 (4)0.478 (16)
N2S1.8026 (13)1.5677 (13)0.3489 (10)0.043 (5)0.478 (16)
H2S11.8644 (18)1.582 (15)0.360 (6)0.051*0.478 (16)
H2S21.757 (6)1.601 (11)0.357 (5)0.051*0.478 (16)
C3S1.840 (2)1.4626 (19)0.2806 (14)0.034 (4)0.478 (16)
H3S1.89721.45130.30650.041*0.478 (16)
C4S1.813 (2)1.418 (3)0.2278 (17)0.039 (6)0.478 (16)
H4S1.85141.37210.21710.046*0.478 (16)
C5S1.7279 (16)1.4377 (14)0.1872 (10)0.036 (4)0.478 (16)
H5S1.70651.40690.15010.044*0.478 (16)
C6S1.684 (2)1.5034 (18)0.2079 (13)0.037 (5)0.478 (16)
H6S1.62581.51750.18380.044*0.478 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.040 (5)0.035 (4)0.038 (5)0.001 (4)0.003 (4)0.003 (4)
C2A0.032 (5)0.029 (5)0.034 (5)0.001 (4)0.003 (4)0.002 (4)
N2A0.042 (5)0.033 (4)0.036 (4)0.001 (4)0.002 (4)0.002 (3)
N3A0.034 (4)0.028 (4)0.039 (5)0.001 (3)0.002 (4)0.004 (3)
C4A0.036 (5)0.024 (4)0.039 (5)0.001 (4)0.005 (4)0.000 (4)
O4A0.044 (4)0.032 (4)0.039 (4)0.005 (3)0.001 (3)0.004 (3)
C5A0.043 (6)0.032 (5)0.029 (5)0.003 (4)0.003 (4)0.002 (4)
C6A0.035 (5)0.035 (5)0.039 (5)0.002 (4)0.001 (4)0.002 (4)
Cl6A0.0614 (17)0.0336 (13)0.0381 (13)0.0053 (11)0.0092 (12)0.0035 (10)
N1B0.042 (5)0.025 (4)0.039 (4)0.000 (3)0.005 (4)0.004 (3)
C2B0.032 (5)0.026 (4)0.034 (5)0.003 (4)0.004 (4)0.004 (4)
N2B0.051 (5)0.024 (4)0.038 (5)0.011 (4)0.001 (4)0.004 (3)
N3B0.033 (4)0.024 (4)0.037 (4)0.003 (3)0.006 (3)0.007 (3)
C4B0.037 (5)0.026 (4)0.030 (5)0.007 (4)0.001 (4)0.005 (4)
O4B0.060 (5)0.032 (4)0.035 (4)0.007 (3)0.001 (3)0.005 (3)
C5B0.042 (6)0.035 (5)0.033 (5)0.000 (4)0.000 (4)0.002 (4)
C6B0.041 (6)0.033 (5)0.036 (5)0.005 (4)0.000 (4)0.001 (4)
Cl6B0.0613 (18)0.0395 (14)0.0401 (14)0.0027 (12)0.0058 (12)0.0081 (11)
N1C0.040 (5)0.027 (4)0.047 (5)0.005 (3)0.004 (4)0.005 (3)
C2C0.029 (5)0.030 (5)0.041 (5)0.000 (4)0.003 (4)0.002 (4)
N2C0.062 (6)0.028 (4)0.032 (4)0.008 (4)0.003 (4)0.002 (3)
N3C0.040 (5)0.028 (4)0.037 (4)0.002 (3)0.003 (4)0.006 (3)
C4C0.029 (5)0.027 (5)0.046 (6)0.010 (4)0.003 (4)0.001 (4)
O4C0.049 (4)0.031 (4)0.041 (4)0.005 (3)0.006 (3)0.003 (3)
C5C0.042 (6)0.037 (5)0.041 (6)0.006 (4)0.008 (5)0.001 (4)
C6C0.036 (5)0.034 (5)0.042 (6)0.007 (4)0.006 (4)0.002 (4)
Cl6C0.0613 (18)0.0417 (14)0.0432 (14)0.0007 (12)0.0101 (13)0.0084 (11)
N1D0.040 (5)0.031 (4)0.034 (4)0.002 (3)0.007 (4)0.004 (3)
C2D0.030 (5)0.033 (5)0.033 (5)0.008 (4)0.004 (4)0.005 (4)
N2D0.052 (6)0.034 (5)0.029 (4)0.008 (4)0.002 (4)0.001 (3)
N3D0.044 (5)0.026 (4)0.031 (4)0.001 (3)0.004 (4)0.001 (3)
C4D0.032 (5)0.030 (5)0.037 (5)0.003 (4)0.003 (4)0.003 (4)
O4D0.049 (4)0.027 (3)0.042 (4)0.002 (3)0.007 (3)0.009 (3)
C5D0.036 (5)0.036 (5)0.035 (5)0.000 (4)0.011 (4)0.001 (4)
C6D0.034 (5)0.037 (5)0.033 (5)0.008 (4)0.001 (4)0.000 (4)
Cl6D0.0604 (17)0.0384 (13)0.0305 (12)0.0029 (12)0.0086 (11)0.0018 (10)
N1E0.044 (5)0.029 (4)0.030 (4)0.001 (3)0.005 (4)0.001 (3)
C2E0.038 (5)0.021 (4)0.038 (5)0.002 (4)0.005 (4)0.000 (4)
N2E0.053 (6)0.031 (4)0.033 (4)0.011 (4)0.008 (4)0.000 (3)
N3E0.042 (5)0.029 (4)0.033 (4)0.002 (3)0.001 (4)0.004 (3)
C4E0.035 (5)0.036 (5)0.050 (6)0.001 (4)0.008 (5)0.005 (5)
O4E0.052 (5)0.035 (4)0.035 (4)0.013 (3)0.004 (3)0.006 (3)
C5E0.037 (5)0.028 (5)0.035 (5)0.002 (4)0.000 (4)0.001 (4)
C6E0.034 (5)0.036 (5)0.034 (5)0.002 (4)0.009 (4)0.002 (4)
Cl6E0.0557 (16)0.0359 (13)0.0351 (12)0.0012 (11)0.0106 (11)0.0025 (10)
N1F0.043 (5)0.022 (4)0.036 (4)0.003 (3)0.005 (4)0.003 (3)
C2F0.034 (5)0.027 (5)0.035 (5)0.001 (4)0.004 (4)0.006 (4)
N2F0.047 (5)0.029 (4)0.039 (5)0.011 (4)0.003 (4)0.002 (3)
N3F0.037 (5)0.022 (4)0.039 (4)0.009 (3)0.001 (4)0.002 (3)
C4F0.043 (6)0.026 (5)0.039 (5)0.006 (4)0.004 (4)0.004 (4)
O4F0.056 (5)0.030 (4)0.039 (4)0.003 (3)0.004 (3)0.006 (3)
C5F0.044 (6)0.041 (6)0.029 (5)0.004 (4)0.003 (4)0.001 (4)
C6F0.033 (5)0.028 (5)0.041 (5)0.001 (4)0.007 (4)0.003 (4)
Cl6F0.0528 (16)0.0386 (13)0.0463 (14)0.0010 (11)0.0107 (12)0.0090 (11)
N1G0.031 (4)0.028 (4)0.032 (4)0.003 (3)0.000 (3)0.005 (3)
C2G0.029 (5)0.038 (5)0.035 (5)0.004 (4)0.003 (4)0.000 (4)
N2G0.034 (5)0.050 (5)0.031 (4)0.009 (4)0.005 (4)0.003 (4)
N3G0.038 (5)0.024 (4)0.038 (4)0.003 (3)0.008 (4)0.004 (3)
C4G0.027 (5)0.044 (6)0.035 (5)0.004 (4)0.003 (4)0.003 (4)
O4G0.030 (4)0.040 (4)0.037 (4)0.005 (3)0.001 (3)0.007 (3)
C5G0.026 (5)0.039 (5)0.032 (5)0.000 (4)0.000 (4)0.005 (4)
C6G0.027 (5)0.030 (5)0.034 (5)0.000 (4)0.001 (4)0.003 (4)
Cl6G0.0363 (13)0.0479 (14)0.0358 (12)0.0048 (10)0.0054 (10)0.0021 (10)
N1H0.036 (4)0.033 (4)0.034 (4)0.001 (3)0.008 (3)0.004 (3)
C2H0.034 (5)0.031 (5)0.037 (5)0.002 (4)0.001 (4)0.007 (4)
N2H0.028 (4)0.043 (5)0.034 (4)0.003 (4)0.003 (3)0.008 (4)
N3H0.028 (4)0.029 (4)0.037 (4)0.004 (3)0.007 (3)0.004 (3)
C4H0.027 (5)0.029 (4)0.029 (4)0.001 (4)0.002 (4)0.007 (4)
O4H0.034 (4)0.046 (4)0.037 (4)0.003 (3)0.005 (3)0.013 (3)
C5H0.042 (6)0.034 (5)0.027 (5)0.001 (4)0.002 (4)0.004 (4)
C6H0.034 (5)0.033 (5)0.033 (5)0.001 (4)0.001 (4)0.004 (4)
Cl6H0.0392 (14)0.0522 (15)0.0357 (13)0.0039 (11)0.0110 (10)0.0020 (11)
N1I0.032 (4)0.032 (4)0.038 (4)0.000 (3)0.008 (3)0.001 (3)
C2I0.032 (5)0.033 (5)0.041 (5)0.001 (4)0.008 (4)0.003 (4)
N2I0.045 (5)0.047 (5)0.038 (5)0.012 (4)0.001 (4)0.006 (4)
N3I0.033 (4)0.030 (4)0.037 (4)0.002 (3)0.009 (3)0.001 (3)
C4I0.033 (5)0.030 (5)0.046 (6)0.009 (4)0.001 (4)0.005 (4)
O4I0.034 (4)0.050 (4)0.043 (4)0.006 (3)0.004 (3)0.007 (3)
C5I0.039 (6)0.037 (5)0.030 (5)0.006 (4)0.002 (4)0.006 (4)
C6I0.038 (5)0.033 (5)0.036 (5)0.001 (4)0.009 (4)0.004 (4)
Cl6I0.0439 (15)0.0499 (15)0.0431 (14)0.0035 (12)0.0136 (12)0.0063 (11)
N1K0.035 (4)0.027 (4)0.032 (4)0.003 (3)0.003 (3)0.000 (3)
C2K0.038 (5)0.029 (5)0.037 (5)0.007 (4)0.005 (4)0.002 (4)
N2K0.036 (5)0.041 (5)0.037 (5)0.000 (4)0.004 (4)0.001 (4)
N3K0.030 (4)0.037 (4)0.027 (4)0.000 (3)0.004 (3)0.000 (3)
C4K0.031 (5)0.027 (5)0.044 (6)0.004 (4)0.006 (4)0.003 (4)
O4K0.036 (4)0.047 (4)0.042 (4)0.005 (3)0.004 (3)0.007 (3)
C5K0.044 (6)0.036 (5)0.031 (5)0.004 (4)0.001 (4)0.005 (4)
C6K0.043 (6)0.029 (5)0.038 (5)0.002 (4)0.013 (4)0.002 (4)
Cl6K0.0470 (15)0.0502 (15)0.0401 (14)0.0031 (12)0.0149 (12)0.0029 (11)
N1L0.031 (4)0.035 (4)0.036 (4)0.005 (3)0.009 (3)0.000 (3)
C2L0.030 (5)0.027 (5)0.041 (5)0.003 (4)0.003 (4)0.008 (4)
N2L0.038 (5)0.045 (5)0.037 (5)0.006 (4)0.001 (4)0.008 (4)
N3L0.027 (4)0.036 (4)0.036 (4)0.008 (3)0.003 (3)0.007 (3)
C4L0.031 (5)0.020 (4)0.032 (5)0.000 (3)0.002 (4)0.002 (3)
O4L0.035 (4)0.039 (4)0.041 (4)0.010 (3)0.005 (3)0.008 (3)
C5L0.038 (5)0.030 (5)0.033 (5)0.005 (4)0.008 (4)0.003 (4)
C6L0.026 (5)0.035 (5)0.035 (5)0.000 (4)0.005 (4)0.003 (4)
Cl6L0.0429 (14)0.0500 (15)0.0403 (13)0.0030 (11)0.0133 (11)0.0018 (11)
N1M0.039 (5)0.033 (4)0.035 (4)0.004 (3)0.002 (4)0.010 (3)
C2M0.027 (5)0.027 (4)0.039 (5)0.000 (4)0.001 (4)0.006 (4)
N2M0.039 (5)0.050 (5)0.029 (4)0.008 (4)0.002 (4)0.015 (4)
N3M0.031 (4)0.029 (4)0.035 (4)0.001 (3)0.001 (3)0.011 (3)
C4M0.034 (5)0.032 (5)0.028 (5)0.006 (4)0.002 (4)0.010 (4)
O4M0.031 (4)0.045 (4)0.037 (4)0.006 (3)0.001 (3)0.007 (3)
C5M0.037 (5)0.044 (6)0.033 (5)0.006 (4)0.002 (4)0.006 (4)
C6M0.034 (5)0.035 (5)0.037 (5)0.006 (4)0.002 (4)0.009 (4)
Cl6M0.0428 (14)0.0506 (15)0.0377 (13)0.0031 (11)0.0125 (11)0.0001 (11)
N1O0.036 (5)0.033 (4)0.031 (4)0.002 (3)0.001 (4)0.001 (3)
C3O0.046 (6)0.034 (5)0.033 (5)0.005 (4)0.007 (4)0.007 (4)
C6O0.038 (6)0.029 (5)0.050 (6)0.009 (4)0.014 (5)0.009 (4)
C2O0.034 (5)0.030 (5)0.030 (5)0.005 (4)0.009 (4)0.005 (4)
N2O0.046 (6)0.048 (6)0.055 (6)0.016 (4)0.006 (5)0.017 (5)
C4O0.035 (5)0.040 (5)0.033 (5)0.005 (4)0.005 (4)0.001 (4)
C5O0.031 (5)0.050 (6)0.036 (5)0.005 (4)0.003 (4)0.006 (5)
N1P0.039 (5)0.033 (4)0.025 (4)0.002 (3)0.001 (3)0.000 (3)
C2P0.042 (6)0.027 (5)0.023 (4)0.000 (4)0.004 (4)0.001 (3)
N2P0.042 (5)0.042 (5)0.037 (5)0.004 (4)0.002 (4)0.009 (4)
C6P0.035 (6)0.051 (7)0.043 (6)0.000 (5)0.002 (5)0.015 (5)
C5P0.046 (7)0.046 (6)0.058 (7)0.012 (5)0.011 (6)0.010 (5)
C4P0.050 (6)0.029 (5)0.036 (5)0.000 (4)0.015 (5)0.005 (4)
C3P0.034 (5)0.039 (5)0.026 (4)0.003 (4)0.005 (4)0.008 (4)
N1R0.047 (5)0.036 (4)0.043 (4)0.005 (4)0.008 (3)0.008 (3)
C2R0.046 (11)0.043 (10)0.034 (9)0.002 (8)0.010 (7)0.007 (7)
N2R0.050 (10)0.032 (9)0.055 (10)0.003 (7)0.003 (8)0.010 (8)
C3R0.045 (12)0.037 (10)0.043 (10)0.003 (8)0.007 (8)0.010 (8)
C4R0.049 (11)0.042 (12)0.044 (11)0.005 (8)0.002 (9)0.007 (8)
C5R0.038 (8)0.038 (9)0.036 (9)0.004 (7)0.006 (7)0.002 (7)
C6R0.043 (9)0.048 (13)0.024 (9)0.002 (9)0.012 (6)0.001 (8)
C2S0.037 (9)0.037 (11)0.031 (9)0.004 (8)0.007 (7)0.003 (7)
N2S0.039 (10)0.035 (10)0.055 (10)0.009 (8)0.006 (8)0.021 (8)
C3S0.040 (10)0.029 (11)0.034 (9)0.004 (7)0.007 (8)0.008 (7)
C4S0.037 (12)0.039 (12)0.039 (11)0.002 (9)0.006 (9)0.010 (8)
C5S0.038 (10)0.032 (9)0.037 (9)0.002 (7)0.000 (7)0.002 (7)
C6S0.042 (12)0.030 (9)0.036 (10)0.000 (8)0.002 (9)0.001 (7)
Geometric parameters (Å, º) top
N1A—C6A1.337 (13)C2I—N2I1.316 (13)
N1A—C2A1.350 (12)C2I—N3I1.356 (12)
C2A—N2A1.323 (13)N2I—H2I10.881 (5)
C2A—N3A1.360 (12)N2I—H2I20.880 (5)
N2A—H2A10.880 (5)N3I—C4I1.378 (13)
N2A—H2A20.881 (5)N3I—H3I0.880 (5)
N3A—C4A1.380 (13)C4I—O4I1.260 (12)
N3A—H3A0.880 (5)C4I—C5I1.410 (14)
C4A—O4A1.262 (11)C5I—C6I1.361 (14)
C4A—C5A1.418 (13)C5I—H5I0.9500
C5A—C6A1.361 (14)C6I—Cl6I1.742 (10)
C5A—H5A0.9500N1K—C2K1.330 (12)
C6A—Cl6A1.742 (10)N1K—C6K1.339 (13)
N1B—C6B1.328 (13)C2K—N2K1.345 (13)
N1B—C2B1.362 (12)C2K—N3K1.349 (13)
C2B—N2B1.325 (13)N2K—H2K10.880 (5)
C2B—N3B1.357 (11)N2K—H2K20.880 (5)
N2B—H2B10.880 (5)N3K—C4K1.382 (13)
N2B—H2B20.880 (5)N3K—H3K0.880 (5)
N3B—C4B1.321 (12)C4K—O4K1.240 (11)
C4B—O4B1.300 (11)C4K—C5K1.413 (14)
C4B—C5B1.433 (13)C5K—C6K1.337 (14)
C5B—C6B1.355 (14)C5K—H5K0.9500
C5B—H5B0.9500C6K—Cl6K1.754 (10)
C6B—Cl6B1.757 (10)N1L—C2L1.334 (12)
N1C—C2C1.335 (13)N1L—C6L1.376 (12)
N1C—C6C1.347 (13)C2L—N2L1.322 (13)
C2C—N2C1.337 (13)C2L—N3L1.343 (12)
C2C—N3C1.357 (12)N2L—H2L10.880 (5)
N2C—H2C10.880 (5)N2L—H2L20.880 (5)
N2C—H2C20.880 (5)N3L—C4L1.412 (12)
N3C—C4C1.404 (13)N3L—H3L0.77 (11)
N3C—H3C0.880 (5)C4L—O4L1.241 (11)
C4C—O4C1.251 (11)C4L—C5L1.412 (13)
C4C—C5C1.398 (14)C5L—C6L1.355 (13)
C5C—C6C1.347 (14)C5L—H5L0.9500
C5C—H5C0.9500C6L—Cl6L1.718 (10)
C6C—Cl6C1.743 (10)N1M—C2M1.325 (12)
N1D—C2D1.335 (12)N1M—C6M1.346 (12)
N1D—C6D1.360 (12)C2M—N3M1.352 (12)
C2D—N2D1.335 (12)C2M—N2M1.353 (12)
C2D—N3D1.349 (12)N2M—H2M10.880 (5)
N2D—H2D10.880 (5)N2M—H2M20.880 (5)
N2D—H2D20.879 (5)N3M—C4M1.378 (11)
N3D—C4D1.362 (12)N3M—H3M0.96 (11)
N3D—H3D0.880 (5)C4M—O4M1.252 (11)
C4D—O4D1.277 (11)C4M—C5M1.430 (14)
C4D—C5D1.436 (13)C5M—C6M1.345 (14)
C5D—C6D1.342 (14)C5M—H5M0.9500
C5D—H5D0.9500C6M—Cl6M1.752 (10)
C6D—Cl6D1.744 (10)N1O—C2O1.326 (13)
N1E—C2E1.324 (12)N1O—C6O1.336 (13)
N1E—C6E1.352 (13)N1O—H1O0.97 (11)
C2E—N2E1.335 (13)C3O—C4O1.349 (15)
C2E—N3E1.359 (12)C3O—C2O1.417 (14)
N2E—H2E10.880 (5)C3O—H3O0.9500
N2E—H2E20.880 (5)C6O—C5O1.390 (15)
N3E—C4E1.389 (14)C6O—H6O0.9500
N3E—H3E0.880 (5)C2O—N2O1.353 (13)
C4E—O4E1.244 (12)N2O—H2O10.881 (5)
C4E—C5E1.408 (14)N2O—H2O20.881 (5)
C5E—C6E1.375 (13)C4O—C5O1.374 (16)
C5E—H5E0.9500C4O—H4O0.9500
C6E—Cl6E1.726 (10)C5O—H5O0.9500
N1F—C2F1.344 (12)N1P—C6P1.377 (12)
N1F—C6F1.350 (13)N1P—C2P1.400 (11)
C2F—N2F1.319 (13)N1P—H1P0.891 (5)
C2F—N3F1.361 (11)C2P—N2P1.296 (13)
N2F—H2F10.881 (5)C2P—C3P1.408 (12)
N2F—H2F20.880 (5)N2P—H2P10.880 (5)
N3F—C4F1.371 (13)N2P—H2P20.880 (5)
N3F—H3F0.880 (5)C6P—C5P1.316 (16)
C4F—O4F1.251 (11)C6P—H6P0.9500
C4F—C5F1.424 (13)C5P—C4P1.409 (16)
C5F—C6F1.375 (14)C5P—H5P0.9500
C5F—H5F0.9500C4P—C3P1.318 (15)
C6F—Cl6F1.723 (10)C4P—H4P0.9500
N1G—C6G1.331 (12)C3P—H3P0.9500
N1G—C2G1.366 (12)N1R—C2S1.32 (3)
C2G—N3G1.332 (12)N1R—C2R1.33 (3)
C2G—N2G1.341 (13)N1R—C6R1.35 (3)
N2G—H2G10.880 (5)N1R—C6S1.38 (3)
N2G—H2G20.880 (5)C2R—N2R1.37 (3)
N3G—C4G1.348 (12)C2R—C3R1.37 (4)
C4G—O4G1.287 (11)N2R—H2R10.880 (5)
C4G—C5G1.406 (13)N2R—H2R20.880 (5)
C5G—C6G1.361 (13)C3R—C4R1.38 (4)
C5G—H5G0.9500C3R—H3R0.9500
C6G—Cl6G1.740 (9)C4R—C5R1.45 (3)
N1H—C2H1.323 (12)C4R—H4R0.9500
N1H—C6H1.347 (12)C5R—C6R1.30 (3)
C2H—N2H1.335 (12)C5R—H5R0.9500
C2H—N3H1.350 (12)C6R—H6R0.9500
N2H—H2H10.881 (5)C2S—C3S1.27 (4)
N2H—H2H20.880 (5)C2S—N2S1.41 (3)
N3H—C4H1.377 (12)N2S—H2S10.880 (5)
N3H—H3H0.880 (5)N2S—H2S20.880 (5)
C4H—O4H1.240 (11)C3S—C4S1.35 (4)
C4H—C5H1.430 (13)C3S—H3S0.9500
C5H—C6H1.359 (13)C4S—C5S1.43 (3)
C5H—H5H0.9500C4S—H4S0.9500
C6H—Cl6H1.736 (10)C5S—C6S1.30 (4)
N1I—C6I1.336 (13)C5S—H5S0.9500
N1I—C2I1.355 (12)C6S—H6S0.9500
C6A—N1A—C2A115.0 (8)C2I—N2I—H2I1123.8 (19)
N2A—C2A—N1A118.8 (8)C2I—N2I—H2I2124.2 (19)
N2A—C2A—N3A119.2 (8)H2I1—N2I—H2I2112 (4)
N1A—C2A—N3A122.0 (9)C2I—N3I—C4I124.3 (9)
C2A—N2A—H2A1123.2 (18)C2I—N3I—H3I122 (7)
C2A—N2A—H2A2123.0 (18)C4I—N3I—H3I114 (7)
H2A1—N2A—H2A2113 (3)O4I—C4I—N3I118.9 (9)
C2A—N3A—C4A122.8 (8)O4I—C4I—C5I125.3 (10)
C2A—N3A—H3A119 (7)N3I—C4I—C5I115.7 (9)
C4A—N3A—H3A118 (7)C6I—C5I—C4I116.0 (9)
O4A—C4A—N3A118.4 (8)C6I—C5I—H5I122.0
O4A—C4A—C5A125.7 (9)C4I—C5I—H5I122.0
N3A—C4A—C5A115.9 (8)N1I—C6I—C5I128.6 (9)
C6A—C5A—C4A116.8 (9)N1I—C6I—Cl6I112.6 (7)
C6A—C5A—H5A121.6C5I—C6I—Cl6I118.8 (8)
C4A—C5A—H5A121.6C2K—N1K—C6K114.2 (8)
N1A—C6A—C5A127.5 (9)N1K—C2K—N2K118.7 (9)
N1A—C6A—Cl6A113.7 (7)N1K—C2K—N3K122.6 (9)
C5A—C6A—Cl6A118.8 (8)N2K—C2K—N3K118.7 (9)
C6B—N1B—C2B113.9 (8)C2K—N2K—H2K1120.8 (18)
N2B—C2B—N3B118.8 (8)C2K—N2K—H2K2121.0 (18)
N2B—C2B—N1B116.0 (8)H2K1—N2K—H2K2118 (3)
N3B—C2B—N1B125.2 (9)C2K—N3K—C4K122.9 (8)
C2B—N2B—H2B1123.0 (18)C2K—N3K—H3K118 (7)
C2B—N2B—H2B2123.0 (18)C4K—N3K—H3K118 (7)
H2B1—N2B—H2B2112 (4)O4K—C4K—N3K119.3 (9)
C4B—N3B—C2B118.3 (8)O4K—C4K—C5K125.8 (10)
O4B—C4B—N3B118.7 (8)N3K—C4K—C5K114.9 (8)
O4B—C4B—C5B120.7 (8)C6K—C5K—C4K117.1 (9)
N3B—C4B—C5B120.6 (8)C6K—C5K—H5K121.4
C6B—C5B—C4B115.3 (9)C4K—C5K—H5K121.4
C6B—C5B—H5B122.4C5K—C6K—N1K128.2 (9)
C4B—C5B—H5B122.4C5K—C6K—Cl6K118.8 (8)
N1B—C6B—C5B126.6 (9)N1K—C6K—Cl6K113.1 (7)
N1B—C6B—Cl6B115.1 (7)C2L—N1L—C6L115.2 (8)
C5B—C6B—Cl6B118.3 (8)N2L—C2L—N1L118.7 (8)
C2C—N1C—C6C114.0 (8)N2L—C2L—N3L119.2 (9)
N1C—C2C—N2C119.2 (8)N1L—C2L—N3L122.1 (9)
N1C—C2C—N3C122.9 (9)C2L—N2L—H2L1123.6 (19)
N2C—C2C—N3C118.0 (9)C2L—N2L—H2L2123.4 (19)
C2C—N2C—H2C1121.9 (18)H2L1—N2L—H2L2108 (5)
C2C—N2C—H2C2121.6 (18)C2L—N3L—C4L124.2 (9)
H2C1—N2C—H2C2116 (4)C2L—N3L—H3L127 (9)
C2C—N3C—C4C122.4 (8)C4L—N3L—H3L109 (9)
C2C—N3C—H3C119 (7)O4L—C4L—N3L118.8 (8)
C4C—N3C—H3C118 (7)O4L—C4L—C5L127.5 (9)
O4C—C4C—C5C127.0 (10)N3L—C4L—C5L113.7 (8)
O4C—C4C—N3C117.8 (9)C6L—C5L—C4L119.0 (9)
C5C—C4C—N3C115.0 (9)C6L—C5L—H5L120.5
C6C—C5C—C4C117.7 (10)C4L—C5L—H5L120.5
C6C—C5C—H5C121.1C5L—C6L—N1L125.8 (9)
C4C—C5C—H5C121.1C5L—C6L—Cl6L121.2 (8)
N1C—C6C—C5C128.0 (10)N1L—C6L—Cl6L113.0 (7)
N1C—C6C—Cl6C113.4 (7)C2M—N1M—C6M113.3 (8)
C5C—C6C—Cl6C118.6 (8)N1M—C2M—N3M123.5 (9)
C2D—N1D—C6D114.7 (8)N1M—C2M—N2M119.0 (8)
N2D—C2D—N1D118.6 (8)N3M—C2M—N2M117.6 (9)
N2D—C2D—N3D119.2 (8)C2M—N2M—H2M1120.2 (17)
N1D—C2D—N3D122.2 (8)C2M—N2M—H2M2120.2 (17)
C2D—N2D—H2D1121.8 (18)H2M1—N2M—H2M2120 (3)
C2D—N2D—H2D2122.2 (18)C2M—N3M—C4M122.4 (9)
H2D1—N2D—H2D2114 (4)C2M—N3M—H3M121 (6)
C2D—N3D—C4D123.3 (8)C4M—N3M—H3M117 (6)
C2D—N3D—H3D112 (7)O4M—C4M—N3M119.4 (9)
C4D—N3D—H3D125 (7)O4M—C4M—C5M124.4 (9)
O4D—C4D—N3D120.3 (9)N3M—C4M—C5M116.2 (9)
O4D—C4D—C5D123.6 (9)C6M—C5M—C4M114.9 (9)
N3D—C4D—C5D116.1 (8)C6M—C5M—H5M122.5
C6D—C5D—C4D116.0 (9)C4M—C5M—H5M122.5
C6D—C5D—H5D122.0C5M—C6M—N1M129.8 (10)
C4D—C5D—H5D122.0C5M—C6M—Cl6M117.8 (8)
C5D—C6D—N1D127.6 (9)N1M—C6M—Cl6M112.4 (7)
C5D—C6D—Cl6D119.5 (8)C2O—N1O—C6O121.3 (9)
N1D—C6D—Cl6D112.9 (7)C2O—N1O—H1O124 (7)
C2E—N1E—C6E115.7 (8)C6O—N1O—H1O115 (7)
N1E—C2E—N2E119.1 (8)C4O—C3O—C2O118.9 (9)
N1E—C2E—N3E122.4 (9)C4O—C3O—H3O120.5
N2E—C2E—N3E118.6 (8)C2O—C3O—H3O120.5
C2E—N2E—H2E1122.2 (18)N1O—C6O—C5O121.2 (9)
C2E—N2E—H2E2121.8 (18)N1O—C6O—H6O119.4
H2E1—N2E—H2E2116 (3)C5O—C6O—H6O119.4
C2E—N3E—C4E122.9 (8)N1O—C2O—N2O119.7 (9)
C2E—N3E—H3E123 (7)N1O—C2O—C3O119.6 (9)
C4E—N3E—H3E114 (7)N2O—C2O—C3O120.7 (9)
O4E—C4E—N3E117.6 (9)C2O—N2O—H2O1120.2 (18)
O4E—C4E—C5E126.9 (10)C2O—N2O—H2O2120.0 (18)
N3E—C4E—C5E115.5 (9)H2O1—N2O—H2O2114 (6)
C6E—C5E—C4E117.4 (9)C3O—C4O—C5O121.1 (9)
C6E—C5E—H5E121.3C3O—C4O—H4O119.5
C4E—C5E—H5E121.3C5O—C4O—H4O119.5
N1E—C6E—C5E126.1 (9)C4O—C5O—C6O117.8 (10)
N1E—C6E—Cl6E113.9 (7)C4O—C5O—H5O121.1
C5E—C6E—Cl6E120.0 (8)C6O—C5O—H5O121.1
C2F—N1F—C6F115.6 (8)C6P—N1P—C2P119.0 (7)
N2F—C2F—N1F119.7 (8)C6P—N1P—H1P116.3 (11)
N2F—C2F—N3F119.0 (8)C2P—N1P—H1P124.7 (12)
N1F—C2F—N3F121.2 (9)N2P—C2P—N1P117.3 (8)
C2F—N2F—H2F1123.6 (19)N2P—C2P—C3P125.7 (9)
C2F—N2F—H2F2123.8 (19)N1P—C2P—C3P117.0 (9)
H2F1—N2F—H2F2112 (4)C2P—N2P—H2P1126 (2)
C2F—N3F—C4F124.6 (8)C2P—N2P—H2P2126 (2)
C2F—N3F—H3F123 (7)H2P1—N2P—H2P2107 (4)
C4F—N3F—H3F112 (7)C5P—C6P—N1P124.5 (10)
O4F—C4F—N3F120.7 (9)C5P—C6P—H6P117.8
O4F—C4F—C5F124.6 (10)N1P—C6P—H6P117.8
N3F—C4F—C5F114.7 (8)C6P—C5P—C4P115.9 (11)
C6F—C5F—C4F117.6 (9)C6P—C5P—H4P122.0
C6F—C5F—H5F121.2C4P—C5P—H4P122.0
C4F—C5F—H5F121.2C3P—C4P—C5P123.2 (10)
N1F—C6F—C5F126.1 (9)C3P—C4P—H4P118.4
N1F—C6F—Cl6F114.4 (7)C5P—C4P—H4P118.4
C5F—C6F—Cl6F119.4 (8)C4P—C3P—C2P120.4 (10)
C6G—N1G—C2G113.9 (8)C4P—C3P—H3P119.8
N3G—C2G—N2G118.6 (9)C2P—C3P—H3P119.8
N3G—C2G—N1G125.4 (9)C2R—N1R—C6R109.7 (17)
N2G—C2G—N1G115.9 (8)C2S—N1R—C6S108.3 (17)
C2G—N2G—H2G1121.4 (18)N1R—C2R—N2R113 (2)
C2G—N2G—H2G2121.4 (18)N1R—C2R—C3R130 (3)
H2G1—N2G—H2G2109 (6)N2R—C2R—C3R118 (3)
C2G—N3G—C4G118.6 (8)C2R—N2R—H2R1118 (3)
O4G—C4G—N3G118.9 (9)C2R—N2R—H2R2118 (3)
O4G—C4G—C5G121.3 (9)H2R1—N2R—H2R2122 (8)
N3G—C4G—C5G119.8 (9)C2R—C3R—C4R114 (3)
C6G—C5G—C4G116.4 (9)C2R—C3R—H3R122.9
C6G—C5G—H5G121.8C4R—C3R—H3R122.9
C4G—C5G—H5G121.8C3R—C4R—C5R121 (3)
N1G—C6G—C5G125.8 (9)C3R—C4R—H4R119.7
N1G—C6G—Cl6G113.7 (7)C5R—C4R—H4R119.7
C5G—C6G—Cl6G120.5 (8)C6R—C5R—C4R114 (2)
C2H—N1H—C6H115.6 (8)C6R—C5R—H5R123.0
N1H—C2H—N2H118.8 (8)C4R—C5R—H5R123.0
N1H—C2H—N3H122.3 (9)C5R—C6R—N1R132 (2)
N2H—C2H—N3H118.8 (9)C5R—C6R—H6R114.2
C2H—N2H—H2H1121.7 (18)N1R—C6R—H6R114.2
C2H—N2H—H2H2122.1 (18)C3S—C2S—N1R131 (3)
H2H1—N2H—H2H2116 (3)C3S—C2S—N2S120 (3)
C2H—N3H—C4H123.3 (8)N1R—C2S—N2S109 (2)
C2H—N3H—H3H116 (7)C2S—N2S—H2S1115 (3)
C4H—N3H—H3H121 (7)C2S—N2S—H2S2115 (3)
O4H—C4H—N3H120.8 (8)H2S1—N2S—H2S2124 (10)
O4H—C4H—C5H123.8 (8)C2S—C3S—C4S115 (3)
N3H—C4H—C5H115.3 (8)C2S—C3S—H3S122.3
C6H—C5H—C4H116.5 (9)C4S—C3S—H3S122.3
C6H—C5H—H5H121.7C3S—C4S—C5S123 (3)
C4H—C5H—H5H121.7C3S—C4S—H4S118.7
N1H—C6H—C5H126.9 (9)C5S—C4S—H4S118.7
N1H—C6H—Cl6H114.2 (7)C6S—C5S—C4S111 (3)
C5H—C6H—Cl6H118.8 (7)C6S—C5S—H5S124.6
C6I—N1I—C2I114.8 (8)C4S—C5S—H5S124.6
N2I—C2I—N1I119.8 (9)C5S—C6S—N1R131 (2)
N2I—C2I—N3I119.6 (9)C5S—C6S—H6S114.6
N1I—C2I—N3I120.5 (9)N1R—C6S—H6S114.6
C6A—N1A—C2A—N2A178.3 (10)C4H—C5H—C6H—N1H2.1 (16)
C6A—N1A—C2A—N3A2.3 (15)C4H—C5H—C6H—Cl6H179.5 (7)
N2A—C2A—N3A—C4A179.0 (10)C6I—N1I—C2I—N2I178.7 (10)
N1A—C2A—N3A—C4A0.3 (15)C6I—N1I—C2I—N3I0.3 (14)
C2A—N3A—C4A—O4A178.2 (9)N2I—C2I—N3I—C4I179.4 (10)
C2A—N3A—C4A—C5A2.5 (14)N1I—C2I—N3I—C4I0.9 (15)
O4A—C4A—C5A—C6A178.8 (10)C2I—N3I—C4I—O4I179.5 (9)
N3A—C4A—C5A—C6A1.9 (14)C2I—N3I—C4I—C5I1.8 (14)
C2A—N1A—C6A—C5A2.9 (16)O4I—C4I—C5I—C6I179.5 (10)
C2A—N1A—C6A—Cl6A177.1 (7)N3I—C4I—C5I—C6I1.9 (13)
C4A—C5A—C6A—N1A0.8 (17)C2I—N1I—C6I—C5I0.7 (16)
C4A—C5A—C6A—Cl6A179.2 (8)C2I—N1I—C6I—Cl6I178.9 (7)
C6B—N1B—C2B—N2B178.5 (9)C4I—C5I—C6I—N1I1.5 (16)
C6B—N1B—C2B—N3B0.1 (14)C4I—C5I—C6I—Cl6I178.0 (7)
N2B—C2B—N3B—C4B179.1 (9)C6K—N1K—C2K—N2K178.9 (9)
N1B—C2B—N3B—C4B0.5 (15)C6K—N1K—C2K—N3K2.2 (14)
C2B—N3B—C4B—O4B180.0 (9)N1K—C2K—N3K—C4K2.6 (15)
C2B—N3B—C4B—C5B1.3 (14)N2K—C2K—N3K—C4K178.5 (9)
O4B—C4B—C5B—C6B179.8 (10)C2K—N3K—C4K—O4K179.8 (9)
N3B—C4B—C5B—C6B1.5 (15)C2K—N3K—C4K—C5K1.5 (14)
C2B—N1B—C6B—C5B0.1 (16)O4K—C4K—C5K—C6K178.5 (10)
C2B—N1B—C6B—Cl6B179.9 (7)N3K—C4K—C5K—C6K0.4 (14)
C4B—C5B—C6B—N1B0.9 (17)C4K—C5K—C6K—N1K0.2 (17)
C4B—C5B—C6B—Cl6B179.1 (8)C4K—C5K—C6K—Cl6K179.8 (7)
C6C—N1C—C2C—N2C179.7 (10)C2K—N1K—C6K—C5K1.1 (15)
C6C—N1C—C2C—N3C0.6 (15)C2K—N1K—C6K—Cl6K178.9 (7)
N1C—C2C—N3C—C4C0.9 (16)C6L—N1L—C2L—N2L179.3 (9)
N2C—C2C—N3C—C4C180.0 (9)C6L—N1L—C2L—N3L0.9 (14)
C2C—N3C—C4C—O4C177.5 (9)N2L—C2L—N3L—C4L179.9 (9)
C2C—N3C—C4C—C5C2.6 (14)N1L—C2L—N3L—C4L0.3 (15)
O4C—C4C—C5C—C6C178.4 (10)C2L—N3L—C4L—O4L178.4 (9)
N3C—C4C—C5C—C6C4.1 (14)C2L—N3L—C4L—C5L1.2 (14)
C2C—N1C—C6C—C5C2.6 (16)O4L—C4L—C5L—C6L177.5 (9)
C2C—N1C—C6C—Cl6C177.8 (7)N3L—C4L—C5L—C6L2.0 (13)
C4C—C5C—C6C—N1C4.5 (17)C4L—C5L—C6L—N1L1.7 (15)
C4C—C5C—C6C—Cl6C175.9 (8)C4L—C5L—C6L—Cl6L176.4 (7)
C6D—N1D—C2D—N2D178.7 (9)C2L—N1L—C6L—C5L0.1 (15)
C6D—N1D—C2D—N3D0.7 (14)C2L—N1L—C6L—Cl6L178.1 (7)
N2D—C2D—N3D—C4D177.5 (10)C6M—N1M—C2M—N3M0.2 (14)
N1D—C2D—N3D—C4D0.5 (15)C6M—N1M—C2M—N2M179.4 (9)
C2D—N3D—C4D—O4D177.0 (9)N1M—C2M—N3M—C4M0.2 (15)
C2D—N3D—C4D—C5D0.8 (14)N2M—C2M—N3M—C4M179.9 (9)
O4D—C4D—C5D—C6D177.7 (10)C2M—N3M—C4M—O4M178.6 (9)
N3D—C4D—C5D—C6D0.1 (14)C2M—N3M—C4M—C5M1.3 (13)
C4D—C5D—C6D—N1D1.2 (16)O4M—C4M—C5M—C6M178.0 (10)
C4D—C5D—C6D—Cl6D179.2 (7)N3M—C4M—C5M—C6M1.9 (13)
C2D—N1D—C6D—C5D1.6 (15)C4M—C5M—C6M—N1M1.7 (17)
C2D—N1D—C6D—Cl6D178.8 (7)C4M—C5M—C6M—Cl6M179.5 (7)
C6E—N1E—C2E—N2E179.2 (10)C2M—N1M—C6M—C5M0.6 (16)
C6E—N1E—C2E—N3E0.4 (15)C2M—N1M—C6M—Cl6M178.5 (7)
N1E—C2E—N3E—C4E0.9 (16)C2O—N1O—C6O—C5O0.3 (14)
N2E—C2E—N3E—C4E179.6 (10)C6O—N1O—C2O—N2O179.4 (10)
C2E—N3E—C4E—O4E178.6 (10)C6O—N1O—C2O—C3O2.8 (14)
C2E—N3E—C4E—C5E1.2 (15)C4O—C3O—C2O—N1O2.5 (14)
O4E—C4E—C5E—C6E178.7 (11)C4O—C3O—C2O—N2O179.6 (10)
N3E—C4E—C5E—C6E1.1 (15)C2O—C3O—C4O—C5O0.2 (15)
C2E—N1E—C6E—C5E0.4 (16)C3O—C4O—C5O—C6O2.5 (15)
C2E—N1E—C6E—Cl6E179.2 (7)N1O—C6O—C5O—C4O2.3 (15)
C4E—C5E—C6E—N1E0.8 (16)C6P—N1P—C2P—N2P178.7 (9)
C4E—C5E—C6E—Cl6E178.9 (8)C6P—N1P—C2P—C3P1.3 (13)
C6F—N1F—C2F—N2F179.7 (10)C2P—N1P—C6P—C5P1.2 (15)
C6F—N1F—C2F—N3F1.8 (14)N1P—C6P—C5P—C4P0.2 (16)
N2F—C2F—N3F—C4F177.6 (10)C6P—C5P—C4P—C3P1.6 (16)
N1F—C2F—N3F—C4F0.4 (16)C5P—C4P—C3P—C2P1.6 (16)
C2F—N3F—C4F—O4F179.4 (10)N2P—C2P—C3P—C4P180.0 (10)
C2F—N3F—C4F—C5F1.5 (15)N1P—C2P—C3P—C4P0.0 (14)
O4F—C4F—C5F—C6F179.5 (10)C2S—N1R—C2R—N2R177.6 (13)
N3F—C4F—C5F—C6F0.4 (15)C6R—N1R—C2R—N2R173.9 (13)
C2F—N1F—C6F—C5F2.9 (15)C6S—N1R—C2R—N2R15 (3)
C2F—N1F—C6F—Cl6F178.6 (7)C2S—N1R—C2R—C3R0 (2)
C4F—C5F—C6F—N1F1.8 (17)C6R—N1R—C2R—C3R9 (2)
C4F—C5F—C6F—Cl6F179.8 (8)C6S—N1R—C2R—C3R162 (4)
C6G—N1G—C2G—N3G2.2 (14)N1R—C2R—C3R—C4R7 (4)
C6G—N1G—C2G—N2G180.0 (9)N2R—C2R—C3R—C4R176 (2)
N2G—C2G—N3G—C4G175.7 (9)C2R—C3R—C4R—C5R1 (4)
N1G—C2G—N3G—C4G2.1 (15)C3R—C4R—C5R—C6R1 (4)
C2G—N3G—C4G—O4G177.3 (9)C4R—C5R—C6R—N1R1 (3)
C2G—N3G—C4G—C5G4.5 (14)C2S—N1R—C6R—C5R14 (3)
O4G—C4G—C5G—C6G179.3 (9)C2R—N1R—C6R—C5R6 (3)
N3G—C4G—C5G—C6G2.6 (15)C6S—N1R—C6R—C5R1 (4)
C2G—N1G—C6G—C5G4.3 (14)C2R—N1R—C2S—C3S7 (3)
C2G—N1G—C6G—Cl6G178.2 (7)C6R—N1R—C2S—C3S154 (7)
C4G—C5G—C6G—N1G2.1 (15)C6S—N1R—C2S—C3S14 (4)
C4G—C5G—C6G—Cl6G179.4 (8)C2R—N1R—C2S—N2S178.4 (18)
C6H—N1H—C2H—N2H178.6 (9)C6R—N1R—C2S—N2S17 (3)
C6H—N1H—C2H—N3H1.6 (14)C6S—N1R—C2S—N2S174.5 (18)
N1H—C2H—N3H—C4H3.5 (15)N1R—C2S—C3S—C4S12 (5)
N2H—C2H—N3H—C4H179.6 (9)N2S—C2S—C3S—C4S178 (3)
C2H—N3H—C4H—O4H178.7 (9)C2S—C3S—C4S—C5S3 (5)
C2H—N3H—C4H—C5H4.2 (14)C3S—C4S—C5S—C6S1 (4)
O4H—C4H—C5H—C6H179.6 (9)C4S—C5S—C6S—N1R3 (4)
N3H—C4H—C5H—C6H3.4 (13)C2S—N1R—C6S—C5S9 (3)
C2H—N1H—C6H—C5H1.1 (15)C2R—N1R—C6S—C5S9.1 (17)
C2H—N1H—C6H—Cl6H178.6 (7)C6R—N1R—C6S—C5S2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A1···N1Fi0.88 (1)2.25 (2)3.107 (11)166 (6)
N2A—H2A2···O4B0.88 (1)1.95 (2)2.829 (11)173 (5)
N3A—H3A···N3B0.88 (1)2.03 (3)2.900 (11)168 (10)
N2B—H2B1···O4A0.88 (1)2.09 (2)2.960 (11)169 (3)
N2B—H2B2···N1C0.88 (1)2.28 (2)3.140 (11)167 (7)
N2C—H2C1···N1B0.88 (1)2.09 (4)2.936 (11)160 (11)
N3C—H3C···O4D0.88 (1)1.96 (2)2.839 (11)175 (11)
N2D—H2D1···N1E0.88 (1)2.13 (2)2.991 (11)167 (6)
N3D—H3D···O4C0.88 (1)1.86 (2)2.732 (10)169 (10)
C5D—H5D···Cl6Gii0.952.883.769 (11)156
N2E—H2E1···N1D0.88 (1)2.05 (2)2.917 (11)169 (5)
N3E—H3E···O4F0.88 (1)1.92 (3)2.772 (11)164 (11)
N2F—H2F1···N1Aiii0.88 (1)2.06 (2)2.930 (11)171 (6)
N2F—H2F2···N2R0.88 (1)2.44 (4)3.29 (2)162 (9)
N3F—H3F···O4E0.88 (1)1.90 (3)2.761 (11)166 (10)
N2G—H2G1···O4H0.88 (1)2.03 (3)2.892 (11)166 (10)
N2G—H2G2···N1Miv0.88 (1)2.27 (3)3.120 (11)162 (9)
C5G—H5G···Cl6Dii0.952.733.638 (10)161
N2H—H2H1···N1I0.88 (1)2.18 (2)3.045 (11)169 (3)
N2H—H2H2···O4G0.88 (1)1.97 (2)2.842 (11)175 (9)
N3H—H3H···N3G0.88 (1)2.00 (2)2.870 (11)169 (10)
C5H—H5H···Cl6Ev0.952.933.837 (10)161
N2I—H2I1···N1H0.88 (1)2.04 (3)2.900 (12)165 (9)
N3I—H3I···O4K0.88 (1)1.89 (2)2.764 (11)173 (10)
N2K—H2K2···N2Svi0.88 (1)2.28 (4)3.13 (2)161 (8)
N3K—H3K···O4I0.88 (1)1.88 (1)2.761 (11)176 (10)
N2L—H2L1···N1K0.88 (1)2.14 (3)2.999 (11)164 (9)
N2L—H2L2···N2O0.88 (1)2.59 (4)3.436 (14)162 (10)
N3L—H3L···O4M0.77 (11)2.02 (12)2.782 (11)169 (12)
N2M—H2M1···N1Gvii0.88 (1)2.05 (1)2.927 (11)175 (6)
N3M—H3M···O4L0.96 (11)1.83 (11)2.794 (11)175 (10)
N1O—H1O···O4Gviii0.97 (11)1.64 (12)2.598 (11)167 (10)
N2O—H2O1···O4M0.88 (1)1.98 (1)2.810 (12)157 (3)
N2O—H2O2···N1Rix0.88 (1)2.27 (8)2.971 (13)136 (10)
N1P—H1P···O4Ax0.89 (1)2.01 (1)2.769 (10)143 (2)
N2P—H2P1···O4B0.88 (1)1.89 (3)2.719 (11)157 (8)
N2P—H2P2···O4H0.88 (1)2.11 (5)2.872 (11)144 (7)
C3P—H3P···O4Lviii0.952.493.186 (11)130
N2R—H2R1···O4Fxi0.88 (1)2.36 (5)3.05 (2)136 (6)
N2R—H2R2···O4E0.88 (1)2.12 (6)2.92 (2)152 (12)
C3R—H3R···O4Dxii0.952.443.37 (4)167
C5R—H5R···O4Ixiii0.952.453.28 (2)145
C4O—H4O···O4Cxiv0.952.643.577 (12)171
Symmetry codes: (i) x1, y+2, z; (ii) x+2, y1, z+1; (iii) x+1, y2, z; (iv) x+2, y1, z; (v) x+2, y1, z; (vi) x2, y+2, z+1; (vii) x2, y+1, z; (viii) x, y+1, z+1; (ix) x+1, y1, z; (x) x+2, y, z; (xi) x+3, y3, z; (xii) x+3, y2, z; (xiii) x+2, y2, z1; (xiv) x+1, y, z.
(II) 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one–2-amino-5-bromo-6-methylpyrimidin-4(1H)-one (1/1) top
Crystal data top
C5H6BrN3OF(000) = 800
Mr = 204.04Dx = 2.034 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.8154 (13) ÅCell parameters from 6792 reflections
b = 9.9532 (8) Åθ = 3.6–26.1°
c = 14.344 (2) ŵ = 6.10 mm1
β = 108.021 (11)°T = 173 K
V = 1332.6 (3) Å3Block, colourless
Z = 80.35 × 0.30 × 0.25 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
1986 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.103
ω scansθmax = 25.7°, θmin = 3.6°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1111
Tmin = 0.220, Tmax = 0.310k = 1210
6144 measured reflectionsl = 1717
2480 independent reflections
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)] = 0.076Hydrogen site location: mixed
wR(F2) = 0.228H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.1394P)2 + 4.545P]
where P = (Fo2 + 2Fc2)/3
2480 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 1.06 e Å3
11 restraintsΔρmin = 1.50 e Å3
Crystal data top
C5H6BrN3OV = 1332.6 (3) Å3
Mr = 204.04Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.8154 (13) ŵ = 6.10 mm1
b = 9.9532 (8) ÅT = 173 K
c = 14.344 (2) Å0.35 × 0.30 × 0.25 mm
β = 108.021 (11)°
Data collection top
Stoe IPDSII two-circle
diffractometer
2480 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
1986 reflections with I > 2σ(I)
Tmin = 0.220, Tmax = 0.310Rint = 0.103
6144 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07611 restraints
wR(F2) = 0.228H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 1.06 e Å3
2480 reflectionsΔρmin = 1.50 e Å3
201 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.4704 (7)0.8846 (7)0.3227 (4)0.0251 (14)
H1A0.425 (9)0.904 (9)0.261 (3)0.030*
C2A0.4096 (8)0.7796 (8)0.3524 (5)0.0239 (16)
N2A0.2973 (8)0.7214 (7)0.2890 (5)0.0317 (17)
H2A10.240 (9)0.672 (9)0.311 (7)0.038*
H2A20.275 (11)0.744 (10)0.227 (3)0.038*
N3A0.4543 (7)0.7329 (7)0.4441 (4)0.0238 (14)
C4A0.5692 (8)0.7914 (8)0.5109 (5)0.0232 (16)
O4A0.6128 (6)0.7470 (6)0.5970 (3)0.0246 (12)
C5A0.6353 (8)0.9042 (8)0.4775 (5)0.0246 (16)
Br5A0.79004 (11)0.98982 (11)0.56837 (7)0.0460 (4)
C6A0.5873 (8)0.9487 (8)0.3859 (6)0.0239 (16)
C61A0.6417 (10)1.0653 (9)0.3425 (6)0.0326 (19)
H61A0.70551.11950.39500.049*
H61B0.56071.12050.30470.049*
H61C0.69451.03250.29920.049*
N1B0.2832 (8)0.3906 (7)0.6420 (4)0.0275 (14)
C2B0.3494 (8)0.4851 (7)0.6073 (5)0.0227 (16)
N2B0.4640 (8)0.5476 (7)0.6676 (5)0.0311 (16)
H2B10.501 (4)0.520 (4)0.7294 (16)0.037*
H2B20.507 (7)0.613 (7)0.645 (3)0.037*
N3B0.3046 (7)0.5243 (7)0.5121 (4)0.0228 (14)
H3B0.364 (8)0.577 (8)0.495 (6)0.027*
C4B0.1891 (8)0.4675 (8)0.4436 (5)0.0225 (16)
O4B0.1563 (6)0.5068 (5)0.3564 (4)0.0257 (12)
C5B0.1158 (9)0.3701 (8)0.4818 (5)0.0271 (17)
Br5B0.04808 (10)0.29445 (10)0.39310 (6)0.0411 (4)
C6B0.1655 (9)0.3341 (8)0.5791 (5)0.0267 (17)
C61B0.0923 (11)0.2293 (9)0.6207 (6)0.0339 (19)
H61D0.15180.20720.68750.051*
H61E0.07780.14850.57980.051*
H61F0.00060.26350.62220.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.029 (3)0.033 (3)0.011 (3)0.000 (3)0.002 (2)0.006 (2)
C2A0.023 (4)0.032 (4)0.011 (3)0.003 (3)0.003 (3)0.000 (3)
N2A0.034 (4)0.039 (4)0.011 (3)0.010 (3)0.009 (3)0.008 (3)
N3A0.032 (4)0.028 (3)0.009 (3)0.003 (3)0.001 (2)0.002 (2)
C4A0.022 (4)0.030 (4)0.013 (3)0.004 (3)0.000 (3)0.003 (3)
O4A0.026 (3)0.033 (3)0.009 (2)0.001 (2)0.003 (2)0.003 (2)
C5A0.022 (4)0.030 (4)0.019 (3)0.004 (3)0.002 (3)0.000 (3)
Br5A0.0473 (7)0.0508 (6)0.0325 (6)0.0059 (4)0.0017 (4)0.0039 (4)
C6A0.020 (4)0.026 (4)0.024 (4)0.000 (3)0.006 (3)0.001 (3)
C61A0.035 (4)0.032 (4)0.031 (4)0.002 (3)0.010 (3)0.011 (3)
N1B0.036 (4)0.030 (3)0.016 (3)0.006 (3)0.008 (3)0.003 (3)
C2B0.025 (4)0.024 (4)0.017 (3)0.000 (3)0.005 (3)0.002 (3)
N2B0.039 (4)0.035 (4)0.015 (3)0.003 (3)0.001 (3)0.001 (3)
N3B0.023 (3)0.029 (3)0.015 (3)0.004 (3)0.003 (2)0.001 (2)
C4B0.024 (4)0.024 (3)0.016 (3)0.003 (3)0.002 (3)0.002 (3)
O4B0.027 (3)0.036 (3)0.011 (2)0.004 (2)0.002 (2)0.000 (2)
C5B0.031 (4)0.032 (4)0.018 (3)0.001 (3)0.008 (3)0.002 (3)
Br5B0.0366 (6)0.0474 (6)0.0333 (5)0.0106 (4)0.0020 (4)0.0013 (4)
C6B0.040 (5)0.025 (4)0.016 (3)0.000 (3)0.011 (3)0.005 (3)
C61B0.041 (5)0.035 (4)0.026 (4)0.006 (4)0.012 (4)0.000 (3)
Geometric parameters (Å, º) top
N1A—C2A1.337 (11)N1B—C2B1.325 (11)
N1A—C6A1.380 (10)N1B—C6B1.349 (10)
N1A—H1A0.88 (2)C2B—N2B1.342 (10)
C2A—N2A1.325 (10)C2B—N3B1.355 (10)
C2A—N3A1.335 (9)N2B—H2B10.891 (16)
N2A—H2A10.87 (2)N2B—H2B20.894 (16)
N2A—H2A20.88 (2)N3B—C4B1.372 (9)
N3A—C4A1.365 (9)N3B—H3B0.87 (2)
C4A—O4A1.256 (9)C4B—O4B1.254 (9)
C4A—C5A1.450 (11)C4B—C5B1.415 (12)
C5A—C6A1.327 (11)C5B—C6B1.376 (10)
C5A—Br5A1.873 (7)C5B—Br5B1.873 (8)
C6A—C61A1.492 (11)C6B—C61B1.491 (12)
C61A—H61A0.9800C61B—H61D0.9800
C61A—H61B0.9800C61B—H61E0.9800
C61A—H61C0.9800C61B—H61F0.9800
C2A—N1A—C6A121.0 (6)C2B—N1B—C6B117.6 (6)
C2A—N1A—H1A111 (6)N1B—C2B—N2B119.8 (7)
C6A—N1A—H1A128 (6)N1B—C2B—N3B122.6 (7)
N2A—C2A—N3A118.3 (7)N2B—C2B—N3B117.6 (7)
N2A—C2A—N1A118.8 (6)C2B—N2B—H2B1120.1 (16)
N3A—C2A—N1A122.9 (7)C2B—N2B—H2B2120.0 (16)
C2A—N2A—H2A1120 (7)H2B1—N2B—H2B2119.8 (15)
C2A—N2A—H2A2118 (7)C2B—N3B—C4B122.8 (7)
H2A1—N2A—H2A2121 (10)C2B—N3B—H3B115 (6)
C2A—N3A—C4A119.5 (7)C4B—N3B—H3B122 (6)
O4A—C4A—N3A119.8 (7)O4B—C4B—N3B119.2 (7)
O4A—C4A—C5A123.1 (6)O4B—C4B—C5B126.6 (7)
N3A—C4A—C5A117.1 (6)N3B—C4B—C5B114.2 (6)
C6A—C5A—C4A121.9 (7)C6B—C5B—C4B120.6 (7)
C6A—C5A—Br5A120.0 (6)C6B—C5B—Br5B123.0 (7)
C4A—C5A—Br5A118.2 (5)C4B—C5B—Br5B116.4 (5)
C5A—C6A—N1A117.7 (7)N1B—C6B—C5B122.1 (8)
C5A—C6A—C61A127.6 (7)N1B—C6B—C61B116.3 (7)
N1A—C6A—C61A114.7 (7)C5B—C6B—C61B121.7 (8)
C6A—C61A—H61A109.5C6B—C61B—H61D109.5
C6A—C61A—H61B109.5C6B—C61B—H61E109.5
H61A—C61A—H61B109.5H61D—C61B—H61E109.5
C6A—C61A—H61C109.5C6B—C61B—H61F109.5
H61A—C61A—H61C109.5H61D—C61B—H61F109.5
H61B—C61A—H61C109.5H61E—C61B—H61F109.5
C6A—N1A—C2A—N2A179.8 (8)C6B—N1B—C2B—N2B177.7 (7)
C6A—N1A—C2A—N3A1.9 (12)C6B—N1B—C2B—N3B1.1 (11)
N2A—C2A—N3A—C4A179.7 (8)N1B—C2B—N3B—C4B1.4 (11)
N1A—C2A—N3A—C4A1.8 (12)N2B—C2B—N3B—C4B179.8 (7)
C2A—N3A—C4A—O4A179.2 (7)C2B—N3B—C4B—O4B178.2 (7)
C2A—N3A—C4A—C5A0.9 (11)C2B—N3B—C4B—C5B3.5 (11)
O4A—C4A—C5A—C6A179.8 (8)O4B—C4B—C5B—C6B178.5 (8)
N3A—C4A—C5A—C6A0.4 (12)N3B—C4B—C5B—C6B3.3 (11)
O4A—C4A—C5A—Br5A1.6 (11)O4B—C4B—C5B—Br5B0.9 (11)
N3A—C4A—C5A—Br5A178.3 (6)N3B—C4B—C5B—Br5B177.3 (5)
C4A—C5A—C6A—N1A0.5 (12)C2B—N1B—C6B—C5B1.2 (12)
Br5A—C5A—C6A—N1A178.1 (6)C2B—N1B—C6B—C61B179.2 (7)
C4A—C5A—C6A—C61A178.1 (8)C4B—C5B—C6B—N1B1.1 (13)
Br5A—C5A—C6A—C61A0.5 (12)Br5B—C5B—C6B—N1B179.5 (6)
C2A—N1A—C6A—C5A1.2 (12)C4B—C5B—C6B—C61B178.5 (8)
C2A—N1A—C6A—C61A179.1 (8)Br5B—C5B—C6B—C61B1.0 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.88 (2)1.92 (4)2.765 (8)160 (9)
N1A—H1A···Br5Bi0.88 (2)3.03 (9)3.525 (7)118 (7)
N2A—H2A1···O4B0.87 (2)2.04 (4)2.871 (9)160 (10)
N2A—H2A2···O4Aii0.88 (2)2.05 (6)2.807 (8)144 (9)
N2B—H2B1···Br5Aiii0.89 (2)3.00 (1)3.852 (6)160 (2)
N2B—H2B2···O4A0.89 (2)1.94 (2)2.831 (10)176 (9)
N3B—H3B···N3A0.87 (2)2.03 (3)2.883 (10)164 (9)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+3/2, y1/2, z+3/2.
(III) 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one–2-amino-5-bromo-6-methylpyrimidin-4(1H)-one N-methylpyrrolidin-2-one monosolvate (1/1/1) top
Crystal data top
2C5H6BrN3O·C5H9NOF(000) = 1016
Mr = 507.21Dx = 1.780 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.7075 (14) ÅCell parameters from 7488 reflections
b = 14.0308 (11) Åθ = 3.4–26.0°
c = 11.8308 (14) ŵ = 4.32 mm1
β = 103.096 (10)°T = 173 K
V = 1892.8 (4) Å3Block, colourless
Z = 40.30 × 0.20 × 0.18 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
2736 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.113
ω scansθmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 1414
Tmin = 0.350, Tmax = 0.525k = 1616
10611 measured reflectionsl = 1314
3544 independent reflections
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)] = 0.054Hydrogen site location: mixed
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0855P)2]
where P = (Fo2 + 2Fc2)/3
3544 reflections(Δ/σ)max < 0.001
265 parametersΔρmax = 0.77 e Å3
6 restraintsΔρmin = 0.76 e Å3
Crystal data top
2C5H6BrN3O·C5H9NOV = 1892.8 (4) Å3
Mr = 507.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.7075 (14) ŵ = 4.32 mm1
b = 14.0308 (11) ÅT = 173 K
c = 11.8308 (14) Å0.30 × 0.20 × 0.18 mm
β = 103.096 (10)°
Data collection top
Stoe IPDSII two-circle
diffractometer
3544 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2736 reflections with I > 2σ(I)
Tmin = 0.350, Tmax = 0.525Rint = 0.113
10611 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0546 restraints
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.77 e Å3
3544 reflectionsΔρmin = 0.76 e Å3
265 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.3491 (4)0.3717 (3)0.4327 (4)0.0263 (9)
H1A0.319 (4)0.365 (4)0.493 (3)0.032*
C2A0.3699 (4)0.4617 (4)0.4005 (4)0.0259 (10)
N2A0.3510 (4)0.5313 (3)0.4707 (4)0.0313 (10)
H21A0.337 (5)0.509 (4)0.535 (3)0.038*
H22A0.361 (5)0.5922 (14)0.457 (6)0.038*
N3A0.4043 (4)0.4821 (3)0.3052 (4)0.0283 (9)
C4A0.4219 (4)0.4090 (4)0.2328 (4)0.0285 (11)
O4A0.4562 (4)0.4274 (3)0.1431 (3)0.0376 (9)
C5A0.3990 (4)0.3132 (4)0.2654 (4)0.0279 (10)
Br5A0.42174 (5)0.21464 (4)0.16649 (5)0.0404 (2)
C6A0.3644 (4)0.2947 (4)0.3641 (5)0.0266 (11)
C61A0.3440 (5)0.1991 (4)0.4112 (5)0.0316 (11)
H61A0.31410.15520.34680.047*
H61B0.28650.20480.45950.047*
H61C0.41800.17450.45820.047*
N1B0.4629 (4)0.7805 (3)0.0949 (4)0.0300 (9)
C2B0.4586 (4)0.6934 (4)0.1339 (4)0.0284 (11)
N2B0.4706 (4)0.6193 (4)0.0674 (4)0.0342 (10)
H21B0.477 (5)0.626 (5)0.004 (2)0.041*
H22B0.473 (6)0.5607 (19)0.094 (6)0.041*
N3B0.4399 (4)0.6735 (3)0.2403 (3)0.0259 (9)
H3B0.434 (5)0.6126 (13)0.254 (5)0.031*
C4B0.4228 (4)0.7424 (4)0.3187 (4)0.0262 (10)
O4B0.4063 (3)0.7201 (3)0.4155 (3)0.0306 (8)
C5B0.4275 (4)0.8372 (4)0.2757 (4)0.0265 (10)
Br5B0.40471 (5)0.93712 (4)0.37292 (5)0.0385 (2)
C6B0.4470 (4)0.8528 (4)0.1661 (5)0.0311 (11)
C61B0.4519 (6)0.9497 (4)0.1177 (5)0.0403 (13)
H61D0.52720.97940.15340.060*
H61E0.38790.98840.13420.060*
H61F0.44390.94550.03360.060*
N1X0.2378 (4)0.3841 (3)0.8124 (4)0.0329 (10)
C11X0.2429 (6)0.4830 (5)0.8452 (6)0.0448 (14)
H11A0.28300.51930.79490.067*
H11B0.28600.48950.92610.067*
H11C0.16310.50770.83700.067*
C2X0.2593 (4)0.3522 (4)0.7141 (5)0.0314 (11)
O2X0.2856 (4)0.4009 (3)0.6376 (3)0.0397 (9)
C3X0.2452 (5)0.2454 (4)0.7119 (5)0.0359 (12)
H3X10.31670.21410.69830.043*
H3X20.17760.22620.64950.043*
C4X0.2248 (5)0.2179 (4)0.8297 (5)0.0391 (13)
H4X10.29390.18410.87620.047*
H4X20.15520.17620.82110.047*
C5X0.2049 (5)0.3134 (5)0.8881 (5)0.0390 (13)
H5X10.12180.32070.89210.047*
H5X20.25510.31780.96740.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.031 (2)0.027 (2)0.022 (2)0.0008 (17)0.0095 (16)0.0001 (16)
C2A0.025 (2)0.022 (3)0.029 (2)0.0012 (18)0.0046 (18)0.0028 (19)
N2A0.051 (3)0.026 (2)0.021 (2)0.002 (2)0.0175 (19)0.0013 (17)
N3A0.035 (2)0.025 (2)0.026 (2)0.0021 (18)0.0091 (17)0.0010 (17)
C4A0.034 (2)0.029 (3)0.022 (2)0.001 (2)0.0063 (19)0.005 (2)
O4A0.058 (2)0.033 (2)0.0282 (19)0.0012 (18)0.0223 (17)0.0012 (16)
C5A0.028 (2)0.029 (3)0.025 (2)0.002 (2)0.0022 (19)0.001 (2)
Br5A0.0498 (3)0.0357 (3)0.0353 (3)0.0039 (2)0.0092 (2)0.0080 (2)
C6A0.022 (2)0.024 (3)0.031 (3)0.0005 (18)0.0003 (19)0.002 (2)
C61A0.035 (3)0.029 (3)0.031 (3)0.000 (2)0.009 (2)0.001 (2)
N1B0.034 (2)0.033 (2)0.024 (2)0.0006 (18)0.0088 (17)0.0010 (18)
C2B0.030 (2)0.032 (3)0.022 (2)0.000 (2)0.0054 (19)0.002 (2)
N2B0.049 (3)0.033 (3)0.024 (2)0.005 (2)0.016 (2)0.0011 (18)
N3B0.036 (2)0.025 (2)0.0174 (19)0.0021 (18)0.0068 (16)0.0009 (16)
C4B0.026 (2)0.025 (3)0.027 (3)0.0004 (19)0.0040 (19)0.003 (2)
O4B0.045 (2)0.029 (2)0.0204 (17)0.0012 (16)0.0120 (15)0.0034 (14)
C5B0.029 (2)0.027 (3)0.024 (2)0.003 (2)0.0083 (18)0.001 (2)
Br5B0.0531 (3)0.0284 (3)0.0349 (3)0.0024 (2)0.0122 (2)0.0022 (2)
C6B0.030 (2)0.031 (3)0.033 (3)0.003 (2)0.008 (2)0.002 (2)
C61B0.059 (3)0.032 (3)0.033 (3)0.004 (3)0.017 (3)0.005 (2)
N1X0.039 (2)0.039 (3)0.025 (2)0.007 (2)0.0152 (18)0.0029 (19)
C11X0.051 (3)0.045 (4)0.040 (3)0.002 (3)0.013 (3)0.004 (3)
C2X0.027 (2)0.038 (3)0.029 (3)0.001 (2)0.006 (2)0.004 (2)
O2X0.056 (2)0.038 (2)0.031 (2)0.0020 (19)0.0205 (17)0.0044 (17)
C3X0.041 (3)0.034 (3)0.034 (3)0.003 (2)0.011 (2)0.006 (2)
C4X0.043 (3)0.036 (3)0.037 (3)0.004 (2)0.008 (2)0.009 (2)
C5X0.049 (3)0.051 (4)0.022 (3)0.005 (3)0.017 (2)0.007 (2)
Geometric parameters (Å, º) top
N1A—C2A1.356 (7)C4B—O4B1.243 (7)
N1A—C6A1.387 (7)C4B—C5B1.429 (7)
N1A—H1A0.876 (10)C5B—C6B1.384 (7)
C2A—N3A1.312 (7)C5B—Br5B1.871 (5)
C2A—N2A1.332 (7)C6B—C61B1.482 (8)
N2A—H21A0.876 (10)C61B—H61D0.9800
N2A—H22A0.881 (10)C61B—H61E0.9800
N3A—C4A1.381 (7)C61B—H61F0.9800
C4A—O4A1.244 (7)N1X—C2X1.322 (7)
C4A—C5A1.440 (8)N1X—C11X1.439 (8)
C5A—C6A1.345 (8)N1X—C5X1.446 (7)
C5A—Br5A1.869 (5)C11X—H11A0.9800
C6A—C61A1.493 (7)C11X—H11B0.9800
C61A—H61A0.9800C11X—H11C0.9800
C61A—H61B0.9800C2X—O2X1.228 (7)
C61A—H61C0.9800C2X—C3X1.508 (8)
N1B—C2B1.312 (7)C3X—C4X1.516 (8)
N1B—C6B1.357 (7)C3X—H3X10.9900
C2B—N2B1.330 (7)C3X—H3X20.9900
C2B—N3B1.354 (7)C4X—C5X1.548 (9)
N2B—H21B0.875 (10)C4X—H4X10.9900
N2B—H22B0.878 (10)C4X—H4X20.9900
N3B—C4B1.386 (7)C5X—H5X10.9900
N3B—H3B0.876 (10)C5X—H5X20.9900
C2A—N1A—C6A120.4 (4)C4B—C5B—Br5B117.1 (4)
C2A—N1A—H1A118 (4)N1B—C6B—C5B122.5 (5)
C6A—N1A—H1A122 (4)N1B—C6B—C61B115.1 (5)
N3A—C2A—N2A120.1 (5)C5B—C6B—C61B122.4 (5)
N3A—C2A—N1A123.6 (5)C6B—C61B—H61D109.5
N2A—C2A—N1A116.2 (5)C6B—C61B—H61E109.5
C2A—N2A—H21A112 (4)H61D—C61B—H61E109.5
C2A—N2A—H22A124 (5)C6B—C61B—H61F109.5
H21A—N2A—H22A124 (6)H61D—C61B—H61F109.5
C2A—N3A—C4A119.3 (5)H61E—C61B—H61F109.5
O4A—C4A—N3A119.8 (5)C2X—N1X—C11X124.0 (5)
O4A—C4A—C5A122.5 (5)C2X—N1X—C5X116.3 (5)
N3A—C4A—C5A117.7 (5)C11X—N1X—C5X119.7 (5)
C6A—C5A—C4A121.5 (5)N1X—C11X—H11A109.5
C6A—C5A—Br5A121.0 (4)N1X—C11X—H11B109.5
C4A—C5A—Br5A117.5 (4)H11A—C11X—H11B109.5
C5A—C6A—N1A117.5 (5)N1X—C11X—H11C109.5
C5A—C6A—C61A127.1 (5)H11A—C11X—H11C109.5
N1A—C6A—C61A115.4 (5)H11B—C11X—H11C109.5
C6A—C61A—H61A109.5O2X—C2X—N1X126.2 (5)
C6A—C61A—H61B109.5O2X—C2X—C3X125.8 (5)
H61A—C61A—H61B109.5N1X—C2X—C3X108.0 (5)
C6A—C61A—H61C109.5C2X—C3X—C4X106.0 (5)
H61A—C61A—H61C109.5C2X—C3X—H3X1110.5
H61B—C61A—H61C109.5C4X—C3X—H3X1110.5
C2B—N1B—C6B117.2 (5)C2X—C3X—H3X2110.5
N1B—C2B—N2B120.2 (5)C4X—C3X—H3X2110.5
N1B—C2B—N3B123.1 (5)H3X1—C3X—H3X2108.7
N2B—C2B—N3B116.7 (5)C3X—C4X—C5X105.1 (5)
C2B—N2B—H21B122 (5)C3X—C4X—H4X1110.7
C2B—N2B—H22B121 (5)C5X—C4X—H4X1110.7
H21B—N2B—H22B117 (6)C3X—C4X—H4X2110.7
C2B—N3B—C4B123.8 (5)C5X—C4X—H4X2110.7
C2B—N3B—H3B114 (4)H4X1—C4X—H4X2108.8
C4B—N3B—H3B122 (4)N1X—C5X—C4X103.3 (4)
O4B—C4B—N3B121.1 (5)N1X—C5X—H5X1111.1
O4B—C4B—C5B126.1 (5)C4X—C5X—H5X1111.1
N3B—C4B—C5B112.8 (5)N1X—C5X—H5X2111.1
C6B—C5B—C4B120.6 (5)C4X—C5X—H5X2111.1
C6B—C5B—Br5B122.3 (4)H5X1—C5X—H5X2109.1
C6A—N1A—C2A—N3A0.3 (7)C2B—N3B—C4B—C5B0.3 (6)
C6A—N1A—C2A—N2A178.9 (4)O4B—C4B—C5B—C6B179.7 (5)
N2A—C2A—N3A—C4A179.1 (4)N3B—C4B—C5B—C6B0.2 (6)
N1A—C2A—N3A—C4A0.6 (7)O4B—C4B—C5B—Br5B0.9 (7)
C2A—N3A—C4A—O4A178.9 (5)N3B—C4B—C5B—Br5B179.6 (3)
C2A—N3A—C4A—C5A1.2 (6)C2B—N1B—C6B—C5B0.3 (7)
O4A—C4A—C5A—C6A178.5 (5)C2B—N1B—C6B—C61B179.7 (5)
N3A—C4A—C5A—C6A1.6 (7)C4B—C5B—C6B—N1B0.2 (7)
O4A—C4A—C5A—Br5A0.3 (7)Br5B—C5B—C6B—N1B179.6 (4)
N3A—C4A—C5A—Br5A179.5 (3)C4B—C5B—C6B—C61B179.7 (5)
C4A—C5A—C6A—N1A1.3 (7)Br5B—C5B—C6B—C61B0.3 (7)
Br5A—C5A—C6A—N1A179.9 (3)C11X—N1X—C2X—O2X0.5 (8)
C4A—C5A—C6A—C61A176.4 (5)C5X—N1X—C2X—O2X178.1 (5)
Br5A—C5A—C6A—C61A2.4 (7)C11X—N1X—C2X—C3X180.0 (5)
C2A—N1A—C6A—C5A0.7 (6)C5X—N1X—C2X—C3X1.4 (6)
C2A—N1A—C6A—C61A177.4 (4)O2X—C2X—C3X—C4X174.5 (5)
C6B—N1B—C2B—N2B178.3 (4)N1X—C2X—C3X—C4X6.0 (6)
C6B—N1B—C2B—N3B0.3 (7)C2X—C3X—C4X—C5X10.3 (6)
N1B—C2B—N3B—C4B0.3 (7)C2X—N1X—C5X—C4X7.9 (6)
N2B—C2B—N3B—C4B178.4 (4)C11X—N1X—C5X—C4X173.4 (5)
C2B—N3B—C4B—O4B179.8 (5)C3X—C4X—C5X—N1X10.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2X0.88 (1)1.90 (3)2.723 (6)155 (6)
N2A—H21A···O2X0.88 (1)2.11 (3)2.919 (6)153 (6)
N2A—H22A···O4B0.88 (1)1.97 (2)2.839 (6)170 (6)
N2B—H21B···O4Ai0.88 (1)2.11 (4)2.887 (6)147 (6)
N2B—H22B···O4A0.88 (1)1.98 (2)2.855 (6)172 (6)
N3B—H3B···N3A0.88 (1)1.98 (2)2.850 (6)170 (6)
Symmetry code: (i) x+1, y+1, z.
(IV) 2-amino-5-bromo-6-methylpyrimidin-4(3H)-one–2-amino-5-bromo-6-methylpyrimidin-4(1H)-one–2-amino-6-chloropyrimidin-4(3H)-one (0.635/1/0.365) top
Crystal data top
C4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3OF(000) = 762
Mr = 386.58Dx = 1.953 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.270 (5) ÅCell parameters from 1316 reflections
b = 11.423 (4) Åθ = 4.4–25.8°
c = 12.559 (7) ŵ = 5.13 mm1
β = 98.61 (4)°T = 173 K
V = 1314.9 (11) Å3Block, colourless
Z = 40.29 × 0.22 × 0.20 mm
Data collection top
Stoe IPDSII two-circle
diffractometer
2241 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray sourceRint = 0.086
ω scansθmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
h = 119
Tmin = 0.310, Tmax = 0.435k = 1313
7577 measured reflectionsl = 1515
2517 independent reflections
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)] = 0.093Hydrogen site location: mixed
wR(F2) = 0.202H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + 18.9797P]
where P = (Fo2 + 2Fc2)/3
2517 reflections(Δ/σ)max < 0.001
206 parametersΔρmax = 0.55 e Å3
9 restraintsΔρmin = 1.13 e Å3
Crystal data top
C4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3OV = 1314.9 (11) Å3
Mr = 386.58Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.270 (5) ŵ = 5.13 mm1
b = 11.423 (4) ÅT = 173 K
c = 12.559 (7) Å0.29 × 0.22 × 0.20 mm
β = 98.61 (4)°
Data collection top
Stoe IPDSII two-circle
diffractometer
2517 independent reflections
Absorption correction: multi-scan
X-AREA (Stoe & Cie, 2001)
2241 reflections with I > 2σ(I)
Tmin = 0.310, Tmax = 0.435Rint = 0.086
7577 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0939 restraints
wR(F2) = 0.202H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + 18.9797P]
where P = (Fo2 + 2Fc2)/3
2517 reflectionsΔρmax = 0.55 e Å3
206 parametersΔρmin = 1.13 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.2550 (8)0.1571 (7)0.3913 (6)0.0347 (17)
H1A0.181 (7)0.140 (5)0.342 (4)0.042*
C2A0.3287 (11)0.2569 (9)0.3750 (8)0.042 (2)
N2A0.2840 (9)0.3198 (8)0.2871 (7)0.0403 (19)
H2A10.318 (11)0.391 (4)0.283 (9)0.048*
H2A20.197 (5)0.293 (9)0.262 (8)0.048*
N3A0.4456 (8)0.2911 (7)0.4432 (6)0.0345 (17)
C4A0.4908 (10)0.2266 (8)0.5322 (8)0.038 (2)
O4A0.6055 (7)0.2560 (6)0.5926 (5)0.0395 (16)
C5A0.4105 (11)0.1243 (9)0.5528 (8)0.038 (2)
Br5A0.46972 (13)0.03390 (12)0.67526 (10)0.0596 (4)
C6A0.2934 (10)0.0890 (9)0.4817 (8)0.039 (2)
C61A0.2038 (12)0.0148 (10)0.4914 (10)0.051 (3)
H61A0.12700.01980.42890.076*
H61B0.15930.00920.55730.076*
H61C0.26510.08500.49470.076*
N1B0.8520 (9)0.5851 (7)0.4223 (7)0.0384 (18)
C2B0.7625 (11)0.5008 (9)0.4461 (8)0.041 (2)
N2B0.8076 (11)0.4262 (8)0.5297 (8)0.051 (2)
H2B10.903 (2)0.423 (11)0.545 (10)0.062*
H2B20.752 (11)0.366 (7)0.539 (10)0.062*
N3B0.6243 (9)0.4849 (7)0.3897 (7)0.0387 (19)
H3B0.557 (8)0.436 (7)0.405 (8)0.046*
C4B0.5682 (10)0.5539 (8)0.3050 (8)0.036 (2)
O4B0.4456 (8)0.5313 (6)0.2556 (6)0.0443 (17)
C6B0.7984 (10)0.6560 (8)0.3389 (8)0.039 (2)
C5B0.6645 (11)0.6431 (9)0.2799 (8)0.042 (2)
H5B0.63320.69310.21730.050*0.365 (5)
Cl6B0.9109 (11)0.7634 (9)0.3097 (10)0.044 (2)0.365 (5)
Br5B0.60463 (19)0.73940 (14)0.15832 (14)0.0444 (6)0.635 (5)
C61B0.89989 (19)0.74996 (14)0.33160 (14)0.042 (9)0.635 (5)
H61D0.98800.73710.38400.064*0.635 (5)
H61E0.85490.82450.34710.064*0.635 (5)
H61F0.92590.75220.25880.064*0.635 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.031 (4)0.031 (4)0.040 (4)0.005 (3)0.001 (3)0.003 (3)
C2A0.039 (5)0.040 (5)0.045 (5)0.001 (4)0.002 (4)0.007 (5)
N2A0.039 (5)0.038 (5)0.039 (4)0.004 (4)0.010 (4)0.001 (4)
N3A0.033 (4)0.028 (4)0.038 (4)0.004 (3)0.007 (3)0.002 (3)
C4A0.028 (5)0.032 (5)0.052 (6)0.009 (4)0.005 (4)0.005 (4)
O4A0.036 (4)0.038 (4)0.039 (4)0.005 (3)0.009 (3)0.001 (3)
C5A0.043 (5)0.036 (5)0.035 (5)0.001 (4)0.001 (4)0.007 (4)
Br5A0.0529 (7)0.0667 (8)0.0558 (7)0.0105 (6)0.0027 (5)0.0191 (6)
C6A0.028 (5)0.036 (5)0.053 (6)0.002 (4)0.003 (4)0.001 (5)
C61A0.043 (6)0.047 (6)0.062 (7)0.013 (5)0.004 (5)0.008 (6)
N1B0.038 (4)0.037 (4)0.041 (4)0.005 (4)0.006 (4)0.006 (4)
C2B0.033 (5)0.045 (6)0.041 (5)0.002 (4)0.001 (4)0.001 (5)
N2B0.064 (6)0.035 (5)0.051 (5)0.012 (5)0.004 (5)0.018 (4)
N3B0.035 (4)0.034 (4)0.046 (5)0.007 (3)0.001 (4)0.001 (4)
C4B0.033 (5)0.034 (5)0.039 (5)0.002 (4)0.004 (4)0.005 (4)
O4B0.045 (4)0.031 (4)0.054 (4)0.004 (3)0.002 (3)0.006 (3)
C6B0.038 (5)0.034 (5)0.048 (6)0.001 (4)0.012 (4)0.000 (4)
C5B0.046 (6)0.040 (5)0.038 (5)0.008 (5)0.003 (4)0.002 (4)
Cl6B0.048 (5)0.042 (5)0.044 (4)0.015 (4)0.014 (4)0.015 (4)
Br5B0.0484 (10)0.0365 (9)0.0478 (10)0.0031 (7)0.0060 (7)0.0066 (7)
C61B0.039 (12)0.037 (12)0.055 (16)0.004 (9)0.022 (9)0.036 (9)
Geometric parameters (Å, º) top
N1A—C2A1.360 (12)N1B—C6B1.358 (13)
N1A—C6A1.378 (12)C2B—N2B1.368 (13)
N1A—H1A0.879 (9)C2B—N3B1.380 (12)
C2A—N2A1.330 (13)N2B—H2B10.882 (11)
C2A—N3A1.335 (12)N2B—H2B20.881 (10)
N2A—H2A10.878 (10)N3B—C4B1.363 (13)
N2A—H2A20.879 (10)N3B—H3B0.880 (10)
N3A—C4A1.352 (12)C4B—O4B1.238 (11)
C4A—O4A1.256 (11)C4B—C5B1.421 (14)
C4A—C5A1.429 (13)C6B—C5B1.355 (14)
C5A—C6A1.360 (13)C6B—C61B1.439 (9)
C5A—Br5A1.865 (9)C6B—Cl6B1.686 (15)
C6A—C61A1.464 (14)C5B—Br5B1.896 (10)
C61A—H61A0.9800C5B—H5B0.9799
C61A—H61B0.9800C61B—H61D0.9800
C61A—H61C0.9800C61B—H61E0.9800
N1B—C2B1.335 (13)C61B—H61F0.9800
C2A—N1A—C6A121.5 (8)N1B—C2B—N3B122.7 (9)
C2A—N1A—H1A116.4 (19)N2B—C2B—N3B117.8 (9)
C6A—N1A—H1A122.1 (19)C2B—N2B—H2B1112 (8)
N2A—C2A—N3A119.8 (9)C2B—N2B—H2B2118 (8)
N2A—C2A—N1A118.5 (9)H2B1—N2B—H2B2122 (10)
N3A—C2A—N1A121.8 (9)C4B—N3B—C2B122.7 (8)
C2A—N2A—H2A1119 (8)C4B—N3B—H3B110 (7)
C2A—N2A—H2A2105 (7)C2B—N3B—H3B127 (7)
H2A1—N2A—H2A2128 (10)O4B—C4B—N3B119.0 (9)
C2A—N3A—C4A119.5 (8)O4B—C4B—C5B126.8 (9)
O4A—C4A—N3A118.9 (8)N3B—C4B—C5B114.1 (8)
O4A—C4A—C5A121.7 (9)C5B—C6B—N1B123.8 (9)
N3A—C4A—C5A119.3 (9)C5B—C6B—C61B126.9 (9)
C6A—C5A—C4A120.6 (9)N1B—C6B—C61B109.0 (8)
C6A—C5A—Br5A119.0 (8)C5B—C6B—Cl6B120.4 (9)
C4A—C5A—Br5A120.3 (7)N1B—C6B—Cl6B115.8 (8)
C5A—C6A—N1A117.2 (9)C6B—C5B—C4B120.8 (9)
C5A—C6A—C61A126.3 (10)C6B—C5B—Br5B120.7 (8)
N1A—C6A—C61A116.5 (8)C4B—C5B—Br5B118.5 (7)
C6A—C61A—H61A109.5C6B—C5B—H5B120.8
C6A—C61A—H61B109.5C4B—C5B—H5B118.4
H61A—C61A—H61B109.5C6B—C61B—H61D109.5
C6A—C61A—H61C109.5C6B—C61B—H61E109.5
H61A—C61A—H61C109.5H61D—C61B—H61E109.5
H61B—C61A—H61C109.5C6B—C61B—H61F109.5
C2B—N1B—C6B115.8 (8)H61D—C61B—H61F109.5
N1B—C2B—N2B119.5 (9)H61E—C61B—H61F109.5
C6A—N1A—C2A—N2A178.7 (9)N1B—C2B—N3B—C4B0.1 (16)
C6A—N1A—C2A—N3A2.9 (15)N2B—C2B—N3B—C4B180.0 (9)
N2A—C2A—N3A—C4A179.8 (9)C2B—N3B—C4B—O4B177.1 (9)
N1A—C2A—N3A—C4A1.3 (14)C2B—N3B—C4B—C5B0.2 (13)
C2A—N3A—C4A—O4A176.2 (9)C2B—N1B—C6B—C5B1.6 (15)
C2A—N3A—C4A—C5A1.4 (14)C2B—N1B—C6B—C61B173.2 (8)
O4A—C4A—C5A—C6A174.7 (10)C2B—N1B—C6B—Cl6B179.4 (8)
N3A—C4A—C5A—C6A2.8 (15)N1B—C6B—C5B—C4B1.9 (15)
O4A—C4A—C5A—Br5A2.8 (14)C61B—C6B—C5B—C4B171.9 (8)
N3A—C4A—C5A—Br5A179.7 (7)Cl6B—C6B—C5B—C4B179.1 (9)
C4A—C5A—C6A—N1A1.3 (15)N1B—C6B—C5B—Br5B175.3 (8)
Br5A—C5A—C6A—N1A178.8 (7)C61B—C6B—C5B—Br5B10.8 (14)
C4A—C5A—C6A—C61A178.5 (10)Cl6B—C6B—C5B—Br5B3.6 (13)
Br5A—C5A—C6A—C61A1.0 (15)O4B—C4B—C5B—C6B177.8 (10)
C2A—N1A—C6A—C5A1.5 (14)N3B—C4B—C5B—C6B1.1 (14)
C2A—N1A—C6A—C61A178.7 (9)O4B—C4B—C5B—Br5B0.4 (14)
C6B—N1B—C2B—N2B179.4 (9)N3B—C4B—C5B—Br5B176.2 (7)
C6B—N1B—C2B—N3B0.6 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.88 (1)1.99 (3)2.810 (10)154 (7)
N1A—H1A···Br5Bi0.88 (1)2.88 (9)3.429 (8)122 (8)
N2A—H2A1···O4B0.88 (1)2.05 (3)2.901 (12)163 (10)
N2A—H2A2···O4Aii0.88 (1)2.24 (8)2.872 (11)129 (9)
N2A—H2A2···Br5Aii0.88 (1)2.97 (10)3.469 (8)118 (9)
N2B—H2B1···N1Biii0.88 (1)2.24 (2)3.125 (13)178 (12)
N2B—H2B2···O4A0.88 (1)2.03 (4)2.890 (11)164 (11)
N3B—H3B···N3A0.88 (1)2.04 (3)2.903 (11)165 (10)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+2, y+1, z+1.
Isothermal solvent evaporation experiments top
StructureCompound 1 (mg, mmol)Compound 2 (mg, mmol)Solvent (µL)Temperature (K)
(Ia)CIC: 3.4, 0.023AHP: 3.3, 0.034DMF: 50323
(Ib)CIC: 3.4, 0.023AHP: 3.3, 0.034DMAC: 50323
(II)BMIC: 4.6, 0.023ACMP: 3.5, 0.024DMSO: 75323
(III)BMIC: 4.2, 0.021NMP: 170277
(IV)CIC: 3.4, 0.023BMIC: 7.0, 0.034DMAC: 500296
CIC is 6-chloroisocytosine, AHP is 2-aminopyridine, ACMP is 2-amino-4-chloro-6-methylpyrimidine, BMIC is 5-bromo-6-methylisocytosine, DMF is N,N-dimethylformamide, DMAC is N,N-dimethylacetamide, DMSO is dimethylsulfoxide and NMP is N-methylpyrrolidin-2-one.

Experimental details

(Ia)(Ib)(II)(III)
Crystal data
Chemical formulaC5H7N2+·C4H3ClN3O·3C4H4ClN3O2C5H7N2+·2C4H3ClN3O·10C4H4ClN3O·C5H6N2C5H6BrN3O2C5H6BrN3O·C5H9NO
Mr676.322028.97204.04507.21
Crystal system, space groupTriclinic, P1Triclinic, P1Monoclinic, P21/nMonoclinic, P21/n
Temperature (K)173173173173
a, b, c (Å)10.8229 (11), 11.7395 (14), 12.7637 (13)14.0097 (7), 14.0185 (7), 21.4229 (11)9.8154 (13), 9.9532 (8), 14.344 (2)11.7075 (14), 14.0308 (11), 11.8308 (14)
α, β, γ (°)62.633 (8), 70.877 (8), 81.182 (9)83.774 (4), 84.000 (4), 83.554 (4)90, 108.021 (11), 9090, 103.096 (10), 90
V3)1360.7 (3)4137.9 (4)1332.6 (3)1892.8 (4)
Z2284
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.500.496.104.32
Crystal size (mm)0.26 × 0.09 × 0.070.24 × 0.10 × 0.040.35 × 0.30 × 0.250.30 × 0.20 × 0.18
Data collection
DiffractometerStoe IPDSII two-circle
diffractometer
Stoe IPDSII two-circle
diffractometer
Stoe IPDSII two-circle
diffractometer
Stoe IPDSII 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)
Tmin, Tmax0.880, 0.9600.890, 0.9800.220, 0.3100.350, 0.525
No. of measured, independent and
observed [I > 2σ(I)] reflections
22097, 5228, 3077 20468, 16871, 10620 6144, 2480, 1986 10611, 3544, 2736
Rint0.1250.0260.1030.113
(sin θ/λ)max1)0.6150.6260.6100.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.149, 0.92 0.136, 0.379, 1.08 0.076, 0.228, 1.08 0.054, 0.145, 1.00
No. of reflections52281687124803544
No. of parameters4301350201265
No. of restraints14313116
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 refinement
w = 1/[σ2(Fo2) + (0.0722P)2]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.1287P)2 + 31.8979P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.1394P)2 + 4.545P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0855P)2]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.42, 0.431.51, 1.231.06, 1.500.77, 0.76


(IV)
Crystal data
Chemical formulaC4.64H5.27Br0.64Cl0.37N3O·C5H6BrN3O
Mr386.58
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.270 (5), 11.423 (4), 12.559 (7)
α, β, γ (°)90, 98.61 (4), 90
V3)1314.9 (11)
Z4
Radiation typeMo Kα
µ (mm1)5.13
Crystal size (mm)0.29 × 0.22 × 0.20
Data collection
DiffractometerStoe IPDSII two-circle
diffractometer
Absorption correctionMulti-scan
X-AREA (Stoe & Cie, 2001)
Tmin, Tmax0.310, 0.435
No. of measured, independent and
observed [I > 2σ(I)] reflections
7577, 2517, 2241
Rint0.086
(sin θ/λ)max1)0.614
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.093, 0.202, 1.19
No. of reflections2517
No. of parameters206
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + 18.9797P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.55, 1.13

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

Hydrogen-bond geometry (Å, º) for (Ia) top
D—H···AD—HH···AD···AD—H···A
N2A—H21A···O4B0.885 (19)2.08 (2)2.960 (4)173 (4)
N2A—H22A···N1C0.880 (19)2.14 (2)3.014 (4)172 (4)
N2B—H21B···N1D0.873 (19)2.14 (2)3.016 (4)178 (4)
N2B—H22B···O4A0.897 (19)1.92 (2)2.820 (4)177 (4)
N3B—H3B···N3A0.875 (19)2.03 (2)2.893 (4)167 (4)
N2C—H21C···N1A0.880 (19)2.12 (2)2.999 (4)174 (4)
N3C—H3C···O4Di0.884 (19)1.85 (2)2.730 (4)174 (4)
N2D—H21D···N1B0.888 (19)2.06 (2)2.936 (4)171 (4)
N3D—H3D···O4Cii0.891 (19)1.88 (2)2.760 (4)170 (4)
N1E—H1E···O4A0.890 (19)1.70 (2)2.554 (4)160 (4)
N2E—H21E···O4Biii0.862 (19)2.08 (2)2.905 (4)161 (4)
N2E—H22E···O4Biv0.889 (19)2.26 (2)3.086 (4)155 (3)
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z1; (iii) x, y1, z; (iv) x+1, y+1, z+1.
Root mean-square deviations (r.m.s.d.) for (Ib) for non-H atoms (Å) top
Moleculer.m.s.d.Moleculer.m.s.d.Moleculer.m.s.d.
A0.0176G0.0226O0.0134
B0.0076H0.0147P0.0079
C0.0191I0.0104R0.0384
D0.0167K0.0093S0.0439
E0.0083L0.0204
F0.0109M0.0107
Hydrogen-bond geometry (Å, º) for (Ib) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A1···N1Fi0.880 (5)2.25 (2)3.107 (11)166 (6)
N2A—H2A2···O4B0.881 (5)1.953 (15)2.829 (11)173 (5)
N3A—H3A···N3B0.880 (5)2.03 (3)2.900 (11)168 (10)
N2B—H2B1···O4A0.880 (5)2.091 (15)2.960 (11)169 (3)
N2B—H2B2···N1C0.880 (5)2.28 (2)3.140 (11)167 (7)
N2C—H2C1···N1B0.880 (5)2.09 (4)2.936 (11)160 (11)
N3C—H3C···O4D0.880 (5)1.962 (16)2.839 (11)175 (11)
N2D—H2D1···N1E0.880 (5)2.13 (2)2.991 (11)167 (6)
N3D—H3D···O4C0.880 (5)1.86 (2)2.732 (10)169 (10)
C5D—H5D···Cl6Gii0.952.883.769 (11)155.7
N2E—H2E1···N1D0.880 (5)2.048 (16)2.917 (11)169 (5)
N3E—H3E···O4F0.880 (5)1.92 (3)2.772 (11)164 (11)
N2F—H2F1···N1Aiii0.881 (5)2.057 (17)2.930 (11)171 (6)
N2F—H2F2···N2R0.880 (5)2.44 (4)3.29 (2)162 (9)
N3F—H3F···O4E0.880 (5)1.90 (3)2.761 (11)166 (10)
N2G—H2G1···O4H0.880 (5)2.03 (3)2.892 (11)166 (10)
N2G—H2G2···N1Miv0.880 (5)2.27 (3)3.120 (11)162 (9)
C5G—H5G···Cl6Dii0.952.733.638 (10)160.9
N2H—H2H1···N1I0.881 (5)2.176 (15)3.045 (11)169 (3)
N2H—H2H2···O4G0.880 (5)1.965 (15)2.842 (11)175 (9)
N3H—H3H···N3G0.880 (5)2.00 (2)2.870 (11)169 (10)
C5H—H5H···Cl6Ev0.952.933.837 (10)161.1
N2I—H2I1···N1H0.881 (5)2.04 (3)2.900 (12)165 (9)
N3I—H3I···O4K0.880 (5)1.889 (17)2.764 (11)173 (10)
N2K—H2K2···N2Svi0.880 (5)2.28 (4)3.13 (2)161 (8)
N3K—H3K···O4I0.880 (5)1.882 (14)2.761 (11)176 (10)
N2L—H2L1···N1K0.880 (5)2.14 (3)2.999 (11)164 (9)
N2L—H2L2···N2O0.880 (5)2.59 (4)3.436 (14)162 (10)
N3L—H3L···O4M0.77 (11)2.02 (12)2.782 (11)169 (12)
N2M—H2M1···N1Gvii0.880 (5)2.050 (14)2.927 (11)175 (6)
N3M—H3M···O4L0.96 (11)1.83 (11)2.794 (11)175 (10)
N1O—H1O···O4Gviii0.97 (11)1.64 (12)2.598 (11)167 (10)
N2O—H2O1···O4M0.881 (5)1.978 (12)2.810 (12)157 (3)
N2O—H2O2···N1Rix0.881 (5)2.27 (8)2.971 (13)136 (10)
N1P—H1P···O4Ax0.891 (5)2.007 (13)2.769 (10)142.8 (16)
N2P—H2P1···O4B0.880 (5)1.89 (3)2.719 (11)157 (8)
N2P—H2P2···O4H0.880 (5)2.11 (5)2.872 (11)144 (7)
C3P—H3P···O4Lviii0.952.493.186 (11)130.3
N2R—H2R1···O4Fxi0.880 (5)2.36 (5)3.05 (2)136 (6)
N2R—H2R2···O4E0.880 (5)2.12 (6)2.92 (2)152 (12)
C3R—H3R···O4Dxii0.952.443.37 (4)166.8
C5R—H5R···O4Ixiii0.952.453.28 (2)144.7
C4O—H4O···O4Cxiv0.952.643.577 (12)170.5
Symmetry codes: (i) x1, y+2, z; (ii) x+2, y1, z+1; (iii) x+1, y2, z; (iv) x+2, y1, z; (v) x+2, y1, z; (vi) x2, y+2, z+1; (vii) x2, y+1, z; (viii) x, y+1, z+1; (ix) x+1, y1, z; (x) x+2, y, z; (xi) x+3, y3, z; (xii) x+3, y2, z; (xiii) x+2, y2, z1; (xiv) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.88 (2)1.92 (4)2.765 (8)160 (9)
N1A—H1A···Br5Bi0.88 (2)3.03 (9)3.525 (7)118 (7)
N2A—H2A1···O4B0.87 (2)2.04 (4)2.871 (9)160 (10)
N2A—H2A2···O4Aii0.88 (2)2.05 (6)2.807 (8)144 (9)
N2B—H2B1···Br5Aiii0.891 (16)3.004 (13)3.852 (6)160 (2)
N2B—H2B2···O4A0.894 (16)1.938 (19)2.831 (10)176 (9)
N3B—H3B···N3A0.87 (2)2.03 (3)2.883 (10)164 (9)
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+3/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2X0.876 (10)1.90 (3)2.723 (6)155 (6)
N2A—H21A···O2X0.876 (10)2.11 (3)2.919 (6)153 (6)
N2A—H22A···O4B0.881 (10)1.968 (17)2.839 (6)170 (6)
N2B—H21B···O4Ai0.875 (10)2.11 (4)2.887 (6)147 (6)
N2B—H22B···O4A0.878 (10)1.983 (15)2.855 (6)172 (6)
N3B—H3B···N3A0.876 (10)1.983 (16)2.850 (6)170 (6)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.879 (9)1.99 (3)2.810 (10)154 (7)
N1A—H1A···Br5Bi0.879 (9)2.88 (9)3.429 (8)122 (8)
N2A—H2A1···O4B0.878 (10)2.05 (3)2.901 (12)163 (10)
N2A—H2A2···O4Aii0.879 (10)2.24 (8)2.872 (11)129 (9)
N2A—H2A2···Br5Aii0.879 (10)2.97 (10)3.469 (8)118 (9)
N2B—H2B1···N1Biii0.882 (11)2.244 (18)3.125 (13)178 (12)
N2B—H2B2···O4A0.881 (10)2.03 (4)2.890 (11)164 (11)
N3B—H3B···N3A0.880 (10)2.04 (3)2.903 (11)165 (10)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+2, y+1, z+1.
 

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